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Production of balofloxacin and purification process thereof

A technology of balofloxacin and purification method, applied in the field of preparation and purification of balofloxacin, can solve the problems of long steps, unsuitable for industrial production, low yield and the like

Inactive Publication Date: 2011-10-26
河南康泰药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the electron-pushing effect of the 8-position methoxy group, the reaction inevitably produces the competitive substitution of 6-fluorine and 7-fluorine, so that some 6-fluorine substituted by-products appear, so the yield is low, about 40 % or so (see US: 4980470, 4997943, EP: 0421668)
[0005] 2. Using 2.3.4.5-tetrafluorobenzoic acid as a raw material, first introduce 3-methylaminopiperidinyl, then cyclize to form a quinolone ring, and then introduce 8-methoxy. The problem is that the steps are long (12 steps) , the low yield is only 1.3%, which is very unsuitable for industrialized production (see Japanese Open Patent 1993: 117238)

Method used

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  • Production of balofloxacin and purification process thereof
  • Production of balofloxacin and purification process thereof

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Embodiment Construction

[0020] In a dry 250ml reaction flask, add 3.1g boric acid and 16.6ml acetic anhydride, stir, slowly heat to dissolve, slowly raise the temperature to 110°C, stir the reaction at 110-105°C for 1.5 hours, then cool to 80°C, add 8 -10.8 g of methoxyquinoline carboxylate, continue to heat up to 80° C. for 3 hours. After the reaction was completed, the solvent was recovered under reduced pressure, cooled to room temperature, and 150 ml of ice water was added and stirred for 30 minutes. Filter, and wash with ice water to neutrality, dry to obtain chelate (II), weigh 13.7g, about 97% of yield, appearance is off-white powder; Then in the dry reaction bottle of 250ml, add 65ml acetonitrile, 24.8ml 16.0 g of triethylamine and chelate compound (II) and 9.2 g of 3-methylaminopiperidine were heated to 60° C. for 5 hours, the solvent was recovered by distillation under reduced pressure, and the residue was reacted at 70° C. with water and dilute sodium hydroxide solution for 2 Hours, after...

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Abstract

The invention relates to a preparation and purification method of balofloxacin, which comprises preparing boric acid ester from boric acid to be reacted with 8-methoxy quinoline carboxylic ester (III) to form a chelate complex (III) to be reacted with 3-methylaminopiperidine in polar solvent at a certain temperature and time, hydrolyzing via acid removal agent, and treating via acid and diluted alkali solution, to obtain balofloxacin (I) white powder. The balofloxacin has good appearance, high reaction yield, and high purity (HPLC analysis result is not lower than 99.5%). The inventive method is simple and effective with easy industrialized production.

Description

technical field [0001] The present invention relates to a kind of baloxacin namely 1-cyclopropyl-6-fluoro-8-methoxy-7-[(3-methylamino)-piperidinyl]-1.4-dihydro-4-oxo Preparation and purification method of quinoline-3-carboxylic acid. Background technique [0002] Balofloxacin, namely 1-cyclopropyl-6-fluoro-8-methoxy-7-[(3-methylamino)-piperidinyl]-1.4-dihydro-4-oxo Quinoline-3-carboxylic acid is a new quinolone antibacterial agent, which has the characteristics of broad antibacterial spectrum, strong antibacterial activity and high safety in clinical application. Baloxacin has a broad antibacterial spectrum, and its in vitro antibacterial activity is 2-24 times that of ciprofloxacin and ofloxacin. Gram-positive bacteria, such as Streptococcus pneumoniae and Staphylococcus aureus; Gram-negative bacteria, such as Neisseria gonorrhoeae, Mona catarrhalis, most Enterobacteriaceae, Haemophilus influenzae, maltophilia Pseudomonas dentition, Campylobacter jejuni, etc. have strong...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07D215/00C07D211/00
Inventor 周海龙
Owner 河南康泰药业有限公司