NO332195B1 - Purinforbindelse samt farmasoytisk preparat inneholdende det samme - Google Patents
Purinforbindelse samt farmasoytisk preparat inneholdende det samme Download PDFInfo
- Publication number
- NO332195B1 NO332195B1 NO20052512A NO20052512A NO332195B1 NO 332195 B1 NO332195 B1 NO 332195B1 NO 20052512 A NO20052512 A NO 20052512A NO 20052512 A NO20052512 A NO 20052512A NO 332195 B1 NO332195 B1 NO 332195B1
- Authority
- NO
- Norway
- Prior art keywords
- chlorophenyl
- compound
- compounds
- purin
- alkyl
- Prior art date
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- -1 Purine compound Chemical class 0.000 title claims description 87
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 19
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 239000008177 pharmaceutical agent Substances 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 14
- 239000000883 anti-obesity agent Substances 0.000 claims description 12
- 229940125710 antiobesity agent Drugs 0.000 claims description 11
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 6
- UNAZAADNBYXMIV-UHFFFAOYSA-N otenabant Chemical compound C1CC(NCC)(C(N)=O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 UNAZAADNBYXMIV-UHFFFAOYSA-N 0.000 claims description 6
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- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
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- QOJJSCQRJYEFSQ-UHFFFAOYSA-N 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(ethylamino)piperidine-4-carbonitrile Chemical compound C1CC(NCC)(C#N)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 QOJJSCQRJYEFSQ-UHFFFAOYSA-N 0.000 claims 1
- QZZWJLDYTGHBIW-UHFFFAOYSA-N 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(propan-2-ylamino)piperidine-4-carbonitrile Chemical compound C1CC(NC(C)C)(C#N)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 QZZWJLDYTGHBIW-UHFFFAOYSA-N 0.000 claims 1
- DNPSMAHBGIQJNC-UHFFFAOYSA-N 4-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-n-methylpiperazine-2-carboxamide Chemical compound C1CNC(C(=O)NC)CN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 DNPSMAHBGIQJNC-UHFFFAOYSA-N 0.000 claims 1
- IYSWVAJFXMALEB-UHFFFAOYSA-N 4-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]piperazine-2-carboxamide Chemical compound C1CNC(C(=O)N)CN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 IYSWVAJFXMALEB-UHFFFAOYSA-N 0.000 claims 1
- PCPIJEMLUIUYOR-UHFFFAOYSA-N methyl 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(ethylamino)piperidine-4-carboxylate Chemical compound C1CC(NCC)(C(=O)OC)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 PCPIJEMLUIUYOR-UHFFFAOYSA-N 0.000 claims 1
- MPCQTVSPZHIQGD-UHFFFAOYSA-N methyl 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(methylamino)piperidine-4-carboxylate Chemical compound C1CC(NC)(C(=O)OC)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 MPCQTVSPZHIQGD-UHFFFAOYSA-N 0.000 claims 1
- VPRIMHHZSUECRF-UHFFFAOYSA-N methyl 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-hydroxypiperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 VPRIMHHZSUECRF-UHFFFAOYSA-N 0.000 claims 1
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- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42187402P | 2002-10-28 | 2002-10-28 | |
| PCT/IB2003/004619 WO2004037823A1 (en) | 2002-10-28 | 2003-10-21 | Purine compounds and uses thereof as cannabinoid receptor ligands |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20052512L NO20052512L (no) | 2005-05-25 |
| NO20052512D0 NO20052512D0 (no) | 2005-05-25 |
| NO332195B1 true NO332195B1 (no) | 2012-07-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20052512A NO332195B1 (no) | 2002-10-28 | 2005-05-25 | Purinforbindelse samt farmasoytisk preparat inneholdende det samme |
Country Status (45)
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GEP20043303B (en) * | 1999-11-12 | 2004-01-12 | Biogen Idec Inc | Polycycloalkylpurines as Adenosine Receptor Antagonists |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| US7241890B2 (en) * | 2001-10-30 | 2007-07-10 | Conforma Therapeutics Corporation | Purine analogs having HSP90-inhibiting activity |
| CA2499497A1 (en) | 2002-09-27 | 2004-04-08 | Merck & Co., Inc. | Substituted pyrimidines |
| 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 |
| EA011009B1 (ru) * | 2003-01-14 | 2008-12-30 | Арена Фармасьютикалз Инк. | 1,2,3-тризамещённые арильные и гетероарильные производные в качестве модуляторов метаболизма и профилактика и лечение расстройств, связанных с ним, таких как диабет и гипергликемия |
| 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 |
| US7094572B2 (en) | 2003-03-14 | 2006-08-22 | Bristol-Myers Squibb | Polynucleotide encoding a novel human G-protein coupled receptor variant of HM74, HGPRBMY74 |
| 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 |
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | 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 |
| CA2524397A1 (en) * | 2003-05-07 | 2004-11-18 | Pfizer Products Inc. | Cannabinoid receptor ligands and uses thereof |
| US20040224962A1 (en) * | 2003-05-09 | 2004-11-11 | Pfizer Inc | Pharmaceutical composition for the treatment of obesity or to facilitate or promote weight loss |
| US7232823B2 (en) * | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| AR045697A1 (es) | 2003-07-14 | 2005-11-09 | Arena Pharm Inc | Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo |
| US20050026983A1 (en) * | 2003-07-30 | 2005-02-03 | Pfizer Inc | Imidazole 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 |
| US7151097B2 (en) * | 2003-11-07 | 2006-12-19 | Pfizer Inc. | Bicyclic pyrazolyl and imidazolyl compounds and uses thereof |
| US7649002B2 (en) | 2004-02-04 | 2010-01-19 | Pfizer Inc | (3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| BRPI0516932A (pt) * | 2004-10-22 | 2008-09-23 | Pfizer Prod Inc | processo para a preparação de compostos de purina |
| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| AR051596A1 (es) * | 2004-10-26 | 2007-01-24 | Irm Llc | Compuestos heterociclicos condensados nitrogenados como inhibidores de la actividad del receptor canabinoide 1; composiciones farmaceuticas que los contienen y su empleo en la preparacion de medicamentos para el tratamiento de trastornos alimentarios |
| EP1811983B1 (en) | 2004-11-16 | 2020-10-07 | GW Pharma Limited | New use for cannabinoid |
| GB0425248D0 (en) * | 2004-11-16 | 2004-12-15 | Gw Pharma Ltd | New use for cannabinoid |
| PA8660701A1 (es) | 2005-02-04 | 2006-09-22 | Pfizer Prod Inc | Agonistas de pyy y sus usos |
| JP2008536909A (ja) * | 2005-04-20 | 2008-09-11 | 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としてのアシルアミノ二環複素芳香族化合物 |
| EP1890767A2 (en) * | 2005-05-27 | 2008-02-27 | Pfizer Products Inc. | Combination of a cannabinoid-1- receptor-antagonist and a microsomal triglyceride transfer protein inhibitor for treating obesity or mainataining weight loss |
| AU2006264649A1 (en) | 2005-06-30 | 2007-01-11 | Prosidion Limited | GPCR agonists |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| 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 |
| JP2009521446A (ja) * | 2005-12-22 | 2009-06-04 | コンフォーマ・セラピューティクス・コーポレイション | 熱ショックタンパク質９０の経口活性なプリンベースの阻害剤 |
| EP1986638A2 (en) * | 2006-02-21 | 2008-11-05 | Ampla Pharmaceuticals Inc. | Cb1 antagonists and inverse agonists |
| WO2007096763A2 (en) | 2006-02-23 | 2007-08-30 | Pfizer Limited | Melanocortin type 4 receptor agonist piperidinoylpyrrolidines |
| EP3719018A1 (en) | 2006-04-25 | 2020-10-07 | Astex Therapeutics Ltd | Purine and deazapurine derivatives as pharmaceutical compounds |
| 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 |
| ES2382009T3 (es) | 2006-12-01 | 2012-06-04 | Bristol-Myers Squibb Company | Derivados de N-((3-bencil)-2,2-(bis-fenil-)-propan-1-amina como inhibidores de CETP para el tratamiento de aterosclerosis y enfermedades cardiovasculares |
| 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 |
| PE20081849A1 (es) | 2007-01-04 | 2009-01-26 | Prosidion Ltd | Derivados de piperidin-4-il-propoxi-benzamida como agonistas de gpcr |
| CA2674360A1 (en) | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| AR064735A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr y composicion farmaceutica en base al compuesto |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| US20080220104A1 (en) * | 2007-03-08 | 2008-09-11 | Cappello John V | Compositions for producing satiety |
| MX2010003668A (es) | 2007-10-05 | 2010-07-02 | S Bio Pte Ltd | Derivados de purina sustituidas con primidina. |
| GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
| GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
| JP5693229B2 (ja) * | 2007-11-21 | 2015-04-01 | アッヴィ・バハマズ・リミテッド | ニコチンアセチルコリン受容体活性モジュレータとしてのビアリール置換アザ二環式アルカン誘導体 |
| 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 |
| CN102271515B (zh) | 2008-10-31 | 2014-07-02 | 健泰科生物技术公司 | 吡唑并嘧啶jak抑制剂化合物和方法 |
| 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 |
| EP2414362B1 (en) | 2009-04-03 | 2014-06-11 | 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 |
| WO2011059207A2 (en) | 2009-11-13 | 2011-05-19 | Green Cross Corporation | Arylpiperazine-containing purine derivatives and uses thereof |
| KR20130001272A (ko) * | 2010-03-17 | 2013-01-03 | 에프. 호프만-라 로슈 아게 | 이미다조피리딘 및 푸린 화합물, 조성물 및 사용 방법 |
| 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 |
| BR112012024587A2 (pt) * | 2010-03-31 | 2016-05-31 | Lilly Co Eli | compostos de purina usados como agonistas de cb2 |
| JP2013528598A (ja) | 2010-05-11 | 2013-07-11 | ファイザー・インク | ミネラルコルチコイド受容体拮抗薬としてのモルホリン化合物 |
| CA2812087A1 (en) | 2010-09-15 | 2012-03-22 | F. Hoffmann-La Roche Ag | Azabenzothiazole compounds, compositions and methods of use |
| WO2012040279A1 (en) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| CA2817785A1 (en) | 2010-11-19 | 2012-05-24 | Toby Blench | Pyrazolopyridines and pyrazolopyridines and their use as tyk2 inhibitors |
| EP2758397A1 (en) * | 2011-09-20 | 2014-07-30 | 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 |
| US9187480B2 (en) | 2012-02-17 | 2015-11-17 | 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 |
| PT2991987T (pt) | 2013-05-02 | 2018-07-13 | Hoffmann La Roche | Derivados de purina como agonistas do recetor cb2 |
| CA2939575A1 (en) | 2014-02-17 | 2015-08-20 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents |
| PE20211782A1 (es) | 2014-05-23 | 2021-09-08 | Hoffmann La Roche | Compuestos de 5-cloro-2-difluorometoxifenil pirazolopirimidina, composiciones y metodos de uso de los mismos |
| MX2021011472A (es) | 2015-01-06 | 2022-08-17 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| 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 |
| US10301262B2 (en) | 2015-06-22 | 2019-05-28 | 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(Compund1) for use in SIPI receptor-associated disorders |
| CA3036382A1 (en) * | 2016-12-21 | 2018-06-28 | Research Triangle Institute | Diaryl purine derivatives with improved bioavailability |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| PE20200341A1 (es) | 2017-05-22 | 2020-02-14 | Hoffmann La Roche | Composiciones y compuestos terapeuticos y metodos para utilizarlos |
| WO2020148760A1 (en) * | 2019-01-15 | 2020-07-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Cb1r receptor blockers with acyclic backbones |
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 |
| EP0268554B1 (de) * | 1986-10-22 | 1991-12-27 | Ciba-Geigy Ag | 1,5-Diphenylpyrazol-3-carbonsäurederivate zum Schützen von Kulturpflanzen |
| 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 |
| DE69717453T2 (de) * | 1996-06-06 | 2003-07-10 | Otsuka Pharma Co Ltd | Amid derivate |
| 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 |
| EP1054012B1 (en) | 1998-01-05 | 2003-06-11 | Eisai Co., Ltd. | Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes |
| 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 |
| KR100694684B1 (ko) * | 1999-07-02 | 2007-03-13 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 축합 이미다졸 화합물 및 당뇨병 치료약 |
| FR2799124B1 (fr) | 1999-10-01 | 2004-08-13 | Sanofi Synthelabo | Utilisation des antagonistes des recepteurs aux cannabinoides centraux pour la preparation de medicaments |
| WO2001028557A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Cannabimimetic indole derivatives |
| DE60023167T2 (de) | 1999-10-18 | 2006-06-14 | Univ Connecticut Farmington | Pyrazol-derivate als cannabinoidrezeptor-antagonisten |
| 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 |
| US6653304B2 (en) * | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| US6566356B2 (en) * | 2000-03-03 | 2003-05-20 | Aventis Pharma S.A. | Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation |
| 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 |
| ATE346047T1 (de) * | 2000-03-23 | 2006-12-15 | Solvay Pharm Bv | 4,5-dihydro-1h-pyrazolderivate mit cb1- antagonistischer aktivität |
| 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 |
| ATE526330T1 (de) | 2000-12-28 | 2011-10-15 | Ono Pharmaceutical Co | Heterotrizyklische verbindungen als antagonisten des crf-rezeptors |
| PL363751A1 (en) | 2001-03-22 | 2004-11-29 | 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 |
| 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 |
| EP1421077A4 (en) | 2001-08-31 | 2004-11-17 | Univ Connecticut | NEW PYRAZOLANALOGS ON CANNABINOID RECEPTORS |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| CN101659639A (zh) | 2001-09-21 | 2010-03-03 | 索尔瓦药物有限公司 | 具有cb1-拮抗活性的新的4,5-二氢-1h-吡唑衍生物 |
| JP4313672B2 (ja) | 2001-09-21 | 2009-08-12 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | 強力なｃｂ１−拮抗活性を有する４，５−ジヒドロ−１ｈ−ピラゾール誘導体 |
| US6509367B1 (en) * | 2001-09-22 | 2003-01-21 | Virginia Commonwealth University | Pyrazole cannabinoid agonist and antagonists |
| EP1432679A1 (en) | 2001-09-24 | 2004-06-30 | Bayer Pharmaceuticals Corporation | Preparation and use of pyrrole derivatives for treating obesity |
| ATE311386T1 (de) | 2001-09-24 | 2005-12-15 | Bayer Pharmaceuticals Corp | Verfahren zur herstellung von 1,5,6,7- tetrahydropyrrolo(3,2-c)derivaten zur behandlung der fettleibigkeit |
| PE20030547A1 (es) | 2001-09-24 | 2003-08-18 | Bayer Corp | Derivados de imidazol para el tratamiento de la obesidad |
| 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 |
| WO2003075660A1 (en) | 2002-03-06 | 2003-09-18 | Merck & Co., Inc. | Method of treatment or prevention of obesity |
| NZ534757A (en) | 2002-03-12 | 2006-07-28 | Merck & Co Inc | Substituted amides |
| 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. |
| 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 |
| AU2003225964B2 (en) | 2002-03-28 | 2008-11-20 | Merck Sharp & Dohme Corp. | Substituted 2,3-diphenyl pyridines |
| JP2005527586A (ja) | 2002-04-05 | 2005-09-15 | メルク エンド カムパニー インコーポレーテッド | 置換アリールアミド |
| FR2838439B1 (fr) | 2002-04-11 | 2005-05-20 | Sanofi Synthelabo | Derives de terphenyle, leur preparation, les compositions pharmaceutqiues en contenant |
| CA2481313A1 (en) | 2002-04-12 | 2003-10-23 | 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 |
| ES2287476T3 (es) | 2002-05-10 | 2007-12-16 | Smithkline Beecham Corporation | Pirazolopirimidinas sustituidas. |
| BR0314872A (pt) | 2002-10-18 | 2005-08-02 | Pfizer Prod Inc | Ligandos do receptor canabinóide e usos dos mesmos |
| 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 |
| BRPI0516932A (pt) * | 2004-10-22 | 2008-09-23 | Pfizer Prod Inc | processo para a preparação de compostos de purina |
-
2003
- 2003-10-20 US US10/689,381 patent/US7129239B2/en not_active Expired - Fee Related
- 2003-10-21 EP EP03751149A patent/EP1558615B8/en not_active Expired - Lifetime
- 2003-10-21 ES ES03751149T patent/ES2291669T3/es not_active Expired - Lifetime
- 2003-10-21 AP AP2005003290A patent/AP1916A/xx active
- 2003-10-21 CN CNA2006101625782A patent/CN1955181A/zh active Pending
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