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Preparation method of andrographolide compound

A compound, the technology of Yanhuning, which is applied in the field of preparation of Yanhuning compounds, can solve the problems of side reactions, increased product impurities, complicated preparation process, etc., and achieves mild and controllable reaction conditions, high stability and simple process. Effect

Active Publication Date: 2014-11-19
REYOUNG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process improves the stability and content of the product, but the preparation process is complicated and the production cost is high
[0007] To sum up, among the preparation methods of Yanhuning disclosed in the prior art, the synthesis yield of Yanhuning is low by using andrographolide as the starting material through esterification and salt formation, and the pharmaceutical cost is high. High temperature and alkaline conditions in industrial production are likely to cause product degradation, resulting in unqualified quality; using Chuanhuning as the starting material and inorganic sodium salt as the salt-forming agent to prepare Yanhuning, the product yield is high, but this process is likely to cause Chuanhuning The salt formation is not complete, there are Chuanhuning residues in the product, its aqueous solution is not completely dissolved, and insoluble matter appears, which affects the clinical application of the drug; the salt forming agent sodium bicarbonate is easy to precipitate in the ethanol solution, resulting in a low content of the product, and it needs to be placed for a long time Increased product impurities, high incidence of adverse reaction accidents such as side effects and even death caused by clinical medication, pose a risk to clinical safety

Method used

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  • Preparation method of andrographolide compound
  • Preparation method of andrographolide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Put 100 g of Chuanhuning into the reaction flask, add 500 ml of ethanol, and stir for 20 minutes, the reaction solution is a white suspension; the reaction solution is maintained at room temperature, and sodium formate ethanol solution (11.9 g / 50 ml) is slowly added to the reaction solution, After the addition, stir until the solution is clear, the reaction time is 1 hour, then add activated carbon to the solution, filter, lower the temperature of the filtrate to -10°C, cool down and crystallize, grow the crystal for 2 hours, filter with suction, and rinse with a small amount of absolute ethanol Wash and then dry the crystals to obtain 95.0g of off-white crystals of Yanhuning finished product, with a yield of 91.5%, a single compound of 0.05%, a purity of 99.89%, and a color of 1Y(-). Other items are in line with the internal control requirements of the enterprise .

Embodiment 2

[0030] Put 200g of Chuanhuning into the reaction flask, add 2000ml of tetrahydrofuran, stir for 30 minutes, the reaction solution is a white suspension; keep the reaction solution at room temperature, slowly add sodium butyrate tetrahydrofuran solution (49.9g / 100ml ), stirred until the basic solution was clear, and the reaction time was 8 hours, then added activated carbon to the solution, filtered, the temperature of the filtrate was lowered to 10°C, a large amount of product was precipitated, and the crystal was grown for 8 hours, suction filtered, rinsed with a small amount of tetrahydrofuran, and then The crystals were dried to obtain 193.7g of off-white crystals of Yanhuning finished product, with a yield of 93.2%, a single compound of 0.04%, a purity of 99.92%, and a color of 1Y(-). Other items met the internal control requirements of the enterprise.

Embodiment 3

[0032] Put 50g of Chuanhuning into the reaction bottle, add 400ml of polyethylene glycol, stir for 20 minutes, the reaction solution is a white suspension; keep the reaction solution at room temperature, slowly add sodium benzenesulfonate polyethylene glycol to the reaction solution Alcohol solution (18.1g / 40ml), after adding, stir until the reaction solution is clear, the reaction time is 5 hours, then add activated carbon to the solution, filter; the temperature of the filtrate is reduced to 0°C, a large amount of solids are precipitated, and the crystal is grown for 4 hours, Suction filtration, rinse with a small amount of absolute ethanol, and then dry the crystals to obtain 48.1 g of off-white crystals of Yanhuning finished product, with a yield of 93.7%, a single compound of 0.05%, a purity of 99.91%, and a color of 1Y (- ), other items are in compliance with the internal control requirements of the enterprise.

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Abstract

The invention relates to a preparation method of an andrographolide compound, and belongs to the technical field of pharmaceutical synthesis. In the preparation method, andrographolide is taken as a raw material and reacts with a sodium salt of an organic acid in a polar organic solvent to prepare the andrographolide compound, wherein the sodium salt of the organic acid is the sodium salt of formic acid, acetic acid, butyric acid, pentanoic acid, isocaprylic acid, maleic acid, fumaric acid, sulfonic acid or tartaric acid. The preparation method is thorough in salt forming reaction, simple in process and low in cost, so that industrial production can be achieved easily; a prepared targeted product is high in yield, purity and stability.

Description

technical field [0001] The invention relates to a preparation method of Yanhuning compound, which belongs to the technical field of medicine synthesis. Background technique [0002] The chemical name of Yanhuning is: 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester potassium sodium salt, and the molecular formula is C 28 h 34 KNaO 10 ·H 2 O, andrographolide extracted from the leaves of the traditional Chinese medicine Andrographis paniculata is obtained through esterification, dehydration, and salt formation. It has the functions of clearing away heat, antibacterial, anti-inflammatory, and antiviral. It is mainly used for viral pneumonia, upper respiratory tract infection, acute and chronic bronchitis, Gastrointestinal infection, etc. Due to the presence of bridge-type conjugated structures and α, β unsaturated lactone bonds in the molecular structure of Yanhuning, its stability is poor, and it is very easy to cause impurities to exceed the sta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 高峰黄文涛曹光伟陈雪亮
Owner REYOUNG PHARMA
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