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Preparation method of E-type isomer of cefcapene pivoxil

A technology for cefcapine pivoxil and isomers, which is applied in the field of preparation of cefcapine pivoxil E isomers, and can solve the problems of no introduction of the synthesis method of cefcapine pivoxil E isomers and the like

Active Publication Date: 2022-04-15
湖北凌晟药业股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The E-type isomer of cefcapene pivoxil hydrochloride is a reaction by-product produced in the production process of cefcapene pivoxil hydrochloride, and is a key impurity in the cefcapene pixil hydrochloride bulk drug. Introduction of Synthetic Method of Esters E-Isomer

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[0022] The invention provides a kind of preparation method of cefcapene pivoxil E-type isomer, comprising the following steps:

[0023] The organic solution of cefcapene pivoxil raw material is heated to reflux, obtains cefcapene pivoxil E-type isomer, and described cefcapene pivoxil raw material comprises the inorganic salt of cefcapene pivoxil and / or cefcapene pivoxil, and described heating reflux The insulation temperature is ≥40°C.

[0024] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known to those skilled in the art.

[0025] In the present invention, the organic solution of the raw material of cefcapene pivoxil preferably includes the raw material of cefcapene axetil and an organic solvent (hereinafter referred to as the first organic solvent).

[0026] In the present invention, the raw material of cefcapene pivoxil preferably includes an inorganic salt of cefcapene pivoxil.

[0027] In a specifi...

Embodiment 1

[0069] At 20°C, add 10g of cefcapene pivoxil hydrochloride and 100mL of methanol into a 500mL flask, stir until the system dissolves, raise the temperature in a water bath to 50°C, stir for 3-4 hours, and monitor cefcapene pivoxil E by thin-layer chromatography and HPLC. The reaction can be stopped when the isomer content does not increase. Concentrate the reaction solution under reduced pressure at 40°C to a yellow solid. Dissolve the yellow solid in 100mL of ethyl acetate and stir evenly. Then add 50mL of pure water and add 10% Adjust the sodium hydroxide solution to pH = 6, stir for 30 minutes, separate layers, dry over anhydrous sodium sulfate, filter, and concentrate to dryness under reduced pressure at 30-45°C to obtain the crude product of cefcapine isomer type E; wet-packed silica gel Column, separate and purify the sample with the mobile phase of dichloromethane:methanol=35:1 (v:v), concentrate under reduced pressure, and dry the material with 30°C to obtain 6.0g of dr...

Embodiment 2

[0071] At 20°C, add 10g of cefcapene axetil hydrochloride and 90mL of methanol into a 500mL flask, stir until the system dissolves, raise the temperature in a water bath to 50°C, stir for 3-4 hours, and monitor cefcapene axetil E by thin-layer chromatography and HPLC. The reaction can be stopped when the isomer content does not increase. Concentrate the reaction solution under reduced pressure at 40°C to a yellow solid. Dissolve the yellow solid in 90mL of dichloromethane and stir evenly. Then add 50mL of pure water and add 10% Adjust the sodium hydroxide solution to pH = 6, stir for 30 minutes, separate layers, dry over anhydrous sodium sulfate, filter, and concentrate to dryness under reduced pressure at 30-45°C to obtain the crude product of cefcapine isomer type E; wet-packed silica gel Column, separate and purify the sample with the mobile phase of dichloromethane:methanol=40:1 (v:v), concentrate under reduced pressure, and dry the material with 30°C to obtain 5.8g of dry ...

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Abstract

The invention relates to the technical field of medicine synthesis, in particular to a preparation method of a cefcapene pivoxil E-type isomer. According to the preparation method, an organic solution of a cefcapene pivoxil raw material is heated and refluxed to obtain the E-type isomer of the cefcapene pivoxil, the cefcapene pivoxil raw material comprises the cefcapene pivoxil and / or inorganic salt of the cefcapene pivoxil, and the heat preservation temperature of heating and refluxing is larger than or equal to 40 DEG C. According to the preparation method provided by the invention, the cefcapene pivoxil E-type isomer is successfully prepared by heating and refluxing the cefcapene pivoxil solution when the holding temperature is greater than or equal to 40 DEG C, and the yield of the cefcapene pivoxil E-type isomer is high.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of cefcapene pivoxil E-type isomer. Background technique [0002] Cefcapene Pivoxil Hydrochloride (Cefcapene Pivoxil Hydrochloride), the chemical name is 7-[2-(2-amino-1,3-thiazol-4-yl)pent-3-enamido]-3-(carbamoyloxy Methyl)-8-oxo-5-thio-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethylpropionyloxymethyl ester hydrochloride, which The chemical structure is shown in formula 1: [0003] [0004] Cefcapene pivoxil hydrochloride is a third-generation oral cephalosporin antibiotic, developed by Shionogi Co., Ltd. of Japan, and first listed in 1997 under the trade name of Flomox. The results of pharmacological studies have shown that cefcapene hydrochloride has stronger antibacterial activity and lower dosage than the existing oral cephalosporins. Mainly suitable for respiratory infections caused by sensitive bacteria such as pneumonia, bronc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/12
CPCY02P20/55
Inventor 何健卢超金联明门万辉黄金果
Owner 湖北凌晟药业股份有限公司
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