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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Oncology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (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)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8846683B2 (en) 2007-07-05 2014-09-30 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
US8618097B2 (en) * 2007-07-05 2013-12-31 Array Biopharma, Inc. Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
CN101959887B (zh) 2008-01-08 2013-07-31 阵列生物制药公司 作为激酶抑制剂的吡咯并吡啶
CA2711782C (en) 2008-01-09 2017-01-03 Array Biopharma Inc. 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors
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
EP2552920B1 (en) 2010-04-02 2017-03-15 Ogeda Sa Novel nk-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in nk-3 receptors mediated disorders
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
HUE028858T2 (hu) 2011-10-03 2017-01-30 Euroscreen Sa Új királis N-acil-5,6,7,(8-szubsztituált)-tetrahidro-[1,2,4]triazolo[4,3-A]pirazinok mint szelektív NK-3 receptor antagonisták, gyógyászati készítmény és eljárások NK-3 receptor által közvetített rendellenességek során történõ alkalmazásra
WO2014105958A2 (en) * 2012-12-26 2014-07-03 Medivation Technologies, Inc. Fused pyrimidine compounds and use thereof
CA2928568A1 (en) 2013-07-26 2015-01-29 Update Pharma Inc. Combinatorial methods to improve the therapeutic benefit of bisantrene
US20170137410A1 (en) * 2014-07-02 2017-05-18 Medivation Technologies, Inc Fused cycloalkyl-pyrimidine compounds and uses thereof
ES2711095T3 (es) 2014-09-25 2019-04-30 Ogeda Sa Nueva síntesis quiral de N-acil-(3-sustituida)-(8-sustituida)-5,6-dihidro-[1,2,4]triazolo [4,3-a] pirazinas
PL3919491T3 (pl) * 2019-01-29 2025-10-20 Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. Inhibitor akt
KR20220066332A (ko) * 2019-10-22 2022-05-24 알파라 컴퍼니 리미티드 피리미딘 아미드 화합물 및 이의 용도
GB201918815D0 (en) * 2019-12-19 2020-02-05 Imperial College Innovations Ltd Treatment of cancer
CN118530260A (zh) 2020-03-17 2024-08-23 江苏恒瑞医药股份有限公司 稠合二环类衍生物、其制备方法及其在医药上的应用
WO2021228223A1 (zh) * 2020-05-15 2021-11-18 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
AU2021314419B2 (en) 2020-07-22 2023-12-07 Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. Salt of dihydropyrido[2,3-d]pyrimidinone derivative, preparation method therefor, and use thereof
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
TW202400598A (zh) * 2022-06-14 2024-01-01 昊運股份有限公司 嘧啶醯胺化合物及其用途

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5543523A (en) 1994-11-15 1996-08-06 Regents Of The University Of Minnesota Method and intermediates for the synthesis of korupensamines
ES2266258T3 (es) * 2000-09-15 2007-03-01 Vertex Pharmaceuticals Incorporated Compuestos de pirazol utiles como inhibidores de proteina cinasas.
WO2004052862A1 (ja) * 2002-12-10 2004-06-24 Ono Pharmaceutical Co., Ltd. 含窒素複素環化合物およびその医薬用途
US20050130954A1 (en) 2003-11-21 2005-06-16 Mitchell Ian S. AKT protein kinase inhibitors
WO2005113762A1 (en) 2004-05-18 2005-12-01 Pfizer Products Inc. CRYSTAL STRUCTURE OF PROTEIN KINASE B-α (AKT-1) AND USES THEREOF
US7994172B2 (en) * 2004-12-28 2011-08-09 Exelixis, Inc. [1H-pyrazolo[3, 4-D]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-theoronine kinase modulators (P70s6k, Atk1 and Atk2) for the treatment of immunological, inflammatory and proliferative diseases
EP1968568A4 (en) * 2005-12-22 2011-04-13 Glaxosmithkline Llc HEMMER OF NUTS ACTIVITY
US20090124610A1 (en) * 2006-04-25 2009-05-14 Gordon Saxty Pharmaceutical compounds
US7851468B2 (en) * 2006-05-15 2010-12-14 Cephalon, Inc. Substituted pyrazolo[3,4-d]pyrimidines
US8063050B2 (en) 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
CN101511842B (zh) 2006-07-06 2012-10-31 阵列生物制药公司 作为akt蛋白激酶抑制剂的二氢呋喃并嘧啶
WO2008006032A1 (en) 2006-07-06 2008-01-10 Array Biopharma Inc. Cyclopenta [d] pyrimidines as akt protein kinase inhibitors
US20130065908A1 (en) 2009-12-07 2013-03-14 Array Biopharma Inc. Dihydrofuro pyrimidines as akt protein kinase inhibitors
UA95641C2 (xx) * 2006-07-06 2011-08-25 Эррей Биофарма Инк. Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы
ATE532789T1 (de) 2006-07-06 2011-11-15 Array Biopharma Inc Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren
US20090118135A1 (en) 2007-06-08 2009-05-07 The Burnham Institute Methods and compounds for regulating apoptosis
US8618097B2 (en) 2007-07-05 2013-12-31 Array Biopharma, Inc. Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
SI2173723T1 (sl) 2007-07-05 2011-12-30 Array Biopharma Inc Pirimidil ciklopentani kot inhibitorji AKT-protein-kinaze
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
JP5346345B2 (ja) 2008-01-09 2013-11-20 アレイ バイオファーマ、インコーポレイテッド Ａｋｔタンパク質キナーゼ阻害剤としての水酸化されたピリミジルシクロペンタン類
CA2711782C (en) 2008-01-09 2017-01-03 Array Biopharma Inc. 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors
US20160152574A9 (en) 2008-01-09 2016-06-02 Array Biopharma Inc. Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors
EP2240455B1 (en) 2008-01-09 2012-12-26 Array Biopharma, Inc. Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor
EP2265610B1 (en) 2008-02-29 2012-12-12 Array Biopharma, Inc. Pyrazole [3, 4-b]pyridine raf inhibitors
JPWO2009154207A1 (ja) * 2008-06-17 2011-12-01 出光興産株式会社 アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
US20150051217A1 (en) 2010-07-07 2015-02-19 Array Biopharma Inc. Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor

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

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