DE60202270T2 - 4,5-dihydro-1h-pyrazolderivate mit cb1-antagonistischer wirkung - Google Patents
4,5-dihydro-1h-pyrazolderivate mit cb1-antagonistischer wirkung Download PDFInfo
- Publication number
- DE60202270T2 DE60202270T2 DE60202270T DE60202270T DE60202270T2 DE 60202270 T2 DE60202270 T2 DE 60202270T2 DE 60202270 T DE60202270 T DE 60202270T DE 60202270 T DE60202270 T DE 60202270T DE 60202270 T2 DE60202270 T2 DE 60202270T2
- Authority
- DE
- Germany
- Prior art keywords
- chlorophenyl
- compound
- phenyl
- formula
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 title claims description 5
- 230000000694 effects Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 50
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- 239000003557 cannabinoid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 230000005062 synaptic transmission Effects 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003814 drug Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
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- XPJPCDIVXGVHLY-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound N=1N(C(=N)N)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 XPJPCDIVXGVHLY-UHFFFAOYSA-N 0.000 description 3
- AXJQVVLKUYCICH-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AXJQVVLKUYCICH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
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- AXJQVVLKUYCICH-OAQYLSRUSA-N (4s)-5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AXJQVVLKUYCICH-OAQYLSRUSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WSTGSFBSMRBHTJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(4-chlorophenyl)sulfonyl-4-phenylpyrazolidine-1-carboximidamide Chemical compound NC(=N)N1CC(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)C1=CC=C(Cl)C=C1 WSTGSFBSMRBHTJ-UHFFFAOYSA-N 0.000 description 2
- PMFKSNJVULPDBR-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-fluorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=N)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 PMFKSNJVULPDBR-UHFFFAOYSA-N 0.000 description 2
- SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
-
- 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201062 | 2001-03-22 | ||
| EP01201062 | 2001-03-22 | ||
| PCT/EP2002/003079 WO2002076949A1 (en) | 2001-03-22 | 2002-03-18 | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60202270D1 DE60202270D1 (de) | 2005-01-20 |
| DE60202270T2 true DE60202270T2 (de) | 2005-05-19 |
Family
ID=8180044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60202270T Expired - Lifetime DE60202270T2 (de) | 2001-03-22 | 2002-03-18 | 4,5-dihydro-1h-pyrazolderivate mit cb1-antagonistischer wirkung |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1373216B1 (enExample) |
| JP (1) | JP4373675B2 (enExample) |
| KR (1) | KR100846614B1 (enExample) |
| CN (1) | CN100366614C (enExample) |
| AR (1) | AR033046A1 (enExample) |
| AT (1) | ATE284872T1 (enExample) |
| AU (1) | AU2002256690B2 (enExample) |
| BR (1) | BR0205602A (enExample) |
| CA (1) | CA2422708C (enExample) |
| CZ (1) | CZ2003698A3 (enExample) |
| DE (1) | DE60202270T2 (enExample) |
| ES (1) | ES2229132T3 (enExample) |
| HU (1) | HUP0303148A3 (enExample) |
| IL (1) | IL153508A (enExample) |
| MX (1) | MXPA03003534A (enExample) |
| NO (1) | NO324953B1 (enExample) |
| NZ (1) | NZ524633A (enExample) |
| PL (1) | PL363751A1 (enExample) |
| PT (1) | PT1373216E (enExample) |
| RU (1) | RU2281941C2 (enExample) |
| SI (1) | SI1373216T1 (enExample) |
| SK (1) | SK287592B6 (enExample) |
| UA (1) | UA74066C2 (enExample) |
| WO (1) | WO2002076949A1 (enExample) |
| ZA (1) | ZA200307322B (enExample) |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| ATE486842T1 (de) | 2002-03-12 | 2010-11-15 | Merck Sharp & Dohme | Substituierte amide |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| AR045533A1 (es) * | 2003-09-02 | 2005-11-02 | Solvay Pharm Gmbh | Uso de un compuesto antagonista de receptor de cb1, composicion farmaceutica y metodo de tratamiento y/o profilaxis de enfermedades relacionadas con dicho receptor de cb1 |
| WO2005028438A1 (ja) | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | 新規ピペリジン誘導体 |
| BRPI0415851A (pt) * | 2003-10-24 | 2007-01-02 | Solvay Pharm Gmbh | utilizações médicas de compostos que apresentam atividade antagonìstica de cb1 e tratamento de combinação envolvendo os referidos compostos |
| AR046132A1 (es) * | 2003-10-24 | 2005-11-23 | Solvay Pharm Gmbh | Composicin farmaceutica que contiene al menos un compuesto con actividad de receptor de cb1, o un profarmaco , tautomero o sal del mismo, como componente activo adecuado para el tratamiento y/o profilaxis de enfermedades relacionadas con el receptor cb1 en pacientes juveniles y/o para el tratamiento |
| WO2005049615A1 (en) * | 2003-11-21 | 2005-06-02 | Pfizer Products Inc. | Pyrazolo`1,5-a!`1,3,5! triazin -4-one derivatives as cb1 receptor antagonists |
| WO2005075450A2 (en) | 2004-01-28 | 2005-08-18 | F. Hoffmann-La Roche Ag | Spiro-benzodioxoles and their use as cb1 antagonists |
| EP1713475B1 (en) * | 2004-01-30 | 2008-07-30 | Solvay Pharmaceuticals B.V. | 1,3,5-trisubstituted 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| US7649002B2 (en) | 2004-02-04 | 2010-01-19 | Pfizer Inc | (3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists |
| WO2005097759A1 (en) | 2004-03-29 | 2005-10-20 | Merck & Co., Inc. | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| JP2008509146A (ja) | 2004-08-06 | 2008-03-27 | メルク エンド カムパニー インコーポレーテッド | １１−ベータ−ヒドロキシステロイドデヒドロゲナーゼ−１の阻害剤としてのスルホニル化合物 |
| EP1784390A2 (en) | 2004-08-13 | 2007-05-16 | Amgen Inc. | Substituted benzofused heterocycles |
| RU2007119315A (ru) * | 2004-10-25 | 2008-11-27 | Зольвай Фармасьютиклз Гмбх (De) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний |
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