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Synthetic technological process of bilobalide B derivates

A technology of ginkgolide and synthesis process, which is applied in the field of medicine, can solve problems such as retention, actual production operation and hidden safety hazards, and achieve the effects of cost simplification, cost reduction, and increased reaction rate

Active Publication Date: 2008-12-17
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its synthesis method only stays in the experimental stage, and the output is very small and limited to the gram level. The synthesis process needs to involve strong reducing agent sodium hydride and inert gas protection, which brings huge hidden dangers to its actual production operation and safety.

Method used

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  • Synthetic technological process of bilobalide B derivates
  • Synthetic technological process of bilobalide B derivates
  • Synthetic technological process of bilobalide B derivates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation of 10-O-(dimethylaminoethyl) ginkgolide B

[0015] 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%).

[0016] Reaction route:

[0017]

Embodiment 2

[0018] Example 2 Preparation of 10-O-(N-ethylmorpholide) ginkgolide B

[0019] 60g (0.14mol) of ginkgolide B was dissolved in 4L of acetonitrile, followed by adding 37g of N-(2-chloroethyl)morpholine hydrochloride, 250g of potassium carbonate, 25g of potassium iodide, cetyltrimethylammonium bromide 20g, heated to reflux until 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 37 g of solid (yield 49%).

[0020] Reaction route:

[0021]

Embodiment 3

[0022] Example 3 Preparation of 10-O-(diethylaminoethyl) ginkgolide B

[0023] 250g (0.59mol) of ginkgolide B was dissolved in 8.6L of tetrahydrofuran, followed by adding 155g of diethylamino ethyl chloride hydrochloride, 800g of potassium carbonate, 100g of potassium iodide, and 18g of triethylbenzyl ammonium chloride, and heated to reflux for 1 Hours, the reaction was 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 125 g of solid (yield 41%).

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PUM

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Abstract

The invention discloses a technological method for synthesizing a bilobalide B derivative. Under alkaline condition and presence of an organic solvent, a homogeneous catalyst and a compound of X-R1-N (R2)-R3 are added into for reaction to obtain a derivative after the C10 hydroxyl of the bilobalide B is etherified; wherein, X represents halogen, R1, R2 and R3 represent alkane or naphthenic hydrocarbon with 1-8 carbon atoms and decorate the C10 hydroxyl of the bilobalide B. The technological method for synthesizing the bilobalide B derivative of the invention is safe, economical and applicable to industrialized production, thus bring promising prospect to the market-oriented development of the bilobalide B.

Description

technical field [0001] The invention relates to a synthesis process for a class of compounds, in particular to a synthesis process for derivatives of ginkgolide B, and belongs to the technical field of medicine. Background technique [0002] Ginkgo biloba has been used as a medicinal plant for a long time. Around 1000 AD, Chinese folks used ginkgo leaves to treat asthma and bronchitis. With the standardization of drug extraction process and the in-depth study of pharmacological activity, countries all over the world, especially European countries such as Germany and France, have widely used Ginkgo biloba extract (GBE) to treat respiratory system, cardiovascular and cerebrovascular system and other diseases. Ginkgolides are a series of diterpenoid compounds present in Ginkgo biloba leaves and rhizomes, and their chemical properties are quite stable. Ginkgolide is a strong antagonist of platelet-activating factor (PAF), which is a strong physiological regulator and plays an i...

Claims

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Application Information

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