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Processes For the preparation of different forms of (S)-(+)-Clopidogrel besylate

a technology of clopidogrel and process, which is applied in the field of processes for the preparation of different forms of (s)(+)clopidogrel besylate, can solve problems such as difficulties in industrialization

Inactive Publication Date: 2010-04-01
CADILA HEALTHCARE LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The processes result in stable, free-flowing, and easily scalable forms of Clopidogrel besylate with improved handling and operational simplicity, achieving melting points of 85-95°C for amorphous and 130-135°C for crystalline forms, enhancing industrial applicability and pharmacological effectiveness.

Problems solved by technology

However, according to the patent, these salts usually precipitated in amorphous form and / or they were hygroscopic, making them difficult to handle on an industrial scale.

Method used

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  • Processes For the preparation of different forms of (S)-(+)-Clopidogrel besylate
  • Processes For the preparation of different forms of (S)-(+)-Clopidogrel besylate

Examples

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example 1

Preparation of Amorphous Clopidogrel Besylate

[0031]Clopidogrel base was dissolved in THF, to which benzene sulfonic acid was added at 20° C., and the reaction mixture was heated to reflux temperature for 2 to 10 hr. The solvent was evaporated to dryness under reduced pressure to obtain Clopidogrel besylate, which on characterization showed to be the amorphous form.

[0032]The above process for preparing amorphous Clopidogrel besylate is carried out using methyl isobutyl ketone and the like or a mixture of THF and methyl isobutyl ketone as a solvent.

example 2

Preparation of Crystalline Clopidogrel Besylate

[0033]Clopidogrel base (10 g) was dissolved in decan-1-ol at 50-55° C., to which benzene sulfonic acid (5 g) was added at 50-55° C. and the reaction mixture was stirred for about 20 hr. The solid was filtered and washed with methyl tertiary butyl ether and dried in a vacuum oven for at least 20 hr. to give Clopidogrel besylate, which on characterization was found to be crystalline form. M.P. 130-135° C.

example 3

Preparation of Crystalline Clopidogrel Besylate

[0034]Clopidogrel base (10 g) was dissolved in decan-1-ol at 50-55° C., to which benzene sulfonic acid (5 g) was added at 50-55° C. The reaction mixture was seeded with crystalline Clopidogrel besylate and the reaction mixture was stirred for about 10 hr. The solid was filtered and washed with methyl tertiary butyl ether dried in a vacuum oven for at least 20 hr. to give Clopidogrel besylate, which on characterization was found to be crystalline form. M.P. 130-135° C.

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Abstract

Improved processes for the preparation of different forms of (S)-(+)-Clopidogrel besylate, pharmaceutical compositions containing them and their use in medicine.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a division of co-pending U.S. Ser. No. 12 / 065,386 filed Feb. 29, 2008, which was the U.S. national phase of International Application No. PCT / IN2006 / 000322, filed 28 Aug. 2006, which designated the U.S. and claimed priority based on IN 1072 / MUM / 2005, filed 5 Sep. 2005, the entire contents of all of which are hereby incorporated by reference.BACKGROUND[0002]1. Technical Field[0003]The present invention relates to an improved processes for the preparation of different forms of (S)-(+)-Clopidogrel besylate, pharmaceutical compositions containing them and their use in medicine.[0004]Clopidogrel has the following structure (1):[0005]It is available in the market as its bisulfate salt and is marketed by Sanofi-Synthelabo as “Plavix” having the general formula (II):[0006]Clopidogrel is an inhibitor of platelet aggregation and is marketed as an anti-anginal agent and an anti-platelet agent, and is found to decrease morbid even...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D495/04
CPCC07D495/04A61P9/10
Inventor LOHRAY, BRAJ BHUSHANLOHRAY, VIDYA BHUSHANPANDEY, BIPINDAVE, MAYANK GHANSHYAMBHAIDHOLAKIA, PARIND NARENDRA
Owner CADILA HEALTHCARE LTD