WO2021111462A1 - Procédé amélioré pour la préparation de mésylate d'osimertinib - Google Patents

Procédé amélioré pour la préparation de mésylate d'osimertinib Download PDF

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Publication number
WO2021111462A1
WO2021111462A1 PCT/IN2020/050982 IN2020050982W WO2021111462A1 WO 2021111462 A1 WO2021111462 A1 WO 2021111462A1 IN 2020050982 W IN2020050982 W IN 2020050982W WO 2021111462 A1 WO2021111462 A1 WO 2021111462A1
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WO
WIPO (PCT)
Prior art keywords
osimertinib
methyl
preparation
mesylate
imp
Prior art date
Application number
PCT/IN2020/050982
Other languages
English (en)
Inventor
Shyam Sunder Reddy TALASANI
Nagendra MALA
Sahu Arabinda
Shankar Reddy BUDIDETI
Pulla Reddy Muddasani
Venkaiah Chowdary Nannapaneni
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
Publication of WO2021111462A1 publication Critical patent/WO2021111462A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group

Definitions

  • the present invention relates to an improved process for the preparation of Osimertinib mesylate with high purity and high yield.
  • Osimertinib is a kinase inhibitor, chemically known as N-(2- ⁇ 2- dimethylaminoethyl-methylamino ⁇ -4-methoxy-5- ⁇ [4-(l-methylindol-3-yl) pyrimidin-2-yl] amino ⁇ phenyl) prop-2-enamide mesylate and structurally represent as below:
  • Osimertinib is marketed as Osimertinib mesylate under the brand name TAGRISSO ® and it is indicated for treatment of locally advanced or metastatic non small cell lung Cancer.
  • Osimertinib mesylate is disclosed in US 8946235. Also disclosed the process for the preparation of the same by reactingNl-(2-(dimethylamino)ethyl)-5- methoxy-Nl-methyl-N4-(4-(l-methyl-lH-indol-3-yl)pyrimidin-2-yl)benzene-
  • US Patent No. 8946235 discloses Osimertinib mesylate salt and the process for its preparation. This patent also discloses crystalline form-A and B of Osimertinib mesylate as well as crystalline form-A, B, C, D, E and K of Osimertinib free base.
  • One Aspect of the present invention is to provide a process for the preparation of Osimertinib mesylate.
  • Another aspect of the present invention is to provide a process for the preparation of Osimertinib mesylate comprising the steps of: a) reacting Nl-(2-(dimethylamino)ethyl)-5-methoxy-Nl-methyl-N4-(4-(l- methyl- lH-indol-3-yl)pyrimidin-2-yl)benzene- 1 ,2,4-triamine with 3- chloropropanoyl chloride in presence of ketone solvent and water and without use of any base to obtain 3-chloro-N-[2-[2- dimethylaminoethyl- methyl-4-methoxy-5-[[4-(l-methylindol-3-yl)pyrimiddin-2-yl]amino] phenyl]propanamide, b) in-situ reacting the 3-chloro-N-[2-[2-dimethylaminoethyl-methyl-4- methoxy-5 - [ [
  • One embodiment of the present invention is to provide a process for the preparation of Osimertinib mesylate.
  • Another embodiment of the present invention is to provide a process for the preparation of Osimertinib mesylate comprising the steps of: a) reacting Nl-(2-(dimethylamino)ethyl)-5-methoxy-Nl-methyl-N4-(4-(l- methyl-lH-indol-3-yl) pyrimidin-2-yl)benzene- 1,2,4-triamine with 3- chloropropanoyl chloride in presence of ketone solvent and water and without use of any base to obtain 3-chloro-N-[2-[2- dimethylaminoethyl- methyl-4-methoxy-5-[[4-(l-methylindol-3-yl)pyrimiddin-2-yl]amino] phenyl]propanamide, b) in-situ reacting the 3-chloro-N-[2-[2-dimethylaminoethyl-methyl-4- methoxy-5 - [ [4-
  • the ketone solvent employed is selected from acetone, Methyl isobutyl ketone and methyl ethyl ketone, preferably acetone.
  • Osimertinib mesylate produced according to the present invention having the following impurities less than about 0.05% by HPLC:

Landscapes

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

Abstract

La présente invention concerne un procédé amélioré pour la préparation de mésylate d'osimertinib avec une pureté élevée et un rendement élevé.
PCT/IN2020/050982 2019-12-02 2020-11-27 Procédé amélioré pour la préparation de mésylate d'osimertinib WO2021111462A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201941049483 2019-12-02
IN201941049483 2019-12-02

Publications (1)

Publication Number Publication Date
WO2021111462A1 true WO2021111462A1 (fr) 2021-06-10

Family

ID=76221498

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2020/050982 WO2021111462A1 (fr) 2019-12-02 2020-11-27 Procédé amélioré pour la préparation de mésylate d'osimertinib

Country Status (1)

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WO (1) WO2021111462A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115433169A (zh) * 2022-11-07 2022-12-06 北京鑫开元医药科技有限公司 一种甲磺酸奥希替尼二聚体的制备方法
WO2024064091A1 (fr) * 2022-09-19 2024-03-28 Advenchen Pharmaceuticals, LLC Nouveau composé de pyrimidine utilisé en tant qu'inhibiteurs de kinases à activités biologiques sur des mutants d'egfr

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8946235B2 (en) * 2011-07-27 2015-02-03 Astrazeneca Ab 2-(2,4,5-substituted-anilino) pyrimidine compounds
WO2017134051A1 (fr) * 2016-02-01 2017-08-10 Astrazeneca Ab Procédé amélioré de préparation d'osimertib (azd9291) ou d'un sel de celui-ci, et "aniline azd9291" ou sel de celle-ci

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8946235B2 (en) * 2011-07-27 2015-02-03 Astrazeneca Ab 2-(2,4,5-substituted-anilino) pyrimidine compounds
WO2017134051A1 (fr) * 2016-02-01 2017-08-10 Astrazeneca Ab Procédé amélioré de préparation d'osimertib (azd9291) ou d'un sel de celui-ci, et "aniline azd9291" ou sel de celle-ci

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024064091A1 (fr) * 2022-09-19 2024-03-28 Advenchen Pharmaceuticals, LLC Nouveau composé de pyrimidine utilisé en tant qu'inhibiteurs de kinases à activités biologiques sur des mutants d'egfr
CN115433169A (zh) * 2022-11-07 2022-12-06 北京鑫开元医药科技有限公司 一种甲磺酸奥希替尼二聚体的制备方法

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