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Preparation method of officinal 4-trifluoromethyl acetylsalicylic acid

A technology of trifluoromethyl acetylsalicylic acid and trifluoromethyl salicylic acid, applied in the field of medicine, can solve the problem that the product purity is difficult to meet the purity requirements for medicinal use, and achieves the advantages of large-scale production operation, quality Stable, easy-to-use effects

Inactive Publication Date: 2011-07-27
武汉长联来福制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the product purity that makes according to this method is difficult to reach the purity requirement of medicine

Method used

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  • Preparation method of officinal 4-trifluoromethyl acetylsalicylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Put 20g of 4-trifluoromethylsalicylic acid and 50g of acetic anhydride into the reaction axe, start stirring, and slowly add 3g of concentrated sulfuric acid dropwise. After the dropwise addition, slowly raise the temperature to 30°C, and keep it warm for 3 hours, add the reaction liquid dropwise into 100g of water, stir, and a white solid precipitates, continue to stir for 1h after the dropwise addition, suction filter, and wash with a large amount of deionized water Filter cake until the pH reaches about 7 to obtain white crystals, and vacuum-dry at 45° C. for 10 hours to obtain 15.0 g of crude 4-trifluoromethylacetylsalicylic acid.

[0031] Add 15.0g of the crude product into the reaction flask, add 45g of petroleum ether (60-90°C), add 15g of ethyl acetate, heat to reflux, the crude product is basically completely dissolved, filter out a small amount of insoluble matter, naturally cool to room temperature for crystallization, cool to After room temperature, crystall...

Embodiment 2

[0038] Put 20g of 4-trifluoromethylsalicylic acid and 50g of acetic anhydride into the reaction axe, start stirring, and slowly add 3g of concentrated sulfuric acid dropwise. After the dropwise addition, slowly raise the temperature to 30°C, and keep it warm for 2 hours, add the reaction liquid dropwise into 100g of water, stir, and a white solid precipitates, continue to stir for 1h after the dropwise addition, filter with suction, and wash with a large amount of deionized water Filter cake until the pH reaches about 7 to obtain white crystals, and vacuum-dry at 45° C. for 10 hours to obtain 15.2 g of crude 4-trifluoromethylacetylsalicylic acid.

[0039] Add 15.2g of the crude product to the reaction flask, add 60g of petroleum ether (60-90°C), add 15g of ethyl acetate, heat to reflux, the crude product is basically completely dissolved, filter out a small amount of insoluble matter, naturally cool to room temperature for crystallization, cool to After room temperature, cryst...

Embodiment 3

[0046] Put 20g of 4-trifluoromethylsalicylic acid and 50g of acetic anhydride into the reaction axe, start stirring, and slowly add 3g of concentrated sulfuric acid dropwise. After the dropwise addition, slowly raise the temperature to 30°C, and keep it warm for 2 hours, add the reaction liquid dropwise into 100g of water, stir, and a white solid precipitates, continue to stir for 1h after the dropwise addition, filter with suction, and wash with a large amount of deionized water Filter cake until the pH reaches about 7 to obtain white crystals, and vacuum-dry at 45° C. for 10 hours to obtain 14.9 g of crude 4-trifluoromethylacetylsalicylic acid.

[0047] Add 14.9g of the crude product to the reaction flask, add 60g of petroleum ether (60-90°C), add 30g of ethyl acetate, heat to reflux, the crude product is basically completely dissolved, filter out a small amount of insoluble matter, naturally cool to room temperature for crystallization, and cool to After room temperature, c...

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Abstract

The invention belongs to the field of medical technologies and particularly relates to a preparation method of officinal 4-trifluoromethyl acetylsalicylic acid. The preparation method comprises the following steps: a. 4-trifluoromethyl salicylic acid and acetic anhydride react under the catalysis of concentrated sulfuric acid so as to obtain reaction liquid; b. the reaction liquid of step a is added into water, the mixture is filtered, and then filter residue obtained from the filtration is 4-trifluoromethyl acetylsalicylic acid crude product; and c. the 4-trifluoromethyl acetylsalicylic acidcrude product obtained in step b is added in and then reflows in a mixed liquid of ethyl acetate and petroleum ether, filtration is then carried out, the filtrate is cooled till -15 DEG C- -10 DEG C so as to filter out crystals, and the officinal 4-trifluoromethyl acetylsalicylic acid is obtained by drying the crystals; wherein the dosage proportion of the ethyl acetate and the petroleum ether is1-2 weight parts of ethyl acetate and 3-4 weight parts of petroleum ether. The purity of the 4-trifluoromethyl acetylsalicylic acid prepared according to the method is higher than 99.8 percent and ishigher than the quality requirements of European Pharmacopoeia (Version 6.0).

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a preparation method of medicinal 4-trifluoromethylacetylsalicylic acid. Background technique [0002] 4-Trifluoromethylacetylsalicylic acid is an antithrombotic drug developed and marketed by a Spanish company. It is widely used clinically to prevent stroke and myocardial infarction. , Portugal, Greece, Argentina and more than ten countries listed. 4-trifluoromethylacetylsalicylic acid is an anti-platelet aggregation agent, which reduces the biogenesis of thrombus through irreversible inhibition of platelet cyclooxygenase, and its main metabolite HTB (3-hydroxy-4-trifluorobenzoic acid) It is a reversible inhibitor of platelet cyclooxygenase, and its half-life is very long (about 34 hours), which is beneficial to the antiplatelet activity of trifluxalone; it can also inhibit platelet phosphodiesterase by inhibiting platelet phosphodiesterase. cAMP content, thereby producing an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/63C07C67/08
Inventor 张海杨勇庄惠祥
Owner 武汉长联来福制药股份有限公司
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