WO2013120852A4 - Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors - Google Patents

Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors Download PDF

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Publication number
WO2013120852A4
WO2013120852A4 PCT/EP2013/052790 EP2013052790W WO2013120852A4 WO 2013120852 A4 WO2013120852 A4 WO 2013120852A4 EP 2013052790 W EP2013052790 W EP 2013052790W WO 2013120852 A4 WO2013120852 A4 WO 2013120852A4
Authority
WO
WIPO (PCT)
Prior art keywords
intermediates
tyrosine kinase
kinase inhibitors
methyl
general formula
Prior art date
Application number
PCT/EP2013/052790
Other languages
French (fr)
Other versions
WO2013120852A1 (en
Inventor
Viesturs Lusis
Svetlana STUPNIKOVA
Dzintra Muceniece
Armands Zandersons
Deniss LAIPNIEKS
Edvards LAVRINOVICS
Indra JONANE-OSA
Original Assignee
Grindeks, A Joint Stock Company
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 Grindeks, A Joint Stock Company filed Critical Grindeks, A Joint Stock Company
Priority to GB1414378.8A priority Critical patent/GB2514285B/en
Publication of WO2013120852A1 publication Critical patent/WO2013120852A1/en
Publication of WO2013120852A4 publication Critical patent/WO2013120852A4/en

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

4-Oxo-2-phenylaminopyrimidine derivatives as intermediates for synth of tyrosine kinase inhibitors, in particular imatinib and nilotinib.

Claims

AMENDED CLAIMS received by the International Bureau on 14 August 2013 (14.08.13)
1. 2-Phenylaminopyrimidines of general formula (I)
Figure imgf000002_0001
(I)
wherein:
X is selected from II), (III)
Figure imgf000002_0002
(II) (III),
and alkoxycarbonyl group or amino group.
2. 2-Phenylaminopyrimidines of general formula (I) according to claim 1 , wherein X is a group of formula (II), namely 4-[(4-methyl-1- piperazinyl)methyl]-N-[4-methyl-3-[(4-oxo-2-pyrimidinyl)amino]phenyl]- benzamide.
3. 2-Phenylaminopyrimidines of general formula (I) according to claim 1 , wherein X is a group of formula (III), namely is 4-methyl-N-(3-(4-methyl- 1 H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3- (6-oxo-1 ,6- dihydropyrimidin-2-ylamino)benzamide.
4. 2-Phenylaminopyrimidine of general formula (I)
Figure imgf000002_0003
as intermediates for preparing tyrosine kinase inhibitors of general formula (IV) 29
Figure imgf000003_0001
Figure imgf000003_0002
PCT/EP2013/052790 2012-02-13 2013-02-12 Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors WO2013120852A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1414378.8A GB2514285B (en) 2012-02-13 2013-02-12 Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP12155116 2012-02-13
EP12155116.2 2012-02-13
EP12155117.0 2012-02-13
EP12155117 2012-02-13
EP12198885.1 2012-12-21
EP12198885 2012-12-21

Publications (2)

Publication Number Publication Date
WO2013120852A1 WO2013120852A1 (en) 2013-08-22
WO2013120852A4 true WO2013120852A4 (en) 2013-10-10

Family

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Family Applications (1)

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PCT/EP2013/052790 WO2013120852A1 (en) 2012-02-13 2013-02-12 Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors

Country Status (2)

Country Link
GB (1) GB2514285B (en)
WO (1) WO2013120852A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105985293B (en) * 2015-03-04 2018-04-03 埃斯特维华义制药有限公司 The preparation method of AMN107 intermediate
WO2016187824A1 (en) * 2015-05-26 2016-12-01 凯莱英医药集团（天津）股份有限公司 Method of preparing nilotinib
EP3609882B1 (en) 2017-03-17 2022-07-13 Cardio Therapeutics Pty Ltd Heterocyclic inhibitors of pcsk9

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5521184A (en) 1992-04-03 1996-05-28 Ciba-Geigy Corporation Pyrimidine derivatives and processes for the preparation thereof
TW225528B (en) 1992-04-03 1994-06-21 Ciba Geigy Ag
GB0202873D0 (en) 2002-02-07 2002-03-27 Novartis Ag Organic compounds
US7507821B2 (en) 2004-12-30 2009-03-24 Chemagis Ltd. Process for preparing Imatinib
SA06270147B1 (en) 2005-06-09 2009-12-22 نوفارتيس ايه جي Process for the Synthesis Of 5-(methyl-1h-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine
GT200600315A (en) 2005-07-20 2007-03-19 CRYSTAL FORMS OF 4-METHYL-N- [3- (4-METHYL-IMIDAZOL-1-ILO) -5-TRIFLUOROMETILO-PHENYL] -3- (4-PYRIDINA-3-ILO-PIRIMIDINA-2-ILOAMINO) -BENZAMIDA
US8466154B2 (en) * 2006-10-27 2013-06-18 The Board Of Regents Of The University Of Texas System Methods and compositions related to wrapping of dehydrons
WO2008059551A2 (en) 2006-11-16 2008-05-22 F.I.S. Fabbrica Italiana Sintetici S.P.A. Process for the preparation of imatinib and intermediates thereof
CN100451015C (en) 2007-02-14 2009-01-14 杭州盛美医药科技开发有限公司 Preparing method of imatinib
RU2329260C1 (en) 2007-02-20 2008-07-20 Юрий Иосифович Копырин Method of obtaining 2-anilinopyrimidines or their salts (options)
US7550591B2 (en) * 2007-05-02 2009-06-23 Chemagis Ltd. Imatinib production process
EP2062885A1 (en) * 2007-11-21 2009-05-27 Eczacibasi-Zentiva Kimyasal Ürünler Sanayi ve Ticaret A.S. Acid addition salts of imatinib and formulations comprising the same
CN101497601B (en) 2008-01-29 2012-11-07 福建南方制药股份有限公司 Process for synthesizing imatinib
EP2305667A3 (en) * 2008-07-17 2011-05-11 Teva Pharmaceutical Industries Ltd. Nilotinib intermediates and preparation thereof
PL215042B1 (en) 2008-08-01 2013-10-31 Temapharm Spolka Z Ograniczona Odpowiedzialnoscia Method of imatinib manufacturing
JP2014509642A (en) 2011-03-31 2014-04-21 アイエヌディー−スイフト ラボラトリーズ リミテッド An improved method for the formation of imatinib and its mesylate

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Publication number Publication date
GB201414378D0 (en) 2014-09-24
GB2514285B (en) 2018-07-18
GB2514285A (en) 2014-11-19
WO2013120852A1 (en) 2013-08-22

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