CA2692506C - Pyrimidyl cyclopentanes as akt protein kinase inhibitors - Google Patents

Pyrimidyl cyclopentanes as akt protein kinase inhibitors Download PDF

Info

Publication number
CA2692506C
CA2692506C CA2692506A CA2692506A CA2692506C CA 2692506 C CA2692506 C CA 2692506C CA 2692506 A CA2692506 A CA 2692506A CA 2692506 A CA2692506 A CA 2692506A CA 2692506 C CA2692506 C CA 2692506C
Authority
CA
Canada
Prior art keywords
compound
alkyl
formula
optionally substituted
group
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
CA2692506A
Other languages
English (en)
French (fr)
Other versions
CA2692506A1 (en
Inventor
Josef R. Bencsik
James F. Blake
Nicholas C. Kallan
Ian S. Mitchell
Keith L. Spencer
Dengming Xiao
Rui Xu
Christine Chabot
Jun Liang
Brian S. Safina
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 CA2692506A1 publication Critical patent/CA2692506A1/en
Application granted granted Critical
Publication of CA2692506C publication Critical patent/CA2692506C/en
Expired - Fee Related 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Reproductive Health (AREA)
  • Vascular Medicine (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Endocrinology (AREA)
  • Hospice & Palliative Care (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Epidemiology (AREA)
  • Enzymes And Modification Thereof (AREA)
CA2692506A 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors Expired - Fee Related CA2692506C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US94814707P 2007-07-05 2007-07-05
US60/948,147 2007-07-05
PCT/US2008/069147 WO2009006569A1 (en) 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Publications (2)

Publication Number Publication Date
CA2692506A1 CA2692506A1 (en) 2009-01-08
CA2692506C true CA2692506C (en) 2015-11-24

Family

ID=39830222

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2692506A Expired - Fee Related CA2692506C (en) 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Country Status (15)

Country Link
US (1) US8377937B2 (https=)
EP (2) EP2404907B1 (https=)
JP (2) JP5542282B2 (https=)
KR (2) KR101624361B1 (https=)
CN (1) CN101918373B (https=)
AT (1) ATE522509T1 (https=)
AU (1) AU2008272832B2 (https=)
BR (1) BRPI0813993A2 (https=)
CA (1) CA2692506C (https=)
ES (1) ES2533557T3 (https=)
IL (1) IL202617A0 (https=)
MX (1) MX2009014013A (https=)
SI (1) SI2173723T1 (https=)
WO (1) WO2009006569A1 (https=)
ZA (1) ZA200908901B (https=)

Families Citing this family (20)

* 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
CN103396409B (zh) * 2007-07-05 2015-03-11 阵列生物制药公司 作为akt蛋白激酶抑制剂的嘧啶基环戊烷
US8841304B2 (en) 2008-01-08 2014-09-23 Array Biopharma, Inc. Pyrrolopyridines as kinase inhibitors
CN101965347B (zh) 2008-01-09 2013-01-02 阵列生物制药公司 作为激酶抑制剂的吡唑并吡啶
US8853216B2 (en) 2008-01-09 2014-10-07 Array Biopharma, Inc. Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor
CA2711782C (en) 2008-01-09 2017-01-03 Array Biopharma Inc. 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors
GB201110546D0 (en) * 2011-06-22 2011-08-03 Imp Innovations Ltd Compositions
RU2014151017A (ru) 2012-05-17 2016-07-10 Аррэй Байофарма Инк. Способ получения гидроксилированных циклопентилпиримидинов
US10722484B2 (en) 2016-03-09 2020-07-28 K-Gen, Inc. Methods of cancer treatment
EP3532464A4 (en) 2016-10-28 2020-07-08 Icahn School of Medicine at Mount Sinai COMPOSITIONS AND METHODS FOR THE TREATMENT OF EZH2 MEDIATION CANCER
JP2020514252A (ja) 2016-12-08 2020-05-21 アイカーン スクール オブ メディスン アット マウント シナイ Cdk4/6媒介性がんを治療するための組成物および方法
CA3092677A1 (en) 2018-03-06 2019-09-12 Icahn School Of Medicine At Mount Sinai Serine threonine kinase (akt) degradation / disruption compounds and methods of use
CA3104298A1 (en) 2018-06-21 2019-12-26 Icahn School Of Medicine At Mount Sinai Wd40 repeat domain protein 5 (wdr5) degradation / disruption compounds and methods of use
CN118908962A (zh) 2019-05-06 2024-11-08 西奈山伊坎医学院 作为hpk1的降解剂的异双功能化合物
TWI908780B (zh) * 2020-03-17 2025-12-21 大陸商江蘇恆瑞醫藥股份有限公司 稠合二環類衍生物、其製備方法及其在醫藥上的應用
CN113444110B (zh) * 2020-03-25 2023-05-12 江苏恒瑞医药股份有限公司 四氢吡咯并吡唑类衍生物、其制备方法及其在医药上的应用
US12103924B2 (en) 2020-06-01 2024-10-01 Icahn School Of Medicine At Mount Sinai Mitogen-activated protein kinase kinase (MEK) degradation compounds and methods of use
CN117940410A (zh) * 2021-09-17 2024-04-26 江苏恒瑞医药股份有限公司 一种稠合二环类衍生物的可药用盐、晶型及其制备方法
CN116514739B (zh) * 2023-05-09 2025-07-22 天津绿菱气体股份有限公司 一种1,4-二甲基哌嗪及其制备方法

Family Cites Families (86)

* 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
MX19185A (es) 1989-01-20 1993-12-01 Pfizer Procedimiento para preparar 3-(1,2,5,6-tretrahidropiridil)-pirrolopiridinas.
WO1994007890A1 (fr) 1992-10-05 1994-04-14 Ube Industries, Ltd. Compose pyrimidine
WO1995003286A1 (en) 1993-07-23 1995-02-02 The Green Cross Corporation Triazole derivative and pharmaceutical use thereof
GB9416189D0 (en) 1994-08-10 1994-09-28 Merck Sharp & Dohme Therapeutic agents
JP2896532B2 (ja) 1994-08-13 1999-05-31 ユーハン コーポレーション 新規なピリミジン誘導体およびその製造方法
US5543523A (en) 1994-11-15 1996-08-06 Regents Of The University Of Minnesota Method and intermediates for the synthesis of korupensamines
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
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
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
NZ501276A (en) 1997-07-01 2000-10-27 Warner Lambert Co 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors in treating proliferative disorders
CA2290509A1 (en) 1997-07-01 1999-01-14 Warner-Lambert Company 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as mek inhibitors
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
DE69943144D1 (de) 1998-03-31 2011-03-03 Kyowa Hakko Kirin Co Ltd Stickstoffenthaltende heterocyclische verbindungen
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
JP2002534380A (ja) 1999-01-07 2002-10-15 ワーナー−ランバート・カンパニー Mek阻害剤による喘息の治療
AU2203800A (en) 1999-01-07 2000-07-24 Warner-Lambert Company Antiviral method using mek inhibitors
EP1150950A2 (en) 1999-01-13 2001-11-07 Warner-Lambert Company Anthranilic acid derivatives
HUP0105092A3 (en) 1999-01-13 2003-12-29 Warner Lambert Co 1-heterocycle substituted diarylamines and medicaments containing them
EP1144372B1 (en) 1999-01-13 2005-11-30 Warner-Lambert Company Llc Sulphohydroxamic acids and sulphohydroxamates and their use as mek inhibitors
CA2355470C (en) 1999-01-13 2008-09-30 Warner-Lambert Company Benzoheterocycles and their use as mek inhibitors
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
CA2349832A1 (en) 1999-01-13 2000-07-20 Warner-Lambert Company Benzenesulfonamide derivatives and their use as mek inhibitors
GB9910577D0 (en) 1999-05-08 1999-07-07 Zeneca Ltd Chemical compounds
JP2003504401A (ja) 1999-07-16 2003-02-04 ワーナー−ランバート・カンパニー Mek阻害剤を用いる慢性疼痛の治療方法
EP1202732A2 (en) 1999-07-16 2002-05-08 Warner-Lambert Company Llc Method for treating chronic pain using mek inhibitors
JP2003504400A (ja) 1999-07-16 2003-02-04 ワーナー−ランバート・カンパニー Mek阻害剤を用いた慢性痛の治療方法
CA2377092A1 (en) 1999-07-16 2001-01-25 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
BR0109188A (pt) 2000-03-15 2003-03-18 Warner Lambert Co Diarilaminas 5-amida substituìdas como inibidores de mex
DZ3401A1 (fr) 2000-07-19 2002-01-24 Warner Lambert Co Esters oxygenes d'acides 4-iodophenylamino benzhydroxamiques
KR20030059115A (ko) 2000-08-25 2003-07-07 워너-램버트 캄파니 엘엘씨 N-아릴-안트라닐산 및 그의 유도체의 제조 방법
EP1317450B1 (en) * 2000-09-15 2006-11-22 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
EP1337524A1 (en) 2000-11-02 2003-08-27 AstraZeneca AB Substituted quinolines as antitumor agents
WO2002083139A1 (en) 2001-04-10 2002-10-24 Merck & Co., Inc. Inhibitors of akt activity
IL158062A0 (en) 2001-04-30 2004-03-28 Glaxo Group Ltd Fused pyrimidines as antagonists of the corticotropin releasing factor (crf)
AU2002336462A1 (en) 2001-09-06 2003-03-24 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
SG2013013339A (en) 2002-03-13 2014-12-30 Array Biopharma Inc N3 alkylated benzimidazole derivatives as mek inhibitors
EP1482944A4 (en) 2002-03-13 2006-04-19 Array Biopharma Inc NZ ALKYL BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS
US7235537B2 (en) 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
EP1494675A4 (en) 2002-04-08 2006-07-19 Merck & Co Inc HEMMER OF ACT ACTIVITY
CA2481241C (en) 2002-04-08 2010-07-27 Merck & Co., Inc. Fused quinoxaline derivatives as inhibitors of akt activity
CA2480880C (en) 2002-04-08 2011-03-22 Merck & Co., Inc. Inhibitors of akt activity
US7223738B2 (en) 2002-04-08 2007-05-29 Merck & Co., Inc. Inhibitors of Akt activity
JP2005534632A (ja) 2002-05-10 2005-11-17 ニューロクライン バイオサイエンセズ, インコーポレイテッド メラノコルチンレセプターリガンドとしての置換ピペラジン
US20050045867A1 (en) * 2002-10-30 2005-03-03 Ozkan Cengiz S. Nanoscale heterojunctions and methods of making and using thereof
JP2006507299A (ja) 2002-10-30 2006-03-02 メルク エンド カムパニー インコーポレーテッド Akt活性の阻害薬
US20040102360A1 (en) 2002-10-30 2004-05-27 Barnett Stanley F. Combination therapy
EP1428793B1 (en) * 2002-12-12 2011-02-09 Sony Deutschland GmbH Soluble carbon nanotubes
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
DE602004022819D1 (de) 2003-06-06 2009-10-08 Vertex Pharma Von atp-bindende kassette transportern
ZA200601859B (en) 2003-08-05 2008-03-26 Vertex Pharma Condensed pyrimidine compounds as inhibitors of voltagegated ion channels
JP2007501821A (ja) 2003-08-12 2007-02-01 エフ.ホフマン−ラ ロシュ アーゲー Cfrアンタゴニストとしてのテトラヒドロキナゾリン誘導体
MXPA06002618A (es) 2003-09-09 2006-06-05 Ono Pharmaceutical Co Antagonistas del factor de liberacion de corticotropina (crf) y compuestos heterobiciclicos.
US20050182061A1 (en) 2003-10-02 2005-08-18 Jeremy Green Phthalimide compounds useful as protein kinase inhibitors
CA2546754A1 (en) * 2003-11-21 2005-06-09 Array Biopharma Inc. Akt protein kinase inhibitors
WO2005117909A2 (en) 2004-04-23 2005-12-15 Exelixis, Inc. Kinase modulators and methods of use
WO2005113762A1 (en) 2004-05-18 2005-12-01 Pfizer Products Inc. CRYSTAL STRUCTURE OF PROTEIN KINASE B-α (AKT-1) AND USES THEREOF
US7556746B2 (en) * 2004-06-03 2009-07-07 Nantero, Inc. Method of making an applicator liquid for electronics fabrication process
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
CA2590961C (en) 2004-12-28 2013-11-26 Exelixis, Inc. [1h-pyrazolo[3,4-d]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-threonine kinase modulators (p70s6k, atk1 and atk2) for the treatment of immunological, inflammatory and proliferative diseases
US20090111805A1 (en) 2005-02-24 2009-04-30 Pfizer Inc. Bicyclic heteroaromatic derivatives useful as anticancer agents
WO2006127587A1 (en) 2005-05-20 2006-11-30 Vertex Pharmaceuticals Incorporated Pyrrolopyridines useful as inhibitors of protein kinase
UY29610A1 (es) 2005-06-21 2007-01-31 Cancer Rec Tech Ltd Aril-alquilaminas y heteroaril-alquilaminas como inhibidores de la quinasa proteínica
WO2007042298A1 (en) 2005-10-13 2007-04-19 Glaxo Group Limited Pyrrolopyrimidine derivatives as syk inhibitors
CA2635541A1 (en) 2005-12-28 2007-07-12 Takeda Pharmaceutical Company Limited Fused heterocyclic compounds and their use as mineralocorticoid receptor ligands
JP2009534454A (ja) 2006-04-25 2009-09-24 アステックス、セラピューティックス、リミテッド 医薬化合物
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
EP2049500B1 (en) 2006-07-06 2011-09-07 Array Biopharma, Inc. Cyclopenta [d] pyrimidines as akt protein kinase inhibitors
GB0613518D0 (en) 2006-07-06 2006-08-16 Phytopharm Plc Chemical compounds
CA2655675A1 (en) 2006-07-06 2008-01-10 Glaxo Group Limited Substituted n-phenylmethyl -5-oxo-proline-2-amides as p2x7-receptor antagonists and their methods of use
TW200808325A (en) 2006-07-06 2008-02-16 Astrazeneca Ab Novel compounds
US8063050B2 (en) 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
US7910747B2 (en) 2006-07-06 2011-03-22 Bristol-Myers Squibb Company Phosphonate and phosphinate pyrazolylamide glucokinase activators
WO2008012635A2 (en) 2006-07-26 2008-01-31 Pfizer Products Inc. Amine derivatives useful as anticancer agents

Also Published As

Publication number Publication date
EP2173723B3 (en) 2014-11-19
JP2010532387A (ja) 2010-10-07
SI2173723T1 (sl) 2011-12-30
MX2009014013A (es) 2010-01-28
AU2008272832A1 (en) 2009-01-08
WO2009006569A1 (en) 2009-01-08
EP2404907B1 (en) 2015-01-14
CN101918373B (zh) 2013-06-05
JP5542282B2 (ja) 2014-07-09
CA2692506A1 (en) 2009-01-08
BRPI0813993A2 (pt) 2015-06-16
HK1136832A1 (en) 2010-07-09
JP2014040489A (ja) 2014-03-06
US8377937B2 (en) 2013-02-19
AU2008272832B2 (en) 2014-02-20
EP2173723A1 (en) 2010-04-14
ES2533557T3 (es) 2015-04-13
EP2173723B1 (en) 2011-08-31
KR101624361B1 (ko) 2016-05-25
CN101918373A (zh) 2010-12-15
RU2010103811A (ru) 2011-08-10
ATE522509T1 (de) 2011-09-15
KR20100029846A (ko) 2010-03-17
US20110160221A1 (en) 2011-06-30
KR20150091196A (ko) 2015-08-07
HK1166078A1 (en) 2012-10-19
IL202617A0 (en) 2010-06-30
EP2404907A1 (en) 2012-01-11
ZA200908901B (en) 2011-10-26

Similar Documents

Publication Publication Date Title
CA2692506C (en) Pyrimidyl cyclopentanes as akt protein kinase inhibitors
US8618097B2 (en) Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
KR101578877B1 (ko) AKT 단백질 키나제 억제제로서의 히드록실화 및 메톡실화 시클로펜타[d]피리미딘
US8846683B2 (en) Pyrimidyl cyclopentanes as Akt protein kinase inhibitors
US9409886B2 (en) Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
RU2486178C2 (ru) Пиримидилциклопентаны в качестве ингибиторов akt-протеинкиназы
HK1166078B (en) Pyrimidyl cyclopentanes as akt protein kinase inhibitors
HK1136832B (en) Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130702

MKLA Lapsed

Effective date: 20210705