JP5711270B2 - アポトーシスシグナル調節キナーゼ１阻害剤 - Google Patents
アポトーシスシグナル調節キナーゼ１阻害剤 Download PDFInfo
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- JP5711270B2 JP5711270B2 JP2012551994A JP2012551994A JP5711270B2 JP 5711270 B2 JP5711270 B2 JP 5711270B2 JP 2012551994 A JP2012551994 A JP 2012551994A JP 2012551994 A JP2012551994 A JP 2012551994A JP 5711270 B2 JP5711270 B2 JP 5711270B2
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- Prior art keywords
- alkyl
- pyrrolo
- pyridin
- benzamide
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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| MA41252A (fr) | 2014-12-23 | 2017-10-31 | Gilead Sciences Inc | Formes solides d'un inhibiteur d'ask 1 |
| CA3100432C (en) | 2014-12-23 | 2023-08-08 | Gilead Sciences, Inc. | Processes for preparing ask1 inhibitors |
| US10849911B2 (en) | 2015-06-10 | 2020-12-01 | Galmed Research And Development Ltd. | Low dose compositions of Aramachol salts |
| WO2017169503A1 (ja) * | 2016-04-01 | 2017-10-05 | 国立大学法人 千葉大学 | 含窒素芳香族アミドの製造方法、ピロール・イミダゾールポリアミドの製造方法、及び化合物 |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| RU2019107162A (ru) | 2016-08-15 | 2020-09-15 | Байер Кропсайенс Акциенгезельшафт | Конденсированные бициклические гетероциклические производные в качестве средств для борьбы с вредителями |
| TWI752155B (zh) | 2017-02-01 | 2022-01-11 | 德商菲尼克斯製藥股份有限公司 | 芳香烴受體(AhR)調節劑化合物 |
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| JOP20190221A1 (ar) * | 2017-04-05 | 2019-09-23 | Seal Rock Therapeutics Inc | مركبات مثبطات كيناز منظم لإشارات الاستماتة 1 (ask1) واستخداماتها |
| EP3621615B1 (en) | 2017-05-12 | 2023-11-15 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10246439B2 (en) | 2017-05-25 | 2019-04-02 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218042A1 (en) * | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
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| CN110770233B (zh) * | 2017-06-19 | 2022-07-26 | 广东东阳光药业有限公司 | 稠合双环类化合物及其在药物中的应用 |
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| US11434249B1 (en) | 2018-01-02 | 2022-09-06 | Seal Rock Therapeutics, Inc. | ASK1 inhibitor compounds and uses thereof |
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| US11008304B2 (en) | 2018-05-02 | 2021-05-18 | Enanta Pharmaceuticals, Inc. | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
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| US10968199B2 (en) | 2018-08-22 | 2021-04-06 | Enanta Pharmaceuticals, Inc. | Cycloalkyl-containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020106707A1 (en) | 2018-11-19 | 2020-05-28 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US11466033B2 (en) | 2019-03-25 | 2022-10-11 | Enanta Pharmaceuticals, Inc. | Substituted pyridines as apoptosis signal-regulating kinase 1 inhibitors |
| WO2020229982A1 (en) * | 2019-05-10 | 2020-11-19 | Takeda Pharmaceutical Company Limited | Antibody drug conjugates |
| CN111808079A (zh) * | 2020-08-05 | 2020-10-23 | 中国药科大学 | 吲哚类ask1小分子抑制剂及其制备方法和应用 |
| JP2024500989A (ja) * | 2020-12-28 | 2024-01-10 | セルジーン コーポレーション | 寄生虫症のためのヘテロ環化合物およびそれらの使用 |
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| CN115368352B (zh) * | 2022-10-25 | 2023-08-15 | 南京盛德瑞尔医药科技有限公司 | 一种葡萄糖激酶激动剂及其制备方法和应用 |
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| GB1429184A (en) | 1972-04-20 | 1976-03-24 | Allen & Hanburys Ltd | Physically anti-inflammatory steroids for use in aerosols |
| USRE28819E (en) | 1972-12-08 | 1976-05-18 | Syntex (U.S.A.) Inc. | Dialkylated glycol compositions and medicament preparations containing same |
| US4062950A (en) | 1973-09-22 | 1977-12-13 | Bayer Aktiengesellschaft | Amino sugar derivatives |
| US4328245A (en) | 1981-02-13 | 1982-05-04 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4410545A (en) | 1981-02-13 | 1983-10-18 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4358603A (en) | 1981-04-16 | 1982-11-09 | Syntex (U.S.A.) Inc. | Acetal stabilized prostaglandin compositions |
| US4409239A (en) | 1982-01-21 | 1983-10-11 | Syntex (U.S.A.) Inc. | Propylene glycol diester solutions of PGE-type compounds |
| DE3347565A1 (de) | 1983-12-30 | 1985-07-11 | Thomae Gmbh Dr K | Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JPS6354321A (ja) | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
| DE3543999A1 (de) | 1985-12-13 | 1987-06-19 | Bayer Ag | Hochreine acarbose |
| US5118666A (en) | 1986-05-05 | 1992-06-02 | The General Hospital Corporation | Insulinotropic hormone |
| US5120712A (en) | 1986-05-05 | 1992-06-09 | The General Hospital Corporation | Insulinotropic hormone |
| US5071773A (en) | 1986-10-24 | 1991-12-10 | The Salk Institute For Biological Studies | Hormone receptor-related bioassays |
| US4981784A (en) | 1987-12-02 | 1991-01-01 | The Salk Institute For Biological Studies | Retinoic acid receptor method |
| WO1991006677A1 (en) | 1989-10-25 | 1991-05-16 | The Salk Institute For Biological Studies | Receptor infection assay |
| CA2073856C (en) | 1990-01-24 | 2002-12-03 | Douglas I. Buckley | Glp-1 analogs useful for diabetes treatment |
| JPH06503642A (ja) | 1990-09-21 | 1994-04-21 | ザ ソーク インスティテュート フォア バイオロジカル スタディーズ | プロトオンコタンパク質ｃ−ＪＵＮとホルモン受容体との間の機能的拮抗作用 |
| ES2100291T3 (es) | 1991-07-30 | 1997-06-16 | Ajinomoto Kk | Cristales de n-(trans-4-isopropilciclohexilcarbonil)-d-fenilalanina y metodos para prepararlos. |
| US5866563A (en) | 1991-09-30 | 1999-02-02 | The University Of British Columbia | Vanadium compositions |
| JPH07503609A (ja) | 1991-12-06 | 1995-04-20 | ザ ソールク インスチチュート フォア バイオロジカル スタディズ | リセプターのステロイド／甲状腺スーパーファミリーのメンバーの多量体型 |
| EP0745121B1 (en) | 1992-05-14 | 2007-06-20 | Baylor College Of Medicine | Mutated steroid hormone receptors, methods for their use and molecular switch for gene therapy |
| JPH08512197A (ja) | 1993-04-07 | 1996-12-24 | リガンド・ファーマシューティカルズ・インコーポレーテッド | 受容体アゴニストのスクリーニング方法 |
| US6074861A (en) | 1993-04-15 | 2000-06-13 | National Jewish Center For Immunology And Respiratory Medicine | MEKK proteins |
| US5981265A (en) | 1993-04-15 | 1999-11-09 | National Jewish Center For Immunology And Respiratory Medicine | Methods for regulating MEKK protein activity |
| US5506102A (en) | 1993-10-28 | 1996-04-09 | Ligand Pharmaceuticals Incorporated | Methods of using the A form of the progesterone receptor to screen for antagonists of steroid intracellar receptor-mediated transcription |
| EP0737314A4 (en) | 1993-12-30 | 1999-11-03 | Salk Inst For Biological Studi | USES FOR GAL 4 RECEPTOR CONSTRUCTS |
| US5705515A (en) | 1994-04-26 | 1998-01-06 | Merck & Co., Inc. | Substituted sulfonamides as selective β-3 agonists for the treatment of diabetes and obesity |
| DE4416433A1 (de) | 1994-05-10 | 1995-11-16 | Hoechst Ag | Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung der Verbindungen zur Behandlung von Krankheiten |
| US5488510A (en) | 1994-07-26 | 1996-01-30 | Lemay; Edward J. | Enhanced depth perception viewing device for television |
| US5512549A (en) | 1994-10-18 | 1996-04-30 | Eli Lilly And Company | Glucagon-like insulinotropic peptide analogs, compositions, and methods of use |
| ATE206702T1 (de) | 1995-06-06 | 2001-10-15 | Pfizer | Substituierte n-(indol-2-carbonyl)-glycinamide und derivate als glycogen phosphorylase inhibitoren |
| EP0832066B1 (en) | 1995-06-06 | 2001-09-12 | Pfizer Inc. | Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors |
| WO1997010224A1 (en) | 1995-09-13 | 1997-03-20 | Takeda Chemical Industries, Ltd. | Benzoxazepine compounds, their production and use as lipid lowering agents |
| AU702887B2 (en) | 1995-10-31 | 1999-03-11 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| WO1997031901A1 (en) | 1996-02-29 | 1997-09-04 | Mikael Bols | Hydroxyhexahydropyridazines |
| US5770615A (en) | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| JP3839103B2 (ja) | 1996-04-19 | 2006-11-01 | 財団法人癌研究会 | アポトーシス誘導タンパク質およびそれをコードする遺伝子 |
| WO1997041854A1 (en) | 1996-05-07 | 1997-11-13 | The Trustees Of The University Of Pennsylvania | Inhibitors of glycogen synthase kinase-3 and methods for identifying and using the same |
| WO1997046556A1 (en) | 1996-06-07 | 1997-12-11 | Merck & Co., Inc. | OXADIAZOLE BENZENESULFONAMIDES AS SELECTIVE β3 AGONISTS FOR THE TREATMENT OF DIABETES AND OBESITY |
| AR008789A1 (es) | 1996-07-31 | 2000-02-23 | Bayer Corp | Piridinas y bifenilos substituidos |
| DE69711519T2 (de) | 1996-09-05 | 2002-10-31 | Eli Lilly And Co., Indianapolis | Carbazolanaloge als selektive beta3-adrenergische Agonisten |
| US5776954A (en) | 1996-10-30 | 1998-07-07 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| FR2755439B1 (fr) | 1996-11-05 | 1998-12-24 | Virbac Sa | Derives aryloxypropanolamines, leur procede de preparation et leurs applications |
| WO1998021957A1 (en) | 1996-11-20 | 1998-05-28 | Merck & Co., Inc. | Triaryl substituted imidazoles, compositions containing such compounds and methods of use |
| WO1998022109A1 (en) | 1996-11-20 | 1998-05-28 | Merck & Co., Inc. | Triaryl substituted imidazoles as glucagon antagonists |
| JP2001504489A (ja) | 1996-11-20 | 2001-04-03 | メルク エンド カンパニー インコーポレーテッド | トリアリール置換イミダゾール及び使用方法 |
| US5880139A (en) | 1996-11-20 | 1999-03-09 | Merck & Co., Inc. | Triaryl substituted imidazoles as glucagon antagonists |
| US5952322A (en) | 1996-12-05 | 1999-09-14 | Pfizer Inc. | Method of reducing tissue damage associated with non-cardiac ischemia using glycogen phosphorylase inhibitors |
| HUP0002053A3 (en) | 1997-01-28 | 2001-09-28 | Merck & Co Inc | Thiazole benzenesulfonamides as beta3 agonists for the treatment of diabetes and obesity |
| ES2210728T3 (es) | 1997-03-07 | 2004-07-01 | Metabasis Therapeutics, Inc. | Nuevos inhibidores bencimidazol de la fructosa-1, 6-bifosfatasa. |
| WO1998040385A1 (en) | 1997-03-07 | 1998-09-17 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO[3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
| WO1998039344A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| WO1998039342A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| AU749271B2 (en) | 1997-07-01 | 2002-06-20 | Agouron Pharmaceuticals, Inc. | Glucagon antagonists/inverse agonists |
| US6169087B1 (en) | 1997-09-23 | 2001-01-02 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPases) |
| UA57811C2 (uk) | 1997-11-21 | 2003-07-15 | Пфайзер Продактс Інк. | Фармацевтична композиція, що містить інгібітор альдозоредуктази та інгібітор глікогенфосфорилази (варіанти), комплект, який її включає, та способи лікування ссавців зі станом інсулінорезистентності |
| US6232337B1 (en) | 1997-12-05 | 2001-05-15 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| AU2610299A (en) | 1998-02-05 | 1999-08-23 | Novo Nordisk A/S | Hydrazone derivatives |
| US5998463A (en) | 1998-02-27 | 1999-12-07 | Pfizer Inc | Glycogen phosphorylase inhibitors |
| WO1999046267A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| AU2713699A (en) | 1998-03-12 | 1999-09-27 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| HUP0102612A2 (hu) | 1998-03-12 | 2001-11-28 | Novo Nordisk A/S | Fehérje-tirozinfoszfatázokat moduláló vegyületek és ezeket tartalmazó gyógyászati készítmények |
| EP1062218A1 (en) | 1998-03-12 | 2000-12-27 | Novo Nordisk A/S | MODULATORS OF PROTEIN TYROSINE PHOSPHATASES (PTPases) |
| WO1999046244A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| WO1999047549A1 (en) | 1998-03-16 | 1999-09-23 | Ontogen Corporation | PIPERAZINES AS INHIBITORS OF FRUCTOSE-1,6-BISPHOSPHATASE (FBPase) |
| DE69828445D1 (de) | 1998-04-23 | 2005-02-03 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
| US6057316A (en) | 1998-05-12 | 2000-05-02 | American Home Products Corporation | 4-aryl-1-oxa-9-thia-cyclopenta[b]fluorenes |
| US6001867A (en) | 1998-05-12 | 1999-12-14 | American Home Products Corporation | 1-aryl-dibenzothiophenes |
| WO1999058522A1 (en) | 1998-05-12 | 1999-11-18 | American Home Products Corporation | Naphtho[2,3-b]heteroar-4-yl derivatives |
| ATE229015T1 (de) | 1998-05-12 | 2002-12-15 | Wyeth Corp | Zur behandlung von insulin-resistenz und hyperglycemie geeignete biphenyl-oxo-essigsäuren |
| EP0978279A1 (en) | 1998-08-07 | 2000-02-09 | Pfizer Products Inc. | Inhibitors of human glycogen phosphorylase |
| AU5154699A (en) | 1998-09-02 | 2000-03-27 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno(2,3-c)pyridine derivatives |
| HK1042496B (zh) | 1998-09-09 | 2006-01-27 | 症变治疗公司 | 新的果糖1，6-二磷酸酶的杂芳族抑制剂 |
| DE69922526T2 (de) | 1998-10-08 | 2005-06-02 | Smithkline Beecham Plc, Brentford | 3-(3-chloro-4-hydroxyphenylamino)-4-(2-nitrophenyl)-1h-pyrrol-2,5-dion als glykogen synthase kinase-3 inhibitor (gsk-3) |
| GB9905416D0 (en) | 1999-03-09 | 1999-05-05 | Allelix Biopharma | Small molecules having GLP-2 like activity |
| GB2351081A (en) | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Pharmaceutically active imidazoline compounds and analogues thereof |
| US6080546A (en) | 1999-07-23 | 2000-06-27 | Isis Pharmaceuticals Inc. | Antisense modulation of MEKK5 expression |
| US6030837A (en) | 1999-08-03 | 2000-02-29 | Isis Pharmaceuticals Inc. | Antisense inhibition of PEPCK-mitochondrial expression |
| AR035016A1 (es) | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
| GB9930882D0 (en) | 1999-12-30 | 2000-02-23 | Nps Allelix Corp | GLP-2 formulations |
| EP1572720A4 (en) | 2002-05-24 | 2008-12-24 | Nps Allelix Corp | PROCESS FOR THE ENZYMATIC PRODUCTION OF GLP-2 (1-34) AND GLP-2 (1-33) PEPTIDES |
| EP2058309A4 (en) * | 2006-08-04 | 2010-12-22 | Takeda Pharmaceutical | CONDENSED HETEROCYCLIC COMPOUND |
| CN101878212A (zh) * | 2007-08-31 | 2010-11-03 | 默克雪兰诺有限公司 | 三唑并吡啶化合物及其作为ask抑制剂的用途 |
| US8461163B2 (en) * | 2008-03-31 | 2013-06-11 | Takeda Pharmaceutical Company Limited | Substituted N-(pyrazolo[1,5-a]pyrimidin-5-yl)amides as inhibitors of apoptosis signal-regulating kinase 1 |
| EP2531501B1 (en) | 2010-02-03 | 2013-11-20 | Takeda Pharmaceutical Company Limited | Apoptosis signal-regulating kinase 1 inhibitors |
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| Publication number | Publication date |
|---|---|
| US20120316194A1 (en) | 2012-12-13 |
| RS53176B (sr) | 2014-06-30 |
| CN102834393A (zh) | 2012-12-19 |
| ES2445917T3 (es) | 2014-03-06 |
| CA2787360C (en) | 2019-03-05 |
| HRP20140114T1 (hr) | 2014-03-14 |
| PL2531501T3 (pl) | 2014-05-30 |
| EP2531501A1 (en) | 2012-12-12 |
| EP2531501B1 (en) | 2013-11-20 |
| DK2531501T3 (en) | 2014-02-24 |
| WO2011097079A1 (en) | 2011-08-11 |
| US8802695B2 (en) | 2014-08-12 |
| US9403819B2 (en) | 2016-08-02 |
| CN102834393B (zh) | 2015-07-22 |
| CA2787360A1 (en) | 2011-08-11 |
| SI2531501T1 (sl) | 2014-04-30 |
| PT2531501E (pt) | 2014-02-17 |
| JP2013518881A (ja) | 2013-05-23 |
| SMT201400012B (it) | 2014-03-07 |
| US20140329850A1 (en) | 2014-11-06 |
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