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

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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
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compound
pharmaceutically acceptable
aliphatic
acceptable salt
optionally substituted
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Expired - Lifetime
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CA2566461A
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English (en)
French (fr)
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CA2566461A1 (en
Inventor
Gabriel Martinez-Botella
Michael R. Hale
Francois Maltais
Qing Tang
Judith Straub
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Vertex Pharmaceuticals Inc
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Vertex Pharmaceuticals Inc
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    • 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

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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)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Cardiology (AREA)
  • Oncology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Vascular Medicine (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Urology & Nephrology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine 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

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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) EP3943489A1 (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=)

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US7456190B2 (en) * 2003-03-13 2008-11-25 Vertex Pharmaceuticals Incorporated Compositions useful as protein kinase inhibitors
US7462612B2 (en) * 2004-03-26 2008-12-09 Vertex Pharmaceuticals Incorporated Pyridine inhibitors of ERK2 and uses thereof
UA84930C2 (ru) * 2004-05-14 2008-12-10 Вертекс Фармасьютикалс Инкорпорейтед Пиррольные соединения как ингибиторы протеинкиназ erk, их синтез и соответствующие промежуточные соединения
US8546404B2 (en) 2005-12-13 2013-10-01 Merck Sharp & Dohme Compounds that are ERK inhibitors
JP2009528280A (ja) * 2006-02-16 2009-08-06 シェーリング コーポレイション Erkインヒビターとしてのピロリジン誘導体
MY148609A (en) * 2007-06-05 2013-05-15 Merck Sharp & Dohme Polycyclic indazole derivatives and their use as erk inhibitors for the treatment of cancer
US8716483B2 (en) 2008-02-21 2014-05-06 Merck Sharp & Dohme Corp. 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
RU2696481C2 (ru) 2013-10-14 2019-08-02 Индиана Юниверсити Рисерч Энд Текнолоджи Корпорейшн Применение акампросата для модулирования активации erk1/2 в животных моделях fxs и asd и людей с диагностированными fxs и asd
US20160264536A1 (en) 2013-10-23 2016-09-15 Takeda Pharmaceutical Company Limited Heterocyclic compound
AU2014368925A1 (en) * 2013-12-20 2016-07-21 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of MEK type I 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
WO2015095833A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Treatment of hematologic cancers
US10668055B2 (en) * 2013-12-20 2020-06-02 Biomed Valley Discoveries, Inc. Cancer treatment using combinations of ERK and RAF inhibitors
WO2015095842A2 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Methods and compositions for treating non-erk mapk pathway inhibitor-resistant cancers
US11007183B2 (en) * 2013-12-20 2021-05-18 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of PI3K/Akt pathway and ERK inhibitors
WO2015095840A1 (en) 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of cdk and erk inhibitors
WO2015095831A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of mtor and erk inhibitors
EP4389225A3 (en) 2013-12-20 2024-10-09 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of type 2 mek and erk inhibitors
WO2015095807A1 (en) * 2013-12-20 2015-06-25 Biomed Valley Discoveries, Inc. Cancer treatments using combinations of egfr and erk inhibitors
HK1244274A1 (zh) * 2015-01-30 2018-08-03 生物医学谷探索股份有限公司 C21h22ci2n4o2的晶型
WO2016123581A1 (en) * 2015-01-30 2016-08-04 Biomed Valley Discoveries, Inc. Crystalline c21h22c12n4o2 malonate
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
HUE068392T2 (hu) 2015-10-21 2024-12-28 Otsuka Pharma Co Ltd Benzolaktám vegyületek mint fehérje kináz gátlók
EP3170822A1 (en) 2015-11-18 2017-05-24 AGV Discovery Azaindole derivatives and their use as erk kinase inhibitors
AU2017339890A1 (en) * 2016-10-05 2019-04-11 Recurium Ip Holdings, Llc Spirocyclic compounds
GB201706327D0 (en) 2017-04-20 2017-06-07 Otsuka Pharma Co Ltd A pharmaceutical compound
EP3694518A1 (en) * 2017-10-12 2020-08-19 Novartis AG Combinations of mdm2 inhibitors with inhibitors of erk for treating 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
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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
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US7304061B2 (en) * 2002-04-26 2007-12-04 Vertex Pharmaceuticals Incorporated Heterocyclic inhibitors of ERK2 and uses thereof
US7361665B2 (en) * 2002-07-09 2008-04-22 Vertex Pharmaceuticals Incorporated Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases
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UA84930C2 (ru) * 2004-05-14 2008-12-10 Вертекс Фармасьютикалс Инкорпорейтед Пиррольные соединения как ингибиторы протеинкиназ erk, их синтез и соответствующие промежуточные соединения

Also Published As

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

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