AU2014223547B2 - A benzoic acid derivative MDM2 inhibitor for the treatment of cancer - Google Patents
A benzoic acid derivative MDM2 inhibitor for the treatment of cancer Download PDFInfo
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- AU2014223547B2 AU2014223547B2 AU2014223547A AU2014223547A AU2014223547B2 AU 2014223547 B2 AU2014223547 B2 AU 2014223547B2 AU 2014223547 A AU2014223547 A AU 2014223547A AU 2014223547 A AU2014223547 A AU 2014223547A AU 2014223547 B2 AU2014223547 B2 AU 2014223547B2
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US201361770901P | 2013-02-28 | 2013-02-28 | |
| US61/770,901 | 2013-02-28 | ||
| PCT/US2014/018759 WO2014134201A1 (en) | 2013-02-28 | 2014-02-26 | A benzoic acid derivative mdm2 inhibitor for the treatment of cancer |
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Families Citing this family (43)
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| PL2118123T3 (pl) | 2007-01-31 | 2016-06-30 | Dana Farber Cancer Inst Inc | Stabilizowane peptydy p53 i ich zastosowania |
| KR101525754B1 (ko) | 2007-03-28 | 2015-06-09 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 스티칭된 폴리펩티드 |
| JO2998B1 (ar) | 2010-06-04 | 2016-09-05 | Amgen Inc | مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان |
| WO2013049250A1 (en) | 2011-09-27 | 2013-04-04 | Amgen Inc. | Heterocyclic compounds as mdm2 inhibitors for the treatment of cancer |
| TW201806968A (zh) | 2011-10-18 | 2018-03-01 | 艾利倫治療公司 | 擬肽巨環化合物 |
| BR112014020103A2 (pt) | 2012-02-15 | 2018-10-09 | Aileron Therapeutics, Inc. | macrociclos peptidomiméticos |
| CA2864120A1 (en) | 2012-02-15 | 2013-08-22 | Aileron Therapeutics, Inc. | Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles |
| US11407721B2 (en) | 2013-02-19 | 2022-08-09 | Amgen Inc. | CIS-morpholinone and other compounds as MDM2 inhibitors for the treatment of cancer |
| WO2014138429A2 (en) | 2013-03-06 | 2014-09-12 | Aileron Therapeutics, Inc. | Peptidomimetic macrocycles and use thereof in regulating hif1alpha |
| EP2970237B1 (en) | 2013-03-14 | 2017-09-27 | Amgen Inc. | Heteroaryl acid morpholinone compounds as mdm2 inhibitors for the treatment of cancer |
| JOP20200296A1 (ar) | 2013-06-10 | 2017-06-16 | Amgen Inc | عمليات صنع وأشكال بلورية من mdm2 مثبط |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201311888D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| MX393610B (es) | 2013-11-11 | 2025-03-24 | Amgen Inc | Terapia de combinacion que incluye un inhibidor mdm2 y uno o mas agentes farmaceuticamente activos adicionales para el tratamiento de canceres |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| MX2017003797A (es) | 2014-09-24 | 2017-06-15 | Aileron Therapeutics Inc | Macrociclos peptidomimeticos y usos de los mismos. |
| US12312316B2 (en) | 2015-01-20 | 2025-05-27 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| KR102564925B1 (ko) | 2015-01-20 | 2023-08-07 | 아비나스 오퍼레이션스, 인코포레이티드 | 안드로겐 수용체의 표적화된 분해를 위한 화합물 및 방법 |
| US10253067B2 (en) | 2015-03-20 | 2019-04-09 | Aileron Therapeutics, Inc. | Peptidomimetic macrocycles and uses thereof |
| EP3302482A4 (en) | 2015-06-05 | 2018-12-19 | Arvinas, Inc. | Tank-binding kinase-1 protacs and associated methods of use |
| EP3337476A4 (en) | 2015-08-19 | 2019-09-04 | Arvinas, Inc. | Compounds and methods for the targeted degradation of bromodomain-containing proteins |
| US9962380B2 (en) * | 2015-09-23 | 2018-05-08 | Wisconsin Alumni Research Foundation | Methods for treating cognitive deficits associated with fragile X syndrome |
| CN113788818A (zh) * | 2016-04-06 | 2021-12-14 | 密执安大学评议会 | Mdm2蛋白质降解剂 |
| UA123168C2 (uk) * | 2016-04-12 | 2021-02-24 | Дзе Ріджентс Оф Дзе Юніверсіті Оф Мічіган | Деструктори білка вет |
| EP3535265A4 (en) | 2016-11-01 | 2020-07-08 | Arvinas, Inc. | PROTACS TARGETING ON TAU PROTEIN AND RELATED METHODS FOR USE |
| PL3689868T3 (pl) | 2016-12-01 | 2024-03-11 | Arvinas Operations, Inc. | Pochodne tetrahydronaftalenu i tetrahydroizochinoliny jako degradery receptorów estrogenowych |
| WO2018118598A1 (en) | 2016-12-23 | 2018-06-28 | Arvinas, Inc. | Compounds and methods for the targeted degradation of fetal liver kinase polypeptides |
| CN110753693A (zh) | 2016-12-23 | 2020-02-04 | 阿尔维纳斯运营股份有限公司 | Egfr蛋白水解靶向嵌合分子和相关使用方法 |
| US11173211B2 (en) | 2016-12-23 | 2021-11-16 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of rapidly accelerated Fibrosarcoma polypeptides |
| CN117510491A (zh) | 2016-12-23 | 2024-02-06 | 阿尔维纳斯运营股份有限公司 | 用于迅速加速性纤维肉瘤多肽的靶向降解的化合物和方法 |
| US11191741B2 (en) | 2016-12-24 | 2021-12-07 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of enhancer of zeste homolog 2 polypeptide |
| IL300417A (en) | 2017-01-26 | 2023-04-01 | Arvinas Operations Inc | Bifunctional benzothiophene compounds, preparations containing them and their use in therapy |
| WO2019099926A1 (en) | 2017-11-17 | 2019-05-23 | Arvinas, Inc. | Compounds and methods for the targeted degradation of interleukin-1 receptor-associated kinase 4 polypeptides |
| MX2020010420A (es) | 2018-04-04 | 2020-12-11 | Arvinas Operations Inc | Moduladores de la proteólisis y métodos asociados de uso. |
| IL319432A (en) * | 2018-04-30 | 2025-05-01 | Kartos Therapeutics Inc | Methods of treating cancer |
| AU2019273850B2 (en) * | 2018-05-25 | 2024-11-14 | Kartos Therapeutics, Inc. | Methods of treating myeloproliferative neoplasms |
| CN112912376A (zh) | 2018-08-20 | 2021-06-04 | 阿尔维纳斯运营股份有限公司 | 用于治疗神经变性疾病的具有E3泛素连接酶结合活性并靶向α-突触核蛋白的蛋白水解靶向嵌合(PROTAC)化合物 |
| CN110963958B (zh) * | 2018-09-30 | 2025-10-10 | 上海长森药业有限公司 | 一种mdm2抑制剂，及其制备方法、药物组合物和应用 |
| MX2022002415A (es) | 2019-08-26 | 2022-03-22 | Arvinas Operations Inc | Metodos de tratamiento del cancer de mama con derivados de tetrahidronaftaleno como degradadores del receptor de estrogenos. |
| JP2023539663A (ja) | 2020-08-28 | 2023-09-15 | アルビナス・オペレーションズ・インコーポレイテッド | 急速進行性線維肉腫タンパク質分解化合物及び関連する使用方法 |
| BR112023004656A2 (pt) | 2020-09-14 | 2023-05-09 | Arvinas Operations Inc | Formas cristalinas e amorfas de um composto para a degradação direcionada do receptor de estrogênio |
| WO2024054591A1 (en) | 2022-09-07 | 2024-03-14 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use |
| US12448399B2 (en) | 2023-01-26 | 2025-10-21 | Arvinas Operations, Inc. | Cereblon-based KRAS degrading PROTACs and uses related thereto |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110319378A1 (en) * | 2010-06-04 | 2011-12-29 | Amgen Inc. | Piperidinone derivatives as mdm2 inhibitors for the treatment of cancer |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH436295A (de) | 1961-11-13 | 1967-05-31 | Mcneilab Inc | Verfahren zur Herstellung neuer 3-Morpholinone |
| DE3246148A1 (de) | 1982-12-14 | 1984-06-14 | Troponwerke GmbH & Co KG, 5000 Köln | Pyrazolo(4.3-b)(1.4)oxazine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| WO1995023135A1 (en) | 1991-03-07 | 1995-08-31 | Fisons Corporation | Diphenyl-2-piperidinone and -2-pyrrolidinone derivatives having anti-convulsant and neuroprotective activity |
| US5334720A (en) | 1991-03-07 | 1994-08-02 | Fisons Corporation | Diphenyl-1-(aminoalkyl)-2-piperidinone and -2-pyrrolidinone derivatives having anticonvulsant properties |
| ATE219077T1 (de) | 1994-08-19 | 2002-06-15 | Abbott Lab | Endothelin antagoniste |
| DE69735710T2 (de) | 1996-02-13 | 2007-03-29 | Abbott Laboratories, Abbott Park | Neue benzo-1,3-dioxolyl-und benzofuranyl substituierte pyrrolidinederivate als endothelin antagonisten |
| US6159990A (en) | 1997-06-18 | 2000-12-12 | Synaptic Pharmaceutical Corporation | Oxazolidinones as α1A receptor antagonists |
| TR200000993T2 (tr) | 1997-08-04 | 2000-12-21 | Abbott Laboratories | Endotelin antagonistleri. |
| AU1910299A (en) | 1997-12-18 | 1999-07-05 | Eli Lilly And Company | Peptidomimetic template-based combinatorial libraries |
| US6770658B2 (en) | 1998-09-09 | 2004-08-03 | Inflazyme Pharmaceuticals Ltd. | Substituted γ-phenyl-Δ-lactams and uses related thereto |
| WO2002017912A1 (en) | 2000-08-31 | 2002-03-07 | Abbott Laboratories | Endothelin antagonists |
| WO2002060894A2 (en) | 2001-01-30 | 2002-08-08 | Bristol-Myers Squibb Company | Sulfonamide lactam inhibitors of factor xa |
| EP1408986B1 (en) | 2001-05-08 | 2008-09-24 | Yale University | Proteomimetic compounds and methods |
| WO2002094787A1 (en) | 2001-05-23 | 2002-11-28 | Ucb, S.A. | 2-oxo-piperidinyl- and 2-oxo-azepanyl alkanoic acid derivativ es for the treatment of epilepsy and other neurological disorders |
| RU2305095C2 (ru) | 2001-12-18 | 2007-08-27 | Ф.Хоффманн-Ля Рош Аг | Цис-2,4,5-трифенилимидазолины и фармацевтическая композиция на их основе |
| US7425638B2 (en) | 2003-06-17 | 2008-09-16 | Hoffmann-La Roche Inc. | Cis-imidazolines |
| CN1953965B (zh) | 2004-05-18 | 2012-07-04 | 霍夫曼-拉罗奇有限公司 | 新型顺式咪唑啉类化合物 |
| US7893278B2 (en) | 2004-06-17 | 2011-02-22 | Hoffman-La Roche Inc. | CIS-imidazolines |
| US7579368B2 (en) | 2005-03-16 | 2009-08-25 | Hoffman-La Roche Inc. | Cis-imidazolines |
| WO2006107860A2 (en) | 2005-04-04 | 2006-10-12 | Eisai Co., Ltd. | Dihydropyridine compounds and compositions for headaches |
| EP2130822A1 (en) | 2005-12-01 | 2009-12-09 | F. Hoffmann-La Roche AG | 2,4,5-triphenyl imidazoline derivatives as inhibitors of the interaction between p53 and mdm2 proteins for use as anticancer agents |
| US20070213341A1 (en) | 2006-03-13 | 2007-09-13 | Li Chen | Spiroindolinone derivatives |
| BRPI0713119A2 (pt) | 2006-06-30 | 2012-04-17 | Schering Corp | piperidinas substituìdas que aumentam a atividade de p53 e os usos destas |
| MX2009000661A (es) | 2006-07-19 | 2009-03-27 | Univ Georgia Res Found | Piridinon-diceto-acidos: inhibidores de replicacion de vih en terapia de combinacion. |
| US20080045560A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Pyrrolidine and related derivatives useful as PR modulators |
| WO2008021338A2 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
| TW200831080A (en) | 2006-12-15 | 2008-08-01 | Irm Llc | Compounds and compositions as inhibitors of cannabinoid receptor 1 activity |
| GB0722769D0 (en) | 2007-11-21 | 2008-01-02 | Biolipox Ab | New compounds |
| US7625895B2 (en) | 2007-04-12 | 2009-12-01 | Hoffmann-Le Roche Inc. | Diphenyl-dihydro-imidazopyridinones |
| WO2008130614A2 (en) | 2007-04-20 | 2008-10-30 | University Of Pittsburg-Of The Commonwealth System Of Higher Education | Selective and dual-action p53/mdm2/mdm4 antagonists |
| US7834179B2 (en) | 2007-05-23 | 2010-11-16 | Hoffmann-La Roche Inc. | Spiroindolinone derivatives |
| WO2009004430A1 (en) | 2007-06-29 | 2009-01-08 | Pfizer Inc. | N-benzyl oxazolidinones and related heterocycleic compounds as potentiators of glutamate receptors |
| MX2010003868A (es) | 2007-10-09 | 2010-04-27 | Hoffmann La Roche | Cis-imidazolinas quirales. |
| US7776875B2 (en) | 2007-12-19 | 2010-08-17 | Hoffman-La Roche Inc. | Spiroindolinone derivatives |
| EP2222296A2 (en) | 2007-12-26 | 2010-09-01 | Eisai R&D Management Co., Ltd. | Ampa receptor antagonists and zonisamide for epilepsy |
| AU2009225984A1 (en) | 2008-03-21 | 2009-09-24 | Chlorion Pharma, Inc. | Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain |
| GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
| TW201011009A (en) | 2008-09-15 | 2010-03-16 | Priaxon Ag | Novel pyrrolidin-2-ones |
| AU2009294673B2 (en) | 2008-09-18 | 2014-08-14 | F. Hoffmann-La Roche Ag | Substituted pyrrolidine-2-carboxamides |
| US8076482B2 (en) | 2009-04-23 | 2011-12-13 | Hoffmann-La Roche Inc. | 3,3′-spiroindolinone derivatives |
| KR20120050492A (ko) | 2009-08-26 | 2012-05-18 | 노파르티스 아게 | 테트라-치환된 헤테로아릴 화합물 및 ｍｄｍ2 및/또는 ｍｄｍ4 조절제로서의 그의 용도 |
| US8088815B2 (en) * | 2009-12-02 | 2012-01-03 | Hoffman-La Roche Inc. | Spiroindolinone pyrrolidines |
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| US20120010235A1 (en) * | 2010-07-12 | 2012-01-12 | Xin-Jie Chu | N-substituted pyrrolidines |
| US20120046306A1 (en) * | 2010-08-18 | 2012-02-23 | David Joseph Bartkovitz | Substituted Heteroaryl Spiropyrrolidine MDM2 Antagonists |
| CN102153557B (zh) | 2011-01-21 | 2013-03-20 | 中国科学院上海有机化学研究所 | 具有乙二胺骨架的多手性中心氮杂环卡宾前体盐、合成方法及用途 |
| WO2013049250A1 (en) | 2011-09-27 | 2013-04-04 | Amgen Inc. | Heterocyclic compounds as mdm2 inhibitors for the treatment of cancer |
-
2014
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- 2014-02-26 MX MX2015011245A patent/MX368703B/es active IP Right Grant
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110319378A1 (en) * | 2010-06-04 | 2011-12-29 | Amgen Inc. | Piperidinone derivatives as mdm2 inhibitors for the treatment of cancer |
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| AU2014223547A1 (en) | 2015-09-03 |
| CN105121407A (zh) | 2015-12-02 |
| JP6266659B2 (ja) | 2018-01-24 |
| TW201505630A (zh) | 2015-02-16 |
| MX2015011245A (es) | 2016-05-31 |
| US8952036B2 (en) | 2015-02-10 |
| CN105121407B (zh) | 2017-07-18 |
| UY35353A (es) | 2014-09-30 |
| JP2016510028A (ja) | 2016-04-04 |
| AR094970A1 (es) | 2015-09-09 |
| CA2902856A1 (en) | 2014-09-04 |
| EP2961735A1 (en) | 2016-01-06 |
| EP2961735B1 (en) | 2017-09-27 |
| US20140243372A1 (en) | 2014-08-28 |
| WO2014134201A1 (en) | 2014-09-04 |
| CA2902856C (en) | 2021-02-16 |
| MX368703B (es) | 2019-10-11 |
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