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Method for improving purity of cyclovirobuxine D

A Cyclovitamin, high-purity technology, applied in the direction of steroids, organic chemistry, etc., can solve the problem of unsatisfactory cyclobuxine D removal, and achieve the effect of improving purity and saving resources

Inactive Publication Date: 2019-09-24
荆门市锦秀天成医药技术服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] According to the types and structural characteristics of boxwood alkaloids, the author once used potassium permanganate, nitrous acid, sodium hypochlorite to oxidize demethylation and silver nitrate dimethylformamide to reflux demethylation, but was unsuccessful; Demethylation of ethyl esters, chloroformate esters, etc. is also unsuccessful, and the removal of cyclobuxicine D with a silver nitrate complexed silica gel column is also not ideal

Method used

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Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0024] Dissolve 2 g of the boxwood alkaloid raw material in 100 ml of acetic acid, adjust the pH to 5 with ammonia water, extract twice 50 ml x 2 with refined chloroform, dry over anhydrous sodium sulfate, and recover the solvent to obtain 0.4 g of the weak base. Adjust the pH to 9 with ammonia water, extract twice 50ml×2 with refined chloroform, dry over anhydrous sodium sulfate, and recover the solvent to obtain 1.58g of strong base. Dissolve 1.58 g of the strong base into 30 ml of isoamyl nitrite, add 1 ml of concentrated hydrochloric acid dropwise under ice-cold conditions, stir and mix well, and then add a small amount of ethanol until the crystal adduct precipitates. filter. Recover isoamyl nitrite to obtain 1.4 g of Cyclovirubuxin D. Dissolve 0.4g of the weak base in 10ml of anhydrous tetrahydrofuran, add 0.4g of cyanogen bromide dropwise at room temperature, stir for 15 hours, add 5ml of 6% sodium carbonate solution and stir for 3 hours, reflux for 1 hour, let cool, a...

specific Embodiment 2

[0026]Dissolve 3 g of the boxwood alkaloid raw material in 120 ml of acetic acid, adjust the pH to 5 with ammonia water, extract twice 50 ml x 2 with refined chloroform, dry over anhydrous sodium sulfate, and recover the solvent to obtain 0.58 g of the weak base. Adjust the pH to 9 with ammonia water, extract twice 50ml×2 with refined chloroform, dry over anhydrous sodium sulfate, and recover the solvent to obtain 2.35g of strong base. Dissolve 2.35 g of the strong base in 50 ml of anhydrous ether, add 0.9 g of zinc diiodomethane, stir and mix, and then reflux for 4 hours. Allow to cool to room temperature, add 0.1 g of 5% palladium carbon, and inject hydrogen until no absorption occurs. Filter, wash ether twice with acidic water and water, dry over anhydrous sodium sulfate, and recover ether to obtain 2.13 g of Cyclovirubuxin D. Dissolve 0.58g of the weak base in 60ml of methanol, add 0.7g of anhydrous sodium acetate, 0.6g of iodine, stir and dissolve at 50°C, add 12ml of wa...

specific Embodiment 3

[0029] Dissolve 3 g of boxwood alkaloid raw material in 100 ml of chloroform, stir and mix with 0.9 ml of methyl iodide reagent, leave it overnight, filter to remove insoluble matter; recover solvent to obtain 1.8 g of secondary amine alkaloid part. It was dissolved in 50ml of anhydrous ether, and then 1.5g of zinc diiodomethane was added, stirred and mixed, and then refluxed for 4 hours. Allow to cool to room temperature, add 0.1 g of 5% palladium carbon, and inject hydrogen until no absorption occurs. Filter, wash ether twice with water, dry over anhydrous sodium sulfate, and recover ether to obtain 1.7 g of Cyclovirubuxin D. Dissolve 1.5 g of insoluble matter into 10 ml of anhydrous dimethyl sulfoxide, add 20 ml of anhydrous tetrahydrofuran solution of lithium triethylborohydride (containing 0.4 g of lithium triethylborohydride), and react for 3 hours at room temperature with nitrogen gas , and then poured into 50ml of water. Extract 40ml x 2 times with chloroform, dry ov...

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Abstract

The invention discloses a method for improving the purity of cyclovirobuxine D. The method comprises the following steps: (1), dividing a boxwood alkaloid raw material into secondary amine alkaloid and tertiary amine alkaloid by using a pH gradient extraction method or using methyl iodide and a lithium triethylborohydride reagent; (2), dissolving the secondary amine alkaloid in an organic solvent, adding a carbenoid reagent for a reaction, then adding palladium-carbon, introducing hydrogen for a reaction, or adding a nitroso acyl chloride reagent to the secondary amine alkaloid for a reaction so as to obtain high-purity cyclovirobuxine D; and (3), adding a cyanogen bromide reagent to the tertiary amine alkaloid, performing a Von Braun reaction so as to remove methyl groups in the tertiary amine alkaloid, or performing an iodine oxidation reaction on the tertiary amine alkaloid so as to remove the methyl groups in the tertiary amine alkaloid, and then performing column chromatography treatment so as to obtain the high-purity cyclovirobuxine D and cyclovirobuxine C. Through the method for improving the purity of the cyclovirobuxine D, not only can resources be saved, but also the purity of the cyclovirobuxine D can be improved.

Description

technical field [0001] The invention relates to the field of traditional Chinese medicines, in particular to a method for improving the purity of cyclovirbuxin D. Background technique [0002] Ring-dimensional Buxus D is Buxus microphylla Sieb.et Zucc. var. sinica Rehd. et Wils and the alkaloids extracted from plants of the same genus are the national basic cardiovascular therapeutic drugs included in the Chinese Pharmacopoeia in 2005, 2010, and 2015. The above-mentioned symptoms are often seen in chest pain and heart pain caused by stagnant blood stasis, pulse stagnation, coronary heart disease, and arrhythmia. Dosage: 1~2mg, 2~3 times a day, 2~6mg per day, which belongs to the scope of trace dosage. As a natural drug, such a small dosage has strong cardiovascular physiological activity and good safety, which indicates that the drug is extraordinary and has great potential value for further development. The composition of Buyang Ning is mainly cyclovirboxic star D. ...

Claims

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Application Information

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IPC IPC(8): C07J53/00
CPCC07J53/001
Inventor 张秀梅
Owner 荆门市锦秀天成医药技术服务有限公司
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