Preparation method for Prulifloxacin

A production method and compound technology, applied in the field of preparation of prulifloxacin, can solve problems such as low reaction yield, impact on yield, environmental pollution, etc., avoid the use of chlorosulfonic acid or sulfonyl chloride, and reduce damage to the body , Ease of industrial production

Active Publication Date: 2011-11-09
湖南欧亚药业有限公司
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  • Abstract
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Problems solved by technology

[0010] The first route requires high temperature and the use of toxic ClCO 2 Et, the protection-deprotection reaction affects the yield; although route two and three have been optimized and improved, and the reaction conditions are relatively mild, they still need to use toxic chlorosulfonic acid or sulfuryl chloride, which not only easily causes Environmental pollution, and the whole reaction yield is low

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  • Preparation method for Prulifloxacin
  • Preparation method for Prulifloxacin
  • Preparation method for Prulifloxacin

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Embodiment Construction

[0025] In order to make the technical means, creative features, work flow, and use methods of the present invention achieve the purpose and effect easily understood, the present invention will be further described below in conjunction with specific illustrations.

[0026] The preparation method of prulifloxacin comprises the following steps:

[0027]

[0028]

[0029] Synthesis of Formula I Compounds

[0030] (a) In the reaction bottle, add 360g of 3,4-difluoroaniline and 1200ml of triethylamine, and cool to -5 in ice-water bath o C, add dropwise 200ml carbon disulfide. After dropping, stir overnight under cooling. Filter, wash the filter cake with isopropyl ether, dry in vacuum at room temperature to obtain 560 g of light yellow powder, place and crystallize the mother liquor to obtain 170 g of yellow product, combine, yield: 85.5%;

[0031] (b) In the reaction flask, add 530g of the compound reacted in (a), 900ml of dichloromethane and 300ml of triethylamine, and ...

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Abstract

The invention discloses an industrialization production method for Prulifloxacin. By carrying out chlorination on N-Chlorosuccinimide and BF3 to generate an intermediate ethyl 6,7-difuoro-1-methyl-4-oxo-4H-[1,3]thiazete[3,2-a]quinoline-3-carboxylate, the invention not only greatly improves yield, but also avoids utilization of poisonous and volatile chlorosulfonic acid or sulfonyl chloride, and is suitable for the industrialization production.

Description

technical field [0001] The invention relates to a synthesis method of a compound, in particular to a preparation method of prulifloxacin. Background technique [0002] Prulifloxacin is a fluoroquinolone antibacterial drug, the chemical name is 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxole- 4-yl)-methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid. This product is a fat-soluble prodrug, which exerts a broad-spectrum antibacterial effect after being hydrolyzed into ulifloxacin by esterase in vivo, and is active against Gram-positive bacteria, Gram-negative bacteria, anaerobic bacteria, Legionella and Chlamydia. [0003] 6,7-Difluoro-1-methyl-4-oxo-4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid ethyl ester is a common synthetic The key intermediate of lulifloxacin can be synthesized mainly through the following three routes at present. [0004] Route 1: [0005] [0006] Route two: [0007] [0008] Route three: [0009]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04C07D215/56
Inventor 林开朝李兴民陶友妮王艳
Owner 湖南欧亚药业有限公司
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