Cefazolin sodium pentahydrate compound of new route

A technology of cefazolin sodium and compound, applied in the field of pharmaceutical synthesis, can solve the problems of low product purity, low yield and high cost, and achieve the effects of simplifying operation steps, reducing cost, and improving yield and purity

Inactive Publication Date: 2010-04-21
HAINAN MEIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are two ways for the 3-position substitution reaction, but both produce a large number of by-products, which affect the purity of the product
This method

Method used

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  • Cefazolin sodium pentahydrate compound of new route
  • Cefazolin sodium pentahydrate compound of new route
  • Cefazolin sodium pentahydrate compound of new route

Examples

Experimental program
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Effect test

Embodiment 1 4

[0034] The synthesis of embodiment 1 tetrazoleacetic acid 2-mercapto-5-methyl-1,3,4-thiadiazole

[0035] 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 264 grams of 2-mercapto-1,3,4-thiadiazole in 800ml 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 464 g of a yellow solid product, with a yield of 96%.

Embodiment 2 5

[0036] The synthesis of embodiment 2 cefazolin sodium pentahydrate

[0037] Under the protection of nitrogen, 272 grams of 7-ACA and sodium bicarbonate are added to water to form a clear solution, then add 242 grams of the product obtained in Example 1 (tetrazolium acetic acid 2-mercapto-5-methyl-1 , 3,4-thiadiazole) and 2 liters of acetone, then the mixed solution was reacted at 60°C for 4 hours, and the pH was adjusted to 7.5 with 3% aqueous sodium bicarbonate solution. After the reaction, 4L of ethanol was added to control the reaction The temperature was 15° C., stirred for 2 hours, crystals were precipitated, filtered, the filter cake was washed with ethanol, and dried at 40° C. for 3 hours to obtain 515 grams of cefazolin sodium pentahydrate, with a yield of 91%.

[0038] Elemental Analysis C 14 h 13 N 8 NaO 4 S 3 ·5H 2 o

[0039] Theoretical value C: 29.67%, H: 4.09%, N: 19.77%, O: 25.41%, S: 16.97%,

[0040] Experimental values ​​C: 29.72%, H: 4.05%, N: 19.80%, O...

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Abstract

The invention relates to a cefazolin sodium pentahydrate compound of a new route, and particularly provides a method for synthesizing the cefazolin sodium pentahydrate compound. The method comprises the following steps: synthesizing tetrazolyl acetic acid 2-mercapto-5-methyl-1,3,4-thiadiazole ester by using tetrazolyl acetic acid and 2-mercapto-5-methyl-1,3,4-thiadiazole as raw materials; and generating cefazolin sodium through the reaction between the tetrazolyl acetic acid 2-mercapto-5-methyl-1,3,4-thiadiazole ester and 7-aminocephalosporanic acid. Compared with that the method for synthesizing tetrazole acetic acid 2-mercapto-1,3,4-thiadiazole ester in the prior art uses expensive reagents such as trifluoroacetic anhydride, aluminium trimethide or DCC and the like as a condensation agent, the method improves the synthesis method, not only simplifies the operation steps, but also, surprisingly, greatly improves the product yield and the purity, reduces the cost, and lays a foundation for industrialization.

Description

technical field [0001] The invention relates to a new route of cephalosporin compounds, in particular to a method for synthesizing a new route of cefazolin sodium pentahydrate compound, which belongs to the field of drug synthesis. Background technique [0002] Cefazolin sodium pentahydrate, its chemical name is: (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfur]methyl]-7- [(1H-tetrazol-1-yl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt pentahydrate, molecular formula For: C 14 h 13 N 8 NaO 4 S 3 ·5H 2 O, molecular weight: 566.57, structural formula: [0003] [0004] Cefazolin sodium pentahydrate is the first-generation cephalosporin with a broad antibacterial spectrum. Its antibacterial mechanism is to bind to the target protein on the inner membrane of the bacterial cell membrane, that is, penicillin-binding proteins (PBPs) (mainly acting on PBP1 and PBP3). Inhibits bacterial cell wall biosynthesis, thereby acting as an ant...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04
Inventor 邱民
Owner HAINAN MEIDA PHARMA
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