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

A technology of cefoxidone sodium and fooxidone sodium powder, which is applied in the directions of pharmaceutical formulations, antibacterial drugs, powder delivery, etc., can solve the problems of unsuitability for industrialized large-scale production, low cefoxidone yield, shortened synthesis route, etc. problem, to achieve the effect of easy control, simplified purification process and short synthesis route

Active Publication Date: 2009-11-25
SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK 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,

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), and add dichloromethane / DMF= 1 / 1 (v / v) solution 200ml, cool down to 0°C in an ice bath, add 17.6g (0.0793mol) of 3,5-dichloropyridoneacetic acid, and add 3,5-dichloropyridoneacetic acid per minute After adding 1 / 20 of the total amount, 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 from diethyl ether, refrigerated for crystallization for more than 8 hours, filtered, and vacuum-dried at 50°C to obtain 33.1 g of intermediate I, with a yield of 94.5%. The infrared characteristic absorption peak that obtains 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), and add dichloromethane solution 200ml, cool down to -5°C in an ice bath, add 19.6g (0.0882mol) of 3,5-dichloropyridoneacetic acid, and add 1 / 10 of the total amount of 3,5-dichloropyridoneacetic acid per minute. , and stirred at 25°C for 0.5 hours. After filtration, the filtrate was evaporated to dryness under reduced pressure at 50°C, recrystallized from diethyl ether, refrigerated for crystallization for more than 8 hours, filtered, and vacuum-dried at 50°C to obtain 33.7g of intermediate I, with a yield of 96.4%. The infrared characteristic absorption peak that obtains 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, and 15.2g (0.0735mol) of dicyclohexylcarbodiimide (DCC), Add 200ml of dichloromethane / DMF=1 / 1 (v / v) solution, cool down to 0°C in an ice bath, add 24.47g (0.11mol) of 3,5-dichloropyridoneacetic acid, and add 3 , 1 / 15 of the total amount of 5-dichloropyridoneacetic acid was added, and 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, recrystallized from diethyl ether, refrigerated for crystallization for more than 8 hours, filtered, and vacuum-dried at 50°C to obtain 31.7g of intermediate I, with a yield of 90.6%. The infrared characteristic absorption peak that obtains 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 product I 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 the bulk drug thereof, in particular to a cefazedone sodium powder injection and a method for synthesizing the cefazedone sodium. Background technique [0002] Cefazedone sodium (cefazedone sodium) was developed by E Merck, Darmstadt laboratory in the late 1970s and is the first generation of cephalosporin antibiotics. In 1979, Merck was the first to go public in Germany, and then it was listed in neighboring countries, South Korea, Romania, Taiwan and other countries and regions. Cefozione sodium is a semi-synthetic cephalosporin antibiotic, which mainly inhibits and kills bacteria by interfering with and preventing the synthesis of bacterial cell walls. It has good antibacterial activity against common clinical Gram-positive and some Gram-negative bacteria, and some anaerobic bacteria, and can be used for respiratory system, urinary system, gastrointes...

Claims

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Application Information

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IPC IPC(8): A61K9/19A61K31/546A61P31/04C07D501/36C07D501/06
Inventor 李明华张世伟范丽
Owner SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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