CN100478343C - 嘌呤化合物及其作为大麻素受体配体的用途 - Google Patents
嘌呤化合物及其作为大麻素受体配体的用途 Download PDFInfo
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- CN100478343C CN100478343C CNB2006101625797A CN200610162579A CN100478343C CN 100478343 C CN100478343 C CN 100478343C CN B2006101625797 A CNB2006101625797 A CN B2006101625797A CN 200610162579 A CN200610162579 A CN 200610162579A CN 100478343 C CN100478343 C CN 100478343C
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- Prior art keywords
- alkyl
- chloro
- phenyl
- group
- compound
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Cited By (1)
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| CN104581617A (zh) * | 2015-01-22 | 2015-04-29 | 小米科技有限责任公司 | 无线通信方法和智能设备 |
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| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| WO2007070872A1 (en) | 2005-12-15 | 2007-06-21 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
| AU2006331917A1 (en) * | 2005-12-22 | 2007-07-05 | Conforma Therapeutics Corporation | Orally active purine-based inhibitors of heat shock protein 90 |
| EP1986638A2 (en) * | 2006-02-21 | 2008-11-05 | Ampla Pharmaceuticals Inc. | Cb1 antagonists and inverse agonists |
| EA200801738A1 (ru) | 2006-02-23 | 2008-12-30 | Пфайзер Лимитед | Пиперидиноилпирролидиновые агонисты меланокортинового рецептора 4 типа |
| FI3719018T3 (fi) | 2006-04-25 | 2025-10-07 | Astex Therapeutics Ltd | Puriini- ja deatsapuriinijohdannaisia farmaseuttisina yhdisteinä |
| WO2008044111A1 (en) * | 2006-10-13 | 2008-04-17 | Pfizer Products Inc. | Pharmaceutical formulation tablet |
| KR20090064478A (ko) | 2006-11-13 | 2009-06-18 | 화이자 프로덕츠 인크. | 디아릴, 디피리디닐 및 아릴-피리디닐 유도체, 및 이들의 용도 |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| BRPI0806312A2 (pt) | 2007-01-04 | 2011-09-06 | Prosidion Ltd | agonistas cgpr piperidina |
| 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 |
| 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 |
| JP2010514828A (ja) | 2007-01-04 | 2010-05-06 | プロシディオン・リミテッド | ピペリジンgpcrアゴニスト |
| US20080220104A1 (en) * | 2007-03-08 | 2008-09-11 | Cappello John V | Compositions for producing satiety |
| KR20160116045A (ko) | 2007-10-05 | 2016-10-06 | 베라스템, 인코포레이티드 | 피리미딘 치환된 퓨린 유도체 |
| 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 |
| WO2009067579A1 (en) | 2007-11-21 | 2009-05-28 | Abbott Laboratories | Biaryl substituted azabicyclic alkane derivatives as nicotinic acetylcholine receptor activity modulators |
| SG157299A1 (en) | 2008-05-09 | 2009-12-29 | Agency Science Tech & Res | Diagnosis and treatment of kawasaki disease |
| JP5530438B2 (ja) | 2008-08-06 | 2014-06-25 | ファイザー・リミテッド | Mc4作動薬としてのジアゼピンおよびジアゾカン化合物 |
| WO2010019762A1 (en) * | 2008-08-13 | 2010-02-18 | Jenrin Discovery | Purine compounds as cannabinoid receptor blockers |
| JP5769199B2 (ja) | 2008-10-31 | 2015-08-26 | ジェネンテック, インコーポレイテッド | ピラゾロピリミジンjak阻害剤化合物と方法 |
| UA104010C2 (en) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| EP2246335A1 (de) * | 2009-02-17 | 2010-11-03 | Bayer CropScience AG | Aminopyrimidinamide als Schädlingsbekämpfungsmittel |
| CA2950529C (en) | 2009-04-03 | 2019-04-30 | Verastem, Inc. | Pyrimidine substituted purine compounds as kinase (s) inhibitors |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| US8785453B2 (en) | 2009-11-13 | 2014-07-22 | Green Cross Corporation | Arylpiperazine-containing purine derivatives and uses thereof |
| WO2011113802A2 (en) * | 2010-03-17 | 2011-09-22 | F. Hoffmann-La Roche Ag | Imidazopyridine compounds, compositions and methods of use |
| AR080711A1 (es) * | 2010-03-31 | 2012-05-02 | Lilly Co Eli | Compuesto de piperazin-purina composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento o prevencion del dolor |
| EA020565B1 (ru) | 2010-03-31 | 2014-12-30 | Эли Лилли Энд Компани | Пуриновые соединения |
| CA2798831A1 (en) | 2010-05-11 | 2011-11-17 | Pfizer Inc. | Morpholine compounds as mineralocorticoid receptor antagonists |
| BR112013006016A2 (pt) | 2010-09-15 | 2016-06-07 | Hoffmann La Roche | compostos de azabenzotiazol, composições e métodos de uso |
| SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| KR20140009259A (ko) | 2010-11-19 | 2014-01-22 | 에프. 호프만-라 로슈 아게 | 피라졸로피리딘 및 tyk2 억제제로서 이의 용도 |
| HK1198365A1 (en) * | 2011-09-20 | 2015-04-10 | F. Hoffmann-La Roche Ag | Imidazopyridine compounds, compositions and methods of use |
| CZ305750B6 (cs) * | 2012-01-26 | 2016-03-02 | Ústav Organické Chemie A Biochemie Akademie Věd Čr, V.V.I. | Způsob výroby N-9 substituovaných analogů purinu |
| EP2814828B9 (en) | 2012-02-17 | 2020-10-07 | Research Triangle Institute | Peripherally restricted diphenyl purine derivatives |
| RU2485939C1 (ru) * | 2012-06-19 | 2013-06-27 | Станислав Анатольевич Кедик | Офтальмологический препарат в виде глазных капель, содержащий дисульфирам и таурин |
| BR112015027396B1 (pt) | 2013-05-02 | 2023-04-11 | F. Hoffmann-La Roche Ag | Derivados de purina como agonistas do receptor de cb2 |
| WO2015121136A1 (de) | 2014-02-17 | 2015-08-20 | Bayer Cropscience Ag | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| US9346815B2 (en) | 2014-05-23 | 2016-05-24 | Genentech, Inc. | 5-chloro-2-difluoromethoxyphenyl pyrazolopyrimidine compounds, compositions and methods of use thereof |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| CA3002551A1 (en) | 2015-06-22 | 2016-12-29 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(com pound 1)for use in s1p1 receptor-associated disorders |
| AU2017382217B2 (en) * | 2016-12-21 | 2021-07-08 | Research Triangle Institute | Diaryl purine derivatives with improved bioavailability |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| BR112019024322A2 (pt) | 2017-05-22 | 2020-06-16 | F. Hoffmann-La Roche Ag | Compostos e composições terapêuticos e métodos de uso dos mesmos |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| IL317596A (en) * | 2019-01-15 | 2025-02-01 | Yissum Res Dev Co Of Hebrew Univ Jerusalem Ltd | Peripheral CB1 receptor inhibitors |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018378A (en) * | 1954-09-20 | 1962-01-23 | North American Aviation Inc | Radiant energy scanning system |
| US3016378A (en) | 1959-07-01 | 1962-01-09 | Thomae Gmbh Dr K | Amino-substituted purine derivatives |
| GB1165283A (en) | 1967-01-17 | 1969-09-24 | Science Union & Cie | New Purine Derivatives and processes for prepararing them |
| AT321295B (de) | 1971-11-11 | 1975-03-25 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Thiazolo[5,4-d]-pyrimidin-Derivaten und ihren Salzen |
| CH653021A5 (fr) | 1981-04-24 | 1985-12-13 | Delalande Sa | Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant. |
| JPS60260579A (ja) | 1984-01-13 | 1985-12-23 | Yoshitomi Pharmaceut Ind Ltd | プリン誘導体 |
| GB8613591D0 (en) | 1986-06-04 | 1986-07-09 | Roussel Lab Ltd | Chemical compounds |
| US5078780A (en) | 1986-10-22 | 1992-01-07 | Ciba-Geigy Corporation | 1,5-diphenylpyrazole-3-carboxylic acid derivatives for the protection of cultivated plants |
| AU611437B2 (en) | 1987-05-29 | 1991-06-13 | Ortho Pharmaceutical Corporation | Pharmacologically active 2- and 3-substituted (1',5'-diaryl-3-pyrazolyl)-n-hydroxypropanamides and method for synthesizing the same |
| US5057517A (en) | 1987-07-20 | 1991-10-15 | Merck & Co., Inc. | Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents |
| PH27357A (en) | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| FR2665898B1 (fr) | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5256398A (en) | 1990-11-08 | 1993-10-26 | Whitby Research, Inc. | Composition for determining viability of tissue |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2714057B1 (fr) | 1993-12-17 | 1996-03-08 | Sanofi Elf | Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| US5596106A (en) | 1994-07-15 | 1997-01-21 | Eli Lilly And Company | Cannabinoid receptor antagonists |
| FR2741621B1 (fr) | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2742148B1 (fr) | 1995-12-08 | 1999-10-22 | Sanofi Sa | Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant |
| CA2257222C (en) | 1996-06-06 | 2002-08-20 | Otsuka Pharmaceutical Factory, Inc. | Amide derivatives |
| ES2213892T3 (es) | 1997-01-21 | 2004-09-01 | Smithkline Beecham Corporation | Nuevos moduladores del receptor de canabinoides. |
| FR2758723B1 (fr) | 1997-01-28 | 1999-04-23 | Sanofi Sa | Utilisation des antagonistes des recepteurs aux cannabinoides centraux pour la preparation de medicaments |
| US6284748B1 (en) | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| FR2761266B1 (fr) | 1997-03-28 | 1999-07-02 | Sanofi Sa | Composition pharmaceutique formee par granulation humide pour l'administration orale d'un derive du n-piperidino-3- pyrazolecarboxamide, de ses sels et de leurs solvates |
| JP3990061B2 (ja) * | 1998-01-05 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | プリン誘導体および糖尿病の予防・治療剤としてのアデノシンa2受容体拮抗剤 |
| DE69815554T2 (de) | 1998-01-05 | 2004-05-06 | Eisai Co., Ltd. | Purinderivate und antagonisten des adenosin-a2-rezeptors, welche zur vorsorge oder heilung von diabetes dienen |
| FR2783246B1 (fr) | 1998-09-11 | 2000-11-17 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les medicaments les contenant |
| KR100652994B1 (ko) | 1998-09-11 | 2006-11-30 | 아방티 파르마 소시에테 아노님 | 아제티딘 유도체, 이의 제조방법 및 이를 함유하는 약제 |
| FR2789079B3 (fr) | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
| CA2376835C (en) * | 1999-07-02 | 2009-09-15 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| FR2799124B1 (fr) | 1999-10-01 | 2004-08-13 | Sanofi Synthelabo | Utilisation des antagonistes des recepteurs aux cannabinoides centraux pour la preparation de medicaments |
| CA2387892A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| DE60030303T2 (de) | 1999-10-18 | 2007-10-11 | The University Of Connecticut, Farmington | Cannabimimetische indolderivate |
| FR2800375B1 (fr) | 1999-11-03 | 2004-07-23 | Sanofi Synthelabo | Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant |
| FR2800372B1 (fr) | 1999-11-03 | 2001-12-07 | Sanofi Synthelabo | Derives tricycliques d'acide 1-benzylpyrazole-3- carboxylique, leur preparation, les medicaments en contenant |
| FR2804604B1 (fr) | 2000-02-09 | 2005-05-27 | Sanofi Synthelabo | Utilisation d'un antagoniste des recepteurs aux cannabinoides centraux pour la preparation de medicaments utiles pour faciliter l'arret de la consommation de tabac |
| EP1254115A2 (en) | 2000-02-11 | 2002-11-06 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| US6355631B1 (en) | 2000-03-03 | 2002-03-12 | Aventis Pharma S.A. | Pharmaceutical compositions containing azetidine derivatives, novel azetidine derivatives and their preparation |
| US6479479B2 (en) | 2000-03-03 | 2002-11-12 | Aventis Pharma S.A. | Azetidine derivatives, their preparation and pharmaceutical compositions containing them |
| US6566356B2 (en) | 2000-03-03 | 2003-05-20 | Aventis Pharma S.A. | Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation |
| HUP0204519A3 (en) | 2000-03-23 | 2003-07-28 | Solvay Pharm Bv | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity, pharmaceutical compositions containing them and process for their preparations |
| FR2809621B1 (fr) | 2000-05-12 | 2002-09-06 | Sanofi Synthelabo | Utilisation d'un antagoniste des recepteurs aux cannabinoides centraux pour la preparation de medicaments utiles comme antidiarrheiques |
| US20020019421A1 (en) | 2000-07-05 | 2002-02-14 | Roni Biberman | Compositions and therapy for substance addiction |
| US20020091114A1 (en) | 2000-10-04 | 2002-07-11 | Odile Piot-Grosjean | Combination of a CB1 receptor antagonist and of sibutramine, the pharmaceutical compositions comprising them and their use in the treatment of obesity |
| PT1354884E (pt) | 2000-12-28 | 2007-12-24 | Ono Pharmaceutical Co | Composto de ciclopenta (d) pirazolo [1,5-a] piramida como antagonista de receptor de crf |
| SI1373216T1 (en) | 2001-03-22 | 2005-06-30 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| ITMI20011483A1 (it) | 2001-07-11 | 2003-01-11 | Res & Innovation Soc Coop A R | Uso di composti come antagonisti funzionali ai recettori centrali deicannabinoidi |
| AU2002319627A1 (en) | 2001-07-20 | 2003-03-03 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| 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 |
| 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 |
| JP2005507875A (ja) | 2001-08-31 | 2005-03-24 | ユニバーシティ オブ コネチカット | カンナビノイド受容体に作用する新規なピラゾール類似体 |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| KR100903760B1 (ko) | 2001-09-21 | 2009-06-19 | 솔베이 파마슈티칼스 비. 브이 | Cb1-길항 작용을 가지는 신규한4,5-디하이드로-1h-피라졸 유도체 |
| HUP0402113A3 (en) | 2001-09-21 | 2012-05-29 | Solvay Pharm Bv | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity, preparation and use thereof |
| US6509367B1 (en) | 2001-09-22 | 2003-01-21 | Virginia Commonwealth University | Pyrazole cannabinoid agonist and antagonists |
| UY27450A1 (es) | 2001-09-24 | 2003-04-30 | Bayer Corp | Preparación y uso de derivados de imidazol para el tratamiento de la obesidad |
| CA2461142A1 (en) | 2001-09-24 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives for treatment of obesity |
| EP1432679A1 (en) | 2001-09-24 | 2004-06-30 | Bayer Pharmaceuticals Corporation | Preparation and use of pyrrole derivatives for treating obesity |
| SE0104330D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| SE0104332D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| US20030139386A1 (en) | 2001-12-21 | 2003-07-24 | Sophie Cote | Pharmaceutical compositions based on azetidine derivatives |
| AU2003219934A1 (en) | 2002-03-06 | 2003-09-22 | Merck And Co., Inc. | Method of treatment or prevention of obesity |
| JP3813152B2 (ja) | 2002-03-12 | 2006-08-23 | メルク エンド カムパニー インコーポレーテッド | 置換アミド類 |
| 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. |
| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| FR2837706A1 (fr) | 2002-03-28 | 2003-10-03 | Sanofi Synthelabo | Utilisation d'un antagoniste des recepteurs aux cannabinoides cb1 pour la preparation de medicaments utiles pour traiter les dysfonctionnements sexuels et/ou ameliorer les performances sexuelles |
| CA2480856A1 (en) | 2002-04-05 | 2003-10-23 | Merck & Co., Inc. | Substituted aryl amides |
| 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 |
| WO2003095455A2 (en) | 2002-05-10 | 2003-11-20 | Smithkline Beecham Corporation | Substituted pyrazolopyrimidines |
| JP2006506366A (ja) | 2002-10-18 | 2006-02-23 | ファイザー・プロダクツ・インク | カンナビノイド受容体リガンドおよびその使用方法 |
| US7129239B2 (en) * | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US20050043327A1 (en) * | 2003-08-21 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
| JP2008517898A (ja) * | 2004-10-22 | 2008-05-29 | ファイザー・プロダクツ・インク | プリン化合物を調製するための方法 |
-
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Non-Patent Citations (2)
| Title |
|---|
| Synthess, Corticotropin-Releasing Factor Recptor BindingAffinity. R. J. Chorvat, et al.J. MED. CHEM.,,Vol.42 . 1999 |
| Synthess, Corticotropin-Releasing Factor Recptor BindingAffinity. R. J. Chorvat, et al.J. MED. CHEM.,Vol.42. 1999 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104581617A (zh) * | 2015-01-22 | 2015-04-29 | 小米科技有限责任公司 | 无线通信方法和智能设备 |
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