Novel resinate complex of S-clopidogrel and production method thereof

A technology of clopidogrel and resinate, applied in the directions of non-active ingredient medical preparations, active ingredients-containing medical preparations, drug combinations, etc., can solve problems such as affecting the stability of esters, achieve good safety, excellent The effect of liquidity

Inactive Publication Date: 2008-08-27
CHONG KUN DONG CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0032] The use of certain acidic substances in the prior art for crystallization (+)-clopidogrel isomers may affect the stability of the ester in the clopidogrel molecule, so the inventors of the present invention are committed to the research of the formula to ensure drug safety and efficacy

Method used

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  • Novel resinate complex of S-clopidogrel and production method thereof
  • Novel resinate complex of S-clopidogrel and production method thereof
  • Novel resinate complex of S-clopidogrel and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: Methyl (+)-(S)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate- Styrene Sulfonate Polymer Compound

[0083] 2.40 g (7.45 mmole) of (+)-clopidogrel isomer (free base) was dissolved in 50 ml of acetone, cooled and stirred. 1.25 mL of 18% styrene sulfonate polymer solution was slowly added dropwise to the cooled solution. The resulting solution was stirred for a period of time during which time a precipitate formed. After decanting the supernatant of the solution, 20 mL of cooled acetone was added and stirred. The solid precipitate was then collected by filtration and dried in a vacuum oven. In the collected resinate complexes, approximately 54.2% of the total dry solids were (+)-clopidogrel isomers as determined by high performance liquid chromatography (HPLC) analysis.

Embodiment 2

[0084] Example 2: Methyl (+)-(S)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate- Styrene Sulfonate Polymer Compound

[0085] 0.44 g (1.35 mmole) of (+)-clopidogrel isomer (free base) was dissolved in 50 ml of acetone, cooled and stirred. 1.2 mL of 18% styrene sulfonate polymer solution was slowly added dropwise to the cooled solution. The resulting solution was stirred for a period of time during which time a precipitate formed. After decanting the supernatant of the solution, 20 mL of cooled acetone was added and stirred. The solid precipitate was then collected by filtration and dried in a vacuum oven. As determined by HPLC analysis, about 52.1% of the total dry solids in the collected resinate complexes were (+)-clopidogrel isomers.

Embodiment 3

[0086] Example 3: Methyl (+)-(S)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate- Styrene Sulfonate Polymer Compound

[0087] 2.40 g (7.45 mmole) of (+)-clopidogrel isomer (free base) was dissolved in 100 ml acetone, cooled and stirred. 1.2 mL of 18% styrene sulfonate polymer solution was slowly added dropwise to the cooled solution. The resulting solution was stirred for a period of time during which time a precipitate formed. After decanting the supernatant of the solution, 50 mL of cooled acetone was added and stirred. The solid precipitate was then collected by filtration and dried in a vacuum oven. As determined by HPLC analysis, about 53.6% of the total dry solids in the collected resinate complexes were (+)-clopidogrel isomers.

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Abstract

The present invention is a novel resinate complex of (+)-clopidogrel optical isomer, wherein the (+)-clopidogrel isomer is bounded to a water-soluble cation exchange resin having sulfonic acid groups. The novel resinate complex has recognized some advantages in that (1) its chemical structure is stable, and (2) it can be formulated into a solid form that may provide taste-masking capabilities associated with bitter drugs (e.g., strong irritation, bitterness and sour taste), thus requiring no drink of water.

Description

technical field [0001] The present invention relates to a novel (+)-clopidogrel (clopidogrel) optical isomer resinate complex, wherein the (+)-clopidogrel isomer is combined with a water-soluble compound containing a sulfonic acid group combined with cation exchange resins. Background technique [0002] Clopidogrel has been shown to inhibit platelet aggregation and is useful in the treatment and prevention of thromboembolism, such as stroke or myocardial infarction. Dexclopidogrel or the racemate exhibited activity on platelet aggregation, while the levoisomer was less active and less well tolerated. [0003] Clopidogrel (free base) is a semi-solid (oily) form with high viscosity fluidity, which is not conducive to storage or handling. Its low solubility in water makes it difficult to develop industrially into medicinal products. [0004] In order to make clopidogrel a medicine for human body, it is necessary to use a solid state (preferably a powder form) that can be dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCA61K31/4365A61K47/585A61P7/00C07D495/04A61K31/60C08F12/30C08F12/36C08J5/20
Inventor 申熙钟奇旻孝崔美花
Owner CHONG KUN DONG CORP
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