Preparation method of andrographolide

A technology of Yanshuning and succinic acid, applied in the field of preparation of Yanshuning, can solve the problems of high pyridine residue, low product purity, product hydrolysis, etc., and achieves the advantages of improving product purity, avoiding pyridine residue, and reducing reaction temperature. Effect

Active Publication Date: 2013-01-09
CHONGQING LUMMY PHARMA
View PDF3 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, in the process of preparing Yanhuning intermediate dehydroandrographolide succinate half ester, the above-mentioned preparation method uses highly toxic and unpleasant-smelling pyridine as a solvent and catalyst, which tends to make the residual amount of pyridine in the final product too high, resulting in Product purity is low
In addition, the post-treatment of the final product needs to use a large amount of water to wash pyridine. Since pyridine is difficult to remove, it takes a long time to wash, and long-term washing, especially when washing with acid water, easily leads to product hydrolysis and reduced yield. The large amount of pyridine wastewater produced has brought great pressure to environmental protection

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of andrographolide
  • Preparation method of andrographolide

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0034] The embodiment of the invention discloses a preparation method of Yanhuning. Those skilled in the art can refer to the content of this article to appropriately improve the process parameters to achieve. In particular, it should be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention. The method of the present invention has been described through preferred embodiments, and relevant personnel can obviously make changes or appropriate changes and combinations to the method described herein without departing from the content, spirit and scope of the present invention to realize and apply the technology of the present invention .

[0035] For realizing the purpose of the present invention, the present invention adopts following technical scheme:

[0036] A preparation method of Yanhuning, comprising:

[0037] Step 1. Under the protection of inert gas, use an...

Embodiment 1

[0042] Add andrographolide (70g), succinic anhydride (105g), triethylamine (84g) and dioxane (350mL) into the reaction flask, seal it and start stirring. After vacuuming, argon gas was introduced to replace the air in the system, so that the system was under the protection of argon gas. Slowly heat up to 60±2°C with an oil bath, and after 7 hours of temperature-controlled reaction, cool down to 50±2°C, distill out the solvent dioxane and the catalyst triethylamine under reduced pressure. After completion, add 350mL 85% ethanol to dissolve and dilute. After adding activated carbon for decolorization and filtration, the filtrate was slowly added dropwise to 130mL potassium bicarbonate-sodium carbonate solution (sodium ion concentration: 2mol / L) using a constant pressure dropping funnel, and the temperature of the reaction was controlled at 30°C. After the addition, continue to stir 2h. 920 mL of acetone was added thereto for crystallization. Filter with suction, wash the filt...

Embodiment 2

[0044] Add andrographolide (100g), succinic anhydride (200g), triethylamine (150g) and ethyl acetate (1000mL) into the reaction flask, seal it and start stirring. After vacuuming, nitrogen gas was introduced to replace the air in the system, so that the system was under the protection of nitrogen gas. Slowly heat up to 80±2°C with an oil bath, and after a temperature-controlled reaction for 5 hours, lower the temperature to 40±2°C, distill off the solvent ethyl acetate and the catalyst triethylamine under reduced pressure. After completion, add 500mL 90% ethanol to dissolve and dilute. After adding activated carbon for decolorization and filtration, the filtrate was slowly added dropwise to 228mL potassium bicarbonate-sodium bicarbonate solution (sodium ion concentration is 1.5mol / L) with a constant pressure dropping funnel, and the temperature of the reaction was controlled to be 40°C. After the addition, Stirring was continued for 1 h. 1272 mL of acetone was added thereto ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to a preparation method of andrographolide. Andrographolidume and succinic anhydride serve as raw materials under protection of inert gas, in an aprotic solvent, aliphatic series micromolecule amine serves as a catalytic agent, an ester forming reaction is carried out to prepare dehydroandrograpolide succinate, dehydroandrograpolide succinate is subjected to salt forming reaction with an alkaline compound of sodium and an alkaline compound of potassium to prepare andrographolide, and the aprotic solvent is selected from halogenate hydrocarbon, esters, ethers and cyclic ether or a ketone or nitrile compound containing 1-4 carbon atoms. According to the invention, the low-toxicity aprotic solvent is used for replacing high-toxicity bad-smell pyridine to serve as a solvent, and simultaneously, the low-boiling-point low-toxicity aliphatic series micromolecule amine is used to replace pyridine to serve as the reacted catalyst, so that pyridine residues of finished products can be avoided, product purity and productivity are improved, and simultaneously, the pressure of environmental protection is lightened.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of Yanhuning. Background technique [0002] Yanhuning, the chemical name is 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester potassium sodium salt, and its structural formula is: [0003] [0004] Modern pharmacological experiments have shown that Yanhuning has low toxicity and no irritation, and has pharmacological effects such as heat-clearing, anti-bacterial, anti-inflammatory, and anti-viral. Adrenal cortex functions, promotes ACTH release, increases ACTH biosynthesis in the anterior pituitary. Clinical etiology diagnostic experiments and tissue culture inactivation tests show that Yanhuning is effective against influenza virus A I, A III, pneumonia adenovirus (Adv) III, IV, enteric syncytial virus and respiratory syncytial virus (Rsv) and many other viruses have inactivation effect. [0005] Yanhuning is refined from An...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
Inventor 周和平黄文峰杨俊喻秀英黄雄鸠李胜伟覃培福
Owner CHONGQING LUMMY PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap