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Clathrate compound of artemisinin series and alkaline cyclodextrin and method for preparing same

A cyclodextrin inclusion complex and cyclodextrin technology are applied in the directions of pharmaceutical combinations, non-active components of polymer compounds, medical preparations containing active components, etc. The effect of mild reaction conditions and easy operation

Inactive Publication Date: 2012-10-10
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these clathrates have limited solubilization of artemisinin series, which limits the preparation of the drug into liquid preparations (such as oral solutions and injections); α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin Ethyl alcohol, hydroxypropyl β-cyclodextrin, hydroxyethyl β-cyclodextrin, methyl β-cyclodextrin and artemisinin inclusion complex of sulfobutyl ether-β-cyclodextrin, 25°C The solubility in water is 6~20mg / mL (calculated based on the amount of artemisinin series)

Method used

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  • Clathrate compound of artemisinin series and alkaline cyclodextrin and method for preparing same
  • Clathrate compound of artemisinin series and alkaline cyclodextrin and method for preparing same
  • Clathrate compound of artemisinin series and alkaline cyclodextrin and method for preparing same

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Example 1: The clathrates of artemisinin series and basic cyclodextrin, including artemisinin and mono-[6-(ethylenediamine)-6-deoxy]-β-cyclodextrin, artemisinin and mono The weight ratio of -[6-(ethylenediamino)-6-deoxy]-β-cyclodextrin is 1:3.

[0046] During preparation, proceed as follows:

[0047] 1. Preparation of sulfonylated cyclodextrin

[0048] Take 210g of recrystallized β-cyclodextrin and dissolve it in 1300mL of distilled water. After fully stirring, the solution turns into a white emulsion. Add sodium hydroxide solution (17.2g, 50mL) and stir for 1.5h. Weigh 26.0g of p-toluenesulfonyl chloride, dissolve it in 80mL of acetonitrile solution, slowly add the solution dropwise to β-cyclodextrin lye, stir at room temperature for 2 hours, remove a small amount of insoluble matter by suction filtration, and adjust the pH value of the filtrate with 2M hydrochloric acid To 7.5, at this time a large amount of precipitation occurs, and the filtrate is removed by suc...

Embodiment 2

[0054] Example 2: The inclusion complexes of artemisinin series and alkaline cyclodextrin, including artemisinin and mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin, artemisinin and The weight ratio of mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin is 1:98.

[0055] Preparation: Dissolve 1g of artemisinin in 30mL of methanol to form a solution; dissolve 98g of mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin in 500mL of water to prepare a solution Mix the above two solutions under stirring conditions, stir at 40°C for 9h, filter the resulting solution, concentrate under reduced pressure at 40°C, and dry to obtain artemisinin clathrates, which can be dissolved in water at 25°C The solubility is 38mg / mL (calculated based on the amount of artemisinin).

[0056]

Embodiment 3

[0057] Example 3: In the clathrate compound of artemisinin series and alkaline cyclodextrin, the weight ratio of artemisinin to mono-[6-(amino)-6-deoxy]-β-cyclodextrin is 1:50.

[0058] 1g artemisinin was dissolved in 20mL dimethyl sulfoxide to form a solution; 50g mono-[6-(amino)-6-deoxy]-β-cyclodextrin was dissolved in 200mL water to prepare a solution; Mix the above two solutions under stirring conditions, stir at 20°C for 18 hours, filter the obtained solution, concentrate under reduced pressure at 40°C, and dry to obtain artemisinin clathrate. The solubility of clathrate in water at 25°C is 22mg / mL (calculated based on the amount of artemisinin).

[0059]

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Abstract

The invention discloses a clathrate compound of artemisinin series (artemisinin, dihydroartemisinin and artesunate) and alkaline cyclodextrin and a method for preparing the same. The alkaline cyclodextrin in the clathrate compound refers to an amido-substituted cyclodextrin; and due to the amido substituting of the cyclodextrin, an alkaline environment is formed in an aqueous solution apart from clathration between the cavity of the cyclodextrin and the artemisinin series, and forms ionic interaction with hydroxyls or carboxyls on the artemisinin series; and therefore, the artemisinin series can be dissolved in water to form a solution within an extremely wide concentration range so that liquid artemisinin series preparations can be formed. The clathrate compound provided by the invention is high in stability, high in bioavailability, simple in preparation, easy for operation, moderate in condition, and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to the inclusion compound of artemisinin series and basic cyclodextrin and its preparation method. technical background [0002] Malaria has a very large impact on human health in tropical regions of the world. Each year, there are approximately 300 to 500 million clinical cases, often resulting in 1.5 to 1.7 million deaths, almost all of which are due to Plasmodium. With the increase of drug-resistant strains, many traditional alkaloid drugs, such as chloroquine and quinine, are now largely ineffective, allowing further spread of malaria. The World Health Organization (WHO) predicts that malaria cases will double by 2013 without the use of new antimalarial drugs due to the frightening spread of drug resistance in the parasite. In 1979, a new generation of antimalarial drug artemisinin, a sesquiterpene lactone containing a peroxide group isolated from the Chinese herbal medicine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/40A61K31/366A61P33/06A61P35/00
Inventor 杨波肖丹廖霞俐赵榆林杨健
Owner KUNMING UNIV OF SCI & TECH
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