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Preparation method of prulifloxacin

A technology of prulifloxacin and compound, which is applied in the field of preparation of quinolone antibacterial drugs, can solve the problems of affecting the yield and purity of condensation reaction, poor stability of the compound of formula V, easy loss of piperazine groups in the product, etc. Production cycle time, simplified post-processing steps, effects of improved yield and purity

Active Publication Date: 2013-05-22
JUMPCAN PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the applicant found that after the hydrolysis reaction was carried out using the above solvent system, the product easily lost piperazinyl groups, resulting in higher impurities
[0007] In addition, the stability of the compound of formula V is not good, and the applicant found that directly carrying out the condensation reaction after preparation is conducive to improving the output of prulifloxacin
Patent 200810061290 discloses a synthesis method of a compound of formula V, using carbon tetrachloride as a solvent, but its yield and purity are not high, which will affect the yield and purity of the condensation reaction

Method used

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  • Preparation method of prulifloxacin
  • Preparation method of prulifloxacin
  • Preparation method of prulifloxacin

Examples

Experimental program
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Effect test

Embodiment 1

[0038] (1) Preparation of the compound of formula (III)

[0039] Add 8.0kg of the compound of formula (II), 104kg of water, and 5.6kg of potassium hydroxide into the reaction kettle, and heat to 60-70°C for hydrolysis reaction for 2-3 hours. After the reaction is completed, cool to room temperature, wash with 28.8kg of ethyl acetate, separate the water layer, adjust to pH=6~7 with concentrated hydrochloric acid under stirring, continue to stir for 0.5 hours, filter with suction to obtain a filter cake, wash with an appropriate amount of ethyl acetate and filter Cake, dried, collected filter cake, 60 ~ 70 ℃ hot air circulation drying, that is, 7.32kg of the finished compound of formula (III), yield (mole) 94.8%, purity 96.2%;

[0040] (2) preparation of formula (V) compound

[0041] Add 5.0kg of compound of formula (IV), 7.5kg of N-bromosuccinimide (NBS), 0.25kg of azobisisobutyronitrile into the reaction kettle, add 90L of chloroform as the reaction solvent, stir and heat up ...

Embodiment 2

[0046] (1) Preparation of the compound of formula (III)

[0047] Add 8.0kg of the compound of formula (II), 120kg of water, and 6.4kg of potassium hydroxide into the reactor, and heat to 60-70° C. for hydrolysis reaction for 2-3 hours. After the reaction is completed, cool to room temperature, wash with 32kg of ethyl acetate, separate the water layer, adjust the pH to 6-7 with concentrated hydrochloric acid under stirring, continue stirring for 0.5 hours, filter with suction to obtain a filter cake, wash the filter cake with an appropriate amount of ethyl acetate , dried, collected the filter cake, and dried with hot air circulation at 60-70°C to obtain 7.30kg of the finished product of the compound of formula (III), with a yield (mol) of 93.6% and a purity of 95.1%;

[0048] (2) preparation of formula (V) compound

[0049] Add 5.0kg of compound of formula (IV), 7.5kg of N-bromosuccinimide (NBS), 0.35kg of azobisisobutyronitrile into the reaction kettle, add 110L of chlorofor...

Embodiment 3

[0054] (1) Preparation of the compound of formula (III)

[0055] Add 8.0kg of the compound of formula (II), 112kg of water, and 6.0kg of potassium hydroxide into the reaction kettle, and heat to 60-70° C. to carry out the hydrolysis reaction for 2-3 hours. After the reaction is completed, cool to room temperature, wash with 30.4kg ethyl acetate, separate the water layer, adjust to pH=6~7 with concentrated hydrochloric acid under stirring, continue stirring for 0.5 hours, filter with suction to obtain a filter cake, wash with appropriate amount of ethyl acetate and filter Cake, dried, collected filter cake, 60 ~ 70 ℃ hot air circulation drying, that is, 7.36kg of the finished compound of formula (III), the yield (mole) 96.4%, the purity 97.3%;

[0056] (2) preparation of formula (V) compound

[0057] Add 5.0kg of compound of formula (IV), 8.0kg of N-bromosuccinimide (NBS), 0.30kg of azobisisobutyronitrile into the reaction kettle, add 100L of chloroform as the reaction solvent...

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Abstract

The invention relates to a prepration method of a compound prulifloxacin as shown in the formula (I), wherein the chemical name of prulifloxacin is 6-floro-1-methyl-7-[4-(5-methyl-2-oxo1,3-dioxo hetercyclopentene-4-yl)methyl-1-piperazinyl-4-oxo-4H-[1,3] thiaazacyclobutane[3,2-a] quinoline-3-carboxylic acid. The preparation method provided by the invention is a preparation method of prulifloxacin suitable for industrialized production, simple in process, high in purity and high in yield.

Description

technical field [0001] The present invention relates to the preparation method of quinolone antibacterial drug, more particularly, the present invention relates to a kind of preparation following formula (I) prulifloxacin (prulifloxacin), chemical name is: 6-fluoro-1-methyl-7-[ 4-(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]sulfur A new method for azetidino[3,2-a]quinoline-3-carboxylic acids. [0002] Background technique [0003] Since the advent of quinolone antibacterial drugs in the 1960s, they have become a large class of commonly used anti-infection drugs widely used in clinical practice. Due to the advantages of broad antibacterial spectrum, strong antibacterial power, simple structure, convenient administration, no cross-resistance with other commonly used antibacterial drugs, and high curative effect and price ratio, this kind of drugs has attracted more and more attention and has become the field of research and development of anti-infect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
Inventor 曹龙祥董自波牛犇邵建国
Owner JUMPCAN PHARMA GRP
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