Method of producing n-[4-(thi)oxo-1,3,5-triazinan-1-yl]arylamides

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing N-[4-(thi)oxo-1,3,5-triazinan-1-yl]arylamides of general formula (1), where R=m-C5H4N, o-MeOC6H4, m-MeOC6H4, X=O, S, which includes reacting N,N'-bis[dimethylaminomethyl](thio)urea of general formula (Me)2NCH2C(X)CH2N(Me)2, where X=S, O, with a hydrazide of general formula RC(O)NHNH2 in the presence of a samarium chloride crystalline hydrate catalyst SmCl3·6H2O with molar ratio N,N'-bis[dimethylaminomethyl](thio)urea:RC(O)NHNH2:SmCl3·6H2O=10:10:(0.8-1.2) in ethanol at 75-85°C and atmospheric pressure for 22-26 hours.

EFFECT: obtaining novel N-[4-(thi)oxo-1,3,5-triazinan-1-yl]arylamides.

1 tbl, 1 ex

 

The present invention relates to the field of organic chemistry, specifically to a method of obtaining N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1):

1,3,5-Triazine-2-(ti)ons promising as an effective pesticide [O. P. Gorbatov, A. V. Gerbi, O. V. Koroleva. Triazinone pesticides: structure, effect on living organisms, the processes of dehydration. The success of biological chemistry, vol. 46, 2006, pp. 323-348], as well as synthons for obtaining alkaloid Agelastatina A [M. Movassaghi, D. S. Siegel, and S. Han. Total Synthesis of all (-)-Agelastatin Alkaloids. J. of the Royal Society of Chemistry, 2010, p.1-140).

The known method [Bunnenberg R., J. C. Jochims Oxalyl-isothiocyanate und Carbonyl-halogenid-isothiocyanate. Chem. Ber., 1981, 114, s.1746] obtain the substituted 1,3,5-triazine-2-she (2) by condensation of N-methyl-thiourea with the isocyanate with the release of 69%.

The known method cannot be obtained N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

The known method [Wm. J. Burke. Synthesis oftetrahydro-5-substituted-2(1)-s-triazones. JACS, 1947, 69, p.2136] obtain 5-alkyl-1,3,5-triazine-2-ones (3) condensation of dimethylamine with primary amines with access 36-62%.

The known method does not allow to obtain N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

The known method [Lazarev D. B., Rams S. M., Ivanenko A. G. Cyclic thiocarbamide as inhibitors Oki�tion of cumene. The Doha, 2000, 70, 3, p. 475] obtain 1,3,5-triazine-2-thiones (4) condensation of primary alkyl amines with formaldehyde and thiourea to the outputs of 5-40%.

The known method cannot be obtained N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

Thus, the literature contains no information on the selective obtaining N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

We propose a new selective method of obtaining N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

The method consists in the interaction of N,N'-bis - [dimethylaminomethyl](thio)urea of the General formula (Me)2NCH2C(X)CH2N(Me)2where X=S, O, hydrazides arylcarbamoyl acids of the General formula RC(O)NHNH2where R=m-C5H4N, o-MeOC6H5m-mios6N5in the presence of a catalyst of crystalline samarium chloride SmCl3·6H2O, taken in a molar ratio of N,N'-bis - [dimethylaminomethyl](thio)urea : RC(O)NHNH2: SmCl3·6H2O=10:10:(0.8-1.2), preferably 10:10:1, at a temperature of 75-85°C, preferably 80°C and atmospheric pressure for 22-26 h, preferably 24 h. the Yield of N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides (1) is 52-66%. The reaction proceeds according to the scheme:

Target products (1) are formed only at the sites�eat arylhydrazines acids and N,N'-bis - [dimethylaminomethyl](thio)urea, taken in a stoichiometric ratio. Increase or decrease the content of N,N'-bis - [dimethylaminomethyl](thio)urea relative to the hydrazides of carboxylic acids leads to a decrease in the yield of the target product (1).

The conduct of a specified reaction in the presence of a catalyst SmCl3·6H2O more than 1.2 mmol does not lead to a substantial increase in the yield of the target product (1). The use of the catalyst SmCl3·6H2O less than 0.8 mmol reduces output (1), which is connected, possibly, with a reduction of catalytically active sites in the reaction mass. Without catalyst the reaction does not pass.

Reactions were carried out at a temperature of 75-85°C. At temperatures above 85°C (for example, 100°C) decreases the selectivity and increase the energy consumption and at a lower temperature (e.g. 50°C) decreases the reaction rate. As the solvent used ethyl alcohol, since it is highly soluble reactants.

Significant differences of the proposed method

In the proposed method, in the reaction with N,N'-bis - [dimethylaminomethyl](thio)urea are involved arylhydrazines in the presence of SmCl3·6H2O as a catalyst. The reaction proceeds with the selective formation of N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

In the known method of 1,3,5-triazine of the General formula (4) is prepared by condensation of primary and�of Kalamanov with formaldehyde and thiourea.

The proposed method has the following advantages:

The method allows to obtain high selectivity and good yields N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1).

The method is illustrated by the following examples.

Example 1. In a glass reactor, mounted on a magnetic stirrer was 0.167 g (10 mmol) of N,N'-bis - [dimethylaminomethyl]urea in 3 ml of ethanol, 0.036 g (1 mmol) of the catalyst SmCl3·6H2O and 0.174 g (10 mmol) of o-methoxybenzaldehyde in 2 ml of ethanol. The reaction mixture was stirred 24 h at 80°C. From the reaction mass there are N-[4-oxo-1,3,5-triazine-1-yl]-ortho-methoxybenzamide with the release of 60%.

Other examples of the method are shown in table.1

Table 1
No.
p/p
Source originatedThe original N,N'-bis - [dimethylaminomethyl]-(thio)ureaThe ratio of ArC(O)NHNH2: N,N'-bis - [dimethylaminomethyl](thio)urea : SmCl3·6H2O, mmolReaction time, hT, °COutput (1), %
1 10:10:1248060
2-//--//-10:10:1.2248066
3-//--//-10:10:0.8248052
4-//--//-10:10:1268061
5-//--//-10:10:1228057
6-//--//-10:10:1247555
7-//--//- 248564
810:10:1248063
9-//-10:10:1248059

All experiments were performed in ethanol.

A method of producing N-[4-(ti)oxo-1,3,5-triazine-1-yl]arylamides of the General formula (1):

where R =m-C5H4N,o-MeOC6H4,m-MeOC6H4,X = O, S, wherein N,N'-bis - [dimethylaminomethyl](thio)urea of the General formula (Me)2NCH2C(X)CH2N(Me)2where X = S, O, is subjected to the interaction with the hydrazide of General formula RC(O)NHNH2[R = above] in the presence of a catalyst of crystalline samarium chloride SmCl3·6H2O with a molar ratio of N,N'-bis - [dimethylaminomethyl](thio)urea:RC(O)NHNH2:SmCl3·6H2O=10:10:(0.8-1.2) in ethanol at 75-85°C and atmospheric Yes�perfect for 22-26 h.



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to organic chemistry, namely to compounds of formula (I), wherein R1 and R2 independently represent C6-C10 aryl optionally substituted by -OH, halogen, -OC1-C3 alkyl, -NO2, -CF3 or C1-C3 alkyl, or 5- or 6-merous heteroaryl containing one heteroatom specified in N, S and O; A and M independently represent a methylene group or a single bond; an adjacent aromatic cycle is attached directly to an amide group; the group Y=Z represents together and irregularly oxygen atom (-O-), cis-vinylidene group (-CH=CH-), iminogroup (-N=CH- or -CH=N-) or methylene group with sp2-hybridised carbon atom (=CH-); X irregularly represents methine group (=CH-), cis-vinylidene group (-CH=CH-) or carbon atom (=N-), and W represents hydroxyl group (-OH), C1-C6 alkyl optionally substituted by -SH, 5- or 6-merous heteroaryl containing 1 to 2 nitrogen heteroatoms, or C6-C10 aryl, optionally substituted by -SH, -NH2, and their pharmaceutically acceptable salts.

EFFECT: described are the methods for preparing the compounds, using as a drug for treating cancer and the based pharmaceutical composition.

14 cl, 6 tbl, 49 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of formula , wherein Y and Z are independently specified in a group of a) or b) so that one of Y or Z is specified in the group a), and another one - in the group b); the group a) represents i) substituted C6-10aryl; ii) C3-8cycloalkyl; iii) trifluoromethyl or iv) heteroaryl specified in a group consisting of thienyl, furanyl, thiazolyl, isothiazolyl, oxazolyl, pyrrolyl, pyridinyl, isoxazolyl, imidazolyl, furasan-3-yl, benzothienyl, thieno[3,2-b]thiophen-2-yl, pyrazolyl, triazolyl, tetrazolyl and [1,2,3]thiadiazolyl; the group b) represents i) C6-10aryl; ii) heteroaryl specified in a group consisting of thiazolyl, pyridinyl, indolyl, pyrrolyl, benzoxazolyl, benzothiazolyl, benzothienyl, benzofuranyl, imidazo[1,2-a]pyridin-2-yl, furo[2,3-b]pyridinyl, pyrrolo[2,3-b]pyridinyl, pyrrolo[3,2-b]pyridinyl, thieno[2,3-b]pyridinyl, quinolinyl, quinazolinyl, thienyl and benzimidazolyl; iii) benzofused heterocyclyl attached through a carbon atom, and when a heterocyclyl component contains a nitrogen atom, the carbon atom is optionally substituted by one substitute specified in a group consisting of C3-7cycloalkylcarbonyl; C3-7cycloalkylsulphonyl; phenyl; phenylcarbonyl; pyrrolylcarbonyl; phenylsulphonyl; phenyl(C1-4)alkyl; C1-6alkylcarbonyl; C1-6alkylsulphonyl; pyrimidinyl and pyridinyl; C3-7cycloalkylcarbonyl, phenyl, phenylcarbonyl, phenyl(C1-4)alkyl and phenylsulphonyl are optionally substituted by trifluoromethyl, or by one or two fluor-substitutes; iv) phenoxatiynyl; vi) fluoren-9-on-2-yl; vii) 9,9-dimethyl-9H-fluorenyl; viii) 1-chlornaphtho[2,1-b]thiophen-2-yl; ix) xanthen-9-on-3-yl; x) 9-methyl-9H-carbazol-3-yl; xi) 6,7,8,9-tetrahydro-5H-carbazol-3-yl; xiii) 3-methyl-2-phenyl-4-oxochromen-8-yl; or xiv) 1,3-dihydrobenzimidazol-2-on-5-yl optionally substituted by 1-phenyl, 1-(2,2,2-trifluoroethyl), 1-(3,3,3-trifluoropropyl) or 1-(4,4-difluorocyclohexyl); 1-phenyl is optionally substituted by one or more fluor-substitutes or trifluoromethyl; or xv) 4-(3-chlorophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl; R1 represents C6-10aryl, C1-3alkyl, benzyloxymethyl, hydroxy(C1-3)alkyl, aminocarbonyl, carboxy, trifluoromethyl, spirofused cyclopropyl, 3-oxo or aryl(C1-3)alkyl; or when s is equal to 2 and R1 represents C1-3alkyl, the substitutes C1-3akyl is taken with a piperazine ring to form 3,8-diazabicyclo[3.2.1]octanyl or 2,5-diazabicyclo[2.2.2]octanyl ring system, and its pharmaceutical compositions.

EFFECT: preparing the new pharmaceutical compositions.

20 cl, 7 tbl, 72 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: general formula I involves both new, and known compounds. The compounds can be used for treating neuropathic pain mediated by Ih channel modulation and related inflammatory pain. In a compound of formula I. Ar means phenyl or a 6-merous heteroaryl group containing 1 or 2 nitrogen atoms, each of which can be optionally substituted by one or more substitute(s) specified in a group consisting of a halogen, (C1-4)alkyl, halogen(C1-4)alkyl, (C1-4)alkyloxy, halogen(C1-4)alkyloxy and (C1-4)alkylthio; X means O, S or NR1; R1 means H; R2 means (C1-4)alkyl, halogen(C1-4)alkyl or (C1-4)alkyloxy(C1-4)alkyl; R3 means H, (C1-4)alkyl, halogen(C1-4)alkyl or (C1-4)alkyloxy(C1-4)alkyl; Y1 means N; and Y2 and Y3 mean N or Y3 means CH, and Y2 independently means CH or N; R4 and R5 independently mean H, (C1-4)alkyl, halogen(C1-4)alkyl or (C1-4)alkyloxy(C1-4)alkyl; or R4 and R5 form a 3-7-merous saturated cycle together with a nitrogen atom which they are attached to.

EFFECT: invention refers to aminoheteroaryl derivatives having the general formula I, or their pharmaceutically acceptable salts.

12 cl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, specifically to bensyl aralkyl ether of formula or to its pharmaceutically acceptable salt, where: Ar represents imidazolil; R1, R2, R4 and R5 independently stand for hydrogen; R3 stands for a halogen; R6 stands for trifluoromethyl or trichloromethyl; n is an integer from 0 to 2; and m is 1. The invention also relates to the use of the compound of formula (1) for the treatment and/or prevention of diseases caused by fungi, or bacteria.

EFFECT: obtained new heterocyclic compounds with useful biological properties.

4 cl, 4 dwg, 9 tbl, 8 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to organic chemistry, namely to new quinolin-4-one derivatives of formula (1) or to its pharmaceutically acceptable salt, wherein R1 represents: (1) hydrogen, (2) C1-C6 alkyl, (35) carbamoyl-C1-C6 alkyl optionally containing morpholinyl-C1-C6 alkyl, or (36) phosphonoxy-C1-C6 alkyl optionally containing one or two C1-C6 alkyl groups on a phosphonoxy group; R2 represents: (1) hydrogen or (2) C1-C6 alkyl; R3 represents phenyl, thienyl or furyl, wherein a phenyl ring presented by R3, can be substituted by one C1-C6 alkoxy group; R4 and R5 are bound to form a group presented by any of the following formulas: , , , , , , or a group presented by the following formula: a group optionally containing one or more substitutes specified in a group consisting of C1-C6 alkyl groups and oxogroups; R6 represents hydrogen; and R7 represents C1-C6 alkoxy group. The invention also refers to a pharmaceutical composition based on the compound of formula , to a preventive and/or therapeutic agent based on the compound of formula (1), using the compound of formula (1), a method for preparing the compound of formula , as well as to specific compounds.

EFFECT: there are prepared new quinolin-4-one derivatives effective in treating neurodegenerative diseases, diseases caused by neurological dysfunction, or diseases caused by mitochondrial dysfunction.

18 cl, 1 tbl, 257 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to 1-(2-{[4-(4-{[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester of biphenyl-2-ylcarbamic acid or to its pharmaceutically acceptable salt. The invention also refers to a pharmaceutical composition based on the above compound, a method and an intermediate compound for producing the above compound.

EFFECT: produced is the new heterocyclic compound effective in treating pulmonary disorders, including in chronic obstructive pulmonary disease or asthma.

9 cl, 3 tbl, 170 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to specific compounds or to their therapeutically acceptable salt presented in the patent claim and representing sulphonyl benzamide derivatives. The invention also refers to a pharmaceutical composition inhibiting the activity of anti-apoptotic proteins of the family Bcl-2, containing an excipient and an effective amount of a specific sulphonyl benzamide derivative.

EFFECT: sulphonyl benzamide derivatives inhibiting the activity of anti-apoptotic Bcl-2 proteins.

2 cl, 3 tbl, 558 ex

Antiviral compounds // 2541571

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new compounds of formula I, such as below, or its pharmaceutically acceptable salts. What is described is a method for preparing them.

,

wherein: A independently from B means phenyl,

, or ,

and B independently from A means phenyl,

, or ,

and the values Z, Y, D, L1, L2, L3, Z1, Z2 are presented in the patent claim.

EFFECT: compounds are effective for hepatitis C virus (HCV) replication inhibition.

17 cl, 3 tbl, 8 dwg, 177 ex

FIELD: chemistry.

SUBSTANCE: invention relates to field of organic chemistry, namely to heterocyclic compounds of formula I

and to their pharmaceutically acceptable salts, where A is selected from CH or N; R1 is selected from the group, consisting of C3-6-cycloalkyl, C3-6-cycloalkyl-C1-7-alkyl, C1-7-alkoxy-C1-7-alkyl, halogen-C1-7-alkyl; R2 and R6 independently on each other represent hydrogen of halogen; R3 and R5 independently on each other are selected from the group, consisting of hydrogen, C1-7-alkyl and halogen; R4 is selected from the group, consisting of hydrogen, C1-7-alkyl, halogen and amino; R7 is selected from the group, consisting of C1-7-alkyl, C1-7alkoxy-C1-7-alkyl, C1-7-alkoxyimino-C1-7-alkyl, 4-6-membered heterocyclyl, containing one heteroatom O, phenyl, with said phenyl being non-substituted or substituted with one hydroxy group, and 5-10-membered heteroaryl, containing 1-3 heteroatoms, selected from N, S and O, said heteroaryl is not substituted or is substituted with one or two groups, selected from the group, consisting of C1-7-alkyl, hydroxy, C1-7-alkoxy, cyano, C1-7-alkylaminocarbonyl and halogen. Invention also relates to pharmaceutical composition based on formula I compound and to method of obtaining formula I compound.

EFFECT: obtained are novel heterocyclic compounds, which are agents, increasing level of LDLP.

17 cl, 2 tbl, 89 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formula I , II or IV , wherein the radical values W, V, Ra, Rb, X, L, Rt, A are presented in the patent claim.

EFFECT: declared compounds identify and bind the CA-IX protein; they can contain a radioactive element for radionuclide imaging or therapeutic application.

27 cl, 1 tbl, 5 dwg, 25 ex

FIELD: chemistry.

SUBSTANCE: described is a novel method for selective production of 5-alkyl-1,3,5-triazinan-2(thi)ones of general formula , where X=O, S; R=t-Bu, cyclohexyl; R'=H, allyl, where a primary aliphatic amine RNH2, where R has values given above, reacts with bis(N,N-dimethylamino)methane and (thio)urea in the presence of a copper chloride crystalline hydrate CuCl2·2H2O catalyst in molar ratio (thio)urea:bis(N,N-dimethylamino)methane:RNH2:CuCl2·2H2O=10:20:10:(0.3-0.7) at temperature of 80°C and atmospheric pressure in a mixture of solvents CHCl3-ethyl alcohol (1:1, by volume) for 6-10 hours.

EFFECT: obtained compounds have potential for use as effective pesticides and can serve as synthons for producing alkaloid Agelastatina A; output of 5-alkyl-1,3,5-triazinan-2(thi)ones is 22-50%.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: described is a novel method for selective production of 5-alkyl-1,3,5-triazinan-2(thi)ones of general formula , where X=O, S; Alkyl=t-Bu, cyclohexyl; R=H, allyl, involving reaction of N,N-bis(methoxymethyl)alkylamine of general formula Alkyl-N(CH2OMe)2, where Alkyl has values given above, with (thio)urea of general formula H2NC(X)NHR, where X and R are given above, in the presence of samarium chloride crystalline hydrate SmCl3·6H2O catalyst in molar ratio Alkyl-N(CH2OMe)2:(thio)urea:SmCl3·6H2O = 10:10:(0.3-0.7) at temperature of 60°C and atmospheric pressure in a mixture of solvents CHCl3-EtOH (1:1, by volume) for 6-10 hours.

EFFECT: obtained compounds have potential for use as effective pesticides and can also serve as synthons for producing alkaloid Agelastatina A.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: described is a novel method for selective production of 5-alkyl-1,3,5-triazinan-2(thi)ones of general formula , where X=O, S; Alkyl=t-Bu, cyclohexyl; R=H, allyl, involving reaction of N,N-bis(methoxymethyl)alkylamine of general formula Alkyl-N(CH2OMe)2, where Alkyl has values given above, with (thio)urea of general formula H2NC(X)NHR, where X and R are given above, in the presence of samarium chloride crystalline hydrate SmCl3·6H2O catalyst in molar ratio Alkyl-N(CH2OMe)2:(thio)urea:SmCl3·6H2O = 10:10:(0.3-0.7) at temperature of 60°C and atmospheric pressure in a mixture of solvents CHCl3-EtOH (1:1, by volume) for 6-10 hours.

EFFECT: obtained compounds have potential for use as effective pesticides and can also serve as synthons for producing alkaloid Agelastatina A.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: described is a novel method for selective production of 5-alkyl-1,3,5-triazinan-2(thi)ones of general formula , where X=O, S; R=t-Bu, cyclohexyl; R'=H, allyl, where a primary aliphatic amine RNH2, where R has values given above, reacts with bis(N,N-dimethylamino)methane and (thio)urea in the presence of a copper chloride crystalline hydrate CuCl2·2H2O catalyst in molar ratio (thio)urea:bis(N,N-dimethylamino)methane:RNH2:CuCl2·2H2O=10:20:10:(0.3-0.7) at temperature of 80°C and atmospheric pressure in a mixture of solvents CHCl3-ethyl alcohol (1:1, by volume) for 6-10 hours.

EFFECT: obtained compounds have potential for use as effective pesticides and can serve as synthons for producing alkaloid Agelastatina A; output of 5-alkyl-1,3,5-triazinan-2(thi)ones is 22-50%.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing N-[4-(thi)oxo-1,3,5-triazinan-1-yl]arylamides of general formula (1), where R=m-C5H4N, o-MeOC6H4, m-MeOC6H4,X=O, S, which includes reacting N,N'-bis[dimethylaminomethyl](thio)urea of general formula (Me)2NCH2C(X)CH2N(Me)2, where X=S, O, with a hydrazide of general formula RC(O)NHNH2 in the presence of a samarium chloride crystalline hydrate catalyst SmCl3·6H2O with molar ratio N,N'-bis[dimethylaminomethyl](thio)urea:RC(O)NHNH2:SmCl3·6H2O=10:10:(0.8-1.2) in ethanol at 75-85°C and atmospheric pressure for 22-26 hours.

EFFECT: obtaining novel N-[4-(thi)oxo-1,3,5-triazinan-1-yl]arylamides.

1 tbl, 1 ex

FIELD: organic chemistry, chemical technology, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of sulfonamides of the formula (I) or their pharmaceutically acceptable salts wherein R1 means -OH or -NHOH; R2 means hydrogen atom; R3 means alkyl, alkoxyalkyl, arylalkyl, pyridylalkyl or morpholinylalkyl; A means piperidyl or tetrahydrofuranyl; n = 0; E means a covalent bond; (C1-C4)-alkylene, -C(=O)-, -C(=O)O- or -SO2-; X means hydrogen atom, alkyl, aryl, arylalkyl, alkoxyalkyl, morpholinyl or tetrahydropyranyl; each among G and G' means -C(R5)=C(R5') wherein R5 and R5' mean hydrogen atom; M means the group -CH-; z means the group -(CR7R7')a-L-R8 wherein a = 0 and each among R7 and R7' means hydrogen atom; L means a covalent bond; R8 means halogen atom or alkoxy-group. Compounds of the formula (I) are inhibitors of metalloproteases and can be used for treatment of arthritis, cancer tumors and other diseases.

EFFECT: valuable medicinal properties of compounds.

15 cl, 7 tbl, 56 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to a group of new derivatives of 4,5-dihydro-1H-pyrazole of the general formula (I):

wherein R means phenyl, thienyl or pyridyl and these indicated groups can be substituted with (C1-C3)-alkoxy-group or halogen atom; R1 means phenyl that can be substituted with (C1-C3)-alkoxy-group or pyridyl group; R2 means hydrogen atom or hydroxy-group; Aa means one group among the following groups: (i) , (ii) , (iii) , (iv) or (v) ; R4 and R5 mean independently from one another hydrogen atom or (C1-C8)-branched or unbranched alkyl; or R4 means acetamido- or dimethylamino-group or 2,2,2-trifluoroethyl, or phenyl, or pyridyl under condition that R5 means hydrogen atom; R6 means hydrogen atom at (C1-C3)-unbranched alkyl; Bb means sulfonyl or carbonyl; R3 means benzyl, phenyl or pyridyl that can be substituted with 1, 2 or 3 substitutes Y that can be similar or different and taken among the group including (C1-C3)-alkyl or (C1-C3)-alkoxy-group, halogen atom, trifluoromethyl; or R3 means naphthyl, and its racemates, mixtures of diastereomers and individual stereoisomers and as well as E-isomers, Z-isomers and mixture of E/Z-compounds of the formula (I) wherein A has values (i) or (ii), and its salt. These compounds are power antagonists of Cannbis-1 (CB1) receptor and can be used for treatment of psychiatric and neurological diseases. Except for, invention relates to a pharmaceutical composition used for treatment of some diseases mediated by CB1-receptor, to a method for preparing this composition, a method for preparing representatives of compounds of the formula (I) wherein Aa means group of the formulae (i) or (ii), intermediate compounds used for preparing compounds of the formula (I) and to a method for treatment of some diseases mediated by CB1-receptor.

EFFECT: valuable medicinal properties of compounds.

16 cl, 9 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of benzodiazepine. Invention describes a derivative of benzodiazepine of the formula (I): wherein dotted lines show the possible presence of a double bond; R1, R2, R3, R4 and R5 are given in the invention claim; n represents 0, 1, 2, 3 or 4; X represents sulfur atom (S) or -NT wherein T is give in the invention claim; A represents hydrogen atom, (C6-C18)-aryl group substituted optionally with one or more substitutes Su (as given in the invention claim) or (C1-C12)-alkyl; or in alternative variant R4 and R5 form in common the group -CR6=CR7 wherein CR6 is bound with X and wherein R6 and R7 are given in the invention claim, and their pharmaceutically acceptable salts with acids or bases. It is implied that compounds corresponding to one of points (a)-(e) enumerated in the invention claim are excluded from the invention text. Also, invention describes methods for preparing compounds of the formula (I) and a pharmaceutical composition eliciting the hypolipidemic activity. Invention provides preparing new compounds eliciting the useful biological properties.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

20 cl, 6 tbl, 192 ex

FIELD: organic chemistry, chemical technology, medicine, pharmacy.

SUBSTANCE: invention proposes two variants of the improved method for preparing anti-ulcerous therapeutic agents of the formula (I): wherein radicals R1-R6 have values given in cl. 1 and cl. 2 of the invention claim. Method involves interaction of corresponding sulfides with m-chloroperoxybenzoic acid in acetone or a mixture acetone/water as a solvent. According to the first variant pH value of the reaction mixture is increased to the value above 7 after the reaction interaction and solvent is removed and crystals of compound of the formula (I) are separated. According to the second variant the interaction is carried out at pH ≥ 7.0 followed by addition of water if necessary and compound of the formula (I) crystals are separated. Invention is directed for preparing omeprazole or pantoprazole preferably. Invention provides preparing the end products of high purity and with high yield.

EFFECT: improved preparing method.

9 cl, 3 ex

FIELD: organic chemistry, heterocyclic compounds, medicine, pharmacy.

SUBSTANCE: invention relates to nitrogen-containing heterocyclic derivatives of the formula (I): A-B-D-E (I) wherein A means 5- or 6-membered heteroaryl comprising one or two nitrogen atoms in ring; B means ethenylene; D mean phenylene; E means group -N(COR)-SO2-G wherein G means phenyl; R means 5- or 6-membered heteroaryl or heteroarylmethyl comprising one or two nitrogen atoms in ring, or group -(CH2)n-N(R5)R6 wherein n means a whole number from 1 to 5; R5 and R6 are similar or different and mean: hydrogen atom, (C1-C6)-alkyl, hydroxyalkyl, aminoalkyl; or R5 and R6 in common with nitrogen atom can form 5-7-membered cyclic amino-group -N(R5)R6 that can comprise, except for nitrogen atom, also oxygen, sulfur or nitrogen atom as a component forming the ring, or their N-oxides. Compounds of the formula (I) elicit anticancer activity and can be used in medicine.

EFFECT: valuable medicinal properties of compounds.

10 cl, 1 tbl, 24 ex

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