A kind of preparation method of cefminox sodium

A technology of cefminox sodium and cephem, which is applied in the field of preparation of pharmaceutical compounds, can solve the problems of expensive raw materials, low yield, and unsuitability for industrialized large-scale production, and achieves a small amount of impurity generation, a small amount of impurity generation, and finished products The effect of improving quality and stability

Inactive Publication Date: 2011-12-07
HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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  • Abstract
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Problems solved by technology

[0024] Some of the above methods use expensive raw materials, some are not suitable for large-scale industrial production, and some yields are relativel

Method used

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  • A kind of preparation method of cefminox sodium
  • A kind of preparation method of cefminox sodium
  • A kind of preparation method of cefminox sodium

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Embodiment 1

[0055] 1. Synthesis of 7β-amino-3-(1-methyl-1H-tetrazole-5-thiomethyl)-3-cephem-4-carboxylic acid (3-TZ) at room temperature with 37.5g (0.138mol) 7-Aminocephalosporanic acid (7-ACA) and 16g (0.138mol) methylmercaptotetrazolium are mixed evenly with 200g acetonitrile as a solvent, (wet feeding is used to reduce the spread of 7-ACA dust and reduce the risk of 7-ACA allergy ). Add 100g of 20% boron trifluoride acetonitrile to the system and react at 35-40°C for 2 hours, add dropwise 20g of concentrated hydrochloric acid for crystallization, filter, wash with acetonitrile, and dry to obtain about 48.8g of intermediate 3-TZ with a yield of 130%.

[0056] 2. Synthesis of 7β-dichloroacetamido-3-(1-methyl-1H-tetrazole-5-thiomethyl)-3-cephem-4-carboxylic acid (DCT)

[0057] Mix 33g (0.1mol) 3-TZ and 200g ethanol evenly at room temperature, add 17g dichloroacetyl chloride at 15-20°C, and react at the same temperature for 30 minutes. The liquid phase monitoring shows that the residual ...

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Abstract

The present invention relates to a kind of preparation of medicinal compound, particularly a kind of preparation method of cefminox sodium. The present invention adopts a synthesis route using 7-ACA as a starting material, and the cost of raw materials is lower than that of a synthesis route using 7-MAC as a starting material. The new synthetic route uses dichloroacetyl chloride instead of bromoacetyl bromide, which reduces the toxicity and cost of raw materials. The new synthetic route increases the intermediate treatment process, reduces the amount of impurities brought by the intermediate into the next reaction, and improves the quality and stability of the finished product. The present invention overcomes the shortcomings of the synthetic route using 7-MAC as the starting material through the above improvements.

Description

Technical field: [0001] The present invention relates to a kind of preparation of medicinal compound, particularly a kind of preparation method of cefminox sodium. Background technique: [0002] Cefminox is a cephalosporin antibiotic, [0003] English name: Cefminox [0004] Chinese name: cefminox [0005] Chemical name: (6R,7S)-7-[2-[(S)-2-amino-2-carboxyethylthio]acetamido]-7-methoxy-3-[[(1-methyl- 1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; aminocarboxymethoxy Cephalosporin; (6R,7S)-7-[2-[(S)-2-amino-2-carboxyethylthio]acetamido]-7-methoxy-3-[[(1-methyl -1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [0006] Molecular formula: C16H21N7O7S3 [0007] Molecular weight: 519.58 [0008] CAS number: 75481-73-1 [0009] [0010] Cefminox is highly stable to β-lactamase. This product has a strong affinity with penicillin-binding protein at the point of action of β-lactam antibio...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04
Inventor 吴志军赵玉新王喜军杨槐李国峰王安娜李刚陈桂芹房新连刘治林
Owner HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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