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Water-soluble derivative of anesthetic 2,6-diisopropyl phenol and preparation method thereof

A technology of diisopropylphenyl and derivatives, applied in anesthetics, drug combinations, pharmaceutical formulations, etc., can solve problems such as poor water solubility

Inactive Publication Date: 2007-02-07
重庆医科大学医药研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of prodrug can be quickly hydrolyzed to release 2,6-diisopropylphenol after injection into the body, which produces an anesthetic effect and overcomes the disadvantage of poor water solubility of 2,6-diisopropylphenol

Method used

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  • Water-soluble derivative of anesthetic 2,6-diisopropyl phenol and preparation method thereof
  • Water-soluble derivative of anesthetic 2,6-diisopropyl phenol and preparation method thereof
  • Water-soluble derivative of anesthetic 2,6-diisopropyl phenol and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Preparation of 2,6-diisopropylphenyl-2-chloroacetate from chloroacetyl chloride:

[0024] Under the flow of dry N2, 30 ml of anhydrous ether, 5.13 g of 2,6-diisopropylphenol, and 3.0 ml of chloroacetyl chloride were added to a 100 ml dry three-necked flask. Cool down to about -5°C; slowly add 5g of pyridine. Control the internal temperature at -5°C ± 2°C. After the dropwise addition, the ice-salt bath was removed, and the temperature was naturally raised at room temperature, and the reaction was continued at room temperature for 4 hours until the reaction was complete. Suction filtration, the filtrate was washed with ice-brine until the water layer was neutral, and then dried with anhydrous Na2SO4; suction filtration, the filtrate was concentrated under reduced pressure, and diethyl ether was evaporated to obtain 7.2 g of oil, with a yield of 95%.

Embodiment 2

[0026] Preparation of 2,6-diisopropylphenyl-2-chloroacetate from chloroacetic acid:

[0027] Under the flow of dry N2, 30 ml of dichloromethane, 5.13 g of 2,6-diisopropylphenol, and 2.8 g of chloroacetic acid were added to a 100 ml dry three-necked flask. Appropriate amount of DCC. React at room temperature for more than 3 hours, add 10 ml of dilute hydrochloric acid and stir for more than 1 hour, separate the water layer, and evaporate the solvent under reduced pressure to obtain 6.5 g of oil, with a yield of 88%.

Embodiment 3

[0029] Preparation of N,N-2,6-diisopropylphenyl-2-dimethylaminoacetate hydrochloride from 2,6-diisopropylphenyl-2-chloroacetate

[0030] Dissolve 7.2g of 2,6-diisopropylphenyl-2-chloroacetate in 50ml of acetone, under stirring, pass through dry dimethylamine gas, and react to the end; concentrate under reduced pressure, add 20ml of ether to dissolve the oil The liquid was washed with 10ml of saturated sodium bicarbonate solution, and then washed with saturated ice brine until the water layer was neutral; the organic layer was dried with anhydrous Na2SO4, filtered with suction, stirred, and slowly fed with dry hydrogen chloride gas, filtered with suction , to obtain 6.8g of white solid, yield 80%; take 0.66g of crude product, add 45ml of acetone, a small amount of activated carbon is stirred and heated to reflux for decolorization, filter, add an appropriate amount of ether, freeze crystallization, suction filter, wash with a small amount of ether, and place in an oven at 50°C ...

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Abstract

The invention discloses a series of esters containing 2, 6-diisopropylphenyl and tert-amine and the water-soluble derivatives (II) through reaction with acid, and their preparation method. The method takes the 2,6-diisopropylphenol (I) as raw materials to obtain the water-soluble derivatives (II) with a formula (II), wherein n = 0-7, R = hydrogen, methyl, ethyl, and D is the organic groups containing tertiary amine and the salts through reaction with the corresponding acids. The disclosed water-soluble derivatives can release 2, 6-diisopropylphenol (I) with narcotic effect after hydrolysis in vivo, thus the derivatives can be used as narcotic drugs before injection.

Description

technical field [0001] The invention relates to a series of water-soluble derivatives containing 2,6-diisopropylphenol and a preparation method thereof. Background technique [0002] 2,6-diisopropylphenol (propofol, propofol), is a short-acting intravenous general anesthetic, with rapid onset, no obvious accumulation, quick and complete recovery, and its injection is clinically used for general anesthesia induce and maintain. But because of its low solubility in water, it can only be used clinically in the form of emulsion. However, emulsions have 1. Poor physical stability; 2. May cause embolism due to large oil droplet size; 3. Injection causes pain; 4. Can only be selectively mixed with a few injectable products before administration; 5. Emulsions are prone to bacterial growth 6. Shortcomings such as causing toxic and side effects on the heart limit the use of 2,6-diisopropylphenol. Contents of the invention [0003] The purpose of the present invention is to provide...

Claims

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Application Information

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IPC IPC(8): C07C229/12C07D295/00A61K31/223A61P23/00
CPCC07C229/12A61P23/00
Inventor 李勤耕李代华田睿万敬员王涛陈攀孙扬强何亮
Owner 重庆医科大学医药研究所
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