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Refining method for cefcapene pivoxil hydrochloride

A technology of cefcapine hydrochloride and a refining method, applied in the direction of organic chemistry and the like, can solve the problems of poor stability, increased impurities in the finished product, influence on the quality of the finished product, etc., and achieves the effects of mild reaction conditions, reduced production costs, and environmental friendliness.

Inactive Publication Date: 2015-04-29
SHANDONG LUKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Since multiple parts of the β-lactam ring in the structure of cefcapene pivoxil hydrochloride are prone to degradation reactions, the stability of cefcapene pivoxil hydrochloride is poor. The impurities in the finished product will increase. In addition, the crystallization temperature, the time of crystal growth, the concentration of hydrochloric acid, and the choice of crystallization solvent will also have a certain impact on the quality of the finished product.

Method used

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  • Refining method for cefcapene pivoxil hydrochloride

Examples

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Effect test

Embodiment 1

[0021] In a 250ml four-neck bottle, add 9.4g of cefcapene axetil hydrochloride crude product, 50ml of methanol, and 100ml of chloroform, stir at room temperature, add 5% sodium hydroxide solution to adjust the pH to neutral, let stand to separate layers, and take the organic layer through Concentrate under reduced pressure to recover the organic solvent, add 100ml of methyl acetate to the residue, control the temperature at 10°C, add 17.5ml of pre-prepared 5% hydrochloric acid solution dropwise, keep stirring for 4 hours, cool to 0°C, filter, and use cold methyl acetate The ester was washed and dried to obtain the fine product of cefcapene hydrochloride. The product is in the form of white powder, the product purity is 99.8%, and the weight yield is 82%.

Embodiment 2

[0023] In a 250ml four-necked bottle, add 9.4g of crude product of cefcapene axetil hydrochloride, 50ml of isopropanol, and 100ml of dichloromethane, stir at room temperature, add 5% sodium bicarbonate solution to adjust the pH to neutral, let stand for stratification, and take the organic The layer was concentrated under reduced pressure to recover the organic solvent, and the residue was added with 100ml of ethyl acetate, the temperature was controlled at 15°C, 8.7ml of a pre-prepared 10% hydrochloric acid solution was added dropwise, kept stirring for 5 hours, cooled to 10°C, filtered, cold acetic acid Wash with ethyl ester and dry to obtain the fine product of cefcapene hydrochloride. The product is white powder, the product purity is 99.6%, and the weight yield is 79%.

Embodiment 3

[0025] In a 250ml four-necked bottle, add 9.4g of cefcapene axetil hydrochloride crude product, 75ml of acetone, and 100ml of chloroform, stir at room temperature, add 5% potassium carbonate solution to adjust the pH to neutral, let stand to separate layers, take the organic layer and reduce Concentrate under pressure to recover the organic solvent, add 100ml of butyl acetate to the residue, control the temperature at 20°C, add 8.7ml of pre-prepared 10% hydrochloric acid solution dropwise, keep stirring for 6 hours, cool down to 5°C, filter, and wash with cold butyl acetate , dried to obtain cefcapene hydrochloride white powder, product purity 99.5%, weight yield 75%.

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Abstract

The invention relates to a refining method for cefcapene pivoxil hydrochloride, and belongs to the technical field of pharmaceutical synthesis. A crude cefcapene pivoxil hydrochloride product is dissolved, the pH is regulated, the product is subjected to standing layering, a water layer is abandoned, an organic layer is taken and subjected to reduced pressure distillation, an organic solvent is recovered, then an ester crystallization solvent is added to distillation residues, the temperature is controlled, a hydrochloric acid solution is added for salifying, and a refined cefcapene pivoxil hydrochloride product is obtained after crystal growing, filtering, washing and drying. According to the refining method for cefcapene pivoxil hydrochloride, single ester solvent is used for crystallization, an ester solvent can be recovered from filtered ester mother liquor through reduced pressure distillation and be reused, the production cost is reduced greatly, reaction raw materials are simple and easy to obtain, the process is simple, reaction conditions are mild, and the method is environment-friendly and suitable for large-scale popularization and application.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for refining cefcapene hydrochloride. Background technique [0002] Cefcapene Proxil Hydrochloride, chemical name: (6R,7R)-3-(((carbamoyl)oxy)methyl)-7-(((2Z)-2-(2-amino-4-thiazolyl) -1-oxo-2-pentene)amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-ene-2-carboxylic acid-2,2-di Methyl pivaloyloxymethyl ester hydrochloride monohydrate, its structural formula is: [0003] [0004] Cefcapene pivoxil hydrochloride is a broad-spectrum cephalosporin antibiotic. It was first developed by Shionogi Pharmaceutical Co., Ltd. in Japan. It was listed in Japan for the first time in 1997 under the trade name Flomox. Broad-spectrum antibiotic drugs, the product is mainly suitable for respiratory infections caused by sensitive bacteria such as pneumonia, bronchitis, pharyngitis, tonsillitis, otitis media, sinusitis, urinary tract infections such as gonorrhea, pyelonephritis, cy...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/12
CPCC07D501/34C07D501/12
Inventor 唐磊贾玲晓王文笙张淑婷张冬梅高占文张宪生
Owner SHANDONG LUKANG PHARMA
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