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Method for synthesizing quinolone medicaments

A synthetic method and quinolone technology, applied in the direction of organic chemistry, etc., can solve the problems of increasing post-processing procedures and related processing equipment, increasing the difficulty of safety production management, increasing material types and unit consumption, etc., to solve the problem of environmental protection, odor, The effect of shortening the recovery time and simplifying the production operation

Inactive Publication Date: 2010-07-21
ZHEJIANG JINGXIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Third, other liquid alkaline materials other than reaction raw materials such as triethylamine, triethylenediamine or pyridine are used as acid-binding agents. First, the types of materials and unit consumption are increased, which increases the difficulty of safety production management and the cost of raw materials. ; Second, post-processing procedures and related processing equipment need to be added during recycling

Method used

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  • Method for synthesizing quinolone medicaments
  • Method for synthesizing quinolone medicaments
  • Method for synthesizing quinolone medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Weigh respectively 25g levofluorocarboxylic acid (0.0889 mole), 33g N-methylpiperazine (0.3294 mole), 0.2g cerium trichloride heptahydrate and 12g water (0.6666 mole), drop into 250ml reaction bottle successively, Stir, heat up to 97°C, and keep the reaction at 97±2°C for 9 hours, and monitor the completion of the reaction by HPLC. After shrinking the piperidine, recover the N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90~110°C and -0.09~-0.095MPa until there is basically no flow, then add 160ml of methanol to the reaction bottle, heat and reflux for 0.5 hours, and cool down to At about 5°C, keep warm at 5-8°C for 1 hour, filter with suction, rinse the filter cake with an appropriate amount of methanol until the filtrate is colorless, and drain it. Put the obtained pale yellow solid in a 500ml flask, add 160g of purified water, stir and beat for 45 minutes, then add 30% liquid caustic soda dropwise into the bottle, stir at 25±1°C un...

Embodiment 2

[0051] Weigh respectively 25g levofluorocarboxylic acid (0.0889 mole), 30g N-methylpiperazine (0.2995 mole), 0.2g tetrabutylammonium bromide and 11g water (0.6111 mole), drop into 250ml reaction bottle successively, stir , heated to 100°C, and kept at 102±2°C for 8 hours, and monitored by HPLC to complete the reaction. After shrinking the piperidine, recover the N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90~110°C and -0.09~-0.095MPa until there is basically no flow, then add 160ml of acetone to the reaction bottle, heat and reflux for 0.5 hours, and cool down to At about 5°C, keep warm at 5-8°C for 1 hour, filter with suction, rinse the filter cake with an appropriate amount of acetone until the filtrate is colorless, and then drain it. Put the obtained pale yellow solid in a 500ml flask, add 160g of purified water, stir and beat for 45 minutes, then add 30% liquid caustic soda dropwise into the bottle, stir at 25±1°C until clear, and th...

Embodiment 3

[0053] Weigh respectively 25g levofluorocarboxylic acid (0.0889 mole), 37g N-methylpiperazine (0.3694 mole), 0.2g N, N-carbonyldiimidazole and 12g water (0.6666 mole), drop into 250ml reaction bottle successively, stir , heated to 105°C, and kept at 104±1°C for 10 hours, and monitored by HPLC to complete the reaction. After shrinking the piperidine, recover the N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90-110°C and -0.09-0.095MPa until there is basically no flow, then add 180ml of ethyl acetate to the reaction bottle, and heat to reflux for 0.5 hours. Cool down to about 5°C, keep warm at 5-8°C for 1 hour, filter with suction, rinse the filter cake with an appropriate amount of ethyl acetate until the filtrate is colorless, and drain it. Put the obtained pale yellow solid in a 500ml flask, add 160g of purified water, stir and beat for 45 minutes, then add potassium hydroxide solution dropwise into the bottle, stir at 25±1°C until clear, ...

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Abstract

The invention discloses a method for preparing quinolone medicaments. The conventional methods using organic solvents with a high boiling pint and a large polarity, adopting other solid alkali materials except reaction materials or using other liquid alkali materials except the reaction materials have obvious defects. The method of the invention adopts a technical scheme that: quinolone compounds are prepared by a piperazidine reduction of quinolone carboxylate nuclear parent and piperazidine derivates in water; the piperazidine reduction is completed in the presence of a catalyst which may be one or a mixture of more than two of cerous chloride heptahydrate, N,N-carbonyldiimidazole, 4-dimethylamino pyridine, tetrabutylammonium bromide, benzyl triethylammonium chloride and tetrabutyl ammonium hydroxide. The method for preparing the quinolone medicaments radically solves the problems of terrible smell, realizes clean production, avoids using the other alkali substances except the reaction materials as an acid-binding agent and overcomes the defects of the prior art.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of quinolones. Background technique [0002] The drugs covered by quinolones are free levofloxacin, ciprofloxacin, enrofloxacin, gatifloxacin or their hydrates or their salts with acids, and quinolones are artificially synthesized 4-quinolone core Antibacterial drugs that selectively inhibit bacterial DNA helicase (DNA-gyrase), thereby inhibiting bacterial DNA synthesis, leading to DNA degradation and death. This type of drug has been widely used clinically because of its broad antibacterial spectrum, strong antibacterial activity, and few adverse reactions (according to the latest report, some varieties have broken through the concept of antibacterial, and have made new progress in antiviral and antitumor aspects). And it has become a hot drug that many pharmaceutical companies at home and abroad are competing to develop and produce. [0003] The structura...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06C07D215/56C07D401/04
Inventor 张永塘蒋栋张敬拯孙海林曹凌峰
Owner ZHEJIANG JINGXIN PHARMA
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