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Novel antiviral andrographolide derivative and preparation method and application thereof

A technology of andrographolide, derivatives, applied in the directions of antiviral agents, anti-inflammatory agents, drug combinations, etc., can solve problems such as unsatisfactory solubility, and achieve the effects of high oral bioavailability, simple production process, and good water solubility

Active Publication Date: 2014-04-23
太阳升(亳州)生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But above-mentioned known medicines are all unsatisfactory in solubility in water

Method used

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  • Novel antiviral andrographolide derivative and preparation method and application thereof
  • Novel antiviral andrographolide derivative and preparation method and application thereof
  • Novel antiviral andrographolide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A novel antiviral andrographolide derivative, the general formula of the derivative is as follows:

[0033]

[0034] Wherein, R1, R2, R3 can be the same or different amino acid residues of glycyl, L-alanyl, L-leucyl, L-valyl or L-isoleucyl;

[0035] The preparation method comprises the following steps:

[0036] Using andrographolide as the raw material, it undergoes esterification reaction with succinic anhydride under the action of a catalyst at a vacuum degree of 520~620 mm Hg, 60°C~200°C, reflux for 0.5~10 hours, remove the vacuum after cooling, add water and stir until complete Suction filtration until the solidification and crystallization are dispersed, and the obtained filter cake is vacuum-dried at room temperature. The dried filter cake is dissolved in aqueous sodium bicarbonate solution, filtered to obtain the filtrate, and the pH of the filtrate is adjusted to 1 with 0.1~12mol / L hydrochloric acid. ~6, the pH is preferably 4, a white precipitate is precipi...

Embodiment 2

[0048] This embodiment is a preferred scheme based on Example 1, and this embodiment is the preparation of andrographolide trisuccinate half ester and andrographolide trisuccinate half ester glycinate.

[0049]Described preparation method is: with andrographolide 40g (0.12mol), succinic anhydride 40g (0.40mol), sodium sulfite 4.0g, be placed in reaction bottle, mix, install reflux device and drying tube, start heating, adjust Vacuum degree is 520~620 mm Hg, 100 ℃, reflux reaction for 5 hours, vacuumize after cooling. Add 800ml of water to the reaction bottle, and stir well until all solidification and crystallization are dispersed. Suction filtration, vacuum-dry the obtained filter cake at room temperature, dissolve the dried filter cake with aqueous sodium bicarbonate solution, filter to obtain the filtrate, use 0.1~12mol / L hydrochloric acid to adjust the pH of the filtrate to 4, precipitate a white precipitate, and suction filter , drying to obtain andrographolide trisuccin...

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Abstract

The invention provides a novel antiviral andrographolide derivative and a preparation method and application thereof. The novel antiviral andrographolide derivative, non-toxic pharmaceutically acceptable salts and compositions thereof have good application prospects in aspects such as infection resistance, virus resistance, inflammation diminishment and antipyretic analgesics. The derivative has high water solubility and high oral bioavailability. According to the novel antiviral andrographolide derivative, the andrographolide serves as a raw material, the preparation process is simple, the cost is low, and industrial production can be performed.

Description

technical field [0001] The invention belongs to the field of heterocyclic compounds, in particular to a novel antiviral andrographolide derivative and its preparation method and application. Background technique [0002] Andrographolide is a diterpene lactone compound extracted from the plant Andrographis paniculata of the Acanthaceae family. It is one of the main active ingredients of the traditional Chinese medicine Andrographis paniculata. It has the functions of clearing heat and detoxification, cooling blood and reducing swelling. [0003] Oral administration of andrographolide can cause vomiting due to extreme bitterness. This product and various preparations can cause epigastric discomfort and loss of appetite when taken orally in larger doses. There have been reports of drug eruption, upper abdominal pain and anaphylactic shock after intramuscular injection of Andrographis paniculata injection. Symptoms of severe reactions can be seen: chest tightness, shortness of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60A61K31/365A61P31/00A61P31/12A61P29/00
CPCC07D307/60
Inventor 郭鸿旭缪也夫
Owner 太阳升(亳州)生物医药科技有限公司
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