JP5184887B2 - ｂｃｒ−ａｂｌキナーゼの阻害剤としての新規フェニルアミノピリミジン誘導体 - Google Patents

ｂｃｒ−ａｂｌキナーゼの阻害剤としての新規フェニルアミノピリミジン誘導体 Download PDF

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JP5184887B2
JP5184887B2 JP2007530854A JP2007530854A JP5184887B2 JP 5184887 B2 JP5184887 B2 JP 5184887B2 JP 2007530854 A JP2007530854 A JP 2007530854A JP 2007530854 A JP2007530854 A JP 2007530854A JP 5184887 B2 JP5184887 B2 JP 5184887B2
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methyl
formula
compound
trifluoromethyl
phenyl
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JP2008512448A5 (https=
JP2008512448A (ja
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アマラ・キシャン・コンペラ
ブージャンガ・ラオ・アディバートラ・カリ・サトヤ
スレーニヴァス・ラチャコンダ
カードガパティ・ポディリ
ナンナパネニ・ヴェンカイアー・チョウダリー
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ナトコ ファーマ リミテッド
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D401/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2007530854A 2004-09-09 2005-07-19 ｂｃｒ−ａｂｌキナーゼの阻害剤としての新規フェニルアミノピリミジン誘導体 Expired - Fee Related JP5184887B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN908/CHE/2004 2004-09-09
IN908CH2004 2004-09-09
PCT/IN2005/000243 WO2006027795A1 (en) 2004-09-09 2005-07-19 Novel phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase

Publications (3)

Publication Number Publication Date
JP2008512448A JP2008512448A (ja) 2008-04-24
JP2008512448A5 JP2008512448A5 (https=) 2011-08-18
JP5184887B2 true JP5184887B2 (ja) 2013-04-17

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ID=35395645

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JP2007530854A Expired - Fee Related JP5184887B2 (ja) 2004-09-09 2005-07-19 ｂｃｒ−ａｂｌキナーゼの阻害剤としての新規フェニルアミノピリミジン誘導体

Country Status (25)

Country Link
US (2) US7910598B2 (https=)
EP (2) EP1786799B1 (https=)
JP (1) JP5184887B2 (https=)
KR (1) KR100948453B1 (https=)
CN (1) CN101068805B (https=)
AP (1) AP2470A (https=)
AU (1) AU2005281299B2 (https=)
BR (1) BRPI0515081B8 (https=)
CA (1) CA2591321C (https=)
CY (1) CY1113617T1 (https=)
DK (1) DK1786799T3 (https=)
EA (1) EA013328B1 (https=)
ES (1) ES2390227T3 (https=)
HR (1) HRP20070146B1 (https=)
IL (1) IL181811A (https=)
MA (1) MA28922B1 (https=)
MX (1) MX2007002819A (https=)
NO (1) NO337598B1 (https=)
NZ (1) NZ554361A (https=)
PL (1) PL1786799T3 (https=)
PT (1) PT1786799E (https=)
SI (1) SI1786799T1 (https=)
UA (1) UA94570C2 (https=)
WO (1) WO2006027795A1 (https=)
ZA (2) ZA200701942B (https=)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6667300B2 (en) * 2000-04-25 2003-12-23 Icos Corporation Inhibitors of human phosphatidylinositol 3-kinase delta
SI2612862T1 (sl) 2004-05-13 2017-04-26 Icos Corporation Kinazolini kot inhibitorji humane fosfatidilinozitol 3-kinaze delta
US20110190328A1 (en) * 2004-09-09 2011-08-04 Natco Pharma Limited Acid addition salts of (3,5-bis trifluoromethyl)-n-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
US8735415B2 (en) 2004-09-09 2014-05-27 Natco Pharma Limited Acid addition salts of (3,5-Bis trifluoromethyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
UA94570C2 (en) 2004-09-09 2011-05-25 Натко Фарма Лимитед Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
US7939541B2 (en) * 2004-09-09 2011-05-10 Natco Pharma Limited Intermediates and a process employing the intermediates for the preparation of (3-trifluoromethylsulfonyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
WO2008031534A1 (en) * 2006-09-11 2008-03-20 Syngenta Participations Ag Insecticidal compounds
WO2008058037A1 (en) * 2006-11-03 2008-05-15 Irm Llc Compounds and compositions as protein kinase inhibitors
ES2396160T3 (es) * 2006-12-14 2013-02-19 Bayer Intellectual Property Gmbh Derivados de DIHIDROPIRIDINA que utiliza como inhibidores de la proteina quinasa
EP2152688A1 (en) * 2007-05-04 2010-02-17 Irm Llc Compounds and compositions as c-kit and pdgfr kinase inhibitors
EP2148874B1 (en) * 2007-05-04 2012-02-08 Irm Llc Pyrimidine derivatives and compositions as c-kit and pdgfr kinase inhibitors
CA2697077C (en) 2007-08-22 2012-10-16 Irm Llc 2-heteroarylamino-pyrimidine derivatives as kinase inhibitors
CA2697081C (en) 2007-08-22 2013-04-23 Irm Llc 5-(4-(haloalkoxy)phenyl)pyrimidine-2-amine compounds and compositions as kinase inhibitors
US8067422B2 (en) 2008-03-04 2011-11-29 Natco Pharma Limited Crystal form of phenylamino pyrimidine derivatives
MY183331A (en) * 2008-03-04 2021-02-18 Natco Pharma Ltd Crystal form of phenylamino pyrimidine derivatives
WO2012004801A1 (en) * 2010-07-07 2012-01-12 Hetero Research Foundation Process for imatinib mesylate
GB2488788B (en) 2011-03-07 2013-07-10 Natco Pharma Ltd Oral formulation of phenylaminopyrymidine compound with enhanced bioavailability and pharmacological response
CN103797011B (zh) 2011-09-01 2016-03-30 诺华股份有限公司 作为c-Kit激酶抑制剂的化合物和组合物
US9061028B2 (en) 2012-02-15 2015-06-23 Natco Pharma Limited Process for the preparation of Nilotinib
CN104379582A (zh) * 2012-06-15 2015-02-25 巴斯夫欧洲公司 包含达沙替尼和所选择的共晶体形成剂的多组分晶体
PT3389633T (pt) 2015-12-18 2021-08-05 Natco Pharma Ltd Composições farmacêuticas compreendendo derivados de fenilaminopirimidina
US10722484B2 (en) 2016-03-09 2020-07-28 K-Gen, Inc. Methods of cancer treatment
JP2023534963A (ja) 2020-07-15 2023-08-15 サード ハーモニック バイオ， インコーポレイテッド 選択的ｃ－ｋｉｔキナーゼ阻害剤の結晶質形態
US11744823B2 (en) 2020-11-19 2023-09-05 Third Harmonic Bio, Inc. Pharmaceutical compositions of a selective c-kit kinase inhibitor and methods for making and using same
CN113125689B (zh) * 2021-03-29 2022-02-22 创芯国际生物科技(广州)有限公司 一种新型mtt细胞活力检测试剂盒及其应用

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW225528B (https=) 1992-04-03 1994-06-21 Ciba Geigy Ag
US5516775A (en) 1992-08-31 1996-05-14 Ciba-Geigy Corporation Further use of pyrimidine derivatives
KR100330553B1 (ko) 1993-10-01 2002-11-27 노파르티스 아게 약물학적활성피리딘유도체및그의제조방법
JPH08503971A (ja) 1993-10-01 1996-04-30 チバ−ガイギー アクチェンゲゼルシャフト ピリミジンアミン誘導体及びその調製のための方法
WO1995009851A1 (en) 1993-10-01 1995-04-13 Ciba-Geigy Ag Pharmacologically active pyrimidineamine derivatives and processes for the preparation thereof
CO4940418A1 (es) 1997-07-18 2000-07-24 Novartis Ag Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso
AU739066B2 (en) * 1997-09-23 2001-10-04 Astrazeneca Ab Amide derivatives for the treatment of diseases mediated by cytokines
CA2338121A1 (en) * 1998-08-04 2000-02-17 Astrazeneca Ab Amide derivatives useful as inhibitors of the production of cytokines
GB0022438D0 (en) 2000-09-13 2000-11-01 Novartis Ag Organic Compounds
WO2004002963A1 (ja) * 2002-06-28 2004-01-08 Nippon Shinyaku Co., Ltd. アミド誘導体及び医薬
GB0222514D0 (en) 2002-09-27 2002-11-06 Novartis Ag Organic compounds
AU2003242988A1 (en) * 2003-06-06 2005-01-04 Adibhatla Kali Sathya Bhujanga Rao Process for the preparation of the anti-cancer drug imatinib and its analogues
AU2004246800B2 (en) * 2003-06-13 2008-12-04 Novartis Ag 2-aminopyrimidine derivatives as Raf kinase inhibitors
UA94570C2 (en) 2004-09-09 2011-05-25 Натко Фарма Лимитед Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
WO2008058037A1 (en) * 2006-11-03 2008-05-15 Irm Llc Compounds and compositions as protein kinase inhibitors

Also Published As

Publication number Publication date
EP1786799B1 (en) 2012-07-04
CY1113617T1 (el) 2016-06-22
ZA200701942B (en) 2008-10-29
US20070232633A1 (en) 2007-10-04
MA28922B1 (fr) 2007-10-01
SI1786799T1 (sl) 2012-12-31
PL1786799T3 (pl) 2012-12-31
IL181811A (en) 2013-07-31
NZ554361A (en) 2009-03-31
ES2390227T3 (es) 2012-11-07
MX2007002819A (es) 2007-08-14
AP2007003944A0 (en) 2007-04-30
UA94570C2 (en) 2011-05-25
EA013328B1 (ru) 2010-04-30
AU2005281299A1 (en) 2006-03-16
IL181811A0 (en) 2007-07-04
KR100948453B1 (ko) 2010-03-17
NO337598B1 (no) 2016-05-09
DK1786799T3 (da) 2012-10-01
JP2008512448A (ja) 2008-04-24
HRP20070146A2 (en) 2007-08-31
EP2295424B1 (en) 2015-10-14
NO20071521L (no) 2007-06-11
US7910598B2 (en) 2011-03-22
US8183253B2 (en) 2012-05-22
WO2006027795A1 (en) 2006-03-16
PT1786799E (pt) 2012-09-18
CN101068805A (zh) 2007-11-07
AU2005281299B2 (en) 2012-03-15
ZA200703123B (en) 2008-10-29
EA200700601A1 (ru) 2008-02-28
HRP20070146B1 (hr) 2015-12-04
EP2295424A1 (en) 2011-03-16
CA2591321A1 (en) 2006-03-16
HK1110588A1 (en) 2008-07-18
CN101068805B (zh) 2013-04-03
KR20070106681A (ko) 2007-11-05
BRPI0515081A (pt) 2008-07-08
BRPI0515081B8 (pt) 2021-05-25
AP2470A (en) 2012-09-17
BRPI0515081B1 (pt) 2021-05-04
US20080306100A1 (en) 2008-12-11
CA2591321C (en) 2013-09-24
EP1786799A1 (en) 2007-05-23

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