Synthesis method of prulifloxacin key intermediate

A synthesis method and technology of pulifloxacin, which are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of increased cost, complicated reaction operation, etc., and achieve simple operation, simple process and mild reaction conditions. Effect
CN113185533APending Publication Date: 2021-07-30ZHEJIANG UNIV OF TECH +1
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV OF TECH
Publication Date
2021-07-30

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Abstract

The invention discloses a synthesis method of a prulifloxacin key intermediate. The prulifloxacin key intermediate is 7-chloro-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazolo[3,2-a]quinoline-3-carboxylic acid ethyl ester (I), the synthesis method comprises the following steps: taking 1-(4-chloro-2,5-difluorophenyl)ethanone (II) as an initial raw material, carrying out Claisen condensation to obtain a compound (III), carrying out ethylation on the compound (III) to obtain a compound (IV), carrying out ammonolysis on the compound (IV) and an ammoniation reagent, carrying out cyclization reaction under the action of potassium carbonate to obtain a compound (VI), carrying out hydroxyl protection on the compound (VI) by using acetyl chloride to obtain a compound (VII), carrying out chlorination reaction on the compound (VII) and a chlorination reagent, and then performing cyclization reaction under the action of sodium acetate to obtain an intermediate target product. The synthesis method disclosed by the invention has the characteristics of simple process, simplicity and convenience in operation, mild reaction conditions, avoidance of use of toxic and harmful reagents, reduction of environmental pollution, higher total yield and the like, thereby having higher implementation value and social and economic benefits.
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Description

technical field

[0001] The invention relates to the field of synthesis of pharmaceutical and chemical intermediates, in particular to the preparation of prifloxacin key intermediate 7-chloro-6-fluoro- A new method for ethyl 1-methyl-4-oxo-1H,4H-[1,3]thiazolo[3,2-a]quinoline-3-carboxylate. Background technique

[0002] Prulifloxacin (PUFX for short) is a new generation of fluoroquinolone antibacterial drugs jointly developed by Nippon Shinyaku and Meiji Seika. It was approved for listing in Japan on July 31, 2002. The mechanism of action of the drug targets the DNA of the bacteria. By blocking the DNA topoisomerase, the bacterial DNA cannot form superhelixes, further causing irreversible damage to the chromosomes, resulting in the inability of the bacterial cells to divide and reproduce. Toxicological data show that when prifloxacin is administered orally, the rough median lethal dose of mice, rats and beagle dogs is not less than 5000mg / kg. No obvious reproductive toxicit...

Claims

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