CA2731368C - 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors - Google Patents

6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors Download PDF

Info

Publication number
CA2731368C
CA2731368C CA2731368A CA2731368A CA2731368C CA 2731368 C CA2731368 C CA 2731368C CA 2731368 A CA2731368 A CA 2731368A CA 2731368 A CA2731368 A CA 2731368A CA 2731368 C CA2731368 C CA 2731368C
Authority
CA
Canada
Prior art keywords
fluorine
chlorine
further substituted
alkyl
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2731368A
Other languages
English (en)
French (fr)
Other versions
CA2731368A1 (en
Inventor
Sacha Ninkovic
John Frederick Braganza
Michael Raymond Collins
John Charles Kath
Hui Li
Daniel Tyler Richter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Inc
Original Assignee
Pfizer Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of CA2731368A1 publication Critical patent/CA2731368A1/en
Application granted granted Critical
Publication of CA2731368C publication Critical patent/CA2731368C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic 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
    • C07D513/02—Heterocyclic 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
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Oncology (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)
CA2731368A 2008-08-06 2009-08-04 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors Expired - Fee Related CA2731368C (en)

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 (2)

Publication Number Publication Date
CA2731368A1 CA2731368A1 (en) 2010-02-11
CA2731368C true CA2731368C (en) 2013-05-14

Family

ID=41171261

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2731368A Expired - Fee Related CA2731368C (en) 2008-08-06 2009-08-04 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors

Country Status (7)

Country Link
US (1) US8518952B2 (enExample)
EP (1) EP2328890B1 (enExample)
JP (1) JP5576370B2 (enExample)
AT (1) ATE542813T1 (enExample)
CA (1) CA2731368C (enExample)
ES (1) ES2378513T3 (enExample)
WO (1) WO2010016005A1 (enExample)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3354650T3 (pl) 2008-12-19 2022-06-13 Vertex Pharmaceuticals Incorporated Związki przydatne jako inhibitory kinazy atr
CA2755285C (en) * 2009-03-20 2014-02-11 Yunxin Y. Bo Inhibitors of pi3 kinase
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
EP2360158A1 (en) * 2010-02-18 2011-08-24 Almirall, S.A. Pyrazole derivatives as jak inhibitors
UY33213A (es) * 2010-02-18 2011-09-30 Almirall Sa Derivados de pirazol como inhibidores de jak
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
JP5836367B2 (ja) 2010-05-12 2015-12-24 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Vertex Pharmaceuticals Incorporated Atrキナーゼ阻害剤として有用な化合物
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
JP6115962B2 (ja) 2011-06-27 2017-04-19 ヤンセン ファーマシューティカ エヌ.ベー. 1−アリール−4−メチル−[1,2,4]トリアゾロ[4,3−a]キノキサリン誘導体
EP2554544A1 (en) 2011-08-01 2013-02-06 Almirall, S.A. Pyridin-2(1h)-one derivatives as jak inhibitors
RU2018147217A (ru) 2011-09-30 2019-01-18 Вертекс Фармасьютикалз Инкорпорейтед Способы получения соединений, которые можно использовать в качестве ингибиторов киназы atr
AU2012315384B2 (en) 2011-09-30 2017-08-10 Vertex Pharmaceuticals Incorporated Treating pancreatic cancer and non-small cell lung cancer with ATR inhibitors
EP2773207B1 (en) 2011-10-31 2018-03-07 Merck Sharp & Dohme Corp. Aminopyrimidinones as interleukin receptor-associated kinase inhibitors
CN104582795B (zh) 2012-04-05 2018-04-20 沃泰克斯药物股份有限公司 可用作atr激酶抑制剂的化合物及其组合疗法
WO2014001314A1 (en) 2012-06-26 2014-01-03 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders
AU2013289284B2 (en) 2012-07-09 2017-03-30 Janssen Pharmaceutica Nv Inhibitors of phosphodiesterase 10 enzyme
DK2904406T3 (en) 2012-10-04 2018-06-18 Vertex Pharma METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE
PH12015501130B1 (en) 2012-11-21 2023-01-27 Ptc Therapeutics Inc Substituted reverse pyrimidine bmi-1 inhibitors
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
US10584115B2 (en) * 2013-11-21 2020-03-10 Ptc Therapeutics, Inc. Substituted pyridine and pyrazine BMI-1 inhibitors
LT3077395T (lt) 2013-12-05 2018-02-12 Pfizer Inc. Pirolo[2,3-d]pirimidinilo, pirolo[2,3-b]pirazinilo ir pirolo[2,3-d]piridinilo akrilamidai
US9145393B2 (en) * 2014-01-24 2015-09-29 Confluence Life Sciences, Inc. Arylpyridinone ITK inhibitors for treating inflammation and cancer
BR112016026150B1 (pt) 2014-05-09 2019-11-05 Pimera, Inc. compostos carboxílicos e seu uso na preparação de medicamentos ou composições farmacêuticas para tratar câncer
US9758518B2 (en) 2015-03-04 2017-09-12 Pimera, Inc. Compositions, uses and methods for making them
AU2016209046A1 (en) 2015-01-23 2017-07-20 Aclaris Therapeutics, Inc. Heterocyclic ITK inhibitors for treating inflammation and cancer
CA2984183C (en) 2015-05-01 2021-11-09 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
US11464774B2 (en) 2015-09-30 2022-10-11 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors
MX383747B (es) 2016-02-24 2025-03-14 Pfizer Derivados de pirazolo[1,5-a]pirazin-4-ilo como inhibidores de quinasas janus (jak)
WO2018140648A1 (en) 2017-01-25 2018-08-02 Eric Jon Jacobsen Pyrrolopyrimidine itk inhibitors for treating inflammation and cancer
JP2020512975A (ja) 2017-03-28 2020-04-30 ピメラ,インク. Pol1阻害剤の新規な結晶形態
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
JP7478142B2 (ja) * 2018-06-07 2024-05-02 ディスアーム セラピューティクス, インコーポレイテッド Sarm1阻害剤
EP3801503A4 (en) 2018-06-07 2021-12-08 Disarm Therapeutics, Inc. INHIBITORS OF SARM1
EP3608326A1 (en) 2018-08-10 2020-02-12 Irbm S.P.A. Tricyclic inhibitors of hepatitis b virus
JP2021535198A (ja) 2018-08-17 2021-12-16 ピーティーシー セラピューティクス, インコーポレイテッド 膵臓癌を治療する方法
UY38705A (es) 2019-05-23 2020-12-31 Irbm S P A Inhibidores tricíclicos sustituidos con oxalamido del virus de hepatitis b
EP3825318A1 (en) 2019-11-25 2021-05-26 Promidis S.r.l. Oxalamido-substituted tricyclic inhibitors of hepatitis b virus
EP3741762A1 (en) 2019-05-23 2020-11-25 Irbm S.P.A. Oxalamido-substituted tricyclic inhibitors of hepatitis b virus
IL298941A (en) 2020-06-11 2023-02-01 Chdi Foundation Inc Heterocyclic compounds and imaging agents for the imaging of huntingtin protein
WO2022026935A1 (en) * 2020-07-31 2022-02-03 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
JP2024529453A (ja) * 2021-07-30 2024-08-06 チルドレンズ ホスピタル メディカル センター 多環式irak及びflt3阻害化合物並びにその使用
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
EP4608836A1 (en) 2022-10-27 2025-09-03 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
JP4652648B2 (ja) 1999-08-27 2011-03-16 ノバルティス バクシンズ アンド ダイアグノスティックス,インコーポレーテッド キメラアンチセンスオリゴヌクレオチド、およびその細胞トランスフェクション処方物
DE60019318T2 (de) 1999-09-22 2006-03-09 Canbas Co., Ltd., Numazu Zusammensetzungen und verfahren zur inhibierung vom zellulären g2-übergang und sensitisierung von zellen gegen dna-schädigenden wirkstoffe
US6211164B1 (en) 2000-03-10 2001-04-03 Abbott Laboratories Antisense oligonucleotides of the human chk1 gene and uses thereof
NZ527302A (en) 2001-01-05 2006-10-27 Abgenix Inc Antibodies to insulin-like growth factor I receptor
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
US7704995B2 (en) 2002-05-03 2010-04-27 Exelixis, Inc. Protein kinase modulators and methods of use
AU2003234464B2 (en) * 2002-05-03 2009-06-04 Exelixis, Inc. Protein kinase modulators and methods of use
EA009337B1 (ru) 2003-01-09 2007-12-28 Пфайзер Инк. Трициклические соединения, представляющие собой ингибиторы протеинкиназ, для увеличения эффективности противоопухолевых агентов и лучевой терапии
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
US20080070930A1 (en) * 2006-08-24 2008-03-20 Huang Kenneth H Pyrimidine and Pyrazine Derivatives
JP2011500806A (ja) 2007-10-25 2011-01-06 メルク・シャープ・エンド・ドーム・コーポレイション 治療用化合物

Also Published As

Publication number Publication date
WO2010016005A1 (en) 2010-02-11
ES2378513T3 (es) 2012-04-13
US20110144084A1 (en) 2011-06-16
EP2328890B1 (en) 2012-01-25
CA2731368A1 (en) 2010-02-11
JP2011530500A (ja) 2011-12-22
EP2328890A1 (en) 2011-06-08
US8518952B2 (en) 2013-08-27
JP5576370B2 (ja) 2014-08-20
ATE542813T1 (de) 2012-02-15

Similar Documents

Publication Publication Date Title
EP2328890B1 (en) 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors
AU2019259653B2 (en) 2-amino-pyridine or 2-amino-pyrimidine derivatives as cyclin dependent kinase inhibitors
AU2007297212B2 (en) Pyrido (2, 3-D) pyrimidinone compounds and their use as PI3 inhibitors
CA2958262C (en) 1-cyano-pyrrolidine derivatives as deubiquitinase inhibitors (dub) and use thereof
CA2735932C (en) Imidazo[1,5]naphthyridine compounds, their pharmaceutical use and compositions
WO2007023382A2 (en) Pyrimidine amino pyrazole compounds, potent kinase inhibitors
EP4003980A1 (en) Heterobicyclic amides as inhibitors of cd38
AU2008281543A1 (en) Pyrazole compounds and their use as Raf inhibitors
CA2677365A1 (en) 2-amino-5, 7-dihydro-6h-pyrrolo [3, 4-d] pyrimidine derivatives as hsp- 90 inhibitors for treating cancer
WO2022003575A1 (en) Her2 mutation inhibitors
CA3225045A1 (en) Her2 mutation inhibitors
MX2012010050A (es) Inhibidores de pirrolopirazina cinasa.
WO2022207924A1 (en) (s)-1-(5-((pyridin-3-yl)thio)pyrazin-2-yl)-4'h,6'h-spiro[piperidine-4,5'-pyrrolo [1,2-b]pyrazol]-4'-amine derivatives and similar compounds as shp2 inhibitors for the treatment of e.g. cancer
CA3236550A1 (en) Spirotricycle ripk1 inhibitors and methods of uses thereof
CA3246917A1 (en) C-MYC MESSENGER RIBONUCLE ACID (MRNA) TRANSLATION MODULATORS AND THEIR USES IN CANCER TREATMENT

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20170804