Leucinocaine 10-O-(dimethylaminoethyl)ginkgolide B semihydrate crystal and preparation method thereof

A technology of dimethylaminoethyl and ginkgolide, which is applied in the field of medicine and chemical industry, can solve the problems of dangerous operation, cumbersome synthesis steps, and difficult production, and achieve the effect of easy operation, simple preparation steps, and good stability

Active Publication Date: 2009-12-09
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ginkgolides are strong antagonists of platelet-activating factor (PAF), among which ginkgolide B has the strongest activity. Platelet-activating factor is a strong physiological regulator and plays an important role in many physiological phenomena. Roles, such as allergies, inflammation and asthma, etc., but ginkgolides are not soluble in water, and ginkgolide B cannot exert its optimal efficacy. Therefore, finding appropriate PAF antagonists for medical use is an important task in the medical field. very important subject
[0003] The patent (publication number CN 1749257A) has reported the synthesis of ginkgolide B derivative compound 10-O-(dimethylaminoethyl) ginkgolide B and its salts, which played an important role in the efficacy of ginkgolide B. Effects, such as 10-O-(dimethylaminoethyl) ginkgolide B hydrochloride, 10-O-(dimethylaminoethyl) ginkgolide B sulfate, 10-O-(two Methylaminoethyl) ginkgolide B acetylsalicylate and 10-O-(dimethylaminoethyl) ginkgolide B citrate, these compounds are either unstable, especially in aqueous solutions Easy to degrade in medium, such as 10-O-(dimethylaminoethyl) ginkgolide B acetylsalicylate and 10-O-(dimethylaminoethyl) ginkgolide B citrate; Or the synthesis steps are cumbersome and dangerous to operate, such as 10-O-(dimethylaminoethyl) ginkgolide B hydrochloride and 10-O-(dimethylaminoethyl) ginkgolide B sulfate , need to use hydrochloric acid gas and concentrated sulfuric acid, which brings certain difficulties to production

Method used

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  • Leucinocaine 10-O-(dimethylaminoethyl)ginkgolide B semihydrate crystal and preparation method thereof
  • Leucinocaine 10-O-(dimethylaminoethyl)ginkgolide B semihydrate crystal and preparation method thereof
  • Leucinocaine 10-O-(dimethylaminoethyl)ginkgolide B semihydrate crystal and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Example 1 Preparation of 10-O-(dimethylaminoethyl) ginkgolide B

[0016] 250g (0.59mol) of ginkgolide B was dissolved in 8.6L of acetonitrile, followed by adding 130g of dimethylaminoethyl chloride hydrochloride, 800g of potassium carbonate, 100g of potassium iodide, and 20g of tetrabutylammonium bromide, and heated to reflux for 1 hour. The reaction is almost complete. Cool, filter, and concentrate the filtrate under reduced pressure to obtain a crude solid. The crude product was purified, recrystallized from methanol, and dried to obtain 117 g of solid (yield 40%).

Embodiment 2

[0017] Example 2 Preparation of methanesulfonic acid 10-O-(dimethylaminoethyl) ginkgolide B hemihydrate crystallization 10-O-(dimethylaminoethyl) ginkgolide B 10g, methanol 100ml, stirring, Add 41g of 4.8% methanol solution of methanesulfonic acid dropwise, heat slightly, add a small amount of activated carbon after fully dissolved, reflux, filter while hot, cool and crystallize, filter, wash with methanol, add the obtained solid to 100ml of 90% methanol, heat Dissolve, then cool to crystallize, filter, and wash with 90% methanol to obtain methanesulfonic acid 10-O-(dimethylaminoethyl) ginkgolide B hemihydrate crystals.

Embodiment 3

[0018] The preparation of embodiment 3 methanesulfonic acid 10-O-(dimethylaminoethyl) ginkgolide B hemihydrate crystals

[0019] 10g of 10-O-(dimethylaminoethyl) ginkgolide B, 100ml of ethanol, stir, add dropwise 41g of 4.8% methanesulfonic acid ethanol solution, heat slightly, add a small amount of activated carbon after fully dissolved, reflux, while hot Filtration, crystallization by cooling, filtration, washing with ethanol, the resulting solid was added to 100ml of 90% ethanol, heated to dissolve, then cooled to crystallize, filtered, washed with 90% ethanol to obtain methanesulfonic acid 10-O-(dimethylaminoethyl Base) Ginkgolide B hemihydrate crystallization.

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Abstract

The invention provides a methanesulfonic acid 10-O-(dimethyl amido ethyl) bilobalide B calcium sulfate hemihydrate compound and a relative preparation method, while the compound formula is represented as right. The preparation method comprises crystallizing methanesulfonic acid 10-O-(dimethyl amido ethyl) bilobalide B in organic solvent containing water, while the compound has the advantages of better stability, solubility and drug effect, which can treat the diseases as ischemic stroke, inflammation and asthma relative with PAF factor.

Description

technical field [0001] The invention relates to a methanesulfonic acid 10-O-(dimethylaminoethyl) ginkgolide B hemihydrate crystal and a preparation method thereof, in particular to methanesulfonic acid 10-O-(dimethylaminoethyl) ) Ginkgolide B hemihydrate crystalline compound and a preparation method thereof belong to the field of medicine and chemical industry. Background technique [0002] Ginkgolides are a series of diterpenoid compounds present in Ginkgo biloba leaves and rhizomes, and their chemical properties are quite stable. Ginkgolides are strong antagonists of platelet-activating factor (PAF), among which ginkgolide B has the strongest activity. Platelet-activating factor is a strong physiological regulator and plays an important role in many physiological phenomena. Roles, such as allergies, inflammation and asthma, etc., but ginkgolides are not soluble in water, and ginkgolide B cannot exert its optimal efficacy. Therefore, finding appropriate PAF antagonists for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/22
Inventor 秦引林
Owner JIANGSU CAREFREE PHARM CO LTD
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