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Propofol hydroxy acid ester compound with ester constitutional terminal, preparation method for same and application thereof

A technology of propofol hydroxy acid and ester compounds, which is applied in the field of propofol derivatives, and can solve the problems of inability to exert pharmacological effects

Active Publication Date: 2013-10-30
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the modified propofol derivatives cannot quickly release the original drug of propofol, they will not be able to play the desired pharmacological effect.

Method used

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  • Propofol hydroxy acid ester compound with ester constitutional terminal, preparation method for same and application thereof
  • Propofol hydroxy acid ester compound with ester constitutional terminal, preparation method for same and application thereof
  • Propofol hydroxy acid ester compound with ester constitutional terminal, preparation method for same and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of Acetate of Propofol Hydroxybutyrate:

[0025] Dissolve 4 g of propofol 4-hydroxybutyrate prepared in the manner of publication number CN101906039A in 20 ml of dichloromethane, add 10 ml of acetic anhydride, cool to 0°C, add dropwise 3 ml of triethylamine, and keep the temperature Stir the reaction for 24 h. After the reaction is complete, pour the reaction solution into 100 ml of water, stir for 10 min, let stand to separate layers, separate the organic layer, wash the organic layer once with saturated sodium carbonate solution and water, separate the organic layer, and reduce After concentration under pressure, it was separated and eluted by column chromatography (eluent (v / v, the same below): cyclohexane / ethyl acetate=95 / 5), and the eluent containing the product was evaporated to remove the solvent. 3.7 g of a colorless oil was obtained, with a yield of 79.7%. Product structure detection results:

[0026] 1) Nuclear Magnetic Resonance Apparatus: BRUKE...

Embodiment 2

[0034] Preparation of Acetate of Propofol Hydroxybutyrate:

[0035] Dissolve 5 g of propofol 4-hydroxybutyrate in 15 ml of acetic anhydride, add 3 ml of triethylamine dropwise, and stir at room temperature for 3 h. After the reaction is completed, pour the reaction solution into 100 ml of water, add 50 ml of ethyl acetate ester, stirred for 10 min, allowed to stand and separate the layers, separated the organic layer, washed the organic layer once with saturated sodium carbonate solution and water, separated the organic layer, concentrated under reduced pressure and eluted by column chromatography, the eluted product containing After distilling off the solvent under reduced pressure, 4.84 g of a colorless oil was obtained, with a yield of 83.5%.

Embodiment 3

[0037] Preparation of Acetate of Propofol Hydroxybutyrate:

[0038] Dissolve 5 g propofol 4-hydroxybutyrate in 15 ml acetic anhydride, add 3 ml triethylamine dropwise, stir and react at 50°C for 1 h, after the reaction is completed, pour the reaction solution into 100 ml water, add 50 ml Ethyl acetate, stirred for 10 min, allowed to stand for stratification, separated the organic layer, washed the organic layer once with saturated sodium carbonate solution and water, separated the organic layer, concentrated under reduced pressure and eluted by column chromatography, the product containing After the solvent was evaporated from the eluent under reduced pressure, 4.25 g of a colorless oily substance was obtained, with a yield of 73.3%.

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Abstract

Disclosed are a propofol hydroxy acid ester compound with an ester constitutional terminal, a preparation method for the same and application thereof. As shown in the constitutional formula (I) of the compound, Y refers to a C1-4 linear carbon chain, and R refers to acetyl or propiono. The propofol hydroxy acid ester compound can be prepared by utilizing corresponding propofol hydroxy acid ester as raw materials and is obtained by means of esterification reaction with corresponding acid anhydride. As experiments show, the compound is stable in vitro but capable of quickly releasing propofol with sedation and hypnogenesis and / or narcotism in blood plasma. Since hydroxy in propofol hydroxy butyric ester molecules is protected by means of shielding, heat stability of the propofol hydroxy acid ester compound is improved, and self-decomposition of the propofol hydroxy acid ester compound caused by lactonization is reduced.

Description

technical field [0001] The invention relates to a derivative of propofol, specifically a propofol hydroxy ester compound with an ester structure terminal, a preparation method thereof and an application in pharmacy. Background technique [0002] Propofol, whose chemical name is 2,6-diisopropylphenol, is a sedative drug widely used clinically for the induction, maintenance and intensive care of general anesthesia. features. Since the first clinical report of this compound was made in 1977, it has gradually been promoted and applied all over the world. In addition to its pharmacological effects in anesthesia, propofol has also been found to have other pharmacological effects, such as anti-epilepsy, treatment of migraine, etc. Therefore, research on oral propofol derivatives has become a research hotspot. Since propofol has a very significant first-pass effect, it needs to be modified to reduce the first-pass effect. However, if the modified propofol derivatives cannot rapi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/67C07C67/08A61K31/222A61P25/20A61P23/00
Inventor 张文胜杨俊刘进
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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