Preparation method of fosfomycin monoamine butantriol

A technology of monotromethamine and bistromethamine, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve incomplete reactions, easy hydrolysis, intermediates Fosfomycin acid instability and other problems, to achieve the effect of simple reaction, high product content, great application value

Inactive Publication Date: 2012-02-15
SHANXI C&Y PHARMACEUTICAL GROUP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] But there are some deficiencies in the above-mentioned method: as: sulfonate tromethamine salt recovery difficulty, fosfomycin calcium poor solubility in water and organic solvent, reaction is incomplete, and the intermediate fosfomycin acid of generation is unstable, easily hydrolyzed Wait

Method used

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  • Preparation method of fosfomycin monoamine butantriol

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Effect test

Embodiment 1

[0019] Add 480ml of anhydrous methanol to the reaction bottle, add 80g of fosfomycin bis tromethamine salt under stirring, control the temperature at 20°C, add sulfuric acid and adjust the pH to 6.7, stir for half an hour, filter, add 1000ml of ethyl acetate to the filtrate After crystallization occurs, keep warm (at a temperature of 20° C.) and stir for 2 hours, filter, wash with 10 ml of ethyl acetate, drain and dry (put in an oven for drying at a constant temperature of 40° C.) to obtain 47.5 g of fosfomycin monotromethamine , Yield: 87.0%. The content of fosfomycin monotromethamine detected by liquid phase HPLC was 99.5%.

Embodiment 2

[0021] Add 500ml of anhydrous methanol to the reaction bottle, add 80g of fosfomycin bis tromethamine salt under stirring, control the temperature at 15°C, add trichloroacetic acid and adjust the pH to 6.2, stir for half an hour, filter, and add methyl acetate to the filtrate 1200ml of ester, after crystallization occurs, keep warm (at 20°C) and stir for 2 hours, filter, wash with 10ml of methyl acetate, drain and dry (put in an oven at 40°C for constant temperature drying) to obtain fosfomycin monotromethamine 47.1 g, yield: 86.3%. The detected content of fosfomycin monotromethamine was 99.0%.

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Abstract

The invention provides a preparation method of fosfomycin monoamine butantriol. The method comprises the following steps of: adding fosfomycin diamine butantriol salt into methanol, adding acid to adjust the pH to be between 4 and 7 at the temperature of between 5 DEG C below zero and 30 DEG C, filtering, removing filter residue, adding an organic solvent into the filtrate to separate out crystal, filtering, drying, and thus obtaining a fosfomycin monoamine butantriol finished product. The method is simple in reaction, the yield can reach 85 to 90 percent, the product content (the detection content can reach over 99 percent) is high, and the method is suitable for industrialized production and has great application value.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to a preparation method of fosfomycin monotromethamine. Background technique [0002] Fosfomycin monotromethamine, its chemical name: mono(2-amino-2-hydroxymethyl-1,3-propanediol)(2R-cis)(3-methyl-1,2-epoxypropylene base) phosphate, the chemical structural formula is: [0003] [0004] Fosfomycin monotromethamine salt was invented by Zambon Company in Italy in 1981. This salt has the characteristics of good water solubility, fast oral absorption and high bioavailability. This product belongs to antibiotics, and its molecular structure is similar to phosphoenolpyruvate , so it can compete with the same transferase, hindering the early synthesis of bacterial cell wall, resulting in cell rupture and bacterial death. When this product is used in combination with penicillins, cephalosporins, aminoglycosides and other antibiotics, it has a synergistic effect and enhances the effect and delays t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655
Inventor 李志成贾佩骞侯伟
Owner SHANXI C&Y PHARMACEUTICAL GROUP CO LTD
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