Derivative of cyclo membranousol kind and application thereof

A technology of cycloastragenol and derivatives, which is applied in the field of medicine, can solve the problems of application limitation, irritating reaction, dosage limitation, etc., and achieve the effect of improving bioavailability and water solubility

Inactive Publication Date: 2008-04-30
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dosage of organic solvents is strictly limited in clinical application, and injections containing alcoholic organic solvents are likely to cause irritation to the injection site, which limits the clinical application of such preparations

Method used

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  • Derivative of cyclo membranousol kind and application thereof
  • Derivative of cyclo membranousol kind and application thereof
  • Derivative of cyclo membranousol kind and application thereof

Examples

Experimental program
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preparation example Construction

[0081] In the preparation method described herein, cycloastragenol or its naturally derived derivative astragaloside IV is used as a raw material.

[0082] Among them, cycloastragenol is obtained by hydrolyzing total saponins of astragalus through known conventional hydrolysis technology (enzyme hydrolysis, acid hydrolysis); astragaloside IV is prepared according to the patented technology with application number 200410007963.0.

Embodiment 1

[0083] The preparation of embodiment 1 cycloastragenol phosphate ester salt

[0084] a. Add 1g of cycloastragenol, 3g of dibenzyl phosphate, 2.7g of triphenylphosphine and 200ml of ethyl acetate in the reaction flask, cool to 15°C under stirring, add dropwise 1g of diethyl azodicarboxylate (DEAD ), lasted about 30 minutes, the dropwise addition was completed, continued to stir for 1 hour, raised the temperature to 35 ° C, and kept the reaction for 5 hours. After the reaction was completed, the ethyl acetate layer was washed with aqueous sodium bicarbonate and dried overnight over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure to obtain an oil. After silica gel column chromatography and dichloromethane / methanol solvent system elution and separation, the dibenzyl phosphate of cycloastragenol was obtained.

[0085] b. Debenzylation: take 0.5 g of cycloastragenol dibenzyl phosphate, add 50 ml of methanol, add 0.2 g of 10% palladium carbon, ventilat...

Embodiment

[0089] The preparation of embodiment 2 cycloastragenol 3-O-sulfonate salt

[0090] a. Take 6g of cycloastragenol that has been ground through a 40-mesh sieve, add 300ml of absolute ethanol, cool to 5°C-10°C under stirring, slowly add 50ml of concentrated sulfuric acid dropwise, after the addition is complete, heat up to 20°C-25°C, Insulated and stirred for 48 hours. After the reaction is complete, add 300ml of absolute ethanol, take an ice-water bath, under stirring, adjust the pH value to 7 with 40% sodium hydroxide, and let stand for 24 hours. Add an appropriate amount of activated carbon, filter, and evaporate the filtrate under reduced pressure to obtain the sulfonated cycloastragenol.

[0091] b. Separation and purification: Dissolve 5 g of the sulfonated cycloastragenol in 25 ml of water, filter and apply to a D101 macroporous resin column, and elute with water, 10%, 30%, 50%, 70%, and 90% ethanol in sequence (TLC trace). The combined Rf values ​​are comparable to the...

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Abstract

The invention supplies eye-astragalus alcohols compounding ramification that could improve the water solubility of parent substance compounding. The invention could improve the biology availability of the drug, and make it possible to develop the constituent into oral dosing agent. It could be used in curing cardiovascular disease and cerebrovascular disease, myocarditis, nephritis, diabetes, rheumatism and hepatitis. It could be also used to anti virus.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to new cycloastragenol derivatives and their preparation methods and pharmaceutical compositions containing them, and the use of cycloastragenol derivatives in the preparation and treatment of cardiovascular and cerebrovascular diseases, myocarditis, nephritis and diabetes , rheumatism, hepatitis and antiviral applications. Background technique [0002] Cycloastragenol (Cycloastragenol) compounds belong to lanosterane-type tetracyclic triterpenoid structure. Since they were discovered from the leguminous Astragalus plants, they have attracted extensive attention because of their unique biological activities. In nature, such compounds mainly exist in the form of glycosides, and the linked sugars include xylose, glucose, and rhamnose. Due to the difference in the position of the sugar on the aglycone, the type of sugar, and the sugar chain, different properties are formed....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/04A61K31/341A61K9/00A61P9/00A61P3/10A61P1/16A61P31/12
Inventor 刘登科韩英梅徐为人黄长江赵娜夏张士俊任戎刘鹏刘颖夏广萍王玉丽付晓丽赵专友刘默汤立达
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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