Substituted heteroaryl derivatives

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new substituted heteroaryl derivatives of general formula I: , wherein: A means N, CR7-10, with A at the most twice meaning N; W means O, S or NR4, the values B, C, R7-10 are presented in clause 1 of the patent claim. The method for preparing the compound I is described.

EFFECT: compounds show analgesic activity that enables using them for a variety of diseases, especially acute pain, neuropathic, chronic or inflammatory pain.

16 cl, 2 tbl, 307 ex

 

The text descriptions are given in facsimile form.

1. Substituted heteroaryl derivatives of General formula I,

in which A denotes N or CR7-10and A most double-means N;
W denotes O, S or NR4indicating that if W denotes O or S, A mean CR7-10;
one of the residues a, B, or C is H; C1-8-alkyl every time saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; COR12; SO2R12; associated C1-3the alkyl aryl, C3-8-cycloalkyl, 3-8-membered heterocyclyl ring in which one or two carbon atoms replaced by one heteroatom S, N or O, where the ring may be condensed with another ring which may be saturated, unsaturated or aromatic, unsubstituted or monosubstituted and and polyamidine, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted, aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members every time monosubstituted or politeley or unsubstituted; C3-8-cycloalkyl, every time monosubstituted or politeley or unsubstituted; 3-8-membered heterocyclyl ring in which one or two carbon atoms replaced by one heteroatom S, N or O, where the ring may be condensed with another ring which may be saturated, unsaturated or aromatic, unsubstituted or monosubstituted or polyamidine; and every time another residue B or C means
,
andmeans the ordinary bond or a double bond;
R1and R2independently from one another mean H, C1-5-alkyl every time saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; C3-8-cycloalkyl, each time Voznesenie or politeley or unsubstituted; aryl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted; or bound C1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted;
or the remains of R1and R2together mean CH2CH2OCH2CH2CH2CH2NR11CH2CH2or (CH2)3-6,
and R11means H; C1-5-alkyl, each time a saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; C3-8-cycloalkyl, every time monosubstituted or politeley or unsubstituted; aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted; or bound C 1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted; C(O)phenyl, C(O) 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system in conjunction with up to 12 ring members, C(O)C1-5-alkyl, each time a substituted or unsubstituted; and
R3means C1-8-alkyl, each time a saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; C3-8-cycloalkyl, every time monosubstituted or politeley or unsubstituted;
aryl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time unsubstituted or monosubstituted or politeley; associated C1-3is an alkyl group, aryl, 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system the volumes in conjunction with up to 12 ring members, or C3-8-cycloalkyl, every time unsubstituted or monosubstituted or politeley;
R4means H; C1-5-alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or monosubstituted or politeley; aryl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time a substituted or unsubstituted; associated C1-3is an alkyl group, aryl, 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members; or C3-8cycloalkyl, every time monosubstituted or politeley or unsubstituted; COR12; SO2R12,
and R12means H; C1-5-alkyl, each time a saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; C3-8-cycloalkyl, every time a saturated or unsaturated, monosubstituted or politeley or unsubstituted;
aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of Bicycle eskay system in conjunction with up to 12 ring members, every time monosubstituted or politeley or unsubstituted; or bound C1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time monosubstituted or politeley or unsubstituted; OR13; NR14R15;
R7, R8, R9and R10independently from each other denote H, F, Cl, Br, I, NO2, CF3, OR13, SR13, SO2R13, SO2OR13, CN, COOR13, NR14R15, NHC(O)other13, NHC(O)R13, NH(CNR13)Other13, SO2Other13; C1-5-alkyl, C3-8-cycloalkyl, unsubstituted or monosubstituted or politeley; aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, unsubstituted or monosubstituted or politeley; or associated With1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, independently researched ewenny or monosubstituted or politeley;
and R13means H; C1-5-alkyl every time saturated or unsaturated, branched or unbranched, unsubstituted or monosubstituted or politeley; C3-8-cycloalkyl, every time a saturated or unsaturated, unsubstituted or monosubstituted or politeley; aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, unsubstituted or monosubstituted or politeley; or associated With1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, unsubstituted or monosubstituted or politeley;
or R7, R8and R9have the above significance and R10with B together represent-CH2CH2CH2and R10and B thus form a six-membered ring,
R14and R15independently of one another denote H; C1-5-alkyl, each time a saturated or unsaturated, branched or unbranched, unsubstituted or monosubstituted or politeley; or (C3-8-cycloalkyl, every time saturated and the unsaturated, unsubstituted or monosubstituted or politeley; aryl-, or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, unsubstituted or monosubstituted or politeley; or associated With1-3the alkyl aryl, C3-8-cycloalkyl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, unsubstituted or monosubstituted or politeley;
or R14and R15together form CH2CH2OCH2CH2CH2CH2NR16CH2CH2or (CH2)3-6,
and R16means H; C1-5-alkyl saturated or unsaturated, branched or unbranched, unsubstituted or monosubstituted or politeley;
moreover, the above C1-8-alkali, C1-5-alkali, C1-3-alkali, C1-3-alkylene, C3-8-cycloalkyl, heterocyclyl remains each time can be mono - or polyamideimide by F, Cl, Br, I, -CN, NH2, NH-C1-6-alkyl, NH-C1-6-alkyl-OH, N(C1-6-alkyl)2N(C1-6alkyl-OH)2, NO2, SH, S-C1-6-alkyl, S-benzyl, OCF3 O-C1-6-alkyl, OH, O-C1-6-alkyl-OH, =O, C1-6-alkyl, S-benzyl, O-benzyl, O-phenyl, C(=O)C1-6-alkyl, CO2H, NHC(=O)C1-6-alkyl, OC(=O)C1-6-alkyl, CO2-C1-6-alkyl,
and the above aryl or heteroaryl residues each time can be monosubstituted or polyamideimide by F, Cl, Br, I, CN, NH2, NH-C1-6-alkyl, NH-C1-6-alkyl-OH, N(C1-6-alkyl)2N(C1-6-alkyl-OH)2, NO2, SH, S-C1-6-alkyl, OH, O-C1-6-alkyl, O-C1-6-alkyl-OH, C(=O)C1-6-alkyl, CO2H, CO2-C1-6-alkyl, CF3, OCF3C1-6-alkyl or phenoxy, in the form of a racemate, diastereomers, bases and/or salts of physiologically compatible acids.

2. Heteroaryl derivative according to claim 1, in which R1and R2independently of one another denote H; C1-5-alkyl, saturated or unsaturated, branched or unbranched, monosubstituted or politeley or unsubstituted; or residues R1and R2together form a ring and CH2CH2OCH2CH2CH2CH2NR11CH2CH2or (CH2)3-6and R11means H; C1-5-alkyl, saturated or unsaturated,
branched or unbranched, monosubstituted, or politeley or unsubstituted.

3. Heteroaryl derivative according to claim 2, in which R1and Rsup> 2independently from each other mean CH2or H, and R1and R2do not simultaneously denote H.

4. Substituted heteroaryl derivative according to claim 1, in which R3means butyl, phenyl, thiophenyl, thiazolyl, cyclopentyl, cyclohexyl, naphthyl, benzyl, benzofuranyl, 1,2,4-triazolyl, benzimidazolyl, benzodioxolyl, benzodioxolyl, pyridyl or benzothiophene, every time unsubstituted or monosubstituted or politeley; linked saturated, unbranched C1-3is an alkyl group, phenyl, furyl or thiophenyl, every time unsubstituted or monosubstituted or politeley.

5. Substituted heteroaryl derivative according to claim 4, in which R3means phenyl, 4-forfinal, benzyl, butyl or benzothiophene.

6. Substituted heteroaryl derivative according to claim 1, in which B or C means (CH2)1-4-R21and R21means H, OH, SH, COOC1-6-alkyl, COOH, OC(O)C1-6-alkyl, NH2, NHC(=O)C1-6-alkyl; or C3-8-cycloalkyl, aryl or 5-, 6 - or 7-membered heteroaryl containing from 1 to 4 heteroatoms independently selected from N, O and S, each of which may be part of a bicyclic system, in conjunction with up to 12 ring members, each time unsubstituted or monosubstituted or politeley.

7. Substituted heteroaryl derivative according to claim 6, in which R21means O, SH, COOCH3, COOH, OC(=O)CH3, NH2, NHC(=O)CH3, NHC(=O)CH2C(CH3)3; or benzimidazole, pyridyl, triazolyl, phenyl, pyrazolyl, tetrazolyl or imidazolyl, every time unsubstituted or substituted by COOCH3CH3; or cyclopropyl, cyclohexyl, pyrrolidinyl, tetrahydropyranyl, piperidyl, tetrahydroisoquinoline, isoindolines, piperazinil, morpholinyl or thiazolyl every time unsubstituted or substituted by =O, or CH3.

8. Substituted heteroaryl derivative according to claim 1, in which R7R8, R9and R10independently of one another denote H; methyl; ethyl; propyl; butyl; pyridyl, O-benzyl, F, Cl, Br, I, CN, CF3, OCF3, OH, OCH3, NH2, COOH, COOCH3, NHCH3or N(CH3)2or NO2.

9. Substituted heteroaryl derivative according to claim 8, in which R7R8, R9and R10independently from each other denote H, F, Cl, NO2CN, CF3, OCH3, OCF3or OH.

10. Substituted heteroaryl derivative according to claim 1 of the group
(1) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol, citrate
(3) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethyl acetate hydrochloride
(4) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(3-aminopropyl)-1H-indole, citrate
(6) (±) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)disappear to the-1-ol hydrochloride
(7) (±) 2-(5,6-dichloro-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethanol, citrate
(8) (±) 2-(2-(4-morpholino-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethanol, citrate
(9) (±) 2-(4,6-dichloro-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethanol, citrate
(10) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol, citrate
(11) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-5-(pyridin-3-yl)-1H-indol-3-yl)ethanol, citrate
(13) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-5-nitro-1H-indol-3-yl)ethanol, citrate
(14) (±) 2-(2-(4-(benzo[b]thiophene-2-yl)-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)ethanol, citrate
(15) (±) 2-(2-(4-(benzo[b]thiophene-2-yl)-4-(dimethylamino)cyclohex-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol, citrate
(16) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-1H-indole, citrate
(17) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(19) 2-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione, citrate
(20) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)acetamide", she citrate
(22) (±)-2-(4-benzyl-4-(dimethylamino)cyclohex-1-enyl)-3-methyl-1H-indol-5-carbonitril
(23) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-1H-indol-5-carbonitril
(24) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-methyl-5-trifluoromethyl-1H-indole
(25) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-5-trifluoromethyl-1H-indole, CIT is at
(26) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate
(27) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate
(28) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate
(29) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-5-methoxy-1H-indole, citrate
(30) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-methyl-1H-indole, citrate
(31) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-methyl-1H-indole, citrate
(32) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine, citrate
(33) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-cyclopropyl-1H-indole hydrochloride
(34) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-cyclopropyl-1H-indole
(35) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-cyclopropyl-1H-indole
(36) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-(cyclohexylmethyl)-1H-indole
(37) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-benzyl-1H-indole hydrochloride
(38) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-(cyclohexylmethyl)-1H-indole hydrochloride
(39) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-benzyl-1H-indol
(40) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(cyclohexylmethyl)-1H-indole hydrochloride
(41) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-benzyl-1H-indole hydrochloride
(42) (±)-2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-propyl-1H-br/> (43) (±)-2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-propyl-1H-indol
(44) (±)-2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-propyl-1H-indol
(45) (±) 2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(46) (±) 2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(47) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(48) (±)-3-(2-(4-benzyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)propan-1-ol, citrate
(49) (±)-3-(2-(4-butyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)propan-1-ol, citrate
(51) (±) 2-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione
(52) (±) 2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol
(53) (±) 2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol
(54) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol
(55) (±)2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-(2-(piperidine-1-yl)ethyl)-5-fluoro-1H-indol
(56) (±) 2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-(2-(piperidine-1-yl)ethyl)-5-fluoro-1H-indol
(57) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(piperidine-1-yl)ethyl)-5-fluoro-1H-indol
(58) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(piperidine-1-yl)ethyl)-1H-indole, citrate
(59) (±) 2-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-3-(2-(1H-1,2,3-triazole-1-yl)et is l)-5-fluoro-1H-indol
(60) (±) 2-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol
(61) (±) 2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol
(62) N-(2-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)ethyl)-3,3-dimethylbutyramide, citrate
(63) (±) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-3-yl)ethyl)ndimethylacetamide
(64) (±) N-(2-(2-(4-butyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)ethyl)-3,3-dimethylbutyramide;
(65) (±)-2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-5-fluoro-6-methoxy-1H-indol-3-yl)ethanol, citrate
(66) (±)-2-(2-(4-benzyl-4-(4-methylpiperazin-1-yl)cyclohex-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol
(67) (±)-2-(5-fluoro-2-(4-phenyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-1H-indol-3-yl)ethanol
(68) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-carbonitril, citrate
(70) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-carbonitril, citrate
(72) 2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-5-carbonitril, citrate
(73) 1-benzyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(75) 1-butyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(76) N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(77) 1-benzyl-4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(79) 1-butyl-4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohex the amine hydrochloride
(80) 4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(82) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate
(83) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(85) 1-benzyl-4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(89) 4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(91) 1-benzyl-4-(5-fluoro-3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(92) 1-benzyl-4-(5-fluoro-3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate (2:3)
(93) 1-butyl-4-(5-fluoro-3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate (4:3)
(94) 1-butyl-4-(5-fluoro-3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(95) 4-(5-fluoro-3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(97) 4-(3-(2-(1H-pyrazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate (2:3)
(98) 4-(3-(2-(1H-pyrazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate
(101) 4-(3-(2-(1H-pyrazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(103) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate
(105) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-in the ol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate (2:3)
(106) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate
(107) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(108) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate (2:3)
(109) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate (4:3)
(110) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate (2:3)
(111) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate (2:3)
(112) 4-(3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate (4:1)
(113) 4-(3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexylamine, citrate
(114) 4-(3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate
(116) 4-(3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(118) 2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-5-ol
(120) 1-benzyl-N,N-dimethyl-4-(3-methyl-5-(triptoreline)-1H-indol-2-yl)cyclohexanamine, citrate
(121) 1-butyl-N,N-dimethyl-4-(3-methyl-5-(triptoreline)-1H-indol-2-yl)cyclohexanamine, citrate
(123) N,N-dimethyl-4-(3-methyl-5-(triptoreline)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(125) 1-butyl-4-(5-labels and-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(127) 4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(128) 4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate (4:3)
(129) 1-benzyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate
(131) 1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate
(133) 1-benzyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(135) 1-butyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexylamine hydrochloride
(136) 4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(137) methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)acetate, citrate
(139) 1-benzyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(141) 1-benzyl-4-(3-benzyl-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(143) 1-butyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine, citrate
(144) 1-butyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexylamine hydrochloride
(145) 4-(3-benzyl-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexylamine, citrate
(147) 4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(149) 4-(3-benzyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(151) N,N-dimethyl-1-phenyl-4-(3-(pyridine-2-ylmethyl)-1H-indol-2-yl)cyclohexanamine
(153) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propionic acid hydrochlo the ID
(156) 1-benzyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate
(157) 1-butyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine hydrochloride
(158) 1-butyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate
(159) N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate
(161) 1-benzyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(163) 1-butyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(165) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate (1:4)
(166) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(167) N,N-dimethyl-4-(3-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(169) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-2-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(170) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-2-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate (2:3)
(171) 4-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butane acid hydrochloride
(172) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butane acid hydrochloride
(173) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butane-1-ol hydrochloride
(174) 4-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride
(176) 4-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride
(178) 4-(2-(4-(l is methylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride
(180) 3-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol, citrate
(181) 3-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride
(183) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride
(185) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propyl acetate hydrochloride
(187) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)pyrrolidin-2,5-dione
(189) 4-(3-(2-(3,4-dihydroquinoline-1(2H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate (4:3)
(190) 4-(3-(2-(3,4-dihydroquinoline-1(2H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(191) methyl 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-1H-1,2,3-triazole-4-carboxylate, citrate
(193) 4-(3-(2-(isoindoline-2-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(195) 4-(3-(2-(3,4-dihydroisoquinoline-2(1H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(196) 4-(3-(2-(3,4-dihydroisoquinoline-2(1H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate (2:3)
(197) N,N-dimethyl-1-phenyl-4-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(199) N,N-dimethyl-1-phenyl-4-(3-(2-(piperidine-1-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(200) N,N-dimethyl-4-(3-(2-(4-methylpiperazin-1-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(201) N,N-dimethyl-4-(3-(2-morpholinoethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, qi is Rath
(203) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(205) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(207) 4-(3-(2-(1H-1,2,4-triazole-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(209) N,N-dimethyl-1-phenyl-4-(3-(2-(thiazolidin-3-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(211) N,N-dimethyl-4-(3-(2-(5-methyl-2H-tetrazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(213) 4-(3-(2-(1H-pyrazole-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(215) 4-(3-(2-(1H-1,2,3-triazole-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(217) N,N-dimethyl-4-(3-(2-(5-methyl-1H-tetrazol-1-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(219) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol
(220) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl acetate
(221) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[3,2-C]pyridine-2-yl)-1-phenylcyclohexylamine, citrate
(223) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-phenylcyclohexylamine, citrate
(225) N,N-dimethyl-4-(3-methylbenzofuran-2-yl)-1-phenylcyclohexylamine, citrate
(227) 4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(228) (±)-3-(4-(dimethylamino)-4-benzyltoluene-1-enyl)-1H-pyrrolo[2,3-b]pyridine
(229) (±)-3-(4-(dimethylamino)-4-butylcyclohexyl-1-enyl)-1H-pyrrolo[2,3-b]pyridine
(230) (±)-3-(4-(dimethylamino)-4-paneltitle the CEN-1-enyl)-1H-pyrrolo[2,3-b]pyridine, citrate
(231) (±)-4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohexane-3-enamine, citrate
(232) (±)-4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohexane-3-enamine
(233) (±)-2-(3-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)benzo[b]thiophene-2-yl)ethanol hydrochloride
(234) (±)-2-(3-(4-(dimethylamino)-4-(pyridin-2-yl)cyclohex-1-enyl)benzo[b]thiophene-2-yl)ethanol hydrochloride
(235) 4-(1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane, citrate
(237) 1-benzyl-N,N-dimethyl-4-(1H-pyrrolo[2,3-b]pyridine-3-yl)cyclohexanamine hydrochloride
(238) 1-butyl-N,N-dimethyl-4-(1H-pyrrolo[2,3-b]pyridine-3-yl)cyclohexanamine hydrochloride
(239) (±)-4-(benzofuran-2-yl)-1-benzyl-N,N-dimethylcyclohex-3-enamine hydrochloride
(240) (±)-N,N-dimethyl-4-(3-methylbenzofuran-2-yl)-1-phenylcyclohexyl-3-enamine, citrate
(241) (±)-2-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)benzofuran-3-yl)ethanethiol, citrate
(242) (±)-N,N-dimethyl-4-(3-methylbenzo[b]thiophene-2-yl)-1-phenylcyclohexyl-3-enamine, citrate
(243) N,N-dimethyl-4-(3-methylbenzo[b]thiophene-2-yl)-1-phenylcyclohexylamine, citrate
(244) N,N-dimethyl-1-phenyl-4-(1H-pyrrolo[2,3-b]pyridine-3-yl)cyclohexanamine, citrate
(246) 1-(dimethylamino)-3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)propan-2-ol
(247) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine
(248) 4-(1,3-dimethyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexane
(249) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate
(251) (±-2-(4-(dimethylamino)-4-(thiophene-2-yl)-cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(252) (±)-2-(4-(dimethylamino)-4-(3-forfinal)-cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(253) (±)-2-(4-butyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(254) (±)-2-(4-(methylamino)-4-phenylcyclohexyl-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole
(255) (±)-2-(4-(dimethylamino)-4-(thiophene-2-yl)-cyclohex-1-enyl)-3-methyl-1H-indole, citrate:
(256) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-(thiophene-2-yl)cyclohexanamine, citrate
(258) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-3-methyl-1H-indol
(259) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexanecarboxylic
(260) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(261) 1-(3-forfinal)-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate
(263) (±)-2-(4-(dimethylamino)-4-(3-forfinal)-cyclohex-1-enyl)-3-methyl-1H-indol
(264) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate
(266) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole, citrate
(268) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-methyl-1H-indole, citrate
(270) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole hydrochloride
(272) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-methyl-1H-indole, citrate
(273) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-pyrrolo[2,3-b]pyridine-3-yl)propan-1-ol, citrate
(274) 1-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)-3-(methylamino)propan-2-ol, citrate
(275) 1-benzyl-3-(2-(2-(4-(di is ethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate
(277) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-3-phenylacetone, citrate
(279) 1-cyclopentyl-3-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate
(281) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)cyclopentanemethanol, citrate
(283) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)benzenesulfonamide, citrate
(284) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)thiophene-2-sulfonamide, citrate
(286) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)nicotinamide, citrate
(288) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)benzamide, citrate
(289) 1-(3-forfinal)-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine
(290) 1-(3-forfinal)-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(291) N-methyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate
(293) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-methyl-1H-indole, citrate
(294) N,N-dimethyl-1-phenyl-4-(1-(phenylsulfonyl)-1H-indol-2-yl)cyclohexanamine
(296) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohexyl-3-enamine
(297) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohexylamine, citrate
(298) 1-(dimethylamino)-3-(2-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-3-methyl-1H-indol-1-yl)propan-2-ol, citrate
(299) 1-(dimethylamino)-3-(2-(4-(is metilamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)propan-2-ol, citrate
(300) 2-(3-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-1H-indol-1-yl)ethanol hydrochloride
(301) (±) 3-(4-(dimethylamino)-4-phenylcyclohexyl-1-enyl)-(1-(phenylsulfonyl)-1H-indole)hydrochloride
(302) 1-benzyl-N,N-dimethyl-4-(1-methyl-1H-indol-2-yl)cyclohex-3-enamine hydrochloride
(303) N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)-1-(thiophene-2-yl)cyclohexanamine hydrochloride
(305) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-(4-methylthiazole-2-yl)cyclohexanamine
(307) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol
in the form of a racemate, diastereomers, bases and/or salts of physiologically compatible acids.

11. The method of obtaining substituted heteroaryl derivatives of formula Ic

where the values of A, B, W, R1, R2, R3given in claim 1, and ketones of General formula B is subjected to interaction with heteroaromatic General formula A in an organic solvent or mixture of solvents, such as ethyl acetate, chloroform, dichloromethane (DHM), ethylene dichloride (EDC), diethyl ether (Et2O), acetonitrile (MeCN) or nitromethane adding organic or inorganic acids, for example HCl, HBr, triftormetilfullerenov acid, methanesulfonic acid, acetic acid, triperoxonane acid or without solvents in organic or inorganic acid or acid mixtures at temperatures between 0°C and 150°C PR is necessary with the use of microwave irradiation and then adding an organic or inorganic reducing agent, for example, triethylsilane or tin powder at a temperature between 0°C and 150°C, optionally using microwave irradiation.

12. The method of obtaining substituted heteroaryl derivatives of the General formula Id or Ie,


where the values of A, B, W, C, R1, R2, R3given in claim 1, and heteroaromatic General formula A or A' is subjected to interaction with cyclohexane General formula B in an organic solvent or mixture of solvents, such as chloroform, dichloromethane (DHM), ethylene dichloride (EDC), diethyl ether (Et2O), acetonitrile (MeCN) or nitromethane adding organic or inorganic acids, for example HCl, HBr, triftormetilfullerenov acid, methanesulfonic acid, acetic acid, triperoxonane acid at temperatures between 0°C and 150°C, optionally using microwave irradiation
or heteroaromatic General formula A or A' is subjected to interaction with cyclohexane General formula B when adding a base, for example KOH or NaOH, in an organic solvent, for example methanol, at temperatures between 20 and 100°C.

13. The method of obtaining substituted heteroaryl derivatives of the General formula Ic, or If

where the values of A, B, W, C, R1, R2, R3given in claim 1, by restoring the connection Id or Ie

using hydrogen in the form of HBr/glacial acetic acid/Sn or HCl/Sn (hydrogen at the time of allocation) or H2in the presence of a metal catalyst such as palladium on charcoal, platinum on charcoal, platinum oxide, Raney Nickel, rhodium or complexes of ruthenium in a solvent or mixture of solvents such as methanol, ethanol, acetone, ethyl ether, acetic acid, HBr or acetic acid at temperatures between 0°C and 150°C.

14. The drug showing an analgesic effect, containing at least one substituted heteroaryl derivative according to one of claims 1 to 10, optionally in the form of its racemate, diastereomers, in any mixing ratio; in the form of its bases or in the form of its salts with physiologically compatible acids, and optionally contain suitable additives and/or auxiliary substances.

15. The use of substituted heteroaryl derivative according to one of claims 1 to 10, optionally in the form of its racemate, diastereomers, in any mixing ratio; in the form of bases or salts of physiologically compatible acids; to obtain drugs for the treatment of pain, in particular acute, neuropathic, chronic Bo and or inflammatory pain.

16. The use of substituted heteroaryl derivative according to one of claims 1 to 10 to obtain drugs for the treatment of States of fear, stress and stress-related syndromes, depression, epilepsy, Alzheimer's disease, senile dementia, catalepsy, General cognitive dysfunctions, disorders of learning and memory (as nootrop), withdrawal, abuse and/or dependence of alcohol and/or drug and/or medication, sexual dysfunctions, cardiovascular diseases, hypotension, hypertension, tinnitus, pruritus, migraine, hearing loss, lack of bowel motility, impaired food intake, anorexia, obesity, locomotor disorders, diarrhoea, cachexia, urinary incontinence or as a muscle relaxant, anticonvulsive or anaesthetic or for co-admission for treatment with an opioid analgesic or with an anaesthetic, for diuresis or antinatriuretic, anxiolysis, for modulation of motor activity, for modulation of the distribution of neurotransmitters and treatment related neurodegenerative diseases, for the treatment of withdrawal symptoms and/or to reduce the narcotic potential of opioids.



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: there are produced new diazepane substituted compounds representing various heterocyclic systems, including condensed, pharmaceutical compositions containing said compounds.

EFFECT: producing the compounds and compositions for preventing and treating neurological and mental disorders and diseases with involved orexin receptors.

13 cl, 1 tbl

New compounds // 2458920

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of formula or to its pharmaceutically acceptable salts wherein -A-(R1)a means a group; -B-(R2)b means a group specified in the patent claim 1, R3 means hydrogen; X means CH2 or O; and Y means CH2. Also, the invention refers to a pharmaceutical composition exhibiting FGFR inhibitor activity on the basis of the declared compound.

EFFECT: there are produced new compounds and based pharmaceutical composition which can find application in medicine for preparing a cancer drug.

8 cl, 1 tbl, 180 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to to new compounds of formula (1) or their pharmaceutically acceptable salts, optionally in the form of (1S)-isomers showing the properties of polo-like kinase (serine-threonine kinase) PLK1 inhibitor. In the compounds of formula (1) , R1 represents a halogen atom; a lower alkyl group having 1-2 carbon atoms, which can be substituted by 3 fluorine atoms; or a cyclopropyl group; R2 represents a hydrogen atom; one of R3 and R4 represents a hydrogen atom while the other one of R3 and R4 represents: a) a lower alkyl group substituted by NRaRb wherein each Ra and Rb, which can be identical or different, represent a lower alkyl group, or each Ra and Rb, which can be different, represent a hydrogen atom, a lower alkyl group or a cycloalkyl group having 3-6 carbon atoms wherein a cycloalkyl group can be substituted by one ore more substitutes which can be identical or different and specified in a group 1): a lower alkyl; b) a 4-6-member aliphatic heterocyclic group specified in an azetidinyl group, a pyrrolidinyl group and a piperidinyl group; c) a lower alkyl group substituted by a 4-6-member aliphatic heterocyclic group specified in an azetidinyl group, a pyrrolidinyl group and a piperidinyl group; d) a 6-member aromatic heterocyclic group specified in a pyridyl group wherein each of an aliphatic heterocyclic group and an aromatic heterocyclic group can be substituted by substitutes specified in a group 1) described above; R5 represents a hydrogen atom, a cyano group, a halogen atom or a lower alkyl group.

EFFECT: compounds can find application in treating oncological diseases.

10 cl, 4 dwg, 8 tbl, 42 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to organic chemistry, namely new 1H-pyrrolo[3,4-b]quinoline-3,9(2H, 4H)-dione derivatives of general formula 1

wherein R1=Alk, Ar; R2=H, Alk, halogen; R3=H, Alk, halogen; R4=H, Alk, halogen; R5=H, Alk, halogen; R6=CH2Ar, R7=Ar, Also, the invention refers to a method for preparing them.

EFFECT: there are prepared new 1H-pyrrolo[3,4-b]quinoline-3,9(2H, 4H)-dione derivatives possessing anti-tuberculosis activity.

3 cl, 1 tbl, 9 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula I , and pharmaceutically acceptable salts thereof, where L denotes O, S, or CH2; Y denotes N or CH; Z denotes CR3; G denotes CH; R1 denotes a heteroaryl ring of formula , where D1 denotes S, O; D2 denotes N or CR12; D3 denotes CR12; R2 denotes (C6-C10)-aryl; 5-9-member mono- or bicyclic heteroaryl with 1 or 2 heteroatoms independently selected from N or S; a saturated or partially saturated (C3-C7)-cycloalkyl; or a saturated 5-6-member heteocyclyl with 1 heteroatom selected from N, where said aryl, heteroaryl, cycloalkyl and heterocyclyl are optionally substituted with one or two groups independently selected from (C1-C6)-alkyl, F, Cl, Br, CF3, CN, NO2, OR6, C(-O)R6, C(=O)OR6, C(=O)NR6R7, saturated 6-member heterocyclyl with 2 heteroatoms independently selected from N or O, and S(O)2R6, and where said alkyl is optionally substituted with one -OR8 group; R3 denotes H; (C1-C6)-alkyl; (C2-C6)-alkenyl; Cl; Br; OR6; SR6; phenyl; or a 6-member heteroaryl with 1 heteroatom selected from N, where said alkyl and alkenyl are optionally substituted with one group selected from C(=O)OR8, -OR8, -NR8R9; or a saturated 6-member heterocyclyl with 1 heteroatom selected from N or O.

EFFECT: disclosed compounds are used in treating and preventing diseases mediated by insufficient level of glucokinase activity, such as sugar diabetes.

16 cl, 479 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to new benzimidazole derivatives of general formula (I) or to its pharmacologically acceptable salts wherein R1 represents a C6-aryl group which can be substituted by 1-3 groups optionally specified in a group of substitutes (a), or a heterocyclic group which represents pyridyl, dihydrobenzofuranyl, 1,3-benzodioxolyl, tetrahydropyranyl, tetrahydrofuranyl which can be substituted by 1-3 groups optionally specified in a group of substitutes (a), R2 represents a C1-C6 alkyl group, R3 represents a C6-aryl group which can be substituted by 1-2 groups optionally specified in a group of substitutes (a), Q represents a group represented by formula =CH-, or a nitrogen atom and a group of substitutes (a) represents a group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 halogenated alkyl group, a carboxyl group, a C2-C7 alkylcarbonyl group, a C2-C7 alkoxycarbonyl group, a C1-C6 alkoxy group, a C1-C6 halogenated alkoxy group, an amino group, a 4-morpholinyl group and a di-C1-C6 alkyl)amino group. Also, the invention refers to a pharmaceutical composition based on a compound of formula (I), to a PPARγ activator/modulator based on the compound of formula (I), to using the compound of formula (I), to a method of reducing blood glucose, to a method of activating PPARγ, a method of treating and/or preventing said pathological conditions.

EFFECT: there are produced new benzimidazole derivatives showing PPARγ modulatory activity.

41 cl, 2 dwg, 6 tbl, 76 ex

FIELD: chemistry.

SUBSTANCE: described are novel benzotriazole UV-absorbers, having absorption spectrum shifted towards the long-wave side with considerable absorption in the region up to 410-420 nm, having general formulae (a)-(k) (structural formula and values of radicals are given in the description), composition which is stabilised with respect to UV radiation and containing novel UV-absorbers, and use of the novel compounds as UV light stabilisers for organic materials.

EFFECT: obtaining novel benzotriazole UV-absorbers, having absorption spectrum shifted towards the long-wave side.

13 cl, 23 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel azaindole derivatives, having JAK-2 and JAK-3 kinase inhibiting activity, or pharmaceutically acceptable salts thereof. In formula (I): R3 denotes H; X1 denotes N or CR4; R2 denotes H, COOH, COOR' or CONHR'; R4 denotes H, F, R, OH, OR', COR', COOH, COOR', CONH2 or CN; or R2 and R4, taken together, form a benzene ring optionally substituted with 1-2 R10; R' denotes C1-3-alkyl or C1-3-alkenyl, each optionally substituted 1-2 R5; each R5 is independently selected from CN, unsubstituted C1-2alkyl, or two groups R5 together with a carbon atom with which they are bonded form a cyclopropyl ring; each R10 is independently selected from halogen, OCH3 or OH; R1 denotes or , R is H or denotes C1-2alkyl, optionally substituted with 1-3 R11; R6 denotes C1-4alkyl, optionally substituted with 1-5 R12; values of radicals R7 -R9, ring A, R11 -R14. The invention also relates to a pharmaceutical composition containing said compounds and a method of treating or reducing severity of a pathological condition such as allergy, asthma, amyotrophic lateral sclerosis, multiocular sclerosis, graft rejection, rheumatoid arthritis, solid malignant tumour, haematologic malignant disease, leukaemia, lymphoma and myeloproliferative disorders.

EFFECT: high efficiency of using the compounds.

41 cl, 6 ex, 6 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula , where R1 denotes OH, OPO3H2 or OCOR5; R2 denotes H, OH or OPO3H2; A denotes N or CR6; R3 denotes fluorine; R4 denotes H, C1-3alkyl or C3-6cycloalkyl; R5 denotes an alanine residue; R6 denotes H, C1-6alkoxy group or halogen; and n=0 or 1; and to pharmaceutically acceptable salts of compounds of formula I. The invention also relates to a pharmaceutical composition having antibacterial activity, and to use of compounds of formula I to obtain a medicinal agent for preventing or treating bacterial infections.

EFFECT: compounds of formula I, having antibacterial activity.

14 cl, 3 dwg, 2 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound having chemical structure of formula II , all salts and stereoisomers thereof, where the value of radicals D, A2 and B are as described in paragraph 1 of the claim. The invention also relates to a composition having activity as a c-kit and c-fms modulator, a method of treating a subject suffering from a disease or condition mediated by c-kit and c-fms and a kit for modulating c-kit and c-fms.

EFFECT: novel compounds which can be useful in treating c-kit-mediated diseases or conditions and/or c-fms-mediated diseases or conditions are obtained and described.

21 cl, 44 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I),

, where groups and radicals R1, R2 independently denote H, C1-8-alkyl or C3-7-cycloalkyl, where the alkyl or cycloalkyl group can be mono- or poly-substituted with identical or different groups R11; or R2 denotes a -CH2- or -CH2-CH2- bridge which is bonded with a group Y, and R1 is as defined above, or denotes a group selected from C1-4-alkyl-CO-, C1-4-alkyl-O-CO-, (C1-4-alkyl)NH-CO- or (C1-4-alkyl)2N-CO-, where the alkyl groups can be mono- or polyfluorinated; or R1 and R2 form an alkylene bridge such that R1R2N- denotes a group selected from: azetidine, pyrrolidine, piperdine, azepan, 2,5-dihydro-1H-pyrrole, 1,2,3,6-tetrahydropyridine, 2,3,4,7-tetrahydro-1H-azepine, 2,3,6,7-tetrahydro-1H-azepine, piperazine, in which the free amino group is substituted with R13, piperidin-4-one, morpholine, thiomorpholine, 4-C1-4-alkoxy iminopiperidin-1-yl and 4-hydroxy iminopiperidin-1-yl. Wherein, when R1 and R2 form an alkylene bridge, one or more H atoms in the alkylene bridge can be substituted with identical or different groups R14, and X denotes a C1-3-alkylene bridge which can contain one, two or three identical or different C1-3-alkyl substitutes; and Y denotes a group of subformula selected from: and , where the group can be mono-substituted with a substitute R20; Z denotes -CH2-CH2- or -C(=O)-CH2-; U, V both denote CH, one of groups U, V denotes N, and the other of U, V denotes CH, where CH can be substituted with L; and L independently denotes halogen, cyano or C1-3-alkyl; and k equals 0, 1 or 2; W is selected from a group consisting of -CH2-O- and -O-CH2-; B is selected from a group consisting of phenyl, pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, thiophenyl and thiazolyl; each of which can be mono- or poly-substituted with identical or different substitutes R20; radicals R11, R13, R14, R20 assume values given in claim 1. The invention also relates to a pharmaceutical composition containing at least one compound of formula I and having action on MCH receptor.

EFFECT: disclosed pharmaceutical compositions are useful in treating metabolic disorders or eating disorders, especially obesity, bulimia, anorexia, hyperphagia and diabetes.

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted pyrimidine derivatives, having HIV replication inhibiting properties, or pharmaceutically acceptable salts thereof. In formula (1): R1 denotes hydrogen; R2 and R3 independently denote hydrogen; R7 and R8 denote C1-6alkyl; R4 denotes cyano; R9 denotes C1-6alkyl optionally substituted with cyano, C2-6alkenyl substituted with cyano, C2-6alkynyl optionally substituted with cyano; R5 denotes C1-6alkyl optionally substituted with Ar or Het; C2-6alkenyl optionally substituted with Ar or Het; C2-6alkynyl optionally substituted with Ar or Het; C3-7cycloalkyl; Ar; Het; R6 denotes H, Het; Y denotes -OR11, -NR12R13; R11 denotes hydrogen or C1-6alkyl optionally substituted with hydroxy, C1-6alkoxy or pyridyl; R12 denotes hydrogen or C1-6alkyl; R13 denotes hydrogen or C1-6alkyl; or R12 and R13 together with a nitrogen atom, which is substituted by said two substitutes, form a morpholinyl; imidazolyl; X denotes -NR1-; Het denotes 5- or 6-member completely saturated ring, where one or two ring members are heteroatoms, each independently selected from nitrogen and sulphur, and where the rest of the ring members are carbon atoms; and where any member of the heterocycle with a nitrogen heteroatom can optionally be substituted with C1-6alkyl; where the 5- or 6-member ring can optionally be annelated with a benzene or thiophene ring; each aryl independently denotes phenyl or phenyl substituted with one substitute selected from C1-6alkoxy.

EFFECT: high efficiency of using said compounds.

7 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing mono-(di-, tetra-)methyl-1,2-bis-(1,3,5-dithiazinan-5-yl)ethanes of general formula (1-3): , (1) R1=CH3, R2, R3, R4=H (2) R1, R3=CH3, R2, R4=H (3) R1, R2, R3, R4=CH3, which involves reaction of hydrogen sulphide-saturated aqueous solution of (37%) formaldehyde and acetaldehyde with 1,2-diaminoethane with molar ratio of initial reagents 1,2-diaminoethane: formaldehyde: acetaldehyde: hydrogen sulphide equal to 10:50:10:40 to obtain (1), 10:40:20:40 to obtain (2), 10:20:40:40 to obtain (3), at temperature 40°C and atmospheric pressure for 2.5-3.5 hours.

EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1,2-bis-(2,4,6-trialkyl-1,3,5-dithiazinan-5-yl)ethanes of general formula (1): . The method involves reaction of a hydrogen sulphide-saturated aldehyde of formula RCHO, where R=CH3, C2H5, n-C3H7, n-C4H9, n-C5H11, with 1,2-diaminoethane with molar ratio of initial reagents 1,2-diaminoethane: aldehyde: hydrogen sulphide equal to 10:60:40 at temperature 40°C and atmospheric pressure for 2.5-3.5 hours.

EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 2(3H)-benzothiazolone. The method is realised by boiling bis-(2,2'-dimethoxycarboxamido)-phenyl disulphide with zinc dust for 7,5 hours in glacial acetic acid, followed by separating zinc salts, diluting the filtrate with ice water, filtering the crystalline product and washing said product with diluted HCl (1:1) and water and then drying on air and recrystallising from ethanol. The invention also relates to a method of producing 3-2-[2-oxo-1,3-benzothiazol-3(2H)-yl]ethyl-1,3-benzothiazol-2(3H)-one. The method is realised by boiling 2(3H)-benzothiazolone with 1,2-dibromoethane in acetone in the presence of K2CO3. Water is then added and the mixture is treated with diethyl ether, followed by washing the organic phase with 10% aqueous NaOH solution and water, drying with anhydrous potassium carbonate, removing the solvent and recrystallising from methanol. The invention relates to a method of producing 3-(2-chloroacetyl)-1,3-benzothiazol-2(3H)-one. The method is realised by boiling 2(3H)-benzothiazolone in anhydrous benzene with chloroacetyl chloride for 10 hours, then washing the cooled reaction mass with 2% aqueous NaOH solution, extracting with benzene, washing the merged extracts with water, drying with anhydrous calcium chloride and removing the solvent, followed by recrystallisation from chloroform.

EFFECT: improved method of producing 2(3H)-benzothiazolone derivatives.

3 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to tetrahydroquinoline derivatives of formula (I), where values of C3-C4, R2, R3, R4, R5, L1, L2, Y and X are given in claim 1, as muscarinic receptor agonists; compositions containing said compounds; methods of inhibiting muscarinic receptor activity using said compounds; methods of treating diseased conditions associated with the muscarinic receptor using said compounds, and methods of identifying a subject suitable for treatment using said compounds.

EFFECT: improved properties of compounds.

22 cl, 1 tbl, 3 ex, 3 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to novel carbostyril compounds of general formula (1) or salts thereof with common pharmaceutically acceptable acids or pharmaceutically acceptable basic compounds, having activity on promotion of TFF2 production, a pharmaceutical composition based on said compounds, an agent based on disclosed compounds used in case of a disorder where up-regulation of TFF has a prophylactic and/or therapeutic effect, use of disclosed compounds to prepare said agent and a method of producing disclosed compounds. The invention also relates to novel specific carbostyril compounds or salts thereof with common pharmaceutically acceptable acids or pharmaceutically acceptable basic compounds. In structural formula (1), A is a direct bond, a lower alkylene group or lower alkylidene group, X is an oxygen or sulphur atom, the bond between positions 3 and 4 of the carbostyril backbone is a single bond or a double bond, R4 and R5 each denotes a hydrogen atom provided that, when the bond between positions 3 and 4 of the carbostyril backbone is a double bond, R4 and R5 can instead be bonded to each other in form of a -CH=CH-CH=CH- group, and R1, R2 and R3 assume values given in the claims.

EFFECT: high efficiency of compositions based on said compounds.

32 cl, 23 dwg, 184 tbl, 1535 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general structural formula:

or to pharmaceutically acceptable salts, where Z denotes -O- or -CH2- or -CH2-CH2-; X1 denotes a covalent bond or -O-; Y1 denotes a covalent bond or C1-C10 alkylene, provided that Y1 is a covalent bond only when X1 denotes a covalent bond; R1 denotes a) (C3-C7)cycloalkyl or b) phenyl or heteroaryl, which is a monovalent heteroatomatic monocyclic radical ring containing 1-2 heteroatoms, independently selected from nitrogen and sulphur, possibly substituted with 1-3 groups, independently selected from fluorine, chlorine, bromine, (C1-C6)alkyl or (C1-C6)-alkoxy; R2 denotes -OC(O)(NH2), -OC(O)(NHR9), -NHC(O)OR9, -C(O)R9, -C(O)(NH2), -C(O)(NHR9) or -NHC(O)H, where R9 denotes a linear or branched C1-C5 alkyl or a linear or branched (C1-C5)alkoxyalkyl; R3 denotes H, C1-C5 alkyl, -NHC(O)R10 or OH, where R10 denotes C1-C3 alkyl, provided that when R3 denotes -OH, X1 is not O and R2-Y1-X1 is not -OC(O)(NH2), -OC(O)(NHR9), -NHC(O)OR9 or -NHC(O)H; -Q denotes

, where N and N are bonded by bonds denoted by a wavy line; R4 denotes H; R5 and R6 independently denote: a) H, (C1-C10)alkyl, (C4-C10)cycloalkylalkyl, hydroxylated (C4-C10)cycloalkylalkyl, halo(C4-C10)cycloalkylalkyl, (C1-C2)alkyl(C4-C10)cycloakylalkyl, (C4-C10)bicycloalkyl(C1-C3)alkyl, (C1-C5)alkoxy(C1-C5)alkyl; or a saturated heterocyclyl(C1-C3)alkyl, where the saturated heterocyclic ring is selected from 5-, 6- or 7-member heterocyclic rings which contain 1 heteroatom independently selected from N and O; or b) phenyl(C1-C2)alkyl, phenoxymethyl, each of which is possibly with 1-3 groups independently selected from fluorine, chlorine, (C1-C3)alkyl, (C1-C3)alkoxy; provided that both R5 and R6 are not H; G denotes NH2 or NHR7; R7 denotes (C1-C6)alkyl; or R5 and R7 together denote -CH2, -(CH2)2 or -(CH2)3, possibly substituted with 1-2 groups independently selected from (C1-C8)-alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C2)alkyl or (C1-C8)alkoxy. The invention also relates to compounds selected from the group, pharmaceutical compositions, a method for antagonising one or more aspartate proteases, as well as methods of treating aspartate protease-mediated disorders.

EFFECT: obtaining novel biologically active compounds having activity towards rennin.

35 cl, 33 ex, 4 dwg

FIELD: medicine.

SUBSTANCE: compounds can be used for treating neurological conditions, more specifically for treating neurodegenerative conditions, such as Alzheimer's disease. In a compound of formula I R2 represents H or CH2NR1R4 where R1 and R4 are independently selected from H, unsubstituted C1-6alkyl, substituted or unsubstituted C3-6 cycloalkyl, R3 represents H; substituted or unsubstituted C1-4alkyl; substituted or unsubstituted C2-4alkenyl; substituted or unsubstituted 6-members aryl condensed or uncondensed with substituted or unsubstituted 6-members aryl or 5-6-members heteroaryl, containing 1-2 nitrogen atoms in a cycle; substituted or unsubstituted saturated or unsaturated 5 or 6-members N-containing heterocycle which can additionally contain nitrogen, oxygen or the sulphur atom condensed or ucondensed with substituted or unsubstituted 6-members aryl or 5-6-members heteroaryl containing nitrogen in a cycle; (CH2)nR6 where n is an integer from 1 to 6, and the values of R6 and the values of other radicals are specified in the patent claim.

EFFECT: increased antiamyloidogenic action.

20 cl, 20 tbl, 6 dwg, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula (I) or pharmaceutically acceptable salts thereof, where Q is CH or N; R2 is C1-C4 alkyl or C3-C4-cycloalkyl; Y is R5-O; where R5 is propynyl; X is selected from a group consisting of aryl, heteroaryl, C1-C5-alkyloxy, heterocycloalkyl, arylamino, heteroarylamino, heteroaryl-C1-C4-alkylamino, aryloxy, aryl-C1-C2-alkyloxy or C3-C6-cycloalkyl-C1-C4-alkyloxy, each of which is optionally substituted with 1-3 times; the optional substitute(s) for X is(are) independently selected from a group comprising halogen, cyano, trifluoromethyl, nitro, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkyloxy-C1-C4-alkoxy, -SMe, SO2-C1-C2-alkyl, -NMe2, - C(O)O-C1-C5-alkyl, -SCF3, -SO2-NH2, -SO2-C2-alkyl-OH, -CONH2, -COMe, - CONH-C1-C4-alkyl, -CONMe2, -NHCOMe, -CH2COOEt, -OCH2COOEt, -CH2- cyclopropyl, and each R3 and R4 is H; where aryl denotes phenyl or naphthyl; heteroaryl denotes monocyclic or bicyclic hydrocarbon containing 5-10 ring atoms, one or more of which are heteroatoms selected from O, N or S; heterocyclyl denotes piperidinyl or benzodioxolyl; or a compound or pharmaceutically acceptable salt thereof, selected from a group comprising (4-dimethylaminophenyl)-[4-(4-cyclopropylphenyl)-6-propargyloxyquinazolin-2-yl]methanone, (3-sulphamoylphenyl)amide 4-(4-isopropylphenyl)-6-prop-2-ynyloxy-3,4-dihydroquinazoline-2-carboxylic acid, [3-(2-hydroxyethanesulphonyl)phenyl]amide 4-(4-isopropylphenyl)-6-prop-2-ynyloxy-3,4-dihydroquinazoline-2-carboxylic acid, (3-methylsulphanylphenyl)amide 4-(4-isopropylphenyl)-6-prop-2-ynyloxy-3,4-dihydroquinazoline-2-carboxylic acid, (3-methanesulphonylphenyl)amide 4-(4-isopropylphenyl)-6-prop-2-ynyloxy-3,4-dihydroquinazoline-2-carboxylic acid, and (5-ethanesulphonyl-2-hydroxyphenyl)amide 4-(4-isopropylphenyl)-6-prop-2-ynyloxy-3,4- dihydroquinazoline -2-carboxylic acid. The invention also relates to a pharmaceutical composition based on the compound of formula (I) and use of the compound of formula (I).

EFFECT: novel benzoquinazoline derivatives, which are useful in treating bone disorders, are obtained.

6 cl, 128 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to new imidazole derivatives of formula I wherein R1 represents a hydrogen atom or C1-7alkyl; R2 represents C1-7alkyl; R3 represents C1-7alkyl, C1-7alkoxy, phenyloxy, benzyloxy, a halogen atom or C1-7alkyl substituted by a halogen atom; R4 represents a hydrogen atom or C1-7alkyl; X represents -CH2-, -CHR2 - or -O; Y represents -CH2-, -CH2CH2- or a bond; provided X represents -O-, Y represents -CH2-; Z represents -CH2- or -CHR2-; provided R2 is found twice, simultaneously for X and Z which are CHR2 , then R2 can be identical alkyls or different; n has the value 0, 1 or 2; provided n has the value 2, R3 can be identical or different; and its pharmaceutically acceptable acid addition salts, except for the following compounds: 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline and 1-(3H-imidazol-4-ylmethyl)-2,3-dihydro-1H-indole. Also, the invention refers to a method for preparing the compounds of formula I, to a drug based on the compound of formula I and applying the compound of formula I in preparing the drug.

EFFECT: there are prepared new imidazole derivatives effective in treating such pathological conditions, as bipolar disorder, stress-induced disorder, psychotic disorders, schizophrenia, neurological conditions, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease.

13 cl, 61 ex

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