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Ceftezole sodium compound with novel route

A technology of ceftezole sodium and compounds, applied in the direction of organic chemistry, etc., can solve the problems of low overall yield, unfavorable industrial production, lengthy synthesis steps, etc., and achieve the effects of improving yield and purity, simplifying operation steps, and reducing costs

Inactive Publication Date: 2010-06-16
HAINAN LINGKANG PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0008] The preparation method of above-mentioned ceftezole sodium all takes 7-aminocephalosporanic acid (7-ACA) as raw material, synthesizes by a series of reactions, but all there are some defects, as reported in the literature in the synthetic tetrazoleacetic acid 2-mercapto- In the method of 1,3,4-thiadiazole ester, expensive reagents such as trifluoroacetic anhydride, trimethylaluminum or DCC are used as condensation agents, the synthesis steps are tedious, and the total yield is low, which is not conducive to industrial production

Method used

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  • Ceftezole sodium compound with novel route
  • Ceftezole sodium compound with novel route
  • Ceftezole sodium compound with novel route

Examples

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Effect test

Embodiment 1

[0025] Embodiment 1: Synthesis of 2-mercapto-1,3,4-thiadiazole ester of tetrazoleacetic acid

[0026] Add 275ml of isopropyl chloroformate to 1 liter of tetrahydrofuran solution containing 256 grams (2mol) of tetrazoleacetic acid, cool to 10°C, add 243ml of N-methylpiperidine, keep the reaction temperature not exceeding 15°C, Stir, add 236 grams of 2-mercapto-1,3,4-thiadiazole in 700ml of tetrahydrofuran solution, react at 15°C for 2 hours, then concentrate the reaction solution to a viscous state, add 2 liters of petroleum ether Vigorously stirred for 2 hours, a solid was formed. After continuing to stir for 2 hours, it was filtered to obtain 433 g of a yellow solid product, with a yield of 95%.

Embodiment 2

[0027] Embodiment 2: the synthesis of ceftezole sodium

[0028] Under the protection of nitrogen, 272 grams of 7-ACA and 84 grams of sodium bicarbonate were added to 1 liter of water to form a clear solution, and then 228 grams of tetrazoleacetic acid 2-mercapto-1,3,4-thiadiazole ester was added and 2 liters of acetone, then the mixture was reacted at 60°C for 4 hours, while adjusting the pH to 7.5 with 3% aqueous sodium bicarbonate solution, after the reaction, add 4L isopropanol, control the reaction temperature to 15°C, and stir After 2 hours, crystals were precipitated, filtered, the filter cake was washed with 500 ml of ethanol, and vacuum-dried at 40° C. to obtain 430 g of ceftezole sodium product, with a yield of 93%.

[0029] Elemental Analysis Molecular Formula: C 13 h 11 N 8 NaO 4 S 3

[0030] Theoretical value C: 33.76%, H: 2.39%, N: 24.23%, O: 13.83%, S: 20.79%,

[0031] Experimental values ​​C: 33.82%, H: 2.42%, N: 24.32%, O: 13.85%, S: 20.87%.

[0032] 1...

Embodiment 3 4

[0033] Synthesis of embodiment 3 tetrazolium acetic acid 2-mercapto-1,3,4-thiadiazole ester

[0034] Add 275ml of isopropyl chloroformate to 1 liter of tetrahydrofuran solution containing 256 grams (2mol) of tetrazoleacetic acid, cool to 15°C, add 245ml of N-methylpiperidine, keep the reaction temperature not exceeding 15°C, Stir, add 236 grams of 2-mercapto-1,3,4-thiadiazole in 700ml of tetrahydrofuran solution, react at 15°C for 2.5 hours, then concentrate the reaction solution to a viscous state, add 2 liters of petroleum ether Vigorously stirred for 2.5 hours, a solid was formed. After continuing to stir for 2 hours, it was filtered to obtain 427.5 g of a yellow solid product, with a yield of 93.8%.

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Abstract

The invention relates to a cephalo class compound, in particular to a Ceftezole sodium compound which belongs to the technical field of medicine. Tetrazolyl acetic acid is adopted to condense with 2-mercapto-1,3,4-thiadiazole to generate tetrazolyl acetic acid 2-mercapto-1,3,4-thiadiazole ester, and the tetrazolyl acetic acid 2-mercapto-1,3,4-thiadiazole ester and 7-aminoce-phalosporanic acid (7-ACA) react to directly obtain a target compound of Ceftezole sodium. The multi-step reaction and the complicated postprocessing of the prior art are avoided, the problems existing in the prior art are solved, the steps are simplified, the cost is lowered, and the yield is enhanced greatly.

Description

technical field [0001] The invention relates to a cephalosporin compound, in particular to a ceftezole sodium compound, and belongs to the technical field of medicine. Background technique [0002] Ceftezole sodium, its chemical name is: (6R,7R)-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-8-oxo-7-[2- (1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2carboxylic acid sodium salt, molecular formula: C 13 h 11 N 8 NaO 4 S 3 , molecular weight: 462.45, structural formula: [0003] [0004] Ceftezole sodium is a semi-synthetic cephalosporin derivative, and its mechanism of action is to exert antibacterial activity by inhibiting the synthesis of bacterial cell walls. The effect of this product on gram-positive bacteria is similar to that of cefazolin, but it has a good effect on gram-negative bacteria, such as Haemophilus, Escherichia coli, Klebsiella, and Proteus mirabilis. Acid bacilli, indole-positive proteus, etc. also have antibacterial effects. Clinically...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/04C07D501/06
Inventor 王明
Owner HAINAN LINGKANG PHARMA CO LTD
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