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Preparation of Prunin and derivative thereof and application of Prunin derivative in drugs for relieving cough and reducing phlegm

A technology of pronin derivative and pronin reaction, applied in the preparation of pronin and its derivatives and its application in cough and phlegm drugs, can solve the problem of low solubility and fat solubility, which limit the application of pronin , Pronin low bioavailability and other issues, to achieve stable quality, good cough and phlegm, rapid curative effect

Inactive Publication Date: 2018-02-23
MEIZHOU GOLDEN POMELO HEALTH TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented new chemical compound called prunein was found effective against respiratory problems such as breathing difficulties due to cold or flu virus attacks on humans who are sick with these conditions. Its properties make this substance useful in developing drugs targeting them specifically.

Problems solved by technology

This patented technical problem addressed in this patents is how to enhance the dissolution and release properties of certain substances like quaternary alcohol called prunes during biologics applications related to improves their ability to deliver medications safely over time without causing side reactions.

Method used

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  • Preparation of Prunin and derivative thereof and application of Prunin derivative in drugs for relieving cough and reducing phlegm
  • Preparation of Prunin and derivative thereof and application of Prunin derivative in drugs for relieving cough and reducing phlegm
  • Preparation of Prunin and derivative thereof and application of Prunin derivative in drugs for relieving cough and reducing phlegm

Examples

Experimental program
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Effect test

preparation example 1

[0023] Preparation Example 1: Take 100 mg of Pronin, add 5 ml of ethanol (95%), and 30 mg of dimethyl sulfate, and then add 15 mg of sodium hydroxide. Stir at room temperature for 5 hours. After the reaction was complete, 20ml of water was added, followed by extraction with ether. The ether layer was dried over anhydrous sodium sulfate. After removing the ether, the crude product was dissolved in 95% ethanol, and purified by column chromatography (silica gel column) to obtain the desired R 3 Prunin compounds whose group is methoxy group (P-3J, it is allowed to contain no more than 10% of R 4 group is methoxy). The chemical structure of the product has passed 1 Identification by H NMR and MS. See the specific reaction figure 1 .

preparation example 2

[0024] Preparation example 2: Take 100 mg of Pronin, add 5 ml of isopropanol containing 5% water and 30 mg of diisopropyl sulfate, and then add 15 mg of sodium hydroxide. Stir at room temperature for 2-20 hours. After the reaction was completed, 20ml of water was added, and then extracted with a mixed solvent of petroleum ether: ethyl acetate = 2:1. The organic solvent layer was dried over anhydrous sodium sulfate. After removing the mixed solvent, after the crude product is dissolved in 95% ethanol, use column chromatography (silica gel column) to purify, can obtain required R3 base is the prunin derivative (P-3B, allowing containing not more than 10% of the R4 groups are isopropoxy). The chemical structure of the product has been identified by 1H NMR and MS. See the specific reaction figure 2 .

preparation example 3

[0025] Preparation Example 3: Take 100 mg of Pronin, add 5 ml of isopropanol containing 5% water and 1 ml of formaldehyde, and then add 15 mg of sodium hydroxide or potassium hydroxide. Stir at room temperature for 1-5 hours. After the reaction was completed, 20 ml of water was added, and then extracted with a mixed solvent of petroleum ether: ethyl acetate = 1:3. The organic solvent layer was dried over anhydrous sodium sulfate. After removing the mixed solvent, the crude product is dissolved in 95% ethanol, and then purified by column chromatography (silica gel column) to obtain the desired R 3 Pronin derivatives whose group is deoxymethyl group (P-3J-1, allowed to contain no more than 10% of R 4The group is deoxymethyl). The chemical structure of the product has been identified by 1HNMR and MS. See the specific reaction image 3 .

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Abstract

The invention relates to preparation of a Prunin derivative and application thereof in drugs for relieving a cough and reducing phlegm. The Prunin derivative is obtained by introducing glycosyl or aliphatic chains or an amine group or an ether group, and the water solubility, the dissolving-out speed and the bioavailability are significantly improved. The Prunin derivative has better cough relieving and phlegm reducing effects, the curative effects on various coughs and asthma caused by acute bronchitis, chronic bronchitis, colds and the like are significant, and no toxic or side effect exists; compared with traditional cough medicine Nin Jiom Pei Pa Koa, the curative effect is more significant, and the Prunin derivative is an ideal drug for relieving the cough and reducing the phlegm, andhas a wide market prospect. The formula is defined in the description.

Description

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Claims

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Application Information

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Owner MEIZHOU GOLDEN POMELO HEALTH TECH CO LTD
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