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Cefpodoxime proxetil impurity, preparation method thereof and application of cefpodoxime proxetil impurity

A technology of cefpodoxime axetil and impurities, applied in the field of drug preparation, to achieve the effect of high application value

Inactive Publication Date: 2018-09-14
SHANDONG RUIYING PIONEER PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report about this impurity in other literatures

Method used

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  • Cefpodoxime proxetil impurity, preparation method thereof and application of cefpodoxime proxetil impurity
  • Cefpodoxime proxetil impurity, preparation method thereof and application of cefpodoxime proxetil impurity
  • Cefpodoxime proxetil impurity, preparation method thereof and application of cefpodoxime proxetil impurity

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Experimental program
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Effect test

Embodiment 1

[0046] Embodiment 1, the present embodiment provides the concrete preparation method of formula I cefpodoxime axetil impurity, and the steps are as follows:

[0047] Add 10.0g of formula II compound and 16.4g of 2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetic acid thiobenzothiazolyl ester (AE active ester) to 20ml tetrahydrofuran and 100ml dihydrofuran In methyl chloride, the temperature was controlled at 20°C to 25°C, 4.7g of triethylamine was added, and the reaction was stirred for 5h.

[0048] Add the reaction solution into 100ml of ice water, extract and separate the layers, take the water phase and adjust the pH to 2.5-3.0 with 2mol / L hydrochloric acid, filter, and dry the filter cake under reduced pressure at 40°C to obtain 8.6g of a yellow solid (compound of formula IV), with a purity of 81.5 %.

[0049] Dissolve 8.0g of the compound of formula IV in 50ml of N,N-dimethylacetamide under stirring, control the temperature at -5°C to -10°C, slowly add 4.06g of 1-iodoethyl i...

Embodiment 2

[0051] Embodiment 2, this embodiment provides the specific preparation method of formula I cefpodoxime axetil impurity, the steps are as follows:

[0052] 10.0g formula VI compound and 43.7g 2-[2-[2-(2-amino-4-thiazolyl)-2-(methoxyimino)]acetamido-4-thiazolyl]-2-( Methoxyimino) thiobenzothiazolyl acetate was added to 20ml of tetrahydrofuran and 100ml of dichloromethane, the temperature was controlled at 20°C to 25°C, 8.3g of triethylamine was added, and the reaction was stirred for 5h.

[0053] Add the above reaction solution into 100ml of ice water, extract and separate the layers, take the water phase and adjust the pH to 2.5-3.0 with 2mol / L hydrochloric acid, filter, and dry the filter cake under reduced pressure at 40°C to obtain 16.2g of a yellow solid (compound of formula IV), with a purity of 83.1%.

[0054] Dissolve 8.0g of the compound of formula IV in 50ml of N,N-dimethylacetamide under stirring, control the temperature at -5°C to -10°C, slowly add 4.06g of 1-iodoet...

Embodiment 3

[0056] Embodiment 3, this embodiment provides the specific preparation method of formula I cefpodoxime axetil impurity, and the steps are as follows:

[0057] Add 10.0g of the compound of formula VIII and 12.5g of AE active ester into 100ml of dichloromethane, control the temperature at 25°C to 30°C, add 3.6g of triethylamine, and stir for 8h.

[0058] The reaction solution was added to 100ml of ice water, and the layers were extracted. Take the organic phase and add 50ml of water, and use hydrochloric acid to adjust the pH to 0.5-1.0. After standing for stratification, take the water phase, adjust the pH to neutral with 5% sodium bicarbonate solution, filter, and dry the filter cake under reduced pressure at 40°C to obtain a yellow solid. (Cefpodoxime axetil impurity) 2.6g, purity 75.5%. MS showed that the component m / z: [M+H]+ was 741, and the corresponding molecular weight was 740, which was consistent with the HPLC-MS data of the impurity in the chromatogram of the cefpod...

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Abstract

The invention relates to a cefpodoxime proxetil impurity, a preparation method thereof and an application of the cefpodoxime proxetil impurity, discovers a novel impurity of cefpodoxime proxetil in the preparation process, and discloses a preparation method and an application of the impurity. A pair of mono-impurities of the cefpodoxime proxetil are analyzed, forming processes of the impurities are derived, a synthetic method is designed, an impurity monomer is acquired and can be used for quality research and process research of raw medicines and preparations of cefpodoxime proxetil, researchof impurity comparison products and the like, effective data support is provided for improvement of the quality of the cefpodoxime proxetil, and effective guarantee is provided for safe clinical useof the cefpodoxime proxetil. Quality research of the medicines is important, and research of the impurities is particularly important along with popularization of consistency evaluation of generic medicines. Research of the impurities has great significance for product quality control and medication safety of people.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and relates to a cefpodoxime axetil impurity and a preparation method and application thereof. Background technique [0002] Cefpodoxime axetil, chemical name (6R,7R)-3-methoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-[(Z)-methoxyimino]acetyl Amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-(RS)-1-(isopropoxyformyloxy) Ethyl ester is the third-generation oral broad-spectrum cephalosporin developed by Japan's Sankyo Company. It has a broad antibacterial spectrum and strong antibacterial power. It requires less dosage and less frequent administration, which can improve patients' medication compliance. Its chemical structural formula is as follows, wherein cefpodoxime axetil is in C * The epimer at also belongs to cefpodoxime axetil. [0003] [0004] In the 2015 edition of the "Chinese Pharmacopoeia", the quality standards for cefpodoxime axetil, especially the relate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04G01N30/88
CPCC07D501/04C07D501/34G01N30/88G01N2030/8872
Inventor 彭继先宁小荣杨胜男李茜茜付喜成
Owner SHANDONG RUIYING PIONEER PHARMA
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