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Method for preparing sitafloxacin

A technology for sitafloxacin and compound, which is applied in the field of preparation of sitafloxacin, can solve the problems of many impurities, low yield, complicated post-processing and the like, and achieves the effects of high yield, reduced reaction rate and easy operation.

Active Publication Date: 2017-01-25
SHANDONG QIDU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the present invention has carried out further research on the method for preparing sitafloxacin, aiming to solve the problems of more impurities generated in the one-step reaction process of de-tert-butoxycarbonyl, cumbersome post-treatment, and low yield.

Method used

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  • Method for preparing sitafloxacin
  • Method for preparing sitafloxacin
  • Method for preparing sitafloxacin

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Dissolve 50.0 g of compound II and 40.0 g of compound III in 600 ml of acetonitrile, add 20.5 g of triethylamine, raise the temperature to 80° C., and react for 2 hours. TLC detects that the reaction is complete. Cool down to 0°C, stir for 2 hours, then filter with suction, and dry the filter cake with hot air at 45°C for 6 hours to obtain 70.2 g of pale yellow product IV. Yield: 87.4%.

[0032] Dissolve 50.0g of compound IV in 500ml of dichloromethane, and drop it into 250ml of 37% concentrated hydrochloric acid that has been cooled to 0°C in advance. During the dropwise addition, the temperature was controlled at 0°C to 5°C. After dropping, the temperature was raised to 20°C to 30°C for 1 hour. After the reaction is complete. Separate the water layer, adjust the pH value to 6∼7 with 20% sodium hydroxide, then adjust the pH value to 9∼10 with 28% concentrated ammonia water, concentrate under reduced pressure at room temperature to remove ammonia, and suction filter ...

Embodiment 2

[0035] Dissolve 100.0 g of compound II and 80.0 g of compound III in 1200 ml of acetonitrile, add 41.0 g of triethylamine, raise the temperature to 80° C., and react for 2 hours. TLC detects that the reaction is complete. Cool down to 0°C, stir for 2 hours, then filter with suction, and dry the filter cake with hot air at 45°C for 6 hours to obtain 143.0 g of pale yellow product IV. Yield: 89.0%.

[0036] 100.0g of compound IV was dissolved in 2000ml of ethyl acetate, and dropped into 1000ml of 37% concentrated hydrochloric acid which had been cooled to 0°C in advance. During the dropwise addition, the temperature was controlled at 0°C to 5°C. After dropping, the temperature was raised to 20°C to 30°C for 1 hour. After the reaction is complete. Separate the water layer, adjust the pH value to 2∼3 with 15% sodium hydroxide, then adjust the pH value to 9∼10 with 28% concentrated ammonia water, concentrate under reduced pressure at room temperature to remove ammonia, and sucti...

Embodiment 3

[0039] Dissolve 100.0 g of II and 80.0 g of III in 2000 ml of acetonitrile, add 41.0 g of triethylamine, raise the temperature to 80°C, and react for 2 hours. TLC detects that the reaction is complete. Cool down to 0°C, stir for 2 hours, then filter with suction, and dry the filter cake with hot air at 45°C for 6 hours to obtain 147.0 g of pale yellow product IV. Yield: 91.5%.

[0040] 100.0 g of compound IV was dissolved in 1600 ml of methyl acetate, and dropped into 800 ml of 37% concentrated hydrochloric acid that had been cooled to 0°C in advance. During the dropwise addition, the temperature was controlled at 0°C to 5°C. After dropping, the temperature was raised to 20°C to 30°C for 1 hour. After the reaction is complete. Separate the water layer, adjust the pH value to 6∼7 with 10% potassium hydroxide, then adjust the pH value to 10∼11 with 28% concentrated ammonia water, concentrate under reduced pressure at room temperature to remove ammonia gas, and suction filter ...

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Abstract

The invention discloses a method for preparing sitafloxacin. The method comprises the following steps: (1) dissolving a compound II and a compound III in acetonitrile, adding triethylamine, heating to reflux, slowly cooling to the temperature of 0 DEG C after reaction is completed, filtering, drying, thereby obtaining a light yellow compound IV; (2) dissolving a compound IV in a non-protonic solvent, slowly adding the compound into the pre-cooled hydrochloric acid, standing and layering the reaction solution after reaction is completed, regulating the pH value of an aqueous phase by using a strong alkaline solution, regulating the pH value by using ammonium hydroxide, performing vacuum concentration on the system at room temperature so as to remove ammonia gas, separating out lots of white solids, filtering and drying, thereby obtaining sitafloxacin. According to the method for preparing sitafloxacin, disclosed by the invention, impurities produced in the reaction process can be effectively reduced, and the method is simple and convenient in after-treatment, good in refining effect, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of sitafloxacin, which belongs to the field of medicine and chemical industry. Background technique [0002] Sitafloxacin hydrate is a quaternary fluoroquinolone with a chemical name of 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 was purchased from Daiichi Sankyo Co., Ltd. ) developed a broad-spectrum quinolone antibacterial drug. The research on it began in 1992, and it was first listed in Japan in 2008. There are two dosage forms of 50mg tablet and 10% fine granule. [0003] Sitafloxacin has a wide antibacterial spectrum, not only has antibacterial activity against Gram-negative bacteria, but also has strong antibacterial activity against Gram-positive bacteria, anaerobic bacteria, mycoplasma, chlamydia, etc., and is also effective against many common clinical fluoroquinolone-resistant strains. It has good ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 杨学谦张涛李宗涛郑亮刘文坤郑向楠
Owner SHANDONG QIDU PHARMA
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