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Cefpodoxime proxetil compound and preparation method thereof

A technology of cefpodoxime axetil and compounds, which is applied in the field of refining cefpodoxime axetil compounds, can solve the problems that the purity of cefpodoxime axetil is not fundamentally improved, the purity of cefpodoxime axetil is low, and it is difficult to prepare preparations, etc., and achieves low cost, Ease of operation and the effect of ensuring safety

Inactive Publication Date: 2009-10-07
HAINAN MEIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] About the synthetic method of cefpodoxime axetil, all have report in U.S. Patent 5498787, Korean Patent No.99-54751, patent WO01 / 34611 and literature (J.ofAnbitiotics, Vol 40370 (1987)), but the preparation of above-mentioned literature method A common problem of cefpodoxime axetil is that the purity is low, which cannot reach the limit required by the preparation standard, and it is difficult to prepare qualified preparations, and the general refining method of dissolution and crystallization cannot fundamentally improve its purity.

Method used

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  • Cefpodoxime proxetil compound and preparation method thereof
  • Cefpodoxime proxetil compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] (1) Dissolve 100 g of cefpodoxime axetil crude product in 500 ml of N, N-dimethylformamide, add 180 ml of 2mol / L sodium hydroxide solution, stir and react at room temperature for 60 minutes, hydrolyze to separate crystals, filter, and ethanol Washing and drying under reduced pressure at 50°C gave 96.7 g of cefpodoxime sodium salt, with a yield of 96.7%;

[0019] 1 H-NMR (δ, D 2 O): 3.15(s, 3H, C-OCH 3 ), 3.37 (ABq, 2H, C-2), 3.85 (s, 3H, =N-OCH 3 ), 4.07 (d, 2H, -CH 2 -OCH 3 ), 5.09 (d, 1H, C-6), 5.66 (d, 1H, C-7), 6.88 (s, 1H, aminothiazole ring-H).

[0020] (2) Dissolve the above-mentioned cefpodoxime sodium salt in 800ml of water, add 5g of activated carbon for adsorption for 30 minutes, filter and decarburize, then add 77.4g of 1-iodoethyl isopropyl carbonate and 200ml of tetrahydrofuran, and react with stirring at room temperature for 60 minutes, Then add 800ml of ethyl acetate and 200ml of water, stir and extract, separate layers, wash the organic phase with...

Embodiment 2

[0024] (1) Dissolve 100 g of cefpodoxime axetil crude product in 300 ml of methanol and 500 ml of chloroform, add 50 ml of 5 mol / L sodium acetate solution, stir and react at room temperature for 30 minutes, hydrolyze to precipitate crystals, filter, wash with ethanol, 50 ° C Dry under reduced pressure to obtain 97.2 g of cefpodoxime sodium salt, with a yield of 97.2%;

[0025] 1 H-NMR (δ, D 2 O): 3.16 (s, 3H, C-OCH 3 ), 3.36 (ABq, 2H, C-2), 3.87 (s, 3H, =N-OCH 3 ), 4.06 (d, 2H, -CH 2 -OCH 3 ), 5.10 (d, 1H, C-6), 5.68 (d, 1H, C-7), 6.89 (s, 1H, aminothiazole ring-H).

[0026] (2) Dissolve the above-mentioned cefpodoxime sodium salt in 1000ml of water, add 8g of activated carbon for adsorption for 30 minutes, filter for decarburization, then add 116.1g of 1-iodoethyl isopropyl carbonate and N,N-dimethylacetamide 300ml, stirred at room temperature for 30 minutes, then added 1200ml ethyl acetate and 200ml water, stirred and extracted, layered, the organic phase was washed wi...

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Abstract

The invention relates to a cefpodoxime proxetil compound and a preparation method thereof. In the method, the crude product of cefpodoxime proxetil prepared by the prior art is processed by the following steps to obtain a relatively pure cefpodoxime proxetil compound: the crude product of cefpodoxime proxetil dissolves in an organic solvent A; alkali or an organic alkalescent saline solution is added and the mixture is stirred for reaction and hydrolyzed to obtain cefpodoxime salt; the cefpodoxime salt is absorbed with added active carbon and filtered; and then 1-iodoethyl isopropyl carbonic ester is added and reaction is conducted in the presence of an organic solvent B to obtain cefpodoxime proxetil.

Description

technical field [0001] The invention relates to a method for refining cefpodoxime axetil compound, belonging to the technical field of medicine. Background technique [0002] Cefpodoxime axetil, its chemical name is: (6R, 7R)-7-[2-(2-amino-4-thiazolyl)-(Z)-2-(methoxyimino)-acetamido]-3 -Methoxymethyl-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid isopropoxycarbonyloxyethyl ester, molecular formula: C 21 h 27 N 5 o 9 S 2 , molecular weight: 557.61, structural formula: [0003] [0004] It is a third-generation cephalosporin orally administered with a broad antibacterial spectrum. After entering the body, it is hydrolyzed by non-specific esterase into cefpodoxime to exert antibacterial effect. It has a wide range of antibacterial spectrum against Gram-positive bacteria and Gram-negative bacteria. β-lactamase stable. It is clinically applicable to upper respiratory tract infection, lower respiratory tract infection, simple urinary tract infection, simple...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/12A61P31/04
Inventor 郑仙锋
Owner HAINAN MEIDA PHARMA
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