3, 5-dihydroxy-4-isopropyl diphenyl ethylene-ethyl bromoacetate-polyoxyethylene compound and synthetic method thereof

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

Inactive Publication Date: 2011-05-25
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
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Problems solved by technology

[0002] 3,5-dihydroxy-4-isopropyl stilbene, namely styrenic modad, is a newly developed antifungal drug in Canada, but due to its poor water solubility, short biological half-life and low absolute bioavailability , clinical application requires large doses and multiple administrations to achieve the therapeutic purpose, and cannot maintain the effective blood concentration to exert a lasting therapeutic effect

Method used

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

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Embodiment Construction

[0026]

[0027] The synthetic route of embodiment 1-embodiment 5 is as follows:

[0028]

[0029] in

[0030] Its synthetic method is carried out according to the following step order:

[0031] (1) Preparation of polyethylene glycol-ethyl diacetate

[0032] Its reaction formula is as follows:

[0033]

[0034] The operation process is as follows: take dry polyethylene glycol, dissolve in toluene, add sodium hydride or potassium tert-butoxide at a molar ratio of 1:3, stir at room temperature, add ethyl bromoacetate, and reflux for 22-25 hours; evaporate under reduced pressure Toluene was extracted with dichloromethane, concentrated under reduced pressure, anhydrous ether was added, and a white solid A was precipitated, namely polyethylene glycol-ethyl diacetate;

[0035] (2) polyethylene glycol-diacetate hydrolysis prepares polyethylene glycol-diacetate reaction formula as follows:

[0036]

[0037] The operation process is as follows: Take A and add it to ...

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Abstract

The invention discloses a 3, 5-dihydroxy-4-isopropyl diphenyl ethylene-ethyl bromoacetate-polyoxyethylene compound, namely polyoxyethylene-di(acetic acid-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 ethyl bromoacetate, the molecular weight of polyoxyethylene is 4000 to 8000. The synthetic method of the compound includes three reactions, namely esterification reaction, hydrolysis reaction and esterification reaction. 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-ethyl bromoacetate-polyoxyethylene compound can be easily made.

Description

technical field [0001] The invention relates to a prodrug of an antifungal drug, specifically a 3,5-dihydroxy-4-isopropyl stilbene-ethyl bromoacetate-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, but due to its poor water solubility, short biological half-life and low absolute bioavailability , clinical application requires large doses and multiple administrations to achieve the therapeutic purpose, and cannot maintain the effective blood concentration 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 modified drugs. Using polyethylene glycol to modify some drugs can effectively solve the problems of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K31/047A61P31/10A61K47/60
Inventor 张越于奕峰韩玉翠赵小林
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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