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Acid-addition salt of Prasugrel, preparation method and application

A technology of benzenesulfonate and hydroxybenzenesulfonate, which is applied in the preparation of sulfonate, medical preparations containing active ingredients, pharmaceutical formulations, etc., and can solve the problems of properties such as solubility, stability, and biological activity. Detailed evaluation, no advantages and other problems were found, to achieve the effect of simple and easy preparation method, good stability and safety, and good product quality

Inactive Publication Date: 2013-01-30
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In addition to the discovery of prasugrel hydrochloride and maleate, most of the above-mentioned predecessors’ patents relate to the preparation method of prasugrel salt, and the properties of various salts such as solubility, stability, biological activity, etc. are not given. After a detailed evaluation, no obvious advantages were found

Method used

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  • Acid-addition salt of Prasugrel, preparation method and application
  • Acid-addition salt of Prasugrel, preparation method and application
  • Acid-addition salt of Prasugrel, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: Synthesis of prasugrel 2,5-dihydroxybenzenesulfonate

[0062] Add prasugrel (17.2g, 0.046mol) and 2,5-dihydroxybenzenesulfonic acid (10.5g, 0.055mol) into a reaction flask filled with acetone (170ml), control the temperature at 30°C, and stir to make it Dissolved to give a clear solution. Concentrate the reaction solution to 1 / 2 volume, let it stand, cool to 0°C, and precipitate a single crystal, which is the 2,5-dihydroxybenzenesulfonate of prasugrel, that is, prasugrel 2,5-dihydroxybenzenesulfonate , weight: 22.2g, yield: 85.6%. The crystal form corresponding to the product is named Form A.

[0063] The following are the characterization data of prasugrel 2,5-dihydroxybenzenesulfonate:

[0064] m.p.175.3-176.5°C.

[0065] IR(KBr) v :3303(O-H),3185,3021(C=C-H),2929(C-H),1751(O-C=O),1700(C=O),1209,1076(SO3-NH + ), 1193(C-F).

[0066] ESI-MS (positive): m / z=374, [M+H] + ;m / z=396,[M+Na] + .

[0067] ESI-MS (negative): m / z=189, [M-H] - .

[0068] 1 ...

Embodiment 2

[0071] Example 2: Synthesis of prasugrel 2,5-dihydroxybenzenesulfonate

[0072] Add prasugrel (17.2g, 0.046mol) and 2,5-dihydroxybenzenesulfonic acid (10.5g, 0.055mol) into a reaction flask filled with acetone (300ml), control the temperature at 10°C, and stir to make it Dissolved to give a clear solution. Concentrate the reaction solution to 1 / 2 volume, let it stand, cool to 10°C, and crystallize, which is 2,5-dihydroxybenzenesulfonate of prasugrel, weight: 21.0g, yield: 81.1%.

[0073] The characterization results of the product are the same as in Example 1.

Embodiment 3

[0074] Example 3: Synthesis of prasugrel 2,5-dihydroxybenzenesulfonate

[0075] Add prasugrel (17.2g, 0.046mol) and 2,5-dihydroxybenzenesulfonic acid (10.5g, 0.055mol) into a reaction flask filled with acetone (100ml), heat to 56°C, stir to dissolve , a clear solution was obtained. Concentrate the reaction solution to 1 / 2 volume, let stand, cool to 25°C, and crystallize, which is 2,5-dihydroxybenzenesulfonate of prasugrel, weight: 21.8g, yield: 83.9%.

[0076] The characterization results of the product are the same as in Example 1.

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Abstract

The invention discloses an acid-addition salt of Prasugrel, a preparation method and an application. The preparation method comprises the following steps: respectively adding Prasugrel and hydroxyl substituted benzenesulfonic acid in an organic solvent, stirring and dissolving to obtain a settled solution, reacting under certain temperature, concentrating, standing, precipitating crystals, and filtrating to obtain the acid-addition salt of Prasugrel. Compared with Prasugrel, the acid-addition salt of Prasugrel provided by the invention has good stability, the preparation method is simple and easy to be carried out, a single crystal with high purity and a crystal form suitable for drug use can be obtained, the product quality is good, and the yield is high.

Description

technical field [0001] The invention relates to the field of medicine, in particular to 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothiophene with platelet aggregation inhibitory effect Hydroxy-substituted benzenesulfonate of [3,2-c]pyridine (i.e. Prasugrel, Prasugrel), its preparation method and pharmaceutical composition with the compound as an active ingredient, and their use in the preparation of thrombus or embolism Use in medicines for the prevention or treatment of diseases. Background technique [0002] In recent years, the incidence of cardiovascular and cerebrovascular diseases has been on the rise, which has seriously endangered human health. Among them, related diseases caused by thrombus or embolism are the primary factors leading to disability and death. The prevention and treatment of thrombosis and its complications has become an important issue faced by the world medical community. Inhibiting platelet aggregation can effectively im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07C309/42C07C303/32A61K31/4365A61P7/02A61P9/10
CPCC07D495/04C07C303/32C07C309/42A61K31/4365A61P7/02A61P9/10
Inventor 邹永陈洪陈大峰王勇袁辛娅
Owner SICHUAN HAISCO PHARMA CO LTD
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