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Prasugrel hydrochloride ethanol solvate and preparation method thereof

A technology of prasugrel hydrochloride and hydrochloride ethanol, applied in organic chemistry, drug combination, pharmaceutical formula, etc., can solve the problems of difficult filtration, viscous crystal slurry, small crystal size, etc., and achieve crystal surface smoothness and product quality The effect of large particle size and efficiency improvement

Active Publication Date: 2013-04-03
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The inventors of the present application have studied various acid addition salts of prasugrel and their solvates, and found that prasugrel hydrochloride has problems such as small crystal size, viscous magma, and difficulty in filtration, which urgently need to be solved by those skilled in the art

Method used

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  • Prasugrel hydrochloride ethanol solvate and preparation method thereof
  • Prasugrel hydrochloride ethanol solvate and preparation method thereof
  • Prasugrel hydrochloride ethanol solvate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 3g of prasugrel in 20ml of sec-butanol, add 0.74ml of 12mol / L concentrated hydrochloric acid dropwise under stirring at room temperature, stir for 1h, filter the precipitated crystals, and dissolve the filtered crystals in 10ml of absolute ethanol at 70°C , the initial concentration of the solution was 0.3g / ml, the temperature was lowered to -10°C, the precipitated crystals were filtered, and dried at a vacuum of 0.08MPa and 60°C for 8h to obtain 1.76g of white crystalline prasugrel hydrochloride ethanol solvate. The product has high crystallinity, large crystal size and smooth surface.

[0028] The powder X-ray diffraction pattern of the product is as figure 1 As shown, there are characteristic peaks at diffraction angles (2θ) of 8.22, 11.48, 12.16, 13.00, 13.69, 14.32, 15.96, 17.38, 18.54, 21.70, 23.56, 24.34, 24.98, 26.38 and 28.66 degrees. Infrared spectrum picture as figure 2 Shown at 475, 589, 658, 772, 884, 958, 1035, 1082, 1123, 1287, 1379, 1495, 159...

Embodiment 2

[0030] Dissolve 3g of prasugrel in 25ml of isopropanol, add 0.54ml of 12mol / L concentrated hydrochloric acid dropwise under stirring at room temperature, stir for 1h, filter the precipitated crystals, and dissolve the filtered crystals in 10ml of absolute ethanol at 50°C , the initial concentration of the solution was 0.3g / ml, the temperature was lowered to -5°C, the precipitated crystals were filtered, and dried at 40°C at a vacuum of 0.09MPa for 3h to obtain 1.74g of white crystal prasugrel hydrochloride ethanol solvate. The product has high crystallinity, large crystal size and smooth surface.

[0031] The XRD pattern of the product shows that there are characteristic peaks at diffraction angles (2θ) of 8.23, 11.49, 12.26, 13.12, 13.69, 14.35, 15.98, 17.48, 18.56, 21.75, 23.59, 24.40, 24.99, 26.39 and 28.65 degrees. The infrared spectrum shows that at 475, 507, 589, 658, 668, 693, 735, 771, 813, 8432, 883, 923, 957, 1005, 1035, 1081, 1095, 1123, 1208, 1286, 1326, 1379, 142...

Embodiment 3

[0033]Dissolve 2 g of prasugrel in 15 ml of tetrahydrofuran, add 0.49 ml of 12 mol / L concentrated hydrochloric acid dropwise under stirring at room temperature, stir for 1 h, filter the precipitated crystals, and dissolve the filtered crystals in 10 ml of absolute ethanol at 60°C, and the solution The initial concentration of prasugrel was 0.2g / ml, the temperature was lowered to 0°C, the precipitated crystals were filtered, and dried at a vacuum of 0.1MPa and 50°C for 5h to obtain 1.48g of white crystalline prasugrel hydrochloride ethanol solvate. The product has high crystallinity, large crystal size and smooth surface.

[0034] The XRD pattern of the product shows that there are characteristic peaks at diffraction angles (2θ) of 8.23, 11.49, 12.27, 13.10, 13.68, 14.36, 15.98, 17.48, 18.59, 21.77, 23.50, 24.35, 24.97, 26.38 and 28.66 degrees. The infrared spectrum shows that at 475, 507, 589, 658, 668, 693, 735, 771, 813, 8432, 883, 923, 957, 1005, 1035, 1081, 1095, 1123, 120...

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Abstract

The invention relates to a prasugrel hydrochloride ethanol solvate and a preparation method thereof. The prasugrel hydrochloride ethanol solvate and the crystal thereof are defined on the aspects of X-ray powder diffraction pattern, diffraction angle 2 theta degrees, infrared spectroscopy and thermogravimetric curve. The preparation method comprises the following steps of: dissolving prasugrel into a solvent, wherein the ratio of prasugrel to solvent in the solution is 0.08-0.2g / mL; adding hydrochloric acid; filtering; cooling and crystallizing the obtained solid in anhydrous ethanol, wherein the concentration of the initial solution is 0.1 to 0.3g / mL; and filtering the crystal mush, drying, thus obtaining the product. X-ray diffraction (XRD) spectrograms and stereoscan photographs can prove that the crystallinity of the product is high, the granularity of the crystal is large, the surface of the crystal is smooth and clean, the filtering and drying speed is high, the efficiency of the preparation process is improved, and the solvate is beneficial to application to preparation of medicinal preparations.

Description

technical field [0001] The invention relates to a prasugrel hydrochloride ethanol solvate and a preparation method thereof. Background technique [0002] In February 2009, the European Commission approved a new oral antiplatelet drug, prasugrel / Efient, jointly developed by Eli Lilly and Company of the United States and Sankyo Corporation of Japan, for the prevention of patients who have received emergency treatment and will undergo delayed percutaneous coronary intervention. Atherothrombotic events in patients with acute coronary syndrome undergoing surgery. This is the first time prasugrel has been approved globally. [0003] Prasugrel is a novel thienopyridine P2Y12 antagonist with the chemical name 2-[2-(acetyloxy)-6,7-dihydrothieno[3,2-c]pyridine-5 (4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone, also known as 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4 ,5,6,7-Tetrahydrothieno[3,2-c]pyridine, the molecular formula is C 20 h 20 FNO 3 S, the molecular weig...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/4365A61P7/02A61P9/10
Inventor 尹秋响杜威龚俊波侯宝红张美景王永莉鲍颖郝红勋王召谢闯
Owner TIANJIN UNIV
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