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Method for preparing ginkgolide K

A technology of ginkgolide and organic solvent, which is applied in the field of preparation of ginkgolide K, can solve the problems of difficult scale-up production, high reaction temperature, and unknown yield, and achieve high yield and purity, and simple operation

Active Publication Date: 2015-10-28
CHENGDU BAIYU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Patent CN101824041A reports a method for preparing ginkgolide K by high-temperature reaction of ginkgolide B in an organic solvent under the conditions of inorganic acids such as hydrochloric acid and sulfuric acid. The reaction temperature is relatively high, and the yield is unknown, so it is difficult to scale up production

Method used

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  • Method for preparing ginkgolide K
  • Method for preparing ginkgolide K
  • Method for preparing ginkgolide K

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Dissolve 5 g of ginkgolide B (GB) in 100 mL of dry dichloromethane, stir and mix evenly, then cool down to -25°C under nitrogen protection. Add 10mL of DAST dropwise (that is, the volume-to-weight ratio of ginkgolide B is 2mL / g), and keep the reaction for 0.5h; then raise the temperature to room temperature, and stir the reaction until the raw material of ginkgolide B (GB) is completely reacted. Add 50 mL of purified water to the reaction solution, quench the reaction and remove the organic solution by rotary evaporation, extract the aqueous layer with ethyl acetate, wash the organic layer with saturated sodium bicarbonate solution and sodium chloride solution, and then dry it, and remove the organic solution by rotary evaporation to obtain Oil. Purification by column chromatography (petroleum ether / ethyl acetate = 2:1) yielded 1.2 g of ginkgolide K as a white solid, with a yield of 25% and an HPLC purity of 99.24%.

[0040] Liquid mass (LC-MS) and hydrogen spectrum of...

Embodiment 2

[0045] Dissolve 5 g of ginkgolide B in 100 mL of dry dichloromethane, stir and mix evenly, then cool down to -25°C under nitrogen protection. Add 50mL DAST dropwise (that is, the volume-to-weight ratio of ginkgolide B is 10mL / g), and keep it warm for 0.5h; Add 50 mL of purified water to the reaction solution, quench the reaction and remove the organic solution by rotary evaporation, extract the aqueous layer with ethyl acetate, wash the organic layer with saturated sodium bicarbonate solution and sodium chloride solution, and then dry it, and remove the organic solution by rotary evaporation to obtain Oil. Purification by column chromatography (petroleum ether / ethyl acetate = 2:1) yielded 1.08 g of ginkgolide K as a white solid, with a yield of 23% and an HPLC purity of 99.51%.

Embodiment 3

[0047]Dissolve 5 g of ginkgolide B in 100 mL of dry acetonitrile, stir and mix evenly, then cool down to -25°C under nitrogen protection. Add 15mL of DAST dropwise (that is, the volume-to-weight ratio of ginkgolide B is 3mL / g), and keep it warm for 0.5h; then raise the temperature to room temperature, and stir until the raw material of ginkgolide B reacts completely. Add 50mL of purified water to the reaction solution, quench the reaction, remove the organic solution by rotary evaporation, extract the aqueous layer with ethyl acetate, wash the organic layer with saturated sodium bicarbonate solution and sodium chloride solution, and dry it, then remove the organic solution by rotary evaporation Get oil. Purification by column chromatography (petroleum ether / ethyl acetate=2:1) ​​yielded 1.3 g of ginkgolide K as a white solid, with a yield of 27% and an HPLC purity of 99.38%.

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Abstract

The invention discloses a method for preparing ginkgolide K. The method includes the following steps: 1, ginkgolide B is dissolved into organic solvents to obtain a solution; 2, fluorinating agents are added into the solution obtained in the step 1 for conducting a dehydration reaction, and the ginkgolide K is obtained through separation and purification. The method for preparing the ginkgolide K is easy to operate; meanwhile, the high yield and the high purity are achieved, and convenience is brought to industrialization large-scale production. (please see the specification for the formula).

Description

technical field [0001] The invention relates to a preparation method of ginkgolide K. Background technique [0002] Ginkgolides are the main active ingredients in Ginkgo biloba, and they have been proved to have a wide range of pharmacological effects and pharmaceutical value. The ginkgolide compounds that have been discovered so far include ginkgolide A, ginkgolide B, ginkgolide C, bilobalide, ginkgolide J, ginkgolide M, ginkgolide L, ginkgolide K and the like. Among them, Ginkgolide K (English name Ginkgolide K, abbreviated as GK) has received widespread attention since Lou Fengchang et al. obtained trace samples by means of liquid preparation and carried out structural characterization by nuclear magnetic and infrared means. The structure of Ginkgolide K (GK) is as follows: [0003] [0004] At present, many literatures have reported the pharmacological effects of ginkgolide K, which is not only a strong platelet activating factor (PAF) receptor antagonist, but also ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 李大雄柯鸿樊小波孙毅
Owner CHENGDU BAIYU PHARMA CO LTD
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