Preparation method of compound 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester and febuxostat

A technology of isobutoxyphenyl and isobutoxybenzonitrile, which is applied in the field of compound preparation, can solve problems such as low safety, high price, and uneasy control of conditions, and achieve high yield, high safety, and simple operation Effect
CN103880775BActive Publication Date: 2016-02-10ZHEJIANG AUSUN PHARMA
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
ZHEJIANG AUSUN PHARMA
Publication Date
2016-02-10

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Abstract

The invention provides a preparation method of 2-(3-formyl-4-isobutoxy phenyl)-4-methyl thiazole-5-ethyl formate which is obtained by using 4-isobutoxy cyanophenyl as an initial raw material and through a series of reactions. The invention also provides a preparation method of febuxostat, which comprises the following steps: reacting 2-(3-formyl-4-isobutoxy phenyl)-4-methyl thiazole-5-ethyl formate with hydroxylamine hydrochloride under the action of a catalyst to obtain a compound with a structure as shown in formula (VIII); hydrolyzing the compound with the structure as shown in formula (VIII) under an alkaline condition, and performing acidification to obtain febuxostat. The preparation method of the invention prepares febuxostat without using cyanides, and is high in safety. The preparation methods of the invention are simple in operation and high in yield. Experiment results show that the yield of step (A) is up to 90%, the yield of step (B) is up to 85%, the yield of step (C) is up to 90%, the yield of step (D) is up to 90%, and the yield of step (E) is up to 97%.
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Description

technical field

[0001] The invention relates to the field of compound preparation, in particular to a preparation method of the compound 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester and febuxostat. Background technique

[0002] The chemical name of febuxostat is 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid, and its chemical structure is shown in formula (IX):

[0003]

[0004] Febuxostat is a non-purine xanthine oxidase selective inhibitor for the treatment of hyperuricemia in gout patients. Febuxostat inhibits the activity of xanthine oxidase, prevents and reduces the synthesis of uric acid from hypoxanthine or xanthine, so as to achieve the purpose of reducing blood uric acid. Compared with allopurine drugs for the treatment of gout, febuxostat has obvious advantages: first, it has a significant inhibitory effect on xanthine oxidase, and the effect of lowering uric acid is stronger and more durable; second, it will n...

Claims

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