Cefmenoxime compound and synthetic method thereof

A synthetic method, cefmenoxime technology, applied in the field of drug synthesis, can solve problems such as no literature and patent reports

Inactive Publication Date: 2010-12-29
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, domestic manufacturers of cefmenoxime preparations mainly rely on imported raw materials for sub-packaging, but there are no literature or patent reports on the production process of cefmenoxime

Method used

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  • Cefmenoxime compound and synthetic method thereof
  • Cefmenoxime compound and synthetic method thereof
  • Cefmenoxime compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of embodiment 12-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid hydrochloride

[0031] The 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid of 201 grams and the triphenylchloromethane of 280 grams are joined in the DMF of 600ml, reacted at room temperature for 4 hours, then slowly added 1 Liter diisopropyl ether, stirred, precipitated solid, filtered, washed with a small amount of diisopropyl ether, and dried to obtain 460 g of the product, with a yield of 96%.

Embodiment 2

[0032] The synthesis of embodiment 2 cefotaxime hydrochloride

[0033] 326 grams of 2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid hydrochloride and 120 ml of N,N-diisopropylethylamine were added to 500 ml of DMF In, reactant is cooled to 10 ℃, add 130 grams (0.68mol) p-toluenesulfonyl chloride, stir reaction at this temperature for 1 hour, then add 185 grams (0.68mol) 7-ACA and 300ml triethylamine, in 5 Stir vigorously at -10°C for 0.5 hours, then add 500ml of 6mol / L hydrochloric acid, raise the temperature to 45°C, stir for 1.5 hours, cool to room temperature, then add 4 liters of acetone and 300ml of water and stir at room temperature to precipitate a solid, filter, Wash with acetone and dry under vacuum at 40° C. to obtain 314 g of product, yield: 94%.

Embodiment 3

[0034] The synthesis of embodiment 3 cefmenoxime

[0035] Dissolve 200 grams of cefotaxime hydrochloride in a mixed solvent of 5000 ml of distilled water and 2500 ml of acetone, add 47.2 grams of 1-methyl-5-mercapto-1H-tetrazolium, stir and heat up to 55 ° C, and then use 3% carbonic acid Sodium aqueous solution adjusts the pH of the reaction system to 6.5-7, reacts at this temperature for 4 hours, adds activated carbon to decolorize, then cools to room temperature, filters, and the filtrate is adjusted to PH=6 with 2mol / L hydrochloric acid, and 500ml of ethyl acetate The ester was extracted twice, and the water phase was adjusted to PH=2.5 with 2 mol / L hydrochloric acid, the solid was precipitated by stirring, filtered, the filter cake was washed with water, and dried to obtain 202 g of the product, with a yield of 93.7%.

[0036] Product properties: off-white crystalline powder.

[0037] Purity: 99.4%.

[0038] Elemental Analysis C 16 h 17 N 9 o 5 S 3 , molecular weig...

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Abstract

The invention relates to a cefmenoxime compound and a synthetic method thereof, in particular to a synthetic method of a cefmenoxime compound, pertaining to the field of drug synthesis technology. Themethod comprises the following steps: (1) aminothiazoly loximate and triphenylchloromethane react in DMF to obtain 2-(2-triphenylmethylaminothiazol-4-yl)-2-methoxy imido acetic acid hydrochloride; (2) the 2-(2- triphenylmethylaminothiazol-4-yl)-2-methoxy imido acetic acid hydrochloride and N, N-diisopropylethylamine are added into the DMF and then paratoluensulfonyl chloride is added and the mixture is stirred for reaction, and then 7-ACA and triethylamine are added for reaction. The pH value is adjusted with hydrochloric acid to obtain hydrochloric cefotaxime acid; and (3) the hydrochloric cefotaxime acid and 1-methyl-5- hydrosulphonyl-1H-tetrazolium react in a mixed solvent and the pH value is adjusted respectively with sodium carbonate and hydrochloric acid to obtain cefmenoxime.

Description

technical field [0001] The invention relates to a method for synthesizing cephalosporin compounds, in particular to a method for synthesizing cefmenoxime compounds, and belongs to the technical field of drug synthesis. Background technique [0002] Cefmenoxime, its chemical name is: (6R,7R)-7-[2-(2-amino-4-thiazolyl)(methoxyimino)acetamido]-3-[[(1-methyl- 1H-tetrazol-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, molecular formula: C 16 h 17 N 9 o 5 S 3 , molecular weight: 511.55, structural formula: [0003] [0004] Cefmenoxime is the third-generation cephalosporin developed by Takeda Corporation of Japan. It was first listed in Japan in 1983. It is a broad-spectrum antibiotic that achieves bactericidal effect by inhibiting the biosynthesis of bacterial cell walls. In vitro tests have shown that cefmenoxime has effects on both gram-positive and gram-negative bacteria, and its strong antibacterial effect on gram-negative bacteria is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04
Inventor 张锡芬
Owner HAINAN LINGKANG PHARMA CO LTD
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