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Method for synthesizing cefoselis sulfate

A kind of technology of cefotaxime sulfate and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems such as difficulty in purchasing cefa mother nucleus raw material, unfavorable continuity, large-scale industrial production, limited application prospect and the like

Active Publication Date: 2013-04-17
SICHUAN KELUN PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yields of these methods are not high, and the cephalosporin nuclei raw materials are difficult to purchase, and the reaction conditions are harsh, which is not conducive to continuous and large-scale industrial production, so that its application prospects are limited
Although there has been some progress in domestic research on its synthesis technology, the cost is high and the quality is not good

Method used

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  • Method for synthesizing cefoselis sulfate

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Embodiment 1

[0022] The synthetic method of embodiment 1 cefotaxime sulfate of the present invention

[0023]In the 2000ml four-neck flask equipped with stirrer, thermometer, nitrogen conduit and constant pressure dropping funnel, add 80g (0.295mol) 7-aminocephalosporanic acid (7-ACA), 800g dichloromethane, stir and cool to 10 ℃ or so. Add 110g (0.68mol) hexamethyldisilazane amine, 1g iodotrimethylsilane, 1g N,N-dimethylformamide under stirring, then naturally rise to room temperature, and stir and react at room temperature for 5-12 hours; Then the temperature was lowered to about -5°C, and under the protection of nitrogen, 125 g (0.625 mol) of iodotrimethylsilane was added dropwise. After the addition was complete, the reaction temperature was controlled at 0-5°C, and the reaction was stirred for 2 hours. Within this temperature range, 80 g (0.44 mol) of 5-formamidoamino-1-(2-formyloxyethyl)pyrazole was slowly added in portions. The reaction was stirred overnight at 0 °C. The next day,...

Embodiment 2

[0025] The synthetic method of embodiment 2 cefotaxime sulfate of the present invention

[0026] 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolamine methyl]-3-cephem-4-carboxylic acid hydrochloride synthesis: in 2000ml four Add 40g (0.147mol) of 7-aminocephalosporanic acid (7-ACA) and 800g of acetonitrile into the flask, stir and cool to about 10°C. Add 80g (0.5mol) hexamethyldisilazane amine, 1g iodotrimethylsilane, 1g N,N-dimethylformamide under stirring, then naturally rise to room temperature, and stir and react at room temperature for 5-12 hours; Then cool down to about -5°C, under the protection of nitrogen, add 80g (0.4mol) of iodotrimethylsilane dropwise, after the addition is completed, the reaction temperature is controlled at 0~-5°C, and the reaction is stirred for 2h; within this temperature range, Slowly add in batches, 80g (0.437mol) 5-formamidoamino-1-(2-formyloxyethyl)pyrazole; stir and react overnight at 0°C; slowly raise the temperature to 14°C the next da...

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Abstract

The invention discloses a method for synthesizing cefoselis sulfate. The method takes 7-aminocephalosporanic acid (7-ACA) as a raw material to synthesize a key intermediate of 7beta-amido-3-[3-amido-2-(2-ethoxyl)-1-methylpyrazole]-3-cephem-4-carboxylic acid hydrochloride; and the key intermediate and 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetic thiobenzothiazole ester are condensed together to obtain the cefoselis sulfate. The method has the advantages of easily obtained raw materials, simplicity in synthesizing way, convenience in operation, high synthesizing yield, low cost and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of medicine, particularly a kind of synthetic method of cefotaxime sulfate. Background technique [0002] Cefotaxime sulfate (cefoselis, FK-037) is the fourth-generation injection cephalosporin jointly developed by Fujisawa Pharmaceutical Co., Ltd. of Japan and Johnson Company of the United States. It was first listed in Japan in 1998. It has good activity against Gram-positive bacteria and Gram-negative bacteria, especially against methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa, and has strong antibacterial activity against β-lactamase Very stable, clinically against aerobic G+ bacterial isolates, the effect is similar to that of cefopim, but stronger than that of ceftazidime, cefoperazone and ceftizoxime. It is highly effective against methicillin-resistant Staphylococcus aureus, and its effect on methicillin-sensitive Staphylococcus aureus is similar to that of cefe...

Claims

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Application Information

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IPC IPC(8): C07D501/46C07D501/04C07D501/06
Inventor 崔德修李重阳李明研
Owner SICHUAN KELUN PHARMA CO LTD
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