CA2711782C - 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors - Google Patents

5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors Download PDF

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Publication number
CA2711782C
CA2711782C CA2711782A CA2711782A CA2711782C CA 2711782 C CA2711782 C CA 2711782C CA 2711782 A CA2711782 A CA 2711782A CA 2711782 A CA2711782 A CA 2711782A CA 2711782 C CA2711782 C CA 2711782C
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CA
Canada
Prior art keywords
compound
methyl
dihydro
cyclopenta
pyrimidin
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
CA2711782A
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English (en)
French (fr)
Other versions
CA2711782A1 (en
Inventor
Anna Banka
Josef R. Bencsik
James F. Blake
Martin F. Hentemann
Nicholas C. Kallan
Jun Liang
Ian S. Mitchell
Stephen T. Schlachter
Eli M. Wallace
Rui Xu
Tony P. Tang
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.)
Genentech Inc
Array Biopharma Inc
Original Assignee
Genentech Inc
Array Biopharma Inc
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Filing date
Publication date
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Publication of CA2711782A1 publication Critical patent/CA2711782A1/en
Application granted granted Critical
Publication of CA2711782C publication Critical patent/CA2711782C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/10—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 aromatic rings
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/10—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 two hetero rings linked by a carbon chain containing aromatic rings
    • 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

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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)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2711782A 2008-01-09 2009-01-09 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors Expired - Fee Related CA2711782C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US2012908P 2008-01-09 2008-01-09
US61/020,129 2008-01-09
PCT/US2009/030617 WO2009089462A1 (en) 2008-01-09 2009-01-09 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors

Publications (2)

Publication Number Publication Date
CA2711782A1 CA2711782A1 (en) 2009-07-16
CA2711782C true CA2711782C (en) 2017-01-03

Family

ID=40578062

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2711782A Expired - Fee Related CA2711782C (en) 2008-01-09 2009-01-09 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors

Country Status (7)

Country Link
US (3) US8329709B2 (enExample)
EP (1) EP2250155B1 (enExample)
JP (2) JP5635910B2 (enExample)
CN (2) CN104876921A (enExample)
CA (1) CA2711782C (enExample)
ES (1) ES2426092T3 (enExample)
WO (1) WO2009089462A1 (enExample)

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CA2692502C (en) * 2007-07-05 2016-03-01 Array Biopharma Inc. Pyrimidyl cyclopentanes as akt protein kinase inhibitors
US9409886B2 (en) 2007-07-05 2016-08-09 Array Biopharma Inc. Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
US8846683B2 (en) 2007-07-05 2014-09-30 Array Biopharma, Inc. Pyrimidyl cyclopentanes as Akt protein kinase inhibitors
WO2009089352A1 (en) 2008-01-08 2009-07-16 Array Biopharma Inc. Pyrrolopyridines as kinase inhibitors
CN104876921A (zh) 2008-01-09 2015-09-02 阵列生物制药公司 作为AKT蛋白激酶抑制剂的5H-环戊二烯并[d]嘧啶
EP2242757B1 (en) 2008-01-09 2012-08-01 Array Biopharma, Inc. Pyrazolopyridines as kinase inhibitors
WO2010016554A1 (ja) * 2008-08-07 2010-02-11 武田薬品工業株式会社 環状アミン化合物
US10065960B2 (en) 2010-04-02 2018-09-04 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
CA2793313C (en) 2010-04-02 2018-01-23 Euroscreen Sa Nk-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in nk-3 receptors mediated disorders
CA2849751C (en) * 2011-10-03 2019-06-11 Euroscreen Sa Chiral n-acyl-5,6,7,(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective nk-3 receptor antagonists, pharmaceutical composition, methods for use in nk-3 receptormediated disorders and chiral synthesis thereof
US9422267B2 (en) 2012-12-26 2016-08-23 Medivation Technologies, Inc. Fused pyrimidine compounds and use thereof
AU2014293013A1 (en) 2013-07-26 2016-03-17 Race Oncology Ltd. Combinatorial methods to improve the therapeutic benefit of bisantrene
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JP6469214B2 (ja) 2014-09-25 2019-02-13 オゲダ エス．エー． Ｎ−アシル−（３−置換）−（８−置換）−５，６−ジヒドロ−［１，２，４］トリアゾロ［４，３−ａ］ピラジンの新規キラル合成
US12617784B2 (en) 2019-01-29 2026-05-05 Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. AKT inhibitor
JP7397183B2 (ja) * 2019-10-22 2023-12-12 昊運股▲フン▼有限公司 ピリミジンアミド化合物及びその使用
GB201918815D0 (en) * 2019-12-19 2020-02-05 Imperial College Innovations Ltd Treatment of cancer
JP2023520140A (ja) 2020-03-17 2023-05-16 江蘇恒瑞医薬股▲ふん▼有限公司 縮合二環系誘導体、その調製方法及びその医薬的応用
CN115485276B (zh) * 2020-05-15 2024-05-31 南京正大天晴制药有限公司 氘代akt激酶抑制剂
CN111533745A (zh) * 2020-05-20 2020-08-14 成都药明康德新药开发有限公司 叔丁基-3-(氨基甲基)二氢-5h-三唑并二氮杂卓-8(9h)-甲酸基酯制法
EP4186902A4 (en) 2020-07-22 2024-06-05 Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. DIHYDROPYRIDO[2,3-D]PYRIMIDINONE DERIVATIVE SALT, PREPARATION METHOD AND USE THEREOF
US12673061B2 (en) 2020-07-22 2026-07-07 Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. Unit dosage composition of AKT inhibitor
WO2023109540A1 (zh) * 2021-12-17 2023-06-22 中国医药研究开发中心有限公司 具有akt激酶抑制活性的杂环化合物及其制备方法和医药用途
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US9409886B2 (en) 2007-07-05 2016-08-09 Array Biopharma Inc. Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
CN104876921A (zh) 2008-01-09 2015-09-02 阵列生物制药公司 作为AKT蛋白激酶抑制剂的5H-环戊二烯并[d]嘧啶
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Also Published As

Publication number Publication date
US8895566B2 (en) 2014-11-25
CN101970415A (zh) 2011-02-09
US20110251181A1 (en) 2011-10-13
US8329709B2 (en) 2012-12-11
EP2250155A1 (en) 2010-11-17
JP2015007097A (ja) 2015-01-15
US20130085135A1 (en) 2013-04-04
WO2009089462A1 (en) 2009-07-16
CN104876921A (zh) 2015-09-02
US9328091B2 (en) 2016-05-03
US20150266852A1 (en) 2015-09-24
JP5635910B2 (ja) 2014-12-03
HK1150605A1 (en) 2012-01-06
EP2250155B1 (en) 2013-07-03
JP2011509309A (ja) 2011-03-24
ES2426092T3 (es) 2013-10-21
CA2711782A1 (en) 2009-07-16

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