WO2009060463A1 - Procédé écologique de préparation de l'imatinib base - Google Patents

Procédé écologique de préparation de l'imatinib base Download PDF

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Publication number
WO2009060463A1
WO2009060463A1 PCT/IN2007/000520 IN2007000520W WO2009060463A1 WO 2009060463 A1 WO2009060463 A1 WO 2009060463A1 IN 2007000520 W IN2007000520 W IN 2007000520W WO 2009060463 A1 WO2009060463 A1 WO 2009060463A1
Authority
WO
WIPO (PCT)
Prior art keywords
imatinib
formula
preparation
imatinib base
acetonitrile
Prior art date
Application number
PCT/IN2007/000520
Other languages
English (en)
Inventor
Kompella Amala
Bhujanga Rao Adibhatla Kali Satya
Sreenivas Rachakonda
Nannapaneni Venkaiah Chowdary
Original Assignee
Natco Pharma Limited
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 Natco Pharma Limited filed Critical Natco Pharma Limited
Priority to PCT/IN2007/000520 priority Critical patent/WO2009060463A1/fr
Publication of WO2009060463A1 publication Critical patent/WO2009060463A1/fr

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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

Definitions

  • the present invention relates to an environmentally friendly and novel process for the preparation of highly pure (>99.8) (Imatinib) of formula (I)
  • Imatinib mesylate which is the methane sulfonate salt of N- ⁇ 5-[4-(4-methylpiperazino- methyl)- benzoylamido]-2-methylphenyl ⁇ -4- (3-pyridyl) 2-pyrimidine-amine having the Formula I (a)
  • I is approved under the trademark "Gleevec ®" by the US Food and Drug Administration for the treatment of Chronic Myelogenous Leukemia before and after the failure of interferon alpha. It has also been approved for the treatment of patients with kit (CDl 17) positive unresectable and / or metastatic malignant Gastro Intestinal Stromal Tumors (GISTs). It has also been approved for the treatment of pediatric patients with Philadelphia chromosome positive (Ph+) Chronic Myeloid Leukemia (CML) in chronic phase.
  • Imatinib mesylate I(a) The preparation of Imatinib mesylate I(a) and the use thereof especially as an antitumour agent is described in WO99/03854, ( Assignee : Novartis).
  • This application describes two polymorphic forms of imatinib mesylate, the ⁇ -form and the ⁇ -form,
  • WO 2005/075454 describes acid addition salts imatinib such as tartrate, citrate, malate, fumarate, etc., which are prepared by treatment of imatinib base with the corresponding acid.
  • EP 0564409 and in its equivalent US 55211584 the following route is described (Scheme-1)
  • reaction vessels generally used in pharmaceutical and chemical industry should be applicable for the carrying out the process. In other words there should not be any special or complicated or sophisticated apparatus required for carrying out the process.
  • Imatinib base is the precursor of the salt forms of imatinib. As such, there is a need for imatinib base of high purity which may be conveniently used as a precursor in the preparation of highly pure imatinib mesylate for therapeutic application. Summary of the invention:
  • N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine amine of the formula (II) and 4-(4-methyl-piperazinomethyl)benzoic acid of the formula (IV) can be prepared by the prior art processes
  • the Imatinib is produced in more than 99.8% purity.

Landscapes

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

Abstract

L'invention porte sur un nouveau procédé écologique de préparation de l'imatinib base extrêmement pur (> 99,8 %) de Formule (I). L'imatinib base de cette invention est approprié pour être converti en sels acceptables du point de vue pharmaceutique.
PCT/IN2007/000520 2007-11-05 2007-11-05 Procédé écologique de préparation de l'imatinib base WO2009060463A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/IN2007/000520 WO2009060463A1 (fr) 2007-11-05 2007-11-05 Procédé écologique de préparation de l'imatinib base

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2007/000520 WO2009060463A1 (fr) 2007-11-05 2007-11-05 Procédé écologique de préparation de l'imatinib base

Publications (1)

Publication Number Publication Date
WO2009060463A1 true WO2009060463A1 (fr) 2009-05-14

Family

ID=39737570

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000520 WO2009060463A1 (fr) 2007-11-05 2007-11-05 Procédé écologique de préparation de l'imatinib base

Country Status (1)

Country Link
WO (1) WO2009060463A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010133976A3 (fr) * 2009-05-22 2011-01-27 Actavis Group Ptc Ehf Imatinib sensiblement pure ou sel de celui-ci pharmaceutiquement acceptable
CN104974134A (zh) * 2015-05-19 2015-10-14 连云港宏创药业有限公司 甲磺酸伊马替尼的精制方法
CN105732582A (zh) * 2016-04-13 2016-07-06 安徽海康药业有限责任公司 一种伊马替尼的合成方法
CN108752314A (zh) * 2018-06-02 2018-11-06 安徽海康药业有限责任公司 一种伊马替尼的合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0564409A1 (fr) * 1992-04-03 1993-10-06 Ciba-Geigy Ag Dérivés de pyrimidine et procédé pour leur préparation
GB2398565A (en) * 2003-02-18 2004-08-25 Cipla Ltd Imatinib preparation and salts

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0564409A1 (fr) * 1992-04-03 1993-10-06 Ciba-Geigy Ag Dérivés de pyrimidine et procédé pour leur préparation
GB2398565A (en) * 2003-02-18 2004-08-25 Cipla Ltd Imatinib preparation and salts

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010133976A3 (fr) * 2009-05-22 2011-01-27 Actavis Group Ptc Ehf Imatinib sensiblement pure ou sel de celui-ci pharmaceutiquement acceptable
CN104974134A (zh) * 2015-05-19 2015-10-14 连云港宏创药业有限公司 甲磺酸伊马替尼的精制方法
CN105732582A (zh) * 2016-04-13 2016-07-06 安徽海康药业有限责任公司 一种伊马替尼的合成方法
CN108752314A (zh) * 2018-06-02 2018-11-06 安徽海康药业有限责任公司 一种伊马替尼的合成方法

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