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Prasugrel hydrochloride acetic acid solvate as well as crystal and preparation method thereof

A technology of hydrochloride acetic acid and solvates, which is applied in the direction of drug combinations, pharmaceutical formulas, medical preparations containing active ingredients, etc., can solve the problems of poor water solubility, achieve good stability and solubility, and have a simple preparation process Effect

Inactive Publication Date: 2011-10-12
SHANGHAI INST OF PHARMA IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The patent application of Chinese Publication No. CN1452624 discloses a hydrochloride and maleate of prasugrel, which has good oral absorbability, metabolic activity and inhibition of platelet aggregation, weak toxicity, and good storage and handling stability. However, the hydrochloride and maleate of this prasugrel have the problem of poor water solubility, which urgently needs to be solved by those skilled in the art

Method used

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  • Prasugrel hydrochloride acetic acid solvate as well as crystal and preparation method thereof
  • Prasugrel hydrochloride acetic acid solvate as well as crystal and preparation method thereof
  • Prasugrel hydrochloride acetic acid solvate as well as crystal and preparation method thereof

Examples

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Effect test

Embodiment 1

[0025] 2-Acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride acetic acid solvate

[0026] 2-Acetoxy group-5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (compound of formula I) ( 2g) was dissolved in 16ml of acetic acid, and an acetic acid solution containing 1 equivalent of hydrogen chloride was added dropwise with stirring at room temperature, crystals were precipitated in about 10 minutes, and stirred at the same temperature for 2 hours. The precipitated crystals were filtered off, washed with ethyl acetate, and dried under reduced pressure at 60°C for 4 hours to obtain 2.2 g of the title compound as white crystals (yield 87.3%).

Embodiment 2

[0028] 2-Acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride acetic acid solvate

[0029] Dissolve 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (2g) in 8ml In a mixed solvent of acetic acid and 8 ml of ethyl acetate, an ethyl acetate solution containing 1 equivalent of hydrogen chloride was added dropwise with stirring at room temperature, a small amount of seed crystals (crystals obtained in Example 1) were added, and stirred at the same temperature for 2 hours. The precipitated crystals were filtered off, washed with ethyl acetate, and dried under reduced pressure at 60°C for 4 hours to obtain 2.3 g of the title compound as white crystals (91.3% yield).

Embodiment 3

[0031] 2-Acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride acetic acid solvate

[0032] Dissolve 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (2g) in 16ml In acetic acid, an aqueous solution containing 1 equivalent of hydrogen chloride was added dropwise with stirring at room temperature, a small amount of seed crystals (crystals obtained in Example 1) were added, and the mixture was stirred at the same temperature for 2 hours. The precipitated crystals were filtered, washed with ethyl acetate, and dried under reduced pressure at 60°C for 4 hours to obtain 2.2 g of the title compound as white crystals (yield 87.3%).

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Abstract

The invention discloses a novel hydrochloride acetic acid solvate which is 2-acetoxyl-5-(alpha-cyclopropyl carbonyl-2-luorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine shown as formula (I) or a crystal of the solvate and a preparation method of the solvate or the crystal thereof. Compared with prasugrel hydrochloride, the hydrochloride acetic acid solvate or the crystal thereof has higher stability and solubility and better contributes to the application to the preparation of a pharmaceutical preparation.

Description

technical field [0001] The present invention relates to a novel 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Hydrochloride acetic acid solvate, crystals of the solvate and process for their preparation. Background technique [0002] Prasugrel (2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, formula I Compound) is a new generation of ADP receptor antagonist, which is a new type of prodrug antiplatelet drug, and its drug effect is stronger than the ADP receptor antagonist clopidogrel that has been on the market. For example, it is induced by ADP in rats. The platelet aggregation of oral prasugrel is ten times stronger than that of clopidogrel. The plasma concentration of the active metabolite of prasugrel was also ten times higher than that of clopidogrel, suggesting a high market potential for prasugrel. [0003] [0004] The patent application of Chinese Publication No. CN1452624 ...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/4365A61P7/02
CPCA61K31/4365A61P7/02C07D495/04
Inventor 程兴栋袁哲东杨玉雷朱雪焱潘红娟童玲俞雄
Owner SHANGHAI INST OF PHARMA IND
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