Process for the preparation of solifenacin and salts thereof

A solifenacin and diastereomeric technology, which is applied in the field of preparation of solifenacin and its salts, can solve the problems of expensive and difficult preparation, and achieve the effects of mild conditions, short time and reduced total cost
CN103702997AInactive Publication Date: 2014-04-02ISOCHEM SA
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ISOCHEM SA
Publication Date
2014-04-02
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention provides a new process for the preparation of solifenacin or a pharmaceutically acceptable acid addition salt thereof, comprising reacting (R)-quinuclidin-3-yl phenethylcarbamate with benzaldehyde in the presence of an acid to obtain a diasteroisomeric mixture (S,R)-((R)-quinuclidin-3-yl)1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate of formula (IV) which can be resolved and the solifenacin or a pharmaceutically acceptable acid addition salt thereof recovered. The invention also provides the new key intermediate (R)-quinuclidin-3-yl phenethylcarbamate involved in the process. Further the invention provides a method for the transformation of (R)-((R)-quinuclidin-3-yl)1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate into a diasteroisomeric mixture (S,R)-((R)-quinuclidin-3-yl)1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate.
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Description

technical field

[0001] The present invention relates to obtaining (S)-1-phenyl-3,4-dihydroisoquinoline-2 (1H)-carboxylic acid ((R)-quinuclidin-3-yl) ester (sofenacin ( solifenacin)) or an acid addition salt thereof, in particular an improved method of a pharmaceutically acceptable acid addition salt thereof. The present invention also relates to novel intermediate compounds for the synthesis of solifenacin. The present invention also relates to the conversion of (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylic acid ((R)-quinuclidin-3-yl)ester into diastereomeric Method for isomerizing mixture (S,R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylic acid ((R)-quinuclidin-3-yl)ester. Background technique

[0002] Solifenacin, namely (3R)-1-azabicyclo[2.2.2]oct-3-yl-(1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H )-carboxylic acid ((R)-quinuclidin-3-yl) ester or 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)- The quinuclidinyl ester, also known as YM-905 ...

Claims

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