Cefazedone sodium medicament powder injection and method for synthesizing raw medicine of Cefazedone sodium

A technology of cefoxidone sodium and cefoxidone is applied in directions such as pharmaceutical formulations, antibacterial drugs, powder delivery, etc., and can solve problems such as being unsuitable for industrialized large-scale production, low yield of cefoxidone, and increased synthesis cost, and achieves the The effect of easy control, simplified purification process and short synthesis route

Active Publication Date: 2011-03-16
SHANDONG LUOXIN PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] This synthetic route is shortened relatively, but the productive rate of final cefoxizone is on the low side, and its synthetic cost will increase accordingly, is not suitable for industrialized large-scale production
[0012] In view of defects such as long synthetic routes for synthesizing cefazedone in the prior art, relatively expensive raw materials or low yields, the present invention provides a method for synthesizing cefazedone with short synthetic route, easy reaction control and high product yield and purity. Method, and the obtained cefzidone sodium obtained a kind of cefzidone sodium powder injection through aseptic treatment

Method used

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  • Cefazedone sodium medicament powder injection and method for synthesizing raw medicine of Cefazedone sodium
  • Cefazedone sodium medicament powder injection and method for synthesizing raw medicine of Cefazedone sodium
  • Cefazedone sodium medicament powder injection and method for synthesizing raw medicine of Cefazedone sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of Intermediate I:

[0055] Put 20g (0.0735mol) of 7-ACA into the flask, add 200ml of tetrahydrofuran, 7.5g of triethylamine, add 17.2g (0.085mol) of dicyclohexylcarbodiimide (DCC), add dichloromethane / DMF= 1 / 1(v / v) solution 200ml, cooling to 0℃ in an ice bath, adding 17.6g (0.0793mol) of 3,5-dichloropyridone acetic acid, adding 3,5-dichloropyridone acetic acid every minute After 1 / 20 of the total amount was added, the reaction was stirred at 20°C for 0.5 hour. After filtration, the filtrate was evaporated to dryness under reduced pressure at 50°C, recrystallized with ether, crystallized under refrigeration for more than 8 hours, filtered, and dried under vacuum at 50°C to obtain 33.1g of intermediate I with a yield of 94.5%. The infrared characteristic absorption peak of Intermediate I is: 3400cm -1 , 1654.48cm -1 , 1600cm -1 , 1400cm -1 .

Embodiment 2

[0057] Synthesis of Intermediate I:

[0058] Put 20g (0.0735mol) of 7-ACA into the flask, add 200ml of dichloromethane, 7.5g of triethylamine, add 19.68g (0.0955mol) of dicyclohexylcarbodiimide (DCC), add dichloromethane solution 200ml, cooled to -5°C in an ice bath, add 19.6g (0.0882mol) of 3,5-dichloropyridone acetic acid at a rate of 1 / 10 of the total amount of 3,5-dichloropyridone acetic acid added per minute. , The reaction was stirred at 25°C for 0.5 hour. After filtration, the filtrate was evaporated to dryness under reduced pressure at 50°C, recrystallized with ether, crystallized under refrigeration for more than 8 hours, filtered, and dried under vacuum at 50°C to obtain 33.7g of intermediate I, with a yield of 96.4%. The infrared characteristic absorption peak of Intermediate I is: 3400cm -1 , 1654.48cm -1 , 1600cm -1 , 1400cm -1 .

Embodiment 3

[0060] Synthesis of Intermediate I:

[0061] Put 20g (0.0735mol) of 7-ACA into the flask, add 200ml of N,N-dimethylformamide, 7.5g of triethylamine, add 15.2g (0.0735mol) of dicyclohexylcarbodiimide (DCC), Add 200ml of dichloromethane / DMF=1 / 1(v / v) solution, cool to 0℃ in an ice bath, add 24.47g (0.11mol) of 3,5-dichloropyridone acetic acid, add 3 per minute After adding 1 / 15 of the total amount of 5-dichloropyridone acetic acid, the reaction was stirred at 35°C for 0.5 hours. After filtration, the filtrate was evaporated to dryness under reduced pressure at 50°C, ether was recrystallized, crystallized under refrigeration for more than 8 hours, filtered, and dried under vacuum at 50°C to obtain 31.7g of intermediate I with a yield of 90.6%. The infrared characteristic absorption peak of Intermediate I is: 3400cm -1 , 1654.48cm -1 , 1600cm -1 , 1400cm -1 .

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Abstract

The present invention provides a cefazedone sodium medicament powder injection composed of 100% of cefazedone sodium. The cefazedone sodium is prepared by a method as follows: (1) 7-ACA and 3, 5-dichloro pyridine acetic acid react with each other with the action of an anhydrating agent, a mixture after the reaction is post-processed to obtain an intermediate product I; (2) the intermediate productI and 2-mercapto-5-methyl-1, 3, 4-thiadiazoles react with each other with the protection of nitrogen at a temperature of 50 to 90 DEG C, a mixture after the reaction is purified to obtain a water solution which is added with an inorganic acid to regulate pH value to be equal to 1 to 3, a precipitation is extracted from the water solution and is post-processed to obtain cefazedone; (3) the cefazedone and sodium hydrogen carbonate react with each other in water to obtain a cefazedone sodium solid body after an aftertreatment. The powder injection has single component and perfect dissolution performance, the raw medicine has a short synthetic route, the aftertreatment of the intermediate product or final product are all simple, and the yield and purity of the whole reaction process are all high.

Description

Technical field [0001] The invention relates to a cephalosporin antibiotic powder injection and a method for synthesizing its raw material medicine, in particular to a powder injection of cephalosporin sodium and a method for synthesizing cephalosporin sodium. Background technique [0002] Cefazedone sodium was developed by E Merck, Darmstadt laboratory in the late 1970s, and is the first-generation cephalosporin antibiotic. In 1979, Merck & Co. took the lead in listing in Germany, and then listed in neighboring countries, South Korea, Romania, Taiwan and other countries and regions. Cefazidone sodium is a semi-synthetic cephalosporin antibiotic, which achieves the purpose of inhibition and sterilization by interfering with and preventing the synthesis of bacterial cell walls. It has good antibacterial activity against clinically common Gram-positive and some Gram-negative bacteria and some anaerobic bacteria. It can be used for respiratory system, urinary system, gastrointestin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K9/19A61K31/546A61P31/04C07D501/36C07D501/06
Inventor 李明华张世伟范丽
Owner SHANDONG LUOXIN PHARMA GRP CO LTD
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