TW201835089A - 靶向蛋白質之化合物、組合物、方法及其用途 - Google Patents
靶向蛋白質之化合物、組合物、方法及其用途 Download PDFInfo
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2990061T3 (es) | 2016-05-10 | 2024-11-28 | C4 Therapeutics Inc | Degronímeros espirocíclicos para la degradación de proteínas diana |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3641762A4 (en) | 2017-06-20 | 2021-03-10 | C4 Therapeutics, Inc. | N / O-LINKED DEGRONES AND DEGRONIMERS FOR PROTEIN DEGRADATION |
| WO2019043214A1 (en) | 2017-09-04 | 2019-03-07 | F. Hoffmann-La Roche Ag | glutarimide |
| CN111315735B (zh) | 2017-09-04 | 2024-03-08 | C4医药公司 | 二氢苯并咪唑酮 |
| CN111278816B (zh) | 2017-09-04 | 2024-03-15 | C4医药公司 | 二氢喹啉酮 |
| CN111372585A (zh) | 2017-11-16 | 2020-07-03 | C4医药公司 | 用于靶蛋白降解的降解剂和降解决定子 |
| JP2021519337A (ja) | 2018-03-26 | 2021-08-10 | シー4 セラピューティクス, インコーポレイテッド | Ikarosの分解のためのセレブロン結合剤 |
| WO2019191451A1 (en) * | 2018-03-30 | 2019-10-03 | Biotheryx, Inc. | Thienopyrimidinone compounds |
| CN119751456A (zh) | 2018-04-16 | 2025-04-04 | C4医药公司 | 螺环化合物 |
| EP3578561A1 (en) | 2018-06-04 | 2019-12-11 | F. Hoffmann-La Roche AG | Spiro compounds |
| US11191769B2 (en) * | 2018-06-13 | 2021-12-07 | Biotheryx, Inc. | Fused thiophene compounds |
| US11969472B2 (en) | 2018-08-22 | 2024-04-30 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (TRK) degradation compounds and methods of use |
| AU2019323446B2 (en) | 2018-08-22 | 2025-01-30 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (TRK) degradation compounds and methods of use |
| WO2020132561A1 (en) | 2018-12-20 | 2020-06-25 | C4 Therapeutics, Inc. | Targeted protein degradation |
| CN113874016A (zh) | 2019-01-29 | 2021-12-31 | 福宏治疗公司 | 化合物及其用途 |
| FR3092581A1 (fr) * | 2019-02-12 | 2020-08-14 | Impact Biomedicines, Inc | Formes cristallines d'un inhibiteur de jak2 |
| EA202192738A1 (ru) | 2019-04-12 | 2022-03-17 | С4 Терапьютикс, Инк. | Трициклические соединения, обеспечивающие разрушение белка ikaros и белка aiolos |
| CN114502543A (zh) | 2019-05-24 | 2022-05-13 | 拜欧斯瑞克斯公司 | 靶向蛋白化合物、其药物组合物及治疗应用 |
| KR20220103753A (ko) | 2019-11-19 | 2022-07-22 | 브리스톨-마이어스 스큅 컴퍼니 | 헬리오스 단백질의 억제제로서 유용한 화합물 |
| IL293999B1 (en) | 2019-12-20 | 2025-10-01 | C4 Therapeutics Inc | Isoindolinone compounds with a phenylaminoglutarimide residue for degradation of EGFR |
| EP4096651A4 (en) | 2020-01-29 | 2024-01-24 | Foghorn Therapeutics Inc. | COMPOUNDS AND THEIR USES |
| WO2023205701A1 (en) | 2022-04-20 | 2023-10-26 | Kumquat Biosciences Inc. | Macrocyclic heterocycles and uses thereof |
| CA3173262A1 (en) | 2020-02-26 | 2021-09-02 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (trk) degradation compounds and methods of use |
| CA3165309A1 (en) | 2020-03-05 | 2021-09-10 | Christopher G. Nasveschuk | Compounds for targeted degradation of brd9 |
| US11787800B2 (en) | 2020-07-29 | 2023-10-17 | Foghorn Therapeutics Inc. | BRD9 degraders and uses thereof |
| US20240025863A1 (en) | 2020-09-16 | 2024-01-25 | Biotheryx, Inc. | Sos1 protein degraders, pharmaceutical compositions thereof, and their therapeutic applications |
| WO2022072538A1 (en) * | 2020-09-30 | 2022-04-07 | Biotheryx, Inc. | Antibody-drug conjugates, pharmaceutical compositions thereof, and their therapeutic applications |
| US20240050428A1 (en) * | 2020-10-07 | 2024-02-15 | Cullgen (Shanghai), Inc. | Compounds and methods of treating cancers |
| WO2022087335A1 (en) | 2020-10-23 | 2022-04-28 | Biotheryx, Inc. | Kras protein degraders, pharmaceutical compositions thereof, and their therapeutic applications |
| AU2021402911A1 (en) | 2020-12-14 | 2023-07-06 | Biotheryx, Inc. | Pde4 degraders, pharmaceutical compositions, and therapeutic applications |
| EP4277901A1 (en) | 2021-01-13 | 2023-11-22 | Monte Rosa Therapeutics, Inc. | Isoindolinone compounds |
| WO2022216644A1 (en) | 2021-04-06 | 2022-10-13 | Bristol-Myers Squibb Company | Pyridinyl substituted oxoisoindoline compounds |
| IL308314A (en) | 2021-05-07 | 2024-01-01 | Kymera Therapeutics Inc | CDK2 compounds and their uses |
| CN117940133A (zh) | 2021-06-08 | 2024-04-26 | C4医药公司 | 用于突变braf的降解的治疗剂 |
| US11767330B2 (en) | 2021-07-06 | 2023-09-26 | Foghorn Therapeutics Inc. | Citrate salt, pharmaceutical compositions, and methods of making and using the same |
| US12419962B2 (en) | 2022-03-16 | 2025-09-23 | Biotheryx, Inc. | Quinazolines, pharmaceutical compositions, and therapeutic applications |
| AU2023283735A1 (en) | 2022-06-06 | 2024-10-31 | C4 Therapeutics, Inc. | Bicyclic-substituted glutarimide cereblon binders |
| CA3267079A1 (en) * | 2022-09-09 | 2024-03-14 | Innovo Therapeutics, Inc. | CK1α AND DOUBLE CK1α/GSPT1 DEGRADATION COMPOUNDS |
| WO2024096753A1 (en) | 2022-11-02 | 2024-05-10 | Captor Therapeutics S.A. | Nek7 degraders and methods of use thereof |
| AU2024276994A1 (en) | 2023-05-24 | 2025-10-23 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| TW202502779A (zh) | 2023-06-30 | 2025-01-16 | 美商金橘生物科技公司 | 取代的雜芳族胺及其用途 |
| WO2025096855A1 (en) | 2023-11-02 | 2025-05-08 | Kumquat Biosciences Inc. | Degraders and uses thereof |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5153192A (en) | 1990-04-09 | 1992-10-06 | Alcon Laboratories, Inc. | Thiophene sulfonamides useful as carbonic anhydrase inhibitors |
| US5585377A (en) | 1990-04-09 | 1996-12-17 | Alcon Laboratories, Inc. | Sulfonamides useful as carbonic anhydrase inhibitors |
| US5378703A (en) | 1990-04-09 | 1995-01-03 | Alcon Laboratories, Inc. | Sulfonamides useful as carbonic anhydrase inhibitors |
| DE4023048A1 (de) | 1990-07-20 | 1992-01-23 | Basf Ag | Dicarbonsaeureimide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| AU677577B2 (en) | 1992-02-21 | 1997-05-01 | Alcon Laboratories, Inc. | Topical antiglaucoma compositions comprising carbonic anhydrase inhibitors and beta-blockers |
| US5420923A (en) | 1993-02-16 | 1995-05-30 | Scientific-Atlanta, Inc. | Addressed messaging in a cable television system |
| US5334596A (en) | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5698579A (en) | 1993-07-02 | 1997-12-16 | Celgene Corporation | Cyclic amides |
| US5605914A (en) | 1993-07-02 | 1997-02-25 | Celgene Corporation | Imides |
| US5463063A (en) | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
| US5750471A (en) | 1994-06-08 | 1998-05-12 | E. I. Du Pont De Nemours And Company | Cyclic sulfonamide herbicides |
| EP0785939A1 (en) | 1994-10-11 | 1997-07-30 | Takeda Chemical Industries, Ltd. | Substituted heterobicyclic alkyl amines and their use as squalene oxide cyclase inhibitors |
| BR9707674A (pt) | 1996-02-26 | 2000-01-04 | Advanced Res & Tech Inst | Uso de inibidores de anidrase carbÈnico para tratamento de edema macular. |
| ZA98371B (en) | 1997-01-31 | 1999-07-16 | Du Pont | Genetically transformed plants demonstrating resistance to porphyrinogen biosynthesis-inhibiting herbicides. |
| JPH10264532A (ja) | 1997-03-24 | 1998-10-06 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| US6906245B1 (en) | 1998-04-30 | 2005-06-14 | Sumitomo Chemical Company, Limited | Method for producing transgenic plants resistant to weed control compounds which disrupt the porphyrin pathways of plants |
| AU753020B2 (en) | 1998-04-30 | 2002-10-03 | Sumitomo Chemical Company, Limited | Method for giving resistance to weed control compounds to plants |
| JP2000159761A (ja) | 1998-11-30 | 2000-06-13 | Yoshio Takeuchi | フルオロサリドマイド |
| US6492380B1 (en) | 1999-05-17 | 2002-12-10 | Queen's University At Kingston | Method of inhibiting neurotrophin-receptor binding |
| US6468990B1 (en) | 1999-05-17 | 2002-10-22 | Queen's University At Kingston | Method of inhibiting binding of nerve growth factor to p75 NTR receptor |
| JP4821038B2 (ja) | 1999-10-29 | 2011-11-24 | 住友化学株式会社 | 除草剤耐性植物 |
| JP4821036B2 (ja) | 1999-10-29 | 2011-11-24 | 住友化学株式会社 | 除草剤耐性植物 |
| US7091353B2 (en) * | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| DE10133665A1 (de) | 2001-07-11 | 2003-01-30 | Boehringer Ingelheim Pharma | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| JP2004018434A (ja) | 2002-06-14 | 2004-01-22 | Mitsui Chemicals Inc | 新規なフッ素化イミド化合物、および該化合物を用いた電子写真感光体、電子写真装置、有機電界発光素子 |
| AU2003293914B2 (en) | 2002-12-23 | 2010-09-23 | Panoptes Pharma Ges.M.B.H. | Aromatic compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| US7247736B2 (en) | 2002-12-23 | 2007-07-24 | 4Sc Ag | Method of identifying inhibitors of DHODH |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| CN100398534C (zh) | 2003-09-15 | 2008-07-02 | 天津和美生物技术有限公司 | 合成酞胺哌啶酮及其衍生物的方法 |
| SE0400970D0 (sv) | 2004-04-14 | 2004-04-14 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| WO2006058088A2 (en) | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| CN1939922B (zh) * | 2005-09-27 | 2010-10-13 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3,4-c]吡咯-4,6-二酮衍生物 |
| US8877780B2 (en) * | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| PL2061765T3 (pl) | 2006-09-01 | 2015-04-30 | Senhwa Biosciences Inc | Modulatory białkowych kinaz serynowo-treoninowych i PARP |
| WO2008045529A1 (en) | 2006-10-12 | 2008-04-17 | Serenex, Inc. | Purine and pyrimidine derivatives for treatment of cancer and inflammatory diseases |
| CN101186612B (zh) * | 2006-11-15 | 2012-10-03 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的吡咯啉衍生物及其制备和应用 |
| CN101186611B (zh) * | 2006-11-15 | 2011-05-18 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的吡咯啉-2-酮衍生物及其制备和应用 |
| EP1975165A1 (de) | 2007-03-27 | 2008-10-01 | Boehringer Ingelheim Pharma GmbH & Co. KG | Substituierte Pyrrolidinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| JP2008273924A (ja) | 2007-03-30 | 2008-11-13 | Meiji Seika Kaisha Ltd | 2位チエニルカルバペネム誘導体 |
| KR101128943B1 (ko) | 2007-04-13 | 2012-03-27 | 주식회사 엘지화학 | 디옥시피롤기를 포함하는 헤테로고리 화합물 및 이를이용한 유기 전자 소자 |
| EP2346860B1 (en) | 2008-10-08 | 2012-09-19 | Bristol-Myers Squibb Company | Pyrrolone melanin concentrating hormone receptor-1 antagonists |
| US20120028985A1 (en) | 2008-11-07 | 2012-02-02 | 4Sc Ag | Combinational therapy for treating autoimmune disease |
| JP5651681B2 (ja) | 2009-04-03 | 2015-01-14 | 大日本住友製薬株式会社 | 代謝型グルタミン酸受容体5介在障害の治療のための化合物、およびその使用方法 |
| US8975260B2 (en) | 2010-09-01 | 2015-03-10 | Genetech, Inc | Pyridazinones, method of making, and method of use thereof |
| US20120085992A1 (en) | 2010-09-30 | 2012-04-12 | The Regents Of The University Of California | Furan Conjugated Polymers Useful for Photovoltaic Applications |
| WO2012082893A2 (en) | 2010-12-15 | 2012-06-21 | Plextronics, Inc. | Fluoro monomers, oligomers, and polymers for inks and organic electronic devices |
| CN103889985A (zh) | 2011-04-15 | 2014-06-25 | 乔治亚州技术研究公司 | 作为有机半导体的萘-二酰亚胺-杂环-萘二酰亚胺低聚物以及自其产生的晶体管 |
| ITMI20110881A1 (it) | 2011-05-18 | 2012-11-19 | E T C Srl | Materiale semiconduttore organico |
| WO2013052153A1 (en) | 2011-10-05 | 2013-04-11 | Georgia Tech Research Corporation | Blends of organic semiconductor compounds and electrically insulating amorphous polymers, methods and devices |
| JP2014047192A (ja) | 2012-09-03 | 2014-03-17 | Sumitomo Chemical Co Ltd | 化合物、並びに、該化合物を含有する有機半導体材料、有機半導体素子 |
| JP2014047196A (ja) | 2012-09-03 | 2014-03-17 | Sumitomo Chemical Co Ltd | 化合物及び高分子化合物、並びに、該化合物又は該高分子化合物を含有する有機半導体材料及び該有機半導体材料を用いた有機半導体素子 |
| CN103664916B (zh) | 2012-09-12 | 2016-08-24 | 中国科学院化学研究所 | 基于联噻吩亚二吡咯及其衍生物的共轭小分子材料及其制备方法与应用 |
| ITMI20121691A1 (it) | 2012-10-09 | 2014-04-10 | E T C Srl | Materiale semiconduttore organico |
| ITMI20121939A1 (it) | 2012-11-15 | 2014-05-16 | E T C Srl | Materiale organico semiconduttore |
| ITMI20121952A1 (it) | 2012-11-16 | 2014-05-17 | E T C Srl | Materiale semiconduttore organico |
| WO2014089324A1 (en) | 2012-12-07 | 2014-06-12 | Calitor Sciences, Llc | Substituted cyclic compounds and methods of use |
| JP2014185147A (ja) | 2013-02-22 | 2014-10-02 | Mitsubishi Chemicals Corp | イミド縮合環化合物及びイミド縮合環化合物の製造方法 |
| JP6248400B2 (ja) | 2013-03-15 | 2017-12-20 | 株式会社リコー | 感光体及び画像形成装置 |
| JP2015013989A (ja) | 2013-06-05 | 2015-01-22 | 三菱化学株式会社 | コポリマー、半導体層形成用組成物、有機電子デバイス及び太陽電池モジュール |
| WO2014204082A1 (ko) | 2013-06-20 | 2014-12-24 | 경상대학교산학협력단 | 유기 반도체 화합물, 이의 제조방법 및 이를 채용한 유기 태양전지 |
| KR101595919B1 (ko) | 2013-08-30 | 2016-02-29 | 한국과학기술연구원 | 전도성 유기 반도체 화합물 및 이를 포함하는 유기태양전지 |
| WO2015038671A2 (en) | 2013-09-10 | 2015-03-19 | University Of Washington | Non-fullerene electron acceptors for organic photovoltaic devices |
| KR101732220B1 (ko) | 2014-03-31 | 2017-05-02 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 태양 전지 |
| CN105294536B (zh) | 2014-06-30 | 2018-06-29 | 中国科学院上海有机化学研究所 | 一种制备3-亚氨基异吲哚啉酮类化合物的方法 |
| HRP20230265T1 (hr) * | 2014-08-22 | 2023-04-14 | Celgene Corporation | Postupci liječenja multiplog mijeloma imunomodulatornim spojevima u kombinaciji s protutijelima |
| CN104230953B (zh) | 2014-08-25 | 2016-08-17 | 中国科学院上海有机化学研究所 | 含2-(1,3-二硫/硒-2-亚基)乙氰共轭结构单元的萘二酰亚胺及其衍生物 |
| WO2016061751A1 (en) | 2014-10-22 | 2016-04-28 | Merck Sharp & Dohme Corp. | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
| CN105693745B (zh) | 2014-11-27 | 2019-07-05 | 中国科学院苏州纳米技术与纳米仿生研究所 | 有机π-共轭化合物、其制备方法及应用 |
| JP6629885B2 (ja) * | 2015-05-22 | 2020-01-15 | バイオセリックス, インコーポレイテッド | タンパク質を標的とする化合物、その組成物、方法、および使用 |
| CN110099907A (zh) * | 2016-12-21 | 2019-08-06 | 拜欧赛里克斯公司 | 靶向蛋白质的噻吩并吡咯衍生物、组合物、方法及其用途 |
-
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- 2017-12-19 JP JP2019526486A patent/JP2020504711A/ja active Pending
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2018
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2021
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI756957B (zh) * | 2016-12-21 | 2022-03-01 | 美商拜歐斯瑞克斯公司 | 靶向蛋白質之化合物、組合物、方法及其用途 |
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| RU2771166C2 (ru) | 2022-04-27 |
| KR20190093205A (ko) | 2019-08-08 |
| ZA201903479B (en) | 2021-09-29 |
| MX387646B (es) | 2025-03-18 |
| US20180170948A1 (en) | 2018-06-21 |
| RU2019115392A3 (enExample) | 2021-05-14 |
| CN110099907A (zh) | 2019-08-06 |
| US10889593B2 (en) | 2021-01-12 |
| US20190322683A1 (en) | 2019-10-24 |
| US20180298027A1 (en) | 2018-10-18 |
| EP3559005A1 (en) | 2019-10-30 |
| RU2019115392A (ru) | 2021-01-22 |
| WO2018118947A1 (en) | 2018-06-28 |
| US10040804B2 (en) | 2018-08-07 |
| US11345714B2 (en) | 2022-05-31 |
| TWI756957B (zh) | 2022-03-01 |
| CA3043938A1 (en) | 2018-06-28 |
| US20210139500A1 (en) | 2021-05-13 |
| MX2019007434A (es) | 2019-08-16 |
| TW202120514A (zh) | 2021-06-01 |
| US10336771B2 (en) | 2019-07-02 |
| AU2017382176A1 (en) | 2019-05-30 |
| IL267323A (en) | 2019-08-29 |
| JP2020504711A (ja) | 2020-02-13 |
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