Preparation method of sitafloxacin hydrate

A technology of sitafloxacin hydrate and compounds, which is applied in the field of preparation of sitafloxacin hydrate, can solve the problems of cumbersome operation, poor safety, and low yield, and achieve simplified process operation, reduced dosage, and improved reaction yield. rate effect

Inactive Publication Date: 2017-12-26
SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention solves the problems of cumbersome operation, poor safety, high cost and low yield in the preparation method of sitafloxacin hydrate in the prior art, and further provides a method with simple operation, no potential safety hazard and low cost The preparation method of sitafloxacin hydrate with high yield

Method used

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  • Preparation method of sitafloxacin hydrate
  • Preparation method of sitafloxacin hydrate
  • Preparation method of sitafloxacin hydrate

Examples

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Embodiment 1

[0030] The preparation method of sitafloxacin hydrate described in the present embodiment comprises the following steps:

[0031] (1) Put 3.09g of compound II and 30.9mL of ethanol into a 50ml reaction flask, add 0.31g of 10% Pd / C and 1.93g of ammonium acetate under stirring, reflux for 1 hour, filter the reaction system after cooling, and use ethanol The filter cake was washed three times, the filtrate was collected, and concentrated under reduced pressure to obtain 2.12 g of off-white solid, namely compound III, with a yield of 97.7%;

[0032] (2) Under stirring, add 24.0mL of acetonitrile, 2.40g of compound IV, 1.89g of triethylamine and 2.10g of compound III to the 100mL reaction flask in sequence, and heat to reflux for reaction. After the reaction is completed, the reaction solution is cooled to room temperature , add 72.0mL of purified water to it, stir evenly, filter, the obtained filter cake is washed with water, and vacuum-dried at 40°C to obtain 3.66g of off-white s...

Embodiment 2

[0042] The preparation method of sitafloxacin hydrate described in the present embodiment comprises the following steps:

[0043] (1) Put 3.09g of compound II and 30.9mL of methanol into a 50ml reaction flask, add 0.11g of 10% Pd / C and 4.81g of ammonium acetate under stirring, and react at 50°C. After the reaction is completed, cool and filter , washed the filter cake three times with methanol, collected the filtrate, and concentrated under reduced pressure to obtain 2.17 g of off-white solid, which was Compound III, with a yield of 100%;

[0044] (2) Under stirring, add 24.0mL of acetonitrile, 2.83g of compound IV, 2.58g of N,N-diisopropylethylamine and 2.10g of compound III to a 100mL reaction flask in sequence, and react at 25°C until the reaction is complete Finally, 96.0 mL of purified water was added thereto, stirred evenly, filtered, the obtained filter cake was washed with water, and dried under vacuum at 40°C to obtain 4.37 g of an off-white solid, namely Compound V, ...

Embodiment 3

[0048] The preparation method of sitafloxacin hydrate described in the present embodiment comprises the following steps:

[0049] (1) Put 3.09g of compound II and 30mL of isopropanol into a 50ml reaction flask, add 0.58g of 10% Pd / C and 1.89g of ammonium formate under stirring, and react at 20°C. After the reaction is completed, filter, The filter cake was washed three times with isopropanol, the filtrate was collected, and concentrated under reduced pressure to obtain 2.17 g of off-white solid, namely compound III, with a yield of 100%;

[0050] (2) Under stirring, add 24.0mL of acetonitrile, 1.42g of Compound IV, 2.04g of aqueous ammonia and 2.10g of Compound III with an ammonia content of 25wt% to a 100mL reaction flask, and react at 55°C. After the reaction is complete, cool , adding 24.0 mL of purified water to it, stirring evenly, filtering, washing the obtained filter cake with water, and drying in vacuum at 40°C to obtain 2.19 g of an off-white solid, namely Compound V...

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Abstract

The invention provides a preparation method of a sitafloxacin hydrate. The preparation method takes a compound II as a raw material, debenzylation, substitution, chlorination and removal of t-butyloxycarboryl are sequentially carried out, and finally the sitafloxacin hydrate is obtained. The preparation method provided by the invention has the advantages that use of hydrogen and an autoclave is avoided, technological operation is greatly simplified, and hidden danger is also eliminated; and reaction in each technological step is rapid, no side reaction is generated, and separation and purification are simple and rapid, so that the preparation method provided by the invention not only has high yield, more importantly, the preparation method also has the advantages of environment friendliness, simple technology and low cost, and industrial large-scale mass production requirement can be met.

Description

technical field [0001] The invention relates to a preparation method of sitafloxacin hydrate, which belongs to the field of medicine and chemical industry. technical background [0002] Sitafloxacin (Sitafloxacin), its structure is shown in formula I, and its chemical name 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, from Daiichi Pharmaceutical Sankyo Co., Ltd. A powerful broad-spectrum quinolone antibacterial drug was developed, which was first launched in Japan in 2008. Its sesquihydrate was clinically used to treat severe and refractory bacterial infections, recurrent infections and certain drug-resistant bacterial infections, making sitasalox Star is expected to become an important drug for the treatment of single or mixed bacterial infections of the respiratory tract, genitourinary tract, abdominal cavity and skin and soft tissues. [0003] [0004] At present, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 陈言德徐凌燕袁卫东臧建英朱余苏陈东华高怡蓉吴子怡李喜峰顾静燕
Owner SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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