Sulphonamide derivative having pgd2 receptor antagonist activity

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (III): , in which D is a benzene ring, 2-pyridone ring, pyridine ring, benzoxalone ring, benzoxadinone ring or benzimidazole ring; R1 denotes carboxy or hydroxy; R2 independently denotes a halogen atom; alkyl optionally substituted with a halogen atom, aryl or alkylamine; alkynyl, optionally substituted alkoxy; hydroxy; carboxy; alkoxy optionally substituted with phenyl, aromatic heterocyclic ring which denotes a 5-6-member aromatic monocyclic carbocyclic ring containing one or two heteroatoms, independently selected from oxygen and nitrogen atoms; alkylsulphonyl; aryloxy; amino optionally substituted with alkyl; acyl optionally substituted with alkyl or alkyloxy; alkyloxycarbonyl; alkanesulphonyl; arylsulphonyl or alkylcarbamoyl; carbamoyl optionally substituted with alkyl, phenyl, cycloalkyl, acetyl, alkanesulphonyl, heteroarylalkyl, cycloalkylalkyl, heteroaryl which denotes a 5-6-member aromatic monocyclic ring containing one or three heteroatoms independently selected from oxygen and nitrogen atoms, and which is optionally substituted with alkyl or cycloalkyl; acylcyano; nitro, aryl; heteroaryl which denotes a 5-6-member aromatic ring containing one or more heteroatoms independently selected from oxygen, sulphur and nitrogen atoms, and which is optionally substituted with alkyl; alkylsulphonyl; morpholinylsulphonyl; non-aromatic heterocyclic group which denotes a 5-6-member non-aromatic heterocyclic ring containing one or more nitrogen atoms and optionally an oxygen and/or sulphur atom; R3 denotes C1-C6alkyloxy, C1-C6alkylthio; R4 denotes a halogen atom or alkyloxy; R5 denotes alkyl; M denotes sulphonyl; L3 independently denotes alkylene optionally containing one oxygen or nitrogen atom, alkenylene, or -N(R7)-; R7 independently denotes a hydrogen atom, alkyl; Y denotes a single bond or CO; Z denotes CH or N; n equals 0 or 1; p equals 0, 1, or 2; q equals 0 or 1; provided that R1 does not denote carboxy when ring D is a benzene ring, -L3- denotes -(O-alkylene)- and the substitution position of L3 and Y is an ortho-position in ring D; to pharmaceutically acceptable salts thereof. The invention also relates to compounds of formula (IV), a pharmaceutical composition, a method of treating diseases associated with the DP receptor, use of compounds in any of the claims 1-17, as well as compounds of general formula (V).

EFFECT: obtaining novel biologically active compounds having DP receptor antagonist activity.

30 cl, 8 ex, 62 tbl

 

The technical field to which the invention relates

The present invention relates to a derived sulfonamida, which has antagonistic activity against DP receptor, and to the use of specified substances in medicine.

The level of technology

Prostaglandin D2 (PGD2) is a product of the metabolism of arachidonic acid through PGG2 and PGH2 and, as you know, has different strengths physiological actions. For example, in non-patent literature 1 describes that PGD2 mediates sleep, and the secretion of hormones in the Central nervous system, inhibits platelet aggregation, smooth muscle contraction of the bronchi, the expansion and contraction of blood vessels, etc. in the peripheral system. In addition, it is believed that PGD2 mediates pathological condition in the case of allergies, such as asthma, as it is the main product of the metabolism of arachidonic acid formed by mastocytoma, and has a strong bronchoconstrictive effect, increasing vascular permeability and migration of inflammatory cells infiltration, such as eosinophils.

The DP receptor (also known as DP1 receptor or receptor CRTH2 (also known as DP2 receptor) is known as the receptor for PGD2. A derivative of phenylacetic acid, which has antagonistic activity against receptor DP described in the patent is literature 1, derived sulfonamida, which has antagonistic activity against receptor CRTH2 described in patent literature 2, and the derived phenoxyalkanoic acid, which has antagonistic activity against receptor CRTH2 described in patent literature 3-6.

In addition, derivatives sulfonamida with activity, non-antagonistic activity against PGD2 receptor described in patent literature 7-12 and non-patent literature 2-3.

Patent literature 1: publication WO 2003/078409

Patent literature 2: publication WO 2003/097598

Patent literature 3: publication WO 2004/089884

Patent literature 4: publication WO 2004/089885

Patent literature 5: publication WO 2005/106302

Patent literature 6: publication WO 2006/056752

Patent literature 7: publication WO 1993/012086

Patent literature 8: publication WO 2004/073606

Patent literature 9: publication EP A

Patent literature 10: publication WO 2006/059801

Patent literature 11: publication JP 3-275678A

Patent literature 12: publication JP 3-A

Non-patent literature 1: Pharmacol. Rev., 1994, Vol.46, p.205-22

Non-patent literature 2: Chem. & Pharm. Bull., 1994, Vol.42, p.521-29

Non-patent literature 3: Chem. & Pharm. Bull., 2000, Vol.48, p.1978-85

Description of the invention

The problem to be solved

The present invention relates whom I derived sulfonamida, having antagonistic activity against the DP receptor, and pharmaceutical compositions that contain the compound as an active ingredient. Specified pharmaceutical composition suitable for use as a drug for the treatment of allergic diseases.

Solutions to problems

The authors of the present invention found that discussed below is derived sulfonamida has a strong antagonistic activity against receptor DP and pharmaceutical composition containing the specified connection as the active ingredient, suitable for use as a drug for the treatment of allergic diseases.

Objects of the present invention are:

1) a PGD2 receptor antagonist containing a compound of General formula (I):

in which ring a is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

ring b is a nitrogen-containing non-aromatic heterocyclic ring or a nitrogen-containing aromatic heterocyclic ring;

the ring is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

R1means hydroxyalkyl, carboxy, alkyloxyaryl the sludge, optionally substituted carbarnoyl, cyano or equivalent carboxyl group;

R2independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl not necessarily replaced cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, neobythites is but substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3means a hydrogen atom, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, optionally substituted, aryloxy, optionally substituted, heteroaromatic, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted, cycloalkyl, optionally substituted, cycloalkenyl, optionally substituted, aaltio or optionally substituted, heteroaromatic;

4independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl not necessarily replaced cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optional the part replaced carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, oxo, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

M means a carbonyl or sulfonyl;

Y represents a simple bond, optionally substituted alkylene, optionally containing one or two heteroatom, an oxygen atom, a sulfur atom or-N(R6)-;

L1L2and L3independently mean a simple link, optionally substituted alkylene, optional the part containing one or two heteroatoms, optionally substituted albaniles, optionally containing one or two heteroatoms, optionally substituted akinyan, optionally containing one or two heteroatom, or-N(R7)-;

R6and R7independently mean a hydrogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, acyl, optionally substituted, alkyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

k is 0, 1, 2, 3 or 4;

n means 0, 1 or 2;

q is 0, 1, 2 or 3; provided that (a) k is not equal to 0, when ring b is a 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and ring C is benzene ring, b) the ring is not an indole ring or isoindoline ring, C) R1does not mean carboxy, when the ring C is benzene ring, -L3means -(O-alkylene), and the position of substitution of the L3and Y is ortho-position in the ring, and d) the position of substitution of the L3and Y is para-position in the ring when the ring is In thiazolidinone ring and ring C is benzene ring;

its pharmaceutically acceptable salt or MES as the active ingredient;

2) a PGD2 receptor antagonist according to claim 1, in which R1means carboxy-L3means -(O-optionally substituted alkylene)-;

3) a PGD2 receptor antagonist of claim 1 or 2, in which ring C is benzene ring or pyridine ring;

4) a PGD2 receptor antagonist according to any one of items 1)-3)in which R3means optionally substituted, alkyloxy or optionally substituted, alkylthio;

5) a PGD2 receptor antagonist according to any one of items 1)-4), in which M means sulfonyl;

6) a PGD2 receptor antagonist according to any one of items 1)to (5), in which M means sulfonyl, L1means of simple communication and L2means of a simple connection;

7) a PGD2 receptor antagonist according to any one of items 1)to (6), in which Y represents a simple bond;

8) a PGD2 receptor antagonist according to any one of items 1)to 7), in which R2means halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted nonaromatic heterocyclic group, and k is 1 or 2;

9) a PGD2 receptor antagonist according to any one of items 1)to 7), in which R2means halogen atom, optionally substituted amino, optionally substituted carbarnoyl, it is certainly substituted aryl, optionally substituted heteroaryl or optionally substituted nonaromatic heterocyclic group, and k is 1 or 2;

10) a PGD2 receptor antagonist according to any one of items 1)to 9)in which R4means halogen atom, optionally substituted alkyl or optionally substituted, alkyloxy and q is 0 or 1;

11) a PGD2 receptor antagonist according to any one of items 1)to (10), in which the position of substitution of Y and L3is the meta-position in the ring;

12) a PGD2 receptor antagonist according to any one of items 1)-11), which is a drug for the treatment of allergies;

13) a PGD2 receptor antagonist according to any one of items 1)-11), which is a drug for the treatment of asthma;

14) the compound of General formula (II):

in which ring a is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

ring b is a nitrogen-containing non-aromatic heterocyclic ring or a nitrogen-containing aromatic heterocyclic ring;

the ring is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

R1means hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl, cyano or equivalent carboxyl group;

R2independent means the AET halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, neobythites is but substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3means a hydrogen atom, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, optionally substituted, aryloxy, optionally substituted, heteroaromatic, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted, cycloalkyl, optionally substituted, cycloalkenyl, optionally substituted, aaltio or optionally substituted, heteroaromatic;

R4independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, long is correctly substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted aryl is XI, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, oxo, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

M means a carbonyl or sulfonyl;

Y represents a simple bond, optionally substituted alkylene, optionally containing one or two heteroatom, an oxygen atom, a sulfur atom or-N(R6)-;

L1L2and L3independently mean a simple link, optionally substituted alkylene, optionally containing one or two heteroatoms, optionally substituted albaniles, optionally containing one or dueteronomy, optionally substituted akinyan, optionally containing one or two heteroatom, or-N(R7)-;

R6and R7independently mean a hydrogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, acyl, optionally substituted, alkyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

k is 0, 1, 2, 3 or 4;

n means 0, 1 or 2;

q is 0, 1, 2 or 3; provided that (a) k is not equal to 0, when ring b is a 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and ring C is benzene ring, b) the ring is not an indole ring or isoindoline ring, C) Y, L1and L2mean simple relationship, the ring is piperazinyl ring and R3means2-C4alkyloxy when the ring C is benzene ring, -L3means -(O-alkylene)-, the position of substitution of the L2and Y is ortho-position in the ring and R1means carboxy, d) the position of substitution of the L3and Y is para-position in the ring when the ring is In thiazolidinone ring and ring C is benzene ring, and (e) a group of the formula

is not a group of the formula

when the ring C is benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is a para-position in the ring, and f) the ring is not diazepinone ring;

its pharmaceutically acceptable salt or MES;

15) the compound according to 14), in which R1means carboxy-L3means -(O-optionally substituted alkylene)-;

its pharmaceutically acceptable salt or MES;

16) connection 14) or 15), in which ring C is benzene ring or pyridine ring;

its pharmaceutically acceptable salt or MES;

17) the compound according to any one of paragraphs 14)-16), in which R3means optionally substituted, alkyloxy or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or MES;

18) the compound according to any one of paragraphs 14)-17), in which M means sulfonyl;

its pharmaceutically acceptable salt or MES;

19) the compound according to any one of paragraphs 14)-17), in which M means sulfonyl, L1means of simple communication and L2means of a simple connection;

its pharmaceutically acceptable salt or MES;

20) the compound according to any one of paragraphs 14)-19), in which Y represents a simple bond;

its pharmaceutically acceptable salt or salt is at;

21) the compound according to any one of paragraphs 14)-20), in which R2means halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted nonaromatic heterocyclic group, and k is 1 or 2;

its pharmaceutically acceptable salt or MES;

22) the compound according to any one of punktow 14)-20), in which R2means halogen atom, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted nonaromatic heterocyclic group, and k is 1 or 2;

its pharmaceutically acceptable salt or MES;

23) the compound according to any one of paragraphs 14)-22), in which R4means halogen atom, optionally substituted alkyl or optionally substituted, alkyloxy and q is 0 or 1;

its pharmaceutically acceptable salt or MES;

24) the compound according to any one of paragraphs 14)-23), in which the position of substitution of Y and L3is the meta-position in the ring;

its pharmaceutically acceptable salt or MES;

25) the compound of General formula (III):

in which the ring is D is a benzene ring, naphthalene ring, 2-peritoneum ring, pyridine ring, benzoxazole ring, benzoxazinone ring or a benzimidazole ring;

R1means hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl, cyano or equivalent carboxyl group;

R2independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted CEC alkanesulfonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3means optionally substituted C1-C6alkyloxy, optionally substituted C2-C6alkenylacyl, optionally substituted C2-C6alkyloxy, optionally substituted C3-C6cycloalkane, optionally substituted C3-C6cycloalkenyl, optionally substituted, aryloxy, optional is substituted on heteroaromatic, optionally substituted C1-C6alkylthio, optionally substituted C2-C6alkanity, optionally substituted C2-C6alkylthio, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C6cycloalkenyl, optionally substituted, aaltio or optionally substituted, heteroaromatic;

R4independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, long is correctly substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, oxo, optionally substituted aryl, optionally substituted heteroaryl or NeoMaster is but substituted non-aromatic heterocyclic group;

M means a carbonyl or sulfonyl;

L3independently means a simple link, optionally substituted alkylene, optionally containing one or two heteroatoms, optionally substituted albaniles, optionally containing one or two heteroatoms, optionally substituted akinyan, optionally containing one or two heteroatom, or-N(R7)-;

R7means a hydrogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, acyl, optionally substituted, alkyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

Y represents a simple bond or optionally substituted alkylene, optionally containing one or two heteroatoms;

Z denotes CH, C(R4or N;

n means 0, 1 or 2;

p denotes 1, 2, 3 or 4;

q is 0, 1, 2 or 3, provided that R1does not mean carboxy, when ring D is a benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is ortho-position to ring D;

its pharmaceutically acceptable salt or hydrate;

26) connection A.25, in which R1means carboxy-L3means -(O-optional samewe the hydrated alkylene)-;

its pharmaceutically acceptable salt or MES;

27) connection on p. 25) or 26)in which ring D is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or MES;

28) the compound according to any one of items 25)-27)in which R3means optionally substituted C1-C6alkyloxy or optionally substituted C1-C6alkylthio;

its pharmaceutically acceptable salt or MES;

29) the compound according to any one of items 25)to (28), in which M means sulfonyl;

its pharmaceutically acceptable salt or MES;

30) the compound according to any one of items 25)-29), in which Y represents a simple bond;

its pharmaceutically acceptable salt or MES;

31) the compound according to any one of items 25)-30), in which R2means halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group and R is 1 or 2;

its pharmaceutically acceptable salt or MES;

32) the compound according to any one of items 25)-31), in which R2means halogen atom, optionally substituted amino, optionally substituted carbarnoyl,optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group and R is 1 or 2;

its pharmaceutically acceptable salt or MES;

33) the compound according to any one of items 25)-32), in which R4means halogen atom, optionally substituted alkyl or optionally substituted, alkyloxy and q is 0 or 1;

its pharmaceutically acceptable salt or MES;

34) the compound according to any one of items 25)-33), in which the position of substitution of Y and L3is the meta-position to ring D;

its pharmaceutically acceptable salt or MES;

35) the compound of General formula (IV):

in which ring D is a benzene ring, naphthalene ring, 2-peritoneum ring, pyridine ring, benzoxazole ring, benzoxazinone ring or a benzimidazole ring;

ring E is a ring of the formula

R1means hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl, cyano or equivalent carboxyl group;

R2independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl is, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cellalbaniaalbania, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl is, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3means optionally substituted C1-C6alkyloxy, optionally substituted C2-C6alkenylacyl, optionally substituted C2-C6alkyloxy, optionally substituted C3-C6cycloalkane, optionally substituted C3-C6cycloalkenyl, optionally substituted, aryloxy, optionally substituted, heteroaromatic, optionally substituted C1-C6alkylthio, optionally substituted C2-C6alkanity, optionally substituted C2-C6alkylthio, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C6cycloalkenyl, optionally substituted, aaltio or optionally substituted, heteroaromatic;

R4independently denotes a halogen atom, optionally substituted alkyl, optionally substituted Elke the sludge, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted and the sludge optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5independently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, oxo, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

M means a carbonyl or sulfonyl;

L3independently means a simple link, optionally substituted alkylene, optionally containing one or two heteroatoms, optionally substituted albaniles, optionally containing one or two heteroatoms, optionally substituted akinyan, optionally containing one or two heteroatom, or-N(R7)-;

R7means the volume of hydrogen, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, acyl, optionally substituted, alkyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

Y represents a simple bond or optionally substituted alkylene, optionally containing one or two heteroatoms;

Z denotes CH, C(R4or N;

n means 0, 1 or 2;

p denotes 1, 2, 3 or 4;

q is 0, 1, 2 or 3; provided that (a) R1does not mean carboxy, when ring D is a benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is ortho-position in the ring D, b) a group of the formula

is not a group of the formula

when ring D is a benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is para-position to ring D;

its pharmaceutically acceptable salt or MES;

36) connection p), in which R1means carboxy-L3means -(O-optionally substituted alkylene)-;

its pharmaceutically acceptable salt or MES;

37) connection p) or 36), in which ring D is a benzene ring is olicom or pyridine ring;

its pharmaceutically acceptable salt or MES;

38) the compound according to any one of paragraphs 35)-37), in which R3means optionally substituted C1-C6alkyloxy or optionally substituted C1-C6alkylthio;

its pharmaceutically acceptable salt or MES;

39) the compound according to any one of paragraphs 35)-38), in which M means sulfonyl;

its pharmaceutically acceptable salt or MES;

40) the compound according to any one of paragraphs 35)-39), in which Y represents a simple bond;

its pharmaceutically acceptable salt or MES;

41) the compound according to any one of paragraphs 35)-40), in which R2means halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group and R is 1 or 2;

its pharmaceutically acceptable salt or MES;

42) the compound according to any one of paragraphs 35)-41), in which R2means halogen atom, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group and R is 1 is 2;

its pharmaceutically acceptable salt or MES;

43) the compound according to any one of paragraphs 35)-42), in which R4means halogen atom, optionally substituted alkyl or optionally substituted, alkyloxy and q is 0 or 1;

its pharmaceutically acceptable salt or MES;

44) the compound according to any one of paragraphs 35)-43), in which the position of substitution of Y and L3is the meta-position to ring D;

its pharmaceutically acceptable salt or MES;

45) a pharmaceutical composition comprising a compound according to any one of paragraphs 14)-44), its pharmaceutically acceptable salt or MES as an active ingredient;

46) the pharmaceutical composition according to item 45, which is a DP receptor antagonist;

47) the pharmaceutical composition according to item 45, which is a drug for the treatment of allergies;

48) the pharmaceutical composition according to item 45, which is a drug for the treatment of asthma;

49) a method of treating diseases caused by the DP receptor, characterized by introducing the compound according to any one of items 1)-11) and (14)-44), its pharmaceutically acceptable salt or MES;

50) the method according to § 49, in which the disease is due to DP receptor is asthma;

51) the use of compounds according to any one of items 1)-11) and (14)-44), its pharmaceutically acceptable salt or MES d the I preparation of drugs for the treatment of diseases, due to the DP receptor;

52) the use of compounds according to § 51, its pharmaceutically acceptable salt or MES, in which the disease is due to DP receptor is asthma;

53) the compound of General formula (V):

in which ring D is a benzene ring, naphthalene ring, 2-peritoneum ring, pyridine ring, benzoxazole ring, benzoxazinone ring or a benzimidazole ring;

R1means hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl, cyano or equivalent carboxyl group;

R2independently means a hydrogen atom, halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl the XI, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

L3means easy St is z, optionally substituted alkylene, optionally containing one or two heteroatoms, optionally substituted albaniles, optionally containing one or two heteroatoms, optionally substituted akinyan, optionally containing one or two heteroatom, or-N(R7)-;

R7means a hydrogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, acyl, optionally substituted, alkyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

R8means halogen atom, tripterocalyx or piperazine derivatives;

p denotes 1, 2, 3 or 4; provided that the position of substitution of piperidinium and L3is not ortho-position to the D ring, when ring D is a benzene ring and the-L3means -(O-alkylene)-;

its pharmaceutically acceptable salt or hydrate;

54) the compound according to item 53), in which ring D is a benzene ring and R8means halogen atom;

its pharmaceutically acceptable salt or MES;

55) the compound according to item 53), in which ring D is a benzene ring and R8means piperazine derivatives;

its pharmaceutically acceptable salt or MES;

56) with the unity according to any one of paragraphs 53)-55), in which R1means carboxy or allyloxycarbonyl and-L3means -(O-methylene)-;

its pharmaceutically acceptable salt or MES;

57) the compound according to any one of paragraphs 53)-56), in which R2means halogen atom, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic group;

its pharmaceutically acceptable salt or hydrate; and

58) the compound according to any one of paragraphs 53)-57), in which the position of the substitution R8and L3is the meta-position to ring D;

its pharmaceutically acceptable salt or MES.

In the scope of the present invention includes the following inventions:

(1) a PGD2 receptor antagonist containing a compound of General formula (I-b):

in which ring Ab is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

ring Bb is a 3-8-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom;

ring Cb is a benzene ring, naphthalene ring, 2-peritoneum ring or pyridine ring;

R1bmeans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted, carbamoyl optionally substituted tetrazolyl;

R2bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or neobyazatel is substituted non-aromatic heterocyclic group;

R3bmeans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, it is certainly replaced arylsulfonate, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5bindependent means optionally substituted alkyl or optionally substituted aryl;

Ybmeans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zbmeans of simple communication, alkylen, albaniles, akinyan, -O-alkylene - or-S-alkylene-;

kb means 0, 1, 2, 3 or 4;

mb stands for 0, 1 or 2;

nb is 0, 1 or 2;

pb denotes 0 or 1; provided that k is not equal to 0, when ring b is a 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and ring C is benzene ring;

its pharmaceutically acceptable salt or hydrate;

(2) a PGD2 receptor antagonist under item(1), in which the ring Cb is a benzene ring or a pyridine ring;

(3) a PGD2 receptor antagonist under item(1) or (2)in which the ring Bb is a ring of the formula

nb is 0 or 1;

(4) a PGD2 receptor antagonist according to any one of items (1)to(3), in which the Ab ring is a benzo is a d ring or pyridine ring;

(5) a PGD2 receptor antagonist according to any one of items (1)to(4)where pb denotes 1;

(6) a PGD2 receptor antagonist according to any one of items (1)to(5), in which Ybmeans of a simple bond or-O-;

(7) a PGD2 receptor antagonist according to any one of items (1)to(6), in which R1bmeans carboxy;

(8) a PGD2 receptor antagonist according to any one of items (1)to(7), which is a drug for the treatment of allergies;

(9) a PGD2 receptor antagonist according to any one of items (1)to(7), which is a drug for the treatment of asthma;

(10) the compound of General formula (II-b):

in which ring Ab is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

ring Bb is a 3-8-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom;

ring Cb is a benzene ring, naphthalene ring, 2-peritoneum ring or pyridine ring;

R1bmeans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, hydroxy, optionally substituted ALK is lexi, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3bmeans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, n is necessarily replaced by aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, neoba is consequently replaced heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5bindependent means optionally substituted alkyl or optionally substituted aryl;

Ybmeans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zbmeans of simple communication, alkylen, albaniles, akinyan, -O-alkylene - or-S-alkylene-;

kb means 0, 1, 2, 3 or 4;

mb stands for 0, 1 or 2;

nb is 0, 1 or 2; provided that (a) k is not equal to 0, when ring b is a 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and ring C is benzene ring, b) a group of the formula

is not a group of the formula

when Z denotes-O-alkylene;

its pharmaceutically acceptable salt or hydrate;

(11) a connection on p.(10), in which the ring Bb is a group of the formula

and n means 0 or 1;

its pharmaceutically acceptable salt or hydrate;

(12) the compound under item(10) or (11), in which ring C is benzene ring or pyridine ring;

its pharmaceutically acceptable salt or hydrate;

(13) the compound according to any one of items (10)-(12), in which R3bmeans optional samisen the th alkyloxy or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or hydrate;

(14) the compound according to any one of items (10)to(13), in which R1bmeans carboxy;

its pharmaceutically acceptable salt or hydrate;

(15) the compound of General formula (III-b):

in which the ring Cb is a benzene ring, naphthalene ring, 2-peritoneum ring or pyridine ring;

R1bmeans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyan is, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3bmeans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, long is Ino replaced alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5bindependent means optionally substituted alkyl or optionally substituted aryl;

Xbdenotes CH or N;

Ybmeans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zbmeans of simple communication, alkylen, albaniles, akinyan, -O-alkylene - or-S-alkylene-;

mb stands for 0, 1 or 2;

nb is 0, 1 or 2;

qb means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

(16) the connection under item(15), in which the ring Cb is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

(17) the connection under item(15) or (16), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, cycloalkane (Deputy is a halogen atom, alkyl, aryl or heteroaryl), optionally substituted, cycloalkyl (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, aryloxy (Deputy is a halogen atom, alkyl or alkyloxy), optionally substituted, arieti (Deputy is a halogen atom, alkyl or alkyloxy), optionally substituted, heteroaromatic (Deputy atom is halogen, alkyl or halogenated) or optionally substituted, heteroaromatic (Deputy is a halogen atom, alkyl or halogenated);

its pharmaceutically acceptable salt or hydrate;

(18) the compound under item(15) or (16), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, and is Biloxi, aryl or heteroaryl) or alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl);

its pharmaceutically acceptable salt or hydrate;

(19) the compound according to any one of items (15)-(18), in which R2bmeans halogen atom, cyano, nitro or optionally substituted heteroaryl;

its pharmaceutically acceptable salt or hydrate;

(20) the compound according to any one of items (15)-(19), in which R2bmeans optionally substituted 5-membered heteroaryl;

its pharmaceutically acceptable salt or hydrate;

(21) the compound according to any one of items (15)to(20), in which R1bmeans carboxy;

its pharmaceutically acceptable salt or hydrate;

(22) the compound of General formula (IV-b):

in which the ring Cb is a benzene ring, naphthalene ring, 2-peritoneum ring or pyridine ring;

ring Db is a ring of the formula

R1bmeans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, hydroxy, optionally substituted, alkyloxy, obazatelno replaced alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3bmeans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, it is certainly replaced aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroaryl who were radioactive, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5bindependent means optionally substituted alkyl or optionally substituted aryl;

Xbdenotes CH or N;

Ybmeans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zbmeans of simple communication, alkylen, albaniles, akinyan, -O-alkylene - or-S-alkylene-;

mb stands for 0, 1 or 2;

nb is 0, 1 or 2;

sb means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

(23) a connection on p.(22), in which the ring Cb is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

(24) the connection under item(22) or (23), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, cycloalkane (Deputy is a halogen atom, alkyl, aryl or heteroaryl), optionally substituted, cycloalkyl (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, aryloxy (Deputy is a halogen atom, alkyl or alkalo the si), optionally substituted, arieti (Deputy is a halogen atom, alkyl or alkyloxy), optionally substituted, heteroaromatic (Deputy is a halogen atom, alkyl or halogenated) or optionally substituted, heteroaromatic (Deputy is a halogen atom, alkyl or halogenated);

its pharmaceutically acceptable salt or hydrate;

(25) the compound under item(22) or (23), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl);

its pharmaceutically acceptable salt or hydrate;

(26) the compound according to any one of items (22)to(25), in which R1bmeans carboxy;

its pharmaceutically acceptable salt or hydrate;

(27) the compound of General formula (V-b):

in which the ring Cb is a benzene ring, naphthalene ring or a pyridine ring;

ring Eb is a ring of the formula

R1bmeans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2bindependently denotes a halogen atom, optionally substituted alkyl, optionally Sames the config of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3bmeans optionally substituted, alkyloxy, n is necessarily replaced by alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4bindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, not necessarily for ewenny heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

Xbdenotes CH or N;

Wbmeans of simple communication, alkylene or-O-;

Zbmeans of simple communication, alkylen, albaniles, akinyan, -O-alkylene - or-S-alkylene-;

mb stands for 0, 1 or 2;

sb means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

(28) the connection p.(27), in which the ring Cb is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

(29) a connection on p.(27) or (28), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, cycloalkane (Deputy is a halogen atom, alkyl, aryl or heteroaryl), optionally substituted, cycloalkyl (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, aryloxy (Deputy is a halogen atom, alkyl or alkyloxy), optionally substituted ar is LTI (Deputy is a halogen atom, alkyl or alkyloxy), optionally substituted, heteroaromatic (Deputy is a halogen atom, alkyl or halogenated) or optionally substituted, heteroaromatic (Deputy is a halogen atom, alkyl or halogenated);

its pharmaceutically acceptable salt or hydrate;

(30) a connection on p.(27) or (28), in which R3bmeans optionally substituted, alkyloxy (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl), optionally substituted, alkylthio (Deputy is a halogen atom, alkyloxy, aryl or heteroaryl);

its pharmaceutically acceptable salt or hydrate;

(31) the compound according to any one of items (27)to(30), in which R1bmeans carboxy;

its pharmaceutically acceptable salt or hydrate;

(32) a pharmaceutical composition comprising a compound according to any one of items (10)-(31), its pharmaceutically acceptable salt or hydrate as an active ingredient;

(33) the pharmaceutical composition according to p.(32), which is a DP receptor antagonist;

(34) the pharmaceutical composition according to p.(32), which is a drug for the treatment of allergies;

(35) the pharmaceutical composition according to p.(32), which is a drug for the treatment of asthma;

(36) a method of treating diseases caused by the DP receptor, characterized by the introduction of the soedineniya according to any one of items (1)to(7) and (10)-(31), its pharmaceutically acceptable salt or hydrate;

(37) the method according to p.(36), in which the disease is due to DP receptor is asthma;

(38) use of the compound according to any one of items (1)to(7) and (10)-(31), its pharmaceutically acceptable salt or hydrate for the preparation of drugs for the treatment of diseases caused by the DP receptor; and

(39) application connection p.(38), its pharmaceutically acceptable salt or hydrate, in which the disease is due to DP receptor is asthma.

In the scope of the present invention includes the following inventions:

[1] a PGD2 antagonist containing a compound of General formula (I-a):

in which ring a-a is an aromatic carbocyclic ring or an aromatic heterocyclic ring;

the ring is 4 to 8-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom;

the ring is a benzene ring, naphthalene ring or a pyridine ring;

R1ameans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, neobythites is but substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3ameans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, neoba is consequently replaced by cycloalkylation, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, not necessarily for ewenny heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5aindependent means optionally substituted alkyl or optionally substituted aryl;

Yameans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zameans of simple communication, alkylen, albaniles, akinyan, -O-alkylene or-S-alkylene-;

ka means 0, 1, 2, 3 or 4;

ma means 0, 1 or 2;

na denotes 0, 1 or 2;

RA denotes 0 or 1; provided that ka is not equal to 0, when the ring is 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and the ring is a benzene ring;

its pharmaceutically acceptable salt or hydrate as an active ingredient;

[2] a PGD2 antagonist on p.[1], in which a ring is a benzene ring or a pyridine ring;

[3] a PGD2 antagonist on p. [1] or [2], in which a ring is a ring of the formula

and n means 0;

[4] a PGD2 antagonist according to any one of paragraphs [1]-[3], in which ring a-a is a benzene ring or a pyridine ring;

[5] a PGD2 antagonist according to any one of paragraphs [1]-[4], in which RA means 1;

[6] a PGD2 antagonist according to any one of paragraphs [1]-[5], in the cat the rum Y ameans of a simple bond or-O-;

[7] a PGD2 antagonist according to any one of paragraphs [1]-[6], in which R1ameans carboxy;

[8] a PGD2 antagonist according to any one of paragraphs [1]-[7], which is a drug for the treatment of allergies;

[9] a PGD2 antagonist according to any one of paragraphs [1]-[7], which is a drug for the treatment of asthma;

[10] the compound of General formula (II-a):

in which the ring is 4 to 8-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom;

the ring is a benzene ring, naphthalene ring or a pyridine ring;

R1ameans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted alcalali is aryloxy, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3ameans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, neobyazatelnostyu cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5aindependent means optionally substituted alkyl or optionally substituted aryl;

Yameans a simple link, Alki the Yong, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zameans of simple communication, alkylen, albaniles, akinyan, -O-alkylene or-S-alkylene-;

ka means 0, 1, 2, 3 or 4;

ma means 0, 1 or 2;

na denotes 0, 1 or 2; provided that (a) ka is not equal to 0, when the ring is 6-membered nitrogen-containing heterocyclic ring containing one or two nitrogen atom, and the ring is a benzene ring and (b) a group of the formula

is not a group of the formula

when Zameans-Of-alkylen;

its pharmaceutically acceptable salt or hydrate;

[11] the connection on p.[10], in which a ring is a ring of the formula

and na denotes 0;

its pharmaceutically acceptable salt or hydrate;

[12] a connection on p.[10] or [11], in which a ring is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

[13] the compound according to any one of items [10]-[12], in which R3ameans optionally substituted, alkyloxy or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or hydrate;

[14] the compound according to any one of items [10]-[13], in which R1ameans carboxy;

its pharmaceutically acceptable salt or hydrate;

[15] the connection about the formula (III-a):

in which the ring-and means a benzene ring, naphthalene ring or a pyridine ring;

R1ameans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonate, optional samisen the th heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3ameans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkene is oxycarbonyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5aindependent means optionally substituted alkyl or optionally substituted aryl;

Yameans of simple communication, alkylen, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zameans of simple communication, alkylen, albaniles, akinyan, -O-alkylene or-S-alkylene-;

ma means 0, 1 or 2;

na denotes 0, 1 or 2;

qa means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

[16] the connection on p.[15], in which a ring is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

[17] the connection on p.[15] or [16], in which R3ameans Ala is lexi, which may be substituted by one to three substituents selected from the group of substituents Q-a, including a halogen atom, alkyloxy, aryl and heteroaryl or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or hydrate;

[18] the compound according to any one of items [15]-[17], in which R1ameans carboxy;

its pharmaceutically acceptable salt or hydrate;

[19] the compound of General formula (IV-a):

in which the ring is a benzene ring, naphthalene ring or a pyridine ring;

ring D is a ring of the formula

R1ameans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonyl is hydroxy, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3ameans optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, neobyazatelnostyu cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5aindependent means optionally substituted alkyl or optionally substituted aryl;

Yameans a simple link, Alki the Yong, albaniles, akinyan, -O-, -S-, -O-alkylene - or-S-alkylene-;

Zameans of simple communication, alkylen, albaniles, akinyan, -O-alkylene or-S-alkylene-;

ma means 0, 1 or 2;

na denotes 0, 1 or 2;

sa means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

[20] the connection on p.[19], in which a ring is a benzene ring or a pyridine ring;

its pharmaceutically acceptable salt or hydrate;

[21] the connection on p.[19] or [20], in which R3ameans alkyloxy, which can be substituted one to three substituents selected from the group of substituents Q-a, including a halogen atom, alkyloxy, aryl and heteroaryl or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or hydrate;

[22] the compound according to any one of paragraphs [19]-[21], in which R1ameans carboxy;

its pharmaceutically acceptable salt or hydrate;

[23] the compound of General formula (V-a):

in which the ring is a benzene ring, naphthalene ring or a pyridine ring;

ring D is a ring of the formula

R1ameans hydroxyalkyl, carboxy, alkylaminocarbonyl, optionally substituted carbarnoyl or optionally substituted tetrazolyl;

R2aindependently denotes a halogen atom,optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R3ameans neobyazatel is replaced by alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane, optionally substituted, cycloalkyl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted, heteroaromatic or optionally substituted, heteroaromatic;

R4aindependently denotes a halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optional substituted arylsulfonyl, optionally substituted, arylsulfonate, optional replacement of the military heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group;

R5aindependent means optionally substituted alkyl or optionally substituted aryl;

Wameans of simple communication, alkylen, albaniles, akinyan, -O - or-S-;

Zameans of simple communication, alkylen, albaniles, akinyan, -O-alkylene or-S-alkylene-;

ma means 0, 1 or 2;

na denotes 0, 1 or 2;

sa means 1, 2, 3 or 4;

its pharmaceutically acceptable salt or hydrate;

[24] the connection on p.[23], in which a ring is a benzene ring or a pyridine ring;

it farmatsevticheskii acceptable salt or hydrate;

[25] the connection on p.[23] or [24], in which R3ameans alkyloxy, which can be substituted one to three substituents selected from the group of substituents Q-a, including a halogen atom, alkyloxy, aryl and heteroaryl or optionally substituted, alkylthio;

its pharmaceutically acceptable salt or hydrate;

[26] the compound according to any one of items [23]-[25], in which R1ameans carboxy;

its pharmaceutically acceptable salt or hydrate;

[28] the pharmaceutical composition according to p.[27], which is a DP receptor antagonist;

[29] the pharmaceutical composition according to p.[27], which is a drug for the treatment of allergies;

[30] the pharmaceutical composition according to p.[27], which is a drug for the treatment of asthma;

[31] a method of treating diseases caused by the DP receptor, characterized by introducing the compound according to any one of paragraphs [1]-[7] and [10]-[26], its pharmaceutically acceptable salt or hydrate;

[32] the method according to p.[31], in which the disease is due to DP receptor is asthma;

[33] the use of compounds according to any one of paragraphs [1]-[7] and [10]-[26], its pharmaceutically acceptable salt or hydrate for the preparation of drugs for the treatment of diseases caused by the DP receptor;

[34] the use of compounds on p.[33], its pharmaceutically acceptable salt or hydrate, in which the disease is due to DP receptor is asthma.

Below is the meaning of the terms used in the present description of the invention. In the present description of the invention, each term has the same definition and the same meaning when used alone or in combination with one the mi terms.

In the present description, the term “halogen atom” means a fluorine atom, chlorine atom, bromine atom and iodine atom. Preferred atoms are fluorine atom, chlorine atom and bromine atom.

In the present description, the term “heteroatom” means an oxygen atom, a sulfur atom and a nitrogen atom.

In the present description, the term “alkyl” means a monovalent hydrocarbon group with a straight or branched chain, containing one to eight carbon atoms. Such groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, n-octyl and the like. The preferred group is1-C6alkyl. A more preferred group is1-C4alkyl. In case the number of carbon atoms such group means “alkyl” with the number of carbon atoms in the specified range.

In the present description, the term “hydroxyalkyl” means the above “alkyl”, in which a hydrogen atom is substituted by a hydroxyl group. Such groups include, for example, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, and the like. The preferred group is hydroxymethyl.

In the present description, the term “alkenyl” means ml is valentno hydrocarbon group with a straight or branched chain, containing two to eight carbon atom and one or more double bonds. Such groups include, for example, vinyl, allyl, 1-propenyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-heptenyl, 2-octenyl and the like. The preferred group is2-C6alkenyl. In addition, the preferred group is2-C4alkenyl.

In the present description, the term “quinil” means a monovalent hydrocarbon group with a straight or branched chain containing two to eight carbon atom and one or more triple bonds. Such groups include, for example, ethinyl, 1-PROPYNYL, 2-PROPYNYL, 2-butynyl, 2-pentenyl, 2-hexenyl, 2-heptenyl, 2-octenyl and the like. The preferred group is2-C6quinil. In addition, the preferred group is2-C4quinil.

In the present description, the term “cycloalkyl” means cycloalkyl containing three to eight carbon atoms, and includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and similar groups. The preferred group is3-C6cycloalkyl.

In the present description, the term “cycloalkenyl” means cycloalkenyl containing three to eight carbon atoms, and includes, for example, cyclopropyl, cyclobutyl, qi is lofentanil, cyclohexenyl, cycloheptenyl, cyclooctyl and similar groups. The preferred group is3-C6cycloalkenyl.

In the present description, the term “alkyloxy” means a group in which an oxygen atom is substituted by one of the above “alkyl”, and includes, for example, metiloksi, ethyloxy, n-propyloxy, isopropoxy, n-Butylochka, isobutoxy, sec-Butylochka, tert-Butylochka, n-pentyloxy, isopentane, 2-pentyloxy, 3-pentyloxy, n-hexyloxy, isohexane, 2-hexyloxy, 3 hexyloxy, n-heptyloxy, n-octyloxy and the like groups. The preferred group is1-C6alkyloxy. In addition, the preferred group is1-C4alkyloxy. In case the number of carbon atoms such group is alkyloxy” with the number of carbon atoms in the specified range.

In the present description, the term “alkenylacyl” means a group in which an oxygen atom is substituted by one of the above “alkenyl”, and includes, for example, vinyloxy, allyloxy, 1 propenyloxy, 2-butenyloxy, 2-pentyloxy, 2-hexenoate, 2-heptyloxy, 2-octenoate and similar groups. The preferred group is2-C6alkenylacyl. In addition, the preferred group is2-C4alkenylacyl. In case the number of atoms ug is erode this group is alkenylacyl” with the number of carbon atoms in the specified range.

In the present description, the term “alkyloxy” means a group in which an oxygen atom is substituted by one of the above “quinil”, and includes, for example, itineracy, 1 propenyloxy, 2-propenyloxy, 2-butenyloxy, 2-pentyloxy, 2-hexyloxy, 2-heptyloxy, 2-octyloxy and similar groups. The preferred group is2-C6alkyloxy. In addition, the preferred group is2-C4alkyloxy. In case the number of carbon atoms such group is alkyloxy” with the number of carbon atoms in the specified range.

In the present description, the term “cycloalkane” means a group in which an oxygen atom is substituted by one of the above “cycloalkyl”, and includes, for example, cyclopropane, CYCLOBUTANE, cyclopentyloxy, cyclohexyloxy, cycloheptylamine, cyclooctylamine. The preferred group is3-C6cycloalkane. In case the number of carbon atoms such group is cycloalkane” with the number of carbon atoms in the specified range.

In the present description, the term “cycloalkenyl” means a group in which an oxygen atom is substituted by one of the above “cycloalkenyl”, and includes, for example, cyclopropenone, cyclobutanone, Cyclopentanone, cyclohexanone cycloheptanone, cyclooctanone. The preferred group is3-C6cycloalkenyl. In case the number of carbon atoms such group is cycloalkenyl” with the number of carbon atoms in the specified range.

In the present description, the term “alkylthio” means a group in which a sulfur atom is substituted by one of the above “alkyl”, and includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutyric, sec-butylthio, tert-butylthio, n-pentylthio, isopentyl, 2-pentylthio, 3 pentylthio, n-hexylthio, isohexyl, 2-hexylthio, 3-hexylthio, n-Reptilia, n-octylthio and similar groups. The preferred group is1-C6alkylthio. In addition, the preferred group is1-C4alkylthio. In case the number of carbon atoms such group is alkylthio” with the number of carbon atoms in the specified range.

In the present description, the term “alkanity” means a group in which a sulfur atom is substituted by one of the above “alkenyl”, and includes, for example, VINITI, allylthio, 1 propylthio, 2-butylthio, 2-pentylthio, 2-hexanite, 2-gattelli, 2-actinistia and similar groups. The preferred group is2-C6alkanity. In addition, the preferred group is2-C4alkylthio. In case the Azania number of carbon atoms such group is alkanity” with the number of carbon atoms in the specified range.

In the present description, the term “alkylthio” means a group in which a sulfur atom is substituted by one of the above “quinil”, and includes, for example, etenity, 1 propylthio, 2-propylthio, 2-butylthio, 2-pentylthio, 2-hexylthio, 2-Latinity, 2-octylthio and similar groups. The preferred group is2-C6alkylthio. In addition, the preferred group is2-C4alkylthio. In case the number of carbon atoms such group is alkylthio” with the number of carbon atoms in the specified range.

In the present description, the term “alkylsulfonyl” means a group in which sulfinil replaced by one of the above “alkyl”, and includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl, tert-butylsulfonyl, n-pentylaniline, isopentylamine, 2-pentylaniline, 3-pentasulfide, n-hexylsilane, isohexanol, 2-hexylaniline, 3-hexylaniline, n-heptylaniline, n-octylaniline and similar groups. The preferred group is1-C6alkylsulfonyl. In addition, the preferred group is1-C4alkylsulfonyl.

In the present description, the term “alkylsulfonyl” OSN which denotes the group in which sulfonyl replaced by one of the above “alkyl”, and includes, for example, methylsulphonyl, ethylsulfonyl, n-propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl, tert-butylsulfonyl, n-peterculter, isopentylamine, 2-peterculter, 3-peterculter, n-hexylsilane, isohexanol, 2-hexylsilane, 3-hexylsilane, n-heptylaniline, n-octylsilane and similar groups. The preferred group is1-C6alkylsulfonyl. In addition, the preferred group is1-C4alkylsulfonyl.

In the present description, the term “alkylsulfonate” means a group in which the atom kislorod replaced by one of the above “alkylsulfonyl”, and includes, for example, methylsulfonylamino, ethylsulfonyl, n-propylsulfonyl, isopropylcarbonate, n-butylsulfonyl, isobutyronitrile, sec-butylsulfonyl, tert-butylsulfonyl, n-pentylaniline, isopentylamine, 2-pentylaniline, 3 interconference, n-hexylaniline, isohexanoate, 2-hexylaniline, 3 hexylaniline, n-heptylaniline, n-octylaniline and similar groups. The preferred group is1-C6alkylsulfonyl. In addition, bol is e preferred group is 1-C4alkylsulfonyl.

In the present description, the term “cycloalkyl” means a group in which a sulfur atom is substituted by one of the above “cycloalkyl”, and includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexylthio, cycloheptyl, cyclooctyl and similar groups. The preferred group is3-C6cycloalkylation. In case the number of carbon atoms such group is cycloalkyl” with the number of carbon atoms in the specified range.

In the present description, the term “cycloalkylcarbonyl” means a group in which sulfinil replaced by one of the above “cycloalkyl”. Such groups include, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl and cyclooctasulfur. The preferred group is3-C6cycloalkylcarbonyl.

In the present description, the term “cycloalkylcarbonyl” means a group in which sulfonyl replaced by one of the above “cycloalkyl”. Such groups include, for example, cyclopropanesulfonyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl and cyclooctasulfur. The preferred group is3-C6cycloalkylcarbonyl.

In the present description, the term “cycloalkylcarbonyl” means the group in which the oxygen atom is substituted by one of the above “cycloalkylcarbonyl”. Such groups include, for example, cyclopropylmethoxy, cyclobutylmethyl, cyclopentylmethyl, cyclohexylsulfamate, cyclohexylsulfamate, cyclooctylmethyl. The preferred group is3-C6cycloalkylcarbonyl.

In the present description, the term “cycloalkenyl” means a group in which a sulfur atom is substituted by one of the above “cycloalkenyl”. Such groups include, for example, cyclopropanation, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctene. The preferred group is3-C6cycloalkenyl. In case the number of carbon atoms such group is cycloalkenyl” with the number of carbon atoms in the specified range.

In the present description, the term “cycloalkylcarbonyl” means a group in which sulfinil replaced by one of the above “cycloalkenyl”. Such groups include, for example, cyclopropanesulfonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanesulfonyl, cycloheptylmethyl and cyclohexanesulfonyl. The preferred group is3-C6cycloalkylcarbonyl.

In the present description of the invention t is pmin “cycloalkylcarbonyl” means the group in which sulfonyl replaced by one of the above “cycloalkenyl”. Such groups include, for example, cyclopropanesulfonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanesulfonyl, cycloheptylmethyl and cyclohexanesulfonyl. The preferred group is3-C6cycloalkylcarbonyl.

In the present description, the term “cycloalkylcarbonyl” means a group in which an oxygen atom is substituted by one of the above “cycloalkylcarbonyl”. Such groups include, for example, cyclopropanesulfonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanesulfonic, cycloheptylmethyl, cyclohexanesulfonic. The preferred group is3-C6cycloalkylcarbonyl.

In the present description, the term “alkylaminocarbonyl” means a group in which a carbonyl substituted one above alkyloxy”. Such groups include, for example, methyloxycarbonyl, ethoxycarbonyl, n-propylenecarbonate, isopropoxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl and n-pentyloxybenzoyl. The preferred group is1-C4allyloxycarbonyl. In addition, the preferred group is1-C2allyloxycarbonyl.

In this is the description of the invention, the term “alkenylacyl” means the group in which the carbonyl is substituted by one of the above “alkenylacyl”. Such groups include, for example, vinyloxycarbonyl, allyloxycarbonyl, 1-propenylboronic, 2-butyloxycarbonyl and 2-interracialanal. The preferred group is2-C4allyloxycarbonyl.

In the present description, the term “alkyloxyalkyl” means a group in which a carbonyl substituted one above alkyloxy”. Such groups include, for example, ethinylestradiol, 1-propenylboronic, 2-propenylboronic, 2-butyloxycarbonyl and 2-intenrational. The preferred group is2-C4alkyloxyaryl.

In the present description, the term “acyl” means alkylsulphonyl, in which the alkyl portion is the above “alkyl”, alkenylboronic in which Alchemilla part is above the “alkenyl”, alkenylboronic in which Alchemilla part is above the “quinil”, cycloalkylcarbonyl in which cycloalkyl part is above the “cycloalkyl”, arylcarbamoyl, in which the aryl part is below the “aryl”, heteroarylboronic, in which the heteroaryl portion is below the “heteroaryl”, and non-aromatic heterocyclic carbonyl, in which the non-aromatic hetero is Ilichevsky group is below the “nonaromatic heterocyclic group”. “Alkyl”, “alkenyl”, “quinil”, “cycloalkyl”, “aryl”, “heteroaryl” and “non-aromatic heterocyclic group may be respectively substituted for the placeholder groups listed in the definition of such terms as “optionally substituted alkyl”, “optional substituted alkenyl”, “optionally substituted quinil”, “optionally substituted cycloalkyl”, “optionally substituted aryl”, “optionally substituted heteroaryl” and “optionally substituted non-aromatic heterocyclic group”. Examples of acyl groups include acetyl, propionyl, butteroil, cyclohexylcarbonyl, benzoyl, pyridylcarbonyl and the like.

In the present description, the term “optionally substituted amino” means an amino group which may be substituted by one or two groups of the above “alkyl”, the “alkenyl”above “quinil”above “cycloalkyl”above “cycloalkenyl”, below “aryl”, below “heteroaryl”, the above “acyl”, the above “allyloxycarbonyl”above “alkenylcarbazoles”above “alkyloxyalkyl”, “alkylsulfonyl”, “alkanesulfonyl”, “alkylsulfonyl”, “arylsulfonyl” and/or the above-mentioned “heteroarylboronic”. The use of the s optionally substituted amino group include amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, benzylamino, acetylamino, benzoylamine, methoxycarbonylamino, methanesulfonamido. The preferred groups are amino, methylamino, dimethylamino, ethylmethylamino, diethylamino, acetylamino, methanesulfonamido.

In the present description, the term “optionally substituted carbarnoyl” means aminocarbonyl group, which is optionally substituted amino group is the above-mentioned “optionally substituted amino”, and examples of the optionally substituted carbamoyl groups include carbarnoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, N-benzylcarbamoyl, N-acetylmuramyl, N-methylsulfonylamino etc. Preferred groups are carbarnoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-methylsulfonylamino etc.

In the present description, the term “optionally substituted sulfamoyl” means aminosulfonyl group, which is optionally substituted amino group is the above-mentioned “optionally substituted amino”, and examples of the optionally substituted sulfamoyl group include sulfamoyl, N-methylcarbamoyl, N,N-dimethylsulphamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, N-benzyl who sulfamoyl, N-acetylmuramyl, N-methylsulfonylamino etc. Preferred groups are sulfamoyl, N-methylcarbamoyl, N,N-dimethylsulphamoyl, N-methylsulfonylamino etc.

In the present description, the term “alkylene” means alkylenes group with a straight or branched chain, containing one to ten carbon atoms, and includes, for example, methylene, 1-METROTILE, 1,1-dimethylmethylene, ethylene, 1-mutilation, 1-ethylethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, 1,1-diethylethylene, 1,2-diethylethylene, 1-ethyl-2-mutilation, trimethylene, 1-metallisation, 2-metallisation, 1,1-dimethyltrimethylene, 1,2-dimethyltrimethylene, 2,2-dimethyltrimethylene, 1-ethyltryptamine, 2-ethyltryptamine, 1,1-determination, 1,2-determination, 2,2-determination, 2-ethyl-2-metallisation, tetramethylene, 1-methyltyramine, 2-methyltyramine, 1,1-dimethyltrimethylene, 1,2-dimethyltrimethylene, 2,2-dimethyltrimethylene, 2,2-di-n-propertisation etc. Preferred groups are, in particular, alkylene group with straight or branched chain containing two to six carbon atoms.

In the present description, the term “albaniles” means alkenylamine group with straight or branched chain containing two to ten carbon atoms, and includes, for example, ethenylene, 1-methyladenine, 1-utilitarian, 1,2-dimethylethylene, 1,2-di is tretinoin, 1-ethyl-2-methyladenine, propylen, 1-methyl-2-propanole, 2-methyl-2-propanole, 1,1-dimethyl-2-propanole, 1,2-dimethyl-2-propanole, 1-ethyl-2-propanole, 2-ethyl-2-propanole, 1,1-diethyl-2-propanole, 1,2-diethyl-2-propanole, 1-butylen, 2-butylen, 1-methyl-2-butylen, 2-methyl-2-butylen, 1,1-dimethyl-2-butylen, 1,2-dimethyl-2-butylen etc. Preferred groups are, in particular, alkenylamine group with straight or branched chain containing two to six carbon atoms.

In the present description, the term “akinyan” means alkynylamino group with straight or branched chain containing two to ten carbon atoms, and includes, for example, ethynylene, propylen, 1-methyl-2-propylen, 1-ethyl-2-propylen, Butyrin, 1-methyl-2-Butylin, 2-methyl-3-Butylin, 1,1-dimethyl-2-Butylin, 1,2-dimethyl-3-Butylin, 2,2-dimethyl-3-Butylin etc. Preferred groups are, in particular, akinleye groups with straight or branched chain containing two to six carbon atoms.

In the present description, the term “-O-alkylene” in the definition of Y means of the above alkylenes group, the end of which is connected with, and includes, for example, -O-methylene-1-mutilation-, -O-1,1-dimethylmethylene-, -O -, ethylene-, -O-1-mutilation-, -O-trimethylene etc. Preferred groups are-O-methylene-1-methylation - and-About-1,1-dime ylmethylene-. In addition, the ring and the ring are connected as follows : “ring-O-alkylene-ring”.

In the present description, the term “-O-alkylene” group “-O-alkylene-R1” in the definition-Z-R1means above alkylenes group, the end of which is connected with, and includes, for example, -O-methylene-, -O-1-mutilation-, -O-1,1-dimethylmethylene-, -O -, ethylene-, -O-1-mutilation-, -O-trimethylene etc. Preferred groups are-O-methylene-, -O-1-mutilation and-About-1,1-dimethylmethylene-.

In the present description, the term “-S-alkylene” in the definition of Y means of the above alkylenes group, the end of which is connected with S, and includes, for example, -S-methylene-S-1-mutilation, -S-1,1-dimethylmethylene-, -S -, ethylene-, -S-1-mutilation-, -S-trimethylene etc. Preferred groups are-S-methylene-S-1-mutilation-, -S-1,1-dimethylmethylene-. In addition, the ring and the ring are connected as follows : “ring-S-alkylen-ring”.

In the present description, the term “-S-alkylene” group “-S-alkylen-R1” in the definition-Z-R1means above alkylenes group, the end of which is connected with S, and includes, for example, -S-methylene-, -S-1-mutilation-, -S-1,1-dimethylmethylene-, -S -, ethylene-, -S-1-mutilation-, -S-trimethylene etc. Predpochtitelnye groups are-S-methylene-, -S-1-methylation - and-S-1,1-dimethylmethylene-.

In this OPI is assured of the invention, the term “aryl” means an aromatic monocyclic or condensed aromatic cyclic hydrocarbon, which may be condensed with the above-mentioned “cycloalkyl”above “cycloalkenyl” or below “non-aromatic heterocyclic group” in any possible position. As the monocyclic ring and the condensed ring may be substituted at any position and includes, for example, phenyl, 1-naphthyl, 2-naphthyl, antril, tetrahydronaphthyl, 1,3-benzodioxolyl, 1,4-benzodioxane etc. Preferred groups are phenyl, 1-naphthyl and 2-naphthyl. In addition, the preferred group is phenyl.

In the present description, the term “non-aromatic heterocyclic group” means a 5-7 membered non-aromatic heterocyclic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen, or polycyclic ring formed by condensation of two or more rings. Such groups include, for example, pyrrolidinyl (for example, 1-pyrrolidinyl, 2-pyrrolidinyl), pyrrolyl (for example, 3-pyrrolidyl), imidazolidinyl (for example, 2-imidazolidinyl), imidazolyl (for example, imidazolyl), pyrazolidine (for example, 1-pyrazolidone, 2-pyrazolidone), pyrazolyl (for example, pyrazolines), piperidyl (for example, piperidino, 2-piperidyl), piperazinil (naprimer, 1-piperazinil), indolinyl (for example, 1-indolinyl), isoindoline (for example, ISO doliner), morpholinyl (for example, morpholino, 3-morpholinyl) etc.

In the present description, the term “heteroaryl” in the definition of R2, R2aand R2bmeans 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen, which may be condensed with the above-mentioned “cycloalkyl”, the aforementioned “aryl”, “non-aromatic heterocyclic group” or other heteroaryl in any possible position. Heteroaryl group may be substituted in any position when it is monocyclic ring or a condensed ring. Such groups include, for example, pyrrolyl (for example, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl), furyl (e.g. 2-furyl, 3-furyl), thienyl (for example, 2-thienyl, 3-thienyl), imidazolyl (for example, 2-imidazolyl, 4-imidazolyl), pyrazolyl (for example, 1-pyrazolyl, 3-pyrazolyl), isothiazole (for example, 3-isothiazole), isoxazolyl (for example, 3-isoxazolyl), oxazolyl (for example, 2-oxazolyl), thiazolyl (for example, 2-thiazolyl), pyridyl (e.g. 2-pyridyl, 3-pyridyl, 4-pyridyl), pyrazinyl (for example, 2-pyrazinyl), pyrimidinyl (for example, 2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl (for example, 3-pyridazinyl), tetrazolyl (for example, 1H-tetrazolyl), oxadiazolyl (e.g., 1,3,4-oxadiazolyl), thiadiazolyl (e.g., 1,3,4-thiadiazolyl), in which original (for example, 2-indolizinyl, 6-indolizinyl), isoindoline (for example, 2-isoindolyl), indolyl (e.g., 1-indolyl, 2-indolyl, 3-indolyl), indazole (for example, 3-indazole), purines (for example, 8-purinol), hinolinol (for example, 2-hinolinol), ethanolic (for example, 3-ethanolic), chinolin (for example, 2-chinolin, 5-chinolin), parasini (for example, 1-fcarsenal), naphthylidine (for example, 2-naphthylidine), hanalani (for example, 2-hanalani), hintline (for example, 2-hintline), indolinyl (for example, 3-indolinyl), pteridinyl (for example, 2-pteridinyl), carbazoles (for example, 2-carbazolyl, 4-carbazolyl), phenanthridine (for example, 2-phenanthridines, 3-phenanthridine), acridines (for example, 1-acridine, 2-acridines), dibenzofurans (for example, 1-dibenzofuran, 2-dibenzofuran), benzoimidazolyl (for example, 2-benzoimidazolyl), benzisoxazole (for example, 3-benzisoxazole), benzoxazolyl (for example, 2-benzoxazolyl), benzoxadiazole (naprimer, 4-benzoxadiazole), benzothiazolyl (for example, 3-benzothiazolyl), benzothiazolyl (for example, 2-benzothiazolyl), benzofuran (for example, 3-benzofuran), sensational (for example, 2-benzothiazyl), dibenzothiazyl (for example, 2-dibenzothiazyl), benzodioxolyl (for example, 1,3-benzodioxolyl) etc.

In the present description, the term “heteroaryl” in the definition of R3, R3a, R3b, R4, R4a, R4b, R5R 5a, R5b, R6and R7means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen, which may be condensed with the above-mentioned “cycloalkyl”, the aforementioned “aryl”, “non-aromatic heterocyclic group” or other heteroaryl in any possible position. Heteroaryl group may be substituted in any position when it is monocyclic ring or a condensed ring. Such groups include, for example, furyl (e.g. 2-furyl, 3-furyl), thienyl (for example, 2-thienyl, 3-thienyl), imidazolyl (for example, 2-imidazolyl, 4-imidazolyl), pyrazolyl (for example, 1-pyrazolyl, 3-pyrazolyl), isothiazole (for example, 3-isothiazole), isoxazolyl (for example, 3-isoxazolyl), oxazolyl (for example, 2-oxazolyl), thiazolyl (for example, 2-thiazolyl), pyridyl (e.g. 2-pyridyl, 3-pyridyl, 4-pyridyl), pyrazinyl (for example, 2-pyrazinyl), pyrimidinyl (for example, 2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl (for example, 3-pyridazinyl), oxadiazolyl (e.g., 1,3,4-oxadiazolyl), thiadiazolyl (e.g., 1,3,4-thiadiazolyl), benzoimidazolyl (for example, 2-benzoimidazolyl), benzisoxazole (for example, 3-benzisoxazole), benzoxazolyl (for example, 2-benzoxazolyl), benzofuran (for example, 3-benzofuran), sensational (for example, 2-benzothiazyl) is so

In the present description, the term “2-pyridone” means pyridine-2-it.

In the present description, the term “aryloxy” means a group in which an oxygen atom is substituted by one of the above “aryl”, and includes, for example, phenyloxy, naphthyloxy etc.

In the present description, the term “aristeo” means a group in which a sulfur atom is substituted by one of the above “aryl”, and includes, for example, phenylthio, naphthylthio etc.

In the present description, the term “arylsulfonyl” means a group in which sulfinil replaced by one of the above “aryl”, and includes, for example, phenylsulfinyl, naphthylmethyl etc.

In the present description, the term “arylsulfonyl” means a group in which sulfonyl replaced by one of the above “aryl”, and includes, for example, phenylsulfonyl, aftercooler etc.

In the present description, the term “arylsulfonyl” means vinylsulfonate, naftiliaki etc.

In the present description, the term “aryloxyalkyl” means a group in which a carbonyl substituted one above aryloxy”, and includes, for example, phenoxycarbonyl, 1-naphthaleneboronic, 1-naphthaleneboronic etc.

In the present description, the term “heteroaromatic” means a group in which an oxygen atom is and replaced by one of the above “heteroaryl”. Such groups include, for example, pyrrolidone, forelocks, titilate, imidazolinone, pyrazolinone, isothiazolinone, isoxazolidine, oxazolidine, thiazolidine, pyridyloxy, pyrazinone, pyrimidinone, pyridazinone, tetrazolate, oxadiazolidine, thiadiazolidine, indolizinyl, isoindolyl, intolerance, indazolinone, purinox, finalizirate, athinaiki, hinomisaki, Tarasenoks, naphthylidine, Himalayas, girasolereale, cinnolines, peridiniales, carbonyloxy, phenanthridinone, greenlake, dibenzofurans, benzimidazolinone, benzisoxazoles, benzoxazolinone, benzoxadiazole, benzisothiazolinone, benzothiazolinone, benzoperylene, benzothiazolone, dibenzodioxin, benzodioxolyl. The preferred groups are forelocks, titilate, imidazolinone, pyrazolinone, isothiazolinone, isoxazolidine, oxazolidine, thiazolidine, pyridyloxy, pyrazinone, pyrimidinone, pyridazinone.

In the present description, the term “heteroaromatic” means a group in which a sulfur atom is substituted by one of the above “heteroaryl”. Such groups include, for example, pyrolytic, furylthio, tianity, imidazolidine, personilty, isothiazoline, isoxazolyl, oxazolyl, thiazolino, is aridity, personilty, pyrimidinyl, pyridazinyl, tetrazolyl, oxadiazolyl, thiadiazolyl, indolizinyl, isoindolyl, indelity, indicolite, puricelli, hinayanistic, izochinolina, finality, parasiliti, naphthylidine, ginolandia, chinazolinei, cinnoline, pteridinyl, carbazolyl, phenanthridinium, criminally, dibenzofurane, benzimidazolylthio, benzisoxazole, benzoxazole, benzoxadiazole, benzothiazolylthio, benzothiazolylthio, benzopyrylium, bestiality, dibenzothiazyl, benzodioxolyl etc. Preferred groups are furylthio, tianity, imidazolidine, personilty, isothiazoline, isoxazolyl, oxazolyl, thiazolino, pyridylthio, personilty, pyrimidinyl, pyridazinyl etc.

In the present description, the term “heteroarylboronic” means a group in which sulfinil replaced by one of the above “heteroaryl”. Such groups include, for example, pyrrolidinyl, fullsurface, thienylmethyl, imidazolylalkyl, personalservice, isothiazolinones, isoxazolidine, oxazolidinyl, triazolylmethyl, pyridylsulfonyl, personalservice, pyrimidinemethanol, pyridinylmethyl, tetraallyltin, oxadiazolidine, thiadiazolidine, and goldenlines, isoindolines, indolylfulgides, indazolinone, polnischen, finalizeanypolyline, ethynodiolthinyl, henrisellier, farazinlublin, naphthalideneaniline, rhinolaryngology, ChineseSimplified, cinnaminson, peridiniales, carbosulfan, phenanthridinone, greenisland, dibenzoylresorcinol, benzimidazolylthio, benzisoxazoles, benzoxazolinone, benzoxadiazole, benzothiazolylsulfenamide, benzothiazolylsulfenamide, benzofuranyl, benzothiazoline, dibenzoylmethanes, benzodioxolyl etc. Preferred groups are fullsurface, thienylmethyl, imidazolylalkyl, personalservice, isothiazolinones, isoxazolidine, oxazolidinyl, triazolylmethyl, pyridylsulfonyl, personalservice, pyrimidinemethanol, pyridinylmethyl etc.

In the present description, the term “heteroarylboronic” means a group in which sulfonyl replaced by one of the above “heteroaryl”. Such groups include, for example, pyrrolidinyl, fullcolor, thienylmethyl, imidazolylalkyl, pyrazolinones, isothiazolinones, isoxazolidinone, oxazolidinyl, triazolylmethyl, pyridylsulfonyl personalality, pyrimidinemethanol, pyridinylmethyl, tetraallylsilane, oxadiazolidine, thiadiazolidine, indonesianisation, isoindolines, indolylmethane, indazolinone, polnischer, finalizemillion, ethynodiolthinyl, chinaillon, ftesinisw.html, naftiridinelor, rhinolaryngology, girasolereale, cinlinefilter, peridiniales, carbosulfan, financeminister, criminality, dibenzobarrelenes, benzimidazolecarbamic, benzisoxazole, benzoxazolinone, benzoxadiazole, benzothiazolylsulfenamide, benzothiazolylsulfenamide, benzofuranyl, benzothiazolone, dibenzoylmethanes and benzodioxolyl. The preferred groups are fullcolor, thienylmethyl, imidazolylalkyl, pyrazolinones, isothiazolinones, isoxazolidinone, oxazolidinyl, triazolylmethyl, pyridylsulfonyl, personalality, pyrimidinemethanol and pyridinylmethyl.

In the present description, the term “heteroarylboronic” means a group in which an oxygen atom is substituted by one of the above “heteroarylboronic”. Such groups include, for example, pyrrolidinyloxy, fuelsolutions, the enterprise is ylsulphonyl, imidazolylalkyl, pyrazolylborate, isothiazolinones, isoxazolecarboxylic, oxazolidinones, thiazolidinedione, pyridylsulfonyl, personalcashadvance, pyrimidinecarbonitrile, pyridinylmethyl, tetraallylsilane, oxadiazolones, thiadiazolidine, indonesiamalaysia, isoindolines, indolylmethane, industrysolutions, puenylalanine, hinayanistic, ethynodiolthinyl, chinaincorporated, fcarininsurance8, naftalinsulfokisloty, rhinolaryngology, hiazolidinedione, indolinecarboxylic, peridiniales, carbonylchloride, financinginsurance, accidentinsurance, dibenzoylacetylene, benzimidazolecarboxylate, benzisoxazoles, benzoxazolinone, benzoxazolinone, benzothiazolylsulfenamide, benzothiazolylsulfenamide, benzotrichloride, benzothiazolesulfonamide, dibenzoylmethanes, benzodioxolyl etc. Preferred groups are fuelsolutions, thienylboronic, imidazolylalkyl, pyrazolylborate, isothiazolinones, isoxazolecarboxylic, ACS is polysulphonate, thiazolidinethione, pyridylsulfonyl, personalcashadvance, pyrimidinecarbonitrile, pyridinecarboxylic etc.

In the present description, the term “aromatic carbocyclic ring” means an aromatic monocyclic or condensed aromatic carbocyclic ring and includes, for example, benzene ring, naphthalene ring and anthracene ring. The preferred ring is a benzene ring.

In the present description, the term “aromatic heterocyclic ring” means an aromatic monocyclic or condensed aromatic heterocyclic ring. Such rings include, for example, pyrrole ring, furan ring, thiophene ring, a pyrazol ring, imidazole ring, isothiazol ring, isoxazole ring, oxazole ring, thiazole ring, pyrazinone ring, pyrimidine ring, pyridazine ring, tetrazole ring, oxadiazole ring, thiadiazole ring, indolizine ring, isoindoline ring, indole ring, indazol ring, purine ring, chinolinowe ring, isoquinoline ring, quinoline ring, tarasieve ring, naphthyridine ring, chinolinowe ring, hintline ring, cinnoline ring, pteridine ring, carbazole the ring, phenanthridinium ring, acridine ring, dibenzofurane ring, benzoxazole ring, benzoxazinone ring, benzoimidazole ring, benzisoxazole ring, benzooxazole ring, benzoxadiazole ring, benzothiazoline ring, benzothiazoline ring, benzopyrrole ring, benzothiophene ring, dibenzothiophene ring and benzodioxole ring. Preferred rings are pyridine ring, furan ring and a thiophene ring.

In the present description, the term “isoindol” means 4-azaindole, 5-azaindole, 6-azaindole, 7-azaindole, 4,5-diakanda, 4,6-diakanda, 4,7-diakanda, 5,6-diakanda, 5,7-diakanda, 6,7-diakanda, 4,5,6-triethanol, 4,5,7-triethanol and 5,6,7-trasando.

In the present description, the term “C1-C6alkylene” means alkylenes group with a straight or branched chain containing one to six carbon atoms, and includes, for example, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH2CH2-, -CH(CH3)CH2-, -C(CH3)2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- and-CH2CH2CH2CH2CH2CH2-. The preferred groups are-CH2-, -CH2CH2 -, -CH2CH2CH2- and-CH2CH2CH2CH2-.

In the present description, the term “alkylene, optionally containing one or two heteroatoms” in the expression “optionally substituted alkylene, optionally containing one or two heteroatom” means alkylenes group with a straight or branched chain having one to six carbon atoms, which optionally contains one or two heteroatoms and may be substituted by the above “alkyl”, and includes, for example, -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2CH2-, -CH2O-, -och2-, -CH2CH2O-, -och2CH2-, -CH2S-, -SCH2-, -CH2CH2S-, -SCH2CH2-, -CH2CH2OCH2CH2-, -OCH2CH2O-, -OCH2O-, -NHCH2-, -N(CH3)CH2-, -N+(CH3)2CH2-, -NHCH2CH2CH2-, -N(CH3)CH2CH2CH2and so the Preferred groups are-CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -Och2CH2O-, -och2O - and-N(CH3)CH2CH2CH2-.

N is a small description of the invention, the term “albaniles, optionally containing one or two heteroatoms” in the expression “optionally substituted alkylene, optionally containing one or two heteroatom” means alkenylamine group with a straight or branched chain having two to six carbon atoms, which optionally contains one or two heteroatoms and may be substituted by the above “alkyl”, and includes, for example, -CH=SSN=CH-, -CH=Cho-, -och=CH-, -CH=CHS-, -SCH=CH-, -CH=CHNH-, -NHCH=CH-, -CH=CH-CH=N - and-N=CH-CH=CH-. The preferred groups are-CH=SSN=CH-, -CH=CHCH=N - and-N=CHCH=CH-.

In the present description, the term “akinyan, optionally containing one or two heteroatom” means alkynylamino group with a straight or branched chain having two to six carbon atoms, which optionally contains one or two heteroatoms and may be substituted by the above “alkyl”, and includes, for example, -C≡CLO2-, -CH2With≡CLO2-, -CH2With≡CLO2O-, -och2With≡CH-, -CH2With≡CCH2S-SCH2C≡CH-, -CH2C≡CCH2NH-, -NHCH2C≡CH-, -CH2C≡CCH2N(CH3)- and-N(CH3)CH2C≡CH. Particularly preferred groups are-CH2With≡CLO2- and-co2WITH≡CH-.

In the present description, the term “nitrogen-containing non-aromatic geterotsiklicheskikh ring” means a 3-12-membered nonaromatic the heterocyclic ring, containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom, which has the formula:

In the present description, the term “nitrogen-containing aromatic heterocyclic ring” means a 3-12-membered aromatic heterocyclic ring containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom in the ring. Such groups include, for example, pyrrolyl (for example, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl), imidazolyl (for example, 2-imidazolyl, 4-imidazolyl), pyrazolyl (for example, 1-pyrazolyl, 3-pyrazolyl), isothiazole (for example, 3-isothiazole), isoxazolyl (for example, 3-isoxazolyl), oxazolyl (for example, 2-oxazolyl), thiazolyl (for example, 2-thiazolyl), pyridyl (e.g. 2-pyridyl, 3-pyridyl, 4-pyridyl), pyrazinyl (for example, 2-pyrazinyl), pyrimidinyl (for example, 2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl (for example, 3-pyridazinyl), tetrazolyl (for example, 1H-tetrazolyl), oxadiazolyl (e.g., 1,3,4-oxadiazolyl) and thiadiazolyl (e.g., 1,3,4-thiadiazolyl).

In the present description of the invention, the term “3-8-membered nitrogen-containing aromatic heterocyclic ring containing one or two nitrogen atom”means a ring expressed by the formula:

In the present description, the term “4-to 8-membered azo is containing aromatic heterocyclic ring, containing one or two nitrogen atom”means a ring expressed by the formula:

In the present description of the invention ortho-, meta - and para-position substitution L3and Y means the relationship of the formula:

when the ring C is benzene ring.

In the present description of the invention, examples of the substituents in “optionally substituted alkyl”, “optionally substituted, alkyloxy”, “optionally substituted, alkylthio”, “optionally substituted alkylsulfonyl”, “optionally substituted alkylsulfonyl”, “optionally substituted, alkylsulfonate” and “optionally substituted allyloxycarbonyl include cycloalkyl, alkylene, optionally containing one or two heteroatoms, hydroxy, oxo, alkyloxy, optionally substituted foster group And one of the three positions, mercapto, alkylthio, halogen atom, nitro, cyano, carboxy, alkylaminocarbonyl, optionally substituted amino, optionally substituted carbamoyl, acyl, aryl, optionally substituted foster group In one of three positions (for example, phenyl), heteroaryl, optionally substituted foster group With one to three positions (for example, pyridyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl), optionally substituted aeromatic the civil heterocyclic ring, which may be substituted by the replacement by the group With one to three positions (for example, morpholinyl, pyrrolidinyl, piperazinil), aryloxy, optionally substituted foster group In one of three positions (for example, phenyloxy), alkylsulfonyl and the like. These groups can be substituted one to three substituents at any possible position.

In the present description of the invention, examples of substituents in the “optionally substituted alkenyl”, “optionally substituted quinil”, “optionally substituted, alkenylacyl”, “optionally substituted, alkyloxy”, “optionally substituted, alkanity”, “optionally substituted, alkylthio”, “optionally substituted alkenylcarbazoles”, “optionally substituted alkyloxyaryl”, “optionally substituted cycloalkyl”, “optionally substituted cycloalkenyl”, “optionally substituted, cycloalkane”, “optionally substituted, cycloalkenyl”, “optionally substituted, cycloalkyl”, “optionally substituted, cycloalkenyl”, “optionally substituted cycloalkylcarbonyl”, “optionally substituted cycloalkylcarbonyl”, “optionally substituted cycloalkylcarbonyl”, “optionally substituted cycloalkylcarbonyl”, “optionally substituted, cycloalkylcarbonyl”, “obazatelno replaced cycloalkylcarbonyl”, “optionally substituted alkenylcarbazoles”, “optionally substituted C1-C6alkylene”, “optionally substituted alkylene”, “optionally substituted alkeneamine” and “optionally substituted alkylamine” include alkyl, optionally substituted foster group D in one of three positions, cycloalkyl, alkylene, optionally containing one or two heteroatoms, hydroxy, oxo, alkyloxy, optionally substituted foster group And one of the three positions, mercapto, alkylthio, halogen atom, nitro, cyano, carboxy, alkylaminocarbonyl, optionally substituted amino, optionally substituted carbarnoyl, acyl, acyloxy, aryl, optionally substituted foster group In one to three provisions (e.g., phenyl), heteroaryl, optionally substituted foster group With one to three positions (for example, pyridyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl), non-aromatic heterocyclic group optionally substituted by the replacement by the group With one to three positions (for example, morpholinyl, pyrrolidinyl, piperazinil), aryloxy, optionally substituted foster group With one to three positions (for example, phenyloxy), alkylsulfonyl and the like. These groups may be substituted by one or more substituents at any possible put the I.

In the present description of the invention, examples of substituents in the “optionally substituted aryl”, “optionally substituted, phenoxy”, “optionally substituted, aryloxy”, “optionally substituted, phenylthio”, “optionally substituted, aristeo”, “optionally substituted arylsulfonyl”, “optionally substituted arylsulfonyl”, “optionally substituted, arylsulfonyl”, “optionally substituted heteroaryl”, “optionally substituted, heteroaromatic”, “optionally substituted, heteroaromatic”, “optionally substituted heteroarylboronic”, “optionally substituted heteroarylboronic”, “optionally substituted, heteroarylboronic” and “optionally substituted non-aromatic heterocyclic group” include alkyl not necessarily replaced by the replacement by the group D in one of three positions, cycloalkyl, alkenyl, quinil, hydroxy, alkyloxy, optionally substituted foster group And one of the three positions, aryloxy, optionally substituted foster group In one of three positions (for example, phenoxy), mercapto, alkylthio, halogen atom, nitro, cyano, carboxy, allyloxycarbonyl, acyl, alkylsulfonyl, optionally substituted amino, optionally substituted carbarnoyl, aryl, optionally substituted foster group In one to three position is the deposits (for example, phenyl), heteroaryl, optionally substituted foster group With one to three positions (for example, pyridyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl), non-aromatic heterocyclic group optionally substituted by the replacement by the group With one to three positions (for example, morpholinyl, pyrrolidinyl, piperazinil) and the like. These groups may be substituted by one or more substituents at any possible position.

Proxy group includes a halogen atom and phenyl, optionally substituted with one to three substituents selected from foster group C.

Replacement group include halogen atom, alkyl, alkyloxy, cyano and nitro.

Replacement group includes a halogen atom and alkyl.

Replacement group D includes a halogen atom, alkyloxy.

In the present description, the term “equivalent of carboxyl group” means a biological equivalent and includes the substituents having the same polar action, and carboxyl group. Such groups include, for example, CONHCN-, -CONHOH-, -CONHOMe, -CONHOt-Bu-CONHOCH2Ph, -SO3H, -SO2NH2, -SO2NHMe, -NHCONH2, -NHCONMe2, -P(=O)(OH)2, -P(=O)(OH)(OEt), -P(=O)(OH)NH2, -P(=O)(OH)NHMe, -CONHSO2Ph, -SO2NHCOMe, -SO2NHCOPh and groups of the formulas:

Preferred FCU is the groups are CONHOt-Bu, -CONHOCH2Ph, -SO3H-CONHSO2Ph, -SO2NHCOMe, -SO2NHCOPh and groups of the formulas:

The compound of General formula (I) includes compounds of the General formula:

where R2A, R2B, R2C, R2Dand R2Eindependently mean a hydrogen atom, halogen atom, optionally substituted alkyl, optionally substituted of alkenyl, optionally substituted quinil, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxy, optionally substituted, alkyloxy, optionally substituted, alkenylacyl, optionally substituted, alkyloxy, optionally substituted, cycloalkane, optionally substituted, cycloalkenyl, mercapto, optionally substituted, alkylthio, optionally substituted, alkanity, optionally substituted, alkylthio, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyl, optionally substituted, alkylsulfonate, optionally substituted, cycloalkyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted, cycloalkylcarbonyl, optionally substituted, cycloalkenyl, optionally substituted cycloalkylcarbonyl, optionally substituted cycloalkylcarbonyl, neo is Astelin replaced cycloalkylcarbonyl, optionally substituted amino, acyl, optionally substituted allyloxycarbonyl, optionally substituted alkenylacyl, optionally substituted alkyloxyaryl, optionally substituted aryloxyalkyl, optionally substituted carbarnoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted, aryloxy, optionally substituted, aaltio, optionally substituted arylsulfonyl, optionally substituted arylsulfonyl, optionally substituted, arylsulfonyl, optionally substituted heteroaryl, optionally substituted, heteroaromatic, optionally substituted, heteroaromatic, optionally substituted heteroarylboronic, optionally substituted heteroarylboronic, optionally substituted, heteroarylboronic or optionally substituted non-aromatic heterocyclic group; L3matter referred to in paragraph (1);

where R2A, R2B, R2C, R2Dand R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1);

where R2A, R2B, R2C, R2D/sup> and R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1);

where R2A, R2B, R2C, R2Dand R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1);

where R2A, R2B, R2C, R2Dand R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1);

where R2A, R2B, R2C, R2Dand R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1);

Among the compounds of the above General formulas, the preferred compounds are compounds of the General formula:

where R2A, R2B, R2C, R2Dand R2Ethey who have the above meanings; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1); and the most preferred compounds are compounds of the General formula:

where R2A, R2B, R2C, R2Dand R2Ehave the values indicated above; R3matter referred to in paragraph (1); R4A, R4B, R4Cand R4Dhave the above values; L3matter referred to in paragraph (1).

In the General formula (I), examples of groups of the formula:

include groups of the formula

where R3matter referred to in paragraph (1); R4Aand R4Bhave the above values; and groups of formula

where R3matter referred to in paragraph (1); R4Ahas the above values.

Among the above-mentioned preferred groups are groups of the formula

where R3matter referred to in paragraph (1); R4Aand R4Bhave the above values.

Preferred values of ring A, ring B, ring C, R1-R5, M, Y, L1L2L3, k, n and q in the compound of General formula (I) before the taulani as (Ia) - (IIl). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of rings And preferred value (Ia) are benzene ring, furan ring, thiophene ring or a pyridine ring and a more preferred value of (Ib) is a benzene ring or a pyridine ring.

In the denition of the ring In the preferred value (Ic) is a group of the formula:

the preferred value (Id) is a group of the formula:

and the most preferred value (Ie) is a group of the formula:

In the denition of the ring With a preferred value (If) is a benzene ring, naphthalene ring, pyridine ring or a benzimidazole ring, and more preferred group (Ig) is a benzene ring.

In the definition of R1the preferred value (Ih) is carboxy, alkoxycarbonyl, optionally substituted carbarnoyl or equivalent carboxyl group, and more preferred value of (Ii) is carboxy.

In the definition of R2the preferred value (Ij) is a halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optional the part replaced carbarnoyl, cyano, nitro, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic ring, more preferred is (Ik) is a halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, optionally substituted carbarnoyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted non-aromatic heterocyclic ring, and the most preferred value (Il) is a halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted aryl or optionally substituted heteroaryl.

In the definition of R3the preferred value (Im) is optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane or optionally substituted, aryloxy, the preferred value (In) is optionally substituted C1-C6alkyloxy or optionally substituted C1-C6alkylthio and the most preferred value (Io) is a C2-C4alkyloxy or optionally substituted C2-C4alkylthio.

In the definition of R4the preferred value of (Ip) is a halogen atom,optionally substituted alkyl, optionally substituted, alkyloxy, cyano, nitro, optionally substituted aryl or optionally substituted heteroaryl, the preferred value (Iq) is a halogen atom, optionally substituted alkyl or optionally substituted, alkyloxy and the most preferred value (Ir) is a halogen atom or optionally substituted alkyl.

In the definition of R5the preferred value (Is) is optionally substituted alkyl or oxo, and a more preferred value (It) is alkyl.

In the definition of M preferred value (Iu) is sulfonyl or carbonyl and the preferred value (Iv) is sulfonyl.

In determining the preferred value of Y (Iw) is a simple bond or optionally substituted alkylene, optionally containing one or two heteroatoms, and a more preferred value of (Ix) is a simple link.

In the definition of L1the preferred value (Iy) is a simple bond or optionally substituted alkylene, optionally containing one or two heteroatom, or-NH -, and more preferred is (Iz) is a simple link.

In the definition of L2the preferred value (IIa) is a simple bond or optionally substituted alkylene, optionally containing one or two heteroatoms, Il is-NH -, and more preferred is (IIb) is a simple link.

In the definition of L3the preferred value (IIc) is a simple bond, methylene, -O -, methylene or-NH-methylene preferred value (IId) is-O -, methylene or-NH-methylene and the most preferred value (IIe) is-O-methylene.

In determining the preferred value of k (IIf) is 0, 1 or 2, and more preferred is (IIg) is 1 or 2.

In determining the preferred value of n (IIh) is 0, 1 or 2, and more preferred is (IIi) is 0.

In determining the preferred value of q (IIj) is 0 or 1, and more preferred value is (IIk) 1 or (IIl) 0.

Preferred values of ring A, ring B, ring C, R1-R5, M, Y, L1L2L3, k, n and q in the compound of General formula (II) represented by (Ia) - (IIl). Preferred compounds are compounds containing the possible combinations of the specified values.

In the denition of the ring And the preferred value is above the value (Ia) and the preferred value is above the value (Ib).

In the denition of the ring In the preferred value is the ring of the above formula (Ic), the preferred value is the ring of the above formula (Id) and the most preferred value is the ring of the above formula Ie).

In the denition of the ring With the preferred value is above the value (If) and the preferred value is above the value (Ig).

In the definition of R1the preferred value is above the value (Ih) and the preferred value is above the value of (Ii).

In the definition of R2the preferred value is above the value (Ij), the preferred value is above the value (Ik) and the most preferred value is above the value (Il).

In the definition of R3the preferred value is above the value (Im), the preferred value is above the value (In) and the most preferred value is above the value (Io).

In the definition of R4the preferred value is above the value (Ip), the preferred value is above the value (Iq) and the most preferred value is above the value (Ir).

In the definition of R5the preferred value is above the value (Is) and the preferred value is above the value (It).

In the definition of M preferred value is above a value (Iu) or more predpochtite the d value is above the value (Iv).

In the definition of Y, the preferred value is above the value (Iw) and the preferred value is above the value of (Ix).

In the definition of L1the preferred value is above the value (Iy) and the preferred value is above the value (Iz).

In the definition of L2the preferred value is above the value of (IIa) and the preferred value is above the value (IIb).

In the definition of L3the preferred value is above the value (IIc), the preferred value is above the value (IId) and the most preferred value is above the value (IIe).

In determining the preferred value of k is above the value (IIf) and the preferred value is above the value (IIg).

In determining the preferred value of n is above the value (IIh) and the preferred value is the value of (IIi).

In the definition of q, the preferred value is above the value (IIj) and the preferred value is above the value (IIk) or (IIl).

Preferred values of ring D, R1-R5, M, Y, Z, L3, p, n and q in the compound of General formula (III), not only the us how (If)to(Ix), (IIc-IIe) and (IIg)-(IIn). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring D preferred value is above the value (If) and the preferred value is above the value (Ig).

In the definition of R1the preferred value is above the value (Ih) and the preferred value is the value of (Ii).

In the definition of R2the preferred value is above the value (Ij), the preferred value is above the value (Ik) and the most preferred value is above the value (Il).

In the definition of R3the preferred value is above the value (Im), the preferred value is the value (In) and the most preferred value is the value (Io).

In the definition of R4the preferred value is above the value (Ip), the preferred value is above the value (Iq) and the most preferred value is the value of (Ir).

In the definition of R5the preferred value is above the value (Is) and the preferred value is above the value (It).

In the definition of M preferred C is achenium is above a value (Iu) and the preferred value is above the value (Iv).

In the definition of Y, the preferred value is above the value (Iw) and the preferred value is above the value of (Ix).

In determining the preferred value of Z (IIm) is CH, C-R4or N and the preferred value (IIn) is the value of SN.

In the definition of L3the preferred value is above the value (IIc), the preferred value is above the value (IId) and the most preferred value is above the value (IIe).

In determining the preferred value of n is above the value (IIh) and the preferred value is above the value of (IIi).

In the definition of q, the preferred value is above the value (IIj) and the preferred value is above the value (IIk) or (IIl).

In the definition of R, the preferred value is above the value (IIg).

Preferred values of ring D, ring E, R1-R5, M, Y, Z, L3, p, n and q in the compound of General formula (IV) is represented as (If)to(Ix), (IIc)-(IIe) and (IIg)-(IIp). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring D preferred value is above the value (If) and more pre is reverent value is above the value (Ig).

In the definition of R1the preferred value is above the value (Ih) and the preferred value is above the value of (Ii).

In the definition of R2the preferred value is above the value (Ij), the preferred value is above the value (Ik) and the most preferred value is above the value (Il).

In the definition of R3the preferred value is above the value (Im), the preferred value is above the value (In) and the most preferred value is above the value (Io).

In the definition of R4the preferred value is above the value (Ip), the preferred value is above the value (Iq) and the most preferred value is above the value (Ir).

In the definition of R5the preferred value is above the value (Is) and operation for the preferred value is above the value (It).

In the definition of M preferred value is above a value (Iu) and the preferred value is above the value (Iv).

In the definition of Y, the preferred value is above the value (Iw) and more preferred z is achenium is above the value of (Ix).

In determining the preferred value of Z (IIm) is CH, C-R4or N and the preferred value (IIn) is the value of SN.

In the definition of L3the preferred value is above the value (IIc), the preferred value is above the value (IId) and the most preferred value is above the value (IIe).

In determining the preferred value of n is above the value (IIh) and the preferred value is above the value of (IIi).

In the definition of q, the preferred value is above the value (IIj) and the preferred value is above the value (IIk) or (IIl).

In the definition of R, the preferred value is above the value (IIg).

In determining the E ring, the preferred value (II ° series) is a ring of the formula:

and a more preferred value (IIp) is a ring of the formula:

The preferred values of the Ab ring, ring Bb, ring Cb, R1b-R5b, Yb, Zb, kb, mb, nb, and p in the compound of General formula (I-b) represented as (IIIa)-(IVc). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring Ab, prepact the positive value (IIIa) is a benzene ring, furan ring, thiophene ring or a pyridine ring, and more preferred is (IIIb) is a benzene ring or a pyridine ring.

In the definition of ring Bb preferred value (IIIc) is a ring of the formula:

the preferred value (IIId) is a ring of the formula:

and the most preferred value (IIIe) is a ring of the formula:

In the definition of ring Cb preferred value (IIIf) is a benzene ring, naphthalene ring or a pyridine ring, and more preferred is (IIIg) is a benzene ring.

In the definition of R1bthe preferred value (IIIh) is hydroxyalkyl, carboxy or alkoxycarbonyl and preferred value (IIIi) is carboxy.

In the definition of R2bthe preferred value (IIIj) is a halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted amino, cyano, nitro, optionally substituted aryl or optionally substituted heteroaryl and preferred value (IIIk) is a halogen atom, optionally substituted alkyl, optionally substituted, alkyloxy, optionally substituted aryl or optionally replacing the military heteroaryl.

In the definition of R3bthe preferred value (IIIl) is optionally substituted, alkyloxy, optionally substituted, alkylthio, optionally substituted, cycloalkane or optionally substituted, aryloxy and preferred value (IIIm) is optionally substituted C2-C4alkyloxy or optionally substituted C2-C4alkylthio.

In the definition of R4bthe preferred value (IIIn) is a halogen atom, optionally substituted alkyl, cyano, nitro, optionally substituted aryl or optionally substituted heteroaryl and preferred value (IIIo) is a halogen atom or optionally substituted alkyl.

In the definition of R5bthe preferred value (IIIp) is optionally substituted alkyl and the most preferable value (IIIq) is alkyl.

In the definition of Ybthe preferred value (IIIr) is a simple connection, alkylene or-O -, and more preferred is (IIIs) is a simple bond or-O-.

In the definition of the Zbthe preferred value (IIIt) is alkylen, albaniles or-O-alkylene and preferred value (IIIu) is methylene or-O-alkylene.

In determining kb the preferred value (II-IV) is 1, 2 or 3 and the preferred value (IIIw) is 1 ili.

In defining mb preferred value (IIIx) is 0, 1 or 2, and more preferred is (IIIy) is 0 or 1.

In determining nb preferred value (IIIz) is 0, 1 or 2 and the preferred value (IVa) is 0.

In determining pb preferred value (IVb) is 0 or 1, and more preferred is (IVc) is 1.

The preferred values of the Ab ring, ring Bb, ring Cb, R1b-R5b, Yb, Zb, kb, mb and nb in the compound of General formula (II-b) is represented as (IIIa)-(IVa). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring Ab preferred value is above the value (IIIa) and the preferred value is above the value (IIIb).

In the definition of ring Bb preferred value is the ring of the above formula (IIIc), the preferred value is the ring of the above formula (IIId) and the most preferred value is the ring of the above formula (IIIe).

In the definition of ring Cb preferred value is above the value (IIIf) and the preferred value is above the value (IIIg).

In the definition of R1bthe preferred value is above the value(IIIh), and the preferred value is above the value (IIIi).

In the definition of R2bthe preferred value is above the value (IIIj) and the preferred value is above the value (IIIk).

In the definition of R3bthe preferred value is above the value (IIIl) and the preferred value is above the value (IIIm).

In the definition of R4bthe preferred value is above the value (IIIn) and the preferred value is above the value (IIIo).

In the definition of R5bthe preferred value is above the value (IIIp) and the preferred value is above the value (IIIq).

In the definition of Ybthe preferred value is above the value (IIIr) and the preferred value is above the value (IIIs).

In the definition of the Zbthe preferred value is above the value (IIIt) and the preferred value is above the value (IIIu).

In determining kb the preferred value is above the value of (II-IV) and the preferred value is above the value (IIIw).

In defining mb the preferred value is above the value (IIIx), and the preferred value is above the value is s (IIIy).

In determining nb preferred value is above the value (IIIz) and the preferred value is videocasino value (IVa).

Preferred values of ring Cb, R1b-R5bXb, Yb, Zb, mb, nb and qb in the compound of General formula (III-b) is represented as (IIIf)-(IIIu), (IIIx)-(IVa) and (IVd)-(IVg). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring Cb preferred value is above the value (IIIf) and the preferred value is above the value (IIIg).

In the definition of R1bthe preferred value is above the value (IIIh), and the preferred value is above the value (IIIi).

In the definition of R2bthe preferred value is above the value (IIIj) and the preferred value is above the value (IIIk).

In the definition of R3bthe preferred value is above the value (IIIl) and the preferred value is above the value (IIIm).

In the definition of R4bthe preferred value is above the value (IIIn) and the preferred value is above the value (IIIo).

In the definition of R5bpredpochtitel the s value is above the value (IIIp) and the preferred value is above the value (IIIq).

In the definition of Ybthe preferred value is above the value (IIIr) and the preferred value is above the value (IIIs).

In the definition of the Zbthe preferred value is above the value (IIIt) and the preferred value is above the value (IIIu).

In defining mb the preferred value is above the value (IIIx), and the preferred value is above the value (IIIy).

In determining nb preferred value is above the value (IIIz) and the preferred value is videocasino value (IVa).

In determining qb preferred value (IVd) is 1, 2 or 3 and the preferred value (IVe) is 1 or 2.

In the definition of Xbthe preferred value is (IVf) SN or (IVg) N.

Preferred values of ring Cb, ring Db, R1b-R5bXb, Yb, Zb, mb, nb, and sb in the compound of General formula (IV-b) is represented as (IIIf)-(IIIu), (IIIx)-(IVa) and (IVf)-(IVk). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring Cb preferred value is above the value (IIIf) and the preferred value is above the value (IIIg).

the definition of R 1bthe preferred value is above the value (IIIh), and the preferred value is above the value (IIIi).

In the definition of R2bthe preferred value is above the value (IIIj) and the preferred value is above the value (IIIk).

In the definition of R3bthe preferred value is above the value (IIIl) and the preferred value is above the value (IIIm).

In the definition of R4bthe preferred value is above the value (IIIn) and the preferred value is above the value (IIIo).

In the definition of R5bthe preferred value is above the value (IIIp) and the preferred value is above the value (IIIq).

In the definition of Ybthe preferred value is above the value (IIIr) and the preferred value is above the value (IIIs).

In the definition of the Zbthe preferred value is above the value (IIIt) and the preferred value is above the value (IIIu).

In defining mb the preferred value is above the value (IIIx), and the preferred value is above the value (IIIy).

the determination of nb preferred value is above the value (IIIz) and the preferred value is above the value (IVa).

In the definition of Xbthe preferred value is above the value (IVf) or (IVg).

In the definition of ring Db preferred value (IVh) is a ring of the formula:

and a more preferred value (IVi) is a ring of the formula:

In the definition of sb's preferred value (IVj) is 1, 2 or 3 and the preferred value (IVk) is 1 or 2.

Preferred values of ring Cb, rings, Eb, R1b-R4bXb, Wb, Zb, mb, nb, and sb in the compound of General formula (V-b) is represented as (IIIf)-(IIIo), (IIIt)-(IIIu), (IIIx)-(IVa), (IVf)-(IVg) and (IVj)-(IVo). Preferred compounds are compounds containing the possible combinations of the specified values.

In the definition of ring Cb preferred value is above the value (IIIf) and the preferred value is above the value (IIIg).

In the definition of R1bthe preferred value is above the value (IIIh), and the preferred value is above the value (IIIi).

In the definition of R2bthe preferred value is above the value (IIIj) and the preferred value is above the value (IIIk).

In the definition of R3bthe preferred value is above the defined value (IIIl) and the preferred value is above the value (IIIm).

In the definition of R4bthe preferred value is above the value (IIIn) and the preferred value is above the value (IIIo).

In the definition of the Zbthe preferred value is above the value (IIIt) and the preferred value is above the value (IIIu).

In defining mb the preferred value is above the value (IIIx), and the preferred value is above the value (IIIy).

In determining nb preferred value is above the value (IIIz) and the preferred value is videocasino value (IVa).

In the definition of Xbthe preferred value is above the value (IVf) or (IVg).

In the definition of sb preferred value is above the value (IVj) and more predpochtitelnei value is above the value (IVk).

In the definition of ring Eb preferred value (IVl) is a ring of the formula:

and a more preferred value (IVm) is a ring of the formula:

In determining Wbthe preferred value (IVn) is a simple connection, alkylene or-O -, and more preferred is (IVo) is a simple bond or-O-.

The effect of the Britania

Compounds of the present invention can be used as a medicine, in particular for the treatment of allergic diseases, as these compounds have excellent antagonistic activity against receptor DP and high security.

The best option of carrying out the invention

Compounds of the present invention can be obtained with the following method a, b or C. in Addition, the structural formulas of the compounds (IV)-(XV), (XVII), (XVIII), (XIX) and (XX) include a racemate or optical isomer.

The following describes the method:

where ring A, ring B, ring C, R1, R2, R3, R4, R5, M, Y, L1L2L3, k, n and q have the meanings specified above in paragraph (1); La means a halogen atom or a hydroxyl group; Lb denotes a hydrogen atom, halogen atom, hydroxyl group, methylsulfonylamino, paratoluenesulfonyl or tert-butyloxycarbonyl.

The educt of the formula (VI) can be purchased commercially or obtained by chemical modification of the substituent in the compound of formula (VI), such as alkylation, esterification, amidation, hydrolysis, reductive reaction, oxidation reaction, Suzuki reaction mix, the introduction and removal of protective groups and things like the haunted.

In stage 1, the compound of formula (VI) is subjected to interaction with the compound of the formula (VII) with the formation of the compounds of formula (VIII).

This reaction can be carried out by using 0.5 to 5 equivalents of compound (VII) with respect to compound (VI) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

This reaction can be performed in the presence of 1-5 equivalents of the base. Examples of preferred bases include sodium hydride, potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, triethylamine and the like.

Examples of preferred solvents include tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide, water and the like, which can be used separately or as a mixed solvent.

When Lb means tert-butyloxycarbonyl from the specified connection can be removed protective group in a solvent such as ethyl acetate, etc. at 0°C-150°C for a period of time from 5 minutes to 48 hours using hydrochloric acid.

In stage 2, the compound of formula (VIII) is condensed with the compound of the formula (IX) and the product, if necessary, hydrolyzing in basic conditions to form compounds of formula (I).

This reaction can be carried out by using 0.5 to 5 equivalents of compound (IX) with respect of the part of the compound (VIII) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include ethyl acetate, methylene chloride, tetrahydrofuran, toluene, N,N-dimethylformamide, methanol, dioxane, water and the like, which can be used separately or as a mixed solvent.

If necessary, as a condensing agent can be used 0.05 to 5 equivalents (a) 1,1'-azodicarbon)dipiperidino and tributylphosphine or (b) Tris(dibenzylideneacetone)diplegia(0), Xanthos and tert-butoxide sodium relative to the compounds of formula (VIII).

The hydrolysis may be performed using 1-5 equivalents of a base with respect to the compounds of formula (VII) at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include tetrahydrofuran, methanol, N,N-dimethylformamide, water and the like, which can be used separately or as a mixed solvent.

Examples of preferred bases include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, and the like.

In addition, each Deputy may be converted into another Deputy with the help of such reactions as alkylation, esterification, amidation, hydrolysis, reductive reaction, oxidation reaction, Suzuki reaction mix, the introduction and removal is their protective groups and the like. Products (VIII) and (I)obtained at each stage, can be cleaned by a conventional method such as chromatography on columns or recrystallization.

The following describes the method:

where ring A, ring C, R1, R2, R3, R4, R5L3, k, n and q have the meanings specified above in paragraph (1).

In stage 1, the compound of formula (X) is subjected to interaction with the compound of the formula (XI) with the formation of the compounds of formula (XII).

This reaction can be carried out by using 0.5 to 5 equivalents of compound (XI) with respect to compound (X) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

This reaction can be performed in the presence of 1-5 equivalents of the base. Examples of preferred bases include sodium hydride, potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, triethylamine and the like.

Examples of preferred solvents include tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide, water and the like, which can be used separately or as a mixed solvent.

In stage 2, the compound of formula (XII) is subjected to interaction with the compound of the formula (XIII) and the product, if necessary, hydrolyzing in basic conditions to form compounds of formula (XIV)

This reaction can be carried out by using 0.5 to 5 equivalents of compound (XIII) with respect to compound (XII) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include ethyl acetate, methylene chloride, tetrahydrofuran, N,N-dimethylformamide, methanol, dioxane, water and the like, which can be used separately or as a mixed solvent.

If necessary, this reaction may be performed in the presence of 1-5 equivalents of the base. Examples of preferred bases include sodium hydride, potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, triethylamine and the like.

In addition, can be used from 0.2 to 4 equivalents of potassium iodide relative to the compounds of formula (XIII).

The hydrolysis may be performed using 1-5 equivalents of a base with respect to the compounds of formula (XII) at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include tetrahydrofuran, methanol, N,N-dimethylformamide, water and the like, which can be used separately or as a mixed solvent.

Examples of preferred bases include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, potassium bicarbonate,sodium bicarbonate, and the like.

In addition, each Deputy may be converted into another Deputy with the help of such reactions as alkylation, esterification, amidation, hydrolysis, reductive reaction, oxidation reaction, Suzuki reaction mix, the introduction and removal of protective groups and the like. Products (XII) and (XIV)obtained at each stage, can be cleaned by a conventional method such as chromatography on columns or recrystallization.

Below is a description of the method:

where ring A, ring B, ring C, R1, R2, R3, R4, R5, Y, L3, k, n and q have the meanings specified above in paragraph (1); Lb denotes a hydrogen atom, halogen atom, hydroxyl group, methylsulfonylamino, paratoluenesulfonyl or tert-butyloxycarbonyl.

In stage 1, the compound of formula (X) is subjected to interaction with the compound of the formula (XV) with the formation of the compounds of formula (XVI).

This reaction can be carried out by using 0.5 to 5 equivalents of compound (XV) with respect to compound (X) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

This reaction can be performed in the presence of 1-5 equivalents of the base. Examples of preferred bases include sodium hydride, potassium carbonate, sodium carbonate, potassium bicarbonate, bicarbonate, the triethylamine and the like.

Examples of preferred solvents include tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide, water and the like, which can be used separately or as a mixed solvent.

When Lb means tert-butyloxycarbonyl from the specified connection can be removed protective group in a solvent such as ethyl acetate, etc. at 0°C-150°C for a period of time from 5 minutes to 48 hours using hydrochloric acid.

In stage 2, the compound of formula (XVI) is condensed with the compound of the formula (XVII) with the formation of the compounds of formula (XVIII).

This reaction can be carried out by using 0.5 to 5 equivalents of compound (XVII) with respect to compound (XVI) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include ethyl acetate, methylene chloride, tetrahydrofuran, N,N-dimethylformamide, methanol, dioxane, water and the like, which can be used separately or as a mixed solvent.

If necessary, as a condensing agent can be used at 0.5-5 equivalents of 1,1'-(azodicarbon)dipiperidino and tributylphosphine relative to the compounds of formula (XVI).

In stage 3, the compound of formula (XVIII) condense and, if necessary, reset nalivajut and/or hydrolyzing in basic conditions to form compounds of formula (XIX).

The condensation reaction can be carried out by using 0.5 to 5 equivalents of a condensing agent relative to the compound (XVIII) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include ethyl acetate, methylene chloride, tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide, water and the like, which can be used separately or as a mixed solvent.

As the condensing agent can be used carbethoxymethylthio and the like.

Double or triple bond, resulting from the condensation reaction can be restored to rich communication using conventional redox reaction.

The hydrolysis may be performed using 1-5 equivalents of a base with respect to the compounds of formula (XVIII) in a solvent at 0°C-150°C for a period of time from 5 minutes to 48 hours.

Examples of preferred solvents include tetrahydrofuran, methanol, N,N-dimethylformamide, water and the like, which can be used separately or as a mixed solvent.

Examples of preferred bases include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, and the like.

In addition,each Deputy may be converted into another Deputy with the help of this reaction, as alkylation, esterification, amidation, hydrolysis, reductive reaction, oxidation reaction, Suzuki reaction mix and the like.

Products (XVI), (XVIII) and (XIX)obtained at each stage, if necessary, can be purified by conventional methods such as chromatography on columns, recrystallization, etc.

In addition, the compound of General formula (X) can be obtained in the following way:

where ring A, R3, R4and q have the meanings specified above in paragraph (1), and W3means a halogen atom.

When performing the method of obtaining the compounds of formula (X) from the compound of formula (XX) a compound of the formula (XX) 1) turn in a derived SO3H, producing processing ClSO3Cl, and 2) glorious hydroxyl group, interacting with POCl3or PCl5with the formation of the compound of formula (X).

When performing the method of obtaining the compounds of formula (X) from the compound of formula (XXI) a compound of the formula (XIX) 1) is treated with lithium, using n-BuLi, 2) then in turn derived SO2Li, interacting with SO2and finally 3) is subjected to interaction with the SO2Cl2thus the compound of formula (XX). As W3preferably use a bromine atom or an iodine atom.

In addition, at each stage each is the first Deputy may be converted into another Deputy with the help of this reaction, as alkylation, esterification, amidation, hydrolysis, reductive reaction, oxidation reaction, Suzuki reaction mix and the like.

In the present description, the term “MES” means, for example, MES in an organic solvent, hydrate, and the like. In the case of formation of MES in an organic solvent coordination relationship may be due to any number of molecules of an organic solvent. In the case of hydrate formation coordination, communication can be related to any number of water molecules. The hydrate is usually the preferred product.

The term “compound of the present invention includes pharmaceutically acceptable salt and MES. Examples of the salt include salts with an alkali metal (lithium, sodium, potassium etc), alkaline earth metal (magnesium, calcia etc), ammonium, organic bases and amino acids, and salts with inorganic acids (hydrochloric acid, Hydrobromic acid, phosphoric acid, sulfuric acid, etc. and organic acids (acetic acid, citric acid, maleic acid, fumaric acid, benzosulfimide acid, paratoluenesulfonyl acid and so on). These salts can be obtained by usual method.

The compound of the present invention is not limited to konkretnym isomer, but includes all possible isomers and racemates.

The compound of the present invention has excellent antagonistic activity against the DP receptor, as described in the following examples. The pharmaceutical composition according to the present invention can be used as a drug for prevention and/or treatment of allergic diseases such as asthma, allergic rhinitis, allergic dermatitis, allergic conjunctivitis, food Allergy, and so podobnie; systemic mastocytosis; systematic violation of activation mastocytes; emphysema; chronic bronchitis; chronic obstructive pulmonary disease; skin disease, itching, such as atopic dermatitis and urticaria; secondary disease resulting from the itching, such as cataract and retinal detachment; brain, such as stroke, degenerative disorder brain and demyelination; insomnia; syndrome charge-Strauss; papular dermatitis, such as filariasis; vasculitis; polyarteritis; cutaneous eosinophilic granuloma; autoimmune diseases such as multiple sclerosis and transplant rejection; eosinophilic pneumopathy; histiocytosis; pneumonia; aspergillosis; pleurisy; sarcoidosis; pulmonary fibrosis; eosinophilia; g is paremia skin, like a rush of blood to the person under the influence of nicotinic acid; filariasis; schistosomiasis; trichinosis; AIDS; tuberculosis; cancer of bronchus; lymphoma; Hodgkin's disease and the like.

The compound of the present invention can be supplied by the person for treatment of the above diseases orally in the form of powder, granules, tablets, capsules, pills, liquid drug and the like or parenterally in the form of an injection solution, suppository, percutaneous drug, pharmaceutical forms for inhalation and the like.

The pharmaceutical composition can be obtained by mixing a therapeutically effective amount of the compounds of the present invention with pharmaceutical additives such as filler, binder, wetting agent, disintegrator, grease and the like, suitable for the selected drug. Injection solution can be obtained by sterilization together with an acceptable carrier.

In the treatment of the above diseases caused by PGD2 receptor, the compound of the present invention can be used in combination with another drug. In the case of treatment of inflammatory diseases including allergies, this connection can be used in combination with such drugs as antagonis the receptor leukotriene (e.g., montelukast sodium, zafirlukast, hydrate pranlukast, receptor antagonist leukotriene B4); inhibitor of leukotriene synthesis such as zileuton, the inhibitor of PDE IV (e.g., theophylline, cilomilast, roflumilast), corticosteroid (eg, prednisone, fluticasone, budesonide, ciclesonide), β2-agonist (e.g. salbutamol, salmeterol, formoterol), antibody against IgE (e.g. omalizumab), an antagonist of histamine receptors H1 (e.g., chlorpheniramine, loratadine, cetirizine), immunosuppressant (tacrolimus, cyclosporine), receptor antagonist of thromboxane A2 (for example, ramatroban), the antagonist of chemokine receptors (in particular, CCR-1, CCR-2, CCR-3), another receptor antagonist prostanoid (for example, the CRTH2 antagonist), an antagonist of adhesion molecules (e.g., antagonist VLA-4), a cytokine antagonist (e.g., antibody against IL-4, antibody against IL-3), non-steroidal anti-inflammatory agent (for example, a derivative of propionic acid, such as ibuprofen, Ketoprofen, naproxen, etc.; derived acetic acids such as indomethacin, diclofenac, etc.; salicylic acid, such as acetylsalicylic acid, an inhibitor of cyclooxygenase-2 such as celecoxib, etoricoxib).

In addition, the compound of the present invention can be used in combination with antitussive agent (such as codeine, hydrocodeine), medium, the PTO, lower cholesterol (such as lovastatin, simvastatin, fluvastatin, rosuvastatin), anticholinergic agent (such as Tiotropium, ipratropium, flutropium, oxitropium).

The dose of the compounds of the present invention depends on the severity of the disease, the route of administration, age and body weight of the subject. In the case of oral administration adult dose is typically in the range from 0.1 to 100 mg/kg/day, preferably from 1 to 20 mg/kg/day.

Examples

The present invention is hereinafter illustrated in more detail below by examples and test examples, but the scope of the invention is not limited to these examples.

In the examples used the following abbreviations:

IU:methyl
Et:ethyl
n-Pr:n-propyl
i-Pr:isopropyl
Ac:acetyl
Ph:phenyl
Bn:benzil
Boc: tert-butyloxycarbonyl
MOM:methoxymethyl
THF (THF):tetrahydrofuran
DMF (DMF):N,N-dimethylformamide
MeOH:methanol
HOBt:1-hydroxybenzotriazole
WSCD HCl:hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

Example 1. Receiving compound I-1:

Stage 1

4-Isopropoxybenzonitrile (2,34 g, 10.0 mmol) and triethylamine (of 4.2 ml, 30.0 mmol) at 0°C was added to a solution of 4-hydroxypiperidine (1.01 g, 10.0 mmol) in THF (20 ml) and the mixture was stirred for one hour. To the reaction solution was added dilute hydrochloric acid (60 ml) and ethyl acetate (60 ml), the mixture was extracted, the organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated salt solution, dried and concentrated. To the residue was added n-hexane and the resulting crystalline material was filtered, thus obtaining the compound (2) (2.8 g, yield 94%).

1H-NMR (CDCl3) δ ppm: 1,36 (q, j =6.0 Hz, 6H), 1,71 (m, 2H), 1.93 and (m, 2H), 2,84 (m, 2H), 3,23 (m, 2H), of 3.77 (m, 1H), 4,06 (m, 1H), 6,95 (d, J=8.7 Hz, 2H), 7,66 (d, J=8.7 Hz, 2H).

Stage 2

Carbethoxymethylthio (920 mg, 2.6 mmol) was added to a solution of 2-hydroxy-4-methylbenzaldehyde (3) (300 mg, 2.2 mmol) in THF (5 ml) and the mixture was heated under reflux for one hour. The reaction mixture was cooled and the solvent evaporated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=5:1) and concentrated, thus obtaining the compound (4) (320 mg, yield 70%).

1H-NMR (CDCl3) δ ppm: of 1.34 (t, J=7.2 Hz, 3H), of 2.28 (s, 3H), 4,27 (m, 2H), 6,09 (s, 1H), 6,60 (d, J=16.2 Hz, 1H), 6,74 (d, J=8,1 Hz, 1H),? 7.04 baby mortality (DD, J=2,1, 8,1 Hz, 1H), 7,27 (d, J=2.1 Hz, 1H), 8,00 (d, J=16.2 Hz, 1H).

Stage 3

Connection (2) (218 mg, 0.7 mmol), obtained in stage 1, 1,1'-(azodicarbon)dipiperidino (238 mg, 0.9 mmol) and tributylphosphine (or 0.57 ml, 2.2 mmol)was added to a solution of compound (4) (150 mg, 0.7 mmol) in THF (10 ml) and the mixture was stirred at room temperature for 4 hours. To the reaction solution was added water, the mixture was extracted with ethyl acetate, the organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=3:1), thus obtaining the compound (5) (130 m is, yield 37%).

Stage 4

2 M Aqueous solution of sodium hydroxide (0.4 ml, 0.8 mmol) was added to a solution of compound (5) (40 mg, 0.08 mmol) in THF (6 ml) and Meon (2 ml) and the mixture was stirred at room temperature for 18 hours. The reaction solution was acidified by adding diluted hydrochloric acid, the mixture was extracted with ethyl acetate, the extract washed with water, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound I-1 (15 mg, yield 40%).

1H-NMR (CDCl3) δ ppm: to 1.35 (d, 6H, J=9.0 Hz), a 2.01 (m, 4H), of 2.28 (s, 3H), 3.15 in (m, 4H), to 4.62 (m, 1H), 6,38 (d, J=16.2 Hz, 1H), 6,74 (d, J=8,4 Hz, 1H), of 6.96 (d, J=9.0 Hz, 2H), 7,11 (DD, J=1,8, and 8.4 Hz, 1H), 7,31 (d, J=1.8 Hz, 1H), 7,68 (d, J=9.0 Hz, 2H), 7,89 (d, J=16.2 Hz, 1H).

Example 2. Obtain compound II-9 and III-1:

Stage 1

4-Isopropoxybenzonitrile (2.35 g, 10.0 mmol) and triethylamine (3,7 ml of 22.0 mmol) was added to a solution of the hydrochloride of bis(2-chloroethyl)amine (6) (1.78 g, 10.0 mmol) in DMF (20 ml) and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added dilute hydrochloric acid (200 ml), the mixture was extracted with ethyl acetate (200 ml), the organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated salt solution, dried and concentrated. The resulting residue is ciali chromatography on a column of silica gel (hexane:ethyl acetate=8:1), thus obtaining the compound (7) (1,79 g, yield 53%).

1H-NMR(CDCl3) δ ppm: to 1.37 (d, J=6.3 Hz, 6H), 2,98 (m, 4H),3,74 (m, 4H), with 4.64 (m, 1H), 6,97 (d, J=9.0 Hz, 2H), 7,66 (d, J=9.0 Hz, 2H).

Stage 2

Methylbromide (7,1 ml of 75.0 mmol), potassium carbonate (13.8 g, 100.0 mmol) and potassium iodide (0,83 g, 5.0 mmol) was added to a solution of 2-methoxy-5-NITROPHENOL (8) (8,46 g, 50.0 mmol) in DMF (80 ml) and the mixture was stirred at 30°C for 2 hours. To the reaction mixture were added water and the precipitated crystalline substance was washed with water and dried, thus obtaining the compound (9) (11.9 g, yield of 99.9%).

1H-NMR (CDCl3) δ ppm: a 3.83 (s, 3H), 3,99 (s, 3H), 4,78 (s, 2H), of 6.96 (d, J=9.0 Hz, 1H), 7,69 (d, J=2.4 Hz, 1H), 7,98 (DD, J=2,4, and 9.0 Hz, 1H).

Stage 3

To a solution of compound (9) (5,95 g 25,0 mmol) in a mixture of THF (60 ml) and Meon (60 ml) was added 10% palladium carbon (1.2 g) and the mixture was stirred in hydrogen atmosphere at room temperature for 5 hours. The reaction mixture was filtered through celite and the filtrate was concentrated, thus obtaining the compound (10) (5,28 g, yield of 99.9%).

1H-NMR (CDCl3) δ ppm: 3,20 (users, 2H), 3,79 (s, 3H), 3,81 (s, 3H)and 4.65 (s, 3H), 6,28-6,34 (m, 2H), 6.73 x (d, J=8,4 Hz, 1H).

Stage 4

Compound (7) (749 mg, 2.2 mmol), potassium carbonate (1,11 g, 8.0 mmol) and potassium iodide (66,4 mg, 0.4 mmol) was added to a solution of compound (10) (422 mg, 2.0 mmol) in DMF (5 ml) and the mixture was stirred at room temperature for 18 hours. The reaction is ionic solution was added dilute hydrochloric acid (50 ml), the mixture was extracted with ethyl acetate (50 ml), the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=2:1), thus obtaining the compound III-1 (43 mg, yield 5%).

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.0 Hz, 6H), 3.15 in (users, 8H), of 3.78 (s, 3H), 3,83 (s, 3H), 4,60 (m, 1H)and 4.65 (s, 2H), 6,60-6,63 (m, 2H), for 6.81 (d, J=7.8 Hz, 1H), of 6.96 (d, J=9.0 Hz, 2H), 7,69 (d, J=9.0 Hz, 2H).

Soedinenie III-1 (40 mg, 0,084 mmol) was dissolved in Meon (1.0 ml) and THF (1.0 ml). Added 2 M aqueous sodium hydroxide solution (0,12 ml, 0.25 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with water and acidified by adding diluted hydrochloric acid, the mixture was extracted with ethyl acetate and the extract was washed with water, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound II-9 (35 mg, yield 91%).

1H-NMR (CDCl3) δ ppm: to 1.38 (d, J=6.0 Hz, 6H), 1,95 (users, 1H), and 3.16 (users, 8H), 3,86 (s, 3H), 4,60-4,69 (m, 3H), 6,60-6,63 (m, 2H), 6,85 (d, J=9.0 Hz, 1H), 6,98 (d, J=9.0 Hz, 2H), of 7.70 (d, J=9.0 Hz, 2H).

Example 3. Obtain compound II-6 and III-2:

Stage 1

4-Isopropoxybenzonitrile (4,46 g, 19.0 mmol) and triethylamine (5.6 ml, 40.0 mmol) was added to dissolve the 1-(tert-butoxycarbonyl)piperazine (11) (of 3.73 g, 20.0 mmol) in THF (40 ml) and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added dilute hydrochloric acid (200 ml), the mixture was extracted with ethyl acetate (200 ml), the organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution and saturated salt solution, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound (12) (of 6.78 g, yield 88%).

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.0 Hz, 6H), of 1.41 (s, 9H), 2.95 and (m, 4H), 3,51 (m, 4H), 4,63 (m, 1H), of 6.96 (d, J=8.7 Hz, 2H), 7,65 (d, J=8.7 Hz, 2H).

Stage 2

4 M hydrochloric acid Solution in ethyl acetate was added to a solution of compound (12) (of 6.78 g, 17.6 mmol) in ethyl acetate (30 ml), the mixture was stirred at room temperature within 2 hours and continued to stir at 50°C for 1 hour. To the reaction solution were added water (200 ml) and was extracted with ethyl acetate (200 ml). The aqueous layer was brought to pH 11 by adding 2 M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate (400 ml). The organic layer was sequentially washed with water and saturated salt solution, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound (13) (4,58 g, yield 92%).

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.0 Hz, 6H), 2.95 and (m, 8H), 4,63 (m, 1H), 6,94 (d, J=8.7 Hz, H), the 7.65 (d, J=8.7 Hz, 2H).

Stage 3

Tris(dibenzylideneacetone)dipalladium(0) (71 mg, 0.08 mmol), Xanthos (134 mg, 0.23 mmol) and tert-piperonyl sodium (288 mg, 3.0 mmol) was added to a solution of 3-bromo-2-chloropyridine (14) (192,4 mg, 1.0 mmol) and compound (3) (219 mg, 0.77 mmol) in toluene (10 ml) and the mixture was heated under reflux in nitrogen atmosphere for 3 hours. The reaction solution was cooled, poured into water (40 ml) and was extracted with ethyl acetate (100 ml). The organic layer is successively washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=3:1), thus obtaining the compound (15) (189 mg, yield 62%).

1H-NMR (CDCl3) δ ppm: 1,39 (d, J=6.0 Hz, 6H), 3,17 (m, 8H)and 4.65 (m, 1H), 6,98 (d, J=8.7 Hz, 2H), 7,19-7,34 (m, 2H), 7,65 (d, J=8.7 Hz, 2H), 8,08 (DD, J=1.5 and 4.5 Hz, 1H).

Stage 4

60% sodium Hydride (150 mg, 3.7 mmol) was added to a solution of benzyl alcohol (0.35 ml, 3.4 mmol) in DMF (10 ml) at 0°C and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of compound (15) (673 mg, 3.4 mmol) in DMF (5 ml) at 0°C and the mixture was stirred at 90°C. the Reaction solution was cooled, poured into water (100 ml) and was extracted with ethyl acetate (100 ml). The organic layer pic is edutella washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=3:1) and concentrated, thus obtaining a residue that was used in the next stage without further purification.

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.0 Hz, 6H), 3,17 (users, 8H), 4,63 (m, 1H), 4,70 (s, 2H), 6.87 in (DD, J=2,4, and 7.8 Hz, 1H), of 6.96 (d, J=9.0 Hz, 2H), to 7.09 (m, 1H), 7,28-7,34 (m, 5H), to 7.68 (d, J=9.0 Hz, 2H), 8,08 (DD, J=1,5, 4,8 Hz, 1H).

Stage 5

To the residue obtained in stage 4, was added THF (2 ml), Meon (2 ml) and 10% palladium carbon (150 mg) and the mixture was stirred in hydrogen atmosphere at room temperature for 1.5 hours. The reaction solution was filtered through celite and the filtrate was concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound (17) (365 mg, yield 57%/two stage).

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.0 Hz, 6H), of 3.25 (m, 8H), 4,63 (m, 1H), of 6.26 (m, 1H), 6,94? 7.04 baby mortality (m, 4H), to 7.67 (d, J=8.7 Hz, 2H).

Stage 6

Acilitated (0.95 ml, 0.8 mmol) and silver carbonate (166 mg, 0.6 mmol) was added to a solution of compound (17) (151 mg, 0.4 mmol) in toluene (20 ml) and the mixture was heated under reflux for 3 hours in nitrogen atmosphere. The reaction solution was cooled and filtered through a glass filter. The filtrate was concentrated and the resulting estato which was purified by chromatography on a column of silica gel (hexane:ethyl acetate=5:1), while receiving the compound III-2 (83 mg, yield 45%).

1H-NMR (CDCl3) δ ppm: 1,25 (t, J=7.2 Hz, 3H), 1,38 (d, J=6.0 Hz, 6H), 3,23 (users, 8H), 4,20 (m, 2H), 4,63 (m, 1H), is 4.93 (s, 2H), 6,85-6,98 (m, 3H), 7,18 (m, 1H), 7.68 per-7,76 (m, 3H).

Stage 7

The compound III-2 (80 mg, 0,17 mmol) was dissolved in Meon (1.0 ml) and THF (1.0 ml). To the mixture was added 2 M aqueous sodium hydroxide solution (0,34 ml, 0.69 mmol) and stirred at room temperature for 2 hours. The reaction solution was diluted with water and acidified by adding diluted hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed with water, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound II-6 (53 mg, yield 70%).

1H-NMR (DMSO-d6) δ ppm: 1,31 (d, J=6.0 Hz, 6H), 2,99 (users, 4H), 3,13 (users, 4H), 4.72 in-4,79 (m, 3H), 6,92 (DD, J=5,1, 7.5 Hz, 1H), 7,15 (d, J=8.7 Hz, 2H), 7.23 percent (d, J=7.8 Hz, 1H), to 7.67-of 7.70 (m, 3H), was 12.75 (users, 1H).

Example 4. Obtaining the compounds I-3, I-4, III-3 and III-4:

Stage 1

Sodium hydride (5.6 ml, 40.0 mmol) was added to a solution of 2-bromophenol (18) (5,19 g, 30.0 mmol) in DMF (50 ml) at 0°C and the mixture was stirred for 0.5 hour. To the mixture was added dropwise a simple chloromethylation ether (3.4 ml, 45,0 mmol) at 0°C and stirred at room temperature for one hour. To the reaction solution were added water (300 ml) and was extracted with dieti the new ether (300 ml). The extract was sequentially washed with water and saturated salt solution, dried and concentrated, thus obtaining the compound (19) (6.6 g, yield 99%).

1H-NMR (CDCl3) δ ppm: to 3.52 (s, 3H), of 5.25 (s, 2H), 6.89 in (m, 1H), 7,13-7,28 (m, 2H), 7,55 (m, 1H).

Stage 2

A solution of compound (19) (2.17 g, 10.0 mmol) in THF (125 ml) was cooled to -78°C for 10 minutes was added dropwise a solution of n-utility in hexane (7.5 ml, of 12.0 mmol) and the mixture was stirred at the same temperature for 30 minutes. The solution was heated to -50°C was added dropwise a solution of 1-(tert-butoxycarbonyl)piperidine (3,79 g, 19.0 mmol) in THF (100 ml) at -50°C and the mixture was stirred at -20°C for 30 minutes. In the reaction solution was poured into a saturated aqueous solution of NH4Cl (300 ml) and the mixture was extracted with diethyl ether (300 ml). The extract was sequentially washed with water and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=2:1), thus obtaining the compound (20) (650 mg, yield 19%).

1H-NMR (CDCl3) δ ppm: to 1.48 (s, 9H), from 2.00 (m, 4H), of 3.28 (m, 2H), 3,51 (s, 3H), 4,01 (m, 2H), and 5.30 (s, 2H), 7,01 (m, 1H), 7,14-7,30 (m, 3H).

Stage 3

Triperoxonane acid (3.0 ml) was added to a solution of compound (20) (650 mg, 10.0 mmol) in dichloromethane (10 ml), cooled to 0°C., and the mixture was stirred at room temperature for 18 hours. Reacts the traditional solution was cooled to 0°C, brought to pH 7 by adding saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate (100 ml). The extract was sequentially washed with water and saturated salt solution, dried and concentrated. The resulting residue [compound (21)] was used in the next stage without further purification.

Stage 4

To the residue, obtained in stage 3, was added THF (7 ml), 4-isopropoxybenzonitrile (435 mg, of 1.85 mmol) and triethylamine (of 1.03 ml, 7.4 mmol) and stirred at room temperature for 2 hours. To the reaction solution was added dilute hydrochloric acid (200 ml) and was extracted with ethyl acetate (200 ml). The organic layer was sequentially washed with a saturated aqueous solution of bicarbonate sodium and saturated salt solution, dried and concentrated. The resulting residue was purified by chromatography on a column of silica gel (hexane:ethyl acetate=5:1), thus obtaining the compound (22) (150 mg, yield 21%/two stage).

1H-NMR (CDCl3) δ ppm: to 1.37 (d, J=6.3 Hz, 6H), 2,33 (m, 2H), 3,35 (t, J=5.7 Hz, 2H), of 3.77 (m, 2H), with 4.64 (m, 1H), 5,79 (m, 1H), 6,83-7,00 (m, 5H), 7,14 (m, 1H), 7,73 (d, J=9.0 Hz, 2H).

Stage 5

Methylbromide (29 μl, 0.31 mmol), potassium carbonate (70 mg, 0.51 mmol) and potassium iodide (4.2 mg, of 0.025 mmol) was added to a solution of compound (22) (95 mg, 0.25 mmol) in DMF (1 ml) and the mixture was stirred at room temperature within 2 hours. To the reaction solution were added water (200 ml) and was extracted with ethyl acetate (20 ml). The organic layer was washed with saturated salt solution, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound III-3 (90,7 mg, yield 80%).

Stage 6

Compound I-3 (25 mg, 0.06 mmol) was dissolved in Meon (1.0 ml) and THF (1.0 ml). Added 2 M aqueous solution of sodium hydroxide (84 μl) and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with water, acidified by adding diluted hydrochloric acid, and was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound (I-XX (15 mg, yield 62%).

1H-NMR (DMSO-d6) δ ppm: 1.30 on (d, J=4.5 Hz, 6H), 2,50 (users, 2H), 3,14 (users, 2H), 3,61 (users, 2H), 4,63 (s, 2H), 4,74 (users, 1H), 5,72 (s, 1H), 6,82-6,92 (m, 2H), 7,02-7,19 (m, 4H), 7,71 (d, J=7.5 Hz, 2H), 13,01 (users, 1H).

Stage 7

To compound III-3 (61,6 mg, was 0.138 mmol) was added THF (1 ml), Meon (1 ml) and 10% palladium carbon (18 mg) and the mixture was stirred in hydrogen atmosphere at room temperature for 1.5 hours. The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound III-4 (62 mg, yield 99%).

The study is 8

Compound III-4 (62 mg, was 0.138 mmol) was dissolved in Meon (1.0 ml) and THF (1.0 ml). Added 2 M aqueous solution of sodium hydroxide (207 μl) and the solution was stirred at room temperature for 2 hours. The reaction solution was diluted with water, acidified by adding diluted hydrochloric acid and was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was led from hexane-ethyl acetate, thus obtaining the compound I-4 (20 mg, yield 33%).

1H-NMR (DMSO-d6) δ ppm: 1,32 (d, J=6.0 Hz, 6H), 1.60-to 1,71 (m, 2H), 1,82 (d, J=11.7 Hz, 2H), and 2.26 (t, J=10.5 Hz, 2H), 2,84 (t, J=11.7 Hz, 1H, in), 3.75 (d, J=11,4 Hz, 2H), with 4.64 (s, 2H), 4.72 in-4,80 (m, 1H), 6,80 (d, J=8,4 Hz, 1H), 6.90 to (t, J=7.2 Hz, 1H), 7,11-to 7.15 (m, 4H), to 7.67 (d, J=8.7 Hz, 2H), 13,00 (users, 1H).

Example 5. Obtain compound II-13, III-13 and (26):

Stage 1

To the compound (23) (15.7 g, 100 mmol) was added 1-(tert-butylcarbamoyl)piperazin (46.6 g, 250 mmol) and stirred at 80°C for one hour. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed 2 N. a solution of hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent is evaporated, thus obtaining the product (24) (28.4 g, yield 88%) as a yellow powder.

Stage 2

Potassium carbonate (5.53 g, 40.0 mmol), potassium iodide (0.33 g, 2.0 mmol) and methylbromacetate (2.8 ml, 30.0 mmol) to allali to a solution of compound (24) (6,47 g, 20.0 mmol)obtained in stage 1, in DMF (60,0 ml) and stirred at room temperature for one hour. The reaction solution was poured into water, the precipitated crystalline substance was collected by filtration and washed with water. The crude crystalline material was washed with hexane, thus obtaining the product (25) (9,9 g) as a yellow powder.

Stage 3

4 n hydrochloric acid in dioxane (40,0 ml) was added to a solution of compound (25) (9,9 g)obtained in stage 2, in ethyl acetate (50,0 ml) and stirred at 50°C for 0.5 hour. The reaction solution was filtered, the crude crystalline material was washed with hexane and ethyl acetate, thus obtaining the product (26) (6,38 g, yield 96%) as a yellow powder.

Stage 4

A solution of compound (26) (3,32 g, 10.0 mmol), obtained in stage 3, in THF (10.0 ml) was cooled to 0°C was added triethylamine (of 4.2 ml, 30.0 mmol) and 4-isopropoxybenzonitrile (2.58 g, 11.0 mmol). The reaction solution was stirred at room temperature for 15 hours, poured into water and was extracted with ethyl acetate. The organic layer was sequentially washed 2 N. a solution of hydrochloric acid, water and saturated salt solution and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product III-13 (4,17 g, yield 85%) as Zheltov the powder.

Stage 5

2 M Aqueous solution of sodium hydroxide (to 0.60 ml, 1.2 mmol) was added to a solution of compound III-13 (197 mg, 0.40 mmol)obtained in stage 4, the Meon (2.0 ml) and THF (2.0 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water and washed simple ether. The aqueous layer was acidified by adding 2 n hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The crude crystalline substance precrystallization from hexane-ethyl acetate, thus obtaining the product II-13 (166 mg, yield 87%) as a yellow powder.

1H-NMR (CDCl3) δ ppm: to 1.37 (d, 6H, J=6.3 Hz), 3.15 in (ushort, 4H, J=4,8 Hz), 3,50 (ushort, 4H, J=4, 2 Hz), 4,60-4,70 (m, 1H), and 4.75 (s, 2H), 6,24, (s, 1H), of 6.49 (DD, 1H, J=2.1 a, and 9.3 Hz), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=8.7 Hz), of 8.06 (d, 2H, J=9.6 Hz).

Example 6. Obtain compound II-24 III-24:

Stage 1

To a solution of compound (23) (3,14 g, 20.0 mmol) in DMF (150 ml) was added triethylamine (5.6 ml, 40.0 mmol) and parasupersymmetric (8.53 g, 30.0 mmol) and stirred at 80°C for 4 hours. To the reaction solution was added 2 n hydrochloric acid solution at room temperature. The precipitated crystalline substance was collected by filtration and washed with water the th. The crude crystalline material was washed with hexane, thus obtaining the product (27) (9,06 g) as a yellow powder.

Stage 2

10% Palladium carbon (1.35 g) was added to a solution of compound (27) (9.0 g)obtained in stage 1, in the Meon (90,0 ml) and THF (90,0 ml) and was first made at room temperature for 2 hours. The catalyst was filtered through celite and the filtrate was concentrated in vacuum. The resulting crude crystalline material was washed with a simple ether, thus obtaining the product (28) (5,00 g, yield 77%) as a purple powder.

Stage 3

A solution of compound (28) (1,17 g, 3.0 mmol), obtained in stage 2, in pyridine (5.0 ml) was cooled to 0°C and added chloride 2-fullaway acid (0,28 ml, to 2.85 mmol). The reaction solution was stirred at room temperature for 18 hours, poured into water and was extracted with ethyl acetate. The organic layer was washed with 0.5 M citric acid solution and water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product (29) (660 mg, yield 45%) as a purple powder.

Stage 4

Potassium carbonate (370 mg, 2.68 mmol) and methylbromide (0,19 ml, a 2.01 mmol) was added to a solution of compound (29) (650 mg, of 1.34 mmol), obtained in stage 3, in DMF (5.0 ml) and stirred at room temperature for 2 hours. The reaction rectorville in the water and was extracted with ethyl acetate. The organic layer was washed with 0.5 M citric acid solution and water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was purified by chromatography on a column of silica gel (chloroform:methanol=500:1) and the resulting crude crystalline substance was recrystallized, thus obtaining the compound III-24 (360 mg, yield 48%) as a pale purple powder.

Stage 5

2 M sodium hydroxide Solution (2,39 ml, 4.77 mmol) was added to a solution of compound III-24 (350 mg, of 1.59 mmol)obtained in stage 4, the Meon (3.5 ml) and THF (3.5 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water and washed simple ether. To the aqueous layer was added 2 n hydrochloric acid and the precipitated crystalline substance was collected by filtration. The crude crystalline substance was recrystallized from Meon and then from ethyl acetate, thus obtaining the product II-24 (120 mg, yield 14%) as a pale green powder.

1H-NMR (DMSO-d6) δ ppm: 1.30 on (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,20 (users, 4H), 4,71-4,79 (m, 3H), 6,55 (DD, J=2,4, and 8.7 Hz, 1H), 6,68-6,70 (m, 2H), 7,15 (d, J=8.7 Hz, 2H), 7.23 percent (DD, J=0,6 and 2.2 Hz, 1H), 7,68 (d, J=9.0 Hz, 2H), 7,81 (d, J=8.7 Hz, 1H), 7,89-of 7.90 (m, 1H), of 9.30 (s, 1H).

Example 7. Obtain compound II-33 III-33:

Stage 1

Iron (5,59 g, 100 mmol), ammonium chloride,35 g, 100 mmol) and water (75,0 ml) was added to a solution of compound (30) (11.6 g, 50.0 mmol) in Meon (150 ml) and stirred at 100°C for 6 hours. The reaction solution was filtered through celite to remove the iron, and the filtrate was poured into water. The reaction solution was acidified by adding 2 n hydrochloric acid and washed with simple ether. The reaction solution was podslushivaet by adding 2 M sodium hydroxide solution and was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent evaporated in vacuum, thus obtaining the product (31) (4,20 g, yield 42%) as a brown powder.

Stage 2

Concentrated hydrochloric acid (32,0 ml) was added to the compound (31) (4.12 g, of 20.4 mmol), obtained in stage 1, and stirred at room temperature for 18 hours. The reaction solution was cooled to 0°C. and for 20 minutes was added dropwise an aqueous solution (10.0 ml) nitrate nutria (3,37 g, 48.8 mmol). Then within 20 minutes was added dropwise an aqueous solution (10.0 ml) of potassium iodide (9,96 g, 61,0 mmol). The reaction solution was stirred at 0°C for one hour and was extracted with simple ether. The organic layer was washed with saturated aqueous sodium thiosulfate solution and water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product (2) (5,00 g, yield 65%).

Stage 3

A solution of the compound (32) (5,00 g, 16.0 mmol), obtained in stage 2, DICHLOROSILANE (10.0 ml) was cooled to 0°C. and for 30 minutes was added dropwise a 1 M solution of tribromide boron in dichlormethane (32,0 ml). The reaction solution was stirred at 0°C for one hour and then at room temperature for 3 hours. The reaction solution was poured into a mixture of ice water was added concentrated hydrochloric acid and the mixture was stirred at room temperature for one hour. The mixture was extracted with simple ether and the organic layer was extracted with 2 M aqueous solution of sodium hydroxide. The aqueous layer was acidified by adding 2 n hydrochloric acid, and was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product (33) (4,30 g, yield 90%).

Stage 4

Potassium carbonate (3.98 g, 28.8 mmol) and chloromethylation ether (2.2 ml, 28.8 mmol) was added to a solution of compound (33) (4,30 g, 14.4 mmol), obtained in stage 3, in DMF (40,0 ml) and stirred at room temperature for 18 hours. The reaction solution was poured into water and was extracted with simple ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. OST the current was purified by chromatography on a column of silica gel (hexane), while receiving the product (34) (5,42 g, yield 99%).

Stage 5

Parasupersymmetric (683 mg, 2.4 mmol), Tris(dibenzylideneacetone)dipalladium (91,8 mg, 0.1 mmol), RAC-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (249 mg, 0.4 mmol) and tert-piperonyl sodium (384 mg, 4.0 mmol) was added to a solution of compound (34) (686 mg, 2.0 mmol)obtained in stage 4 in toluene (3.4 ml) and stirred at 50°C for 4 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was purified by chromatography on a column of silica gel (ethyl acetate:hexane=2:1) and the crude crystalline substance was recrystallized, while receiving the product (35) (412 mg, yield 41%).

Stage 6

2 N. hydrochloric acid Solution was added to a solution of compound (35) (300 mg, of 0.60 mmol)obtained in stage 5, in the Meon (2.0 ml) and THF (2.0 ml) and stirred at room temperature for 18 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuum. The resulting residue was dissolved in a simple ether and was extracted with 2 M aqueous solution of sodium hydroxide. The aqueous solution was acidified by adding 2 n hydrochloric acid and extraheavy is and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent evaporated in vacuume, while receiving the product (36) (179 mg, yield 66%) as a colorless powder.

Stage 7

Potassium carbonate (103 mg, 0.75 mmol) and methylbromide (0,042 ml, 0.45 mmol) was added to a solution of compound (36) (170 mg, of 0.37 mmol)obtained in stage 6, in DMF (2.0 ml) and stirred at room temperature for 18 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed 2 N. a solution of hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product III-33 (150 mg, yield 76%) as colorless powder.

Stage 8

2 M Aqueous sodium hydroxide solution (of 0.43 ml, 0.85 mmol) was added to a solution of compound III-33 (150 mg, 0.28 mmol)obtained in stage 7, in the Meon (2.0 ml) and THF (2.0 ml) and stirred at room temperature for 3 hours. The reaction solution was poured into water and was extracted with simple ether. The aqueous layer was acidified by adding 2 n hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The resulting crude crystalline substance was recrystallized from ethyl acetate/hexane, olucha this product II-33 (142 mg, yield 97%) as a colorless powder.

1H-NMR (DMSO-d6) δ ppm: 1.30 on (d, J=6.0 Hz, 6H), 2.95 and (users, 4H), to 3.02 (users, 4H), 4,71-4,79 (m, 3H), 6.42 per (DD, J=2,4, and 9.0 Hz, 1H), is 6.54 (d, J=2.4 Hz, 1H), 7,13 (d, J=9.0 Hz, 2H), 7,32 (d, J=8.7 Hz, 1H), 7,66 (d, J=8.7 Hz, 2H).

Example 8. Obtain compound II-54 III-54:

Stage 1

A solution of the compound (35) (350 mg, 0.70 mmol), 3-Puilboreau acid (94,1 mg, 0.84 mmol), palladium acetate (7.9 mg, 0.035 mmol), triphenylphosphine (to 36.8 mg, 0.14 mmol) and 2 M aqueous potassium carbonate (2.1 ml) in DMF (6.3 ml) was stirred at 80°C for 4 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The aqueous layer was washed with 0.5 M aqueous citric acid solution and water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was purified by chromatography on a column of silica gel (ethyl acetate:hexane=3:1), thus obtaining the product (37) (266 mg, yield 78%) as a yellow powder.

Stage 2

6 N. hydrochloric acid Solution (0.35 ml) was added to a solution of compound (37) (200 mg, 0.41 mmol)obtained in stage 1, in the Meon (3.0 ml) and THF (3.0 ml) and stirred at room temperature for 6 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, receive the I product (38) (151 mg, yield 67%) as a gray powder.

Stage 3

Potassium carbonate (87,3 g to 0.63 mmol) and methylbromide (0.036 ml, 0.38 mmol) was added to a solution of compound (38) (140 mg, 0.32 mmol), obtained in stage 2, in DMF (2.0 ml) and stirred at room temperature for 18 hours. The reaction solution was poured into water and was extracted with ethyl acetate. The organic layer was washed 2 N. a solution of hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product III-54 (110 mg, yield 68%) as a colorless powder.

Stage 4

2 M sodium hydroxide Solution (0,29 ml of 0.58 mmol) was added to a solution of compound III-54 (100 mg, 0,19 mmol), obtained in stage 3, in the Meon (2.0 ml) and THF (2.0 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water and was extracted with simple ether. The aqueous layer was acidified by adding 2 n hydrochloric acid, and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The resulting crude crystalline substance was recrystallized from ethyl acetate/hexane, thus obtaining the compound II-54 (85 mg, yield 88%) as colorless powder.

1H-NMR (DMSO-d6) δ ppm: 1,29 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,26 users, 4H), 4,79-4,70 (m, 3H), of 6.52 (d, J=9.0 Hz, 1H), 6,55 (s, 1H), 6,97 (s, 1H), 7,14 (d, J=9.0 Hz, 2H), 7,44 (d, J=9.0 Hz, 1H), 7,66 (s, 1H), to 7.67 (d, J=9.0 Hz, 2H), at 8.36 (s, 1H).

Example 9. Obtain compound II-63 III-63:

Stage 1

A solution of the compound (39) (5.0 g, a 32.6 mmol) in 15% sulfuric acid (45 ml) was stirred at 5°C. To the reaction solution was added a solution of sodium nitrate (2.25 g, a 32.6 mmol) in water (10 ml) and a solution of potassium iodide (8,13 g) 1 N. sulfuric acid solution (20 ml). The reaction solution was stirred at 5°C for 10 minutes and continued to stir at 90°C for 30 minutes. The reaction solution was cooled to room temperature, the precipitated solid was collected by filtration and dried. The obtained solid substance was dissolved in THF (20 ml) and Meon (20 ml)was added 2 M solution TMSCH2N2in hexane (40 ml)and was stirred for 2 hours. The reaction solution was concentrated in vacuo, the resulting residue was purified by chromatography on a column of silica gel (ethyl acetate/ hexane=1/10) and the crude product is recrystallized from hexane, thus obtaining the product (40) (3,95 g, yield 44%) as a white powder.

Stage 2

A solution of compound (40) (1.8 g, 6,48 mmol)obtained in stage 1, compounds (13) (2,03 g, 7,12 mmol), obtained in stage 2 of example 3, palladium acetate (58 mg, 0.26 mmol), RAC-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (24 mg, 0,39 mmol) and cesium carbonate (2,95 g, 9,07 mmol) in toluene (20 ml) was stirred at 100°C. in a nitrogen atmosphere for 12 hours. The reaction solution was cooled to room temperature and was extracted with chloroform. The organic layer was washed with water and 2 N. a solution of hydrochloric acid and concentrated in vacuum. The residue was led from ethanol-chloroform, thus obtaining the product (41) (1.35 g, yield 48%).

Stage 3

A solution of the compound (41) (380 mg, 0,875 mmol), obtained in stage 2, tert-butoxide potassium (980 mg, is 8.75 mmol) and water (63 μl, 3.5 mmol) in THF (5 ml) was stirred at room temperature for 1.5 hours. The reaction solution was extracted with ethyl acetate and the organic layer was washed with water, 2 N. a solution of hydrochloric acid and a saturated solution of salt. The solvent is evaporated in vacuum and the residue was led from ethyl acetate-hexane, thus obtaining the product (42) (353 mg, yield 96%).

Stage 4

A solution of the compound (42) (250 mg, 0.59 mmol), obtained in stage 3, WSCD hydrochloride (137 mg, 0.71 mmol), HOBt (97 mg), Isopropylamine (61 μl, 0.71 mmol) in DMF (2 ml) was stirred at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate and the organic layer was washed with water and 2 N. a solution of hydrochloric acid. The solvent is evaporated in vacuum and the residue was purified x is matography on a column of silica gel (ethyl acetate/hexane=1/4), while receiving the product (43) (177 mg, yield 64%).

Stage 5

A solution of the compound (43) (170 mg, of 0.37 mmol)obtained in stage 4, cesium carbonate (180 mg, 0.55 mmol) and methylpropanoate (0,052 ml, 0.55 mmol) in DMF (2 ml) was stirred at room temperature for 3 hours. The reaction solution was extracted with ethyl acetate and the organic layer was washed with water, 2 N. a solution of hydrochloric acid and a saturated solution of salt. The solvent is evaporated in vacuum and the residue was purified by chromatography on a column of silica gel (ethyl acetate/hexane=1/1), thus obtaining the product III-63 (195 mg, quantitative yield).

Stage 6

A solution of compound III-63 (190 mg, 0.36 mmol)obtained in stage 5, and 4 N. of an aqueous solution of sodium hydroxide (220 μl, 0.89 mmol) in THF (1 ml) and Meon (1 ml) was stirred over night. To the reaction solution was added 2 n hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water and saturated salt solution. The solvent is evaporated in vacuum, thus obtaining the product III-63 (165 mg, yield 89%).

1H-NMR (CDCl3) δ ppm: 1,24 (d, 6H, J=6.3 Hz), of 1.37 (d, 6H, J=6.0 Hz), 3,14 (t, 4H), to 3.35 (t, 4H)and 4.65 (m, 1H), 4,71 (s, 2H), 6,29 (d, 1H, J=2.4 Hz), 6,53 (DD, 1H, J=8.7 Hz and 2.1 Hz), 6,97 (d, 2H, J=3.0 Hz), 7,66-7,72 (m, 3H), to 7.84 (d, 1H, J=8.7 Hz).

Example 10. Obtain compound II-74 III-74:

Stage

A solution of the compound (44) (15.0 g, 86,92 mmol), WSCD hydrochloride (20,0 g, 104,32 mmol), HOBt (11,70 g, 86,57 mmol), 2,2'-dimethylacetamide (13,70 g, 130,30 mmol) in THF (75 ml) was stirred for 2 hours. To the reaction solution was added water and was extracted with ethyl acetate. The organic layer was washed with saturated salt solution and the solvent evaporated in vacuum. The solution of the resulting solids, potassium carbonate (18.0 g, 130,23 mmol) and benzylbromide (19,20 g, 112,25 mmol) in DMF (50 ml) and ethyl acetate (50 ml) was stirred at 60°C for 2 hours. To the reaction solution was added water and was extracted with ethyl acetate. The organic layer was washed with saturated salt solution and the solvent evaporated in vacuum. The resulting crystalline material was washed with a mixture of 10% ethyl acetate-hexane, thus obtaining the product (45) (23,40 g, yield 76%).

Stage 2

2 N. hydrochloric acid solution (15 ml) was added to a solution of compound (45) (5.0 g, 14,29 mmol)obtained in stage 1, in THF (20 ml) and stirred at 70°C for 2 hours. The reaction mixture was cooled to room temperature and was extracted with ethyl acetate, the organic layer was washed with saturated salt solution and the solvent evaporated in vacuum. To the resulting residue were added acetonitrile (15 ml) and the resulting solution was used in the next stage.

The solution t is Ivanilova (7,45 g, 28,40 mmol) and hexachloroethane (6,72 g, 28,40 mmol) in acetonitrile was stirred for 30 minutes, the solution was added to the obtained residue in acetonitrile (15 ml) and pyridine (4.6 ml, 56,80 mmol) and the mixture was stirred at room temperature for 30 minutes. The mixture continued to stir at 60°C for one hour. To the reaction solution was added water and was extracted with ethyl acetate. The organic layer was washed with water and 10% aqueous citric acid solution and the solvent evaporated in vacuum. The residue was purified by chromatography on a column of silica gel (ethyl acetate/hexane=1/4), while receiving the product (46) (3,35 g, yield 83%).

Stage 3

A solution of compound (46) (200 mg, 0.70 mmol), obtained in stage 2, compounds (13) (239 mg, 0.84 mmol)obtained in stage 2 of example 3, leads to compounds, which lead (3.1 mg, 0.014 mmol), butyldiethanolamine (10.0 mg, 0,028 mmol) and tert-butoxide sodium cases (94.2 mg, 0.98 mmol) in toluene (2 ml) was stirred at 110°C. in a nitrogen atmosphere for 15 hours. The reaction solution was cooled to room temperature and was extracted with chloroform, the organic layer was added citric acid (147 mg, 0.70 mmol) and the organic layer was washed with water and saturated salt solution. The solvent is evaporated in vacuum and the product was led from ethyl acetate-hexane, thus obtaining the product (47) (331 mg, yield 89%).

Stage 4

A solution of the compound (47) (100 mg, 0,187 mmol), obtained in stage 3, and 10% palladium carbon (30 mg) in THF (15 ml) and Meon (15 ml) was stirred in hydrogen atmosphere for 2 hours. The reaction mixture was filtered and the filtrate was concentrated under vacuum, thus obtaining the product (48) (81,3 mg, yield 98%) as a white solid.

Stage 5

A solution of the compound (48) (200 mg, 0.45 mmol)obtained in stage 4, potassium carbonate (93 mg, 0.67 mmol), potassium iodide (15 mmol) and methylpropanoate (0,064 ml of 0.68 mmol) in DMF (1.6 ml) was stirred at 90°C for one hour. The reaction mixture was cooled to 0°C was added 2 n hydrochloric acid (0,23 ml), Meon (5.0 ml) and water (5.0 ml). The resulting crystalline substance was collected by filtration, thus obtaining the product III-74 (212 mg, yield 91%) as a white crystalline substance.

Stage 6

A solution of compound III-74 (65 mg, 0,126 mmol)obtained in stage 5, and 4 N. aqueous sodium hydroxide solution (80 μl, 0,315 mmol) in DMF (1 ml) was stirred over night. To the reaction solution was added 2 n hydrochloric acid (315 μl) and stirred, then added water (20,0 ml) and stirred at 0°C for 30 minutes. The precipitated crystalline substance was collected by filtration, thus obtaining the product II-74 (50,6 mg, yield 80%) as a white crystalline substances is A.

1H-NMR (CDCl3) δ ppm: to 1.37 (d, 6H, J=6.0 Hz), and 3.16 (t, 4H), of 3.42 (t, 4H), 4,63 (m, 1H), of 4.77 (s, 2H), 6,40 (d, 1H, J=2.7 Hz), 6,62 (DD, 1H, J=9,0 Hz, 2.4 Hz), 6,98 (d, 2H, J=3.0 Hz), 7,27 (d, 1H), to 7.67-7,72 (m, 3H), 7,79 (d, 1H, J=3.0 Hz).

Example 11. Obtain compound II-96 III-96:

Stage 1

Compound (49) (19,0 g, 110 mmol) was cooled to 0°C was added acetic anhydride (12.5 ml, 132 mmol). Then add one drop of sulfuric acid. The reaction solution was stirred at room temperature for one hour and poured into it a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted with simple ether, the extract washed with saturated aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuum, thus obtaining the product (50) (24.3 g, yield 99%) (2).

Stage 2

The compound (50) (of 21.5 g, 100 mmol), obtained in stage 1, was cooled to 0°C, the two portions was added aluminum chloride(III) (24,0 g, 180 mmol) and the mixture was stirred at 165°C for 2 hours. The reaction solution was cooled to room temperature and added water. The reaction solution was extracted with chloroform, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was recrystallized from hexane, thus obtaining the product (51) (22.9 grams, in the course 97%) as a yellow powder.

Stage 3

Potassium carbonate (18.7 g, 50.0 mmol), potassium iodide (0,83 g, 5.0 mmol) and benzylbromide (3,21 ml of 65.0 mmol) was added to a solution of compound (51) (10.8 g, 50.0 mmol), obtained in stage 2, in DMF (50,0 ml) and stirred at 60°C for 18 hours. The reaction solution was cooled to room temperature and added water. The precipitated crystalline substance was collected by filtration and washed with water. The resulting crude crystalline material was washed with hexane, thus obtaining the product (52) (13.8 g, yield 90%).

Stage 4

A solution of bromine (2.1 ml, 40.0 mmol) in dioxane (40,0 ml) was added at 15°C for 30 minutes to a solution of compound (52) (12.5 g, 41,0 mmol), obtained in stage 3, in dioxane (20 ml). The reaction solution was heated to 20°C, stirred for 30 minutes and continued to stir at 25°C for 3 hours. The reaction solution was concentrated in vacuo and the resulting residue was recrystallized from dioxane/hexane, thus obtaining the product (53) (9,84 g, yield 64%) as a brown powder.

Stage 5

The ammonium formate (10.3 g, 180 mmol) was added to a solution of compound (53) (9,84 g, or 35.9 mmol)obtained in stage 4, in formic acid (40,0 ml) and was heated under reflux for 12 hours. The reaction solution was poured into 2 M aqueous sodium hydroxide solution was made basic and extragear the Wali chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was purified by chromatography on a column of silica gel (ethyl acetate/hexane=10/1), while receiving the product (54) (1.19 g, yield 10%) as a yellow powder.

Stage 6

Parasupersymmetric (1,23 g, 4,33 mmol), Tris(dibenzylideneacetone)dipalladium (152 mg, 0,17 mmol), RAC-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (414 mg, 0.67 mmol) and tert-piperonyl sodium (640 mg, of 6.66 mmol) was added to a solution of compound (54) (1.10 g, of 3.33 mmol)obtained in stage 5 in toluene (3.4 ml) and stirred at 100°C for 12 hours. To the reaction solution was added water and was extracted with ethyl acetate. The organic layer was filtered through celite, washed 2 N. a solution of hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The residue was purified by chromatography on a column of silica gel (ethyl acetate/hexane=2/1), while receiving the product (55) (450 mg, yield 25%) as a yellow powder.

Stage 7

10% Palladium carbon (20 mg) was added to a solution of compound (55) (200 mg, 0.38 mmol)obtained in stage 6, in THF (2.0 ml) and was first made. The mixture was stirred at room temperature for 2 hours, filtered through celite and the filtrate was concentrated in vacuum. The residue was dissolved in Meon (2.0 ml)was added 20% palladium hydroxide on coal (20 mg) and the mixture was first made. The reaction mixture was stirred at room temperature for 3 hours, was added 2 n hydrochloric acid (0,20 ml) and again was first made. The reaction solution was stirred at room temperature for 9 hours and filtered through celite. The solvent of the filtrate is evaporated in vacuum, thus obtaining the product (56) (135 mg, yield 81%) as a yellow powder.

Stage 8

Potassium carbonate (81,0 g, 0.59 mmol) and methylbromide (0,097 ml, 0.35 mmol) was added to a solution of compound (56) (130 mg, 0.29 mmol)obtained in stage 7, in DMF (2.0 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water, the precipitated crystalline substance was collected by filtration and washed with water. The resulting crude product was washed with hexane, thus obtaining the product III-96 (75%yield) as a colorless powder.

Stage 9

2 M Aqueous sodium hydroxide solution (0.33 ml, 0.66 mmol) was added to a solution of compound (9), III-96 (114 mg, 0.22 mmol)obtained in stage 8, in the Meon (2.0 ml) and THF (2.0 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water and was extracted with simple ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuum. The resulting crude crystalline substance is recristallization from ethyl acetate-hexane, while receiving the product III-96 (15 mg, 14%) as a colorless powder.

1H-NMR (DMSO-d6) δ ppm: 1,29 (d, J=6.0 Hz, 6H), 2,96 (users, 4H), 3,26 (users, 4H), 4,30 (s, 2H), 4,69-of 4.77 (m, 1H), 6,50 (s, 1H), 6,53 (d, J=9.0 Hz, 1H), 7,12 (d, J=8.7 Hz, 2H), 7,65 (d, J=9.0 Hz, 2H), 7,78 (d, J=8.7 Hz, 1H), 8,31 (s, 1H), 9,13 (s, 1H).

Compounds I-2, I-5-I-31, II-1 to II-5, II-7 to II-8, II-10 to II-12, II-14 II-23 II-25 II-32 II-34 II-53, II-55 II-62 II-64 II-73, II-75 II-95 II-99 II-103, II-105 II-106 II-108 II-118 II-122 II-123 II-127 II-131 II-133 II-135 II-140 II-143 were obtained similarly to the above-described methods. Structure and physical properties of these compounds are given in tables 1-41.

Table 26
No. of connections1H-NMR (Solvent) δ
I-1(CDCl3) to 1.35 (d, 6H, J=9.0 Hz), a 2.01 (m, 4H), of 2.28 (s, 3H), 3.15 in (m, 4H), to 4.62 (m, 1H), 6,38 (d, J=16.2 Hz, 1H), 6,74 (d, J=8,4 Hz, 1H), of 6.96 (d, J=9.0 Hz, 2H), 7,11 (DD, J=1,8, and 8.4 Hz, 1H), 7,31 (d, J=1.8 Hz, 1H), 7,68 (d, J=9.0 Hz, 2H), 7,89 (d, J=16.2 Hz, 1H)
I-2(CDCl3) to 1.35 (d, 6H, J=9.0 Hz), to 1.98 (m, 4H), of 2.28 (s, 3H), 2,28 (m, 2H), 2,70 (m, 2H), 3.15 in (m, 4H), to 4.62 (m, 1H), 6,74 (d, J=9.0 Hz, 1H), 6,94 (m, 4H), to 7.68 (d, J=9.0 Hz, 2H)
I-3(DMSO-d6) of 1.30 (d, 6H, J=4.5 Hz), 2,50 (users, 2H), 3,14 (users, 2H), 3,61 (users, 2H), 4,63 (s, 2H), 4,74 (users, 1H), 5,72 (s, 1H), 6,82-6,92 (m, 2H), 7,02-7,19 (m, 4H), 7,71 (d, 2H, J=7.5 Hz), 13,01 (users, 1H)
I-4(DMSO-d6) of 1.32 (d, 6H, J=6.0 Hz), 1.60-to 1,71 (m, 2H), equal to 1.82 (d, 2H, J=11.7 Hz), and 2.26 (t, 2H, J=10.5 Hz), 2,84 (t, 1H, J=11.7 G is), of 3.75 (d, 2H, J=11,4 Hz), with 4.64 (s, 2H), 4.72 in-4,80 (m, 1H), 6,80 (d, 1H, J=8,4 Hz), 6.90 to (t, 1H, J=7,2 Hz), 7,11-to 7.15 (m, 4H), to 7.67 (d, 2H, J=8.7 Hz), 13,00 (users, 1H)
I-5(CDCl3) to 1.37 (d, 6H, J=6.3 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), of 3.78 (s, 3H), 4.26 deaths is 4.35 (m, 1H), 4.63 to-4,70 (m, 1H), 6,37 (d, 1H, J=15,9 Hz), to 6.80 (d, 1H, J=9.0 Hz), 6.87 in (DD, 1H, J=9,0, 2.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,02 (d, 1H, J=2.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 7,86 (d, 1H, J=15,9 Hz)
I-6(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), 4,36 is 4.45 (m, 1H), 4.63 to-4,70 (m, 1H), 6,37 (d, 1H, J=15,9 Hz), 6,78 (d, 1H, J=9.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,20-7,30 (m, 1H), 7,47 (d, 1H, J=2.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 7,83 (d, 1H, J=15,9 Hz)
I-7(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), 4,40-4,48 (m, 1H), 4.63 to-4,70 (m, 1H), 6,37 (d, 1H, J=15,9 Hz), to 6.80 (d, 1H, J=9.0 Hz), 6,92 (d, 1H, J=9.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,33 (t, 1H, J=9.0 Hz), 7,53 (d, 1H, J=9.0 Hz), of 7.70 (d, 2H, J=9.0 Hz), 7,89 (d, 1H, J=15,9 Hz)
I-8(CDCl3) of 1.33 (d, 6H, J=6.3 Hz), 1,90-2,10 (m, 4H), 3,05-3,30 (m, 4H), 3,85 (s, 3H), 4,50-of 4.57 (m, 1H), 4,60-4,70 (m, 1H), 6,47 (d, 1H, J=9.0 Hz), of 6.52 (d, 1H, J=9.0 Hz), 6,78 (d, 1H, J=15,9 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,20 (t, 1H, J=9.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 8,02 (d, 1H, J=15,9 Hz)
I-9(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2.49 USD (t, 2H, J=7.5 Hz), of 2.72 (t, 2H, J=7.5 Hz), 3,05-3,20 (m, 4H), 3,74 (s, 3H), 4.26 deaths is 4.35 (m, 1H), 4.63 to-4,70 (m, 1H), 6,65 (d, 1H, J=2.0 Hz), to 6.67 (s, 1H), 6,95 (d, 1H, J=2.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,86 (d, 2H, J9,0 Hz).

Table 27
No. of connections1H-NMR (Solvent) δ
I-10(CDCl3) of 1.36 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), to 2.46 (t, 2H, J=7.5 Hz), 2,70 (t, 2H, J=7.5 Hz), 3,05-3,20 (m, 4H), 4,35 was 4.42 (m, 1H), 4,60-4,70 (m, 1H), 6,65 (d, 1H, J=8.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,05 (d, 1H, J=8.0 Hz), 7,10 (s, 1H), 7,68 (d, 2H, J=9.0 Hz).
I-11(CDCl3) to 1.35 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2,47 (t, 2H, J=7.5 Hz), a 2.75 (t, 2H, J=7.5 Hz), 3,00-3,20 (m, 4H), 4,40-4,50 (m, 1H), 4.63 to-4,70 (m, 1H), 6.75 in (d, 1H, J=8.0 Hz), at 6.84 (t, 1H, J=8.0 Hz), 6,95 (d, 2H, J=9.0 Hz), 7,13 (d, 1H, J=8.0 Hz), to 7.15 (t, 1H, J=8.0 Hz), to 7.68 (d, 2H, J=9.0 Hz).
I-12(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), of 2.38 (t, 2H, J=7.5 Hz), and 2.79 (t, 2H, J=7.5 Hz), 3,00-3,20 (m, 4H), of 3.78 (s, 3H), 4,40-4,50 (m, 1H), 4.63 to-4,70 (m, 1H), gold 6.43 (d, 1H, J=8.0 Hz), 6,50 (d, 1H, J=8.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,05 (t, 1H, J=8.0 Hz), to 7.68 (d, 2H, J=9.0 Hz).
I-13(CDCl3) of 1.33 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), 4,40-4,48 (m, 1H), 4.63 to-4,70 (m, 1H), 6,92 (d, 1H, J=15,9 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,15-of 7.23 (m, 2H), 7,68 (d, 2H, J=9.0 Hz),7,95 (d, 1H, J=15,9 Hz), of 8.25(d, 1H, J=3,4 Hz).
I-14(CDCl3) of 1.33 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), of 2.50 (s, 3H), 3,05-3,20 (m, 4H), 4,40-4,48 (m, 1H), 4.63 to-4,70 (m, 1H), 6,92 (d, 1H, J=15,9 Hz), 6,95 (who, 2H, J=9.0 Hz), to 7.15 (s, 2H), 7,68 (d, 2H, J=9.0 Hz), 7,95 (d, 1H, J=15,9 Hz).
I-15(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1,95-2,15 (m, 4H), to 2.67 (t, 2H, J=7.5 Hz), 2.95 and (t, 2H, J=7.5 Hz), 3,00-3,25 (m, 4H), 4,42-4,50 (m, 1H), 4.63 to-4,70 (m, 1H), 6,95 (d, 2H, J=9.0 Hz), 7,15-7,22 (m, 2H), 7,68 (d, 2H, J=9.0 Hz), of 8.25(d, 1H, J=3,4 Hz).
I-16(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1,95-2,15 (m, 4H), of 2.50 (s, 3H), to 2.67 (t, 2H,J=7.5 Hz), 2.95 and (t, 2H, J=7.5 Hz), 3,00-3,25 (m, 4H), 4,42-4,50 (m, 1H), 4.63 to-4,70 (m, 1H), 6,95 (d, 2H, J=9.0 Hz), 7,05 (d, 1H, J=8,8 Hz), 7,13 (d, 1H, J=8,8 Hz), to 7.68 (d, 2H, J=9.0 Hz).
I-17(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2,47 (t, 2H, J=7.5 Hz), of 2.72 (t, 2H, J=7.5 Hz), 3,05-3,20 (m, 4H), 4,35 was 4.42 (m, 1H), 4,60-4,70 (m, 1H), 6,62 is 6.67 (m, 1H), 6,78-6,97 (m, 2H), 7,68 (d, 2H, J=9,0 Hz).
I-18(CDCl3) to 1.35 (d, 6H, J=6.3 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), of 3.80 (s, 3H), 4,40-of 4.45 (m, 1H), 4.63 to-4,70 (m, 1H), 6,37 (d, 1H, J=15,9 Hz), 6,37 (d, 1H, J=2.0 Hz), 6,55 (DD, 1H, J=8.0 a, 2.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), was 7.45 (d, 1H, J=8.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 7,82 (d, 1H, J=15,9 Hz).
I-19(CDCl3) to 1.35 (d, 6H, J=6.3 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), of 3.80 (s, 3H), 4,40-of 4.45 (m, 1H), 4.63 to-4,70 (m, 1H), 6,37 (d, 1H, J=15,9 Hz), 6,37 (d, 1H, J=2.0 Hz), 6,55 (DD, 1H, J=8.0 a, 2.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), was 7.45 (d, 1H, J=8.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 7,82 (d, 1H, J=15,9 Hz).

Table 28
No. of connections1H-NMR (Solvent) δ
I-20(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2,42 (t, 2H, J=7.5 Hz), to 2.66 (t, 2H, J=7.5 Hz), 3,05-3,20 (m, 4H), 3,74 (s, 3H), 4,36 is 4.45 (m, 1H), 4.63 to-4,70 (m, 1H), 6,32 (d, 1H, J=2.0 Hz), 6,38 (DD, 1H, J=to 8.0, 2.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,02 (d, 1H, J=8.0 Hz), 7,86 (d, 2H, J=9.0 Hz).
I-21(CDCl3) to 1.35 (d, 6H, J=6.3 Hz), 1,90-2,10 (m, 4H), 2,85-2,95 (m, 2H), 3,35 is-3.45 (m, 2H), 3,80 (s, 3H), 4,06-to 4.15 (m, 1H), 4,60-4,71 (m, 1H), 6,37 (d, 1H, J=16.2 Hz), 6.90 to (t, 1H, J=8.1 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,05 (t, 1H, J=8.1 Hz), 7,17 (d, 1H, J=8.1 Hz), to 7.67 (d, 2H, J=9.0 Hz), 7,82 (d, 1H, J=16.2 Hz).
I-22(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2,52 (t, 2H, J=7.5 Hz), was 2.76 (t, 2H, J=7.5 Hz), 2,78-to 2.85 (m, 2H), 3.33 and is 3.40 (m, 2H), 3,74 (s, 3H), 4,16-of 4.25 (m, 1H), 4.63 to-4,70 (m, 1H), 6.75 in (d, 2H, J=8.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 6,97 (t, 1H, J=8.0 Hz), to 7.67 (d, 2H, J=9.0 Hz).
I-23(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), 2.06 to and 2.14 (m, 2H), 3,35-to 3.50 (m, 2H), 3,60-of 3.80 (m, 2H), 4,50-4,60 (m, 1H), 4,90-to 4.98 (m, 1H), 6,37 (d, 1H, J=16.1 Hz), 6,72 (d, 1H, J=9.0 Hz), to 6.80 (d, 2H, J=9.0 Hz), of 6.99 (t, 1H, J=9.0 Hz), 7,35 (t, 1H, J=9.0 Hz), 7,53 (d, 1H, J=9.0 Hz), the 7.65 (d, 2H, J=9.0 Hz), to 7.67 (d, 1H, J=16.1 Hz).
I-24(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), 2.06 to and 2.14 (m, 2H), 2,43 (t, 2H, J=7.5 Hz), 2,60 (t, 2H, J=7.5 Hz), 3,35-to 3.50 (m, 2H), 3,60-of 3.80 (m, 2H), 4,50-4,60 (m, 1H), 4,90-to 4.98 (m, 1H), 6,62 (d, 1H, J=8.0 Hz), 6,85 (d, 2H, J=9,0 Hz), to 6.88 (t, 1H, J=8.0 Hz), to 7.15 (d, 1H, J=8.0 Hz), and 18 (d, 1H, J=8.0 Hz), 7,71 (d, 2H, J=9.0 Hz).
I-25(CDCl3) of 1.39 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), 3,05-3,20 (m, 4H), 4,35 is 4.45 (m, 1H), 4,62-and 4.68 (m, 1H), to 6.39 (d, 1H, J=15,9 Hz), at 6.84 (d, 1H, J=8.0 Hz), 6,92 (d, 1H, J=8.0 Hz), to 6.95 (d, 2H, J=9.0 Hz), 7,13 (d, 1H, J=8.0 Hz), 7,33 (t, 1H, J=8.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), of 7.70 (d, 1H, J=15,9 Hz).
I-26(CDCl3) to 1.35 (d, 6H, J=6,1 Hz), 1.85 to 2.05 is (m, 4H), 2,60 (t, 2H, J=7.5 Hz), 2,85 (t, 2H, J=7.5 Hz), 3,00-3,20 (m, 4H), 4,30-and 4.40 (m, 1H), 4,60 with 4.65 (m, 1H), to 6.67 (d, 1H, J=8,2 Hz), 6,69 (s, 1H), 6,95 (d, 2H, J=9.0 Hz), 7,18 (t, 1H, J=8,2 Hz), to 7.68 (d, 2H, J=9.0 Hz).
I-27(DMSO-d6) of 1.35 (d, 6H, J=6.0 Hz), 1.70 to 2,00 (m, 4H), 2,60-of 2.75 (m, 2H), 3,40-3,55 (m, 2H), 4,05-to 4.15 (m, 1H), 4,68-of 4.75 (m, 1H), 6.35mm (d, 1H, J=15,9 Hz), 7,50-of 7.70 (m, 4H), 7,33 (t, 1H, J=8.0 Hz), 7,89 (d, 1H, J=15,9 Hz).
I-28(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), 1,90-2,10 (m, 4H), 2,60 (t, 2H, J=7.5 Hz), 2,60-of 2.75 (m, 2H), 2,85 (t, 2H, J=7.5 Hz), 3,45-3,55 (m, 2H), 4,05-to 4.15 (m, 1H), 4,68-of 4.75 (m, 1H), 6,95 (d, 2H, J=9.0 Hz), was 7.08 (d, 1H, J=2.0 Hz), 7,20 (d, 1H, J=2.0 Hz), to 7.68 (d, 2H, J=9.0 Hz).

Table 29
No. of connections1H-NMR (Solvent) δ
I-29(DMSO-d6) of 1.32 (d, J=6.0 Hz, 6H), 1,59 (userd, 2H), 1,94-of 2.08 (m, 2H), 2,54 (ushort, 2H), 3,51(userd, 2H), amounts to 4.76 (m, 1H), 4,82 (s, 2H), is 5.06 (s, 1H),? 7.04 baby mortality (DD,J=1,8, 8,1 Hz, 1H), to 7.09 (d, J=1.8 Hz, 1H), 7,15 (d-like, 2H), 7,35 (d, J=8,1 Hz, 1H), to 7.67 (d-like, 2H), 13,08 (user., 1H)
I-30(DMSO-d6) of 1.28 (d, J=6.0 Hz, 6H), 2,50 (userd, 2H), 3,18 (ushort, 2H), 3,65 (userd, 2H), 4,73 (m, 1H), a 4.83 (s, 2H), 6,11 (ushort, 1H), 6,94 (DD, J=1,8, 8,1 Hz, 1H), 7,00 (d, J=1.8 Hz, 1H), 7,11 (d-like, 2H), was 7.36 (d, J=8,1 Hz, 1H), 7,71 (d-like, 2H), 13,06 (user., 1H)
I-31(DMSO-d6) of 1.31 (d, J=6.0 Hz, 6H), 1,60-1,80 (m, 4H), 2,20-to 2.29 (m, 2H), 2,47 (m, 1H), 3.72 points userd, 2H), and 4.75 (m, 1H), 4,79 (s, 2H), 6,78 (DD, J=1,8, and 8.4 Hz, 1H), make 6.90 (d, J=1.8 Hz, 1H), 7,13 (d-like, 2H), 7,30 (d, J=8,4 Hz, 1H), 7,66 (d-like, 2H), 13,04 (user., 1H)
II-1(DMSO-d6) of 1.31 (d, 6H,J=6.0 Hz), 2,99 (users, 4H), is 3.08 (users, 4H), br4.61 (s, 2H), 4.72 in-4,80 (m, 1H), 6,78 (d, 1H, J=6.9 Hz), 6.87 in-to 6.95 (m, 3H), 7,15 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H, J=9.0 Hz)
II-2(DMSO-d6) of 1.34 (d, 6H, J=6.3 Hz), 3,07 (userd, 8H, J=5.4 Hz), br4.61 (s, 2H), 5,34-of 5.40 (m, 1H), 6,79 (d, 1H, J=7.8 Hz), 6,85-to 6.95 (m, 3H), 6,98 (d, 1H, J=9.0 Hz), 8,01 (DD, 2H, J=2,4, and 8.7 Hz), 8,55 (d, 1H, J=and 2.1 Hz), 13,01 (users, 1H)
II-3(DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), 2,93-2,99 (osirm, 4H), 3,17-3,22 (osirm, 4H), 4,59 (s, 2H), 4,71-rate 4.79 (m, 1H), 6,33 (DD, 1H, J=2,4, 8.1 Hz), to 6.43 (t, 1H, J=2.4 Hz), 6,50 (DD, 1H, J=2,4, 8.1 Hz), was 7.08 (t, 1H, J=8,1 Hz), 7,14 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 12,90 (users, 1H)
II-4(DMSO-d6) of 1.30 (d, 6H, J=6.3 Hz), 2,94-3,00 (ush the RM, 4H), 3,02-is 3.08 (osirm, 4H), 4,55 (s,2H), 4,71-4,80 (m, 1H), 6,78 (d, 2H, J=9,3 Hz), 6,85 (d, 2H, J=9,3 Hz), to 7.15 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H, J=9.0 Hz), 12,89 (users, 1H)
II-5(DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), 2,94 (users, 4H), 3,10 (users, 4H),4,55 (s, 2H), 4,72-to 4.81 (m, 1H), 6,16 (t, 1H, J=7,2 Hz), 6,74 (DD, 1H, J=1.5 and 7.5 Hz), to 7.15 (d, 2H, J=9.0 Hz), 7,30 (DD, 1H, J=1,5, and 6.6 Hz), to 7.67 (d, 2H, J=9.0 Hz), 12,87 (users, 1H)
II-6(DMSO-d6) of 1.31 (d, 6H, J=6.0 Hz), 2,99 (users, 4H), 3,13 (users, 4H), 4.72 in-4,79 (m, 3H), 6,92 (DD, 1H, J=5,1, 7.5 Hz), to 7.15 (d, 2H, J=8.7 Hz), 7.23 percent (d, 1H, J=7.8 Hz), to 7.67-of 7.70 (m,3H), was 12.75 (users, 1H)
II-7(DMSO-d6) of 1.31 (d, 6H, J=6.0 Hz), 2,98 (users, 4H), to 3.02 (users, 4H), of 4.67 (s, 2H), 4.72 in-4,80 (m, 1H), 6,66-6,76 (m, 2H), 6.90 to (DD, 1H, J=6,3,8,7 Hz), to 7.15 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H, J=8.7 Hz)
II-8(CDCl3) to 1.37 (d, 6H, J=6.3 Hz), measuring 2.20 (s, 3H), 2,50 (users, 1H), 3,20 (users, 8H), br4.61-of 4.67 (m, 3H), to 6.43 (s, 1H), 6,51 (d, 1H, J=8.1 Hz), 6,97 (d, 2H, J=9.0 Hz), 7,05 (d, 1H, J=7.8 Hz), 7,69 (d, 2H, J=9.0 Hz)

Table 30
No. of connections1H-NMR (Solvent) δ
II-9(CDCl3) to 1.38 (d, 6H, J=6.0 Hz), 1,95 (users, 1H), and 3.16 (users, 8H), 3,86 (s, 3H), 4,60-4,69 (m, 3H), 6,60-6,63 (m, 2H), 6,85 (d, 1H, J=9.0 Hz), 6,98 (d, 2H, J=9.0 Hz), of 7.70 (d, 2H,=9,0 Hz)
II-10(CDCl3) of 1.37 (d, 6H, J=6.0 Hz), 3,16-3,23 (users, 8H), to 3.73 (users, 1H), 4,60-4,71 (m,3 H), of 6.49-is 6.54 (m, 2H), 6,98 (d, 2H, J=9.0 Hz), 7,24 (d, 1H, J=8.7 Hz), 7,69 (d, 2H, J=9.0 Hz)
II-11(CDCl3) to 1.37 (d, J=6.3 Hz, 6H), 3.00 and (users, 1H), is 3.08 (ushort, J=4,8 Hz, 4H), 3,57 (ushort, J=4,8, 4H), 4,58-of 4.66 (m, 1H), of 4.77 (s, 2H), to 6.19 and 6.25 (m, 2H), of 6.96 (d, J=9.0 Hz, 2H), 7,44 (t, J=7.8 Hz, 1H), to 7.67 (d, J=9,0 Hz, 2H)
II-12(CDCl3) to 1.35 (d, J=5.7 Hz, 6H), is 3.08 (users, 4H), 3,68 (users, 4H), 4,58-of 4.66 (m, 1H), 4,79 (s, 2H), 5,64 (users, 1H), 6,29 (users, 1H), to 6.39 (d, J=6.0 Hz, 1H), 6,95 (d, J=9.0 Hz, 2H), 7,63 (t, J=9.0 Hz, 2H), 7,92 (d, J=6,9 Hz, 1H)
II-13(CDCl3) to 1.37 (d, 6H, J=6.3 Hz), 3.15 in (ushort, 4H, J=4,8 Hz), 3,50 (ushort, 4H, J=4, 2 Hz), 4,60-4,70 (m, 1H), and 4.75 (s, 2H), 6,24,(s, 1H), of 6.49 (DD, 1H, J=2.1 a, and 9.3 Hz), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=8.7 Hz), 8,06 (d, 2H, J=9.6 Hz)
II-14(CDCl3) of 1.36 (d, J=5.7 Hz, 6H), 3,10 (users, 4H), 3,39 (users, 1H), 3,74 (users, 4H), 4,60-and 4.68 (m, 1H), to 4.73 (s, 2H), 6,33 (users, 1H), gold 6.43 (users, 1H), 6,95 (userd, J=8.7 Hz, 2H), 7,63 (userd, J=7.8 Hz, 1H), to $ 7.91 (users, 1H)
II-15(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,17 (m, 4H), of 3.25 (m, 4H), 4,63 (m, 1H), 6,92 (DD, 1H, J=9,0, 3.0 Hz), 6,97 (d, 2H, J=9.9 Hz), 7,26-7,30 (m, 2H), 7,69 (d, 2H).
II-16(CDCl3) to 1.38 (d, J=6.0 Hz, 6H) 3,00 (users, 1H), 3.15 in (s, 8H), 4,60-and 4.68 (m, 1H), 4,71 (s, 2H), 6,27 (users, 1H), 6,32-to 6.39 (m, 1H), 6,98 (d, J=8.7 Hz, 2H), 7,69 (d, J=8.7 Hz, 2H)
II-17(CDCl3) to 1.37 (d, 6H, J=6,1 Hz), 3,09-3,13 (m, 4H), to 4.62 (s, 2H), 4.63 to-4,69 (m, 1H), 6.35mm (s, 1H), 6,51 (s, 1H), 6,65 (s, 1H), 6,98 (d, 2H, J=8.7 Hz), 7,69 (d, 2H, J=8.7 Hz).
II-18(DMSO-d6) of 1.30 (d, 6H, J=5.7 Hz), of 2.97 (t, 4H), to 3.38 (t, 4H), and 4.75 (m, 1H), 6,65 (d, 1H, J=16.2 Hz), of 6.99 (DD, 1H, J=9,0, 2.7 Hz), 7,14 (d, 2H, J=9.0 Hz), 7,32 (d, 1H), 7,35 (d, 1H), 7,68 (d, 2H), 7,78 (d, 1H).
II-19(DMSO-d6) of 1.38 (d, J=5.7 Hz, 6H), 2,96 (users, 4H), 3,29 (users, 4H), br4.61 (s, 2H), 4,71-rate 4.79 (m, 1H), to 6.57 (s, 1H), to 6.67 (s, 1H), 6,76 (s, 1H), 7,14 (d, J=8.7 Hz, 2H), 7,66 (d, J=8.7 Hz, 2H)
II-20(CDCl3) to 1.38 (d, 6H, J=6.3 Hz), 3.25 to 3,26 (m, 8H), of 3.75 (s, 2H), with 4.64 (m, 1H), 6.87 in-6,99 (m, 4H), 7,28 (d, 1H), 7,69 (d, 2H, J=9.0 Hz).
II-21(CDCl3) to 1.38 (d, 6H, J=6.0 Hz), to 2.67 (t, 2H, J=7,8 Hz)of 3.00 (t, 2H), 3,18-is 3.21 (m, 8H), 4,63 (m, 1H), of 6.71-PC 6.82 (m, 3H), 6,97 (d, 2H, J=9.0 Hz), 7,21 (d, 1H, J=8,4 Hz), 7,69 (d, 2H).
II-22(CDCl3) to 1.38 (d, 6H, J=6.3 Hz), to 2.65 (t, 2H, J=7.8 Hz), of 2.92 (t, 2H), 3,29-3,30 (m, 8H), with 4.64 (m, 1H), 6,86-6,99 (m, 5H), of 7.23 (d, 1H, J=7.8 Hz), of 7.70 (d, 2H, J=8.7 Hz).

Table 31
No. of connections 1H-NMR (Solvent) δ
II-23(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,02 (s, 3H), 2,96 (users, 4H), 3,14 (users, 4H), 4,69 (s, 2H), 4,71-rate 4.79 (m, 1H), 6,45 (DD, J=2,4, and 9.0 Hz, 1H), is 6.54 (d, J=2.4 Hz, 1H), 7,14 (d, J=8.7 Hz, 2H), 7,65-to 7.68 (m, 3H), of 9.02 (s, 1H)
II-24(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,20 (users, 4H), 4,71-4,79 (m, 3H), 6,55 (DD, J=2,4, and 8.7 Hz, 1H), 6,68-6,70 (m, 2H), 7,15 (d, J=8.7 Hz, 2H), 7.23 percent (DD, J=0,6 and 2.2 Hz, 1H), 7,68 (d, J=9.0 Hz, 2H), 7,81 (d, J=8.7 Hz, 1H), 7,89-of 7.90 (m, 1H), of 9.30 (s, 1H)
II-25(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), is 3.08-3,17 (m, 4H), 3,20-3,30 (m, 4H), 4,59 (s, 2H), 4,57 with 4.65 (m, 1H), 6,07 (d, 1H, J=8,8 Hz), 6,21 (s, 1H), from 6.22 (d, 1H, J=8,8 Hz), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=9,0 Hz)
II-26(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), is 3.08-3,17 (m, 4H), 3,20-3,30 (m, 4H), 4,60 (s, 2H), 4,58 with 4.65 (m, 1H), of 6.31 (s, 1H), 6,33 (s, 1H), of 6.49 (s, 1H), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=9.0 Hz)
II-27(CDCl3) to 1.32 (d, J=6.3 Hz,6H), 3,01 totaling 3.04 (m, 4H), 3,20 is 3.23 (m, 4H), was 4.76 (s, 2H), 5,34 (Sept., J=6.3 Hz, 1H), 6.48 in (DD, J=2.7, and 8.7 Hz, 1H), return of 6.58 (d, J=2.7 Hz, 1H), of 6.96 (d, J=8.7 Hz, 1H), 7,20 (d, J=8.7 Hz, 1H), 8,00 (DD, J=2.7, and 8.7 Hz, 1H), 8,55 (d, J=2.7 Hz, 1H), 13,03 (user., 1H)
II-28(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,98 (users, 4H), 3,21 (users, 4H), 4.72 in-4,80 (m, 3H), to 6.57 (DD, J=2,4,8,7 Hz, 1H), of 6.71 (d, J=2.4 Hz, 1H), 7,15 (d, J=8.7 Hz, 2H), 7,49-to 7.61 (m, 3H), 7,68 (d, J=8.7 Hz, 2H), 7,74 (d, J=8.7 Hz, 1H), 7.5 (d, J=8,4 Hz, 2H), 9,51 (s, 1H)
II-29(DMSO-d6) of 0.91(t, J=7.2 Hz, 3H), of 1.26 (d, J=6.0 Hz, 6H), 1,53 to 1.76 (m, 2H), 2.91 in-2,99 (m, 4H), 3,16-3,24 (m, 4H), 4,51 (m, 1H), and 4.75 (s, 2H), 6,47 (DD, J=2,4, and 8.7 Hz, 1H), return of 6.58 (d, J=2.4 Hz, 1H), 7,15 (d-similar, 2H), 7,19 (d, J=8.7 Hz, 1H), 7,66 (d-like, 2H), 13,02 (user., 1H)
II-30(DMSO-d6) 2,91-to 2.99 (m, 4H), 3,16-3,24 (m, 4H), 3,86 (s, 3H), and 4.75 (s, 2H), 6,46 (DD, J=2,4, and 8.7 Hz, 1H), to 6.57 (d, J=2.4 Hz, 1H), 7,17 (d-like, 2H), 7,18 (d, J=8.7 Hz, 1H), 7,70 (d-like, 2H), 13,01 (user., 1H)
II-31(DMSO-d6) of 1.33 (d, J=6.0 Hz, 6H), 2.95 and totaling 3.04 (m, 4H), 3,16-3,24 (m, 4H), was 4.76 (s, 2H), to 4.81 (m, 1H), 6,47 (DD, J=2,4, and 8.7 Hz, 1H), return of 6.58 (d, J=2.4 Hz, 1H), 7,20 (d, J=8.7 Hz, 1H), 7,43 (t, J=8,4 Hz, 1H), 7,54 (DD, J=2,1, 9.0 Hz, 1H), 7,60 (DD, J=2,1, 10.5 Hz, 1H), 13,01 (users, 1H)
II-32(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), and 3.16 (users,4H), 3,39 (s,3H),of 3.96 (s, 2H), 4,70-4,80 (m, 3H), of 6.49 (d, J=8,4 Hz, 1H), only 6.64 (s, 1H), 7,14 (d, J=8.7 Hz, 2H), to 7.67 (d, J=8,4 Hz, 2H), to $ 7.91 (d, J=8.7 Hz, 1H), of 8.92 (s, 1H)

Table 32
No. of connections1H-NMR (Solvent) δ
II-33(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2.95 and (users, 4H), to 3.02 (users, 4H), 4,71-4,79 (m, 3H), 6.42 per (DD, J=2,4, and 9.0 Hz, 1H), is 6.54 (d, J=2.4 Hz, 1H), 7,13 (d, J=9.0 Hz, 2H), 7,32 (d, J=8.7 Hz, 1), 7,66 (d, J=8.7 Hz, 2H)
II-34(DMSO-d6) 2,97 totaling 3.04 (m, 4H), 3,17-3,24 (m, 4H), was 4.76 (s, 2H), 6,47 (DD, J=2.7, and 8.7 Hz, 1H), return of 6.58 (d, J=2.7 Hz, 1H), 7,19 (d, J=8.7 Hz, 1H), 7,47-of 7.55 (m, 2H), 7,82-7,89 (m, 2H), 13,00 (user., 1H)
II-35(DMSO-d6) of 1.31 (d, J=6.6 Hz, 6H), 2,94-3,03 (m, 4H), 3.15 and is 3.23 (m, 4H), to 3.73 (m, 1H), and 4.75 (s, 2H), 6,47 (DD, J=2.7, and 8.7 Hz, 1H), return of 6.58 (d, J=2.7 Hz, 1H), 7,19 (d, J=8.7 Hz, 1H), 7,54 (d-like, 2H), to 7.67 (d-similar, 2H), 13,02 (user., 1H)
II-36(DMSO-d6) of 0.98 (d, J=6.6 Hz, 6H), 2,04 (Sept., J=6,6 Hz, 1H), 2.91 in-2,99 (m, 4H), 3,16-3,24 (m, 4H), 3,85 (d, J=6.6 Hz, 2H), and 4.75 (s, 2H), 6,47 (DD, J=2,4, and 8.7 Hz, 1H), to 6.57 (d, J=2.4 Hz, 1H), 7,17 (d-like, 2H), 7,19 (d, J=8.7 Hz, 1H), 7,65 (d-like, 2H), 13,00 (user., 1H)
II-37(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), is 3.08-3,17 (m, 4H), 3,20-3,30 (m, 4H), 3.43 points (s, 3H), 4,29 (s, 2H), 4,60 (s, 2H), 4,58 with 4.65 (m, 1H), of 6.31 (s, 1H), 6,33 (s, 1H), of 6.49 (s, 1H), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=9.0 Hz)
II-38(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 4H), 3.25 to 3.30 is (m, 4H), 4,58 with 4.65 (m, 1H), 4,70 (s, 2H), 6,44 (s, 1H), to 6.57 (s, 1H), is 6.61 (s, 1H), of 6.68 (s, 1H), 6,98 (d, 2H, J=8.6 Hz), 7,45 (s, 1H), 7,69 (d, 2H, J=8.6 Hz).
II-39(DMSO-d6) of 1.37 (d, 6H, J=6.0 Hz), 2,98-of 3.07 (m, 4H), 3,20-3,30 (m, 4H), 4,60 (s, 2H), 4,58 with 4.65 (m, 1H), 6,55 (s, 1H), 6.75 in (s, 1H), 6,95 (s, 1H), 7,18 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=9.0 Hz), the 7.65 to 7.75 (m, 2H), 8,60-8,64 (2H).
II-40 (DMSO-d6) of 1.37 (d, 6H, J=6.0 Hz), 2,98-of 3.07 (m, 4H), 3,20-3,30 (m, 4H), with 4.64 (s, 2H), 4,68-of 4.75 (m, 1H), 6,45 (s, 1H), 6,65 (s, 1H), 6,80 (s, 1H), 7,18 (d, 2H, J=9.0 Hz), 7,39 was 7.45 (m, 1H), 7,69 (d, 2H, J=9,0 Hz), 8,00 (d, 1H, J=8.0 Hz), 8,53 (d, 1H, J=4,8 Hz), 8,80 (users, 1H).
II-41(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), of 2.23 (s, 3H), is 3.08-3,17 (m, 4H), 3,20-3,30 (m, 4H), 4,60 (s, 2H), 4,58 with 4.65 (m, 1H), 6,47 (s, 2H), 6,65 (s, 1H), 6,98 (d, 2H, J=9.0 Hz), 7,69 (d, 2H, J=9.0 Hz).
II-42(DMSO-d6) of 1.30 (d, 6H, J=5.7 Hz), 2,96 (t, 4H), of 3.28 (t, 4H), 4,71 (s, 2H), and 4.75 (m, 1H), 6.87 in (DD, 1H, J=2.1 Hz), 7,14 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H), 7,71 (d, 1H), 7,88 (d, 1H).
II-43(DMSO-d6) of 1.08 (d, 3H, J=6.6 Hz), of 1.29 (d, 6H, J=6.0 Hz), 2,42 was 2.76 (m, 2H), 3,20-3,59 (m, 4H), to 4.01 (m, 1H),4,68 was 4.76 (m, 3H), to 6.43 (m, 2H), was 7.08 (d, 2H, J=9.0 Hz), 7,18 (d, 1H, J=8.7 Hz), 7,73 (d, 2H).
II-44(DMSO-d6) of 0.98 (d, 3H, J=6.3 Hz), of 1.30 (d, 6H, J=6.0 Hz), 2,35-of 2.56 (m, 2H), 3.00 and-3,59 (m, 4H), a 4.03 (m, 1H), 4,71-4,79 (m, 3H), 6,44 (DD, 1H, J=8,7, and 2.1 Hz), 6,53 (d, 1H), 7,14 (d, 2H, J=9.0 Hz), 7,19 (d, 1H), 7,66 (d, 2H).

Table 33
No. of connections1H-NMR (Solvent) δ
II-45(DMSO-d6) of 1.31 (d, J=6.0 Hz, 6H), 2,93-to 3.02 (m, 4H), 3,06-3,14 (m, 4H), with 4.64 (s, 2H), amounts to 4.76 (m, 1H), 6,80 (d, J=8.7 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and 8.7 Hz, 1H), 7,15 (d-podobn the th, 2H), to 7.67 (d-like, 2H), 13,01 (user., 1H)
II-46(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,17 (t, 4H), 3.46 in (t, 4H), 4,63 (m, 1H), amounts to 4.76 (s, 2H), 6,38 (d, 1H, J=2.4 Hz), 6,62 (DD, 1H, J=9,0, 2,1 Hz), 6,98 (d, 2H), to 7.67 to 7.75 (m, 3H), 8,39 (s, 1H).
II-47(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,98 (users, 4H), 3,20 (users, 4H), 4,70-rate 4.79 (m, 1H), around 4.85 (s, 2H), 6,55 (d, J=9.0 Hz, 1H), of 6.68 (s, 1H), 7,14 (d, J=8.7 Hz, 2H), of 7.64-of 7.69 (m, 3H), of 8.06 (d, J=9,3 Hz, 1H), 8,16 (d, J=7.8 Hz, 1H), 8,24 (d, J=7.8 Hz, 1H), 8,68 (d, J=5.7 Hz, 1H), the 10.40 (s, 1H), of 13.05 (users, 1H)
II-48(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,98 (users, 4H), 3,22 (users, 4H), 4.72 in-4,80 (m, 3H), to 6.57 (DD, J=2.1 a, 8,7 Hz, 1H), of 6.68 (d, J=2.4 Hz, 1H), 7,15 (d, J=9.0 Hz, 2H), 7,53-EUR 7.57 (m, 1H), of 7.64-of 7.70 (m, 3H), 8,29 (d, J=8,1 Hz, 1H), total of 8.74 (s, 1H), 9,10 (s, 1H), 9,79 (s, 1H), 13,10 (users, 1H)
II-49(DMSO-d6) of 1.30 (d, J=6.3 Hz, 6H), 2,98 (users, 4H), 3,22 (users, 4H), 4,73-4,80 (m, 3H), to 6.57 (DD, J=2,4, and 9.0 Hz, 1H), 6,69 (d, J=1.8 Hz, 1H), 7,15 (d, J=9.0 Hz, 2H), 7,65-of 7.70 (m, 3H), a 7.85 (d, J=5.4 Hz, 2H), 8,76 (users, 2H), 9,86 (users, 1H), 13,16 (users, 1H)
II-50(DMSO-d6) of 1.37 (d, J=6.0 Hz, 6H), of 2.08 (Quint., J=5.7 Hz, 2H), 2,12 (user., 1H), 3,12-of 3.25 (m, 8H), to 3.89 (t, J=5.7 Hz, 2H), 4,14 (t, J=5.7 Hz, 2H), 4,63 (Sept., J=6.0 Hz, 1H), 6,41 (DD, J=2.7, and an 8.4 Hz, 1H), 6,47 (d, J=2.7 Hz, 1H), 6,97 (d-like, 2H), 7,19 (d, J=8,4 Hz, 1H), 7,69 (d-like, 2H)
II-51(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,183,22 (m, 4H), 3.25 to 3.30 is (m, 4H), 4,58 with 4.65 (m, 1H), 4,70 (s, 2H), 6,41 (s, 1H), 6,65 (s, 1H), 6,77 (s, 1H), 6,98 (d, 2H, J=8.6 Hz), 7.03 is-7,10 (m, 1H), 7,26-7,30 (m, 2H), of 7.70 (d, 2H, J=8.6 Hz).
II-52(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,68 (t, J=6,0,2H), 2,92-3,00 (m, 4H), 3,19-of 3.27 (m, 4H), 4,19 (t, J=6.0 Hz, 2H),4.75 in (Sept., J=6.0 Hz, 1H), 6,46 (DD, J=2,4, and 8.7 Hz, 1H), 6,66 (d, J=2.4 Hz, 1H), 7,14 (d-like, 2H), 7,17 (d, J=8.7 Hz, 1H), to 7.67 (d-like, 2H), 12,37 (user., 1H)
II-53(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,99 (users, 4H), 3,26 (users, 4H), 4,78 (s, 2H), 4,72-rate 4.79 (m, 1H), 6,55-to 6.57 (m, 2H), 7,14-7,17 (m, 3H), of 7.23 (t, J=7.2 Hz, 1H), 7,34 (t, J=7.8 Hz, 2H), 7,51 (d, J=7.8 Hz, 2H), to 7.68 (d, J=9.0 Hz, 2H)
II-54(DMSO-d6) of 1.29 (d, J=6.0 Hz, 6H), 2,97 (users,4H), 3,26 (users, 4H), 4,79-4,70 (m, 3H), of 6.52 (d, J=9.0 Hz, 1H), 6,55 (s, 1H), 6,97 (s, 1H), 7,14 (d, J=9.0 Hz, 2H), 7,44 (d, J=9.0 Hz, 1H), 7,66 (s, 1H), to 7.67 (d, J=9.0 Hz, 2H), at 8.36 (s, 1H)
II-55(DMSO-d6) of 1.33 (d, J=6.0 Hz, 6H), 2,98 was 3.05 (m, 4H), 3,16 is 3.23 (m, 4H), 4,79 (s, 2H), 5,34 (Sept., J=6.0 Hz, 1H), 6.48 in-6,56 (m, 2H),6,97 (d, J=8.7 Hz, 1H), 8,00 (DD, J=2,4, and 8.7 Hz, 1H), 8,55 (d, J=2.4 Hz, 1H), to 13.09 (user., 1H)

Table 34
No. of connections1H-NMR (Solvent) δ
II-56(DMSO-d6) of 1.37 (d, J=6.0 Hz, 6H), 2,18 (user., 1H), 3,13 of 3.28 (m, 8H), 3.96 points (at IRM, 2H), 4,10 (t, J=4.5 Hz, 2H), 4,63 (Sept., J=6.0 Hz, 1H), 6,47 (DD, J=2,4, and 8.7 Hz, 1H), 6,54 (users, 1H), 6,97 (d-like, 2H), 7,22 (d, J=8.7 Hz, 1H), 7,69 (d-like, 2H)
II-57(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 4H), 3.25 to 3.30 is (m, 4H), 4,58 with 4.65 (m, 1H), 4,70 (s, 2H), 6,53 (s, 1H), 6,65 (s, 1H), 6,77 (s, 1H), 6,98 (d, 2H, J=8.6 Hz), 7,34-the 7.43 (m, 3H), 7,46 is 7.50 (m, 2H), 7,70 (d, 2H, J=8.6 Hz),
II-58(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,23 (users, 4H), 4,70-4,80 (m, 3H), 6,48-of 6.65 (m, 3H), 7.03 is-7,16 (m, 3H), 7,65 for 7.78 (m, 3H), 9,60 (s, 1H), 12,98 (users, 1H)
II-59(DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,96 (users, 4H), 3.15 in (users, 4H), 3,61 (s, 3H), 4,66-4,80 (m, 3H), of 6.49 (d, J=8,1 Hz, 1H), return of 6.58 (s, 1H), 7,14 (d, J=9.0 Hz, 2H), 7,41 (s, 1H), to 7.67 (d, J=8,4 Hz, 2H), 8,29 (users, 1H), 13,00 (users, 1H)
II-60(DMSO-d6) of 1.30 (d, J=5.4 Hz, 6H), of 2.50 (s, 3H), 2,97 (users, 4H), 3,20 (users, 4H), 4,65-4,85 (m, 3H), is 6.54 (d, J=7.5 Hz, 1H), 6,66-6,70 (m,2H), 7,15 (d, J=8.7 Hz, 2H), 7,68 (d, J=8,4 Hz, 2H), 7,86 (d, J=9,0 Hz, 1H), for 9.47 (s, 1H), 13,11 (users, 1H)
II-61(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 2,60 (s, 3H), 3,17 (t, 4H), 3,44 (t, 4H), 4,63 (m, 1H), 4,74 (s, 2H), 6,38 (d, 1H, J=2.1 Hz), 6,60 (DD, 1H, J=8,4, 1.8 Hz), 6,98 (d, 2H, J=9.0 Hz), to 7.67-7,71 (m, 3H)
II-62(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,21 (t, 4H), to 3.41 (t, 4H), 4,63 (m, 1H), 4,79 (s, 2H), 6,37 (d, 1H), 6,63 (DD, 1H), 6,99 (d, 2H), to 7.09 (t, 1H), 7,32 (m, 1H), 7,69 (d, 1H, J=9.0 Hz),7,79 (d, 2H, J=8.1 Hz), of 8.09 (d, 1H), 9,80 (s, 1H).
II-63(CDCl3) to 1.24 (d, 6H, J=6.3 Hz), of 1.37 (d, 6H, J=6.0 Hz), 3,14 (t, 4H), to 3.35 (t, 4H)and 4.65 (m, 1H), 4,71 (s, 2H), 6,29 (d, 1H, J=2.4 Hz), 6,53 (DD, 1H, J=8,7, and 2.1 Hz), 6,97 (d, 2H, J=3.0 Hz), 7,66-7,72 (m, 3H), to 7.84 (d, 1H, J=8.7 Hz).
II-64(CDCl3) to 1.22 (d, 6H, J=6.0 Hz), of 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 4H), 3.25 to 3.30 is (m, 4H), 4,28 is 4.36 (m, 1H), 4,58 with 4.65 (m, 1H)and 4.65 (s, 2H), 6,01 (users, 1H), to 6.57 (s, 1H), 6.75 in (s, 1H), 6.89 in (s, 1H), 6,98 (d, 2H, J=8.6 Hz), of 7.70 (d, 2H, J=8.6 Hz).
II-65(DMSO-d6) of 1.29 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,29 (users, 4H), 4,71-4,80 (m, 3H), 6,52-to 6.57 (m, 3H), 7,11 (d, J=3.0 Hz, 1H), 7,14 (d, J=9.0 Hz, 2H), 7,56 (d, J=9,3 Hz, 1H), to 7.61 (d, J=1.2 Hz, 1H), to 7.67 (d, J=9.0 Hz, 2H)
II-66(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 4H), 3.25 to 3.30 is (m, 4H), 4,58 with 4.65 (m, 1H), to 4.73 (s, 2H), only 6.64 (s, 1H), 6,98 (d, 2H, J=8.6 Hz), 7,07 (s, 1H), 7,24 (s, 1H), 7,28 (s, 1H), of 7.70 (d, 2H, J=8.6 Hz), 8,46 (s, 1H).
II-67(DMSO-d6) of 1.21 (d, J=6.3 Hz, 6H), of 1.30 (d, J=6.0 Hz, 6H), 2,96 (users, 4H), 3,14 (users, 4H), to 4.62 (s, 2H), 4,71-4,85 (m, 2H), 6.48 in (d, J=9.9 Hz, 1H), 6,59 (s, 1H), 7,14 (d, J=8.7 Hz, 2H), 7,47 (userd, J=6,6 Hz, 1H), to 7.67 (d, J=8.7 Hz, 2H), compared to 8.26 (users, 1H)

Table 35
No. of connections1H-NMR (Solvent) δ
II-68(DMSO-d6) of 1.06 (d, J=6.6 Hz, 6H), of 1.30 (d, J=6.3 Hz, 6H), 2,96-of 2.97 (m, 4H), 3,06-is 3.08 (m, 4H), 3,65 is 3.76 (m, 1H), 4,71-4,79 (m, 3H), to 6.39 (DD, J=2,4, and 8.7 Hz, 1H), 6,50 (d, J=2.4 Hz, 1H), 6,62 (d, J=7.5 Hz, 1H), 7,14 (d, J=9.0 Hz, 2H), 7,52 (s, 1H), to 7.67 (d, J=9.0 Hz, 2H), 7,81 (d, J=9.0 Hz, 1H), 13,02 (users, 1H)
II-69(DMSO-d6) of 1.31 (d, J=6.0 Hz, 6H), to 3.02 (users, 8H), of 4.67 (s, 1H), 4,73-4,80 (m, 2H), 6,59 (DD, J=3,0, 9.0 Hz, 1H), 6,70 (d, J=2.7 Hz, 1H), 7,16 (d, J=8.7 Hz, 2H), 7,27 (d, J=9.0 Hz, 1H), 7,68 (d, J=8.7 Hz, 2H,)
II-70(CDCl3) to 1.35 (d, 6H, J=6.0 Hz), of 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), 4,48-4,56 (m, 1H), to 4.52 (s, 2H), 4,58 with 4.65 (m, 1H), return of 6.58 (d, 1H, J=8.5 Hz), 6,60 (s, 1H), 6,83 (d, 1H, J=8.5 Hz), of 6.96 (d, 2H, J=8,5 Hz), 7,81 (d, 2H, J=8.5 Hz),
II-71(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), to 4.52 (s, 2H), 4,58 with 4.65 (m, 1H), 5,10 (s, 2H), return of 6.58 (d, 1H, J=8.5 Hz), 6,70 (s, 1H), 6,83 (d, 1H, J=8.5 Hz), of 6.96 (d, 2H, J=8.5 Hz), 7,30-7,40 (m, 5H), 7,81 (d, 2H, J=8.5 Hz),
II-72(DMSO-d6) of 1.30 (d, J=6.3 Hz, 6H), 2,97 (users, 4H), 3.15 in (s, 3H), 3,26 (users, 4H), 4,58-4,80 (m, 3H), 5,71 (d, J=3.3 Hz, 1H), 6,29 (s, 1H), 6,45 (DD, J=2.1 a, 8,7 Hz, 1H), 6,59 (s, 1H), 6,99 (d, J=8,4 Hz, 1H), 7,15 (d, J=9.0 Hz, 2H), 7,62-of 7.69 (m, 3H).
II-73(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 2,43 (s, 3H), and 3.16 (user., 4H), 3.45 points (user., 4H), 4,63 (m, 1H), around 4.85 (s, 2H), to 6.43 (user., 1H), 6,57 (user., 1H), of 6.96-7,01 (m, 3H), 7.68 per to 7.75 (m, 3H).
I-74 (CDCl3) to 1.37 (d, 6H, J=6.0 Hz), and 3.16 (t, 4H), of 3.42 (t, 4H), 4,63 (m, 1H), of 4.77 (s, 2H), 6,40 (d, 1H, J=2.7 Hz), 6,62 (DD, 1H, J=9,0, 2.4 Hz), 6,98 (d, 2H, J=3.0 Hz), 7,27 (d, 1H), to 7.67-7,72 (m, 3H), 7,79 (d, 1H, J=3.0 Hz).
II-75(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), and 2.79 (s, 3H), and 3.16 (t, 4H), 3.43 points (t, 4H), 4,63 (m, 1H), 4,82 (s, 2H), 6,41 (d, 1H, J=2.1 Hz), to 6.57 (DD, 1H,J=8,4, 2.4 Hz), 6,98 (d, 2H, J=8.7 Hz), a 7.62 (d, 1H, J=8,4 Hz), 7,69 (d, 2H).
II-76(DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), 4,59 (s, 2H), 4,58 with 4.65 (m, 1H), 6,38 (d, 1H, J=8.5 Hz), 6,50 (s, 1H), 6,65 (d, 2H, J=8.5 Hz), 7,12 (d, 1H, J=8.5 Hz), to 7.61 (d, 2H, J=8.5 Hz).
II-77(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), to 4.52 (s, 2H), 4,58 with 4.65 (m, 1H), 5,10 (s, 2H), return of 6.58 (d, 1H, J=7.5 Hz), 6,70 (s, 1H),6,83 (d, 1H, J=8.5 Hz), of 6.96 (d, 2H, J=8.5 Hz), 7,41 (s, 1H), of 7.48 (s, 1H), 7,81 (d, 2H, J=8.5 Hz).
II-78(CDCl3) of 1.03 (d, 6H, J=6.0 Hz), of 1.37 (d, 6H, J=6.0 Hz), 2,01-2,11 (m, 1H), 3,18-up 3.22 (m, 8H), of 3.75 (d, 2H, J=6,0), to 4.62 (s, 2H), 4,60-4,69 (m,1H), return of 6.58 (d, 1H, J=7.5 Hz), of 6.65 (s, 1H), 6,83 (d, 1H, J=7.5 Hz), of 6.96 (d, 2H, J=8.5 Hz), 7,81 (d, 2H, J=8.5 Hz).

Table 36
No. of connections1H-NMR (Solvent) δ
II-79(DMSO-d6) of 1.31 (d, J=6.0 Hz, 6H), 2.95 and-to 3.02 (m, 4H), 3,14-3,24 (m, 4H), with 4.64 (s, 2H, 4,76 (Sept., J=6.0 Hz, 1H), 6,44 (DD, J=2,4, and 8.7 Hz, 1H), 6,63 (d, J=2.4 Hz, 1H), 6,78-6,83 (m, 2H), 6.89 in (d, J=8.7 Hz, 1H), of 6.96 (m, 1H), 7,15 (d-like, 2H), 7,22-7,29 (m, 2H), 7,68 (d-like, 2H), 12,88 (user., 1H)
II-80(DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), with 2.93 (t, 4H), 3.43 points (t, 4H), 4,74 (m, 1H), a 4.83 (s, 2H), 6,50 (d, 1H), is 6.54 (DD, 1H, J=8,1, 1.8 Hz), 7,13 (d, 2H, J=8.7 Hz), 7,44 (d, 1H, J=8.7 Hz), the 7.65 (d, 1H).
II-81(DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), 2.95 and (t, 4H), to 3.38 (t, 4H), 4,74 (m, 1H), 4,79 (s, 2H), 6,50 (d, 1H), 6,55 (DD, 1H, J=8.7 Hz), 7,13 (d, 2H, J=9.0 Hz), 7,32 (user., 1H), to 7.67 (d, 2H), to 7.77 (d, 1H), 8,01 (user., 1H).
II-82(DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), 2,78 (d, 3H, 4.5 Hz), 2.95 and (t, 4H), to 3.35 (t, 4H), 4,74 (m, 1H), to 4.81 (s, 2H), 6,50 (d, 1H, J=2.1 Hz), 6,56 (DD, 1H, J=9,0, 2,1 Hz), 7,13 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H), of 7.75 (d, 1H), 8,54 (d, 1H).
II-83(DMSO-d6) to 0.88 (t, 3H, J=7.2 Hz), of 1.29 (d, 6H, J=6.0 Hz), and 1.54 (m, 2H), 2.95 and (t, 4H), to 3.36 (t, 4H), 4,74 (m, 1H), 4,80 (s, 2H), 6,51 (d, 1H), 6,56 (DD, 1H, J=8,4, and 2.1 Hz), 7,13 (d, 2H, J=8.7 Hz), 7,66 (d, 2H), 7,76 (d, 1H), 8,58 (t, 1H).
II-84(DMSO-d6) of 1.29 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3.33 and (users, 4H), 4,70-4,78 (m, 3H), 6,59-of 6.61 (m, 2H), 7,14 (d, J=9.0 Hz, 2H), 7,52 (d, J=9.0 Hz, 1H), to 7.67 (d, J=9.0 Hz, 2H), 7,74 (s, 1H), 8,29 (s, 1H)
II-85(DMSO-d6) of 1.32 (d, J=6.0 Hz, 6H), 3,05 (users, 4H), 3,32 (users, 4H), 4,79 (s, 2H), and 5.30-of 5.40 (m, 1H), 6,61-6,63 (m, 2H),of 6.96 (d, J=8.7 Hz, 1H), 7,52 (d, J=8.7 Hz, 1H), 7,73 (s, 1), of 8.00 (DD, J=2.7, and 8.7 Hz, 1H), 8,29 (s, 1H), 8,55 (d, J=2.4 Hz, 1H), 13,11 (users, 1H)
II-86(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), 4,58 with 4.65 (m, 1H), return of 6.58 (d, 1H, J=15,5 Hz), 6,70-of 6.90 (m, 3H), of 6.96 (d, 2H, J=8.5 Hz), to 7.61 (d, 2H, J=8.5 Hz), 8,96 (d, 1H, J=15,5 Hz).
II-87(CDCl3) to 1.37 (d, 6H, J=6.0 Hz), 3,18-up 3.22 (m, 8H), 4,58 with 4.65 (m, 1H), 5,10 (s, 2H), return of 6.58 (d, 1H, J=15,5 Hz), 6,70-of 6.90 (m, 3H), of 6.96 (d, 2H, J=8.5 Hz), 7,30-7,40 (m, 5H), 7,81 (d, 2H, J=8.5 Hz), 8,96 (d, 1H, J=15,5 Hz).
II-88(DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), of 2.97 (t, 4H), to 3.41 (t, 4H), 4,74 (m, 1H), 4,91 (s, 2H), only 6.64 (d, 1H), of 6.68 (DD, 1H, J=9.0 Hz), 7,14 (d, 2H, J=9.0 Hz), to 7.67 (d, 2H), 8,14 (d, 1H), 9,49 (s, 1H),
II-89(DMSO-d6) of 0.55 (m, 2H), of 0.68 (m, 2H), of 1.29 (d, 6H, J=6.3 Hz), 2,90 (t, 4H), 3,37 (t, 4H), 4,74 (m, 1H), amounts to 4.76 (s, 2H), 6.48 in (d, 1H, J=1.8 Hz), 6,56 (DD, 1H, J=9.0 Hz), 7,13 (d, 2H, J=8.7 Hz), 7,66 (d, 2H), to 7.77 (d, 1H), 8,61 (d, 1H, J=4,8 Hz).
II-90(DMSO-d6) of 1.28 (d, J=6.0 Hz, 6H), 2,88 (users, 4H), 3,53 (users, 4H), 4,66 was 4.76 (m, 3H), 6,30 (d, J=8,4 Hz, 1H), to 7.09 (d, J=9.0 Hz, 2H), to 7.64 (d, J=9,0 Hz, 3H)

Table 37
No. of connections1H-NMR (Solvent) δ
II-91(DMSO-d6) of 1.29 (d, J=6.0 Hz, 6H), of 2.50 (s, 3H), 2,94 (ush the D.C, 4H), 3,42 (users, 4H), 4,70-4,79 (m, 3H), of 6.45 (d, J=2.4 Hz, 1H), of 6.52 (DD, J=2,4, and 8.4 Hz, 1H), 7,13 (d, J=9.0 Hz, 2H), 7,55 (d, J=9.0 Hz, 1H), 7,66 (d, J=8.7 Hz, 2H), 13,07 (users, 1H)
II-92(DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), of 2.97 (t, 4H), to 3.38 (t, 4H), 4,74 (m, 1H), is 4.93 (s, 2H), is 6.61 (d, 1H), only 6.64 (DD, 1H, J=9.3 Hz), 7,14 (d, 2H, J=9.0 Hz), 7,63-of 7.69 (m, 3H), 7,83 (d, 1H, J=3.0 Hz), 8,08 (d, 1H).
II-93(DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), 2.95 and (t, 4H), 3,23 (s, 3H), 3.43 points (t, 4H), 4,74 (m, 1H), a 4.86 (s, 2H), 6,54-6,59 (m, 2H), of 6.68 (DD, 1H, J=9.0 Hz), 7,14 (d, 2H, J=9.0 Hz), 7,54 (d, 1H, J=9.3 Hz), to 7.67 (d, 2H),
II-94(DMSO-d6) of 1.32 (d, J=6.3 Hz, 6H), 3,05 (users, 4H), 3,39 (users, 4H), 4,82 (s, 2H), from 5.29 is 5.38 (m, 1H), 6,59 (s, 1H), only 6.64 (d, J=8,4 Hz, 1H), of 6.96 (d, J=8.7 Hz, 1H), 7,37 (s, 1H), 7,69 (d, J=9.0 Hz, 1H), 8,00 (DD, J=2.7, and 8.7 Hz, 1H), 8,13 (s, 1H), 8,55 (d, J=2.7 Hz, 1H)
II-951H NMR (DMSO-d6) of 1.30 (d, J=6.0 Hz, 6H), 2,97 (users, 4H), 3,25 (users, 4H), 4,70-4,80 (m, 3H), 6,41(s, 1H), to 6.57 (d, 1H), 6,66 (s, 1H), 7,14 (d, J=8.7 Hz, 2H), 7,47 (d, J=8,4 Hz, 1H), to 7.61 (s, 1H), to 7.67 (d, J=to 8.7 Hz, 2H), at 8.36 (s, 1H)
II-961H NMR (DMSO-d6) of 1.29 (d, J=6.0 Hz, 6H), 2,96 (users, 4H), 3,26 (users, 4H), 4,30 (s, 2H), 4,69-of 4.77 (m, 1H), 6,50 (s, 1H), 6,53 (d, J=9.0 Hz, 1H), 7,12 (d, J=8.7 Hz, 2H), 7,65 (d, J=9.0 Hz, 2H), 7,78 (d, J=8.7 Hz, 1H), 8,31 (s, 1H), 9,13 (s, 1H)
II-991H NMR (CDCl3) of 1.36 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), 4,58 with 4.65(m, 1H), 4,69 (s, 2H), 4,78 (d, 2H, J=6.0 Hz), 6,24 (s, 1H), of 6.52 (d, 1H, J=8.5 Hz), 6.87 in-6,91 (m, 1H), of 6.96 (d, 2H, J=8.5 Hz), of 6.96-6,98 (m, 1H), 7,14 (d, 1H, J=8.5 Hz), to 7.68 (d, 2H, J=8.5 Hz), of 7.90 (d, 1H, J=8.5 Hz), 8.30 to-8,35 (m, 1H).
II-1001H NMR (DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), 4,55 (d, 2H, J=6.0 Hz), 4,74-4,84 (m, 1H), 4,79 (s, 2H), 6,53 (s, 1H), return of 6.58 (d, 1H, J=8.5 Hz), 7,14 (d, 2H, J=8.5 Hz), 7,20-7,24 (m, 1H), 7,32 (d, 1H, J=8.5 Hz), to 7.64 (d, 2H, J=8.5 Hz), 7,69-7,72 (m, 1H), 7,79 (d, 1H, J=8.5 Hz), 8,48 (d, 1H, J=4.5 Hz), of 9.30-9,35 (m, 1H).

II-105
Table 38
No. of connections1H-NMR (Solvent) δ
II-1011H NMR (DMSO-d6) of 1.30 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), 4,35 (s, 2H), 4,74-4,84 (m, 1H), 6,12 (d, 1H, J=8.5 Hz), 6,53 (s, 1H), 6,58-6,70 (m, 2H), 7,00 (t, 1H, J=7,6 Hz), 7,13 (t, 1H, J=7,6 Hz), to 7.15 (d, 2H, J=8.5 Hz), 7,28 (d, 1H, J=7,6 Hz), to 7.64 (d, 2H, J=8.5 Hz).
II-1021H-NMR (DMSO-d6) 8,13 (1H, d, J=0.8 Hz), to 7.67 (2H, d, J=8,9 Hz), 7,51 (1H, DD, J=8,2, 1.8 Hz), 7,30-7,30 (2H, m), to 7.15 (2H, d, J=9.0 Hz), 7,01 (1H, d, J=8,4 Hz), 4,77-of 4.75 (3H, m), 3,19-and 3.16 (4H, m), 3,02-2,99 (4H, m)is 1.31 (6H, d, J=6.0 Hz).
II-1031H-NMR (CDCl3) to 1.38 (6H, d, J=6,1 Hz), 3,20 (8H, s), 4,51 (2H, s), br4.61-4,69 (1H, m), 6,56 (1H, s), to 6.67 (1H, d, J=9.0 Hz), 6,98 (2H, d, J=8,9 Hz), 7,11 (1H, d, J=9.0 Hz), 7,69 (2H, d, J=8,9 Hz).
1H-NMR (CDCl3) 8,04 (0,5H, C), a 7.85 (1H, d, J=8.7 Hz), 7,73 (2H, d, J=8,9 Hz), 7,01 (2H, d, J=8,9 Hz), 6,64-of 6.61 (1H, m), 4,78 (2H, s), 4,71-4,63 (1H, m), 4,12-Android 4.04 (1H, m), 3,42-of 3.32 (6H, m), 3,23 (4H, users), of 1.41 (6H, d, J=6.0 Hz), of 1.26 (6H, d, J=6.0 Hz), 1,14-of 1.07 (1H, m), 0,58-of 0.53 (2H, m), 0,32-0,24 (2H, m).
II-1061H NMR (DMSO-d6) of 1.29 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), of 4.45 (d, 2H, J=6.0 Hz), 4,74-4,84 (m, 1H), to 4.81 (s, 2H), from 6.22 (d, 1H, J=2.3 Hz), 6,32 (d, 1H, J=2.3 Hz), 6,50 (s, 1H), return of 6.58 (d, 1H, J=8.5 Hz), 7,14 (d, 2H, J=8.5 Hz), 7,52 (d, 1H, J=2.3 Hz), to 7.64 (d, 2H, J=8.5 Hz), 7,76 (d, 1H, J=8.5 Hz), 8,90-8,95 (m, 1H).
II-1081H-NMR (DMSO-d6) of 1.29 (6H, d, J=6.0 Hz), 2,96 (4H, m), of 3.48 (4H, m), 4,74 (1H, TT, J=6,0, 6,0 Hz), 4,96 (2H, s), 6,60 (1H, d, J=2.1 Hz), of 6.66 (1H, d, J=2,1, 9.0 Hz), 7,13 (2H, d, J=9.0 Hz), 7,22 (1H, d, J=3.6 Hz), 7,47 (1H, d, J=3.6 Hz), 7,66 (2H, d, J=9.0 Hz), to 7.84 (1H, d, J=9.0 Hz), to 11.56 (1H, users).
II-1091H-NMR (DMSO-d6) of 1.29 (6H, d, J=6.0 Hz), 2,95 (4H, m), 3,39 (4H, m), 4,74 (1H, TT, J=6,0, 6,0 Hz), of 4.77 (2H, s), 6,47 (1H, d, J=2.4 Hz), is 6.54 (1H, d, J=2,4, and 9.0 Hz), 7,13 (2H, d, J=9.0 Hz), a 7.62 (1H, d, J=9,0 Hz), 7,66 (2H, d, J=9.0 Hz), and 11.8 (1H, usher.), 13,0 (1H, usher.).
II-1101H-NMR (DMSO-d6) of 1.28 (6H, d, J=6.0 Hz), 2,96 (4H, m), 3,50 (4H, m), to 4.73 (1H, TT, J=6,0, 6,0 Hz), 4,96 (2H, s), is 6.61 (1H, d, J=2.1 Hz), to 6.67 (1H, DD, J=2,1, 9.0 Hz), 7,13 (2H, d, J=9.0 Hz), to 7.67 (2H, d, J=9,0 Hz), to 7.84 (1H, d, J=9.0 Hz), 9,16 (1H, s), 11,88 (1H, users), and 13.5 (1H, usher.).

Table 39
No. of connections1H-NMR (Solvent) δ, or [M+H]+
II-1111H-NMR (DMSO-d6) of 1.28 (6H, d, J=6.0 Hz), 2,96 (4H, m), 3,42 (4H, m), of 3.73 (3H, s), 4,74 (1H, TT, J=6,0, 6,0 Hz), is 4.93 (2H, s), is 6.54 (1H, d, J=2.4 Hz), to 6.57 (1H, d, J=2.4 Hz), is 6.61 (1H, DD, J=2,4, and 9.0 Hz), 7,13 (2H, d, J=9.0 Hz), 7,55 (1H, d, J=2.4 Hz), to 7.67 (2H, d, J=9.0 Hz), 7,81 (1H, d, J=9.0 Hz), 10,32 (1H, s), 13,35 (1H, users).
II-1121H NMR (DMSO-d6) was 0.63 and 0.68 (m, 2H), from 0.88 to 0.92 (m, 2H), of 1.30 (d, 6H, J=6.0 Hz), 1.93 and is 1.96 (m, 1H), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), 4,74-4,84 (m, 1H), 4,90 (s, 2H), 6,18 (s, 1H), 6,53 (s, 1H), return of 6.58 (d, 1H, J=8.5 Hz), 7,14 (d, 2H, J=8.5 Hz), to 7.64 (d, 2H, J=8.5 Hz), 7,79 (d, 1H, J=8.5 Hz), 9,80-9,85 (m, 1H).
II-1131H-NMR (CDCl3) of 7.69 (2H, d, J=6.9 Hz), 7,07 (1H, d, J=9.0 Hz), 6,97 (2H, d, J=6.9 Hz), is 6.54 (2H, d, J=6,7 Hz), of 4.77 (2H, s), 4,67-4,59 (1H, m), 3.72 points-of 3.60 (4H, m), 3,35-to 3.33 (4H, m), 3,18-and 3.16 (4H, m)to 1.38 (6H, d, J=6,1 Hz).
II-1141H-NMR (CDCl3) 7,73 (2H, d, J=8,9 Hz), 7,25 (1H, d, J=9.1 Hz), 7,02 (2H, d, J=8,9 Hz), 6,60 (2H, s), 4,82 (2H, s), 4.72 in with 4.64 (1H, m), 3,71 (4H, m), 3,40-to 3.38 (4H, m), 3,24-up 3.22 (4H, m)to 1.99 (4H, m)of 1.42 (6H, d, J=6,0 Hz).
II-1151H-NMR (CDCl3) 7,73 (2H, d, J=9.4 Hz), 7,16 (1H, d, J=9.1 Hz), 7,02 (2H, d, J=8,9 Hz), 6,59-to 6.57 (2H, m), to 4.81 (2H, s), 4.72 in with 4.64 (1H, m), 3,40-to 3.38 (4H, m), 3,22-3,17 (10H, m)of 1.42 (6H, d, J=6.0 Hz).
II-116[M+H]+ =494
II-117[M+H]+ =480
II-1181H NMR (CDCl3) of 1.36 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), 4,58 with 4.65 (m, 1H), 4,78 (s, 2H), 6.42 per (s, 1H), 6,45 (d, 1H, J=8.5 Hz), of 6.96 (d, 2H, J=8.5 Hz), 7,32 (d, 1H, J=8.5 Hz), 7,44 (t, 2H, J=8.0 Hz,), 7,60 (t, 1H, J=8.0 Hz), 7,74 (d, 2H, J=8.5 Hz), 7,79 (d, 2H, J=8.0 Hz).

Table 40
No. of connections1H-NMR (Solvent) δ, or [M+H]+
II-1221H NMR (CDCl3) of 1.36 (d, 6H, J=6.0 Hz), 3,15-to 3.35 (m, 8H), of 3.94 (s, 2H), to 4.52 (s, 2H), 4,60-of 4.66 (m, 1H), 6.42 per (s, 1H), 6,45 (d, 1H, J=8.5 Hz), of 6.96 (d, 2H, J=8.5 Hz), was 7.08 (d, 1H, J=8.5 Hz), 7,16-7,30 (m, 5H), 7,74 (d, 2H, J=8.5 Hz), of 7.70 (d, 2H, J=8.0 Hz).
II-1231H NMR (CDCl3) of 1.36 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), br4.61-of 4.67 (m, 1H), 4,78 (s, 2H), 6,45 (s, 1H), of 6.52 (d, 1H, J=8.5 Hz), 6,97 (d, 2H, J=8.5 Hz), to 7.15 (t, 1H, J=4.0 Hz), 7,56 (d, 2H, J=8,5 Hz), 7,60 (s, 1H), 7,74 (d, 2H, J=8.5 Hz), of 7.70 (d, 2H, J=4.0 Hz).
II-1271H-NMR (CDCl3) 8,09 (0,5H, s), 7,80-of 7.69 (4H, m), EUR 7.57-7,52 (1H, m), 7,45-7,39 (3H, m), 7,00 (2H, d, J=8,9 Hz), 6,59 (1H, d, J=10.0 Hz), to 6.39 (1H, s), 4,68 with 4.64 (1H, m), 4,36 (2H, s), 3,23 (8H, user. C)of 1.41 (6H, d, J=60 Hz).
II-128[M+H]+ =440
II-1291H NMR (CDCl3) of 1.36 (d, 6H, J=6.0 Hz), is 3.08-3.15 in (m, 4H), of 3.25 to 3.35 (m, 4H), br4.61-of 4.67 (m, 1H), amounts to 4.76 (s, 2H), 6,40 (s, 1H), of 6.52 (d, 1H, J=8.5 Hz), of 6.65 (d, 1H, J=4.0 Hz), 6,97 (d, 2H, J=8.5 Hz), 7,20 (d, 2H, J=4.0 Hz), 7,60-of 7.70 (m, 3H).
II-1301H-NMR (DMSO-d6) 10,48 (1H, s), the 7.65 (2H, d, J=8.5 Hz), 7,14 (2H, d, J=8,4 Hz), 6,72 (1H, d, J=7.8 Hz), 6,53-of 6.49 (2H, m), 4,79-4,71 (1H, m), 4,48 (2H, s), 3,12-to 3.09 (4H, m), 2,96-of 2.93 (4H, m)of 1.30 (6H, d, J=6,1 Hz).
II-1311H-NMR (CDCl3) 7,76-7,71 (2H, m), 7,53-7,51 (1H, m), 7.03 is-7,00 (2H, m), 6,66 (2H, dt, J=5.0 and 2.6 Hz), 4,74-to 4.62 (1H, m), of 4.57 (2H, s), 3,55 (3H, s), 3,31-up 3.22 (8H, m)of 1.42 (6H, d, J=6.0 Hz).
II-1331H-NMR (DMSO-d6) 8,31 (0,5H, s), 7,66 (2H, d, J=8,9 Hz), 7,14 (2H, d, J=8,9 Hz), 7,03 (1H, d, J=8.7 Hz), to 6.58 (1H, d, J=2.6 Hz), 6,50 (1H, DD, J=8,8, 2.4 Hz), 4,79-4,71 (1H, m), 4,48 (2H, s), 3,19-3,17 (4H, m), 2,97-to 2.94 (4H, m), 2,85 (3H, s)of 1.30 (6H, d, J=6.0 Hz).
II-134[M+H]+ =459
II-135[M+H]+ =479

Tablica 41
No. of connections1H-NMR (Solvent) δ, or [M+H]+
II-1401H NMR (CDCl3) to 1.37 (d, J=6.0 Hz, 6H), 3,23 (users, 4H), 3,37 (users, 4H), 4.09 to (users, 2H), 4,63 (m, 1H), 6,16 (users, 1H), 6,39 (m, 1H), 6,97 (d, J=9.0 Hz, 2H), 7,19 (s, 1H), 7,60 (s, 1H), 7,69 (d, J=9.0 Hz, 2H), 7,80 (d, J=9,0 Hz, 1H)
II-1411H-NMR (CDCl3) to 1.37 (6H, d, J=6.0 Hz), 3,06-3,19 (8H, m), 3,40-of 3.46 (4H, m), 3,69 of 3.75 (4H, m), 4,59-of 4.67 (1H, m), 4,70 (2H, s), 6,27 (1H, d, J=1.9 Hz), 6,53 (1H, DD, J=8,9, 1.9 Hz), 6,98 (2H, d, J=8,8 Hz), 7,63 (1H, d, J=8,9 Hz), 7,69 (2H, d, J=8,8 Hz).
II-1421H-NMR (DMSO-d6) of 1.33 (6H, d, J=5.8 Hz), 2,96-to 3.02 (4H, m), 3,11 -, and 3.16 (4H, m), 4,59 (2H, s), to 4.62 (2H, s), 4.72 in-4,84 (1H, m), 6,56 (1H, DD, J=8,8, 2.2 Hz), to 6.67 (1H, d, J=2.2 Hz), make 6.90 (1H, d, J=8,8 Hz), 7,17 (2H, d, J=8,8 Hz), of 7.70 (2H, d, J=8,8 Hz).
II-143[M+H]+ =492

In addition, similarly to the above-described method can be obtained the compounds shown in tables 42-47.

Similarly as described above can be obtained the compounds of formula (IA):

where Z1mean CR2Bor N; Z2mean CR4Bor N; R2B, R2C, R2Dand R2Eindependently mean a hydrogen atom, ATO is fluorine, the chlorine atom, bromine atom, methyl, ethyl, allyl, propargyl, trifluoromethyl, metiloksi, deformations, methylthio, methylsulphonyl, phenyl, phenoxy, phenylthio, amino, methylamino, dimethylamino, methylcobalamine, methylsulfonylamino, nitro, cyano, methylcarbamyl, N-methylcarbamoyl, N-phenylcarbamoyl, 2-furyl, 2-Tennille, 2-pyridyl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, 1,3-thiazol-2-yl, 1,3-the thiazol-4-yl, 1,3-thiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazole-2-yl, imidazol-1-yl, pyrazole-1-yl, morpholino, pyrrolidino or piperidino; R3means metiloksi, acyloxy, isopropoxy, sec-Butylochka, deformations, 1 phenylethylene, phenoxy, methylthio, ethylthio, isopropylthio, sec-butylthio, deformality, 1 feniletilic or phenylthio; R4A, R4B, R4Cand R4Dindependently mean a hydrogen atom, fluorine atom, chlorine atom, methyl or metiloksi; L3means of a simple bond, methylene, 1,1-dimethylmethylene, ethylene, -CH=CH-CH2-, 1-propene-1,3-dienyl, -O-CH2-, -O-CH(Me)-, -O-C(Me)2-, -S-CH2- or-NH-CH2-.

The combination of elements Z1, R2C, R2Dand R2E(part a) are shown in tables 48-53. -L3-COOH (part C) are shown in table 54. The combination of elements of R4A, Z2, R4C, R4D(part C) are shown in tables 55-60.

Table 48
No.Z1R2CR2DR2E
A-1SNNNN
A-2SNFNN
A-3SNClNN
A-4SNBrNN
A-5SNMeNN
A-6SNEtNN
A-7SNallylNN
A-8 SNpropargylNN
A-9SNCF3NN
A-10SNOMeNN
A-11SNOCHF2NN
A-12SNSMeNN
A-13SNSO2MeNN
A-14SNPhNN
A-15SNOPhNN
A-16SNSPh NN
A-17SNNH2NN
A-18SNNHMeNN
A-19SNNMe2NN
A-20SNNHCOMeNN
A-21SNNHSO2MeNN
A-22SNNO2NN
A-23SNCNNN
A-24SNCOMeNN
A-25SNCONHMeNN
A-26SNCONHPhNN
A-27SN2-furylNN
A-28SN2-thienylNN
A-29SN2-pyridylNN
A-30SN1,3-oxazol-2-ylNN
A-31SN1,3-oxazol-4-ylNN
A-32SN1,3-oxazol-5-ylNN
A-33 SN1,3-thiazol-2-ylNN
A-34SN1,3-thiazol-4-ylNN
A-35SN1,3-thiazol-5-ylNN
A-36SN1,3,4-oxadiazol-2-ylNN
A-37SN1,3,4-thiadiazole-2-ylNN
A-38SNimidazol-1-ylNN
A-39SNpyrazole-1-ylNN
A-40SNmorpholinoNN
A-41 SNpyrrolidinoNN
A-42SNpiperidinoNN
A-43SNthe piperazine derivativesNN
A-44SNNFN
A-45SNNClN

Table 49
No.Z1R2CR2DR2E
A-46SNNBrN
A-47SNNMe N
A-48SNNEtN
A-49SNNallylN
A-50SNNpropargylN
A-51SNNCF3N
A-52SNNOMeN
A-53SNNOCHF2N
A-54SNNSMeN
A-55SNNSO2MeN
A-56 SNNPhN
A-57SNNOPhN
A-58SNNSPhN
A-59SNNNH2N
A-60SNNNMe2N
A-61SNNNHCOMeN
A-62SNNNHSO2MeN
A-63SNNNO2N
A-64SNN CNN
A-65SNNCOMeN
A-66SNNCONHMeN
A-67SNNCONHPhN
A-68SNN2-furylN
A-69SNN2-thienylN
A-70SNN2-pyridylN
A-71SNN1,3-oxazol-2-ylN
A-72SNN1,3-oxazol-4-ylN
A-73SNN1,3-oxazol-5-ylN
A-74SNN1,3-thiazol-2-ylN
A-75SNN1,3-thiazol-4-ylN
A-76SNN1,3-thiazol-5-ylN
A-77SNN1,3,4-oxadiazol-2-ylN
A-78SNN1,3,4-thiadiazole-2-ylN
A-79SNNimidazol-1-ylN
A-80SNNpyrazole-1-yl N
A-81SNNmorpholinoN
A-82SNNpyrrolidinoN
A-83SNNpiperidinoN
A-84SNNthe piperazine derivativesN
A-85SNNNF
A-86SNNNCl
A-87SNNNBr
A-88SNNNMe
A-89 SNNNEt
A-90SNNNallyl

N
Table 50
No.Z1R2CR2DR2E
A-91SNNNpropargyl
A-92SNNNCF3
A-93SNNNOMe
A-94SNNNOCHF2
A-95SNNN SMe
A-96SNNNSO2Me
A-97SNNNPh
A-98SNNNOPh
A-99SNNNSPh
A-100SNNNNH2
A-101SNNNNHMe
A-102SNNNNMe2
A-103SNNNNHCOMe
A-104 SNNNNHSO2Me
A-105SNNNNO2
A-106SNNNCN
A-107SNNNCOMe
A-108SNNNCONHMe
A-109SNNNCONHPh
A-110SNNN2-furyl
A-111SNNN2-thienyl
A-112SNN N2-pyridyl
A-113SNNN1,3-oxazol-2-yl
A-114SNNN1,3-oxazol-4-yl
A-115SNNN1,3-oxazol-5-yl
A-116SNNN1,3-thiazol-2-yl
A-117SNNN1,3-thiazol-4-yl
A-118SNNN1,3-thiazol-5-yl
A-119SNNN1,3,4-oxadiazol-2-yl
A-120SNN N1,3,4-thiadiazole-2-yl
A-121SNNNimidazol-1-yl
A-122SNNNpyrazole-1-yl
A-123SNNNmorpholino
A-124SNNNpyrrolidino
A-125SNNNpiperidino
A-126SNNNthe piperazine derivatives
A-127NClNN
A-128NBrN
A-129NOMeNN
A-130NNO2NN
A-131NCNNN
A-132NCONHMeNN
A-133N2-furylNN
A-134N2-thienylNN
A-135N1,3-oxazol-2-ylNN

Table 51
No.Z1R 2CR2DR2E
A-136N1,3-oxazol-4-ylNN
A-137N1,3-oxazol-5-ylNN
A-138N1,3-thiazol-2-ylNN
A-139N1,3-thiazol-4-ylNN
A-140N1,3-thiazol-5-ylNN
A-141N1,3,4-oxadiazol-2-ylNN
A-142N1,3,4-thiadiazole-2-ylNN
A-143N imidazol-1-ylNN
A-144Npyrazole-1-ylNN
A-145NmorpholinoNN
A-146NpyrrolidinoNN
A-147NpiperidinoNN
A-148Nthe piperazine derivativesNN
A-149N2-thienylNN
A-150N2-pyridylNN
A-151Nmorpholino NN
A-152NpyrrolidinoNN
A-153NpiperidinoNN
A-154SNClClN
A-155SNBrClN
A-156SNOMeClN
A-157SNNO2ClN
A-158SNCNClN
A-159SNCONHMeClN
A-160SN2-furylClN
A-161SN2-thienylClN
A-162SN1,3-oxazol-2-ylClN
A-163SN1,3-oxazol-4-ylClN
A-164SN1,3-oxazol-5-ylClN
A-165SN1,3-thiazol-2-ylClN
A-166SN1,3-thiazol-4-ylClN
A-167SN1,3-thiazol-5-ylClN
A-168SN1,3,4-oxadiazol-2-ylClN
A-169SN1,3,4-thiadiazole-2-ylClN
A-170SNimidazol-1-ylClN
A-171SNpyrazole-1-ylClN
A-172SNmorpholinoClN
A-173SNpyrrolidinoClN
A-174SNpiperidinoClN
A-175SNthe piperazine derivativesClN
A-176SNClClN
A-177SNBrClN
A-178SNOMeClN
A-179SNNO2Cl
A-180SNCNClN

Cl
Table 52
No.Z1R2CR2DR2E
A-181SNCONHMeClH
A-182SN2-furyl ClH
A-183SN2-thienylClH
A-184SN1,3-oxazol-2-ylClH
A-185SN1,3-oxazol-4-ylClH
A-186SN1,3-oxazol-5-ylClH
A-187SN1,3-thiazol-2-ylClH
A-188SN1,3-thiazol-4-ylClH
A-189SN1,3-thiazol-5-ylClH
A-190SN1,3,4-oxadiazol-2-yl ClH
A-191SN1,3,4-thiadiazole-2-ylClH
A-192SNimidazol-1-ylClH
A-193SNpyrazole-1-ylClH
A-194SNmorpholinoClH
A-195SNpyrrolidinoClH
A-196SNpiperidinoClH
A-197SNthe piperazine derivativesClH
A-198SNClN
A-199SNBrNCl
A-200SNOMeNCl
A-201SNNO2NCl
A-202SNCNNCl
A-203SNCONHMeNCl
A-204SN2-furylNCl
A-205SN2-thienylNCl
A-206SN1,3-oxazol-2-ylNCl
A-207 SN1,3-oxazol-4-ylNCl
A-208SN1,3-oxazol-5-ylNCl
A-209SN1,3-thiazol-2-ylNCl
A-210SN1,3-thiazol-4-ylNCl
A-211SN1,3-thiazol-5-ylNCl
A-212SN1,3,4-oxadiazol-2-ylNCl
A-213SN1,3,4-thiadiazole-2-ylNCl
A-214SNimidazol-1-ylNCl
A-215 SNpyrazole-1-ylNCl
A-216SNmorpholinoNCl
A-217SNpyrrolidinoNCl
A-218SNpiperidinoNCl
A-219SNthe piperazine derivativesNCl
A-220SNClIUN
A-221SNBrIUN
A-222SNOMeIUN
A-223SN NO2IUN
A-224SNCNIUN
A-225SNCONHMeIUN

Table 53
No.Z1R2CR2DR2E
A-226SN2-furylIUN
A-227SN2-thienylIUN
A-228SN1,3-oxazol-2-ylIUN
A-229SN1,3-oxazol-4-ylIU N
A-230SN1,3-oxazol-5-ylIUN
A-231SN1,3-thiazol-2-ylIUN
A-232SN1,3-thiazol-4-ylIUN
A-233SN1,3-thiazol-5-ylIUN
A-234SN1,3,4-oxadiazol-2-ylIUN
A-235SN1,3,4-thiadiazole-2-ylIUN
A-236SNimidazol-1-ylIUN
A-237SNpyrazole-1-ylN
A-238SNmorpholinoIUN
A-239SNpyrrolidinoIUN
A-240SNpiperidinoIUN
A-241SNthe piperazine derivativesIUN
A-242SNClNIU
A-243SNBrNIU
A-244SNOMeNIU
A-245SNNO2N IU
A-246SNCNNIU
A-247SNCONHMeNIU
A-248SN2-furylNIU
A-249SN2-thienylNIU
A-250SN1,3-oxazol-2-ylNIU
A-251SN1,3-oxazol-4-ylNIU
A-252SN1,3-oxazol-5-ylNIU
A-253SN1,3-thiazol-2-ylNIU
A-254SN1,3-thiazol-4-ylNIU
A-255SN1,3-thiazol-5-ylNIU
A-256SN1,3,4-oxadiazol-2-ylNIU
A-257SN1,3,4-thiadiazole-2-ylNIU
A-258SNimidazol-1-ylNIU
A-259SNpyrazole-1-ylNIU
A-260SNmorpholinoNIU
A-261SNpyrrolidinoN IU
A-262SN4-Me-1,3-oxazol-2-ylNIU
A-263SN5-Me-1,3-oxazol-4-ylNIU
A-264SN2-Me-1,3-oxazol-5-ylNIU
A-265SN4-Me-1,3-thiazol-2-ylNIU
A-266SN5-Me-1,3-thiazol-4-ylNIU
A-267SN2-Me-1,3-thiazol-5-ylNIU
A-268SN5-Me-1,3,4-oxadiazol-2-ylNIU
A-269SN5-Me-1,3,4-thiad the azole-2-yl NIU
A-270SN5-Me-1,3-oxazol-2-ylNIU

Table 54
No.L3-COOHNo.L3-COOH
In-1-COOHIn-2-CH2COOH
B-3- (Me)2COOHB-4-CH2CH2COOH
B-5-CH=CH-COOHB-6-C≡C-COOH
In-7-Och2COOHIn-8-OC(Me)2COOH
In-9-SCH2COOH-10-NHCH2COOH

Below shows the connection of the formula (IA):

(no connection, part a, part b, part C) (IA-1, A-1, B-7, C-15), (IA-2, A-1, B-7, C-52), (IA-3, A-1, B-10, C-15), (IA-4, A-1, B-10, C-52), (IA-5, A-2, B-7, C-15), (IA-6, A-2, B-7, C-52), (IA-7, A-2, B-10, C-15), (IA-8, A-2, B-10, C-52), (IA-9, A-3, B-7, C-15), (IA-10, A-3, B-7, C-52), (IA-11, A-3, B-10, C-15), (IA-12, A-3, B-10, C-52), (IA-13, A-4, B-7, C-15), (IA-14, A-4, B-7, C-52), (IA-15, A-4, B-10, C-15), (IA-16, A-4, B-10, C-52), (IA-17, A-5, B-7, C-15), (IA-18, A-5, B-7, C-52), (IA-19, A-5, B-10, C-15), (IA-20, A-5, B-10, C-52), (IA-21, A-6, B-7, C-15), (IA-22, A-6, B-7, C-52), (IA-23, A-6, B-10, C-15), (IA-24, A-6, B-10, C-52), (IA-25, A-7, B-7, C-15), (IA-26, A-7, B-7, C-52), (IA-27, A-7, B-10, C-15), (IA-28, A-7, B-10, C-52), (IA-29, A-8, B-7, C-15), (IA-30, A-8, B-7, C-52), (IA-31, A-8, B-10, C-15), (IA-32, A-8, B-10, C-52), (IA-33, A-9, B-7, C-15), (IA-34, A-9, B-7, C-52), (IA-35, A-9, B-10, C-15), (IA-36, A-9, B-10, C-52), (IA-37, A-10, B-7, C-15), (IA-38, A-10, B-7, C-52), (IA-39, A-10, B-10, C-15), (IA-40, A-10, B-10, C-52), (IA-41, A-11, B-7, C-15), (IA-42, A-11, B-7, C-52), (IA-43, A-11, B-10, C-15), (IA-44, A-11, B-10, C-52), (IA-45, A-12, B-7, C-15), (IA-46, A-12, B-7, C-52), (IA-47, A-12, B-10, C-15), (IA-48, A-12, B-10, C-52), (IA-49, A-13, B-7, C-15), (IA-50, A-13, B-7, C-52), (IA-51, A-13, B-10, C-15), (IA-52, A-13, B-10, C-52), (IA-53, A-14, B-7, C-15), (IA-54, A-14, B-7, C-52), (IA-55, A-14, B-10, C-15), (IA-56, A-14, B-10, C-52), (IA-57, A-15, B-7, C-15), (IA-58, A-15, B-7, C-52), (IA-59, A-15, B-10, C-15), (IA-60, A-15, B-10, C-52), (IA-61, A-16, B-7, C-15), (IA-62, A-16, B-7, C-52), (IA-63, A-16, B-10, C-15), (IA-64, A-16, B-10, C-52), (IA-65, A-17, B-7, C-15), (IA-66, A-17, B-7, C-52), (IA-67, A-17, B-10, C-15), (IA-68, A-17, B-10, C-52), (IA-69, A-18, B-7, C-15), (IA-70, A-18, B-7, C-52), (IA-71, A-18, B-10, C-15), (IA-72, A-18, B-10, C-52), (IA-73, A-19, B-7, C-15), (IA-74, A-19, B-7, C-52), (IA-75, A-19, B-10, C-15), (IA-76, A-19, B-10, C-52), (IA-77, A-20, B-7, C-15), (IA-78, A-20, B-7, C-52), (IA-79, A-20, B-10, C-15), (IA-80, A-20 B-10, C-52), (IA-81, A-21, B-7, C-15), (IA-82, A-21, B-7, C-52), (IA-83, A-21, B-10, C-15), (IA-84, A-21, B-10, C-52), (IA-85, A-22, B-7, C-15), (IA-86, A-22, B-7, C-52), (IA-87, A-22, B-10, C-15), (IA-88, A-22, B-10, C-52), (IA-89, A-23, B-7, C-15), (IA-90, A-23, B-7, C-52), (IA-91, A-23, B-10, C-15), (IA-92, A-23, B-10, C-52), (IA-93, A-24, B-7, C-15), (IA-94, A-24, B-7, C-52), (IA-95, A-24, B-10, C-15), (IA-96, A-24, B-10, C-52), (IA-97, A-25, B-7, C-15), (IA-98, A-25, B-7, C-52), (IA-99, A-25, B-10, C-15), (IA-100, A-25, B-10, C-52), (IA-101, A-26, B-7, C-15), (IA-102, A-26, B-7, C-52), (IA-103, A-26, B-10, C-15), (IA-104, A-26, B-10, C-52), (IA-105, A-27, B-7, C-15), (IA-106, A-27, B-7, C-52), (IA-107, A-27, B-10, C-15), (IA-108, A-27, B-10, C-52), (IA-109, A-28, B-7, C-15), (IA-110, A-28, B-7, C-52), (IA-111, A-28, B-10, C-15), (IA-112, A-28, B-10, C-52), (IA-113, A-29, B-7, C-15), (IA-114, A-29, B-7, C-52), (IA-115, A-29, B-10, C-15), (IA-116, A-29, B-10, C-52), (IA-117, A-30, B-7, C-15), (IA-118, A-30, B-7, C-52), (IA-119, A-30, B-10, C-15), (IA-120, A-30, B-10, C-52), (IA-121, A-31, B-7, C-15), (IA-122, A-31, B-7, C-52), (IA-123, A-31, B-10, C-15), (IA-124, A-31, B-10, C-52), (IA-125, A-32, B-7, C-15), (IA-126, A-32, B-7, C-52), (IA-127, A-32, B-10, C-15), (IA-128, A-32, B-10, C-52), (IA-129, A-33, B-7, C-15), (IA-130, A-33, B-7, C-52), (IA-131, A-33, B-10, C-15), (IA-132, A-33, B-10, C-52), (IA-133, A-34, B-7, C-15), (IA-134, A-34, B-7, C-52), (IA-135, A-34, B-10, C-15), (IA-136, A-34, B-10, C-52), (IA-137, A-35, B-7, C-15), (IA-138, A-35, B-7, C-52), (IA-139, A-35, B-10, C-15), (IA-140, A-35, B-10, C-52), (IA-141, A-36, B-7, C-15), (IA-142, A-36, B-7, C-52), (IA-143, A-36, B-10, C-15), (IA-144, A-36, B-10, C-52), (IA-145, A-37, B-7, C-15), (IA-146, A-37, B-7, C-52), (IA-147, A-37, B-10, C-15), (IA-148, A-37, B-10, C-52), (IA-149, A-38, B-7, C-15), (IA-150, A-38, B-7, C-52), (IA-151, A-38, B-10, C-15), (IA-152, A-38, B-10, C-52), (IA-153, A-39, B-7, C-15), (IA-154, A-39, B-7, C-52), (IA-155, A-39, B-10, C-15), (IA-156, A-39, B-10, C-52), (IA-157, A-40, B-7, C-15), (IA-158, A-40, B-7, C-52), (IA-159, A-40, B-10, C-15), (IA-160, A-40, B-10, C-52), (IA-161, A-41, B-7, C-15), (IA-162, A-41, B-7, C-52), (IA-163, A-41, B-10, C-15), (IA-164, A-41, B-10, C-52), (IA-165, A-42, B-7, C-15), (IA-166, A-42, B-7, C-52), (IA-167, A-42, B-10, C-15), (IA-168, A-42, B-10,C-52), (IA-169, A-43, B-7, C-15), (IA-170, A-43, B-7, C-52), (IA-171, A-43, B-10, C-15), (IA-172, A-43, B-10, C-52), (IA-173, A-44, B-7, C-15), (IA-174, A-44, B-10, C-15), (IA-175, A-45, B-7, C-15), (IA-176, A-45, B-10, C-15), (IA-177, A-46, B-7, C-15), (IA-178, A-46, B-10, C-15), (IA-179, A-47, B-7, C-15), (IA-180, A-47, B-10, C-15), (IA-181, A-48, B-7, C-15), (IA-182, A-48, B-10, C-15), (IA-183, A-49, B-7, C-15), (IA-184, A-49, B-10, C-15), (IA-185, A-50, B-7 C-15), (IA-186, A-50, B-10, C-15), (IA-187, A-51, B-7, C-15), (IA-188, A-51, B-10, C-15), (IA-189, A-52, B-7, C-15), (IA-190, A-52, B-10, C-15), (IA-191 A-53, B-7, C-15), (IA-192, A-53, B-10, C-15), (IA-193, A-54, B-7, C-15), (IA-194, A-54, B-10, C-15), (IA-195, A-55, B-7, C-15), (IA-196, A-55, B-10, C-15), (IA-197, A-56, B-7, C-15), (IA-198, A-56, B-10, C-15), (IA-199, A-57, B-7, C-15), (IA-200, A-57, B-10, C-15), (IA-201, A-58, B-7, C-15), (IA-202, A-58, B-10, C-15), (IA-203, A-59, B-7, C-15), (IA-204, A-59, B-10, C-15), (IA-205, A-60, B-7, C-15), (IA-206, A-60, B-10, C-15), (IA-207, A-61, B-7, C-15), (IA-208, A-61, B-10, C-15), (IA-209, A-62, B-7, C-15), (IA-210, A-62, B-10, C-15), (IA-211, A-63, B-7, C-15), (IA-212, A-63, B-10, C-15), (IA-213, A-64, B-7, C-15), (IA-214, A-64, B-10, C-15), (IA-215, A-65, B-7, C-15), (IA-216, A-65, B-10, C-15), (IA-217, A-66, B-7, C-15), (IA-218, A-66, B-10, C-15), (IA-219, A-67, B-7, C-15), (IA-220, A-67, B-10, C-15), (IA-221, A-68, B-7, C-15), (IA-222, A-68, B-10, C-15), (IA-223, A-69, B-7, C-15), (IA-224, A-69, B-10, C-15), (IA-225, A-70, B-7, C-15), (IA-226, A-70, B-10, C-15), (IA-227, A-71, B-7, C-15), (IA-228, A-71, B-10, C-15), (IA-229, A-72, B-7, C-15), (IA-230, A-72, B-10, C-15), (IA-231, A-73, B-7, C-15), (IA-232, A-73, B-10, C-15), (IA-233, A-74, B-7, C-15), (IA-234, A-74, B-10, C-15), (IA-235, A-75, B-7 C-15), (IA-236, A-75, B-10, C-15), (IA-237, A-76, B-7, C-15), (IA-238, A-76, B-10, C-15), (IA-239, A-77, B-7, C-15), (IA-240, A-77, B-10, C-15), (IA-241 A-78, B-7, C-15), (IA-242, A-78, B-10, C-15), (IA-243, A-79, B-7, C-15), (IA-244, A-79, B-10, C-15), (IA-245, A-80, B-7, C-15), (IA-246, A-80, B-10, C-15), (IA-247, A-81, B-7, C-15), (IA-248, A-81, B-10, C-15), (IA-249, A-82, B-7, C-15), (IA-250, A-82, B-10, C-15), (IA-251, A-83, B-7, C-15), (IA-252, A-83, B-10, C-15), (IA-253, A-84, B-7, C-15), (IA-254, A-84, B-10, C-15), (IA-255, A-85, B-7, C-15), (IA-256,A-85, B-10, C-15), (IA-257, A-86, B-7, C-15), (IA-258, A-86, B-10, C-15), (IA-259, A-87, B-7, C-15), (IA-260, A-87, B-10, C-15), (IA-261, A-88, B-7, C-15), (IA-262, A-88, B-10, C-15), (IA-263, A-89, B-7, C-15), (IA-264, A-89, B-10, C-15), (IA-265, A-90, B-7, C-15), (IA-266, A-90, B-10, C-15), (IA-267, A-91, B-7, C-15), (IA-268, A-91, B-10, C-15), (IA-269, A-92, B-7, C-15), (IA-270, A-92, B-10, C-15), (IA-271, A-93, B-7, C-15), (IA-272, A-93, B-10, C-15), (IA-273, A-94, B-7, C-15), (IA-274, A-94, B-10, C-15), (IA-275, A-95, B-7, C-15), (IA-276, A-95, B-10, C-15), (IA-277, A-96, B-7, C-15), (IA-278, A-96, B-10, C-15), (IA-279, A-97, B-7, C-15), (IA-280, A-97, B-10, C-15), (IA-281, A-98, B-7, C-15), (IA-282, A-98, B-10, C-15), (IA-283, A-99, B-7, C-15), (IA-284, A-99, B-10, C-15), (IA-285, A-100, B-7, C-15), (IA-286, A-100, B-10, C-15), (IA-287, A-101, B-7, C-15), (IA-288, A-101, B-10, C-15), (IA-289, A-102, B-7, C-15), (IA-290, A-102, B-10, C-15), (IA-291, A-103, B-7, C-15), (IA-292, A-103, B-10, C-15), (IA-293, A-104, B-7, C-15), (IA-294, A-104, B-10, C-15), (IA-295, A-105, B-7, C-15), (IA-296, A-105, B-10, C-15), (IA-297, A-106, B-7, C-15), (IA-298, A-106, B-10, C-15), (IA-299, A-107, B-7, C-15), (IA-300, A-107, B-10, C-15), (IA-301, A-108, B-7, C-15), (IA-302, A-108, B-10, C-15), (IA-303, A-109, B-7, C-15), (IA-304, A-109, B-10, C-15), (IA-305, A-110, B-7, C-15), (IA-306, A-110, B-10, C-15), (IA-307, A-111, B-7, C-15), (IA-308, A-111, B-10, C-15), (IA-309, A-112, B-7, C-15), (IA-310, A-112, B-10, C-15), (IA-311, A-113, B-7, C-15), (IA-312, A-113, B-10, C-15), (IA-313, A-114, B-7, C-15), (IA-314, A-114, B-10, C-15), (IA-315, A-115, B-7, C-15), (IA-316, A-115, B-10, C-15), (IA-317, A-116, B-7, C-15), (IA-318, A-116, B-10, C-15), (IA-319, A-117, B-7, C-15), (IA-320, A-117, B-10, C-15), (IA-321, A-118, B-7, C-15), (IA-322, A-118, B-10, C-15), (IA-323, A-119, B-7, C-15), (IA-324, A-119, B-10, C-15), (IA-325, A-120, B-7, C-15), (IA-326, A-120, B-10, C-15), (IA-327, A-121, B-7, C-15), (IA-328, A-121, B-10, C-15), (IA-329, A-122, B-7, C-15), (IA-330, A-122, B-10, C-15), (IA-331, A-123, B-7, C-15), (IA-332, A-123, B-10, C-15), (IA-333, A-124, B-7, C-15), (IA-334, A-124, B-10, C-15), (IA-335, A-125, B-7, C-15), (IA-336, A-125, B-10, C-15), (IA-337, A-126, B-7, C-15), (IA-338, A-126, B-10, C-15), (IA-339, A-127, B-7, C-15), (IA-340, A-127, B-10, C-15), (IA-341, A-128, B-7, -15), (IA-342, A-128, B-10, C-15), (IA-343, A-129, B-7, C-15), (IA-344, A-129, B-10, C-15), (IA-345, A-130, B-7, C-15), (IA-346, A-130, B-10, C-15), (IA-347, A-131, B-7, C-15), (IA-348, A-131, B-10, C-15), (IA-349, A-132, B-7, C-15), (IA-350, A-132, B-10, C-15), (IA-351, A-133, B-7, C-15), (IA-352, A-133, B-10, C-15), (IA-353, A-134, B-7, C-15), (IA-354, A-134, B-10, C-15), (IA-355, A-135, B-7, C-15), (IA-356, A-135, B-10, C-15), (IA-357, A-136, B-7, C-15), (IA-358, A-136, B-10 C-15), (IA-359, A-137, B-7, C-15), (IA-360, A-137, B-10, C-15), (IA-361, A-138, B-7, C-15), (IA-362, A-138, B-10, C-15), (IA-363, A-139, B-7, C-15), (IA-364 A-139, B-10, C-15), (IA-365, A-140, B-7, C-15), (IA-366, A-140, B-10, C-15), (IA-367, A-141, B-7, C-15), (IA-368, A-141, B-10, C-15), (IA-369, A-142, B-7, C-15), (IA-370, A-142, B-10, C-15), (IA-371, A-143, B-7, C-15), (IA-372, A-143, B-10, C-15), (IA-373, A-144, B-7, C-15), (IA-374, A-144, B-10, C-15), (IA-375, A-145, B-7, C-15), (IA-376, A-145, B-10, C-15), (IA-377, A-146, B-7, C-15), (IA-378, A-146, B-10, C-15), (IA-379, A-147, B-7, C-15), (IA-380, A-147, B-10, C-15), (IA-381, A-148, B-7, C-15), (IA-382, A-148, B-10, C-15), (IA-383, A-149, B-7, C-15), (IA-384, A-149, B-10, C-15), (IA-385, A-150, B-7, C-15), (IA-386, A-150, B-10, C-15), (IA-387, A-151, B-7, C-15), (IA-388, A-151, B-10, C-15), (IA-389, A-152, B-7, C-15), (IA-390, A-152, B-10, C-15), (IA-391, A-153, B-7, C-15), (IA-392, A-153, B-10, C-15), (IA-393, A-154, B-7, C-15), (IA-394, A-154, B-10, C-15), (IA-395, A-155, B-7, C-15), (IA-396, A-155, B-10, C-15), (IA-397, A-156, B-7, C-15), (IA-398, A-156, B-10, C-15), (IA-399, A-157, B-7, C-15), (IA-400, A-157, B-10, C-15), (IA-401, A-158, B-7, C-15), (IA-402, A-158, B-10, C-15), (IA-403, A-159, B-7, C-15), (IA-404, A-159, B-10, C-15), (IA-405, A-160, B-7, C-15), (IA-406, A-160, B-10, C-15), (IA-407, A-161, B-7, C-15), (IA-408, A-161, B-10 C-15), (IA-409, A-162, B-7, C-15), (IA-410, A-162, B-10, C-15), (IA-411, A-163, B-7, C-15), (IA-412, A-163, B-10, C-15), (IA-413, A-164, B-7, C-15), (IA-414 A-164, B-10, C-15), (IA-415, A-165, B-7, C-15), (IA-416, A-165, B-10, C-15), (IA-417, A-166, B-7, C-15), (IA-418, A-166, B-10, C-15), (IA-419, A-167, B-7, C-15), (IA-420, A-167, B-10, C-15), (IA-421, A-168, B-7, C-15), (IA-422, A-168, B-10, C-15), (IA-423, A-169, B-7, C-15), (IA-424, A-169, B-10, C-15), (IA-425, A-170, B-7, C-15), (IA-42, A-170, B-10, C-15), (IA-427, A-171, B-7, C-15), (IA-428, A-171, B-10, C-15), (IA-429, A-172, B-7, C-15), (IA-430, A-172, B-10, C-15), (IA-431, A-173, B-7, C-15), (IA-432, A-173, B-10, C-15), (IA-433, A-174, B-7, C-15), (IA-434, A-174, B-10, C-15), (IA-435, A-175, B-7, C-15), (IA-436, A-175, B-10, C-15), (IA-437, A-176, B-7, C-15), (IA-438, A-176, B-10, C-15), (IA-439, A-177, B-7, C-15), (IA-440, A-177, B-10, C-15), (IA-441, A-178, B-7, C-15), (IA-442, A-178, B-10, C-15), (IA-443, A-179, B-7, C-15), (IA-444, A-179, B-10, C-15), (IA-445, A-180, B-7, C-15), (IA-446, A-180, B-10, C-15), (IA-447, A-181, B-7, C-15), (IA-448, A-181, B-10, C-15), (IA-449, A-182, B-7, C-15), (IA-450, A-182, B-10, C-15), (IA-451, A-183, B-7, C-15), (IA-452, A-183, B-10, C-15), (IA-453, A-184, B-7, C-15), (IA-454, A-184, B-10, C-15), (IA-455, A-185, B-7, C-15), (IA-456, A-185, B-10, C-15), (IA-457, A-186, B-7, C-15), (IA-458, A-186, B-10, C-15), (IA-459, A-187, B-7, C-15), (IA-460, A-187, B-10, C-15), (IA-461, A-188, B-7, C-15), (IA-462, A-188, B-10, C-15), (IA-463, A-189, B-7, C-15), (IA-464, A-189, B-10, C-15), (IA-465, A-190, B-7, C-15), (IA-466, A-190, B-10, C-15), (IA-467, A-191, B-7, C-15), (IA-468, A-191, B-10, C-15), (IA-469, A-192, B-7, C-15), (IA-470, A-192, B-10, C-15), (IA-471, A-193, B-7, C-15), (IA-472, A-193, B-10, C-15), (IA-473, A-194, B-7, C-15), (IA-474, A-194, B-10, C-15), (IA-475, A-195, B-7, C-15), (IA-476, A-195, B-10, C-15), (IA-477, A-196, B-7, C-15), (IA-478, A-196, B-10, C-15), (IA-479, A-197, B-7, C-15), (IA-480, A-197, B-10, C-15), (IA-481, A-198, B-7, C-15), (IA-482, A-198, B-10, C-15), (IA-483, A-199, B-7, C-15), (IA-484, A-199, B-10, C-15), (IA-485, A-200, B-7, C-15), (IA-486, A-200, B-10, C-15), (IA-487, A-201, B-7, C-15), (IA-488, A-201, B-10, C-15), (IA-489, A-202, B-7, C-15), (IA-490, A-202, B-10, C-15), (IA-491, A-203, B-7, C-15), (IA-492, A-203, B-10, C-15), (IA-493, A-204, B-7, C-15), (IA-494, A-204, B-10, C-15), (IA-495, A-205, B-7, C-15), (IA-496, A-205, B-10, C-15), (IA-497, A-206, B-7, C-15), (IA-498, A-206, B-10, C-15), (IA-499, A-207, B-7, C-15), (IA-500, A-207, B-10, C-15), (IA-501, A-208, B-7, C-15), (IA-502, A-208, B-10, C-15), (IA-503, A-209, B-7, C-15), (IA-504, A-209, B-10, C-15), (IA-505, A-210, B-7, C-15), (IA-506, A-210, B-10, C-15), (IA-507, A-211, B-7, C-15), (IA-508, A-211, B-10, C-15), (IA-509, A-212, B-7, C-15), (IA-510, A-212,B-10, C-15), (IA-511, A-213, B-7, C-15), (IA-512, A-213, B-10, C-15), (IA-513, A-214, B-7, C-15), (IA-514, A-214, B-10, C-15), (IA-515, A-215, B-7, C-15), (IA-516, A-215, B-10, C-15), (IA-517, A-216, B-7, C-15), (IA-518, A-216, B-10, C-15), (IA-519, A-217, B-7, C-15), (IA-520, A-217, B-10, C-15), (IA-521, A-218, B-7, C-15), (IA-522, A-218, B-10, C-15), (IA-523, A-219, B-7, C-15), (IA-524, A-219, B-10, C-15), (IA-525, A-220, B-7, C-15), (IA-526, A-220, B-10, C-15), (IA-527, A-221, B-7, C-15), (IA-528, A-221, B-10, C-15), (IA-529, A-222, B-7, C-15), (IA-530, A-222, B-10, C-15), (IA-531, A-223, B-7, C-15), (IA-532, A-223, B-10, C-15), (IA-533, A-224, B-7, C-15), (IA-534, A-224, B-10, C-15), (IA-535, A-225, B-7, C-15), (IA-536, A-225, B-10, C-15), (IA-537, A-226, B-7, C-15), (IA-538, A-226, B-10, C-15), (IA-539, A-227, B-7, C-15), (IA-540, A-227, B-10, C-15), (IA-541, A-228, B-7, C-15), (IA-542, A-228, B-10, C-15), (IA-543, A-229, B-7, C-15), (IA-544, A-229, B-10, C-15), (IA-545, A-230, B-7, C-15), (IA-546, A-230, B-10, C-15), (IA-547, A-231, B-7, C-15), (IA-548, A-231, B-10, C-15), (IA-549, A-232, B-7, C-15), (IA-550, A-232, B-10, C-15), (IA-551, A-233, B-7, C-15), (IA-552, A-233, B-10, C-15), (IA-553, A-234, B-7, C-15), (IA-554, A-234, B-10, C-15), (IA-555, A-235, B-7, C-15), (IA-556, A-235, B-10, C-15), (IA-557, A-236, B-7, C-15), (IA-558, A-236, B-10, C-15), (IA-559, A-237, B-7, C-15), (IA-560, A-237, B-10, C-15), (IA-561, A-238, B-7, C-15), (IA-562, A-238, B-10, C-15), (IA-563, A-239, B-7, C-15), (IA-564, A-239, B-10, C-15), (IA-565, A-240, B-7, C-15), (IA-566, A-240, B-10, C-15), (IA-567, A-241, B-7, C-15), (IA-568, A-241, B-10, C-15), (IA-569, A-242, B-7, C-15), (IA-570, A-242, B-10, C-15), (IA-571, A-243, B-7, C-15), (IA-572, A-243, B-10, C-15), (IA-573, A-244, B-7, C-15), (IA-574, A-244, B-10, C-15), (IA-575, A-245, B-7, C-15), (IA-576, A-245, B-10, C-15), (IA-577, A-246, B-7, C-15), (IA-578, A-246, B-10, C-15), (IA-579, A-247, B-7, C-15), (IA-580, A-247, B-10, C-15), (IA-581, A-248, B-7, C-15), (IA-582, A-248, B-10, C-15), (IA-583, A-249, B-7, C-15), (IA-584, A-249, B-10, C-15), (IA-585, A-250, B-7, C-15), (IA-586, A-250, B-10, C-15), (IA-587, A-251, B-7, C-15), (IA-588, A-251, B-10, C-15), (IA-589, A-252, B-7, C-15), (IA-590, A-252, B-10, C-15), (IA-591, A-253, B-7, C-15), (IA-592, A-253, B-10, C-15), (IA-593, A-254, B-7, C-15), (IA-594, A-254, B-10, C-15),(IA-595, A-255, B-7, C-15), (IA-596, A-255, B-10, C-15), (IA-597, A-256, B-7, C-15), (IA-598, A-256, B-10, C-15), (IA-599, A-257, B-7, C-15), (IA-600, A-257, B-10, C-15), (IA-601, A-258, B-7, C-15), (IA-602, A-258, B-10, C-15), (IA-603, A-259, B-7, C-15), (IA-604, A-259, B-10, C-15), (IA-605, A-260, B-7, C-15), (IA-606, A-260, B-10, C-15), (IA-607, A-261, B-7, C-15), (IA-608, A-261, B-10, C-15), (IA-609, A-262, B-7, C-15), (IA-610, A-262, B-10, C-15), (IA-611, A-263, B-7, C-15), (IA-612, A-263, B-10, C-15), (IA-613, A-264, B-7, C-15), (IA-614, A-264, B-10, C-15), (IA-615, A-265, B-7, C-15), (IA-616, A-265, B-10, C-15), (IA-617, A-266, B-7, C-15), (IA-618, A-266, B-10, C-15), (IA-619, A-267, B-7, C-15), (IA-620, A-267, B-10, C-15), (IA-621, A-268, B-7, C-15), (IA-622, A-268, B-10, C-15), (IA-623, A-269, B-7, C-15), (IA-624, A-269, B-10, C-15), (IA-625, A-270, B-7, C-15), (IA-626, A-270, B-10, C-15)

Similarly to the above-described methods can be obtained compound of the formula (IB):

where Z1mean CR2Bor N; Z2mean CR4Bor N; R2B, R2C, R2Dand R2Eindependently mean a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, ethyl, allyl, propargyl, trifluoromethyl, metiloksi, deformations, methylthio, methylsulphonyl, phenyl, phenoxy, phenylthio, amino, methylamino, dimethylamino, methylcobalamine, methylsulfonylamino, nitro, cyano, 2-furyl, 2-thienyl, 2-pyridyl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazole-2-yl, imidazol-1-yl, pyrazole-1-yl, morpholino, pyrrolidino or piperidino; R3means metiloksi, acyloxy, isopropoxy, sec-Butylochka, deformity the XI, 1 phenylethylene, phenoxy, methylthio, ethylthio, isopropylthio, sec-butylthio, deformality, 1 feniletilic or phenylthio; R4A, R4B, R4Cand R4Dindependently mean a hydrogen atom, fluorine atom, chlorine atom, methyl or metiloksi; L3means of a simple bond, methylene, 1,1-dimethylmethylene, ethylene, -CH=CH-CH2-, 1-propene-1,3-dienyl, -O-CH2-, -O-CH(Me)-, -O-C(Me)2-, -S-CH2- or-NH-CH2-.

The following table indicating combinations of part a, part b and part C is similar to the table for compounds of formula (IA).

Below shows the connection of the formula (IB):

(no connection, part a, part b, part C) (IB-1, A-1, B-1, C-15), (IB-2, A-1, B-2, C-15), (IB-3, A-1, B-3, C-15), (IB-4, A-1, B-4, C-15), (IB-5, A-1, B-5, C-15), (IB-6, A-1, B-6, C-15), (IB-7, A-1, B-7, C-15), (IB-8, A-1, B-7, C-52), (IB-9, A-1, B-8, C-15), (IB-10, A-1, B-9, C-15), (IB-11, A-1, B-10, C-15), (IB-12, A-1, B-10, C-52), (IB-13, A-2, B-1, C-15), (IB-14, A-2, B-2, C-15), (IB-15, A-2, B-3, C-15), (IB-16, A-2, B-4, C-15), (IB-17, A-2, B-5, C-15), (IB-18, A-2, B-6, C-15), (IB-19, A-2, B-7, C-15), (IB-20, A-2, B-7, C-52), (IB-21, A-2, B-8, C-15), (IB-22, A-2, B-9, C-15), (IB-23, A-2, B-10, C-15), (IB-24, A-2, B-10, C-52), (IB-25, A-3, B-1, C-15), (IB-26, A-3, B-2, C-15), (IB-27, A-3, B-3, C-15), (IB-28, A-3, B-4, C-15), (IB-29, A-3, B-5, C-15), (IB-30, A-3, B-6, C-15), (IB-31, A-3, B-7, C-1), (IB-32, A-3, B-7, C-2), (IB-33, A-3, B-7, C-3), (IB-34, A-3, B-7, C-4), (IB-35, A-3, B-7, C-5), (IB-36, A-3, B-7, C-6), (IB-37, A-3, B-7, C-7), (IB-38, A-3, B-7, C-8), (IB-39, A-3, B-7, C-9), (IB-40, A-3, B-7, C-10), (IB-41, A-3, B-7, C-11), (IB-42, A-3, B-7, C-12), (IB-43, A-3, B-7, C-13), (IB-44, A-3, B-7, C-14), (IB-45, A-3, B-7, C-15), (IB-46, A-3, B-7, C-16), (IB-47, A-3, B-7, C-17), (IB-48, A-3, B-7, C-18), (IB-49, A-3, B-7, C-19), (IB-50, A-3, B-7, C-20), (IB-51, A-3, B-7, C-21), (IB-5, A-3, B-7, C-22), (IB-53, A-3, B-7, C-23), (IB-54, A-3, B-7, C-24), (IB-55, A-3, B-7, C-25), (IB-56, A-3, B-7, C-26), (IB-57, A-3, B-7, C-27), (IB-58, A-3, B-7, C-28), (IB-59, A-3, B-7, C-29), (IB-60, A-3, B-7, C-30), (IB-61, A-3, B-7, C-31), (IB-62, A-3, B-7, C-32), (IB-63, A-3, B-7, C-33), (IB-64, A-3, B-7, C-34), (IB-65, A-3, B-7, C-35), (IB-66, A-3, B-7, C-36), (IB-67, A-3, B-7, C-37), (IB-68, A-3, B-7, C-38), (IB-69, A-3, B-7, C-39), (IB-70, A-3, B-7, C-40), (IB-71, A-3, B-7, C-41), (IB-72, A-3, B-7, C-42), (IB-73, A-3, B-7, C-43), (IB-74, A-3, B-7, C-44), (IB-75, A-3, B-7, C-45), (IB-76, A-3, B-7, C-46), (IB-77, A-3, B-7, C-47), (IB-78, A-3, B-7, C-48), (IB-79, A-3, B-7, C-49), (IB-80, A-3, B-7, C-50), (IB-81, A-3, B-7, C-51), (IB-82, A-3, B-7, C-52), (IB-83, A-3, B-7, C-53), (IB-84, A-3, B-7, C-54), (IB-85, A-3, B-7, C-55), (IB-86, A-3, B-7, C-56), (IB-87, A-3, B-7, C-57), (IB-88, A-3, B-7, C-58), (IB-89, A-3, B-7, C-59), (IB-90, A-3, B-7, C-60), (IB-91, A-3, B-7, C-61), (IB-92, A-3, B-7, C-62), (IB-93, A-3, B-7, C-63), (IB-94, A-3, B-7, C-64), (IB-95, A-3, B-7, C-65), (IB-96, A-3, B-7, C-66), (IB-97, A-3, B-7, C-67), (IB-98, A-3, B-7, C-68), (IB-99, A-3, B-7, C-69), (IB-100, A-3, B-7, C-70), (IB-101, A-3, B-7, C-71), (IB-102, A-3, B-7, C-72), (IB-103, A-3, B-7, C-73), (IB-104, A-3, B-7, C-74), (IB-105, A-3, B-7, C-75), (IB-106, A-3, B-7, C-76), (IB-107, A-3, B-7, C-77), (IB-108, A-3, B-7, C-78), (IB-109, A-3, B-7, C-79), (IB-110, A-3, B-7, C-80), (IB-111, A-3, B-7, C-81), (IB-112, A-3, B-7, C-82), (IB-113, A-3, B-7, C-83), (IB-114, A-3, B-7, C-84), (IB-115, A-3, B-7, C-85), (IB-116, A-3, B-7, C-86), (IB-117, A-3, B-7, C-87), (IB-118, A-3, B-7, C-88), (IB-119, A-3, B-7, C-89), (IB-120, A-3, B-7, C-90), (IB-121, A-3, B-7, C-91), (IB-122, A-3, B-7, C-92), (IB-123, A-3, B-7, C-93), (IB-124, A-3, B-7, C-94), (IB-125, A-3, B-7, C-95), (IB-126, A-3, B-7, C-96), (IB-127, A-3, B-7, C-97), (IB-128, A-3, B-7, C-98), (IB-129, A-3, B-7, C-99), (IB-130, A-3, B-7, C-100), (IB-131, A-3, B-7, C-101), (IB-132, A-3, B-7, C-102), (IB-133, A-3, B-7, C-103), (IB-134, A-3, B-7, C-104), (IB-135, A-3, B-7, C-105), (IB-136, A-3, B-7, C-106), (IB-137, A-3, B-7, C-107), (IB-138, A-3, B-7, C-108), (IB-139, A-3, B-7, C-109), (IB-140, A-3, B-7, C-110), (IB-141, A-3, B-7, C-111), (IB-142, A-3, B-7, C-112), (IB-143, A-3, B-7, C-113), (IB-144, A-3, B-7, C-114), (IB-145, A-3, B-7, C-11), (IB-146, A-3, B-7, C-116), (IB-147, A-3, B-7, C-117), (IB-148, A-3, B-7, C-118), (IB-149, A-3, B-7, C-119), (IB-150, A-3, B-7, C-120), (IB-151, A-3, B-7, C-121), (IB-152, A-3, B-7, C-122), (IB-153, A-3, B-7, C-123), (IB-154, A-3, B-7, C-124), (IB-155, A-3, B-7, C-125), (IB-156, A-3, B-7, C-126), (IB-157, A-3, B-7, C-127), (IB-158, A-3, B-7, C-128), (IB-159, A-3, B-7, C-129), (IB-160, A-3, B-7, C-130), (IB-161, A-3, B-7, C-131), (IB-162, A-3, B-7 C-132), (IB-163, A-3, B-7, C-133), (IB-164, A-3, B-7, C-134), (IB-165, A-3, B-7, C-135), (IB-166, A-3, B-7, C-136), (IB-167, A-3, B-7, C-137), (IB-168 A-3, B-7, C-138), (IB-169, A-3, B-7, C-139), (IB-170, A-3, B-7, C-140), (IB-171, A-3, B-7, C-141), (IB-172, A-3, B-7, C-142), (IB-173, A-3, B-7, C-143), (IB-174, A-3, B-7, C-144), (IB-175, A-3, B-7, C-145), (IB-176, A-3, B-7, C-146), (IB-177, A-3, B-7, C-147), (IB-178, A-3, B-7, C-148), (IB-179, A-3, B-7, C-149), (IB-180, A-3, B-7, C-150), (IB-181, A-3, B-7, C-151), (IB-182, A-3, B-7, C-152), (IB-183, A-3, B-7, C-153), (IB-184, A-3, B-7, C-154), (IB-185, A-3, B-7, C-155), (IB-186, A-3, B-7, C-156), (IB-187, A-3, B-7, C-157), (IB-188, A-3, B-7, C-158), (IB-189, A-3, B-7, C-159), (IB-190, A-3, B-7, C-160), (IB-191, A-3, B-7, C-161), (IB-192, A-3, B-7, C-162), (IB-193, A-3, B-7, C-163), (IB-194, A-3, B-7, C-164), (IB-195, A-3, B-7, C-165), (IB-196, A-3, B-7, C-166), (IB-197, A-3, B-7, C-167), (IB-198, A-3, B-7, C-168), (IB-199, A-3, B-7, C-169), (IB-200, A-3, B-7, C-170), (IB-201, A-3, B-7, C-171), (IB-202, A-3, B-7, C-172), (IB-203, A-3, B-7, C-173), (IB-204, A-3, B-7, C-174), (IB-205, A-3, B-7, C-175), (IB-206, A-3, B-7, C-176), (IB-207, A-3, B-7, C-177), (IB-208, A-3, B-7, C-178), (IB-209, A-3, B-7, C-179), (IB-210, A-3, B-7, C-180), (IB-211, A-3, B-7, C-181), (IB-212, A-3, B-7 C-182), (IB-213, A-3, B-7, C-183), (IB-214, A-3, B-7, C-184), (IB-215, A-3, B-7, C-185), (IB-216, A-3, B-7, C-186), (IB-217, A-3, B-7, C-187), (IB-218 A-3, B-7, C-188), (IB-219, A-3, B-7, C-189), (IB-220, A-3, B-7, C-190), (IB-221, A-3, B-7, C-191), (IB-222, A-3, B-7, C-192), (IB-223, A-3, B-7, C-193), (IB-224, A-3, B-7, C-194), (IB-225, A-3, B-7, C-195), (IB-226, A-3, B-7, C-196), (IB-227, A-3, B-7, C-197), (IB-228, A-3, B-7, C-198), (IB-229, A-3, B-7, C-199), (IB-230, A-3, B-7, C-200), (IB-231, A-3, B-7, C-201), (IB-232, A-3, B-7, C-202), (IB-233, A-3, B-7, C-203), (IB-234, A-3, B-7, C-204, (IB-235, A-3, B-7, C-205), (IB-236, A-3, B-7, C-206), (IB-237, A-3, B-7, C-207), (IB-238, A-3, B-7, C-208), (IB-239, A-3, B-7, C-209), (IB-240, A-3, B-7, C-210), (IB-241, A-3, B-7, C-211), (IB-242, A-3, B-7, C-212), (IB-243, A-3, B-7, C-213), (IB-244, A-3, B-7, C-214), (IB-245, A-3, B-8, C-15), (IB-246, A-3, B-9, C-15), (IB-247, A-3, B-10, C-15), (IB-248, A-3, B-10, C-52), (IB-249, A-4, B-1, C-15), (IB-250, A-4, B-2, C-15), (IB-251, A-4, B-3 C-15), (IB-252, A-4, B-4, C-15), (IB-253, A-4, B-5, C-15), (IB-254, A-4, B-6, C-15), (IB-255, A-4, B-7, C-1), (IB-256, A-4, B-7, C-2), (IB-257 A-4, B-7, C-3), (IB-258, A-4, B-7, C-4), (IB-259, A-4, B-7, C-5), (IB-260, A-4, B-7, C-6), (IB-261, A-4, B-7, C-7), (IB-262, A-4, B-7, C-8), (IB-263, A-4, B-7, C-9), (IB-264, A-4, B-7, C-10), (IB-265, A-4, B-7, C-11), (IB-266, A-4, B-7, C-12), (IB-267, A-4, B-7, C-13), (IB-268, A-4, B-7, C-14), (IB-269, A-4, B-7, C-15), (IB-270, A-4, B-7, C-16), (IB-271, A-4, B-7, C-17), (IB-272, A-4, B-7, C-18), (IB-273, A-4, B-7, C-19), (IB-274, A-4, B-7, C-20), (IB-275, A-4, B-7, C-21), (IB-276, A-4, B-7, C-22), (IB-277, A-4, B-7, C-23), (IB-278, A-4, B-7, C-24), (IB-279, A-4, B-7, C-25), (IB-280, A-4, B-7, C-26), (IB-281, A-4, B-7, C-27), (IB-282, A-4, B-7, C-28), (IB-283, A-4, B-7, C-29), (IB-284, A-4, B-7, C-30), (IB-285, A-4, B-7, C-31), (IB-286, A-4, B-7, C-32), (IB-287, A-4, B-7, C-33), (IB-288, A-4, B-7, C-34), (IB-289, A-4, B-7, C-35), (IB-290, A-4, B-7, C-36), (IB-291, A-4, B-7, C-37), (IB-292, A-4, B-7, C-38), (IB-293, A-4, B-7, C-39), (IB-294, A-4, B-7, C-40), (IB-295, A-4, B-7, C-41), (IB-296, A-4, B-7, C-42), (IB-297, A-4, B-7, C-43), (IB-298, A-4, B-7, C-44), (IB-299, A-4, B-7, C-45), (IB-300, A-4, B-7, C-46), (IB-301, A-4, B-7 C-47), (IB-302, A-4, B-7, C-48), (IB-303, A-4, B-7, C-49), (IB-304, A-4, B-7, C-50), (IB-305, A-4, B-7, C-51), (IB-306, A-4, B-7, C-52), (IB-307 A-4, B-7, C-53), (IB-308, A-4, B-7, C-54), (IB-309, A-4, B-7, C-55), (IB-310, A-4, B-7, C-56), (IB-311, A-4, B-7, C-57), (IB-312, A-4, B-7, C-58), (IB-313, A-4, B-7, C-59), (IB-314, A-4, B-7, C-60), (IB-315, A-4, B-7, C-61), (IB-316, A-4, B-7, C-62), (IB-317, A-4, B-7, C-63), (IB-318, A-4, B-7, C-64), (IB-319, A-4, B-7, C-65), (IB-320, A-4, B-7, C-66), (IB-321, A-4, B-7, C-67), (IB-322, A-4, B-7, C-68), (IB-323, A-4, B-7, C-69), (IB-324, A-4, B-7, C-70), (IB-325, A-4, B-7, C-71), (IB-326, A-4, B-7, C-72), (IB-37, A-4, B-7, C-73), (IB-328, A-4, B-7, C-74), (IB-329, A-4, B-7, C-75), (IB-330, A-4, B-7, C-76), (IB-331, A-4, B-7, C-77), (IB-332, A-4, B-7, C-78), (IB-333, A-4, B-7, C-79), (IB-334, A-4, B-7, C-80), (IB-335, A-4, B-7, C-81), (IB-336, A-4, B-7, C-82), (IB-337, A-4, B-7, C-83), (IB-338, A-4, B-7, C-84), (IB-339, A-4, B-7, C-85), (IB-340, A-4, B-7, C-86), (IB-341, A-4, B-7, C-87), (IB-342, A-4, B-7, C-88), (IB-343, A-4, B-7, C-89), (IB-344, A-4, B-7, C-90), (IB-345, A-4, B-7, C-91), (IB-346, A-4, B-7, C-92), (IB-347, A-4, B-7, C-93), (IB-348, A-4, B-7, C-94), (IB-349, A-4, B-7, C-95), (IB-350, A-4, B-7, C-96), (IB-351, A-4, B-7, C-97), (IB-352, A-4, B-7, C-98), (IB-353, A-4, B-7, C-99), (IB-354, A-4, B-7, C-100), (IB-355, A-4, B-7, C-101), (IB-356, A-4, B-7, C-102), (IB-357, A-4, B-7, C-103), (IB-358, A-4, B-7, C-104), (IB-359, A-4, B-7, C-105), (IB-360, A-4, B-7, C-106), (IB-361, A-4, B-7, C-107), (IB-362, A-4, B-7, C-108), (IB-363, A-4, B-7, C-109), (IB-364, A-4, B-7, C-110), (IB-365, A-4, B-7, C-111), (IB-366, A-4, B-7, C-112), (IB-367, A-4, B-7, C-113), (IB-368, A-4, B-7, C-114), (IB-369, A-4, B-7, C-115), (IB-370, A-4, B-7, C-116), (IB-371, A-4, B-7, C-117), (IB-372, A-4, B-7, C-118), (IB-373, A-4, B-7, C-119), (IB-374, A-4, B-7, C-120), (IB-375, A-4, B-7, C-121), (IB-376, A-4, B-7, C-122), (IB-377, A-4, B-7, C-123), (IB-378, A-4, B-7, C-124), (IB-379, A-4, B-7, C-125), (IB-380, A-4, B-7, C-126), (IB-381, A-4, B-7, C-127), (IB-382, A-4, B-7, C-128), (IB-383, A-4, B-7, C-129), (IB-384, A-4, B-7, C-130), (IB-385, A-4, B-7, C-131), (IB-386, A-4, B-7, C-132), (IB-387, A-4, B-7, C-133), (IB-388, A-4, B-7, C-134), (IB-389, A-4, B-7, C-135), (IB-390, A-4, B-7, C-136), (IB-391, A-4, B-7, C-137), (IB-392, A-4, B-7, C-138), (IB-393, A-4, B-7, C-139), (IB-394, A-4, B-7, C-140), (IB-395, A-4, B-7, C-141), (IB-396, A-4, B-7, C-142), (IB-397, A-4, B-7, C-143), (IB-398, A-4, B-7, C-144), (IB-399, A-4, B-7, C-145), (IB-400, A-4, B-7, C-146), (IB-401, A-4, B-7, C-147), (IB-402, A-4, B-7, C-148), (IB-403, A-4, B-7, C-149), (IB-404, A-4, B-7, C-150), (IB-405, A-4, B-7, C-151), (IB-406, A-4, B-7, C-152), (IB-407, A-4, B-7, C-153), (IB-408, A-4, B-7, C-154), (IB-409, A-4, B-7, C-155), (IB-410, A-4, B-7, C-156), (IB-411, A-4, B-7, C-157), (IB-412, A-4, B-7, C-158), (IB-413, A-4, B-7, C-159), (IB-414, A-4, B-7, C-160), (IB-415, A-4, B-7, C-161), (IB-416, A-4, B-7, C-162), (IB-41, A-4, B-7, C-163), (IB-418, A-4, B-7, C-164), (IB-419, A-4, B-7, C-165), (IB-420, A-4, B-7, C-166), (IB-421, A-4, B-7, C-167), (IB-422, A-4, B-7, C-168), (IB-423, A-4, B-7, C-169), (IB-424, A-4, B-7, C-170), (IB-425, A-4, B-7, C-171), (IB-426, A-4, B-7, C-172), (IB-427, A-4, B-7, C-173), (IB-428, A-4, B-7, C-174), (IB-429, A-4, B-7, C-175), (IB-430, A-4, B-7, C-176), (IB-431, A-4, B-7, C-177), (IB-432, A-4, B-7, C-178), (IB-433, A-4, B-7, C-179), (IB-434, A-4, B-7, C-180), (IB-435, A-4, B-7, C-181), (IB-436, A-4, B-7, C-182), (IB-437, A-4, B-7, C-183), (IB-438, A-4, B-7, C-184), (IB-439, A-4, B-7, C-185), (IB-440, A-4, B-7, C-186), (IB-441, A-4, B-7, C-187), (IB-442, A-4, B-7, C-188), (IB-443, A-4, B-7, C-189), (IB-444, A-4, B-7, C-190), (IB-445, A-4, B-7, C-191), (IB-446, A-4, B-7, C-192), (IB-447, A-4, B-7, C-193), (IB-448, A-4, B-7, C-194), (IB-449, A-4, B-7, C-195), (IB-450, A-4, B-7, C-196), (IB-451, A-4, B-7, C-197), (IB-452, A-4, B-7, C-198), (IB-453, A-4, B-7, C-199), (IB-454, A-4, B-7, C-200), (IB-455, A-4, B-7, C-201), (IB-456, A-4, B-7, 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(IB-1183, A-22, B-7, C-85), (IB-1184, A-22, B-7, C-86), (IB-1185, A-22, B-7 C-87), (IB-1186, A-22, B-7, C-88), (IB-1187, A-22, B-7, C-89), (IB-1188, A-22, B-7, C-90), (IB-1189, A-22, B-7, C-91), (IB-1190, A-22, B-7, C-92), (IB-1191 A-22, B-7, C-93), (IB-1192, A-22, B-7, C-94), (IB-1193, A-22, B-7, C-95), (IB-1194, A-22, B-7, C-96), (IB-1195, A-22, B-7, C-97), (IB-1196, A-22, B-7, C-98), (IB-1197, A-22, B-7, C-99), (IB-1198, A-22, B-7, C-100), (IB-1199, A-22, B-7, C-101), (IB-1200, A-22, B-7, C-102), (IB-1201, A-22, B-7, C-103), (IB-1202, A-22, B-7, C-104), (IB-1203, A-22, B-7, C-105), (IB-1204, A-22 B-7, C-106), (IB-1205, A-22, B-7, C-107), (IB-1206, A-22, B-7, C-108), (IB-1207, A-22, B-7, C-109), (IB-1208, A-22, B-7, C-110), (IB-1209, A-22, B-7, C-111), (IB-1210, A-22, B-7, C-112), (IB-1211, A-22, B-7, C-113), (IB-1212, A-22, B-7, C-114), (IB-1213, A-22, B-7, C-115), (IB-1214, A-22, B-7, C-116), (IB-1215, A-22, B-7, C-117), (IB-1216, A-22, B-7, C-118), (IB-1217, A-22, B-7, C-119), (IB-1218, A-22, B-7, C-120), (IB-1219, A-22, B-7, C-121), (IB-1220, A-22, B-7, C-122), (IB-1221, A-22, B-7, C-123), (IB-1222, A-22, B-7, C-124), (IB-1223, A-22, B-7, C-125), (IB-1224, A-22, B-7, C-126), (IB-1225, A-22, B-7, C-127), (IB-1226, A-22, B-7, C-128), (IB-1227, A-22, B-7, C-129), (IB-1228, A-22, B-7, C-130), (IB-1229, A-22, B-7, C-131), (IB-1230, A-22, B-7, C-132), (IB-1231, A-22, B-7, C-133), (IB-1232, A-22, B-7, C-134), (IB-1233, A-22, B-7, C-135), (IB-1234, A-22, B-7, C-136), (IB-1235, A-22, B-7, C-137), (IB-1236, A-22, B-7, C-138), (IB-1237, A-22, B-7, C-139), (IB-1238, A-22, B-7, C-140), (IB-1239, A-22, B-7, C-141), (IB-1240, A-22, B-7, C-142), (IB-1241, A-22, B-7, C-143), (IB-1242, A-22, B-7, C-144), (IB-1243, A-22, B-7, C-145), (IB-1244, A-22, B-7, C-146), (IB-1245, A-22, B-7, C-147), (IB-1246, A-22, B-7, C-148), (IB-1247, A-22, B-7, C-149), (IB-1248, A-22, B-7, C-150), (IB-1249, A-22, B-7, C-151), (IB-1250, A-22, B-7, C-152), (IB-1251, A-22, B-7, C-153), (IB-1252, 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C-188), (IB-1287, A-22 B-7, C-189), (IB-1288, A-22, B-7, C-190), (IB-1289, A-22, B-7, C-191), (IB-1290, A-22, B-7, C-192), (IB-1291, A-22, B-7, C-193), (IB-1292, A-22, B-7, C-194), (IB-1293, A-22, B-7, C-195), (IB-1294, A-22, B-7, C-196), (IB-1295, A-22, B-7, C-197), (IB-1296, A-22, B-7, C-198), (IB-1297, A-22, B-7, C-199), (IB-1298, A-22, B-7, C-200), (IB-1299, A-22, B-7, C-201), (IB-1300, A-22, B-7, C-202), (IB-1301, A-22, B-7, C-203), (IB-1302, A-22, B-7, C-204), (IB 1303, A-22, B-7, C-205), (IB-1304, A-22, B-7, C-206), (IB-1305, A-22, B-7, C-207), (IB-1306, A-22, B-7, C-208), (IB-1307, A-22, B-7, C-209), (IB-1308, A-22, B-7, C-210), (IB-1309, A-22, B-7, C-211), (IB-1310, A-22, B-7, C-212), (IB-1311, A-22, B-7, C-213), (IB-1312, A-22, B-7, C-214), (IB-1313, A-23, B-1, C-15), (IB-1314, A-23, B-2, C-15), (IB-1315, A-23, B-3, C-15), (IB-1316, A-23, B-4, C-15), (IB-1317, A-23, B-5, C-15), (IB 1318, A-23, B-6, C-15), (IB-1319, A-23, B-7, C-15), (IB-1320, A-23, B-7, C-52), (IB-1321, A-23, 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C-62), (IB-1429, A-27, B-7, C-63), (IB-1430, A-27, B-7, C-64), (IB-1431, A-27, B-7, C-65), (IB-1432, A-27, B-7, C-66), (IB-1433, A-27, B-7, C-67), (IB-1434, A-27, B-7, C-68), (IB-1435, A-27, B-7, C-69), (IB-1436, A-27, B-7, C-70), (IB-1437, A-27, B-7, C-71), (IB-1438, A-27, B-7, C-72), (IB-1439, A-27, B-7, C-73), (IB-1440, A-27, B-7, C-74), (IB-1441, A-27, B-7, C-75), (IB-1442, A-27, B-7, C-76), (IB-1443, A-27, B-7, C-77), (IB-1444, A-27, B-7, C-78), (IB-1445, A-27, B-7, C-79), (IB-1446, A-27, B-7, C-80), (IB-1447, A-27, B-7, C-81), (IB-1448, A-27, B-7, C-82), (IB-1449, A-27, B-7, C-83), (IB-1450, A-27, B-7, C-84), (IB-1451, A-27, B-7, C-85), (IB-1452, A-27, B-7, C-86), (IB-1453, A-27, B-7, C-87), (IB-1454, A-27, B-7, C-88), (IB-1455, A-27, B-7, C-89), (IB-1456, A-27, B-7, C-90), (IB-1457, A-27, B-7, C-91), (IB-1458, A-7, B-7, C-92), (IB-1459, A-27, B-7, C-93), (IB-1460, A-27, B-7, C-94), (IB-1461, A-27, B-7, C-95), (IB-1462, A-27, B-7, C-96), (IB-1463, A-27, B-7, C-97), (IB-1464, 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A-29, B-7, C-70), (IB-1885, A-29, B-7, C-71), (IB-1886, A-29, B-7, C-72), (IB-1887, A-29, B-7, C-73), (IB-1888, A-29, B-7, C-74), (IB-1889, A-29, B-7, C-75), (IB-1890, A-29, B-7, C-76), (IB-1891, A-29, B-7, C-77), (IB-1892, A-29, B-7, C-78), (IB-1893, A-29, B-7, C-79), (IB-1894, A-29, B-7, C-80), (IB-1895, A-29, B-7, C-81), (IB-1896, A-29, B-7, C-82), (IB-1897, A-29, B-7, C-83), (IB-1898, A-29, B-7, C-84), (IB-1899, A-29, B-7, C-85), (IB-1900, A-29, B-7, C-86), (IB-1901, A-29, B-7, C-87), (IB-1902, A-29, B-7, C-88), (IB-1903, A-29, B-7, C-89), (IB-1904, A-29, B-7, C-90), (IB-1905, A-29, B-7, C-91), (IB-1906, A-29, B-7, C-92), (IB-1907, A-29, B-7, C-93), (IB-1908, A-29, B-7, C-94), (IB-1909, A-29, B-7, C-95), (IB-1910, A-29, B-7, C-96), (IB-1911, A-29, B-7, C-97), (IB-1912, A-29, B-7, C-98), (IB-1913, A-29, B-7, C-99), (IB-1914, A-29, B-7, C-100), (IB-1915, A-29, B-7, C-101), (IB-1916, A-29, B-7, C-102), (IB-1917, A-29, B-7, C-103), (IB-1918, A-29, B-7, C-104), (IB-1919, A-29, B-7, C-105), (IB-1920, A-29, B-7, C-106), (IB-1921, A-29, B-7, C-107), (IB-1922, A-29, B-7, C-108), (IB-1923, A-29, B-7, C-109), (IB-1924, A-29, B-7, C-110), (IB-1925, A-29, B-7, C-111), (IB-1926, A-29, B-7, C-112), (IB-1927, A-29, B-7, C-113), (IB-1928, A-29, B-7, C-114), (IB-1929, A-29, B-7, C-115), (IB-1930, A-29, B-7, C-116), (IB-1931, A-29, B-7, C-117), (IB-1932, A-29, B-7, C-118), (IB-1933, A-29, B-7, C-119), (IB-1934, A-29, B-7, C-120), (IB-1935, A-29, B-7, C-121), (IB-1936, A-29, B-7, C-122), (IB-1937, A-29, B-7, C-123), (IB-1938, A-29, B-7, C-124), (IB-1939, A-29, B-7, C-125), (IB-1940, A-29, B-7, C-126), (IB-1941, A-29, B-7, C-127), (IB-1942, A-29, B-7, C-128), (IB-1943, A-29, B-7, C-129), (IB-1944, A-29, B-7, C-130), (IB-1945, A-29, B-7, C-131), (IB-1946, A-29, B-7, C-132), (IB-1947, A-29, B-7, C-133), (IB-1948, A-29, B-7, C-134), (IB-1949, A-29, B-7, C-135), (IB-1950, A-29, B-7, C-136), (IB-1951, A-29, B-7, C-137), (IB-1952, A-29, B-7, C-138), (IB-1953, A-29, B-7, C-139), (IB-1954, A-29, B-7, C-140), (IB-1955, A-29, B-7, C-141), (IB-1956, A-29, B-7, C-142), (IB-1957, A-29, B-7, C-143), (IB-1958, A-29, B-7, C-144), (IB-1959, A-29, B-7, C-145), (IB-1960, A-29, B-7, C-146), (IB-1961, A-29, B-7, C-147), (IB-1962, A-29, B-7, C-148), (IB-1963, A-29, B-7, C-149), (IB-1964, A-29 B-7, C-150), (IB-1965, A-29, B-7, C-151), (IB-1966, A-29, B-7, C-152), (IB-1967, A-29, B-7, C-153), (IB-1968, A-29, B-7, C-154), (IB-1969, A-29, B-7, C-155), (IB-1970, A-29, B-7, C-156), (IB-1971, A-29, B-7, C-157), (IB-1972, A-29, B-7, C-158), (IB-1973, A-29, B-7, C-159), (IB-1974, A-29, B-7, C-160), (IB-1975, A-29, B-7, C-161), (IB-1976, A-29, B-7, C-162), (IB-1977, A-29, B-7, C-163), (IB-1978, A-29, B-7, C-164), (IB-1979, A-29, B-7, C-165), (IB-1980, A-29, B-7, C-166), (IB-1981, A-29, B-7, C-167), (IB-1982, A-29, B-7, C-168), (IB-1983, A-29, B-7, C-169), (IB-1984, A-29, B-7, C-170), (IB-1985, A-29, B-7, C-171), (IB-1986, A-29, B-7, C-172), (IB-1987, A-29, B-7, C-173), (IB-1988, A-29, B-7, C-174), (IB-1989, A-29, B-7, C-175), (IB-1990, A-29, B-7, C-176), (IB-1991, A-29, B-7, C-177), (IB-1992, A-29, B-7, C-178), (IB-1993, A-29, B-7, C-179), (IB-1994, A-29, B-7, C-180), (IB-1995, A-29, B-7, C-181), (IB-1996, A-29, B-7, C-182), (IB-1997, A-29, B-7, C-183), (IB-1998, A-29, B-7, C-184), (IB-1999, A-29, B-7, C-185), (IB-2000, A-29, B-7, C-186), (IB-2001, A-29, B-7, C-187), (IB-2002, A-29, B-7, C-188), (IB-2003, A-29, B-7, C-189), (IB-2004, A-29, B-7, C-190), (IB-2005, A-29, B-7, C-191), (IB-2006, A-29, B-7, C-192), (IB-2007, A-29, B-7, C-193), (IB-2008, A-29, B-7, C-194), (IB-2009, A-29, B-7, C-195), (IB-2010, A-29, B-7, C-196), (IB-2011, A-29, B-7, C-197), (IB-2012, A-29, B-7, C-198), (IB-2013, A-29, B-7, C-199), (IB-2014, A-29, B-7, C-200), (IB-2015, A-29, B-7, C-201), (IB-2016, A-29, B-7, C-202), (IB-2017, A-29, B-7, C-203), (IB-2018, A-29, B-7, C-204), (IB-2019, A-29, B-7, C-205), (IB-2020, A-29, B-7, C-206), (IB-2021, A-29, B-7, C-207), (IB-2022, A-29, B-7, C-208), (IB-2023, A-29, B-7, C-209), (IB-2024, A-29, B-7, C-210), (IB-2025, A-29, B-7, C-211), (IB-2026, A-29, B-7, C-212), (IB-2027, A-29, B-7, C-213), (IB-2028, A-29, B-7, C-214), (IB-2029, A-29, B-8, C-15), (IB-2030, A-29, B-9, C-15), (IB-2031, A-29, B-10, C-15), (IB-2032, A-29, B-10, C-52), (IB-2033, A-30, B-1, C-15), (IB-2034, A-30, B-2, C-15), (IB-2035, A-30, B-3, C-15), (IB-2036, A-30, B-4, C-15), (IB-2037, A-30, B-5, C-15), (IB-2038, A-30, B-6, C-15), (IB-2039, A-30, B-7, C-1), (IB-2040, A-30, B-7, C-2), (IB-2041, A-30, B-7, C-3), (IB-2042, A-30, B-7, C-4), (IB-2043, A-30, B-7, C-5), (IB-2044, A-30, B-7, C-6), (IB-2045, A-30, B-7, C-7), (IB-2046, A-30, B-7, C-8), (IB-2047, A-30, B-7, C-9), (IB-2048, A30, B-7, C-10), (IB-2049, A-30, B-7, C-11), (IB-2050, A-30, B-7, C-12), (IB-2051, A-30, B-7, C-13), (IB-2052, A-30, B-7, C-14), (IB-2053, A-30, B-7, C-15), (IB-2054, A-30, B-7, C-16), (IB-2055, A-30, B-7, C-17), (IB-2056, A-30, B-7, C-18), (IB-2057, A-30, B-7, C-19), (IB-2058, A-30, B-7, C-20), (IB-2059, A-30, B-7, C-21), (IB-2060, A-30, B-7, C-22), (IB-2061, A-30, B-7, C-23), (IB-2062, A-30, B-7, C-24), (IB-2063, A-30, B-7, C-25), (IB-2064, A-30, B-7, C-26), (IB-2065, A-30, B-7, C-27), (IB-2066, A-30, B-7, C-28), (IB-2067, A-30, B-7, C-29), (IB-2068, A-30, B-7, C-30), (IB-2069, A-30, B-7, C-31), (IB-2070, A-30, B-7, C-32), (IB-2071, A-30, B-7, C-33), (IB-2072, A-30, B-7, C-34), (IB-2073, A-30, B-7, C-35), (IB-2074, A-30, B-7, C-36), (IB-2075, A-30, B-7, C-37), (IB-2076, A-30, B-7, C-38), (IB-2077, A-30, B-7, C-39), (IB-2078, A-30, B-7, C-40), (IB-2079, A-30, B-7, C-41), (IB-2080, A-30, B-7, C-42), (IB-2081, A-30, B-7, C-43), (IB-2082, A-30, B-7, C-44), (IB-2083, A-30, B-7, C-45), (IB-2084, A-30, B-7, C-46), (IB-2085, A-30, B-7, C-47), (IB-2086, A-30, B-7, C-48), (IB-2087, A-30, B-7, C-49), (IB-2088, A-30, B-7, C-50), (IB-2089, A-30, B-7, C-51), (IB-2090, A-30, B-7, C-52), (IB-2091, A-30, B-7, C-53), (IB-2092, A-30, B-7, C-54), (IB-2093, A-30, B-7, C-55), (IB-2094, A-30, B-7, C-56), (IB-2095, A-30, B-7, C-57), (IB-2096, A-30, B-7, C-58), (IB-2097, A-30, B-7, C-59), (IB-2098, A-30, B-7, C-60), (IB-2099, A-30, B-7, C-61), (IB-2100, A-30, B-7, C-62), (IB-2101, A-30, B-7, C-63), (IB-2102, A-30, B-7, C-64), (IB-2103, A-30, B-7, C-65), (IB-2104, A-30, B-7, C-66), (IB-2105, A-30, B-7, C-67), (IB-2106, A-30, B-7, C-68), (IB-2107, A-30, B-7, C-69), (IB-2108, A-30, B-7, C-70), (IB-2109, A-30, B-7, C-71), (IB-2110, A-30, B-7, C-72), (IB-2111, A-30, B-7, C-73), (IB-2112, A-30, B-7, C-74), (IB-2113, A-30, B-7, C-75), (IB-2114, A-30, B-7, C-76), (IB-2115, A-30, B-7, C-77), (IB-2116, A-30, B-7, C-78), (IB-2117, A-30, B-7, C-79), (IB-2118, A-30, B-7, C-80), (IB-2119, A-30, B-7, C-81), (IB-2120, A-30, B-7, C-82), (IB-2121, A-30, B-7, C-83), (IB-2122, A-30, B-7, C-84), (IB-2123, A-30, B-7, C-85), (IB-2124, A-30, B-7, C-86), (IB-2125, A-30, B-7, C-87), (IB-2126, A-30, B-7, C-88), (IB-2127, A-30, B-7, C-89), (IB-2128, A-30, B-7, C-90), (IB-2129, A-30, B-7, C-91), (IB-2130, A-30, B-7, C-92), (IB-2131, A-30, B-7, C-93), (IB-2132, A-30, B-7, C-94), (IB-2133, A-30, B-7, C-95), (IB-2134 A-30, B-7, C-96), (IB-2135, A-30, B-7, C-97), (IB-2136, A-30, B-7, C-98), (IB-2137, A-30, B-7, C-99), (IB-2138, A-30, B-7, C-100), (IB-2139, A-30, B-7, C-101), (IB-2140, A-30, B-7, C-102), (IB-2141, A-30, B-7, C-103), (IB-2142, A-30, B-7, C-104), (IB-2143, A-30, B-7, C-105), (IB-2144, A-30, B-7, C-106), (IB-2145, A-30, B-7, C-107), (IB-2146, A-30, B-7, C-108), (IB-2147, A-30, B-7, C-109), (IB-2148, A-30, B-7, C-110), (IB-2149, A-30, B-7, C-111), (IB-2150, A-30, B-7, C-112), (IB-2151, A-30, B-7, C-113), (IB-2152, A-30, B-7, C-114), (IB-2153, A-30, B-7, C-115), (IB-2154, A-30, B-7, C-116), (IB-2155, A-30, B-7, C-117), (IB-2156, A-30, B-7, C-118), (IB-2157, A-30, B-7, C-119), (IB-2158, A-30, B-7, C-120), (IB-2159, A-30, B-7, C-121), (IB-2160, A-30, B-7, C-122), (IB-2161, A-30, B-7, C-123), (IB-2162, A-30, B-7, C-124), (IB-2163, A-30, B-7, C-125), (IB-2164, A-30, B-7, C-126), (IB-2165, A-30, B-7, C-127), (IB-2166, A-30, B-7, C-128), (IB-2167, A-30, B-7, C-129), (IB-2168, A-30, B-7, C-130), (IB-2169, A-30, B-7, C-131), (IB-2170, A-30, B-7, C-132), (IB-2171, A-30, B-7, C-133), (IB-2172, A-30, B-7, C-134), (IB-2173, A-30, B-7, C-135), (IB-2174, A-30, B-7, C-136), (IB-2175, A-30, B-7, C-137), (IB-2176, A-30, B-7, C-138), (IB-2177, A-30, B-7, C-139), (IB-2178, A-30, B-7, C-140), (IB-2179, A-30, B-7, C-141), (IB-2180, A-30, B-7, C-142), (IB-2181, A-30, B-7, C-143), (IB-2182, A-30, B-7, C-144), (IB-2183, A-30, B-7, C-145), (IB-2184, A-30, B-7, C-146), (IB-2185, A-30, B-7, C-147), (IB-2186, A-30, B-7, C-148), (IB-2187, A-30, B-7, C-149), (IB-2188, A-30, B-7, C-150), (IB-2189, A-30, B-7, C-151), (IB-2190, A-30, B-7, C-152), (IB-2191, A-30, B-7, C-153), (IB-2192, A-30, B-7, C-154), (IB-2193, A-30, B-7, C-155), (IB-2194, A-30, B-7, C-156), (IB-2195, A-30, B-7, C-157), (IB-2196, A-30, B-7, C-158), (IB-2197, A-30, B-7, C-159), (IB-2198, A-30, B-7, C-160), 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(IB-2970, A-34, B-7, C-36), (IB-2971, A-34, B-7, C-37), (IB-2972, A-34, B-7, C-38), (IB-2973, A-34, B-7, C-39), (IB-2974, A-34, B-7, C-40), (IB-2975, A-34, B-7, C-41), (IB-2976, A-34, B-7, C-42), (IB-2977, A-34, B-7, C-43), (IB-278, A-34, B-7, C-44), (IB-2979, A-34, B-7, C-45), (IB-2980, A-34, B-7, C-46), (IB-2981, A-34, B-7, C-47), (IB-2982, A-34, B-7, C-48), (IB-2983, A-34, B-7, C-49), (IB-2984, A-34, B-7, C-50), (IB-2985, A-34, B-7, C-51), (IB-2986, A-34, B-7, C-52), (IB-2987, A-34, B-7, C-53), (IB-2988, A-34, B-7, C-54), (IB-2989, A-34, B-7, C-55), (IB-2990, A-34, B-7, C-56), (IB-2991, A-34, B-7, C-57), (IB-2992, A-34, B-7, C-58), (IB-2993, A-34, B-7, C-59), (IB-2994, A-34, B-7, C-60), (IB-2995, A-34, B-7, C-61), (IB-2996, A-34, B-7, C-62), (IB-2997, A-34, B-7, C-63), (IB-2998, A-34, B-7, C-64), (IB-2999, A-34, B-7, C-65), (IB-3000, A-34, B-7, C-66), (IB-3001, A-34, B-7, C-67), (IB-3002, A-34, B-7, C-68), (IB-3003, A-34, B-7, C-69), (IB-3004, A-34, B-7, C-70), (IB-3005, A-34, B-7, C-71), (IB-3006, A-34, B-7, C-72), (IB-3007, A-34, B-7, C-73), (IB-3008, A-34, B-7, C-74), (IB-3009, A-34, B-7, C-75), (IB-3010, A-34, B-7, C-76), (IB-3011, A-34, B-7, C-77), (IB-3012, A-34, B-7, C-78), (IB-3013, A-34, B-7, C-79), (IB-3014, A-34, B-7, C-80), (IB-3015, A-34, B-7, C-81), (IB-3016, A-34, B-7, C-82), (IB-3017, A-34, B-7, C-83), (IB-3018, A-34, B-7, C-84), (IB-3019, A-34, B-7, C-85), (IB-3020, A-34, B-7, C-86), (IB-3021, A-34, B-7, C-87), (IB-3022, A-34, B-7, C-88), (IB-3023, A-34, B-7, C-89), (IB-3024, A-34, B-7, C-90), (IB-3025, A-34, B-7, C-91), (IB-3026, A-34, B-7, C-92), (IB-3027, A-34, B-7, C-93), (IB-3028, A-34, B-7, C-94), (IB-3029, A-34, B-7, C-95), (IB-3030, A-34, B-7, C-96), (IB-3031, A-34, B-7, C-97), (IB-3032, A-34, B-7, C-98), (IB-3033, A-34, B-7, C-99), (IB-3034, A-34, B-7, C-100), (IB-3035, A-34, B-7, C-101), (IB-3036, A-34, B-7, C-102), (IB-3037, A-34, B-7, C-103), (IB-3038, A-34, B-7, C-104), (IB-3039 A-34, B-7, C-105), (IB-3040, A-34, B-7, C-106), (IB-3041, A-34, B-7, C-107), (IB-3042, A-34, B-7, C-108), (IB-3043, A-34, B-7, C-109), (IB-3044, A-34, B-7, C-110), (IB-3045, A-34, B-7, C-111), (IB-3046, A-34, B-7, C-112), (IB-3047, A-34, B-7, C-113), (IB-3048, A-34, B-7, C-114), (IB-3049, A-34, B-7, C-115), (IB-3050, A-34, B-7, C-116), (IB-3051, A-34, B-7, C-117), (IB-3052, A-34, B-7, C-118), (IB-3053, A-34, B-7, C-119), (IB-3054, A-34, B-7, C-120), (IB-3055, A-34, B-7, C-121), (IB-3056, A-34, B-7, C-122), (IB-3057, A-34, B-7, C-123), (IB-3058, A-34, B-7, C-124), (IB-3059, A-34, B-7, C-125), (IB-3060, A-34, B-7, C-126), (IB-3061, A-34, B-7, C-127), (IB-3062, A-34, B-7, C-128), (B-3063, A-34, B-7, C-129), (IB-3064, A-34, B-7, C-130), (IB-3065, A-34, B-7, C-131), (IB-3066, A-34, B-7, C-132), (IB-3067, A-34, B-7, C-133), (IB-3068, A-34, B-7, C-134), (IB-3069, A-34, B-7, C-135), (IB-3070, A-34, B-7, C-136), (IB-3071, A-34, B-7, C-137), (IB-3072, A-34, B-7, C-138), (IB-3073, A-34, B-7, C-139), (IB-3074, A-34, B-7, C-140), (IB-3075, A-34, B-7, C-141), (IB-3076, A-34, B-7, C-142), (IB-3077, A-34, B-7, C-143), (IB-3078, A-34, B-7, C-144), (IB-3079, A-34, B-7, C-145), (IB-3080, A-34, B-7, C-146), (IB-3081, A-34, B-7, C-147), (IB-3082, A-34, B-7, C-148), (IB-3083, A-34, B-7, C-149), (IB-3084, A-34, B-7, C-150), (IB-3085, A-34, B-7, C-151), (IB-3086, A-34, B-7, C-152), (IB-3087, A-34, B-7, C-153), (IB-3088, A-34, B-7, C-154), (IB-3089, A-34, B-7, C-155), (IB-3090, A-34, B-7, C-156), (IB-3091, A-34, B-7, C-157), (IB-3092, A-34, B-7, C-158), (IB-3093, A-34, B-7, C-159), (IB-3094, A-34, B-7, C-160), (IB-3095, A-34, B-7, C-161), (IB-3096, A-34, B-7, C-162), (IB-3097, A-34, B-7, C-163), (IB-3098, A-34, B-7, C-164), (IB-3099, A-34, B-7, C-165), (IB-3100, A-34, B-7, C-166), (IB-3101, A-34, B-7, C-167), (IB-3102, A-34, B-7, C-168), (IB-3103, A-34, B-7, C-169), (IB-3104, A-34, B-7, C-170), (IB-3105, A-34, B-7, C-171), (IB-3106, A-34, B-7, C-172), (IB-3107, A-34, B-7, C-173), (IB-3108, A-34, B-7, C-174), (IB-3109, A-34, B-7, C-175), (IB-3110, A-34, B-7, C-176), (IB-3111, A-34, B-7, C-177), (IB-3112, A-34, B-7, C-178), (IB-3113, A-34, B-7, C-179), (IB-3114, A-34, B-7, C-180), (IB-3115, A-34, B-7, C-181), (IB-3116, A-34, B-7, C-182), (IB-3117, A-34, B-7, C-183), (IB-3118, A-34, B-7, C-184), (IB-3119, A-34, B-7, C-185), (IB-3120, A-34, B-7, C-186), (IB-3121, A-34, B-7, C-187), (IB-3122, A-34, B-7, C-188), (IB-3123, A-34, B-7, C-189), (IB-3124, A-34, B-7, C-190), (IB-3125, A-34, B-7, C-191), (IB-3126, A-34, B-7, C-192), (IB-3127, A-34, B-7, C-193), (IB-3128, A-34, B-7, C-194), (IB-3129, A-34, B-7, C-195), (IB-3130, A-34, B-7, C-196), (IB-3131, A-34, B-7, C-197), (IB-3132, A-34, B-7, C-198), (IB-3133, A-34, B-7, C-199), (IB-3134, A-34, B-7, C-200), (IB-3135, A-34, B-7, C-201), (IB-3136, A-34, B-7, C-202), (IB-AT 3,137, A-34, B-7, C-203), (IB-3138, A-34, B-7, C-204), (IB-3139, A-34, B-7, C-205), (IB-3140, A-34, B-7, C-206), (IB-3141, A-34, B-7, C-207), (IB-3142, A-34, B-7, C-208), (IB-3143, A-34, B-7, C-209), (IB-3144, A-34, B-7, C-210), (IB-3145, A-34, B-7, C-211), (IB3146, A-34, B-7, C-212), (IB-3147, A-34, B-7, C-213), (IB-3148, A-34, B-7, C-214), (IB-3149, A-34, B-8, C-15), (IB-3150, A-34, B-9, C-15), (IB-3151, A-34, B-10, C-15), (IB-3152, A-34, B-10, C-52), (IB-3153, A-35, B-1, C-15), (IB-3154, A-35, B-2, C-15), (IB-3155, A-35, B-3, C-15), (IB-3156, A-35, B-4, C-15), (IB-3157, A-35, B-5, C-15), (IB-3158, A-35, B-6, C-15), (IB-3159, A-35, B-7, C-1), (IB-3160, A-35, B-7, C-2), (IB-3161, A-35, B-7, C-3), (IB-3162, A-35, B-7, C-4), (IB-3163, A-35, B-7, C-5), (IB-3164, A-35, B-7, C-6), (IB-3165, A-35, B-7, C-7), (IB-3166, A-35, B-7, C-8), (IB-3167, A-35, B-7, C-9), (IB-3168, A-35, B-7, C-10), (IB-3169, A-35, B-7, C-11), (IB-3170, A-35, B-7, C-12), (IB-3171, A-35, B-7, C-13), (IB-3172, A-35, B-7, C-14), (IB-3173, A-35, B-7, C-15), (IB-3174, A-35, B-7, C-16), (IB-3175, A-35, B-7, C-17), (IB-3176, A-35, B-7, C-18), (IB-3177, A-35, B-7, C-19), (IB-3178, A-35, B-7, C-20), (IB-3179, A-35, B-7, C-21), (IB-3180, A-35, B-7, C-22), (IB-3181, A-35, B-7, C-23), (IB-3182, A-35, B-7, C-24), (IB-3183, A-35, B-7, C-25), (IB-3184, A-35, B-7, C-26), (IB-3185, A-35, B-7, C-27), (IB-3186, A-35, B-7, C-28), (IB-3187, A-35, B-7, C-29), (IB-3188, A-35, B-7, C-30), (IB-3189, A-35, B-7, C-31), (IB-3190, A-35, B-7, C-32), (IB-3191, A-35, B-7, C-33), (IB-3192, A-35, B-7, C-34), (IB-3193, A-35, B-7, C-35), (IB-3194, A-35, B-7, C-36), (IB-3195, A-35, B-7, C-37), (IB-3196, A-35, B-7, C-38), (IB-3197, A-35, B-7, C-39), (IB-3198, A-35, B-7, C-40), (IB-3199, A-35, B-7, C-41), (IB-3200, A-35, B-7, C-42), (IB-3201, A-35, B-7, C-43), (IB-3202, A-35, B-7, C-44), (IB-3203, A-35, B-7, C-45), (IB-3204, A-35, B-7, C-46), (IB-3205, A-35, B-7, C-47), (IB-3206, A-35, B-7, C-48), (IB-3207, A-35, B-7, C-49), (IB 3208, A-35, B-7, C-50), (IB-3209, A-35, B-7, C-51), (IB-3210, A-35, B-7, C-52), (IB-3211, A-35, B-7, C-53), (IB-3212, A-35, B-7, C-54), (IB-3213, A-35, B-7, C-55), (IB-3214, A-35, B-7, C-56), (IB-3215, A-35, B-7, C-57), (IB-3216, A-35, B-7, C-58), (IB-3217, A-35, B-7, C-59), (IB-3218, A-35, B-7, C-60), (IB-3219, A-35, B-7, C-61), (IB-3220, A-35, B-7, C-62), (IB-3221, A-35, B-7, C-63), (IB-3222, A-35, B-7, C-64), (IB-3223, A-35, B-7, C-65), (IB-3224, A-35, B-7, C-66), (IB-3225, A-35, B-7, C-67), (IB-3226, A-35, B-7, C-68), (IB-3227, A-35, B-7, C-69), (IB-3228, A-35, B-7, C-70), (IB-3229, A-35, B-7, C-71), (IB-3230, A-35, B-7, C-72), (IB-3231, A-35, B-7, C-73), (IB-322, A-35, B-7, C-74), (IB-3233, A-35, B-7, C-75), (IB-3234, A-35, B-7, C-76), (IB-3235, A-35, B-7, C-77), (IB-3236, A-35, B-7, C-78), (IB-3237, A-35, B-7, C-79), (IB-3238, A-35, B-7, C-80), (IB-3239, A-35, B-7, C-81), (IB-3240, A-35, B-7, C-82), (IB-3241, A-35, B-7, C-83), (IB-3242, A-35, B-7, C-84), (IB-3243, A-35, B-7, C-85), (IB-3244, A-35, B-7, C-86), (IB-3245, A-35, B-7, C-87), (IB-3246, A-35, B-7, C-88), (IB-3247, A-35, B-7, C-89), (IB-3248, A-35, B-7, C-90), (IB-3249, A-35, B-7, C-91), (IB-3250, A-35, B-7, C-92), (IB-3251, 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(IB-3286, A-35, B-7, C-128), (IB-3287, A-35, B-7, C-129), (IB-3288, A-35, B-7, C-130), (IB-3289, A-35, B-7, C-131), (IB-3290, A-35, B-7, C-132), (IB-3291, A-35, B-7, C-133), (IB-3292, A-35, B-7, C-134), (IB-3293, A-35, B-7, C-135), (IB-3294, A-35, B-7, C-136), (IB-3295, A-35, B-7, C-137), (IB-3296, A-35, B-7, C-138), (IB-3297, A-35, B-7, C-139), (IB-3298, A-35, B-7, C-140), (IB-3299, A-35, B-7, C-141), (IB-3300, A-35, B-7, C-142), (IB-3301, A-35, B-7, C-143), (IB-3302, A-35, B-7, C-144), (IB-3303, A-35, B-7, C-145), (IB-3304, A-35, B-7, C-146), (IB 3305, A-35, B-7, C-147), (IB-3306, A-35, B-7, C-148), (IB 3307, A-35, B-7, C-149), (IB-3308, A-35, B-7, C-150), (IB 3309, A-35, B-7, C-151), (IB-3310, A-35, B-7, C-152), (IB-3311, A-35, B-7, C-153), (IB-3312, A-35, B-7, C-154), (IB 3313, A-35, B-7, C-155), (IB-3314, A-35, B-7, C-156), (IB 3315, A-35, B-7, C-157), IB 3316, A-35, B-7, C-158), (IB 3317, A-35, B-7, C-159), (IB-3318, A-35, B-7, C-160), (IB 3319, A-35, B-7, C-161), (IB-3320, A-35, B-7, C-162), (IB-3321, A-35, B-7, C-163), (IB-3322, A-35, B-7, C-164), (IB-3323, A-35, B-7, C-165), (IB-3324, A-35, B-7, C-166), (IB 3325, A-35, B-7, C-167), (IB-3326, A-35, B-7, C-168), (IB 3327, A-35, B-7, C-169), (IB-3328, A-35, B-7, C-170), (IB-3329, A-35, B-7, C-171), (IB 3330, A-35, B-7, C-172), (IB-3331, A-35, B-7, C-173), (IB-3332, A-35, B-7, C-174), (IB-3333, A-35, B-7, C-175), (IB-3334, A-35, B-7, C-176), (IB-3335, A-35, B-7, C-177), (IB-3336, A-35, B-7, C-178), (IB-3337, A-35, B-7, C-179), (IB-3338, A-35, B-7, C-180), (IB-3339, A-35, B-7, C-181), (IB-3340, A-35, B-7, C-182), (IB-3341, A-35, B-7, C-183), (IB-3342, A-35, B-7, C-184), (IB-3343, A-35, B-7, C-185), (IB-3344, A-35, B-7, C-186), (IB-3345, A-35, B-7, C-187), (IB-3346, A-35, B-7, C-188), (IB-3347, A-35, B-7, C-189), (IB-3348, A-35, B-7, C-190), (IB-3349, A-35, B-7, C-191), (IB-3350, A-35, B-7, C-192), (IB-3351, A-35, B-7, C-193), (IB-3352, A-35, B-7, C-194), (IB-3353, A-35, B-7, C-195), (IB-3354, A-35, B-7, C-196), (IB-3355, A-35, B-7, C-197), (IB-3356, A-35, B-7, C-198), (IB-3357, A-35, B-7, C-199), (IB-3358, A-35, B-7, C-200), (IB-3359, A-35, B-7, C-201), (IB-3360, A-35, B-7, C-202), (IB-3361, A-35, B-7, C-203), (IB-3362, A-35, B-7, C-204), (IB-3363, A-35, B-7, C-205), (IB-3364, A-35, B-7, C-206), (IB-3365, A-35, B-7, C-207), (IB-3366, A-35, B-7, C-208), (IB-3367, A-35, B-7, C-209), (IB-3368, A-35, B-7, C-210), (IB-3369, A-35, B-7, C-211), (IB-3370, A-35, B-7, C-212), (IB-3371, A-35, B-7, C-213), (IB-3372, A-35, B-7, C-214), (IB-3373, A-35, B-8, C-15), (IB-3374, A-35, B-9, C-15), (IB-3375, A-35, B-10, C-15), (IB-3376, A-35, B-10, C-52), (IB-3377, A-36, B-1, C-15), (IB-3378, A-36, B-2, C-15), (IB-3379, A-36, B-3, C-15), (IB-3380, A-36, B-4, C-15), (IB-3381, A-36, B-5, C-15), (IB-3382, A-36, B-6, C-15), (IB-3383, A-36, B-7, C-1), (IB-3384, A-36, B-7, C-2), (IB-3385, A-36, B-7, C-3), (IB-3386, A-36, B-7, C-4), (IB-3387, A-36, B-7, C-5), (IB-3388, A-36, B-7, C-6), (IB-3389, A-36, B-7, C-7), (IB-3390, A-36, B-7, C-8), (IB-3391, A-36, B-7, C-9), (IB-3392, A-36, B-7, C-10), (IB-3393, A-36, B-7, C-11), (IB-3394, A-36, B-7, C-12), (IB-3395, A-36, B-7, C-13), (IB-3396, A-36, B-7, C-14), (IB-3397, A-36, B-7, C-15), (IB-3398, A-36, B-7, C-16), (IB-3399, A-36, B-7, C-17), (IB-3400 A-36, B-7, C-18), (IB-3401, A-36, B-7, C-19), (IB-3402, A-36, B-7, C-20), (IB-3403, A-36, B-7, C-21), (IB 3404, A-36, B-7, C-22), (IB-3405, A-36, B-7, C-23), (IB 3406, A-36, B-7, C-24), (IB-3407, A-36, B-7, C-25), (IB 3408, A-36, B-7, C-26), (IB 3409, A-36, B-7, C-27), (IB-3410, A-36, B-7, C-28), (IB-3411, A-36, B-7, C-29), (IB-3412, A-36, B-7, C-30), (IB 3413, A-36, B-7, C-31), (IB-3414, A-36, B-7, C-32), (IB 3415, A-36, B-7, C-33), (IB 3416, A-36, B-7, C-34), (IB-3417, A-36, B-7, C-35), (IB-3418, A-36, B-7, C-36), (IB-3419, A-36, B-7, C-37), (IB 3420, A-36, B-7, C-38), (IB-3421, A-36, B-7, C-39), (IB 3422, A-36, B-7, C-40), (IB-3423, A-36, B-7, C-41), (IB-3424, A-36, B-7, C-42), (IB-3425, A-36, B-7, C-43), (IB 3426, A-36, B-7, C-44), (IB-3427, A-36, B-7, C-45), (IB 3428, A-36, B-7, C-46), (IB-3429, A-36, B-7, C-47), (IB 3430, A-36, B-7, C-48), (IB-3431, A-36, B-7, C-49), (IB-3432, A-36, B-7, C-50), (IB-3433, A-36, B-7, C-51), (IB-3434, A-36, B-7, C-52), (IB-3435, A-36, B-7, C-53), (IB-3436, A-36, B-7, C-54), (IB-3437, A-36, B-7, C-55), (IB-3438, A-36, B-7, C-56), (IB-3439, A-36, B-7, C-57), (IB-3440, A-36, B-7, C-58), (IB-3441, A-36, B-7, C-59), (IB-3442, A-36, B-7, C-60), (IB-3443, A-36, B-7, C-61), (IB-3444, A-36, B-7, C-62), (IB-3445, A-36, B-7, C-63), (IB-3446, A-36, B-7, C-64), (IB-3447, A-36, B-7, C-65), (IB-3448, A-36, B-7, C-66), (IB-3449, A-36, B-7, C-67), (IB-3450, A-36, B-7, C-68), (IB-3451, A-36, B-7, C-69), (IB-3452, A-36, B-7, C-70), (IB-3453, A-36, B-7, C-71), (IB-3454, A-36, B-7, C-72), (IB-3455, A-36, B-7, C-73), (IB-3456, A-36, B-7, C-74), (IB-3457, A-36, B-7, C-75), (IB-3458, A-36, B-7, C-76), (IB-3459, A-36, B-7, C-77), (IB-3460, A-36, B-7, C-78), (IB-3461, 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C-15), (IB-4406, A-86, B-10, C-15), (IB-4407, A-87, B-7, C-15), (IB-4408, A-87, B-10, C-15), (IB-4409, A-88, B-7, C-15), (IB-4410, A-88, B-10, C-15), (IB-4411, A-89, B-7, C-15), (IB-4412, A-89, B-10, C-15), (IB-4413, A-90, B-7, C-15), (IB-444, A-90, B-10, C-15), (IB-4415, A-91, B-7, C-15), (IB-4416 A-91, B-10, C-15), (IB-4417, A-92, B-7, C-15), (IB-4418, A-92, B-10, C-15), (IB-4419, A-93, B-7, C-15), (IB-4420, A-93, B-10, C-15), (IB-4421, A-94, B-7, C-15), (IB-4422, A-94, B-10, C-15), (IB-4423, A-95, B-7, C-15), (IB-4424, A-95, B-10, C-15), (IB-4425, A-96, B-7, C-15), (IB-4426, A-96, B-10, C-15), (IB-4427, A-97, B-7, C-15), (IB-4428, A-97, B-10, C-15), (IB-4429, A-98, B-7, C-15), (IB-4430, A-98, B-10, C-15), (IB-4431, A-99, B-7, C-15), (IB-4432, A-99, B-10, C-15), (IB-4433, A-100, B-7, C-15), (IB-4434, A-100, B-10, C-15), (IB-4435, A-101, B-7, C-15), (IB-4436, A-101, B-10, C-15), (IB-4437, A-102, B-7, C-15), (IB-4438, A-102, B-10, C-15), (IB-4439, A-103, B-7, C-15), (IB-4440, A-103, 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(IB-4677, A-222, B-7, C-15), (IB-4678, A-222, B-10, C-15), (IB-4679, A-223, B-7, C-15), (IB-4680, A-223, B-10, C-15), (IB-4681, A-224, B-7, C-15), (IB-4682 A-224, B-10, C-15), (IB-4683, A-225, B-7, C-15), (IB-4684, A-225, B-10, C-15), (IB-4685, A-226, B-7, C-15), (IB-4686, A-226, B-10, C-15), (IB-4687, A-227, B-7, C-15), (IB-4688, A-227, B-10, C-15), (IB-4689, A-228, B-7, C-15), (IB-4690, A-228, B-10, C-15), (IB-4691, A-229, B-7, C-15), (IB-4692, A-229, B-10, C-15), (IB-4693, A-230, B-7, C-15), (IB-4694, A-230, B-10, C-15), (IB-4695, A-231, B-7, C-15), (IB-4696, A-231, B-10, C-15), (IB-4697, A-232, B-7, C-15), (IB-4698, A-232, B-10, C-15), (IB-4699, A-233, B-7, C-15), (IB-4700, A-233, B-10, C-15), (IB-4701, A-234, B-7, C-15), (IB-4702, A-234, B-10, C-15), (IB-4703, A-235, B-7, C-15), (IB-4704, A-235, B-10, C-15), (IB-4705, A-236, B-7, C-15), (IB-4706, A-236, B-10, C-15), (IB-4707, A-237, B-7, C-15), (IB-4708, A-237, B-10, C-15), (IB-4709, A-238, B-7, C-15), (IB-4710, A-238, B-10, C-15), (IB-4711, A-239, B-7, C-15), (IB-4712, A-239, B-10, C-15), (IB-4713, A-240, B-7, C-15), (IB-4714, A-240, B-10, C-15), (IB-4715, A-241, B-7, C-15), (IB-4716, A-241, B-10, C-15), (IB-4717, A-242, B-7, C-15), (IB-4718, A-242, B-10, C-15), (IB-4719, A-243, B-7, C-15), (IB-4720, A-243, B-10, C-15), (IB-4721, A-244, B-7, C-15), (IB-4722, A-244, B-10, C-15), (IB-4723, A-245, B-7, C-15), (IB-4724, A-245, B-10, C-15), (IB-4725, A-246, B-7, C-15), (IB-4726, A-246, B-10 C-15), (IB-4727, A-247, B-7, C-15), (IB-4728, A-247, B-10, C-15), (IB-4729, A-248, B-7, C-15), (IB-4730, A-248, B-10, C-15), (IB-4731, A-249, B-7, C-15), (IB-4732 A-249, B-10, C-15), (IB-4733, A-250, B-7, C-15), (IB-4734, A-250, B-10, C-15), (IB-4735, A-251, B-7, C-15), (IB-4736, A-251, B-10, C-15), (IB-4737, A-252, B-7, C-15), (IB-4738, A-252, B-10, C-15), (IB-4739, A-253, B-7, C-15), (IB-4740, A-253, B-10, C-15), (IB-4741, -254, B-7, C-15), (IB-4742, A-254, B-10, C-15), (IB-4743, A-255, B-7, C-15), (IB-4744, A-255, B-10, C-15), (IB-4745, A-256, B-7, C-15), (IB-4746, A-256, B-10, C-15), (IB-4747, A-257, B-7, C-15), (IB-4748, A-257, B-10, C-15), (IB-4749, A-258, B-7, C-15), (IB-4750, A-258, B-10, C-15), (IB-4751, A-259, B-7, C-15), (IB-4752, A-259, B-10, C-15), (IB-4753, A-260, B-7, C-15), (IB-4754, A-260, B-10, C-15), (IB-4755, A-261, B-7, C-15), (IB-4756, A-261, B-10, C-15), (IB-4757, A-262, B-7, C-15), (IB-4758, A-262, B-10, C-15), (IB-4759, A-263, B-7, C-15), (IB-4760, A-263, B-10, C-15), (IB-4761, A-264, B-7, C-15), (IB-4762, A-264, B-10, C-15), (IB-4763, A-265, B-7, C-15), (IB-4764, A-265, B-10, C-15), (IB-4765, A-266, B-7, C-15), (IB-4766, A-266, B-10, C-15), (IB-4767, A-267, B-7, C-15), (IB-4768, A-267, B-10, C-15), (IB-4769, A-268, B-7, C-15), (IB-4770, A-268, B-10, C-15), (IB-4771, A-269, B-7, C-15), (IB-4772 A-269, B-10, C-15), (IB-4773, A-270, B-7, C-15), (IB-4774, A-270, B-10, C-15)

Test example 1. Inhibitory activity against the DP receptor in vitro

1) preparation of platelets and method of analysis camp

Using a syringe one-ninth of which was filled with 3.8% sodium citrate in a healthy volunteer was collected 30 ml of peripheral blood. The obtained blood was centrifuged with acceleration 180 g for 10 minutes at room temperature, the supernatant was collected and used as a plasma with a high concentration of platelets (PRP). Received PRP was washed with wash buffer and centrifuged three times (washed platelets (WP), and then made calculations of platelets by means of a counter miniature cells. Washed platelets (WP) was injected into the Cup in the amount of 1.5 × 108(analysis and the Cup was treated with 3-isobutyl-1-metil what Antin (IBMX; 0.5 mm) for 5 minutes. The interaction was initiated by adding 100 nm PGD2 after 5 minutes after administration of the test compounds. The interaction was stopped by adding 2 minutes later, 1 N. hydrochloric acid solution, after which the cells were destroyed 12% Triton X-100. The amount of camp in the supernatant was determined by the method of uniform non-specific fluorescence (HTRF).

2) Analysis of the receptor binding

Received the washed platelets (WP) homogenized and the result of performing high-speed centrifugation of the collected membrane fraction. In the Cup entered the compound of the present invention or reference compound (No. IC-73, described in WO 2003/097598) and [3H]-PGD2. Then added to the membrane fraction of platelets with a protein concentration of 2 mg/ml, were mixed in the Cup and placed on ice for 2 hours. The reaction solution was transferred to a filter for adsorption of protein in small quantities and washed eight times with wash solution using harvester cells. After the last wash was carefully removed the water and entered the scintillator. Inhibitory activity against the DP receptor was determined by measuring [3H] device Micro Beta.

Table 61 shows the values of 50% DP-inhibitory concentration (IC50)obtained when performing analysis of camp, and the Ki values obtained in the analysis of the receptor binding.

3) Analysis of agonists and antagonists of prostanoid

Agonistic and antagonistic activity of the compounds of the present invention in respect of prostanoid receptors was determined on the basis of intracellular calcium flux or production of camp, serving as an indicator, with SOME cells 293 expressing respectively ER, ER, ER, ER, FP, TP and IP man. Tested compound showed no agonistic activity towards these prostanoids. On the other hand, the tested compounds was detected strong antagonistic activity (IC50), which is more than twenty times higher than the IC50 value obtained in the analysis of camp in washed platelets (WP).

Table 61
No. of connectionsIC50 (nm)Ki (nm)No. of connectionsIC50 (nm)Ki (nm)
I-72,4II-600,882,6
I-82,1 II-612,11,4
I-102,730II-621,1the 4.7
I-113,0II-650,1416
I-124,2II-671,7
I-181,6II-6817
I-300,51II-691,4
I-310,163,6II-714,1
II-84,6II-731,0 1,1
II-100,410,65II-740,520,24
II-112,3II-750,580,58
II-130,280,81II-773,6
II-160,250,87II-792,3
II-170,230,57II-800,200,23
II-18a 4.9II-811,82,6
II-191,12,0II-821,15,0
II-20 4,3II-832,020
II-240,511,7II-840,180,33
II-250,671,6II-850,511,7
II-260,430,63II-880,231,5
II-271,01-4II-892,120
II-282,5the 3.8II-900,59
II-290,380,74II-911,3
II-290,38 0,74II-911,3
II-310,813,7II-920,360,58
II-330,301,9II-942,01,7
II-350,473,1II-952,4the 4.7
II-371,5II-960,290,33
II-380,650,25II-990,5911
II-413,5II-1002,412,8
II-430,742,3II-101 0,2122
II-440,691,6II-1051,516
II-460,790,87II-1061,619
II-473,12,2II-1080,1313
II-484,6II-1100,369,8
II-510,640,52II-1110,7036
II-532,3II-1120,129,3
II-540,420,27II-1342,7 8,5
II-553,0II-1350,130,49
II-571,2
II-583,5
II-594,3

Test example 2. A test using a model of asthma in rats induced by ovalbumin (OVA)

Gray (BN) rats were senzibilizirani by intraperitoneal administration of 0.1 mg/ml ovalbumin (OVA) and 1 mg gel of aluminum hydroxide. A solution of 1% OVA was sprayed using an ultrasonic nebulizer (NE-U17), exposing rats exposed to inhalation aerosol for 30 minutes in the chamber for inhalation through 12, 19, 26 and 33 days after sensitization. One hour before the 4th antigen exposure to rats orally was administered compounds of the present invention in the dose of 10 mg/kg once a day during the AI three consecutive days. In the control group rats were injected with 0.5% methylcellulose instead of the compounds of the present invention.

In the jugular vein of the rats, shot by pentobarbital (80 mg/kg, intraperitoneally), consistently were injected with acetylcholine(3,9, 7,8, 15,6, 31,3, 62,5, 125, 250 and 500 µg/kg), starting with lower doses, at intervals of 5 minutes three days after the fourth antigen exposure and measured the immediate contractile response of the respiratory tract (increased pressure insufflation) using a modified method of Konzett and Ressler. The intensity of inhibition of hypersensitivity compared with the control group was calculated based on the area under the curve (AUC) according to the reaction on the concentration of acetylcholine.

After the measurement is increased hypersensitivity of the Airways bronchi and alveoli of rats three times washed with 5 ml of physiological solution. The total number of cells in the lavage was calculated using hemocytometer under a light microscope and determined the intensity of inhibition of infiltration of inflammatory cells infiltration in comparison with the control group. In addition, the ELISA method was measured by the mucin in the wash fluid of the respiratory tract using jacalin, mucin-binding lectin, and calculated the intensity of inhibiting mucus secretion compared to the control g is uppoi.

The results are shown in table 62:

Table 62
no modifications indose (mg/kg)the intensity of inhibition (%)
hypersensitivity of the Airwaysinfiltration of inflammatory cells infiltratethe secretion of mucus
II-110597679
II-310507878
II-1310994647
II-16101316776
II-1710895349
II-1910 545159
II-2410776789
II-26109737121
II-27104949118
II-29108960110
II-3310725776
II-3510886084
II-3810396971
II-4310563398
II-541011939106
II-6310415979
II-74101116592
II-8010395782
II-8410825456
II-9210534644
II-96101054652

Test example 3. A test using a model of edema of the nasal cavity in Guinea pigs

Below is illustrated the methods of measuring the resistance of the nasal cavity and activity against edema of the nasal cavity using Guinea pigs.

Male Guinea pigs HART who was her senzibilizirani by aerosol inhalation, containing 1% solution of ovalbumin (OVA), within 10 minutes two times with an interval of one week and initiated the reaction, subjecting animals to exposure to antigen after 7 days. Guinea pigs, shot by pentobarbital (30 mg/kg, intraperitoneally), cut the trachea and entered the cannula from the nasal cavity and lungs. From light was added the ventilator, feeding 4 ml of air at a time with a speed of 60 times/min Spontaneous breathing Guinea pigs stopped by introducing gallamine (2 mg/kg, intravenously) and with the help of the ventilator through the cannula from the side of the nose was filed in the nose 4 ml of air at a time with a speed of 70 times/min air Pressure required for air supply, measured using a sensor attached to a side branch, and used as an indicator of the resistance of the nasal cavity. Guinea pigs were subjected to antigen, spraying aerosol containing 3% solution of OVA, between the ventilator and the cannula in the nose for three minutes. Compounds of the present invention was administered intravenously 10 minutes prior to antigen exposure. The resistance of the nasal cavity is constantly measured during the time period from 0 to 30 minutes and the intensity of inhibition compared to the filler was determined is based on the area under the curve (AUC), built within 30 minutes, indicating the resistance of the nasal cavity (cm H2A) on the y axis and time (from 0 to 30 minutes) on the x-axis.

Examples of preparation of medicines

The following examples of preparation of medicines 1-8 are shown for illustrative purposes only and do not limit the scope of the present invention. The term “active ingredient” means the compounds of the present invention, their pharmaceutically acceptable salt or hydrate.

Example of preparation of medicines 1

Hard gelatin capsule get, using the following ingredients:

Quantity (mg/capsule)
the active ingredient250
starch (dry)200
magnesium stearate10
Only460 mg

Example preparation of the medicinal product 2

Pill get, using the following ingredients:

Quantity (mg/tablet)
the active ingredient250
cellulose (microcrystalline)400
silicon dioxide (fuming)10
stearic acid5
Only665 mg

The above ingredients are mixed and pressed to form tablets weighing 665 mg/tablet.

Example of preparation of medicines 3

Aerosol solution get, using the following ingredients:

weight
the active ingredient0,25
ethanol25,75
the propellant 22 (hardifort)74,00
Only100,00

The active ingredient and ethanol are mixed, the mixture was added to a portion of the propellant 22, the resulting solution was cooled to -30°C. and transferred to a filling device. In the cylinder stainless steel input the appropriate amount of the mixture and the contents of the container of Rabb who make the rest of the propellant. Cylinder set valve device.

Example of preparation of medicines 4

Tablet containing 60 mg of active ingredient, was prepared as follows:

the active ingredient60 mg
starch45 mg
microcrystalline cellulose35 mg
polyvinylpyrrolidone (10% aqueous solution)4 mg
carboxymethylate starch sodium4.5 mg
magnesium stearate0.5 mg
talc1 mg
Only150 mg

The active ingredient, starch and cellulose sieved through a sieve with openings No. 45 U.S. standard and thoroughly mix. The resulting powder was mixed with a solution containing polyvinylpyrrolidone, and the mixture is sieved through a sieve with openings of No. 14 U.S. standard. The granulated powder is dried at 50°C and sieved through a sieve with openings No. 18 U.S. standard. Carboxymethyl the wet starch sodium, magnesium stearate and talc sift through a sieve hole size No. 60 U.S. standard and add to granular powder, are mixed and pressed into teletrauma machine to form tablets weighing 150 mg/tablet.

Example of preparation of medicines 5

Capsule containing 80 mg of the active ingredient, was prepared as follows:

the active ingredient80 mg
starch59 mg
microcrystalline cellulose59 mg
magnesium stearate2 mg
Only200 mg

The active ingredient, starch, cellulose and magnesium stearate are mixed, sieved through a sieve with openings No. 45 standard USA and is administered in gelatin capsules, while receiving the drug in a capsule containing 200 mg/capsule.

Example of preparation of a medicinal product 6

Suppository containing 225 mg of active ingredient, was prepared as follows:

the active ingredient 225 mg
the glycerides of saturated fatty acids2000 mg
Only2225 mg

The active ingredient is sifted through a sieve with openings No. 60 U.S. standard and suspended in the glycerides of saturated fatty acid, melted at minimum heat. The mixture is then cooled in the form of the number 2,

Example of preparation of medicines 7

The suspension containing 50 mg of active ingredient, was prepared as follows:

the active ingredient50 mg
sodium carboxymethylcellulose50 mg
syrup1.25 ml
a solution of benzoic acid0.10 ml
flavorin any quantity
pigmentin any quantity
All (with the addition of purified water)5 ml

The active ingredient is sifted through a sieve with openings no thangata USA and is mixed with the sodium carboxymethyl cellulose and syrup with the formation of a homogeneous paste. A solution of benzoic acid and the flavor is diluted with a part of water, add to the pasta and mix. Add the required amount of water, thus obtaining the desired suspension.

Example of preparation of a medicinal product 8

Drug for intravenous injection was prepared as follows:

the active ingredient100 mg
the glycerides of saturated fatty acids1000 ml

The solution containing the above active ingredient, usually injected to a subject intravenously at a rate of 1 ml/min

Industrial applicability

It is established that the new derived sulfonamida has an antagonistic activity against DP receptor and exerts effective in the treatment of allergic diseases.

1. The compound of General formula (III)

in which ring D is a benzene ring, 2-peritoneum ring, pyridine ring, benzoxazole ring, benzoxazinone ring or a benzimidazole ring;
R1means carboxy or hydroxy;
R2independently denotes a halogen atom;
alkyl, optionally substituted by a halogen atom, aryl or al is aluminum;
quinil, optionally substituted, alkyloxy;
hydroxy;
carboxy;
alkyloxy, optionally substituted phenyl, an aromatic heterocyclic ring, which means 5-6-membered aromatic monocyclic carbocyclic ring containing one or two heteroatoms independently selected from oxygen atoms and nitrogen;
alkylsulfonyl;
aryloxy;
amino, optionally substituted alkyl; acyl, optionally substituted alkyl or alkyloxy; allyloxycarbonyl; alkanesulfonyl; arylsulfonyl or allylcarbamate;
carbarnoyl, optionally substituted by alkyl, phenyl, cycloalkyl, acetyl, alkanesulfonyl, heteroallyl, cycloalkylation, heteroaryl, which means 5-6-membered monocyclic aromatic ring containing one to three heteroatoms independently selected from oxygen atoms and nitrogen and which is optionally substituted by alkyl or cycloalkyl;
acyl;
cyano;
nitro;
aryl;
heteroaryl, which means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen and which is optionally substituted by alkyl;
alkylsulfonyl;
morpholinylcarbonyl;
non-aromatic heterocyclic group, which means 5-6-membered nonaromatic heterotic the practical ring, containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom;
R3means C1-C6alkyloxy,1-C6alkylthio;
R4means a halogen atom or alkyloxy;
R5means alkyl;
M means sulfonyl;
L3independent means alkylene, optionally containing one oxygen atom or nitrogen, albaniles, or-N(R7)-;
R7independently means a hydrogen atom, alkyl;
Y represents a simple bond or CO;
Z denotes CH or N;
n means 0 or 1;
p denotes 0, 1 or 2;
q indicates 0 or 1; provided that R1does not mean carboxy, when ring D is a benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is orthopantogram in the ring D;
its pharmaceutically acceptable salt.

2. The compound according to claim 1, in which R1means carboxy-L3means -(O-optionally substituted alkylene)-;
its pharmaceutically acceptable salt.

3. The compound according to claim 1, in which ring D is a benzene ring or a pyridine ring;
its pharmaceutically acceptable salt.

4. The compound according to claim 1, in which R3means optionally substituted C1-C6alkyloxy or optionally substituted C1-C6alkylthio;
its pharmaceutically acceptable salt.

5. Connect the s according to claim 1, in which Y represents a simple bond;
its pharmaceutically acceptable salt.

6. The compound according to claim 1, in which R2means halogen atom; alkyl, optionally substituted by a halogen atom, aryl or alkylamino;
alkyloxy, optionally substituted phenyl, an aromatic geterotsiklicheskikh ring, which means 5-6-membered aromatic monocyclic carbocyclic ring containing one or two heteroatoms independently selected from oxygen atoms and nitrogen;
amino, optionally substituted alkyl, acyl, optionally substituted alkyl or alkyloxy, allyloxycarbonyl, alkanesulfonyl, arylsulfonyl or allylcarbamate;
carbarnoyl, optionally substituted by alkyl, phenyl, cycloalkyl, acetyl, alkanesulfonyl, heteroallyl, cycloalkylation, heteroaryl, which means 5-6-membered monocyclic aromatic ring containing one to three heteroatoms independently selected from oxygen atoms and nitrogen and which is optionally substituted by alkyl or cycloalkyl;
aryl;
heteroaryl, which means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen and which is optionally substituted by alkyl; or
non-aromatic heterocyclic group, which means the AET 5-6-membered non-aromatic heterocyclic ring, containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom; and
p is 1 or 2;
its pharmaceutically acceptable salt.

7. The compound according to claim 1, in which R2means a halogen atom; amino, optionally substituted alkyl, acyl, optionally substituted alkyl or alkyloxy, allyloxycarbonyl, alkanesulfonyl, arylsulfonyl or allylcarbamate;
carbarnoyl, optionally substituted by alkyl, phenyl, cycloalkyl, acetyl, alkanesulfonyl, heteroallyl, cycloalkylation, heteroaryl, which means 5-6-membered monocyclic aromatic ring containing one to three heteroatoms independently selected from oxygen atoms and nitrogen and which is optionally substituted by alkyl or cycloalkyl;
aryl;
heteroaryl, which means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen and which is optionally substituted by alkyl; or
non-aromatic heterocyclic group, which means 5-6-membered non-aromatic heterocyclic ring containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom; and
p is 1 or 2;
its pharmaceutically acceptable salt.

8. The compound according to claim 1, in which R2oznachaet is a halogen atom; alkyl, optionally substituted by halogen atom, aryl or alkylamino; alkyloxy, optionally substituted phenyl, an aromatic heterocyclic ring, which means 5-6-membered aromatic monocyclic carbocyclic ring containing one or two heteroatoms independently selected from oxygen atoms and nitrogen; and
q indicates 0 or 1;
its pharmaceutically acceptable salt.

9. The compound according to any one of claims 1 to 8, in which the position of substitution between Y and L3is metaprogram in the ring D;
its pharmaceutically acceptable salt.

10. The compound of General formula (IV)

in which ring D is a benzene ring or a pyridine ring;
ring E is a ring of the formula
,or
R1means carboxy;
R2means halogen atom, alkyl, alkyloxy;
R3means C1-C6alkyloxy;
M means sulfonyl;
L3means alkylene, optionally containing one oxygen atom, or albaniles;
Y represents a simple bond or oxygen;
Z denotes CH;
n means 0;
p denotes 0 or 1;
q is 0;
provided that (a) R1does not mean carboxy, when ring D is a benzene ring, -L3means -(O-alkylene)and position is the substitution of L 3and Y is ortho-position in the ring D, b) a group of the formula

is not a group of the formula

when ring D is a benzene ring, -L3means -(O-alkylene)and the position of substitution of the L3and Y is paraboloidal in the ring D;
its pharmaceutically acceptable salt.

11. The connection of claim 10, in which R1means carboxy-L3means - (O-optionally substituted alkylene)-;
its pharmaceutically acceptable salt.

12. The connection of claim 10, in which ring D is a benzene ring or a pyridine ring; its pharmaceutically acceptable salt.

13. The connection of claim 10, in which R3means C1-C6alkyloxy or C1-C6alkylthio;
its pharmaceutically acceptable salt.

14. The connection of claim 10, in which Y represents a simple bond; its pharmaceutically acceptable salt.

15. The connection of claim 10, in which R2means halogen atom, alkyl or alkyloxy; and p is 1; its pharmaceutically acceptable salt.

16. The connection of claim 10, in which R2means a halogen atom, and p is 1;
its pharmaceutically acceptable salt.

17. The connection of claim 10, in which the position of substitution between Y and L3is metaprogram in the ring D;
its pharmaceutically acceptable salt.

18. The pharmacy is practical composition, having antagonistic activity against receptor DP containing the compound according to any one of claims 1 to 17, its pharmaceutically acceptable salt as an active ingredient.

19. The pharmaceutical composition according p, which is a drug for the treatment of allergies.

20. The pharmaceutical composition according to claim 19, in which the medicinal product for the treatment of allergies is a drug for the treatment of asthma.

21. A method of treating diseases caused by the DP receptor, characterized by introducing the compound according to any one of claims 1 to 17, its pharmaceutically acceptable salt.

22. The method according to item 21, in which the disease is due to DP receptor is asthma.

23. The use of compounds according to any one of claims 1 to 17, its pharmaceutically acceptable salt for a medicinal product for the treatment of diseases caused by the DP receptor.

24. The use of compounds according to item 23, its pharmaceutically acceptable salts, in which the disease is due to DP receptor is asthma.

25. The compound of General formula (V)

in which ring D is a benzene ring, 2-peritoneum ring, pyridine ring, benzoxazole ring, benzoxazinone ring or a benzimidazole ring;
R1means carboxy or hydroxy;
R2the independent which IMO means a halogen atom;
alkyl, optionally substituted by a halogen atom, aryl or alkylamino;
quinil, optionally substituted, alkyloxy;
hydroxy;
carboxy;
alkyloxy, optionally substituted phenyl, an aromatic heterocyclic ring, which means 5-6-membered aromatic monocyclic carbocyclic ring containing one or two heteroatoms independently selected from oxygen atoms and nitrogen;
alkylsulfonyl;
aryloxy;
amino, optionally substituted alkyl; acyl, optionally substituted alkyl or alkyloxy; allyloxycarbonyl; alkanesulfonyl; arylsulfonyl or allylcarbamate;
carbarnoyl, optionally substituted by alkyl, phenyl, cycloalkyl, acetyl, alkanesulfonyl, heteroallyl, cycloalkylation, heteroaryl, which means 5-6-membered monocyclic aromatic ring containing one to three heteroatoms independently selected from oxygen atoms and nitrogen and which is optionally substituted by alkyl or cycloalkyl;
acyl;
cyano;
nitro;
aryl;
heteroaryl, which means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen and which is optionally substituted by alkyl;
alkylsulfonyl;
morpholinylcarbonyl;
nah Goethe is acyclically group, which means 5-6-membered non-aromatic heterocyclic ring containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom;
R8means halogen atom, tripterocalyx or piperazine derivatives;
L3independent means alkylene, optionally containing one oxygen atom or nitrogen, albaniles, or-N(R7)-;
R7means a hydrogen atom, alkyl;
p is 1 or 2;
provided that the position of substitution of piperidinium and L3is not ortho-position to the D ring, when ring D is a benzene ring and the-L3means -(O-alkylene)-;
its pharmaceutically acceptable salt.

26. Connection A.25, in which ring D is a benzene ring and R8means halogen atom; its pharmaceutically acceptable salt.

27. Connection A.25, in which ring D is a benzene ring and R8means piperazine derivatives; its pharmaceutically acceptable salt.

28. Connection A.25, in which R1means carboxy-L3means -(O-methylene)-; its pharmaceutically acceptable salt.

29. Connection A.25, in which R2means halogen atom;
amino, optionally substituted alkyl; acyl, optionally substituted alkyl or alkyloxy; allyloxycarbonyl; alkanesulfonyl; arylsulfonyl or alkylaryl the sludge;
carbarnoyl, optionally substituted by alkyl, phenyl, cycloalkyl, acetyl, alkanesulfonyl, heteroallyl, cycloalkylation, heteroaryl, which means 5-6-membered monocyclic aromatic ring containing one to three heteroatoms independently selected from oxygen atoms and nitrogen and which is optionally substituted by alkyl or cycloalkyl;
aryl;
heteroaryl, which means 5-6-membered aromatic ring containing one or more heteroatoms independently selected from oxygen atoms, sulfur and nitrogen and which is optionally substituted by alkyl; or
non-aromatic heterocyclic group, which means 5-6-membered non-aromatic heterocyclic ring containing one or more nitrogen atoms and optionally an oxygen atom and/or sulfur atom; and
p is 1 or 2;
its pharmaceutically acceptable salt.

30. Connection A.25, in which the position of substitution between R8and L3the ring D is metaprogram;
its pharmaceutically acceptable salt.



 

Same patents:

FIELD: medicine.

SUBSTANCE: invention refers to derivatives of 2-pyridylmethylenecarboxamide of formula (I), where: -A represents a substituted or unsubstituted 5-member heterocyclyl group bound with carbonyl through carbon atom; -Z1 and Z2 which can be equal or different, represent hydrogen atom; C1-C5-alkyl; C5-alkoxycarbonyl; -Z3 represents substituted or unsubstituted C3-C7cycloalkyl; -Y represents C1-C5-halogenalkyl, containing to 5 halogen atoms which can be equal or different; X which can be equal or different, represents halogen atom, - n=0, 1, 2 or 3; and to their salts. Besides the invention describes a method of plant pathogenic fungi control with the use of such compounds.

EFFECT: there are prepared and described new derivatives of 2-pyridylmethylenecarboxamide which can be effective as fungicidal active agents.

8 cl, 96 ex, 4 tbl

FIELD: medicine.

SUBSTANCE: invention refers to new compounds exhibiting antiproliferative activity of formula (1) where W means N or C-R2; X means -NH-; Y means CH; Z means halogen, -NO2, C2-C3alkynyl-, halogen-C1-C3alkyl- and -C(=O)-C1-C3alkyl, A means a group of formula (i), (ii) or (iii) Q1 means phenyl; B1, B2, B3 and B4 independently mean C-RgRh, N-Ri or O; R1 means hydrogen; R2 means a residue specified from the group including hydrogen, halogen and -OR4; Ra, Rb, Rc, Rd, Re and Rf independently mean hydrogen; Rg and Rh independently mean a residue specified from the group including hydrogen, =O, -OR4 and -NR4C(=O)R5; or mean optionally a residue monosubstituted or twice-substituted with equal or different substitutes and specified from the group including C1-C6alkyl and phenyl, the substitute/substitutes is/are specified from the group including R8/, -OR4, -C(=O)R4, -C(=O)OR4 and -C(=O)NR4R5 where R8/ and other values of radicals are specified in the patent claim, optionally in the form of their pharmacologically noncontaminating acid addition salts. The invention also concerns a pharmaceutical composition.

EFFECT: new compounds have effective biological properties.

8 cl, 6 dwg, 1086 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: there are described novel compounds of formula (I), where R1 represents hydroxymethyl; R2 is selected from -C(O)NR4R5; HET-1 represents 5- or 6-member heteroaryl ring, bound by atom C; R3 represents halogeno; R4 and R5 together with nitrogen atom, to which they are bound, can form heterocyclyl ring system, as it is defined for HET-3; HET-3 represents possibly substituted azetidinyl; m equals 1; n equals 0, 1 or 2; or their pharmaceutically acceptable salt, which can be applied as glucokinase (GLK) activators or active ingredient of pharmaceutical compositions, also described are methods of obtaining them.

EFFECT: creation of novel compounds applied as glucokinase (GLK) activators in treatment of diabetes.

13 cl, 40 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: there are described novel acylsulfonamide peri-substituted condensed bicyclic compounds of general formula (I), values of radicals are given in invention formula. Also described is pharmaceutical composition based on formula (I) compound.

EFFECT: compounds can be used for inhibition of prostaglandin E2 binding with receptor EP3.

30 cl, 371 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: in embodiments of the invention, specific compounds are used to prepare a medicinal agent for treating, relieving and preventing conditions associated with dysfunction of monoamine transmission. The compounds have general formula (1) , where: R1 and R2 are identical or different and denote hydrogen, alkyl, alkenyl, alkynyl, aryl, thio or alkylthio, or R1 and R2 may have extra substitutes which are selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkyloxy, morpholin-4-ylalkoxy, piperidin-1-ylalkyloxy, alkylamino, dialkylamino, arylamino.

EFFECT: more efficient use of compounds in preparing medicinal agents.

8 cl, 3 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to novel quinoline or quinazoline derivatives of general formula

Ib, where R1 is C1-6-alkyl or C1-6-alkoxy; X is N or CH; R3 and R4 independently denote hydrogen, C1-6-alkyl, C1-6-alkylsulphonyl or a group of formula (IIa), where A is oxygen or sulphur; D is -(CH2)t, -(CH2)tO- or -O(CH2)t, where t equals 0, 1, 2, 3 or 4; and E is C1-6-alkyl, C3-7-cycloalkyl, or a 3-7-member monocyclic aromatic ring or a 6-10-member bicyclic aromatic ring in which 1-3 carbon atoms in the ring(s) are optionally substituted with a heteroatom which is independently selected from nitrogen, oxygen and sulphur, (optionally substituted with 1 or 2 substitutes independently selected from halogen, C1-6-alkyl, CF3, cyano, hydroxy and C1-6-alkoxy); or a group of formula (IIb), where A is oxygen or sulphur; D is -(CH2)t-, -(CH2)tO- or -O(CH2)t, where t equals 0, 1, 2, 3 or 4; and E is C1-6-alkyl, C3-7-cycloalkyl, or a 3-7-member monocyclic aromatic ring or a 6-10-member bicyclic aromatic ring in which 1-3 carbon atoms in the ring(s) are optionally substituted with a heteroatom which is independently selected from nitrogen, oxygen and sulphur (optionally substituted with 1 or 2 substitutes independently selected from halogen, C1-6-alkyl, CF3, cyano, hydroxy and C1-6-alkoxy); or R3 and R4 together with the nitrogen atom with which they are bonded form a 3-7-member ring or a 6-10-member bicyclic ring which can be saturated, partially saturated or unsaturated and contain 1, 2 or 3 heteroatoms selected from nitrogen, sulphur and oxygen, where each group is optionally substituted with 1 or 2 substitutes selected from oxo, C1-6-alkyl, C1-6-alkoxy, aryl and aryl-C1-6-alkyl (where aryl and aryl-C1-6-alkyl are also optionally substituted with 1 or 2 with C1-6-alkyls or C1-6-alkoxy). The invention also relates to use of formula Ib compounds in preparing a medicinal agent, to a pharmaceutical composition based on formula Ib compound and preparation method thereof.

EFFECT: obtaining novel quinoline and quinazoline derivatives having high affinity to 5-HT1-receptors.

12 cl, 171 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to medication, reducing desire for alcohol, which represents substituted 1H-benzimidazoles of general formula 1 or their pharmaceutically acceptable salts and/or hydrates, pharmaceutical composition, and medication on their basis. Compounds can be applied in treatment of alcohol abuse with application of ethanol-containing products, if necessary, together with antidepressants. In compounds of general formula 1 , where: W represents sulfur atom or group S=O; R1 represents one or more substituents, selected from hydrogen, halogen, C1-C4alkyl, C1-C4alkyloxy, optionally substituted 5-6-member azaheterocyclyl with 1-2 atoms of nitrogen and/or oxygen in cycle; R2 represents atom of hydrogen or optionally substituted C1-C4alkyl; R3 and R4 independently on each other represent optionally similar substituents, selected from hydrogen, optionally substituted C1-C4alkyl, C3-C6cycloalkyl; R5 represents alkyl substituent, selected from hydrogen or optionally substituted C1-C7alkyl, C1-C7alkenyl, C1-C4alkynyl, optionally substituted phenyl, optionally substituted 5-6-member heterocyclyl with 1-3 heteroatoms, selected from nitrogen, oxygen and sulfur, possibly condensed with benzene ring; C1-C4-alkoxycarbonyl, optionally substituted amino carbonyl, or group CR3R4R together stands for group , where Alk stands for C1-C4alkyl.

EFFECT: medication allows to reduce symptoms of alcohol abuse considerably as compared with earlier known compounds and does not produce unfavorable effect on liver function.

12 cl, 3 tbl, 2 ex, 1 dwg

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel 5-6-member nitrogen-containing heterocyclic compounds, selected form derivatives of pyridine, pyrimidine, imidasoline, oxadiasoline, such as, for instance , which possess inhibiting activity with respect to aspartylprotease, such as "ВАСЕ-1".

EFFECT: obtaining pharmaceutical composition, method of aspartylprotease inhibition aimed at application of compounds for preparation of medication intended for treatment of state, mediated by aspartylprotease, such as "ВАСЕ-1".

4 cl, 1 tbl, 1832 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel pyrimidine derivatives having FAK inhibitory activity of formula (I), where R0 is hydrogen; R1 is a 5- or 6-member heterocycle containing 1 or 2 nitrogen atoms substituted with (C1-C7)alkyl, hydroxyl group, dialkylamino group or a 6-member heterocycle containing one nitrogen atom; R2 is hydrogen; R3 is carbamoyl substituted once or twice with (C1-C7)alkyl; a 5-member heterocycle containing 4 nitrogen atoms; SO2N(R12)R13, where R12 is hydrogen or (lower)alkyl, and R13 is hydrogen, (C1-C7)alkyl, (C1-C7)alkoxy(C1-C7)alkyl, di(C1-C7)alkylamino(C1-C7)alkyl, hydroxy(C1-C7)alkyl, or R12 and R13 together a nitrogen atom with which they are bonded form a 6-member heterocycle containing two nitrogen atoms, where the said heterocycle is not substituted or substituted with (C1-C7)alkyl; R4 is hydrogen; R5 is a halide; R6 is hydrogen; R7 is hydrogen; (C1-C7)alkoxy; carbamoyl which is not substituted or substituted with (lower)alkyl; a 5- or 6-member heterocycle containing 1 or 2 nitrogen or oxygen atoms, unsubstituted or substituted with di(C1-C7)alkylamino, (C1-C7)alkyl, hydroxy, 6-member heterocycle containing 1 or 2 nitrogen or oxygen ring atoms, unsubstituted or substituted with (C1-C7)alkyl; 6-member heterocycle-oxy containing 1 nitrogen ring atom, unsubstituted or substituted with (C1-C7)alkyl; heterocycle(C1-C7)alkyloxy, where heterocycle denotes a 5- or 6-member heterocycle containing 1 or 2 nitrogen or oxygen ring atoms which is not substituted or substituted with (C1-C7)alkyl; R8 is hydrogen; halide; (C1-C7)alkoxy, carbamoyl unsubstituted or substituted with (C1-C7)alkyl; heterocycle(C1-C7)alkyloxy, where heterocycle denotes a 5-member heterocycle containing 1 nitrogen ring atom, unsubstituted or substituted with (C1-C7)alkyl; 5- or 6-member heterocycle containing 1 or 2 nitrogen or oxygen atoms, unsubstituted or substituted with one or two substitutes independently selected from hydroxy, (C1-C7)alkyl, aminocarbonyl and (C1-C7)alkylamino; 6-member heterocycle-oxy, containing 1 nitrogen ring atom, unsubstituted or substituted 1-5 times with (C1-C7)alkyl or di(C1-C7)alkylamino; or R7 and R8 together with atoms with which they are bonded form a 6-member heterocycle containing two nitrogen or oxygen atoms, unsubstituted or substituted once or twice with (C1-C7)alkyl or oxo group; R9 is hydrogen; R10 is (C1-C7)alkoxy, as well as to their pharmaceutically acceptable salts. The invention also relates to a pharmaceutical composition and synthesis method.

EFFECT: novel compounds have useful biological activity.

4 cl, 167 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to organic chemistry, and specifically to compounds of general formula I , where A is an oxygen atom, an alkylene, alkenyl or hetero alkylene group, in which the CH2 group is substituted with a NH group, where the said groups can be optionally substituted with OH, =O or CH2OH groups, X1, X2, X3, X4 and X5 independently represent nitrogen atoms or groups of formula CH or CR4, Cy is cycloalkylene or heterocycloalkylene group containing at least one nitrogen atom, R1 is a hydrogen atom, an alkyl or alkyloxy group, R2 is a halogen atom, a hydroxy group, an alkyl or heteroalkyl residue, where the said groups can be optionally substituted with OH, NH2 groups and/or a =O group, R3 is a group of formula -B-Y, in which B denotes an alkylene, alkenyl or heteroalkylene group, where the said groups can be optionally substituted with OH, NH2, COOH groups or a =O group, and Y is an optionally substituted phenyl, optionally substituted heteroaryl group containing 5 or 6 ring atoms, or an optionally substituted bicyclic heterocycle in which one ring is phenyl or pyridyl, and the other is a 5-, 6- or 7-member heteroaryl or heterocycloalkyl group which contains up to 3 heteroatoms selected from nitrogen, oxygen and sulphur atoms, R4 is a halogen atom, n equals 0, 1 or 2 and m equals 0 or 1, or their pharmaceutically acceptable salts, solvates and hydrates. The invention also relates to a pharmaceutical composition based on the formula I compound and use of the compound or the pharmaceutical composition to treat bacterial infections.

EFFECT: obtaining novel compounds possessing useful biological properties.

12 cl, 7 ex

FIELD: medicine.

SUBSTANCE: invention refers to derivatives of 2-pyridylmethylenecarboxamide of formula (I), where: -A represents a substituted or unsubstituted 5-member heterocyclyl group bound with carbonyl through carbon atom; -Z1 and Z2 which can be equal or different, represent hydrogen atom; C1-C5-alkyl; C5-alkoxycarbonyl; -Z3 represents substituted or unsubstituted C3-C7cycloalkyl; -Y represents C1-C5-halogenalkyl, containing to 5 halogen atoms which can be equal or different; X which can be equal or different, represents halogen atom, - n=0, 1, 2 or 3; and to their salts. Besides the invention describes a method of plant pathogenic fungi control with the use of such compounds.

EFFECT: there are prepared and described new derivatives of 2-pyridylmethylenecarboxamide which can be effective as fungicidal active agents.

8 cl, 96 ex, 4 tbl

FIELD: medicine.

SUBSTANCE: invention refers to new compounds exhibiting antiproliferative activity of formula (1) where W means N or C-R2; X means -NH-; Y means CH; Z means halogen, -NO2, C2-C3alkynyl-, halogen-C1-C3alkyl- and -C(=O)-C1-C3alkyl, A means a group of formula (i), (ii) or (iii) Q1 means phenyl; B1, B2, B3 and B4 independently mean C-RgRh, N-Ri or O; R1 means hydrogen; R2 means a residue specified from the group including hydrogen, halogen and -OR4; Ra, Rb, Rc, Rd, Re and Rf independently mean hydrogen; Rg and Rh independently mean a residue specified from the group including hydrogen, =O, -OR4 and -NR4C(=O)R5; or mean optionally a residue monosubstituted or twice-substituted with equal or different substitutes and specified from the group including C1-C6alkyl and phenyl, the substitute/substitutes is/are specified from the group including R8/, -OR4, -C(=O)R4, -C(=O)OR4 and -C(=O)NR4R5 where R8/ and other values of radicals are specified in the patent claim, optionally in the form of their pharmacologically noncontaminating acid addition salts. The invention also concerns a pharmaceutical composition.

EFFECT: new compounds have effective biological properties.

8 cl, 6 dwg, 1086 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel improved method for synthesis of N-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidine-sulphone)-N'-isonictinoyl hydrazide, which can be used as a substance of medicinal agents for treating and preventing secondary immunodeficiencies, mycobacterial and viral infections, by reacting 6- methyluracil-5-sulphochloride with isonicotinic acid hydraside, characterised by that reaction of 6- methyluracil-5-sulphochloride with isonicotinic acid hydrazide in equimolar ratio takes place in a γ- butyrolacton medium at 90-100°C for 2 hours, followed by purification of the desired product in aqueous ammonium solution at 75-80°C and extraction from the solution at pH 4.5.

EFFECT: method shortens duration the process and increases output of the desired product.

1 cl, 2 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel compounds of formula: I, where R1 is selected from group, consisting of ethyl, 2-fluorethyl and isopropyl; R2 is selected from group, consisting of hydrogen, C1-7-alkyl, hydroxy, C1-7-alkoxy, C3-7-cycloalkyl, halogen, -C(O)OR6, where R6 represents C1-7-alkyl, amino, phenyl, phenyl, substituted with 1-3 substituents, selected from group, consisting of halogen, halogen-C1-7-alkyl and halogen-C1-7-alkoxy, pyridyl, imidazolyl, triazolyl and pyrrolyl; R3 is selected from group, consisting of hydrogen, C1-7-alkoxy, amino, -O-benzyl and -o-tetrahydropyranyl; or R2 and R3 are bound to each other with formation of cycle together with carbon atoms to which they are bound, and R2 and R3 together represent -CH=CH-NH-; R4 is selected from group, consisting of hydrogen, halogen, pyridyl and pyrimidyl; R5 and R5' independently on each other are selected from hydrogen or methyl; A is selected from group, consisting of isphenyl; phenyl, substituted with 1-3 substituents, selected from group, consisting of C1-7-alkyl, C3-7-cycloalkyl, C1-7-alkylsulfonyl, -O-C1-7-alkylsulfonyl, hydroxy, C1-7-alkoxy, hydroxy-C1-7-alkyl, hydroxy-C2-7-alkoxy, dihydroxy-C3-7-alkoxy, C1-7-alkylamino, di-C1-7-alkylamino, amino-C2-7-alkoxy, amino-C1-7-alkyl, -C(O)NR10R11, -O-C1-7-alkylene-C(O)NR10R11, -C(O)OR10, -C1-7-alkylene-C(O)OR10, -O-C1-7-alkylene-C(O)OR10, halogen, halogen-C1-7-alkoxy, cyano- C1-7-alkoxy, fluorphenyl, pyridyl, tetrazolyl and tetrazolyl- C1-7-alkoxy; 1,3-benzodioxolyl; naphtyl; pyrimidinyl; pyridyl, substituted with one or two substituents, selected from group, consisting of C1-7-alkyl, C1-7-alkoxy, amino, C1-7-alkylamino, di-C1-7-alkylamino, C3-7-cycloalkylamino, halogen, cyano, morpholinyl, imidazolyl and -NH-C(O)-R9, where R9 represents C1-7-alkyl or C3-7-cycloalkyl, and indolyl; R10 and R11 independently on each other represent hydrogen or C1-7-alkyl; and to their pharmaceutically accdeptable salts. Invention also relates to pharmaceutical compositions.

EFFECT: obtaining novel biologically active compounds, which are antagonists of somatostatin receptor subtype 5 (SSTR5).

26 cl, 266 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to 2-methyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives of formula 1 , in which R1 represents (1-6C)alkyl; R2 represents halogen; R3 represents SO2NR5R6 or (1-4C)alkoxy; X represents O or NR7; R4 represents R8-(2-8C)alkyl, R8-(3-8C)alkenyl or R8-(2-4C)alkoxy-(2-4C)alkyl; Z represents CN or NO2; R5 and R6 independently on each other represent H or (1-4C)alkyl; or R5 together with R6 and N, to which they are bound, form 5-6-member saturated ring, optionally containing additional heteroatom, selected from O; R8 represents OH, (1-4C)alkoxy, NH2; NR9C(O)R11, NR9SO2R11 or C(O)NR9R10; R7 and R9 independently represent H or (1-4C)alkyl; R10 represents (1-4C)alkyl; R11 represents (1-4C)alkyl, (1-4C)alkoxy(1-4C)alkyl, (3-6C)cycloalkyl, (1-4C)alkoxy or phenyl, or (4-5C)heteroaryl, and (4-5C)heteroaryl stands for aromatic group, which has 4-5 carbon atoms and at least one heteroatom, selected from N and O; or to their pharmaceutically acceptable salts. Invention also relates to pharmaceutical composition, as well as to application of 2-methyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives.

EFFECT: obtaining novel biologically active compounds, possessing agonistic activity with respect to FSH receptor.

8 cl, 33 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: claimed invention relates to compound of general formula (I) and its pharmaceutically acceptable salts. In general formula (I) , Y represents group -CONH(Q)- or -NHCONH(Q)-; Q represents 6-member aromatic ring or 5-10-member heteroaromatic ring, containing one or two N heteroatoms or two O heteroatoms; R represents hydrogen, halogen, linear or branched (C1-C6)alkyl; (C1-C6)alkoxy; di-(C1-C6)alkylamino, 5-member heteroaromatic ring, containing one O or S heteroatom; 6- or 9-member heteroaromatic ring, containing one or two N heteroatoms; phenyl, mono- or disubstituted with halogen, (C1-C6)alkyl, halogeno(C1-C6)alkyl, (C1-C6)alkoxy, acyl; hydroxy; piano; di-(C1-C6)alkylamino, acylamino' carbamoyl; X represents group : where Z represents CH2, N or O; m represents integer number from 1 to 3; p is equal 0, 1; R" is selected from group, consisting of di-( C1-C6)alkylaminocarbonyl, (C1-C6)alkyl, acyl. Invention also relates to pharmaceutical composition, containing as active ingredient, invention compound, to application of invention compound for manufacturing pharmaceutical composition, to method of inhibition of nicotinic acetylcholine receptor α7.

EFFECT: obtaining compound, which possesses agonistic activity with respect to nicotinic acetylcholine receptor (nAChR) α7.

7 cl, 2 tbl, 4 dwg, 270 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel compounds, which possess properties inhibiting HIV replication, of general formula (I) , in form of E-isomer, in which -a1=a2-a3=a4- represents bivalent radical of formula -CH=CH-CH=CH- (a-1); -b1=b2-b3=b4. Represents bivalent radical of formula -CH=CH-CH=CH- (b-1); n equals 0; m equals 2; each of R1 radicals independently on each other stands for hydrogen atom; C1-6alkyl; R2a stands for cyanogroup; X1 stands for -NR1-; R3 represents C2-6alkenyl, substituted with cyanogroup; R4 stands for C1-6alkyl; R5 represents radical of formula -Y-Alk-L, -Alk'-Y-L or -Alk'-Y-Alk-L; each of radicals Alk or Alk' independently represents bivalent C1-6alkyl or C2-6 alkenyl group; L stands for aryl or Het; Y stands for NR1; -CH=N-O-; Het stands for 5- or 6-member fully saturated ring system, in which one, two or three ring elements represent heteroatoms, each of which is independently selected from group, including nitrogen, oxygen and sulphur, and in which other ring elements represent carbon atoms; and, if possible, any nitrogen ring element can be optionally substituted with C1-6alkyl; and ring system can be optionally bound with benzene ring; and in which any carbon atom of ring, including any carbon atom of optionally bound benzene ring, each independently can be substituted with substituent selected from such groups as halogen atom, C1-6alkyl, hydroxyC1-4alkyl, carboxyC1-4alkyl, C1-4 alkylcarbonyloxyC1-4alkyl, di(C1-4alkyl)aminoC1-4alkyl, aryloxy, morpholinyl, aryl, Het1; Het1 stands for thienyl, isoxazolyl, thiadiazolyl, each of which can be optionally substituted with one or two C1-4alkyl radicals; Q stands for hydrogen atom; each aryl represents phenyl or phenyl, substituted with one, two substituents, each of which is independently selected from such groups as halogen atom, C1-6alkyl, C2-6alkinyl, cyano, polyhalogen C1-6alkyl or Het1, as well as to its pharmaceutically acceptable additive salts Invention also relates to pharmaceutical composition.

EFFECT: creation of novel compounds, which possess properties inhibiting HIV replication

5 cl, 7 tbl, 14 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel derivatives of 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline, represented by formula , where R1 represents (1-6C)alkyl; R2 represents halogen, (1-4C)alcoxy; R3 represents OH, NO2, CN, fluoridated with (1-4C)alkoxy, (1-4C)alkoxy(2-4C)alkoxy. hydroxy(2-4C)alkoxy, (1-4C)alkoxycarbonyl, R7, R8-amino, R9, R10-amino, R9, R10-aminocarbonyl, R9, R10-aminosulfonyl or phenyl(1-4C)alkoxy, where phenyl ring in composition phenyl(1-4C)alkoxy is optionally substituted with one or several substituents, selected from (1-4C)alkoxy; R4 represents R11-phenyl or R11-(4-5C)heteroaryl, which represents heteroaromatic group, containing 4-5 carbon atoms and at least one heteroatom, selected from N and S, where phenyl or heteroaryl group is optionally additionally substituted with one or several substituents, selected from nitro, (1-4C)alkyl, (1-4C)alkoxy; R7 represents H, (1-4C)alkyl; R8 represents (1-4C)alkylsulfonyl, (1-4C)alkylcarbonyl, (1-4C)alkoxycarbonyl, (1-4C)alkoxy(1-4C)alkylcarbonyl, furylcarbonyl; phenyl(1-4C)alkylcarbonyl, where phenyl ring is optionally substituted with one or several substituents, selected from (1-4C)alkoxy; R9 and R10 are not necessarily selected from H, (1-6C)alkyl and (1-4C)alkoxy(2-4C)alkyl; or R9 and R10 can be bound together with formation of morpholinyl ring; R11 represents H, R12, R13-amino, R14, R15-aminocarbonyl or R14, R15-aminosulfonyl; R12 represents H; R13 represents (1-4C)alkylsulfonyl, (1-4C)alkylcarbonyl, (1-4C)alkoxycarbonyl or pyperazinyl(1-4C)alkylcarbonyl; R14 and R15 are independently selected from H, (1-6C)alkyl, (1-4C)alkoxy(2-4C)alkyl and imidazolyl(1-4C)alkyl; X represents O or R16-N; Y represents CH2 or C(O);Z represents CN; R16 represents H, (1-4C)alkyl, (1-4C)alkylcarbonyl; or their pharmaceutically acceptable salts. Invention also relates to pharmaceutical composition, as well as to application of 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydrochinoline derivatives by any of i.i. 1-10.

EFFECT: obtaining novel biologically active compounds, which possess agonistic activity with respect to FSH receptor.

13 cl, 43 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: there are described novel acylsulfonamide peri-substituted condensed bicyclic compounds of general formula (I), values of radicals are given in invention formula. Also described is pharmaceutical composition based on formula (I) compound.

EFFECT: compounds can be used for inhibition of prostaglandin E2 binding with receptor EP3.

30 cl, 371 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention describes an amide of formula:

where A and B are independently selected from CH or N; D is H; Z is selected from hydrogen, unsubstituted C1-8alkyl, each L is independently selected from -CraRb-, -CRa=, -CO-, -O- or -NRa-; k, m, n, q, x and w are integers independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, provided that k+m+n+q+x+w equals at least 4; R1-R6 are independently selected from hydrogen, CN or halogen; Ra and Rb are independently selected from hydrogen, unsubstituted C1-8alkyl, or its pharmaceutically acceptable salt. The invention describes a pharmaceutical composition, use of the compounds to treat AChE-mediated diseases, a treatment method, as well as an amide synthesis method and use of the formula (I) amide as a chemical agent for inhibiting acetylcholinesterase in biological research.

EFFECT: compounds have high acetylcholinesterase or butyrylcholinesterase inhibiting activity.

24 cl, 27 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I), including its pharmaceutically acceptable salts, solvates, ethers and amides, possessing ability to bind ERα- and ERβ-estrogen receptors, to pharmaceutical composition based on them, to versions of applying claimed compounds in medication preparation and to method of binding ERα- and ERβ-estrogen receptors. (I), where R1 represents H, OH or C1-12alkoxy, or halogen; R2 represents H, OH or halogen; R3 represents C1-12alkyl, halogeno-C1-12alkyl, C3-10cycloalkyl, C1-12alkoxy or C1-12alkoxyC1-12alkyl; R4 represents H or C1-12alkoxy; R5 represents H, halogen or halogeno-C1-12alkyl; R6 represents -(Y)z-R7; R8 represents phenyl or 5- or 6-member heteroaryl, containing N, O or S as heteroatom, where said phenyl and heteroaryl are possibly substituted with OH, halogeno, halogenoC1-12alkyl or C1-12alkoxy. Values R7, Y and z are presented in invention formula.

EFFECT: novel compounds possess useful biological properties.

19 cl, 7 dwg, 1 tbl, 70 ex

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