TW201206907A - Bicyclic acetyl-COA carboxylase inhibitors and uses thereof - Google Patents
Bicyclic acetyl-COA carboxylase inhibitors and uses thereof Download PDFInfo
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- TW201206907A TW201206907A TW100126860A TW100126860A TW201206907A TW 201206907 A TW201206907 A TW 201206907A TW 100126860 A TW100126860 A TW 100126860A TW 100126860 A TW100126860 A TW 100126860A TW 201206907 A TW201206907 A TW 201206907A
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- 125000002619 bicyclic group Chemical group 0.000 title description 9
- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 title description 5
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- 238000000034 method Methods 0.000 claims abstract description 126
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- -1 Oxyl Chemical group 0.000 claims description 264
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 89
- 125000003545 alkoxy group Chemical group 0.000 claims description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
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| TW (1) | TW201206907A (enExample) |
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| WO (1) | WO2012013716A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7745629B2 (en) * | 2005-05-16 | 2010-06-29 | Vertex Pharmaceuticals Incorporated | Bicyclic derivatives as modulators of ion channels |
| TW201300358A (zh) * | 2011-03-14 | 2013-01-01 | 大正製藥股份有限公司 | 含氮縮合雜環化合物 |
| EP2772485A4 (en) * | 2011-10-24 | 2015-06-10 | Takeda Pharmaceutical | BICYCLIC CONNECTION |
| BR112015028152A2 (pt) | 2013-05-10 | 2017-07-25 | Nimbus Apollo Inc | inibidores de acc e usos dos mesmos |
| EA201591962A1 (ru) | 2013-05-10 | 2016-06-30 | Нимбус Аполло, Инк. | Ингибиторы акк и их применение |
| CN105530940A (zh) | 2013-09-12 | 2016-04-27 | 辉瑞大药厂 | 乙酰辅酶a羧化酶抑制剂用于治疗寻常痤疮的用途 |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| HK1243706A1 (zh) * | 2015-02-05 | 2018-07-20 | Dermira, Inc. | 用於制备(5-十四烷氧基)呋喃-2-甲酸2-((2-乙氧基-2-氧代乙基)(甲基)氨基)-2-氧代乙酯的合成方法 |
| US10189785B2 (en) | 2015-04-20 | 2019-01-29 | Takeda Pharmaceuticals Company Limited | Heterocyclic compound |
| HRP20201304T1 (hr) | 2015-07-27 | 2020-11-27 | Chong Kun Dang Pharmaceutical Corp. | Spoj derivata 1,3,4-oksadiazol-amida koji služi kao inhibitor histonske deacetilaze 6 i farmaceutski pripravak koji sadrži taj spoj |
| CN107980040B (zh) | 2015-07-27 | 2021-11-26 | 株式会社钟根堂 | 作为组蛋白去乙酰酶6抑制剂的1,3,4-噁二唑磺酰胺衍生物及含其的医药组合物 |
| FI3328843T3 (fi) * | 2015-07-27 | 2023-01-31 | 1,3,4-oksadiatsolisulfonamidijohdannaisyhdisteitä histonideasetylaasi-6:n inhibiittoreina ja samaa käsittävä farmaseuttinen koostumus | |
| DK3331864T3 (da) | 2015-08-04 | 2021-12-13 | Chong Kun Dang Pharmaceutical Corp | 1,3,4-Oxadiazolderivat-forbindelser som histon-deacetylase-6-hæmmer, og den farmaceutiske sammensætning omfattende disse |
| CN105130893B (zh) * | 2015-09-08 | 2018-04-10 | 大连理工大学 | 一种1‑苄基‑6‑甲氧羰甲基四氢异喹啉衍生物、制备方法及其抗血小板聚集的应用 |
| MY196174A (en) | 2015-10-12 | 2023-03-20 | Chong Kun Dang Pharmaceutical Corp | Oxadiazole Amine Derivative Compounds as Histone Deacetylase 6 Inhibitor, and the Pharmaceutical Composition Comprising the Same |
| WO2017165119A1 (en) * | 2016-03-21 | 2017-09-28 | David Weinstein | Methods for wound healing and scar prevention |
| US10653678B2 (en) | 2016-04-11 | 2020-05-19 | Genfit | Methods of treatment for cholestatic and fibrotic diseases |
| SG11201808402RA (en) | 2016-04-11 | 2018-10-30 | Genfit | Methods of treatment for cholestatic and fibrotic diseases |
| CA3041266A1 (en) | 2016-10-18 | 2018-04-26 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US11572347B2 (en) | 2017-10-20 | 2023-02-07 | The Regents Of The University Of California | Orally available sEH/PDE4 dual inhibitors |
| CA3079819C (en) | 2017-11-06 | 2023-03-14 | Acelot, Inc. | Small molecule drugs and related methods for treatment of diseases related to a.beta.42 oligomer formation |
| CN110041253B (zh) * | 2018-01-17 | 2022-03-29 | 上海翰森生物医药科技有限公司 | 吡啶类n-氧化衍生物及其制备方法和应用 |
| KR102316234B1 (ko) | 2018-07-26 | 2021-10-22 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| CN113056266A (zh) * | 2018-09-18 | 2021-06-29 | 梅塔科林公司 | 用于治疗疾病的法尼醇x受体激动剂 |
| WO2020097398A1 (en) | 2018-11-07 | 2020-05-14 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| PL3947360T3 (pl) | 2019-03-28 | 2024-11-04 | Zoetis Services Llc | Związki hamujące receptor serotoninowy 5-HT2B |
| CN109836385B (zh) * | 2019-04-04 | 2021-12-17 | 上海翰森生物医药科技有限公司 | 四氢喹啉类n-氧化衍生物及其制备方法和应用 |
| CN113874369B (zh) | 2019-05-31 | 2024-08-27 | 株式会社钟根堂 | 作为组蛋白脱乙酰酶6抑制剂的1,3,4-噁二唑高邻苯二甲酰亚胺衍生化合物及包含其的药物组合物 |
| WO2021087077A1 (en) * | 2019-10-29 | 2021-05-06 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of autophagy and histone deactylases and uses thereof |
| CA3181537A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| CN112370455A (zh) * | 2020-10-19 | 2021-02-19 | 济南大学 | 一种磺酰胺衍生物作为α-葡萄糖苷酶抑制剂及其应用 |
| EP4263531A2 (en) * | 2020-12-16 | 2023-10-25 | IFM Due, Inc. | Compounds and compositions for treating conditions associated with sting activity |
| WO2022140527A1 (en) | 2020-12-23 | 2022-06-30 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| CA3234638A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| TW202325289A (zh) | 2021-11-09 | 2023-07-01 | 美商雅捷可斯治療公司 | Jak2抑制劑之形式及組合物 |
| CN116354903B (zh) * | 2021-12-28 | 2025-09-09 | 南京药石科技股份有限公司 | 一种6-苯并噻唑磺酰氯的制备方法 |
| CN114469952B (zh) * | 2022-03-02 | 2023-09-19 | 中南大学湘雅三医院 | 特拉匹韦在制备malt1抑制剂、抗malt1依赖性肿瘤的药物中的应用及抗肿瘤药物 |
| KR20240165402A (ko) | 2022-03-23 | 2024-11-22 | 아이디어야 바이오사이언시스 인코포레이티드 | Parg의 억제제로서의 피페라진 치환된 인다졸 화합물 |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB284425A (en) | 1926-11-22 | 1928-02-02 | James Last | Improvements in and relating to sand or like moulds for making castings |
| JPS5612114B2 (enExample) | 1974-06-07 | 1981-03-18 | ||
| US4231938A (en) | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| DK149080C (da) | 1980-06-06 | 1986-07-28 | Sankyo Co | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| US4450171A (en) | 1980-08-05 | 1984-05-22 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| US4448784A (en) | 1982-04-12 | 1984-05-15 | Hoechst-Roussel Pharmaceuticals, Inc. | 1-(Aminoalkylphenyl and aminoalkylbenzyl)-indoles and indolines and analgesic method of use thereof |
| US4499289A (en) | 1982-12-03 | 1985-02-12 | G. D. Searle & Co. | Octahydronapthalenes |
| CA1327360C (en) | 1983-11-14 | 1994-03-01 | William F. Hoffman | Oxo-analogs of mevinolin-like antihypercholesterolemic agents |
| US4613610A (en) | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
| US4686237A (en) | 1984-07-24 | 1987-08-11 | Sandoz Pharmaceuticals Corp. | Erythro-(E)-7-[3'-C1-3 alkyl-1'-(3",5"-dimethylphenyl)naphth-2'-yl]-3,5-dihydroxyhept-6-enoic acids and derivatives thereof |
| US4647576A (en) | 1984-09-24 | 1987-03-03 | Warner-Lambert Company | Trans-6-[2-(substitutedpyrrol-1-yl)alkyl]-pyran-2-one inhibitors of cholesterol synthesis |
| HU198005B (en) | 1984-12-04 | 1989-07-28 | Sandoz Ag | Process for producing mevqlolakton, derivatives, its indene-analogues and pharmaceutical compositions containing them |
| US4668794A (en) | 1985-05-22 | 1987-05-26 | Sandoz Pharm. Corp. | Intermediate imidazole acrolein analogs |
| KR900001212B1 (ko) | 1985-10-25 | 1990-02-28 | 산도즈 파마슈티칼스 코오포레이숀 | 메바로노락톤 및 그것의 유도체의 헤테로사이클릭 유사체 및 그것의 생산방법 및 약학적인 그것의 용도 |
| FR2596393B1 (fr) | 1986-04-01 | 1988-06-03 | Sanofi Sa | Derives de l'acide hydroxy-3 dihydroxyoxophosphorio-4 butanoique, leur procede de preparation, leur application comme medicament et les compositions les renfermant |
| PT87539B (pt) | 1987-05-22 | 1992-09-30 | Squibb & Sons Inc | Processo para a preparacao de inibidores da reductase de hmg-coa contendo fosforo e novos intermediarios |
| US5506219A (en) | 1988-08-29 | 1996-04-09 | E. R. Squibb & Sons, Inc. | Pyridine anchors for HMG-CoA reductase inhibitors |
| US5753675A (en) | 1989-03-03 | 1998-05-19 | Novartis Pharmaceuticals Corporation | Quinoline analogs of mevalonolactone and derivatives thereof |
| HUT64023A (en) | 1991-03-22 | 1993-11-29 | Sandoz Ag | Process for producing aminoguanidine derivatives and pharmaceutical compositions comprising such compounds |
| TW225528B (enExample) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5488064A (en) | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| US5491134A (en) | 1994-09-16 | 1996-02-13 | Bristol-Myers Squibb Company | Sulfonic, phosphonic or phosphiniic acid β3 agonist derivatives |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| JP3216457B2 (ja) * | 1994-12-28 | 2001-10-09 | 富士レビオ株式会社 | アミド誘導体 |
| EP0873361B1 (en) | 1995-12-13 | 2006-11-02 | The Regents Of The University Of California | Crystals of the ligand-binding domain of the thyroid hormone receptor complexed to a ligand |
| US5770615A (en) | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| GB9713739D0 (en) | 1997-06-27 | 1997-09-03 | Karobio Ab | Thyroid receptor ligands |
| IL140622A0 (en) | 1998-07-06 | 2002-02-10 | Bristol Myers Squibb Co | Biphenyl sufonamide derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof |
| CO5150173A1 (es) | 1998-12-10 | 2002-04-29 | Novartis Ag | Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv |
| DE10139416A1 (de) * | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| TW200303742A (en) | 2001-11-21 | 2003-09-16 | Novartis Ag | Organic compounds |
| GB0215676D0 (en) | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| AU2003264038A1 (en) | 2002-08-12 | 2004-02-25 | Bristol-Myers Squibb Company | Combination pharmaceutical agents as inhibitors of hcv replication |
| MXPA05005425A (es) | 2002-11-22 | 2005-11-23 | Japan Tobacco Inc | Heterociclos que contienen nitrogeno, biciclicos, fusionados. |
| US20040185559A1 (en) | 2003-03-21 | 2004-09-23 | Isis Pharmaceuticals Inc. | Modulation of diacylglycerol acyltransferase 1 expression |
| TWI345974B (en) | 2003-07-30 | 2011-08-01 | Xenon Pharmaceuticals Inc | Pyridazine derivatives and their use in the inhibition of stearoyl-coa desaturase |
| JP2007501801A (ja) | 2003-08-07 | 2007-02-01 | 日本たばこ産業株式会社 | ピロロ[1,2−b]ピリダジン誘導体 |
| GB0325192D0 (en) | 2003-10-29 | 2003-12-03 | Astrazeneca Ab | Method of use |
| WO2005108370A1 (ja) * | 2004-04-16 | 2005-11-17 | Ajinomoto Co., Inc. | ベンゼン化合物 |
| WO2006018662A2 (en) * | 2004-08-16 | 2006-02-23 | Prosidion Limited | Aryl urea derivatives for treating obesity |
| 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 |
| JPWO2007119833A1 (ja) * | 2006-04-14 | 2009-08-27 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| US20090197916A1 (en) | 2007-01-29 | 2009-08-06 | Arete Therapeutics, Inc | Soluble epoxide hydrolase inhibitors for treatment of metabolic syndrome and related disorders |
| US20090005375A1 (en) * | 2007-03-30 | 2009-01-01 | Edcon Chang | Acetyl coenzyme a carboxylase inhibitors |
| PE20091309A1 (es) | 2007-12-21 | 2009-09-30 | Astrazeneca Ab | Derivados de ciclohexilo como inhibidores de acetil coenzima a carboxilasa |
| JP2009173567A (ja) * | 2008-01-23 | 2009-08-06 | Lion Corp | Ppar抑制剤並びに骨形成促進剤及び骨粗鬆症の治療薬 |
| WO2010065800A1 (en) | 2008-12-04 | 2010-06-10 | Palatin Technologies, Inc. | Hydrazine substituted piperidine melanocortin receptor-specific compounds |
| WO2010065802A2 (en) | 2008-12-04 | 2010-06-10 | Palatin Technologies, Inc. | Substituted pyrrolidine or imidazolidine melanocortin receptor-specific compounds |
| WO2010065799A2 (en) | 2008-12-04 | 2010-06-10 | Palatin Technologies, Inc. | Amine substituted piperidine melanocortin receptor-specific compounds |
| WO2010065801A1 (en) | 2008-12-04 | 2010-06-10 | Palatin Technologies, Inc. | Amine substituted piperazine melanocortin receptor-specific compounds |
| WO2010107040A1 (ja) | 2009-03-19 | 2010-09-23 | 塩野義製薬株式会社 | Npyy5受容体拮抗剤を含有する固形製剤 |
| US20120202814A1 (en) | 2009-10-02 | 2012-08-09 | Università Degli Studi Di Siena | Compounds with ddx3 inhibitory activity and uses thereof |
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| UY33536A (es) | 2012-02-29 |
| JP2013533279A (ja) | 2013-08-22 |
| CN103339111A (zh) | 2013-10-02 |
| ES2641833T3 (es) | 2017-11-14 |
| JP5998133B2 (ja) | 2016-09-28 |
| EP2598486A1 (en) | 2013-06-05 |
| WO2012013716A1 (en) | 2012-02-02 |
| EP2598486B1 (en) | 2017-06-28 |
| AR082391A1 (es) | 2012-12-05 |
| US20140171363A1 (en) | 2014-06-19 |
| US20120028969A1 (en) | 2012-02-02 |
| US8697739B2 (en) | 2014-04-15 |
| US9789118B2 (en) | 2017-10-17 |
| CN103339111B (zh) | 2015-12-16 |
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