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Preparation method of type I clopidogrel hydrogen sulfate

A kind of technology of clopidogrel hydrogen sulfate, clopidogrel, applied in the field of chemistry, can solve problems such as low yield

Active Publication Date: 2013-12-11
SICHUAN EMEISHAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

FDA has made strict requirements on the limits of these three impurities, mainly because the existence of these impurities has a certain influence on the efficacy of clopidogrel bisulfate, and the yield is low

Method used

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  • Preparation method of type I clopidogrel hydrogen sulfate
  • Preparation method of type I clopidogrel hydrogen sulfate
  • Preparation method of type I clopidogrel hydrogen sulfate

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Embodiment Construction

[0071] The present invention will be described in further detail below through specific implementation examples and in conjunction with the accompanying drawings.

[0072] The embodiment of the present invention provides a preparation method of type I clopidogrel bisulfate, comprising:

[0073] (1) (S)-α-[(2-thiophene)ethylamino]-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride (S)-clopidogrel free base is generated through Mannich reaction as a raw material, and the (S)-clopidogrel free base is (S)-2-(2-chlorophenyl)-6,7-di Methyl chlorothieno[3,2-c]pyridine-5(4H)-acetate

[0074] (2) Through L-camphorsulfonic acid React with the (S)-clopidogrel free base, and remove impurities to obtain (S)-α-(2-chlorophenyl)-6,7-dichlorothieno[3,2-c]pyridine- 5(4H)-Methyl acetate-(L)-camsylate

[0075] (3) The (S)-α-(2-chlorophenyl)-6,7-dichlorothieno[3,2-c]pyridine-5(4H)-acetic acid methyl ester by acetone-petroleum ether -(L)-Camphorsulfonate is purified to remove impur...

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Abstract

The invention relates to a preparation method of type I clopidogrel hydrogen sulfate. The preparation method comprises the following steps of: generating (S) clopidogrel free alkali from the raw material (S)-alpha-[(2-thiophene)ethylamino]-alpha-(2-chlorphenyl) methyl acetate hydrochloride; reacting L-camphorsulfonic acid with the (S)-clopidogrel free alkali, and removing impurities to obtain (S)-alpha-(2-chlorphenyl)-6,7-dichlorothieno-[3,2-c] pyridine-5(4H)-methyl acetate-(L)-camphosulfonate; performing refining and impurity removal on the (S)-alpha-(2-chlorphenyl)-6,7-dichlorothieno-[3,2-c] pyridine-5(4H)-methyl acetate-(L)-camphosulfonate by using acetone-petroleum ether to obtain (S)-clopidogrel-(L)-camphosulfonate; removing L-camphorsulfonic acid from the (S)-clopidogrel-(L)-camphosulfonate and dropwise adding concentrated sulfuric acid to the type I clopidogrel hydrogen sulfate. The preparation method provided by the invention is capable of obtaining high-purity type I clopidogrel hydrogen sulfate.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a preparation method of type I clopidogrel bisulfate. Background technique [0002] Clopidogrel was successfully researched and developed by Sanofi in 1986. Its trade name is Plavix and its chemical name is (S)-α-(2-chlorophenyl)- 6,7-Dichlorothieno[3,2-c]pyridine-5(4H)-acetic acid methyl ester, which can inhibit ADP-induced platelet aggregation, and its action strength and tolerance are higher than those of the same thienopyridine derivatives The drug ticlopidine (ticlopidine), and the side effects are small. Clopidogrel is clinically used to prevent atherosclerosis in patients with myocardial infarction, stroke or a history of peripheral arterial disease. Its structural formula is as follows: [0003] Three impurities are mentioned in the USP standard of clopidogrel, namely CLPI-A, CLPI-B and CLPI-C (the structural formula is as follows). FDA has made strict requirements to the l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 唐鹤松罗华玲帅仕平
Owner SICHUAN EMEISHAN PHARMA
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