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Cephalosporin compound and preparation method thereof

A technology for compounds and cephalosporins, applied in the field of cephalosporins and their preparation, can solve problems such as restricting the development of antibiotics

Inactive Publication Date: 2013-11-20
SICHUAN INDAL INST OF ANTIBIOTICS CHINA NAT PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the frequent occurrence of antibiotic resistance has affected the use of some major classes of antibiotics, thus directly restricting the development of the antibiotic market, so it is necessary to study new cephalosporins

Method used

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  • Cephalosporin compound and preparation method thereof
  • Cephalosporin compound and preparation method thereof
  • Cephalosporin compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of product 7α-ethoxy-7β-(2-thienylacetamido)-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephalosporanic acid

[0034]

[0035] Step (1): 0.25 g of benzhydryl 7α-ethoxy-7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephem-4-carboxylate Dissolve in 10ml of ethyl acetate, cool down to -5°C, add 0.20g of DMAP (N,N-lutidine), dropwise add 5ml of dichloromethane containing 0.20g of thiopheneacetyl chloride, and monitor the reaction by TLC (benzene: petroleum ether=1:2). After about 6 hours of reaction, wash with water, and then wash the organic layer with 10% sodium bisulfate solution, then wash with water, and spin dry the organic layer.

[0036] Step (2): 7α-ethoxy-7β-(2-thienylacetamido)-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephalosporanic acid

[0037] Step (3): Dissolve the product from the previous step with 20ml of dichloromethane, add 0.2ml of anisole, cool down to -5°C, flow HCl gas, and monitor the reaction by TLC (benzene:petroleum e...

Embodiment 2

[0038] Example 2: Product 7α-ethoxy-7β-[[4-(1-amino-3-hydroxyl-1,3-dioxopropane-2-yl subunit)-1,3-dithioheterocycle Synthesis of butane-2-formyl]amino]-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephalosporanic acid

[0039]

[0040] Step (1): 0.25 g of benzhydryl 7α-ethoxy-7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephem-4-carboxylate Dissolve in 10ml of dichloromethane, cool down to -5°C, add 0.20g of N,N-xylaniline, dropwise add 5ml of dichloromethane containing 0.20g of bromoacetyl bromide, and monitor the reaction by TLC (benzene:petroleum ether=1 :2). After about 2 hours of reaction, wash with water, and then wash the organic layer with 10% sodium bisulfate solution, then wash with water, and spin dry the organic layer.

[0041] Step (2): Dissolve the product from the previous step with 20ml of dichloromethane, add 0.2ml of anisole, cool down to -5°C, add 0.35ml of trifluoroacetic acid dropwise, and monitor the reaction by TLC (benzene:petroleum ether=1:2) , ...

Embodiment 3

[0043] Example 3: 7α-ethoxy-7β-[(S)-2-[(2-amino-2-carboxyethyl)thio]acetamido]-3-[(1-methyl-1H-tetrazole -5-base) thiomethyl] cephalosporanic acid synthesis,

[0044]

[0045] Step (1): Dissolve 0.25 g of benzhydryl 7α-ethoxy-7βamino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]cephem-4-carboxylate In 10ml of dichloromethane, lower the temperature to -5°C, add 0.20g of N,N-xylidine, dropwise add 5ml of dichloromethane containing 0.20g of bromoacetyl bromide, and monitor the reaction by TLC (benzene:petroleum ether=1: 2). After about 2 hours of reaction, wash with water, and then wash the organic layer with 10% sodium bisulfate solution, then wash with water, and spin dry the organic layer.

[0046] Step (2): Dissolve the product from the previous step with 20ml of dichloromethane, add 0.2ml of anisole, cool down to -5°C, add 0.35ml of trifluoroacetic acid dropwise, and monitor the reaction by TLC (benzene:petroleum ether=1:2) , After about 3 hours of reaction, spin dry direc...

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Abstract

The invention relates to a cephalosporin compound and a preparation method thereof. Methoxyl cephalosporin is a cephalosporin derivative where alpha-methoxyl is introduced to position 7. As the methoxyl has the steric hindrance effect to prevent enzyme molecules from approaching beta-lactam ring, so that the stability of the medicine to beta-lactamase is increased, and the activity to anaerobion is improved. In recent years, antibiotic resistive phenomena often occur to affect use of some antibiotics in main categories, so that development of the antibiotic market is directly restricted. Therefore, research of novel cephalosporin compounds is necessary. The cephalosporin compound has the structural formula (I). The invention further relates to the preparation method of the cephalosporin compound and a preparation method of intermediates in the preparation process. The invention provides the cephalosporin compound and the preparation method thereof as well as a novel cephalosporin compound and the preparation method thereof. The cephalosporin compound can be used as an ideal substitutive pharmaceutical compound for conventional antibiotics and antibiotics with microbial resistance.

Description

technical field [0001] The invention relates to a cephalosporin compound and a preparation method thereof. Background technique [0002] β-lactam antibiotics are a class of drugs with the most varieties, the most widely used in clinical practice, outstanding curative effect and good safety, mainly including penicillins and cephalosporins antibiotics, and are an important area of ​​concern for clinicians and the development of new antibiotic drugs. Metoxycephalosporin is a cephalosporin derivative that introduces α-methoxy at the 7-position. Due to the steric hindrance of the methoxy group, it prevents the enzyme molecule from approaching the β-lactam ring, increasing the stability of the drug against β-lactamase , and improve the activity of anaerobic bacteria. In recent years, the frequent occurrence of antibiotic resistance has affected the use of some major classes of antibiotics, thus directly restricting the development of the antibiotic market, so it is necessary to s...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04
CPCY02P20/55
Inventor 曹胜华李少华唐克慧叶家林陈林赵俊杜伟宏
Owner SICHUAN INDAL INST OF ANTIBIOTICS CHINA NAT PHARMA GROUP CORP
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