CA2709536C - Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer - Google Patents

Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer Download PDF

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Publication number
CA2709536C
CA2709536C CA2709536A CA2709536A CA2709536C CA 2709536 C CA2709536 C CA 2709536C CA 2709536 A CA2709536 A CA 2709536A CA 2709536 A CA2709536 A CA 2709536A CA 2709536 C CA2709536 C CA 2709536C
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alkyl
optionally substituted
group
phenyl
halogen
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English (en)
French (fr)
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CA2709536A1 (en
Inventor
Heinz W. Pauls
Bryan T. Forrest
Radoslaw Laufer
Miklos Feher
Peter Brent Sampson
Guohua Pan
Sze-Wan Li
Yong Liu
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University Health Network
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University Health Network
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    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • C07D403/02—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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

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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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2709536A 2007-12-21 2008-12-19 Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer Active CA2709536C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US886507P 2007-12-21 2007-12-21
US61/008,865 2007-12-21
US13171708P 2008-06-11 2008-06-11
US61/131,717 2008-06-11
PCT/CA2008/002227 WO2009079767A1 (en) 2007-12-21 2008-12-19 Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer

Publications (2)

Publication Number Publication Date
CA2709536A1 CA2709536A1 (en) 2009-07-02
CA2709536C true CA2709536C (en) 2016-05-31

Family

ID=40800609

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2709536A Active CA2709536C (en) 2007-12-21 2008-12-19 Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer

Country Status (7)

Country Link
US (1) US8765748B2 (enExample)
EP (1) EP2235004A4 (enExample)
JP (1) JP2011506494A (enExample)
CN (1) CN101970426A (enExample)
AU (1) AU2008340991B2 (enExample)
CA (1) CA2709536C (enExample)
WO (1) WO2009079767A1 (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2235004A4 (en) 2007-12-21 2011-05-04 Univ Health Network INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL-SUBSTITUTED INDOLUND DERIVATIVES AS A KINASE-HEMMER FOR CANCER TREATMENT
WO2010115279A1 (en) 2009-04-06 2010-10-14 University Health Network Kinase inhibitors and method of treating cancer with same
TWI516262B (zh) * 2010-04-06 2016-01-11 健康網路大學 激酶抑制劑及以其治療癌症的方法
CA2803446C (en) 2010-07-02 2019-06-04 University Health Network Use of plk4 antagonists for treating pten mutant diseases
WO2012048411A1 (en) * 2010-10-13 2012-04-19 University Health Network Plk-4 inhibitors and method of treating cancer with same
CN102295640B (zh) * 2011-06-29 2013-09-18 南京工业大学 3-杂环席夫碱-5-氟-吲哚-2-酮类化合物及其制备方法和应用
CN103006642B (zh) * 2013-01-04 2014-10-22 中国药科大学 一类炔亚甲基吲哚-2-酮类衍生物的用途
AU2014331111B2 (en) 2013-10-04 2018-05-31 Bayer Cropscience Aktiencesellschaft Use of substituted dihydro-oxindolyl sulfonamides, or the salts thereof, for increasing the stress tolerance of plants
TR201902875T4 (tr) 2013-10-18 2019-03-21 Univ Health Network Plk-4 inhibitörünün tuz ve kristal formları.
EA030089B1 (ru) 2013-10-18 2018-06-29 Юниверсити Хелс Нетуорк Лечение рака поджелудочной железы
WO2015164956A1 (en) * 2014-04-29 2015-11-05 The University Of British Columbia Benzisothiazole derivative compounds as therapeutics and methods for their use
CN113912586B (zh) 2016-08-31 2023-04-07 江苏恒瑞医药股份有限公司 氧代吡啶酰胺类衍生物、其制备方法及其在医药上的应用
CN106916143B (zh) * 2017-03-14 2019-09-27 哈尔滨医科大学 一种预防和治疗冠心病的药物及其应用
EP3959209A4 (en) 2019-04-24 2022-12-28 University Health Network S4 CRYSTALLINE FORM OF A PLK4 INHIBITOR (1R,2S)-(E)-2-(3-(4-((CIS-2,6-DIMETHYLMORPHOLINO)METHYL)STYRYL)-1H-IMIDAZOL-6-YL )-5'-METHOXYSPIRO[CYCLOPROPANE-L,3'-INDOLIN]-2'-ONE FUMARATE
TW202300485A (zh) * 2021-03-02 2023-01-01 大陸商上海齊魯製藥研究中心有限公司 Plk4抑制劑及其用途
TWI926033B (zh) 2021-05-11 2026-05-21 美商歐瑞克製藥公司 類ｐｏｌｏ激酶４抑制劑
WO2024209363A1 (en) 2023-04-06 2024-10-10 Pfizer Inc. Substituted indazole propionic acid derivative compounds and uses thereof as ampk activators
ES3022196A1 (es) * 2023-11-27 2025-05-28 Univ Madrid Complutense Derivados de 2-indolinona y usos de los mismos

Family Cites Families (21)

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Publication number Priority date Publication date Assignee Title
US1326A (en) * 1839-09-17 Improvement in the mode of setting and arranging sugar-kettles
DE3310891A1 (de) * 1983-03-25 1984-09-27 Boehringer Mannheim Gmbh, 6800 Mannheim Neue indolinon-(2)-derivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und zwischenprodukte
US5182397A (en) 1990-05-31 1993-01-26 American Cyanamid Company Aryloxyspiroalkylindolinone herbicides
GB9507298D0 (en) 1995-04-07 1995-05-31 Pharmacia Spa Substituted indolylmethylene-oxindale analogues as tyrosine kinase inhibitors
US5880141A (en) 1995-06-07 1999-03-09 Sugen, Inc. Benzylidene-Z-indoline compounds for the treatment of disease
EP0929520B1 (en) * 1996-08-23 2005-11-02 Sugen, Inc. Indolinone combinatorial libraries and related products and methods for the treatment of disease
GB9716557D0 (en) 1997-08-06 1997-10-08 Glaxo Group Ltd Benzylidene-1,3-dihydro-indol-2-one derivatives having anti-cancer activity
US6133305A (en) * 1997-09-26 2000-10-17 Sugen, Inc. 3-(substituted)-2-indolinones compounds and use thereof as inhibitors of protein kinase activity
CA2383623A1 (en) * 1998-08-04 2000-02-17 Sugen, Inc. 3-methylidenyl-2-indolinone modulators of protein kinase
AU3770000A (en) 1999-03-24 2000-10-09 Sugen, Inc. Indolinone compounds as kinase inhibitors
US7148249B2 (en) 2002-09-12 2006-12-12 Boehringer Ingelheim Pharma Gmbh & Co. Kg Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments
US7205328B2 (en) 2002-10-21 2007-04-17 Irm Llc Oxindoles with anti-HIV activity
WO2005058309A1 (en) * 2003-12-16 2005-06-30 Leo Pharma A/S Novel therapeutic use of indolinone derivatives
US7309787B2 (en) 2005-07-13 2007-12-18 Allergan, Inc. Kinase inhibitors
US20070135509A1 (en) 2005-12-09 2007-06-14 Blackburn Thomas P Indolone compounds useful to treat cognitive impairment
EP2181108A2 (en) 2007-06-12 2010-05-05 Boehringer Ingelheim International GmbH 3-hetrocyclylidene-indolinone derivatives as inhibitors of specific cell cycle kinases
EP2235004A4 (en) 2007-12-21 2011-05-04 Univ Health Network INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL-SUBSTITUTED INDOLUND DERIVATIVES AS A KINASE-HEMMER FOR CANCER TREATMENT
EP2108641A1 (en) 2008-04-11 2009-10-14 Laboratorios Almirall, S.A. New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors
EP2113503A1 (en) 2008-04-28 2009-11-04 Laboratorios Almirall, S.A. New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors
WO2010115279A1 (en) 2009-04-06 2010-10-14 University Health Network Kinase inhibitors and method of treating cancer with same
TWI516262B (zh) 2010-04-06 2016-01-11 健康網路大學 激酶抑制劑及以其治療癌症的方法

Also Published As

Publication number Publication date
US20110065702A1 (en) 2011-03-17
EP2235004A4 (en) 2011-05-04
JP2011506494A (ja) 2011-03-03
AU2008340991B2 (en) 2012-02-23
WO2009079767A1 (en) 2009-07-02
CN101970426A (zh) 2011-02-09
WO2009079767A9 (en) 2009-10-01
CA2709536A1 (en) 2009-07-02
US8765748B2 (en) 2014-07-01
AU2008340991A1 (en) 2009-07-02
EP2235004A1 (en) 2010-10-06

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