Method of synthesizing 5-(4-chloro-phenyl)-N-hydroxy-1-(4-methoxy-phenyl)-N-methyl-1H-pyrazole-3-propionamide and pharmaceutical use

A compound, butyl technology, applied in the field of organic compound synthesis, can solve problems such as high risk and easy combustion, and achieve the effects of simple steps, high safety, and elimination of environmental pollution problems.

Active Publication Date: 2007-08-08
ZHEJIANG AUSUN PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Murry et al. (Synthesis 1991, P18-20) disclose the use of a variety of lithium diisopropylamide (LDA), LDA·LiCl, magnesium diisopropylamide (MDA), MDA·1LiBr, MDA·2LiBr or The base of lithium bis(trimethylsilyl)amide for the preparation of 4-chloro-γ,e-dioxo-phenylhexanoic acid from p-chloroacetophenone due to LDA, LDA LiCl, MDA, MDA 1LiBr , MDA·2LiBr is extremely flammable, and it is very dangerous to use these alkalis

Method used

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  • Method of synthesizing 5-(4-chloro-phenyl)-N-hydroxy-1-(4-methoxy-phenyl)-N-methyl-1H-pyrazole-3-propionamide and pharmaceutical use
  • Method of synthesizing 5-(4-chloro-phenyl)-N-hydroxy-1-(4-methoxy-phenyl)-N-methyl-1H-pyrazole-3-propionamide and pharmaceutical use
  • Method of synthesizing 5-(4-chloro-phenyl)-N-hydroxy-1-(4-methoxy-phenyl)-N-methyl-1H-pyrazole-3-propionamide and pharmaceutical use

Examples

Experimental program
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Embodiment

[0038] (1) Synthesis of 4-chloro-γ, ε-dioxo-phenylhexanoic acid (compound of formula I)

[0039] Potassium tert-butoxide (22.10 g, 0.20 mol) was dissolved in THF (210 mL) to make a solution. Dissolve p-chloroacetophenone (13.40 g, 0.09 mol) in THF (30 mL) at a temperature of -15-10° C., and add it dropwise to the above-mentioned THF solution of potassium tert-butoxide with a constant pressure funnel within 40 minutes. React for half an hour after dropping. Succinic anhydride (10.51g, 0.11mol) was dissolved in THF (170mL) to make a solution, and was added dropwise to the above reaction solution at a temperature of -15-10°C, and the drop was completed within 3.5 hours, and the reaction was continued for 2 hours.

[0040] At room temperature, the pH value of the reaction solution was adjusted to 4-5 with dilute hydrochloric acid (40 mL) (concentrated hydrochloric acid:water=1:7, volume ratio). The reaction solution was suction-filtered, and the filter cake was washed with a sma...

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Abstract

The invention discloses a making method of specific crystal type of 5-(4-chlorine-phenyl)-N-hydroxy-1-(4-methoxy-phenyl)-N-methyl-1H-pyrazole-3-propionamide (Tepoxalin), which is inhibitor of epoxy oxygenase and lipoxidas in the arachidonic acid cascading reaction.

Description

technical field [0001] The invention relates to a synthesis method of an organic compound and its medicinal application, in particular to a synthesis method of a pyrazole compound and its application in anti-inflammation, treatment of various pains, autoimmune diseases and the like. Background technique [0002] 1,5-Diaryl-3-substituted pyrazoles, a class of compounds with excellent activity in reducing inflammation and inhibiting cyclooxygenase and / or lipoxygenase metabolism of the arachidonic acid cascade reaction, tepo Sarin is one of them. [0003] The method for synthesizing tepoxalin at present comprises as follows: U.S. Patent 4826868 describes 5-(4-chloro-phenyl)-1-(4-methoxyl-phenyl)-1H-pyrazole-3-propanol and The Jones reagent reacts to form the acid, 5-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazole-3-propionic acid, in tetrahydrofuran (THF) with Dimethylformamide reacts with oxalyl chloride, and then reacts with methylhydroxylamine hydrochloride and triethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12A61K31/415A61P29/00A61P37/02
Inventor 常俊标郭晓河陶乐王强陈荣峰赵康张宏伟乔海灵凯西·思维德尔赫斯特
Owner ZHEJIANG AUSUN PHARMA
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