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Salvia miltiorrhiza salvianolic acid F derivative and medicinal use

A technology of drugs and compounds, applied in the field of medicine, can solve problems such as poor membrane permeability, poor stability, and low bioavailability

Inactive Publication Date: 2013-01-16
PHARMA RES INST OF BENCAO TIANYUAN OF BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Salvia miltiorrhiza is a classic traditional Chinese medicine for promoting blood circulation and removing blood stasis. The material basis of its effect of promoting blood circulation and removing blood stasis is water-soluble components. Active ingredients, among which salvianolic acid F is the active compound, but we found in the process of drug research that the structure of salvianolic acid F determines some of its defects, such as poor stability, poor membrane permeability, low bioavailability, etc. Therefore, many medical workers hope to obtain new compounds through structural modification, in order to achieve the purpose of changing these defects

Method used

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  • Salvia miltiorrhiza salvianolic acid F derivative and medicinal use
  • Salvia miltiorrhiza salvianolic acid F derivative and medicinal use
  • Salvia miltiorrhiza salvianolic acid F derivative and medicinal use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0234] The raw material is: salvianolic acid F;

[0235] Preparation method: add salvianolic acid F into distilled water under nitrogen protection, stir to dissolve, then filter, add saturated anhydrous potassium carbonate dropwise to the filtrate, adjust pH value, stir at room temperature, and precipitate solid. The reaction solution was filtered and dried in vacuo to obtain a yellow solid, and the following compound was obtained:

[0236]

[0237] Composing a pharmaceutical composition with the obtained compound as an active ingredient, or preparing it into a pharmaceutical preparation;

[0238] The obtained compound spectrum data are as follows:

[0239] Hydrogen spectrum (ppm): 6.86, 7.16, 7.91, 6.22, 7.12, 6.86, 6.88, 6.72, 7.16.

[0240] Carbon spectrum (ppm): 128.5, 130.2, 148.8, 146.4, 116.4, 120.3, 148.0, 115.6, 170.0, 129.2, 113.6, 147.2, 146.5, 117.2, 120.4, 137.4, 120.2.

Embodiment 2

[0242] The raw material is: salvianolic acid F;

[0243] Preparation method: take salvianolic acid F, add it to methanol, add sulfuric acid dropwise, start magnetic stirring under nitrogen protection, and heat to reflux. The reaction was detected by TLC, and the reaction solution was rotary evaporated to dryness. The residue was added to a mixture of ethyl acetate and water, and the ethyl acetate phase was separated, washed with water, dried over anhydrous magnesium sulfate, filtered, the filtrate was rotary evaporated, and purified by column chromatography. The product phase was collected and rotary evaporated to dryness to obtain a yellow solid to obtain the following compound:

[0244]

[0245] Composing a pharmaceutical composition with the obtained compound as an active ingredient, or preparing it into a pharmaceutical preparation;

[0246] The obtained compound spectrum data are as follows:

[0247] Hydrogen spectrum (ppm): 6.86, 6.99, 7.91, 6.22, 6.92, 6.86, 6.81, ...

Embodiment 3

[0250] The raw material is: salvianolic acid F;

[0251] Preparation method: add salvianolic acid F, anhydrous isopropanol and concentrated sulfuric acid under nitrogen protection; stir and heat up, reflux phenomenon occurs, and TLC detects that the reaction is complete. The reaction solution was rotary evaporated to dryness, the residue was added with ethyl acetate and water mixture, the ethyl acetate phase was separated, washed with water, dried over anhydrous sodium sulfate, filtered, the filtrate was rotary evaporated, purified by column chromatography, the product phase was collected, and spin Evaporate to dryness to obtain a pale yellow foamy solid to obtain the following compound:

[0252]

[0253] Composing a pharmaceutical composition with the obtained compound as an active ingredient, or preparing it into a pharmaceutical preparation;

[0254] The obtained compound spectrum data are as follows:

[0255]Hydrogen spectrum (ppm): 6.85, 7.13, 8.01, 6.25, 7.02, 6.84,...

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Abstract

The invention discloses a newly-found compound and a medicinal use of the compound. The compound is characterized in that salvia miltiorrhiza salvianolic acid F is structurally modified, and a new compound which has high stability, high membrane permeability and high bioavailability is selected by carrying out a stability experiment, Lop measuring and a pharmacodynamic experiment. The new compound disclosed by the invention has a better pharmacologic action on treating diseases such as cardiovascular and cerebrovascular diseases.

Description

[0001] The present invention is a divisional application with the application number 200810246723.4. The original filing date was December 30, 2008, the application number is 200810246723.4, and the title of the invention is a pharmaceutical compound and its medicinal use. technical field [0002] The invention relates to the technical field of medicine, in particular to a series of novel compounds and their medicinal uses. Background technique [0003] Searching for new drugs or lead compounds from natural products is an important research direction and a very active research field for creating new drugs at home and abroad. In addition to the direct research and development of effective new drugs from natural products, natural products are also an inexhaustible source of new lead compounds on which new drug development depends. There are far more new chemical components related to natural products than compounds from other sources. 40% of the published chemical structures f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/20C07D317/60A61K31/357A61K31/496A61K31/36A61P9/00A61P1/16A61P11/00A61P9/06A61P3/06A61P35/00A61P39/00
Inventor 顾群孙学伟李志刚徐春霞
Owner PHARMA RES INST OF BENCAO TIANYUAN OF BEIJING
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