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Method for preparing potassium dehydroandrographolide succinate or potassium sodium dehydroandroan drographolide succinate

A technology of Yanhuning and Chuanhuning, which is applied in the field of medicine, can solve the problems of high consumption, environmental pollution, and low yield, and achieve the effects of protecting the environment, avoiding unpleasant odors, and ensuring product quality

Inactive Publication Date: 2012-08-01
HUBEI HOPE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main reasons for the specific analysis of adverse reactions are (1) individual differences (allergic constitution); (2) andrographolide has poor stability and is prone to hydrolysis, ring opening, isomerization and unsaturated bond oxidation of the lactone
(3) The purity of the initial raw material (andrographolide) is not high, and the main impurities are high-molecular plant protein, andrographolide hydrolysis, oxidation products, and pigments. It is reported in the literature that it is decolorized with activated carbon and carried out with an ultrafiltration membrane with a molecular cut-off of 5000. After ultrafiltration, the LD50 of a single intravenous administration of mice can be increased from 757mg / kg to 910mg / kg; (4) Andrographolide is unstable in product quality due to unstable production process in the process of esterification and dehydration
This method not only needs to consume a large amount of pyridine, and produces environmental pollution, but the quality of the product thus obtained is unstable, the color is darker, and the yield is low (about 41.7%), it is not suitable for industrial production, and it is difficult to ensure product quality

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A preparation method of Chuanhuning, the steps are:

[0048] Add 10kg of succinic anhydride and 5kg of andrographolide into a 100L reactor, add 50L of butanone, heat (50-60°C) and stir to dissolve, then add 0.5kg of anhydrous sodium sulfite and N,N-diisopropylethylamine 2kg is the catalyst, and after heating and refluxing in a water bath for 5 hours, the end point of the reaction is detected by high performance liquid chromatography. When the chromatographic peak of andrographolide in the high performance liquid chromatogram disappears completely and the chromatographic peak of dehydroandrographolide succinic acid half ester no longer increases, stop the heating reaction, and the reaction solution is added into 1000L water to solidify under stirring, 2 hours After filtering, the dehydrated andrographolide succinic acid half ester solid crude product was obtained.

[0049] Add 200 L of water to the obtained solid crude dehydrated andrographolide succinate half ester, st...

Embodiment 2

[0053] A preparation method of Yanhuning, the steps are:

[0054] Add 5kg of succinic anhydride and 5kg of andrographolide into a 50L reactor, add 25L of acetonitrile, heat (50 or 53 or 55 or 57 or 60°C) and stir to dissolve, then add 0.05kg of anhydrous sodium sulfite and 2.5kg of pyridine as a catalyst , and then heated under reflux in a water bath for 4 hours, and the end point of the reaction was detected by high performance liquid chromatography. After the chromatographic peak of andrographolide in the high-performance liquid chromatogram disappears completely, stop the heating reaction, add the reaction solution into 500L water to solidify under stirring, filter after 2 hours, and obtain dehydrated andrographolide succinic acid half ester solid Crude.

[0055] Add 200 L of water to the obtained solid crude dehydrated andrographolide succinate half ester, stir and soak for 2 hours, filter, add 200 L of water, stir and soak for 2 hours, and filter. Repeated soaking and w...

Embodiment 3

[0059] A preparation method of Chuanhuning, the steps are:

[0060] Add 2.5kg of succinic anhydride and 5kg of andrographolide in a 50L reactor, add 10L of butanone and 10L of acetonitrile, heat and stir to dissolve, then add 0.1kg of anhydrous sodium sulfite and 0.5kg of N,N-dimethylaminopyridine as a catalyst , and then heated under reflux in a water bath for 4 hours under the protection of nitrogen, and then detected the end point of the reaction by high performance liquid chromatography. After the chromatographic peak of andrographolide in the high-performance liquid chromatogram disappears completely, stop the heating reaction, add the reaction solution into 300L water to solidify under stirring, filter after 2 hours, and obtain dehydrated andrographolide succinic acid half ester solid Crude.

[0061] Add 200 L of water to the obtained solid crude dehydrated andrographolide succinate half ester, stir and soak for 2 hours, filter, add 200 L of water, stir and soak for 2 h...

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Abstract

The invention discloses a method for preparing potassium dehydroandrographolide succinate or potassium sodium dehydroandroan drographolide succinate, which comprises that firstly, andrographolide serves as a raw material, the andrographolide reacts with succinic anhydride to produce dehydroandroan drographolide disuccinate in a specific non-pyridine solvent under the heating reflux in the presence of a catalyst, and the usage amount ratio (W / W) of the andrographolide and the catalyst is (1:10)-(1:1); and secondly, the purified dehydroandroan drographolide disuccinate reacts with potassium hydroxide, sodium hydroxide, alkalinity sylvite or alkalinity sodium salt to produce the potassium dehydroandrographolide succinate or the potassium sodium dehydroandroan drographolide succinate in methanol, ethanol or hydrosolvent. The method is practical, convenient to operate, low in cost and nontoxic. The potassium dehydroandrographolide succinate or the potassium sodium dehydroandroan drographolide succinate is prepared easily under the normal atmosphere through usage of the solvent, the product quality is guaranteed, and the method is suitable for industrial production particularly.

Description

technical field [0001] The invention belongs to the technical field of medicine. It relates to a preparation method of Chuanhuning or Yanhuning, and specifically relates to a method for industrially producing Chuanhuning or Yanhuning with andrographolide as an initial raw material. It can be applied to the production of Chuanhuning, Yanhuning and dehydroandrographolide disuccinic acid half ester chemical raw materials or pharmaceutical raw materials. technical background [0002] Andrographis paniculata (Burm.F.) Nees is the whole grass or leaves of the plant of Acanthaceae Andrographis paniculata (Burm.F.) Nees. Also known as spring lotus and autumn willow, happy at first sight, elemi, bitter gall grass, golden vanilla, golden ear hook, Indian grass, bitter grass and so on. It has the effects of clearing away heat and detoxification, reducing inflammation, reducing swelling and relieving pain. It is mainly used to treat bacillary dysentery, urinary tract infection, acute...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60C07D307/58
Inventor 张超刘万忠刘铭永
Owner HUBEI HOPE PHARMA
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