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Sitafloxacin hydrate degradation impurity preparation method

A technology for sitafloxacin and impurities, which is applied in the field of preparation of quinolones for degrading impurities of sitafloxacin, achieving the effect of less steps, mild reaction and high commercial value

Inactive Publication Date: 2016-11-23
SHANDONG QIDU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no simple and operable preparation method for degrading impurities P1 and P2 by sitafloxacin

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Take 5.0 g of the compound sitafloxacin and add it to 100 ml of purified water as a solvent, and stir to form a suspension. The temperature was controlled at 20°C, and the product was irradiated under a mercury lamp for 10 hours, and the product was obviously formed by TLC detection. The reaction was stopped, and the crude compound was obtained by distillation under reduced pressure, which was separated by column chromatography, and the eluent was dichloromethane:methanol=5:1, and 536mg of the product (P1) and 604mg (P2), respectively, were obtained with a yield of 12.69% and 11.84% respectively. %.

Embodiment 2

[0021] Take 5.0 g of the compound sitafloxacin and add it into the solvent 200 ml of methanol, and stir to form a suspension. The temperature was controlled at 25°C, and the product was irradiated under a mercury lamp for 15 hours, and the product was obviously formed by TLC detection. The reaction was stopped, and the crude compound was obtained by distillation under reduced pressure, which was separated by column chromatography, and the eluent was dichloromethane:methanol=10:1, and the product was 498mg (P1) with a yield of 11.78% and 573mg (P2), with a yield of 11.23 %.

Embodiment 3

[0023] Take 5.0 g of the compound sitafloxacin and add it into 200 ml of acetone as a solvent, and stir to form a suspension. Control the temperature at 25°C and irradiate for 15 hours under an ultraviolet lamp, and TLC detects that a product is obviously formed. The reaction was stopped, and the crude compound was obtained by distillation under reduced pressure. It was separated by column chromatography, and the eluent was dichloromethane:methanol=5:1. The product was 310mg (P1) with a yield of 7.34% and 405mg (P2), with a yield of 7.94% %.

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PUM

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Abstract

The invention belongs to the field of medicinal chemistry and particularly relates to a sitafloxacin hydrate degradation impurity preparation method. The sitafloxacin hydrate degradation impurity preparation method includes: dissolving sitafloxacin hydrate in a solvent; illuminating for 10-20 hours; performing column chromatography chromatography separation to obtain degradation impurity P1 and impurity P2. The sitafloxacin hydrate degradation impurity preparation method is simple and highly operable, and products conforming to the requirements of the quality standards can be obtained via simple purification.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method for degrading impurities of quinolones sitafloxacin. Background technique [0002] The chemical name of sitafloxacin (sitafloxacin hydrate) is 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R ,2S)-cis-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, a broad-spectrum quinolone developed by Daiichi Sankyo Antibacterial drug, its 3 / 2 hydrate is used clinically. Sitafloxacin is a new oral N-1-fluorocyclopropyl new quinolone antibacterial drug with broad-spectrum antibacterial activity. It is effective against aerobic or anaerobic Gram-positive and Gram-negative bacteria, Mycoplasma Chlamydia, etc. have broad-spectrum antibacterial effects and are used to treat severe and refractory infectious diseases. [0003] Sitafloxacin impurities include different types such as isomer impurities, process impurities and degradation impuri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D215/56
CPCC07D215/56C07D401/04
Inventor 孔令金任继波张涛郑亮刘印翟民林蒙王孟
Owner SHANDONG QIDU PHARMA
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