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Cefpodoxime proxetil compound of new route

A technology for cefpodoxime axetil and cefpodoxime acid, which is applied in the field of medicine, can solve the problems of high isomer content, low product purity, slow reaction and the like, and achieves the effects of high purity, high yield and low cost

Inactive Publication Date: 2010-07-07
HAINAN MEIDA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN1387533A discloses a preparation method of high-purity cefpodoxime axetil, through the reaction of cefpodoxime salt and 1-iodoethyl isopropyl carbonate in an organic solvent under the catalysis of crown ether, crown As a catalyst, ether is more toxic, and in the obtained cefpodoxime axetil raw material, Δ 2 Higher content of isomers
Chinese patent CN1640879A discloses a method for the preparation of high-purity cefpodoxime axetil by one-step method, using cefpodoxime axetil as raw material, reacting sodium acetate or sodium isooctanoic acid organic weak basic salt, adding iodo ester to react, No catalyst is used in this patent, the reaction is relatively slow, the yield is very low, and the product purity is low

Method used

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  • Cefpodoxime proxetil compound of new route
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Examples

Experimental program
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Effect test

Embodiment 1

[0030] The preparation of embodiment 1 cefpodoxime axetil

[0031] (1) Add 201g of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and 110ml triethylamine into 500ml dichloromethane, cool to 10°C, stir, Add 167g of p-nitrophenol, stir and react at this temperature for 1 hour, then add the solution formed by 244g of 7-AMCA, 200ml of triethylamine and 500ml of dichloromethane, react at 10°C for 3 hours, stir, add 3L of water, Regulate the pH with 10% hydrochloric acid to be 5, separate layers, wash the water phase with 500ml dichloromethane once, separate the layers, adjust the pH of the system with 10% hydrochloric acid to be 2.5, stir, precipitate solids, filter, and use Washed with 100ml of acetone and dried under vacuum at 40°C to obtain 397g of the product with a yield of 92.8%.

[0032] (2) Add 397g of cefpodoxamic acid to 2000ml of N,N-dimethylformamide, stir to dissolve, add 91.3g of sodium acetate and 10ml of water, stir at room temperature for 30min, cool to 5°C...

Embodiment 2

[0033] The preparation of embodiment 2 cefpodoxime axetil

[0034] (1) Add 201g of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and 110ml triethylamine into 500ml dichloromethane, cool to 5°C, stir, Add 167g of p-nitrophenol, stir and react at this temperature for 1 hour, then add the solution formed by 244g of 7-AMCA, 200ml of triethylamine and 500ml of dichloromethane, react at 5°C for 3 hours, stir, add 3L of water, Regulate the pH with 5% hydrochloric acid to be 6, separate layers, wash the water phase with 500ml dichloromethane once, separate the layers, adjust the pH of the system with 5% hydrochloric acid to be 3, stir, separate out solids, filter, use Washed with 100ml of acetone and dried under vacuum at 50°C to obtain 402g of the product with a yield of 94%.

[0035](2) Add 402g of cefpodoxamic acid into 2000ml of acetonitrile, stir to dissolve, add 92.5g of sodium acetate and 20ml of water, stir at room temperature for 30min, cool to 6°C, add 38g of PEG600...

Embodiment 3

[0036] The preparation of embodiment 3 cefpodoxime axetil

[0037] (1) Add 201g of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and 110ml of triethylamine into 500ml of acetonitrile, cool to 8°C, stir, and add 167g For p-nitrophenol, stir and react at this temperature for 1 hour, then add a solution formed by 244g of 7-AMCA, 200ml of triethylamine and 500ml of acetonitrile, react at 8°C for 3 hours, stir, add 3L of water, and use 15% Regulate the pH with hydrochloric acid to be 5.5, separate layers, wash the aqueous phase with 500ml acetonitrile once, separate the layers, adjust the pH of the system to 2.8 with 15% hydrochloric acid for the aqueous phase, stir, precipitate solids, filter, wash with 100ml acetone, and wash at 45 Vacuum-dried at °C to obtain 399.6 g of the product, with a yield of 93.5%.

[0038] (2) Add 399.6g of cefpodoxamic acid into 2000ml of tetrahydrofuran, stir to dissolve, add 92g of sodium acetate and 20ml of water, stir at room temperature fo...

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Abstract

The invention relates to a cefpodoxime proxetil compound of new route, which belongs to technology field of medicine. The steps comprise: (1) (Z) -2 - (2 - aminothiazole -4 - ethyl) -2 - methoxyimino aceticacid (AMAA in short) and p-nitrophenol react, 7-AMCA is added to the mixture and is stirred for reacting, the PH value is adjusted with hydrochloric acid to obtain the cefpodoxime acid; (2) PEG6000 is used as catalyst, the cefpodoxime acid reacts with 1 - iodine ethyl isopropyl carbonate to obtain the cefpodoxime proxetil. The advantages of the invention are as follows: the method has high yield, low cost, and obtained product of high purity; the content of delta2 isomer is low, and the invention is suitable for industrial production.

Description

technical field [0001] The invention relates to a new route of cefpodoxime axetil compound, which belongs 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] Cefpodoxime axetil is an oral third-generation cephalosporin with a broad antibacterial spectrum. After entering the body, it is hydrolyzed into cefpodoxime by non-specific esterase to exert antibacterial effect. It has a wide range of antibacterial effects on Gram-positive and Gram-negative bacteria. Antibacterial spectrum, stable to β-lactamase. [0005] 1-iodoethyl isopropyl carbonate is an important intermediate for the synthesis of cefpodoxime axetil, and cefpodoxime a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04
Inventor 王洪胜
Owner HAINAN MEIDA PHARMA
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