NO329617B1 - Tiazolderivater med CB1-antagonistisk, agonistisk eller partiell agonistisk aktivitet - Google Patents
Tiazolderivater med CB1-antagonistisk, agonistisk eller partiell agonistisk aktivitet Download PDFInfo
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- NO329617B1 NO329617B1 NO20044319A NO20044319A NO329617B1 NO 329617 B1 NO329617 B1 NO 329617B1 NO 20044319 A NO20044319 A NO 20044319A NO 20044319 A NO20044319 A NO 20044319A NO 329617 B1 NO329617 B1 NO 329617B1
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- 125000001424 substituent group Chemical group 0.000 claims description 22
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- 239000003557 cannabinoid Substances 0.000 claims description 21
- 229930003827 cannabinoid Natural products 0.000 claims description 20
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- -1 tetrahydropyranyloxy Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
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- 150000003839 salts Chemical class 0.000 claims description 8
- OARHBHCOPBHQDY-UHFFFAOYSA-N 1,2,3,5,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C1NCC2=CCCC21 OARHBHCOPBHQDY-UHFFFAOYSA-N 0.000 claims description 7
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 7
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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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 (2)
Publication Number | Publication Date |
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NO20044319L NO20044319L (no) | 2004-10-12 |
NO329617B1 true NO329617B1 (no) | 2010-11-22 |
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NO20044319A NO329617B1 (no) | 2002-03-18 | 2004-10-12 | Tiazolderivater med CB1-antagonistisk, agonistisk eller partiell agonistisk aktivitet |
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US (1) | US7342032B2 (hr) |
EP (1) | EP1492779A1 (hr) |
JP (2) | JP2005529855A (hr) |
KR (1) | KR100942672B1 (hr) |
CN (2) | CN101550114A (hr) |
AR (1) | AR038966A1 (hr) |
AU (1) | AU2003219164B2 (hr) |
BR (1) | BR0306150A (hr) |
CA (1) | CA2462692C (hr) |
HR (1) | HRP20040274A2 (hr) |
IL (2) | IL160945A0 (hr) |
MX (1) | MXPA04004741A (hr) |
NO (1) | NO329617B1 (hr) |
PL (1) | PL371429A1 (hr) |
RU (1) | RU2301804C2 (hr) |
UA (1) | UA77280C2 (hr) |
WO (1) | WO2003078413A1 (hr) |
ZA (1) | ZA200404742B (hr) |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
GB0230087D0 (en) * | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
GB0302672D0 (en) * | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
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 |
US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
US7292333B2 (en) * | 2003-06-24 | 2007-11-06 | Corning Incorporated | Optical interrogation system and method for 2-D sensor arrays |
AR045651A1 (es) * | 2003-09-19 | 2005-11-02 | Solvay Pharm Bv | Derivados de tiazol como moduladores del receptor de cannabinoide |
FR2860792B1 (fr) * | 2003-10-10 | 2006-02-24 | Sanofi Synthelabo | Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique |
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 |
AU2004299198A1 (en) * | 2003-12-08 | 2005-06-30 | F. Hoffmann-La Roche Ag | Novel thiazole derivates |
CA2553970A1 (en) | 2004-01-28 | 2005-08-18 | F. Hoffmann-La Roche Ag | Spiro-benzodioxoles and their use as cb1 antagonists |
FR2866340B1 (fr) * | 2004-02-13 | 2006-11-24 | Sanofi Synthelabo | Derives d'oxazole, leur preparation et leur utilisation en therapeutique. |
US7173044B2 (en) | 2004-02-19 | 2007-02-06 | Solvay Pharmaceuticals B.V. | Imidazoline derivatives having CB1-antagonistic activity |
TWI335321B (en) * | 2004-02-19 | 2011-01-01 | Solvay Pharm Bv | Imidazoline derivatives having cb1-antagonistic activity |
PL1725536T3 (pl) * | 2004-02-19 | 2009-04-30 | Solvay Pharm Bv | Pochodne imidazoliny mające czynność CB1-antagonistyczną |
TW200626139A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
US7951805B2 (en) | 2004-09-20 | 2011-05-31 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
CA2580856A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
EP1799667B1 (en) | 2004-09-20 | 2013-03-20 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
AU2005286647A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
CN101083992A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 抑制人硬脂酰CoA去饱和酶的哒嗪衍生物 |
BRPI0515483A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos para o tratamento de doenças mediadas por enzimas estearoil-coa desaturase |
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 |
CA2586068A1 (en) | 2004-11-09 | 2006-05-18 | F.Hoffmann-La Roche Ag | Dibenzosuberone derivatives |
EP1845972A4 (en) * | 2005-01-10 | 2010-12-22 | Univ Connecticut | CANNAPINOID RECEPTORS APPLYING NOVEL HETEROPYRROL ANALOGS |
US7361766B2 (en) | 2005-01-12 | 2008-04-22 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid receptor modulators |
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 |
BRPI0611187A2 (pt) | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
CA2613235A1 (en) | 2005-06-30 | 2007-01-11 | Prosidion Limited | Gpcr agonists |
FR2894578B1 (fr) | 2005-12-12 | 2008-02-01 | Sanofi Aventis Sa | Derives heterocycliques, leur preparation et leur application en therapeutique. |
US7763607B2 (en) * | 2006-04-27 | 2010-07-27 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators |
US20070254863A1 (en) * | 2006-04-27 | 2007-11-01 | Jochen Antel | Use of CBx cannabinoid receptor modulators as potassium channel modulators |
AU2007245733A1 (en) * | 2006-04-27 | 2007-11-08 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising CBX cannabinoid receptor modulators and Potassium channel modulators |
PL2114933T3 (pl) | 2007-01-04 | 2012-02-29 | Prosidion Ltd | Piperydyny jako agoniści GPCR |
US20100048625A1 (en) | 2007-01-04 | 2010-02-25 | Matthew Colin Thor Fyfe | Piperidine gpcr agonists |
CL2008000018A1 (es) | 2007-01-04 | 2008-08-01 | Prosidion Ltd | Compuestos derivados de heterociclos de nitrogeno y oxigeno, agonistas de gpcr; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de la obesidad, diabetes, sindrome metabolico, hiperlipidemia, toleranci |
CL2008000017A1 (es) | 2007-01-04 | 2008-08-01 | Prosidion Ltd | Compuestos derivados de heterociclos de nitrogeno y oxigeno, agonistas de gpcr; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de la obesidad, diabetes, sindrome metabolico, hiperlipidemia, toleranci |
GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
WO2010079241A1 (es) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Uso de antagonistas y/o agonistas inversos de los receptores cb1 para la preparación de medicamentos que incrementen la excitabilidad de las motoneuronas |
DE102009038123A1 (de) | 2009-08-17 | 2011-02-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiazolyl-carbonyl)imidazolidinone und ihre Verwendung |
US8461965B2 (en) * | 2010-01-13 | 2013-06-11 | The Boeing Company | Portable radio frequency identification (RFID) reader |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP3003148B2 (ja) | 1989-01-05 | 2000-01-24 | 藤沢薬品工業株式会社 | チアゾール化合物、その製造法およびそれを含有する医薬組成物 |
GB9204958D0 (en) * | 1992-03-06 | 1992-04-22 | Fujisawa Pharmaceutical Co | Thiazole derivatives |
FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
JPH10504542A (ja) * | 1994-07-27 | 1998-05-06 | ジー.ディー.サール アンド カンパニー | 炎症処置用の置換チアゾール化合物 |
JPH11193281A (ja) * | 1997-10-27 | 1999-07-21 | Takeda Chem Ind Ltd | アデノシンa3受容体拮抗剤およびチアゾール化合物 |
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 |
AR045651A1 (es) * | 2003-09-19 | 2005-11-02 | Solvay Pharm Bv | Derivados de tiazol como moduladores del receptor de cannabinoide |
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 |
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- 2003-03-17 UA UA20041008458A patent/UA77280C2/uk unknown
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- 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
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- 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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Also Published As
Publication number | Publication date |
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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 |
UA77280C2 (en) | 2006-11-15 |
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 |
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