ZA200402672B - Lactam derivatives as antagonists for human 11CBy receptors. - Google Patents
Lactam derivatives as antagonists for human 11CBy receptors. Download PDFInfo
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- ZA200402672B ZA200402672B ZA200402672A ZA200402672A ZA200402672B ZA 200402672 B ZA200402672 B ZA 200402672B ZA 200402672 A ZA200402672 A ZA 200402672A ZA 200402672 A ZA200402672 A ZA 200402672A ZA 200402672 B ZA200402672 B ZA 200402672B
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- C—CHEMISTRY; METALLURGY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| GBGB0124627.1A GB0124627D0 (en) | 2001-10-15 | 2001-10-15 | Novel compounds |
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| ZA200402814A ZA200402814B (en) | 2001-10-15 | 2004-04-13 | Pyrimidinones as melanin concentrating hormone receptor 1 |
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| JP (2) | JP2005508966A (ja) |
| KR (2) | KR20050043724A (ja) |
| CN (2) | CN1571774A (ja) |
| AT (2) | ATE356119T1 (ja) |
| BR (2) | BR0213040A (ja) |
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| DE (2) | DE60217147T2 (ja) |
| ES (2) | ES2283647T3 (ja) |
| GB (1) | GB0124627D0 (ja) |
| HU (2) | HUP0402346A2 (ja) |
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| WO (2) | WO2003033476A1 (ja) |
| ZA (2) | ZA200402672B (ja) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005510563A (ja) | 2001-11-26 | 2005-04-21 | シェーリング コーポレイション | 肥満およびｃｎｓ障害の処置のためのピペリジン系ｍｃｈアンタゴニスト |
| US7084156B2 (en) | 2001-11-27 | 2006-08-01 | Merck & Co., Inc. | 2-Aminoquinoline compounds |
| DE10238865A1 (de) * | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US20060194871A1 (en) * | 2003-04-11 | 2006-08-31 | Barvian Kevin K | Heterocyclic mchr1 antagoists |
| CN100418965C (zh) * | 2003-08-15 | 2008-09-17 | 万有制药株式会社 | 咪唑并吡啶衍生物 |
| KR100747042B1 (ko) * | 2003-08-19 | 2007-08-07 | 솔젠트 (주) | 신물질６-메틸-３-펜에틸-３,４-디히드로-１ｈ-큐나졸린-２-티온,이의 제조방법 및 이를 유효성분으로 포함하는 미백 효능조성물 |
| US20070078125A1 (en) * | 2003-10-23 | 2007-04-05 | Glaxo Group Limited | Arylamine mch r1 antagonists |
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| EP1717230B1 (en) * | 2004-02-13 | 2014-08-06 | Msd K.K. | Fused-ring 4-oxopyrimidine derivative |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| DE102004010893A1 (de) * | 2004-03-06 | 2005-09-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue ß-Ketoamid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7902356B2 (en) | 2004-12-17 | 2011-03-08 | Eli Lilly And Company | Thiazolopyridinone derivates as MCH receptor antagonists |
| US7790731B2 (en) * | 2005-02-14 | 2010-09-07 | Banyu Pharmaceutical Co. Ltd. | Crystal form of 2-methyl-3-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-5-trifluoromethyl-4(3H)-quinazolinone |
| US7989445B2 (en) | 2005-04-28 | 2011-08-02 | Takeda Pharmaceutical Company Limited | Thienopyrimidone compound |
| WO2007011286A1 (en) * | 2005-07-15 | 2007-01-25 | Astrazeneca Ab | Therapeutic agents |
| ES2434946T3 (es) * | 2005-08-31 | 2013-12-18 | Celgene Corporation | Compuestos de isoindol imida y composiciones que los comprenden y métodos para usarlo |
| PL1939204T6 (pl) * | 2005-10-19 | 2024-03-25 | Kissei Pharmaceutical Co., Ltd. | Skondensowana pochodna heterocykliczna, zawierająca ją kompozycja oraz jej zastosowanie medyczne |
| US7745447B2 (en) * | 2005-10-26 | 2010-06-29 | Bristol-Myers Squibb Company | Substituted thieno[3,2-D]pyrimidines as non-basic melanin concentrating hormone receptor-1 antagonists |
| AR056155A1 (es) | 2005-10-26 | 2007-09-19 | Bristol Myers Squibb Co | Antagonistas del receptor 1 de la hormona de concentracion de melanina no basica |
| RU2008129679A (ru) | 2005-12-21 | 2010-01-27 | Янссен Фармацевтика Н.В. (Be) | Новые замещенные пиразиноновые производные для применения при мсн-1-опосредованных заболеваниях |
| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| DE602007011897D1 (de) | 2006-02-15 | 2011-02-24 | Sanofi Aventis | Neue aminoalkohol-substituierte aryldihydroisochinolinone, herstellungsverfahren und ihre verwendung als medikamente |
| CN101384583A (zh) * | 2006-02-15 | 2009-03-11 | 塞诺菲-安万特股份有限公司 | 氮杂环基-取代的芳基二氢异喹啉酮、它们的制备方法和它们作为药物的用途 |
| JP2009526792A (ja) * | 2006-02-15 | 2009-07-23 | サノフィ−アベンティス | 新規なアザシクリル置換アリールチエノピリミジノン、それらの製造方法及び薬剤としてのそれらの使用 |
| KR20080096670A (ko) | 2006-02-15 | 2008-10-31 | 사노피-아벤티스 | 신규한 아미노 알콜-치환된 아릴티에노피리미디논, 이의 제조 방법 및 약제로서 이의 용도 |
| WO2007142217A1 (ja) * | 2006-06-07 | 2007-12-13 | Banyu Pharmaceutical Co., Ltd. | １－フェニルピリドン誘導体 |
| CA2652524A1 (en) | 2006-06-08 | 2007-12-21 | Eli Lilly And Company | Novel mch receptor antagonists |
| US8263772B2 (en) | 2006-06-08 | 2012-09-11 | Eli Lilly And Company | MCH receptor antagonists |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| WO2008020799A1 (en) * | 2006-08-18 | 2008-02-21 | Astrazeneca Ab | Thienopyrimidin-4-one and thienopyridazin-7-one derivatives as mch rl antagonists |
| RU2461558C2 (ru) | 2006-12-05 | 2012-09-20 | Янссен Фармацевтика Н.В. | Новые замещенные диазаспиропиридиноновые производные для применения в лечении мсн-1-опосредованных заболеваний |
| CA2671765A1 (en) * | 2006-12-14 | 2008-06-26 | Eli Lilly And Company | 5- [4- (azetidin-3-yloxy) -phenyl] -2-phenyl-5h-thiazolo [5,4-c] pyridin-4-one derivatives and their use as mch receptor |
| WO2008086404A1 (en) | 2007-01-10 | 2008-07-17 | Albany Molecular Research, Inc. | 5-pyridinone substituted indazoles |
| WO2008134480A1 (en) * | 2007-04-25 | 2008-11-06 | Bristol-Myers Squibb Company | Non-basic melanin concentrating hormone receptor-1 antagonists |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| DE102007028925A1 (de) | 2007-06-22 | 2008-12-24 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden |
| JP2010534248A (ja) | 2007-07-21 | 2010-11-04 | アルバニー モレキュラー リサーチ， インコーポレイテッド | ５−ピリジノン置換インダゾール |
| JP5632612B2 (ja) * | 2007-12-05 | 2014-11-26 | あすか製薬株式会社 | ラクタム化合物又はその塩及びｐｐａｒ活性化剤 |
| PE20091928A1 (es) | 2008-05-29 | 2009-12-31 | Bristol Myers Squibb Co | Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010009319A2 (en) | 2008-07-16 | 2010-01-21 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CN102271509A (zh) | 2008-10-31 | 2011-12-07 | 默沙东公司 | 用于抗糖尿病药的新型环苯并咪唑衍生物 |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2689707A1 (en) | 2009-11-16 | 2011-05-16 | Jean-Simon Diallo | Identification of the novel small molecule viral sensitizer vse1 using high-throughput screening |
| CN102482312A (zh) | 2009-08-26 | 2012-05-30 | 赛诺菲 | 新颖的杂芳族氟代糖苷结晶水合物、含有这些化合物的药物和它们的用途 |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| WO2012036233A1 (ja) * | 2010-09-17 | 2012-03-22 | 塩野義製薬株式会社 | メラニン凝集ホルモン受容体アンタゴニスト活性を有する縮合へテロ環誘導体 |
| EP2677869B1 (en) | 2011-02-25 | 2017-11-08 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| KR101236188B1 (ko) * | 2011-03-10 | 2013-02-22 | 한국화학연구원 | 신규한 피롤로피리디논 유도체 및 그의 ｍｃｈ 수용체-1 관련 질환에 대한 치료학적 용도 |
| HUP1100241A3 (en) | 2011-05-06 | 2013-12-30 | Richter Gedeon Nyrt | Oxetane substituted pyrimidones |
| NO3175985T3 (ja) | 2011-07-01 | 2018-04-28 | ||
| UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| CA2880901A1 (en) | 2012-08-02 | 2014-02-06 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2014130608A1 (en) | 2013-02-22 | 2014-08-28 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| EP2970119B1 (en) | 2013-03-14 | 2021-11-03 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| JP6615791B2 (ja) * | 2014-06-05 | 2019-12-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫剤としての二環式化合物 |
| BR112018012914B1 (pt) | 2015-12-22 | 2023-04-18 | SHY Therapeutics LLC | Composto, uso de um composto e composição farmacêutica |
| EP3497089B1 (de) * | 2016-08-12 | 2020-07-29 | Bayer CropScience Aktiengesellschaft | Verfahren zur herstellung von 4-substituierten 2,3-dihydro-1-benzofuranderivaten durch zyklisierung von 2-(2-diazonium-6-substituierten-phenyl)ethanol salzen |
| EP3509587B1 (en) | 2016-09-12 | 2023-12-06 | Valo Health, Inc. | Monocyclic compounds useful as gpr120 modulators |
| EP3509588B1 (en) * | 2016-09-12 | 2023-06-07 | Integral Health,Inc. | Bicyclic compounds useful as gpr120 modulators |
| EP3551176A4 (en) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | ANTIDIABETIC HETEROCYCLIC COMPOUNDS |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| SG11201911929XA (en) | 2017-06-21 | 2020-01-30 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| WO2019063708A1 (en) | 2017-09-29 | 2019-04-04 | Bayer Aktiengesellschaft | SUBSTITUTED 3-PHENYLQUINAZOLIN-4 (3H) -ONES AND USES THEREOF |
| UY37907A (es) | 2017-09-29 | 2019-04-30 | Bayer Ag | 3-fenilquinazolin-4 (3h)-onas sustituidas y sus usos |
| CN110563730B (zh) * | 2019-07-29 | 2022-03-25 | 江苏理工学院 | 高纯度n10-三氟乙酰蝶酸的制备方法 |
| CN113651800B (zh) * | 2021-09-07 | 2022-08-19 | 山东铂源药业股份有限公司 | 一种甲磺酸奥希替尼的制备方法 |
| WO2024054591A1 (en) | 2022-09-07 | 2024-03-14 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use |
Family Cites Families (3)
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| PL137227B2 (en) * | 1984-03-28 | 1986-05-31 | Univ Lodzki | Process for preparing novel n-/dialkylaminoalkoxyphenyl/-imides of tetrahydrophtalic acids |
| WO1997041097A2 (en) * | 1996-12-31 | 1997-11-06 | Dr. Reddy's Research Foundation | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| EP1218336A2 (en) * | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
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