CA2566461C - 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

Info

Publication number
CA2566461C
CA2566461C CA2566461A CA2566461A CA2566461C CA 2566461 C CA2566461 C CA 2566461C CA 2566461 A CA2566461 A CA 2566461A CA 2566461 A CA2566461 A CA 2566461A CA 2566461 C CA2566461 C CA 2566461C
Authority
CA
Canada
Prior art keywords
compound
pharmaceutically acceptable
aliphatic
acceptable salt
optionally substituted
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 - Lifetime
Application number
CA2566461A
Other languages
English (en)
French (fr)
Other versions
CA2566461A1 (en
Inventor
Gabriel Martinez-Botella
Michael R. Hale
Francois Maltais
Qing Tang
Judith Straub
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.)
Vertex Pharmaceuticals Inc
Original Assignee
Vertex Pharmaceuticals 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 Vertex Pharmaceuticals Inc filed Critical Vertex Pharmaceuticals Inc
Publication of CA2566461A1 publication Critical patent/CA2566461A1/en
Application granted granted Critical
Publication of CA2566461C publication Critical patent/CA2566461C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558Heterocyclic 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
    • C07F9/65583Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • 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
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • 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
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/04Immunostimulants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C07D401/04Heterocyclic 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Virology (AREA)
  • Dermatology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2566461A 2004-05-14 2005-05-13 Pyrrole compounds as inhibitors of erk protein kinase, synthesis thereof and intermediates thereto Expired - Lifetime CA2566461C (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
CA2566461A1 CA2566461A1 (en) 2005-12-01
CA2566461C true CA2566461C (en) 2012-07-10

Family

ID=35106760

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2566461A Expired - Lifetime CA2566461C (en) 2004-05-14 2005-05-13 Pyrrole compounds as inhibitors of erk protein kinase, synthesis thereof and intermediates thereto

Country Status (25)

Country Link
US (6) US7354939B2 (https=)
EP (5) EP2799434B1 (https=)
JP (1) JP5132305B2 (https=)
CN (1) CN1976919A (https=)
AR (2) AR051735A1 (https=)
AU (1) AU2005245885B2 (https=)
BR (1) BRPI0511111A (https=)
CA (1) CA2566461C (https=)
CY (1) CY1122336T1 (https=)
DK (1) DK3305776T3 (https=)
ES (4) ES2513965T3 (https=)
HU (1) HUE047130T2 (https=)
IL (1) IL179207A0 (https=)
LT (1) LT3305776T (https=)
MX (1) MXPA06013209A (https=)
NO (1) NO20065727L (https=)
NZ (1) NZ551582A (https=)
PL (1) PL3305776T3 (https=)
PT (1) PT3305776T (https=)
RU (1) RU2376299C2 (https=)
SI (1) SI3305776T1 (https=)
TW (1) TW200607803A (https=)
UA (1) UA84930C2 (https=)
WO (1) WO2005113541A1 (https=)
ZA (1) ZA200609975B (https=)

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
EP1730134A1 (en) * 2004-03-26 2006-12-13 Vertex Pharmaceuticals Incorporated Pyridine inhibitors of erk2 and uses thereof
LT3305776T (lt) * 2004-05-14 2020-01-10 Vertex Pharmaceuticals Incorporated Pirolo junginiai kaip erk baltymo kinazės inhibitoriai, ir farmacinės kompozicijos su šiais junginiais
US8546404B2 (en) 2005-12-13 2013-10-01 Merck Sharp & Dohme Compounds that are ERK inhibitors
MX2008010635A (es) 2006-02-16 2008-10-28 Schering Corp Derivados de pirrolidina como inhibidores de cinasa regulada por señales extracelulares.
AR068046A1 (es) * 2007-06-05 2009-11-04 Schering Corp Derivados policiclicos de indazol y su uso como inhibidores de erk para el tratamiento del cancer
WO2009105500A1 (en) 2008-02-21 2009-08-27 Schering Corporation Compounds that are erk inhibitors
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
EP3058371B1 (en) 2013-10-14 2021-06-16 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
US20160264536A1 (en) 2013-10-23 2016-09-15 Takeda Pharmaceutical Company Limited Heterocyclic compound
WO2015095835A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Methods of modulating radioiodine uptake for the treatment of radioiodine-refractory cancers
WO2015095842A2 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Methods and compositions for treating non-erk mapk pathway inhibitor-resistant cancers
WO2015095807A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of egfr and erk inhibitors
CA3240745A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatment using combinations of erk and raf inhibitors
JP6727127B2 (ja) * 2013-12-20 2020-07-29 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 Pi3k/aktシグナル経路阻害剤およびerk阻害剤の組み合わせを使用するがん処置
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
WO2015095833A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Treatment of hematologic cancers
WO2015095831A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of mtor and erk inhibitors
AU2014368927B2 (en) * 2013-12-20 2018-10-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of CDK and ERK inhibitors
US20160310477A1 (en) * 2013-12-20 2016-10-27 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of mek type 1 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
AU2016211246B2 (en) * 2015-01-30 2020-08-27 Biomed Valley Discoveries, Inc. Crystalline forms of C21H22CI2N4O2
WO2016187028A1 (en) * 2015-05-15 2016-11-24 Celgene Avilomics Research, Inc. Heteroaryl compounds, synthesis thereof, and intermediates thereto
CN107849046B (zh) * 2015-06-03 2020-06-12 常州捷凯医药科技有限公司 作为erk抑制剂的杂环化合物
WO2016192064A1 (en) 2015-06-03 2016-12-08 Js Innopharm (Shanghai) Ltd. Heterocyclic compounds for treating psoriasis
EP3365334B1 (en) 2015-10-21 2024-07-17 Otsuka Pharmaceutical 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
US10934304B2 (en) 2016-10-05 2021-03-02 Recurium Ip Holdings, Llc Spirocyclic compounds
GB201706327D0 (en) 2017-04-20 2017-06-07 Otsuka Pharma Co Ltd A pharmaceutical compound
JP7332589B2 (ja) * 2017-10-12 2023-08-23 ノバルティス アーゲー 癌を治療するためのmdm2阻害剤とerkの阻害剤との組合せ
WO2019180141A1 (en) 2018-03-23 2019-09-26 Bayer Aktiengesellschaft Combinations of rogaratinib
WO2020223177A1 (en) * 2019-04-29 2020-11-05 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
IL315702A (en) * 2022-03-24 2024-11-01 Biomed Valley Discoveries Inc Deuterated pyrrole inhibitory analogs of ERK, their synthesis and their intermediates

Family Cites Families (15)

* 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
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
US6099562A (en) 1996-06-13 2000-08-08 Schneider (Usa) Inc. Drug coating with topcoat
WO2000069847A1 (en) * 1999-05-14 2000-11-23 Ortho-Mcneil Pharmaceutical, Inc. Substituted 3-pyridyl-4-arylpyrroles, and related therapeutic and prophylactic methods
ATE325114T1 (de) * 1999-06-22 2006-06-15 Takeda Pharmaceutical Acylhydrazinderivate, verfahren zu ihrer herstellung und ihre verwendung
MY130778A (en) * 2001-02-09 2007-07-31 Vertex Pharma Heterocyclic inhibitiors of erk2 and uses thereof
AU2003237121A1 (en) * 2002-04-26 2003-11-10 Vertex Pharmaceuticals Incorporated Pyrrole derivatives as inhibitors of erk2 and uses thereof
CA2491895C (en) * 2002-07-09 2011-01-18 Vertex Pharmaceuticals Incorporated Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases
EP1546121B1 (en) * 2002-07-18 2012-08-29 Janssen Pharmaceutica NV Substituted triazine kinase inhibitors
GB0217780D0 (en) * 2002-07-31 2002-09-11 Glaxo Group Ltd Compounds
MXPA05001804A (es) * 2002-08-14 2005-05-27 Vertex Pharma Inhibidores de proteinas cinasas y usos de los mismos.
WO2004083203A1 (en) 2003-03-13 2004-09-30 Vertex Pharmaceuticals Incorporated Compositions useful as protein kinase inhibitors
LT3305776T (lt) * 2004-05-14 2020-01-10 Vertex Pharmaceuticals Incorporated Pirolo junginiai kaip erk baltymo kinazės inhibitoriai, ir farmacinės kompozicijos su šiais junginiais

Also Published As

Publication number Publication date
ES2651439T3 (es) 2018-01-26
DK3305776T3 (da) 2019-12-09
US7354939B2 (en) 2008-04-08
NO20065727L (no) 2006-12-12
PL3305776T3 (pl) 2020-03-31
WO2005113541A1 (en) 2005-12-01
TW200607803A (en) 2006-03-01
US20060106069A1 (en) 2006-05-18
AU2005245885B2 (en) 2011-01-20
LT3305776T (lt) 2020-01-10
US20230183276A1 (en) 2023-06-15
ES2751761T3 (es) 2020-04-01
IL179207A0 (en) 2007-03-08
EP2799434A1 (en) 2014-11-05
EP3305776B1 (en) 2019-09-25
HK1247910A1 (en) 2018-10-05
AU2005245885A1 (en) 2005-12-01
USRE49500E1 (en) 2023-04-25
USRE47318E1 (en) 2019-03-26
USRE48266E1 (en) 2020-10-20
HUE047130T2 (hu) 2020-04-28
PT3305776T (pt) 2019-12-17
EP3608315B1 (en) 2021-08-11
MXPA06013209A (es) 2007-01-16
RU2376299C2 (ru) 2009-12-20
ES2513965T3 (es) 2014-10-27
ZA200609975B (en) 2008-02-27
EP3608315A1 (en) 2020-02-12
NZ551582A (en) 2011-01-28
SI3305776T1 (sl) 2020-01-31
EP1753738B1 (en) 2014-07-09
EP3305776A1 (en) 2018-04-11
CN1976919A (zh) 2007-06-06
ES2897422T3 (es) 2022-03-01
CA2566461A1 (en) 2005-12-01
JP5132305B2 (ja) 2013-01-30
BRPI0511111A (pt) 2007-11-27
USRE46097E1 (en) 2016-08-09
RU2006144445A (ru) 2008-06-20
AR051735A1 (es) 2007-02-07
EP2799434B1 (en) 2017-08-02
CY1122336T1 (el) 2021-01-27
JP2007537295A (ja) 2007-12-20
AR106755A2 (es) 2018-02-14
EP3943489A1 (en) 2022-01-26
UA84930C2 (ru) 2008-12-10
HK1203505A1 (en) 2015-10-30
EP1753738A1 (en) 2007-02-21

Similar Documents

Publication Publication Date Title
USRE49500E1 (en) Pyrrole inhibitors of ERK protein kinase, synthesis thereof and intermediates thereto
WO2005100342A1 (en) Pyridine inhibitors of erk2 and uses thereof
EP1753744B1 (en) Prodrugs of pyrrolylpyrimidine erk protein kinase inhibitors
HK40064501A (en) Pyrrole inhibitors of erk protein kinase, synthesis thereof and intermediates thereto
HK40021464B (en) Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds
HK40021464A (en) Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds
HK1247910B (en) Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds
HK1203505B (en) Pyrrole compounds as inhibitors of erk protein kinases and pharmaceutical compositions containing these compounds
KR20070031934A (ko) Erk 단백질 키나아제의 억제제로서의 피롤 화합물, 이의합성 및 이의 중간체

Legal Events

Date Code Title Description
EEER Examination request