CN103781780B - 作为jak抑制剂的杂环基嘧啶类似物 - Google Patents

作为jak抑制剂的杂环基嘧啶类似物 Download PDF

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Publication number
CN103781780B
CN103781780B CN201280043720.5A CN201280043720A CN103781780B CN 103781780 B CN103781780 B CN 103781780B CN 201280043720 A CN201280043720 A CN 201280043720A CN 103781780 B CN103781780 B CN 103781780B
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amino
base
pyrimidine
chloro
pyrazoles
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CN103781780A (zh
Inventor
J.弗里曼
V.里德
G.阿迪森
N.拉姆斯登
J.E.斯坎隆
R.J.哈里森
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Cellzome Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Transplantation (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CN201280043720.5A 2011-07-28 2012-07-24 作为jak抑制剂的杂环基嘧啶类似物 Expired - Fee Related CN103781780B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP11175807.4 2011-07-28
EP11175807 2011-07-28
US201261635921P 2012-04-20 2012-04-20
US61/635,921 2012-04-20
PCT/EP2012/064515 WO2013014162A1 (en) 2011-07-28 2012-07-24 Heterocyclyl pyrimidine analogues as jak inhibitors

Publications (2)

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CN103781780A CN103781780A (zh) 2014-05-07
CN103781780B true CN103781780B (zh) 2015-11-25

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Country Link
US (1) US20140179664A1 (https=)
EP (1) EP2736901A1 (https=)
JP (1) JP2014521623A (https=)
KR (1) KR20140047092A (https=)
CN (1) CN103781780B (https=)
AU (1) AU2012288892B2 (https=)
BR (1) BR112014000360A2 (https=)
CA (1) CA2843195A1 (https=)
WO (1) WO2013014162A1 (https=)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2440058A4 (en) 2009-06-12 2012-11-21 Dana Farber Cancer Inst Inc MELTED HETEROCYCLIC COMPOUNDS AND APPLICATIONS THEREOF
CA2856291C (en) 2011-11-17 2020-08-11 Dana-Farber Cancer Institute, Inc. Inhibitors of c-jun-n-terminal kinase (jnk)
EP2909194A1 (en) 2012-10-18 2015-08-26 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinase 7 (cdk7)
US10000483B2 (en) 2012-10-19 2018-06-19 Dana-Farber Cancer Institute, Inc. Bone marrow on X chromosome kinase (BMX) inhibitors and uses thereof
US9758522B2 (en) 2012-10-19 2017-09-12 Dana-Farber Cancer Institute, Inc. Hydrophobically tagged small molecules as inducers of protein degradation
EP3057955B1 (en) 2013-10-18 2018-04-11 Syros Pharmaceuticals, Inc. Heteroaromatic compounds useful for the treatment of prolferative diseases
US10047070B2 (en) 2013-10-18 2018-08-14 Dana-Farber Cancer Institute, Inc. Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7)
US9862688B2 (en) 2014-04-23 2018-01-09 Dana-Farber Cancer Institute, Inc. Hydrophobically tagged janus kinase inhibitors and uses thereof
US10017477B2 (en) 2014-04-23 2018-07-10 Dana-Farber Cancer Institute, Inc. Janus kinase inhibitors and uses thereof
AU2015371251B2 (en) 2014-12-23 2020-06-11 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinase 7 (CDK7)
HK1246645A1 (zh) 2015-03-27 2018-09-14 达纳-法伯癌症研究所股份有限公司 细胞周期蛋白依赖性激酶的抑制剂
US10702527B2 (en) 2015-06-12 2020-07-07 Dana-Farber Cancer Institute, Inc. Combination therapy of transcription inhibitors and kinase inhibitors
EP3347018B1 (en) 2015-09-09 2021-09-01 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinases
CN108136010A (zh) 2015-10-08 2018-06-08 宏观基因有限公司 用于治疗癌症的联合疗法
US11214565B2 (en) 2015-11-20 2022-01-04 Denali Therapeutics Inc. Compound, compositions, and methods
US11028080B2 (en) 2016-03-11 2021-06-08 Denali Therapeutics Inc. Substituted pyrimidines as LRKK2 inhibitors
MD3472153T2 (ro) 2016-06-16 2022-03-31 Denali Therapeutics Inc Pirimidin-2-ilamino-1H-pirazoli în calitate de inhibitori L RRK2 pentru utilizare în tratamentul tulburărilor neurodegenerative
AU2018337138B2 (en) 2017-09-21 2021-04-01 Beijing Scitech-Mq Pharmaceuticals Limited 2-substituted pyrazole amino-4-substituted amino-5-pyrimidine formamide compound, composition, and application thereof
CN109535132B (zh) * 2017-09-21 2021-07-20 北京赛特明强医药科技有限公司 2-取代吡唑氨基-4-取代氨基-5-嘧啶甲酰胺类化合物、组合物及其应用
KR20200101389A (ko) 2017-12-20 2020-08-27 얀센 파마슈티카 엔.브이. 메닌-mll 상호작용의 엑소-아자 스피로 억제제
US12187701B2 (en) 2018-06-25 2025-01-07 Dana-Farber Cancer Institute, Inc. Taire family kinase inhibitors and uses thereof
CN110734427B (zh) * 2018-07-20 2021-01-15 北京赛特明强医药科技有限公司 含烯基的嘧啶甲酰胺类化合物、组合物及其应用
CN110845476B (zh) * 2018-08-21 2022-11-18 上海和誉生物医药科技有限公司 一种高选择性csf1r抑制剂、其制备方法和在药学上的应用
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
EP3877371A4 (en) 2018-11-07 2022-07-27 Dana-Farber Cancer Institute, Inc. IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND USES THEREOF
WO2020097396A1 (en) 2018-11-07 2020-05-14 Dana-Farber Cancer Institute, Inc. Benzimidazole derivatives and aza-benzimidazole derivatives as janus kinase 2 inhibitors and uses thereof
WO2020118683A1 (en) * 2018-12-14 2020-06-18 Lynk Pharmaceuticals Co. Ltd. Benzamides of pyrazolyl-amino-pyrimidinyl derivatives, and compositions and methods thereof
JP7660063B2 (ja) 2018-12-28 2025-04-10 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 サイクリン依存性キナーゼ７のインヒビターおよびそれらの使用
MX2021013662A (es) * 2019-05-10 2022-03-11 Deciphera Pharmaceuticals Llc Inhibidores de la autofagia de heteroarilaminopirimidina amida y metodos de uso de estos.
EP3966207B1 (en) 2019-05-10 2023-11-01 Deciphera Pharmaceuticals, LLC Phenylaminopyrimidine amide autophagy inhibitors and methods of use thereof
IL325201A (en) 2019-06-17 2026-02-01 Deciphera Pharmaceuticals Llc Aminopyrimidine amide autophagy inhibitors and methods of using them
JP7554829B2 (ja) 2019-12-19 2024-09-20 ヤンセン ファーマシューティカ エヌ．ベー． 置換直鎖スピロ誘導体
WO2024239282A1 (zh) * 2023-05-24 2024-11-28 凌科药业(杭州)有限公司 一种药物组合物、外用制剂及其制备方法、应用
TW202545932A (zh) * 2024-01-26 2025-12-01 大陸商凌科藥業(杭州)有限公司 一種吡唑基-胺基-嘧啶基衍生物的苯甲醯胺的晶型、製備方法及應用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1054004A1 (en) * 1997-12-15 2000-11-22 Yamanouchi Pharmaceutical Co. Ltd. Novel pyrimidine-5-carboxamide derivatives
CN101218229A (zh) * 2005-05-05 2008-07-09 阿斯利康(瑞典)有限公司 吡唑基-氨基取代的嘧啶及其在癌症治疗中的应用
WO2008129380A1 (en) * 2007-04-18 2008-10-30 Pfizer Products Inc. Sulfonyl amide derivatives for the treatment of abnormal cell growth

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69837529T2 (de) 1997-02-12 2007-07-26 Electrophoretics Ltd., Cobham Proteinmarker für lungenkrebs und deren verwendung
GB9714249D0 (en) 1997-07-08 1997-09-10 Angiogene Pharm Ltd Vascular damaging agents
SK288365B6 (sk) 1999-02-10 2016-07-01 Astrazeneca Ab Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy
CZ301689B6 (cs) 1999-11-05 2010-05-26 Astrazeneca Ab Derivát chinazolinu a farmaceutický prostredek, který ho obsahuje
EP1382339B1 (en) 1999-12-10 2007-12-05 Pfizer Products Inc. Compositions containing pyrrolo ¬2,3-d pyrimidine derivatives
SI1255752T1 (sl) 2000-02-15 2007-12-31 Pharmacia & Upjohn Co Llc S pirolom substituirani zaviralci 2-indolinon protein kinaza
PL1891446T3 (pl) 2005-06-14 2013-08-30 Cellzome Gmbh Sposób identyfikacji nowych związków oddziałujących z enzymami
GB0605691D0 (en) 2006-03-21 2006-05-03 Novartis Ag Organic Compounds
EP1862802B1 (en) 2006-06-01 2008-12-10 Cellzome Ag Methods for the identification of ZAP-70 interacting molecules and for the purification of ZAP-70
MX2009000769A (es) 2006-07-21 2009-01-28 Novartis Ag Compuestos de 2,4-di(arilaminio)-pirimidin-5-carboxamida como inhibidores de cinasas jak.
JP2010510211A (ja) 2006-11-16 2010-04-02 ファーマコペイア・リミテッド・ライアビリティ・カンパニー 免疫抑制用７−置換プリン誘導体
US7947698B2 (en) 2007-03-23 2011-05-24 Rigel Pharmaceuticals, Inc. Compositions and methods for inhibition of the JAK pathway
WO2008118823A2 (en) 2007-03-26 2008-10-02 Rigel Pharmaceuticals, Inc. Compositions and methods for inhibition of the jak pathway
WO2008132502A1 (en) * 2007-04-25 2008-11-06 Astrazeneca Ab Pyrazolyl-amino-substituted pyrimidines and their use for the treatment of cancer
EP2178563A2 (en) 2007-07-06 2010-04-28 OSI Pharmaceuticals, Inc. Combination anti-cancer therapy comprising an inhibitor of both mtorc1 and mtorc2
CL2009001884A1 (es) 2008-10-02 2010-05-14 Incyte Holdings Corp Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco.
US20120040955A1 (en) 2009-04-14 2012-02-16 Richard John Harrison Fluoro substituted pyrimidine compounds as jak3 inhibitors
US9242987B2 (en) 2009-10-20 2016-01-26 Cellzome Limited Heterocyclyl pyrazolopyrimidine analogues as JAK inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1054004A1 (en) * 1997-12-15 2000-11-22 Yamanouchi Pharmaceutical Co. Ltd. Novel pyrimidine-5-carboxamide derivatives
CN101218229A (zh) * 2005-05-05 2008-07-09 阿斯利康(瑞典)有限公司 吡唑基-氨基取代的嘧啶及其在癌症治疗中的应用
WO2008129380A1 (en) * 2007-04-18 2008-10-30 Pfizer Products Inc. Sulfonyl amide derivatives for the treatment of abnormal cell growth

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DFG-in and DFG-out homology models of TrkB kinase receptor: Induced-fit and ensemble docking;Crtomir Podlipnink et al.;《Journal of Molecular Graphics and Modelling》;20101007;第29卷(第3期);309-320 *

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BR112014000360A2 (pt) 2017-02-14
JP2014521623A (ja) 2014-08-28
CA2843195A1 (en) 2013-01-31
WO2013014162A1 (en) 2013-01-31
AU2012288892A1 (en) 2014-02-20
CN103781780A (zh) 2014-05-07
KR20140047092A (ko) 2014-04-21
US20140179664A1 (en) 2014-06-26
EP2736901A1 (en) 2014-06-04
AU2012288892B2 (en) 2016-04-21

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