UA77280C2 - Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 - Google Patents
Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 Download PDFInfo
- Publication number
- UA77280C2 UA77280C2 UA20041008458A UA20041008458A UA77280C2 UA 77280 C2 UA77280 C2 UA 77280C2 UA 20041008458 A UA20041008458 A UA 20041008458A UA 20041008458 A UA20041008458 A UA 20041008458A UA 77280 C2 UA77280 C2 UA 77280C2
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- Ukraine
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- hydroxy
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- 150000007979 thiazole derivatives Chemical class 0.000 title abstract description 7
- 239000000556 agonist Substances 0.000 title abstract description 6
- 239000005557 antagonist Substances 0.000 title abstract description 5
- 230000000694 effects Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 229930003827 cannabinoid Natural products 0.000 claims abstract description 7
- 239000003557 cannabinoid Substances 0.000 claims abstract description 7
- -1 trifluoromethylthio, nitro, amino Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000651 prodrug Chemical group 0.000 claims description 9
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 3
- 235000013599 spices Nutrition 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 abstract 1
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 21
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- 239000000203 mixture Substances 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
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Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02076481 | 2002-03-18 | ||
| PCT/EP2003/050063 WO2003078413A1 (en) | 2002-03-18 | 2003-03-17 | Thiazole derivatives having cb1-antagonistic, agonistic or partial agonistic activity |
Publications (1)
| Publication Number | Publication Date |
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| UA77280C2 true UA77280C2 (en) | 2006-11-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| UA20041008458A UA77280C2 (en) | 2002-03-18 | 2003-03-17 | Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 |
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| US (1) | US7342032B2 (zh) |
| EP (1) | EP1492779A1 (zh) |
| JP (2) | JP2005529855A (zh) |
| KR (1) | KR100942672B1 (zh) |
| CN (2) | CN101550114A (zh) |
| AR (1) | AR038966A1 (zh) |
| AU (1) | AU2003219164B2 (zh) |
| BR (1) | BR0306150A (zh) |
| CA (1) | CA2462692C (zh) |
| HR (1) | HRP20040274A2 (zh) |
| IL (2) | IL160945A0 (zh) |
| MX (1) | MXPA04004741A (zh) |
| NO (1) | NO329617B1 (zh) |
| PL (1) | PL371429A1 (zh) |
| RU (1) | RU2301804C2 (zh) |
| UA (1) | UA77280C2 (zh) |
| WO (1) | WO2003078413A1 (zh) |
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| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
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| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
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| US5229386A (en) * | 1989-01-05 | 1993-07-20 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
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| FR2789079B3 (fr) | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
| JP2001114690A (ja) * | 1999-08-06 | 2001-04-24 | Takeda Chem Ind Ltd | ｐ３８ＭＡＰキナーゼ阻害剤 |
| GB0005357D0 (en) * | 2000-03-06 | 2000-04-26 | Smithkline Beecham Plc | Compounds |
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| US20050124660A1 (en) * | 2003-10-27 | 2005-06-09 | Jochen Antel | Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds |
-
2003
- 2003-03-13 AR ARP030100879A patent/AR038966A1/es unknown
- 2003-03-17 RU RU2004114263/04A patent/RU2301804C2/ru not_active IP Right Cessation
- 2003-03-17 IL IL16094503A patent/IL160945A0/xx unknown
- 2003-03-17 MX MXPA04004741A patent/MXPA04004741A/es active IP Right Grant
- 2003-03-17 UA UA20041008458A patent/UA77280C2/uk unknown
- 2003-03-17 AU AU2003219164A patent/AU2003219164B2/en not_active Ceased
- 2003-03-17 WO PCT/EP2003/050063 patent/WO2003078413A1/en active Application Filing
- 2003-03-17 PL PL03371429A patent/PL371429A1/xx not_active Application Discontinuation
- 2003-03-17 BR BR0306150-7A patent/BR0306150A/pt not_active Application Discontinuation
- 2003-03-17 EP EP03714960A patent/EP1492779A1/en not_active Withdrawn
- 2003-03-17 CN CNA2008101750226A patent/CN101550114A/zh active Pending
- 2003-03-17 CA CA2462692A patent/CA2462692C/en not_active Expired - Fee Related
- 2003-03-17 CN CNA038015587A patent/CN1592744A/zh active Pending
- 2003-03-17 KR KR1020047014698A patent/KR100942672B1/ko not_active IP Right Cessation
- 2003-03-17 JP JP2003576419A patent/JP2005529855A/ja not_active Withdrawn
- 2003-03-17 US US10/490,546 patent/US7342032B2/en not_active Expired - Fee Related
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2004
- 2004-03-18 IL IL160945A patent/IL160945A/en not_active IP Right Cessation
- 2004-03-19 HR HR20040274A patent/HRP20040274A2/hr not_active Application Discontinuation
- 2004-06-15 ZA ZA200404742A patent/ZA200404742B/en unknown
- 2004-10-12 NO NO20044319A patent/NO329617B1/no not_active IP Right Cessation
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2003078413A1 (en) | 2003-09-25 |
| US7342032B2 (en) | 2008-03-11 |
| NO20044319L (no) | 2004-10-12 |
| KR20040106297A (ko) | 2004-12-17 |
| ZA200404742B (en) | 2005-08-29 |
| IL160945A (en) | 2010-02-17 |
| JP2011105734A (ja) | 2011-06-02 |
| HRP20040274A2 (en) | 2005-04-30 |
| CA2462692C (en) | 2010-11-09 |
| AU2003219164B2 (en) | 2008-07-17 |
| AU2003219164A1 (en) | 2003-09-29 |
| AR038966A1 (es) | 2005-02-02 |
| US20040266841A1 (en) | 2004-12-30 |
| CN101550114A (zh) | 2009-10-07 |
| CA2462692A1 (en) | 2003-09-25 |
| MXPA04004741A (es) | 2004-08-02 |
| KR100942672B1 (ko) | 2010-02-17 |
| RU2301804C2 (ru) | 2007-06-27 |
| CN1592744A (zh) | 2005-03-09 |
| BR0306150A (pt) | 2004-10-19 |
| JP2005529855A (ja) | 2005-10-06 |
| RU2004114263A (ru) | 2005-09-10 |
| PL371429A1 (en) | 2005-06-13 |
| IL160945A0 (en) | 2004-08-31 |
| EP1492779A1 (en) | 2005-01-05 |
| NO329617B1 (no) | 2010-11-22 |
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