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Preparation method of high-purity dehydroandrographolide disuccinate

A technology for dehydrating andrographis paniculata and ester disuccinic acid, which is applied in organic chemistry and other fields, and can solve problems such as difficulty in releasing solid substances from the bottom, high impurity content in products, and difficulty in ensuring anhydrous and oxygen-free state, etc.

Pending Publication Date: 2021-09-14
YIBIN VOCATIONAL & TECH COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic method of dehydroandrographolide disuccinic acid half ester must ensure anhydrous and anaerobic conditions. In order to meet the needs of industrialized production, it is difficult for the reaction kettle in the production workshop to ensure an ideal anhydrous and anaerobic state, resulting in high impurity content in the product. need to be purified
[0003] Most of the existing purification methods use a hydrophobic organic solvent to dissolve the product, wash it with an acidic aqueous solution, and finally concentrate to obtain a solid. Impurities

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] This embodiment provides a kind of preparation method of high-purity dehydroandrographolide disuccinic acid half ester, comprising the following steps:

[0018] Add andrographolide, succinic anhydride, and pyrrole with a mass ratio of 1:1:2 into the reactor, stir until the reaction is complete, and obtain a crude product; add 10 kg of ethyl acetate as a solvent in another reactor, and weigh 1 kg of crude Add the product into the solvent, stir and heat up to 60°C, keep it warm for 2h, cool down to 25°C at a rate of 8°C / h, precipitate crystals, filter, and dry at constant temperature to obtain the product. Chromatography (HPLC) was used for determination, and the determination result was 98%.

Embodiment 2

[0020] This embodiment provides a kind of preparation method of high-purity dehydroandrographolide disuccinic acid half ester, comprising the following steps:

[0021] Add andrographolide, succinic anhydride, and pyrrole with a mass ratio of 1:1:2 into the reactor, stir until the reaction is complete, and obtain a crude product; add a mixture of 20kg of ethyl acetate and petroleum ether as a solvent in another reactor , weigh 1kg of crude product and add it to the solvent, stir and raise the temperature to 60°C, keep it warm for 1h, cool down to 25°C at a rate of 10°C / h, precipitate crystals, filter, and dry at constant temperature to obtain the product. The purity of the product is in accordance with the provisions of the Pharmacopoeia Methods Determination by high performance liquid chromatography (HPLC), the determination result was 98.5%.

Embodiment 3

[0023] This embodiment provides a kind of preparation method of high-purity dehydroandrographolide disuccinic acid half ester, comprising the following steps:

[0024] Add andrographolide, succinic anhydride and pyrrole that mass ratio is 1:1:2 in the reactor, stir until reaction is complete, obtain crude product; In another reactor, add the mixture of 10kg dichloromethane and methane as solvent, Weigh 1kg of the crude product and add it to the solvent, stir and raise the temperature to 40°C, keep it warm for 2h, cool down to 25°C at a rate of 15°C / h, precipitate crystals, filter, and dry at constant temperature to obtain the product. It was measured by high performance liquid chromatography (HPLC), and the result was 99%.

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Abstract

The invention discloses a preparation method of high-purity dehydroandrographolide disuccinate, wherein the preparation method comprises the following steps: adding andrographolide, succinic anhydride and pyrrole into a polar solvent, stirring, heating until the materials are completely dissolved, preserving heat, cooling at a constant speed, separating out crystals, and filtering and drying to obtain the purified dehydroandrographolide disuccinate. According to the method, a polar solvent recrystallization method is adopted, in the heating dissolution process of the product, impurity products are dissolved in a solvent due to the principle that like dissolves like, and due to the fact that the impurities and dehydroandrographolide disuccinate are different in separated products in the cooling process, purification of the product is achieved. The whole purification process has the characteristics that the operation is simple, the cost is low, the used reagent can be recycled, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of anti-inflammatory drugs, and in particular relates to a preparation method of high-purity dehydroandrographolide disuccinate half ester. Background technique [0002] Dehydroandrographolide disuccinate half ester is an important intermediate in the production of raw materials for anti-inflammatory preparations such as Chuanhuning and Yanhuning. The chemical name of Yanhuning is 14-dehydroxy-11,12-didehydroandrographolide- 3,19-Disuccinate Half Ester Potassium Sodium Salt has heat-clearing, detoxifying and antiviral effects, and is mainly used for viral upper respiratory tract infection and viral pneumonia. The synthesis method of Yanhuning uses andrographolide as the starting material, dehydration and esterification reaction with succinic anhydride under the catalysis of pyridine to obtain dehydrated andrographolide disuccinic acid half ester, and then salt-forming reaction to obtain Yanhun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 李波沈红李勇辉
Owner YIBIN VOCATIONAL & TECH COLLEGE
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