BR112013018212B1 - Inibidores de tirosino quinase contendo diarilacettleno hidrazida - Google Patents

Inibidores de tirosino quinase contendo diarilacettleno hidrazida Download PDF

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Publication number
BR112013018212B1
BR112013018212B1 BR112013018212-1A BR112013018212A BR112013018212B1 BR 112013018212 B1 BR112013018212 B1 BR 112013018212B1 BR 112013018212 A BR112013018212 A BR 112013018212A BR 112013018212 B1 BR112013018212 B1 BR 112013018212B1
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BR
Brazil
Prior art keywords
alkyl
ring
ethynyl
aryl
methyl
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BR112013018212-1A
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English (en)
Portuguese (pt)
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BR112013018212A2 (pt
Inventor
Prabal Sengupta
Hemant Ashvinbhai Chokshi
Chetan Surjitsingh Puri
Sabbirhusen Yusufbhai Chimanwala
Varun Anilkumar Mehta
Dipali Manubhai Desai
Trinadha Rao Chitturi
Rajamannar Thennati
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Sun Pharma Advanced Research Company Ltd
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Publication of BR112013018212A2 publication Critical patent/BR112013018212A2/pt
Publication of BR112013018212B1 publication Critical patent/BR112013018212B1/pt

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/04—Preparation of hydrazides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (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)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
BR112013018212-1A 2011-01-21 2012-01-23 Inibidores de tirosino quinase contendo diarilacettleno hidrazida BR112013018212B1 (pt)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN184MU2011 2011-01-21
IN184/MUM/2011 2011-01-21
PCT/GB2012/050132 WO2012098416A1 (en) 2011-01-21 2012-01-23 Diarylacetylene hydrazide containing tyrosine kinase inhibitors

Publications (2)

Publication Number Publication Date
BR112013018212A2 BR112013018212A2 (pt) 2020-12-29
BR112013018212B1 true BR112013018212B1 (pt) 2021-12-14

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ID=45540888

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BR112013018212-1A BR112013018212B1 (pt) 2011-01-21 2012-01-23 Inibidores de tirosino quinase contendo diarilacettleno hidrazida

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US (1) US9024021B2 (enExample)
EP (1) EP2665709B1 (enExample)
JP (1) JP5905028B2 (enExample)
KR (1) KR101892574B1 (enExample)
CN (1) CN103502217B (enExample)
AU (1) AU2012208388C1 (enExample)
BR (1) BR112013018212B1 (enExample)
CA (1) CA2825367C (enExample)
EA (1) EA024194B8 (enExample)
ES (1) ES2608829T3 (enExample)
MX (1) MX336051B (enExample)
WO (1) WO2012098416A1 (enExample)

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DK2844256T3 (da) 2012-05-02 2023-03-27 Univ Georgetown Behandling af amyotrofisk lateral sklerose med tyrosinkinase-inhibitorer
CN103664787B (zh) * 2012-09-17 2015-09-09 南京圣和药业股份有限公司 炔杂芳环化合物及其应用
EP2818471A1 (en) * 2013-06-27 2014-12-31 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Nitrogen bicyclic compounds as inhibitors for Scyl1 and Grk5
GB2518873A (en) * 2013-10-03 2015-04-08 Agency Science Tech & Res Bicyclic alkyne derivatives and uses thereof
BR112016011079A2 (pt) 2013-11-15 2017-12-05 Wistar Inst ?inibidores de ebna1 e seu método de uso?
MX2017014550A (es) 2015-05-14 2018-02-26 Wistar Inst Inhibidores del antigeno nuclear epstein-barr 1 (ebna1) y metodos que los utilizan.
CA2985161A1 (en) * 2015-05-18 2016-11-24 Sun Pharma Advanced Research Company Limited Novel amidoheteroaryl aroyl hydrazide ethynes
DK3418275T3 (da) * 2016-02-16 2021-05-10 Korea Inst Sci & Tech Hidtil ukendt 2,3,5-substitueret thiophenforbindelse som proteinkinasehæmmer
HUE059387T2 (hu) 2016-06-02 2022-11-28 Sun Pharma Advanced Res Co Ltd Parkinson-kór kezelése
EA037697B1 (ru) * 2016-06-02 2021-05-12 Сан Фарма Адвансед Ресёрч Компани Лимитед Лечение болезни паркинсона
US11351123B2 (en) 2017-03-15 2022-06-07 Sun Pharma Advanced Research Company Limited Amorphous dispersion of 4-methyl-3-quinolin-3-ylethynyl-benzoic acid n'-(2-chloro-6-methyl-benzoyl) hydrazide
WO2018167803A1 (en) * 2017-03-15 2018-09-20 Sun Pharma Advanced Research Company Limited Novel amorphous dispersion of cyclopropanecarboxylic acid (5-{5-[ n'-(2-chloro-6-methylbenzoyl) hydrazinocarbonyl] -2-methyl-phenylethynyl}-pyridin-2-yl) amide
CN112543634A (zh) 2018-05-17 2021-03-23 威斯达研究所 Ebna1抑制剂晶体形式及其制备和使用方法
AU2019385480B2 (en) 2018-11-20 2025-04-24 Georgetown University Compositions and methods for treating neurodegenerative, myodegenerative, and lysosomal storage disorders
AU2020292703A1 (en) 2019-06-11 2022-01-27 Sun Pharma Advanced Research Company Ltd. Treatment for synucleinopathies
EP4081517A4 (en) 2019-12-26 2024-01-10 Beijing InnoCare Pharma Tech Co., Ltd. CRYSTALLINE FORMS OF (S)-1-(1-ACRYLOYLPYRROLIDINE-3-YL)-3-((3,5-DIMETHOXYPHENYL)ETHINYL)-5-(METHYLAMINO)-1H-PYRAZOLE-4-CARBOXAMIDE
EP4105217A4 (en) 2020-02-28 2023-09-06 Daegu-Gyeongbuk Medical Innovation Foundation 3-((8-((1H-PYRAZOL-4-YL))AMINO)IMIDAZO[1,2-A]PYRIDIN-3-YL)ETHINYL)-N-PHENYLBENZAMIDE DERIVATIVE, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION THE CONTAINER AS AN ACTIVE INGREDIENT FOR THE PREVENTION OR TREATMENT OF CANCER
CA3185939A1 (en) * 2020-07-31 2022-02-03 Nitin Krishnaji Damle N'-(2-chloro-6-methylbenzoyl)-4-methyl-3-[2-(3-quinolyl) ethynyl]-benzohydrazide for treatment of alzheimer's disease
TW202317530A (zh) 2021-06-29 2023-05-01 日商住友化學股份有限公司 雜環化合物及含有其之組成物之抗藥性有害節肢動物防除方法
AU2023331249A1 (en) 2022-08-25 2025-02-27 Sun Pharma Advanced Research Company Limited Methods of treating chronic myeloid leukemia using the tyrosine kinase inhibitor vodobatinib

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US5521184A (en) 1992-04-03 1996-05-28 Ciba-Geigy Corporation Pyrimidine derivatives and processes for the preparation thereof
ID30460A (id) 1999-04-15 2001-12-06 Bristol Myers Squibb Co Inhibitor-inhibitor protein siklik tirosin kinase
MXPA02010231A (es) 2001-11-27 2004-12-13 Warner Lambert Co Inhibidores aminotransferasa dependientes de aminoacidos de cadena ramificada y su uso en el tratamiento de las enfermedades neurodegenerativas.
GB0215676D0 (en) 2002-07-05 2002-08-14 Novartis Ag Organic compounds
ES2332184T3 (es) * 2004-03-22 2010-01-28 ELI LILLY & COMPANY Derivados de piridilo y su uso como antagonistas del receptor mglu5.
CN101389338B (zh) * 2005-12-23 2013-06-26 阿里亚德医药股份有限公司 双环杂芳基化合物
HUE047422T2 (hu) * 2005-12-23 2020-04-28 Ariad Pharma Inc Biciklusos heteroaril vegyületek
US7790756B2 (en) 2006-10-11 2010-09-07 Deciphera Pharmaceuticals, Llc Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases
WO2009100536A1 (en) * 2008-02-15 2009-08-20 Methylgene Inc. Inhibitors of kinase activity with 1,2-di-cyclyl substituted alkyne structures

Also Published As

Publication number Publication date
EP2665709B1 (en) 2016-12-07
MX336051B (es) 2016-01-07
AU2012208388C1 (en) 2017-04-27
KR20140016889A (ko) 2014-02-10
CA2825367A1 (en) 2012-07-26
BR112013018212A2 (pt) 2020-12-29
MX2013008296A (es) 2014-03-21
JP2014510037A (ja) 2014-04-24
CA2825367C (en) 2018-09-25
US9024021B2 (en) 2015-05-05
JP5905028B2 (ja) 2016-04-20
AU2012208388A2 (en) 2013-08-22
EA201370166A1 (ru) 2014-05-30
EA024194B8 (ru) 2016-11-30
ES2608829T3 (es) 2017-04-17
EP2665709A1 (en) 2013-11-27
AU2012208388A1 (en) 2013-08-22
US20130296557A1 (en) 2013-11-07
CN103502217A (zh) 2014-01-08
WO2012098416A1 (en) 2012-07-26
AU2012208388B2 (en) 2017-01-05
EA024194B1 (ru) 2016-08-31
KR101892574B1 (ko) 2018-08-28
CN103502217B (zh) 2015-11-25
ES2608829T8 (es) 2017-04-27

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