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3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound and synthetic method thereof

A technology of isopropyl stilbene and hydroxy stilbene, which is applied in the field of prodrugs of antifungal drugs, can solve the problems of inability to maintain effective blood drug concentration, low absolute bioavailability, short biological half-life, etc. Bioavailability, good water solubility, effect of altering distribution in the body

Inactive Publication Date: 2009-10-28
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3,5-dihydroxy-4-isopropyl stilbene, namely styrene moder, is a newly developed antifungal drug in Canada. Due to its poor water solubility, short biological half-life and low absolute bioavailability, In clinical application, large doses and multiple administrations are required to achieve the therapeutic purpose, and the effective blood drug concentration cannot be maintained to exert a lasting therapeutic effect.

Method used

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  • 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound and synthetic method thereof
  • 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound and synthetic method thereof
  • 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound and synthetic method thereof

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Experimental program
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Embodiment Construction

[0021]

[0022] The synthetic route of embodiment 1-embodiment 5 is as follows:

[0023]

[0024] in

[0025] The synthetic method of embodiment 1-embodiment 5 is carried out according to the following step sequence respectively:

[0026] (1) Preparation of polyethylene glycol succinate

[0027] Take dry polyethylene glycol and succinic anhydride with a molar ratio of 1:3, mix them, dissolve them in acetone, add pyridine with the same molar number as succinic anhydride, heat to reflux; evaporate the solvent, add saturated NaHCO 3 solution, extracted with ethyl acetate, adjusted to pH=2.8-3.2 with dilute hydrochloric acid; extracted with chloroform, dried, concentrated under reduced pressure, added anhydrous ether, and precipitated a white solid A, polyethylene glycol succinate;

[0028] This step reaction formula is as follows:

[0029]

[0030] (2) Preparation of polyethylene glycol-succinic acid-bis(4-isopropyl-5-hydroxyl stilbene-3-phenol ester)

[0031] Take...

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Abstract

The invention discloses a 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound, namely polyoxyethylene-butane diacid-di(4-isopropyl-5-hydroxy diphenyl ethylene-3-phenolic ester). The original medicine is 3, 5-dihydroxy-4-isopropyl diphenyl ethylene (tolylene maud); and the modifier is polyoxyethylene and the linker arm is butanedioic anhydride. The synthetic method of the compound includes two esterification reactions. Compared with the original medicine, the compound has enhanced water-solubility and stability; the internal medicine distribution is changed; the bioavailability is enhanced; the synthetic method is simple; the reaction condition is mild; and the cost is low, without numerous unpleasant experimental procedures. In the method, the 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-butanedioic anhydride-polyoxyethylene compound can be easily made.

Description

technical field [0001] The invention relates to a prodrug of an antifungal drug, in particular to a 3,5-dihydroxy-4-isopropyl stilbene-succinic anhydride-polyethylene glycol complex and a synthesis method thereof. Background technique [0002] 3,5-dihydroxy-4-isopropyl stilbene, namely styrene moder, is a newly developed antifungal drug in Canada. Due to its poor water solubility, short biological half-life and low absolute bioavailability, In clinical application, large doses and multiple administrations are required to achieve the therapeutic purpose, and the effective blood drug concentration cannot be maintained to exert a lasting therapeutic effect. [0003] Polyethylene glycol (PEG) has the incomparable advantages of other polymers such as good water solubility, good biocompatibility, non-toxicity and non-immunogenicity, and plays an important role in the synthesis and preparation of polymer modified drugs. Modifying some drugs with polyethylene glycol can effectively...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K31/047A61P31/10C08G65/48A61K47/60
Inventor 张越韩玉翠赵小林高春辉
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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