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Anti-platelet activating factor compound

An activating factor and anti-platelet technology, applied in anti-inflammatory agents, organic chemistry, drug combination, etc., can solve the problems of changing the solubility and efficacy of ginkgolide B, affecting the clinical application effect, and limiting the full efficacy of the drug, etc. Achieve the effect of enhanced bioavailability, low toxicity and enhanced curative effect

Inactive Publication Date: 2008-11-12
秦引林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Ginkgolide B is a diterpene compound with a six-ring cage structure, and its oral LD50>5g / kg shows a high degree of safety. However, Ginkgolide B has a rigid structure, is insoluble in water, and has poor bioavailability. As a result, the full play of the drug effect is limited, which affects the clinical application effect
[0005] At present, there are some researches (WO9518131) on ginkgolide B derivatives both at home and abroad, and there are some researches on changing the solubility and drug efficacy of ginkgolide B, but all do not involve the research on indicators such as its safety. Some safe, effective and highly bioavailable derivatives will bring a bright future for the market development of ginkgolide B

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation process of 10-O-(N-ethylmorpholino) ginkgolide B and its mesylate

[0015] 600 mg (1.4 mmol) of ginkgolide B was dissolved in 40 mL of acetonitrile, 370 mg (2.0 mmol) of N-(2-chloroethyl) morpholine hydrochloride, 2.5 g of potassium carbonate, and 50 mg of potassium iodide were added successively, and heated to reflux for 1 hour. The reaction is almost complete. Cool, filter, and concentrate the filtrate under reduced pressure. Add chloroform to the obtained solid and wash it to obtain a crude product. The crude product was chromatographed and eluted with ethyl acetate / petroleum ether (1:1) to obtain a colorless oil. Adding an appropriate amount of anhydrous diethyl ether to the oil resulted in the precipitation of a white solid, which was filtered and dried to obtain 300 mg of a white solid (yield Rate 40%), namely 10-O-(N-ethylmorpholino) ginkgolide B. The obtained solid was dissolved in ethanol, an equimolar amount of ethanol solution of metha...

Embodiment 2

[0018] Example 2 10-O-(N-ethylmorpholino) ginkgolide B acetylsalicylate and its preparation process

[0019] 300 mg of 10-O-(N-ethylmorpholino) ginkgolide B was dissolved in ethanol, and an equimolar amount of acetylsalicylic acid in ethanol was added dropwise, stirred, and spin-dried to obtain 10-O-( N-ethylmorpholino) ginkgolide B acetylsalicylate.

[0020] The synthetic route of 10-O-(N-ethylmorpholino) ginkgolide B acetylsalicylate:

[0021]

Embodiment 3

[0022] Example 3 Comparison of water solubility of compounds before and after modification

[0023] A simple comparison of the water solubility of the compound before and after the structural modification was carried out. Similarly, equimolar amounts of ginkgolide B, 10-O-(N-ethylmorpholinyl) ginkgolide B, 10-O-(N-ethyl Morpholinyl) ginkgolide B hydrochloride and 10-O-(N-ethylmorpholino) ginkgolide B methanesulfonate were measured for their dissolution status, and the results are shown in Table 1.

[0024] Table 1 Comparison results of water solubility of compounds before and after modification

[0025] compound

[0026] It shows that after structural modification, the water solubility of the corresponding salt of ginkgolide B derivatives can change the poor water solubility of original ginkgolide B.

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Abstract

The invention discloses an anti-platelet activation factor compound, wherein the compound is connected with N-ethyl morpholine radical on the NO. 10 oxygen atom of ginkgolide B; the molecular structural formula of 10-O-(N-ethyl morpholine radical) ginkgolide B is shown in the graph. The compound can also be reacted with corresponding organic acid or inorganic acid to generate salt, and can be made into appropriate formulation so as to be applied in clinic. Moreover, the anti-platelet activation factor compound has the advantages that: the compound can increase water solubility and is propitious to bring drug effect into full play; meanwhile, the compound can reduce toxicity and increase safety, etc.

Description

technical field [0001] The invention relates to a drug with antagonistic effect on platelet activating factor (PAF), in particular to a compound with a nitrogen-containing group connected to the oxygen atom at the 10-position of ginkgolide B. 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 deepening of pharmacological activity research, countries all over the world, especially European countries such as Germany and France, have widely used Ginkgo biloba extract (GB) 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 phys...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22A61K31/5377A61P9/10A61P25/00A61P29/00A61P11/06
Inventor 秦引林
Owner 秦引林
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