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Method for preparing ceftezole sodium compound

A technology of ceftezole sodium and ceftezole, which is applied in the field of preparation of antibacterial compounds, can solve problems such as environmental pollution and processing difficulties, and achieve the effects of improving product purity, reducing pollution, and facilitating product turbidity

Active Publication Date: 2014-04-16
哈药集团股份有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] However, the methods in the prior art use more toxic organic solvents and reagents, which are difficult to handle and cause some pollution to the environment. In addition, in order to obtain a high-purity product and a high-yield route to eliminate pollution simultaneously, it is necessary Using suitable solvents and reagents in the synthesis process, the present invention has found a synthetic method through screening, which solves the above-mentioned problems

Method used

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  • Method for preparing ceftezole sodium compound
  • Method for preparing ceftezole sodium compound

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Embodiment 1

[0033] Step 1. Ceftezole three-position intermediate TZT (II) is synthesized

[0034] Add 480g of dimethyl carbonate and 500g of boron trifluoride dimethyl carbonate complex to the reaction kettle, add 80g of demethiadiazole and 170g of 7-ACA under stirring conditions, and react at 40°C±5°C for 60 minutes, measure 7-ACA residual was less than 1.0%. Add 1000ml of water into the condensate, stir for 60 minutes, add Na 2 CO 3 The solution was filtered to pH = 3.5, filtered, washed and dried to obtain II with a purity greater than 98.9% and a yield of 106%.

[0035] Step 2. acid anhydride preparation (I)

[0036] Add 500ml of dichloromethane to the reaction kettle, add 78.5g of tetrazoleacetic acid, cool to -10°C with liquid nitrogen, add 120ml of triethylamine dropwise within 10 minutes under stirring, and stir until the tetrazoleacetic acid is completely dissolved. Cool down to -35±5°C, add 5.4ml of pyridine and 71.5ml of pivaloyl chloride, react at -20±2°C for 50 minutes, t...

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Abstract

The invention relates to a method for preparing an antibacterial compound, in particular to a method for preparing a ceftezole sodium compound. The method comprises the following steps of: 1, synthesizing TZT II, and reacting 2-mercapto-1,3,4 thiadiazole and 7-aminocephalosporanic acid (ACA) to obtain TZT, wherein dimethyl carbonate is used as a reaction solvent; a boron trifluoride-dimethyl carbonate complex is used as a catalyst; after reaction, the agent used by adjusting pH of reaction liquid is sodium carbonate; the weight ratio of boron trifluoride to 7-ACA is 0.7 to 1.3; and 2, synthesizing anhydride I, namely reacting 1H-tetrazole-1-acetic acid and pivaloyl chloride to obtain anhydride; 3, synthesizing ceftezole III, namely reacting TZT II and anhydride I to obtain ceftezole; and 4, synthesizing ceftezole sodium IV, namely reacting ceftezole and sodium salt to obtain ceftezole sodium IV, wherein salt is sodium hydroxide.

Description

Technical field: [0001] The invention relates to a preparation method of an antibacterial compound, in particular to a method for preparing ceftezole sodium compound. Background technique: [0002] Ceftezole, its chemical name is: (6R,7R)-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-8-oxo-7-[2-( 1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2carboxylic acid. It is a semi-synthetic cephalosporin derivative, and its mechanism of action is to exert antibacterial activity by inhibiting the synthesis of bacterial cell walls. [0003] Ceftezole sodium has antibacterial activity against the following bacteria: [0004] 1. Aerobic Gram-positive bacteria: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. [0005] 2. Aerobic Gram-negative bacteria: Escherichia coli, Klebsiella pneumoniae, and Proteus. There are many preparation methods about ceftezole, such as Chinese patent: [0006] Preparation method of ceftezole sodium, application number: 20...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36A61P31/04
Inventor 王喜军王彪王威杨新春翁艳军
Owner 哈药集团股份有限公司
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