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The Study on Synthesis of Pranlukast

Author: ChenZuo
Tutor: YangJian；SongXiZuo
School: Zhejiang University
Course: Chemical Engineering
Keywords: Pranlukast Condensation Aminolysis Tetrazolium Acylation reactions
CLC: TQ463.2
Type: Master's thesis
Year: 2010
Downloads: 202
Quote: 1
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Abstract


The new anti- asthma drug pranlukast (Pranlukast) the development by the Japan Ono , and listed in the mid-nineties , is currently widespread international concern three leukotriene receptor antagonists (LTRAs) one . Pranlukast synthetic methods reported in the literature there are many, according to the main intermediates in the synthetic route can be divided into two categories . Class 1 main intermediates; second class of N- (3 - acetyl - 8 - amino - 4 - oxo - -2 - ( 5- 1H - tetrazolyl ) - 4H- 1 - benzopyran 2 - hydroxyphenyl ) -4 - (4 - butoxyphenyl ) benzamide as the main intermediates. This paper mainly with reference to a method for the synthesis of key intermediates to the 8 - amino - 4 - oxo - -2 - (5-1H- four thiazolyl ) - 4H- 1 - benzopyran , the design of a new synthesis route . As raw material, 5 - bromo - 2 - hydroxy-3 - nitrophenyl ethanone ketoester condensation , cyclization, aminolysis amide dehydration of cyanide , and then reaction with sodium azide the tetrazole catalyst , palladium on carbon , reduction of the nitro group and removal of the bromo substituent to give 8 - amino-4 - oxo -2 - ( 5 - 1H -tetrahydroxy- thiazolyl ) - 4H- 1 - benzopyran , and the resulting amino compound with butoxy the phenyl benzoic acylate occur amidation reaction to give pranlukast . And has been reported in the literature , the innovations of this paper is to : a patent infringement Pranlukast synthetic route is designed to reduce the reaction steps , the optimization of the production process , the total yield of 21.25% , which routes ammonia amine solution of the amide compound , a cyano compound, nitro tetrazole compounds not yet reported for CA new compounds. In the preparation process of the 8 - amino - 4 - oxo -2 - ( 5 - 1H -tetrahydroxy- thiazolyl ) - 4H -1 - benzopyran , added triethylamine tetrazol salified , while benzopyrazole the furan ring dehalogenated merged together with the reduction of nitro group , to simplify the reaction steps . In 2 - carboxamide -6 - bromo-8 - nitro - 4 - oxo -4H-benzo pyran process in , select the appropriate post-treatment acid system, to reduce the occurrence of side reactions . Acylation reaction occurs to give the 8 - amino - 4 - oxo -2 - ( 5 - 1H -tetrahydroxy- thiazolyl )-4H-1- benzopyran with butoxyphenyl benzoic acylate escitalopram SECRETARY Laid reaction , the selection of a simple and easy operation of triethylamine - dichloromethane system, reducing the cost of production .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Production of organic compounds in drug > Aliphatic compounds, drugs
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