Synthesis method of cefminox sodium

A cefminox sodium and synthetic method technology, applied in the field of drug synthesis, can solve problems such as corrosive reactors, unfavorable industrial production, environmental pollution, etc., and achieve the goals of avoiding acid waste liquid, increasing yield, improving yield and purity Effect

Active Publication Date: 2018-10-09
GUANGDONG LIGUO PHARMACY
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0007] In the current prior art, 7β-bromoacetamido-7α-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercaptomethyl]-3-cephem-4-carboxylic acid Hydrolysis of diphenylmethyl ester to 7β-bromoacetamido-7α-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercaptomethyl]-3-cephem-4-carboxy A large amount of inorganic or organic acids are used for acid, which is easy to pollute the environment, and is easy to corrode the reactor, which is not conducive to industrial production. The method of introducing D-cysteine ​​on the 7β-acylamino group is used for condensation reaction in aqueous solution, which is easy to produce Side reactions, affecting product yield and purity

Method used

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  • Synthesis method of cefminox sodium

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Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1 A kind of solid preparation method of phosphoric acid loaded activated carbon

[0033] S1: the aqueous solution of sodium hydroxide of 0.1mol / L and the aqueous solution of hydrochloric acid of 0.1mol / L are successively processed to activated carbon, remove the soluble acid-base impurity of activated carbon surface load, obtain the activated carbon after treatment;

[0034] S2: soak the treated activated carbon in 25% sulfuric acid aqueous solution for 3 hours, filter, and vacuum dry to obtain activated activated carbon;

[0035] S3: Mix the activated carbon with 20% phosphoric acid aqueous solution, react at 40°C for 2 hours, cool to room temperature, impregnate at room temperature for 24 hours, filter, and dry to obtain the phosphoric acid-loaded activated carbon catalyst.

[0036] The mass ratio of activated carbon to 20% phosphoric acid aqueous solution in step S3 is 1:3.5.

Embodiment 2

[0037] Embodiment 2 A kind of preparation method of phosphoric acid loaded activated carbon

[0038] S1: the aqueous solution of sodium hydroxide of 0.1mol / L and the aqueous solution of hydrochloric acid of 0.1mol / L are successively processed to activated carbon, remove the soluble acid-base impurity of activated carbon surface load, obtain the activated carbon after treatment;

[0039] S2: soak the treated activated carbon in 25% sulfuric acid aqueous solution for 3 hours, filter, and vacuum dry to obtain activated activated carbon;

[0040] S3: Mix the activated carbon with 20% phosphoric acid aqueous solution, react at 60° C. for 2 hours, cool to room temperature, impregnate at room temperature for 24 hours, filter, and dry to obtain the phosphoric acid-loaded activated carbon catalyst.

[0041] The mass ratio of activated carbon to 20% phosphoric acid aqueous solution in step S3 is 1:4.

Embodiment 3

[0042] Embodiment 3 A kind of preparation method of phosphoric acid loaded activated carbon

[0043] S1: the aqueous solution of sodium hydroxide of 0.1mol / L and the aqueous solution of hydrochloric acid of 0.1mol / L are successively processed to activated carbon, remove the soluble acid-base impurity of activated carbon surface load, obtain the activated carbon after treatment;

[0044] S2: soak the treated activated carbon in 25% sulfuric acid aqueous solution for 3 hours, filter, and vacuum dry to obtain activated activated carbon;

[0045] S3: Mix the activated carbon with 20% phosphoric acid aqueous solution, react at 50°C for 2 hours, cool to room temperature, impregnate at room temperature for 24 hours, filter, and dry to obtain the phosphoric acid-loaded activated carbon catalyst.

[0046] The mass ratio of activated carbon to 20% phosphoric acid aqueous solution in the step S3 is 1:3.8.

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Abstract

The invention aims at providing a synthesis method of cefminox sodium. The synthesis method specifically comprises the following steps: firstly, mixing 7beta-amino-7alpha-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercapto methyl]-3-cephem-4-methyl diphenyl carboxylate and dichloromethane (7-MAC), and bromoacetamide bromine under a certain condition to obtain 7beta-bromoacetyl amino-7alpha-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercapto methyl]-3-cephem-4-methyl diphenyl carboxylate; then removing a carboxylic acid protection group to obtain 7beta-bromoacetyl amino-7alpha-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercapto methyl]-3-cephem-4-carboxylic acid; then enabling the 7beta-bromoacetyl amino-7alpha-methoxy-3-[(1-methyl-1H-5-tetrazolyl)-mercapto methyl]-3-cephem-4-carboxylic acid to react withD-cysteine hydrochloride to obtain the cefminox sodium. According to the synthesis method provided by the invention, the product yield and purity of the synthesized cefminox sodium are high; phosphoric acid loaded activated carbon is used as a solid catalyst and is easy to separate from a reaction system, and the formation of acid waste liquid is avoided.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing cephalosporin compounds, more specifically to a method for synthesizing cefminox sodium. Background technique [0002] Cephalosporin antibiotics are an important antibacterial drug, which can destroy the cell wall of bacteria and kill bacteria during the breeding period, and it also has the advantages of broad antibacterial spectrum, strong antibacterial effect, resistance to penicillinase, and less allergic reactions than penicillins. So far, there are more than 70 varieties of cephalosporin antibiotics in the world, which have been widely used clinically. Since the middle of the last century, the research on cephalosporin antibiotics has been a hot spot in the research and development of antibiotic drugs, and it has gone through four generations since its creation. From the first generation of cephalexin and cefadroxil to the new generation of cefotaxime...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/57C07D501/04
CPCC07D501/04C07D501/57
Inventor 许伟龙王雄强曾建江王宝
Owner GUANGDONG LIGUO PHARMACY
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