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Cefmetazole sodium compound and synthetic method thereof

A technology of cefmetazole sodium and a synthesis method, applied in the field of drug synthesis, can solve the problems of low yield and purity, and achieve the effects of high product purity, low raw material cost and high yield

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

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a synthetic method of cefmetazole sodium compound, which solves the problems of low yield and purity in the prior art, and ensures the safety of clinical application

Method used

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  • Cefmetazole sodium compound and synthetic method thereof
  • Cefmetazole sodium compound and synthetic method thereof
  • Cefmetazole sodium compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 cefmetazole sodium

[0027] 153 grams of sodium cyanomethylthioacetate was added to 500 ml of DMF, the reactant was cooled to 10°C, 192 grams (1mol) of p-toluenesulfonyl chloride was added, the reaction was stirred at this temperature for 1 hour, and then 448 grams (1mol) of ) 7β-amino-7a-methoxyl group-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylate benzyl ester and 300ml triethylamine, in 5 ℃ vigorously stirred for 0.5 hours, then added 500ml of 6mol / L hydrochloric acid, raised the temperature to 35℃, stirred and reacted for 1.5 hours, cooled to room temperature, then adjusted the pH of the reaction system to 7.0 with 4mol / L sodium hydroxide, and used 400ml The ethyl acetate was washed twice, the aqueous phase was concentrated to a small volume, and freeze-dried to obtain 463 g of the product, with a yield of 94%.

Embodiment 2

[0028] The synthesis of embodiment 2 cefmetazole sodium

[0029] 153 grams of sodium cyanomethylthioacetate was added to 600 ml of N,N-dimethylacetamide, the reactant was cooled to 8°C, 192 grams (1mol) of p-toluenesulfonyl chloride was added, and the reaction was stirred at this temperature for 1 hour, then add 448 grams (1mol) of 7β-amino-7a-methoxyl group-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid benzyl ester and 300ml of triethylamine, stirred vigorously at 10°C for 0.5 hours, then added 1000ml of 3mol / L hydrochloric acid, raised the temperature to 40°C, stirred and reacted for 1 hour, cooled to room temperature, and then adjusted the reaction system with 5mol / L sodium hydroxide pH = 8.0, washed twice with 300ml of ethyl acetate, the aqueous phase was concentrated to a small volume, freeze-dried to obtain 427 grams of product, yield: 92.2%.

Embodiment 3

[0030] The synthesis of embodiment 3 cefmetazole sodium

[0031] 306 grams of sodium cyanomethylthioacetate are added to 1000 ml of toluene, the reactant is cooled to 5°C, 385 grams (2mol) of p-toluenesulfonyl chloride are added, the reaction is stirred at this temperature for 1 hour, and then 896 grams (2mol) of p-toluenesulfonyl chloride are added. ) 7β-amino-7a-methoxy-3-(1-methyl-1H-tetrazol-5-thiomethyl)-3-cephem-4-carboxylate and 700ml triethylamine, in 7 ℃ vigorously stirred for 1 hour, then added 1000ml of 6mol / L hydrochloric acid, raised the temperature to 35℃, stirred and reacted for 1.5 hours, cooled to room temperature, then adjusted the pH of the reaction system to 7.5 with 2mol / L sodium hydroxide, and used 1000ml The ethyl acetate was washed twice, the aqueous phase was concentrated to a small volume, and freeze-dried to obtain 919 g of the product, with a yield of 93.3%.

[0032] Elemental Analysis Molecular Formula: C 15 h 16 N 7 NaO 5 S 3

[0033] Theor...

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Abstract

The invention relates to a cefmetazole sodium compound and a synthetic method thereof, 7 Beta-amino-7 Alpha-methoxyl-3-(1-methyl-1H-tetrazole-5-sulfidomethyl)-3-cephem-4-benzyl carboxylate and cyanomethylthio acetic acid sodium are mixed and react in the presence of p-toluenesulfonyl chloride to generate cefmetazole; sodium hydroxide is added to obtain cefmetazole sodium. Compared with the prior art, the invention has the advantages of few reaction steps, high productive rate, high product purity and low cost of raw materials, and has a broad prospect.

Description

technical field [0001] The invention relates to a synthesis method of cephalosporin compounds, in particular to a synthesis method of cefmetazole sodium compound, and belongs to the technical field of drug synthesis. Background technique [0002] Cefmetazole sodium, its English name is Cefmetazole Sudium, its chemical name is: (6R, 7S)-7-[2-[(cyanomethyl)thio]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 - sodium salt of carboxylic acid, molecular formula: [0003] C 15 h 16 N 7 NaO 5 S 3 , molecular weight: 493.52, structural formula: [0004] [0005] Cefmetazole sodium is a second-generation cephalosporin, which has good stability to broad-spectrum β-lactamase produced by negative bacilli, such as Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Shigella, Salmonella Bacteria and other negative bacilli have good sensitivity to this product. Staphylococcus aureus, group A hemolytic strepto...

Claims

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Application Information

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IPC IPC(8): C07D501/57C07D501/06A61P31/04
Inventor 张锡芬
Owner HAINAN LINGKANG PHARMA CO LTD
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