Andrographolide synthetic method

A synthetic method, the technology of Yanhuning, applied in the field of medicine, can solve the problems of large solvent feeding coefficient, cumbersome operation, increased cost and energy consumption, etc., and achieve the effect of improving product purity, increasing yield and reducing production cost

Inactive Publication Date: 2013-05-22
CHENGDU BRILLIANT PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purity of the product is good, but the solvent feeding coefficient is relatively large, and a variet

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) Preparation of 14-deoxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester (dehydroandrographolide succinic acid half ester)

[0044] 144g (0.41mol) andrographolide, 148g succinic anhydride, 6g sodium sulfite, and 160g pyridine were placed in the reaction flask. Stir well, reduce the pressure to a vacuum greater than 0.08MPa, and raise the temperature gradually to keep the internal temperature of the system at 80-90°C. The reaction was maintained in this temperature range for 1.5 hours. After the reaction was completed, an orange-yellow solution was obtained, which was poured into 3000 g of hot water at 50° C. under stirring, and solids gradually precipitated out. Naturally cool down to 20-30°C, continue to cool down to 0-5°C, let stand in this temperature range for 12 hours, filter, rinse the filter cake with 200g of water and drain it, then transfer it to a drying oven for vacuum drying to obtain 205g of white solid. The yield is 93%.

[0045] (2) P...

Embodiment 2

[0048] (1) Preparation of 14-deoxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester (dehydroandrographolide succinic acid half ester)

[0049] 100g (0.29mol) andrographolide, 114g succinic anhydride, 6g sodium sulfite, and 130g pyridine were placed in the reaction flask. Stir well, reduce the pressure to greater than 0.09MPa, and raise the temperature gradually to keep the internal temperature of the system at 80-90°C. The reaction is maintained in this temperature range. After the reaction was completed, it was poured into 2100 g of hot water at 44° C. under stirring, and stirred for half an hour, and solids gradually precipitated out. Naturally cool down to 20-30°C, continue to cool down to 0-5°C, let stand in this temperature range for 12 hours, filter, rinse the filter cake with 130g of water and dry it, then transfer it to a drying oven for vacuum drying to obtain 140g of white solid. The yield is 92%.

[0050] (2) Preparation of 14-dehydro-11,12-didehydr...

Embodiment 3

[0053] (1) Preparation of 14-deoxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester (dehydroandrographolide succinic acid half ester)

[0054] 288g (0.82mol) of andrographolide, 296g of succinic anhydride, 13g of sodium sulfite, and 330g of pyridine were placed in the reaction flask. Stir well, reduce the pressure to greater than 0.08MPa, and raise the temperature gradually to keep the internal temperature of the system at 80-90°C. The reaction is maintained in this temperature range. After the reaction was completed, it was poured into 5000 g of hot water at 50° C. under stirring, and stirred for half an hour. Naturally cool down to 20-30°C, continue to cool down to 0-5°C, let stand in this temperature range for 12 hours, filter, wash the filter cake with 350g of water, drain it and transfer it to a drying oven for vacuum drying to obtain 415g of white solid . The yield is 95%.

[0055] (2) Preparation of 14-dehydro-11,12-didehydroandrographolide-3,19-disucc...

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PUM

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Abstract

The invention belongs to the field of medicaments, in particular relates to an andrographolide synthetic method and aims at providing a synthetic method for improving the synthesis yield of the andrographolide. The andrographolide synthetic method comprises the two following steps of: esterification reaction and satifying reaction, wherein in the esterification reaction, dehydration paniculta lactone succinate half ester is prepared; and in the satifying reaction, dehydration paniculta lactone succinate half ester potassium sodium salt, namely andrographolide, is prepared. The andrographolide synthetic method comprises a first step of esterification reaction as follows: raising the temperature of andrographolide, succinic anhydride, pyridine and anhydrous sodium sulfite to react at a pressure reduction vacuum state; dissolving in a warm heat water; and crystallizing at a low temperature to obtain the dehydration paniculta lactone succinate half ester; and a step of satifying reaction as follows: dissolving the dehydration paniculta lactone succinate half ester into an ethanol solution with the concentration of more than or equal to 95 percent by volume; adding a kali salt solution to react to obtain the dehydration paniculta lactone succinate half ester potassium sodium salt; dissolving the dehydration paniculta lactone succinate half ester potassium sodium salt into absolute ethyl alcohol and adding a sodium salt solution to react, filter and wash to obtain the andrographolide.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a method for synthesizing Yanhuning. Background technique [0002] Yanhuning is the potassium sodium salt of Andrographis paniculata half-ester succinate obtained from the reaction of Chuanhuning with alkali or sodium salt. The common name is Yanhuning for injection, and the trade name is Zhili. This product has heat-clearing, detoxifying and antiviral effects, and is mainly used for viral pneumonia and viral upper respiratory tract infection. [0003] The English name of Yanhuning for injection is: Potassium Sodium Dehydroandroan drographolide Succinate for Injection. The main ingredient is Yanhuning. The chemical name is: 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinate Acid half ester potassium sodium salt. The molecular formula is: C 28 h 34 KNaO 10 ·H 2 O, molecular weight: 610.68. [0004] At present, the synthetic method of Yanhuning mainly has the fo...

Claims

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Application Information

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IPC IPC(8): C07D307/58
Inventor 杨成甫邓曦崔阳文
Owner CHENGDU BRILLIANT PHARMA CO LTD
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