Method for preparing antibacterial cefdinir

A technology of cefdinir and acid anhydride, which is applied in the field of preparation of cefdinir to achieve the effects of simple reaction process, high yield and improved reaction selectivity

Inactive Publication Date: 2014-03-26
CHENGDU YILUKANG MEDICAL TECH & SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] All there is certain drawback in the synthetic method of above-mentioned cefdinir, so need to develop a kind of technique simple, yield height, be applicable to the method for suitability for suitability for industrialized production

Method used

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  • Method for preparing antibacterial cefdinir
  • Method for preparing antibacterial cefdinir
  • Method for preparing antibacterial cefdinir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Preparation of mixed anhydride

[0032] Take (Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetic acid (demethylaminothioxamic acid) 100g (0.53mol), suspend and stir in 200ml dichloromethane, cool to -10℃ , dropwise added 81ml (0.56mol) of triethylamine, the temperature was controlled to be less than -5°C during the dropping process, and after the dropping was completed, a clear solution was obtained. Cool down to -15°C, add 128 g (1.12 mol) of methanesulfonyl chloride dropwise, after the drop is complete, stir and react at -10°C for 1 hour, set aside.

[0033] (2) (6R,7R)-7-[[(2-amino-4-thiazolyl)-(oximino)acetyl]amino]-3-vinyl-8-oxo-5-thia-1 - Preparation of azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefdinir)

[0034] Take 120g (0.53mol) of 7-amino-3-vinyl-3-cephem-4-carboxylic acid, suspend and stir in 2000ml of dichloromethane, cool down to -10°C, add dropwise 81ml of triethylamine (0.56mol ), after dropping, a clear solution was obtained. Add the mixed acid...

Embodiment 2

[0040] 1) Preparation of mixed anhydrides

[0041] Take (Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetic acid (demethylaminothioxamic acid) 100g (0.53mol), suspend and stir in 200ml dichloromethane, cool to -10℃ 134ml (0.56mol) of tri-n-butylamine was added dropwise, the temperature was controlled to be less than -5°C during the dropwise addition process, and a clear solution was obtained after the dropwise addition. Cool down to -15°C, add 128 g (1.12 mol) of methanesulfonyl chloride dropwise, after the drop is complete, stir and react at -10°C for 1 hour, set aside.

[0042] 2) (6R,7R)-7-[[(2-amino-4-thiazolyl)-(oximino)acetyl]amino]-3-vinyl-8-oxo-5-thia-1- Preparation of azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefdinir)

[0043]Take 120g (0.53mol) of 7-amino-3-vinyl-3-cephem-4-carboxylic acid, suspend and stir in 2000ml of dichloromethane, cool down to -10°C, add dropwise 134ml of tri-n-butylamine (0.56 mol), after dropping, a clear solution was obtained. Add the ...

Embodiment 3

[0045] According to Example 1, dichloromethane was replaced with ethyl acetate to obtain 152.6 g (yield 72.8%) of cefdinir slightly yellow crystalline powder, with an HPLC purity of 99.2%.

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Abstract

The invention provides a method for synthesizing antibacterial cefdinir. 2-(2-aminothiazole-4-yl)-2-hydroxyiMinoacetic acid and methylsufonyl chloride form anhydride; and anhydride reacts with 7-amino-3-vinyl-8-oxo-5-thia-azabicyclo [4.2.0]oct-2-ene-2-carboxylate, and cefdinir is obtained through hydrolysis. The method is simple in processing, high in yield and applicable to industrial production.

Description

technical field [0001] The invention relates to a preparation method of antibacterial drugs, in particular to a preparation method of cefdinir. Background technique [0002] Cefdinir is an oral cephalosporin pioneered by Japan Fujisawa Pharmaceutical Co., Ltd. It has good antibacterial activity against a variety of Gram-positive and Gram-negative aerobic bacteria, such as Streptococcus pneumoniae, suppurative Streptococcus, Staphylococcus aureus, Haemophilus influenzae and Moraxella catarrhalis, etc., and is stable to common β-lactamases. It can be used to treat mild to moderate community-acquired pneumonia, acute and chronic bronchitis, streptococcal pyogenes pharyngitis / tonsillitis, acute otitis media in children, acute sinusitis, ophthalmology and ENT infections, skin and soft tissue infections, postoperative infections, urinary Tract infection and gynecological infection etc. [0003] The synthetic method of cefdinir mainly contains following two kinds at present: [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/04
CPCC07D501/04C07D501/22
Inventor 骆均勇彭超
Owner CHENGDU YILUKANG MEDICAL TECH & SERVICE
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