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Method for synthesizing ceftriaxone sodium

A technology of ceftriaxone sodium and a synthesis method, which is applied in the field of synthesis of ceftriaxone sodium, can solve the problems such as the influence of 7-ACT on purity and yield, high toxicity of triethylamine, troublesome operation and the like, and improves yield and quality , the effect of reducing the complexity and speeding up the response speed

Active Publication Date: 2014-11-05
哈药集团股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Chinese patent CN 103539803A uses dimethyl carbonate as a solvent and boron trifluoride dimethyl carbonate as a catalyst to synthesize 7-ACT, but the reaction time is about 50min, which is relatively long, because it reacts at a higher temperature of 30°C to make 7-ACT -The purity and yield of ACT are greatly affected
[0007] Chinese patent CN 100335485C has introduced a kind of method that uses dichloromethane and ethanol as solvent and triethylamine as cosolvent to make 7-ACT react with AE active ester to generate ceftriaxone, but the toxicity of triethylamine used in this method Larger and blanketed with nitrogen makes handling cumbersome and difficult to control

Method used

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  • Method for synthesizing ceftriaxone sodium
  • Method for synthesizing ceftriaxone sodium
  • Method for synthesizing ceftriaxone sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Preparation of 7-ACT

[0037] Add 120g of dimethyl carbonate, 56g of boron trifluoride dimethyl carbonate, and 8g of methanesulfonic acid into the dry four-necked bottle, stir rapidly and cool down to 10°C, add 15g of triazine ring, 25g of 7-ACA, and keep at 10-12°C The reaction was about 23 minutes, and the sample was detected by HPLC (high performance liquid chromatography) to detect that the residual 7-ACA was less than 1%. The reaction was completed. Add 240g of cold water to the four-necked bottle, the solution is clarified, add 0.25g of EDTA-2Na, 1.0g of sodium dithionite to keep the temperature below 13°C, add diluted ammonia water (1:1) dropwise to adjust the pH = 2.3 to 2.6, and a white solid is precipitated. After dripping, grow the crystal at 5-10°C for 1 hour, filter, wash the filter cake twice with 120 g of water, filter, wash the filter cake once with 50 g of ethanol, filter, and vacuum dry at 45°C for 8 hours to obtain 32.5 g of solid, with a mo...

Embodiment 2

[0038] Example 2 Preparation of 7-ACT

[0039] Add 120g of dimethyl carbonate, 56g of boron trifluoride dimethyl carbonate, and 7g of methanesulfonic acid into the dry four-necked bottle, stir quickly and cool down to 10°C, add 15g of triazine ring, 25g of 7-ACA, and keep at 10-12°C The reaction was about 23 minutes, and the sample was detected by HPLC (high performance liquid chromatography) to detect that the residual 7-ACA was less than 1%. The reaction was completed. Add 240g of cold water to the four-necked bottle, the solution is clarified, add 0.25g of EDTA-2Na, 1.0g of sodium dithionite to keep the temperature below 13°C, add diluted ammonia water (1:1) dropwise to adjust the pH = 2.3 to 2.6, and a white solid is precipitated. After dripping, grow the crystal at 5-10°C for 1 hour, filter, wash the filter cake twice with 120 g of water, filter, wash the filter cake once with 50 g of ethanol, filter, and vacuum dry at 45°C for 8 hours to obtain 32.1 g of solid, with a mo...

Embodiment 3

[0040] Example 3 Preparation of 7-ACT

[0041] Add 120g of dimethyl carbonate, 56g of boron trifluoride dimethyl carbonate, and 6g of methanesulfonic acid into the dry four-necked bottle, stir quickly and cool down to 11°C, add 15g of triazine ring, 25g of 7-ACA, and keep at 10-12°C The reaction was about 25 minutes, and the sample was detected by HPLC (high performance liquid chromatography) to detect that the 7-ACA residue was less than 1%. The reaction was completed. Add 240g of cold water to the four-necked bottle, the solution is clarified, add 0.25g of EDTA-2Na, 1.0g of sodium dithionite to keep the temperature below 13°C, add diluted ammonia water (1:1) dropwise to adjust the pH = 2.3 to 2.6, and a white solid is precipitated. After dripping, grow the crystal at 5-10°C for 1 hour, filter, wash the filter cake twice with 120 g of water, filter, wash the filter cake once with 50 g of ethanol, filter, and vacuum dry at 45°C for 8 hours to obtain 32.0 g of solid, with a mol...

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Abstract

The invention discloses a method for synthesizing ceftriaxone sodium. The method comprises the steps of firstly carrying out condensation on 7-ACA and triazine ring by taking dimethyl carbonate and organic acid as a mixed solvent and taking boron trifluoride dimethyl carbonate as a catalyst, so as to produce 7-ACT, then, enabling 7-ACT and AE (Active Ester) to react by taking tetramethyl guanidine as a cosolvent, so as to produce ceftriaxone, and finally, adding sodium acetate, thereby synthesizing the sodium salt. The method has the advantages that the operating method is simple, the conditions are mild, the raw materials are easily available, the pollution is little, the cost is very low, the purity of the finally obtained ceftriaxone sodium product is over 99.6%, and the molar yield is over 94%.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a synthesis method of ceftriaxone sodium. Background technique [0002] Ceftriaxone sodium, also known as ceftriaxone, is the third-generation cephalosporin antibiotic promoted by Rochen Company in Switzerland in the 1980s. The English name is Ceftriaxone Sodium, and the chemical name is (6R, 7R)-7-[ [(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5 , 6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Disodium salt triple hemihydrate. The chemical structural formula is as follows: [0003] [0004] Ceftriaxone sodium has strong antibacterial activity against Gram-positive bacteria and negative bacteria. Staphylococcus etc. Clinically, it is mainly used for meningitis, pneumonia, skin and soft tissue infection, peritonitis, urinary system infection, gonorrhea, liver and gallbladder infection...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04
CPCC07D501/04C07D501/36
Inventor 王喜军石成
Owner 哈药集团股份有限公司
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