JP7014736B2 - がんの処置のためのピラゾロピリジン誘導体 - Google Patents
がんの処置のためのピラゾロピリジン誘導体 Download PDFInfo
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- JP7014736B2 JP7014736B2 JP2018561557A JP2018561557A JP7014736B2 JP 7014736 B2 JP7014736 B2 JP 7014736B2 JP 2018561557 A JP2018561557 A JP 2018561557A JP 2018561557 A JP2018561557 A JP 2018561557A JP 7014736 B2 JP7014736 B2 JP 7014736B2
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Classifications
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| PCT/US2017/034326 WO2017205538A1 (en) | 2016-05-24 | 2017-05-24 | Pyrazolopyridine derivatives for the treatment of cancer |
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Families Citing this family (31)
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| ES2928773T3 (es) | 2017-01-17 | 2022-11-22 | Heparegenix Gmbh | Inhibidores de proteína cinasas para fomentar la regeneración hepática o reducir o prevenir la muerte de hepatocitos |
| RU2020131507A (ru) * | 2018-03-29 | 2022-05-04 | Боард Оф Реджентс, Де Юниверсити Оф Техас Систем | Имидазопиперазиновые ингибиторы белков-активаторов транскрипции |
| WO2019195846A1 (en) | 2018-04-06 | 2019-10-10 | Board Of Regents, The University Of Texas System | Imidazopiperazinone inhibitors of transcription activating proteins |
| CN110878042B (zh) * | 2018-09-05 | 2021-06-01 | 新发药业有限公司 | 一种n-取代基哌啶-3-酮的制备方法 |
| CN111320621B (zh) * | 2018-12-14 | 2022-10-04 | 中国科学院广州生物医药与健康研究院 | 一种吲嗪类化合物及其制备方法和应用 |
| WO2020173440A1 (en) * | 2019-02-27 | 2020-09-03 | Cullgen (Shanghai), Inc. | Cyclic-amp response element binding protein (cbp) and/or adenoviral e1a binding protein of 300 kda (p300) degradation compounds and methods of use |
| US20220135538A1 (en) * | 2019-02-27 | 2022-05-05 | Constellation Pharmaceuticals, Inc. | P300/cbp hat inhibitors and methods for their use |
| SG11202110714VA (en) * | 2019-04-09 | 2021-10-28 | Plexxikon Inc | Condensed azines for ep300 or cbp modulation and indications therefor |
| JP7539382B2 (ja) | 2019-07-29 | 2024-08-23 | 武田薬品工業株式会社 | 複素環化合物 |
| TW202120095A (zh) * | 2019-08-05 | 2021-06-01 | 美商美國禮來大藥廠 | 7,8-二氫-4H-吡唑并[4,3-c]氮呯-6-酮化合物 |
| EP4097105A1 (en) * | 2020-01-27 | 2022-12-07 | Bristol-Myers Squibb Company | 1h-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (tlr7) agonists |
| CN111440161B (zh) * | 2020-05-15 | 2023-04-14 | 中国药科大学 | 一种具有par4拮抗活性的二环杂芳基类化合物及其应用 |
| US12425396B2 (en) * | 2020-06-10 | 2025-09-23 | Beijing Xiaomi Mobile Software Co., Ltd. | Biometric feature verification method and apparatus, electronic device, and storage medium |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| CR20230057A (es) | 2020-07-02 | 2023-08-15 | Incyte Corp | Compuestos tríciclicos de urea como inhibidores de jak2 v617f |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| CN112079826B (zh) * | 2020-09-17 | 2022-07-29 | 广州中医药大学(广州中医药研究院) | 一类甾体合成酶抑制剂及其治疗应用 |
| CA3193745A1 (en) | 2020-10-02 | 2022-04-07 | Kang Le | Imidazopiperazine inhibitors of transcription activating proteins |
| EP4221708A4 (en) | 2020-10-02 | 2024-11-06 | Board of Regents, The University of Texas System | IMIDAZOPIPERAZINE INHIBITORS OF TRANSCRIPTION-ACTIVATING PROTEINS |
| US20230399303A1 (en) * | 2020-10-26 | 2023-12-14 | Yale University | Macrophage Migration Inhibitory Factor Inhibitors, and Methods of Making and Using Same |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| US20240122941A1 (en) * | 2020-12-25 | 2024-04-18 | National Cancer Center | Therapy based on synthetic lethality in swi/snf complex-dysfunction cancer |
| AR125273A1 (es) | 2021-02-25 | 2023-07-05 | Incyte Corp | Lactamas espirocíclicas como inhibidores de jak2 v617f |
| PT4426434T (pt) | 2021-11-02 | 2025-11-24 | Flare Therapeutics Inc | Agonistas inversos de pparg e suas utilizações |
| IL312642A (en) | 2021-11-12 | 2024-07-01 | Insilico Medicine Ip Ltd | Small molecule inhibitors of ubiquitin specific protease 1 (usp1) and uses thereof |
| AU2023235313A1 (en) | 2022-03-17 | 2024-10-03 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| WO2024019698A1 (en) | 2022-07-18 | 2024-01-25 | Jsr Corporation | Photocatalytic synthesis of alpha, beta unsaturated carbonyl compounds and their intermediates |
| CN117843618A (zh) * | 2022-08-29 | 2024-04-09 | 北京沐华生物科技有限责任公司 | 一种ep300/cbp调节剂及其制备方法和用途 |
| CN115710249B (zh) * | 2022-11-14 | 2024-11-19 | 广东工业大学 | 一种多取代异喹啉和1,6-萘啶化合物的制备方法及光电材料常见分子骨架 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011526283A (ja) | 2008-06-25 | 2011-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | 抗−hiv薬としてのジケト縮合アゾロピペリジンおよびアゾロピペラジン |
| JP2014526446A (ja) | 2011-09-12 | 2014-10-06 | サノフイ | インダニル置換の4,5,6,7−テトラヒドロ−1H−ピラゾロ[4,3−c]ピリジン、医薬としてのその使用、及びそれらを含む医薬製剤 |
| JP6771464B2 (ja) | 2014-11-27 | 2020-10-21 | ジェネンテック, インコーポレイテッド | Cbpおよび/またはep300インヒビターとしての、4,5,6,7−テトラヒドロ−1h−ピラゾロ[4,3−c]ピリジン−3−アミン化合物 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CU22545A1 (es) | 1994-11-18 | 1999-03-31 | Centro Inmunologia Molecular | Obtención de un anticuerpo quimérico y humanizado contra el receptor del factor de crecimiento epidérmico para uso diagnóstico y terapéutico |
| DK27383A (da) * | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
| US4943533A (en) | 1984-03-01 | 1990-07-24 | The Regents Of The University Of California | Hybrid cell lines that produce monoclonal antibodies to epidermal growth factor receptor |
| EP0491007B1 (en) | 1989-09-08 | 1996-03-13 | The Johns Hopkins University | Structural alterations of the egf receptor gene in human gliomas |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| DE69428764T2 (de) | 1993-12-24 | 2002-06-20 | Merck Patent Gmbh | Immunokonjugate |
| IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| IL112248A0 (en) | 1994-01-25 | 1995-03-30 | Warner Lambert Co | Tricyclic heteroaromatic compounds and pharmaceutical compositions containing them |
| US5654307A (en) | 1994-01-25 | 1997-08-05 | Warner-Lambert Company | Bicyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
| WO1996003397A1 (en) | 1994-07-21 | 1996-02-08 | Akzo Nobel N.V. | Cyclic ketone peroxide formulations |
| US5804396A (en) | 1994-10-12 | 1998-09-08 | Sugen, Inc. | Assay for agents active in proliferative disorders |
| DE69536015D1 (de) | 1995-03-30 | 2009-12-10 | Pfizer Prod Inc | Chinazolinone Derivate |
| GB9508565D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| JPH11507535A (ja) | 1995-06-07 | 1999-07-06 | イムクローン システムズ インコーポレイテッド | 腫瘍の成長を抑制する抗体および抗体フラグメント類 |
| SI9620103A (sl) | 1995-07-06 | 1998-10-31 | Novartis Ag | Pirolopirimidini in postopki za njihovo pripravo |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| EA001595B1 (ru) | 1996-04-12 | 2001-06-25 | Варнер-Ламберт Компани | Необратимые ингибиторы тирозинкиназ |
| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| ID18494A (id) | 1996-10-02 | 1998-04-16 | Novartis Ag | Turunan pirazola leburan dan proses pembuatannya |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6002008A (en) | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
| WO1998050038A1 (en) | 1997-05-06 | 1998-11-12 | American Cyanamid Company | Use of quinazoline compounds for the treatment of polycystic kidney disease |
| ZA986729B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| TW436485B (en) | 1997-08-01 | 2001-05-28 | American Cyanamid Co | Substituted quinazoline derivatives |
| BR9814116A (pt) | 1997-11-06 | 2000-10-03 | American Cyanamid Co | Uso de derivados de quinazolina como inibidores de cinase de tirosina para tratamento de pólipo colÈnico |
| EA003786B1 (ru) | 1998-11-19 | 2003-10-30 | Варнер Ламберт Компани | N-[4-(3-хлор-4-фторфениламино)-7-(3-морфолин-4-илпропокси)хиназолин-6-ил]акриламид - необратимый ингибитор тирозинкиназ |
| CA2493637A1 (en) | 2002-07-25 | 2004-02-12 | Manuela Villa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| EP1526852A1 (en) | 2002-07-25 | 2005-05-04 | Pharmacia Italia S.p.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| US20070037790A1 (en) | 2003-03-11 | 2007-02-15 | Francesca Abrate | Bicyclo-pyrazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| DK2439273T3 (da) | 2005-05-09 | 2019-06-03 | Ono Pharmaceutical Co | Humane monoklonale antistoffer til programmeret død-1(pd-1) og fremgangsmåder til behandling af cancer ved anvendelse af anti-pd-1- antistoffer alene eller i kombination med andre immunterapeutika |
| PT1907424E (pt) | 2005-07-01 | 2015-10-09 | Squibb & Sons Llc | Anticorpos monoclonais humanos para o ligando 1 de morte programada (pd-l1) |
| EP1968976A1 (en) | 2005-12-12 | 2008-09-17 | NERVIANO MEDICAL SCIENCES S.r.l. | Substituted pyrazolo [4,3-c] pyridine derivatives active as kinase inhibitors |
| WO2007099166A1 (en) | 2006-03-03 | 2007-09-07 | Nerviano Medical Sciences S.R.L. | Pyrazolo-pyridine derivatives active as kinase inhibitors |
| KR101600634B1 (ko) | 2007-12-28 | 2016-03-07 | 미쓰비시 타나베 파마 코퍼레이션 | 항암제 |
| CN101970499B (zh) | 2008-02-11 | 2014-12-31 | 治疗科技公司 | 用于肿瘤治疗的单克隆抗体 |
| EP2262837A4 (en) | 2008-03-12 | 2011-04-06 | Merck Sharp & Dohme | PD-1 BINDING PROTEINS |
| CL2009001158A1 (es) | 2008-05-15 | 2009-10-23 | Nerviano Medical Sciences Srl | Compuestos derivados de los acidos carboxilicos, tales como 5,6-dihiro-4h-pirrolo[3,4-c]pirazol, furo[3,2-c]pirazol, tieno[2,3-c]pirazol, 4,5,6,7-tetrahidropirazol[4,3-c]piridina e indazol; composicion farmaceutica; y su uso en el tratamiento de trastornos proliferativos celulares asociados a la actividad de proteina quinasa alterada, tal como el cancer. |
| JP2012500855A (ja) | 2008-08-25 | 2012-01-12 | アンプリミューン、インコーポレーテッド | Pd−1アンタゴニストおよび感染性疾患を処置するための方法 |
| EP3255060A1 (en) | 2008-12-09 | 2017-12-13 | F. Hoffmann-La Roche AG | Anti-pd-l1 antibodies and their use to enhance t-cell function |
| WO2011066342A2 (en) | 2009-11-24 | 2011-06-03 | Amplimmune, Inc. | Simultaneous inhibition of pd-l1/pd-l2 |
| CN101812063B (zh) | 2010-03-18 | 2012-04-25 | 中国医学科学院医药生物技术研究所 | α-萘磺酰胺基五元杂环类化合物及其抑瘤活性 |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| WO2013148114A1 (en) | 2012-03-30 | 2013-10-03 | University Of Florida Research Foundation, Inc. | P300/cbp inhibitors and methods of use |
| WO2014138727A1 (en) | 2013-03-08 | 2014-09-12 | Board Of Regents, The University Of Texas System | Suppression of malignant mesothelioma by overexpression or stimulation of endothelial protein c receptors (epcr) |
| EP2993174A1 (en) * | 2014-09-08 | 2016-03-09 | Helmholtz Zentrum München Deutsches Forschungszentrum für Gesundheit und Umwelt GmbH | Pyrazolopyridine derivatives and their use in therapy |
-
2017
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- 2017-05-24 MA MA045146A patent/MA45146A/fr unknown
- 2017-05-24 WO PCT/US2017/034326 patent/WO2017205538A1/en not_active Ceased
- 2017-05-24 CN CN201780045658.6A patent/CN109476663B/zh active Active
- 2017-05-24 EP EP17729963.3A patent/EP3464286B1/en active Active
-
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- 2018-11-21 US US16/198,581 patent/US11247989B2/en not_active Expired - Fee Related
-
2022
- 2022-01-06 US US17/570,139 patent/US20220127265A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011526283A (ja) | 2008-06-25 | 2011-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | 抗−hiv薬としてのジケト縮合アゾロピペリジンおよびアゾロピペラジン |
| JP2014526446A (ja) | 2011-09-12 | 2014-10-06 | サノフイ | インダニル置換の4,5,6,7−テトラヒドロ−1H−ピラゾロ[4,3−c]ピリジン、医薬としてのその使用、及びそれらを含む医薬製剤 |
| JP6771464B2 (ja) | 2014-11-27 | 2020-10-21 | ジェネンテック, インコーポレイテッド | Cbpおよび/またはep300インヒビターとしての、4,5,6,7−テトラヒドロ−1h−ピラゾロ[4,3−c]ピリジン−3−アミン化合物 |
Non-Patent Citations (10)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters,2005年,15(6),1687-1691 |
| DATABASE REGISTRY on STN,2011年12月05日,RN 1349159-92-7 |
| DATABASE REGISTRY on STN,2011年12月07日,RN 1350101-01-7 |
| DATABASE REGISTRY on STN,2012年04月13日,RN 1367868-74-3 |
| DATABASE REGISTRY on STN,2015年06月26日,RN 1789047-56-8 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790521-91-3 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790521-98-0 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790625-75-0 |
| European Journal of Medicinal Chemistry,2014年,71,168-184 |
| Journal of Medicinal Chemstry,1985年,28(7),934-940 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3464286B1 (en) | 2021-08-18 |
| CN109476663B (zh) | 2021-11-09 |
| JP2019516759A (ja) | 2019-06-20 |
| MA45146A (fr) | 2021-03-24 |
| CN109476663A (zh) | 2019-03-15 |
| US11247989B2 (en) | 2022-02-15 |
| EP3464286A1 (en) | 2019-04-10 |
| WO2017205538A1 (en) | 2017-11-30 |
| US20220127265A1 (en) | 2022-04-28 |
| US20190241558A1 (en) | 2019-08-08 |
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