AU2005245885B2 - Pyrrole compounds as inhibitors of ERK protein kinase, synthesis thereof and intermediates thereto - Google Patents

Pyrrole compounds as inhibitors of ERK protein kinase, synthesis thereof and intermediates thereto Download PDF

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Publication number
AU2005245885B2
AU2005245885B2 AU2005245885A AU2005245885A AU2005245885B2 AU 2005245885 B2 AU2005245885 B2 AU 2005245885B2 AU 2005245885 A AU2005245885 A AU 2005245885A AU 2005245885 A AU2005245885 A AU 2005245885A AU 2005245885 B2 AU2005245885 B2 AU 2005245885B2
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compound
aliphatic
optionally substituted
compound according
chloro
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AU2005245885A
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AU2005245885A1 (en
Inventor
Michael R. Hale
Francois Maltais
Gabriel Martinez-Botella
Judith Straub
Qing Tang
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Vertex Pharmaceuticals Inc
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Vertex Pharmaceuticals Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • 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
    • 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
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • 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
    • A61P37/04—Immunostimulants
    • 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
    • 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
    • C07D401/04—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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (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)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Transplantation (AREA)
  • Communicable Diseases (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Virology (AREA)
  • Hematology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
AU2005245885A 2004-05-14 2005-05-13 Pyrrole compounds as inhibitors of ERK protein kinase, synthesis thereof and intermediates thereto Expired AU2005245885B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US57130904P 2004-05-14 2004-05-14
US60/571,309 2004-05-14
PCT/US2005/016902 WO2005113541A1 (en) 2004-05-14 2005-05-13 Pyrrole compounds as inhibitors of erk protein kinase, synthesis thereof and intermediates thereto

Publications (2)

Publication Number Publication Date
AU2005245885A1 AU2005245885A1 (en) 2005-12-01
AU2005245885B2 true AU2005245885B2 (en) 2011-01-20

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Application Number Title Priority Date Filing Date
AU2005245885A Expired AU2005245885B2 (en) 2004-05-14 2005-05-13 Pyrrole compounds as inhibitors of ERK protein kinase, synthesis thereof and intermediates thereto

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US (6) US7354939B2 (enExample)
EP (5) EP3305776B1 (enExample)
JP (1) JP5132305B2 (enExample)
CN (1) CN1976919A (enExample)
AR (2) AR051735A1 (enExample)
AU (1) AU2005245885B2 (enExample)
BR (1) BRPI0511111A (enExample)
CA (1) CA2566461C (enExample)
CY (1) CY1122336T1 (enExample)
DK (1) DK3305776T3 (enExample)
ES (4) ES2897422T3 (enExample)
HU (1) HUE047130T2 (enExample)
IL (1) IL179207A0 (enExample)
LT (1) LT3305776T (enExample)
MX (1) MXPA06013209A (enExample)
NO (1) NO20065727L (enExample)
NZ (1) NZ551582A (enExample)
PL (1) PL3305776T3 (enExample)
PT (1) PT3305776T (enExample)
RU (1) RU2376299C2 (enExample)
SI (1) SI3305776T1 (enExample)
TW (1) TW200607803A (enExample)
UA (1) UA84930C2 (enExample)
WO (1) WO2005113541A1 (enExample)
ZA (1) ZA200609975B (enExample)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004083203A1 (en) * 2003-03-13 2004-09-30 Vertex Pharmaceuticals Incorporated Compositions useful as protein kinase inhibitors
JP2007530595A (ja) * 2004-03-26 2007-11-01 バーテックス　ファーマシューティカルズ　インコーポレイテッド Ｅｒｋ２のピリジンインヒビターおよびそれらの使用
EP3305776B1 (en) * 2004-05-14 2019-09-25 Vertex Pharmaceuticals Incorporated Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds
US8546404B2 (en) 2005-12-13 2013-10-01 Merck Sharp & Dohme Compounds that are ERK inhibitors
US7807672B2 (en) 2006-02-16 2010-10-05 Schering Corporation Compounds that are ERK inhibitors
KR20100025553A (ko) * 2007-06-05 2010-03-09 쉐링 코포레이션 암 치료용 ｅｒｋ 억제제로서의 폴리사이클릭 인다졸 유도체 및 이의 용도
ES2556353T3 (es) 2008-02-21 2016-01-15 Merck Sharp & Dohme Corp. Compuestos que son inhibidores de las ERK
CN102146074B (zh) * 2011-01-26 2013-02-06 江苏先声药物研究有限公司 吡咯衍生物的制备方法及应用
WO2012172093A1 (en) 2011-06-17 2012-12-20 Merz Pharma Gmbh & Co. Kgaa Dihydroindolizine derivate as metabotropic glutamate receptor modulators
CA2926645C (en) 2013-10-14 2022-10-25 Indiana University Research And Technology Corporation Use of acamprosate to modulate erk 1/2 activation in animal models for fxs and asd and individuals diagnosed with fxs and asd
EP3061754A4 (en) 2013-10-23 2017-03-22 Takeda Pharmaceutical Company Limited Heterocyclic compound
WO2015095807A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of egfr and erk inhibitors
JP6678583B2 (ja) * 2013-12-20 2020-04-22 バイオメッド バレー ディスカバリーズ，インコーポレイティド ２型ｍｅｋ阻害剤およびｅｒｋ阻害剤の組み合わせを用いるがん処置
WO2015095842A2 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Methods and compositions for treating non-erk mapk pathway inhibitor-resistant cancers
US20160310477A1 (en) * 2013-12-20 2016-10-27 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of mek type 1 and erk inhibitors
WO2015095833A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Treatment of hematologic cancers
BR112016014481B1 (pt) 2013-12-20 2022-11-08 Biomed Valley Discoveries, Inc Uso de uma composição farmacêutica, método in vitro para efetuar a morte de células cancerosas, e kit
WO2015095831A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of mtor and erk inhibitors
WO2015095835A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Methods of modulating radioiodine uptake for the treatment of radioiodine-refractory cancers
EP4062917B1 (en) * 2013-12-20 2025-12-03 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of pi3k/akt pathway and erk inhibitors
AU2014368927B2 (en) * 2013-12-20 2018-10-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of CDK and ERK inhibitors
JP7180977B2 (ja) * 2015-01-30 2022-11-30 バイオメッド バレー ディスカバリーズ，インコーポレイティド 結晶性Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２マロン酸塩
EP3250562B1 (en) 2015-01-30 2024-11-27 Biomed Valley Discoveries, Inc. Crystalline 4-(5-chloro-2-isopropylaminopyridin-4-yl)-1h-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide hydrochloride salt
WO2016187028A1 (en) * 2015-05-15 2016-11-24 Celgene Avilomics Research, Inc. Heteroaryl compounds, synthesis thereof, and intermediates thereto
AU2015396809B2 (en) 2015-06-03 2019-07-11 Js Innopharm (Shanghai) Ltd. Heterocyclic compounds for treating psoriasis
WO2016192063A1 (en) * 2015-06-03 2016-12-08 Changzhou Jiekai Pharmatech Co. Ltd Heterocyclic compounds as erk inhibitors
IL291017B2 (en) 2015-10-21 2023-11-01 Otsuka Pharma Co Ltd Benzolactam compounds as protein kinase inhibitors
EP3170822A1 (en) 2015-11-18 2017-05-24 AGV Discovery Azaindole derivatives and their use as erk kinase inhibitors
WO2018067512A1 (en) 2016-10-05 2018-04-12 Kalyra Pharmaceuticals, Inc. Spirocyclic compounds
GB201706327D0 (en) 2017-04-20 2017-06-07 Otsuka Pharma Co Ltd A pharmaceutical compound
WO2019073435A1 (en) * 2017-10-12 2019-04-18 Novartis Ag COMBINATIONS OF MDM2 INHIBITORS WITH ERK INHIBITORS TO TREAT CANCERS
WO2019180141A1 (en) 2018-03-23 2019-09-26 Bayer Aktiengesellschaft Combinations of rogaratinib
US20230190725A1 (en) * 2019-04-29 2023-06-22 The Board Of Trustees Of The University Of Illinois Mek inhibitors for corneal scarring and neovascularization
WO2021020841A1 (en) * 2019-07-29 2021-02-04 Standigm Inc. Composition for preventing or treating metabolic liver disease
EP4212531A1 (en) 2022-01-14 2023-07-19 AGV Discovery Azaindole derivatives and their use as erk kinase inhibitors
CN118765276A (zh) * 2022-03-08 2024-10-11 甘李药业股份有限公司 氘代化合物，及其制备方法和应用
AU2023238106A1 (en) * 2022-03-24 2024-09-26 Biomed Valley Discoveries, Inc. Deuterated analogs of pyrrole inhibitors of erk, synthesis thereof and intermediates thereto

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5472966A (en) * 1995-03-29 1995-12-05 Bristol-Myers Squibb Company Antidepressant heteroarylaminoalkyl derivatives of naphthyl-monazines
US5565413A (en) * 1994-12-06 1996-10-15 Zeneca Limited Substituted pyridyl phenyl ketone herbicides
EP1188755A1 (en) * 1999-06-22 2002-03-20 Takeda Chemical Industries, Ltd. Acylhydrazine derivatives, process for preparing the same and use thereof
WO2002064586A2 (en) * 2001-02-09 2002-08-22 Vertex Pharmaceuticals Incorporated Heterocyclic inhibitors of erk2 and uses thereof
WO2003091246A1 (en) * 2002-04-26 2003-11-06 Vertex Pharmaceuticals Incorporated Pyrrole derivatives as inhibitors of erk2 and uses thereof
WO2004005283A1 (en) * 2002-07-09 2004-01-15 Vertex Pharmaceuticals Incorporated Imidazoles, oxazoles and thiazoles with protein kinase inhibiting activities
WO2004009562A1 (en) * 2002-07-18 2004-01-29 Janssen Pharmaceutica, Nv Substituted triazine kinase inhibitors
WO2004013125A1 (en) * 2002-07-31 2004-02-12 Smithkline Beecham Corporation Pyridinyl substituted (1,2,3,)triazoles as inhibitors of the tgf-beta signalling pathway
WO2004016597A2 (en) * 2002-08-14 2004-02-26 Vertex Pharmaceuticals Incorporated Protein kinase inhibitors and uses thereof
WO2004083203A1 (en) * 2003-03-13 2004-09-30 Vertex Pharmaceuticals Incorporated Compositions useful as protein kinase inhibitors

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5304121A (en) 1990-12-28 1994-04-19 Boston Scientific Corporation Drug delivery system making use of a hydrogel polymer coating
US5886026A (en) 1993-07-19 1999-03-23 Angiotech Pharmaceuticals Inc. Anti-angiogenic compositions and methods of use
US6099562A (en) 1996-06-13 2000-08-08 Schneider (Usa) Inc. Drug coating with topcoat
CA2374559A1 (en) * 1999-05-14 2000-11-23 Ortho-Mcneil Pharmaceutical, Inc. Substituted 3-pyridyl-4-arylpyrroles, and related therapeutic and prophylactic methods
EP3305776B1 (en) * 2004-05-14 2019-09-25 Vertex Pharmaceuticals Incorporated Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5565413A (en) * 1994-12-06 1996-10-15 Zeneca Limited Substituted pyridyl phenyl ketone herbicides
US5472966A (en) * 1995-03-29 1995-12-05 Bristol-Myers Squibb Company Antidepressant heteroarylaminoalkyl derivatives of naphthyl-monazines
EP1188755A1 (en) * 1999-06-22 2002-03-20 Takeda Chemical Industries, Ltd. Acylhydrazine derivatives, process for preparing the same and use thereof
WO2002064586A2 (en) * 2001-02-09 2002-08-22 Vertex Pharmaceuticals Incorporated Heterocyclic inhibitors of erk2 and uses thereof
WO2003091246A1 (en) * 2002-04-26 2003-11-06 Vertex Pharmaceuticals Incorporated Pyrrole derivatives as inhibitors of erk2 and uses thereof
WO2004005283A1 (en) * 2002-07-09 2004-01-15 Vertex Pharmaceuticals Incorporated Imidazoles, oxazoles and thiazoles with protein kinase inhibiting activities
WO2004009562A1 (en) * 2002-07-18 2004-01-29 Janssen Pharmaceutica, Nv Substituted triazine kinase inhibitors
WO2004013125A1 (en) * 2002-07-31 2004-02-12 Smithkline Beecham Corporation Pyridinyl substituted (1,2,3,)triazoles as inhibitors of the tgf-beta signalling pathway
WO2004016597A2 (en) * 2002-08-14 2004-02-26 Vertex Pharmaceuticals Incorporated Protein kinase inhibitors and uses thereof
WO2004083203A1 (en) * 2003-03-13 2004-09-30 Vertex Pharmaceuticals Incorporated Compositions useful as protein kinase inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Blanchard et al. Tetrahedron 2002 58(18), 3513-3524 *

Also Published As

Publication number Publication date
ES2751761T3 (es) 2020-04-01
US20230183276A1 (en) 2023-06-15
AR106755A2 (es) 2018-02-14
EP2799434B1 (en) 2017-08-02
ES2513965T3 (es) 2014-10-27
RU2006144445A (ru) 2008-06-20
TW200607803A (en) 2006-03-01
PL3305776T3 (pl) 2020-03-31
ZA200609975B (en) 2008-02-27
EP3943489A1 (en) 2022-01-26
USRE48266E1 (en) 2020-10-20
EP1753738A1 (en) 2007-02-21
EP1753738B1 (en) 2014-07-09
JP2007537295A (ja) 2007-12-20
AU2005245885A1 (en) 2005-12-01
NZ551582A (en) 2011-01-28
CY1122336T1 (el) 2021-01-27
CN1976919A (zh) 2007-06-06
EP2799434A1 (en) 2014-11-05
SI3305776T1 (sl) 2020-01-31
USRE47318E1 (en) 2019-03-26
CA2566461A1 (en) 2005-12-01
EP3608315B1 (en) 2021-08-11
IL179207A0 (en) 2007-03-08
DK3305776T3 (da) 2019-12-09
ES2897422T3 (es) 2022-03-01
HUE047130T2 (hu) 2020-04-28
CA2566461C (en) 2012-07-10
EP3305776A1 (en) 2018-04-11
BRPI0511111A (pt) 2007-11-27
NO20065727L (no) 2006-12-12
USRE49500E1 (en) 2023-04-25
WO2005113541A1 (en) 2005-12-01
US20060106069A1 (en) 2006-05-18
USRE46097E1 (en) 2016-08-09
LT3305776T (lt) 2020-01-10
ES2651439T3 (es) 2018-01-26
HK1203505A1 (en) 2015-10-30
MXPA06013209A (es) 2007-01-16
RU2376299C2 (ru) 2009-12-20
EP3608315A1 (en) 2020-02-12
AR051735A1 (es) 2007-02-07
EP3305776B1 (en) 2019-09-25
JP5132305B2 (ja) 2013-01-30
PT3305776T (pt) 2019-12-17
US7354939B2 (en) 2008-04-08
HK1247910A1 (en) 2018-10-05
UA84930C2 (ru) 2008-12-10

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