RU2006129297A - Производные n-(1,5-дифенил-1н-пиразол-3-ил)сульфонамида со сродством к рецепторам cb1 - Google Patents
Производные n-(1,5-дифенил-1н-пиразол-3-ил)сульфонамида со сродством к рецепторам cb1 Download PDFInfo
- Publication number
- RU2006129297A RU2006129297A RU2006129297/04A RU2006129297A RU2006129297A RU 2006129297 A RU2006129297 A RU 2006129297A RU 2006129297/04 A RU2006129297/04 A RU 2006129297/04A RU 2006129297 A RU2006129297 A RU 2006129297A RU 2006129297 A RU2006129297 A RU 2006129297A
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- RU
- Russia
- Prior art keywords
- methyl
- pyrazol
- dichlorophenyl
- bromophenyl
- ethyl
- Prior art date
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- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 title 1
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 title 1
- FTEXIWFTJCMJFB-UHFFFAOYSA-N O=S(=O)Nc1cc(-c2ccccc2)n(n1)-c1ccccc1 Chemical class O=S(=O)Nc1cc(-c2ccccc2)n(n1)-c1ccccc1 FTEXIWFTJCMJFB-UHFFFAOYSA-N 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 18
- -1 trifluoromethoxyl radical Chemical class 0.000 claims 18
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- CYAYCOCJAVHQSD-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid Chemical compound CC=1C(C(O)=O)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 CYAYCOCJAVHQSD-UHFFFAOYSA-N 0.000 claims 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- KCCPXPGXYVBAAP-UHFFFAOYSA-N (2-fluorophenyl)methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1F KCCPXPGXYVBAAP-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000027559 Appetite disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Claims (7)
1. Соединение, отвечающее формуле (I)
в которой R1 означает
(C1-C6)алкил;
(C3-C7)циклоалкил, незамещенный или замещенный один или несколько раз (C1-C3)алкильной группой;
(C3-C7)циклоалкилметил, незамещенный или замещенный один или несколько раз в карбоцикле (C1-C3)алкилом;
фенил, незамещенный или моно-, ди- или тризамещенный заместителем, выбранным независимо из атома галогена, (C1-C4)алкила, (C1-C3)алкокси, циано, трифторметильного радикала, трифторметоксильного радикала, группы S(O)nAlk, (C1-C3)алкилкарбонильной группы, фенила;
бензил, незамещенный или моно- или дизамещенный заместителем, выбранным независимо из атома галогена, (C1-C3)алкила, (C1-C3)алкокси; трифторметильный радикал;
тиенил, незамещенный или замещенный атомом галогена или изоксазолилом;
- R2 означает атом водорода или (C1-C3)алкил;
- R3 означает атом водорода или (C1-C5)алкил;
- R4, R5, R6, R7, R8 и R9 каждый независимо означает атом водорода, атом галогена, (C1-C7)алкил, (C1-C5)алкокси, трифторметильный радикал или группу S(O)nAlk;
- n означает 0,1 или 2;
- Alk означает (C1-C4)алкил,
в состоянии основания или кислотной-аддитивной соли, а также в состоянии гидрата или сольвата.
2. Соединение формулы (I) по п.1, в которой:
- R1 означает
этил, изопропил, н-бутил;
циклогексил;
циклогексилметил;
2-хлорфенил, 3-хлорфенил, 2-фторфенил, 3-хлор-4-фторфенил, 4-бром-2-этилфенил, 3-метилфенил, 4-трет-бутилфенил, 3,5-диметилфенил, 3-метоксифенил, 4-метоксифенил, 3-цианофенил, 4-цианофенил, 2-(трифторметил)фенил, 3-(трифторметил)фенил, 4-(трифторметил)фенил, 3,5-бис(трифторметил)фенил, 2-(трифторметокси)фенил, 3-(трифторметокси)фенил, 2-(метилсульфонил)фенил, 3-(метилсульфонил)фенил, 3-ацетилфенил, 3-бифенил, 2-бифенил;
3-хлорбензил, 2-фторбензил, 4-фторбензил, 3-(трифторметил)бензил, 4-(трифторметил)бензил;
5-бром-2-тиенил; 5-изоксазол-3-ил-2-тиенил;
- R2 означает атом водорода или метил;
- R3 означает метил или этил;
- R4 означает атом водорода;
- R5 находится в положении -4- фенила и означает атом брома, хлора, фтора или метокси;
- R6 означает атом водорода;
- R7 означает атом водорода;
- R8 находится в положении -4- фенила и означает атом водорода, атом хлора, атом фтора;
- R9 находится в положении -2- фенила и означает атом хлора или фтора,
в состоянии основания или кислотно-аддитивной соли, а также в состоянии гидрата или сольвата.
3. Соединение формулы (I) по п.1, выбранное из:
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]бутан-1-сульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]циклогексансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]циклогексилметансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-хлорбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]-4-трет-бутилбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-4-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-4-(трифторметил)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-2-(метилсульфонил)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]-1-(3-хлорфенил)метансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-1-[3-(трифторметил)фенил]метансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-хлор-4-фторбензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-бутан-1-сульфонамида;
- 3-хлор-N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]бензолсульфонамида;
- 4-трет-бутил-N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]бензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-метоксибензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-цианобензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-4-(трифторметил)бензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-2-(трифторметокси)бензолсульфонамида;
- N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-2-(метилсульфонил)бензолсульфонамида;
- 3-хлор-N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]-4-фторбензолсульфонамида;
- 4-бром-N-[[5-(4-хлорфенил)-1-(2,4-дихлорфенил)-4-метил-1H- пиразол-3-ил]метил]-2-этилбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]этансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]пропан-2-сульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]бутан-1-сульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]циклогексансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-1-циклогексилметансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-3-хлорбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-2-хлорбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-3-метилбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-4-трет-бутилбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-4-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-3-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-4-(трифторметил)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-3-(трифторметил)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-2-(трифторметил)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-3-(трифторметокси)бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-2-(трифторметокси)бензолсульфонамида;
- 3-ацетил-N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]бензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]бифенил-3-сульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-1-[4-(трифторметил)фенил]метансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-1-[3-(трифторметил)фенил]метансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-3,5-диметилбензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-3,5-бис(трифторметил)бензолсульфонамида;
- 3-хлор-N-[[1-(2-хлорфенил)-5-(4-хлорфенил)-4-метил-1Н-пиразол-3-ил]метил]бензолсульфонамида;
- N-[[1-(2-хлорфенил)-5-(4-хлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-2-фторбензолсульфонамида;
- N-[[1-(2-хлорфенил)-5-(4-хлорфенил)-4-метил-1H-пиразол-3-ил]метил]-3-цианобензолсульфонамида;
- N-[[1-(2-хлорфенил)-5-(4-хлорфенил)-4-метил-1H-пиразол-3-ил]метил]-3-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1H-пиразол-3-ил]метил]-3-метоксибензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-метил-1Н-пиразол-3-ил]метил]-3-цианобензолсульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-1-(2-фторфенил)метансульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]-1-(4-фторфенил)метансульфонамида;
- 5-бром-N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1H-пиразол-3-ил]метил]тиофен-2-сульфонамида;
- N-[[5-(4-бромфенил)-1-(2,4-дихлорфенил)-4-этил-1Н-пиразол-3-ил]метил]-5-изоксазол-3-илтиофен-2-сульфонамида;
- 3-хлор-N-[[1-(2,4-дихлорфенил)-5-(4-метоксифенил)-4-метил-1Н-пиразол-3-ил]метил]бензолсульфонамида;
- N-[[1-(2,4-дихлорфенил)-5-(4-метоксифенил)-4-метил-1H-пиразол-3-ил]метил]-3-метилбензолсульфонамида,
в состоянии основания или кислотно-аддитивной соли, а также в состоянии гидрата или сольвата.
4. Способ получения соединений формулы (I) по п.1, отличающийся тем, что соединение формулы
в которой R2, R3, R4, R5, R6, R7, R8 и R9 такие, как определено для соединения формулы (I) в п.1,
в присутствии основания и в растворителе приводят в реакцию с сульфонилгалогенидом формулы
в которой R1 такой, как определено для соединения формулы (I) в п.1, и Hal означает атом галогена.
5. Медикамент, отличающийся тем, что он содержит соединение формулы (I) по любому из пп.1-3 или аддитивную соль этого соединения с фармацевтически приемлемой кислотой, а также гидрат или сольват соединения формулы (I).
6. Фармацевтическая композиция, отличающаяся тем, что она содержит соединение формулы (I) по любому из пп.1-3 или фармацевтически приемлемую соль, гидрат или сольват этого соединения, а также, по меньшей мере, один фармацевтически приемлемый эксципиент.
7. Применение соединения формулы (I) по любому из пп.1-3 для получения медикамента, предназначенного для лечения и предупреждения нарушений аппетита, желудочно-кишечных расстройств, воспалительных явлений, болезней иммунной системы, психотических расстройств, алкогольной зависимости, никотиновой зависимости.
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| FR0400257 | 2004-01-12 | ||
| FR0400257A FR2864958B1 (fr) | 2004-01-12 | 2004-01-12 | Derive de n-[(1,5-diphenyl-1h-pyrazol-3-yl)methyl] sulfonamide, leur preparation et leur application en therapeutique. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| FR2880023B1 (fr) * | 2004-12-23 | 2007-02-23 | Sanofi Aventis Sa | Derives de n-[(4,5-diphenyl-3-alkyl-2-thienyl) methyl] amine leur preparation et leur application en therapeutique |
| FR2880890B1 (fr) * | 2005-01-19 | 2007-03-30 | Sanofi Aventis Sa | Derives de n-[(4,5-diphenyl-2-thienyl)methyl]sulfonamide, leur preparation et leur application en therapeutique |
| FR2881744B1 (fr) | 2005-02-09 | 2007-04-27 | Sanofi Aventis Sa | Derives de n-[(4,5-diphenyl-2-thienyl)methyl]amine, leur preparation et leur application en therapeutique |
| FR2894578B1 (fr) * | 2005-12-12 | 2008-02-01 | Sanofi Aventis Sa | Derives heterocycliques, leur preparation et leur application en therapeutique. |
| FR2894579B1 (fr) * | 2005-12-12 | 2008-01-18 | Sanofi Aventis Sa | Derives diaryltriazolmethylamine, leur preparation et leur application en therapeutique. |
| EP1829867A1 (en) * | 2006-03-03 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | Imidazole compounds having pharmaceutical activity towards the sigma receptor |
| FR2899899A1 (fr) * | 2006-04-14 | 2007-10-19 | Sanofi Aventis Sa | Derives d'aminomethyl pyridine, leur preparation et leur application en therapeutique |
| EP1878723B1 (fr) * | 2006-07-11 | 2010-05-26 | Sanofi-Aventis | Dérivés de N-[(1,5-diphényl-1H-pyrazol-3-yl)méthyl]sulfonamide antagonistes des récepteurs CB1 des cannabinoïdes |
| US7297710B1 (en) * | 2006-07-12 | 2007-11-20 | Sanofi-Aventis | Derivatives of N-[(1,5-diphenyl-1H-pyrazol-3-yl)methyl]sulfonamide, their preparation and their application in therapeutics |
| JP2008019205A (ja) * | 2006-07-12 | 2008-01-31 | Sanofi-Aventis | Ｎ−［（１，５−ジフェニル−１ｈ−ピラゾール−３−イル）メチル］スルホンアミド誘導体、その調製法および治療におけるその応用 |
| WO2008062424A2 (en) * | 2006-07-31 | 2008-05-29 | Cadila Healthcare Limited | Substituted 4,5-dihydro-1h-pyrazole derivatives as cannabinoid modulators |
| US7875647B2 (en) | 2006-09-29 | 2011-01-25 | Green Cross Corporation | Heteroaryl-pyrazole derivatives as cannabinoid CB1 receptor antagonists |
| EP1911747A1 (en) * | 2006-10-11 | 2008-04-16 | Laboratorios del Dr. Esteve S.A. | Sulfonamide substituted pyrazoline compounds, their preparation and use as CB1 modulators |
| FR2911136B1 (fr) | 2007-01-05 | 2009-02-20 | Sanofi Aventis Sa | Derives de n-(4-cyano-1h-pyrazol-3-yl)methylamine substitues leur preparation et leur application en therapeutique. |
| FR2919184A1 (fr) * | 2007-07-26 | 2009-01-30 | Sanofi Aventis Sa | L'acide 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4- methylpyrazole-3-carboxylique, ses esters, ses sels pharmaceutiquement acceptables et leurs solvates pour leur utilisation comme medicament. |
| WO2014028800A1 (en) | 2012-08-16 | 2014-02-20 | Janssen Pharmaceutica Nv | Substituted pyrazoles as n-type calcium channel blockers |
| EP2885304B8 (en) * | 2012-08-16 | 2016-12-07 | Janssen Pharmaceutica NV | Pyrrolopyrazoles as n-type calcium channel blockers |
| JP6263553B2 (ja) * | 2013-01-17 | 2018-01-17 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｃｎｓ疾患の処置のためのオキシトシン受容体アゴニスト |
| US9453002B2 (en) | 2013-08-16 | 2016-09-27 | Janssen Pharmaceutica Nv | Substituted imidazoles as N-type calcium channel blockers |
| KR101685993B1 (ko) * | 2014-05-15 | 2016-12-13 | 한국과학기술연구원 | 전압개폐 칼슘이온채널 억제 활성화능을 갖는 ｎ-(피라졸릴메틸)아릴설폰아마이드 화합물 및 이를 포함하는 약학적 조성물 |
| CA3023049A1 (en) | 2016-05-04 | 2017-11-09 | Inmed Pharmaceuticals Inc. | Use of topical formulations of cannabinoids in the treatment of epidermolysis bullosa and related connective tissue disorders |
| WO2019056123A1 (en) | 2017-09-22 | 2019-03-28 | Inmed Pharmaceuticals Inc. | TOPICAL FORMULATIONS OF CANNABINOIDS AND THEIR USE IN THE TREATMENT OF PAIN |
| US20240000806A1 (en) * | 2020-11-20 | 2024-01-04 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Methods and materials for inhibiting cb1 activity |
| WO2025090133A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Compositions and methods for use of cannabinol compounds in neuroprotection |
| WO2025090587A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Cannabinoids compounds and their use in the treatment of neuronal disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2713225B1 (fr) * | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| RU2165542C2 (ru) * | 1999-04-27 | 2001-04-20 | Открытое акционерное общество "АВТОВАЗ" | Модульный агрегат топливоподачи системы питания двигателя транспортного средства |
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