KR101892574B1 - 디아릴아세틸렌 히드라지드 함유 티로신 키나제 억제제 - Google Patents

디아릴아세틸렌 히드라지드 함유 티로신 키나제 억제제 Download PDF

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KR101892574B1
KR101892574B1 KR1020137021626A KR20137021626A KR101892574B1 KR 101892574 B1 KR101892574 B1 KR 101892574B1 KR 1020137021626 A KR1020137021626 A KR 1020137021626A KR 20137021626 A KR20137021626 A KR 20137021626A KR 101892574 B1 KR101892574 B1 KR 101892574B1
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alkyl
methyl
formula
ethynyl
compounds
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KR20140016889A (ko
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라자마나르 텐나티
조나단 데이비드 마크 아트킨슨
프라발 셍굽타
헤만트 아쉬빈브하이 초크시
체탄 수르지츠싱 푸리
사비르후센 유수프브하이 치만왈라
바룬 아닐쿠마르 메타
디팔리 마누브하이 데사이
트리나드하 라오 치투리
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썬 파마 어드밴스트 리서치 컴패니 리미티드
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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
    • C07D215/12—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
    • 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
    • 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020137021626A 2011-01-21 2012-01-23 디아릴아세틸렌 히드라지드 함유 티로신 키나제 억제제 Active KR101892574B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN184/MUM/2011 2011-01-21
IN184MU2011 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
KR20140016889A KR20140016889A (ko) 2014-02-10
KR101892574B1 true KR101892574B1 (ko) 2018-08-28

Family

ID=45540888

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KR1020137021626A Active KR101892574B1 (ko) 2011-01-21 2012-01-23 디아릴아세틸렌 히드라지드 함유 티로신 키나제 억제제

Country Status (12)

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

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WO2013166295A1 (en) 2012-05-02 2013-11-07 Georgetown University Treating neural disease with tyrosine kinase inhibitors
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
MX2016006325A (es) * 2013-11-15 2016-12-02 Wistar Inst Inhibidores del antígeno nuclear 1 de epstein-barr, y su método de uso.
EP3294705B1 (en) 2015-05-14 2021-07-21 The Wistar Institute Of Anatomy And Biology Ebna1 inhibitors and methods using same
US10150733B2 (en) * 2015-05-18 2018-12-11 Sun Pharma Advanced Research Company Ltd. Amidoheteroaryl aroyl hydrazide ethynes
CN108884066B (zh) * 2016-02-16 2021-08-24 韩国科学技术研究院 作为蛋白激酶抑制剂的2，3，5-取代的噻吩化合物
WO2017208267A1 (en) 2016-06-02 2017-12-07 Sun Pharma Advanced Research Company Limited Treatment for parkinson's disease
EA037697B1 (ru) * 2016-06-02 2021-05-12 Сан Фарма Адвансед Ресёрч Компани Лимитед Лечение болезни паркинсона
CA3056348A1 (en) * 2017-03-15 2018-09-20 Sun Pharma Advanced Research Company Limited Novel amorphous dispersion of 4-methyl-3-quinolin-3-ylethynyl-benzoic acid n'-(2-chloro-6-methyl-benzoyl) hydrazide
MA47798A (fr) 2017-03-15 2020-01-22 Sun Pharma Advanced Res Co Ltd Nouvelle dispersion amorphe d'acide cyclopropanecarboxylique (5-{5-[ n'-(2-chloro-6-méthylbenzoyl) hydrazinocarbonyl] -2-méthyl-phényléthynyl}-pyridin-2-yl) amide
WO2019222470A1 (en) 2018-05-17 2019-11-21 The Wistar Institute Ebna1 inhibitor crystalline forms, and methods of preparing and using same
CN113272308B (zh) 2018-11-20 2025-03-18 乔治敦大学 用于治疗神经退行性、肌退行性和溶酶体贮积病症的组合物和方法
BR112021024835A2 (pt) 2019-06-11 2022-01-18 Sun Pharma Advanced Res Co Ltd Tratamento para sinuclenopatias
MX2022007988A (es) 2019-12-26 2022-07-11 Beijing Innocare Pharma Tech Co Ltd Formas cristalinas de (s)-1-(1-acriloilpirrolidin-3-il)-3-((3,5-di metoxifenil)etinil)-5-(metilamino)-1h-pirazol-4-carboxamida.
CN115279759B (zh) 2020-02-28 2025-07-29 大邱庆北尖端医疗产业振兴财团 苯甲酰胺衍生物及其制备方法和用途
IL300044A (en) 2020-07-31 2023-03-01 Sun Pharma Advanced Res Co Ltd 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
CN120018848A (zh) 2022-08-25 2025-05-16 太阳医药高级研究有限公司 使用酪氨酸激酶抑制剂沃多巴替尼治疗慢性髓细胞白血病的方法

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US5521184A (en) 1992-04-03 1996-05-28 Ciba-Geigy Corporation Pyrimidine derivatives and processes for the preparation thereof
NZ513639A (en) 1999-04-15 2004-02-27 Bristol Myers Squibb Co Cyclic protein tyrosine kinase inhibitors
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.
SI1973545T1 (sl) * 2005-12-23 2013-04-30 Ariad Pharmaceuticals, Inc. Spojine bicikličnega heteroarila
DK1973545T3 (da) * 2005-12-23 2013-02-25 Ariad Pharma Inc Bicykliske heteroarylforbindelser
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
KR20140016889A (ko) 2014-02-10
AU2012208388C1 (en) 2017-04-27
US9024021B2 (en) 2015-05-05
AU2012208388A1 (en) 2013-08-22
AU2012208388B2 (en) 2017-01-05
AU2012208388A2 (en) 2013-08-22
EA024194B8 (ru) 2016-11-30
EA201370166A1 (ru) 2014-05-30
ES2608829T8 (es) 2017-04-27
JP2014510037A (ja) 2014-04-24
WO2012098416A1 (en) 2012-07-26
CN103502217A (zh) 2014-01-08
US20130296557A1 (en) 2013-11-07
EA024194B1 (ru) 2016-08-31
EP2665709B1 (en) 2016-12-07
EP2665709A1 (en) 2013-11-27
BR112013018212B1 (pt) 2021-12-14
MX336051B (es) 2016-01-07
BR112013018212A2 (pt) 2020-12-29
CA2825367A1 (en) 2012-07-26
MX2013008296A (es) 2014-03-21
ES2608829T3 (es) 2017-04-17
CN103502217B (zh) 2015-11-25
CA2825367C (en) 2018-09-25
JP5905028B2 (ja) 2016-04-20

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