JP5576370B2 - Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 - Google Patents

Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 Download PDF

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JP5576370B2
JP5576370B2 JP2011521675A JP2011521675A JP5576370B2 JP 5576370 B2 JP5576370 B2 JP 5576370B2 JP 2011521675 A JP2011521675 A JP 2011521675A JP 2011521675 A JP2011521675 A JP 2011521675A JP 5576370 B2 JP5576370 B2 JP 5576370B2
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JP2011530500A (ja
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ニンコヴィック サッシャ
フレデリック ブランガンザ ジョン
レイモンド コリンズ マイケル
チャールズ キャス ジョン
リ ホイ
タイラー リクター ダニエル
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ファイザー・インク
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
JP2011521675A 2008-08-06 2009-08-04 Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 Expired - Fee Related JP5576370B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US8673208P 2008-08-06 2008-08-06
US61/086,732 2008-08-06
US22942809P 2009-07-29 2009-07-29
US61/229,428 2009-07-29
PCT/IB2009/053389 WO2010016005A1 (en) 2008-08-06 2009-08-04 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors

Publications (3)

Publication Number Publication Date
JP2011530500A JP2011530500A (ja) 2011-12-22
JP2011530500A5 JP2011530500A5 (https=) 2012-09-13
JP5576370B2 true JP5576370B2 (ja) 2014-08-20

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JP2011521675A Expired - Fee Related JP5576370B2 (ja) 2008-08-06 2009-08-04 Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物

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US (1) US8518952B2 (https=)
EP (1) EP2328890B1 (https=)
JP (1) JP5576370B2 (https=)
AT (1) ATE542813T1 (https=)
CA (1) CA2731368C (https=)
ES (1) ES2378513T3 (https=)
WO (1) WO2010016005A1 (https=)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2663222T3 (es) 2008-12-19 2018-04-11 Vertex Pharmaceuticals Incorporated Derivados de pirazina útiles como inhibidores de la quinasa ATR
MX2011009796A (es) 2009-03-20 2011-12-14 Amgen Inc Inhibidores de la cinasa pi3.
PH12012500778A1 (en) 2009-10-30 2012-11-26 Janssen Pharmaceutica Nv IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS
EP2338888A1 (en) * 2009-12-24 2011-06-29 Almirall, S.A. Imidazopyridine derivatives as JAK inhibitors
UY33213A (es) * 2010-02-18 2011-09-30 Almirall Sa Derivados de pirazol como inhibidores de jak
EP2360158A1 (en) * 2010-02-18 2011-08-24 Almirall, S.A. Pyrazole derivatives as jak inhibitors
AR080754A1 (es) 2010-03-09 2012-05-09 Janssen Pharmaceutica Nv Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10
US8247436B2 (en) 2010-03-19 2012-08-21 Novartis Ag Pyridine and pyrazine derivative for the treatment of CF
US9630956B2 (en) 2010-05-12 2017-04-25 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase
JP2013526540A (ja) * 2010-05-12 2013-06-24 バーテックス ファーマシューティカルズ インコーポレイテッド Atrキナーゼ阻害剤として有用な化合物
EP2463289A1 (en) 2010-11-26 2012-06-13 Almirall, S.A. Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors
BR112013033375B1 (pt) 2011-06-27 2022-05-10 Janssen Pharmaceutica N.V Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário
EP2554544A1 (en) 2011-08-01 2013-02-06 Almirall, S.A. Pyridin-2(1h)-one derivatives as jak inhibitors
WO2013049859A1 (en) 2011-09-30 2013-04-04 Vertex Pharmaceuticals Incorporated Treating pancreatic cancer and non-small cell lung cancer with atr inhibitors
SG10201606774UA (en) 2011-09-30 2016-10-28 Vertex Pharma Processes for making compounds useful as inhibitors of atr kinase
WO2013066729A1 (en) 2011-10-31 2013-05-10 Merck Sharp & Dohme Corp. Aminopyrimidinones as interleukin receptor-associated kinase inhibitors
CA2869309C (en) 2012-04-05 2021-02-09 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of atr kinase and combination therapies thereof
HK1206250A1 (en) 2012-06-26 2016-01-08 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders
WO2014009305A1 (en) 2012-07-09 2014-01-16 Janssen Pharmaceutica Nv Inhibitors of phosphodiesterase 10 enzyme
US8999632B2 (en) 2012-10-04 2015-04-07 Vertex Pharmaceuticals Incorporated Method for measuring ATR inhibition mediated increases in DNA damage
KR20220143164A (ko) 2012-11-21 2022-10-24 피티씨 테라퓨틱스, 인크. 치환된 리버스 피리미딘 bmi-1 저해제
CN103254121B (zh) * 2013-04-08 2015-08-26 洛阳师范学院 一种合成(3r,4r)-n-pg-4-甲基-3-甲胺基哌啶的方法
WO2015076800A1 (en) 2013-11-21 2015-05-28 Ptc Therapeutics, Inc. Substituted pyridine and pyrazine bmi-1 inhibitors
MX368464B (es) 2013-12-05 2019-10-02 Pfizer Acrilamidas de pirrolo[2,3-d]pirimidinilo, pirrolo[2,3-b]pirazinil o y pirrolo[2,3-d]piridinilo.
US9145393B2 (en) * 2014-01-24 2015-09-29 Confluence Life Sciences, Inc. Arylpyridinone ITK inhibitors for treating inflammation and cancer
US9758518B2 (en) 2015-03-04 2017-09-12 Pimera, Inc. Compositions, uses and methods for making them
PL3140305T3 (pl) 2014-05-09 2018-10-31 Pimera, Inc. Nowe kompozycje, ich zastosowania i sposoby wytwarzania
CA2973597A1 (en) 2015-01-23 2016-07-28 Confluence Life Sciences, Inc. Heterocyclic itk inhibitors for treating inflammation and cancer
US10703756B2 (en) 2015-05-01 2020-07-07 Pfizer Inc. Pyrrolo[2,3-D]pyrimidinyl, pyrrolo[2,3-B]pyrazinyl, pyrrolo[2,3-B]pyridinyl acrylamides and epoxides thereof
CN105130991B (zh) * 2015-07-10 2017-09-19 成都知普莱生物医药科技有限公司 一种合成骨形态发生蛋白受体抑制剂的方法
HK1258570A1 (zh) 2015-09-30 2019-11-15 Vertex Pharmaceuticals Inc. 使用dna损伤剂及atr抑制剂的组合治疗癌症的方法
CR20180372A (es) 2016-02-24 2018-09-19 Pfizer Derivados de pirazolo [1,5-a] pirazin-4-ilo
WO2018140648A1 (en) 2017-01-25 2018-08-02 Eric Jon Jacobsen Pyrrolopyrimidine itk inhibitors for treating inflammation and cancer
CA3057741A1 (en) 2017-03-28 2018-10-04 Pimera, Inc. Novel crystal forms of a pol1 inhibitor
CN107056681B (zh) * 2017-03-30 2019-10-01 广州白云山光华制药股份有限公司 一种托法替布中间体的制备方法
WO2019034973A1 (en) 2017-08-14 2019-02-21 Pfizer Inc. PYRAZOLO [1,5-A] PYRAZIN-4-YL AND RELATED DERIVATIVES
CN107474047B (zh) * 2017-08-29 2019-10-29 浙江工业大学 1,2,4-三唑并杂环类化合物的合成方法
CN107827811B (zh) * 2017-11-15 2021-01-29 上海皓伯化工科技有限公司 一种制备n-取代-1,2,3,6-四氢吡啶的方法
JP2021151955A (ja) * 2018-05-22 2021-09-30 株式会社カネカ 光学活性−cis−アミノピペリジンの製造方法
US12448374B2 (en) 2018-06-07 2025-10-21 Disarm Therapeutics, Inc. Inhibitors of SARM1
EP3608326A1 (en) 2018-08-10 2020-02-12 Irbm S.P.A. Tricyclic inhibitors of hepatitis b virus
CN113164479A (zh) 2018-08-17 2021-07-23 Ptc医疗公司 用于治疗胰腺癌的方法
EP3825318A1 (en) 2019-11-25 2021-05-26 Promidis S.r.l. Oxalamido-substituted tricyclic inhibitors of hepatitis b virus
UY38705A (es) 2019-05-23 2020-12-31 Irbm S P A Inhibidores tricíclicos sustituidos con oxalamido del virus de hepatitis b
EP3741762A1 (en) 2019-05-23 2020-11-25 Irbm S.P.A. Oxalamido-substituted tricyclic inhibitors of hepatitis b virus
WO2021252775A1 (en) * 2020-06-11 2021-12-16 Chdi Foundation, Inc. Heterocyclic compounds and imaging agents for imaging huntingtin protein
EP4188926A4 (en) * 2020-07-31 2024-08-21 Children's Hospital Medical Center Multi-cyclic irak and flt3 inhibiting compounds and uses thereof
KR102473645B1 (ko) * 2020-08-28 2022-12-05 (주)부흥산업사 (2S,5R)-벤질 5-(t-부톡시카르보닐아미노)-2-메틸피페리딘-1-카르복실레이트의 제조방법
IL310425A (en) * 2021-07-30 2024-03-01 Childrens Hospital Med Ct Multi-cyclic irak and flt3 inhibiting compounds and uses thereof
AU2023283393A1 (en) * 2022-06-10 2025-01-02 Interline Therapeutics, Inc. Imidazo(1,2-a)pyridine derivatives as ripk2 inhibitors
AR129535A1 (es) 2022-06-21 2024-09-04 Syngenta Crop Protection Ag Derivados de carboxamida heterocíclicos bicíclicos microbiocidas
WO2024089191A1 (en) 2022-10-27 2024-05-02 Syngenta Crop Protection Ag Microbiocidal heterobicyclic dihydrooxadiazine derivatives
CN116478076A (zh) * 2023-04-26 2023-07-25 南京优氟医药科技有限公司 一种(2s,4s)-1-叔丁氧羰基-2-(二氟甲基)-4-羟基吡咯烷的制备方法
WO2026006247A1 (en) * 2024-06-26 2026-01-02 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services 2-(piperidin-3-yl)isoindole-1,3-dione analogs and uses thereof

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0166088B1 (ko) 1990-01-23 1999-01-15 . 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도
US5376645A (en) 1990-01-23 1994-12-27 University Of Kansas Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
GB9518953D0 (en) * 1995-09-15 1995-11-15 Pfizer Ltd Pharmaceutical formulations
WO2000035298A1 (en) 1996-11-27 2000-06-22 Wm. Wrigley Jr. Company Chewing gum containing medicament active agents
GB9711643D0 (en) 1997-06-05 1997-07-30 Janssen Pharmaceutica Nv Glass thermoplastic systems
GB9722320D0 (en) * 1997-10-22 1997-12-17 Janssen Pharmaceutica Nv Human cell cycle checkpoint proteins
US6383744B1 (en) * 1998-07-10 2002-05-07 Incyte Genomics, Inc. Human checkpoint kinase
EP1135135A4 (en) 1998-09-18 2006-08-09 Smithkline Beecham Corp CHK1 KINASE INHIBITORS
US6682736B1 (en) * 1998-12-23 2004-01-27 Abgenix, Inc. Human monoclonal antibodies to CTLA-4
WO2001016306A2 (en) 1999-08-27 2001-03-08 Chiron Corporation Chimeric antisense oligonucleotides and cell transfecting formulations thereof
JP4610828B2 (ja) 1999-09-22 2011-01-12 株式会社 キャンバス G2期細胞周期停止の阻害、およびdna損傷剤に対する細胞感作のための組成物および方法
US6211164B1 (en) * 2000-03-10 2001-04-03 Abbott Laboratories Antisense oligonucleotides of the human chk1 gene and uses thereof
BRPI0116728B1 (pt) 2001-01-05 2018-10-30 Pfizer Inc. anticorpos para receptor de fator de crescimento i semelhante à insulina
UA76977C2 (en) 2001-03-02 2006-10-16 Icos Corp Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers
AR039067A1 (es) 2001-11-09 2005-02-09 Pfizer Prod Inc Anticuerpos para cd40
EP1501514B1 (en) * 2002-05-03 2012-12-19 Exelixis, Inc. Protein kinase modulators and methods of use
US7704995B2 (en) * 2002-05-03 2010-04-27 Exelixis, Inc. Protein kinase modulators and methods of use
CA2512683C (en) * 2003-01-09 2010-03-16 Pfizer Inc. Tricyclic compounds protein kinase inhibitors for enhancing the efficacy of anti-neoplastic agents and radiation therapy
DK1641780T3 (da) 2003-06-24 2009-02-02 Pfizer Prod Inc Fremgangsmåder til fremstilling af 1-[(benzimidazol-1yl)quinolin-8-yl]-piperidin-4-ylamin-derivater
WO2008024974A1 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Pyrimidine and pyrazine derivatives
US8183245B2 (en) 2007-10-25 2012-05-22 Merck Sharp & Dohme Corp. Pyrazine substituted pyrrolopyridines as inhibitors of JAK and PDK1

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Publication number Publication date
JP2011530500A (ja) 2011-12-22
EP2328890B1 (en) 2012-01-25
ES2378513T3 (es) 2012-04-13
CA2731368A1 (en) 2010-02-11
WO2010016005A1 (en) 2010-02-11
EP2328890A1 (en) 2011-06-08
US20110144084A1 (en) 2011-06-16
US8518952B2 (en) 2013-08-27
CA2731368C (en) 2013-05-14
ATE542813T1 (de) 2012-02-15

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