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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| TW201618781A (zh) | 2014-08-13 | 2016-06-01 | 吉李德科學股份有限公司 | 治療肺高血壓之方法 |
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| MA41252A (fr) | 2014-12-23 | 2017-10-31 | Gilead Sciences Inc | Formes solides d'un inhibiteur d'ask 1 |
| TWI685491B (zh) | 2014-12-23 | 2020-02-21 | 美商基利科學股份有限公司 | 製備５-（４-環丙基-１ｈ-咪唑-１-基）-ｎ-（６-（４-異丙基-４ｈ-１,２,４-三唑-３-基）吡啶-２-基）-２-氟-４-甲基苯甲醯胺之方法 |
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| 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 |
| MA45918A (fr) | 2016-08-15 | 2019-06-19 | Bayer Ag | Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides |
| TWI674260B (zh) | 2017-02-01 | 2019-10-11 | 德商菲尼克斯製藥股份有限公司 | 芳基烴受體(AhR)調節劑化合物 |
| 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 |
| JOP20190221A1 (ar) | 2017-04-05 | 2019-09-23 | Seal Rock Therapeutics Inc | مركبات مثبطات كيناز منظم لإشارات الاستماتة 1 (ask1) واستخداماتها |
| CN110869017B (zh) | 2017-05-12 | 2023-05-05 | 英安塔制药有限公司 | 细胞凋亡信号调节激酶1抑制剂及其使用方法 |
| WO2018218044A2 (en) * | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals Inc | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218051A1 (en) * | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10253018B2 (en) | 2017-05-25 | 2019-04-09 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| 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 |
| WO2019046186A1 (en) | 2017-08-28 | 2019-03-07 | Enanta Pharmaceuticals, Inc. | INHIBITORS OF KINASE 1 REGULATING THE APOPTOTIC SIGNAL CONTAINING TETRAZOLES AND METHODS OF USE THEREOF |
| CN111801314B (zh) | 2018-01-02 | 2023-10-31 | 西尔洛克治疗公司 | Ask1抑制剂化合物及其用途 |
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| WO2019213239A1 (en) | 2018-05-02 | 2019-11-07 | Enanta Pharmaceuticals Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| JP2021529186A (ja) * | 2018-07-03 | 2021-10-28 | ノバルティス アーゲー | Ｎｌｒｐ調節剤 |
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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 |
| MX2021013657A (es) * | 2019-05-10 | 2022-02-21 | Takeda Pharmaceuticals Co | Conjugados de anticuerpo y farmaco. |
| 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 |
| US20240124444A1 (en) * | 2020-12-28 | 2024-04-18 | Celgene Corporation | Heterocyclic Compounds and Their Use for Parasitic Diseases |
| WO2024054749A2 (en) * | 2022-09-08 | 2024-03-14 | Bridge Medicines | Inhibitors of enl/af9 yeats and flt3 |
| 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 |
| CN117122288B (zh) * | 2023-09-08 | 2024-10-18 | 太原理工大学 | 基于锚定卷积网络的癫痫脑电信号预警方法及装置 |
Family Cites Families (87)
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| US4044126A (en) | 1972-04-20 | 1977-08-23 | Allen & Hanburys Limited | Steroidal aerosol compositions and process for the preparation thereof |
| 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 |
| US4410545A (en) | 1981-02-13 | 1983-10-18 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4328245A (en) | 1981-02-13 | 1982-05-04 | 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 |
| US5120712A (en) | 1986-05-05 | 1992-06-09 | The General Hospital Corporation | Insulinotropic hormone |
| US5118666A (en) | 1986-05-05 | 1992-06-02 | 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 |
| EP0497894A4 (en) | 1989-10-25 | 1993-03-31 | The Salk Institute For Biological Studies | Receptor infection assay |
| ATE164852T1 (de) | 1990-01-24 | 1998-04-15 | Douglas I Buckley | Glp-1-analoga verwendbar in der diabetesbehandlung |
| ATE133267T1 (de) | 1990-09-21 | 1996-02-15 | Salk Inst For Biological Studi | Durch protoonkogenischen proteinkomplex ap-1 kontrollierte verfahren |
| DE10199058I2 (de) | 1991-07-30 | 2006-04-27 | Alcm Co | Kristalle von N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanin und Verfahren zu ihrer Herstellung |
| 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 |
| JPH07509694A (ja) | 1992-05-14 | 1995-10-26 | ベイラー・カレッジ・オブ・メディシン | 突然変異したステロイドホルモン受容体，その使用方法および遺伝子治療のための分子スイッチ |
| EP0694078A4 (en) | 1993-04-07 | 1997-06-25 | Ligand Pharm Inc | SORTING PROCESS RELATING TO RECEPTOR AGONISTS |
| 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 |
| CA2180271A1 (en) | 1993-12-30 | 1995-07-06 | Ronald M. Evans | Novel uses for gal4-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 |
| FI974437A7 (fi) | 1995-06-06 | 1997-12-05 | Pfizer | Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogee nifosforylaasi-inhibiittoreina |
| CA2224062C (en) | 1995-06-06 | 2001-09-04 | Pfizer Limited | Substituted n-(indole-2-carbonyl)-glycinamides and derivatives as glycogen phosphorylase inhibitors |
| AU6944296A (en) | 1995-09-13 | 1997-04-01 | Takeda Chemical Industries Ltd. | Benzoxazepine compounds, their production and use as lipid lowering agents |
| EP0859771A4 (en) | 1995-10-31 | 2000-03-15 | Merck & Co Inc | SUBSTITUTED PYRIDYLPYRROLE, PREPARATIONS CONTAINING SUCH COMPOUNDS AND METHOD FOR THE USE THEREOF |
| AU2090897A (en) | 1996-02-29 | 1997-09-16 | 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 |
| EP1019043A4 (en) | 1996-05-07 | 2003-07-30 | Univ Pennsylvania | INHIBITORS OF GLYCOGEN SYNTHESIS KINASE 3 AND METHOD FOR THEIR IDENTIFICATION AND USE |
| CA2257206A1 (en) | 1996-06-07 | 1997-12-11 | Gui-Bai Liang | Oxadiazole benzenesulfonamides as selective .beta.3 agonists for the treatment of diabetes and obesity |
| AR008789A1 (es) | 1996-07-31 | 2000-02-23 | Bayer Corp | Piridinas y bifenilos substituidos |
| EP0827746B1 (en) | 1996-09-05 | 2002-04-03 | Eli Lilly And Company | Carbazole analogues as selective beta3 adrenergic agonists |
| 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 |
| WO1998022109A1 (en) | 1996-11-20 | 1998-05-28 | Merck & Co., Inc. | Triaryl substituted imidazoles as glucagon antagonists |
| US5880139A (en) | 1996-11-20 | 1999-03-09 | Merck & Co., Inc. | Triaryl substituted imidazoles as glucagon antagonists |
| EP0959885A4 (en) | 1996-11-20 | 2002-07-17 | Merck & Co Inc | TRIARYL SUBSTITUTED IMIDAZOLES AND METHODS OF USE |
| WO1998021957A1 (en) | 1996-11-20 | 1998-05-28 | Merck & Co., Inc. | Triaryl substituted imidazoles, compositions containing such compounds and methods of use |
| US5952322A (en) | 1996-12-05 | 1999-09-14 | Pfizer Inc. | Method of reducing tissue damage associated with non-cardiac ischemia using glycogen phosphorylase inhibitors |
| KR20000070568A (ko) | 1997-01-28 | 2000-11-25 | 폴락 돈나 엘. | 당뇨병 및 비만 치료를 위한 β3 효능제로서의 티아졸 벤젠설폰아미드 |
| JP2001514631A (ja) | 1997-03-07 | 2001-09-11 | ノボ ノルディスク アクティーゼルスカブ | ４，５，６，７−テトラヒドロ−チエノ［３，２−ｃ］ピリジン誘導体類、それらの製造方法及び使用 |
| US6054587A (en) | 1997-03-07 | 2000-04-25 | Metabasis Therapeutics, Inc. | Indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| DE69819311T2 (de) | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
| AU6452098A (en) | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| AU749271B2 (en) | 1997-07-01 | 2002-06-20 | Agouron Pharmaceuticals, Inc. | Glucagon antagonists/inverse agonists |
| WO1999015529A1 (en) | 1997-09-23 | 1999-04-01 | Novo Nordisk A/S | MODULES 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 |
| JP2001525398A (ja) | 1997-12-05 | 2001-12-11 | イーライ・リリー・アンド・カンパニー | 選択的β３アドレナリン作動性アゴニスト |
| 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 |
| WO1999046237A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases |
| WO1999046236A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| AU2713799A (en) | 1998-03-12 | 1999-09-27 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| WO1999046267A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| JP2002506073A (ja) | 1998-03-12 | 2002-02-26 | ノボ ノルディスク アクティーゼルスカブ | プロテイン・チロシン・ホスファターゼ（ＰＴＰａｓｅｓ）のモジュレーター |
| WO1999047549A1 (en) | 1998-03-16 | 1999-09-23 | Ontogen Corporation | PIPERAZINES AS INHIBITORS OF FRUCTOSE-1,6-BISPHOSPHATASE (FBPase) |
| ATE286032T1 (de) | 1998-04-23 | 2005-01-15 | 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 |
| JP2002514635A (ja) | 1998-05-12 | 2002-05-21 | アメリカン・ホーム・プロダクツ・コーポレイション | インスリン耐性および高血糖の処置に有用なビフェニルオキソ−酢酸 |
| AU3791699A (en) | 1998-05-12 | 1999-11-29 | American Home Products Corporation | Naphtho{2,3-b}heteroar-4-yl derivatives |
| EP0978279A1 (en) | 1998-08-07 | 2000-02-09 | Pfizer Products Inc. | Inhibitors of human glycogen phosphorylase |
| WO2000014090A1 (en) | 1998-09-02 | 2000-03-16 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno[2,3-c]pyridine derivatives |
| ATE246197T1 (de) | 1998-09-09 | 2003-08-15 | Metabasis Therapeutics Inc | Neue heteroaromatische fructose 1,6- bisphosphatase inhibitoren |
| ATE284387T1 (de) | 1998-10-08 | 2004-12-15 | Smithkline Beecham Plc | 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 |
| US20100029619A1 (en) * | 2006-08-04 | 2010-02-04 | Takeda Pharmaceutical Company Limted | Fused heterocyclic compound |
| CA2691448A1 (en) * | 2007-08-31 | 2009-03-05 | Dominique Swinnen | Triazolopyridine compounds and their use as ask inhibitors |
| EP2271646A1 (en) * | 2008-03-31 | 2011-01-12 | Takeda Pharmaceutical Company Limited | Apoptosis signal-regulating kinase 1 inhibitors |
| PL2531501T3 (pl) * | 2010-02-03 | 2014-05-30 | Takeda Pharmaceuticals Co | Inhibitory kinazy 1 regulującej sygnał apoptotyczny |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2531501B1 (en) | 2013-11-20 |
| US8802695B2 (en) | 2014-08-12 |
| CA2787360C (en) | 2019-03-05 |
| PL2531501T3 (pl) | 2014-05-30 |
| CN102834393A (zh) | 2012-12-19 |
| SMT201400012B (it) | 2014-03-07 |
| WO2011097079A1 (en) | 2011-08-11 |
| CA2787360A1 (en) | 2011-08-11 |
| US9403819B2 (en) | 2016-08-02 |
| PT2531501E (pt) | 2014-02-17 |
| HRP20140114T1 (hr) | 2014-03-14 |
| US20120316194A1 (en) | 2012-12-13 |
| SI2531501T1 (sl) | 2014-04-30 |
| EP2531501A1 (en) | 2012-12-12 |
| DK2531501T3 (en) | 2014-02-24 |
| JP2013518881A (ja) | 2013-05-23 |
| US20140329850A1 (en) | 2014-11-06 |
| CN102834393B (zh) | 2015-07-22 |
| ES2445917T3 (es) | 2014-03-06 |
| RS53176B (sr) | 2014-06-30 |
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