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New phenoxy eicosanoic acid derivative and its medical use

A technology of phenoxyalkanoic acid and derivatives, which is applied in the field of new phenoxyalkanoic acid derivatives and their medical applications, can solve problems such as elevated transaminases, increase high-density lipoprotein, reduce triglyceride Lipid and low-density lipoprotein levels, hepatoprotective effect

Inactive Publication Date: 2007-05-23
BEIJING MEIBEITA DRUG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Phenoxyalkanoic acid lipid-lowering drugs have been widely used clinically, but these compounds are prone to side effects of elevated transaminases in the application

Method used

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  • New phenoxy eicosanoic acid derivative and its medical use
  • New phenoxy eicosanoic acid derivative and its medical use
  • New phenoxy eicosanoic acid derivative and its medical use

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Example 1 2-Methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-propionyl-(2-nitrooxy-ethyl)-ester (III 1 ) preparation

[0017]

[0018] 1.1 Preparation of 2-methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-sodium propionate

[0019] 36 g (0.1 mol) of fenofibrate (purchased from Sigma) was dissolved in 600 ml of ethanol, and 100 ml of 1M sodium hydroxide solution was added dropwise with stirring. After dripping, stir the reaction at room temperature for 1 hour, evaporate the solvent under reduced pressure, add diethyl ether to wash, and filter to obtain 2-methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-propionic acid Sodium 34 grams.

[0020] 1.2 2-Methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-propionyl-(2-nitrooxy-ethyl)-ester (III 1 ) preparation

[0021] 3.4 g (10 mmol) of 2-methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-sodium propionate was suspended in 50 ml of DMF, and 3.0 g (16 mmol) of 1 , 2-dibromoethane, reacted at room temperature for 22 hours, filtered, the filtrate was evaporated to dryne...

Embodiment 2

[0022] Example 2 2-Methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-propionyl-(3-nitrooxy-propyl)-ester (III 2 ) preparation

[0023]

[0024] According to the method of 1.2, replace 1,2-dibromoethane with 1,3-dibromopropane to obtain III 2 , yield 70%; elemental analysis C 20 h 20 ClNO 7 Calculated (%): C 56.95, H 4.78, N 3.32, Cl 8.40; Found (%): C 56.72, H 4.75, N 3.06, Cl 8.19.

Embodiment 3

[0025] Example 3 2-Methyl-2-[4-(p-chloro-benzoyl)-phenoxy]-propionyl-(4-nitrooxy-butyl)-ester (III 3 ) preparation

[0026]

[0027] According to the method of 1.2, replace 1,2-dibromoethane with 1,4-dibromobutane to obtain III 3 , yield 61%; elemental analysis C 21 h 22 ClNO 7 Calculated (%): C 57.87, H 5.09, N 3.21, Cl 8.13; Found (%): C 57.68, H 4.86, N 3.10, Cl 8.22.

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PUM

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Abstract

The invention provides new phenoxy carboxylic acid derivatives represented by the formula A-COX-L-ONO2. The structure is characterized by linking nitrate and carboxyl in phenoxy carboxylic acid molecule through coupling bridge structure. In the formula, A is the role for the phenoxy residues of phenoxy acetic acid compounds with lipid-lowering effect, X represents O or NH, and L is for C2-C6 alkyl and substituted alkyl, C3-C6 naphthene, hydroxyl-containing amino acid residues such as serine and threonine residues, or dialkyl substituted piperazine. The invention also provides the drug combinations using the new phenoxy carboxylic acid derivatives as active components and their applications in liver treatment and lipid-lowering.

Description

technical field [0001] The present invention relates to new phenoxyalkanoic acid derivatives and their medical use for treating hyperlipidemia. This kind of compound can not only effectively reduce the levels of triglyceride and low-density lipoprotein in plasma, but also significantly increase High high-density lipoprotein that is beneficial to the body; moreover, unlike the lipid-lowering drugs commonly used in clinical practice, these new phenoxyalkanoic acid derivatives also have better hepatoprotective effects. Background technique [0002] Hyperlipidemia is a common disease, which can be divided into two types: primary and secondary. When blood lipids increase, a large amount of lipids are deposited on the blood vessel wall, which is an important reason for the formation of atherosclerosis. After the formation of atherosclerosis, the blood vessel wall becomes hard and brittle, and the intima of the blood vessel becomes rough. This pathological change is the basis of h...

Claims

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Application Information

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IPC IPC(8): C07C69/736C07C69/738A61P1/16A61P3/06
Inventor 仲素玲靳雪峰
Owner BEIJING MEIBEITA DRUG RES
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