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Preparation method of high-purity sarpogrelate hydrochloride

A high-purity technology for sarpogrelate hydrochloride, which is applied in the field of preparation of the 5-HT2 receptor blocker sarpogrelate hydrochloride, can solve the problems of not being able to obtain high purity, not mentioning control of the content of a single impurity, etc.

Active Publication Date: 2013-08-14
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the alkane of C2-C10, the ketone of C3-C10, the carboxylate of C2-C10, the halogenated alkane of C1-C10, aromatic hydrocarbon or aromatic hydrocarbon derivative are very little to the solubility of sarcogrelate hydrochloride at room temperature to reflux temperature and should not be alone As the recrystallization solvent of sargrelor hydrochloride, high-purity products cannot be obtained even if water is used as the recrystallization solvent or the organic solvent contains more than 5% water
Existing literature does not mention the issue of individual impurity content control

Method used

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  • Preparation method of high-purity sarpogrelate hydrochloride
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  • Preparation method of high-purity sarpogrelate hydrochloride

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Embodiment 1

[0019] The preparation of embodiment 1 sarcogrelate hydrochloride crude product

[0020] Add 13.7g of 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-2-propanol hydrochloride into a 250ml single-necked bottle, then add water 25ml, stir to dissolve. Adjust the pH value to 9-14 with 20% aqueous sodium hydroxide solution, extract with 30ml of toluene, and concentrate the organic layer under reduced pressure at 50°C until no 0 liquid slips out to obtain a brown oily substance. Then add 30g of tetrahydrofuran, stir to dissolve, add 4.5g of succinic anhydride, stir and heat to reflux, after 1 to 4 hours of reflux reaction, the reaction solution is concentrated to dryness at 40°C under reduced pressure; 25g of ethyl acetate is added to the residue, and stirred After dissolving, add saturated hydrogen chloride ethyl acetate solution dropwise to adjust the pH value to below 1, and stir for 50-60 minutes. Centrifugal filtration to obtain the crude wet product of sarcogrelate h...

Embodiment 2

[0021] The purification of embodiment 2 sarcogrelate hydrochloride crude product

[0022] Take 5g of the crude product of sarcogrelate hydrochloride, add 20ml of butanone, stir and heat up to dissolve, reflux for 20-30min, cool down to 25-35°C, keep stirring for 40-60min, filter, and rinse the filter cake with a small amount of butanone to obtain white fluffy The solid was dried under reduced pressure at 55-65° C. for 24 hours to obtain 4.6 g of sarcogrelate hydrochloride with a yield of 92%, an HPLC purity of 99.9%, and a maximum simple impurity content of 0.04%.

Embodiment 3

[0023] The purification of embodiment 3 sarcogrelate hydrochloride crude product

[0024] Take 5g of the crude product of sarcogrelate hydrochloride, add 30ml of butanone, stir and heat up to dissolve, reflux for 20-30min, cool down to 25-35°C, keep stirring for 40-60min, filter, and rinse the filter cake with a small amount of butanone to obtain white fluffy The solid was dried under reduced pressure at 55-65°C for 24 hours to obtain sargrelate hydrochloride 4.55 with a yield of 91%, a HPLC purity of 99.7%, and a maximum simple impurity content of 0.05%.

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Abstract

The invention provides a preparation method of high-purity sarpogrelate hydrochloride. The method comprises the following steps of: carrying out alkali dissociation on 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy-2-propanol hydrochloride which is taken as a raw material, reacting the dissociated 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy-2-propanol hydrochloride with succinic anhydride to obtain an ester, acidifying the ester to obtain a sarpogrelate hydrochloride crude product, and purifying the sarpogrelate hydrochloride crude product by using butanone as a recrystallization solvent to obtain the sarpogrelate hydrochloride, wherein the purity of the obtained sarpogrelate hydrochloride is higher than 9.9%, the any individual impurity of the obtained sarpogrelate hydrochloride is less than 0.1%, and the yield of the obtained sarpogrelate hydrochloride is higher than 90%. The preparation method adopts the single solvent for recrystallization, which facilitates solvent recovery, so that the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of sagrelate hydrochloride, a 5-HT2 receptor blocker. Background technique [0002] Sagrelate Hydrochloride Tablets was first launched in Japan in 1993 under the trade name Anplag, which is a 5-HT2 receptor blocker that can inhibit platelet aggregation and vasoconstriction, has antithrombotic effect and improves microcirculation. Its indications are to improve ischemic symptoms such as ulcers, pain and cold sensation caused by chronic arterial occlusive disease. The chemical name of sargrelor hydrochloride is 2-(dimethylamino)-1-{[2-(3-methoxyphenyl)phenoxy]methyl}ethylsuccinic acid monoester hydrochloride, which The structural formula is: [0003] [0004] The synthetic route disclosed in Journal of Medicinal Chemistry (J.Med.Chem, 1990, 33: 1818-1823) is: [0005] [0006] The sarcogrelate hydrochloride raw material drug used for the preparation ...

Claims

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Application Information

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IPC IPC(8): C07C219/06C07C213/10C07C213/06
Inventor 肖阳张广明刘立力袁庆
Owner 深圳万乐药业有限公司
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