CA2692502C - Pyrimidyl cyclopentanes as akt protein kinase inhibitors - Google Patents

Pyrimidyl cyclopentanes as akt protein kinase inhibitors Download PDF

Info

Publication number
CA2692502C
CA2692502C CA2692502A CA2692502A CA2692502C CA 2692502 C CA2692502 C CA 2692502C CA 2692502 A CA2692502 A CA 2692502A CA 2692502 A CA2692502 A CA 2692502A CA 2692502 C CA2692502 C CA 2692502C
Authority
CA
Canada
Prior art keywords
cyclopenta
dihydro
pyrimidin
methyl
piperazin
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
CA2692502A
Other languages
English (en)
French (fr)
Other versions
CA2692502A1 (en
Inventor
Josef Bencsik
James F. Blake
James M. Graham
Martin F. Hentemann
Nicholas C. Kallan
Ian S. Mitchell
Stephen T. Schlachter
Keith L. Spencer
Dengming Xiao
Rui Xu
Mike Welch
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 CA2692502A1 publication Critical patent/CA2692502A1/en
Application granted granted Critical
Publication of CA2692502C publication Critical patent/CA2692502C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/28—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • A61P9/10—Drugs 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Communicable Diseases (AREA)
  • Dermatology (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Virology (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Ophthalmology & Optometry (AREA)
CA2692502A 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors Expired - Fee Related CA2692502C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US94813807P 2007-07-05 2007-07-05
US60/948,138 2007-07-05
US2008808P 2008-01-09 2008-01-09
US61/020,088 2008-01-09
PCT/US2008/069144 WO2009006567A2 (en) 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Publications (2)

Publication Number Publication Date
CA2692502A1 CA2692502A1 (en) 2009-01-08
CA2692502C true CA2692502C (en) 2016-03-01

Family

ID=40076864

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2692502A Expired - Fee Related CA2692502C (en) 2007-07-05 2008-07-03 Pyrimidyl cyclopentanes as akt protein kinase inhibitors

Country Status (19)

Country Link
US (1) US8618097B2 (online.php)
EP (1) EP2170863B1 (online.php)
JP (2) JP5628028B2 (online.php)
KR (2) KR20150089099A (online.php)
CN (2) CN103396409B (online.php)
AR (1) AR067413A1 (online.php)
AU (1) AU2008272830B8 (online.php)
BR (1) BRPI0813999A2 (online.php)
CA (1) CA2692502C (online.php)
CO (1) CO6251283A2 (online.php)
CR (1) CR11229A (online.php)
EC (1) ECSP109937A (online.php)
ES (1) ES2551352T3 (online.php)
MA (1) MA31679B1 (online.php)
NZ (1) NZ582692A (online.php)
RU (1) RU2486181C2 (online.php)
SG (1) SG185274A1 (online.php)
TW (1) TWI450720B (online.php)
WO (1) WO2009006567A2 (online.php)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2729424T3 (es) 2006-09-20 2019-11-04 Aerie Pharmaceuticals Inc Inhibidores de Rho cinasa
US8455513B2 (en) 2007-01-10 2013-06-04 Aerie Pharmaceuticals, Inc. 6-aminoisoquinoline compounds
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
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
EP2240455B1 (en) * 2008-01-09 2012-12-26 Array Biopharma, Inc. Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor
EP2242757B1 (en) 2008-01-09 2012-08-01 Array Biopharma, Inc. Pyrazolopyridines as kinase inhibitors
TW200940542A (en) * 2008-01-09 2009-10-01 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
US8450344B2 (en) 2008-07-25 2013-05-28 Aerie Pharmaceuticals, Inc. Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds
EP3828172A1 (en) 2009-05-01 2021-06-02 Aerie Pharmaceuticals, Inc. Dual mechanism inhibitors for the treatment of disease
MX2012011887A (es) 2010-04-16 2012-11-30 Genentech Inc Foxo 3a como biomarcador predictivo para la eficacia del inhibidor de la via de quinasa pi3k/akt.
US20140031259A1 (en) 2011-04-01 2014-01-30 Genentech, Inc. Biomarkers for predicting sensitivity to cancer treatments
DK2858989T3 (da) 2012-05-17 2020-06-02 Genentech Inc Amorf form af en AKT-hæmmende pyrimidinyl-cyclopentan-forbindelse, sammensætninger deraf og fremgangsmåder dertil
AU2013277154A1 (en) 2012-06-20 2014-12-18 Jonathan E. Grob Complement pathway modulators and uses thereof
CA2901126C (en) 2013-02-25 2022-01-25 Genentech, Inc. Methods and compositions for detecting and treating drug resistant akt mutant
US20140275160A1 (en) 2013-03-15 2014-09-18 Aerie Pharmaceuticals, Inc. Combination therapy
JP6832946B2 (ja) 2015-11-17 2021-02-24 アエリエ ファーマシューティカルズ インコーポレイテッド キナーゼ阻害剤およびその中間体の調製方法
US9643927B1 (en) 2015-11-17 2017-05-09 Aerie Pharmaceuticals, Inc. Process for the preparation of kinase inhibitors and intermediates thereof
US10722484B2 (en) 2016-03-09 2020-07-28 K-Gen, Inc. Methods of cancer treatment
WO2017223474A1 (en) 2016-06-23 2017-12-28 St. Jude Children's Research Hospital Small molecule modulators of pantothenate kinases
CN109640966A (zh) 2016-08-31 2019-04-16 爱瑞制药公司 眼用组合物
AU2017348322B8 (en) 2016-10-28 2021-12-23 Icahn School Of Medicine At Mount Sinai Compositions and methods for treating EZH2-mediated cancer
WO2018183911A1 (en) 2017-03-31 2018-10-04 Aerie Pharmaceuticals, Inc. Aryl cyclopropyl-amino-isoquinolinyl amide compounds
MX2020006754A (es) 2017-12-27 2021-01-29 St Jude Childrens Res Hospital Inc Moduladores de molécula pequeña de pantotenato-cinasas.
WO2019173516A1 (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
CN119569702A (zh) * 2018-04-04 2025-03-07 阿尔维纳斯运营股份有限公司 蛋白水解调节剂及相关使用方法
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
US11427563B2 (en) 2018-09-14 2022-08-30 Aerie Pharmaceuticals, Inc. Aryl cyclopropyl-amino-isoquinolinyl amide compounds
WO2020198526A2 (en) * 2019-03-27 2020-10-01 St. Jude Children's Research Hospital Small molecule modulators of pank
US12465648B2 (en) 2019-05-06 2025-11-11 Icahn School Of Medicine At Mount Sinai Heterobifunctional compounds as degraders of HPK1
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
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
CN121419983A (zh) 2023-01-26 2026-01-27 阿尔维纳斯运营股份有限公司 基于小脑蛋白的kras降解protac及其相关用途

Family Cites Families (102)

* 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
JPS6270A (ja) 1985-03-07 1987-01-06 Sankyo Co Ltd シクロペンタ〔ｄ〕ピリミジン誘導体
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
AU688087B2 (en) 1994-08-13 1998-03-05 Yuhan Corporation Novel pyrimidine derivatives and processes for the preparation thereof
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
US7067664B1 (en) 1995-06-06 2006-06-27 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
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
JP2002509536A (ja) 1997-07-01 2002-03-26 ワーナー−ランバート・カンパニー ２−（４−ブロモ又は４−ヨードフェニルアミノ）安息香酸誘導体及びｍｅｋ阻害物質としてのそれらの使用
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
AU757046B2 (en) 1997-07-01 2003-01-30 Warner-Lambert Company 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as 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
AU3053999A (en) 1998-03-31 1999-10-25 Kyowa Hakko Kogyo Co. Ltd. Nitrogenous heterocyclic compounds
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
AU2203800A (en) 1999-01-07 2000-07-24 Warner-Lambert Company Antiviral method using mek inhibitors
DE69924641D1 (de) 1999-01-07 2005-05-12 Warner Lambert Company Llc Mor Behandlung von asthma anhand von 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
IL144214A0 (en) 1999-01-13 2002-05-23 Warner Lambert Co Benzoheterocycles and their use as mek inhibitors
CA2349467A1 (en) 1999-01-13 2000-07-20 Warner-Lambert Company Sulphohydroxamic acids and sulphohydroxamates and their use as mek inhibitors
GEP20032999B (en) 1999-01-13 2003-06-25 Warner Lambert Co 1-Heterocycle Substituted Diarylamines
AU2201500A (en) 1999-01-13 2000-08-01 Warner-Lambert Company Benzenesulfonamide derivatives and their use as mek inhibitors
CA2349180A1 (en) 1999-01-13 2000-07-20 Stephen Douglas Barrett Anthranilic acid derivatives
GB9910577D0 (en) 1999-05-08 1999-07-07 Zeneca Ltd Chemical compounds
EP1202732A2 (en) 1999-07-16 2002-05-08 Warner-Lambert Company Llc Method for treating chronic pain using mek inhibitors
KR20020012315A (ko) 1999-07-16 2002-02-15 로즈 암스트롱, 크리스틴 에이. 트러트웨인 Ｍｅｋ 저해제를 사용한 만성 통증의 치료 방법
AU6068600A (en) 1999-07-16 2001-02-05 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
DK1202724T3 (da) 1999-07-16 2004-01-26 Warner Lambert Co Fremgangsmåde til behandling af kronisk smerte under anvendelse af mek-inhibitorer
AU2001247372A1 (en) 2000-03-15 2001-09-24 Warner Lambert Company 5-amide substituted diarylamines as mex inhibitors
WO2002006213A2 (en) 2000-07-19 2002-01-24 Warner-Lambert Company Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids
KR20030059115A (ko) 2000-08-25 2003-07-07 워너-램버트 캄파니 엘엘씨 Ｎ-아릴-안트라닐산 및 그의 유도체의 제조 방법
ES2266258T3 (es) 2000-09-15 2007-03-01 Vertex Pharmaceuticals Incorporated Compuestos de pirazol utiles como inhibidores de proteina cinasas.
AU2002210714A1 (en) 2000-11-02 2002-06-11 Astrazeneca Ab Substituted quinolines as antitumor agents
WO2002083139A1 (en) 2001-04-10 2002-10-24 Merck & Co., Inc. Inhibitors of akt activity
WO2002088095A1 (en) 2001-04-30 2002-11-07 Glaxo Group Limited Fused pyrimidines as antagonists of the corticotropin releasing factor (crf)
US7115741B2 (en) 2001-09-06 2006-10-03 Levy Daniel E 4-thieno[2,3-D]pyrimidin-4-YL piperazine 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
TWI343377B (en) 2002-03-13 2011-06-11 Array Biopharma Inc N3 alkylated benzimidazole derivatives as mek inhibitors
WO2003077855A2 (en) 2002-03-13 2003-09-25 Array Biopharma, Inc N3 alkylated benzimidazole derivatives as mek inhibitors
US7235537B2 (en) 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
WO2003086279A2 (en) 2002-04-08 2003-10-23 Merck & Co., Inc. Inhibitors of akt activity
WO2003086394A1 (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
WO2003086403A1 (en) 2002-04-08 2003-10-23 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
US20040102360A1 (en) 2002-10-30 2004-05-27 Barnett Stanley F. Combination therapy
US7399764B2 (en) 2002-10-30 2008-07-15 Merck & Co., Inc. Inhibitors of Akt activity
GB0308208D0 (en) 2003-04-09 2003-05-14 Glaxo Group Ltd Chemical compounds
CN1809351A (zh) 2003-04-24 2006-07-26 麦克公司 Akt活性抑制剂
ATE440825T1 (de) 2003-06-06 2009-09-15 Vertex Pharma Pyrimidin-derivate zur verwendung als modulatoren von atp-bindende kassette transportern
NZ545717A (en) 2003-08-05 2009-12-24 Vertex Pharma Hydrogenated quinazoline derivatives as inhibitors of voltage-gated 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.
WO2005039564A1 (en) 2003-10-02 2005-05-06 Vertex Pharmaceuticals Incorporated Phthalimide compounds useful as protein kinase inhibitors
US20050130954A1 (en) * 2003-11-21 2005-06-16 Mitchell Ian S. 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
US20060025074A1 (en) 2004-07-30 2006-02-02 Chih-Ming Liang Bluetooth-based headset
US7521457B2 (en) 2004-08-20 2009-04-21 Boehringer Ingelheim International Gmbh Pyrimidines as PLK inhibitors
GB0419161D0 (en) 2004-08-27 2004-09-29 Novartis Ag Organic compounds
TWM266655U (en) 2004-09-23 2005-06-01 Blueexpert Technology Corp Bluetooth earphone device capable of wirelessly receiving and transmitting stereo sound signal and digital information signal
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
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
WO2006090261A1 (en) 2005-02-24 2006-08-31 Pfizer Products Inc. Bicyclic heteroaromatic derivatives useful as anticancer agents
CA2604284A1 (en) * 2005-04-28 2006-11-02 Supergen, Inc. Protein kinase inhibitors
KR20080016659A (ko) 2005-05-20 2008-02-21 버텍스 파마슈티칼스 인코포레이티드 단백질 키나제의 억제제로서 유용한 피롤로피리딘
AU2006258124B8 (en) 2005-06-10 2010-01-07 Merck Sharp & Dohme Corp. Inhibitors of Akt activity
UY29610A1 (es) 2005-06-21 2007-01-31 Cancer Rec Tech Ltd Aril-alquilaminas y heteroaril-alquilaminas como inhibidores de la quinasa proteínica
US20080004295A1 (en) 2005-10-13 2008-01-03 Gore Paul M Novel compounds
JP2009523701A (ja) 2005-12-28 2009-06-25 武田薬品工業株式会社 縮合複素環化合物およびその用途
US20090124610A1 (en) 2006-04-25 2009-05-14 Gordon Saxty Pharmaceutical compounds
KR20090024834A (ko) 2006-07-05 2009-03-09 인터뮨, 인크. Ｃ형 간염 바이러스 복제의 신규 억제제
US7910747B2 (en) 2006-07-06 2011-03-22 Bristol-Myers Squibb Company Phosphonate and phosphinate pyrazolylamide glucokinase activators
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
WO2008006032A1 (en) * 2006-07-06 2008-01-10 Array Biopharma Inc. Cyclopenta [d] pyrimidines 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
EA016076B1 (ru) 2006-07-06 2012-01-30 Глэксо Груп Лимитед Замещенные n-фенилметил-5-оксопролин-2-амиды в качестве антагонистов р2х7-рецептора и способы их применения
US8063050B2 (en) * 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
GB0613518D0 (en) 2006-07-06 2006-08-16 Phytopharm Plc Chemical compounds
WO2008012635A2 (en) 2006-07-26 2008-01-31 Pfizer Products Inc. Amine derivatives useful as anticancer agents
US7659270B2 (en) * 2006-08-11 2010-02-09 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US8329159B2 (en) * 2006-08-11 2012-12-11 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
JP5228912B2 (ja) * 2006-09-08 2013-07-03 三菱瓦斯化学株式会社 高血圧改善剤
US7741347B2 (en) * 2007-05-17 2010-06-22 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
SI2173723T1 (sl) * 2007-07-05 2011-12-30 Array Biopharma Inc Pirimidil ciklopentani kot inhibitorji AKT-protein-kinaze
US8629171B2 (en) * 2007-08-08 2014-01-14 Bristol-Myers Squibb Company Crystalline form of methyl ((1S)-1-((25)-2-(5-(4'-(2-((25)-1((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt
CA2711782C (en) * 2008-01-09 2017-01-03 Array Biopharma Inc. 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors
EP2240455B1 (en) * 2008-01-09 2012-12-26 Array Biopharma, Inc. Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor
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
US7704992B2 (en) * 2008-02-13 2010-04-27 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US7906655B2 (en) * 2008-08-07 2011-03-15 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
WO2010096462A1 (en) * 2009-02-17 2010-08-26 Enanta Pharmaceuticals, Inc Linked diimidazole derivatives
RS56654B8 (sr) * 2009-05-13 2021-06-30 Gilead Pharmasset Llc Antiviralna jedinjenja

Also Published As

Publication number Publication date
US20110015204A1 (en) 2011-01-20
ES2551352T3 (es) 2015-11-18
AU2008272830B8 (en) 2013-12-12
WO2009006567A2 (en) 2009-01-08
SG185274A1 (en) 2012-11-29
RU2010103813A (ru) 2011-08-10
AU2008272830B2 (en) 2013-12-05
RU2486181C2 (ru) 2013-06-27
JP2010532386A (ja) 2010-10-07
EP2170863A2 (en) 2010-04-07
WO2009006567A3 (en) 2009-03-19
TW200902013A (en) 2009-01-16
TWI450720B (zh) 2014-09-01
CA2692502A1 (en) 2009-01-08
MA31679B1 (fr) 2010-09-01
JP5628028B2 (ja) 2014-11-19
US8618097B2 (en) 2013-12-31
AU2008272830A1 (en) 2009-01-08
ECSP109937A (es) 2010-03-31
JP2014028842A (ja) 2014-02-13
AR067413A1 (es) 2009-10-07
CO6251283A2 (es) 2011-02-21
CN101801955A (zh) 2010-08-11
EP2170863B1 (en) 2015-09-02
KR20100044819A (ko) 2010-04-30
KR20150089099A (ko) 2015-08-04
CN103396409B (zh) 2015-03-11
BRPI0813999A2 (pt) 2019-10-01
CN103396409A (zh) 2013-11-20
CN101801955B (zh) 2013-05-08
CR11229A (es) 2010-02-09
HK1147255A1 (en) 2011-08-05
NZ582692A (en) 2012-05-25
KR101650956B1 (ko) 2016-08-24

Similar Documents

Publication Publication Date Title
US8618097B2 (en) Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
AU2008272832B2 (en) Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
KR20150041164A (ko) Ａｋｔ 단백질 키나제 억제제로서의 시클로펜타〔ｄ〕피리미딘
MX2008016202A (es) Ciclopenta [d] pirimidinas hidroxiladas y metoxiladas como inhibidores de akt proteina quinasa.
US9409886B2 (en) Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
US8846683B2 (en) Pyrimidyl cyclopentanes as Akt protein kinase inhibitors
HK1147255B (en) Pyrimidyl cyclopentanes as akt protein kinase inhibitors
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: 20130627

MKLA Lapsed

Effective date: 20210705