Arctigenin pro-drug, preparation method and use thereof

A technology of arctigenin and prodrug, which is applied in the field of water-soluble arctigenin prodrugs, can solve the problems such as the inability to significantly improve oral absorption, and achieves the expansion of the route of administration, the improvement of oral bioavailability, and the good water solubility. Effect

Inactive Publication Date: 2008-10-15
YANTAI TARGET DRUG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although some ester prodrugs have improved the physical and chemical properties and permeability of the original drug, they still cannot significantly improve oral absorption.

Method used

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  • Arctigenin pro-drug, preparation method and use thereof
  • Arctigenin pro-drug, preparation method and use thereof
  • Arctigenin pro-drug, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0025] Preparation example 1 prepares arctigenin

[0026] After crushing 500g burdock fruit, reflux extraction with 4 liters of 70% ethanol water for 2 times, each time for 2 hours, after recovering ethanol from the extract, apply it to a macroporous adsorption resin, elute with 95% ethanol, 50% ethanol, and 30% ethanol, and collect 50% ethanol The solvent was eluted, and the solvent was recovered to obtain 43 g of the composition. Through silica gel column chromatography 30: 1, ethyl acetate: absolute ethanol (8: 1) was used as the eluent to elute to obtain 20 g of arctiin, which was dissolved in 50% ethanol was hydrolyzed with 4% hydrochloric acid, and the ethanol was recovered. The solution was white and turbid. It was extracted three times with an equal volume of chloroform, the chloroform layers were combined, and the solvent was recovered to obtain 14.4 g of arctigenin. The purity measured by HPLC was 98.2%. .

Embodiment 1

[0027] Embodiment 1 prepares arctigenin succinate monoester

[0028] A certain amount of arctigenin is first dissolved in 25ml of anhydrous dichloromethane, and another round-bottomed flask with a suitable volume is taken, and 1.5 times the succinic anhydride of arctigenin is weighed, injected into 25ml of anhydrous dichloromethane, and the , drop the above-prepared raw material solution into the succinic anhydride solution under stirring conditions, stir for 3 to 7 days, stop the reaction, add an appropriate amount of hydrochloric acid solution, add ethyl acetate for extraction, combine the extracts, and successively use a small amount of Wash with water and saturated brine, dry the ethyl acetate layer in anhydrous sodium sulfate for 2 hours, concentrate under reduced pressure to obtain extract, silica gel column chromatography, petroleum ether ~ ethyl acetate ~ formic acid system [75:24:1] as the washing Remove the agent, concentrate and dry to obtain arctigenin succinic aci...

Embodiment 2

[0036] Embodiment 2: Preparation of Arctigenin Succinate Monoester Tablets

[0037]Weigh 10g of arctigenin succinic acid monoester, mix well, pass through 80 mesh sieve, add 200g of microcrystalline cellulose and 90g of starch as diluent to form the preparation formula, mix well, spray 75% ethanol as binder to make soft material , granulated with a 24-mesh sieve, granulated after drying, mixed evenly, compressed into tablets, made into 1000 tablets, coated, and obtained, each tablet of arctigenin succinic acid monoester 100mg.

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Abstract

The invention relates to the following general formula compound (I) and use of the general formula compound in preparing anti-inflammatory and anti-endotoxin medicines. In formula I, R is an acid solubilizing side chain of hydroxide radical in an arctigenin molecule, and can be an acid group or side chain imported through alkylation reaction or acylating reaction, such as sulphonic acid ester, sulfuric acid ester, organic phosphate, succinate, propionic ether, butyric ester, semi-succinate, semi-glutaric acid ester, semi-tartrate, semi-phthalic acid ester, m-benzene sulfonic acid ester and so on.

Description

technical field [0001] The invention relates to a water-soluble arctigenin prodrug and its application in anti-inflammatory and anti-endotoxin drugs. Background technique [0002] Arctigenin (Arctigenin) is a dibenzylbutyrolactone-type lignan compound, which is a product obtained by degrading a molecule of glucose from arctiin, the main component of Arctium lappa L., the fruit of the Compositae plant. Molecular formula of arctigenin: C 21 h 24 o 6 ; Molecular weight: 372; Structural formula is as follows: [0003] [0004] Arctigenin, a phenylpropanoid dibenzylbutyrolactonelignan, inhibits MAP kinases and AP-1activation via potent MKK inhibition: the role in TNF-ainhibition. International Immunopharmacology 4 (2004): 1419-1429]. However, arctigenin is poorly soluble in water, has poor solubility and low bioavailability, and its injection administration is limited, which limits its research and development as a new drug to a certain extent. [0005] A prodrug is a de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33A61K31/365A61P29/00
Inventor 刘珂关玉昆邵萌赵烽刘军锋韩飞
Owner YANTAI TARGET DRUG RES
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