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Method for preparing cefcapene pivoxil hydrochloride

A technology of cefcapine and picoxil, applied in the direction of organic chemistry, can solve the problems of serious environmental pollution and high cost, and achieve the effects of high yield, low cost, great implementation value and potential social and economic benefits

Inactive Publication Date: 2010-10-06
ZHEJIANG HUAFANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved in the present invention is to overcome the disadvantages of relatively serious environmental pollution and high cost in the prior art, and provide a kind of cefcarpine pivoxil hydrochloride with higher yield, environmental friendliness, lower cost and stable process preparation method

Method used

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  • Method for preparing cefcapene pivoxil hydrochloride
  • Method for preparing cefcapene pivoxil hydrochloride
  • Method for preparing cefcapene pivoxil hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0024] 30g Boc-protected cefcarpine pivoxil was dissolved in 300g 2-methyltetrahydrofuran, and 30g 85% phosphoric acid was added dropwise at -15~-10°C, and after stirring and reacting for 4 hours, it was adjusted to pH = 7.0, separate the water layer, and concentrate the organic layer to dryness under reduced pressure to obtain an oil, add 30g of ethanol to dissolve, add 44g of 15% hydrochloric acid solution dropwise at 10-15°C to form a salt, keep stirring for 3 hours, filter, and take the filter cake for use 90 g of 50% ethanol aqueous solution was rinsed, and the washed filter cake was vacuum-dried at 45° C. to constant weight to obtain 22.0 g of cefcarpine pivoxil hydrochloride with a yield of 78.7% and a HPLC purity of 99.27%.

Embodiment 2

[0026] Dissolve 30g of Boc-protected cefcarpine pivoxil in 180g of ethyl acetate, add 45g of 80% phosphoric acid dropwise at -5~0°C, stir and react for 2.5 hours, adjust to pH=7.0 with 10% sodium hydroxide, divide Remove the water layer, and concentrate the organic layer to dryness under reduced pressure to obtain an oily substance, add 90g of ethanol to dissolve it, add 98g of 5% hydrochloric acid solution dropwise at 15-18°C to form a salt, keep stirring for 4 hours, filter, and take the filter cake with 60g of 30% hydrochloric acid Rinse with ethanol aqueous solution, and vacuum-dry the washed filter cake at 45° C. to constant weight to obtain 24.5 g of cefcarpine pivoxil hydrochloride with a yield of 87.5% and a purity of 99.25% by HPLC.

Embodiment 3

[0028] Dissolve 30g of Boc-protected cefcarpine pivoxil in 150g of 1,2-dichloroethane, add 90g of 60% phosphoric acid dropwise at 5-10°C, stir and react for 2 hours, then adjust the pH with 10% sodium hydroxide =7.0, remove the water layer, and concentrate the organic layer to dryness under reduced pressure to obtain an oily substance, add 30g of methanol to dissolve, add 32g of 5% hydrochloric acid solution dropwise at 15-20°C to form a salt, keep stirring for 4 hours, filter, and take the filter cake Rinse with 120 g of 10% ethanol aqueous solution, and vacuum-dry the washed filter cake at 45° C. to constant weight to obtain 21.7 g of cefcarpine pivoxil hydrochloride with a yield of 77.6% and an HPLC purity of 99.33%.

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Abstract

The invention relates to a method for preparing cefcapene pivoxil hydrochloride, which comprises the following steps: dissolving Boc-protected cefcapene pivoxil shown by a formula (II) in an organic solvent; dripping 60 to 85 mass percent aqueous solution of phosphoric acid at 15 DEG C below zero to 30 DEG C to perform a de-Boc reaction, stirring the solution, and after the reaction is performed for 1 to 4 hours, and adjusting the pH value of the reaction solution with aqueous solution of sodium hydroxide to 7.0; removing the water layer, and concentrating an organic layer under reduced pressure to recover an organic solvent to obtain an oily material; adding an alcohol solvent into the oily material, controlling the temperature between 10 and 20 DEG C, dripping 5 to 15 mass percent solution of hydrochloric acid to form a salt; and keeping the temperature for 1 to 4 hour, filtering the solution, washing the filter cake with 10 to 50 percent aqueous solution of ethanol, drying the filter cake under vacuum at 45 DEG C till the weight of the filter cake is constant and thus, obtaining the cefcapene pivoxil hydrochloride. The method of the invention is high in yield and low in cost and can reduce environmental pollution generated in the production of the Boc-protected cefcapene pivoxil in source.

Description

(1) Technical field [0001] The invention relates to a method for preparing cefcarpine pivoxil hydrochloride by removing the amino protecting group Boc and salt-forming crystallization in the preparation process of cefcarpine pivoxil. (2) Background technology [0002] Cefcapene Pivoxil Hydrochloride Hydrochloride (Cefcapene Pivoxil Hydrochloride Hydrate) is a broad-spectrum, orally effective new third-generation cephalosporin developed by Shionogi Company in Japan. When cefcapene pivoxil hydrochloride is absorbed into the human body, it is rapidly hydrolyzed into cefcapine by the esterase on the intestinal wall, and is distributed in the blood and tissues. Spectrum antibacterial effect, and stable to β-lactamase. According to clinical experiments done on various infections, it has achieved good clinical and bacteriological effects on adults and children, and has good safety. It is an oral cephalosporin with high curative effect. [0003] The chemical name of cefcarpine piv...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/04
Inventor 施智峰崔洁晨顾士崇王光明
Owner ZHEJIANG HUAFANG PHARMA
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