Preparation of paroxetine involving novel intermediates

Details Preparation of paroxetine involving novel intermediates Preparation of paroxetine involving novel intermediates

Category

C - Chemistry, Metallurgy

Subcategory

07

Subsubcategory

D

IPC codes

C07D 405/12 (2006.01) A61K 31/445 (2006.01) A61K 31/4525 (2006.01) A61P 25/24 (2006.01) C07D 261/20 (2006.01)

Type

Patent

Patent number

CA 2476723

Description

Disclosed are processed for preparing novel carbamate intermediates of paroxetine comprising delakylating N-alkylparoxetine by reaction thereof with a haloalkyl ester of a haloformic acid, in a suitable organic solvent. Also disclosed are processed for preparaing paroxetine comprising hydrolyzing the novel carbamate intermediates in a suitable solvent. Paroxetine prepared by the above processes can be neutralized with hydrogen chloride and crystallized as paroxetine hydrochloride anhydrous, hemilhydrate or as a solvate of isopropanol. The invention is further directed to the novel carbamate intermediates formed by the disclosed processes.

L'invention concerne des procédés de préparation de nouveaux intermédiaire carbamates de paroxétine, qui consistent à désalkyler de la N-alkylparoxétine par mise en réaction de celle-ci avec un haloalkylester d'un acide haloformique, dans un solvant organique approprié. L'invention porte également sur des procédés de préparation de la paroxétine, qui consistent à hydrolyser les nouveaux intermédiaires carbamates dans un solvant approprié. La paroxétine préparée selon les procédés susmentionnés peut être neutralisée avec du chlorure d'hydrogène et cristallisée sous forme d'hémihydrate anhydre d'hydrochlorure de paroxétine ou en tant que solvat d'isopropanol. L'invention porte également sur des nouveaux intermédiaires carbamates formés selon les procédés de l'invention.

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