TW202031641A - 經取代之異吲哚啉酮 - Google Patents
經取代之異吲哚啉酮 Download PDFInfo
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- TW202031641A TW202031641A TW108141261A TW108141261A TW202031641A TW 202031641 A TW202031641 A TW 202031641A TW 108141261 A TW108141261 A TW 108141261A TW 108141261 A TW108141261 A TW 108141261A TW 202031641 A TW202031641 A TW 202031641A
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
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- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| TW202140441A (zh) | 2020-03-23 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 經取代之側氧基異吲哚啉化合物 |
| WO2022061348A1 (en) | 2020-09-16 | 2022-03-24 | Biotheryx, Inc. | Sos1 protein degraders, pharmaceutical compositions thereof, and their therapeutic applications |
| TW202231269A (zh) | 2020-10-23 | 2022-08-16 | 美商拜歐斯瑞克斯公司 | Kras蛋白降解劑、其醫藥組合物及其治療應用 |
| AU2021402911A1 (en) | 2020-12-14 | 2023-07-06 | Biotheryx, Inc. | Pde4 degraders, pharmaceutical compositions, and therapeutic applications |
| JP2024504932A (ja) | 2021-01-13 | 2024-02-02 | モンテ ローザ セラピューティクス， インコーポレイテッド | イソインドリノン化合物 |
| PT4320112T (pt) * | 2021-04-06 | 2025-07-07 | Bristol Myers Squibb Co | Compostos de oxoisoindolina substituídos por piridinilo |
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Family Cites Families (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| US20010056114A1 (en) | 2000-11-01 | 2001-12-27 | D'amato Robert | Methods for the inhibition of angiogenesis with 3-amino thalidomide |
| US6228879B1 (en) | 1997-10-16 | 2001-05-08 | The Children's Medical Center | Methods and compositions for inhibition of angiogenesis |
| HU228769B1 (en) | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
| DE69734290T2 (de) | 1996-11-05 | 2006-07-06 | The Children's Medical Center Corp., Boston | Mittel zur hemmung von angiogenese enthaltend thalodomid und einen nsaid |
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| US5874448A (en) | 1997-11-18 | 1999-02-23 | Celgene Corporation | Substituted 2-(2,6 dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing TNFα levels |
| US5955476A (en) | 1997-11-18 | 1999-09-21 | Celgene Corporation | Substituted 2-(2,6-dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing inflammatory cytokine levels |
| US20010006973A1 (en) | 1998-03-16 | 2001-07-05 | Hon-Wah Man | 1-oxo- and 1,3-dioxoisoindolines and method of reducing inflammatory cytokine levels |
| JP2000159761A (ja) | 1998-11-30 | 2000-06-13 | Yoshio Takeuchi | フルオロサリドマイド |
| US7629360B2 (en) | 1999-05-07 | 2009-12-08 | Celgene Corporation | Methods for the treatment of cachexia and graft v. host disease |
| US6388090B2 (en) | 2000-01-14 | 2002-05-14 | Orion Corporation | Imidazole derivatives |
| US6458810B1 (en) | 2000-11-14 | 2002-10-01 | George Muller | Pharmaceutically active isoindoline derivatives |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US7091353B2 (en) * | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| ES2172474B1 (es) | 2001-03-01 | 2004-01-16 | Fundacion Universitaria San Pa | Derivados de glutarimida como agentes terapeuticos. |
| NZ531294A (en) | 2001-08-06 | 2005-11-25 | Childrens Medical Center | Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs |
| TWI298724B (en) | 2001-11-15 | 2008-07-11 | Celgene Corp | Pharmaceutically active isoindoline derivatives |
| EP1336602A1 (en) | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
| US7323479B2 (en) | 2002-05-17 | 2008-01-29 | Celgene Corporation | Methods for treatment and management of brain cancer using 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-methylisoindoline |
| CN1164586C (zh) | 2002-10-28 | 2004-09-01 | 中国科学院长春应用化学研究所 | 沙利度胺及其衍生物的制备方法 |
| EP2258365B1 (en) | 2003-03-28 | 2013-05-29 | Novartis Vaccines and Diagnostics, Inc. | Use of organic compounds for immunopotentiation |
| CH696542A5 (de) | 2003-07-09 | 2007-07-31 | Siegfried Ltd | Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen. |
| 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 |
| WO2005028436A2 (en) | 2003-09-17 | 2005-03-31 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Thalidomide analogs as tnf-alpha modulators |
| US7612096B2 (en) | 2003-10-23 | 2009-11-03 | Celgene Corporation | Methods for treatment, modification and management of radiculopathy using 1-oxo-2-(2,6-dioxopiperidin-3yl)-4-aminoisoindoline |
| MXPA06010699A (es) | 2004-03-22 | 2006-12-15 | Celgene Corp | Metodos de usos y composiciones que contienen compuestos inmunomoduladores para el tratamiento y manejo de enfermedades o alteraciones de la piel. |
| JP2005336157A (ja) | 2004-04-30 | 2005-12-08 | Arigen Inc | 光学活性サリドマイドおよびその誘導体の製造法 |
| ES2437592T3 (es) | 2004-09-03 | 2014-01-13 | Celgene Corporation | Procedimientos para la preparación de 2-(2,6-dioxopiperidin-3-il)-1-oxoisoindolinas sustituidas |
| ZA200704784B (en) | 2004-11-12 | 2008-10-29 | Celgene Corp | Methods and compositions using immunomodulatory compounds for treatment and management of parasitic diseases |
| KR20070108909A (ko) | 2005-02-18 | 2007-11-13 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 알데스류킨과 함께 사용하는 항혈관형성제 |
| CN100383139C (zh) | 2005-04-07 | 2008-04-23 | 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哌啶-2，6-二酮衍生物 |
| US20060270707A1 (en) * | 2005-05-24 | 2006-11-30 | Zeldis Jerome B | Methods and compositions using 4-[(cyclopropanecarbonylamino)methyl]-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione for the treatment or prevention of cutaneous lupus |
| ES2434946T3 (es) * | 2005-08-31 | 2013-12-18 | Celgene Corporation | Compuestos de isoindol imida y composiciones que los comprenden y métodos para usarlo |
| AU2006332680A1 (en) | 2005-12-29 | 2007-07-12 | Anthrogenesis Corporation | Improved composition for collecting and preserving placental stem cells and methods of using the composition |
| US20080064876A1 (en) | 2006-05-16 | 2008-03-13 | Muller George W | Process for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione |
| NZ575061A (en) * | 2006-08-30 | 2011-10-28 | Celgene Corp | 5-substituted isoindoline compounds |
| JP2009001528A (ja) | 2007-06-22 | 2009-01-08 | Nagoya Institute Of Technology | ５’−ヒドロキシサリドマイド誘導体及びその製造方法 |
| US20090155207A1 (en) | 2007-11-29 | 2009-06-18 | Hariri Robert J | Use of Immunomodulatory Compounds for the Treatment of Transverse Myelitis, Multiple Sclerosis, and Other Disorders |
| US7964354B2 (en) | 2007-12-20 | 2011-06-21 | Celgene Corporation | Use of micro-RNA as a biomarker of immunomodulatory drug activity |
| US20100098657A1 (en) | 2007-12-27 | 2010-04-22 | Schafer Peter H | Method of Treating Cancer with Immunomodulatory Compounds and IgG |
| US20090171093A1 (en) | 2007-12-28 | 2009-07-02 | Yoshio Takeuchi | 3'-Fluoro-5'-hydroxythalidomide and derivatives thereof |
| US20090232796A1 (en) | 2008-02-20 | 2009-09-17 | Corral Laura G | Method of treating cancer by administering an immunomodulatory compound in combination with a cd40 antibody or cd40 ligand |
| JP2009215195A (ja) | 2008-03-10 | 2009-09-24 | Nagoya Institute Of Technology | ５’−フルオロサリドマイド誘導体及びその製造方法 |
| JP5561577B2 (ja) | 2009-07-01 | 2014-07-30 | 国立大学法人 名古屋工業大学 | 光学活性３’−フルオロサリドマイド誘導体の製造方法 |
| US9217743B2 (en) | 2009-10-20 | 2015-12-22 | Tokyo Institute Of Technology | Screening method utilizing thalidomide-targeting factor |
| ES2664872T3 (es) | 2010-06-18 | 2018-04-23 | Taiho Pharmaceutical Co., Ltd | Moduladores PRPK-TPRKB y sus usos |
| WO2012027065A2 (en) | 2010-08-27 | 2012-03-01 | Celgene Corporation | Combination therapy for treatment of disease |
| AU2012236655B2 (en) | 2011-03-28 | 2016-09-22 | Deuterx, Llc, | 2',6'-dioxo-3'-deutero-piperdin-3-yl-isoindoline compounds |
| US8927725B2 (en) | 2011-12-02 | 2015-01-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thio compounds |
| WO2014180882A2 (en) | 2013-05-07 | 2014-11-13 | Universitat De Barcelona | Treatment of brain metastasis from cancer |
| WO2015107196A1 (en) | 2014-01-20 | 2015-07-23 | Institut Curie | Use of thalidomide or analogs thereof for preventing neurologic disorders induced by brain irradiation |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| US9931332B2 (en) | 2014-07-30 | 2018-04-03 | University Of Southern California | Compositions and methods for treating primary effusion lymphoma |
| ES2901509T3 (es) * | 2014-10-30 | 2022-03-22 | Kangpu Biopharmaceuticals Ltd | Derivado de isoindolina, compuesto intermedio, métodos de preparación, composición farmacéutica y uso del mismo |
| JP6815318B2 (ja) | 2014-12-23 | 2021-01-20 | ダナ−ファーバー キャンサー インスティテュート，インコーポレイテッド | 二官能性分子によって標的化タンパク質分解を誘導する方法 |
| US9694084B2 (en) | 2014-12-23 | 2017-07-04 | Dana-Farber Cancer Institute, Inc. | Methods to induce targeted protein degradation through bifunctional molecules |
| WO2016191178A1 (en) * | 2015-05-22 | 2016-12-01 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| WO2017007612A1 (en) | 2015-07-07 | 2017-01-12 | Dana-Farber Cancer Institute, Inc. | Methods to induce targeted protein degradation through bifunctional molecules |
| AU2016301196B2 (en) | 2015-08-06 | 2022-09-08 | Dana-Farber Cancer Institute, Inc. | Tunable endogenous protein degradation |
| WO2017024317A2 (en) | 2015-08-06 | 2017-02-09 | Dana-Farber Cancer Institute, Inc. | Methods to induce targeted protein degradation through bifunctional molecules |
| WO2017117473A1 (en) | 2015-12-30 | 2017-07-06 | Dana-Farber Cancer Institute, Inc. | Bifunctional molescules for her3 degradation and methods of use |
| WO2017117474A1 (en) | 2015-12-30 | 2017-07-06 | Dana-Farber Cancer Institute, Inc. | Bifunctional compounds for her3 degradation and methods of use |
| CA3017740A1 (en) | 2016-03-16 | 2017-09-21 | Pearlie BURNETTE | Small molecules against cereblon to enhance effector t cell function |
| AU2017246453A1 (en) | 2016-04-06 | 2018-11-08 | The Regents Of The University Of Michigan | Monofunctional intermediates for ligand-dependent target protein degradation |
| JP7037500B2 (ja) | 2016-04-06 | 2022-03-16 | ザ リージェンツ オブ ザ ユニヴァシティ オブ ミシガン | Ｍｄｍ２タンパク質分解剤 |
| US10696635B2 (en) | 2016-04-18 | 2020-06-30 | The Scripps Research Institute | Versatile ligand for palladium-catalyzed meta-C—H functionalizations of aromatic substrates |
| WO2017185031A1 (en) | 2016-04-22 | 2017-10-26 | Dana-Farber Cancer Institute, Inc. | Degradation of cyclin-dependent kinase 4/6 (cdk4/6) by conjugation of cdk4/6 inhibitors with e3 ligase ligand and methods of use |
| EP3892272B1 (en) | 2016-04-22 | 2024-07-24 | Dana-Farber Cancer Institute, Inc. | Bifunctional molecules for degradation of egfr and methods of use |
| AU2017254702B2 (en) | 2016-04-22 | 2020-12-24 | Dana-Farber Cancer Institute, Inc. | Degradation of cyclin-dependent kinase 9 (CDK9) by conjugation of CDK9 inhibitors with E3 ligase ligand and methods of use |
| JP6921114B2 (ja) | 2016-04-22 | 2021-08-18 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | サイクリン依存性キナーゼ８（ｃｄｋ８）阻害剤のｅ３リガーゼリガンドとのコンジュゲーションによるｃｄｋ８の分解および使用法 |
| EP3455219A4 (en) * | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| WO2017197056A1 (en) * | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Bromodomain targeting degronimers for target protein degradation |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| WO2017201069A1 (en) * | 2016-05-18 | 2017-11-23 | Biotheryx, Inc. | Oxoindoline derivatives as protein function modulators |
| CA3025805A1 (en) | 2016-06-23 | 2017-12-28 | James Bradner | Degradation of tripartite motif-containing protein 24 (trim24) by conjugation of trim24 inhibitors with e3 ligase ligand and methods of use |
| CA3025806C (en) | 2016-06-23 | 2023-04-04 | Dana-Farber Cancer Institute, Inc. | Degradation of bromodomain-containing protein 9 (brd9) by conjugation of brd9 inhibitors with e3 ligase ligand and methods of use |
| US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
| ES2857743T3 (es) * | 2016-09-13 | 2021-09-29 | Univ Michigan Regents | 1,4-diazepinas fusionadas como degradadores de proteína BET |
| CN110062759B (zh) | 2016-09-13 | 2022-05-24 | 密执安大学评议会 | 作为bet蛋白降解剂的稠合的1,4-氧氮杂䓬 |
| WO2018064589A1 (en) | 2016-09-29 | 2018-04-05 | Dana-Farber Cancer Institute, Inc. | Targeted protein degradation using a mutant e3 ubiquitin ligase |
| LT3660004T (lt) * | 2016-10-11 | 2023-06-12 | Arvinas Operations, Inc. | Junginiai ir metodai, skirti tikslinei androgeno receptoriaus degradacijai |
| CN107056772A (zh) | 2017-01-23 | 2017-08-18 | 中国药科大学 | 基于cereblon配体诱导BET降解的双功能分子及其制备和应用 |
| CN107698575A (zh) | 2017-09-26 | 2018-02-16 | 中国药科大学 | cereblon配体介导的新型BET蛋白降解的双功能分子及其制备和应用 |
| CN107739389B (zh) | 2017-11-03 | 2020-03-31 | 华东师范大学 | 3位取代的(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮类化合物及其合成方法 |
| WO2019173224A1 (en) * | 2018-03-05 | 2019-09-12 | Biotheryx, Inc. | Deuterated compounds and chimeras and uses thereof |
| CA3106239A1 (en) * | 2018-07-27 | 2020-01-30 | Biotheryx, Inc. | Bifunctional compounds as cdk modulators |
| CN113423701A (zh) * | 2018-11-13 | 2021-09-21 | 拜欧斯瑞克斯公司 | 取代的异吲哚啉酮 |
| US20230045737A1 (en) | 2018-12-05 | 2023-02-09 | Vividion Therapeutics, Inc. | Substituted isoindolinones as modulators of cereblon-mediated neo-substrate recruitment |
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| CA3119343C (en) | 2024-01-16 |
| EP3880669A1 (en) | 2021-09-22 |
| CN113423701A (zh) | 2021-09-21 |
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