BRPI0806312A2 - agonistas cgpr piperidina - Google Patents
agonistas cgpr piperidina Download PDFInfo
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- BRPI0806312A2 BRPI0806312A2 BRPI0806312-5A BRPI0806312A BRPI0806312A2 BR PI0806312 A2 BRPI0806312 A2 BR PI0806312A2 BR PI0806312 A BRPI0806312 A BR PI0806312A BR PI0806312 A2 BRPI0806312 A2 BR PI0806312A2
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- pharmaceutically acceptable
- acceptable salt
- compound
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Classifications
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0700126A GB0700126D0 (en) | 2007-01-04 | 2007-01-04 | GPCR agonists |
| GB0700126.6 | 2007-01-04 | ||
| GB0708748.9 | 2007-05-08 | ||
| GB0708748A GB0708748D0 (en) | 2007-05-08 | 2007-05-08 | GPCR agonists |
| GB0719765A GB0719765D0 (en) | 2007-10-10 | 2007-10-10 | GPCR agonists |
| GB0719765.0 | 2007-10-10 | ||
| PCT/GB2008/050014 WO2008081208A1 (en) | 2007-01-04 | 2008-01-04 | Piperidine gpcr agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0806312A2 true BRPI0806312A2 (pt) | 2011-09-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0806312-5A BRPI0806312A2 (pt) | 2007-01-04 | 2008-01-04 | agonistas cgpr piperidina |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100048625A1 (show.php) |
| EP (1) | EP2114936A1 (show.php) |
| JP (1) | JP2010514832A (show.php) |
| BR (1) | BRPI0806312A2 (show.php) |
| CA (1) | CA2674360A1 (show.php) |
| EA (1) | EA016507B1 (show.php) |
| WO (1) | WO2008081208A1 (show.php) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20100286112A1 (en) | 2007-09-10 | 2010-11-11 | Oscar Barba | Compounds for the treatment of metabolic disorders |
| GB0812641D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| GB0812649D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| CN102089301A (zh) * | 2008-07-10 | 2011-06-08 | 普洛希典有限公司 | 哌啶gpcr激动剂 |
| GB0812648D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| GB0904285D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB0904284D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB0904287D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| TW201111361A (en) | 2009-06-24 | 2011-04-01 | Boehringer Ingelheim Int | New compounds, pharmaceutical composition and methods relating thereto |
| TW201113269A (en) | 2009-06-24 | 2011-04-16 | Boehringer Ingelheim Int | New compounds, pharmaceutical composition and methods relating thereto |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2547339A1 (en) | 2010-03-18 | 2013-01-23 | Boehringer Ingelheim International GmbH | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
| GB201006166D0 (en) | 2010-04-14 | 2010-05-26 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB201006167D0 (en) | 2010-04-14 | 2010-05-26 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| TW201209054A (en) | 2010-05-28 | 2012-03-01 | Prosidion Ltd | Novel compounds |
| GB2488360A (en) * | 2011-02-25 | 2012-08-29 | Prosidion Ltd | Heterocyclic GPCR agonists |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| GB201114389D0 (en) | 2011-08-22 | 2011-10-05 | Prosidion Ltd | Novel compounds |
| AR083904A1 (es) | 2010-11-18 | 2013-04-10 | Prosidion Ltd | Derivados de 1,4-pirrolidinas disustituidos y 3-il-aminas y sus usos en el tratamiento de desordenes metabolicos |
| US9050347B2 (en) | 2011-01-25 | 2015-06-09 | Viviabiotech, S.L. | 1,2,4-oxadiazole derivatives as drugs modulating the GLP-1 peptide receptor |
| US9181214B2 (en) | 2011-06-09 | 2015-11-10 | Rhizen Pharmaceuticals Sa | Bicyclic compounds as modulators of GPR-119 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2713225B1 (fr) | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| US6100042A (en) * | 1993-03-31 | 2000-08-08 | Cadus Pharmaceutical Corporation | Yeast cells engineered to produce pheromone system protein surrogates, and uses therefor |
| US6221660B1 (en) * | 1999-02-22 | 2001-04-24 | Synaptic Pharmaceutical Corporation | DNA encoding SNORF25 receptor |
| FR2829028B1 (fr) | 2001-08-29 | 2004-12-17 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et d'un produit qui active la neurotransmission dopaminergique dans le cerveau, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de |
| FR2829027A1 (fr) | 2001-08-29 | 2003-03-07 | Aventis Pharma Sa | Association avec un antagoniste du recepteur cb1, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de parkinson |
| AU2002331766A1 (en) | 2001-08-31 | 2003-03-18 | University Of Connecticut | Novel pyrazole analogs acting on cannabinoid receptors |
| NZ528280A (en) | 2001-09-21 | 2005-11-25 | Solvay Pharmaceuticals B | 4,5-dihydro-1H-pyrazole derivatives having potent CB1-antagonistic activity |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| MXPA04002583A (es) | 2001-09-21 | 2004-06-18 | Solvay Pharm Bv | Derivados de 4,5-dihidro-1h-pirazol novedosos que tienen actividad antagonistica del canabinoide (cb1). |
| FR2831883B1 (fr) | 2001-11-08 | 2004-07-23 | Sanofi Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| SE0104330D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| SE0104332D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| FR2833842B1 (fr) | 2001-12-21 | 2004-02-13 | Aventis Pharma Sa | Compositions pharmaceutiques a base de derives d'azetidine |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| WO2003075660A1 (en) | 2002-03-06 | 2003-09-18 | Merck & Co., Inc. | Method of treatment or prevention of obesity |
| DE60334787D1 (de) | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Substituierte amide |
| AR038966A1 (es) | 2002-03-18 | 2005-02-02 | Solvay Pharm Bv | Derivados de tiazol que tienen actividad antagonista, agonista o agonista parcial de cb1 |
| JP2005528366A (ja) | 2002-03-26 | 2005-09-22 | メルク エンド カムパニー インコーポレーテッド | カンナビノイド受容体モジュレータとしてのスピロ環式アミド |
| ES2192494B1 (es) | 2002-03-27 | 2005-02-16 | Consejo Superior De Investigaciones Cientificas | Derivados de 1,2,4-triazol con propiedades cannabinoides. |
| CA2479744A1 (en) | 2002-03-28 | 2003-10-09 | Paul E. Finke | Substituted 2,3-diphenyl pyridines |
| EP1494997A4 (en) | 2002-04-05 | 2007-04-11 | Merck & Co Inc | SUBSTITUTED ARYLAMID |
| FR2838438A1 (fr) | 2002-04-11 | 2003-10-17 | Sanofi Synthelabo | Derives de diphenylpyridine,leur preparation, les compositions pharmaceutiques en contenant |
| FR2838439B1 (fr) | 2002-04-11 | 2005-05-20 | Sanofi Synthelabo | Derives de terphenyle, leur preparation, les compositions pharmaceutqiues en contenant |
| US7667053B2 (en) | 2002-04-12 | 2010-02-23 | Merck & Co., Inc. | Bicyclic amides |
| US6825209B2 (en) | 2002-04-15 | 2004-11-30 | Research Triangle Institute | Compounds having unique CB1 receptor binding selectivity and methods for their production and use |
| HRP20050044A2 (en) | 2002-07-29 | 2005-10-31 | F. Hoffmann - La Roche Ag | Novel benzodioxoles |
| ES2294330T3 (es) | 2002-08-02 | 2008-04-01 | MERCK & CO., INC. | Derivados de furo(2,3-b)piridina sustituidos. |
| AU2003296895A1 (en) | 2002-08-20 | 2004-05-04 | The Regents Of The University Of California | Combination therapy for controlling appetites |
| HRP20050053A2 (en) | 2002-09-19 | 2005-04-30 | Solvay Pharmaceuticals B.V. | 1 h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
| WO2004029204A2 (en) | 2002-09-27 | 2004-04-08 | Merck & Co., Inc. | Substituted pyrimidines |
| EP1556373A1 (en) | 2002-10-18 | 2005-07-27 | Pfizer Products Inc. | Cannabinoid receptor ligands and uses thereof |
| 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 |
| CN1747926A (zh) | 2002-12-19 | 2006-03-15 | 麦克公司 | 取代酰胺化合物 |
| GB0230087D0 (en) | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| EP1583762B1 (en) | 2003-01-02 | 2008-07-09 | F. Hoffmann-La Roche Ag | Pyrrolyl-thiazoles and their use as cb 1 receptor inverse agonists |
| KR100704097B1 (ko) | 2003-01-02 | 2007-04-06 | 에프. 호프만-라 로슈 아게 | 신규 ｃｂ 1 수용체 역작용제 |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| DE502004007000D1 (de) | 2003-02-13 | 2008-06-12 | Sanofi Aventis Deutschland | Stickstoff substituierte hexahydro-pyrazino 1,2-a pyrimidin-4,7-dionderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| ATE472548T1 (de) | 2003-02-13 | 2010-07-15 | Sanofi Aventis Deutschland | Substituierte hexahydro-pyrazino(1,2-a)pyrimidin- 4,7-dionderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| EP1606019A1 (en) | 2003-03-07 | 2005-12-21 | The University Court of The University of Aberdeen | Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| JP4958560B2 (ja) | 2003-12-24 | 2012-06-20 | プロシディオン・リミテッド | Ｇｐｃｒ受容体作動薬としてのヘテロ環誘導体 |
| JP4980928B2 (ja) * | 2004-12-24 | 2012-07-18 | プロシディオン・リミテッド | Ｇタンパク質共役受容体（ｇｐｒ１１６）作動薬および肥満および糖尿病治療のためのその使用 |
| WO2006067532A1 (en) * | 2004-12-24 | 2006-06-29 | Prosidion Ltd | G-protein coupled receptor agonists |
| GB0428514D0 (en) | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| US20090221644A1 (en) | 2005-06-30 | 2009-09-03 | Stuart Edward Bradley | Gpcr Agonists |
| KR20080025190A (ko) | 2005-06-30 | 2008-03-19 | 프로시디온 리미티드 | Ｇ-단백질 결합된 수용체 효능제 |
| EP1907383A1 (en) | 2005-06-30 | 2008-04-09 | Prosidion Limited | Gpcr agonists |
| US20100063081A1 (en) | 2005-06-30 | 2010-03-11 | Stuart Edward Bradly | CPCR Agonists |
| JP2009532453A (ja) * | 2006-04-06 | 2009-09-10 | プロシディオン・リミテッド | ヘテロサイクリックｇｐｃｒアゴニスト |
| JP5330260B2 (ja) * | 2006-12-06 | 2013-10-30 | スミスクライン ビーチャム コーポレーション | 二環式化合物ならびに抗糖尿病薬としての使用 |
-
2008
- 2008-01-04 WO PCT/GB2008/050014 patent/WO2008081208A1/en not_active Ceased
- 2008-01-04 CA CA002674360A patent/CA2674360A1/en not_active Abandoned
- 2008-01-04 EA EA200900878A patent/EA016507B1/ru not_active IP Right Cessation
- 2008-01-04 EP EP08702097A patent/EP2114936A1/en not_active Withdrawn
- 2008-01-04 BR BRPI0806312-5A patent/BRPI0806312A2/pt not_active IP Right Cessation
- 2008-01-04 US US12/522,030 patent/US20100048625A1/en not_active Abandoned
- 2008-01-04 JP JP2009544451A patent/JP2010514832A/ja active Pending
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| Publication number | Publication date |
|---|---|
| EA016507B1 (ru) | 2012-05-30 |
| EA200900878A1 (ru) | 2010-02-26 |
| CA2674360A1 (en) | 2008-07-10 |
| WO2008081208A1 (en) | 2008-07-10 |
| JP2010514832A (ja) | 2010-05-06 |
| US20100048625A1 (en) | 2010-02-25 |
| EP2114936A1 (en) | 2009-11-11 |
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