CN101932564B - 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类 - Google Patents

作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类 Download PDF

Info

Publication number
CN101932564B
CN101932564B CN2009801019017A CN200980101901A CN101932564B CN 101932564 B CN101932564 B CN 101932564B CN 2009801019017 A CN2009801019017 A CN 2009801019017A CN 200980101901 A CN200980101901 A CN 200980101901A CN 101932564 B CN101932564 B CN 101932564B
Authority
CN
China
Prior art keywords
compound
compounds
akt
compound according
disease
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.)
Active
Application number
CN2009801019017A
Other languages
English (en)
Chinese (zh)
Other versions
CN101932564A (zh
Inventor
约瑟夫·R·本西克
詹姆斯·F·布拉克
尼古拉斯·C·卡兰
伊恩·S·米切尔
基思·L·斯潘塞
校登明
徐睿
克里斯廷·沙博
史蒂文·多
梁军
布赖恩·萨菲纳
张碧荣
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
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 Genentech Inc, Array Biopharma Inc filed Critical Genentech Inc
Publication of CN101932564A publication Critical patent/CN101932564A/zh
Application granted granted Critical
Publication of CN101932564B publication Critical patent/CN101932564B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CN2009801019017A 2008-01-09 2009-01-09 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类 Active CN101932564B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US2009208P 2008-01-09 2008-01-09
US61/020,092 2008-01-09
PCT/US2009/030610 WO2009089459A1 (en) 2008-01-09 2009-01-09 Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors

Publications (2)

Publication Number Publication Date
CN101932564A CN101932564A (zh) 2010-12-29
CN101932564B true CN101932564B (zh) 2012-12-26

Family

ID=40552865

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2009801019017A Active CN101932564B (zh) 2008-01-09 2009-01-09 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类

Country Status (18)

Country Link
US (1) US8835434B2 (enExample)
EP (1) EP2247578B1 (enExample)
JP (1) JP5346345B2 (enExample)
KR (1) KR101624753B1 (enExample)
CN (1) CN101932564B (enExample)
AU (1) AU2009204025B2 (enExample)
BR (1) BRPI0906798A2 (enExample)
CA (1) CA2711699A1 (enExample)
CR (1) CR11601A (enExample)
EC (1) ECSP10010389A (enExample)
ES (1) ES2422733T3 (enExample)
IL (1) IL206575A0 (enExample)
MA (1) MA32183B1 (enExample)
NZ (1) NZ586346A (enExample)
RU (1) RU2504542C2 (enExample)
UA (1) UA100545C2 (enExample)
WO (1) WO2009089459A1 (enExample)
ZA (1) ZA201004769B (enExample)

Families Citing this family (9)

* 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
WO2009006567A2 (en) * 2007-07-05 2009-01-08 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
EP2242757B1 (en) 2008-01-09 2012-08-01 Array Biopharma, Inc. Pyrazolopyridines as kinase inhibitors
US8329709B2 (en) 2008-01-09 2012-12-11 Genentech, Inc. 5H-cyclopenta[D]pyrimidines as AKT protein kinase inhibitors
ES2588878T3 (es) 2012-05-17 2016-11-07 Array Biopharma, Inc. Proceso para preparar compuestos de ciclopentilpirimidina hidroxilada
EP3719014A1 (en) * 2012-05-17 2020-10-07 Genentech, Inc. Solid forms of an akt inhibiting pyrimidinyl-cyclopentane compound, compositions and methods thereof
CN112898210B (zh) * 2013-11-15 2025-02-21 豪夫迈·罗氏有限公司 用于制备嘧啶基环戊烷化合物的方法

Family Cites Families (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3885035A (en) 1972-04-05 1975-05-20 Sandoz Ag Method for treating arrhythmia by using 1,4-bis(4 quinazolinyl) piperazines
US3956495A (en) 1973-10-30 1976-05-11 Eli Lilly And Company 2,4-Diaminoquinazolines as antithrombotic agents
US3966936A (en) 1974-02-21 1976-06-29 Pfizer Inc. Piperazino quinazoline bronchodilators
US4060615A (en) 1976-02-18 1977-11-29 Mead Johnson & Company 2-Piperazinyl-6,7-dimethoxyquinazolines
JPS562968A (en) 1979-06-21 1981-01-13 Mitsubishi Yuka Yakuhin Kk Novel pyrimidine derivative
US4749704A (en) 1985-03-07 1988-06-07 Sankyo Company Limited Cyclopenta[d]pyrimidine derivatives and use as antidepressants
WO1990007926A1 (en) 1989-01-20 1990-07-26 Pfizer Inc. 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines
PT664291E (pt) 1992-10-05 2000-11-30 Ube Industries Composto de pirimidina
EP0710654A4 (en) 1993-07-23 1996-08-28 Green Cross Corp TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE
GB9416189D0 (en) 1994-08-10 1994-09-28 Merck Sharp & Dohme Therapeutic agents
CN1102144C (zh) 1994-08-13 2003-02-26 株式会社柳韩洋行 新的嘧啶衍生物及其制备方法
US5525625A (en) 1995-01-24 1996-06-11 Warner-Lambert Company 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders
US7125880B1 (en) 1995-06-06 2006-10-24 Pfizer Inc. Corticotropin releasing factor antagonists
ZA979961B (en) 1996-11-15 1999-05-05 Lilly Co Eli 5-HT1F agonists
UA73073C2 (uk) 1997-04-03 2005-06-15 Уайт Холдінгз Корпорейшн Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція
US6310060B1 (en) 1998-06-24 2001-10-30 Warner-Lambert Company 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors
US6506798B1 (en) 1997-07-01 2003-01-14 Warner-Lambert Company 4-Arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective MEK inhibitors
CA2290506C (en) 1997-07-01 2005-12-27 Warner-Lambert Company 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors
DE69836378T2 (de) 1997-07-01 2007-10-11 Warner-Lambert Co. Llc Benzoesäure- und Benzamid-Derivate von Anthranilsäure und ihre Anwendung als MEK-Inhibitoren
US6821963B2 (en) 1997-07-01 2004-11-23 Warner-Lambert Company 4-Bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors
CA2326324C (en) 1998-03-31 2010-05-11 Kyowa Hakko Kogyo Co., Ltd. Nitrogen-containing heterocyclic compound
DE19853278A1 (de) 1998-11-19 2000-05-25 Aventis Pharma Gmbh Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
HUP0104933A3 (en) 1999-01-07 2003-12-29 Warner Lambert Co Antiviral method using mek inhibitors
BR9916785A (pt) 1999-01-07 2001-10-23 Warner Lambert Co Tratamento de asma com inibidores mek
BR9916894A (pt) 1999-01-13 2001-11-20 Warner Lambert Co ácidos sulfohidroxâmicos e sulfohidroxamatos eseu uso como inibidores de mek
ATE309205T1 (de) 1999-01-13 2005-11-15 Warner Lambert Co Benzenesulfonamid-derivative und ihre verwendung als mek-inhibitoren
CA2348236A1 (en) 1999-01-13 2000-07-20 Stephen Douglas Barrett 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors
DE69926914T2 (de) 1999-01-13 2006-06-29 Warner-Lambert Co. Llc 1-heterozyklus-substituierte diarylaminen
YU49401A (sh) 1999-01-13 2004-07-15 Warner-Lambert Company Benzoheterocikli i njihova upotreba kao inhibitori mek
AU2483400A (en) 1999-01-13 2000-08-01 Warner-Lambert Company 4'heteroaryl diarylamines
GB9910577D0 (en) 1999-05-08 1999-07-07 Zeneca Ltd Chemical compounds
PL352684A1 (pl) 1999-07-16 2003-09-08 Warner-Lambert Company Sposób leczenia chronicznego bólu z użyciem inhibitorów MEK
IL147150A0 (en) 1999-07-16 2002-08-14 Warner Lambert Co Method for treating chronic pain using mek inhibitors
ES2208364T3 (es) 1999-07-16 2004-06-16 Warner-Lambert Company Llc Procedimiento para tratar dolor cronico usando inhibidores de mek.
CA2377100A1 (en) 1999-07-16 2001-01-25 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
CA2403017A1 (en) 2000-03-15 2001-09-20 Warner-Lambert Company 5-amide substituted diarylamines as mex inhibitors
NZ524120A (en) 2000-07-19 2005-08-26 Warner Lambert Co Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids
BR0113520A (pt) 2000-08-25 2003-06-24 Warner Lambert Co Processo de preparação de ácidos n-aril-antranìlicos e seus derivados
WO2002044166A1 (en) 2000-11-02 2002-06-06 Astrazeneca Ab Substituted quinolines as antitumor agents
WO2002083139A1 (en) 2001-04-10 2002-10-24 Merck & Co., Inc. Inhibitors of akt activity
ES2301633T3 (es) 2001-04-30 2008-07-01 Glaxo Group Limited Pirimidinas condensadas como antagonistas del factor de liberacion de corticotropina (crf).
WO2003022214A2 (en) 2001-09-06 2003-03-20 Millennium Pharmaceuticals, Inc. Piperazine and homopiperazine compounds
US20030187026A1 (en) 2001-12-13 2003-10-02 Qun Li Kinase inhibitors
TW200306819A (en) 2002-01-25 2003-12-01 Vertex Pharma Indazole compounds useful as protein kinase inhibitors
PL401638A1 (pl) 2002-03-13 2013-05-27 Array Biopharma Inc. N3 alkilowane pochodne benzimidazolu jako inhibitory MEK
US7235537B2 (en) 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
JP2005526076A (ja) 2002-03-13 2005-09-02 アレイ バイオファーマ、インコーポレイテッド Mek阻害剤としてのn3アルキル化ベンズイミダゾール誘導体
WO2003086403A1 (en) 2002-04-08 2003-10-23 Merck & Co., Inc. Inhibitors of akt activity
US7273869B2 (en) 2002-04-08 2007-09-25 Merck & Co., Inc. Inhibitors of Akt activity
AU2003223467B2 (en) 2002-04-08 2007-10-04 Merck Sharp & Dohme Corp. Inhibitors of Akt activity
CA2481229C (en) 2002-04-08 2010-09-21 Merck & Co., Inc. Substituted pyrazine inhibitors of akt
EP1503761A1 (en) 2002-05-10 2005-02-09 Neurocrine Biosciences, Inc. Substituted piperazines as melanocortin receptor ligands
US20040102360A1 (en) 2002-10-30 2004-05-27 Barnett Stanley F. Combination therapy
CA2501365C (en) 2002-10-30 2011-05-31 Merck & Co., Inc. Inhibitors of akt activity
GB0308208D0 (en) 2003-04-09 2003-05-14 Glaxo Group Ltd Chemical compounds
EP1620095A4 (en) 2003-04-24 2009-04-01 Merck & Co Inc HEMMER OF ACT ACTIVITY
EP1646615B1 (en) 2003-06-06 2009-08-26 Vertex Pharmaceuticals Incorporated Pyrimidine derivatives as modulators of atp-binding cassette transporters
EP1663994B1 (en) 2003-08-05 2012-03-07 Vertex Pharmaceuticals Incorporated Tetrahydroquinazoline compounds as inhibitors of voltage-gated ion channels
ATE374190T1 (de) 2003-08-12 2007-10-15 Hoffmann La Roche Tetrahydrochinazolinderivate als cfr-antagonisten
EP1666468A4 (en) 2003-09-09 2007-03-21 Ono Pharmaceutical Co CRF ANTAGONISTS AND HETEROBICYCLIC COMPOUNDS
WO2005039564A1 (en) 2003-10-02 2005-05-06 Vertex Pharmaceuticals Incorporated Phthalimide compounds useful as protein kinase inhibitors
NO320062B1 (no) * 2003-11-19 2005-10-17 New Interaction Devices And Te Anordning til a detektere naerhet mellom et forste objekt (malobjekt) og et annet objekt (referanseobjekt), samt tegne-, skrive- og/eller pekeredskap for datapresentasjon etc.
NZ547327A (en) * 2003-11-21 2009-08-28 Array Biopharma Inc AKT protein kinase inhibitors
US8076338B2 (en) 2004-04-23 2011-12-13 Exelixis, Inc. Kinase modulators and methods of use
TW200621257A (en) 2004-10-20 2006-07-01 Astellas Pharma Inc Pyrimidine derivative fused with nonaromatic ring
UY29177A1 (es) 2004-10-25 2006-05-31 Astex Therapeutics Ltd Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos
JP5274842B2 (ja) 2004-12-28 2013-08-28 エグゼリクシス, インコーポレイテッド 免疫疾患、炎症疾患および増殖疾患の処置のためのセリン−スレオニンキナーゼモジュレーター(p70S6K、Akt−1およびAkt−2)としての[1H−ピペラゾ[3,4−d]ピリミジン−4−イル]−ピペラジンまたは[1H−ピペラゾ[3,4−d]ピリミジン−4−イル]−ピペラジン化合物
EP1858902A1 (en) 2005-02-24 2007-11-28 Pfizer Products Incorporated Bicyclic heteroaromatic derivatives useful as anticancer agents
NZ564065A (en) 2005-05-20 2011-03-31 Vertex Pharma Pyrrolopyridines useful as inhibitors of protein kinase
AR054485A1 (es) 2005-06-21 2007-06-27 Cancer Rec Tech Ltd ARIL-ALQUILAMINAS Y HETEROARIL-ALQUILAMINAS COMO INHIBIDORES DE PROTEINA QUINASA A Y B, UN PROCESO PARA SU PREPARACION, COMPOSICIONES FARMACEUTICAS QUE LAS CONTIENEN Y SU USO EN LA FABRICACIoN DE MEDICAMENTOS PARA EL TRATAMIENTO O PROFILAXIS DE ENFERMEDADES ORIGINADAS EN EL CRECIMIENTO ANORMAL DE LA
BRPI0617241A2 (pt) 2005-10-13 2016-11-08 Glaxo Group Ltd composto ou um sal ou solvato do mesmo, composição farmacêutica, método para tratar uma doença ou condição mediada por atividade syk inadequada em um mamífero, e, uso de um composto ou um sal ou solvato farmaceuticamente aceitável do mesmo
PE20071164A1 (es) 2005-12-28 2008-01-11 Takeda Pharmaceutical Compuestos heterociclico fusionado como antagonista del receptor mineralocorticoide
US20090124610A1 (en) 2006-04-25 2009-05-14 Gordon Saxty Pharmaceutical compounds
RU2008152171A (ru) 2006-07-05 2010-08-10 Интермьюн, Инк. (Us) Новые ингибиторы вирусной репликации гепатита с
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
SI2049478T1 (sl) 2006-07-06 2012-08-31 Glaxo Group Ltd Substituirani N-fenilmetil-5-okso-prolin-2-amidi kot antagonisti receptorja P2X7 in postopki za njihovo uporabo
TW200808325A (en) 2006-07-06 2008-02-16 Astrazeneca Ab Novel compounds
GB0613518D0 (en) 2006-07-06 2006-08-16 Phytopharm Plc Chemical compounds
US7910747B2 (en) 2006-07-06 2011-03-22 Bristol-Myers Squibb Company Phosphonate and phosphinate pyrazolylamide glucokinase activators
CA2656618C (en) 2006-07-06 2014-08-26 Array Biopharma Inc. Cyclopenta [d] pyrimidines as akt protein kinase inhibitors
US8063050B2 (en) 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
AR061974A1 (es) 2006-07-14 2008-08-10 Novartis Ag Derivados de pirimidina como inhibidores de alk, composiciones farmaceuticas y procesos de obtencion
WO2008012635A2 (en) 2006-07-26 2008-01-31 Pfizer Products Inc. Amine derivatives useful as anticancer agents
WO2009006567A2 (en) 2007-07-05 2009-01-08 Array Biopharma Inc. Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Also Published As

Publication number Publication date
WO2009089459A1 (en) 2009-07-16
RU2504542C2 (ru) 2014-01-20
KR20100118110A (ko) 2010-11-04
JP5346345B2 (ja) 2013-11-20
EP2247578B1 (en) 2013-05-22
EP2247578A1 (en) 2010-11-10
JP2011509308A (ja) 2011-03-24
AU2009204025B2 (en) 2014-02-20
ES2422733T3 (es) 2013-09-13
CR11601A (es) 2010-08-19
AU2009204025A1 (en) 2009-07-16
CN101932564A (zh) 2010-12-29
ZA201004769B (en) 2011-12-28
BRPI0906798A2 (pt) 2015-07-14
ECSP10010389A (es) 2010-11-30
MA32183B1 (fr) 2011-04-01
NZ586346A (en) 2012-02-24
IL206575A0 (en) 2010-12-30
UA100545C2 (ru) 2013-01-10
KR101624753B1 (ko) 2016-05-26
US8835434B2 (en) 2014-09-16
RU2010132911A (ru) 2012-02-20
US20110065716A1 (en) 2011-03-17
CA2711699A1 (en) 2009-07-16

Similar Documents

Publication Publication Date Title
US20250152588A1 (en) Hydroxylated and methoxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors
TWI428335B (zh) 作為akt蛋白質激酶抑制劑之嘧啶環戊烷
CN101932564B (zh) 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类
US9303040B2 (en) Substituted piperazines as AKT inhibitors
CN101932565B (zh) 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷
US20130065908A1 (en) Dihydrofuro pyrimidines as akt protein kinase inhibitors
US20150051217A1 (en) Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor
US20160152574A9 (en) Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors
HK1150201B (en) Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors
HK1150201A (en) Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors
HK1149269B (en) Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant