Substituted phenyl acetate compound and application thereof

A technology of compound and alkyl, which is applied in the field of medicine and chemistry to achieve the effect of strong drug effect, less toxic and side effects, and good anesthesia effect

Inactive Publication Date: 2013-01-09
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Substituted phenyl acetate compound and application thereof
  • Substituted phenyl acetate compound and application thereof
  • Substituted phenyl acetate compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1.1, the synthesis process of (3-trifluoromethoxy-4-hydroxyl) trifluoroethyl phenylacetate (intermediate compound a) The intermediate compound a can be prepared by the following reaction process:

[0049]

[0050] 1.1.1 Intermediate compound a 2 synthesis process

[0051] 2-(trifluoromethoxy)phenol (intermediate compound a 1 ) (35.625g, 0.2mol, 1eq) and 50% glyoxylic acid (29.5g, 0.198mol, 1eq) and 100ml of distilled water were added to a 500ml three-necked flask, and 10% NaOH solution was added dropwise to the there-necked flask under an ice bath (prepared by 16.1g sodium hydroxide and 150ml distilled water), react at room temperature overnight. Stop the reaction, extract 3 times with ethyl acetate, adjust the pH of the aqueous phase to 1 with concentrated hydrochloric acid, extract 3 times with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, spin dry the solvent with a rotary evaporator, and obtain 53.6 g of a white solid , yield 53%, mp 1...

Embodiment 2

[0061]2.1 Synthetic process of 3-trifluoroethoxy-4-phenylacetic acid trifluoroethyl ester (intermediate compound b)

[0062] Using 2-(2,2,2-trifluoroethoxy)phenol instead of 2-(trifluoromethoxy)phenol, it was prepared using a similar process to Example 1.1. The intermediate compound b4.7g was obtained. 1 H-NMR (CDCl 3 )δ3.67 (s 2H), 4.42-4.52 (m, 4H), 5.35 (s, 1H), 6.95 (s, 3H). MS (ESI) m / z 333 ([M+H] + ).

[0063]

[0064] 2.2 Synthetic process of [4-[(N,N-ethylcarbamoyl)methoxy]-3-trifluoroethoxyphenyl]trifluoroethyl acetate (compound 2)

[0065] In a 100 ml round bottom flask equipped with a magnetic stirring bar, intermediate compound b (4.7 g, 14 mmol, 1.0 eq) was dissolved in anhydrous acetone (50 ml) to form a solution. To this solution was added potassium carbonate (3 g, 21 mmol, 1.5 eq) followed by 2-chloro-N,N-diethylacetamide (2.53 g, 16.8 mmol, 1.2 eq). Under magnetic stirring, the suspension was heated to reflux and kept under reflux for 48h. After cooli...

Embodiment 3

[0068] 3.1 Synthetic process of 3-methyl-4-phenylacetic acid trifluoroethyl ester (intermediate compound c)

[0069] Using guaiacol instead of 2-(trifluoromethoxy)phenol, it was prepared using a similar process to Example 1.1. The intermediate compound c3.6g was obtained. 1 H-NMR (CDCl 3 )δ3.67(s 2H), 3.88(s, 3H), 4.46-4.53(m, 2H), 5.35(s, 1H), 6.78-6.86(m, 2H), 6.92(d, 1H, J=4Hz ).MS (ESI) m / z 265 ([M+H] + ).

[0070]

[0071] 3.2, [4-[(N, N-ethylcarbamoyl) methoxyl]-3-methoxyphenyl] trifluoroethyl acetate (compound 3) synthesis process in the 100ml equipped with a magnetic stirring bar Intermediate compound c (3.6g, 13.6mmol, 1.0eq) was dissolved in anhydrous acetone (50ml) to form a solution in a round bottom flask. To this solution was added potassium carbonate (3g, 21.7mmol, 1.5eq) followed by 2-chloro-N,N-diethylacetamide (2.4g, 16mmol, 1.2eq). Under magnetic stirring, the reaction solution was heated to reflux and kept under reflux for 48h. After cooling to ro...

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Abstract

The invention belongs to the fields of medicine and chemistry, and provides a substituted phenyl acetate compound with the structure shown by formula (I), which has short-acting sedative-hypnotic effect so as to be used for preparing anesthetic and sedative. The experiments prove that the substituted phenyl acetate compound has the anesthetic activity stronger than that of propanidid, and has the action time and the recovery time which are shorter and more foreseeable than those of propofol, thus having the characteristics of being high in anesthetic effect and medicine effect, low in toxic and side effects and the like.

Description

technical field [0001] The invention belongs to the fields of medicine and chemistry, and relates to substituted phenyl acetate compounds, which can be used as short-acting sedative hypnotic agents for anesthesia and sedation. The invention also relates to pharmaceutical compositions comprising such compounds; methods of inducing or maintaining anesthesia or sedation using such compounds. Background technique [0002] Propofol, 2,6-diisopropylphenol, is an injectable anesthetic with hypnotic properties. It can be used to induce and maintain general anesthesia and sedation. The action time of propofol after infusion is unknown, and this unpredictable action duration leads to irregular recovery time of patients, and most patients have long recovery time and poor controllability. In addition, propofol has cardiovascular side effects and produces pain reactions when injected. [0003] Propanidid, [4-[(N,N-ethylcarbamoyl)methoxy]-3-methoxyphenyl]propyl acetate, is another inje...

Claims

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Application Information

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IPC IPC(8): C07C235/06C07C231/12A61K31/216A61P25/20A61P23/00
Inventor 张桂森张恒刘笔锋刘欣
Owner HUAZHONG UNIV OF SCI & TECH
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