Tricyclic oxazolidinone antibiotic compounds

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to a compound of formula (I)CE, wherein "-----" means a bond, V represents CH, and U represents CH or N, or "-----" means a bond, V represents CR6 and U represents CH, or also "-----" means a bond, V represents N and U represents CH, or "-----" is absent, V represents CH, and U represents CH2, NH or NR9; R0 represents H, or provided "-----" means a bond, can also represent C1-3alkoxygroup; R1 represents H, halogen, cyanogroup, C1-3alkyl or ethinyl; R2 represents H, acetyl or a group of formula -CH2-R3; R3 represents H, C1-3alkyl or C1-3hydroxyalkyl; R4 represents H, or provided n is other than 0, and R5 means H, can also represent OH; R5 represents H, C1-3alkyl, C1-3hydroxyalkyl, C1-3aminoalkyl, C1-3alkoxyC1-3alkyl, carboxyl group or C1-3alkoxycarbonyl; R6 represents C1-3hydroxyalkyl, carboxyl group, C1-3alkoxycarbonyl or a group -(CH2)q-NR7R8, wherein q is 1, 2 or 3 and each of R7 and R8 independently represents H or C1-3alkyl, or R7 and R8 together with a nitrogen atom to which they are attached, form a pyrrolodinyl or piperidinyl ring; R9 represents C1-3alkyl, 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl; A represents -(CH2)p-, -CH2CH2CH(OH)- or -COCH2CH(OH)-; G represents a phenyl group which is mono- or disubstituted in m- and/or n-position(s)by substitutes independently specified C1-4alkyl, C1-3alkoxygroup and halogen, or G means a group of one of formulas below G1 and G2, wherein Q means O or S, and X means CH or N; and each Y1, Y2 and Y3 represents CH, or one of Y1 and Y3 represents N, and the other one represents CH; and n is equal to 0, provided A represents -CH2CH2CH(OH)- or -COCH2CH(OH)-, and n is equal to 0, 1 or 2, provided A represents (CH2)p, wherein p is equal to 1, 2, 3 or 4, provided a sum of n and p is then equal to 2, 3 or 4; or a pharmaceutically acceptable salt of this compound.

EFFECT: compound of formula (I)CE or its pharmaceutically acceptable salt are applicable as a therapeutic agent for preventing or treating a bacterial infection.

29 cl, 2 tbl, 202 ex

 

The present invention relates to tricyclic oxazolidinone antibiotic compounds, pharmaceutical antibacterial composition containing them and the use of these compounds in the manufacture of a medicinal product for the treatment of infections (e.g. bacterial infections). These compounds are used as antimicrobial agents, effective against a number of pathogens of humans and animals, including, among others, gram-positive and gram-negative aerobic and anaerobic bacteria and mycobacteria.

The intensive use of antibiotics has a selective evolutionary pressure on microorganisms, contributing to the production in them genetically formed of the mechanisms of resistance. Modern medical and socio-economic behavior exacerbates the problem of resistance development, creating conditions for slow growth of pathogenic microorganisms, for example, artificial joints, and in terms of long-term support of the reserves of the owner, such as immunological "compromised" patients.

In the hospital the increasing number of strains of Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus spp. and Pseudomonas aeruginosa, which are the main sources of infections, making them resistant to many drugs and causes difficulties in Les is the situation, until a cure is not possible at all:

S. aureus is resistant against β-lactams, quinolones, and now even to vancomycin;

S. pneumoniae is becoming resistant against penicillin or quinolone antibiotics and even to new macrolides;

- Enteroccocci are resistant against chinolone and vancomycin and β-lactam antibiotics have no effective impact on these strains;

- Enterobacteriacea are resistant against cephalosporin and chinolone;

- P. Aeruginosa are resistant against β-lactam and chinolone.

In addition, the propagation velocity multilocational resistance gram-negative strains, such as Enterobacteriacea and Pseudomonas aeruginosa, is constantly increasing, resulting in the re-emerging organisms, such such organisms like Acinetobacter spp. or Clostridium difficile, which were selected during therapy with the currently used antibiotics, have become a real problem in hospitals. Consequently, there is a great medical need for new antibacterial agents are able to overcome multilocational resistance of gram-negative bacteria, such as A. baumannii, ESBL-producing E. coli and Klebsiella species, and Pseudomonas aeruginosa (George H.Talbot et al., Clinical Infectious Diseases, (2006), 42, 657-68)./p>

In addition, microorganisms resistant infections are increasingly recognized as causes or contributing factors of some chronic diseases such as peptic ulcers or heart disease.

Estrellitas antibiotic compounds have already been described in WO 2007/071936 and WO 2007/122258 (disclosed 3-oxo-1,2-dihydro-3H-2A,6-datacenter-1-methylene derivatives), WO 2007/081597 (disclosed 4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-de]quinoline-1-methylene derivatives), WO 2007/115947 (disclosed 3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-methylene derivatives) and WO 2008/003690 (disclosed, in particular, 1-(7-oxo-5,6,9a,9b-tetrahydro-4H,7H-1,6A-Desafinado-5-yl)piperidine-4-ilen and 1-(5-oxo-2,3,7a,10b-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-yl)piperidine-4-ilen derivatives). Recently been described estrellitas antibiotics in publications WO 2008/120003, WO 2008/128942, WO 2008/128953, WO 2008/128962, WO 2009/000745 and WO 2009/087153 (all filed before, but published after the earliest data about the priority of this application).

Quinoline, naphthyridine or hinoksalinovym spirooxazines antibiotic compounds have already been described in WO 2008/026172. Quite recently some other antibiotic compounds, including oxazolidinones fragment, in the publications WO 2008/126024, WO 2008/126034, WO 2009/077989 and WO 2009/104159 (all filed before, but published after semichronic data about the priority of this application).

In addition, estrellitas antibiotics, including oxazolidinones fragment, have been described in WO 2009/104147 (date of priority or filing date which is earlier than some or all of the data of this application, while the publication took place after the priority date of this application).

The present applicants have discovered a new family of tricyclic antibiotic compounds of the formula (I)below.

Various embodiments of the present invention are presented below:

i) the Invention primarily relates to compounds of formula (I)

,

where

"" means a connection or missing;

R0represents H, or when "" denotes a bond, may also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H, halogen (preferably F, Cl or Br), cyano, C1-3alkyl (preferably methyl) or ethinyl;

U represents CH or N when "" denotes a bond, or in the case where "" no, U represents CH2, NH or NR9;

V represents CH, CR6or N;

R2represents H, C1-3alkyls bonil or a group of formula-CH 2-R3;

R3represents H, C1-3alkyl or C1-3hydroxyalkyl;

R4represents N, or when n is 0 and R5denotes H, can also be a HE;

R5represents H, C1-3alkyl (preferably methyl), C1-3hydroxyalkyl (preferably hydroxymethyl)1-3aminoalkyl (preferably aminomethyl)1-3alkoxyl1-3alkyl (preferably methoxymethyl), carboxyl group or1-3alkoxycarbonyl (preferably methoxycarbonyl);

R6represents a C1-3hydroxyalkyl (preferably hydroxymethyl, carboxypropyl,1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q denotes 1, 2 or 3 and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl, piperidinyl, morpholinyl or thiomorpholine ring;

R9represents a C1-3alkyl (preferably, methyl), 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl;

And represents -(CH2)p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;

G represents a phenyl group, which is samewe the Noah once or twice in the m - and/or p-position(s) substituents, selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and; halogen (preferably F), with C1-3alkoxygroup is a preferably linear C1-3alkoxygroup located in the p-position, or G represents a group of the following formula G1and G2

,

where

Q denotes O or S, and X denotes CH or N; and

Y1, Y2and Y3each represents CH, or Y1and Y3each represents CH and Y2represents N, or Y1represents N, Y2represents CH or N and Y3represents CH, or Y1and Y2each represents CH and Y3represents N; and

n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3, or 4 (for example, when n is 0, p is not equal to 1, when n is 1, p is not equal to 4, and when n is 2, R is not equal to either 3 or 4);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (I).

In the following paragraphs presents the definitions of the various chemical fragments for compounds according to the invention. Specified the distribution are designed for uniform application throughout the description and in the claims, unless otherwise specified, and if the definitions are not subject to wider or, conversely, a narrower interpretation.

The term "alkyl", used alone or in combination, refers to a saturated linear or branched alkyl group containing from one to four carbon atoms. The term "C1-xalkyl" (x represents an integer) refers to a linear or branched alkyl group containing from 1 to x carbon atoms. For example, With1-4alkyl group contains from 1 to 4 carbon atoms. Typical examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. The preferred groups are methyl and ethyl, most preferred is methyl.

The term "alkoxygroup", used alone or in combination, refers to linear or branched alkoxygroup containing from one to four carbon atoms. The term "Cx-yalkoxygroup" (x and y each is an integer) refers to alkoxygroup by definition, above, containing from x to y carbon atoms. For example, C1-3alkoxygroup contains from 1 to 3 carbon atoms. Typical examples of alkoxygroup include a methoxy group, ethoxypropan, n-propoxylate and isopropoxy. Preferred groups are methoxy group and atxigru the PA.

The term "hydroxyalkyl" refers to linear or branched alkyl group containing from one to four carbon atoms, in which one of the hydrogen atoms replaced by a hydroxyl group. The term "C1-xhydroxyalkyl" (x is an integer) refers to a hydroxyalkyl group, where the alkyl group contains from 1 to x carbon atoms. Typical examples of C1-3hydroxyalkyl groups include, but are not limited to, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl and 2-hydroxypropyl. Preferred C1-3hydroxyalkyl groups are hydroxymethyl and 2-hydroxypropyl. The most preferred C1-3hydroxyalkyl group is hydroxymethyl.

The term "aminoalkyl" refers to linear or branched alkyl group containing from one to four carbon atoms, where one of the hydrogen atoms is substituted by an amino group. The term "C1-xaminoalkyl" (x is an integer) refers to aminoalkyl group, where the alkyl group contains from 1 to x carbon atoms. Typical examples of C1-3lipoyllysine groups include, but are not limited to, aminomethyl, 2-amino-ethyl, 1-amidoethyl and 2-aminopropyl. Preferred C1-3aminoalkyl groups are aminomethyl and 2-aminopropyl. The most preferred C1-3aminoalkyl group is aminomethyl./p>

The term "alkoxyalkyl" refers to alkoxyalkyl group, in which alkoxygroup stands With1-4alkoxygroup and denotes an alkyl group With1-4alkyl group. The term "C1-xalkoxy-C1-4alkyl" (x and y each independently of one another are integers) refers to alkoxyalkyl group, where alkoxygroup contains from 1 to x carbon atoms and the alkyl group contains from 1 to y carbon atoms. Typical examples1-3alkoxy-C1-3alkyl groups include, but are not limited to, methoxymethyl and ethoxymethyl. The most preferred1-3alkoxy-C1-3the alkyl group is methoxymethyl.

The term "alkylaryl" refers to alkylcarboxylic group, in which alkyl denotes a linear or branched alkyl group containing from one to four carbon atoms. The term "C1-xalkylsulphonyl" (x is an integer) refers to alkylcarboxylic group, where alkyl is a linear or branched alkyl group containing from 1 to x carbon atoms. Typical examples of C1-3alkylcarboxylic groups include acetyl, ethylcarboxyl, 1-propylboronic and 2-propylmalonic. Preferred C1-3alkylcarboxylic groups are acetyl and ethylcarboxyl. The most preferred C1-3alkylcarboxylic group is what I acetyl.

The term "alkoxycarbonyl" refers to alkoxycarbonyl group, in which alkoxygroup is a linear or branched alkoxygroup containing from one to four carbon atoms. The term "C1-xalkoxycarbonyl" (x is an integer) refers to alkoxycarbonyl group, in which alkoxygroup is a linear or branched alkoxygroup containing from 1 to x carbon atoms. Typical examples1-3alkoxycarbonyl groups include methoxycarbonyl, etoxycarbonyl, 1-propoxycarbonyl and 2-propoxycarbonyl. Preferred C1-3alkylcarboxylic groups are methoxycarbonyl and etoxycarbonyl. The most preferred C1-3alkylcarboxylic group is etoxycarbonyl.

The term "halogen" refers to fluorine, chlorine, bromine or iodine, preferably by fluorine or chlorine.

When in the formula

Rather it represents a radical-CH2CH2CH(OH)-, I mean that CH2-the part of the said moiety is attached to the adjacent nitrogen atom, while CH(OH)-the part of the said moiety is attached to oxazolidinedione ring.

This applies to all radicals denoted by the letter A (for example, the radicals A'referred to in preparative methods). If, for example, stated that in the substructure And represent the screens a-PINES 2CH(OH)radical, this means that the CO-group of the given radical is attached to the adjacent nitrogen atom, while CH(OH)-group specified radical attached to oxazolidinedione ring. In other words, the left part of the radical is always attached to the right side of the radical, which is the closest on the left side.

In this description, the communication is interrupted wavy line indicates the point of attachment of the radical to the rest of the molecule. For example, the radical as shown below,

denotes 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl.

The compounds of formula (I) according to the present invention can contain one or more stereogenic or asymmetric centers, such as one or more asymmetric carbon atoms. The compounds of formula (I) may thus be present as mixtures of stereoisomers or, preferably, in the form of pure stereoisomers. Mixture of stereoisomers can be separated using methods known to experts in the field of engineering.

When the indication of the absolute stereochemical configuration(R)or(S)" is missing in the connection name despite the presence of the corresponding asymmetric carbon atom, this means that the name of this compound is or compound with (R)-configuration, or to connect the Oia, with (S)-configuration.

The relative configuration of stereoisomers having two asymmetric center, denoted in the text as (R*,R*), and applies or a stereoisomer (R,R)-configuration, or a stereoisomer (S,S)-configuration, and the designation (R*,S*) applies or a stereoisomer (R,S)-configuration, or a stereoisomer (S,R)-configuration. So, for example, methyl ester (1R*,2R*)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid is or methyl ether (1R,2R)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2D-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid, or methyl ether (1S,2S)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid.

The present invention also includes isotope-labeled compounds, in particular marked with2H (deuterium) the compounds of formula (I), with labeled compounds are identical to the compounds of formula (I) and differ only in that one or more atoms replaced by an atom having the same atomic number but differing in atomic weight of the atoms occurring in nature. Labeled isotope compounds, in particular labeled2H (deuterium) connection is ormula (I), and their salts included in the scope of the present invention. Substitution of hydrogen heavier isotope2H (deuterium) leads to greater metabolic stability, for example, that in vivo increases the half-life or reduces the required dosage, or may lead to reduced inhibition of P450 enzymes, which improves the security profile. In one embodiment of the invention the compounds of formula (I) are not labeled with an isotope, or they state only one or more deuterium atoms. In modifications of the compounds of formula (I) are not in the state of the isotope. Isotopically labeled compounds of formula (I) can be obtained analogously to the methods described below, but using appropriate isotopic variants of the respective reagents or starting materials.

The term "pharmaceutically acceptable salts" refers to non-toxic additive salts of inorganic or organic acids and/or bases. More detailed information can be found in the publication "Salt selection for basic drugs", Int. J. Pharm., (1986), 33, 201-217.

In addition, the term "room temperature"as used herein, refers to a temperature of 25°C.

When we are not talking about temperatures, the term "approximately", located in front of the numerical value "X"refers in the customary application of the interval, the composition is shining from X minus 10% of X to X plus 10% of X, and preferably, the interval of X minus 5% of X to X plus 5% of X. In the special case regarding temperatures, the term "approximately"in front of the temperature "Y"refers in the customary application to the temperature interval of Y minus 10 C to Y plus 10°C., and preferably to an interval of Y minus 5 to Y plus 5 C.

ii) the Invention applies in particular to compounds of the formula (I)described in embodiment i), which are also compounds of formula (IP3)

,

where

"" means a connection or missing;

R0represents H, or when "" denotes a bond, may also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H, halogen (preferably F or Br), cyano, or C1-3alkyl (preferably, methyl);

U represents CH or N when "" denotes a bond, or in the case where "" no, U represents CH2or NH;

V represents CH, CR6or N;

R2represents H, C1-3alkylsulphonyl or a group of formula-CH2-R3;

R3represents H, C1-3alkyl or C1-3hydrox is alkyl;

R4represents N, or when n is 0 and R5denotes H, can also be a HE;

R5represents H, C1-3alkyl (preferably, methyl), (C1-3hydroxyalkyl (preferably hydroxymethyl)1-3alkoxy-C1-3alkyl (preferably, methoxymethyl) or C1-3alkoxycarbonyl (preferably methoxycarbonyl);

R6represents a C1-3hydroxyalkyl (preferably, hydroxymethyl), a carboxyl group, a C1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q is 1, 2 or 3 and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl, piperidinyl, morpholinyl or thiomorpholine ring;

And represents -(CH2)p-, -CH2CH2CH(OH)- or-COCH2CH(OH)-;

G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen (preferably F), with C1-3alkoxygroup is a preferably linear C1-3alkoxygroup and is the p-position; or G represents a group of one of the following formulas G1and G2

,

where

Q denotes O or S, and X denotes CH or N; and

Y1, Y2and Y3each represents CH, or Y1and Y3each represents CH and Y2represents N, or Y1represents N, Y2represents CH or N and Y3represents CH, or Y1and Y2each represents CH and Y3represents N; and

n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3, or 4 (for example, when n is 0, p is not equal to 1, when n is 1, p is not equal to 4, and when n is 2, R is not equal to either 3 or 4);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (IP3).

iii) the Invention further relates preferably to compounds of formula (I) according to option i) or ii)that are also compounds of formula (IP2)

,

where

"" means a connection or missing;

R0represents H, or when "" the seat is that the connection, can also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H or halogen (preferably F);

U represents CH or N when "" denotes a bond, or in the case where "" no, U represents CH2or NH;

V represents CH or N;

R2represents H or a group of formula-CH2-R3where R3denotes hydrogen, C1-3alkyl or C1-3hydroxyalkyl;

And represents -(CH2)p-, -CH2CH2CH(OH)- or-COCH2CH(OH)-;

G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen (preferably F), With1-3alkoxygroup is a preferably linear C1-3alkoxygroup and is in para-position; or G represents a group of one of the following formulas G1and G2

,

where

Q denotes O or S, and X denotes CH or N; and

Y1, Y2and Y3each represents CH, or Y1and Y3each represents CH and Y2 represents N, or Y1represents N, Y2represents CH or N and Y3represents CH, or Y1and Y2each represents CH and Y3represents N; and

n is 0 when a is a-CH2CH2CH(OH)- or-COCH2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3, or 4 (for example, when n is 0, p is not equal to 1, when n is 1, p is not equal to 4, and when n is 2, R is not equal to either 3 or 4);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (IP2).

iv) the Invention relates also to compounds of formula (I) according to the variant i), ii) or iii)that are also compounds of formula (IP1)

,

where

"" means a connection or missing;

R1represents H or halogen (preferably F);

V represents CH or N;

U represents CH or N, or in the case where "" no, U represents CH; or NH;

G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and is of alogena (preferably, F), With1-3alkoxygroup is a preferably linear C1-3alkoxygroup and is in para-position; or G represents a group of one of the following formulas G1and G2

,

where

Q denotes O or S, and X denotes CH or N; and

Y1, Y2and Y3each represents CH, or Y1and Y3each represents CH and Y2represents N, or Y1represents N, Y2represents CH or N and Y3represents CH, or Y1and Y2each represents CH and Y3represents N; and

n is 0, 1 or 2 and p is 1, 2 or 3, provided that the sum of n and p is equal to or 2, or 3 (for example, when n is 0, p is 2 or 3, when n is 1, p is either 1 or 2 and when n is 2, p is 1);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (IP).

v) In particular, the invention relates to compounds of formula (I) according to option (i) which are also compounds of formula (ICE)

,

where

"" denotes a bond, V represents CH and U represents CH or N, or "" denotes a bond, V represents CR6and U made the focus of a SN, or "" denotes a bond, V represents N and U represents CH, or

"" no, V represents CH and U represents CH2, NH or NR9;

R0represents H, or when "" denotes a bond, may also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H, halogen (preferably F, Cl or Br), cyano, C1-3alkyl (preferably methyl) or ethinyl;

V represents CH, CR6or N;

R2represents H, acetyl or a group of formula-CH2-R3;

R3represents hydrogen, C1-3alkyl or C1-3hydroxyalkyl;

R4represents N, or when n is 0 and R5denotes H, can also be a HE;

R5represents H, C1-3alkyl (preferably methyl), C1-3hydroxyalkyl (preferably, hydroxymethyl), C1-3aminoalkyl (preferably aminomethyl)1-3alkoxy-C1-3alkyl (preferably, methoxymethyl), carboxyl group or C1-3alkoxycarbonyl (preferably methoxycarbonyl);

R6represents a C1-3hydroxyalkyl (preferably, hydroxymethyl), to roxylenol group, C1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q is 1, 2 or 3 (preferably, 1) and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl or piperidinyl ring (preferably, pyrrolidinyl ring);

R9represents a C1-3alkyl (preferably, methyl), 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl;

And represents -(CH2)p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;

G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen (preferably F), With1-3alkoxygroup is a preferably linear C1-3alkoxygroup and is in para-position; or G represents a group of one of the following formulas G1and G2

,

where

Q denotes O or S, and X denotes CH or N; and

each of the Y1and Y3represents CH, or one of the Y1and Y3represents N and the other represents the t a CH; and

n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3, or 4 (for example, when n is 0, p is not equal to 1, when n is 1, p is not equal to 4, and when n is 2, R is not equal to either 3 or 4);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (ICE).

vi) Also, in particular, the invention relates to compounds of formula (I) according to the variant i), (ii) or (v)that are also compounds of formula (ICEP3)

,

where

"" denotes a bond, V represents CH and U represents CH or N, or "" denotes a bond, V represents CR6and U represents CH, or also "" denotes a bond, V represents N and U represents CH, or

"" no, V represents CH and U represents CH2or NH;

R0represents H, or when "" denotes a bond, may also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H, halogen (preferably F or Br), cyano or-3 alkyl (preferably, methyl);

V represents CH, CR6or N;

R2represents H, acetyl or a group of formula-CH2-R3;

R3represents hydrogen, C1-3alkyl or C1-3hydroxyalkyl;

R4represents H or, when n is 0 and R5denotes H, can also be a HE;

R5represents H, C1-3alkyl (preferably, methyl), C1-3hydroxyalkyl (preferably hydroxymethyl)1-3alkoxy-C1-3alkyl (preferably, methoxymethyl) or C1-3alkoxycarbonyl (preferably methoxycarbonyl);

R6represents a C1-3hydroxyalkyl (preferably, hydroxymethyl), a carboxyl group, a C1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q is 1, 2 or 3 (preferably, 1) and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl or piperidinyl ring (preferably, pyrrolidinyl ring);

And represents -(CH2)p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;

G represents a phenyl group which is once or twice Thames is authorized in the m - and/or p-position substituents, selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen (preferably F), with C1-3alkoxygroup preferably represents a linear C1-3alkoxygroup and is in para-position; or G represents a group of one of the following formulas G1and G2

,

where

Q denotes O or S, and X denotes CH or N, and

each of the Y1and Y3represents CH, or one of the Y1and Y3represents N and the other represents CH; and

n is 0 when a is a-CH2CH2CH(OH)- or-COCH2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3, or 4 (for example, when n is 0, p is not equal to 1, when n is 1, p is not equal to 4 and when n is 2, R is not equal to either 3 or 4);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (ICE).

vii) the Invention also relates to compounds of formula (I) options (i), ii), iii), v) or vi)that are also compounds of formula (ICEP2)

,

where

"" denotes a bond, V represents CH and U represents CH or N or V represents Soboh is N and U represents CH, or "" no, V represents CH and U represents CH2or NH;

R0represents H, or when "" means a connection can also be a1-3alkoxygroup (in particular, methoxy group);

R1represents H or halogen (preferably F);

R2represents H or a group of formula-CH2-R3while R3represents a C1-3hydroxyalkyl;

And represents -(CH2)p-, -CH2CH2CH(OH)- or-COCH2CH(OH)-;

G represents a phenyl group which is substituted once in the m-position and once in the p-position substituents, independently selected from each other from C1-4of alkyl and halogen (preferably F), G represents a phenyl group which is substituted once to the p-position of Deputy selected from C1-4the alkyl and C1-3alkoxygroup, or G represents a group of one of the following formulas With1and G2'

,

where

X represents CH or N and Q represents O or S;

each of the Y1and Y3represents CH, or one of the Y1and Y3represents N, and d is ugogo represents CH;

n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)p, p is equal to 1, 2, 3, or 4, provided that when n is 0, p is 2 or 3, when n is 1, p is 1, 2 or 3 and when n is 2, R is 1;

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (ICEP2).

viii) the Invention is related to compounds of formula (I) according to one of the options (i)-(vii), which are also compounds of formula (ICEP1)

,

where

R1represents H or halogen (preferably F);

"" denotes a bond, V represents CH and U represents CH or N, or V represents N and U represents CH, or "" no, V represents CH and U represents CH2;

G represents a phenyl group which is substituted once in the m-position and once in the p-position substituents, independently selected from each other from C1-4of alkyl and halogen (preferably F), or G represents a group having one of the following formulas G1and G2'

,

where Q represents O or S;

n Rav is about 0, 1 or 2 and p is 1, 2 or 3, provided that the sum of n and p is equal to or 2, or 3 (for example, when n is 0, p is 2 or 3, when n is 1, p is 1 or 2 and when n is 2, p is 1);

and to the salts (in particular pharmaceutically acceptable salts) of compounds of formula (ICEP1).

ix) According to one main variant of implementation of the present invention the compounds of formula (I) by one of the following (i)to(viii)above are those in which R1represents a halogen (preferably F, Cl or Br, preferably F or Br, in particular, F).

x) another main variant of implementation of the present invention the compounds of formula (I) by one of the following (i)to(viii)above shall be such that R1represents N.

xi) According to the following main variant of implementation of the present invention the compounds of formula (I) according to the variant (i), (ii), (v) or (vi)above are those in which R1represents a C1-3alkyl (preferably, methyl).

xii) According to yet another the next main option of implementation of the present invention the compounds of formula (I) according to option (i) or (v)above are those in which R1is ethinyl.

xiii) One main variant embodiment of the invention relates to compounds of formu the uly (I) by one of the following (i)to(xii), above, where V represents CH (preferably to compounds of formula (I) according to the variant (iv) or (viii), where V represents CH and R1represents fluorine).

xiv) the Other main variant of implementation of the present invention relates to compounds of formula (I) according to one of the embodiments of the invention (i)to(xii)above, where V represents N (preferably, for compounds of formula (I) according to the variant embodiment of the invention (iv) or (viii), where V represents N and R1represents fluorine).

xv) the Next main option of carrying out the invention relates to compounds of formula (I) according to variants of the invention (i), (ii), (v) or (vi)above, where V represents CR6.

xvi) According to one sub-option of option of carrying out the invention (xv)above, R6represents a C1-3hydroxyalkyl (preferably hydroxymethyl).

xvii) According to another sub-option of option (xv)above, R6represents a carboxyl group.

xviii) According to another sub-option of option of carrying out the invention (xv)above, R6represents a C1-3alkoxycarbonyl (preferably etoxycarbonyl).

xix) According to the following sub-option of option of carrying out the invention (xv) PR is transcribed, R6must be a group)-(CH2)q-NR7R8where q is 1, 2 or 3 (in particular, 1) and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl, piperidinyl, morpholinyl or thiomorpholine ring and, in particular, pyrrolidinyl or piperidinyl ring (the group -(CH2)q-NR7R8represents, preferably, dimethylaminomethyl or pyrrolidin-1-ylmethyl).

XX) the Following variant of the present invention relates to compounds of formula (I) according to one of the embodiments of the invention (i)to(xix)above, where "" indicates the connection; this option is therefore preferably relates to compounds of formula (I) according to the variant (iv) or (viii), where "" means of communication, and

R1represents fluorine, or R1represents fluorine and V represents CH, or R1represents fluorine and V represents n

xxi) One sub-option of option of carrying out the invention (XX)above, refers to compounds of the formula (I) according to the variant (XX)above, where U represents CH (preferably by connecting the m formula (I) according to the variant (xiv), above, where U represents CH and R0represents N).

xxii) Another sub-option of option of carrying out the invention (XX)above, refers to compounds of the formula (I) according to the variant (XX)above, where U represents n

xxiii) According to one variant of the sub-option of carrying out the invention (xxii), the compounds of formula (I) according to the variant (xxii)above shall be such that R0represents N (preferably such that where R0represents N and V represents CH).

xxiv) According to another variant of the sub-option of carrying out the invention (xxii), the compounds of formula (I) according to the variant (xxii)above, are those in which R0represents a C1-3alkoxygroup (in particular, methoxy group); this special case relates preferably to compounds of formula (I) by one of the following (i)to(iii) or (v)to(vii), where

R0represents a C1-3alkoxygroup (in particular, methoxy group), and

R1represents a halogen (preferably F), or

R1represents H, or

R1represents a halogen (preferably F), and V represents CH, or

R1represents a halogen (preferably F), and V represents N,or

R1represents H and V Pres who is a CH, or

R1represents N or V represents N, or

V represents CH, or

V represents n

xxv) Another variant implementation of the present invention relates to compounds of formula (I) by one of the following (i)to(xix)above, where

"" is absent and U represents CH2or NH (preferably CH2); this option is therefore preferably relates to compounds of formula (I) according to the variant (iv) or (viii), where "" no, U represents CH; and:

R1represents fluorine, or

R1represents fluorine and V represents CH, or

R1represents fluorine and V represents N, or

V represents CH, or

V represents n

xxvi) One special variant of implementation of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (v) or (vi)or variant (i), (ii), (v) or (vi)taken together with one of the options (ix)to(xxv), where R4represents N.

xxvii) One sub-option of option of carrying out the invention (xxvi) refers to compounds of the formula (I) according to the variant (xxvi), where each of R4and R5represents N.

xxviii) Other special variant of implementation of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (v) or (vi)or variant (i), (ii), (v) or (vi)taken together with one of the options (ix)to(xxv), where n is 1 or 2, R4HE is a and R5represents N.

xxix) Another another special variant of implementation of the present invention relates to compounds of formula (I) according to option (i) or (v), or option (i) or (v), taken together with one of the options (ix)to(xxv), where R5represents a C1-3alkyl (preferably, methyl), C1-3hydroxyalkyl (preferably hydroxymethyl)1-3aminoalkyl (preferably aminomethyl)1-3alkoxy-C1-3alkyl (preferably, methoxymethyl), carboxyl group or C1-3alkoxycarbonyl (preferably methoxycarbonyl).

xxx) In particular, compounds of formula (I) according to the variant embodiment of the invention (xxix) are such compounds of formula (I) option (ii) or (vi), or option (ii) or (vi), together with one of the options (ix)to(xxv), where R5represents a C1-3alkyl (preferably, methyl), C1-3hydroxyalkyl (preferably hydroxymethyl)1-3alkoxyl1-3alkyl (preferably, methoxymethyl) or (C1-3alkoxycarbonyl (preferably methoxycarbonyl).

xxxi) According to one modification of the embodiments of the invention (xxix) or (xxx) R5represents a C1-3alkyl (pre is respectfully, methyl).

xxxii) According to another variant embodiment of the invention (xxix) or (xxx) R5represents a C1-3hydroxyalkyl (preferably hydroxymethyl or 1-hydroxy-1-methylethyl and, in particular hydroxymethyl).

xxxiii) According to another variant embodiment of the invention (xxix) or (xxx) R5represents a C1-3alkoxyl1-3alkyl (preferably, methoxymethyl).

xxxiv) According to the following variant of the invention (xxix) R5represents a C1-3alkoxycarbonyl (preferably methoxycarbonyl).

xxxv) According to the following variant of the invention (xxix) R5represents a C1-3aminoalkyl (preferably aminomethyl).

xxxvi) According to another following alternative implementation of the invention (xxix) R5represents a carboxyl group.

xxxvii) According to one main variant of implementation of the present invention compounds of formula (I) by one of the following (i)to(xxxvi) are such compounds in which a represents a -(CH2)p- (in this case, the compounds of formula (I), where n is 0 and p is 2 or 3, or n is 1 and p is 1, 2 or 3, or n is 2 and p is equal to 1 should be preferred).

xxxviii) According to one modification of the invention (xxxvii) compounds of formula (I) according to the variant (xxxvii) I is comprised of such compounds, where the sum of n and p is 2.

xxxix) According to one variant embodiment of the invention (xxxviii) compounds of formula (I) are those compounds where n is 0 and p is 2.

xl) According to another variant embodiment of the invention (xxxviii) compounds of formula (I) are those compounds where n is 1 and p is 1.

xli) According to another sub-option of option of carrying out the invention (xxxvii) compounds of formula (I) according to the variant (xxxvii) are such compounds where the sum of n and p is equal to 3 (preferably those in which the sum of n and p is equal to 3, each of R0, R4and R5represents H and G denotes a group of the formula G1or G2for option (i), (ii) or (iii)).

xlii) According to one variant embodiment of the invention (xli) compounds of formula (I) are those compounds where n is 0 and p is 3.

xliii) Compounds of formula (I) according to the variant (xlii) preferred are such compounds where "" means of communication, each of R0, R4and R5represents H, R1represents H or F (in particular F), V represents CH, U represents CH or N, and G denotes a group of the formula G1or G2for option (i), (ii) or (iii) (in particular, a group of the formula G1for option (i), (ii) or (iii), preferably a group of the formula G1where X represents CH and Q Ref is no S).

xliv) According to another variant embodiment of the invention (xli) compounds of formula (I) are those compounds where n is 1 and p is 2.

xlv) Compounds of formula (I) according to the variant (xliv) are preferably those in which "" means of communication, each of R0R and R5represents H, R1represents H or F (in particular F), V represents CH, U represents CH or N and G represents a group of formula G1or G2for option (i), (ii) or (iii) (in particular, a group of the formula G1for option (i), (ii) or (iii), preferably a group of the formula G1where X represents CH, and Q denotes S).

xlvi) According to another variant embodiment of the invention (xli) compounds of formula (I) are those compounds where n is 2 and p is 1.

xlvii) Compounds of formula (I) according to the variant (xlvi) are preferably such compounds, in which "" means of communication, each of R0, R4and R5represents H, R1represents H or F (in particular F), V represents CH, U represents CH or N, and G denotes a group of the formula G1or G2for option (i), (ii) or (iii) (in particular, a group of the formula G1for option (i), (ii) or (iii), preferably a group of the formula G1where X oboznachen and Q denotes S).

xlviii) According to another sub-option of option of carrying out the invention (xxxvii) compounds of formula (I) according to the variant (xxxvii) are such compounds where the sum of n and p is 4.

il) According to one variant embodiment of the invention (xlviii) compounds of formula (I) are those compounds where n is 0 and p is 4.

l) According to another variant embodiment of the invention (xlviii) compounds of formula (I) are those compounds where n is 1 and p is 3.

li) According to another another variant embodiment of the invention (xlviii) compounds of formula (I) are those compounds where n is 2 and p is 2.

lii) the Other main variant of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii), where a represents a-CH2CH2CHCOH), or to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii) in conjunction with one of the options (ix)to(xxxvi), where a represents a-CH2CH2CH(OH)-.

liii) the Other main variant of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii), where a is a-COCH2CH(OH)-, or to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii) in conjunction with one of the options (vii)to(xxxvi), where a is a-COCH2CH(OH)-.

liv) the Following variant of the present invention relates to compounds form the s (I) for option (i), (ii), (iii), (v), (vi) or (vii)where R2represents H, or to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii) in conjunction with one of the options (ix)-(liii), where R2represents N.

lv) the Following variant of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii)in which R2represents a group of formula-CH2-R3where R3represents hydrogen, C1-3alkyl or C1-3hydroxyalkyl, or to compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii) in conjunction with one of the options (ix)-(liii), in which R2represents a group of formula-CH2-R3where R3represents hydrogen, C1-3alkyl or C1-3hydroxyalkyl (in particular, to compounds of formula (I) according to option (iii) or (vii)where R2represents a group of formula-CH2-R3, R3represents a C1-3alkyl or C1-3hydroxyalkyl, or to compounds of formula (I) according to option (iii) or (vii) in conjunction with one of the options (ix), (x), (xiii), (xiv), (xx)to(xxv) and (xxxvii)-(liii), where R2represents a group of formula-CH2-R3, R3represents a C1-3alkyl or C1-3hydroxyalkyl).

lvi) According to one variant embodiment of the invention (lv) compounds of formula (I) according to the variant (lv) are such compounds where R 2represents a group of formula-CH2-R3where R3denotes hydrogen or C1-3alkyl.

lvii) According to another variant embodiment of the invention (lv) compounds of formula (I) according to the variant (lv) are such compounds where R2represents a group of formula-CH2-R3where R3represents C1-3hydroxyalkyl (in particular those in which R2is a group of 2-hydroxyethyl or 3-hydroxypropyl).

lviii) the Following variant of the present invention relates to compounds of formula (I) according to the variant (i), (ii), (v) or (vi), where R2represents a C1-3alkylaryl (preferably acetyl), or to compounds of formula (I) according to the variant (i), (ii), (v) or (vi) together with one of the options (ix)-(liii), where R2is alkylaryl (preferably acetyl).

lix) According to one particular variant of implementation of the present invention compounds of formula (I) options (i)-(lviii), above, are such compounds where

G represents a group of formula G1or, in embodiments relating to option (viii), the group G1'.

lx) Preferably, the compounds of formula (I) according to the variant embodiment of the invention (lix), above, are such compounds where X, if present, represents CH (i.e. G is a 3-ACS is -3,4-dihydro-2H-benzo[1,4]thiazin-6-yl or 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl); special sub-option this option relates to compounds of formula (I) according to the variant (iv) or (viii), where G represents 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl or 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl and:

R1represents fluorine, or

V represents CH, or

V represents N, or

R1represents fluorine and V represents CH, or

R1represents fluorine and V represents N, or

R1represents fluorine and "" denotes a bond, or

R1represents fluorine, "" means a connection and V represents CH,

R1represents fluorine, "" means a connection and V represents N,

"" is absent and U represents CH2or R1represents fluorine, "" is absent and U represents CH2or

R1represents fluorine, V represents CH, "" is absent and U represents CH2or

R1represents fluorine, V represents N, "" is absent and U represents CH2.

lxi) According to another particular variant of the present invention compounds of formula (I) ia is yantam embodiment of the invention (i)-(lviii), shown above are such compounds where G is a group of the formula G, or, in embodiments relating to a variant (v), (vi), (vii) or (viii), the group G2'.

lxii) According to the variant embodiment of the invention (lxi) compounds of formula (I) according to the variant (lxi), above, are such compounds where the or each Y1, Y2and Y3if present, represents CH, or one of the Y1and Y3if present, represents N and Y2and another from Y1and Y3if present, each represents CH (i.e. G is a 2,3-dihydro[1,4]like[2,3-c]pyridine-7-yl, 2,3-dihydro[1,4]like[2,3-b]pyridine-6-yl or 2,3-dihydrobenzo[1,4]dioxin-6-yl).

lxiii) Preferably, the compounds of formula (I) according to the variant embodiment of the invention (lxii), above, are such compounds where each of the Y1, Y2and Y3if present, represents CH (i.e. G is a 2,3-dihydrobenzo[1,4]dioxin-6-yl).

lxiv) According to another particular variant of implementation of the present invention compounds of formula (I) options (i)-(lviii), above, are such compounds where G represents a phenyl group, which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4 of alkyl, C1-3alkoxygroup and halogen (preferably F), and C1-3alkoxygroup? if there is a preferably linear C1-3alkoxygroup located in the p-position, or in variants relating to option (vii) or (viii), such compounds where G represents a phenyl group which is substituted once in the m-position and once in the p-position substituents, independently selected from each other from C1-4of alkyl and halogen (preferably F).

lxv) Preferably, the compounds of formula (I) according to the variant embodiment of the invention (lxiv), above, are such compounds where G represents a phenyl group, which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from methyl, ethyl, metoxygroup, ethoxypropan and halogen (preferably F), and, methoxy - or amoxicillian, if present, is in p-position, or, in embodiments relating to option (vii) or (viii), such compounds where G represents a phenyl group which is substituted once in the m-position and once in the p-position substituents selected independently of one another from methyl and fluorine.

lxvi) In particular, compounds of formula (I) according to variants of the invention (lxiv) (lxv), given the output above, are such compounds in which G represents 3-fluoro-4-were.

lxvii) the Following variant of the present invention relates to compounds of formula (I) according to the variant embodiment of the invention (i), (ii), (v) or (vi) where:

"" denotes a bond, V represents CH and U represents CH or N, or "" is absent and U represents NH;

R0represents H, or when "" means a connection can also be a1-3alkoxygroup (in particular, methoxy group);

R1represents H or halogen, preferably H, F or Br, and, in particular, N or F);

R2represents N;

each of R4and R5represents N;

n is 0;

And represents -(CH2)p-, p is 3;

G denotes a group of the following formula G1

where X denotes CH or N and Q represents O or S;

and to the salts (in particular pharmaceutically acceptable salts) of such compounds.

lxviii) According to one sub-option of option of carrying out the invention (lxvii) compounds of formula (I) according to the variant (lxiv) are such compounds where "" denotes a bond, V represents CH and U represents CH or n

lxix) According to another sub-option of option of carrying out the invention (lxvii) compounds of formula (I) according to the variant (lxiv) are such compounds where "" is absent and U represents NH.

lxx) the Following variant of the present invention relates to compounds of formula (I) according to the variant embodiment of the invention (i), (ii), (v) or (vi)where:

"" denotes a bond, V represents CH and U represents CH or N, or "" is absent and U represents NH;

R0represents H, or when "" denotes a bond, may also be a C1-3alkoxygroup (in particular, methoxy group);

R1represents H or halogen (preferably F or Br, in particular, F);

R2represents N;

R4represents N;

R5represents H, C1-3alkyl (preferably, methyl), C1-3hydroxyalkyl (preferably hydroxymethyl)1-3alkoxyl1-3alkyl (preferably, methoxymethyl) or C1-3alkoxycarbonyl (preferably acetyl);

n is 0;

And represents -(CH2)p-, p is 3; and

G denotes a group of the following formula G2'

where each and the Y 1and Y3represents CH, or one of the Y1and Y3represents N and the other represents CH (in particular, where each of the Y1and Y3represents CH);

and to the salts (in particular pharmaceutically acceptable salts) of such compounds.

lxxi) According to one sub-option of option of carrying out the invention (lxx) compounds of formula (I) according to the variant (lxx) are such compounds where "" denotes a bond, V represents CH and U represents CH or N.

lxxii) According to another sub-option of option of carrying out the invention (lxx) compounds of formula (I) according to the variant (lxx) are such compounds where "" is absent and U represents NH.

lxxiii) One main variant of the present invention relates to compounds of formula (I) according to one of the embodiments of the invention (i)-(xxvii) or (xxix)-(xxxvii), in particular for option (i) or (v), where n is equal to 0 (preferably where n is 0, And represents (CH2)pand p is 2 or 3).

lxxiv) the Other main variant of the present invention relates to compounds of formula (I) according to one of the embodiments of the invention (i)-(xxvii) or (xxix)-(xxxvii), in particular for option (i) or (v), where n is equal to 1 (preferably where n is 1, And represents (CH2)pand p is 1 or 2).

lxxv) the Other main variant of implementation of the present invention relates to compounds of formula (I) according to one of the options (i)-(xxvii) or (xxix)-(xxxvii), in particular for option (i) or (v), where n is equal to 2 (preferably, n is 2, And represents (CH2)pand p is 1 or 2).

lxxvi) the Following variant of the present invention relates to compounds of formula (I) according to the variant embodiment of the invention (i) or (v)where:

"" means a connection and V represents CH and U represents CH or N, or V represents N and U represents CH;

R0represents N;

R1represents H or fluorine (in particular, fluorine);

R2represents N;

R4represents N;

R5represents H, methyl, hydroxymethyl or aminomethyl (in particular, N);

n is 0 and represents -(CH2)p-where p is 2, 3 or 4, or n is 1 and a is a -(CH2)p-where p is 1, 2 or 3; and

G denotes a group of the following formula G1

,

where X denotes CH or N and Q represents O or S;

and to the salts (in particular pharmaceutically acceptable salts) of such compounds.

lxxvii) Another variant of the present invention relates to compounds of formula (I) according to the variant of implementation, the value of the invention (i) or (v), where:

"" is absent and U represents NH or NR9where R9denotes methyl (in particular, NH);

R0represents N;

R1represents H or fluorine (in particular, fluorine);

R2represents N;

each of R4and R5represents N;

n is 0 and represents -(CH2)p-where p is 2, 3 or 4, or n is 1 and a is a -(CH2)p-where p is 1, 2 or 3; and

G denotes a group of the following formula G

,

where X denotes CH or N and Q represents O or S;

and to the salts (in particular pharmaceutically acceptable salts) of such compounds.

lxxviii) According to one particular variant of implementation of the present invention the compounds of formula (I) options (i)-(lxxvii)above, have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxix) According to one sub-option of option of carrying out the invention (lxxviii) compounds of formulas is (I) option (lxxviii) have the stereochemistry, represented in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxx) According to another sub-option of option of carrying out the invention (lxxviii) the compounds of formula (I) according to the variant (lxxviii) have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxxi) According to another particular variant of implementation of the present invention the compounds of formula (I) options (i)-(lxxvii)above, have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry, p is redstavlennye in the following formula

lxxxii) According to one sub-option of option of carrying out the invention (lxxxi) the compounds of formula (I) according to the variant (lxxxi) have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxxiii) According to another sub-option of option of carrying out the invention (lxxxi) the compounds of formula (I) according to the variant (lxxxi) have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxxiv) According to another particular variant of implementation of the present invention the compounds of formula (I) options (i)-(lxxvii)above, have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry, represented in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxxv) According to another particular variant of implementation of the present invention the compounds of formula (I) options (i)-(lxxvii)above, have the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

lxxxvi) Particularly preferred are the following compounds of formula (I) by one of the following (i)to(viii):

9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazol the in-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-Beit[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-od;

9-fluoro-1-{2-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(4R)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-ij][1,5]naphthiridine-7-he;

3-fluoro-4-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)ox is solidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-of the;

9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

and their salts (in particular pharmaceutically acceptable salts).

lxxxvii) in Addition, the object of the present invention includes the following compounds of formula (I) by one of the following (i)to(viii):

(1R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-d is hidropetrol[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino)methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one:

(1R)-9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino)methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({2-[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({2-[(S)-3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino)methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[()-3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(S)-3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one:

(1S)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-Mei is phenyl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(4R)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-3-fluoro-4-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4S)-3-fluoro-4-(2-{[(S) - 2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-3-fluoro-4-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino)ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5] naphthiridine-7-he;

(4S)-3-fluoro-4-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(6R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(6S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(6R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(6S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(1R)-9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]China is n-4-one;

(1R)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo [3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydrate is Rolo[3,2,1-ij]quinoline-4-one;

(4R)-3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(4S)-3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(1R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-1-({[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-1-({[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihyd pyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-({[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-({[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

and their salts (in particular pharmaceutically acceptable salts).

lxxxviii) furthermore, especially preferred compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii) are the following compounds:

4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({[(R)-3-(4-butylphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]enous the n-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

1-({2-[3-(2,3-dihydro-[1,4]like[2,3-C]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[3-(2,3-dihydro-[1,4]like[2,3-6]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino} methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-is)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

9-fluoro-1-{2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]am is but}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]about what ylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-Dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

1-({3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]chapolin-4-one;

3-fluoro-4-{2-[(S)-2-about the co-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl} amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]nafti the one-7-he;

3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-56-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

6-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]Hinckley-3-one;

1-{2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-propionamide;

(R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

6-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

9-fluoro-1-{3-hydroxy-3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin--he;

and their salts (in particular pharmaceutically acceptable salts).

lxxxix) in Addition, the object of the present invention includes the following compounds of formula (I) according to the variant (i), (ii), (iii), (v), (vi) or (vii):

(R)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({[(R)-3-(4-butylphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(R)-3-(4-butylphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-ID)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-1-({2-[(R)-3-(2,3-dihydro-[1,4]like[2,3-C]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-3-(2,3-dihydro-[1,4]like[2,3-c]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(R)-3-(2,3-dihydro-[1,4]like[2,3-c]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(S)-3-(2,3-dihydro-[1,4]dioxime[2,3-C]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(R)-3-(2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-3-(2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(R)-3-(2,3-dihydro-[1L]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-of the;

(S)-1-({2-[(R)-3-(2,3-dihydro-[l,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino} methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazol the DIN-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3 op;

(S)6-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-9-fluoro-1-{2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]oxazin-6-yl)oxazolidin-5-yl]ethyl is Ino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)OK who solidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]nafti the one-7-he;

(R)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({3-[(S)-2-oxo-3-(3-about the co-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-3-fluoro-4-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]hin the Lin-4-one;

(S)-9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydr what-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]Hinckley-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-6-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-{2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}-9-fluoro-1,2-dihydro who irolo[3,2,1-ij]quinoline-4-one;

(S)-1-{2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide;

(R)-N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide;

(S)-N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide;

(S)-N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide;

(R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)ox is solidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(1R)-9-fluoro-1-{(3R)-3-hydroxy-3-[(5R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{(3R)-3-hydroxy-3-[(5S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{(3S)-3-hydroxy-3-[(5R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R)-9-fluoro-1-{(3S)-3-hydroxy-3-[(5S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{(3R)-3-hydroxy-3-[(5R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{(3R)-3-hydroxy-3-[(5S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{(3S)-3-hydroxy-3-[(5R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S)-9-fluoro-1-{(3S)-3-hydroxy-3-[(5S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

and their salts (in particular, the pharmaceutical is Eski acceptable salt).

XC) Other preferred compounds of formula (I) option (ii) or (vi) are the following compounds:

6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

9-bromo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-6][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

ethyl ester of (R)-4-oxo-1-{3-[(5')-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;

(R)-7-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;

(R)-7-dimethylaminomethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]impregnated the amino}-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S) - 2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]tiaii-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo what about[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-Dihydro-2-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

9-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-(methyl-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-Digue is capirola[1,2,3-de]cinoxacin-3-one;

(RS)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

methyl ester of (1R*,2R*)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

methyl ester of (1R*,2R*)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(1R*,2R*)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*2R*)-2-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)OK who solidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2R*)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*2S*)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*2R*)-2-(1-hydroxy-1-methylethyl)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

N-(9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}ndimethylacetamide;

(S)-4-hydroxy-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

9-fluoro-1-hydroxy-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]is Yasin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

and their salts (in particular pharmaceutically acceptable salts).

xci) furthermore, the object according to the invention includes the following compounds of formula (I) according to option (I) or (vi):

(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-9-bromo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-bromo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

(S)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

(R)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

(S)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;

ethyl ester of (R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihyd the on-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;

(R)-7-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;

(R)-7-dimethylaminomethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazo the one-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]PR is palamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-9-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-(methyl-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-(methyl-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyri the olo[1,2,3-de]cinoxacin-3-one;

(R)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[l,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydr what-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

methyl ester (1R,2R)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

methyl ester of (1S,2S)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

methyl ester (1R,2R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

methyl ether (7S,2S)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(1R,2R)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2R)-2-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-2-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-PLN-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2R)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]PR is palamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-2-methyl-l-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2R)-2-(1-hydroxy-1-methylethyl)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]about what ylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-2-(1-hydroxy-1-methylethyl)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

N-((R)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}ndimethylacetamide;

N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}ndimethylacetamide;

(S)-4-hydroxy-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;

(R)-9-fluoro-1-hydroxy-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-hydroxy-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

and their salts (in particular pharmaceutically acceptable salts).

xcii) Other particularly preferred compounds of formula (I) according to the variant i) or v) are the following compounds:

1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-on;

1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-ethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-ethinyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

methyl ester of (1R*,2R*)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(1R*,2R*)-9-fluoro-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-is)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2R*)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R*,2S*)-2-aminomethyl-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]Hino-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

and their salts (in particular pharmaceutically acceptable salts).

xciii) Another object of the present invention includes the following compounds of formula (I) according to option (i) or (v):

(R)-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-1-({[(S)-2-oxo-3-(3-oxo,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-on;

(S)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

(R)-9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-ethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-ethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-ethinyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-ethinyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

metrov the th ether (1R,2R)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

methyl ester of (1S,2S)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(1R,2R)-9-fluoro-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2S)-9-fluoro-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-9-fluoro-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-9-fluoro-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-on;

(1R,2S)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-9-fluoro-4-the CSR-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(1S,2S)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;

(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-l-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;

(1R,2S)-2-aminomethyl-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(1S,2R)-2-aminomethyl-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-l-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]OK Azin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propyl what Mino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;

and their salts (in particular pharmaceutically acceptable salts).

xciv) the Invention also relates to compounds of formula (I) options (i) or (v), which is selected from the group comprising the compounds listed in embodiment (lxxxvi), the compounds listed in embodiment (lxxxviii), compounds listed in option (HS), and connections specified in option (xcii), as well as to the salts (in particular pharmaceutically acceptable salts) of such compounds. In particular, the invention also applies to groups of compounds of formula (I)are selected from the group comprising the compounds is of, specified in option (lxxxvi), the compounds listed in embodiment (lxxxviii), compounds listed in option (HS), and connections specified in option (xcii), when this group of compounds correspond to one of the options (ix)-(lxxxv), as well as to the salts (in particular pharmaceutically acceptable salts) of such compounds.

xcv) the Invention also relates to compounds of formula (I) options (i) or (v), which is selected from the group comprising the compounds listed in embodiment (lxxxvii), the compounds listed in embodiment (lxxxix), the compounds listed in embodiment (xci), and connections specified in option (xciii), as well as to the salts (in particular pharmaceutically acceptable salts) of such compounds. In particular, the invention also applies to groups of compounds of formula (I)are selected from the group comprising the compounds listed in embodiment (lxxxvii), the compounds listed in embodiment (lxxxix), the compounds listed in embodiment (xci), and connections specified in option (xciii), when this group of compounds, in addition, meet one of the options (ix)-(lxxxv), as well as to the salts (in particular pharmaceutically acceptable salts) of such compounds.

The compounds of formula (I) according to the invention, for example, one of the options (i)-(xcv), above, are suitable for use as chemotherapeutic active compounds in medicine and veterinary medicine, as well as the as substances for preserving inorganic and organic materials, in particular all types of organic materials, for example polymers, lubricants, paints, fibres, leather, paper and wool.

Compounds according to the present invention are particularly active against bacteria and bacteria-like organisms and are therefore particularly suitable for humans and animals in the prophylaxis and chemotherapy of local and systemic infections caused by these pathogens, and diseases associated with bacterial infections, including pneumonia, otitis media, sinusitis, bronchitis, tonsillitis, and mastoiditis related to infection caused by Streptococcus pneumoniae, Haemophilus influenzas, Moraxella catarrhalis, Staphylococcus aureus, Enterococcusfaecalis, E. faecium, E. casseliflavus, S. epidermidis, S. haemolyticus, or Peptostreptococcus spp., pharyngitis, rheumatic fever, and glomerulonephritis related to infection caused by Streptococcus pyogenes, groups C and G streptococci, Corynebacterium diphtheriae, or Actinobacillus haemolyticum; infections of the upper respiratory tract associated with infection caused by Mycoplasma pneumoniae, Legionella pneumophila, Streptococcus pneumoniae, Haemophilus injiuenzae or Chlamydia pneumoniae; infections of the blood and tissues, including endocarditis and osteomyelitis, caused by S. aureus, S. haemolyticus, Enterococcus faecalis, E. faecium, E. durans, including hereditary resistance to known antibacterial agents, such as not limited to, β-lactams, vancomycin, aminoglycosides, quinolones, chloramphenicol, tetracycli the s and macrolides; uncomplicated infections of skin and soft tissue abscesses and postpartum sepsis associated with infection caused by Staphylococcus aureus, coagulability susceptible (i.e., S. epidermidis, S. haemolyticus, and the like), Streptococcus pyogenes, Streptococcus agalactiae, Streptococcal groups C-F (the smallest colony streptococci), viridans streptococci, Corynebacterium minutissimum, Clostridium spp. or Bartonella henselae; uncomplicated acute urinary tract infections related to infection caused by Staphylococcus aureus, coagulability species Staphylococcus or Enterococcus spp.; urethritis and cervicitis; sexually transmitted diseases related to infection caused by Chlamydia trachomatis, Haemophilus ducreyi, Treponema pallidum, Ureaplasma urealyticum, or Neiserria gonorrhoeae; toxicosis associated with infection caused by S. aureus (food poisoning and toxic shock syndrome), or groups a, b and C streptococci; ulcers related to infection caused by Helicobacter pylori; systemic febrile syndrome associated with infection caused by Borrelia recurrentis; Lyme disease related to infection caused by Borrelia burgdorferi; conjunctivitis, keratitis, and dacryocystitis associated with infection caused by Chlamydia trachomatis, Neisseria gonorrhoeae, S. aureus, S. pneumoniae, S. pyogenes, H. Injiuenzae or Listeria spp., disseminated Mycobacterium avium complex (MAC)associated with infection caused by Mycobacterium avium, or Mycobacterium intracellulare; infection caused by Mycobacterium tuberculosis, M. leprae, M. paratuberculosis, M. Kansasii, or M. chelonei; gastroenteritis related to infection caused by Campylobacter jejuni; Chechnya protozoal infections associated with infection caused by Cryptosporidium spp.; dental infection related to infection caused by viridans streptococci; persistent cough related to infection caused by Bordetella pertussis; gas gangrene related to infection caused by Clostridium perfringens or Bactero ides spp.; and atherosclerosis or cardiovascular disease related to infection caused by Helicobacter pylori or Chlamydia pneumoniae.

The compounds of formula (I) according to the present invention are applied, in addition, to obtain drugs for the treatment of infections caused by such bacteria as E. coli, Klebsiella pneumoniae and other enterobacteria, Acinetobacter spp., Stenothrophomonas maltophilia, Neisseria meningitidis, Bacillus cereus. Bacillus anthracis, Corynebacterium spp., Propionibacterium acnes and bacteroids spp.

The compounds of formula (I) according to the present invention are applied, in addition, for the treatment of protozoal infections caused by Plasmodium malaria, Plasmodium falciparum, Toxoplasma gondii, Pneumocystis carinii, Trypanosoma brucei and Leishmania spp.

Presents a list of pathogens should be considered only as exemplary and in no way as limiting the list.

The compounds of formula (I) according to the present invention or their pharmaceutically acceptable salts can be applied to obtain drugs for prevention or treatment of bacterial infections.

One aspect of the present izopet the deposits is due to the use of compounds of formula (I) according to one of the options (i)-(xxxix) or its pharmaceutically acceptable salt to obtain drugs for prevention or treatment (particularly, for the treatment of bacterial infections. Another aspect of the present invention relates to the compound of formula (I) according to one of the options (i)-(xxxix) or its pharmaceutically acceptable salts for the prophylaxis or treatment (particularly for the treatment of bacterial infections.

Thus, the compounds of formula (I) according to one of the options (i)-(xxxix) or their pharmaceutically acceptable salts can be applied to obtain medicines and are suitable for prevention or treatment (particularly for the treatment) of a bacterial infection selected from the group including respiratory tract infections, otitis, meningitis, infections of the skin and deep tissues (complicated or uncomplicated), pneumonia (including hospital or acquired pneumonia, bacteremia, endocarditis, intraabdominal infections, infections of the gastrointestinal tract, Clostridium difficile infections, urinary tract infections, infection, sexually transmitted infection caused by a foreign body, osteomyelitis, Lyme disease, topical infections, eye infections, tuberculosis and tropical diseases (e.g. malaria), and especially for the prevention or treatment (in particular treatment) of a bacterial infection selected from the group including respiratory tract infections, otitis, meningitis, infections of the skin and deep tissues (oslojnenny is or uncomplicated), pneumonia (including hospital or acquired pneumonia, bacteremia.

Just as in medicine, a bacterial infection to be treated with the use of compounds of formula (I) or their pharmaceutically acceptable salts) in veterinary medicine for the treatment of these animals, such as pigs, ruminants, horses, dogs, cats and poultry.

The present invention relates to pharmacologically acceptable salts and compositions and formulations based on the compounds of formula (I).

Any reference to a compound of formula (I) includes a reference to salts (in particular pharmaceutically acceptable salts) of such compounds, as appropriate and expedient.

The pharmaceutical composition according to the present invention contains at least one compound of formula (I) or its pharmaceutically acceptable salt as an active agent and optionally carriers and/or diluents and/or additives and may also optionally contain known antibiotics.

The compounds of formula (I) and their pharmaceutically acceptable salts can be used as medicines, for example in the form of pharmaceutical compositions for enteral and parenteral administration.

The manufacture of pharmaceutical compositions is carried out by a method known to anyone skilled in the art (see, for example. Remngton, The Science and Practice of Pharmacy, 21st Edition (2005), Part 5, "Pharmaceutical Manufacturing" [published by Lippincott Williams & Wilkins]) by introduction of the described compounds of formula (I) or their pharmaceutically acceptable salts, optionally in combination with other pharmaceutically acceptable substances in dosage form together with suitable, non-toxic, inert, therapeutically compatible solid or liquid carriers and, if desired, usual pharmaceutical excipients.

Another aspect of the invention relates to a method of treating a bacterial infection in a patient, comprising the introduction of the named patient pharmaceutically active amount of a compound of formula (I) or its pharmaceutically acceptable salt.

In addition, any preferences and modifications specified for the compounds of formula (I) (whether the connection itself, salts thereof, compositions containing the compounds or salts thereof, the use of the compounds or its salts, and the like) are applicable mutatis mutandis to compounds of formula (IP), to compounds of formula (ICEand to compounds of the formula (ICEP).

Moreover, the compounds of formula (I) can be used for disinfection, for example for processing surgical instruments to remove pathogenic bacteria and bacterial or aseptic clean room or surfaces. For these purposes the compounds of formula (I) which may be used in the form of a solution or spray.

The compounds of formula (I) in accordance with the present invention can be obtained using the methods described below.

Obtaining compounds of formula (I)

Abbreviations:

In the description and examples, the following abbreviations are used:

AC is acetyl, Asón - acetic acid, AD-mix α - 1,4-BMS(dihydroquinoline)phthalazine, K3Fe(CN)6To2CO3and K2OsO42H2O, AD-mix β - 1,4-bis(dihydroquinoline)phthalazine, K3Fe(CN)6To2CO3and K2OsO42H2Oh, the Alloch - allyloxycarbonyl, AIBN - azo-bis-isobutyronitrile, 9-BBN - 9-borabicyclo[3.3.1]nonan, Side - tert-butoxycarbonyl, Bu is n-butyl, CBS - benzyloxycarbonyl, KX - column chromatography on silica gel, DAD - detection using a diode matrix, DBU is 1,8-diazabicyclo[5.4.0]undecen-7-ene, CBI - 1,1'-carbonyldiimidazole, DCC - N,N'-dicyclohexylcarbodiimide, EDC - 1,2-dichloroethane, deja - diethylamin, DHM - dichloromethane, (DHQ)2PHAL - 1,4-bis(dihydroquinoline)phthalazine, (DHQD)2PHAL - 1,4-bis(dihydropyridin)phthalazine, DEBUG - diisobutylamine, DYADS - diisobutyldimethoxysilane, DIPEA - N,N-diisopropylethylamine, DMAP - 4-dimethylaminopyridine, DMF is N,N-dimethylformamide, DMSO is dimethylsulfoxide, DPEphos - bis-(2-diphenylphosphinoethyl)ether, DFFA - diphenylphosphinite, EA - ethyl acetate, EKD - hydrochloride 1-(dimethylaminopropyl)-3-ethylcarbodiimide is a, it enantiomeric excess, ELSD - steam scattering of light, ESI is electrospray ionization, EQ. equivalent, ether - diethyl ether, Et is ethyl, EtOH - ethanol, Fmoc - 9-fluorenylmethoxycarbonyl, GATA - hexaphosphate O-(7-asobancaria-1-yl)-N,N,N',N'-tetramethylurea, HOBT - hydrate of 1-hydroxybenzotriazole, HPLC is high performance liquid chromatography, KHMDS - hexamethyldisilazide potassium, LAH - sociallyengaged, Li - hexamethyldisilazide lithium, m-HPBK - m-chloroperbenzoic acid, and Me is methyl, MeCN is acetonitrile, Meon - methanol, min - min, MS - mass spectroscopy, Ms - methanesulfonyl (mesyl), H-BuLi is n-utility, NBS is N-bromosuccinimide, Nf - nonattributable, Ns - 4-nitrobenzenesulfonyl (nosrat), N-MO - N-oxide, N-methylmorpholine, o-Tol - o-tolyl, Pd/C is palladium on coal, Pd(OH)2/C - dihydroxy palladium on coal, Ph is phenyl, Pht - flail, Rog - pyridine, rat. - racemic, CT room temperature, TBAF - tetrabutylammonium, TBDMS - tert-butyldimethylsilyl, TRIPS - tetrabromodiphenylether, TBME - tert-butyl methyl ether, tBu is tert-Bootle, tea is triethylamine, TEMPO is 2,2,6,6-tetramethyl-1-piperidinyloxy, Ti - trifloromethyl (triflic), TPA - triperoxonane acid, THF is tetrahydrofuran, and TLC is thin layer chromatography, TMEDA - tetramethylethylenediamine, TMS is trimethylsilyl, tR- retention time, Ts - p-toluensulfonyl.

Overall sinteticheskie methods

General synthetic method 1 (alkylation of amine):

The ammonia or the appropriate amine derivative is introduced into a reaction with a suitable derivative having a side group L1L2L3or L4where L1L2L3or L4represent OMs, OTf, OTs, ONs, ONf, OBs, Cl, Br or I, in the presence of inorganic bases, such as2CO3or organic base such as tea in a solvent such as THF, DMF or DMSO, at temperatures from 0°C to +80°C. More details of these methods are described in the publications: Comprehensive Organic Transformations. A guide to Functional Group Preparations; 2ndEdition, R.C.Larock, Wiley-VC; New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, (1999). Section Amines, p.779.

General synthetic method 2 (reductive amination):

A solution of amine (1 mmol) and aldehyde or ketone (1 mmol) in a mixture of EDC/Meon in the ratio of 1:1 (10 ml) was stirred at room temperature over night, possibly in the presence of a desiccant, such as MgSO4or 3Å molecular sieves. Then added NaBH4(2-5 EQ.) and the reaction is left for 1 h, then diluted with DHM and aqueous solution of NH4OH. The organic phase is washed with water, dried over MgSO4and concentrate. Alternatively, a solution of amine (1 mmol) and aldehyde or ketone (1 mmol) in a mixture of EDC/Meon in the ratio of 1:1 (10 ml) was treated with NaBH(SLA)3(2 EQ.). With the ect stirred at room temperature until the reaction is completed. The reaction mixture was diluted with DHM and aqueous solution of NH4OH, the organic phase is washed with water, dried over MgSO4and concentrate.

General synthetic method 3 (activation of alcohol):

Alcohol injected into reaction with MsCl, TfCl, NfCl, NsCl, BsCl or TsCl in the presence of a base, such as triethylamine, DIPEA or pyridine, in a dry aprotic solvent such as DHL, THF or pyridine, in a temperature range from -10°C to room temperature. Alternatively, the alcohol also enter into reaction with Ms2O or Tf2O, after which the activated intermediate compound is transformed into the corresponding iodine - or bromine derivatives through reaction of the activated alcohol with NaI or NaBr in a solvent such as acetone.

General synthetic method 4 (removal aminosidine groups):

Benzylcarbamoyl group is removed by hydrogenation over a catalyst made of noble metals (such as Pd/C or Pd(OH)2/C). The BOC-group is removed under acidic conditions such as HCl in an organic solvent such as methyl alcohol or dioxane or TFA (concentrated or diluted), in a solvent such as DHM. In addition, General methods of removal aminosidine groups described in the publication: T.W.Greene, P.G.M. Wuts, Protecting Groups in Organic Synthesis, 3rdEd (1999), 494-653 (Publisher: John Wiley and Sons, Inc., New York, N.Y.).

General synthetic method 5 (restore SL is the author of esters, ketones and aldehydes):

Esters restore using boron or aluminiumhydride reducing agents, such as LiBH4or LiAlH4in a solvent such as THF, at temperatures from -20°C to 40°C. alternatively, the ester group hydrolized to the corresponding acid using an alkali hydroxide, such as NaOH, KOH or LiOH, in water or in mixtures of water with polar proton or aprotic solvent such as THF or Meon, at temperatures from -10°C to 50°C. the Resulting carboxylic acid is then restored to the corresponding alcohol using a derivative of boron, such as complex NR3·THF, in a solvent such as THF, at a temperature of from -10° to 40°C.

Aldehydes and ketones restore using hydrides of boron or aluminum, such as NaBH4, LiBH4or LAH in a solvent such as THF, at a temperature from 20°C to 40°C. More details of these methods are described in the publications: Comprehensive Organic Transformations. A guide to Functional Group Preparations; 2nd Edition, R.C.Larock, Wiley-VC; New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, (1999). Section alcohols and phenols, p.1057-1087.

General synthetic method 6 (CIS-dihydroxypropane):

Diol obtained by dihydroxypropane corresponding ethylene derived using catalytic amounts of potassium osmate in the presence of deoxidant, such as N-MO in aqueous solvent is, such as mixtures of acetone with water or DHM with water (see: Cha, J.K. Chem. Rev. (1995), 95, 1761-1795). Chiral CIS-diols obtained using AD-mix α or AD-mix β in the presence of methanesulfonamide in a mixture of water/2-methyl-2-propanol as described in the publication: Chem. Rev. (1994), 94, 2483. The orientation of the induction depends on the chiral ligand contained in AD mixture: ligand-based dihydroquinine, as in AD-mix α or ligand-based dihydropyridine, as in AD-mix β.

General synthetic method 7 (protection of alcohols):

Alcohols protect, turning them into silyl ethers (usually TBDMS or TRIPS) by introducing alcohol into the reaction with the desired simillarity reagent (Cl or l) in the presence of a base such as imidazole or tea in a solvent such as DHL, THF or DMF, at a temperature from 10°C to 40°C.

In addition, methods other alcohol protective groups described in the publication: Protecting Groups in Organic Synthesis, 3rdEd (1999), 23-147; T.W.Greene, P.G.M. Wins; (Publisher: John Wiley and Sons, Inc., New York, N.Y.).

General synthetic method 8 (removal hydroxyamino group):

Silyl ester group is removed by using either of the sources of the fluoride anion, such as TBAF in THF, at temperatures from 0°C to +40°C, or in acidic conditions using Asón in a mixture of THF/Meon or HCl in the Meon. In addition, the methods of removal TRIMS and TRIPS groups are presented in the publication Protecting Groups in OrganicSynthesis 3 rdEd; 1999, pages 133-139 and 142-143, respectively; T.W.Greene, P.G.M. Wuts; (Publisher: John Wiley and Sons, Inc., New York, N.Y.). Other common methods of removal of the protective spirit of the groups described in the publication Protecting Groups in Organic Synthesis, 3rdEd (1999), 23-147; T.W.Greene, P.G.M. Wuts (Publisher: John Wiley and Sons, Inc., New York, N.Y.). In the special case alkylcarboxylic group free alcohol can be obtained by reaction with inorganic base, such as2CO3in a solvent such as Meon.

General synthetic method 9 (obtaining aldehydes):

Alcohols can be converted into the corresponding aldehydes by oxidation Svernu (see: D. Swern et al., J. Org. Chem. (1978), 43, 2480-2482) or Dess-Martin (see: D.B.Dess and J.C.Martin, J. Org. Chem. (1983), 48, 4155), respectively. Alternatively, the esters can be converted into the corresponding aldehydes by controlled recovery with the volume of hydride reagent, such as DEBUG.

General synthetic method 10 (protection of the amino group):

Amines are usually protect, turning them into carbamates with such groups as the Alloch, CBS, Side or Fmoc. Using the reaction of an amine with allylchloroformate or benzylchloride, di-tert-BUTYLCARBAMATE or Fmoc-Cl in the presence of a base, such as NaOH, tea, DMAP or imidazole. They can also be protected by conversion into N-benzyl derivatives obtained by reaction with benzilla the home or benzylchloride in the presence of a base, such as Na2CO3or tea. Alternatively, N-benzyl derivatives can be obtained by reductive amination in the presence of benzaldehyde and borhydride reagent, such as NaBH4, NaBH3CN or NaBH(SLA)3in a solvent such as Meon, EDC or THF. Other methods of introducing aminosidine groups described in the publications: T.W.Greene, P.G.M. Wins, Protecting Groups in Organic Synthesis, 3rd Ed (1999), 494-653 (Publisher: John Wiley and Sons, Inc., New York, N.Y.).

General synthetic method 11 (hydrogenation of the double bond):

Unsubstituted derivative is dissolved in a solvent such as Meon, EA or THF, hydronaut over a catalyst of a noble metal such as Pd/C or PtO2or over Raney Ni. At the end of the reaction the catalyst is filtered off and the filtrate is evaporated under reduced pressure. Alternatively, the recovery is carried out by exchange of catalytic hydrogenation over Pd/C using ammonium formate as a hydrogen source.

General synthetic method 12 (recovery of azides to amines):

Azides hydronaut over a catalyst of a noble metal such as Pd/C, in a solvent such as Meon or ethyl acetate. In the case where the molecule contains an unsaturated double or triple bond, the recovery may be carried out using PPh3in the presence of water as described in pub the paths: J. Med. Chem. (1993), 36, 2558-68.

General synthetic method 13 (getting Amin):

Carboxylic acid is introduced into the reaction with the amine in the presence of an activating agent such as DCC, EDC, HOBT, anhydride n-propylphosphonic acid, GATA or di-(N-Succinimidyl)carbonate, in a dry aprotic solvent such as DHL, MeCN or DMF, at a temperature from -20°C to +60°C (see G.Benz in Comprehensive Organic Synthesis, B.M.Trost, I.Fleming, Eds; Pergamon Press: New York (1991), vol. 6, p.381). Alternatively, the carboxylic acid is activated by converting it into the corresponding acid chloride by reaction with undiluted or dissolved in, for example, DHM, oxalylamino or thionyl chloride at a temperature of from 20° to +60°C. Other activating agents can be found in the publication Comprehensive Organic Transformations. A guide to Functional Group Preparations; 2nd Edition, R.C.Larock, Wiley-VC; New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, 1999. Section nitriles, carboxylic acid and derivatives, p.1941-1949.

General synthetic method 14 (oxidation of alcohols/aldehydes into acids):

Aldehydes are oxidized to the corresponding acid using various methods described in the publication: Comprehensive Organic Transformations. A guide to Functional Group Preparations; 2nd Edition, R.C.Larock, Wiley-VC; New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, 1999. Section nitriles, carboxylic acid and derivatives, p.1653-1655. Among these methods are frequently used methods with the use of potassium permanganate in a mixture of acetone with water (see: Synthesis 1987, 85) or chlorite sodium 2-methyl-2-propanol in Pris the accordance of 2-methyl-2-butene (see: Tetrahedron 1981, 37, 2091-2096).

The alcohols can be directly oxidized to the corresponding acid using various methods described in the publications: Comprehensive Organic Transformations. A guide to Functionnal Groups Preparations; 2ndEdition, R.C.Larock, Wiley-VC; New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, 1999. Section nitriles, carboxylic acids and derivatives, p.1646-1648. Among these methods are frequently used methods using [bis(acetoxy)iodine] benzene in the presence of TEMPO, reagents Jones (CrO3/H2SO4), NaIO4in the presence of RuCl3, KMnO4or pyridine/H2Cr2O7.

General experimental methods:

Obtaining compounds of formula (I):

The compounds of formula (I) can be obtained using the methods below, the methods described in the examples, or similar methods. Optimum reaction conditions may vary depending on the specific reagents or solvents, but such conditions can be chosen by the expert in the field of technology through optimization techniques.

In sections a)to (r)below, describes the General methods of preparing compounds of formula (I). If not indicated otherwise, the generic groups or integers n, p, R0, R1, U, V, R4, R5, R2And G correspond to the given values for the formula (I). General synthetic methods that are repeatedly used throughout below Exte, are described in the above section entitled "General synthetic methods". Other abbreviations used are defined in the experimental part. In some examples, R0, R1, R2, R4, R5, U, A and G may not coincide with the structures depicted in the methods and diagrams below, as they require the use of protective gruppirovanie protective groups are well known from the prior art (see, for example, "Protective Groups in Organic Synthesis", T.W.Greene, P.G.M. Wuts, Wiley-Interscience, 1999).

a) the compounds of formula (I), where R2represents N and a represents -(CH2)p-receive in accordance with the present invention by reaction of compounds of formula (II)

with compounds of the formula (III)

,

where L1denotes halogen, such as bromine or iodine, or a group OSO2Rawhere Radenotes alkyl, CF3or tolyl, using General synthetic method 1.

b) Compounds of formula (I), where R2represents N and a represents a group-CH2CH2CH(OH)- or -(CH2)p-, p is 3 or 4 are in accordance with the present invention by reaction of compounds of formula (II)described in paragraph (a), with aldehydes of the formula (IV)

,

where a' performance is to place a -(CH 2)p-1- or-CH2CH(OPG)-, PG is a protective group, such as TBDMS or TRIPS using General synthetic method 2, compound, thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

c) the compounds of formula (I), where R2represents H, n is 1 or 2 and a represents -(CH2)p-, p is 1, 2 or 3 are in accordance with the present invention by reaction of compounds of formula (V)

,

where L2denotes halogen, such as bromine or iodine, or a group OSO2Rawhere Radenotes alkyl, CF3or tolyl, with amines of the formula (VI)

,

using the General synthetic method 1.

d) the compounds of formula (I), where R2represents N, a represents a group -(CH2)pand n is 1 or 2, receive in accordance with the present invention by reaction of compounds of formula (VII)

with the previously mentioned amines of the formula (VI), using the General synthetic method 2.

e) the compounds of formula (I), where "" no, R0represents N and U represents CH2or NH, obtained by hydrogenation of compounds of formula (I), where "" hereafter which includes link and U represents CH or N, over a catalyst of a noble metal such as Pd/C, using the General synthetic method 11. In the case where U denotes N, the transformation can also be carried out by reduction with hydride, such as NaBH4.

f) Compounds of the formula (I), where each of R4and R5represents N and a represents -(CH2)p-in addition, can be obtained by the reaction of compounds of formula (VIII)

,

where R20represents N, CH2R3'or aminosidine group, such as CBZ, Side or Fmoc, and R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester), with compounds of the formula (IX)

where L3represents a halogen. In the case of compounds of formula (IX), where G is a group G1and X denotes N or G is a group G2and Y1and/or Y3represents/represent N, the reaction is carried out in the presence of NaH. This reaction can also be carried out under the conditions described for carrying out catalyzed by metal N-arilirovaniya 2-oxazolidinone or amides. In particular, using CuI and 1,1,1-Tris-(hydroxym the Teal)ethane in the presence of Cs 2CO3(Org. Lett. (2006), 8, 5609-5612), or Pd(OAc)2and DPEphos in the presence of K3PO4. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

(g) Compounds of formula (I), where R2is not H, can also be obtained by the reaction of compounds of formula (X)

,

where a' represents -(CH2)p- or-CH2CH2CH(OPG)-, PG denotes a silyl protective group, such as TBDMS or TRIPS, with compounds of the formula (XI)

,

where L4represents halogen or the group OSO2Rawhere Radenotes alkyl, CF3or tolyl, and R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, a hydroxyl group which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester), using the General synthetic method 1. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8. In the special case when R3'denotes H, spend the reaction of compounds of formula (X)above, with dimethylsulfate.

h) Compounds of the formula (I), the de R 2is not H, can be obtained by the reaction of compounds of formula (X)above, with compounds of the formula (XII)

,

where R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester), using the General synthetic method 2. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

i) the compounds of formula (I), where R2is not H, can be obtained by the reaction of compounds of formula (X)above, with compounds of the formula (XIIa)

,

where R3'represents a C1-3alkyl or C1-3hydroxyalkyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester) and L5represents a halogen or is HE using General synthetic method 13. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8. In the special case when R3'denotes methyl, conduct the reaction with the of dinani formula (X), above, with acetic anhydride.

(j) the compounds of formula (I), where R2is not H, can be also obtained by the reaction of compounds of formula (XIII)

,

where R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester), with compounds of the formula (XIV)

,

where a' represents -(CH2)p-1- or-CH2CH(OPG)-, PG this is a silyl protecting group TBDMS or TRIPS, using General synthetic method 13. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

(k) Compounds of formula (I), where R2does not represent H, is obtained by reaction of compounds of formula (XIII)above, with compounds of the formula (III)above, using the General synthetic method 1. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

1) the compounds of formula (I), where R2does not represent H, in addition, can be produced by the reaction is connected to the second formula (V) with compounds of the formula (XV)

,

where R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester), using the General synthetic method 1. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

(m) Compounds of formula (I), where R2does not represent H, is obtained by reaction of compounds of formula (VII), above, with compounds of the formula (XV)above, using the General synthetic method 2. The compounds thus obtained, if necessary, freed from the protective groups using General synthetic method 8.

n) Compounds of the formula (I), where V denotes CR6and R6represents a carboxyl group, get through hydrolysis derivatives of the formula (I), where R6is alkoxycarbonyl (in acidic or basic conditions) or benzyloxycarbonyl (hydrogenation).

(o) Compounds of formula (I), where V denotes CR6and R6represents a group-CH2HE get through the recovery of derivatives of formula (I), where R6is alcok carbonyl or benzyloxycarbonyl, using the General synthetic method 5.

p) the compounds of formula (I), where R5represents a carboxyl group can be obtained from corresponding compounds of formula (I), where R5represents a C1-3alkoxycarbonyl, by treatment with an aqueous solution of HCl.

q) the compounds of formula (I), where R5represents a C1-3aminoalkyl, obtained by reaction of compounds of formula (XVI)

,

where z is an integer from 1 to 3 and L6represents halogen or the group OSO2Rawhere Rarepresents alkyl, CF3or tolyl, with sodium azide and subsequent transformation of the intermediate azides to the corresponding amines of the formula (I), using the General synthetic method 12.

g) Compounds of the formula (I), where "" no, U represents NR9, R9represents a C1-3alkyl, 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl, R0represents H, R2represents N and a represents -(CH2)p- or-CH2CH2CH(OH)-, is obtained by removing aminosidine group PG0the compounds of the formula (XVII)

,

where PG0represents aminosidine group, such as AC, Side, CBS or Fmoc, and R9'depict is to place a C 1-3alkyl, or R9'is a 2-hydroxyethylene, 2-hydroxypropyl or 3-hydroxypropyl group, hydroxyl which is protected silyl ester group (for example, in the form of TBDMS or TRIPS of ester using General synthetic method 4, and this reaction is used in the case when R9'represents a C2-3hydroxyalkyl group, hydroxyl which is protected in the form of a complex silyl ether, removal of the silyl protective group using General synthetic method 8.

Regarding the reactions in the above paragraphs (a)-r), in addition to already selected cases, the use of hydroxy - or aminosidine groups (see General reaction methods 7 and 8 for hydroxyamine groups and the General reaction methods 10 and 4 for aminosidine groups) is likely necessary in the following cases:

when R5represents a C1-3hydroxyalkyl or C1-3aminoalkyl;

when R6represents a C1-3hydroxyalkyl or a group -(CH2)q-NR7R8where at least one of R7and R8represents H;

when "" is absent and U represents NR9where R9represents 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl.

The compounds of formula (I)receiving the data thus can be optionally converted into their salts and especially their pharmaceutically acceptable salts.

In addition, when the compounds of formula (I) are obtained in the form of a mixture of enantiomers, the enantiomers can be separated using methods known to experts in the field of technology, for example, by formation and separation of diastereomeric salts or by HPLC on a chiral stationary phase such as a Regis Whelk-O1(R,R) (10 μm) column, Daicel ChiralCel OD-H (5-10 μm) column, or Daicel ChiralPak IA (10 μm) or AD-H (5 μm) column. Typical conditions of chiral HPLC are: isocrates the application of a mixture of eluent A (EtOH, in the presence or absence of an amine such as triethylamine, diethylamine) and eluent B (hexane)at the expiration of from 0.8 to 150 ml/min When the compounds of formula (I) are obtained as a mixture of diastereomers, they can be separated using an appropriate combination of chromatography on silica gel, HPLC and crystallization methods.

The formation of compounds of formulas (II)to(XV):

The compounds of formula (II) can be obtained either by reaction of compounds of formula (V) with sodium azide, followed by transformation into the corresponding amines of formula (II) using General synthetic method 12, or in accordance with the following schemes 1, 1a, 1b, 1c, 1d and 1e.

The compounds of formula (II), where each of R4and R5is the th N, receive according to the following scheme 1.

In scheme 1, PG1represents aminosidine group, such as the Side or Fmoc, and Rarepresents alkyl, CF3or tolyl.

Protected aminoketone derivatives of the formula (I-1) is transformed into the corresponding mesylates, triflate or tozilaty using General synthetic method 3. Received the sulfonates of the formula (I-2) is subjected to cyclization at a temperature from room temperature up to 110°C, while receiving tricyclic derivative of the formula (I-3). Then aminosidine group is removed using General synthetic method 4, thus obtaining the compounds of formula (II), where "" denotes the connection.

The compounds of formula (II), where "" is absent and U represents CH2or NH, get, using derivatives, are identical to the compounds of formula (I-1), except that U represents CH or N and PG1represents CBS. Can be used the same synthetic route, with the only difference that in the last stage in the reaction of hydrogenation occurs as the restoration of CH=CH or CH=N double bond and removal of CBZ-protective group. In the case of compounds of the formula (II), where "" is absent and U represents NH, restore, CH=N double bond can suscestvitel, using a hydride reagent such as NaBH4.

The compounds of formula (II), where R4represents N and R5represents a C1-3alkyl, C1-3hydroxyalkyl,1-3alkoxy-C1-3alkyl or C1-3alkoxycarbonyl receive according to the following scheme 1A.

In scheme 1a PG2represents aminosidine group, such as the Side or Fmoc, Rbrepresents alkyl or benzyl, Rcrepresents hydrogen or alkyl and each of Rdand Rerepresents alkyl.

The compounds of formula (II), where R4represents N and R5represents a C1-3alkoxycarbonyl get examinerdaniel acrylate derivatives of formula (Ia-1) (K2OsO4, NClNa and (DHQD)2PHAL, or (DQD)2PHAL, described in the publication: J. Org. Chem. (2005), 70, 2847-2850). Intermediate compounds of formula (Ia-2) by cyclization in turn derivative of the formula (Ia-3), using the General synthetic method 3, comprising heating at a temperature of from 50 to 70°C. the Corresponding compounds of formula (II) receive and then removing the protective group using General synthetic method 4.

The compounds of formula (II), where R5represents hydroxymethyl, obtained by reduction of the ester group of intermediate compounds is ormula (Ia-3), using the General synthetic method 5. The corresponding compounds of formula (II) receive and then removing the protective group in the compounds of formula (Ia-4), using the General synthetic method 4.

The compounds of formula (II), where R5represents methyl, get through activation of the alcohol groups of the intermediate compound (Ia-4), using the General synthetic method 3, followed by reaction with a hydride agent such as LAH or Bu3SnH. More generally, the compounds of formula (II), where R5represents C1-3alkyl, obtained by oxidation of the intermediate compounds of formula (Ia-4) into the corresponding aldehydes using General synthetic method 9, with the subsequent carrying out the Wittig reaction with alkyliden-triphenylphosphorane and catalytic hydrogenation using General synthetic method 11. The protective group of the thus obtained intermediate compounds of formula (Ia-5) then removed using General synthetic method 4, in the case of the corresponding compounds of the formula (II).

The compounds of formula (II), where R5is alkoxymethyl, obtained by reaction of the anions of compounds of formula (Ia-4) (generated by reaction with NaH) with the corresponding halides of the formula Rd-X (Rddenotes alkyl and X represents halogen). The protective group of the thus obtained intermediate with the of dinani formula (Ia-6) then remove, using the General synthetic method 4, in the case of the corresponding compounds of the formula (II).

The compounds of formula (II), where R5is dialkylhydroxylamines, obtained by reaction of esters of formula (Ia-3) with a Grignard reagent of formula Re-MgX, where Redenotes alkyl and X represents halogen. The protective group of the thus obtained intermediate compounds of formula (Ia-7) is then removed using General synthetic method 4, in the case of the corresponding compounds of the formula (II).

Compounds of formulas (II) and (V), where R4HE is a receive according to the following scheme (1b).

Accordingly, the compounds of formula (V), where R4HE is a and n is 1 or 2, are obtained by activation of the primary alcohols of the formula (Ib-1) or (Ib-2), using the General synthetic method 3, followed by reaction with NaN3. The compounds of formula (V) transferred to amines of formula (II), using the General synthetic method 12.

In addition, the compounds of formula (II), where each of R4and R5represents N and V represents CR6and R6this represents a hydroxymethyl or a group-CH2-NR7R8receive according to the following scheme 1C.

In scheme 1C PG1represents the amine is a protective group, such as the Side or Fmoc, Rfrepresents alkyl, each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl, piperidinyl, morpholinyl or thiomorpholine ring.

The compounds of formula (II), where each of R4and R5represents N, V represents CR6and R6represents a group-CH2-NR7R8receive (scheme 1C) by reaction of compounds of formula (I-3), where V represents CR6and R6represents a C1-3alkoxycarbonyl using General synthetic method 5, followed sequentially carried out by activation of the alcohol groups of intermediate compounds of formula (Ic-1), using the General synthetic method 3, and reaction with amines of the formula with other7R8using the General synthetic method 1, or, depending on the nature of R7and R8, oxidation of the intermediate compounds of formula (Ic-1), using the General synthetic method 9 followed by reductive amination, using General synthetic method 2. The corresponding compounds of formula (II) receive then removing the protective group using General synthetic method 4.

Derivatives of the formula (II), where each of R4and Rsup> 5represents N, V represents CR6and R6represents -(CH2)q-NR7R8or -(CH2)q-OH, where q is 2 or 3, get similar methods, oxidizing the compounds of formula (Ic-1) into the corresponding aldehydes and then turning them into homologous aldehydes by reaction with Ph3P=CH-OMe or Ph3P=SN-SNO with subsequent hydrolysis or hydrogenation, respectively. These homologous aldehydes can then be processed to obtain the desired compounds of formula (II), where q is 2 or 3.

The compounds of formula (II), where n is 0 and each of R4and R5represents H, receive according to the following scheme Id.

In scheme 1d PG3is an alcohol protective group, such as TBDMS or TRIPS, and Rarepresents alkyl, CF3or tolyl.

The vinyl derivative of formula (Id-1) can be converted (scheme Id) into the corresponding diol derivative of the formula (Id-2) using General synthetic method 6. Received diols selectively converted into the corresponding monomethylated or monotonicity using General synthetic method 3, and the second alcohol group then protect using General synthetic method 7-protected derivative of formula (Id-3) then cyclist term in the economic conditions. Alcohol protective group in the compounds of formula (Id-4) is then removed using General synthetic method 8, receiving the free alcohols of the formula (I) (d-5). The corresponding compounds of formula (II) are obtained after the formation of the corresponding azide derivative (reaction with DFA under the reaction conditions Mitsunobu; see Synthesis (1981), 1) with the subsequent formation of the corresponding amine using General synthetic method 12. The compounds of formula (Id-5), where R0denotes H, also produced by dihydroxypropane vinyl derivative of formula (Id-6)using General synthetic method 6, with the subsequent formation of the corresponding carbonate derivatives of formula (Id-8) after the reaction with the OED or triphosgene and finishing base type Cs2CO3. Compounds of formula (Id-4), (Id-5), and (II)where "" is absent and U represents CH2or NH, obtained by hydrogenation of the corresponding compounds of formula (Id-4), (Id-5), and (II)where "" indicates the link and U represents CH or N.

The compounds of formula (II), where R1is ethinyl receive according to the following scheme 1E.

In scheme 1e Hal represents halogen, such as bromine, and PG4represents aminosidine group, such as the Side or Fmoc

The compounds of formula (Ie-1) can be processed at temperatures from +50°C up to +110°With amenitiesalarm in the presence of PdCl2(PPh3)2, Cul and base type of tea, in a solvent such as dioxane, to obtain the compounds of formula (Ie-2). The compounds of formula (II), where R1is ethinyl get then from compounds of formula (Ie-2) after removal of the TMS group using TBAF in solvent type THF and remove aminosidine group according to General synthetic method 4.

The compounds of formula (III), where p is 1, 2, 3 or 4, compounds of formula (IV), where a' represents -(CH2)p-1and R is 3 or 4, compounds of formula (VI), where p is 1, 2, 3 or 4, and the compounds of formula (XV), where p is 1, 2, 3 or 4, receive according to the following scheme 2.

Figure 2 PG4represents-C(O)Rgwhere Rgdenotes alkyl, or PG4is a silyl protective group, such as TBDMS or TRIPS.

Alcohols of formula (II-2) obtained by reaction of epoxides of the formula (II-1) with the anions of the carbamates of the formula G-NH-COOR, where R represents alkyl or benzyl, in the presence of a base, such as KINDS or tert-Batalla lithium, followed by removing protection from alcohol in accordance with the synthetic method 8. The compounds of formula (III) receive then from alcohols f is rmula (II)-2, using the General synthetic method 3. The compounds of formula (IV), where a' represents -(CH2)p-1and R is 3 or 4, is produced by oxidation of the corresponding alcohol derivatives of formula (II-2), using the General synthetic method 9. The compounds of formula (VI) is obtained by reaction of compounds of formula (III) with sodium azide and subsequent conversion into the corresponding amine according to General synthetic method 12. Finally, the compounds of formula (XV) is obtained by reaction of intermediates of formula (VI) with an aldehyde of the formula R3'CHO, using General synthetic method 2, or with a derivative of formula R3'CH2L4where R3'is a protected silyl ether group, R3and L4is a halogen, such as iodine, bromine or chlorine, or a group of the formula OSO2Rawhere Radenotes alkyl, CF3or tolyl, using General synthetic method 1.

The compounds of formula (IV), where a' represents-CH2CH(OPG)-, PG is a silyl protecting group, such as TBDMS or TRIPS receive according to the following scheme 3.

In scheme 3, Rhrepresents alkyl (preferably tBu) and PG is an alcohol protective group, such as TBDMS or TRIPS.

The compounds of formula (III-1) is injected into the reaction (scheme 3) with Amin the mi formula G-NH 2with the subsequent reaction with the OED, while receiving oxazolidinone formula (III-2). The corresponding alcohols of the formula (III-3) obtained after recovery of ester of the formula (III-2), using the General synthetic method 5. The corresponding aldehydes of the formula (IV) are obtained then by oxidation of the alcohol derivative of the formula (III-3), using the General synthetic method 9.

The compounds of formula (V), where each of R4and R5represents H and n is 1 or 2, receive according to the following scheme 4.

In scheme 4, Rirepresents alkyl or benzyl and n is 1 or 2. Esters of the formula (IV-1) is treated with paraformaldehyde in the presence of a base such as tea or2CO3. The resulting alcohols of the formula (IV-2) can be activated using General synthetic method 3 and cyklinowanie in thermal conditions. The obtained esters of the formula (IV-3) can be restored using the General synthetic method 5, which leads to the alcohols of formula (IV-4), the activation of which according to General synthetic method 3, leads to compounds of the formula (V), where n is 1. Carbanions esters of the formula (IV-1), generated in the presence of sitedisability in THF at -78°C, treated with 4-(iodomethyl)-2,2-dimethyl-1,3-dioxolane (the com is ical product), which leads to esters of the formula (IV-5), which then turn into the corresponding alcohols of the formula (IV-6)using General synthetic method 5. These alcohols activate using General synthetic method 3, and cyclist in thermal conditions, receiving tricyclic derivative of the formula (IV-7). The acetonide protective group can be removed under acidic conditions such as aqueous solution of acetone in dilute aqueous HCl solution or in the presence of ion-exchange resin such as Amberlite® IR120. The corresponding diols break down in the presence of NaIO4to give the corresponding aldehydes, which can be restored into the corresponding alcohols of the formula (IV-8) processing hydride reagent, such as NaBH4with further alcohol activated according to General synthetic method 3, which leads to compounds of the formula (V), where n is equal to 2. Compounds of formula (IV-3), (IV-4), (IV-7), (IV-8), and (V), where "" is absent and U represents CH2or NH, obtained by hydrogenation of the corresponding compounds of formulas (IV-3), (IV-4), (IV-7), (IV-8), and (V), where "" indicates the link and U represents CH or N. Compounds of formula (IV-4), (IV-7), (IV-8), and (V), where "" indicates the link and U represents N, can also be restored to the appropriate connections, where " " is absent and U represents NH, using NaBH4, while the conversion of compounds of formula (IV-4)where U represents NH, the corresponding compounds of formula (V) is preferably carried out after temporary protection NH-group.

The compounds of formula (V), where R4HE is a receive according to the following scheme 4A.

The compounds of formula (V), where R4IT denotes and n is 1, get (scheme 4A) the conversion of compounds of formula (IV-4) in alkenone derivatives of the formula (IVa-1) as a result of activation of the alcohol group using General synthetic method 3 and subsequent treatment with base, such as DBU. Intermediate alkenone derivatives of the formula (IVa-1) can be dihydroxypropane according to General synthetic method 6, the primary alcohol group of the intermediate compounds of formula (Ib-1) then activate using the General synthetic method 3, which leads to compounds of the formula (V), where R4IT denotes and n is 1. The compounds of formula (V), where R4IT denotes and n is 2, is obtained by oxidation derivatives of the formula (Ib-1), using the General synthetic method 9, carrying out a Wittig reaction with ethoxymethyleneamino-postrana, acid hydrolysis of the intermediate compounds of formula (IVa-3) and the recovery obtained as a result is e of the aldehyde to the alcohol of formula (Ib-2), using the General synthetic method 5 before activation of the alcohol function according to General synthetic method 3. The compounds of formula (Ib-2) is also obtained by reaction of aldehydes of the formula (IVa-2) methyltriphenylphosphonium with subsequent gidroborudovaniya intermediate vinyl compounds of the formula (IVa-4) using borhydride reagent such as 9-BBN, NR3·Me2S or NR3·THF, followed by oxidation with N2About2in the presence of NaOH.

Compounds of the formula (IVa-2), and (V), where "" is absent and U represents CH2or NH, obtained by hydrogenation of the corresponding compounds where "" indicates the link and U represents CH or N.

The compounds of formula (VII) is produced by oxidation of the corresponding alcohols of formula (Ib-1), (Ib-2), (IV-4) and (IV-8)using General synthetic method 9.

The compounds of formula (VIII), where R20represents CH2R3'each of R4and R5represents N and p is 1, 2 or 3, receive according to the following scheme 5.

Figure 5 Hal represents halogen, such as chlorine or bromine, R20represents CH2R3'and R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydrox the alkyl group, the hydroxyl group of which is protected in the form of a silyl ether (e.g. as TBDMS or TBDMS ether).

Amines of formula (XIII), where each of R4and R5represents H, is introduced into reaction with halides of the formula (V-1), using the General synthetic method 1. The obtained derivatives of the formula (V-2) dihydroxyaryl using General synthetic method 6, the primary alcohol group activate using General synthetic method 3, and then get the epoxy ring after treatment with base, such as NaH, Na2CO3or tea. The epoxides of the formula (V-3) is treated with sodium azide, followed by obtaining the appropriate amine according to General synthetic method 12, and the subsequent conversion into the corresponding carbamates using KCl or Side2Oh according to General synthetic method 10. Oxazolidinone ring is formed by reaction with NaH. The compounds of formula (VIII) are also obtained by reaction of epoxy derivatives of the formula (V-3) with a complex ether of carbamino acid in the presence of Salins-complex, as described in the publications: Org. Letters (2004), 6, 3973-3975 or Org. Letters (2005), 7, 1983-1985). The compounds of formula (VIII), where U represents CH2or NH and "" no, produced by hydrogenation of the corresponding compounds of the formula (VIII), where "" indicates a tie and U represents CH or N. The compounds of formula (VIII), where "" indicates the link and U represents N, can also be restored to the appropriate connections, where "" is absent and U represents NH, using NaBH4.

Some compounds of formula (IX) are commercially available products (for example, G=G1, Q=O and X=N: CAS 337463-99-7; G=G1Q=S and X=CH: CAS 6376-70-1; G=G1, Q=O and X=CH: CAS 7652-29-1) or can be obtained according to known literature methods (for example, 7-chloro-1,8-naphthiridine-2(1H)-it is described in J. Org. Chem. (1990), 4744-59).

The compounds of formula (IX), where L3denotes Cl, G denotes the group G1X denotes N, and Q denotes S, receive according to the following scheme 6.

Accordingly, the bromo derivatives of formula (VI-1) (obtained according to WO 2008/065198) is injected into the reaction bromoacetylation, then the derivative of formula (VI-2) is reacted with thioacetate sodium in the presence of NaOMe, leading to the compound of formula (IX), where L3=Cl, G=G1X=N and Q=S.

The compounds of formula (X), where a' represents -(CH2)p-are the compounds of formula (I), where R2represents H. the compounds of formula (X), where a' represents-CH2CH2CH(OPG)-, is obtained by reaction of compounds of formula (II), where n is 0, with what soedineniya formula (IV), where a' represents a group-CH2CH(OPG)-using General synthetic method 2.

The compounds of formula (XI) can be obtained by activation of the corresponding commercially available alcohols (for example, 3-[(tert-butyldimethylsilyl)oxy]-1-propanol or 1-tert-butyldimethylsilyloxy) using General synthetic method 3.

The compounds of formula (XII) (such as (tert-butyldimethylsilyloxy)acetaldehyde or 3-[(tert-butyldimethylsilyl)oxy]Propionaldehyde) and (XIIa) are commercially available products.

The compounds of formula (XIII)where R3'represent N or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, a hydroxyl group which is protected in the form of a silyl ether (e.g. as TBDMS or TBDMS ether), can be obtained by reductive amination of aldehydes of the formula (XII) amines of the formula (II) according to General synthetic method 2. These compounds of formula (XIII) is also obtained by alkylation of amines of formula (II) derivatives of the formula (XI)using the General synthetic method 1.

The compounds of formula (XIV)where A' represents -(CH2)p-1-can be obtained by oxidation of compounds of the formula (II-2), or (IV) according to General synthetic method 14. The compounds of formula (XIV)where A' represents a group-CH2CH(OPG), PG this is a silyl protecting group, such as TBDMS or TRIPS, obtained by hydrolysis of the corresponding esters of the formula (III-2) (see scheme 3)using a base, such as LiOH, in the case when Rhdenotes methyl or ethyl, or TFA in case where Rhmeans tBu.

The compounds of formula (XV), where R3'represents hydrogen or C1-3alkyl, or R3'represents a C1-3hydroxyalkyl group, a hydroxyl group which is protected in the form of a silyl ether (e.g. as TBDMS or TBDMS ether), is obtained by alkylation of amines of formula (VI) derivatives of the formula R3'-CH2-X (X represents Cl, Br or I), using the General synthetic method 1.

The compounds of formula (XVI) are obtained from the corresponding compounds of formula (I), where R5represents (CH2)zOH, using the General synthetic method 3.

The compounds of formula (XVII) are obtained according to the following scheme 6A.

In scheme 6A PG0represents aminosidine group, such as AC, Side, CBS or Fmoc, and R9'represents hydrogen or C1-2alkyl, or R9'represents a C1-2hydroxyalkyl group, a hydroxyl function which is protected in the form of a silyl ether (e.g. as TBDMS or TRIP the ether).

The compounds of formula (I)6A (for example, the compounds of formula (I), where "" denotes a bond, R0denotes N; U denotes N and R2denotes N) can be protected aminoadipic group PG0according to General synthetic method 10. The compounds of the formula (6A-1) can be transformed into derivatives of the formula (6A-2) by restoring over a catalyst of a noble metal such as Pd/C, or restoring borhydride reagent, such as NaBH4. Intermediate compounds of formula (6A-2) can be introduced into the reaction with aldehydes of the formula (6A-3) using the General synthetic method 2, which leads to compounds of the formula (XVII). Alternatively, the compounds of formula (6A-2) can be converted into compounds of formula (XVII) by reaction with alkylhalogenide formula R9'-Hal (Hal denotes a halogen atom).

The intermediate compounds of formulae (I-1), (Ia-1), (Id-1), (Id-6), (Ie-1), (II-1), (III-1), (IV-1), and (XIII):

The compounds of formula (I-1) are obtained from compounds of the formula (IV-1) according to the following scheme 7.

In figure 7, Rjdenotes alkyl or benzyl.

Esters of the formula (IV-1) is injected into the reaction (scheme 7) with bromoacetonitrile in the presence of a strong base, such as Li, in a solvent such as THF, at temperatures from -78°C to -20°C. the Floor is Chennai nitrile derivative of formula (VII-1) is injected into the reaction with LAH in a solvent, such as THF or ether, and the amino group of the compounds of the formula (VII-2) protects using General synthetic method 10, which leads to compounds of the formula (I-1), where n is equal to 2. Esters of the formula (IV-1) is injected into the reaction with N-(methyl bromide)phthalamide in the presence of a strong base, such as Li, in a solvent such as THF, at temperatures from -78°C to -20°C. the Obtained phthalimide derivatives of the formula (VII-3) process then the derivatives of hydrazine, such as hydrazinehydrate, which leads to the corresponding primary amines of the formula (VII-4), where n is 1. The amino derivatives of formula (VII-4) protect according to General synthetic method 10 and ester function restore using General synthetic method 5, and receive the compounds of formula (I-1), where n is 1. Esters of the formula (IV-1) by reaction with N-bromosuccinimide to form the corresponding bromides of the formula (VII-5), which enter into reaction with phthalimido potassium. Received tallygaroopna formula (VII-6) is treated with a derivative of hydrazine, such as hydrazinehydrate to give the corresponding primary amines of the formula (VII-4), where n is 0. The amino derivatives of formula (VII-4) then protect using General synthetic method 10, and ester function restore using General synthetic method 5, and receive the connection forms of the crystals (I-1), where n is 0.

The compounds of formula (I-1), where n is 0, can also be obtained from compounds of the formula (III-2) according to the following scheme 7a.

In scheme 7a PG1represents aminosidine group, such as the Side or Fmoc, and PG5represents hydroxyamino group, such as TBDMS or TRIPS.

The compounds of formula (I-1), where n is 0, also get (scheme 7a) of acepromozine formula (III-2). The primary alcohol function of diols of the formula (III-2) protects using General synthetic method 7, before the conversion of the secondary alcohol group into the corresponding azide by activation of the alcohol under the reaction conditions Mitsunobu (in the presence of PPh3and DEAD or DYADS in a solvent such as THF, DMF, DHM or DME, at a temperature from -20°C to 60°C, according to the publication: O. Mitsunobu in Synthesis (1981), 1), reaction with DFA, the conversion of the primary amine according to General synthetic method 12 and the formation of carbamate according to General synthetic method 10 for producing compounds of formula (VIIa-1). Protecting the alcohol group of the intermediate compounds of formula (VIIa-1) can then be removed according to General synthetic method 8.

The compounds of formula (Ia-1) are obtained from aldehydes of the formula (VIII-2)

by Wittig reaction with alkoxycarbonyl what identifizieren.

The compounds of formula (Id-1) can be obtained according to the publications WO 02/08224, WO 2004/058144 or WO 2008/126024 or according to the following scheme 8.

Figure 8 L5represents a halogen (such as bromine) or OTf.

The compounds of formula (VIII-1) (see scheme 8) is injected into the reaction trivinylbenzene in the presence of a palladium catalyst such as tetrakis(triphenylphosphine)palladium, obtaining the compounds of formula (Id-1), where R0represents N. The compounds of formula (Id-1) (including, where R0represents a C1-3alkoxygroup) is also obtained by reaction of aldehydes of the formula (VIII-2) methyltriphenylphosphonium.

The compounds of formula (Id-6) are obtained similarly to obtain compounds of formula (Id-1) based on derivatives of the formula (VIII-3)

(commercially available or can be obtained according to the publications WO 2008/148867, WO 2008/003690, WO 2006/125974 or WO 2008/150827).

The compounds of formula (Ie-1) are obtained by protecting the amino group of the corresponding compounds of the formula (II), where R1represents halogen, using General synthetic method 10.

The compounds of formula (II-1), where p is 1 and PG4denotes-C(O)Rg, Rgthis denotes alkyl, commercially available. The compounds of formula (II-1), where p is 2 or 3 and PG denotes TRIMS, can be perceived by the s according to the publications WO 2007/144423 or HER.

The compounds of formula (III-1), where PG denotes TRIMS, can be obtained according to or analogously published in Bioorganic & Medicinal Chemistry Letters (1996), 6(8), 991-994.

The compounds of formula (IV-1) can be obtained as described in the publications WO 2007/122258, WO 2007/115947 and WO 2007/081597.

The compounds of formula (VIII-1), where R1denotes N and L5denotes the Otf can be obtained according to WO 2004/002490. The compounds of formula (VIII-1), where R1denotes F, can be obtained similarly to obtain compounds of the formula (VIII-1), where R1denotes Cl, according to the description in WO 2006/021448.

The compounds of formula (VIII-2), where R0denotes H or a methoxy group, R1denotes H or F, and one of U and V represents CH, while the other represents CH or N, can be obtained according to the publications WO 98/17672, WO 2006/046552, WO 2008/126024 or WO 2008/152603.

The compounds of formula (VIII-2), where U represents N, V represents N and R0denotes H or a methoxy group, can be obtained according to the following scheme 9.

In scheme 9 X represents halogen, such as bromine or chlorine.

Diaminopropane formula (IX-1) is injected into the reaction bromoxynil acid, receiving the intermediate compounds of formula (IX-2), which is then oxidised using MnO2. Aromatic intermediate compounds of formula (IX-3) then enter into reaction with methyliodide in Pris is accordance CsCO 3getting the compounds of formula (IX-7), where R0means H. the compounds of formula (IX-7), where R0represents OMe, obtained by reaction of compounds of formula (IX-1) diacylglycerol, receiving the intermediate compounds of formula (IX-5), which are then converted into derivatives of the formula (IX-6) by reaction with POCl3and derivatives of the formula (IX-7), where R0represents OMe, after reaction with NaOMe in Meon. The compounds of formula (IX-7) is then converted into derivatives of the formula (VIII-2) after reaction with a strong base such as n-BuLi, and capture the resulting intermediate compounds using DMF.

The compounds of formula (IX-1), where R1denotes H, get on the description in US 5298518. The compound of formula (IX-1), where X is Br and R1denotes F, receive according to the following scheme 10.

Commercially available pyridine derivative of the formula (X-1) is transformed into the corresponding aminopyridine derivative of the formula (X-2) by reaction with l3and then ammonia. The intermediate compound of formula (X-2) then enter into reaction with HNO3/Asón and then restore (for example, using Zn/HCl), thus obtaining the compound of formula (IX-1), where X denotes Br, and R1denotes F.

Separate embodiments of the present invention are described in the following examples which serve to illustrate what subramania, in no way limiting its scope.

Examples

All temperatures are given in °C. Compounds are characterized by means of1H-NMR (300 MHz) (Varian Oxford), or1H-NMR (400 MHz) (Bruker Advance 400); chemical shifts are given in memorial plaques relative to the solvent used; the multiplets: s = singlet, d = doublet, t = triplet, q = quadruplet, p = Pente, Gex = getset, hept = septet, m = multiplet, constant interaction are given in Hz. Alternatively, the compounds were characterized using LC-MS (Sciex API 2000 with Agilent 1100 Binary Pump, DAD and ELSD or Agilent quadrupole MS 6140 with Agilent 1200 Binary Pump, DAD and ELSD); by TLC (TLC-plates from Merck, silica gel 60 F254); or by melting point. Compounds purified by chromatography on silica gel 60A. NH4OH, to be used for column chromatography, represents a 25%aqueous solution.

Analyses by HPLC performed on a stationary phase, such as rapid resolution SB Bond CIS to 1.8 μm) column, or rapid resolution Bond Eclipse Plus C18 (1,8 µm) column. Typical conditions for HPLC: the gradient of eluent A (water/MeCN in the ratio 95:5 with 0.1% formic acid, in the presence or without 5 mmol/l ammonium formate) and eluent B (MeCN/water in a ratio of 95:5 with 0.1% formic acid, in the presence or without 5 mmol/l ammonium formate)at the expiration of from 0.8 to 5 ml/min Racemate can be separated into the enantiomers as described the above. Preferred conditions for chiral HPLC following: column ChiralPak AD (a 4.6×250 mm, 5 μm), using isocrates mixture (for example, in the ratio 10:90) as eluent A (EtOH, in the presence of diethylamine in number, for example, 0.1%) and eluent B (hexane)at room temperature, with the flow rate, for example, 0.8 ml/min

General methods:

Method a: the recovery of esters using LAH

To a solution of ester (1 mmol) in THF (15 ml), cooled to 0°C, add one portion of LAH (3.5 EQ.). The mixture was stirred at the same temperature for 30 min, and then in the interval from 0°C to room temperature until the reaction is completed (1-3 h), then carefully add water (0.4 ml), and then 2-molar solution of NaOH (0.8 ml) and water (0,40 ml). After stirring for 5 min add Na2SO4(1 g) and the mixture is again stirred for 15 minutes, the Solids filtered off and thoroughly washed with ethyl acetate. The filtrate is concentrated without dried under reduced pressure.

Method: remove the BOC-protective group

Side-zasidannya amine (1 mmol) is dissolved in DHM (2 ml) and treated with Et3SiH (optional, 0.2 ml, 1.1 EQ.) and TFA (2 ml). The mixture is stirred at room temperature for 1 h, concentrated in vacuo and transferred to a mixture of DHM with aqueous solution of NH4OH. The organic layer is washed with the ode, dried over MgSO4and concentrate under reduced pressure.

Method: alkylation of amines by mesylates

A solution of amine (1.0 to 2.3 mmol), nelfinavir (1 mmol) and DIPEA (1.1 mmol) in dry DMSO is heated at a temperature of 70°C. until the reaction is completed (1-5 days). After cooling, add water and ethyl acetate, and then separate the phases. The aqueous layer was extracted two times with ethyl acetate and the combined organic layers washed with water (three times) and brine, dried over MgSO4and concentrate under reduced pressure. The residue is purified by column chromatography.

Method D: alkylation of amines iodides

A solution of amine (1 mmol), iodide (1 mmol) and DIPEA (1.1 mmol) in dry DMSO is heated at a temperature of 70°C. until the reaction is completed (1-3 days). After cooling, add water and ethyl acetate, and then separate the phases. The aqueous layer was extracted two times with ethyl acetate and the combined organic layers washed with water (three times) and brine, dried over MgSO4and concentrate under reduced pressure. The residue is purified by column chromatography.

Method E: reductive amination

A solution of amine (1 mmol) and aldehyde (1 mmol) in a solution of EDC/Meon (in a ratio of from 1:1 to 4:1, 10 ml) was treated with NaBH(SLA)3(2 mmol). The mixture is stirred at room temperature until complete C is the conclusion of the reaction (1-4 h), dilute DHM, treated with an aqueous solution of NH4OH, and then the phases are separated. The aqueous layer was extracted several times DHM and the combined organic layers washed with water and brine, dried over MgSO4and concentrate under reduced pressure. The residue is then purified using column chromatography.

Method F: hydrogenation

The solution is unsaturated compounds (1 mmol) in Meon (20 ml) and Asón (optional, 20 ml) hydronaut over 10%Pd/C (200 mg) for 20 hours, the Catalyst is filtered off, washed with a mixture of Meon/DHM and concentrate. Then to the filtrate is added 28%aqueous solution of NH4OH and the mixture is extracted with DHM/Meon in the ratio of 9:1. The organic layer is dried over MgSO4, concentrated and purified by column chromatography.

Method G: the introduction of the BOC-protective group

Side2(Of 1.05 equiv.) and tea (1.5 EQ.) added at room temperature to a solution of the appropriate amine (1.0 EQ.) in THF. The reaction mixture was stirred at room temperature for 1 h, concentrated without dried and purified by column chromatography.

Method N: receiving nelfinavir

The tea or DIPEA (2 EQ.) and MsCl (1.2 EQ.) add at a temperature of 0°C. to a solution of the desired alcohol (1 EQ.) in DGM or EDC, after which the reaction mixture is stirred for 1 h at the same temperature. In SL the tea when formed mesilate is introduced into the reaction of cyclization to obtain the tricyclic system, the reaction mixture continued to stir at a temperature of from room temperature to 45°C for 6 to 72 hours Then add saturated aqueous solution of NaHCO3and the mixture is extracted with DHM (three times). The combined organic layers dried over MgSO4, filtered and concentrated under reduced pressure, obtaining the required mesilate, which is used in the next stage without purification.

Method I: derivatization of oxazolidinone to the OED

The solution required amerosport (1 EQ.) in THF is treated with the OED (1.5 EQ.) and heated at 50°C overnight, after which the mixture is cooled to CT, diluted with ethyl acetate and washed with water. The organic layer was washed with a 0.5-molar solution of HCl (optional) and water, dried over MgSO4and concentrate. The remainder or rubbed with an organic solvent, crystallized from a mixture of heptane/EA or purified using column chromatography.

Method J: delete TBDMS-ether protective groups

The solution TBDMS ester (1 EQ.) in THF is treated TBAF (1-molar solution in THF, 1.2 EQ.) at 0°C. Then the solution is stirred at 0°C for 6 h, then mixed with water and ethyl acetate and the aqueous phase extracted with ethyl acetate (three times). The combined organic layers washed with water (three times) and brine, dried over MgSO4and kontsentriruitesi reduced pressure. The residue is rubbed with an organic solvent or purified by using column chromatography.

Method: the formation of iodides on Finkelstein

Suspension nelfinavir (1 EQ.) and NaI (3 EQ.) 2-butanone is heated at a temperature of 85°C for 3 h to 3 days. After cooling, the mixture is diluted with a solution of ether/EA and treated with 10%aqueous solution of Na2S2O3. After stirring for 10 minutes the phases are separated and the aqueous layer washed with ethyl acetate. The combined organic layers washed with water (twice), dried over MgSO4and concentrate under reduced pressure. The residue is rubbed with an organic solvent.

Method L: asymmetric dihydroxypropane (Chem. Rev. (1994), 94, 2483)

A mixture of olefin (1 mmol) in a mixture of tert-BuOH/H2O (in the ratio 1:1, 10 ml) at room temperature is treated with methylsulfonium (1 EQ.) and AD-mix α or AD-mix β (1.5 g). The mixture is then vigorously stirred at room temperature until completion of the reaction, add Na2S2O3(1.5 g), after which the mixture is diluted with ethyl acetate (30 ml). The phases are separated and the aqueous phase is extracted several times with ethyl acetate. The combined organic layers washed with water and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography.

Method M: introduction TBDMS-protect the Noah group:

To a solution of the alcohol (1 EQ.) and imidazole (1.1 EQ.) in THF (10 ml/mmol) at a temperature of 0°C was added dropwise a solution of l (1 EQ.) in THF. The mixture is stirred at room temperature until the reaction is completed, after which the mixture is diluted with ethyl acetate, washed with water and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography.

Method N: reaction Mitsunobu

To a solution of the alcohol (1 EQ.) and PPh3(1.1 EQ.) in THF (2 ml/mmol)cooled to 0°C, was added dropwise DFFA (1.1 EQ.) and DYADS (1.2 equiv.) the mixture is heated to room temperature within 1 h and stirred at this temperature until completion of the reaction. The mixture is then concentrated under reduced pressure and the residue purified by column chromatography.

Method N': reaction Mitsunobu under the reaction conditions of Staudinger and the introduction of Side-protection

After the implementation of the method N with alcohol (1 EQ.), as described above, azide dissolved in a mixture of THF/water (in the ratio 9:1), treated with PPh3(1.2 equiv.) and the resulting solution is heated at a temperature of 50°C. until complete conversion to the amine. The mixture was then cooled, treated Side2O (1.5 EQ.) and stirred at room temperature overnight. Volatiles are removed under reduced pressure and the residue purified by column chromatography, getting Side-samisen the th Amin.

Experimental method: rat-1-aminomethyl-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

A.i. (7-fluoro-2-methoxyquinoline-8-yl)acetonitrile

To a solution of 8-methyl bromide-7-fluoro-2-methoxyaniline (20,0 g, 74 mmol; obtained according to the description in WO 2007/081597) in DMF (530 ml) was added KCN (22.1 g, 339 mmol) and the mixture is stirred at a temperature of 70°C during the night. The mixture is then concentrated, added water and ethyl acetate and the aqueous layer was extracted with ethyl acetate. The combined organic layers washed with brine, dried over MgSO4and concentrate, getting mentioned in the title intermediate compound in the form of a beige solid (16,13 g, 100%yield).

MS (ESI, m/z): 217,4 [M+H+].

A.ii. Methyl ester (7-fluoro-2-methoxyquinoline-8-yl)acetic acid

To a solution of intermediate compound (A.i) (16,1 g, 75 mmol) in Meon (270 ml) is added TMCCl (32 ml, 3,38 equiv.) the solution is stirred at a temperature of 80°C for 3 h, then concentrated under reduced pressure and transferred to a mixture of etelaat and water. The phases are separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers washed with 2-molar NaOH solution, water and brine, dried over MgSO4, concentrated and purified by column chromatography (DHM), getting mentioned in the title intermediate compound as a colourless solid (8,13 g, 44%of you who ar).

MS (ESI, m/z): 250,2 [M+H+].

A.iii. Methyl ether rat-3-(1,3-dioxo-1,3-dihydroindol-2-yl)-2-(7-fluoro-2-methoxyquinoline-8-yl)propionic acid

To a solution of Li (31,3 ml 1-molar solution in THF) in THF (40 ml) is added at a temperature of -78°C. a solution of intermediate compound (A.ii) (6.50 g, 26 mmol) in THF (50 ml) for 10 minutes After stirring for 1 h at -78°With a solution of N-(methyl bromide)phthalamide in THF (50 ml) is added dropwise within 10 min, after which the mixture was stirred at -78°C for 1 h and then at room temperature throughout the night. The resulting solution was quenched by adding 1 normal HCl solution (260 ml), and extracted with DHM. The combined organic layers washed with water, dried over MgSO4, concentrated and purified by column chromatography (heptane/EA in the ratio 1:1). The obtained solid connection triturated with ethyl acetate, getting mentioned in the title intermediate compound as a colourless solid (2,42 g, 23%yield).

MS (ESI, m/z): 409,3 [M+H+].

A.iv. Methyl ether rat-3-amino-2-(7-fluoro-2-methoxyquinoline-8-yl)propionic acid

To a suspension of intermediate compounds (A.iii) (2,40 g, 5,88 mmol) in EtOH (40 ml) is added dropwise hydrazinoacetate (1,43 ml, 5 EQ.) at room temperature. The mixture is stirred for 2 h at room temperature, before the concentrate. The residue is transferred into ethyl acetate and 10%citric acid solution and the layers separated. The aqueous phase is treated again with ethyl acetate, and then alkalinized NH4OH and extracted twice DHM. United DHM-phase is dried over MgSO4and concentrate, getting mentioned in the title intermediate compound in the form of a pale yellow oil (1,62 g, 99%yield).

MS (ESI, m/z): 279,4 [M+H+].

A.v. Methyl ether rat-3-tert-butoxycarbonylamino-2-(7-fluoro-2-methoxyquinoline-8-yl)propionic acid

On the basis of the intermediate compound (A.iv) (1,62 g of 5.82 mmol) using method G, specified in the header of the intermediate compound obtained as colorless solids (1,87 g, 85%yield).

MS (ESI, m/z): to 379.2 [M+H+].

A.vi. tert-Butyl ether rat-[2-(7-fluoro-2-methoxyquinoline-8-yl)-3-hydroxypropyl]carbamino acid

On the basis of the intermediate compound (A.v) and using the method As specified in the header of the intermediate compound obtained as colorless solids (1,69 g, 98%yield).

MS (ESI, m/z): to 351.3 [M+H+].

A.vii. tert-Butyl ether rat-(9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-ylmethyl)carbamino acid

On the basis of the intermediate compound (A.vi) (1.68 g, 4.8 mmol) and using method H, specified in the header of the intermediate compound obtained as beige solids is (1.56 g, 100%output).

MS (ESI, m/z): 319,3 [M+H+].

A.viii. rat-1-Aminomethyl-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (A.vii) and using the method specified in the title compound obtained as a pale orange solid (1.08 g, quantitative yield).

1H NMR (CDCl3) δ: 7,66 (d, J=9.4 Hz, 1H), 7,40 (dd, J=8,8, 4,7 Hz, 1H), to 6.88 (m, 1H), is 6.61 (d, J=9.4 Hz, 1H), 4.53-in (dd, J=12,9, and 9.4 Hz, 1H), 4,36 (dd, J=12,9, a 4.7 Hz, 1H), 3,95 (m, 1H), of 1.97 (m, 2H), 3.15 in (m, 2H).

MS (ESI, m/z): 219,2 [M+H+].

Experimental method: rat-1-(2-amino-ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

B.i. Methyl ether rat-3-cyano-2-(7-fluoro-2-methoxyquinoline-8-yl)propionic acid

Li (18,4 ml, 1.1 EQ., 1-molar solution in THF) is added at -78°C for 15 min to a solution of intermediate compound (A.ii) (4,17 g, and 16.7 mmol) in THF (40 ml). The resulting mixture was stirred for 2 h at the same temperature, then added dropwise within 20 min bromoacetonitrile (3.0 g, 1.5 EQ.) and stirring is continued at -78°C for 2 h, then the reaction is quenched with water and extracted with ethyl acetate (three times). The combined organic phases are washed with brine, dried over MgSO4filter and concentrate. The residue is purified by column chromatography (heptane/EA ratio from 2:1 to 1:1), obtaining specified in the header intermediate Obedinenie in the form of a yellow solid (3,96 g, 82%yield).

MS (ESI, m/z): 289,4 [M+H+].

V. II. rat-4-Amino-2-(7-fluoro-2-methoxyquinoline-8-yl)butane-1-ol

To a solution of AlCl3(4.0 g, 30 mmol) in ether (150 ml) was added LAH (30 ml, 1-molar solution in THF) dropwise over 10 min at -78°C. After stirring for 15 min add a suspension of intermediate compounds (B.i) (3.94 g, 13.7 mmol) in ether (120 ml) for 15 minutes, the Suspension is then stirred at room temperature for 4 h, cooled to a temperature up to 0°C and quenched with saturated aqueous Na2SO4, after which the mixture is alkalinized NH4OH and extracted with ethyl acetate (three times). The combined organic phases are dried over Na2SO4, filtered and concentrated, obtaining mentioned in the title intermediate compound as a yellow oil (3,86 g, quantitative yield), which without further purification used in the next stage.

MS (ESI, m/z): 265,4 [M+H+].

W. tert-Butyl ether rat-[3-(7-fluoro-2-methoxyquinoline-8-yl)-4-hydroxybutyl]carbamino acid

On the basis of intermediate compounds ((II) (3,85 g of 14.57 mmol) using method G, specified in the header of the intermediate compound obtained as a yellow oil (2,69 g, 51%yield).

MS (ESI, m/z): 365,1 [M+H+].

B.iv. tert-Butyl ether rat-[2-(9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)ethyl]carbonin the howling acid

On the basis of the intermediate compound (B.iii) (2,68 g, 7.4 mmol) and using method H, specified in the header of the intermediate compound obtained as a pale orange solid (2.67 g, quantitative yield), which without further purification used in the next stage.

MS (ESI, m/z): 333,1 [M+H+].

.v. rat-1-(2-amino-ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (B.iv) and using the method specified in the title compound is obtained after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4) as a pale orange solid (1,34 g, 72%yield).

1H NMR (CDCl3) δ: to 7.68 (d, J=9,3 Hz, 1H), 7,40 (dd, J=8,8, 4.8 Hz, 1H), 6.89 in (m, 1H), 6,63 (d, J=9.5 Hz, 1H), 4,56 (dd, J=12,8, and 9.3 Hz, 1H), 4,21 (dd, J=12,5, 4.8 Hz, 1H), 4.00 points (m, 1H), 2,89 (m, 2H), 2,18 (m, 1H), 1,86 m, 1H), 1,24 (m, 2H).

MS (ESI, m/z): 233,5 [M+H+].

Experimental method: rat-1-Amino-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

C.i. Methyl ether rat-bromo-(7-fluoro-2-methoxyquinoline-8-yl)acetic acid

NBS (1.6 g) and AIBN (0.1 g) are added to a mixture of intermediate compound (A) (1.50 g, 6.0 mmol) in triptoreline (30 ml). The mixture is heated at a temperature of 80°C when illuminated with UV light for 5 hours After cooling, the reaction mixture was concentrated, the residue is transferred into ethyl acetate, washed twice with 10%-s ' solution of the thiosulfate is sodium, dried over Na2SO4filter and concentrate without dried. The residue is triturated with a mixture of heptane/EA, getting mentioned in the title intermediate compound as a colourless solid (1.42 g, 72%yield).

MS (ESI, m/z): 328,2 [M+H+].

C.II. Methyl ether rat-(1,3-dioxo-1,3-dihydroindol-2-yl)-(7-fluoro-2-methoxyquinoline-8-yl)acetic acid

To a solution of intermediate compound (C.i) (1.31 g, 4.0 mmol) in dry DMF (25 ml) add phthalamic potassium (1.24 g, 6.6 mmol) in argon atmosphere. The resulting solution is stirred at a temperature of 120°C for 1 h, and after cooling to room temperature, water is added and the mixture extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4and concentrate. The residue is crystallized from a mixture of heptane/EA, getting mentioned in the title intermediate compound in the form of a beige solid (1.04 g, 66%yield).

MS (ESI, m/z): 395,1 [M+H+].

C.iii. Methyl ether rat-amino-(7-fluoro-2-methoxyquinoline-8-yl)acetic acid

To a solution of intermediate compound (C.ii) (714 mg, is 1.81 mmol) in EtOH (10 ml) is added dropwise hydrazinoacetate (0.9 ml, 10 EQ.) at room temperature. The mixture was then stirred for 3 h at the same temperature, then the precipitate is filtered off. The filtrate is concentrated when s is low pressure and distributed between ethyl acetate and 10%aqueous citric acid solution. The aqueous layer was washed several times with ethyl acetate and then alkalinized using NH4OH. The aqueous layer was extracted with DHM and the organic layer concentrated under reduced pressure, obtaining mentioned in the title intermediate compound as a colourless solid (398 mg, 83%yield).

MS (ESI, m/z): 265,5 [M+H+].

C.iv. Methyl ether rat-tert-butoxycarbonylamino-(7-fluoro-2-methoxyquinoline-8-yl)acetic acid

On the basis of the intermediate compound (C.iii) (380 mg, 1.44 mmol) using method G, specified in the header of the intermediate compound obtained as a colorless solid (560 mg, 100%yield).

MS (ESI, m/z): 365,0 [M+H+].

.v. tert-Butyl ether rat-[1-(7-fluoro-2-methoxyquinoline-8-yl)-2-hydroxyethyl]carbamino acid

On the basis of the intermediate compound (C.iv) and using the method As specified in the header of the intermediate compound obtained as blignault solid (473 mg, 92%yield).

MS (ESI, m/z): 337,3 [M+H+].

C.vi. tert-Butyl ether rat-(9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij)quinoline-1-yl)carbamino acid

The tea (0.4 ml, 2 EQ.) and MsCl (of 0.13 ml, 1.2 EQ.) added at a temperature of 0°C. to a solution of intermediate compound (C.v) (470 mg, of 1.40 mmol) in DHM (10 ml). The reaction thus proceeds at this temperature for 20 minutes Then add the bicarbonate of sodium and DF is, layers decanted and the aqueous layer was again extracted with DHM. The combined organic layers are dried over Na2SO4filter and concentrate without dried. The residue is used without further purification. A solution of crude nelfinavir in toluene (20 ml) is heated at a temperature of 85°C. overnight, cooled to room temperature, add water and ethyl acetate, and then the layers separated. The aqueous layer was extracted again with ethyl acetate and the combined organic layers washed with saturated aqueous NaHCO3and concentrate. The residue is triturated with a mixture of ether/EA, getting mentioned in the title intermediate compound as a colourless solid (193 mg, 45%yield).

MS (ESI, m/z): 305,0 [M+H+].

C.vii. rat-1-Amino-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (C.vi), and using the method specified in the title compound obtained as a beige solid (128 mg, 100%yield).

1H NMR (DMSO-d6) δ: 7,88 (d, J=9.4 Hz, 1H), to 7.61 (dd, J=8,5, 5.0 Hz, 1H), 6,99 (dd, J=9,7, 8,8 Hz, 1H), of 6.49 (d, J=9.4 Hz, 1H), 4.92 in (dd, J=8,8, 4,4 Hz, 1H), of 4.44 (dd, J=12,9, 8,8 Hz, 1H), 3,86 (dd, J=12,6, 3.8 Hz, 1H), 2,29 (s, 2H).

MS (ESI, m/z): 205,1 [M+H+].

Experimental method D: (R)-4-Amino-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

D.i. (R)-2-Azido-2-(6-methoxy[1,5]naphthiridine-4-yl)ethanol and (S)-2-azido-1-(6-methoxy[1,5]naphthiridine-4-yl), this is ol

A mixture of (S)-2-methoxy-8-oxiranyl[1,5]naphthiridine (4 g, 20 mmol; obtained according to the description in WO 2006/002047), NH4Cl (2.7 g, 2.5 EQ.) and NaN3(3.2 g, 2.5 EQ.) in the Meon (100 ml) and water (2 ml) is heated at 65°C for 4 h, filtered and concentrated in vacuo. The residue is transferred into ethyl acetate and washed with saturated solution of NaHCO3and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography (heptane/EA ratio of 1:1, 1:2, EA)to give a mixture of regioisomers in a ratio of 3:2 (5 g, 100%yield), which is used in the next stage without purification.

D.ii. tert-Butyl ester [(R)-2-hydroxy-1-(6-methoxy[1,5]naphthiridine-4-yl)ethyl]carbamino acid

A solution of intermediate compound (D.i) (mixture of isomers, 5 g of 20.7 mmol) in a mixture of THF/Meon (in the ratio 1:1) (200 ml) hydronaut over Pd/C (10%, 2.2 g) under hydrogen pressure (1 bar) for 1 h, the Catalyst was then filtered off and the filtrate is concentrated under reduced pressure. The residue is dissolved in DHM (150 ml), then add the Bok2(6.8 g, 1.5 EQ.). The mixture is stirred at room temperature for 2 h, concentrated in vacuo and purified by column chromatography (EA/heptane 2:1, EA, EA/Meon in the ratio 9:1)to give the desired isomer as a colorless foam (2.8 g, 43%yield).

1H NMR (DMSO-d6) δ: 8,72 (d, J=4.4 of the C, 1H), 8,24 (d, J=9.1 Hz, 1H), 7,56 (d, J=4.4 Hz, 1H), 7,33 (d, J=8.5 Hz, 1H), 7,25 (d, J=9.1 Hz, 1H), 5,64 (m, 1H), 3,99 (m, 3H), of 3.78 (m, 1H), to 3.58 (dd, J=10,8, 7,0 Hz, 1H), of 1.35 (s, 9H).

D.iii. tert-Butyl ester ((R)-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-yl)carbamino acid

On the basis of the intermediate compound (D.ii) (2.8 g, 8,8 mmol) using method H, specified in the header of the intermediate compound obtained as off-white solid (1.2 g, 47%yield) after purification using column chromatography (EA, EA/Meon in the ratio 9:1) and crystallization from ether/EA.

MS (ESI, m/z): 288,4 [M+H+].

D.iv. (R)-4-Amino-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

A solution of intermediate compound (D.iii) (1 g, of 3.48 mmol) in dioxane is treated with 4-normal solution of HCl in dioxane (4 ml). The beige suspension is stirred at room temperature overnight, filtered, washed with ether and dried, receiving dihydrochloride (475 mg, 52%yield). Free base exhale, using ion-exchange resin (Dowex 50), elwira methanolic solution of ammonia, and while receiving a beige solid (0.3 g).

1H NMR (DMSO-d6) δ: 8,55 (d, J=4,7 Hz, 1H), to 7.99 (d, J=9.7 Hz, 1H), 7,65 (dd, J=4,7, 0.9 Hz, 1H), PC 6.82 (d, J=9.7 Hz, 2H), 5,12 (ddd, J=8,8, 4,1, 0.9 Hz, 1H), 4.53-in (dd, J=13,2, 8,8 Hz, 1H), 4,05 (m, 3H).

Experimental method E: the rat-4-Aminomethyl-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

E.i. Diethyl ether 2-(3-ft is R-6-methoxy[1,5]naphthiridine-4-yl)malonic acid

Diethylmalonate (12,4 ml of 81.7 mmol) are added to a suspension of NaH (3.0 g, or 47.9 mmol, 60%solution in mineral oil) in dioxane (35 ml). The mixture is stirred at room temperature for 5 min, and then heated at a temperature of 80°C for 1 h After cooling to room temperature, add CuBr (1.4 g, 9.6 mmol) and 8-bromo-7-fluoro-2-methoxy[1,5]naphthiridine (7.0 g, to 27.2 mmol, obtained as described in WO 2007/122258). The mixture is stirred at a temperature of 100°C for 6 h, and after cooling to room temperature, add 10%solution of NaHSO4(100 ml). The mixture is stirred for 30 min at room temperature, both the layer is decanted and the aqueous layer was extracted with ethyl acetate (three times 150 ml). The combined organic layers washed with brine, dried over Na2SO4filter and concentrate without dried. The residue is purified by column chromatography (heptane/EA in the ratio 3:1, then 1:1), obtaining mentioned in the title intermediate compound as a yellow oil (by 8.22 g, 90%yield).

MS (ESI, m/z): 337,3 [M+H+].

E.ii. Ethyl ester of (3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)acetic acid

Water (of 0.53 ml, 1.2 EQ.) and LiCl (2,07 g, 2 EQ.) added to a solution of intermediate compound (E.i) (by 8.22 g, 24.4 mmol) in DMSO (170 ml). The mixture is heated to a temperature of 110°C for 16 h and add the second portion of LiCl (2,34 g). The mixture is then heated the Ute at a temperature of 110°C for 16 h, the solvent is evaporated under reduced pressure (bath temperature 70°C, pressure of 0.5 mbar). The residue is distributed between 10%aqueous solution of NaHSO4(200 ml) and ether (200 ml). The aqueous layer was extracted with ether (twice po ml). The combined organic layers are filtered through a layer of silica gel and the filtrate concentrated without dried, obtaining mentioned in the title intermediate compound as a brown oil (5,62 g, 87%yield).

MS (ESI, m/z): 265,3 [M+H+].

E.iii. Ethyl ester rat-3-(1,3-dioxo-1,3-dihydroindol-2-yl)-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)propionic acid

To a solution of Li (4,54 ml 1-molar solution in THF) in THF (11 ml) is added at a temperature of -78°C. a solution of intermediate compound (E.ii) (1.0 g, of 3.78 mmol) in THF (3 ml) for 10 minutes After stirring for 1 h at the same temperature is added dropwise over 10 min a solution of N-(methyl bromide)phthalamide (1,09 g, 1.2 EQ.) in THF (4 ml). The mixture was stirred at -78°C for 1 h and then at room temperature overnight. The resulting solution was quenched by adding 1 normal HCl solution and extracted with DHM. The combined organic layers washed with water, dried over MgSO4, concentrated and purified by column chromatography (heptane/EA in the ratio 1:1), obtaining specified in the header of the intermediate connection in view of the off-white solids (0,361 g, 43%yield).

MS (ESI, m/z): 424,4 [M+H+].

E.iv. Ethyl ester rat-3-amino-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)propionic acid

To a suspension of intermediate compounds (E.iii) (368 mg, 0.87 mmol) in EtOH (6 ml) is added dropwise hydrazinoacetate (of 0.21 ml, 5 EQ.) at room temperature, and stirred the mixture for 2 h, and then concentrated. The residue is transferred into ethyl acetate and 10%aqueous citric acid solution and the layers separated. The aqueous phase is treated again with ethyl acetate, alkalinized NH4OH and extracted twice DHM. United DHM-phase is dried over MgSO4and concentrate, getting mentioned in the title intermediate compound as a yellow oil (0.21 g, 82%yield).

MS (ESI, m/z): 203,0 [M+H+].

E.v. Ethyl ester rat-3-tert-butoxycarbonylamino-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)propionic acid

On the basis of the intermediate compound (E.iv) (0.21 g, to 0.72 mmol) using method G, specified in the header of the intermediate compound obtained as a pale yellow foam (0,23 g, 83%yield).

MS (ESI, m/z): 394,2 [M+H+].

E.vi. tert-Butyl ether rat-[2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)-3-hydroxypropyl]carbamino acid

On the basis of the intermediate compound (E.v) (0,225 g, or 0.57 mmol) and using the method As specified in the header of the intermediate compound obtained as a yellow foam (0.20 g,100%yield).

MS (ESI, m/z): 202,2 [M+H+].

E.vii. tert-Butyl rat-(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ylmethyl)carbamino acid

On the basis of the intermediate compound (E.vi) (0.20 g, or 0.57 mmol) and using method H, specified in the header of the intermediate compound obtained as a beige solid (0,204 g, quantitative yield), which is used in the next stage without purification.

MS (ESI, m/z): 320,2 [M+H+].

E.viii. rat-4-Aminomethyl-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (E.vii) and using the method specified in the title compound obtained as a brown oil (17 mg, 13%yield).

MS (ESI, m/z): to 220.3 [M+H+].

Experimental method F: rat-4-(2-amino-ethyl)-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

F.i. Ethyl ester rat-3-cyano-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)propionic acid

Li (4,2 ml, 1.1 EQ., 1-molar solution in THF) is added at -78°C for 15 min to a solution of intermediate compound (E.ii) (1.5 g, of 5.68 mmol) in THF (15 ml). The resulting mixture was stirred at -78°C for 2 hours Then add bromoacetonitrile (1,02 g, 1.5 EQ.) within 20 min and stirring is continued at -78°C for 2 h, then the reaction quenched by adding water, and the reaction mixture is extracted with ethyl acetate (three times)Obyedinenie organic phases are washed with brine, dried over MgSO4filter and concentrate. The residue is purified by column chromatography (heptane/EA in the ratio 1:1), obtaining mentioned in the title intermediate compound as a yellow oil (1,30 g, 76%yield).

MS (ESI, m/z): 304,2 [M+H+].

F.ii. rat-4-Amino-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)butane-1-ol

To a solution of AlCl3(1.3 g, 9.9 mmol) in ether (60 ml) was added LAH (9,9 ml 1-molar solution in THF) dropwise over 10 min at -78°C. After stirring for 15 min add a suspension of intermediate compounds (F.i) (1,36 g, 4,50 mmol) in ether (50 ml) for 15 min, after which the suspension is stirred for 1 h at -78°C and for 1 h at -30°C. the Mixture was then stirred for 24 hours at a temperature of 0°C, quenched with saturated aqueous Na2SO4, alkalinized NH4OH and extracted with ethyl acetate (three times). The combined organic phases are dried over Na2SO4filter and concentrate. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:100:8), receiving specified in the header of the intermediate compound as a yellow oil (0,30 g, 25%yield).

MS (ESI, m/z): 266,3 [M+H+].

F.iii. tert-Butyl rat-[3-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)-4-hydroxybutyl]carbamino acid

On the basis of the intermediate with the organisations (F.ii) (424 mg, to 1.60 mmol) using method G, specified in the header of the intermediate compound obtained as yellow solid (360 mg, 62%yield).

MS (ESI, m/z): 366,2 [M+H+].

F.iv. tert-Butyl ether rat-[2-(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-yl)ethyl]carbamino acid

On the basis of the intermediate compound (F.iii) (360 mg, 0,99 mmol) using method H, specified in the header of the intermediate compound obtained as brown solid (360 mg, quantitative yield), which is used in the next stage without purification.

MS (ESI, m/z): 334,1 [M+H+].

F.v. rat-4-(2-amino-ethyl)-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he:

On the basis of the intermediate compound (F.iv) and using the method specified in the title compound is obtained after purification using column chromatography (DHM/MeOH/NH4OH in the ratio of 1000:100:8) as a yellow solid (130 mg, 49%yield).

MS (ESI, m/z): 234,3 [M+H+].

Experimental method G: rat-6-Amino-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Station. rat-2-Azido-2-(3-methoxyaniline-5-yl)ethanol

A mixture of 2-methoxy-8-oxiranylmethyl (4.7 g, 23 mmol; obtained according to the description in WO 2004/002490), NH4Cl (2.2 g, 1.8 EQ.) and NaN3(3.8 g, 2.5 EQ.) in the Meon (60 ml) is heated at 65°C for 5 h, filtered and concentrated in vacuo. The residue is transferred into ethyl shall zitat and washed with saturated aqueous NaHCO 3and brine, dried over MgSO4and concentrated, then purified by column chromatography (heptane/EA in the ratio 1:1), obtaining the desired intermediate compound in the form of a beige solid (4.4 g, 77%yield).

1H NMR (CDCl3) δ: charged 8.52 (s, 1H), 8,02 (dd, J=8,5, 1.5 Hz, 1H), to 7.77 (dd, J=7,3, 1.5 Hz, 1H), 7,60 (m, 1H), 5,90 (dd, J=7,6, 4,1 Hz, 1H), 4,13 (s, 3H), 4,01 (dd, J=11,4, and 3.8 Hz, 1H), a 3.87 (dd, J=11,4, 7.9 Hz, 1H).

G.ii. tert-Butyl ether rat-[2-hydroxy-1-(3-methoxyaniline-5-yl)ethyl]carbamino acid

A solution of intermediate compound (Station) (4,48 g, 18.2 mmol) in THF (100 ml) and water (3.2 ml) is treated with PPh3(5,3 g, 1.1 EQ.) and heated at 50°C for 2 h the Mixture was then concentrated without dried and dissolved in a mixture of ether/EA. The organic phase is twice extracted with 1-molar HCl solution cast, the aqueous phase is alkalinized 6-normal NaOH solution and extracted with DHM, dried over MgSO4and concentrate. The residue is dissolved in DHM (150 ml) and treated Side2O (4.8 g, 1.2 EQ.). The mixture is stirred at room temperature for 1 h, concentrated in vacuo and purified by column chromatography (EA/heptane 2:1, EA)to give the desired intermediate compound as a colourless foam (4.9 g, 84%yield).

1H NMR (DMSO-d6) δ: at 8.60 (s, 1H), 7,87 (dd, J=8,2, 1.5 Hz, 1H), of 7.70 (m, 1H), 7,58 (m, 1H), 7,26 (m, 1H), 5,64 (td, J=,6, the 4.1 Hz, 1H), amounts to 4.76 (t, J=5,9 Hz, 1H), 4,06 (s, 3H), 3,71 (m, 1H), 3,54 (m, 1H), 1,35 (s, 11H).

G.iii. tert-Butyl ether rat-(3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-yl)carbamino acid

On the basis of the intermediate compound (G.ii) (4,47 g, 14 mmol) and using method H, the reaction mixture is heated under reflux in EDC (100 ml) for 3 days, then cooled to room temperature, diluted with DHM, washed with water, dried over MgSO4and concentrate. The residue is crystallized from a mixture of ether/EA, receiving a mixture of the desired intermediate compounds and the corresponding oxazolidinone as off-white solid (2.2 g), which is used in the next stage without further purification or crystallization.

G.iv. rat-6-Amino-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

A solution of intermediate compound (G.iii) (2.17 g, 3.8 mmol) in DHM (10 ml) is treated with TFA (5 ml). The mixture is stirred at room temperature for 1 h, concentrated in vacuo and partitioned between DHM and water. The organic phase containing impurities, cast away, and the aqueous phase is alkalinized NH4OH and extracted several times with a mixture DHM/Meon in the ratio of 9:1. The combined organic phases are dried over MgSO4and concentrate getting the desired compound as an orange solid (0.36 g, 51%yield).

1H NMR (DMSO-d6) δ:8,17 (s, 1 N), to 7.67 (d, J=8,2 Hz, 1H), 7,58 (dt, J=7,3, 0.9 Hz, 1H), 7,32 (dd, J=7,9, and 7.3 Hz, 1H), 4,77 (dd, J=8,5, 4,4 Hz, 1H), 4,50 (dd, J=13,2, 8.5 Hz, 1H), 3,86 (dd, J=13,2, and 4.4 Hz, 1H).

Experimental method H: 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

H.i. tert-Butultimately-[(R)-2-oxiranylmethyl]silane and (2S)-4-(tert-butyldimethylsilyloxy)butane-1,2-diol

Specified in the header of the intermediate compounds get similar to the description in Kishi et al., Org. Lett. (2005), 7, 3997, (the intermediate connection S2-3) method hydrolytic kinetic separation (RS)-tert-butultimately-(2-oxiranylmethyl)silane (obtained as described in J. Org. Chem. (2008), 73, 1093). Two compounds emit after purification using column chromatography (heptane/EA in the ratio 2:1).

First aliremove connection: tert-butultimately-[(R)-2-oxiranylmethyl]silane (colorless oil, 25,3 g, 48%yield).1H NMR (CDCl3) δ: of 3.77 (t, J=6.4 Hz, 2H), 3.04 from (m, 1H), 2,78 (m, 1H), of 2.51 (dd, J=5.0 and 2.9 Hz, 1H), 1,74 (m, 2H), 0,90 (d, J=0.6 Hz, N), is 0.06 (s, 6H).

Second aliremove connection: (2S)-4-(tert-butyldimethylsilyloxy)butane-1,2-diol (colorless oil, 24,9 g, 43%yield).1H NMR (CDCl3) δ: the 3.89 (m, 3H), 3,62 (s, 1H), 3,53 (m, 1H), 3,42 (advanced s, 1H), to 2.29 (m, 1H), 1,70 (m, 2H), 0,90 (s, N), and 0.09 (s, 6H).

H.ii. (S)-4-(tert-Butyldimethylsilyloxy)-2-hydroxybutanoic ester toluene-4-sulfonic acid

To a solution of (2S)-4-(tert-butyldimethylsilyl the si)butane-1,2-diol (23.9 g, 108 mmol, second aliremove connection (H.i), DMAP (2.65 g, 0.2 EQ.) in DHM (80 ml), cooled to 0°C, add the tea (43,8 ml, 2.9 EQ.) and a solution of p-TsCl (20.7 g, 1.1 EQ.) in DHM (15 ml). The mixture is stirred at room temperature for 5 h, transferred into a saturated aqueous solution of NaHCO3and extracted DHM. The organic layer is dried over MgSO4and concentrate. The residue is purified by column chromatography (heptane/EA in the ratio 2:1), obtaining mentioned in the title intermediate compound as a colourless oil (31,3 g, 77%yield).

1H NMR (CDCl3) δ: 7.80 (d, J=7,6 Hz. 2H), 7,34 (d, J=7,6 Hz, 2H), was 4.02 (m, 3H), 3,80 (m. 2H), a 2.45 (s, 3H), of 1.70 (m, 2H), 1.27mm (m, 1H), 0,87 (s, N), of 0.05 (s, 6H).

H.iii. (2S)-tert-Butultimately-(2-oxiranylmethyl)silane

2-Molar solution of NaOH (35 ml) was added to a solution of intermediate compound (H.ii) (31.1 g, 83.1 mmol) in THF (350 ml) and the resulting mixture was vigorously stirred at room temperature for 3 h, then transferred into a 1-molar solution of NaOH (200 ml) and extracted with TBME (twice). The combined organic layers washed with water and brine, dried over MgSO4and concentrate. The resulting oil is purified by distillation through a nozzle Kugele (about 70°C at pressures of 0.1 mbar), getting mentioned in the title intermediate compound as a colourless oil (14,7 g, 87%yield).

1H NMR (CDCl3) δ: of 3.77(t, J=6,4 Hz, 2H), 3.04 from (m, 1H), 2,78 (m, 1H), of 2.51 (dd, J=5.0 and 2.9 Hz, 1H), 1,74 (m, 2H), 0,90 (d, J=0.6 Hz, N), is 0.06 (s, 6H).

H.iv. 6-[(S)-4-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]oxazin-3-one

A solution of 6-amino-4H-benzo[1,4]oxazin-3-one (of 5.03 g of 30.6 mmol; commercial) and intermediate (H.iii) (6.2 g, 1 EQ.) in a mixture of EtOH/H2About (in the ratio of 9:1; 180 ml) is heated at a temperature of 80°C for 2 days. The mixture was then concentrated under reduced pressure. The residual of the original aniline is removed by addition of a mixture of Et2O/MeOH, followed by filtration. The filtrate containing the product are concentrated under reduced pressure, obtaining mentioned in the title intermediate compound as a brown oil (of 9.45 g, 84%yield), which is used in the next stage without purification.

MS (ESI, m/z): 367,2 [M+H+].

H.v. 6-{(S)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (H.iv) (9.4 g, 25.6 mmol) and using the method I mentioned in the title intermediate compound obtained as a beige solid (2,40 g, 24%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 393,4 [M+H+].

H.vi. 6-[(S)-5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (H.v) (2,40 g, 6,11 the mol) and using method J, specified in the header of the intermediate compound obtained as off-white solids (0,82 g, 48%yield) after trituration with a mixture of Et2O/EA.

MS (ESI, m/z): 279,5 [M+H+].

H.vii. 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonate acid

On the basis of the intermediate compound (H.vi) (0,82 g, 2,95 mmol) using method H, specified in the title compound obtained as a beige solid (0,61 g, 58%yield).

1H NMR (DMSO-d6) δ: of 10.72 (s, 1H), 7,30 (d, J=2.1 Hz, 1H), 6,93 (m, 2H), amounts to 4.76 (m, 1H), to 4.52 (s, 2H), 4,34 (m, 2H), 4,11 (t, J=8,8 Hz, 1H), and 3.72 (m, 1H), 3,20 (s, 3H), 2,17 (m, 2H).

MS (ESI, m/z): 357,3 [M+H+].

Experimental method I: 2-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

I.i. 6-[(R)-4-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]oxazin-3-one

A solution of 6-amino-4H-benzo[1,4]oxazin-3-one (commercial product; of 6.49 g of 39.5 mmol) and tert-butultimately-[(R)-2-oxiranylmethyl]silane (first aliremove connection on stage (H.i); 8.0 g, to 39.5 mmol) in a mixture of EtOH/H2O (in the ratio of 9:1; 240 ml) is heated at a temperature of 80°C for 2 days. The mixture was then concentrated under reduced pressure. The residual of the original aniline is removed by addition of a mixture of Et2O/MeOH, followed by filtration. The filtrate containing the product is t, concentrate under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4), receiving specified in the header of the intermediate compound as a brown oil (of 5.82 g, 40%yield).

MS (ESI, m/z): 367,3 [M+H+].

II. 6-{(R)-5-[2-tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (I.i) (5.8 g, 15.8 mmol) and using the method I mentioned in the title intermediate compound obtained as a beige solid (2.7 g, 43%yield) after trituration with Et2O/EA/MeOH.

MS (ESI, m/z): 393,5 [M+H+].

I.iii. 6-[(R)-5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (II) (2.70 g, to 6.88 mmol) and using method J, specified in the header of the intermediate compound obtained as off-white solid (1.25 g, 65%yield) after trituration with Et2O/MeOH.

MS (ESI, m/z): 279,5 [M+H+].

I.iv. 2-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (I.iii) (2.1 g, at 7.55 mmol) and using the method of N indicated in the title compound obtained as off-white solids (1,16 g, 43%yield).

MS (ESI, m/z): 357,2 [M+H+].

Experimental method J: 2-[(R)-2-the CSR-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

J.i. 6-[(R)-4-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]thiazin-3-one

A solution of 6-amino-4H-benzo[1,4]thiazin-3-it is 10.68 g of 59.3 mmol; commercial product) and tert-butultimately-[(R)-2-oxiranylmethyl]silane (first aliremove connection on stage (H.i.); 12.0 g, of 59.3 mmol) in EtOH/H2O (in the ratio of 9:1; 320 ml) is heated at a temperature of 80°C for 2 days. The mixture was then concentrated under reduced pressure. The residual of the original aniline is removed by addition of a mixture of Et2O/MeOH, followed by filtration. The filtrate containing the product are concentrated under reduced pressure, obtaining mentioned in the title intermediate compound as a brown oil (18,8 g, 83%yield), which is used in the next stage without purification.

MS (ESI, m/z): 383,2 [M+H+].

J.ii. 6-{(R)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (J.i) (23,5 g, 49,1 mmol) and using the method I mentioned in the title intermediate compound obtained as colorless solids (8,4 g, 42%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 409,3 [M+H+].

J.iii. 6-[(R)-5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (J.ii) (8,4 g of 20.6 mmol) and using the " J, specified in the header of the intermediate compound obtained as off-white solids (4,79 g, 79%yield) after trituration with Et2O/EA.

MS (ESI, m/z): 295,5 [M+H+].

J.iv. 2-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (J.iii) (4.7 g, 16.0 mmol) and using the method of N indicated in the title compound obtained as off-white solids (5,80 g, 98%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 373,4 [M+H+].

Experimental method: 6-[(S)-5-(2-Iodoethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

K.i. 6-[(S)-4-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]thiazin-3-one

A solution of 6-amino-4H-benzo[1,4]thiazin-3-one (8.0 g, 44,5 mmol; commercial) and intermediate (H.iii) (9.0 g, 1 EQ.) in a mixture of EtOH/H2O in the ratio of 9:1 (250 ml) is heated at a temperature of 80°C for 2 days. The mixture was then concentrated under reduced pressure. The residual of the original aniline is removed by addition of a mixture of Et2O/MeOH, followed by filtration. The filtrate containing the product are concentrated under reduced pressure, obtaining mentioned in the title intermediate compound as a brown oil (14,58 g, 86%yield), which is used in the next stage without purification.

MS (ESI, m/z): 383,2 [M+H+].

K.ii. 6-{(S)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (K.i) (14.5 g, of 37.9 mmol) and using the method I mentioned in the title intermediate compound obtained as colorless solids (5,56 g, 36%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 409,3 [M+H+].

K.iii. 6-[(S)-5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (K.ii) (5.50 g, to 13.6 mmol) and using method J, specified in the header of the intermediate compound obtained as off-white solids (is 3.08 g, 77%yield) after trituration with Et2O/EA.

MS (ESI, m/z): 295,5 [M+H+].

K.iv. 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (K.iii) (3.0 g, 10.2 mmol) and using method H, specified in the header of the intermediate compound obtained as off-white solids (of 3.64 g, 96%yield) after trituration with ether.

MS (ESI, m/z): 373,4 [M+H+].

.v. 6-[(S)-5-(2-Iodoethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (K.iv) (2.5 g, 6.7 mmol) and using the method specified in the header Conn is get out in the form of a light orange solid (2,11 g, 78%yield) after trituration with Et2O/EA.

1H NMR (DMSO-d6) δ: 10,55 (s, 1H), 7,30 (m, 2H),? 7.04 baby mortality (dd, J=8,5, 2.3 Hz, 1H), and 4.68 (m, 1H), 4,10 (t, J=8,8 Hz, 1H), 3,70 (dd, J=8,8, 6,7 Hz, 1H), 3,41 (s, 2H), 3,29 (m, 2H), 2,23 (m, 2H).

MS (ESI, m/z): 405,1 [M+H+].

Experimental method L: 6-[(R)-5-(2-Iodoethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (J.iv) (3.5 g, 9.4 mmol) and using the method specified in the title compound obtained as off-white solids (3,52 g, 93%yield) after trituration with Et2O/EA.

1H NMR (DMSO-d6) δ: 10,55 (s, 1H), 7,30 (m, 2H),? 7.04 baby mortality (dd, J=8,5, 2.3 Hz, 1H), and 4.68 (m, 1H), 4,10 (t, J=8,8 Hz, 1H), 3,70 (dd, J=8,8, 6,7 Hz, 1H), 3,41 (s, 2H), 3,29 (m, 2H), 2,23 (m, 2H).

MS (ESI, m/z): 405,0 [M+H+].

Experimental method M: 2-[2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester of (RS)-methanesulfonic acid

M.i. (RS)-6-[4-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]thiazin-3-one

A solution of 6-amino-4H-benzo[1,4]thiazin-3-one (of 3.56 g of 19.8 mmol; commercial product) and (RS)-tert-butultimately-(2-oxiranylmethyl)silane (obtained as described in J. Org. Chem. (2008), 73, 1093; 4,0 g, to 19.8 mmol) in a mixture of EtOH/H2About (in the ratio of 9:1; 140 ml) is heated at a temperature of 80°C for 2 days. The mixture was then concentrated under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 100:50:4), getting listed in the title intermediate compound as a brown oil (2.20 g, 29%yield).

MS (ESI, m/z): 383,2 [M+H+].

M. (RS)-6-{5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (M.i) (2.20 g, of 5.75 mmol) and using the method I mentioned in the title intermediate compound obtained as a pale orange solid (1,53 g, ± 5%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 409,4 [M+H+].

M.iii. (RS)-6-[5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (M.ii) (1.50 g, to 3.67 mmol) and using method J, specified in the header of the intermediate compound obtained as off-white solid (0.73 g, 68%yield) after trituration with Et2O/EA.

MS (ESI, m/z): 295,1 [M+H+].

M.iv. 2-(2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester of (RS)-methanesulfonic acid

On the basis of the intermediate compound (M.iii) (0,70 g of 2.38 mmol) and using the method of N indicated in the title compound obtained as a beige solid (0,80 g, 90%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 373,1 [M+H+].

Experimental the tion method N: 6-((S)-5-Iodomethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]thiazin-3-one

Sep. 6-((S)-3-Chloro-2-hydroxypropylamino)-4H-benzo[1,4]thiazin-3-one

A suspension of 6-amino-4H-benzo[1,4]thiazin-3-one (18.0 g, 100 mmol; commercial product) and Ca(OTf)2(0.5 EQ.) in MeCN (800 ml) is heated at 50° for 1 h, then add (S)-epichlorohydrin (18.5 g, 200 mmol) and the mixture is stirred at room temperature for 72 h at 45°C for 24 h Volatile fractions are removed under reduced pressure. After water treatment and extraction with ethyl acetate is indicated in the title intermediate compound is crystallized from ethyl acetate, receiving a beige solid (17,38 g, 64%yield).

MS (ESI, m/z): 273,2 [M+H+].

N.ii. 6-((S)-5-Chloromethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (N.i) (39,3 g, 144 mmol) and using the method I mentioned in the title intermediate compound obtained as a beige solid (34,2 g, 79%yield) after purification using column chromatography (EA/heptane 2:1, EA).

MS (ESI, m/z): 299,1 [M+H+].

N.iii. 6-((S)-5-Iodomethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (N.ii) (14.0 g, 46,9 mmol) and using the method specified in the title compound obtained as a light beige solid (15.0 g, 82%yield).

1H NMR (DMSO-d6) δ: 10,56 (s, 1H), 7,31 (m, 2H), 7,12 (dd, J=8,5, 2.3 Hz, 1H), 4,71 (m, 1H), 4,4 (t, J=9.1 Hz, 1H)and 3.59 (m, 3H), and 3.31 (s, 2H).

MS (ESI, m/z): 391,4 [M+H+].

Experimental method A: 6-((R)-5-Iodomethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]thiazin-3-one

O.i. 6-((R)-3-Chloro-2-hydroxypropylamino)-4H-benzo[1,4]thiazin-3-one

A solution of 6-amino-4H-benzo[1,4]thiazin-3-one (18,39 g, 102 mmol; commercial product) and (R)-epichlorohydrin (8.0 ml, 1 EQ.) in EtOH/H2O (in the ratio of 9:1; 450 ml) is heated at a temperature of 80°C during the night. The mixture is concentrated under reduced pressure. The residual of the original aniline is removed by addition of a mixture of Et2O/EA, followed by filtration. The filtrate containing the product are concentrated under reduced pressure, obtaining mentioned in the title intermediate compound in the form of a beige solid (22,52 g, 81%yield), which is used in the next stage without purification.

MS (ESI, m/z): 273,2 [M+H+].

O. 6-((R)-5-Chloromethyl-2-oxoacridine-3~yl)-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (O.i) (22,0 g, 81.0 mmol) and using the method I mentioned in the title intermediate compound obtained as yellow solid (8,79 g, 36%yield) after trituration with DHM/Meon.

MS (ESI, m/z): 299,1 [M+H+].

O.iii. 6-((R)-5-Iodomethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (O.ii) (8,75 g, 29 mmol) and using the method specified in the header connection receive is in the form of off-white solids (9,27 g, 81%yield) after trituration with Et2O/EA.

1H NMR (DMSO-d6) δ: 10,56 (s, 1H), 7,31 (m, 2H), 7,12 (dd, J=8,5, 2.3 Hz, 1H), 4,71 (m, 1H), 4,14 (t, J=9.1 Hz, 1H)and 3.59 (m, 3H), and 3.31 (s, 2H).

MS (ESI, m/z): 390,9 [M+H+].

Experimental method R: (S)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-iodometrically-2-he

Ri. (S)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-hydroxymethylimidazole-2-he:

A solution of benzyl ether (2,3-dihydrobenzo[1,4]dioxin-6-yl)carbamino acid (13,0 g of 45.6 mmol) in THF (220 ml), cooled to -78°C., added dropwise to n-BuLi (29.5 ml 2,3-molar solution in hexane, 1.1 EQ.). The mixture was stirred at -78°C for 1 h, and then warmed to -15°C and added dropwise (S)-glycidylether (7,37 g, 1.1 EQ.). The mixture is stirred at room temperature over night, add Cs2CO3(with a spatula) and heated at 40°C until the reaction is completed. The mixture is then diluted with ethyl acetate and washed with saturated aqueous NH4Cl and water. The organic layer is dried over MgSO4and concentrate. The residue is purified by column chromatography (hexane/EA in the ratio 2:1, 1:1), obtaining mentioned in the title intermediate compound as a gray solid (? 7.04 baby mortality g, 62%yield).

1H NMR (DMSO-d6) δ: 7,13 (d, J=2.5 Hz, 1H), of 6.96 (dd, J=2,5, and 8.9 Hz, 1H), 6,86 (d, J=8,9 Hz, 1H), 5,16 (t, J=5.8 Hz, 1H), 4,70 to 4.0 (m, 1H), 4,30-4,10 (m, 4H), 4,10-3,90 (m, 1H), 4.80 to 4,70 (m, 1H), 4,70-4,60 (m, 1H), 4,60-4,50 (m, 1H).

RII. (S)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ymetray ether methanesulfonate acid

Based on the intermediate (Ri) (7.0 g, and 27.9 mmol) and using method H, specified in the header of the intermediate compound obtained as a colorless solid (9.0 g, 98%yield).

MS (ESI, m/z): 330,3 [M+H+].

P.iii. (S)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-iodometrically-2-he

On the basis of the intermediate compound (R) (9.0 g, 27,3 mmol) and using the method specified in the title compound obtained as off-white solids (6,91 g, 70%yield) after trituration with Et2O/EA.

1H NMR (CDCl3) δ: 7,07 (d, J=2.6 Hz, 1H), 6,98 (dd, J=9,1, 2.6 Hz, 1H), 6,85 (d, J=8,9 Hz, 1H), and 4.68 (m, 1H), 4,24 (s, 4H), 4,10 (t, J=9.1 Hz, 1H), and 3.72 (dd, J=9,1, 5,9 Hz, 1H), 3.46 in (m, 1H), 3.33 and (m, 1H)

MS (ESI, m/z): 362,2 [M+H+].

Experimental method A: (S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ymetray ether methanesulfonate acid

O.i. 6-[(S)-3-(tert-Butyldimethylsilyloxy)-2-hydroxypropylamino]-4H-benzo[1,4]oxazin-3-one

LiClO4(7.20 g, 3 EQ.) added to a solution of tert-butultimately-((S)-1-oxiranylmethyl)silane (commercial product; 4,25 g, and 22.6 mmol) in MeCN (70 ml), then added 6-amino-4H-benzo[1,4]oxazin-3-one (commercial product; 3,70 g, 1 EQ.) and the mixture is stirred is at a temperature of 50°C for 6 hours The solvent is removed under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio 1000/25/2), getting mentioned in the title intermediate compound as a pale brown foam (5,25 g, 66%yield).

MS (ESI, m/z): 353,3 [M+H+].

Q.ii. 6-[(S)-5-(tert-Butyldimethylsilyloxy)-2-oxoacridine-3-yl]-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (Q.i) (10,24 g, 29 mmol) and using the method I mentioned in the title intermediate compound obtained as a pale yellow solid (6,30 g, 57%yield) after trituration with ether.

MS (ESI, m/z): to 379.2 [M+H+].

Q.iii. 6-((S)-5-Hydroxymethyl-2-oxoacridine-3-yl)-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (Q.ii) (6,30 g of 16.6 mmol) and using method J, specified in the header of the intermediate compound obtained as colorless solids (3,49 g, 79%yield) after trituration with ethyl acetate.

MS (ESI, m/z): 265,5 [M+H+].

O.iv. (S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ymetray ether methanesulfonate acid

A suspension of intermediate compounds (Q.iii) (4,93 g, to 18.7 mmol) in anhydrous DHM (110 ml) is treated with DIPEA (12.0 ml of 3.75 EQ.) and cooled to 0°C, after which portions add Ms2O (4,88 g, 1.5 EQ.). The resulting mixture was stirred at 0°With the a period of 15 min, water is added and stirring is continued for 15 min at room temperature. Precipitated precipitated substance was washed with water and DHM. The obtained solid is triturated with DHM/Meon/NH4OH (in the ratio of 1000:25:2), receiving specified in the header of the intermediate compound as a colourless solid (there are 3,785 g, 60%yield).

1H NMR (DMSO-d6) δ: of 10.72 (s, 1H), 7,29 (dd, J=2,1, 0.6 Hz, 1H), 6,94 (m, 2H), 4.95 points (m, 1H), to 4.52 (s, 2H), 4,49 (m, 2H), 4,11 (t, J=9.1 Hz, 1H), to 3.73 (m, 2H), 3,23 (s, 3H).

MS (ESI, m/z): 343,3 [M+H+].

Experimental method R: (S)-3-(3-Fluoro-4-were)-5-iodometrically-2-he

R.i. (S)-3-(3-Fluoro-4-were)-5-hydroxymethylimidazole-2-he

A mixture of 3-fluoro-4-methylaniline (commercial product; a 1.25 g, 10 mmol), saturated aqueous NaHCO3(10 ml) and acetone (10 ml) is treated by adding dropwise benzylchloride (1.70 g, of 1.41 ml, 1 EQ.). After the termination of allocation of CO2the mixture is distributed between ethyl acetate and saturated aqueous NaHCO3, the organic layer is dried over MgSO4and concentrate under reduced pressure. The resulting benzylcarbamoyl dissolved in THF (50 ml) and cooled in an argon atmosphere to a temperature of -78°C. Then was added dropwise n-BuLi (a 2.5 molar solution in hexane, 6,45 ml, 1.1 EQ.) and the solution is stirred for 1 h at the same temperature. The reaction leave then spontaneously the unit's electric is camping to a temperature of -15°C, in which added dropwise (S)-glycidylether (1,69 ml, 1.1 EQ.). The mixture is stirred at room temperature overnight, then using a spatula add Cs2CO3the mixture is again stirred at room temperature for 3 h, add NH4Cl and ethyl acetate, and then the phases are separated. The aqueous phase is extracted again with ethyl acetate and the combined organic extracts are washed several times with saturated aqueous solution of NH4Cl, then brine, dried over Na2SO4and concentrate. The orange solid is triturated with ethyl acetate, getting mentioned in the title intermediate compound as a pale yellow solid (1.18 g, 53%yield).

MS (ESI, m/z): 226,3 [M+H+].

R.ii. (S)-3-(3-Fluoro-4-were)-2-oxoacridine-5-ymetray ether methanesulfonate acid

On the basis of the intermediate compound (R.i) (4,70 g of 20.9 mmol) and using method H, specified in the header of the intermediate compound obtained as yellow solid (6,37 g, 100%yield) after trituration with ether.

1H NMR (CDCl3) δ: of 7.36 (dd, J=11,7, 2.3 Hz, 1H), 7,13 (m, 2H), 4,91 (m, 1H), 4,46 (m, 2H), 4,13 (t, J=9.1 Hz, 1H), 3,92 (dd, J=9,1, 6.2 Hz, 1H), 3,10 (s, 3H), of 2.25 (d, J=1.8 Hz, 3H).

MS (ESI, m/z): 330,3 [M+H+].

R.iii. (S)-3-(3-Fluoro-4-were)-5-iodometrically-2-he

On the basis of the intermediate compound (R.ii) (6,30 g of 20.8 mmol) is using the method To, specified in the title compound obtained as a pinkish solid (6.3 g, 91%yield) after trituration with Et2O/EA.

1H NMR (CDCl3) δ: of 7.36 (dd, J=12,0, 2.1 Hz, 1H), 7,16 (m, 2H), 4,73 (m, 1H), 4,14 (m, 1H), 3,76 (dd, J=9,4, 6.2 Hz, 1H), 3,48 (m, 1H), 3,35 (dd, J=10,3, 8,2 Hz, 1H), 2,25 (d, J=1.8 Hz, 3H).

MS (ESI, m/z): 335,8 [M+H+].

Experimental method S: 2-[3-(3-Fluoro-4-were)-2-oxoacridine-5-yl]ethyl ester of (RS)-methanesulfonic acid

S.i. (RS)-4-(tert-Butyldimethylsilyloxy)-1-(3-fluoro-4-methylphenylimino)butane-2-ol

To a solution of (RS)-tert-butultimately-(2-oxiranylmethyl)silane (4.4 g, 200 mmol; obtained as described in J. Org. Chem. (2008), 73, 1093) in MeCN (60 ml) is added LiClO4(of 6.31 g, 3 EQ.), and then 3-fluoro-4-methylaniline (commercial product; 2.28 g, 0,92 equiv.) then the mixture is stirred at 50°C for 5 hours the Solvent is removed under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:25:2), receiving specified in the header of the intermediate compound as a brown oil (5,56 g, 86%yield).

MS (ESI, m/z): 328,4 [M+H+].

S.ii. (RS)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-3-(3-fluoro-4-were)oxazolidin-2-he

On the basis of the intermediate compound (S.i) (2.50 g, 7,63 mmol) and using the method I mentioned in the title intermediate compound obtained as off-white solid (1.2 g, 45%yield) after trituration with a mixture of ether/EA.

MS (ESI, m/z): 354,2 [M+H+].

S.iii. (RS)-3-(3-Fluoro-4-were)-5-(2-hydroxyethyl)oxazolidin-2-he

On the basis of the intermediate compound (S.ii) (1.20 g, 3,40 mmol) using method J, specified in the header of the intermediate compound obtained as colorless solids (0,478 g, 59%yield) after trituration with a mixture of Et2O/EA/DHL.

MS (ESI, m/z): 240,1 [M+H+].

S.iv. 2-[3-(3-Fluoro-4-were)-2-oxoacridine-5-yl]ethyl ester of (RS)-methanesulfonic acid

On the basis of the intermediate compound (S.iii) (470 mg, 2.0 mmol) and using the method of N indicated in the title compound obtained as off-white solids (0,60 g, 96%yield) after purification using column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4).

MS (ESI, m/z): 318,2 [M+H+].

Experimental method T: 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

T.i. 6-[(R)-5-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]oxazin-3-one

A mixture of (R)-tert-butultimately-(3-oxyaliphatic)silane (13 g, 60 mmol; obtained as described in Org. Lett. (2005), 7, 3997) and 6-amino-4H-benzo[1,4]oxazin-3-one (9,9 g) in EtOH/H2O (in the ratio of 9:1, 325 ml) is heated under reflux during the night. Then volatile fractions are removed under reduced pressure, and the mod is to purify via column chromatography (heptane/EA in the ratio 1:1), getting the desired intermediate compound as a brown oil (8,9 g, 39%yield).

MS (ESI, m/z): 318,2 [M+H+].

T.ii. 6-{(R)-5-[3-(tert-Butyldimethylsilyloxy)propyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]oxazin-3-one

On the basis of the intermediate compound (T.i) (8.8 g, 23 mmol) and using the method I mentioned in the title intermediate compound obtained as an orange solid (9.8 g, quantitative yield) after crystallization from a mixture of heptane/EA.

MS (ESI, m/z): 407,6 [M+H+].

T.iii. 6-[(R)-5-(3-Hydroxypropyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (T.ii) (9,8 g, 24 mmol) and using method J, specified in the header of the intermediate compound obtained as a yellowish solid (5.0 g, 71%yield) after purification using column chromatography (EA, EA/Meon in the ratio 9:1) and subsequent crystallization from a mixture of ether/EA.

MS (ESI, m/z): 293,3 [M+H+].

T.iv. 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

To a solution of intermediate compound (T.iii) (292 mg, 1 mmol) and DIPEA (0.5 ml, 3 EQ.) in DHM (5 ml) at room temperature is added dropwise a solution of the complex SO3·pyridine (318 mg, 2 EQ.) in DMSO (1 ml) for 10 minutes the Mixture is stirred at room temperature for 2 h, diluted with DHM and washed with water. The PR is onicescu phase is washed several times with water, dried over MgSO4and concentrate getting the desired aldehyde in the form of a beige solid (260 mg, 90%yield).

1H NMR (DMSO-d6) δ: 10,71 (s, 1H) 9,68 (d, J=0.9 Hz, 1H), 7,31 (s, 1H), 6,92 (m, 2H), with 4.64 (m, 1H), to 4.52 (d, J=1.2 Hz, 2H), 4,07 (m, 1H), 3,66 (m, 1H), 2,60 (m, 2H), up to 1.98 (m, 2H).

Experimental method U: 3-[(R)-2-Oxo-3-(3-oxo-3.4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

U.i. 6-[(R)-5-(tert-Butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]thiazin-3-one

A mixture of (R)-tert-butultimately-(3-oxyaliphatic)silane (13 g, 60 mmol; obtained as described in Org. Lett. (2005), 7, 3997) and 6-amino-4H-benzo[1,4]thiazin-3-one (10.8 g) in EtOH/H2O (in the ratio of 9:1, 325 ml) is heated under reflux during the night. Volatile fractions are removed under reduced pressure and the residue purified by column chromatography (heptane/EA in the ratio 1:1)to give the desired intermediate compound as a brown oil (6.8 g, 28%yield).

MS (ESI, m/z): 397,1 [M+H+].

U.ii. 6-{(R)-5-[3-(tert-Butyldimethylsilyloxy)propyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (U.i) (6.7 g, 17 mmol) and using the method I mentioned in the title intermediate compound obtained as an orange solid (7.8 g, quantitative yield) after crystallization from a mixture of heptane/EA.

MS (ESI, m/z): 423,4 [M+H+].

U.iii. 6-[(R)-5-(3-Hydroxypropyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (U.ii) (7,1 g, a 16.8 mmol) and using method J, specified in the header of the intermediate compound obtained as a yellowish solid (3.1 g, 60%yield) after purification using column chromatography (EA, EA/Meon in the ratio 9:1).

MS (ESI, m/z): 309,1 [M+H+].

U.iv. 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

To a solution of intermediate compound (U.iii) (500 mg, 1.6 mmol) and DIPEA (0,83 ml, 3 EQ.) in DHM (7 ml) at room temperature is added dropwise a solution of the complex SO3·pyridine (516 mg, 2 EQ.) in DMSO (1.7 ml) for 10 min, after which the mixture was stirred at room temperature for 2 h, diluted with DHM and washed with water. The organic phase is washed several times with water, dried over MgSO4and concentrate getting the desired aldehyde, after trituration with a mixture of ether/EA, in the form of a beige solid (440 mg, 88%yield).

MS (ESI, m/z): 307,5 [M+H+].

Experimental method V: (R)-4-Aminomethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

V.i. 2-(6-Methoxy[1,5]naphthiridine-4-yl)propane-1,3-diol

A mixture of 2-methoxy-8-methyl-[1,5]naphthiridine (2,90 g of 16.6 mmol; obtained according to WO 00/21948) and formaldehyde (37%aqueous solution of 7.8 ml) is heated at a temperature of 100°C for 3 days and then at 110°C for 2 days. After cooling the to room temperature the mixture is concentrated and carry in Meon and again concentrated. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:100:8), receiving specified in the header of the intermediate compound in the form of a pale beige solid (2,78 g, 71%yield).

1H NMR (DMSO-d6) δ: 8,67 (d, J=4.4 Hz, 1H), they were 8.22 (d, J=9.1 Hz, 1H), 7,51 (d, J=4.4 Hz, 1H), 7,22 (d, J=9.1 Hz, 1H), 4,56 (m, 2H), 4.00 points (s, 3H), of 3.84 (m, 3H).

V.ii. (S)-3-Hydroxy-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ester acetic acid

a 0.5-Molar solution of intermediate compound (V.i) (of 5.45 g, with 23.3 mmol) in vinyl acetate (60 ml) is treated with powdered 3Å molecular sieves (350 mg) and stirred at room temperature for 15 min in argon atmosphere. Then add the lipase isolated from Cuida antarctica (269 g printed on acrylic resin), and stirring is continued for 4 h at room temperature. The mixture is filtered; the filter cake washed with ethyl acetate and the filtrate concentrated. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:25:2), receiving specified in the header of the intermediate compound as a colourless oil (2.70 g, 42%yield). The corresponding diacetate (3,81 g, 51%yield) and then again split up diol and again used as the basis.

1H NMR (CDCl3) δ: 8,72 (d, J=4.4 Hz, 1H), 8,23 (d, J=9.1 Hz, 1H), 7,46 (d, J=4.4 Hz, 1H), 7,14 (d, J=9.1 Hz, 1H, the 4.65 (m, 2H), 4,22 (m, 1H), 4,07 (m, 4H), 2,96 (m, 1H), 2,04 (s, 1H),

MC (ESI, m/z): making up 277.3 [M+H+].

Alternative α:

V.iii. (S)-7-Oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether acetic acid

The tea (2.1 ml, 2 EQ.) and MsCl (0,70 ml, 1.2 EQ.) added at a temperature of 0°C. to a solution of intermediate compound (V.ii) (2,05 g, 7.41 mmol) in DHM (40 ml). The reaction mixture was stirred for 20 min at this temperature, add EDC (40 ml), and the solution was slowly heated to a temperature of 60°C and stirred at this temperature for 4 h, After cooling to room temperature, water is added, the layers decanted and the aqueous layer was again extracted with DHM. The combined organic layers are concentrated without dried. The residue is triturated with TBME, getting mentioned in the title intermediate compound as a gray solid (1.40 g, 77%yield).

1H NMR (CDCl3) δ: charged 8.52 (d, J=4,7 Hz, 1H), to 7.93 (d, J=9.7 Hz, 1H), 7,34 (d, J=4,7 Hz, 1H), 6.89 in (d, J=9.7 Hz, 1H), 4,56 (dd, J=12,9, and 9.4 Hz, 1H), 4,36 (m, 2H), 4,27 (dd, J=13,2, 5.0 Hz, 1H), 4,10 (m, 1H), 2.06 to (s, 3H).

MC (ESI, m/z): 245,2 [M+H+].

V.iv. (S)-4-Hydroxymethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

To2CO3(0.40 g, 0.5 EQ.) added to a solution of intermediate compound (V.iii) (1.40 g, 5,73 mmol), cooled to 0°C., and the mixture was vigorously stirred at this temperature for 30 minutes the Mixture is concentrated and statomat using column chromatography (DHM/Meon/NH 4OH in the ratio of 1000:100:8). The product is triturated with a mixture of EA/TBME, getting mentioned in the title intermediate compound as a gray solid (0,98 g, 85%yield).

MS (ESI, m/z): 203,0 [M+H+].

V.v. (S)-7-Oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether methanesulfonate acid

A solution of intermediate compound (V.iv) (0.33 g, and 1.63 mmol) and tea (or 0.57 ml, 2.5 EQ.) in anhydrous DHM (15 ml) cooled to 0°C. and adding dropwise, treated with MsCl (to 0.19 ml, 1.5 EQ.). The resulting mixture was stirred at 0°C for 1 h, after which water is added and DHM and the phases are separated. The organic layer is dried over MgSO4and concentrate under reduced pressure, obtaining mentioned in the title intermediate compound in the form of a colourless resin (0.40 g, 88%yield), which is used in the next stage without further purification.

MS (ESI, m/z): 281,3 [M+H+].

V.vi. (R)-4-Aminomethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

A solution of intermediate compound (V.v) (0.35 g, 1,24 mmol) in DMF (12 ml) is treated with sodium azide (0.65 g, 8 EQ.) and stirred at 50°C for 1.5 h, After cooling to room temperature, water is added and the mixture extracted with DHM. The organic layer is dried over MgSO4and concentrate under reduced pressure, obtaining a yellow oil (crude azide), which is transferred into a T is f (1.5 ml), then add PPh3(390 mg) and water (0,13 ml). The mixture is heated at 50°C for 3 h, concentrated without dried, and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:100:8), receiving specified in the header of the intermediate compound as a yellow oil (30 mg, 12%yield).

MS (ESI, m/z): 202,2 [M+H+].

Alternative β:

V.ii. (R)-3-(tert-Butyldimethylsilyloxy)-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ester acetic acid

To a solution of intermediate compound (V.ii) (1.66 g) in DHM (50 ml) is added imidazole (1 EQ.) and Cl (1 EQ.). The mixture is stirred at room temperature for 3 hours and add another EQ. each reagent, after which the reaction is completed within 15 minutes Then add water and the mixture extracted with DHM. The organic layer is dried over MgSO4and concentrate, getting mentioned in the title intermediate compound as a colourless oil (2,36 g, 100%yield).

MS (ESI, m/z): 391,5 [M+H+].

V.iii. (R)-3-(tert-Butyldimethylsilyloxy)-2-(6-methoxy[1,5]naphthiridine-4-yl)propan-1-ol

A suspension of intermediate compounds (V.vii) (2,36 g) and K2CO3(3,34 g) in the Meon (50 ml) was vigorously stirred at room temperature for 30 min, then add water and DHM, layers decanted and the aqueous layer was extracted again DHM. Unite the military organic layers dried over MgSO 4filter and concentrate without dried, obtaining mentioned in the title intermediate compound as a colourless oil (2.1 g, 100%yield).

MS (ESI, m/z): 349,1 [M+H+].

V.ix. 8-[(R)-2-Azido-1-(tert-butyldimethylsilyloxy)ethyl]-2-methoxy[1,5]naphthiridine

On the basis of the intermediate compound (V.viii) (2,09 g) and using the method of N indicated in the title intermediate compound is isolated in the form of a colorless oil (1,79 g, 80%yield).

MS (ESI, m/z): 374,1 [M+H+].

V.. tert-Butyl ester [(R)-3-(tert-butyldimethylsilyloxy)-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl]carbamino acid

On the basis of the intermediate compound (V.ix) (1,79 g) and using the methods F and G, specified in the header of the intermediate compound obtained as a dark oil (2.14 g, 100%yield).

MS (ESI, m/z): USD 448,2 [M+H+].

V.xi. tert-Butyl ester [(R)-3-hydroxy-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl]carbamino acid

On the basis of the intermediate compound (V.x) (2.14 g) and using method J, specified in the header of the intermediate compound obtained as colorless solids (1,14 g, 72%yield).

MS (ESI, m/z): 334,2 [M+H+].

V.xii. tert-Butyl ester ((R)-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ylmethyl)carbamino acid

On the basis of the intermediate compound (V.xi) (1,14 g) and using method H and then nagrywania 60°C for 2 h in EDC, specified in the header of the intermediate compound obtained as colorless solids (0,91 g, 88%yield).

MS (ESI, m/z): 302,2 [M+H+].

V.xiii. (R)-4-Aminomethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (V.xi) (0,91 g) and using the method specified in the header of the intermediate compound obtained as a pale yellow solid (0,496 g, 82%yield).

MS (ESI, m/z): 202,1 [M+H+].

Experimental method W: 7-Oxo-4,5-dihydro-7-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether (RS)-methanesulfonic acid

W.i. 3-(tert-Butyldimethylsilyloxy)-2-(6-methoxy[1,5]naphthiridine-4-yl)propan-1-ol

A solution of intermediate compound (V.i) (1.10 g) in THF (55 ml) is treated at 0°With imidazole (351 mg) and the solution Cl (707 mg) in THF (10 ml). After stirring at room temperature for 2 days the reaction mixture was diluted with ethyl acetate and extracted with water and brine. The organic phase is dried over MgSO4and purified by column chromatography (heptane/EA ratio from 1:1 to 0:1)to give colorless oil (570 mg; 35%yield).

MS (ESI, m/z): 349,2 [M+H+].

W.ii. 3-(tert-Butyldimethylsilyloxy)-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ether methanesulfonate acid

On the basis of the intermediate compound (W.i) (1.4 g) and MsCl (0,374 ml) and using method H, specified the title compound obtained as a yellow oil (1.4 g, 81%yield).

1H NMR (CDCl3) δ: 8,72 (d, J=4.4 Hz, 1H) 8,23 (d, J=9.1 Hz, 1H), 7,50 (d, J=4,7 Hz, 1H), 7,15 (d, J=9.1 Hz, 1H), 4,78 (m, 2H), of 4.44 (m, 1H), 4,05 (m, 5H), 2,90 (s, 3H), of 0.87 (m, 12H), -0,02 (d, J=8,5 Hz, 6N).

W.iii. 4-(tert-Butyldimethylsilyloxy)-4,5-dihydropyrrolo[3,2,1-de][1,5]paratiritis-7He

A solution of intermediate compound (W.ii) (1.4 g) in EDC (20 ml) is heated at a temperature of 85°C during the night. The reaction mixture was then evaporated under reduced pressure. The residue is purified by column chromatography (EA, EA/Meon in the ratio 9:1)to give colorless oil (340 g; 33%yield).

MS (ESI, m/z): is 317.1 [M+H+].

W.iv. 4-Hydroxymethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (W.iii) (330 mg) and using method J, specified in the title compound obtained as a colorless solid (90 mg, 43%yield).

MS (ESI, m/z): is 203.2 [M+H+].

W.v. 7-Oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether (RS)-methanesulfonic acid

On the basis of the intermediate compound (W.iv) (90 mg) and using the method of N indicated in the title compound obtained as yellow solid (90 mg, 72%yield).

Analytical data allow us to classify the compound obtained (S)-enantiomer (intermediate compound (V.v).

Experimental method X: rat-1-Amino-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

X.i. 2 Azido-2-(2-IU is the oksihinolina-8-yl)ethanol

A solution of 2-methoxy-8-(2-oxiranyl)quinoline (900 mg; obtained according to WO 2006/046552) in a mixture of dioxane/water (in the ratio of 5:1; 60 ml) is injected into the reaction with NaN3at a temperature of 90°C for 5 hours the Solvent is removed under reduced pressure and the residue purified by column chromatography (hexane/EA ratio from 2:1 to 1:1)to give a yellow oil (480 mg; 44%yield).

MS (ESI, m/z): 245,0 [M+H+].

X.ii. rat-2-Amino-2-(2-methoxyquinoline-8-yl)ethanol

On the basis of the intermediate compound (X.i) (470 mg) and using method F, indicated in the title compound obtained as a yellow oil (450 mg, 100%yield).

MS (ESI, m/z): 219,1 [M+H+].

X.iii. tert-Butyl ether rat-[2-hydroxy-1-(2-methoxyquinoline-8-yl)ethyl]carbamino acid

On the basis of the intermediate compound (X.ii) (430 mg) and using method G, specified in the title compound obtained as a yellow oil (720 mg; quantitative yield).

MS (ESI, m/z): 319,1 [M+H+].

X.iv. 2-tert-Butoxycarbonylamino-2-(2-methoxyquinoline-8-yl)ethyl ester rat-methanesulfonic acid

On the basis of the intermediate compound (X.iii) (700 mg) and using the method of N indicated in the title compound obtained as a yellow oil (900 mg, quantitative yield).

MS (ESI, m/z): 397,0 [M+H+].

X.v. tert-Butyl ether rat-(4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

RA is a creation of intermediate compounds (X.iv) (850 mg) in EDC (10 ml) is heated at a temperature of 85°C during the night. The solvent is evaporated under reduced pressure, obtaining a brown oil (780 mg; quantitative yield), which is used in the next stage without further purification.

MS (ESI, m/z): 287,1 [M+H+].

X.vi. rat-1-Amino-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (X.v) (572 mg) and using the method specified in the title compound obtained as a beige solid (230 mg, 62%yield).

MS (ESI, m/z): 187,0 [M+H+].

Experimental method Y: (S)-4-Amino-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Y.i. (S)-2-Azido-2-(6-methoxy[1,5]naphthiridine-4-yl)ethanol

This connection receive similar synthetic method of the X stage X.i, but on the basis of 2-methoxy-8-[2R)-2-oxiranyl]-1,5-naphthiridine (obtained according to WO 02/08224). The connection is cleaned by column chromatography (heptane/EA ratio from 1:1 to 2:1 to 0:1), getting it in the form of a yellow solid (3.9 g (87%; polluted its spatial isomer).

MS (ESI, m/z): 246,3 [M+H+].

Y.ii. (S)-2-Amino-2-(6-methoxy[1,5]naphthiridine-4-yl)ethanol

On the basis of the intermediate compound (Y.i) (3,90 g) and using method F, indicated in the title compound obtained as a yellow oil (2,80 g, 80%yield).

MS (ESI, m/z): 220,0 [M+H+].

Y.iii. tert-Butyl ether (S)-[2-hydroxy-1-(6-methoxy[1,5]naphthiridine-4-yl)ethyl]carbamino acid

Proceeding and the intermediate compounds (Y.ii) (2,90 g) using method G, specified in the title compound obtained as a colorless foam (1.40 g, 33%yield).

MS (ESI, m/z): 320,1 [M+H+].

Y.iv. tert-Butyl ester ((S)-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-yl)carbamino acid

On the basis of the intermediate compound (Y.iii) (1.40 g) and using method H followed by heating at a temperature of 80°C for 7 h, specified in the title compound obtained as a beige solid (570 mg, 45%yield).

MS (ESI, m/z): 288,4 [M+H+].

Y.v. (S)-4-Amino-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (Y.iv) (570 mg) and using the method specified in the title compound obtained as a beige solid (470 mg, quantitative yield).

1H NMR (CDCl3) δ: 8,43 (d, J=4,7 Hz, 1H), 7,79 (d, J=9.7 Hz, 1H), 7,43 (dd, J=4,7, 0.9 Hz, 1H), 6,74 (d, J=10.0 Hz, 1H), 4,91 (m, 1H), to 4.52 (dd, J=13,2, 8.5 Hz, 1H), was 4.02 (dd, J=13,5, a 4.7 Hz, 1H).

Experimental method Z: (S)-6-Amino-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Z.i. 2-Methoxy-8-virilisation

A suspension of the bromide methyltriphenylphosphonium (22,78 g) in THF (200 ml) is treated with tBuOK (7,15 g) and then stirred at room temperature for 1 h the Mixture is cooled to 0°C, treated with a solution of 3-methoxy-5-chynoxalinilmethylen (10.0 g; obtained according to WO 2006/021448) in THF (100 ml), stirred at room temperature for 3 h, diluted with EPE is om and washed with water and saturated aqueous NH 4Cl. The organic phase is dried over MgSO4and concentrate under reduced pressure. The residue is crystallized from ether and the crystals filtered off. The mother liquor is purified by column chromatography (hexane/EA in the ratio 1:1)to give a light orange solid (8,70 g; 88%yield).

1H NMR (CDCl3) δ: 8,48 (s, 1H), 7,92 (m, 2H), 7,78 (dd, J=17,9 and 11.1 Hz, 1H), 7,54 (m, 1H), 6,03 (dd, J=17,9, 1.5 Hz, 1H), 5,48 (dd, J=11,4, 1.5 Hz, 1H), 4,12 (s, 3H).

Z.ii. (R)-1-(3-Methoxyaniline-5-yl)ethane-1,2-diol

On the basis of the intermediate compound (Z.i) (8,70 d) and using the method of L with AD-mix β, specified in the title compound obtained as a beige solid (7,60 g, 74%yield) after crystallization from a mixture of ether/EA.

MS (ESI, m/z): to 221.1 [M+H+].

Z.iii. (R)-2-(tert-Butyldimethylsilyloxy)-1-(3-methoxyaniline-5-yl)ethanol

On the basis of the intermediate compound (Z.ii) (7,60 g) and using method M that is listed in the title compound obtained as a yellow oil (8,80 g, 76%yield).

MS (ESI, m/z): 335,0 [M+H+].

Z.iv. (S)-2-Amino-2-(3-methoxyaniline-5-yl)ethanol

On the basis of the intermediate compound (Z.iii) (8,80 d) and using method N get the desired azide (20 g), which is used PA next stage of the synthesis without purification. The solution of this azide (20 g, contaminated PPh3O) in THF (228 ml) is treated with PPh3(7.50 g) and water (4,68 ml). The reaction to shift the ü then stirred at 50°C for 2 days, then extracted with 3-molar HCl solution. The aqueous phase is alkalinized with an aqueous solution of NaOH and extracted with ethyl acetate. The organic layer is dried over MgSO4and evaporated under reduced pressure, obtaining a yellow oil (6,10 g; specified in the title compound, contaminated with traces of PPh3O).

MS (ESI, m/z): 220,0 [M+H+].

Z.v. tert-Butyl ester [(S)-2-hydroxy-1-(3-methoxyaniline-5-yl)ethyl]carbamino acid

On the basis of the intermediate compound (Z.iv) (6,00 g) using method G, specified in the title compound obtained as a yellowish foam (5,90 g, 67%yield).

MS (ESI, m/z): 320,1 [M+H+].

Z.vi. tert-Butyl ester ((S)-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-yl)carbamino acid

A solution of intermediate compound (Z.v) (5,80 g) and tea (3.0 ml) in EDC (45 ml) is treated dropwise at 0°C, adding MsCl (1,55 ml). The reaction mixture was then heated under reflux overnight, diluted with DHM, washed with water and brine, dried over MgSO4and evaporated under reduced pressure, obtaining after crystallization from a mixture of ether/EA beige solid (3.50 g; 67%yield), including an undivided mixture (in the ratio 2:1) of the desired substance and 4-(3-methoxyaniline-5-yl)oxazolidin-2-it, which is used in the next stage without purification.

MS (ESI, m/z): 288,0 and 246,0 M+N +].

Z.vii. (S)-6-Amino-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

On the basis of the intermediate compound (Z.vi) (3.50 g) and using the method specified in the title compound obtained as a beige solid (780 mg, 34%yield). A by-product of the cyclization is removed by extraction (acid/base).

MS (ESI, m/z): 188,1 [M+H+].

Experimental method AA: (R)-6-Amino-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Specified in the header connection receive similar synthetic method Z using AD-mix and in the second stage.

Analytical data identical to the data connection of the experimental method Z.

Experimental method AB: 4-Oxo-1,2-dihydro-H-pyrrolo[3,2,1-ij]quinoline-1-ymetray ether rat-methanesulfonic acid

AB.i. Dimethyl 2-(2-methoxyquinoline-8-yl)malonic acid

A mixture of 8-bromo-2-methoxyquinoline (4,76 g; obtained according to WO 2008/125594) and diethylmalonate (36 ml) Tegaserod by passing through the reaction mixture of N2within 10 min, and then treated by adding CuBr (3,47 g) and NaOMe (2.6 g). The mixture is heated at a temperature of 100°C for 20 h, and then distributed between ethyl acetate and water. The organic phase is washed with brine, dried over MgSO4and excess diethylmalonate removed by distillation. The residue is purified by column chromatography (heptane/EA in soo is wearing 4:1, 2:1)to give oil (2,80 g; 48%yield).

1H NMR (CDCl3) δ: 7,98 (d, J=8,8 Hz, 1H), 7,71 (dd, J=8,2, 1.5 Hz, 1H), 7,66 (m, 1H), 7,39 (m, 1H), 6,92 (d, J=8,8 Hz, 1H), 6,00 (s, 1H), a 4.03 (s, 3H), 3,76 (s, 3H).

AB.ii. 2-(2-Methoxyquinoline-8-yl)propane-1,3-diol

On the basis of the intermediate compound (AB.i) (5,80 g) and using the method As specified in the title compound obtained as a light yellow oil (1.06 g, 23%yield).

MS (ESI, m/z): of 234.2 [M+H+].

AB.iii. 4-Oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-ymetray ether rat-methanesulfonic acid

On the basis of the intermediate compound (AB.ii) (840 mg) and following the method b, but using 3 EQ. anhydride methanesulfonic acid instead of MsCl and 4 EQ. pyridine as base, intermediate dimesylate stirred at 70°C for 1 h, after which the reaction mixture is diluted with 2-normal HCl solution and extracted with DHM. The organic phase is dried over MgSO4and evaporated under reduced pressure, obtaining after purification using column chromatography (EA/Meon in the ratio 9:1) beige foam (1.10 g; 76%yield).

MS (ESI, m/z): 280,4 [M+H+].

Experimental method AC: rat-6-Aminomethyl-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

AC.i. Methyl ether (3-methoxyaniline-5-yl)acetic acid

Cl (2.4 ml) is added dropwise to a solution of 3-methoxy-5-chynoxalinilmethylen (1.08 g, obtained according to WO 208/126024) in dry Meon (20 ml). The solution is stirred at reflux overnight, then add Cl (2.4 ml)and the reaction mixture is stirred for 8 hours Then add another portion of Cl (2.4 ml) and the reaction mixture is stirred at reflux over night. The mixture is concentrated under reduced pressure and distributed between ethyl acetate and water. The organic layer was washed with 2-molar aqueous solution of NaOH, water and brine, dried over MgSO4concentrate under reduced pressure and purified by column chromatography (heptane/EtOAc to 1:1 ratio)to give a yellow oil (520 mg, 41%yield).

MS (ESI, m/z): 233,3 [M+H+].

AC.ii. Methyl ether rat-3-(1,3-dioxo-1,3-dihydroindol-2-yl)-2-(3-methoxyaniline-5-yl)propionic acid

A solution of intermediate compound (AC.i) (2,03 g) in THF (19 ml) is added dropwise at a temperature of -78°C. to the solution Li (1-molar solution in THF; 10,5 ml) in THF (10 ml). Then the solution was stirred at the same temperature for 1 h and treated, adding dropwise, a solution of N-(methyl bromide)phthalamide (2.6 g) in THF (19 ml), after which the reaction mixture is stirred at -78°C for 1 h and at room temperature over night. The solution is then quenched with 1 normal HCl solution (30 ml) and extracted with ethyl acetate. Organically the layer washed with water and brine, dried over MgSO4concentrate under reduced pressure and purified by column chromatography (heptane/EA in the ratio 1:1)to give after crystallization from ethyl acetate beige solid (2.28 g; 66%yield).

MS (ESI, m/z): 392,3 [M+H+].

AC.iii. Methyl ether rat-3-amino-2-(3-methoxyaniline-5-yl)propionic acid

Hydrazinoacetate (1,42 ml) is added dropwise at room temperature to a suspension of intermediate compounds (AC.ii) (2.28 g) in EtOH (38 ml). After stirring at room temperature for 2 h the solvent is evaporated under reduced pressure, and the residue is transferred to the ethyl acetate and aqueous citric acid solution (10%). The aqueous layer was washed with NH4OH and extracted with DHM. The organic layer is dried over MgSO4and evaporated under reduced pressure, obtaining a yellow oil (1,16 g; 77%yield), which is used further without any purification.

MS (ESI, m/z): 262,3 [M+H+].

AC.iv. Methyl ether rat-3-tert-butoxycarbonylamino-2-(3-methoxyaniline-5-yl)propionic acid

On the basis of the intermediate compound (AC.iii) (1,16 g) using method G, specified in the title compound obtained as a colorless solid (1,34 g, 83%yield).

MS (ESI, m/z): 362,0 [M+H+].

.v. tert-Butyl ether rat-[3-hydroxy-2-(3-methoxy-1,2-dihydroquinoxaline-5-yl)propyl]karbaminovoi acid

On the basis of the intermediate compound (AC.iv) (701 mg) and using the method As specified in the title compound obtained as a colorless foam (554 mg, 85%yield).

MS (ESI, m/z): 336,2 [M+H+].

AC.vi. tert-Butyl ether rat-[3-hydroxy-2-(3-methoxyaniline-5-yl)propyl]carbamino acid

A solution of intermediate compound (AC.v) (553 mg) in DHM (30 ml) is treated with MnO2(1.35 g). The mixture is stirred at room temperature for 2 h, filtered and concentrated in vacuo, obtaining the desired intermediate compound as a pale orange foam (489 mg, 89%yield).

MS (ESI, m/z): 334,1 [M+H+].

AC.vii. tert-Butyl ether rat-(3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-ylmethyl)carbamino acid

On the basis of the intermediate compound (AC.vi) (486 mg) and using the method of N indicated in the title compound obtained as a beige solid (393 mg, 89%yield).

MS (ESI, m/z): 302,1 [M+H+].

AC.viii. rat-6-Aminomethyl-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

On the basis of the intermediate compound (AC.viii) (388 mg) and using the method specified in the title compound obtained as yellow solid (172 mg, 66%yield).

MS (ESI, m/z): 202,3 [M+H+].

Experimental method AD: (S)-6-Amino-7-fluoro-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

AD.i. (R)-1-(6-Fluoro-3-methoxyaniline-5-yl)ethane-1,2-diol

And the walking of 7-fluoro-2-methoxy-8-(2-propen-1-yl)finokalia (3,24 g; obtained according to WO 2008/003690) and using the method of L with AD-mix β, specified in the title compound is obtained after purification using column chromatography (heptane/EA ratio of 1:1, then 0:1) as a beige solid (3,39 g, 90%yield).

1H NMR (DMSO d6) δ: to 8.57 (s, 1H), of 7.96 (dd, J=9,1, 5.6 Hz, 1H), of 7.48 (dd, J=10,3, 9.1 Hz, 1H), 5,64 (d, J=6,7 Hz, 1H), 5,26 (d, J=6,4 Hz, 1H), and 4.75 (m, 1H), of 4.05 (s, 3H), 3,88 (m, 1H), to 3.73 (m, 1H).

AD.ii. (R)-2-(tert-Butyldimethylsilyloxy)-1-(6-fluoro-3-methoxyaniline-5-yl)ethanol

On the basis of the intermediate compound (AD.i) (3,39 g) and using method M that is listed in the title compound obtained as a colorless oil (4.83 g, 96%yield).

1H NMR (CDCl3) δ: of 8.47 (s, 1H), 7,95 (m, 1H), 7,35 (m, 1H), 5,5 (m, 1H), 4.09 to (s, 3H), a 4.03 (m, 2H), 0,76 (s, 9H), -0,12 (d, J=5.0 Hz, 6N).

AD.iii. tert-Butyl ether (S)-[2-(tert-butyldimethylsilyloxy)-1-(6-fluoro-3-methoxyaniline-5-yl)ethyl]carbamino acid

On the basis of the intermediate compound (AD.ii) (4,73 g) and using method N'mentioned in the title compound is obtained after purification using column chromatography (heptane/EA ratio 4:1) as a colourless foam (3,48 g; 84%yield).

1H NMR (CDCl3) δ: to 8.45 (s, 1H), to 7.93 (dd, J=9,1, 5.6 Hz, 1H), 7,30 (m, 1H), 6,60 (m, 1H), to 5.85 (m, 1H), 4,12 (s, 4H), of 3.94 (m, 2H), USD 1.43 (s, 9H), 0.75 in (s, 9H), -0,08 (s, 3H), -0,12 (s, 3H).

AD.iv. tert-Butyl ether (S)-[1-(6-fluoro-3-methoxyaniline-5-yl)-2-hydroxyethyl]carbamino acid

Basedfrom intermediate compounds (AD.iii) (5,54 g) and using method J, specified in the title compound obtained as a colorless foam (3,48 g, 84%yield).

1H NMR (CDCl3) δ: 8.45 (s, 1H), 7,95 (dd, J=9,4, 5,9 Hz, 1H), 7,34 (m, 1H), 6,60 (m, 1H), to 5.85 (m, 1H), 4,11 (s, 3H), 3,92 (m, 2H). of 1.42 (s, 9H).

AD.v. tert-Butyl ether (S)-(7-fluoro-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-yl)carbamino acid

On the basis of the intermediate compound (AD.iv) (3,45 g) and using method H, followed by heating under reflux for 12 h, get a foam (2.64 g), which contains the desired product mixed with (S)-4-(6-fluoro-3-methoxyaniline-5-yl)oxazolidin-2-one in 1:1 ratio and used without purification in the next stage.

AD.vi. (S)-6-Amino-7-fluoro-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

From the mixture obtained in stage AD.v (2.64 g, purity 50%), and using the method In the following extraction (acid/base)specified in the title compound obtained as an orange solid (550 mg, 60%yield).

1H NMR (DMSO-d6) δ: 8,12 (s, 1H), 7,74 (dd, J=8,8, 4,4 Hz, 1H), 7,11 (m, 1H), 4,94 (dd, J=8,5, 3.8 Hz, 1 H), 4,50 (dd, J=13,2, 8.5 Hz, 1H), 3,90 (dd, J=13,2, and 3.8 Hz, 1H), 2,32 (advanced, 2H).

Experimental method AE: rat-1-Aminomethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

AE.i. rat-1-Azidomethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

A solution of the compound of the experimental method AB (1,00 g) in DMF (16 ml) is heated at 60°C for 3 h in prisutstvie and NaN 3(2,80 g). The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4and evaporated, receiving a yellow powder (800 mg, 99%yield).

1H NMR (CDCl3) δ: 7,72 (d, J=9.4 Hz, 1H), 7,45 (m, 2H), 7,19 (m, 1H), 6,69 (d, J=9.4 Hz, 1H), 4,55 (dd, J=13,2, and 9.4 Hz, 1 H), 4.26 deaths (dd, J=13,2, a 4.7 Hz, 1H), 3,91 (m, 1H), to 3.67 (m, 2H).

AE.ii. rat-1-Aminomethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (AE.i) (800 mg) and using method F, indicated in the title compound obtained as a yellow oil (310 mg, 44%yield).

1H NMR (CDCl3) δ: of 7.70 (d, J=9.4 Hz, 1H), 7,41 (m, 2H), 7,17 (t, J=7,6 Hz, 1H), to 6.67 (d, J=9.4 Hz, 1H), 4,54 (dd, J=13,2, 9.7 Hz, 1H), 4,32 (dd, J=12,6, a 4.7 Hz, 1H), 3,80 (m, 1H), 3,10 (d, J=6.2 Hz, 2H).

Experimental method AF: 6-[(R)-5-(2-amino-ethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

AF.i. 6-[(R)-5-(2-Azidoethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

A solution of the compound of the experimental method J (2.5 g) and NaN3(523 mg) in DMF (12 ml) is heated at a temperature of 80°C during the night. The reaction mixture was diluted with ethyl acetate and extracted with water and brine. The organic layer is dried over MgSO4and evaporated under reduced pressure. The residue is stirred in a mixture of ether/Meon, receiving a beige solid (1.9 g; 89%yield).

MS (ESI, m/z): 320,2 [M+H+].

AF.ii. 6-[(R)-5-(2-amino-ethyl)-2-oxoacridine-3-yl]-4H-is Enzo[1,4]thiazin-3-one

On the basis of the intermediate compound (AF.i) (1.8 g) and using method F, indicated in the title compound obtained as a colorless solid (1.40 g, 85%yield).

MS (ESI, m/z): 294,4 [M+H+].

Experimental method AG: (S)-2-Oxo-3-(4-propylphenyl)oxazolidin-5-ymetray ether methanesulfonate acid

AG.i. (S)-5-Hydroxymethyl-3-(4-propylphenyl)oxazolidin-2-he

On the basis of 4-propylaniline and using the method described for intermediate compounds (R.i)specified in the title compound obtained as yellow solid (4.3 g; 63%yield).

MS (ESI, m/z): 235,9 [M+H+].

AG.ii. (S)-2-Oxo-3-(4-propylphenyl)oxazolidin-5-ymetray ether methanesulfonate acid

On the basis of the intermediate compound (AG.i) (4,25 g) and using the method of N (but with 1.5 EQ. Ms2J instead of MsCl)specified in the title compound obtained as off-white solid (4.3 g, 76%yield).

MS (ESI, m/z): 314,1 [M+H+].

Experimental method an: (S)-3-(4-Butylphenyl)-2-oxoacridine-5-ymetray ether methanesulfonate acid

AH.i. (S)-5-Hydroxymethyl-3-(4-butyl)oxazolidin-2-he

On the basis of 4-butylaniline and using the method described for intermediate compounds (R.i)specified in the title compound obtained as yellow solid (2,99 g; 58%yield).

1H NMR (CDCl3) δ: the 7.43 (d, J=8,8 Hz, 2H), 7,17 (d, J=8,8 Hz, 2H), 4,73 (m, 1H), 3,99 (m, 3H), 3,76 (m, 1H), 2,58 (m, 2H), 2.00 (evens advanced s, 1H), 1.57 in (m, 2H), of 1.34 (m, 2H), to 0.92 (t, J=7.0 Hz, 3H).

AH.ii. (S)-3-(4-Butylphenyl)-2-oxoacridine-5-ymetray ether methanesulfonate acid

On the basis of the intermediate compound (AH.i) (2,90 g) and using the method of N (but with 1.5 EQ. Ms2O instead of MsCl)specified in the title compound obtained as off-white solids (2,48 g, 65%yield).

MS (ESI, m/z): 328,3 [M+H+].

Experimental method AI: 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

Specified in the header connection receive similar synthetic method J using, however, tert-butultimately-[(S)-2-oxiranylmethyl]silane.

Analytical data allow us to identify this substance with the connection of the experimental method J.

Experimental method AJ: 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

AJ.i. tert-Butyl ether (2,3-dihydro-[1,4]like[2,3-C]pyridine-7-yl)carbamino acid

A suspension of 2,3-dihydro-1,4-like[2,3-C]pyridine-7-carboxylic acid (3,20 g; obtained according to WO 2007/016610) in tBuOH (100 ml) is treated with DFFA (4,60 ml) and tea (3.0 ml) and heated at 80°C overnight. The solvent is evaporated under reduced pressure and the residue races is Radelet between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4and evaporated under reduced pressure. The residue is stirred in ether, receiving a beige solid (2,90 g; 65%yield).

1H NMR (CDCl3) δ: to 7.84 (s, 1H), 7,49 (s, 1H), or 4.31 (m, 2H), 4,23 (m, 2H), of 1.52 (s, 11H).

AJ.ii. rat-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-3-(2,3-dihydro-[1,4]like[2,3-C]pyridine-7-yl)oxazolidin-2-he

A solution of intermediate compound (AJ.i) (3,30 g) and 1-{1-{[(tert-butyl)dimethylsilane]oxy]ethyl]oxirane (2.65 g; obtained according to J. Org. Chem. (2008), 73(3), 1093-1098) in DMF (42 ml) cooled to 0°C and treated tBuOLi (18 ml; 2,2-molar solution in THF). The reaction mixture is left to spontaneously warm to room temperature and then stirred at a temperature of 80°C for 2 days. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer is dried over MgSO4and purified by column chromatography (hexane/EA in the ratio 1:1)to give a yellow oil (2.70 g; 54%yield).

MS (ESI, m/z): 381,0 [M+H+].

AJ.iii. rat-3-(2,3-Dihydro-[1,4]like[2,3-C]pyridine-7-yl)-5-(2-hydroxyethyl)oxazolidin-2-he

On the basis of the intermediate compound (AJ.ii) and using method J, specified in the title compound obtained as yellow solid (1.10 g, 58%yield).

MS (ESI, m/z): 267,1 [M+H+].

AJ.iv. 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[14]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (AJ.iii) and using the method of N indicated in the title compound obtained as a beige solid (1,30 g, 100%yield).

MS (ESI, m/z): 345,2 [M+H+].

Experimental method AK: 2-[3-(2,3-Dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethyl ester rat-methanesulfonic acid

AK.i. Benzyl ether (2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)carbamino acid

A solution of 2,3-dihydro-1,4-like[2,3-b]pyridine-6-amine (commercial product; 2.70 g) in a mixture of acetone/water in a ratio of 1:1 (40 ml) is treated at 0°With 1-molar aqueous solution of NaHCO3(35 ml) and CBZ-Cl (2,63 ml). The reaction mixture was stirred at room temperature for 3 h, the organic solvent is evaporated under reduced pressure and the residue partitioned between water and ether/EA. The organic layer is dried over MgSO4and evaporated under reduced pressure, obtaining a beige solid (5.3 g; 100%yield).

1H NMR (CDCl3) δ: 7,50 (d, J=8.5 Hz, 1H), was 7.36 (m, 5H), 7,20 (d, J=8,8 Hz, 1H), 7,15 (advanced, 1H), 4,37 (m, 2H), 4,19 (m, 2H).

AK.ii. rat-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-3-(2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)oxazolidin-2-he

On the basis of the intermediate compound (AK.i) and 2-[2-[[(tert-butyl)dimethylsilane]oxy]ethyl]oxirane connection receive similar method AJ, stage AJ.ii. Receiving the hydrated product was then purified using column chromatography (hexane/EA in the ratio 1:1), getting a brown oil (2,90 g; 73%yield).

MS (ESI, m/z): 381,2 [M+H+].

AK.iii. rat-3-(2,3-Dihydro-[1,4]like[2,3-b]pyridine-6-yl)-5-(2-hydroxyethyl)oxazolidin-2-he

On the basis of the intermediate compound (AK.ii) and using method J, specified in the title compound obtained as yellow solid (1.10 g, 56%yield).

MS (ESI, m/z): to 266.8 [M+H+].

AK.iv. 2-[3-(2,3-Dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethyl ester rat-methanesulfonic acid

On the basis of the intermediate compound (AK.iii) and using the method of N indicated in the title compound obtained as a beige solid (1.24 g, 96%yield).

1H NMR (CDCl3) δ: 7,71 (d, J=8,8 Hz, 1H), 7,24 (m, 1H), 4,79 (m, 1H), 4,43 (m, 4H), to 4.33 (m, 1H), 4,23 (m, 2H), with 3.89 (dd, J=10,3, 6,7 Hz, 1H), 3.04 from (s, 3H), of 2.20 (m, 2H).

Experimental method AL: 2-[(R)-3-(4-Ethoxyphenyl)-2-oxoacridine-5-yl]ethyl ester methanesulfonic acid

AL.i. (R)-4-(tert-Butyldimethylsilyloxy)-1-(4-ethoxybenzylidene)butane-2-ol

A solution of 4-ethoxyaniline (commercial product; 3.2 ml) in a mixture of EtOH/water (in the ratio of 9:1; 150 ml) is injected into the reaction with (2R)-2-{2-[(tert-butyldimethylsilyloxy]ethyl}oxirane (obtained according to WO 2007/144423), after which the reaction mixture is heated at a temperature of 80°C during the night. The solvents are then removed under reduced pressure and the residue purified by column chromatography (Eagerton in the ratio 1:1), getting a brown oil (5,22 g; 62%yield).

MS (ESI, m/z): 340,2 [M+H+].

AL.ii. (R)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-3-(4-ethoxyphenyl)oxazolidin-2-he

On the basis of the intermediate compound (AL.i) and using the method I mentioned in the title compound obtained as off-white solids (4,30 g, 76%yield).

MS (ESI, m/z): 366,1 [M+H+].

AL.iii. (R)-3-(4-Ethoxyphenyl)-5-(2-hydroxyethyl)oxazolidin-2-he

On the basis of the intermediate compound (AL.ii) and using method J, specified in the title compound obtained as off-white solids (1,53 g, 52%yield).

MS (ESI, m/z): 251,9 [M+H+].

AL.iv. 2-[(R)-3-(4-Ethoxyphenyl)-2-oxoacridine-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (AL.iii) and using the method of N indicated in the title compound obtained as off-white solid (1.89 g, 96%yield).

MS (ESI, m/z): 330,0 [M+H+].

Experimental method AM: 2-[(R)-2-Oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

AM.i. (R)-4-(tert-Butyldimethylsilyloxy)-1-(4-propylaniline)butane-2-ol

On the basis of 4-propylaniline specified in the header connection receive similar synthetic method (AL), stage AL.i, in the form of a brown oil (6,99 g; 84%yield).

MS (ESI, m/z): 338,2 [M+H+].

AM.ii. (R)-5-[2-(tert-Boutilimit is silanolate)ethyl]-3-(4-propylphenyl)oxazolidin-2-he:

On the basis of the intermediate compound (AM.i) and using the method I mentioned in the title compound obtained as a brown oil (4,50 g, 60%yield).

MS (ESI, m/z): 364,1 [M+H+].

AM.iii. (R)-5-(2-Hydroxyethyl)-3-(4-propylphenyl)oxazolidin-2-he

On the basis of the intermediate compound (AM.ii) and using method J, specified in the title compound obtained as a yellowish solid (1,76 g, 57%yield).

MS (ESI, m/z): 249,9 [M+H+].

AM.iv. 2-[(R)-2-Oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (AM.iii) and using the method of N indicated in the title compound obtained as off-white solids (2,13 g, 93%yield).

MS (ESI, m/z): 328,4 [M+H+].

Experimental method'AN: 2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethyl ester methanesulfonic acid

AN.i. (R)-4-(tert-Butyldimethylsilyloxy)-1-(2,3-dihydrobenzo[1,4]dioxin-6-ylamino)butane-2-ol

On the basis of 2,3-dihydro-1,4-benzodioxin-6-amine (commercial product) specified in the header connection receive similar experimental method AL, stage AL.i, in the form of a brown oil (4,50 g; 51%yield).

MS (ESI, m/z): 354,3 [M+H+].

AN.ii. (R)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)oxazolidin-2-he

On the basis of the intermediate is about connections (AN.i) and using method I, specified in the title compound obtained as yellow solid (3.42 g, 71%yield).

MS (ESI, m/z): 380,2 [M+H+].

AN.iii. (R)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-(2-hydroxyethyl)oxazolidin-2-he

On the basis of the intermediate compound (AN.ii) and using method J, specified in the title compound obtained as off-white solids (1,72 g, 72%yield).

1H NMR (CDCl3) δ: 7,06 (d, J=2.6 Hz, 1H), 6,97 (dd, J=8,8, 2.6 Hz, 1H), 6,84 (m, 1H), to 4.81 (m, 1H), 4,24 (m, 4H), 4,06 (t, J=8,8 Hz, 1H), 3,88 (m, 2H), 3,69 (dd, J=8,8, 7,3 Hz, 1H), 2,03 (m, 2H), 1,82 (advanced s, 1H).

AN.iv. 2-[(R)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (AN.iii) and using the method of N indicated in the title compound obtained as off-white solids (2,03 g, 92%yield).

MS (ESI, m/z): 344,2 [M+H+].

Experimental method AO: 2-{3-[4-(4-Methoxybenzyl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-2-oxoacridine-5-yl}ethyl ester rat-methanesulfonic acid

AO.i. 6-Bromo-4-(4-methoxybenzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

A suspension of 6-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-she (2.0 g; obtained according to WO 01/30782) in DMF (40 ml) is treated with 4-methoxybenzylamine (1,18 ml) and Cs2CO3(8.5 g) and stirred at room temperature for 2 hours the Solvent is then evaporated under decreased the pressure and the residue distributed between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4and evaporated under reduced pressure. The residue is triturated with heptane, receiving a beige solid (2.8 g; 92%yield).

1H NMR (CDCl3) δ: 7,49 (d, J=8,8 Hz, 2H), 7,05 (s, 2H), 6,83 (d, J=8,8 Hz, 2H), 6,83 (d, J=8,8 Hz, 2H), 6,83 (d, J=8,8 Hz, 2H), 4,67 (s, 2H), of 3.77 (s, 3H).

AO.ii. rat-1 Azido-4-(tert-Butyldimethylsilyloxy)butane-2-ol

A solution of 2-[2-[[(tert-butyl)dimethylsilane]oxy]ethyl]oxirane (5.0 g; obtained according to WO 2007/144423) in the Meon (150 ml) is injected into the reaction with NaN3(3,95 g) and NH4Cl (2.37 g). The reaction mixture is then stirred at a temperature of 80°C overnight, then the solvent is evaporated under reduced pressure and the residue distributed between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4and evaporated under reduced pressure, obtaining a yellow oil (4.9 g; 81%yield).

1H NMR (CDCl3) δ: 4,01 (m, 1H), a 3.87 (m, 2H), 3,30 (m, 2H), 1,72 (m, 2H), of 0.90 (m, 9H), 0.06 to (m, 6H).

AO.iii. rat-1-Amino-4-(tert-butyldimethylsilyloxy)butane-2-ol

A solution of intermediate compound (AO.ii) (4,85 g) in THF (100 ml) hydronaut for 3 h over 10%Pd/C (1.0 g). The catalyst is filtered off and the filtrate is evaporated under reduced pressure, obtaining a yellow oil (4.1 g; 94,5%yield).

MS (ESI, m/z): 219,8 [M+H+].

AO.iv. rat-5-[2-(tert-Butyldimethylsilyloxy)ethyl]oxazolidin-2-he

the demise of the intermediate compound (AO.iii) (4.0 g) and using method I, specified in the title compound obtained as a light yellow oil (3.3 g; 74%yield).

1H NMR (CDCl3) δ: 5,22 (advanced, 1H), 4,80 (m, 1H), 3,74 (m, 3H), of 3.33 (m, 1H), 1.93 and (m, 2H), 0,89 (m, 9H), 0,07 (m, 6H).

AO.v. rat-6-{5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4-(4-methoxybenzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

Intermediate compounds (AO.iv) (1.97 g) and (AO.i) (2.8 g), CuI (305 mg) and K2CO3(2.2 g) is loaded into a round bottom flask, which was then rinsed with argon. TRANS-1,2-diaminocyclohexane (1.2 ml) and dioxane (60 ml) is added to the mixture, after which the reaction vessel is rinsed with argon. Then the reaction mixture is stirred at a temperature of 100°C for 2 days and distributed between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4and evaporated under reduced pressure. The residue is purified by column chromatography (DHM/Meon in the ratio 19:1)to give after crystallization from heptane colourless solid (1.7 g; 41%yield).

1H NMR (CDCl3) δ: 7,81 (d, J=8,8 Hz, 1H), 7,28 (m, 3H), for 6.81 (m, 2H), 5,20 (s, 2H), 4,82 (m, 1H), 4,28 (m, 1H), 3,85 (m, 3H), of 3.77 (s, 3H), 2,00 (m, 2H), 0,89 (s, 9H), of 0.07 (s, 6H).

AO.vi. rat-6-[5-(2-hydroxyethyl)-2-oxoacridine-3-yl]-4-(4-methoxybenzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one:

On the basis of the intermediate compound (AO.v) (1.7 g) and using method J, specified in the title compound is obtained after about isdi using column chromatography (EA, then EA/Meon in the ratio 9:1) as a yellow oil (1.4 g; 100%yield).

MS (ESI, m/z): 400,0 [M+H+].

AO.vii. 2-{3-[4-(4-Methoxybenzyl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-2-oxoacridine-5-yl}ethyl ester rat-methanesulfonic acid

On the basis of the intermediate compound (AO.vi) (1,32 g) and using the method of N indicated in the title compound obtained as a colorless foam (1.3 g; 82,5%yield).

MS (ESI, m/z): 477,8 [M+H+].

Experimental method AR: 6-[(S)-5-(2-amino-ethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

AP.i. 6-[(S)-5-(2-Azidoethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

A solution of intermediate compound (L) (1.90 g) in DMF (8 ml) is treated with NaN3(400 mg) and stirred at 80°C during the night. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4and evaporated under reduced pressure. The residue is stirred in a mixture of ether/Meon, receiving a beige solid (1.30 grams; 80%yield).

MS (ESI, m/z): 320,3 [M+H+].

Ar. 6-[(S)-5-(2-amino-ethyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (AP.i) and using method F, indicated in the title compound obtained as a beige solid (0,90 g, 82%yield).

MS (ESI, m/z): 294,4 [M+H+].

The experimental is orbital method AQ: 2-[(S)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethyl ester methanesulfonic acid

On the basis of (2S)-2-[2-[[(tert-butyl)dimethylsilane]oxy]ethyl]oxirane specified in the header connection receive similarly, AN experimental method.

Analytical data identical to the data connection of AN experimental method.

Experimental method AR: 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

AR.i. (R)-1-Azido-5-(tert-butyldimethylsilyloxy)pentane-2-ol

On the basis of (R)-2-[2-[[(tert-butyl)dimethylsilane]oxy]propyl]oxirane (5.0 g; obtained according to Organic Letters (2005), 7(18), 3997-4000) and NaN3specified in the header connection receive similar experimental method JSC, stage AO.ii, in the form of oil (of 5.17 g; 86%yield).

1H NMR (CDCl3) δ: 3,79 (m, 1H), 3,68 (m, 2H), 3,29 (m, 2H), of 1.66 (m, 4H), of 0.90 (m, 9H), 0,07 (m, 6H).

AR.ii. (R)-5-[2-(tert-Butyldimethylsilyloxy)propyl]oxazolidin-2-he

Specified in the header connection receive similar experimental method JSC, stage AO.iii and AO.iv, by hydrogenation of the intermediate compound (AR.ii)using method F, reaction to the OED, using method I, as a colourless solid (3,48 g; 67%yield).

1H NMR (CDCl3) δ: 5,22 (advanced, 1H), and 4.68 (m, 1H), 3,66 (m, 3H), of 3.25 (t, J=7,6 Hz, 1H), 1,72 (m, 4H), to 0.89 (m, 9H), of 0.05 (m, 6H).

AR.iii. (R)-6-{5-[2-(tert-Butyldimethylsilyloxy)propyl]-2-oxoacridine-3-yl}-4-(4-methoxybenzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

Recognize the I of the intermediate compounds (AO.i) (1.97 g) and (AR.ii) specified in the header connection receive similar experimental method JSC, stage AO.v, in the form of a colourless foam (4,43 g; 70%yield).

1H NMR (CDCl3) δ: 7,80 (d, J=8.5 Hz, 1H), 7,28 (m, 3H), for 6.81 (d, J=8,8 Hz, 2H), 5,20 (s, 2H), 4,67 (m, 3H), 4,22 (dd, J=10,0, 8.5 Hz, 1H), of 3.77 (s, 3H), 3,70 (m, 2H), 1,78 (m, 4H), of 0.90 (m, 9H), is 0.06 (s, 6H).

AR.iv. (R)-6-[5-(2-Hydroxypropyl)-2-oxoacridine-3-yl]-4-(4-methoxybenzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

Specified in the header connection receive similar experimental method JSC, stage AO.vi on the basis of intermediate compounds (AR.iii), as a colourless solid (640 mg, 38%yield).

1H NMR (DMSO d6) δ: 11,16 (s, 1H), EUR 7.57 (m, 1H), 7,40 (d, J=8,8 Hz, 1H), and 4.68 (s, 1H), 4,59 (s, 2H), 4,47 (t, J=5.0 Hz, 1H), 4,19 (m, 1H), 3,69 (dd, J=10,0, 7,0 Hz, 1H), 3.43 points (q, J=6.2 Hz, 2H), 1,73 (m, 2H)and 1.51 (dd, J=9,7, 6,7 Hz, 2H).

AR.v 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-v][1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

The solution SO3·Rog-complex (900 mg) in DMSO (3 ml) is added dropwise at room temperature over 10 min to a suspension of intermediate compounds (AR.iv) (830 mg) and DIPEA (1,45 ml) in DHM/DMSO (1:1 ratio; 5 ml). The mixture was then stirred at room temperature for 1 h, diluted with water and extracted with DHM. The organic layer is successively washed with water and brine, dried over MgSO4concentrate under reduced pressure and crystallized from a mixture of ether/EA, receiving a colorless solid (618 mg; 75%yield).

1H NMR (DMSO d6

Experimental method AS: (S)-1-Amino-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

AS.i. 2-Methoxy-8-vinylphenol

(PPh3)4Pd (578 mg) is added at room temperature to a solution of the complex of the anhydride vinylboronic acid with pyridine (1.2 g) in DME (80 ml). The solution is then Tegaserod, passing through him N2within 20 minutes, then add To the2CO3(1,38 g), water (24 ml) and 2-methoxyquinoline-8-silt ether triftormetilfullerenov acid (of 3.07 g). The mixture is heated under reflux overnight, cooled to room temperature and partitioned between water and ether. The aqueous phase is then washed with ether and the combined organic phases are washed with water and brine, dried over MgSO4concentrate under reduced pressure and purified by column chromatography (heptane/EA ratio 4:1)to give a yellow liquid (1.18 g; 64%yield).

1H NMR (CDCl3) δ: of 7.97 (d, J=8,8 Hz, 1H), 7,88 (m, 2H), to 7.64 (dd, J=7,9, 1.5 Hz, 1H), was 7.36 (t, J=7,6 Hz, 1H), 6,91 (d, J=8,8 Hz, 1H), 6,02 (dd, J=17,9, 1.8 Hz, 1H), the 5.45 (dd, J=11,1, 1.8 Hz, 1H), 4,10 (s, 3H).

AS.ii. (R)-1-(2-Methoxyquinoline-8-yl)ethane-1.2-diol

On the basis of the intermediate compound (AS.i) and AD-mix β and using method L, is specified in the title compound obtained as a beige solid (3,22 g, to the quantitative output).

MS (ESI, m/z): 279,3 [M+H+].

AS.iii. (R)-2-(tert-Butyldimethylsilyloxy)-1-(2-methoxyquinoline-8-yl)ethanol

On the basis of the intermediate compound (AS.ii) and using method M that is listed in the title compound obtained as a yellow oil (4,16 g, quantitative yield).

MS (ESI, m/z): 334,0 [M+H+].

AS.iv. tert-Butyl ester [(S)-2-(tert-butyldimethylsilyloxy)-1-(2-methoxyquinoline-8-yl)ethyl]carbamino acid

On the basis of the intermediate compound (AS.iii) (4,70 d) specified in the header connection receive similar synthetic method of the Z stage Z.iv (reaction Mitsunobu with subsequent restoration azide) and (Z.v) (introduction BOC-protective group, method G)as a pale yellow oil (8,4 g; quantitative yield; dirty Side2O).

MS (ESI, m/z): 359,3 [M+H+].

AS.v. tert-Butyl ester [(S)-2-hydroxy-1-(2-methoxyquinoline-8-yl)ethyl]carbamino acid

On the basis of the intermediate compound (AS.iv) (6,48 g) and using method J, specified in the title compound obtained as a colorless foam (2,99 g; 63%yield).

MS (ESI, m/z): 319,0 [M+H+].

AS.vi. tert-Butyl ester ((S)-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (AS.v) (3,34 g) and using method H (but heating the reaction mixture at 50°C)specified in the title compound obtained as a demon who Vatan solid (2.64 g; 88%yield).

MS (ESI, m/z): 287,1 [M+H+].

AS.vii. (S)-1-Amino-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (AS.vi) (2,63 g) and using the method specified in the title compound obtained as a colorless solid (1,58 g; 93%yield).

MS (ESI, m/z): 187,1 [M+H+].

Experimental method AT: (S)-4-Aminomethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

AT.i. (S)-3-Azido-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ester acetic acid

On the basis of the intermediate compound (V.ii) (1.65 g) and using the same method applied to obtain the intermediate compound (Z.iv)specified in the title compound obtained as a colorless oil (1.63 g; 90%yield).

MS (ESI, m/z): 302,0 [M+H+].

AT.ii. (S)-3-tert-Butoxycarbonylamino-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ester acetic acid

On the basis of the intermediate compound (AT.i) (1.63 g) and using sequentially the methods F and G, is listed in the title compound obtained as a pale yellow oil (2,04 g; 100%yield).

MS (ESI, m/z): 376,2 [M+H+].

AT.iii. tert-Butyl ester [(S)-3-hydroxy-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl]carbamino acid

A suspension of intermediate compounds (AT.ii) (2,05 g) and K2CO3(to 3.02 g) in the Meon (72 ml) was stirred at room temperature for 30 minutes the Solvent is removed when igenom pressure and the residue is transferred into the mixture DHM/water. The organic layer was washed with brine, dried over MgSO4, concentrated and purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4)to give a colorless foam (1.28 g; 70%yield).

MS (ESI, m/z): 334,2 [M+H+].

AT.iv. tert-Butyl ester ((S)-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ylmethyl)carbamino acid

On the basis of the intermediate compound (AT.iii) (1.28 g) and using method H to get nelfinavir followed by heating the reaction mixture for 2 h at 60°C for completion of the cyclization, specified in the title compound obtained as a colorless foam (985 mg, 85%yield).

MS (ESI, m/z): 302,2 [M+H+].

AT.v. (S)-4-Aminomethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (AT.iv) (980 mg) and using the method specified in the title compound obtained as a pale yellow solid (522 mg; 80%yield).

MS (ESI, m/z): 202,2 [M+H+].

Experimental method AU: 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

On the basis of (S)-tert-butultimately-(3-oxyaliphatic)silane (obtained according to Org. Lett. (2005), 7(19), 4083-4086) specified in the header of the connection (in the form of a pink solid) receive similar experimental method U in stage 4 (disclosure of resin: 50%output; the education of oxazolidinone: 100%; exemption of alcohol from the protective groups: 71%yield; the formation of aldehyde: 91%yield).

Analytical data identical to the data connection of the experimental method U.

Experimental method AV: 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

On the basis of (S)-tert-butultimately-(3-oxyaliphatic)silane (obtained according to Org. Lett. (2005), 7(19), 4083-4086)specified in the header of the connection (in the form of a beige solid) receive similar experimental method T in stage 4 (disclosure of epoxide: 45%; education oxazolidinone: 100%; exemption of alcohol from the protective groups: 65%; the formation of aldehyde: 87%yield).

Analytical data identical to the data connection of the experimental method So

Experimental method AW: 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl ether methanesulfonate acid

AW.i. 6-[(S)-5-(tert-butyldimethylsilyloxy)-2-hydroxyethylamino]-4H-benzo[1,4]thiazin-3-one

A mixture of (S)-tert-butultimately-(3-oxyaliphatic)silane (28,3 g, obtained according to Org. Lett. (2005), 7, 3997) and 6-amino-4H-benzo[1,4]thiazin-3-one (23,6 g) in MeCN (390 ml) is treated with LiClO4(41.8 g) and heated at 60°C for 4 h Volatile fractions are removed under reduced pressure and the residue distributed between ethyl acetate and p is SOLOM. The organic phase is dried over MgSO4and concentrate. The residue is purified by column chromatography (heptane/EA ratio of 1:1, EA)to give the desired intermediate compound in the form of a yellowish foam (8,4 g; 16%yield).

MS (ESI, m/z): 397,1 [M+H+].

AW.ii. 6-{(S)-5-[3-(tert-Butyldimethylsilyloxy)propyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

A solution of intermediate compound (AW.i) (8.0 g) in THF (500 ml) is treated with CBI (4.9 g) and heated at 50°C over night. The mixture is then cooled to room temperature, diluted with ethyl acetate and washed with water and brine, dried over MgSO4and concentrate. The resulting material is crystallized from a mixture of heptane/EA getting the desired oxazolidinone in the form of a beige solid (4.5 g; 53%yield).

MS (ESI, m/z): 423,4 [M+H+].

AW.iii. 6-[(S)-5-(3-Hydroxypropyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

A suspension of intermediate compounds (AW.ii) (4.5 g) in THF (42 ml) is treated with 1-molar solution TBAF in THF (1 EQ.). The brown solution was stirred at room temperature for 4 h, diluted with ethyl acetate, washed with water and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography (EA then EA/Meon in the ratio 9:1)to give the desired alcohol as a yellowish foam (3.6 g; 100%is ihod).

MS (ESI, m/z): 309,3 [M+H+].

AW.iv. 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl ether methanesulfonate acid

A suspension of intermediate compounds (AW.iii) (3.0 g) in DHM process of tea (2.8 ml), adding dropwise MsCl (1,37 g). The mixture is stirred at room temperature for 2 h, diluted with DHM, washed with water, dried over MgSO4and concentrate. The residue is crystallized from a mixture of ether/EA, receiving required mesilate in the form of a beige solid (3.6 g; 93%yield).

MS (ESI, m/z): 387,2 [M+H+].

Experimental method AH: rat-4-Amino-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Ah. 7-fluoro-2-methoxy-8-vinyl - [1,5]naphthiridine

To a solution of 8-bromo-7-fluoro-2-methoxy-1,5-naphthiridine (5.0 g; commercial product) in 1,2-DME (150 ml) is added tetrakis-(PPh3)RA (1.1 g), after which the mixture is blown with N2for 20 min and added To a2CO3(2,69 g), water (50 ml) and the complex of the anhydride vinylboronic acid with pyridine (2,34 g). The mixture is stirred at a temperature under reflux for 3 hours After cooling to room temperature, water is added and the mixture extracted with ethyl acetate. The combined organic phases are washed with brine, dried over MgSO4, concentrated and purified by column chromatography (EA/heptane 1:1), produces the specified in the header of the intermediate compound as a brown oil (3.12 g, 79%yield).

MS (ESI, m/z): 205,0 [M+H+].

AX.ii. (R)-1-(3-Fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethane-1,2-diol

On the basis of the intermediate compound (AHL) (3.12 g) and using the method of L with AD-mix β, specified in the title compound obtained as off-white solid (4 g, quantitative yield).

MS (ESI, m/z): 239,0 [M+H+].

AX.iii. (R)-2-(tert-Butyldimethylsilyloxy)-1-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethanol

To a solution of intermediate compound (AX.ii) (3,96 g) in DHM (160 ml) was added imidazole (of 1.05 equiv.) Cl (of 1.05 equiv.) and DMAP (0.1 EQ.). The mixture is stirred at room temperature for 1 h, water is added and extracted with DHM. The organic layer is dried over MgSO4and concentrate, getting mentioned in the title intermediate compound as a yellow oil (4.52 g, 77%).

MS (ESI, m/z): 353,2 [M+H+].

AX.iv. tert-Butyl ester [(S)-2-(tert-butyldimethylsilyloxy)-1-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethyl]carbamino acid

On the basis of the intermediate compound (AX.iii) (4.52 g) and using method N', specified in the header of the intermediate compound obtained as a light yellow oil (6,76 g, quantitative yield).

MS (ESI, m/z); 452,2 [M+H+].

AX.v. tert-Butyl ester [(S)-1-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)-2-hydroxyethyl]carbamino acid

On the basis of the intermediate compound (AX.iv) (6,76 g) and use the method I J, specified in the header of the intermediate compound obtained as a yellow oil (3,96 g, 78%yield).

MS (ESI, m/z): 338,2 [M+H+].

AX.vi. tert-Butyl ester ((S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-yl)carbamino acid

On the basis of the intermediate compound (AX.v) (of 3.46 g) and using method H followed by heating at a temperature of 80°C for 18 h in EDC specified in the header of the intermediate compound obtained as a yellow oil (0,90 g, 28%yield).

MS (ESI, m/z): 306,2 [M+H+].

AX.vii. rat-4-Amino-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (AX.vi) (0,875 g) and using the method specified in the header of the intermediate compound obtained as a pale yellow solid (0,42 g, 71%yield). Analysis ofher-values showed that the obtained substance is a racemate. Asher-identify at an earlier stage was not carried out, it is possible that racemization occurs at an earlier stage of the synthesis.

MS (ESI, m/z): 206,1 [M+H+].

Experimental method AY: 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of tert-butultimately-[(S)-2-oxiranylmethyl]silane specified in the header connection receive similar experimental method I.

Analytical journal is their data identical to the data connection of the experimental method I.

Experimental method AZ: (R)-6-Amino-7-fluoro-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Specified in the header connection receive according to experimental method AD, but using AD-mix α at the first stage.

Analytical data identical to the data connection of the experimental method AD.

Experimental method VA: 6-(5-[(1RS}-1-(tert-Butyldimethylsilyloxy)-3-hydroxypropyl]-((5RS)-2-oxoacridine-3-yl)}-4H-benzo[1,4]thiazin-3-one

VA. tert-Butyl ether (3RS)-3-(tert-butyldimethylsilyloxy)-3-((2RS)-oxiran-2-yl)propionic acid

A solution of tert-butyl ester 3-[[(tert-butyldimethylsilyl]oxy]-4-pentenol acid (3,60 g; obtained according to J. Org. Chem. (1994), 59, 4760-4764) in DHM (100 ml) is injected into the reaction with m-HPFB (3,96 g) for 2 days. The reaction mixture was partitioned between DHM, 10%aqueous solution of Na2S2O3and saturated aqueous NaHCO3, after which the organic phase is separated, dried over MgSO4that is evaporated under reduced pressure and purified by column chromatography (heptane/EA ratio from 9:1 to 4:1)to give a colorless liquid (2.55 g; 67%yield; mixture of diastereoisomers in the ratio 3:2).

1H NMR (CDCl3) δ: was 4.02 (m, 1H, diast)3,76 (d, J=6,4 Hz, 1H, dust, A)to 3.02 (m, 1H, dist, A, 2,99 (m, 1H, diast)of 2.8 and 2.4 (m, 4H, dust, a and b), of 1.45 (s, 9H, dust, a and b), to 0.88 (m, 9H, dust, a and b), 0,10 (m, 6H, dust A and b).

BA.ii. tert-Butyl ether (3RS)-3-(/tert-butyldimethylsilyloxy)-(4RS)-4-hydroxy-5-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-ylamino)pentanol acid

A solution of intermediate compound (V) (6,05 g) and 6-amino-4H-benzo[1,4]thiazin-3-one (of 3.60 g) in a mixture of EtOH/water (in the ratio of 9:1; 100 ml) is heated under reflux for 30 minutes the Organic solvent is removed under reduced pressure, the residue is transferred into ethyl acetate (20 ml) and filtered. The filtrate is concentrated under reduced pressure and purified by column chromatography (heptane/EA ratio from 1:1 to 1:2)to give after trituration with a mixture of EA/ether colourless solid (3,26 g; 34%yield).

MS (ESI, m/z): 483,2 [M+H+].

BA.iii. tert-Butyl ether (3RS)-3-(tert-butyldimethylsilyloxy)-3-[((5RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl))oxazolidin-5-yl]propionic acid

On the basis of the intermediate compound (BA.ii) (3.25 g) and using the method I mentioned in the title compound obtained as a colorless solid (3,27 g; 95%yield).

MS (ESI, m/z): 509,1 [M+H+].

BA.iv. 6-{5-[(1RS)-1-tert-Butyldimethylsilyloxy)-3-hydroxypropyl]-((5RS)-2-oxoacridine-3-yl)}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (BA.iii) (1.01 g) and using the method As specified in the title compound is obtained after purification using a column of chromatography the (heptane/EA in the ratio 2:1, then 0:1) as a colourless foam (205 mg, 23%yield).

MS (ESI, m/z): 439,1 [M+H+].

Experimental method BB: (R)-6-Amino-7-fluoro-2-methoxy-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

BB.i. 6-Fluoro-2,3-dimethoxyaniline-5-carbaldehyde

The solution tetramethylpiperidine (16.4 ml) in dry THF (100 ml) cooled to a temperature of -78°C and added dropwise n-BuLi (a 2.5 molar solution in hexane; 39 ml). Then the solution was stirred at the same temperature for 30 min, after which a solution of 6-fluoro-2,3-dimethoxyaniline (15.6 g; obtained from commercially available 2,3-dichloro-6-forination according to Egyptian Journal of Chemistry (1980), Volume Date 1977, 20, 427-39) in dry THF (450 ml), cooled down to -78°C., added dropwise to the first solution and then stirred at the same temperature for 30 minutes, the Reaction mixture was treated with DMF (to 11.56 ml), stirred at -78°C for 15 min, transferred into a mixture of saturated solution of NH4Cl and ice and extracted with ether. The organic layer was washed with brine, dried over MgSO4that is evaporated under reduced pressure and crystallized from a mixture of hexane/EA, receiving light yellow solid (12.5 g; 71%yield).

1H NMR (CDCl3) δ: 11,10 (d, J=0.6 Hz, 1H), of 7.96 (dd, J=9,1, a 5.3 Hz, 1H), 7,30 (m, 1H), 4,19 (m, 3H), 4,15 (m, 3H).

BB.ii. 6-Fluoro-2,3-dimethoxy-5-virilisation

A suspension of the bromide of methyltriphenylphosphonium the (18,15 g) in THF (200 ml) is treated with tBuOK (5.7 g). After stirring for 1 h, the solution was cooled to 0°C, treated with a solution of intermediate compound (BB.i) (10.0 g) in THF (100 ml). The reaction mixture was then stirred at room temperature for 3 h, and then successively washed with water and a saturated solution of NH4Cl. The organic layer is dried over MgSO4, evaporated and purified by column chromatography (hexane/EA ratio from 4:1 to 2:1)to give a colorless solid (8,80 g; 89%yield).

1H NMR (CDCl3) δ: a 7.62 (dd, J=8,8, 5.3 Hz, 1H), 7,46 (m, 1H), 7,25 (m, 1H), 6,34 (m, 1H), 5,69 (m, 1H), 4,17 (s, 3H), 4,13 (s, 3H).

BB.iii. (S)-1-(6-fluoro-2,3-dimethoxyaniline-5-yl)ethane-1,2-diol

On the basis of the intermediate compound (BB.ii) (8,70 d) and using the method of L with AD-mix α, specified in the title compound obtained as a beige solid (the ceiling of 5.60 g; 56%yield) after crystallization from ether.

1H NMR (DMSO d6) δ: to 7.67 (dd, J=9,1, 5.6 Hz, 1H), 7,35 (dd, J=10,3, 9.1 Hz, 1H), 5.56mm (m, 1H), 5,20 (d, J=6,4 Hz, 1H), 4,73 (t, J=6.2 Hz, 1H), of 4.05 (s, 3H), 4,01 (s, 3H), a 3.87 (m, 1H), 3,69 (m, 1H).

BB.iv. (S)-2-(tert-Butyldimethylsilyloxy)-1-(6-fluoro-2,3-dimethoxyaniline-5-yl)ethanol

On the basis of the intermediate compound (BB.iii) (5.50 g) and using method M that is listed in the title compound is obtained after purification using column chromatography (heptane/EA in the ratio 2:1) as a yellow oil (yield of 7.40 g; 94%yield.

MS (ESI, m/z): 383,2 [M+H+].

.v. tert-Butyl ester [(R)-2-(tert-butyldimethylsilyloxy)-1-(6-fluoro-2,3-dimethoxyaniline-5-yl)ethyl]carbamino acid

On the basis of the intermediate compound (BB.iv) (7.30 g) and using method N'mentioned in the title compound is obtained after purification using column chromatography (heptane/EA ratio from 9:1 to 4:1) as a yellow oil (6.7 g, 73%yield).

1H NMR (CDCl3) δ: 7,66 (dd, J=9,1, 5.6 Hz, 1H), 7.23 percent (m, 1H), 6,50 (m, 1H), 4,17 (s, 3H), 4,13 (s, 3H), 3,92 (d, J=6,4 Hz, 2H), of 1.42 (s, 9H), 0.76 to (s, 9H), -0,09 (s, 3H), -0,14 (s, 3H).

BB.vi. tert-Butyl ester [(R)-1-(6-fluoro-2,3-dimethoxyaniline-5-yl)-2-hydroxyethyl]carbamino acid

On the basis of the intermediate compound (BB.v) (6,70 g) and using method J, specified in the header connection receive, after crystallization from a mixture of heptane/EA ratio of 1:1, in the form of a colorless solid (3,60 g; 70%yield).

1H NMR (CDCl3) δ: of 7.69 (dd, J=9,1, 5.6 Hz, 1H) 7,26 (m, 1H), 6,60 (m, 1H), 5,80 (m, 1H), 4,17 (s, 3H), 4,13 (s, 3H), 3,95 (m, 2H), USD 1.43 (s, 9H).

BB.vii. tert-Butyl ester ((R)-7-fluoro-2-methoxy-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-yl)carbamino acid

On the basis of the intermediate compound (BB.vi) (3.50 g) and using method H, receive intermediate mesilate. The reaction mixture was stirred at reflux for 12 h, cooled to room temperature and washed in the Oh. The organic layer is dried over MgSO4and concentrate under reduced pressure to give crude solid (2.70 g, 84%yield), containing specified in the title compound in the form of a mixture (in the ratio 3:2) with (R)-4-(6-fluoro-2,3-dimethoxyaniline-5-yl)oxazolidin-2-one. The mixture is used without further purification in the next stage.

BB.viii. (R)-6-Amino-7-fluoro-2-methoxy-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

On the basis of the intermediate compound (BB.vii) (2.70 g) and using the method specified in the title compound is obtained after purification using column chromatography (mixture of EA/Meon in the ratio of 9:1 containing 1% NH4OH) as a colourless solid (469 mg, 25%yield).

MS (ESI, m/z): 236,2 [M+H+].

Experimental method SU: (R)-1-Amino-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Specified in the header connection receive similar synthetic method AS, but using AD-mix and in the second stage.

Analytical data identical to the data connection of the experimental method AS well.

Experimental method BD: (R)-4-Hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ester toluene-4-sulfonic acid

BD.i. 2-(6-Methoxy[1,5]naphthiridine-4-yl)propane-1,3-diol

A solution of 2-methoxy-8-methyl-1,5-naphthiridine (2,90 g; obtained according to WO 00/21948) in aqueous formaldehyde (37%; 7,8 ml) is heated under those is the temperature of 100°C for 3 days. After cooling to room temperature the reaction mixture is concentrated without dried, the residue is transferred in the Meon (10 ml) and again concentrated. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:100:8)to give a colorless solid (2,78 g; 71%yield).

1H NMR (DMSO-d6) δ: 8,67 (d, J=4.4 Hz, 1H), they were 8.22 (d, J=9.1 Hz, 1H), 7,51 (d, J=4.4 Hz, 1H), 7,22 (d, J=9.1 Hz, 1H), 4,56 (m, 2H), 4.00 points (m, 4H), of 3.84 (m, 4H).

BD.ii. (S)-3-Hydroxy-2-(6-methoxy[1,5]naphthiridine-4-yl)propyl ester acetic acid

A solution of intermediate compound (BD.i) (1,34 g) in vinyl acetate (10 ml) is treated with powdered 3Å molecular sieves (78 mg) and stirred at room temperature for 15 min in nitrogen atmosphere. Then add the lipase, mobilized an acrylic resin that is obtained from Candida antarctica (600 mg, Sigma L4777), and stirring is continued for 4 h at room temperature. The polymer associated with the enzyme is filtered off, the filter cake washed with THF and the filtrate concentrated. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:25:2)to give colorless oil (0,688 g; 44%yield).

1H NMR (CDCl3) δ: 8,72 (d, J=4,7 Hz, 1H), 8,23 (d, J=9.1 Hz, 1H), 7,46 (d, J=4,7 Hz, 1H), 7,15 (d, J=9.1 Hz, 1H), with 4.64 (m, 2H), 4,24 (m, 1H), 4,08 (m, 5H), was 2.05 (s, 3H).

BD.iii. (S)-7-Oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether in ssnoi acid

A solution of intermediate compound (BD.ii) (2,05 g) in DHM (40 ml) is transformed into the corresponding mesilate, using the method N. After complete consumption of alcohol added EDC (40 ml) and the solution is further stirred at 60°C for 4 h After cooling to room temperature, water is added, the layers decanted and the aqueous layer was again extracted with DHM. The combined organic layers are concentrated without dried, and the residue is triturated with TBME, getting a grey solid (1.40 g; 77%yield).

1H NMR (CDCl3) δ: 8,53 (d, J=4,7 Hz, 1H), to 7.93 (d, J=9.7 Hz, 1H), 7,34 (dd, J=4,7, 0.9 Hz, 1H), make 6.90 (d, J=9.7 Hz, 1H), 4,57 (dd, J=12,9, and 9.4 Hz, 1H), 4,37 (d, J=6,4 Hz, 2H), 4,27 (dd, J=13,2, 5.0 Hz, 1H), 4.09 to (m, 1H), to 2.06 (s, 3H).

BD.iv. (S)-4-Hydroxymethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

To a solution of intermediate compound (BD.iii) (1,11 g) in the Meon (30 ml), cooled to -10°C, add To the2CO3(313 mg, 0.5 equiv.) the mixture is vigorously stirred at 0°C for 20 min, concentrated and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:100:8)to give a colorless solid (773 mg; 84%yield).

MS (ESI, m/z): 203,0 [M+H+].

BD.v. (S)-7-Oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether methanesulfonate acid

A solution of intermediate compound (BD.iv) (600 mg) in DHM (30 ml) is transformed into the corresponding mesyl is t, using the method N. The crude substance (1,03 g) used in the next stage without further purification.

MS (ESI, m/z): 281,2 [M+H+].

BD.vi. 4-Methylene-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

A solution of intermediate compound (BD.v) (1,03 g) in DMF (10 ml) was stirred at room temperature in the presence of DBU (1,12 ml) for 2 hours, the Reaction mixture was then diluted with ethyl acetate and water, the aqueous layer was extracted with ethyl acetate (twice 100 ml) and the mixture DHM/Meon (three times 50 ml; the ratio of 9:1). The combined organic layers are successively washed with water and brine and dried over MgSO4. The solvent is evaporated under reduced pressure, obtaining a yellow solid (490 mg; 72%yield).

1H NMR (CDCl3) δ: 8,55 (d, J=5.0 Hz, 1H), of 7.96 (d, J=9.7 Hz, 1H), 7,44 (d, J=5.0 Hz, 1H), 6,92 (d, J=9.7 Hz, 1H), 6,00 (td, J=2,9, 0.9 Hz, 1H), 5,65 (td, J=2,6, 0.9 Hz, 1H), 5,02 (t, J=2,6 Hz, 2H).

BD.vii. (R)-4-Hydroxy-4-hydroxymethyl-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

A solution of intermediate compound (BD.vi) (240 mg) dihydroxyaryl in the presence of AD-mix α, using method L. Crude yellow solid (216 mg, 76%yield) used in the next stage without further purification.

1H NMR (CDCl3) δ: 8,55 (d, J=4,7 Hz, 1H), of 7.90 (m, 1H), 7,53 (d, J=4,7 Hz, 1H), for 6.81 (m, 1H), 4,35 (m, 2H), with 3.89 (m, 3H).

BD.viii. (R)-4-Hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de][1,5]naphthiridine-4-ymetray ether Tolu is l-4-sulfonic acid

A solution of intermediate compound (BD.vii) (210 mg) was stirred at room temperature overnight in the presence of tea (0,20 ml), TsCl (185 mg) and oxide dibutyrate (12 mg). The reaction mixture was diluted with water (3 ml), the organic layer was washed with a saturated solution of NaHCO3and brine and dried over MgSO4. The solvent is then evaporated under reduced pressure, obtaining off-white solid (172 mg; 48%yield).

MS (ESI, m/z): 373,0 [M+H+].

Experimental method IN rat-1-Amino-9-bromo-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one:

BE.i. (7-Bromo-2-methoxyquinoline-8-yl)methanol

A suspension of 7-bromo-8-methyl bromide-2-(metiloksi)quinoline (35.2 g; obtained according to WO 2007/081597; containing 20% dibromononane connection) in a mixture of acetone/water (1:1 ratio; 860 ml) is heated under reflux for 6 h in the presence of NaHCO3(14,63 g). The organic solvent is removed under reduced pressure and the residue extracted with ethyl acetate, then the organic layer was washed with brine and dried over Na2SO4. The solvent is then evaporated and the residue crystallized from CRIME, receiving off-white solid (16.0 g; 56%yield).

MS (ESI, m/z): 268,0 [M+H+].

BE.ii. 7-Bromo-2-methoxyquinoline-8-carbaldehyde

The solution oxalicacid (for 9.47 ml) in DHM (200 ml), cooled down to -78°C, was added to ply to a solution of DMSO (9,52 ml) in DHM (80 ml). After stirring for 15 min the solution is treated with a solution of the intermediate (BE.i) (10.0 g) in DHM (80 ml). After stirring at -78°C for 3 h, the reaction mixture is treated dropwise with a solution of tea (39,0 ml) in DHM (80 ml) for 1 h Then the reaction mixture was stirred for 40 min and leave spontaneously warm to room temperature, then treated with saturated aqueous NaHCO3. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent is evaporated, and the residue is dissolved in ethyl acetate and filtered through a layer of silica gel, obtaining a pale yellow solid (3,74 g; 38%yield).

1H NMR (DMSO-d6) δ: 11,06 (s, 1H), at 8.36 (d, J=8,8 Hz, 1H), 8,04 (d, J=8,8 Hz, 1H), 7,74 (m, 1H), 7,17 (d, J=8,8 Hz, 1H), 4,01 (s, 4H).

BE.iii. 7-Bromo-2-methoxy-8-vinylphenol

To a solution of bromide methyltriphenylphosphonium (1,00 g) in THF (8 ml), cooled down to -78°C. add n-BuLi (a 2.5 molar solution in hexane, of 1.09 ml, 1.5 EQ.). The mixture is stirred for 15 min at this temperature and then 45 min at 0°C, then cooled to -78°C and rapidly added a solution of intermediate compound (BE.ii) (500 mg) in THF (8 ml). The reaction proceeds during the night, slowly reaching room temperature. After that add Meon to stop the reaction and see what camping concentrated under reduced pressure. The residue is purified by column chromatography (heptane/EA ratio from 4:1 to 2:1), obtaining mentioned in the title compound as a yellowish oil (411 mg; 83%yield).

MS (ESI, m/z): 264,3 [M+H+].

BE.iv. rat-1-(7-Bromo-2-methoxyquinoline-8-yl)ethane-1,2-diol

On the basis of the intermediate compound (BE.iii) (5.50 g) is analogous synthetic method AH, stage AX.ii, using, however, K2OsO4/NMO instead of AD-mix β, and excluding the use of methylsulfonate specified in the title compound obtained as a beige solid (5.75 g, 93%yield) after crystallization from CRIME.

1H NMR (CDCl3) δ: 8,01 (d, J=9.1 Hz, 1H), 7,58 (m, 1H), 7,50 (m, 1H), 6,97 (m. 1H), of 5.53 (m, 1H), 4,07 (s, 3H), 3,91 (m, 2H).

BE.v. rat-1-(7-Bromo-2-methoxyquinoline-8-yl)-2-(tert-butyldimethylsilyloxy)ethanol

On the basis of the intermediate compound (BE.iv) (5,70 g) and using method M that is listed in the title compound obtained as a brown oil (7,79 g, 99%yield).

1H NMR (CDCl3) δ: of 7.97 (d, J=8,8 Hz, 1H), 7,55 (m, 1H), 7,45 (m, 1H), 6,93 (d, J=8,8 Hz, 1H), 5,54 (t, J=5.6 Hz, 1H), 4,12 (m, 1H), Android 4.04 (s, 3H), 3,98 (m, 1H), 0.75 in (m, 9H), -0,14 (d, J=0.9 Hz, 6N).

BE.vi. rat-1-(7-Bromo-2-methoxyquinoline-8-yl)-2-(tert-butyldimethylsilyloxy)ethylamine

On the basis of the intermediate compound (BE.v) (7,75 g) specified in the header connection receive similar synthetic method of the Z stage Z.iv, in the form of a yellow oil (2.6 g; 33%yield).

MS (ESI, m/z): 411,3 [M+H+].

BE.vii. tert-Butyl ether rat-[1-(7-bromo-2-methoxyquinoline-8-yl)-2-(tert-butyldimethylsilyloxy)ethyl]carbamino acid

On the basis of the intermediate compound (BE.vi) (2,60 g) using method G, specified in the title compound obtained as a yellow oil (3,20 g, 99%yield).

1H NMR (CDCl3) δ: of 7.95 (d, J=9.1 Hz, 1H), 7,55 (m, 1H), 7,44 (m, 1H), 6,92 (d, J=9.1 Hz, 1H), 6.35mm (m, 1H), equal to 4.97 (m, 1H), 4,06 (m, 3H), a 4.03 (m, 1H), 3,74 (m, 1H), 1,25 (m, 9H), 0.75 in (s, 9H), -0,11 (s, 6H).

BE.viii. tert-Butyl ether rat-[1-(7-bromo-2-methoxyquinoline-8-yl)-2-hydroxyethyl]carbamino acid

On the basis of the intermediate compound (BE.vii) (3,20 g) and using method J, specified in the title compound obtained as off-white solid (1.70 g, 68%-PY output).

1H NMR (CDCl3) δ: 7,98 (d, J=9.1 Hz, 1H), 7,60 (m, 1H), 7,49 (m, 1H), of 6.96 (d, J=8,8 Hz, 1H), of 5.92 (m, 1H), 4,08 (m, 4H), a 4.03 (m, 2H), of 1.44 (s, 9H).

BE.ix. tert-Butyl ether rat-(9-bromo-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid:

On the basis of the intermediate compound (BE.viii) (400 mg) and using the same method described for intermediate compounds (Z.vi)specified in the title compound obtained as yellow solid (372 mg, 100%yield).

1H NMR (CDCl3) δ: to 7.67 (d, J=9.4 Hz, 1H), 7,32 (m, 2H), of 6.68 (m, 1H), 5,58 (m, 1H), equal to 4.97 (m, 1H), with 4.64 (m, 1H), 4,32 (m, 1H), 1,24 (m, 9H).

MS (ESI, m/z): 365,3 [M+H+].

Veh rat-1-Amino-9-bromo-,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BE.ix) (100 mg) and using the method specified in the title compound obtained as off-white solid (52 mg, 72%yield).

1H NMR (CDCl3) δ: to 7.67 (d, J=9.7 Hz, 1H), 7,33 (m, 2H), of 6.68 (d, J=9.7 Hz, 1H), 4,89 (dd, J=8,8, 3.5 Hz, 1H), to 4.62 (dd, J=13,5, 8.5 Hz, 1H), 4,17 (dd, J=13,5, and 3.8 Hz, 1H), 1,80 (m, 2H).

Experimental method BF: Ethyl ester of (R)-1-amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid

BF.i. Ethyl ester of 2-methoxy-8-vinylphenol-5-carboxylic acid

The solution of the complex of the anhydride vinylboronic acid with pyridine (1:1 ratio; 3,81 g) in DMF (240 ml) is treated with tetrakis-(triphenylphosphine)palladium(0) (731 mg) and stirred under nitrogen atmosphere for 20 minutes Then the reaction mixture was sequentially treated To a2CO3(4,372 g), water (73 ml) and ethyl ether 2-methoxy-8-[[(trifluoromethyl)sulfonyl]oxy]-5-quinoline-carboxylic acid (12.0 g; obtained similarly to the corresponding n-butyl ester according to the description in WO 2006/046552), and then stirred at a temperature of 85°C during the night. The reaction mixture is then diluted with water and extracted with ether. The organic layer is dried over MgSO4concentrate without dried and purified by column chromatography (hexane/EA, in the ratio 4:1)to give a yellow oil (of 5.40 g; 66%yield).

1H NMR (CDCl3 ) δ: 9,20 (d, J=9.1 Hz, 1H), 8,08 (dd, J=7,9, 0.6 Hz, 1H), of 7.96 (dd, J=18.2, and to 11.1 Hz, 1H), 7,86 (d, J=7.9 Hz, 1H), 7,02 (d, J=9.4 Hz, 1H), equal to 6.05 (dd, J=18.2, and 1.5 Hz, 1H), 5,54 (dd, J=11,1,1,5 Hz, 1H), of 4.45 (q, J=7,3 Hz, 2H), 4,10 (s, 3H), of 1.45 (t, J=7.0 Hz, 3H).

BF.ii. Ethyl ester 8-((S)-1,2-dihydroxyethyl)-2-methoxyaniline-5-carboxylic acid

A solution of intermediate compound (BF.i) (5,40 g) dihydroxyaryl in the presence of AD-mix α, using method L. After crystallization from ether, the product is obtained as white solids (4,30 g; 70%yield; the enantiomeric excess was not determined, the yield is 100%).

1H NMR (DMSO d6) δ: 9,05 (d, J=9.4 Hz, 1H), 8,04 (m, 1H), 7,87 (d, J=7.9 Hz, 1H), 7,15 (d, J=9.4 Hz, 1H), to 5.66 (m, 1H), 5,35 (m, 1H), 4,67 (m, 1H), 4,37 (q, J=7,0 Hz, 2H), 4.00 points (s, 3H), 3,79 (m, 1H), 3.43 points (m, 1H), of 1.35 (t, J=7,3 Hz, 3H).

BF.iii. Ethyl ester of 8-[(S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-2-methoxyaniline-5-carboxylic acid

On the basis of the intermediate compound (BF.ii) (4,20 g) and using method M that is specified in the header of the intermediate compound obtained as a yellow oil (5,48 g; 94%yield).

MS (ESI, m/z): 406,2 [M+H+].

BF.iv. Ethyl ester of 8-[(R)-1-tert-butoxycarbonylamino-2-(tert-butyldimethylsilyloxy)ethyl]-2-methoxyaniline-5-carboxylic acid

A solution of intermediate compound (BF.iii) (5.30 g) and PPh3(4.11 g) in THF (130 ml) cooled to 0°C and added dropwise, DFFA (3.4 ml) and DYADS (3,36 ml). The reaction mixture was stirred at the rate which the temperature 0°C for 15 min, and then at room temperature for 1.5 h, evaporated without dried and purified by column chromatography (heptane/EA in the ratio 2:1), obtaining the intermediate azide as a yellow oil (6.0 g)which is dissolved in a mixture of THF/water (in the ratio of 9:1; 50 ml), treated with PPh3(4.1 g) and stirred at 50°C for 1.5 h, the Reaction mixture is then injected into the reaction Side2Of (5.7 g) and stirred at room temperature for 2 days, after which the reaction mixture is concentrated under reduced pressure and purified by column chromatography (heptane/EA ratio from 9:1 to 4:1)to give a yellow oil (9,20 g; polluted by Side2O).

1H NMR (CDCl3) δ: of 9.21 (d, J=9.4 Hz, 1H), with 8.05 (d, J=7.9 Hz, 1H), to 7.59 (d, J=7,6 Hz, 1H), 7,01 (d, J=9.4 Hz, 1H), 5,64 (t, J=4,7 Hz, 1H), of 4.44 (q, J=7,0 Hz, 2H), 4,07 (m, 5H), 1,50 (m, 3H), of 1.44 (s, 9H), 0.76 to (s, 9H), -0,23 (m, 6H).

BF.v. Ethyl ester 8-((R)-1-tert-butoxycarbonylamino-2-hydroxyethyl)-2-methoxyaniline-5-carboxylic acid

On the basis of the intermediate compound (BF.iv) (6,56 g) and using method J, specified in the header of the intermediate compound obtained as colorless solids (2,60 g; 51%yield).

1H NMR (CDCl3) δ: which 9.22 (d, J=9.4 Hz, 1H), of 8.06 (d, J=7,6 Hz, 1H), 7.62mm (d, J=7.9 Hz, 1H),? 7.04 baby mortality (d, J=9.4 Hz, 1H), of 5.55 (m, 1H), of 4.44 (q, J=7,3 Hz, 2H), a 4.03 (m, 5H), of 1.44 (s, 9H).

BF.vi. Ethyl ester of (R)-1-tert-butoxycarbonylamino-4-ox is -1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid

On the basis of the intermediate compound (BF.v) (2,40 g) and using method H, specified in the header of the intermediate compound obtained as a colorless solid after trituration with ether (2.10 g; 95%yield).

MS (ESI, m/z): 359,2 [M+H+].

BF.vii. Ethyl ester of (R)-1-amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid

On the basis of the intermediate compound (BF.vi) (1,00 g) and using the method specified in the title compound obtained as a beige solid (690 mg; 96%yield).

MS (ESI, m/z): 259,2 [M+H+].

Experimental method BG: (R)-1-Amino-7-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BG.i. tert-Butyl ester ((R)-7-hydroxymethyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (BF.vi) (250 mg) and using the method As specified in the header of the intermediate compound obtained as a yellowish solid after trituration with ether (190 mg; 86%yield).

MS (ESI, m/z): 317,2 [M+H+].

BG.ii. (R)-1-Amino-7-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BG.i) (180 mg) and using the method specified in the title compound separated from the aqueous phase (after evaporation without dried) and suspension in DHM/Meon (in the ratio 9:1)to give 400 mg of a beige solid (zagryazneniemenee salts). The resulting substance is used in the following stages without any treatment.

1H NMR (DMSO-d6) δ: 8,10 (d, J=9.7 Hz, 1H), 7,65 (d, J=7,6 Hz, 1H), 7,27 (d, J=7,6 Hz, 1H), is 6.61 (d, J=9.7 Hz, 1H), 5,41 (m, 1H), 5.19 (m, 1H), 4,79 (m, 2H), 4,55 (dd, J=13,5, 8.5 Hz, 1H), 4,22 (dd, J=13,5, and 3.2 Hz, 1H), 4,07 (ddd, J=3.2, and to 2.1, 0.9 Hz, 1H).

Experimental method NR: (R)-1-Amino-7-dimethylaminomethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BH.i. tert-Butyl ester ((R)-7-formyl-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A solution of intermediate compound (BG.i) (640 mg) in a mixture DHM/THF (40 ml; in the ratio 2:1) is stirred in the presence of MnO2(3.75 g) for 30 min, after which the reaction mixture is filtered through Celite® and the filtrate is evaporated without dried. The residue is triturated with a mixture of ether/heptane, receiving a yellow solid (480 mg; 75%yield).

1H NMR (CDCl3) δ: 10,19 (s, 1H), 8,84 (d, J=9.7 Hz, 1H), 7,69 (m, 2H), for 6.81 (d, J=9.7 Hz, 1H), to 5.66 (m, 1H), 5,11 (m, 1H), 4,74 (dd, J=13,8, and 9.1 Hz, 1H), 4,25 (m, 1H), 1,45 (m, 9H).

BH.ii. tert-Butyl ester ((R)-7-dimethylaminomethyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (BH.i) (200 mg) and NHMe2(0,11 ml; 5,6-molar solution in EtOH) and using method E, specified in the header of the intermediate compound obtained as yellow solid (140 mg, 64%yield).

MS (ESI, m/z): 344,6 [M+H+].

BH.iii. (R)-1-Amino-7-dimethyl isomethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BH.ii) (140 mg) and using the method specified in the title compound obtained as an orange oil (74 mg, 76%yield).

MS (ESI, m/z): 244,3 [M+H+].

Experimental method BI: (R)-1-Amino-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BI.i. tert-Butyl ester ((R)-4-oxo-7-pyrrolidin-1-ylmethyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid.

On the basis of the intermediate compound (BH.i) (200 mg) and pyrrolidine (52 μl) and using method E, specified in the header of the intermediate compound obtained as yellow solid (190 mg; 80%yield).

MS (ESI, m/z): 370,4 [M+H+].

BI.ii. (R)-1-Amino-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BI.i) (190 mg) and using the method specified in the title compound obtained as an orange oil (100 mg; 72%yield).

MS (ESI, m/z): 269, [M+H+].

Experimental method BJ: 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]Propionaldehyde

Specified in the header connection receive similar experimental method AR on the basis of (S)-2-{2-[(tert-butyldimethylsilyloxy]propyl}-oxirane, with the same outputs and identical analytical data (MS,1H NMR).

Experimental method VK: 3-[(R)-2-Oxo-3-(3-oxo-3,4-is ihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

BK.i. Ethyl ester of (2-tert-butoxycarbonylamino-6-chloropyridin-3-ylsulphonyl)acetic acid

To a solution of TMEDA (1,677 ml) in THF (20 ml), cooled to a temperature of -20°C., added dropwise 2,3-molar solution of n-BuLi and 4.75 ml). After stirring at this temperature for 20 min the solution was cooled to a temperature to -78°C, treated, adding dropwise a solution of 2-tert-butoxycarbonylamino-6-chloropyridine (1,14 g; commercial product) in THF (7.5 ml). The solution is stirred at this temperature for 1 h and treated with sulfur (S8). After stirring at this temperature for 20 min, the reaction mixture is treated with ethylbromoacetate (0,86 ml), then stirred for 2 h at -78°C and leave spontaneously heat up to a temperature of -45°C and then quenched with ethyl acetate and water. The organic phase is successively washed with 1 normal HCl solution, a concentrated aqueous solution of NH4Cl and brine, dried over MgSO4and the solvent is evaporated. The residue is purified by column chromatography (heptane/EA ratio from 4:1 to 2:1)to give colorless oil (1,05 g; 60%yield).

1H NMR (CDCl3) δ: 8,01 (s, 1H), 7,79 (d, J=8,2 Hz, 1H), 6,98 (d, J=8,2 Hz, 1H), 4,14 (q, J=7.0 Hz, 3H), 3,47 (s, 2H), and 1.54 (s, 12H), 1.22 (t, J=7.0 Hz, 3H).

BK.ii. 6-Chloro-4H-pyrido[3,2-b][1,4]thiazin-3-one

A solution of intermediate compound(BK.i) (1.0 g) in DHM (6 ml) was stirred at room temperature overnight in the presence of TFA (6 ml). The reaction mixture is evaporated without dried, the residue is dissolved in EtOH and heated under reflux for 2 days. The reaction mixture is again evaporated without dried, and the residue is transferred into ethyl acetate and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried over MgSO4concentrate under reduced pressure and crystallized from a mixture of ether/heptane, receiving a yellow solid (400 mg, 69%yield).

1H NMR (CDCl3) δ: 8,28 (d, J=1.5 Hz, 1H), EUR 7.57 (dd, J=8,2, 0.6 Hz, 1H), 6,98 (d, J=8,2 Hz, 1H), 3,50 (m, 2H).

BK.iii. 6-{(R)-5-[3-(tert-Butyldimethylsilyloxy)propyl]-2-oxoacridine-3-yl}-4H-pyrido[3,2-b][1,4]thiazin-3-one

In the ampoule download intermediate connection (BK.ii) (2 g), palladium(II)acetate (224 mg), DPEphos (1.08 g), rejonowy potassium phosphate (powdered; 4,33 g) and intermediate compound (AR.ii) (3.1 g). Then add dioxane (dried over molecular sieves, 50 ml) with a syringe and through the resulting suspension for 5 min bubbled argon. The mixture was then heated in a sealed vessel at a temperature of 80°C during the night. The residue is extracted with a mixture of ethyl acetate/water. The organic layer was washed with brine, dried over MgSO4and concentrate. The residue is purified by column chromatography (heptane/EA in the ratio 2:1, 1:1)to give a yellowish solid (3.58 g; 84%yield).

H NMR (DMSO-d6) δ: 10,81 (s, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 4,71 (m, 1H), 4,20 (m, 1H), 3,69 (dd, J=10,5, 7,3 Hz, 1H), 3,62 (t, J=6.4 Hz, 2H), 3,51 (s, 2H), 1,74 (m, 2H), and 1.56 (dd, J=9,4, 7,3 Hz, 2H), 0,85 (m, 9H), 0,02 (s, 6H).

BK.iv. 6-[(R)-5-(3-Hydroxypropyl)-2-oxoacridine-3-yl]-4H-pyrido[3,2-b][1,4]thiazin-3-OI

On the basis of the intermediate compound (BK.iii) (3.58 g) and using method J, specified in the header of the intermediate compound obtained as a colorless solid (2.0 g; 76%yield).

1H NMR (DMSO-d6) δ: 10,83 (s, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 4,70 (m, 1H), 4,48 (t, J=5.3 Hz, 1H), 4,20 (m, 1H), 3,70 (dd, J=10,3, 7,0 Hz, 1H), 3,51 (s, 2H), 3.43 points (q, J=6.2 Hz, 2H), or 3.28 (s, 3H), of 1.75 (m, 2H)and 1.51 (m, 2H).

BK.v. 3-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

On the basis of the intermediate compound (BK.iv) (250 mg) and using the experimental method U, stage U.iv specified in the title compound obtained as a colorless solid (200 mg; 80%yield).

MS (ESI, m/z): 308,3 [M+H+].

Experimental method BL: 3-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde

Specified in the header connection receive similar experimental method VC on the basis of (S)-2-[2-[[(tert-butyl)dimethylsilane]oxy]propyl]-oxirane, with similar outputs and identical analytical data (MS,1H NMR).

Experimental method the VM: (R)-4-Amino-3-fluoro-4,5-dihydropyrrolo[3,21-de][1,5]naphthiridine-7-he

BM.i. rat-1-(3-Fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethane-1,2-diol

On the basis of the intermediate compound (Ax.i) (was 12.75 g) is similar experimental method AH, stage AX.ii, using the K2OsO4/N-MO instead of AD-mix β and excluding methylsulfonate specified in the title compound is isolated in the form of a light brown solid (9.80 g; 66%yield).

MS (ESI, m/z): 238,4 [M+H+].

BM.ii. rat-2-(tert-Butyldimethylsilyloxy)-1-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethanol

On the basis of the intermediate compound (BM.i) (12,35 g) and using method M that is specified in the header of the intermediate compound obtained as a brown oil (18,85 g; 100%yield).

MS (ESI, m/z): 353,4 [M+H+].

BM.iii. rat-8-[1-Azido-2-(tert-butyldimethylsilyloxy)ethyl]-7-fluoro-2-methoxy[1,5]naphthiridine

On the basis of the intermediate compound (BM.ii) (18,85 g) and using the method of N indicated in the header of the intermediate compound obtained as an orange oil (22,2 g; contaminated PPh3O).

1H NMR (CDCl3) δ: 8,66 (d, J=1.5 Hz, 1H), to 8.20 (d, J=9.1 Hz, 1H), 7,11 (d, J=9.1 Hz, 1H), to 5.85 (m, 1H), 4,36 (m, 1H), 4,11 (m, 3H), Android 4.04 (m, 1H), 0,87 (s, 9H), 0,06 (d, J=8,8 Hz, 6N).

BM.iv. rat-2-Azido-2-(3-fluoro-6-methoxy[1,5]naphthiridine-4-yl)ethanol

On the basis of the intermediate compound (BM.iii) (20,0 g) and using method J, specified in the header of the intermediate compound obtained as a yellowish solid (13,g; 99%yield).

1H NMR (CDCl3) δ: 8,69 (m, 1H), 8,23 (dd, J=9,1, 0.9 Hz, 1H), 7,13 (d, J=9.1 Hz, 1H), of 5.92 (dd, J=7,9, 4,7 Hz, 1H), 4,29 (m, 1H), 4,11 (m, 3H), 4,06 (d, J=4.4 Hz, 1H), 1,25 (m, 1H).

BM.v. rat-4-Azido-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the intermediate compound (BM.iv) (17,75 g) and using method H, specified in the header of the intermediate compound obtained as orange solids (7,94 g; 51%yield).

1H NMR (CDCl3) δ: 8,45 (m, 1H), 7,88 (m, 1H), 6,84 (m, 1H), to 5.66 (dd, J=8,5, 3.5 Hz, 1H), to 4.62 (dd, J=13,8, 8.5 Hz, 1H), 4,35 (dd, J=13,8, 3.5 Hz, 1H).

BM.vi. (R)-4-Amino-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

A solution of intermediate compound (BM.v) (7,93 g) in THF (140 ml) is stirred at 60°C for 3 h in the presence of PPh3(9,90 g) and water (6,17 ml). The reaction mixture is concentrated without dried and the residue purified by column chromatography (DHM/Meon/NH4OH in a ratio of from 1000:50:4 to 1000:100:8)to give after stirring in TBME (RS)-4-amino-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he (6,37 g; 91%yield). This racemic product (6,22 g) separated using preparative chiral HPLC using a 5 μm (R,R)-Whelk-01 column (50×250 mm) and elwira mixture (in the ratio 4:1) MeCN-EtOH containing 0.1% diethylamine, with tR=to 5.21 min for named the title compound (compound of the experimental method VMS) and tR=6,13 min for optical ant the hearth (the connection of the experimental method BN). Selected 3.00 g (first eluruumis enantiomer, compound experimental method VM, 100% EE) and of 2.92 g (second eluruumis enantiomer, compound experimental method, BN, 100% EE).

The absolute configuration named in the title compounds were determined by x-ray analysis of the corresponding carboxamide, obtained from (S)-almond acid.

MS (ESI, m/z): 206,1 [M+H+].

Experimental method BN: (S)-4-Amino-3-fluoro-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Specified in the title compound obtained as the second aliremove enantiomer (tR=6,13 min) the experimental method VM, stage BM.vi.

MS (ESI, m/z): 206,1 [M+H+].

Experimental method: rat-1-Amino-9-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

VA. (7-Bromo-2-methoxyquinoline-8-yl)methanol

A suspension of 7-bromo-8-methyl bromide-2-methoxyaniline (35.2 g; obtained according to WO 2007/081597) and NaHCO3(14,63 g) in acetone (430 ml) and water (430 ml) is heated under reflux for 6 hours the Organic solvent is removed under reduced pressure, after which the aqueous layer was extracted twice with ethyl acetate. The combined organic layers are successively washed with water and brine and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is crystallized from CRIME, getting dirty-white is e solid (16,01 g; 56%yield).

MS (ESI, m/z): 268,0 [M+H+].

BO.ii. 7-Bromo-2-methoxypoly-8-carbaldehyde

The solution oxalicacid (5,68 ml) in DHM (265 ml), cooled down to -78°C, treated, adding dropwise, a solution of DMSO (5,71 ml) in DHM (50 ml). The resulting solution is treated with a solution of the intermediate (VA) (6,00 g) in DHM (50 ml). After stirring for 1 h at a temperature of -78°C. the reaction mixture is treated with a solution of tea (and 23.4 ml) in DHM (50 ml) and left to spontaneously warm to room temperature. The reaction mixture is treated then saturated aqueous NaHCO3(300 ml) and the organic layer separated and dried over Na2SO4. The solvent is evaporated under reduced pressure and the crude product is stirred with TBME, receiving a yellow solid (4.68 g; 79%yield; contaminated with traces of the original substance).

MS (ESI, m/z): 266,0 [M+H+].

BO.iii. 7-Bromo-2-methoxy-8-vinylphenol

On the basis of the intermediate compound (BO.ii) (500 mg) and bromide methyltriphenylphosphonium (1.01 g), using the experimental method Z stage Z.i specified in the title compound obtained as a colorless solid (411 mg; 83%yield).

MS (ESI, m/z): 264,3 [M+H+].

.iv. rat-1-(7-Bromo-2-methoxyquinoline-8-yl)ethane-1,2-diol

On the basis of the intermediate compound (BO.iii) (5.50 g) similarly syntheti is dedicated method AH, stage AX.ii, but using the K2OsO4/N-MO instead of AD-mix β and excluding methylsulfonate specified in the title compound obtained as a beige solid (5.75 g; 93%yield).

1H NMR (CDCl3) δ: 8,01 (d, J=9.1 Hz, 1H), 7,58 (m, 1H), 7,50 (m, 1H), 6,97 (m, 1H), of 5.53 (m, 1H), 4,07 (m, 3H), 3,91 (m, 2H).

BO.v. rat-1-(7-Bromo-2-methoxypoly-8-yl)-2-(tert-butyldimethylsilyloxy)ethanol

On the basis of the intermediate compound (BO.iv) (5,71 g) and using method M that is listed in the title compound obtained as a brown oil (7,79 g; 99%yield).

1H NMR (CDCl3) δ: of 7.97 (d, J=8,8 Hz, 1H), 7,55 (m, 1H), 7,45 (m, 1H), 6,93 (d, J=8,8 Hz, 1H), 5,54 (t, J=5.6 Hz, 1H), 4,12 (m, 1H), Android 4.04 (s, 3H), 3,98 (m, 1H), 0.75 in (m, 9H), -0,14 (d, J=0.9 Hz, 6N).

BO.vi. rat-8-[1-Azido-2-(tert-butyldimethylsilyloxy)ethyl]-7-bromo-2-methoxyquinoline

On the basis of the intermediate compound (BO.v) (of 7.75 g) and using the method of N indicated in the header of the intermediate compound obtained as a yellow oil (of 8.47 g; 100%yield).

MS (ESI, m/z): 437,2 [M+H+].

BO.vii. rat-1-(7-Bromo-2-methoxyquinoline-8-yl)-2-(tert-butyldimethylsilyloxy)ethylamine

On the basis of the intermediate compound (BO.vi.) (8,45 g), similar to the experimental method VM, stage BM.vi specified in the header of the intermediate compound obtained as a yellow oil (2,60 g; 33%yield).

MS (ESI, m/z): 411,3 [M+H+].

BO.viii. tert-Butyl ether rat-[1-(7-bromo-2-metoxy the Olin-8-yl)-2-(tert-butyldimethylsilyloxy)ethyl]carbamino acid

On the basis of the intermediate compound (BO.vii) (2,60 g) using method G, specified in the header of the intermediate compound obtained as a yellow oil (3,20 g; 99%yield).

1H NMR (CDCl3) δ: of 7.95 (d, J=9.1 Hz, 1H), 7,55 (m, 1H), 7,44 (m, 1H), 6,92 (d, J=9.1 Hz, 1H), 6.35mm (m, 1H), equal to 4.97 (m, 1H), 4,06 (m, 3H), a 4.03 (m, 1H), 3,74 (m, 1H), 1,25 (m, 9H), 0.75 in (s, 9H), -0,11 (s, 6N).

BO.ix. tert-Butyl ether rat-[1-(7-bromo-2-methoxyquinoline-8-yl)-2-hydroxyethyl]carbamino acid

On the basis of the intermediate compound (BO.viii) (3,20 g) and using method J, specified in the header of the intermediate compound obtained as off-white solid (1.70 g; 68%yield).

MS (ESI, m/z): 396,9 [M+H+].

VOH tert-Butyl ether rat-(9-bromo-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (BO.ix) (400 mg) and using method H, specified in the header of the intermediate compound obtained as yellow solid (372 mg, 100%yield).

MS (ESI, m/z): 365,3 [M+H+].

BO.xi. tert-Butyl ether rat-(9-methyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A solution of intermediate compound (VOH) (90 mg) in DME (1.5 ml) is treated with tetrakis-(triphenylphosphine)palladium, and the solution was rinsed with N2and then treated To a2CO3(34 mg), water (0.5 ml) and trimethylboroxine (25 mg) and stirred at tempera is ur 80°C during the night. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic layer is successively washed with water, brine and dried over MgSO4. The solvent is removed under reduced pressure and the residue purified by column chromatography (EA)to give a colorless solid (82 mg, 100%yield).

MS (ESI, m/z): 301,2 [M+H+].

BO.xii. rat-1-Amino-9-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BO.xi) (81 mg) and using the method specified in the title compound obtained as a gray solid (34 mg; 79%yield).

MS (ESI, m/z): 201,5 [M+H+].

Experimental method BP: rat-4-[2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Butyraldehyde

BP.i. rat-6-[6-(tert-Butyldimethylsilyloxy)-2-hydroxyacetylamino]-4H-benzo[1,4]thiazin-3-one

A solution of 2-[4-[(tert-butyl)dimethylsiloxy]butyl]oxirane (10.0 g) and 6-amino-4H-benzo[1,4]thiazin-3-one (7,81 g; commercial product) in a mixture of EtOH/water (300 ml; in the ratio 9:1) is heated under reflux for 2 days. The solvents are then removed under reduced pressure and the residue is transferred into a mixture of EA/hexane (at a ratio of 1:1; 100 ml) and filtered. The filtrate is concentrated under reduced pressure and purified by column chromatography (EA/hexane; 1:1 ratio)to give an orange solid vases is in (7,40 g; 42%yield).

MS (ESI. m/z): 411,3 [M+H+].

BP.ii. rat-6-{5-[4-(tert-Butyldimethylsilyloxy)butyl]-2-oxoacridine-3-yl}-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (BP.i) (7.30 g) and using the method I mentioned in the title intermediate compound obtained as colorless solids (4,40 g; 79%yield).

MS (ESI, m/z): 437,4 [M+H+].

BP.iii. rat-6-[5-(4-Hydroxybutyl)-2-oxoacridine-3-yl]-4H-benzo[1,4]thiazin-3-one

On the basis of the intermediate compound (BP.ii) (4,40 g) and using method J, specified in the header of the intermediate compound obtained as a colorless solid (3.00 g; 92%yield).

MS (ESI, m/z): 323,4 [M+H+].

BP.iv. rat-4-[2-Oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Butyraldehyde

On the basis of the intermediate compound (BP.iii) (3.0 g) and using the experimental method U, stage U.iv specified in the header of the intermediate compound obtained as a colorless solid (2.30 g; 77%yield).

MS (ESI, m/z): 321,3 [M+H+].

Experimental method: Methyl ether rat-(1R*,2R*)-1-amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

BQ.i. Methyl ester (E)-3-(2-methoxyquinoline-8-yl)acrylic acid

A solution of 8-bromo-2-methoxyquinoline (10.0 g), Pd(OAc)2(311 mg), P(o-Tol)3(1.28 g) in DMF (100 ml) is treated with the tea (17.6 ml) and methylacrylate the (18,93 ml). The solution is rinsed three times with nitrogen and stirred at a temperature of 120°C for 1 h, the Reaction mixture was diluted with water (200 ml) and extracted with a mixture of ether/EA. The organic layer was washed with water (three times 200 ml) and brine and dried over MgSO4. The solvent is removed under reduced pressure and the residue purified by column chromatography (heptane/EA ratio 4:1)to give pale yellow solid (9,34 g; 91%yield).

1H NMR (CDCl3) δ: 8,00 (d, J=9.1 Hz, 1H), 7,66 (dd, J=7,9, 1.5 Hz, 1H), EUR 7.57 (d, J=6,7 Hz, 1H), was 7.36 (m, 1H), 6,92 (d, J=8,8 Hz, 1H), 6,24-6,05 (m, 2H), 4,84 (m, 1H), 4,10 (s, 3H), with 3.89 (d, J=5.0 Hz, 1H), of 3.78 (s, 3H), was 1.43 (m, 9H).

VA. Methyl ester of (2S*,3R*)-3-tert-butoxycarbonylamino-2-hydroxy-3-(2-methoxyquinoline-8-yl)propionic acid

A solution of tert-BUTYLCARBAMATE (7,06 g) in n-propanol (120 ml) was sequentially treated with 0.4-molar aqueous solution of NaOH (218 ml) and tert-butylhypochlorite a (10.6 ml, freshly prepared as described in Org. Lett. (2003), 5(12), 2123-2126 (S-2)). The reaction mixture is treated then the solution of (DHQD)2PHAL (565 mg) and (DHQ)2PHAL (565 mg) in n-propanol (100 ml)over 5 min, cooled to a temperature of 10°C. and sequentially treated with a suspension of intermediate compounds (BQ.i) (7,07 g) in a mixture of water/n-propanol (1:1 ratio; 140 ml) and the osmate dihydrate(VI) potassium (428 mg). After stirring at a temperature of +10°C for 20 min, the reaction mixture formation is anywayt Na 2SO3(15 g) and then stirred at room temperature for 10 min, after which the reaction mixture is extracted with ethyl acetate and the organic layer is successively washed with 5%aqueous solution of K2CO3, saturated aqueous NaHCO3and brine. After drying over MgSO4and evaporation of the solvent the residue is purified by column chromatography (mixture DHM/Meon in the ratio of 10:1 containing 1% NH4OH), while receiving specified in the title compound as a pale yellow foam (6.85 g; 63%yield).

MS (ESI, m/z): 377,6 [M+H+].

BQ.iii. Methyl ether rat-(1R*,2R*)-1-tert-butoxycarbonylamino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

On the basis of the intermediate compound (BQ.ii) (7,80 g) and using method H, specified in the header of the intermediate compound obtained as colorless solids (6,24 g; 87%yield).

MS (ESI, m/z): 345,5 [M+H+].

BQ.iv. Methyl ether rat-(1R*,2R*)-1-amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

On the basis of the intermediate compound (BQ.iii) (1,00 g) and using the method specified in the title compound obtained as a colorless solid (684 mg; 96%yield).

MS (ESI, m/z): 245,2 [M+H+].

Experimental method BR: rat-(1R*,2R*)-1-Amino-2-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]Hino is in-4-one

BR.i. tert-Butyl ether rat-((1R*,2R*)-2-hydroxymethyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (BQ.iii) (3,20 g) and using the method As specified in the header of the intermediate compound obtained as a colorless solid (2.67 g; 91%yield).

MS (ESI, m/z): 317,3 [M+H+].

BR.ii. rat-(1R*,2R*)-1-Amino-2-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of intermediate compounds (BR ii) (600 mg) and using the method specified in the title compound obtained as a colorless oil (400 mg, 98%yield).

MS (ESI, m/z): 217,3 [M+H+].

Experimental method BS: rat-(1R*,2R*)-1-Amino-2-methoxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BS.i. tert-Butyl ether rat-((1R*,2R*)-2-methoxymethyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A solution of intermediate compound (BR.i) (400 mg) in THF (anhydrous; 4 ml) is treated at a temperature of 0°C. NaH (60%dispersion in oil; 51 mg). After a few minutes the reaction mixture was treated with MeI (83 μl) and stirred at room temperature for 30 min, then treated with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over MgSO4. The solvent is evaporated under reduced pressure and the residue is purified is by column chromatography (DHM/Meon/NH 4OH in the ratio of 1000:50:4)to give a pale yellow solid (42 mg, 10%yield).

MS (ESI, m/z): 331,2 [M+H+].

BS.ii. rat-(1R*,2R*)-1-Amino-2-methoxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BS.i) (42 mg) and using the method specified in the title compound obtained as a pale yellow oil (28 mg; 96%yield).

MS (ESI, m/z): 231,2 [M+H+].

Experimental method W: rat-(1R*,2S*)-1-Amino-2-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BT.i. tert-Butyl ether rat-((1R*,2R*)-2-methyl-4-oxo-1,2-dihydro-4-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (BR.i) (800 mg) and using method H, receive intermediate mesilate, which is then injected into the reaction after conventional treatment. It is dissolved in DME (45 ml) and heated under reflux in the presence of NaI (1,21 g). After 1.5 h, the reaction mixture is treated with Bu3SnH (3 ml), then heated under reflux for 3 h, diluted with ether and stirred in the presence of an 8%aqueous solution of KF for 16 hours the Mixture is filtered, the phases are separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers washed with water and brine and dried over MgSO4. The solvents are removed under reduced pressure and the residue purified by column chromatography (heptane/EA in aspect] is to 1:1), getting a colourless solid (476 mg, 63%yield).

MS (ESI, m/z): 301,3 [M+H+].

BT.ii. rat-(1R*,2S*)-1-amino-2-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BT.i) (467 mg) and using the method specified in the title compound obtained as a yellow oil (274 mg; 88%yield).

MS (ESI, m/z): 201,3 [M+H+].

Experimental method BU: rat-(1R*,2R*)-1-Amino-2-(1-hydroxy-1-methylethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BU.i. tert-Butyl ether rat-[(1R*,2R*)-2-(1-hydroxy-1-methylethyl)-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl]carbamino acid

Solution (BQ.iii) (422 mg) in THF (anhydrous; 8 ml) is treated by adding dropwise, at a temperature of 0°C. MeMgBr (1,4-molar solution in a mixture of toluene/THF in a ratio of 3:1; 3,1 ml). After stirring for 2 h at 0°C, the reaction mixture is left to spontaneously warm to room temperature and treated with MeMgBr (1,4-molar solution in a mixture of toluene/THF in a ratio of 3:1; 5 ml). The reaction mixture was then stirred at room temperature overnight, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic layer is successively washed with water and brine and dried over MgSO4. The solvent is evaporated under reduced pressure and the residue purified by column chromatography (DHM/EON/NH 4OH in the ratio of 1000:50:4)to give a pale yellow foam (74 mg, 17%yield).

MS (ESI, m/z): 345,5 [M+H+].

BU.ii. rat-(1R*,2R*)-1-Amino-2-(1-hydroxy-1-methylethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BU.i) (74 mg) and using the method specified in the title compound obtained as a brown oil (22 mg, 42%yield).

MS (ESI, m/z): 245,3 [M+H+].

Experimental method BV: rat-1-Amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile

BV.i. tert-Butyl ether rat-(9-cyano-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A mixture of intermediate compound (BE.ix) (135 mg), Zn(CN)2(52 mg) and Pd(PPh3)4(21 mg) in DMF (2 ml) is heated at 110°C overnight in an argon atmosphere in a sealed vessel. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over MgSO4. The solvent is removed under reduced pressure and the residue triturated with TBME, getting a pinkish solid (88 mg, 76%yield).

MS (ESI, m/z): 312,3 [M+H+].

BV.ii. rat-1-Amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile

On the basis of the intermediate compound (BV.i) (88 mg) and using the method specified in the title compound obtained as bescoto the solid (57 mg, 95%yield).

MS (ESI, m/z): 212,1 [M+H+].

Experimental method BW: (R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ymetray ether methanesulfonate acid

BW.i. 6-[(R)-5-(tert-Butyldimethylsilyloxy)-2-oxoacridine-3-yl]-4H-pyrido[3,2-b][1,4]thiazin-3-one

On the basis of (5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2-oxazolidinone (1.20 g; obtained as described in Org. Letters (2005), 7, 1983-1985) and intermediate (BK.ii) (867 mg) specified in the header connection receive similar intermediate compounds (BK.iii) after processing by means of column chromatography (heptane/EA in the ratio 1:1) as a beige solid (1.20 g; 70%yield).

1H NMR (CDCl3) δ: of 7.90 (d, J=8.5 Hz, 1H), 7,80 (s, 1H), 7,60 (d, J=8.5 Hz, 1H), 4,67 (m, 1H), 4,11 (m, 2H), 3,90 (m, 1H), 3,78 (m, 1H), 3,48 (s, 2H), from 0.84 (s, 9H), of 0.07 (s, 6H).

BW.ii. 6-((R)-5-Hydroxymethyl-2-oxoacridine-3-yl)-4H-pyrido[3,2-b][1,4]thiazin-3-one

On the basis of the intermediate compound (BW.i) (1.20 g) and using method J, specified in the title compound obtained as a beige solid (880 mg, 100%yield).

MS (ESI, m/z):of 282.3 [M+H+].

BW.iii. (R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ymetray ether methanesulfonate acid

On the basis of the intermediate compound (BW.ii) (850 mg) and using the method of N indicated in the title compound obtained as beige is th solid (850 mg; 78%yield).

1H NMR (DMSO-d6) δ: 10,88 (s, 1H), 7,79 (m, 1H), 7,66 (m, 1H), 5,00 (m, 1H), 4,50 (m, 2H), 4,21 (m, 1H), 3,86 (dd, J=10,5, 6.2 Hz, 1H), 3,51 (s, 2H), 3,23 (s, 3H).

Experimental method I: 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

BX.i. (S)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]oxazolidin-2-he

On the basis of 2-{2-[(tert-butyldimethylsilyl)oxy]ethyl}of oxirane (7,00 g; obtained according to WO 2007/144423), ethyl ether of carbamino acid (1,46 g), 4-nitrobenzoic acid (347 mg), (R,R)-(salen)CoIIcomplex (626 mg) and NaH (1,676 g), following methods described in Org. Letters (2005), 7, 1983-1985 specified in the title compound obtained as a dark orange solid (880 mg, 11%yield).

1H NMR (DMSO-d6) δ: 7,39 (s, 1H), 4,59 (m, 1H), to 3.67 (m, 2H), 3,53 (m, 1H), 3,13 (m, 1H), 1,79 (m, 2H), of 0.85 (s, 9H), of 0.02 (s, 6H).

BX.ii. 6-{(S)-5-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoacridine-3-yl}-4H-pyrido[3,2-b][1,4]thiazin-3-one

On the basis of the intermediate compound (BX.i) (880 mg) and intermediate (BK.ii) (720 mg) specified in the header connection receive similar intermediate compounds (BK.iii) after processing by means of column chromatography (heptane/EA in the ratio 1:1) as a beige solid (1,00 g; 68%yield).

MS (ESI, m/z): 410,4 [M+H+].

BX.iii. 6-[(S)-5-(2-Hydroxyethyl)-2-oxoacridine-3-yl]-4H-pyrido[,2-b][1,4]thiazin-3-one

On the basis of the intermediate compound (BX.ii) (1,00 g) and using method J, specified in the title compound obtained as a colorless solid (640 mg; 89%yield).

MS (ESI, m/z): usd296.4 [M+H+].

BX.iv. 2-[(S)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

On the basis of the intermediate compound (BX.iii) (600 mg) and using the method of N indicated in the title compound obtained as a beige solid (649 mg; 81%yield).

MS (ESI, m/z): 374,4 [M+H+].

Experimental method BY: rat-1-Amino-9-chloro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BY.i. tert-Butyl ether rat-(9-chloro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A suspension of intermediate compounds (BE.ix) (140 mg), CuCl (152 mg) and pyridine (0.5 ml) in dry DMSO is heated at a temperature of 120°C for 1 h After cooling to room temperature the reaction mixture was transferred into a mixture of 1-molar HCl solution and etelaat. The aqueous layer was extracted with ethyl acetate and the combined organic layers are successively washed with water, NH4Cl, NaHCO3, dried over MgSO4and concentrate under reduced pressure. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4)to give a pale orange solid (104 mg, 85%yield).

MS (ESI, m/z): 321,5 [M+H+].

BY.ii. rat-1-Amino-9-chloro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BY.i) (90 mg) and using the method specified in the title compound obtained as off-white solid (55 mg, 89%yield).

MS (ESI, m/z): to 221.1 [M+H+].

Experimental method BZ: rat-1-Amino-9-ethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

BZ.i. tert-Butyl ether rat-(4-oxo-9-trimethylsilylethynyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

PdCl2(PPh3)2(23 mg) and CuI (7.8 mg) are added to a suspension of intermediate compounds (BE.ix) (300 mg) in a mixture of tea/dioxane (3 ml; in the ratio 4:1). The reaction mixture is heated to a temperature of 70°C, add one portion of amenitieseven (0,14 ml), then heated in a sealed glass ampoule at a temperature of 100°C for 2 days. After cooling to room temperature, transferred into a mixture of 1-molar solution of HCl and DHM. The organic layer is successively washed with water, NH4Cl and NaHCO3, dried over MgSO4and concentrate under reduced pressure. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50.4)to give a beige solid (132 mg, 42%yield).

MS (ESI, m/z): 383,4 [M+H+].

BZ.ii. tert-Butyl ether rat-(9-ethinyl-4-oxo-1,2-dihydro-4H-feast of the olo[3,2,1-ij]quinoline-1-yl)carbamino acid

A solution of intermediate compound (BZ.i) (115 mg) in THF (2 ml) is treated TBAF (1-molar solution in THF; 0.33 ml) at room temperature. After 15 min the mixture is concentrated, water is added and extracted with DHM. The organic layer is dried over MgSO4filter and concentrate. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4)to give a yellow solid (82 mg; 88%yield).

MS (ESI, m/z): 311,6 [M+H+].

BZ.iii. tert-Butyl ether rat-(9-ethyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

A solution of intermediate compound (BZ.ii) (40 mg) in the Meon (1 ml) hydronaut over Pd/C for 2 h, after which the suspension was filtered using a glass fiber filter. The precipitate on the filter is washed DHM/Meon and the filtrate concentrated under reduced pressure, obtaining a pale yellow solid (37 mg, 91%yield).

MS (ESI, m/z): 315,3 [M+H+].

BZ.iv. rat-1-Amino-9-ethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BZ.iii) (30 mg) and using the method specified in the title compound obtained as a colorless solid (13 mg, 64%yield).

MS (ESI, m/z): 215,5 [M+H+].

Experimetally SA method: rat-1-Amino-9-ethinyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (BZ.ii) (40 mg) and ispolzuyet, specified in the title compound obtained as a beige solid (20 mg, 74%yield).

MS (ESI, m/z): 211,3 [M+H+].

Experimental method MW: Methyl ether rat-(1R*,2R*)-1-amino-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

CB.i. Methyl ester of (2S*,3R*)-3-tert-butoxycarbonylamino-2-hydroxy-3-(7-fluoro-2-methoxyquinoline-8-yl)propionic acid

Based on the methyl ester (E)-3-(7-fluoro-2-methoxyquinoline-8-yl)acrylic acid (7,07 g; obtained by analogy to obtain the corresponding n-butyl ester according to the description in WO 2008/128953) similarly, to obtain the intermediate (BQ.ii)specified in the title compound obtained as a light yellow semi-solid substances (7,621 g; 84%yield).

MS (ESI, m/z): 395,4 [M+H+].

CB.ii. Methyl ether rat-(1R*,2R*)-1-tert-butoxycarbonylamino-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

On the basis of the intermediate compound (CB.i) (4,60 g) and using method H, specified in the header of the intermediate compound obtained as a beige solid (81 mg; 19%yield).

MS (ESI, m/z): 363,4 [M+H+].

CB.iii. Methyl ether rat-[1R*,2R*)-1-amino-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

On the basis of the intermediate compound (CB.ii) (100 mg) and using the method specified in the header connection get in the ideal colorless solid (58 mg; 80%yield).

1H NMR (CDCl3) δ: 7,71 (dd, J=9,4, 0.9 Hz, 1H), 7,49 (m, 1H), 6,92 (m, 1H), 6,63 (d, J=9.4 Hz, 1H), 5,02 (m, 2H), 3,83 (d, J=1.2 Hz, 3H).

Experimental method SS: rat-(1R*,2R*)-1-Amino-9-fluoro-2-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

CC.i. tert-Butyl ether rat-((1R*,2R*)-9-fluoro-2-hydroxymethyl-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (CB.ii) (200 mg) and using the method As specified in the header of the intermediate compound obtained as a colorless solid (112 mg; 61%yield).

MS (ESI, m/z): 335,4 [M+H+].

CC.ii. rat-(1R*,2R*)-1-Amino-9-fluoro-2-hydroxymethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (CC.i) (104 mg) and using the method specified in the title compound obtained as a colorless solid (60 mg; 82%yield).

MS (ESI, m/z): 235,1 [M+H+].

Experimental method CD: the rat-(1R*,2S*)-1-Amino-9-fluoro-2-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

CD.i. tert-Butyl ether rat-((1R*,2R*)-9-fluoro-2-methyl-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)carbamino acid

On the basis of the intermediate compound (CC.i) (495 mg) and using method H, receive intermediate mesilate, which is injected into the reaction after the usual processing, dissolving it in DME (25 ml) and heating under reflux in the presence of NaI (710 mg). After 5 h the reaction mixture was treated with Bu 3SnH (0,96 ml) and heated under reflux for 3 h Then the reaction mixture is diluted with ether and stirred in the presence of an 8%aqueous solution of KF for 16 h, then filtered, the phases are separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers washed with water and brine and dried over MgSO4. The solvents are removed under reduced pressure and the residue purified by column chromatography (heptane/EA ratio from 1:1 to 0:1)to give a colorless solid (374 mg; 79%yield).

MS (ESI, m/z): 319,3 [M+H+].

CD.ii. rat-(1R*,2S*)-1-Amino-9-fluoro-2-methyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (CD.i) (370 mg) and using the method specified in the title compound obtained as a colorless solid (198 mg, 78%yield).

MS (ESI, m/z): 218,9 [M+H+].

Experimental method CE: 1-Amino-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-ymetray ether rat-(1R*,2R*)-methanesulfonic acid

Se. 1-tert-Butoxycarbonylamino-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-ymetray ether rat-(1R*,2R*)-methanesulfonic acid

On the basis of the intermediate compound (CC.i) (200 mg) and using the method of N indicated in the title compound obtained as a yellow foam (285 mg, 100%yield).

MS (ESI, m/z): 413,3 [M+H+].

CE.ii. 1 And the eno-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-ymetray ether rat-(1R*,2R*)-methanesulfonic acid

On the basis of the intermediate compound (Se) (280 mg) and using the method specified in the title compound obtained as a beige foam (140 mg; 77%yield).

MS (ESI, m/z): 313,5 [M+H+].

Experimental method CF: (S)-1-Amino-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

The intermediate compound (C) was isolated using chiral preparative HPLC (column: Daicel, ChiralPak IA, 20×50 mm; eluent: 5% EtOH in MeCN + 0.1% of deja; flow rate: 16,00 ml/min). Specified in the title compound obtained as the first outerwear connection (tR=of 7.36 min). The absolute stereochemistry is established on the basis of the NMR of the corresponding Mosher amide.

MS (ESI, m/z): 205,2 [M+H+].

Experimental method CG: (R)-1-Amino-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

The intermediate compound (C) allocate using girlyyy preparative HPLC (column: Daicel, ChiralPak IA, 20×250 mm; eluent: 5% EtOH in MeCN + 0.1% of deja; flow rate: 16,00 ml/min). Specified in the title compound obtained as the second aliremove connection (tR=8,94 min). The absolute stereochemistry is established on the basis of the NMR of the corresponding Mosher amide.

MS (ESI, m/z): 205,2 [M+H+].

Experimental method SN: 2-[(R)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl ester methanesulfonic acid

This intermediate connection receive similar synthetic the WMD method I, stage BX.i-BX.iii, but using (S,S)-(salen)CoIIcomplex.

Analytical data identical to the data connection of the experimental method REF.

Experimental method CI: (RS)-6-Amino-7-fluoro-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Specified in the header connection receive in accordance with the experimental method AD, but using N-MO and K2OsO4as dihydroxycinnamic agents (Cha, J.K., Chem. Rev. (1995), 95, 1761-1795) in the first stage.

Analytical data identical to the data connection of the experimental method AD.

Example 1: (1RS)-9-Fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and N, and using the method specified in the title compound obtained as a pale yellow solid (39 mg, 18%yield).

1H NMR (DMSO-d6) δ: 10,71 (s, 1H), 7,89 (d, J=9.4 Hz, 1H), 7,58 (m, 1H), 7,32 (m, 1H), 6,94 (m, 3H), of 6.50 (d, J=9.4 Hz, 1H), 4,67 (m, 1H), 4.53-in (s, 2H), 4,36 (m, 2H), 4.00 points (m, 2H), to 3.67 (m, 1H), to 3.02 (m, 1H), 2,74 (m, 3H), 2,04 (m, 1H), is 1.81 (m, 2H).

MC (ESI, m/z): 479,3 [M+H+].

Example 2: (1RS)-9-Fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino)methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and I, and using the method specified in the header connection on ucaut in the form of a pale yellow solid (35 mg; 16%yield).

1H NMR (DMSO-d6) δ: 10,71 (s, 1H), 7,88 (d, J=9.4 Hz, 1H), to 7.59 (dd, J=8,8, 4,7 Hz, 1H), 7,32 (m, 1H), of 6.96 (m, 3H), of 6.50 (d, J=9.4 Hz, 1H), and 4.68 (m, 1H), 4.53-in (s, 2H), 4,32 (m, 2H), 4.00 points (m, 2H), 3,65 (m, 1H), 3,02 (m, 1H), 2,74 (m, 3H), 2,04 (m, 1H)and 1.83 (m, 2H).

MC (ESI, m/z): 479,3 [M+H+].

Example 3: (1RS)-9-Fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and J, and using the method specified in the title compound obtained as off-white solid (34 mg, 15%yield).

1H NMR (DMSO-d6) δ: 10,56 (s, 1H), 7,88 (d, J=9.4 Hz, 1H), to 7.59 (m, 1H), 7,32 (m, 2H), 7,01 (m, 2H), 6,50 (dd, J=9,7, 0.9 Hz, 1H), 4,69 (m, 1H), 4,32 (m, 2H), was 4.02 (m, 2H), 3,66 (m, 1H), 3.43 points (s, 2H), to 3.02 (m, 1H), 2,74 (m, 3H), 1,90 (m, 3H).

MC (ESI, m/z): 495,3 [M+H+].

Example 4: (1RS)-9-Fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods And and and using method D, indicated in the title compound obtained as off-white solid (79 mg; 35%yield).

1H NMR (DMSO-d6) δ: 10,55 (s, 1H), 7,88 (d, J=9.7 Hz, 1H), EUR 7.57 (m, 1H), 7,32 (m, 2H), 7,01 (m, 2H), 6,50 (dd, J=9,4, 0.6 Hz, 1H), 4,69 (m, 1H), 4,34 (m, 2H), a 4.03 (m, 2H), 3,66 (m, 1H), 3,42 (s, 2H), to 3.02 (s, 1H), 2,72 (m, 3H), 1,99 (m, 1H), of 1.84 (m, 2H).

MC (ESI, m/z): 495,3 [M+H+].

Example 5: (1RS)-9-Fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)who oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and N and using method D, indicated in the title compound obtained as yellow solid (31 mg; 37%yield).

MC (ESI, m/z): 481,1 [M+H+].

Example 6: (1RS)-9-Fluoro-1-({2-[(RS)-3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and S, and using the method specified in the title compound obtained as yellow solid (94 mg, 47%yield).

MC (ESI, m/z): 440,5 [M+H+].

Example 7: (1RS)-1-(2-{[(R)-3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and R and using method D, indicated in the title compound obtained as a pale yellow solid (45 mg, 28%yield).

MC (ESI, m/z): 466,2 [M+H+].

Example 8: (1RS)-9-Fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods In and About and using method D, indicated in the title compound obtained as yellow solid (50 mg; 29%yield).

MC (ESI, m/z): 495.1 [M+H+].

Example 9: (1RS)-9-Fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]the Mino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and Q and using the method specified in the title compound obtained as a pale yellow solid (47 mg, 20%yield).

MS (ESI, m/z): 479,2 [M+H+].

Example 10: (1RS)-9-Fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino)ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods In both N and using method D, indicated in the title compound obtained as a pale yellow solid (38 mg; 16%yield).

MS (ESI, m/z): 494,9 [M+H+].

Example 11: (1RS)-9-Fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and R and using method D, indicated in the title compound obtained as yellow solid (29 mg; 19%yield).

MS (ESI, m/z): 440,5 [M+H+].

Example 12: (1RS)-9-Fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and T and using method E, specified in the title compound obtained as a colorless solid (42 mg; 45%yield).

1H NMR (CDCl3) δ: of 7.70 (d, J=9.4 Hz, 1H), 7,47 (m, 1H), 7,32 (m, 1H), 6,92 (m, 2H), 6,76 (m, 1H), 6,62 (d, J=9.4 Hz, 1H), 4,96 (m, 1H), with 4.64 (m, 1H), 4,5 (m, 3H), 4.26 deaths (m, 1H), Android 4.04 (m, 1H), 3,60 (m, 1H), 3,42 (m, 2H), by 2.73 (m, 2H), 1,76 (m, 4H).

MS (ESI, m/z): 479,2 [M+H+].

Example 13: (1RS-9-Fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and U and using method E, specified in the title compound obtained as a pale beige solid (48 mg, 50%yield).

1H NMR (CDCl3) δ: of 7.69 (d, J=9.7 Hz, 1H), 7,47 (dd, J=8,5, a 4.7 Hz, 1H), 7,35 (d, J=2.3 Hz, 1H), 7,24 (m, 2H), 6,91 (m, 2H), is 6.61 (d, J=9.4 Hz, 1H), 4.95 points (dd, J=8,2, 3.2 Hz, 1H)and 4.65 (m, 1H), 4,49 (dd, J=13,5, 8,2 Hz, 1H), 4.26 deaths (dd, J=13,2,, 3.5 Hz, 1H), 4,06 (m, 1H), 3,60 (m, 1H), 3,36 (s, 2H), by 2.73 (m, 2H), 1.77 in (m, 5H).

MS (ESI, m/z): 495,0 [M+H+].

Example 14: (1RS)-Fluoro-1-{2-[(RS)-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and M and using the method specified in the title compound is isolated in the form of a pale yellow solid (13 mg, 12%yield).

1H NMR (CDCl3) δ: 8,76 (m, 1H), 7,66 (d, J=9.4 Hz, 1H), 7,44 (m, 2H), 7,24 (m, 1H), 6,91 (m, 2H), is 6.61 (d, J=9.7 Hz, 1H), 4,96 (m, 1H), 4,80 (m, 1H), 4,50 (m, 1H), 4,28 (m, 1H), 4,08 (m, 1H), 3,68 (m, 1H), 3,38 (s, 2H), equal to 2.94 (m, 2H), of 1.97 (m, 3H).

MS (ESI, m/z): 481,1 [M+H+].

Example 15: (4R)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

On the basis of the connection is on the experimental methods V and J, and using the method, specified in the title compound obtained as a colorless solid (9 mg, 12%yield).

MS (ESI, m/z): 478,0 [M+H+].

Example 16: (4RS)-3-Fluoro-4-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods F and About and using method D, indicated in the title compound obtained as yellow solid (6 mg, 7%yield).

MS (ESI, m/z): 496,3 [M+H+].

Example 17: (4RS)-3-fluoro-4-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods F and N and using method D, indicated in the title compound obtained as yellow solid (8 mg, 9%yield).

MS (ESI, m/z): 496,4 [M+H+].

Example 18: (4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Based on dihydrochloride salts of the compounds of the experimental method D (112 mg) and the compound of the experimental method U (153 mg) and using method E, specified in the title compound obtained as an orange solid (27 mg, 11%yield).

MS (ESI, m/z): 478,1 [M+H+].

Example 19: (4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin--yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Based on dihydrochloride salts of the compounds of the experimental method D (78 mg) and the compound of the experimental method T (101 mg) and using method E, specified in the title compound obtained as an orange solid (17 mg, 11%yield).

MS (ESI, m/z): 462,1 [M+H+].

Example 20: (6RS)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods G (93 mg) and U (153 mg) and using method E, specified in the title compound obtained as yellow solid (210 mg; 88%yield).

MS (ESI, m/z): 478,0 [M+H+].

Example 21: (6RS)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods G and T and using method E, specified in the title compound obtained as yellow solid (276 mg, 70%yield).

MS (ESI, m/z): 462,1 [M+H+].

Example 22: (1RS)-9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 8 hydronaut using method F, and receiving a colorless solid (10 mg, 23%yield).

MS (ESI, m/z): 497,3 [M+H+].

Example 23: (1RS)-9-Fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-digitron-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

23.1. tert-butyl ether rat-(9-fluoro-4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-1-ylmethyl)carbamino acid

A solution of intermediate compound (A.vii) experimental method And (47 mg, 0.15 mmol) in Meon (5 ml) hydronaut over 10%Pd/C (31 mg) for 2 hours the Catalyst is filtered off and washed with Meon. The filtrate is concentrated and receiving specified in the header of the intermediate compound as a colourless solid (48 mg, 100%yield).

MS (ESI, m/z): 321,3 [M+H+].

23.ii. rat-1-aminomethyl-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (23.i) and using the method specified in the header of the intermediate compound obtained as yellow solid (29 mg; 88%yield).

MS (ESI, m/z): 221,2 [M+H+].

23.iii. (1RS)-9-Fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (23.ii) and compounds of the experimental method L and using method D, indicated in the title compound obtained as a pale brown solid (8 mg, 14%yield).

MS (ESI, m/z): 497.4 m [M+N+].

Example 24: (1RS)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 10 GI is their, using method F, and receiving specified in the title compound as off-white solid (8 mg; 16%yield).

MS (ESI, m/z): 497,2 [M+H+].

Example 25: (1RS)-9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 9 hydronaut using method F, and receiving specified in the title compound as a colourless solid (12 mg, 32%yield).

MS (ESI, m/z): 481,2 [M+H+].

Example 26: (1RS)-1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 7 hydronaut using method F, and receiving specified in the title compound as off-white solid (21 mg, 52%yield).

MS (ESI, m/z): 468,2 [M+H+].

Example 27: (1RS-9-fluoro-1-(2-{[(R)-3-(3-Fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 11 hydronaut using method F, and receiving specified in the title compound as off-white solid (17 mg, 74%yield).

MS (ESI, m/z): 442,2 [M+H+].

Example 28: (4RS)-3-Fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of the experiment is selected methods E and L, and using method D, specified in the title compound obtained as yellow solid (7 mg, 18%yield).

MS (ESI, m/z): 496,2 [M+H+].

Example 29: (1RS)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

The compound of example 4 hydronaut using method F, and receiving specified in the title compound as a colourless solid (17 mg, 39%yield).

MS (ESI, m/z): 497,2 [M+H+].

Example 30: (1RS)-9-fluoro-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and on and On and using method D, indicated in the title compound obtained as yellow solid (49 mg; 37%yield).

MS (ESI, m/z): 481,2 [M+H+].

Example 31: (1RS)-1-({[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij']quinoline-4-one:

Proceeding from compounds of experimental methods a and P and using method D, indicated in the title compound obtained as yellow solid (33 mg; 27%yield).

MS (ESI, m/z): 452,2 [M+H+].

Example 32: (1RS)-9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Based on sedimentational methods a and Q, and using the method, specified in the title compound obtained as yellow solid (35 mg; 27%yield).

MS (ESI, m/z): 465,2 [M+H+].

Example 33: (1RS)-9-fluoro-1-({[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and R and using method D, indicated in the title compound obtained as yellow solid (17 mg, 15%yield).

MS (ESI, m/z): to 426.2 [M+H+].

Example 34: (RS)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods W and AF, and using the method specified in the title compound obtained as a beige solid (13 mg, 8%yield).

MS (ESI, m/z): 478,0 [M+H+].

Example 35: (RS)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods in X and U and using method E, specified in the title compound obtained as a beige solid (30 mg, 24%yield).

MS (ESI, m/z): of 476.9 [M+H+].

Example 36: (RS)-1-({[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Based on the connection of the experimental method and (5S)3-(4-ethoxyphenyl)-5-{[(methylsulphonyl)oxy]methyl}-2-oxazolidinone (obtained according to WO 2008/126034) and using the method, specified in the title compound obtained as yellow solid (44 mg; 27%yield).

MS (ESI, m/z): 472,3 [M+H+].

Example 37: (RS)-9-fluoro-1-({[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AG, and using the method specified in the title compound obtained as yellow solid (46 mg; 29%yield).

MS (ESI, m/z): 436,1 [M+H+].

Example 38: (RS)-1-({[(R)-3-(4-butylphenyl)-oxoacridine-3-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and an and using the method specified in the title compound obtained as yellow solid (36 mg, 22%yield).

MS (ESI, m/z): of 450.1 [M+H+].

Example 39: (S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods Y and U and using method E, specified in the title compound obtained as a beige solid (90 mg, 23%yield).

MS (ESI, m/z): 477,9 [M+H+].

Example 40: (S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods Y and T and use the Zuya method E, specified in the title compound obtained as a beige foam (55 mg, 15%yield).

MS (ESI, m/z): 461,9 [M+H+].

Example 41: (S)-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods Y and AI and using the method specified in the title compound obtained as yellow solid (10 mg, 2%yield).

MS (ESI, m/z): 464,1 [M+H+].

Example 42: (RS)-1-({2-[(RS)-3-(2,3-dihydro-[1,4]like[2,3-C]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AJ and using the method specified in the title compound obtained as yellow solid (48 mg; 34%yield).

MS (ESI, m/z): 467,1 [M+H+].

Example 43: (RS)-1-({2-[(RS)-3-(2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AK and using the method specified in the title compound obtained as a yellow foam (42 mg; 30%yield).

MS (ESI, m/z): 467,1 [M+H+].

Example 44: (RS)-1-({2-[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and AL and IP is by using a method, specified in the title compound obtained as a yellow foam (20 mg, 14%yield).

1H NMR (CDCl3) δ: the 7.65 (dd, J=9,4, 1.5 Hz, 1H), 7,38 (m, 3H), 6.87 in (m, 3H), 6,60 (d, J=9.7 Hz, 1H), 4,70 (m, 1H), of 4.44 (m, 2H), 4,01 (m, 4H), 3,61 (td, J=9,1, 7,3 Hz, 1H), 3,14 (m, 1H), 2,90 (m, 3H), of 1.92 (m, 2H), 1,39 (t, J=6,7 Hz, 3H).

MC (ESI, m/z): 452,1 [M+H+].

Example 45: (RS)-9-fluoro-1-({2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AM using a method specified in the title compound obtained as a yellow foam (24 mg, 17%yield).

1H NMR (CDCl3) δ: the 7.65 (dd, J=9,7, 1.5 Hz, 1H), 7,39 (m, 3H), 7,16 (d, J=8.5 Hz, 2H), 6.87 in (td, J=9,1, 1.8 Hz, 1H), 6,60 (d, J=9.4 Hz, 1H), 4.72 in (m, 1H), of 4.44 (m, 2H), was 4.02 (m, 2H), to 3.64 (m, 1H), 3,14 (m, 1H), 2,90 (m, 3H), by 2.55 (m, 2H), 1.91 a (m, 2H), 1.61 of (m, 2H), to 0.92 (t, J=7,3 Hz, 3H).

MC (ESI, m/z): of 450.1 [M+H+].

Example 46: (RS)-1-({2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and AN and using the method specified in the title compound obtained as off-white solid (32 mg; 21%yield).

1H NMR (CDCl3) δ: to 7.64 (dd, J=9,4, 1.2 Hz, 1H), 7,38 (dd, J=8,8, 4,7 Hz, 1H), 7,03 (t, J=2.3 Hz, 1H), 6.89 in (m, 3H), return of 6.58 (d, J=9.4 Hz, 1H), and 4.68 (m, 1H), 4,48 (m, 1H), 4,36 (m, 1H), 4,22 (m, 4H), of 3.97 (m, 2H), 3,56 (m, 1H), 3,12 (m, 1H), 2,88 (m, 3H), 1,90 (m, 2H).

MC (ESI, m/z): 466,0 [M+H+].

Example 47: (RS)-9-fluoro-1-({2-[(RS)-2-the CSR-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AO and using method C, the intermediate compound (RS)-9-fluoro-1-[(2-{3-[(RS)-4-(4-methoxybenzyl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-2-oxoacridine-5-yl}ethylamino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one obtained as a yellowish foam (148 mg, 36%yield). Specified intermediate compound is treated with TFA (4 ml) at reflux for 2 days. The solvent is removed under reduced pressure and the residue partitioned between DHM and aqueous solution of NH4OH. The organic phase is washed with water and brine and dried over MgSO4. The residue is purified by column chromatography (mixture of EA/Meon in the ratio of 9:1 containing 1% NH4OH)to give after trituration in a mixture of ether/Meon beige solid (55 mg, 17%yield).

MS (ESI, m/z): 480,0 [M+H+].

Example 48: (S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods Z and U and using method E, specified in the title compound obtained as a beige solid (135 mg, 53%yield).

1H NMR (DMSO-d6) δ: 10,54 (s, 1H), 8,17 (s, 1H), of 7.70 (d, J=7.9 Hz, 1H), 7,60 (d, J=7,3 Hz, 1H), 7,31 (m, 3H), 7,06 (dd, J=8,5, 2.3 Hz, 1H), 4,70 (m, 2H), of 4.44 (m, 1H), 4,07 (m, 2H), 3,62 (dd, J=8,8, 7,3 Hz, 1H), 3,41 (s, 2H), 2.63 in (m, 2H), 1,76 (m, 2H, of 1.53 (m, 2H).

Examples 49 and 50: (S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AI and using the method mentioned in the title compound obtained as a light yellow solid (466 mg, 26%, mixture of diastereoisomers; MS (ESI, m/z): 495,1 [M+H+]). This mixture (75 mg) separated on a chiral HPLC column (ChiralPak IA, a 4.6×250 mm, 5 μm; eluent: MeCN and EtOH containing 0.1% deja), receiving the appropriate diastereoisomeric:

First aliremove compound (27 mg):1H NMR (CDCl3) δ: of 7.69 (d, J=9.4 Hz, 1H), 7,41 (dd, J=8,5, 4,4 Hz, 1H), 7.23 percent (m, 1H), 7,12 (m, 2H), 6.89 in (t, J=9.1 Hz, 1H), 6,62 (d, J=9.7 Hz, 1H), 4,71 (m, 1H), 4,45 (m, 2H), a 4.03 (m, 2H), 3,62 (m, 2H), 3,34 (s, 2H,), 2,95 (m, 3H), 2,00 (m, 1H), 1,78 (m, 1H).

Second aliremove compound (20 mg):1H NMR (CDCl3) δ: of 7.69 (d, J=9.4 Hz, 1H), 7,41 (dd, J=8,8, 4,4 Hz, 1H), 7,22 (m, 2H), was 7.08 (dd, J=8,5, 2.3 Hz, 1H), 6.89 in (t, J=9.1 Hz, 1H), 6,60 (d, J=9.4 Hz, 1H), to 4.62 (m, 1H), 4,48 (m, 1H), 4,35 (m, 1H), 3.96 points (m, 2H,), 3,71 (m, 1H), 3,34 (s, 2H), 3,10 (dd, J=12,0, 4,4 Hz, 1H), 2,88 (m, 3H), 1.91 a (m, 2H).

Example 51: (RS)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and U and use the UYa method E, specified in the title compound obtained as a light yellow foam (69 mg, 59%yield).

MS (ESI, m/z): 509,2 [M+H+].

Example 52: (RS)-9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and T and using method E, specified in the title compound obtained as a light yellow foam (60 mg, 53%yield).

MS (ESI, m/z): 493,2 [M+H+].

Example 53: (RS)-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AB and AF, and using the method specified in the title compound obtained as a light yellow foam (10 mg, 8%yield).

MS (ESI, m/z): of 476.9 [M+H+].

Example 54: (S)-6-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods Z and J, and using the method specified in the title compound obtained as an orange solid (30 mg, 14%yield).

MS (ESI, m/z): 464,1 [M+H+].

Example 55: (S)-6-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental method is as Z and intermediate compounds (K.iv) and using the method, specified in the title compound obtained as an orange solid (50 mg, 20%yield).

MS (ESI, m/z): rub464.3 [M+H+].

Example 56: (RS)-6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AU and AI and using the method specified in the title compound obtained as a yellow foam (98 mg, 28%yield).

MS (ESI, m/z): 477,9 [M+H+].

Example 57: (S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, AD and T and using method E, specified in the title compound obtained as a colorless solid (70 mg; 29%yield).

MS (ESI, m/z): 480,1 [M+H+].

Example 58: (S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, AD and U and using method E, specified in the title compound obtained as a colorless solid (85 mg; 34%yield).

MS (ESI, m/z): 469,1 [M+H+].

Example 59: (RS)-9-fluoro-1-{2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Based on the experimental compounds the methods and AM using method C, specified in the title compound obtained as yellow solid (46 mg, 31%yield).

1H NMR (CDCl3) δ: to 7.68 (dd, J=9,4, 0.9 Hz, 1H), 7,45 (m, 3H), 7,17 (d, J=8,2 Hz, 2H), 6,92 (t, J=8,8 Hz, 1H), is 6.61 (d, J=9.4 Hz, 1H), 4,99 (m, 1H), 4,78 (m, 1H), to 4.52 (m, 1H), or 4.31 (dd, J=13,2, and 3.2 Hz, 1H), 4,10 (t, J=8,5 Hz, 1H), 3,69 (m, 1H), 2.95 and (m, 2H), has 2.56 (m, 2H), 2,02 (m, 2H), 1,62 (m, 2H), to 0.92 (t, J=7,3 Hz, 3H).

MS (ESI, m/z): 436,2 [M+H+].

Example 60: (RS)-1-({2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AQ and using the method specified in the title compound obtained as a yellow foam (29 mg; 34%yield).

1H NMR (CDCl3) δ: the 7.65 (dd, J=9,7, 0.9 Hz, 1H), 7,39 (dd, J=8,8, 4,7 Hz, 1H), 7,02 (t, J=2.1 Hz, 1H), 6.87 in (m, 3H), return of 6.58 (d, J=9.4 Hz, 1H), 4,70 (m, 1H), of 4.44 (m, 2H), 4,22 (m, 4H), 3,98 (m, 2H), to 3.58 (m, 2H), 3.15 in (m, 1H), 2.91 in (m, 3H), of 1.92 (m, 2H).

MC (ESI, m/z): 466,2 [M+H+].

Example 61: (RS)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and AI and using the method specified in the title compound obtained as a beige solid (110 mg, 46%yield).

1H NMR (DMSO-d6) δ: of 10.58 (s, 1H), of 7.90 (d, J=9.7 Hz, 1H), 7,54 (m, 2H), 7,32 (m, 2H), 7,18 (t, J=7.9 Hz, 1H), was 7.08 (m, 1H), 6,55 (d, J=9.7 Hz, 1H), to 4.81 (m, 1H), 4,39 (m, 2H), 4,08 (m, 3H), and 3.72 (m, 1H), 3,42 (s, 3H), was 3.05 (m, 4H), 2,12 (m, 2H).

MC (ESI, m/): 476,8 [M+H +].

Example 62: (RS)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and H, and using the method specified in the title compound obtained as a beige solid (90 mg, 39%yield).

MC (ESI, m/z): are 460.9 [M+H+].

Example 63: (RS)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and N and using method D, indicated in the title compound obtained as a beige solid (44 mg; 19%yield).

MC (ESI, m/z): 462,9 [M+H+].

Example 64: (R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AA and U and using method E, specified in the title compound obtained as an orange solid (100 mg, 42%yield).

MS (ESI, m/z): 477,8 [M+H+].

Example 65: (R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AA and T and using method E, specified in the title compound obtained as an orange solid which CSOs substances (140 mg; 61%yield).

MS (ESI, m/z): 461,9 [M+H+].

Example 66: (S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from the compound of example 58 (tert-butyldimethylsilyloxy)-acetaldehyde and using method E, with subsequent treatment of the thus obtained intermediate compound in an aqueous solution of TFA (50%; 2 ml)specified in the title compound obtained as a colorless foam (45 mg; 40%yield).

MS (ESI, m/z): 539,9 [M+H+].

Example 67: (S)-7-Fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from the compound of example 57 (tert-butyldimethylsilyloxy)-acetaldehyde and using method E, with subsequent treatment of the thus obtained intermediate compound in an aqueous solution of TFA (50%; 2 ml)specified in the title compound obtained as a colorless foam (80 mg; 45%yield).

MS (ESI, m/z): 523,9 [M+H+].

Example 68: (RS)-9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

68.i. (RS)-1-(2-{[3-(tert-butyldimethylsilyloxy)propyl]-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl) - 9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 10 and 3-(tert-butyldimethylsilyloxy)-Propionaldehyde and using method E, specified in the title compound obtained as a colorless solid (101 mg; 75%yield).

MS (ESI, m/z): 667,4 [M+H+].

68.ii. (RS)-9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (68.i) and using method J, specified in the title compound obtained as off-white solid (70 mg, 87%yield).

MS (ESI, m/z): 553,2 [M+H+].

Example 69: (RS)-9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

69.i. (RS)-1-(2-{[2-(tert-butyldimethylsilyloxy)ethyl]-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 10 and tert-butyldimethylchlorosilane and using method E, specified in the title compound obtained as a colourless solid (100 mg, 76%yield).

MS (ESI, m/z): 653,4 [M+H+].

69.ii. (RS)-9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding and the intermediate compounds (69.i) and using method J, specified in the title compound obtained as off-white solid (54 mg, 69%yield).

MS (ESI, m/z): 539,2 [M+H+].

Example 70: (RS)-9-Fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AR and using method E, specified in the title compound obtained as a colorless solid (175 mg, 73%yield).

MS (ESI, m/z): 480,0 [M+H+].

Example 71: (S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, AD and AR and using method E, specified in the title compound obtained as a colorless solid (87 mg; 36%yield).

MS (ESI, m/z): 481,1 [M+H+].

Example 72: (S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and U and using method E, specified in the title compound obtained as a colorless solid (223 mg; 72%yield).

MS (ESI, m/z): 477,2 [M+H+].

Example 73: (S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and T and using method E, specified in the title compound obtained as a colorless solid (259 mg, 87%yield).

MS (ESI, m/z): 461,2 [M+H+].

Example 74: (S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and AR and using method E, specified in the title compound obtained as a colorless solid (190 mg; 83%yield).

MS (ESI, m/z): 462,2 [M+H+].

Example 75: (R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AA and AR and using method E, specified in the title compound obtained as an orange solid (54 mg, 23%yield).

MS (ESI, m/z): 463,0 [M+H+].

Example 76: (S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods AT and J, and using the method specified in the title compound obtained as a pale yellow solid (24 mg, 7%yield).

1H NMR (DMSO-d6) δ: 10,54 (s, 1H), 8,44 (d, J=4.4 Hz, 1H), 7,94 (d, J=9.7 Hz, 1H), 7,52 (dd, J=4,4, 0.6 Hz, 1H), 7,31(m, 2H),? 7.04 baby mortality (m, 1H), 6,77 (d, J=9.7 Hz, 1H), 4,74 (m, 1H), to 4.38 (m, 1H), 4,10 (m, 2H), 3,90 (m, 1H), 3,66 (m, 1H), 3,42 (s, 2H), 2,90 (m, 2H), 2,69 (m, 2H), to 1.86 (m, 2H).

MS (ESI, m/z): 478,2 [M+H+].

Example 77: (S)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods AT and using method D, indicated in the title compound obtained as a beige solid (25 mg, 7%yield).

MS (ESI, m/z): 478,2 [M+H+].

Example 78: (R)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods V and using method D, indicated in the title compound obtained as a pale yellow solid (150 mg, 42%yield).

MS (ESI, m/z): 478,2 [M+H+].

Example 79: (S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, AD and AU and using method E, specified in the title compound obtained as a pale yellow foam (195 mg; 79%yield).

1H NMR (DMSO-d6) δ: 10,53 (s, 1H), 8,13 (m, 1H), 7,76 (dd, J=8,8, 4,1 Hz, 1H), 7,34 (d, J=2.3 Hz, 1H), 7,29 (d, J=8.5 Hz, 1H), 7,10 (m, 2H), 4,87 (m, 1H)and 4.65 (m, 1H), of 4.44 (dd, J=12,9, 8,2 Hz, 1H), 4,08 (m, 2H), 3,62 (dd, J=8,8, 7,0 Hz, 1H), 3,41 (s, 2H), 2,60 (m, 2H), 1,74(m, 2H), 1,74 (m, 2H).

Example 80: (S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, AD and AV and using method E, specified in the title compound obtained as a pale yellow solid (215 mg; 90%yield).

1H NMR (DMSO-d6) δ: 10,69 (s, 1H), 8,13 (s, 1H), 7,76 (dd, J=8,8, 4,4 Hz, 1H), 7,31 (d, J=2.3 Hz, 1H), 7,13 (t, J=9.1 Hz, 1H), 6,91 (m, 2H), 4,51 (s, 2H), 4,43 (m, 1H), 4,07 (m, 2H), 2,60 (m, 2H), of 1.75 (m, 2H), 1.55V (m, 2H).

Example 81: (RS)-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and About and using method D, indicated in the title compound obtained as a pale yellow solid (42 mg, 18%yield).

MS (ESI, m/z): 463,2 [M+H+].

Example 82: (RS)-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and Q and using the method specified in the title compound obtained as a beige solid (65 mg; 29%yield).

MS (ESI, m/z): 447,3 [M+H+].

Example 83: (RS)-1-({3-[(RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and AW, and using the method specified in the title compound obtained as a beige solid (40 mg; 16%yield).

MS (ESI, m/z): 490,9 [M+H+].

Example 84: (RS)-3-fluoro-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]paratiritis-7-he

Based on the connection of the experimental method OH and intermediate compounds (K.iv) and using the method specified in the title compound obtained as a light brown solid (4 mg, 3%yield).

MS (ESI, m/z): RUB 482.2 [M+H+].

Example 85: (S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and AU and using method E, specified in the title compound obtained as off-white solid (182 mg; 77%yield).

MS (ESI, m/z): of 476.9 [M+H+].

Example 86: (S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and AV and using method E, specified in the title compound obtained as off-white solid (167 mg; 72%yield).

MS (ESI, m/z): are 460.9 [M+H+].

Example 87: (S)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-di is Idro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and J, and using the method specified in the title compound obtained as a light brown solid (82 mg; 27%yield).

MS (ESI, m/z): 462,9 [M+H+].

Example 88: (S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Based on the connection of the experimental method and AS intermediate compounds (K.iv) and using the method specified in the title compound obtained as a light brown solid (99 mg; 33%yield).

MS (ESI, m/z): 463,0 [M+H+].

Example 89: (S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and AY and using the method specified in the title compound obtained as a light brown solid (76 mg, 26%yield).

MS (ESI, m/z): 447,0 [M+H+].

Example 90: (RS)-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

90.i. (RS)-1-[([3-(tert-butyldimethylsilyloxy)propyl]-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 4 and 3-(tre is butyldimethylsilyloxy)-Propionaldehyde and using method E, specified in the title compound obtained as a yellow foam (82 mg; 87%yield).

MS (ESI, m/z): 667,4 [M+H+].

90.ii. (RS)-9-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (90.i) and using method J, specified in the title compound obtained as a light yellow foam (46 mg, 68%yield).

MS (ESI, m/z): 553,2 [M+H+].

Example 91: (RS)-9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

91.i. (RS)-1-[([2-(tert-butyldimethylsilyloxy)ethyl]-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 4 and tert-butyldimethylchlorosilane and using method E, specified in the title compound obtained as a yellow foam (55 mg, 59%yield).

MS (ESI, m/z): 653,4 [M+H+].

91.ii. (RS)-9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (91.i) and using method J, specified in the title compound obtained as off-white foam (25 mg; 55%yield).

MS (ESI, mz): 539,2 [M+H +].

Example 92: (RS)-9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

92.i. (RS)-1-([3-(tert-butyldimethylsilyloxy)propyl]-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 13 and 3-(tert-butyldimethylsilyloxy)-Propionaldehyde and using method E, specified in the title compound obtained as a yellow foam (62 mg, 46%yield).

MS (ESI, m/z): 667,4 [M+H+].

92.ii. (RS)-9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (92.i) and using method J, specified in the title compound obtained as off-white foam (20 mg, 39%yield).

MS (ESI, m/z): 553,2 [M+H+].

Example 93: (RS)-9-fluoro-1-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

93.1. (RS)-1-([2-(tert-butyldimethylsilyloxy)ethyl]-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from the compound of example 13 tert-butyldimethylchlorosilane and using method E, asanee in the title compound obtained as a yellow foam (57 mg; 43%yield).

MS (ESI, m/z): 653,4 [M+H+].

93.ii. (RS)-9-fluoro-1-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of the intermediate compound (93.i) and using method J, specified in the title compound obtained as a yellowish foam (15 mg, 32%yield).

MS (ESI, m/z): 539,2 [M+H+].

Example 94: (RS)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods OH and U and using method E, specified in the title compound obtained as a light yellow solid (44 mg; 36%yield).

MS (ESI, m/z): 496,2 [M+H+].

Example 95: (RS)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods AH and T and using method E, specified in the title compound obtained as a light yellow foam (43 mg; 37%yield).

MS (ESI, m/z): of 480.2 [M+H+].

Example 96: (RS)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods AH and AU and using method E, specified in the header is VCE compound obtained as off-white foam (53 mg; 44%yield).

MS (ESI, m/z): 496,2 [M+H+].

Example 97: (RS)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods AH and AV and using method E, specified in the title compound obtained as a light yellow foam (44 mg, 38%yield).

MS (ESI, m/z): of 480.2 [M+H+].

Example 98: (RS)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and S, and using the method specified in the title compound obtained as a yellow foam (12 mg, 6%yield).

MS (ESI, m/z): 466,2 [M+H+].

Example 99: (RS)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and AI, and using the method specified in the title compound obtained as yellow solid (48 mg; 21%yield).

MS (ESI, m/z): 496,2 [M+H+].

Example 100: (RS)-3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and N and using method D, specified the title compound obtained as a yellow foam (27 mg; 12%yield).

MS (ESI, m/z): RUB 482.2 [M+H+].

Example 101: (RS)-3-fluoro-4-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and About and using method D, indicated in the title compound obtained as a yellow foam (19 mg, 9%yield).

MS (ESI, m/z): RUB 482.2 [M+H+].

Example 102: (RS)-3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and H, and using the method specified in the title compound obtained as a yellow foam (15 mg, 7%yield).

MS (ESI, m/z): of 480.2 [M+H+].

Example 103: (RS)-3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods E and I, and using the method specified in the title compound obtained as yellow solid (16 mg, 11%yield).

MS (ESI, m/z): of 480.2 [M+H+].

Example 104: (R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AZ and T and using method E, the specified reception in the e compound obtained as a beige solid (97 mg; a 40%yield).

MS (ESI, m/z): of 480.2 [M+H+].

Example 105: (R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AZ and U and using method E, specified in the title compound obtained as a beige solid (81 mg, 32%yield).

MS (ESI, m/z): 496,2 [M+H+].

Example 106: (2RS)-6-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AU and About and using method D, indicated in the title compound obtained as a beige solid (158 mg, 31%yield).

MS (ESI, m/z): 464,2 [M+H+].

Example 107: (RS)-1-{2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AQ and using the method specified in the title compound obtained as a light brown solid (20 mg, 23%yield).

MS (ESI, m/z): 452,2 [M+H+].

Example 108: (RS)-N-((S)-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide

108.i. (RS)-3-(tert-butyldimethylsilyloxy)-(3RS)-[2-oxo-3-(3-oxo-3,4-dihydro-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionic acid

Based on the solution of the intermediate (BA.iii) (400 mg; see experimental method In DHM treated with TFA specified in the header of the intermediate compound obtained after water treatment and trituration with ether as a colourless solid (0.2 g, 56%yield).

MS (ESI, m/z): 453,0 [M+H+].

108.ii. (RS)-N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[(RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide

Anhydride propylphosphonic acid (50%solution in EA, 0,31 ml) is added dropwise to a solution of compounds of the experimental method (0.1 g), intermediate (108 l) (0,22 g), DIPEA (of 0.26 ml) in DMF (4 ml). The mixture is stirred at room temperature for 1 h and transferred into a mixture of water and ethyl acetate. The organic phase is washed with diluted aqueous HCl solution and brine, dried over MgSO4and concentrate. Purification of the crude product using column chromatography (EA/Meon in the ratio 19:1) gives a mixture of diastereomeric compounds (ratio and relative stereochemistry not shown) as a colourless solid (245 mg). This intermediate compound is treated with HCl in the Meon (1,25-molar solution), stirred at room temperature for 1 h, concentrated in vacuo and transferred to a mixture of water and bicarbonate solution three is. Product dropped from this mixture, filtered and dried in a high vacuum, getting mentioned in the title compound as a colourless solid (20 mg, mixture of diastereoisomers).

MS (ESI, m/z): 525,1 [M+H+].

Example 109: (R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and U and using method E, specified in the title compound obtained as a colorless solid (96 mg; 67%yield).

MS (ESI, m/z): 477,2 [M+H+].

Example 110: (RS)-6-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AU and N and using method D, indicated in the title compound obtained as a colorless solid (15 mg, 3%yield).

MS (ESI, m/z): 464,2 [M+H+].

Example 111: (R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, BB and T, and using method E, specified in the title compound obtained as a colourless solid (100 mg, 39%yield).

MS (ESI, m/z): 510,2 [M+H+].

Example 112: (R)-7-fluoro-2-methoxy-6-{3-[(R)-2-ox is-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of the experimental methods, CC and U and using method E, specified in the title compound obtained as a colorless solid (75 mg, 28%yield).

MS (ESI, m/z): 526,2 [M+H+].

Example 113: (1RS)-9-fluoro-1-{(3RS)-3-hydroxy-3-[(5RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

113.i. 3-(tert-butyldimethylsilyloxy)-3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]Propionaldehyde (mixture of diastereomers)

To a solution of compounds of the experimental method VA (0.2 g) and DIPEA (0,23 ml) in DHM (5 ml) at room temperature is added dropwise a solution of the complex SO3·Pyr (0,145 g) in DMSO (0.5 ml) for 2 min, after which the mixture was stirred at room temperature for 1.5 h and transferred into a mixture of water and DHM. The organic phase is washed several times with water, dried over MgSO4and concentrate. The crude product used in the next stage without purification (yield approaching quantitative yield).

MS (ESI, m/z): 437,1 [M+H+].

113.ii. (1RS)-9-Fluoro-1-{(3RS)-3-hydroxy-3-[(5RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Based on the connection of the experimental method and intermediate 20 connections (113.i)using method E, followed TBDMS races what Elenium and method J, specified in the title compound obtained as a yellowish solid (21 mg, 9%yield).

MS (ESI, m/z): 510,6 [M+H+].

Example 114: (S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

A solution of the compound of example 48 (33 mg) in a mixture of Meon/EDC (5 ml; in the ratio 4:1) was treated with NaBH4(3 mg) for 30 min, and then quenched with a 1-molar solution of HCl (1 ml) and transferred into a mixture DHM and an aqueous solution of 30 NH4OH. The organic layer was washed with water and brine, dried over MgSO4and purified by column chromatography (mixture of EA/Meon in the ratio from 19:1 to 9:1, containing 1% NH4OH)to give a colorless solid (26 mg, 78%yield).

MS (ESI, m/z): 480,4 [M+H+].

Example 115: (RS)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de)cinoxacin-3-one

Proceeding from compounds of experimental methods G and VK and using method E, specified in the title compound obtained as an orange solid (95 mg, 40%yield).

1H NMR (DMSO-d6) δ: was 10.82 (s, 1H), 8,17 (s, 1H), to 7.77 (m, 1H), 7,68 (m, 2H), 7,60 (d, J=7,3 Hz, 1H), 7,31 (dd, J=7,9, and 7.3 Hz, 1H), 4,71 (m, 2H), of 4.44 (m, 1H), 4,19 (m, 1H), of 4.05 (dd, J=12,9, and 3.8 Hz, 1H), 3,69 (dd, J=10,3, 7,0 Hz, 1H), 3,51 (s, 2H), 2,64 (m, 2H), 1,76 (m, 2H), 1,50 (m, 2H).

MS (ESI, m/z): 479,4 [M+H+].

Example 116: (RS)-9-b is ω-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods BE and U and using method E, specified in the title compound obtained as a colorless solid (10 mg, 9%yield).

MS (ESI, m/z): 555,2 [M+H+].

Example 117: (RS)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile

Proceeding from compounds of experimental methods BV and U and using method E, specified in the title compound obtained as a colorless solid (14 mg, 21%yield).

MS (ESI, m/z): 502,5 [M+H+]

Example 118: (RS)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile

Proceeding from compounds of experimental methods BV and VK and using method E, specified in the title compound obtained as a colorless solid (15 mg, 22%yield).

1H NMR (CDCl3) δ: 7,83 (dd, J=8,5, 1.2 Hz, 1H), of 7.75 (d, J=9.4 Hz, 1H), 7,58 (m, 2H), 7,41 (d, J=7.9 Hz, 1H), for 6.81 (d, J=9.4 Hz, 1H), 5,02 (m, 1H), 4,69 (m, 1H), 4.53-in (m, 1H), 4,28 (m, 2H), 3,76 (dd, J=10,5, 7,3 Hz, 1H), of 3.43 (s, 2H), 2,75 (m, 2H), 1,92 (m, 5H).

MC (ESI, m/z): 503,6 [M+H+].

Example 119: ethyl ester of (R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid

Based on the experimental compounds the different methods BF and AU and using method E, specified in the title compound obtained as a colorless solid (910 mg, 66%yield).

MC (ESI, m/z): 549,2 [M+H+]

Example 120: (R)-7-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AU BG and using method E, specified in the title compound obtained as a beige solid (40 mg, 16%yield).

MC (ESI, m/z): 507,2 [M+H+].

Example 121: hydrochloride (R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid

A suspension of compound of example 119 (100 mg) in 6-molar HCl solution (0.6 ml) is stirred at 90°C for 6 hours Then the reaction mixture is evaporated under reduced pressure, the residue is transferred in the Meon and allocate specified in the title compound by filtration as a beige solid (37 mg; 36%yield).

MC (ESI, m/z): 521,5 [M+H+].

Example 122: (R)-7-dimethylaminomethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and AU NR and using method E, specified in the title compound obtained as a beige solid (mg; 30%output).

MS (ESI, m/z): 534,5 [M+H+].

Example 123: (R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of the experimental methods, BI and AU and using method E, specified in the title compound obtained as a beige foam (50 mg, 27%yield).

MS (ESI, m/z): 560,6 [M+H+].

Example 124: (RS)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BJ and using method E, specified in the title compound obtained as a colorless foam (87 mg, 60%yield).

MS (ESI, m/z): 480,5 [M+H+].

Example 125: (RS)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and VK and using method E, specified in the title compound obtained as a colorless solid (84 mg, 49%yield).

1H NMR (CDCl3) δ: 8,04 (m, 1H), 7,88 (dd, J=8,5, 2,9 Hz, 1H), 7,68 (dd, J=9,4, 1.2 Hz, 1H), 7,60 (dd, J=8,5, 1.5 Hz, 1H), 7,47 (dd, J=8,8, 4,7 Hz, 1H), 6,91 (t, J=9.1 Hz, 1H), 6,63 (d, J=9.4 Hz, 1H), 5,00 (m, 1H), 4,66 (m, 1H), 4,51 (m, 1H), 4,27 (m, 2H), of 3.77 (dt, J=10,3, 6,7 Hz, 1H), 3,47 (s, 2H), 2,77 (m, 2H), 1,80 (m, 4H).

MS (ESI, m/z): 496,6 [M+H+].

Example 126: (RS)-9-fluoro-1{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BL and using method E, specified in the title compound obtained as a colorless solid (54 mg, 32%yield).

1H NMR (CDCl3) δ: 8,03 (m, 1H), 7,88 (dd, J=8,8, 2,9 Hz, 1H), 7,68 (dd, J=9,4, 0.9 Hz, 1H), 7,60 (dd, J=8,5, 1.5 Hz, 1H), 7,47 (dd, J=8,8, 4,7 Hz, 1H), 6,91 (t, J=9.1 Hz, 1H), 6,63 (d, J=9.4 Hz, 1H), 5,00 (m, 1H), 4,66 (m, 1H), 4,51 (m, 1H), 4,28 (m, 2H), of 3.77 (dt, J=10,5, 7,0 Hz, 1H), 3,47 (s, 2H), 2,77 (m, 2H), 1,80 (m, 4H).

MS (ESI, m/z): 496,6 [M+H+].

Examples 127 and 128: (R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl}propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

The product of example 13 allocate using preparative chiral HPLC using a 5 μm (R,R)-Whelk-01 column (or 21.1×250 mm), elwira a mixture of MeCN-EtOH at a ratio of 1:1 containing 0.1% diethylamine with tR=7,25 min (compound of example 127, 100% EE) and tR=10,26 min (compound of example 128, 100% EE).

The data obtained for the compound of example 127:

1H NMR (CDCl3) δ: of 7.69 (d, J=9.7 Hz, 1H), 7,47 (dd, J=8,8, 4,7 Hz, 1H), 7,31 (d, J=2.3 Hz, 1H), 7,22 (d, J=8.5 Hz, 1H), 6,91 (m, 2H), 6,60 (d, J=9.4 Hz, 1H), 4.95 points (dd, J=8,2, 3.5 Hz, 1H), with 4.64 (m, 1H), 4,48 (m, 1H), 4.26 deaths (dd, J=13,5, 3.5 Hz, 1H), Android 4.04 (t, J=8,8 Hz, 1H)and 3.59 (dd, J=8,8, 7,0 Hz, 1H), 3,34 (s, 2H), by 2.73 (m, 2H), 1,76 (m, 4H).

MS (ESI, m/z): 495,3 [M+H+].

The data obtained for the compound of example 128:

1 H NMR (CDCl3) δ: to 7.68 (d, J=9.4 Hz, 1H), 7,46 (dd, J=8,5, a 4.7 Hz, 1H), 7,31 (d, J=2.3 Hz, 1H), 7,21 (d, J=8.5 Hz, 1H), 6.90 to (m, 2H), 6,59 (d, J=9.4 Hz, 1H), 4,94 (dd, J=8,2, 2,9 Hz, 1H), to 4.62 (m, 1H), 4,47 (dd, J=13,2 and 8.2 Hz, 1H), 4,24 (dd, J=13,5, 3.5 Hz, 1H), was 4.02 (t, J=8.5 Hz, 1H), 3,60 (m, 1H), 3.33 and (s, 2H), 2,72 (m, 2H), 1,74 (m, 4H).

MC (ESI, m/z): 495,3 [M+H+].

Examples 129 and 130: (R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

First stage:

Proceeding from the compound of example 4 and 3-(tert-butyldimethylsilyloxy)-Propionaldehyde and using method E, specified in the title compound obtained as a yellow foam (82 mg; 87%yield).

MC (ESI, m/z): 667,4 [M+H+].

Second stage:

The product of the first stage allocate using preparative chiral HPLC using a 5 μm (R,R)-Whelk-01 column (21.1 × 250 mm), elwira a mixture of MeCN-EtOH at a ratio of 1:1 containing 0.1% diethylamine with tR=7,41 min (compound of example 129, 100% EE) and tR=10,35 min (compound of example 130, 100% EE).

The data obtained for the compound of example 129:

1H NMR (CDCl3) δ: to 7.68 (d, J=9.4 Hz, 1H), 7,46 (dd, J=8,8, 4,7 Hz, 1H), 7,30 (d, J=2.1 Hz, 1H), 7,20 (d, J=8.5 Hz, 1H), 6.90 to (m, 2H), return of 6.58 (d, J=9.4 Hz, 1H), 4,94 (dd, J=8,2, 3.2 Hz, 1H), 4,63 (m, 1H), 4,46 (dd, J=13,5 that 8.5 Hz, 1H), 4,23 (dd, J=13,5, 3.5 Hz, 1H), was 4.02 (t, J=8.5 Hz, 1H), to 3.58 (dd, J=7,9, 7,0 Hz, 1H), 3.33 and (s, 2H), 2,72 (m, 2H), 1,74 (m,4H).

MC (ESI, m/z): 495,4 [M+H+].

The data obtained for the compound of example 130:

1H NMR (CDCl3) δ: to 7.68 (d, J=9.4 Hz, 1 H), 7,46 (dd, J=8,8, 4,7 Hz, 1H), 7,30 (d, J=2.3 Hz, 1H), 7,21 (d, J=8.5 Hz, 1H), 6.90 to (m, 2H), 6,59 (d, J=9.4 Hz, 1H), 4,94 (dd, J=8,5, 3.5 Hz, 1H), with 4.64 (m, 1H), 4,47 (m, 1H), 4,24 (dd, J=13,2,, 3.5 Hz, 1H), a 4.03 (t, J=8.5 Hz, 1H)and 3.59 (dd, J=8,8, 7,0 Hz, 1H), 3.33 and (s, 2H), 2,71 (m, 2H), of 1.75 (m, 4H).

MC (ESI, m/z): 495,4 [M+H+].

Example 131: (R)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AA and BJ and using method E, specified in the title compound obtained as a yellowish solid (61 mg, 42%yield).

1H NMR (DMSO-d6) δ: 11,14 (s, 1H), 8,13 (s, 1H), 7,76 (dd, J=8,8, 4,4 Hz, 1H), 7,56 (m, 1H), 7,39 (d, J=8,8 Hz, 1H), 7,13 (t, J=9.1 Hz, 1H), 4,66 (s, 1H), 4,58 (s, 3H), of 4.44 (m, 1H), 4,18 (m, 1H), 4,08 (dd, J=13,2, 3,2 Hz, 1H), to 3.67 (dd, J=10,0, 7,0 Hz, 1H), 2,60 (m, 2H), 1,74 (m, 2H), 1,49 (m, 2H).

MC (ESI, m/z): 481,4 [M+H+].

Example 132: (R)-7-Fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AA and VK and using method E, specified in the title compound obtained as a colorless solid (50 mg, 50%yield).

1H NMR (DMSO-d6) δ: 10,81 (s, 1H), 8,13 (s, 1H), to 7.77 (m, 2H), 7,66 (m, 1H), 7,13 (t, J=9.1 Hz, 1H), 4,90 (m, 1H), 4,69 (m, 1H), of 4.44 (dd, J=12,9, and 8.2 Hz, H), 4,19 (m, 1H), 4,08 (m, 1H), 3,68 (dd, J=10,0, 7,0 Hz, 1H), 3,51 (s, 2H), 2,60 (dd, J=1,2, 0.6 Hz, 2H), of 1.75 (m, 2H), 1,50 (m, 2H).

Example 133: (R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and AU and using method E, specified in the title compound obtained as yellow solid (54 mg, 45%yield).

MC (ESI, m/z): 477,2 [M+H+].

Example 134: (R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and AV and using method E, specified in the title compound obtained as a colorless solid (80 mg, 69%yield).

MS (ESI, m/z): 461,2 [M+H+].

Example 135: (R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and BJ and using method E, specified in the title compound obtained as off-white solid (75 mg, 65%yield).

MS (ESI, m/z): 462,1 [M+H+].

Example 136: (S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and BL and using method specified in the title compound obtained as a beige solid (31 mg, 33%yield).

1H NMR (DMSO-d6) δ: was 10.82 (s, 1H), 7,89 (d, J=9.7 Hz, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 7,55 (m, 2H), 7,18 (t, J=7,6 Hz, 1H), is 6.54 (d, J=9.4 Hz, 1H), 4,70 (m, 2H), 4,37 (m, 1H), 4,19 (m, 1H), 4.00 points (m, 1H), 3,69 (m, 1H), 3,51 (s, 2H), 2,64 (m, 2H), 1,76 (m, 2H), of 1.52 (m, 2H).

MS (ESI, m/z): 478,2 [M+H+].

Example 137: (S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AS and VK and using method E, specified in the title compound obtained as off-white foam (143 mg, 60%yield).

MS (ESI, m/z): 478,2 [M+H+].

Example 138: (R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl)propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods VMS and U and using method E, specified in the title compound obtained as off-white foam (17 mg, 14%yield).

1H NMR (CDCl3) δ: 9,04 (s, 1H), at 8.36 (s, 1H), 7,87 (m, 1H), 7,41 (d, J=2.1 Hz, 1H), 7.23 percent (m, 1H), 6,84 (m, 2H), 5,04 (dd, J=8,5, 3.8 Hz, 1H), 4,59 (m, 2H), 4,28 (dd, J=13,5, and 3.8 Hz, 1H), Android 4.04 (t, J=8,8 Hz, 1H)and 3.59 (m, 1H), 3,36 (s, 2H), 2,80 (m, 2H)and 1.83 (m, 5H).

MC (ESI, m/z): 496,3 [M+H+].

Example 139: (R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Based on connected the th experimental methods VM and AU and using method E, specified in the title compound obtained as a yellowish foam (10 mg, 8%yield).

1H NMR (CDCl3) δ: of 8.37 (s, 1H), of 7.90 (m, 1H), 7,32 (d, J=2.6 Hz, 1H), 7,24 (m, 2H), 6.90 to (m, 1H), PC 6.82 (d, J=9.7 Hz, 1H), is 5.06 (m, 1H), 4,60 (m, 2H), 4,30 (m, 1H), of 4.05 (t, J=8,8 Hz, 1H), 3,61 (m, 1H), 3,35 (s, 2H,), of 2.81 (m, 2H), 1,79 (m, 4H).

MC (ESI, m/z): 496,6 [M+H+].

Example 140: (R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of the experimental methods, VM and T and using method E, specified in the title compound obtained as a yellowish foam (6 mg, 5%).

1H NMR (CDCl3) δ: at 8.36 (d, J=1.2 Hz, 1H), 7,89 (d, J=9.7 Hz, 1H), 7,30 (d, J=2.6 Hz, 1H), for 6.81 (m, 3H), of 5.03 (m, 1H), 4,59 (m, 4H), 4.26 deaths (dd, J=13,2, and 3.8 Hz, 1H), a 4.03 (t, J=8.5 Hz, 1H), to 3.58 (m, 1H), 2,77 (m, 2H), to 1.77 (m, 5H).

MC (ESI, m/z): 480,6 [M+H+]

Example 141: (R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods VM and AV and using method E, specified in the title compound obtained as a yellowish foam (8 mg, 7%yield).

1H NMR (CDCl3) δ: of 8.37 (d, J=1.5 Hz, 1H), of 7.90 (d, J=9.7 Hz, 1H), was 7.36 (d, J=2.3 Hz, 1H), 6.90 to (m, 1H), 6,83 (d, J=9.4 Hz, 1H), 6.73 x (dd, J=8,8, 2.6 Hz, 1H), to 5.03 (m, 1H), 4,59 (m, 4H), 4,25 (dd, J=13,2, and 3.8 Hz, 1H), Android 4.04 (t, J=8.5 Hz, 1H)and 3.59 (m, 1H), was 2.76 (m, 2H), 1,78 (m, 5H).

MC (ESI, m/z): 480,6 [M+H+].

Example 142: (R)-3-fluoro-4-{3-[(R)-2-oxo-3(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods VM and K and using method E, specified in the title compound obtained as a yellowish solid (24 mg, 20%yield).

1H NMR (DMSO-d6) δ: 10,81 (s, 1H), 8,45 (d, J=0.9 Hz, 1H), of 7.96 (d, J=9.7 Hz, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 6.75 in (d, J=9.7 Hz, 1H), 4.95 points (m, 1 H), 4,70 (m, 1H), of 4.44 (dd, J=12,9, 8.5 Hz, 1H), 4,19 (m, 1H), Android 4.04 (dd, J=12,9, 3.5 Hz, 1H), 3,69 (dd, J=10,3, 7,0 Hz, 1H), 3,51 (s, 2H), to 2.67 (m, 3H), of 1.75 (m, 2H)and 1.51 (m, 2H).

MC (ESI, m/z): 497.4 m [M+H+].

Example 143: (R)-3-Fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of the experimental methods, BM and BL and using method E, specified in the title compound obtained as off-white solid (26 mg, 21%yield).

1H NMR (DMSO-d6) δ: 10,81 (s, 1H), 8,45 (d, J=0.6 Hz, 1H), of 7.96 (dd, J=9,7, 0.6 Hz, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 6.75 in (d, J=9.7 Hz, 1H), 4.95 points (m, 1H), 4,70 (m, 1H), of 4.44 (m, 1H), 4,19 (m, 1H), Android 4.04 (dd, J=12,6, 3.5 Hz, 1H), 3,69 (m, 1H), 3,51 (s, 3H), to 2.67 (m, 3H), of 1.76 (m, 2H), of 1.52 (m, 2H).

MS (ESI, m/z): 497,3 [M+H+].

Example 144: (R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BM and BJ and using method E, specified in the title compound obtained as a colorless solid (20 mg, 17%yield).

sup> 1H NMR (DMSO-d6) δ: of 11.15 (s, 1H), 8,45 (d, J=1.5 Hz, 1H), of 7.96 (d, J=9.7 Hz, 1H), EUR 7.57 (m, 1H), 7,40 (m, 1H), 6.75 in (d, J=9.7 Hz, 1H), 4.95 points (m, 1H), 4,67 (m, 1H), 4,58 (s, 2H), of 4.44 (dd, J=12,9, 8.5 Hz, 1H), 4,18 (m, 1H), Android 4.04 (dd, J=12,6, 3.5 Hz, 1H), 3,69 (m, 1H), 2,68 (m, 3H), of 1.75 (m, 2H), of 1.52 (m, 2H).

MS (ESI, m/z): 481,5 [M+H+].

Example 145: (S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and U and using method E, specified in the title compound obtained as a yellowish foam (16 mg, 13%yield).

1H NMR (CDCl3) δ: of 8.37 (d, J=1.2 Hz, 1H), 7,89 (d, J=9.7 Hz, 1H), 7,31 (d, J=2.3 Hz, 1H), 7,22 (d, J=8.5 Hz, 1H), 6,91 (dd, J=8,5, 2.3 Hz, 1H), for 6.81 (d, J=9.7 Hz, 1H), 5,08 (m, 1H), 4,60 (m, 2H), 4,32 (m, 1H), 4,05 (m, 1H), 3,60 (m, 1H), 3,34 (s, 2H), and 2.83 (m, 2H), of 1.85 (m, 4H).

MS (ESI, m/z): 496,5 [M+H+].

Example 146: (S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and T and using method E, specified in the title compound obtained as a yellow foam (7 mg, 6%yield).

MS (ESI, m/z): 480,6 [M+H+].

Example 147: (S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and BK and using method E, specified in the connection obtained as a colorless solid (13 mg, 11%yield).

1H NMR (DMSO-d6) δ: was 10.82 (s, 1H), 8,45 (s, 1H), of 7.96 (d, J=10.0 Hz, 1H), to 7.77 (m, 1H), 7,66 (m, 1H), 6.75 in (d, J=10.0 Hz, 1H), 4,96 (m, 1H), 4,69 (m, 1H), of 4.44 (m, 1H), 4,19 (m, 1H), Android 4.04 (m, 1H), 3,69 (m, 1H), 3,50 (s, 2H), 2,66 (m, 2H), of 1.75 (m, 2H)and 1.51 (m, 2H).

MS (ESI, m/z): 497,6 [M+H+].

Example 148: (S)-3-Fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and AU and using method E, specified in the title compound obtained as a yellowish foam (30 mg, 25%yield).

1H NMR (CDCl3) δ: at 8.36 (d, J=1.5 Hz, 1H), 7,89 (d, J=10.0 Hz, 1H), 7,32 (d, J=2.3 Hz, 1H), 7,22 (d, J=8.5 Hz, 1H), 6.90 to (dd, J=8,5, 2.3 Hz, 1H), for 6.81 (d, J=9.7 Hz, 1H), 5,04 (ddd, J=8,5, 4,1, 0.6 Hz, 1H), 4,59 (m, 2H), 4,27 (dd, J=13,2, and 3.8 Hz, 1H), of 4.05 (m, 1H), 3,60 (dd, J=9,1, 7,3 Hz, 1H), 3,35 (s, 2H), and 2.79 (m, 2H), 1,78 (m, 5H).

MS (ESI, m/z): 496,6 [M+H+].

Example 149: (S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and AV and using method E, specified in the title compound obtained as a yellow foam (8 mg, 7%yield).

MS (ESI, m/z): 480,5 [M+H+].

Example 150: (S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methodology the BN and BL and using method E, specified in the title compound obtained as an orange foam (6 mg, 5%yield).

MS (ESI, m/z): 497.4 m [M+N+].

Example 151: (S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

Proceeding from compounds of experimental methods BN and BJ and using method E, specified in the title compound obtained as a yellowish solid (11 mg, 9%yield).

1H NMR (DMSO-d6) δ: of 11.15 (s, 1H), 8,45 (s, 1H), of 7.96 (d, J=9.7 Hz, 1H), EUR 7.57 (m, 1H), 7,40 (m, 1H), 6.75 in (d, J=10.0 Hz, 1H), 4,96 (m, 1H), 4,67 (m, 1H), 4,58 (s, 2H), of 4.44 (m, 1H), 4,19 (m, 1H), of 4.05 (m, 1H), 3,68 (m, 1H), 2,66 (m, 2H), 1,76 (m, 2H)and 1.51 (m, 3H),

MS (ESI, m/z): 481,5 [M+H+].

Example 152: (RS)-9-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods IN and U and using method E, specified in the title compound obtained as a colorless solid (32 mg, 38%yield).

MS (ESI, m/z): 491,2 [M+H+].

Example 153: (RS)-9-fluoro-1-(methyl-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

A suspension of compound of example 152 (20 mg) in Meon (2 ml) is treated with an aqueous solution of formaldehyde (37%; 16 μl) for 10 min, then treated with NaBH3CN (2.5 mg), premesis the Ute for 3 h at room temperature, transferred into water and extracted with ethyl acetate. The organic layer is washed with water, brine and dried over MgSO4. The organic layer is filtered and evaporated under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH in the ratio of 100:50:4)to give a colorless foam (9 mg; 44%yield).

1H NMR (CDCl3) δ: 8,50 (s, 1H), of 7.70 (d, J=9.7 Hz, 1H), of 7.48 (dd, J=8,5, 4,4 Hz, 1H), 7,40 (d, J=2.1 Hz, 1H), 7,27 (m, 1H), 6,94 (m, 2H), only 6.64 (d, J=9.4 Hz, 1H), 5,03 (t, J=6,4 Hz, 1H), 4,67 (m, 1H), to 4.38 (d, J=6,4 Hz, 2H), 4,08 (m, 1H), 3,62 (m, 1H), 3,40 (s, 2H), 2,50 (m, 2H), 2,22 (d, J=4,1 Hz, 3H), 1.77 in (m, 4H).

MC (ESI, m/z): 509,3 [M+H+].

Example 154: (RS)-6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods AU and N, and using the method specified in the title compound obtained as a yellowish foam (82 mg, 35%yield).

MC (ESI, m/z): 462,1 [M+H+].

Example 155: (RS)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods SA and I and using the method specified in the title compound obtained as a yellow foam (90 mg, 39%yield).

MC (ESI, m/z): 462,1 [M+H+].

Example 156: (RS)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]atilim is but}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods SA and J, and using the method specified in the title compound obtained as a brown foam (270 mg, 37%yield).

MC (ESI, m/z): 478,2 [M+H+].

Example 157: (R)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and H, and using the method specified in the title compound obtained as a yellowish foam (59 mg, 26%yield).

MS (ESI, m/z): 447,2 [M+H+].

Example 158: (R)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SU and J, and using the method specified in the title compound obtained as a brown foam (81 mg, 35%yield).

MS (ESI, m/z): 463,2 [M+H+].

Example 159: (RS)-9-fluoro-1-{4-[(RS)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BP and using method E, specified in the title compound obtained as a colorless foam 20 (84 mg, 55%yield).

MS (ESI, m/z): 509,1 [M+H+].

Example 160: (S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]chinox the Lin-3-one

A solution of the compound of example 79 (42 mg) in DHM/Meon (in the ratio 2:1; 6 ml) was treated with NaBH- (3.2 mg). After stirring at room temperature for 30 min, the reaction mixture was quenched by adding 1-molar solution of HCl (1 ml) and transferred into a mixture DHM and aqueous solution of NH4OH. The organic layer is washed with water, dried over MgSO4concentrate under reduced pressure and purified by column chromatography (EA/Meon in the ratio from 19:1 to 9:1)to give a beige solid (29 mg, 69%yield).

MS (ESI, m/z): 498,2 [M+H+].

Example 161: methyl ester of (1R,2R)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid and methyl ester of (1S,2S)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

Proceeding from compounds of experimental methods BQ and U and using method E, the mixture is named in the title compounds are obtained as a yellowish solid (46 mg, 23%yield).

MS (ESI, m/z): 535,6 [M+H+].

Example 162: methyl ester of (1R,2R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid and methyl ester of (1S,2S)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihyd the on-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

Proceeding from compounds of experimental methods BQ and AU and using method E, the mixture is named in the title compounds are obtained as a colorless solid (67 mg, 32%yield).

MS (ESI, m/z): 535,7 [M+H+].

Example 163: (1R,2R)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2S)-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of the experimental methods, BR and U and using method E, the mixture is named in the title compounds are obtained as a colorless solid (99 mg, 54%yield).

MS (ESI, m/z): 507,2 [M+H+].

Example 164: (1R,2R)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2S)-2-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of the experimental methods, BR and AU and using method E, the mixture is named in the title compounds are obtained as a colorless solid (110 mg, 60%yield).

MS (ESI, m/z): 507,2 [M+H+].

Example 165: (1R,2R)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-and the]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2S)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods BS and U and using method E, the mixture is named in the title compounds are obtained as a colorless solid (20 mg, 32%yield).

MS (ESI, m/z): 521,6 [M+H+].

Example 166: (1R,2S)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2R)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods W and U and using method E, the mixture is named in the title compounds are obtained as a colorless solid (56 mg, 38%yield).

1H NMR (CDCl3) δ: to 8.57 (s, 1H), 7,71 (dd, J=9,4, 0.6 Hz, 1H), 7,52 (m, 2H), 7,33 (m, 1H), 7.23 percent (m, 2H), 6,99 (m, 1H), 6,69 (dd, J=9,4, 1.5 Hz, 1H), 4,82 (d, J=6,4 Hz, 1H)and 4.65 (m, 1H), 4.26 deaths (s, 1H), 4,05 (td, J=8,5, 6.2 Hz, 1H), 3,63 (m, 1H), 3,39 (s, 2H), 2,80 (m, 2H), to 1.87 (m, 5H), and 1.56 (d, J=6,7 Hz, 3H).

MS (ESI, m/z): 491,3 [M+H+].

Example 167: (1R,2S)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2R)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods W and AU and using method E, the mixture is named in the title compounds are obtained as colorless TV is Gogo substances (59 mg, a 40%yield).

1H NMR (CDCl3) δ: at 8.60 (dd, J=2,3, 0.6 Hz, 1H), 7,71 (dd, J=9,4, 0.9 Hz, 1H), 7,51 (m, 2H), 7,33 (dd, J=14,4, 2.3 Hz, 1H), 7,24 (m, 2H), 6,98 (td, J=8,2, 2.3 Hz, 1H), 6,69 (dd, J=9,4, 1.8 Hz, 1H), 4,80 (dt, J=6,4, 1.8 Hz, 1H), with 4.64 (m, 1H), 4,24 (s, 1H), 4,05 (td, J=8,5 and 5.9 Hz, 1H), 3,61 (dd, J=8,8, 7,0 Hz, 1H), 3,39 (s, 2H), 2,80 (m, 2H), 1,79 (m, 5H), of 1.55 (d, J=6.4 Hz, 3H).

MS (ESI, m/z): 491,3 [M+H+].

Example 168: (1R,2S)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2R)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods W and VK and using method E, the mixture is named in the title compounds are obtained as a colorless solid (42 mg, 24%yield).

1H NMR (CDCl3) δ: 8,50 (s, 1H), 7,81 (m, 1H), 7,68 (dd, J=9,4, 5.6 Hz, 1H), 7,51 (m, 3H), 7,19 (m, 1H), 6,63 (dd, J=9,4, 5.0 Hz, 1H), amounts to 4.76 (m, 1H), to 4.62 (d, J=7.9 Hz, 1H), 4,18 (m, 2H), 3.72 (m, 1H), 3.43 points (s, 2H), was 2.76 (m, 2H), 1.77 in (m, 5H), 1,53 (d, J=6.4 Hz, 3H).

MS (ESI, m/z): 492,3 [M+H+].

Example 169: (1R,2S)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2R)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods W and BL and using IU is od E, the mixture is named in the title compounds are obtained as a colorless solid (43 mg, 24%yield).

1H NMR (CDCl3) δ: 8,10 (m, 1H), 7,86 (dd, J=8,8, 3.8 Hz, 1H), 7,71 (dd, J=9,4, 1.5 Hz, 1H), 7,55 (m, MN), 7,22 (m, 1H), to 6.67 (d, J=9.4 Hz, 1H), a 4.83 (m, 1H), with 4.64 (m, 1H), 4,22 (m, 2H, in), 3.75 (dt, J=10,5, 7,3 Hz, 1H), 3.46 in (s, 2H), and 2.79 (m, 2H), to 1.87 (m, 5H), of 1.57 (dd, J=6,4, 1.2 Hz, 3H).

MS (ESI, m/z): 492,4 [M+H+].

Example 170: (1R,2R)-2-(1-hydroxy-1-methylethyl)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one and (1S,2S)-2-(1-hydroxy-1-petiatil)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods BU and U and using method E, the mixture is named in the title compounds are obtained as a colourless foam (22 mg, 46%yield).

MS (ESI, m/z): 535,6 [M+H+].

Example 171: (R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from the compound of example 132 and using the methodology of example 160, specified in the title compound obtained as a colorless foam (36%yield).

MS (ESI, m/z): 499,4 [M+H+].

Example 172 N-((RS)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}ndimethylacetamide and (RS)-1-{-[(R)-3-(4-acetyl-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-2-oxoacridine-5-yl]propylamino}-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

A solution of the compound of example 13 (20 mg) and DIPEA (14 μl) is injected into the reaction at a temperature of 0°C With Ac2O (6 ml). The reaction mixture was stirred at room temperature for 5 h, the solvent is removed under reduced pressure and the residue is dissolved in DHM and sequentially washed with water and brine. The organic layer is dried over MgSO4. The solvent is removed under reduced pressure and the residue purified by column chromatography (DHM/Meon/NH4OH; ratio of 1000:50:4)to give a mixture of the two possible N-acetates in the ratio of 1:1 as off-white foam (18 mg; 83%yield).

MS (ESI, m/z): 537,5 [M+H+].

Example 173: (S)-4-hydroxy-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he

To a solution of compounds of the experimental method BD (75 mg) in EtOH (3 ml) was added the compound of the experimental method AR (89 mg, 1.5 EQ.) and K2CO3(65 mg, 3 EQ.) and the mixture is stirred at room temperature for 3 days, after which the solvent is removed under reduced pressure and the residue is transferred into a mixture of water and DHM-Meon (in the ratio 9:1). The phases are separated and the aqueous layer was twice extracted with a mixture DHM-Meon (in the ratio 9:1). The combined organic layers dried over MgSO4and concentrate. The residue is purified polosukhina chromatography (DHM/Meon/NH 4OH in the ratio of 1000:100:8), receiving specified in the title compound as a yellow solid (26 mg, 26%yield).

MS (ESI, m/z): 494,2 [M+H+].

Example 174: (RS)-9-fluoro-1-hydroxy-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

On the basis of 9-fluoro-1-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl]methyl-4-methylbenzenesulfonate (obtained according to EP 1980251) experimental AR method and using the method specified in the title compound obtained as yellow solid (85 mg, 65%yield).

MS (ESI, m/z): 511,2 [M+H+].

Example 175: (RS)-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods AE and BW and using a method specified in the title compound obtained as a beige solid (70 mg, 20%yield).

MS (ESI, m/z): 464,4 [M+H+].

Example 176: (RS)-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods in AE and I, and using the method specified in the title compound obtained as a colorless solid (130 mg; 36%yield).

MS (ESI, m/z): 478,2 [M+the +].

Example 177: (RS)-9-chloro-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BY VK and using method E, specified in the title compound obtained as a pale yellow solid (31 mg; 58%yield).

1H NMR (CDCl3) δ: 8,33 (m, 1H), to 7.84 (dd, J=8,8, 4,4 Hz, 1H), 7,66 (dd, J=9,4, 3.5 Hz, 1H), EUR 7.57 (dd, J=8,5, 2.3 Hz, 1H), 7,41 (dd, J=8,2, 1.8 Hz, 1H), 7,11 (dd,J=8,5, 1.5 Hz, 1H), 6,66 (dd, J=9,4, 3.8 Hz, 1H), 4,91 (m, 1H), to 4.62 (m, 1H), 4,45 (m, 1H), 4,25 (m, 2H, in), 3.75 (m, 1H), 3.45 points (s, 2H), 2,61 (m, 2H), 1,78 (m, 5H).

MS (ESI, m/z): 512,3 [M+H+].

Example 178: (RS)-9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BY U and using method E, specified in the title compound obtained as a colorless solid (14 mg, 26%yield).

1H NMR (CDCl3) δ: 8,73 (s, 1H), 7,68 (d, J=9.7 Hz, 1H), 7,39 (m, 2H), 7,25 (m, 1H), 7,12 (d, J=8,2 Hz, 1H), 6,98 (m, 1H), of 6.68 (d, J=9.4 Hz, 1H), 4,91 (dd, J=8,2, 3.5 Hz, 1H)and 4.65 (m, 1H), 4,46 (m, 1H), 4,30 (dd, J=to 13.2, 3.2 Hz, 1H), 4,06 (m, 1H), 3,61 (m, 1H), 3,39 (s, 2H), 2,64 (m, 2H), to 1.86 (m, 5H).

MS (ESI, m/z): 511,3 [M+H+].

Example 179: (RS)-9-ethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods BZ and U and ispolzuyet E, specified in the title compound obtained as a colorless solid (11 mg; 36%yield).

1H NMR (CDCl3) δ: 8,56 (m, 1H), 7,68 (d, J=9.4 Hz, 1H), 7,39 (m, 2H), 7,26 (m, 1H), 7,01 (m, 2H), only 6.64 (d, J=9.4 Hz. 1H), 4,82 (t, J=5.3 Hz, 1H)and 4.65 (m, 1H), 4,37 (d, J=5.3 Hz, 2H), 4,06 (m, 1H), 3,61 (dd, J=8,5, 7,0 Hz, 1H), 3,39 (s, 2H), 2,80 (m, 4H), 1,71 (m, 5H), of 1.29 (m, 3H).

MS (ESI, m/z): 505,5 [M+H+].

Example 180: (RS)-9-ethinyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SA and U and using method E, specified in the title compound obtained as a colorless solid (10 mg; 21%yield).

MS (ESI, m/z): 501,2 [M+H+].

Example 181: methyl ester of (1R*,2R*)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

Proceeding from compounds of experimental methods ST and U and using method E, specified in the title compound obtained as off-white foam (23 mg, 20%yield).

MS (ESI, m/z): 553,6 [M+H+].

Example 182: (1R*,2R*)-9-fluoro-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods SS and U and using method E, specified in the title compound floor is given in the form of a white foam (44 mg; 38%yield).

MS (ESI, m/z): 525,3 [M+H+].

Example 183: (1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CD and U and using method E, specified in the title compound obtained as off-white foam (12 mg, 10%yield).

MS (ESI, m/z): 509,3 [M+H+].

Example 184: (1R*,2S*)-9-fluoro-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CD and AU and using method E, specified in the title compound obtained as off-white foam (21 mg, 18%yield).

MS (ESI, m/z): 509,3 [M+H+].

Example 185: (1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CD and VK and using method E, specified in the title compound obtained as off-white foam (64 mg; 55%yield).

MS (ESI, m/z): 510,3 [M+H+].

Example 186: hydrochloride (1R*,2R*)-9-fluoro-4-oxo-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

A solution of the compound of example 181 (20 mg) in dioxane (1 ml treated with an aqueous solution of HCl (37%; 0,142 ml), stirred at 50°C for 3 h, concentrated under reduced pressure and the residue suspended in EA/Meon (in the ratio 4:1), filtered, washed, TBME and dried in a high vacuum, getting a grey solid (6 mg; 29%yield).

MS (ESI, m/z): 539,2 [M+H+].

Example 187: (RS)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one

A solution of the compound of example 2 (60 mg) in Meon/Asón (in the ratio 1:1, 2 ml) hydronaut over Pd/C (133 mg) during the night. The catalyst was then filtered off and washed with Meon and Meon/DHM. The filtrate is concentrated under reduced pressure. The residue is transferred into the water and 28%aqueous solution of NH4OH, filtered, washed with water, TBME and dried under reduced pressure, obtaining off-white foam (45 mg; 75%yield).

MS (ESI, m/z): 481,5 [M+H+].

Example 188: (1R*,2R*)-2-aminomethyl-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

188.i. 9-fluoro-4-oxo-1-{3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-ymetray ether (1R*,2S*)-methanesulfonic acid

Proceeding from compounds of experimental methods in CE and U and using method E, specified in the header of the connection p is to obtain in the form of off-white foam (79 mg; 30%output).

MS (ESI, m/z): 603,3 [M+H+].

188.ii. (1R*,2S*)-2-azidomethyl-9-fluoro-1-{3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

NaN3(25 mg) are added to a solution of intermediate compound (188 l) (77 mg) in DMF (1.5 ml) and the resulting mixture is stirred at a temperature of 80°C for 1 h, then add water and ethyl acetate and the phases are separated. The aqueous layer was again extracted with ethyl acetate and the combined organic layers washed with water and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography (DHM/Meon/NH4OH in the ratio of 1000:50:4)to give a light yellow foam (57 mg; 81%yield).

MS (ESI, m/z): 550,5 [M+H+].

188.iii. (1R*,2S*)-2-aminomethyl-9-Fluoro-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

A solution of intermediate compound (188.ii) (57 mg) in THF (1.5 ml) is treated with PPh3(30 mg) and water (19 ml). The mixture is heated at 70°C overnight, concentrated under reduced pressure and the residue is transferred in DHM. The organic layer is extracted with 1-molar HCl solution and the aqueous layer was alkalinized NH4OH. The aqueous layer was extracted with DHM/Meon (in the ratio 9:1) and the combined organic layers dried over MgSO4, conc the shape and purified by column chromatography (DHM/Meon/NH 4OH in the ratio of 1000:100:8)to give a light yellow foam (26 mg; 48%yield).

MS (ESI, m/z): 524,3 [M+H+].

Example 189: (S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and BJ CF and using method E, specified in the title compound obtained as off-white foam (52 mg, 32%yield).

MS (ESI, m/z): 480,5 [M+H+].

Example 190: (S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CF and AR and using method E, specified in the title compound obtained as off-white foam (64 mg; 34%yield).

MS (ESI, m/z): 480,5 [M+H+].

Example 191: (S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CF and BL and using method E, specified in the title compound obtained as off-white foam (53 mg; 27%yield).

MS (ESI, m/z): 496,1 [M+H+].

Example 192: (S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods is s CF and VC and using method E, specified in the title compound obtained as off-white solid (73 mg, 38%yield).

MS (ESI, m/z): 496,6 [M+H+].

Example 193: (R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CG and BJ and using method E, specified in the title compound obtained as off-white foam (56 mg; 34%yield).

MS (ESI, m/z): 480,6 [M+H+].

Example 194: (R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CG and AR and using method E, specified in the title compound obtained as off-white foam (71 mg, 38%yield).

MS (ESI, m/z): 480,6 [M+H+].

Example 195: (R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods CG and BL and using method E, specified in the title compound obtained as a light yellow solid (52 mg; 27%yield).

MS (ESI, m/z): 496,5 [M+H+].

Example 196: (R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

IP is odya of compounds of experimental methods CG and VK and using method E, specified in the title compound obtained as a light yellow solid (55 mg, 28%yield).

MS (ESI, m/z): 496,6 [M+H+].

Example 197: (RS)-9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods and CH and using the method specified in the title compound obtained as a pale yellow solid (40 mg, 22%yield).

MS (ESI, m/z): 496,6 [M+H+].

Example 198: (RS)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one

Proceeding from compounds of experimental methods a and I, and using the method specified in the title compound obtained as a pale yellow solid (10 mg, 11%yield).

MS (ESI, m/z): 496,4 [M+H+].

Example 199: (RS)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one

Proceeding from compounds of experimental methods CI and VK and using method E, specified in the title compound obtained as a light yellow solid (650 mg, 26%yield).

MS (ESI, m/z): 497,5 [M+H+].

Example 200: (RS)-7-fluoro-6-{3-[[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]impregnated the amino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

A solution of the compound of the experimental method CI (0.2 g, 0,975 mmol) and the compound of the experimental method VK (0.3 g, 0,975 mmol) in a mixture of EDC/Meon (in the ratio 1:1.8 ml) was stirred at room temperature overnight, then added NaBH4(110 mg) and the mixture is stirred at room temperature for 1 h Then the reaction mixture was quenched by adding HCl (1-molar solution), and transferred to the mixture DHM and diluted solution of NH4OH. The organic phase is dried over MgSO4and concentrate. The residue is purified by column chromatography (mixture DHM/Meon in the ratio 19:1, containing 1% NH4OH). Specified in the title compound obtained as a light pink foam (78 mg; 16%yield).

MS (ESI, m/z): 499,5 [M+H+].

Example 201: dihydrochloride (RS)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

201.i. tert-butyl ether ((RS)-7-fluoro-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]cinoxacin-6-yl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}carbamino acid

A suspension of compound of example 199 (0.6 g, 1.2 mmol) in DHM (10 ml), Meon (2 ml) and THF (5 ml) is treated Side2O (526 mg, 2 EQ.) and heated under reflux overnight. Volatile fractions are removed under reduced pressure and the residue purified by column chromatography (EA), getting the desired intermediate compound in the form of a beige foam (0,61 g, 85%yield).

MS (ESI, m/z): 597,7 [M+H+].

201.ii. tert-butyl ether ((RS)-7-fluoro-3-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2,3-de]cinoxacin-6-yl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}carbamino acid

A solution of intermediate compound (201.1) (610 mg) in Meon/DHM (in the ratio 4:1; 20 ml) was treated with NaBH4(77 mg, 2 EQ.) and stirred at room temperature for 2 h, after which the mixture is quenched by adding HCl (1-molar solution) and transferred into a mixture DHM and diluted solution of NH4OH. The organic phase is dried over MgSO4and concentrate. The residue is purified by column chromatography (EA). Specified in the title compound obtained as a beige foam (410 mg; 67%yield).

MS (ESI, m/z): 599,6 [M+H+].

201.iii. tert-butyl ester ((R)-7-fluoro-1-methyl-3-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2,3-de]cinoxacin-6-yl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}carbamino acid

A solution of intermediate compound (201.ii) (100 mg) in Meon (3 ml) is treated Asón is 0.019 ml), aqueous solution of formaldehyde (37%, was 0.026 ml) and NaCNBH3(30 mg). The mixture is stirred at room temperature for 3 h, diluted with ethyl acetate and water and the organic phase is washed with NaHCO3and p is SOLOM, dried over MgSO4and concentrate. The residue is crystallized from ether, obtaining the desired intermediate compound as a colourless solid (0.075 g, 73%yield).

MS (ESI, m/z): 613,7 [M+H+].

201.iv. the dihydrochloride (RS)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

A suspension of intermediate compounds (201.iii) (0,068 g, 0.1 mmol) in HCl (4-molar solution in dioxane, 1 ml) was stirred at room temperature for 15 min, after which the volatile fractions are removed under reduced pressure and the solid is washed with ether and dried in high vacuum. Specified in the header of the salt is isolated in the form of a gray solid (0,068 g; quantitative yield).

MS (ESI, m/z): 513,6 [M+H+].

Example 202: dihydrochloride (RS)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

202.i. tert-butyl ester ((R)-7-fluoro-1-(3-hydroxypropyl)methyl-3-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2,3-de]cinoxacin-6-yl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}carbamino acid

A solution of intermediate compound (201.ii) (100 mg) in Meon (3 ml) is treated Asón is 0.019 ml), aqueous solution of formaldehyde is (37%, 0,026 ml) and 3-[(tert-butyldimethylsilyl)oxy]-1-propanal (88 mg, a commercial product). The mixture is stirred at room temperature for 5 h, diluted with ethyl acetate and water and the organic phase is washed with NaHCO3and brine, dried over MgSO4and concentrate. The residue is purified by column chromatography (EA), obtaining the desired intermediate compound in the form of a yellowish oil (0.11 g, 62%yield).

MS (ESI, m/z): 771,6 [M+H+].

202.ii. the dihydrochloride (RS)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one

A suspension of intermediate compounds (202.i) (0.11 g, 0.14 mmol) in HCl (4-molar solution in dioxane, 1.5 ml) was stirred at room temperature for 15 minutes of Volatile fractions are removed under reduced pressure and the solid is washed with ether and dried in high vacuum. Named in the title salt is isolated in the form of a gray solid (0,071 g; 78%yield).

MS (ESI, m/z): 557,3 [M+H+].

Pharmacological properties of the compounds according to the invention

Analyses by the method of in vitro

Experimental methods:

The minimum inhibition concentration (MICs; mg/l) were determined in cation-regulated nutrient medium Mueller-Hinton Broth (BBL) using the method of microrasbora, opican the th in "Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically", Approved Standard, 7thed. Clinical and Laboratory Standards Institute (CLSI) Document M7-A7, Wayne, PA, USA, 2006.

The results:

Join all of the above examples are tested regarding the effects on gram-positive and gram-negative bacteria, such as S. aureus, E. faecalis, S. pneumonias, M. catarrhalis, A. baumanii, Escherichia coli or P. aeruginosa.

Typical results of antibacterial tests are presented in the table below (MIC in mg/l).

Example No.MIC for M catarrhalis A894Example No.MIC for M catarrhalis A894
1≤0,0312≤0,031
3≤0,0314≤0,031
5≤0,03160,125
7≤0,0318≤0,031
9≤0,03110≤0,031
110,063 12≤0,031
13≤0,03114≤0,031

Example No.MIC for M catarrhalis A894Example No.MIC for M catarrhalis A894
15≤0,03116≤0,031
17≤0,03118≤0,031
19≤0,03120≤0,031
21≤0,03122≤0,031
23≤0,03124≤0,031
25≤0,031260,25
270,528≤0,031
29 ≤0,031300,031
3116320,031
331634≤0,031
35≤0,031368
3713816
39≤0,031400,125
410,5422
431440,125
450,06346≤0,031
47≤0,03148≤0,031
49≤0,03150≤0,031
51≤0,03152≤0,031
53≤0,031540,25
55≤0,03156≤0,031
57≤0,03158≤0,031
59460≤0,031
61≤0,03162≤0,031
630,03164≤0,031
65≤0,03166≤0,031
67≤0,06368≤0,031
69≤0,03170≤0,031
71≤0,031 72≤0,031
73≤0,03174≤0,031
75≤0,03176≤0,031
770,03178≤0,031
79≤0,03180≤0,031
81≤0,031820,25
83≤0,031840,063
85≤0,03186≤0,031
87≤0,03188≤0,031
890,06390≤0,031
91≤0,03192≤0,031
93≤0,03194≤0,031
95≤0,03196≤0,031
97≤0,031980,25
99≤0,0311000,031
101≤0,031102≤0,031
103≤0,031104≤0,031

≤0,031
Example No.MIC for M catarrhalis A894Example No.MIC for M catarrhalis A894
105≤0,031106≤0,031
1078108≤0,031
109≤0,031110 ≤0,031
1110,125112≤0,031
113≤0,031114≤0,031
115≤0,031116≤0,031
117≤0,031118≤0,031
119≤0,0311200,125
1210,1251220,5
1230,125124≤0,031
125≤0,031126≤0,031
127≤0,031128≤0,031
129≤0,031130≤0,031
131 ≤0,031132≤0,031
133≤0,031134≤0,031
135≤0,031136≤0,031
137≤0,031138≤0,031
139≤0,031140≤0,031
141≤0,031142≤0,031
143≤0,031144≤0,031
145≤0,031146≤0,031
147≤0,031148≤0,031
149≤0,031150≤0,031
151≤0,031152
153≤0,031154≤0,031
155≤0,031156≤0,031
1572158≤0,031
159≤0,031160≤0,031
1610,1251620,25
1630,0311640,031
1650,125166≤0,031
167≤0,031168≤0,031
169≤0,0311700,25
171≤0,0311720,25
173 0,125174≤0,031
175≤0,031176≤0,031
177≤0,031178≤0,031
179≤0,031180≤0,031
181≤0,031182≤0,031
183≤0,031184≤0,031
185≤0,0311860,5
187≤0,031188≤0,031
189≤0,031190≤0,031
191≤0,031192≤0,031
193≤0,031194 ≤0,031

Example No.MIC for M catarrhalis A894Example No.MIC for M catarrhalis A894
195≤0,031196≤0,031
197≤0,031198≤0,031
199≤0,031200≤0,031
201≤0,0312020,063

Data MIC obtained for compounds of the examples presented in the description of the application.

By applying the method described on page 298 description, the corresponding experimental results for compounds of the examples presented in the application (MIC in mg/l).

Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
1≤0.031≤0.0310.125≤0.0310.125
2≤0.031≤0.0310.125≤0.0310.031
3≤0.031≤0.0310.031≤0.031≤0.031
4≤0.031≤0.0310.25≤0.0310.063
5≤0.031≤0.0310.063≤0.0310.125
6≤0.0310.0630.250.1251
7≤0.031≤0.0310.063≤0.0318≤0.031≤0.031≤0.031≤0.031≤0.031
9≤0.031≤0.0310.063≤0.031≤0.031
10≤0.031≤0.031≤0.031≤0.031≤0.031
11≤0.031≤0.0310.250.0630.5
12≤0.031≤0.0310.125≤0.0310.25
13≤0.031≤0.0310.031≤0.0310.063
14≤0.031≤0.0310.125≤0.031 0.125
150.0630.0631≤0.0312
16≤0.031≤0.0310.063≤0.0310.125
17≤0.031≤0.0310.125≤0.0310.125
180.1250.0630.5≤0.0311
190.50.252≤0.0318
20≤0.031≤0.0310.125≤0.0310.125
21≤0.0310.0630.5≤0.0310.5
22≤0,031≤0.0310.125≤0.0310.063
23≤0.031≤0.0310.063≤0.031≤0.031

4td align="center"> 42
Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
24≤0.031≤0.0310.125≤0.031≤0.031
25≤0.031≤0.0310.25≤0.0310.063
260.250.510.258
270.510.516
28≤0.031≤0.031≤0.031≤0.0310.125
29≤0.031≤0.0310.125≤0.031≤0.031
30≤0.031≤0.031≤0.0310.031≤0.031
310.520.516>16
32≤0.0310.250.0630.0310.5
330.5>16216>16
340.0630.06312
35≤0.031≤0.0310.063≤0.031≤0.031
360.5228>8
37≤0.0160.1250.1251>8
380.58216>16
390.1250.1251≤0.0318
400.50.540.125>8
412240.5>8
1422>8
430.252218
440.0630.1250.250.1252
45≤0.0160.0310.0630.0632
46≤0.016≤0.0160.125≤0.0310.125
47≤0.016≤0.0160.031≤0.031≤0.016
480.031≤0.0160.25≤0.0310.5
49≤0.0160.125≤0.0310.031
50≤0.016≤0.0160.063≤0.0310.031
51≤0.016≤0.0160.063≤0.031≤0.016
52≤0.016≤0.0160.5≤0.031≤0.016
53≤0.016≤0.0160.063≤0.031≤0.016
541210.258
550.0630.0630.25≤0.0310.5

Example No.
MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
56≤0.016≤0.0160.125≤0.0310.031
57≤0.016≤0.0160.125≤0.0310.063
58≤0.016≤0.016≤0.016≤0.0310.031
590.1250.250.54>8
60≤0.016≤0.0160.25≤0.0310.125
61≤0.016≤0.0160.063 ≤0.031≤0.016
620.0310.0310.25≤0.0310.125
630.0310.0310.250.0310.25
64≤0.016≤0.0160.125≤0.0310.25
650.0630.0310.5≤0.0310.5
660.0310.0310.5≤0.0312
670.1250.0631≤0.0632
68≤0.016≤0.0160.063≤0.031 0.125
69≤0.016≤0.0160.063≤0.0310.125
70≤0.016≤0.0160.031≤0.031≤0.016
71≤0.016≤0.0160.125≤0.0310.125
72≤0.016≤0.0160.125≤0.0310.063
730.0310.0310.5≤0.0310.25
74≤0.016≤0.0160,125≤0.0310.031
750.031≤0.0160.125≤0.031 0.063
760.0630.0630.5≤0.0314
770.250.2520.0318
780.0630.0630.5≤0.0312
79≤0.016≤0.0160.031≤0.0310.031
800.0310.0310.25≤0.0310.5
81≤0.0160.0310.063≤0.0310.063
820.50.50.50.252
830.1250.1251≤0.0310.25
840.250.12510.0632
85≤0.016≤0.0160.125≤0.0310.063
860.0310.0630.25≤0.0310.25
870.0310.0310.125≤0.0310.5

Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
88≤0.016≤0,016 0.125≤0.0310.25
890.250.250.50.0632
90≤0.016≤0.0160.125≤0.0310.25
91≤0.016≤0.0160.063≤0.0310.125
92≤0.016≤0.0160.25≤0.0310.5
93≤0,016≤0.0160.063≤0.0310.25
94≤0.016≤0.0160.125≤0.0310.5
950.031≤0.0160.25 ≤0.0311
96≤0.016≤0.0160.125≤0.0310.25
970.0310.0310.25≤0.0310.5
988820.25>8
99≤0.016≤0.0160.063≤0.0310.125
1000.250.250.50.0318
1010.0310.0310.125≤0.0312
1020.0310.0310.25 ≤0.0311
1030.031≤0.0160.25≤0.0310.5
104≤0.016≤0.0160.063≤0,0310.125
105≤0.016≤0.016≤0.016≤0.0310.031
106≤0.016≤0.0160.125≤0.0310.25
1078888>8
1080.50.54≤0.031>8
109≤0.016≤0.0160.125≤0.031 0.031
1100.0310.0310.031≤0.0310.25
1110.1250.0630.50.1250.5
112≤0.016≤0.0160.125≤0.0310.25
113≤0.016≤0.0160.125≤0.0310.5
114≤0.016≤0.0160.063≤0.0310.125
115≤0.016≤0.0160.031≤0.031≤0,016
116≤0.016≤0.016≤0.016 ≤0.0310.031
117≤0.016≤0.0160.031≤0.0310.063
118≤0.016≤0.016≤0.016≤0.031≤0.016
1190.0310.0310.5≤0.0311

2
Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
12024>80.125>8
1210.250.2540.1258
122480.52
1231280.1252
124≤0.016≤0.0160.031≤0.0310.031
125≤0.016≤0.0160.031≤0.0310.031
126≤0.016≤0.016≤0.016≤0.031≤0.016
127≤0.016≤0.0160.031≤0.0310.031
128≤0.016≤0.0160.031≤0.0310.063
129≤0.016 ≤0.0160.031≤0.0310.063
130≤0.016≤0.0160.063≤0.0310.25
131≤0.016≤0.0160.125≤0.0310.063
132≤0.016≤0.0160.063≤0.0310.063
133≤0.016≤0.0160.125≤0.0310.125
1340.1250.51≤0.0310.5
135≤0.0160.0310.125≤0.0310.031
136 ≤0.016≤0.0160.063≤0.0310.063
137≤0.016≤0.0160.063≤0.031≤0.016
138≤0.016≤0.0160.063≤0.0310.063
139≤0.016≤0.0160.125≤0.0310.125
1400.031≤0,0160.25≤0.0310.25
1410.1250.1250.5≤0.0310.5
142≤0.016≤0.0160.031≤0.0310.031
143 ≤0.016≤0.0160.063≤0.0310.063
144≤0.016≤0.0160.063≤0.0310.063
145≤0.016≤0.0160.125≤0.0310.125
1460.0630.0310.5≤0.0311
147≤0.016≤0.0160.063≤0.0310.031
148≤0.016≤0.0160.125≤0.0310.125
1490.1250.1250.5≤0.0311
150 ≤0.016≤0.0160.063≤0.0310.125
151≤0.016≤0.0160.125≤0.0310.125

Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
152≤0.016≤0.0160.125≤0.0310.125
153≤0.016≤0.0160.031≤0.0310.063
1540.0630.1250.5≤0.0311
1550.0310.031 0.5≤0.0310.125
156≤0.016≤0.0160.063≤0.0310.031
1578882>8
1580.0310.0310.25≤0.0310.5
159≤0.016≤0.0160.125≤0.0310.125
160≤0.016≤0.0160.125≤0.0310.25
1610.1250.12520.125>8
1620.522 0.25>8
1630.1250.2510.0311
1640.1250.2510.0318
1650.1250.12510.1251
166≤0.016≤0.0160.25≤0.0310.125
167≤0.016≤0.0160.25≤0.0310.25
168≤0.016≤0.0160.25≤0.0310.125
169≤0.016≤0.0160.25≤0.031 0.25
1700.250.2540.258
171≤0.016≤0.0160.063≤0.0310.063
1720.50.580.25>8
1731180.125>8
1740.0630.1250.5≤0.0312
175≤0.016≤0.0160.031≤0.0310.063
176≤0.016≤0.0160.031≤0.031≤0.016
177≤0.016≤0.016≤0.016≤0.031≤0.016
178≤0.016≤0.016≤0.016≤0.031≤0.016
179≤0.016≤0.016≤0.016≤0.0310.5
180≤0.016≤0.0160.063≤0.0310.063
181≤0.016≤0.0160.5≤0.0310.5
1820.0310.0310.25≤0.0310.5
183≤0.016≤0.0160.063≤0.0310.125

Example No.MIC for S. aureus ATCC29213MIC for S. aureus A798MIC for E. faecalis ATCC29212MIC for M. catarrhalis A894MIC for A. baumannii T
184≤0.016≤0.0160.063≤0.0310.125
185≤0.016≤0.0160.063≤0.0310.063
1860.50.580.58
1870.0310.0310.5≤0.0310.125
1880.1250.1251≤0.0312
1890.0630.125≤0.0310.125
190≤0.016≤0.0160.125≤0.0310.125
191≤0.016≤0.016≤0.016≤0.031≤0.016
192≤0.016≤0.016≤0.016≤0.0310.031
193≤0.016≤0.0160.125≤0.0310.125
194≤0.016≤0.0160.063≤0.0310.063
195≤0.016≤0.016≤0.016≤0.0310.016
196≤0.016 ≤0.016≤0.016≤0.031≤0.016
197≤0.016≤0.016≤0.016≤0.031≤0.016
198≤0.016≤0.016≤0.016≤0.031≤0.016
199≤0.016≤0.016≤0.016≤0.0310.031
200≤0.016≤0.0160.031≤0.0310.031
201≤0.016≤0.0160.5≤0.0310.25
2020.0630.03120.0631

1. The compound of formula (I)CE

where
"-----" means a bond, V represents CH and U represents CH or N, or "-----" means a bond, V represents CR6and U represents CH, or also "-----" means a bond, V represents N and U represents CH, or
"-----" is absent, V represents CH and U represents CH2, NH or NR9;
R0represents H or, in the case when "-----" means a connection can also be a C1-3alkoxygroup;
R1represents H, halogen, cyano, C1-3alkyl or ethinyl;
R2represents H, acetyl or a group of formula-CH2-R3;
R3represents H, C1-3alkyl or C1-3hydroxyalkyl;
R4represents H or, in the case when n is 0 and R5denotes H, can also be a HE;
R5represents H, C1-3alkyl, C1-3hydroxyalkyl,1-3aminoalkyl,1-3alkoxyl1-3alkyl, carboxyl group or1-3alkoxycarbonyl;
R6represents a C1-3hydroxyalkyl, a carboxyl group, a C1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q is 1, 2 or 3 and each of R7and R8independently from each other represents H or C1-3alkyl, or R7and Rsup> 8together with the nitrogen atom to which they are attached, form pyrrolidinyl or piperidinyl ring;
R9represents a C1-3alkyl, 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl;
And represents -(CH2)p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;
G represents a phenyl group which is substituted once or twice in the m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen, or G represents a group of the following formula G1and G2

where
Q denotes O or S, and X denotes CH or N; and
Y1, Y2and Y3each represents CH, or one of the Y1and Y3represents N and the other represents CH; and
n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3 or 4;
or pharmaceutically acceptable salt of such compounds.

2. The compound of formula (I)CEaccording to claim 1, which is a compound of formula (I)P3

where
"-----" means a bond, V represents CH and U Ave dstanley a CH or N, or "-----" means a bond, V represents CR6and U represents CH, or also "-----" means a bond, V represents N and U represents CH, or
"-----" is absent, V represents CH and U represents CH2or NH;
R0represents H or, in the case when "-----" means a connection can also be a1-3alkoxygroup;
R1represents H, halogen, cyano or1-3alkyl;
R2represents H, acetyl or a group of formula-CH2-R3;
R3represents H, C1-3alkyl or C1-3hydroxyalkyl;
R4represents H or, in the case when n is 0 and R5denotes H, can also be a HE;
R5represents H, C1-3alkyl, C1-3hydroxyalkyl,1-3alkoxyl1-3alkyl or C1-3alkoxycarbonyl;
R6represents a C1-3hydroxyalkyl, carboxyl group, With1-3alkoxycarbonyl or a group -(CH2)q-NR7R8where q is 1, 2 or 3 and each of R7and R8independently from each other represents N or C1-3alkyl, or R7and R8together with the nitrogen atom to which they are attached, form pyrrolidinyl or piperidinyl ring;
And represents -(CH2 )p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;
G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen, or G is a group one of the following formulas G1and G2

where
Q denotes O or S, and X denotes CH or N; and
Y1, Y2and Y3each represents CH, or one of the Y1and Y3represents N and the other represents CH; and
n is 0 when a is a-CH2CH2CH(OH)- or-PINES2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3 or 4;
or pharmaceutically acceptable salt of such compounds.

3. The compound of formula (I)CEaccording to claim 1, which is also a compound of the formula (I)P2

where
"-----" means a bond, V represents CH and U represents CH or N, or "-----" means a connection or "-----" means a bond, V represents N and U represents CH, or
"-----" is absent, V represents CH and U represents CH2or NH;
R0the present is the focus of a N or, in the case when "-----" means a connection can also be a C1-3alkoxygroup;
R1represents H or halogen;
R2represents H or a group of formula-CH2-R3where R3denotes hydrogen, C1-3alkyl or C1-3hydroxyalkyl;
And represents -(CH2)p-, -CH2CH2CH(OH)- or-PINES2CH(OH)-;
G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected
independently from each other from C1-4of alkyl, C1-3alkoxygroup and halogen; or G represents a group of one of the following formulas G1and G2

where
Q denotes O or S, and X denotes CH or N; and
Y1, Y2and Y3each represents CH, or one of the Y1and Y3represents N and the other represents CH; and
n is 0 when a is a-CH2CH2CH(OH)- or-COCH2CH(OH)-, and n is 0, 1 or 2 when a is a (CH2)pwhere p is 1, 2, 3, or 4, provided that the sum of n and p are equal then 2, 3 or 4;
or pharmaceutically acceptable salt of such compounds.

4. The compound of formula (I)CEaccording to claim 1, which is also a compound of the formula (I)P1

where
"-----" means a bond, V represents CH and U represents CH or N, or "-----" means a connection or "-----" means a bond, V represents N and U represents CH, or
"-----" is absent, V represents CH and U represents CH2or NH;
R1represents H or halogen;
G represents a phenyl group which is once or twice substituted in m - and/or p-position(s) by substituents selected independently of one another from C1-4of alkyl, C1-3alkoxygroup and halogen; or G represents a group of one of the following formulas G1and G2

where
Q denotes O or S, and X denotes CH or N; and
Y1, Y2and Y3each represents CH, or one of the Y1and Y3
represents N and the other represents CH; and
n is 0, 1 or 2 and p is 1, 2 or 3, provided that the sum of n and p is equal to or 2, or 3;
or pharmaceutically acceptable salt of such compounds.

5. The compound of formula (I)CEaccording to one of claims 1 to 4, where R1represents fluorine; or a pharmaceutically acceptable salt of such compounds.

6. The compound of formula (I)CEaccording to one of claims 1 to 4, where V represents CH; or a pharmaceutically acceptable salt of such compounds.

7. The connection is of the formula (I) CEaccording to one of claims 1 to 4, where V represents N; or a pharmaceutically acceptable salt of such compounds.

8. The compound of formula (I)CEaccording to one of claims 1 to 4, where "-----" indicates a relationship and U represents CH or N; or a pharmaceutically acceptable salt of such compounds.

9. The compound of formula (I)CEaccording to one of claims 1 to 4, where "-----" is absent and U represents CH2, NH or NR9; or a pharmaceutically acceptable salt of such compounds.

10. The compound of formula (I)CEaccording to one of claims 1 to 4, where a represents -(CH2)pis, the sum of n and p is equal to 3, each of R0, R4and R5represents H and G denotes a group of the formula G1or G2according to claim 1; or a pharmaceutically acceptable salt of such compounds.

11. The compound of formula (I)CEaccording to paragraph 10, where n is 0 And represents -(CH2)pand p is 3; or a pharmaceutically acceptable salt of such compounds.

12. The compound of formula (I)CEaccording to one of claims 1 to 4, which has the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry shown in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following four the ule

or pharmaceutically acceptable salt of such compounds.

13. The compound of formula (I)CEaccording to one of claims 1 to 4, which has the stereochemistry shown in the following formula

or, in the special case of the compounds of formula (IP2)have the stereochemistry,
represented in the following formula

or also, in the special case of the compounds of formula (IP1)have the stereochemistry shown in the following formula

or pharmaceutically acceptable salt of such compounds.

14. The compound of formula (I)CEaccording to one of claims 1 to 4, where G is a group of the formula

where Q represents O or S; or a pharmaceutically acceptable salt of such compounds.

15. The compound of formula (I)CEaccording to claim 1, where
"-----" means a connection and V represents CH and U represents CH or N, or V represents N and U represents CH;
R0represents H;
R1represents H or fluorine;
R2represents H;
R4represents H;
R5represents H, methyl, hydroxymethyl or aminomethyl;
n is 0 and represents -(CH2)p-where p is 2, 3 or 4, or n is 1 and a is a -(CH2 )p-where p is 1, 2 or 3; and
G represents a group of the following formula G1

where X denotes CH or N and Q represents O or S;
or pharmaceutically acceptable salt of such compounds.

16. The compound of formula (I)CEaccording to claim 1, where
"-----" is absent and U represents NH or NR9where R9
represents methyl;
R0represents H;
R1represents H or fluorine;
R2represents H;
each of R4and R5represents H;
n is 0 and represents -(CH2)p-where p is 2, 3 or 4, or n is 1 and a is a -(CH2)p-where p is 1, 2 or 3; and
G represents a group of the following formula G1

where X denotes CH or N and Q represents O or S;
or pharmaceutically acceptable salt of such compounds.

17. The compound of formula (I)CEaccording to claim 1, which is selected from the following compounds:
9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxaz is lidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[3-(3-fluoro-4-were)-2-oxoacridine-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{2-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(4R)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]the Mino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(4R)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
9-fluoro-1-(2-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
1-(2-{[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}ethyl)-9-fluoro-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{[(R)--(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}ethyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;
9-fluoro-1-({[(R)-3-(3-fluoro-4-were)-2-oxoacridine-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(R)-3-(4-butylphenyl)-2-oxoacridine-5-ylmethyl]amino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthyridin-he;
(S)-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
1-({2-[3-(2,3-dihydro-[1,4]like[2,3-c]pyridine-7-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[3-(2,3-dihydro-[1,4]like[2,3-b]pyridine-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(R)-3-(4-ethoxyphenyl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(R)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylaminomethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-6-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-6-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
9-fluoro-1-{2-[(R)-2-oxo-3-(4-propylphenyl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}methyl)-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]atrami what about the}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-7-fluoro-6-((2-hydroxyethyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propyl}amino)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
9-fluoro-1-(2-{(3-hydroxypropyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(2-{(2-hydroxyethyl)-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}ethyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-di is itapira[1,2,3-de]cinoxacin-3-one;
(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de] [1,5]naphthiridine-7-he;
(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
3-fluoro-4-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-[((3-hydroxypropyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-[((2-hydroxyethyl)-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethyl}amino)methyl]-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-((3-hydroxypropyl)-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-((2-hydroxyethyl)-{3-[(R-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo [3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo [3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-4,5-dihydropyrrolo[3,2,1-de] [1,5]naphthiridine-7-he;
3-fluoro-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
3-fluoro-4-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
6-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
1-{2-[(S)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxoacridine-5-yl]ethylamino}-9-fluoro-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one
N-((S)-9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-3-hydroxy-3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propionamide;
(R)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
6-({[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-7-fluoro-2-methoxy-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
9-fluoro-1-{3-hydroxy-3-[2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
9-bromo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile
4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-9-carbonitrile;
ethyl ester of (R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;
(R)-7-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid;
(R)-7-dimethylaminomethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-7-pyrrolidin-1-ylmethyl-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-6][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-is)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-BAA is zo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de] [1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de] [1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(R)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-di is itapira[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
(S)-3-fluoro-4-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-4,5-dihydropyrrolo[3,2,1-de] [1,5]naphthiridine-7-he;
9-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-(methyl-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}amino)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
6-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(RS)-6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
6-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one;
(R)-1-{2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-1-{2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-{4-[(S)-2-oxo-3-(3-ACS is -3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]-butylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-7-fluoro-6-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
methyl ester of (1R*,2R*)-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;
methyl ester of (1R*,2R*)-4-oxo-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;
(1R*,2R*)-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2R*)-2-hydroxymethyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;
(1R*,2R*)-2-methoxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo,4-dihydro-2H-pyrido[3,2-b] [1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2R*)-2-(1-hydroxy-1-methylethyl)-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-7-fluoro-6-{3-[((R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
N-(9-fluoro-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-yl)-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propyl}ndimethylacetamide;
(S)-4-hydroxy-4-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-4,5-dihydropyrrolo[3,2,1-de][1,5]naphthiridine-7-he;
9-fluoro-1-hydroxy-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-ylmethyl]amino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-chloro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-dij]quinoline-4-one;
9-ethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-digitope is Rolo[3,2,1-ij]quinoline-4-one;
9-ethinyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
methyl ester of (1R*,2R*)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;
(1R*,2R*)-9-fluoro-2-hydroxymethyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-9-fluoro-2-methyl-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2R*)-9-fluoro-4-oxo-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid;
9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinoline-4-one;
(1R*,2S*)-2-aminomethyl-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(S)-2-oxo-3(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo [3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
(R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
9-fluoro-1-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]thiazin-6-yl)oxazolidin-5-yl]ethylamino}methyl)-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one;
7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]henok is Aline-3-one;
7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-methyl-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1-(3-hydroxypropyl)-1,2,5,6-tetrahydropyrrolo[1,2,3-de]cinoxacin-3-one;
or pharmaceutically acceptable salt of such compounds.

18. The compound of formula (I)CEaccording to claim 1, which means (S)-7-fluoro-6-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one, or pharmaceutically acceptable salt of such compounds.

19. The compound of formula (I)CEaccording to claim 1, which means (S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

20. The compound of formula (I)CEaccording to claim 1, which means (S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

21. The compound of formula (I)CEaccording to claim 1, which means that (R)-7-fluoro-6-{3-[(S)--oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-5,6-dihydropyrrolo[1,2,3-de]cinoxacin-3-one, or pharmaceutically acceptable salt of such compounds.

22. The compound of formula (I)CEaccording to claim 1, which means (S)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

23. The compound of formula (I)CEaccording to claim 1, which means (S)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

24. The compound of formula (I)CEaccording to claim 1, which means that (R)-9-fluoro-1-{3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl) oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

25. The compound of formula (I)CEaccording to claim 1, which means that (R)-9-fluoro-1-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]propylamino}-1,2-dihydropyrrolo[3,2,1-ij]quinoline-4-one, or pharmaceutically acceptable salt of such compounds.

26. The compound of formula (I)CEaccording to one of claims 1 to 4, or its pharmaceutically acceptable salt as a medicine for the prevention or treatment of bacterial infections.

27. Pharmaceutical composition for prevention or treatment of the bacterium is the first infection, containing as an active ingredient a compound of the formula (I)CEaccording to one of claims 1 to 4, or its pharmaceutically acceptable salt, and at least one therapeutically inert excipient.

28. The use of the compounds of formula (I)CEaccording to one of claims 1 to 4, or its pharmaceutically acceptable salt to obtain drugs for prevention or treatment of bacterial infections.

29. The compound of formula (I)CEaccording to one of claims 1 to 4, or its pharmaceutically acceptable salt for the prevention or treatment of bacterial infections.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to antibacterial compounds of formula

,

where R1 is an alkoxy group; R2 is H or F; each of R3, R4, R5 and R6 is independently H or D; V is CH and W is CH or N, or V is N and W is CH; Y is CH or N; Z is O, S or CH2 and A is CH2, CH2CH2 or CD2CD2; or a salt of said compound. The invention also describes a antibacterial pharmaceutical composition which contains the compound of formula (I) as a basic component, and use of the compound of formula (I).

EFFECT: obtaining novel compounds possessing useful biological properties.

25 cl, 2 tbl, 24 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (I) where R1 is phenyl, imidazo[2,1-b][1,3]thiazolyl, pyridinyl, pyrazolo[1,5-a]pyridinyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, imidazo[2,1-b][1,3,4]thiadiazolyl, 1H-indazolyl, pyridazinyl, imidazo[1,2-b][1,2,4]triazinyl, 1H-pyrazolo[3,4-b]pyridinyl, imidazo[1,2-b]pyridazinyl, 2,3-dihydro[1,4]dioxino[2,3-b]pyridinyl, oxadiazolyl or imidazo[1,2-a]pyridinyl; each of which is optionally substituted with 1-3 substitutes, independently selected from methyl, methoxy, cyano, cyclopropyl, -C(O)NH2 and -NHC(O)CH3; Ra in each case is hydrogen; each of Z, Z1 and Z2 is independently CH; L is a direct bond; and R2 is hydrogen, phenyl, phenoxy, pyrimidinyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, thiadiazolyl, pyridinyl, oxazolyl, oxadiazolyl, pyrazolyl, pyridazinyl, triazinyl or pyrazinyl, each optionally substituted with 1-3 substitutes independently selected from methyl, trifluoromethyl, ethyl, methoxy, cyano or -C(O)NH2; or pharmaceutically acceptable salts thereof, which act as ghrelin antagonists or inverse agonists.

EFFECT: obtaining novel derivatives.

13 cl, 1 dwg, 11 tbl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula I, having cell proliferation inhibitor properties. In formula I , Y1 and Y2 each independently denote N or C(R1), but Y1 and Y2 do not simultaneously denote N or do not simultaneously denote C(R1), where R1 is selected from a group consisting of a hydrogen atom, C1-6alkyl, where R1 is substituted with 0 or 1 substitutes RR1, selected from a group consisting of -ORa; where Ra is selected from a hydrogen atom; R2 is selected from a group consisting of a hydrogen atom, C1-6alkyl; R3 is a 6-7-member monocyclic or bridge heterocycloalkyl ring containing 2 heteroatoms, selected from N and O, where the group R3 is substituted with 0-3 substitutes RR3, selected from a group consisting of -Ri, Ri is selected from C1-6alkyl; A1, A2, A3 and A4 each denote C(H); and D denotes -NR4C(O)NR5R6, where R4 is selected from a group consisting of a hydrogen atom; R5 and R6 are each independently selected from a group consisting of a hydrogen atom, C1-6alkyl, C4-6heterocycloalkyl containing one oxygen heteroatom; and where R5 and R6 are further substituted with RD, where RD is selected from -S(O)2Rm, where Rm is selected from C1-6alkyl.

EFFECT: compounds can be used to produce medicine for treating cancer.

21 cl, 1 tbl, 21 ex

FIELD: biotechnologies.

SUBSTANCE: invention refers to derivatives of oxazolopyrimidine in any of their stereoisomeric forms, or in the form of a mixture of stereoisomeric forms specified in Claim 1.

EFFECT: oxazolopyrimidine derivatives having agonistic activity in relation to Edg-1 receptor.

5 tbl, 319 ex

FIELD: chemistry.

SUBSTANCE: invention relates to use of novel pyrrolopyrazine derivatives of formula , where variables Q and R are as defined in the claim, which inhibit JAK and SYK.

EFFECT: high effectiveness when treating autoimmune and inflammatory diseases.

11 cl, 59 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (I) where "----" denotes a bond or is absent; R1 is a C1-4alkoxy group or halogen; R1b is H or C1-3alkyl; U and V each independently denote CH or N; W is CH or N, or, if "----" is absent, W is CH2 or NH; under the condition that at least one of U, V and W is CH or CH2; A is -CH2-CH(R2)-B-NH-* or -CH(R3)-CH2-N(R4)-[CH2]m-*; where asterisks indicate a bond which binds said fragments through a CH2-group with an oxazolidinone fragment; B is CH2 or CO; and R2 is hydrogen, OH or NH2; R3 and R4 both denote hydrogen, or R3 and R4 together form a methylene bridge; m equals 0, 1 or 2; and G is a phenyl which is monosubstituted in position 3 or 4, or disubstituted in positions 3 and 4, where each substitute is independently selected from a group comprising C1-4alkyl, C1-3alkoxy group and halogen; or G is a group selected from groups G1 and G5 where M is CH or N; Q' is S or O; Z1 is N, Z2 is CH and Z3 is CH; or Z1 is CH, Z2 is N and Z3 is CH or N; or Z1 is CH, Z2 is CR5 and Z3 is CH; or Z1 is CH, Z2 is CH and Z3 is N; and R5 is hydrogen or fluorine; or a pharmaceutically acceptable salt thereof. The compound of formula (I) or a pharmaceutically acceptable salt thereof are used as a medicinal agent for preventing or treating bacterial infections.

EFFECT: oxazolidinone derivatives used as antimicrobial agents.

15 cl, 2 tbl, 44 ex

FIELD: chemistry.

SUBSTANCE: invention relates to dihydrothienopyrimidinesulphoxides of formula 1, and pharmaceutically acceptable salts thereof , where X denotes SO, R1 denotes H, R2 denotes H or a residue selected from C1-C10alkyl, which is optionally substituted with one or more residues selected from OR2.1, where R2.1 denotes H or C1-C6alkyl, R2.2 and R2.3 independently denote H or C1-C6alkyl, where Het is a 6-member monocyclic, saturated heterocycle containing 1 heteroatom selected from N or O, and where the hetaryl is a 5-11-member mono- or bicyclic, optionally anellated heteroaryl containing 1, 2 or 3 heteroatoms independently selected from N, S or O, and where the cycloalkyl can be saturated, or R2 denotes a monocyclic C3-cycloalkyl, which is optionally substituted with a residue selected from a branched or linear C1-C6alkanol, C1-C3alkylene-OR2.1, or R2 denotes phenyl which is optionally substituted with a halogen, or R2 denotes a residue selected from Het and hetaryl, each optionally substituted with one or more residues selected from halogen, OH, oxo group and OR2.1, C1-C6alkyl, and where R3 denotes a bicyclic 9-11-member unsaturated or partially saturated heterocycle which is optionally substituted with one or more residues selected from a group comprising F, O, Br, CF3, CN, OH, methyl, ethyl, propyl, isopropyl, -O-methyl, -O-ethyl, phenyl, NR2.2R2.3, where the phenyl is optionally substituted with F, Cl or Br. The invention also relates to pharmaceutical compositions based on said compounds, having phosphodiesterase 4 (PDE4) inhibiting activity.

EFFECT: obtaining novel compounds and pharmaceutical compositions based thereon, which can be used in medicine to treat respiratory or gastrointestinal complaints or diseases, inflammatory diseases of joints, skin or eyes, diseases of the peripheral or central nervous system or cancers.

20 cl, 1 tbl, 156 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a new compound, namely 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluor-1,5-naphthyridin-2(1H)-one monohydrate which possess strong antibacterial activity. This compound is highly safe and applicable in the production of pharmaceutical preparations as a parent drug. What is furthermore described is a method for preparing 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluor-1,5-naphthyridin-2(1H)-one monohydrate of formula 19 and methods for preparing intermediate compounds.

EFFECT: preparing the compounds possessing strong antibacterial activity.

8 cl, 1 tbl, 17 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to novel quinoline compounds of formula (I) and physiologically acceptable acid addition salts and N oxides thereof, wherein R denotes a polycyclic group of formula (R) wherein * indicates the quinolinyl radical binding site; A denotes (CH2)a, where a equals 0, 1, 2 or 3; B denotes (CH2)b, where b equals 0, 1, 2 or 3; X' denotes (CH2)x where x equals 0, 1, 2 or 3; Y denotes (CH2)y where y equals 0, 1, 2 or 3; provided that a+b=1, 2, 3 or 4, x+y=1, 2, 3 or 4, and a+b+x+y=3, 4, 5, 6 or 7; Q denotes N; R1 denotes hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, phenoxycarbonyl or benzyloxycarbonyl, where phenyl rings in last two said groups are unsubstituted or carry 1, 2 or 3 substitutes selected from halogen, C1-C4-alkyl or C1-C4-halogenalkyl; R2 denotes hydrogen; R3 denotes hydrogen; p=0, 1 or 2; R4, if present, denotes C1-C4-alkyl and is bonded with X and/or Y, if p=2, two radicals R4, which are bonded with adjacent carbon atoms of X or Y, together can also denote a straight C2-C5-alkylene; q=0; n=0; m=0; X denotes S(O)2; which is located in position 3 of quinoline; Ar denotes a radical Ar1, wherein Ar1 is a phenyl, wherein the phenyl can be unsubstituted or can carry 1 substitute Rx wherein Rx denotes halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, NRx1 Rx2, wherein Rx1 and Rx2 independently denote hydrogen, C1-C6-alkyl, or Rx1 and Rx2 together with a nitrogen atom form an N-bonded 5-, 6- or 7-member saturated heteromonocyclic ring or an N-boned 7-, 8-, 9- or 10-member saturated heterobicyclic ring, which are unsubstituted or carry 1, 2, 3 or 4 radicals selected from C1-C4-alkyl. The invention also relates to a pharmaceutical composition based on the compound of formula (I), a method of treatment using the compound of formula (I) and use of the compound of formula (I).

EFFECT: novel quinoline derivatives are obtained, which respond to modulation of the serotonin 5-HT6 receptor.

23 cl, 2 tbl, 44 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula 1 , where X and T are N or C, Q is a (3-7)-member aromatic ring which contains 0-3 nitrogen atoms as ring members, and which is optionally benzo-condensed and is substituted with oxo; C1-C6-alkyl; halogen- C1-C6-alkyl; hydroxy-C1-C6-alkyl; C1-C6-alkoxy; C6-C10-aryl; or a (3-7)-member heteroaryl containing 1-3 oxygen atoms, P is C1-C6-alkyl, optionally substituted with a halogen, and R is a group selected from: (i) -C1-C6-alkyl-R1, (ii) -NR2R3, (iii) -O-R4, (iv) -S-R5, (v) -C (=O))-R6, (vi) optionally substituted (3-7)-member heteroaryl containing 1-4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulphur atom, (vi) optionally substituted (3-7)-member heteroatom containing 1-4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulphur atom, (vii) optionally substituted, saturated or partially unsaturated, separate or condensed (3-10)-member heterocyclic ring containing 1-4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulphur atom, (viii) azido; where each R1, R2, R3, R4, R3, R6, is as described in the claim. The invention also relates to a pharmaceutical composition for preventing and treating a vascular disease, which contains a compound of formula 1.

EFFECT: compounds of formula 1 with inhibitory activity with reference to aggregation of thrombocytes.

7 cl, 7 dwg, 2 tbl, 519 ex

FIELD: chemistry.

SUBSTANCE: invention refers to the means of production of zilpaterol and its salts including: production of chlorine 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate (or its salt) by means of the method including interaction between 4-(2-oxo-2,3-dihydrobenzimidazol-1-yl)butanoic acid (or its salt) and at least one chlorating agent chosen from the group consisting of oxalyl chloride, phosgene and triphosgene, and production of 8,9-dihydro-2H,7H-2,9a-diabenzo[c,d]azulene-1,6-dione or its salt, by means of the method including interaction between chlorine 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate (or its salt) with the Lewis acid, production of 4,5-dihydro-imidazo[4,5,l-jk][1]benzazepin-2,6,7[1H]-thrion-6-oxime (or its salt) by means of the method including interaction between 8,9-dihydro-2H,7H-2,9a-diazabenzo[cd]azulene-1,6-dione (or its salt) with nonorganic nitrite, production of alkamine salt by means of the method including interaction between 4,5-dihydro-imidazo[4,5,l-jk][1]benzazepin-2,6,7[1H]-thrion-6-oxime (or its salt) with the base and further interacton with H2 with the presence of hydrogenation catalyst; the alkamine salt corresponds to the structural formula WO-2): and Z denotes a cation, production of izopropilidenamino compound be means of the method including combination of the alkamine salt with acetone and acetic acid; the izopropilidenamino compound structurally corresponds to the formula (WO-1): and production of zilpaterol by interaction between the izopropilidenamino compound (or its salt) and H2 with the presence of hydrogenation catalyst, with further combination with the base and alcohol, and to the ways of production of intermediate compounds that may be used in productioin of zilpaterol and its salts.

EFFECT: new way of production of zilpaterol and its salt that can be used for acceleration of weight gain, improvement of feed efficiency and/or increase of meagreness of a great cattle, poultry and fish carcass.

12 cl, 9 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method for selective synthesis of 6R,7R trans-stereoisomer of 6-amino-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2[1H]-one and 6R,7R trans-stereoisomer of zilpaterol or salts thereof for preparing medicinal agents. The disclosed method of producing 6R,7R trans-stereoisomer of 6-amino-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2[1H]-one involves reaction of 4,5-dihydroimidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime or salt thereof with H2 in the presence of a catalyst which contains a complex of at least one phosphine ligand with at least one metal selected from a group comprising rhodium, ruthenium and iridium. The disclosed method for selective synthesis of the 6R,7R trans-stereoisomer of zilpaterol involves reaction of 4,5-dihydroimidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime with H2 in the presence of a catalyst to form 6-amino-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2[1H]-one and conversion of the latter to zilpaterol.

EFFECT: novel method of producing biologically active compounds.

24 cl, 7 ex, 2 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to a compound of formula

, or its pharmaceutically and veterinary acceptable salts, where: A represents -CH2-; and B represents -CH2-, -C(CH3)2-; or -A-B- represents -CH=CH-; one of R1 and R2 represents CH3 and another represents H; R3, R4, R5, R6 and R7, each is independently selected from H, R8 and R9; or R4 and R5 together represent -OCH2-CH2-, -CH2-CH2-O- or -O-CH2-O- and R3, R6 and R7, each represents H; R8 represents halogen, -CN, C1-C4alkyl, C1-C4haloalkyl, -CH2OH, -O-(C1-C4 alkyl), -O-CH2-(C3-C5) cycloalkyl, -CO2H, -CO2(C1-C4 alkyl), -CON2H -CONH(C1-C4alkyl), -CONH(C1-C4 haloalkyl), -COKH(C3-C6 cycloalkyl) or NH2; and R9 represents OH, -NHSO2(C1-C3 alkyl), -NHCO(C1-C4 alkyl), -NHCO(C1-C4 haloalkyl), -NHSO2(C1-C3 haloalkyl) or -NHSO2(phenyl). Also, the invention refers to a pharmaceutical composition based on the compound of formula (I) which exhibits bovine and swine adrenergic beta-2-receptor agonist activity.

EFFECT: there are produced new compounds showing effective biological properties.

12 cl, 101 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: described is novel derivative of pyrimidinotetrazole-methyl 6-acetyl-7-(2,5-dimetoxyphenyl)-4,7-dihydrotetrasolo[1,5-a]pyrimidine-5-carboxylate of formula

EFFECT: obtaining medication which possesses anti-fever action.

1 cl, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel pyrroloquinolinyl-pyrrolidine-2,5-diones of formula IVa, IVb, Va or Vb or pharmaceutically acceptable salts thereof: where: R1, R2, R3 and R4 independently denote H; Q denotes a benzo-condensed 5-member heteroaryl with one N atom; X denotes -(CH2)-; Y denotes -(CH2)-, a bond; m equals 1 or 2.

EFFECT: compounds inhibit growth of cancerous cells, which enables their use in pharmaceutical compositions.

12 cl, 2 tbl, 12 dwg, 88 ex

FIELD: chemistry.

SUBSTANCE: invention relates to use of poly (ADP-ribose) polymerase inhibitors of formulae I, II and III in treating cancerous growths in cells with genetic defect of a homologous recombination mediating gene. When using compounds of formulae I, II and III, a mammal with a genetic defect of a homologous recombination mediating gene is selected first and said compounds are then used to induce opoptosis in cells with said defect

EFFECT: method of treating cancer in mammals with genetic defect of a homologous recombination mediating gene.

23 cl, 9 dwg, 1 tbl

FIELD: chemistry.

SUBSTANCE: described is a method for preparation of a new class compounds represented by 1,2,3,6-tetrahydropropyrrolo[1,2-d][1,4]diazocine derivatives with a general formula of I-VI , where: I R1=Me R2=Me R3=CHO X=CO2Me; II R1=Et R2=MeR3=CHO X=CO2Me; III R1=Et R2=Me R3=CF3CO a) X=CO2Me, b) X=COMe; IV R1=Bn R2=Me R3=CHO X=CO2Me; V R1=Me R2=Ph R3=CHO a) X=CO2Me, b) X=COMe; VI R1=Me R2=Ph R3=CF3CO a) X=CO2Me, b) X=COMe that may be of interest in the capacity of nootropic preparations. The proposed method is as follows: the relevant 1,2,3,4-tetrahydropropyrrolo[1,2-a][1,4]diazocine derivative becomes dissolved in acetonitrile and undergoes interaction with two moles of H-C≡C-X compound in combination with boiling during at least 7 hours, the residue produced after the reaction termination the solvent removal becomes purified by way of aluminium oxide column chromatography.

EFFECT: method for preparation of a new class compounds.

1 cl, 9 ex

FIELD: chemistry.

SUBSTANCE: invention concerns novel polymorphous and amorphous forms of 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-on phosphate of the formula (I) and pharmaceutical composition based on them, with modulation effect on poly(adenosine-5-diphosphate(AOP)-ribose)polymerase activity.

EFFECT: obtaining novel polymorphous and amorphous forms of compound phosphate of the formula (I) and pharmaceutical composition based on them for the purpose of treatment of disease state conditioned by poly(AOP ribose)polymerase activity, including such disease as cancer.

8 cl, 3 tbl, 24 dwg, 8 ex

FIELD: chemistry.

SUBSTANCE: invention concerns new derivatives of 1,3,4-triazaphenalene and 1,3,4,6-tetraazaphenalene of formula I and their pharmaceutically acceptable salts with inhibition effect on epidermal growth factor receptor (EGFR) of tyrosinekynase and with antiproliferation activity. E.g. compounds can be applied in treatment and prevention of cancer, particularly solid tumours. In formula I , Z is C or N; R1 and R2 are independently selected out of H, lower alkyl; R3 and R4 are independently selected out of H, F, Cl or Br; R5 is selected out of H, oxo group, thione, C1-C3alkyl. Invention also concerns pharmaceutical compositions containing the claimed compounds.

EFFECT: obtaining compounds with inhibition effect on EGFR of tyrosinekynase and with antiproliferation activity.

22 cl, 5 dwg, 23 ex

FIELD: medicine; pharmacology.

SUBSTANCE: invention refers to new condensed derivatives of azolpyrimidine of formula (I), their tautomeric or stereoisomeric form and their physiologically accepted salts. Compounds of this invention have improved activity of phosphatidyl inositol-3-kinase (P13K) inhibiting, specifically of P13K-γ inhibiting, and can be applied for production of medicinal agents for prevention and treatment of P13K- and P13K-γ activity based diseases. Those diseases are inflammatory and immunoregulatory diseases such as asthma and others. In compounds of formula (I) . X means CR5R6 or NH; Y1 means CR3 or N; chemical bond between means single bond or double bond, as long as means double bond, then Y2 and Y3 mean CH, and as long as mean single bond, then Y2 and Y3 mean regardless CR3R4; Z1, Z2, Z3 and Z4 mean redardless CH , CR2 or N; R1 means phenyl, optionally containing 1 to 3 substitutes selected from group including R11, C3-8cycloalkyl, optionally containing 1 to 3 substitutes selected from group including R11, C1-6alkyl, optionally containing as substitutes one or more halogen atoms, or 3-15-component mono- or bicyclic heterocyclic ring being saturated or non-saturated, optionally containing 1 to 3 substitutes selected from group including R11, and containing 1 to 3 heteroatoms selected from group including N, O and S, where R11 means halogen, nitro-, hydroxyl-, cyano-, carboxy-, amino-, N-(C1-6alkyl)amino-, K-(hydroxyC1-6alkyl)amino-, N,N-di(C1-6alkyl)amino-, N(C1-6acyl)amino-, N-(formyl)-N-(C1-6 alkyl) amino-, N-(C1-6alkansulphonyl)amino-, N-(carboxy C1-6 alkyl)-N-(C1-6 alkyl) amino-, N-(C1-6 alkansulphonyl)amino-, N-[N,N-di(C1.6 alkyl)aminomethylene] amino-, N-[N,N-di(C1-6 alkyl)amino(C1-6 alkyl)methylene]amino-, N-[N,N-di(C1-6 alkyl)aminoC1-6alkenyl]amides, aminocarbonyl, N-(C1-6 alkyl)aminocarbonyl, N,N-di(C1-6 alkyl)aminocarbonyl, C3-8 cycloalkyl, C1-6alkylthio, C1-6 alkansulphonyl, sulphamoyl, C1-6alkoxycarbonyl, phenylC1-6alkoxycarbonyl, where specified phenylic fragment optionally contains 1 to 3 substitutes selected from group including R101, C1-6alkyl, optionally containing as substitutes 1, 2 or 3 halogen atoms, C1-6alkoxy, optionally containing as substitutes 1, 2 or 3 halogen atoms, or 5- 7-component saturated or non-saturated ring containing 1 to 3 heteroatoms selected from group containing N, and optionally containing 1 to 3 substitutes selected from group including and R101, where R101 means halogen, carboxy, amino-, N-(C1-6alkyl)amino-, N,N-di(C1-6alkyl)amino-, aminocarbonyl, N-(C1-6alkyl)aminocarbonyl, N,N-di(C1-6alkyl)aminocarbonyl, C1-6alkyl, and C1-6alkoxy; R2 mean hydroxy, halogen, nitro-, cyano-, amino-, N-(C1-6alkyl)amino-, N,N-di(C1-6alkyl)amino-, N-(hydroxyC1-6alkyl)amino-, N-(hydroxyC1-6alkyl)-N-(C1-6alkyl)amino-, C1-6 acoxy, aminoC1-6 acoxy, C2-6alkenyl, phenyl, 5-7-compound saturated or non-saturated heterocyclic ring containing 1 to 2 heteroatoms selected from group including O and N, and optionally containing as substitutes: hydrohy, d-balkyl, N-(C1-6acyl)amino-, phenyl, phenylC1-6alkyl, C1-6alkyl, optionally containing as substitutes R21, or C1-6alkoxy, optionally containing as substitutes R21, where R21 means cyano group, 1, 2 or3 halogen atoms, hydroxy, amino-, N-(C1-6alkyl)amino-, N,N-di(C1-6alkyl)amino-, C1-6alkoxy, hydroxyC1-6alkoxy, -C(O)-R201, -NHC(O)-R201, C3-8 cycloalkyl, phthalymidil, 2-oxo-1,3-oxazolidinyl, phenyl or 5- or 6-compound saturated or non-saturated heterocyclic ring containing 1 to 4 heteroatoms selected from group including O and N, and optionally containing as substitutes hydroxy, C1-6alkyl, N-(C1-6acyl)amides or benzyl, where R201 means hydroxyl, amino-, N-(C1-6alkyl)amino-, N,N-di(C1-6alkyl)amino-, N-(halogenphenylC1-6 alkyl)amides, C1-6alkyl, aminoC1-6alkyl, C1-6alkoxy, 5- or 6-compound saturated or non-saturated heterocyclic ring containing 1 to 2 heteroatoms selected from group including O and N; R3 means hydrogen, halogen, aminocarbonyl or C1-6alkyl, optionally containing as substitutes phenylC1-6alkoxy or 1, 2 or 3 halogen atoms; R4 means hydrogen or C1-6alkyl; R5 means hydrogen or C1-6alkyl; and R means halogen, hydrogen or C1-6alkyl. Invention also refers to medicinal agent, inhibition method and compound application.

EFFECT: compounds under this invention have improved activity.

16 cl, 2 tbl, 18 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds of formula , to their salts, where R1 and R2 each independently is hydrogen or C1-10alkyl which can be optionally substituted with substitutes selected from a group comprising a hydroxyl group, NR4R5, pyrrolidinyl, piperidinyl, morpholinyl; R3 is a radical of formula , where n equals 1; R3a is nitro; X is -NR7 - or -O-; R4 and R5 each independently is C1-6alkyl; R7 is hydrogen, C1-6alkyl, optionally substituted with pyrrolidinyl. The invention also pertains to use of the compounds, to a pharmaceutical composition, to a method of preparing the pharmaceutical composition, as well as to a method of obtaining the chemical compound in any of paragraphs 1-3.

EFFECT: obtaining new biologically active compounds with antiviral activity.

7 cl, 4 ex, 2 tbl

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