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Cefdinir compound and new preparation method thereof

A technology for cefdinir and a preparation method, applied in the field of cefdinir compounds and new preparation methods thereof, can solve the problems of high requirements for activated esters, environmental pollution, large structural differences of pentafluorophenol and the like

Inactive Publication Date: 2012-01-11
HAINAN MEIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But when above-mentioned patent is to (Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetic acid activation, the activated ester group selected is the same as the pentafluorophenol structure of the present invention There are large differences, strict restrictions on anhydrous conditions, high requirements on activated esters, complicated operations, and great pollution to the environment, and the prepared products have low purity

Method used

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  • Cefdinir compound and new preparation method thereof
  • Cefdinir compound and new preparation method thereof
  • Cefdinir compound and new preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 Cefdinir

[0029] (1) 215g (0.5mol) (Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetic acid and 80ml of triethylamine are added to 350ml of DMF, and the reaction Thing was cooled to 10 ℃, added 93g (0.5mol) pentafluorophenol, stirred reaction at this temperature for 1 hour, then added 113g (0.5mol) 7-AVCA and 140ml triethylamine, stirred vigorously at 10 ℃ for 0.5 hour, then Add 4L of water, adjust the pH of the reaction to 6.5 with 2mol / L hydrochloric acid, stir at room temperature for 1 hour, a solid precipitates, filters, washes with water, and vacuum-dries at 40°C to obtain 287g of the product, yield: 90%.

[0030] (2) 200g (0.31mol) of the above product and 600ml of 99% formic acid were mixed and refluxed for 5 hours, cooled to room temperature, 600ml of water, 300ml of tetrahydrofuran and 600ml of ethyl acetate were added, and the pH was adjusted with 10% aqueous sodium bicarbonate solution to 6.8, Fractionally distill off the water ...

Embodiment 2

[0030] (2) 200g (0.31mol) of the above product and 600ml of 99% formic acid were mixed and refluxed for 5 hours, cooled to room temperature, 600ml of water, 300ml of tetrahydrofuran and 600ml of ethyl acetate were added, and the pH was adjusted with 10% aqueous sodium bicarbonate solution to 6.8, Fractionally distill off the water phase, then wash with 600ml of ethyl acetate, separate the layers, adjust the pH of the water phase to 2.6 with 2mol / L hydrochloric acid, precipitate a solid, stir in an ice bath for 1.5 hours, filter, wash with 200ml of water, at 40 ℃ vacuum drying to obtain 114 g of the product, yield: 92%, purity 99.9%. The synthesis of embodiment 2 Cefdinir

[0031] (1) 215g (0.5mol) (Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetic acid and 80ml of triethylamine are added to 350ml of DMF, and the reaction Thing was cooled to 5 ℃, added 93g (0.5mol) pentafluorophenol, stirred reaction at this temperature for 1 hour, then added 113g (0.5mol) 7-AVCA and 140ml tri...

Embodiment 3

[0033] The synthesis of embodiment 3 Cefdinir

[0034] (1) 430g (1mol) (Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetic acid and 150ml of triethylamine are added to 700ml of DMF, and the reactant Cool to 8°C, add 186g (1mol) pentafluorophenol, stir the reaction at this temperature for 1 hour, then add 226g (1mol) 7-AVCA and 280ml triethylamine, stir vigorously at 8°C for 0.5 hour, then add 8L water , adjusted the reaction pH to 6.5 with 5mol / L hydrochloric acid, stirred at room temperature for 1.5 hours, precipitated solid, filtered, washed with water, and dried in vacuum at 45°C to obtain 579g of product, yield: 90.8%.

[0035] (2) 318.8g (0.5mol) of the above product and 1000ml of 99% formic acid were mixed and refluxed for 5 hours, cooled to room temperature, 1000ml of water, 500ml of tetrahydrofuran and 1000ml of ethyl acetate were added, and the pH was adjusted with 10% aqueous sodium bicarbonate to 6.7, the fractional distillation of the aqueous phase was then washed ...

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Abstract

The invention discloses a cefdinir compound and a new preparation method thereof. The method prepares the cefdinir by performing reaction on (Z)-2-(2-aminothiazole-4-group)-2-triphenylmethyl iminoacetic acid serving as an initial raw material, pentafluorophenol serving as an activating group and 7-AVCA.

Description

technical field [0001] The invention relates to a cefdinir compound and a new preparation method thereof, belonging to the technical field of medicine. Background technique [0002] Cefdinir, its chemical name is: (6R,7R)-7-[(2-amino-4-thiazolyl)-(oximino)acetoxy]amino]-3-vinyl-8-oxo-5 -Thia-1-azabicyclo[4.2.0]oct-2-ene-2-hydroxy acid, molecular formula: C 14 h 13 N 5 0 5 S 2 , molecular weight: 395.42, structural formula: [0003] [0004] Cefdinir is a broad-spectrum antibiotic that inhibits the synthesis of bacterial cell walls and has a broad antibacterial spectrum against most Gram-positive and Gram-negative bacteria, especially Staphylococcus and Streptococcus among Gram-positive bacteria. , has stronger antibacterial activity than previous oral cephalosporins, and its mode of action is bactericidal. It is stable against β-lactamase produced by various bacteria and has excellent antibacterial activity against β-lactamase-producing bacteria. [0005] Chinese ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/22C07D501/04
Inventor 郝志艳
Owner HAINAN MEIDA PHARMA
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