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Method for synthesizing cefalotin sodium drug intermediate 7-(2-thiophene acetamino) cefoperazone sodium

A technology of thiophene acetamido and cefalotin sodium, which is applied in the direction of organic chemistry, can solve the problems of aggravating nephrotoxicity, achieve the effects of reducing reaction temperature and reaction time, reducing intermediate links, and improving reaction yield

Inactive Publication Date: 2017-02-22
厦门莱恩斯特信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Cefalotin sodium has a wide antibacterial spectrum and strong activity against Gram-positive bacteria. It is suitable for respiratory tract infections, soft tissue infections, urinary Road infection, sepsis, etc. In severe cases, it can be combined with aminoglycoside antibiotics, but it should be vigilant that it may aggravate nephrotoxicity

Method used

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  • Method for synthesizing cefalotin sodium drug intermediate 7-(2-thiophene acetamino) cefoperazone sodium

Examples

Experimental program
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Effect test

example 1

[0011] Add 7-aminocephalosporin acid 0.04mol, sodium sulfite 0.12mol in reaction vessel, be dissolved in 600ml mass fraction and be the mixed solution of 40% sodium bromide solution and 500ml mass fraction be 90% methylamine solution, reduce solution temperature to 5 ℃, dropwise add a solution of 0.06mol of 2-thiophene acetylethanol dissolved in 200ml of methylamine, the dropping time is controlled at 60min, after the addition, keep the reaction for 3h, distill under reduced pressure at 1.5kPa to remove methylamine, add a mass fraction of 60% nitric acid Add 120ml of oxalic acid solution to make the pH of the solution at 3, separate the organic layer, extract the water layer with nitromethane, combine the nitromethane layer, add 200ml of water, add sodium carbonate solution to keep the pH of the solution at 6-6.5, divide The aqueous layer was concentrated under reduced pressure at 1.8 kPa until the solution was completely evaporated to dryness, added methylamine to dissolve the...

example 2

[0013] Add 7-aminocephalosporin acid 0.04mol in reaction vessel, sodium sulfite 0.121mol, be dissolved in 600ml mass fraction and be the mixed solution of 45% sodium bromide solution and 500ml mass fraction be 92% methylamine solution, reduce solution temperature to 7 ℃, dropwise add a solution of 0.061mol of 2-thiophene acetylethanol dissolved in 200ml of methylamine, the dropping time is controlled at 80min, after the addition is completed, keep the reaction for 3.2h, 1.55kPa vacuum distillation, remove methylamine, add a mass fraction of 63% Nitromethane 120ml, add oxalic acid solution, make the solution pH at 4, separate the organic layer, extract the water layer with nitromethane, combine the nitromethane layer, add water 200ml, add sodium carbonate solution to keep the solution pH at 6-6.5, Separate the water layer, concentrate under reduced pressure at 1.85kPa until the solution is completely evaporated to dryness, add methylamine to dissolve the solid, filter, and dry u...

example 3

[0015] Add 7-aminocephalosporin acid 0.04mol in reaction vessel, sodium sulfite 0.123mol, be dissolved in 600ml mass fraction and be the mixed solution of 50% sodium bromide solution and 500ml mass fraction be 95% methylamine solution, reduce solution temperature to 9 ℃, dropwise add a solution of 0.062mol of 2-thiophene acetylethanol dissolved in 200ml of methylamine, the dropping time is controlled at 90min, after the addition is complete, keep the reaction for 3.5h, distill under reduced pressure at 1.6kPa, remove methylamine, and add a mass fraction of 65% Nitromethane 120ml, add oxalic acid solution, make the solution pH at 4, separate the organic layer, extract the water layer with nitromethane, combine the nitromethane layer, add water 200ml, add sodium carbonate solution to keep the solution pH at 6-6.5, Separate the water layer, concentrate under reduced pressure at 1.9 kPa until the solution is completely evaporated to dryness, add methylamine to dissolve the solid, f...

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Abstract

The invention discloses a method for synthesizing a cefalotin sodium drug intermediate 7-(2-thiophene acetamino) cefoperazone sodium. The method comprises the following steps: (i) adding 0.04mol of 7-amino cephalosporin acid and 0.12-0.123mol of sodium sulfite into a reaction reactor, dissolving in a mixed solution of 600ml of a sodium bromide solution and 500ml of a methylamine solution, reducing the temperature of the solution to be 5-9 DEG C, dropwise adding 0.06-0.062mol of 2-thiophene acetyl ethyl alcohol, dissolving into 200ml of a methylamine solution within 60-90 minutes, keeping the reaction for 3-3.5 hours after addition, performing reduced pressure distillation to remove methylamine, adding 120ml of nitromethane, adding an oxalic acid solution, adjusting the pH value of the solution to be 3-4, separating an organic layer, extracting a water layer with nitromethane, combining nitromethane layers, adding 200ml of water, adding a sodium carbonate solution to keep the pH value to be 6-6.5, separating a water layer, performing vacuum concentration till the solution is completely dried, adding methylamine to dissolve the solid, filtering, and performing reduced pressure drying, thereby obtaining white 7-(2-thiophene acetamino) cefoperazone sodium.

Description

technical field [0001] The invention relates to a method for synthesizing 7-(2-thiopheneacetylamino) cephalosporin sodium, a drug intermediate of cefalotin sodium. Background technique [0002] Cefalotin sodium has a wide antibacterial spectrum and strong activity against Gram-positive bacteria. It is suitable for respiratory tract infections, soft tissue infections, urinary Road infection, sepsis, etc., in severe cases, it can be combined with aminoglycoside antibiotics, but it should be vigilant that it may aggravate nephrotoxicity. This product should not be used in patients with bacterial meningitis. By inhibiting the synthesis of cell walls, the contents of the cells are expanded to rupture and dissolve, thereby achieving the bactericidal effect. 7-(2-thiophene acetylamino) cephalosporin sodium is used as a pharmaceutical intermediate of cefalotin sodium, and the advantages and disadvantages of its synthesis method are of great economic significance for improving the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/06C07D501/34
CPCC07D501/06C07D501/34
Inventor 储冬红
Owner 厦门莱恩斯特信息科技有限公司