New method for synthesizing fosfomycin trometamol

A technology for fosfomycin tromethamine and synthesizing fosfomycin, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problem of time-consuming, high cost of raw materials, and four impurities in finished products exceeding the standard And other issues

Inactive Publication Date: 2012-09-12
FARMASINO PHARMA ANHUI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Disadvantages: The above two methods use fosfomycin salt (fosfomycin levophosphorylamine salt, fosfomycin sodium, fosfomycin calcium, etc.) as raw materials. , the ineffective compound dexfosfomycin and levophenethylamine salt accounted for half of the composition, and dexfosfomycin was not utilized, resulting in a waste of resources
When the ion exchange method is preparing fosfomycin trometamol, the activation process of D001 resin is increased, and the workload of wastewater treatment is increased; during the free process of fosfomycin acid, the epoxy double bond is easy to ring-opening and hydrolyzed, resulting in The four impurities in the finished product exceed the standard, affecting the quality
In a word, the above preparation methods of fosfomycin trometamol all have the disadvantages of high raw material cost, more reaction steps, longer time consumption, and difficult handling of reaction by-products.

Method used

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  • New method for synthesizing fosfomycin trometamol
  • New method for synthesizing fosfomycin trometamol

Examples

Experimental program
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Embodiment 1

[0017] 1. Synthesis of Chiral Ligands

[0018] Dissolve 1.06 g of chiral bispiperidine derivatives in 10 mL of methanol, slowly add 2.49 g of methyl rhenium trioxide dropwise under stirring, and stir overnight at room temperature under nitrogen protection. The pH was adjusted to 4 with 2M methanolic hydrochloric acid, and a large amount of off-white solid was precipitated. After washing with methanol, dry in vacuum at room temperature before use.

[0019] 2. Preparation of Crude Fosfomycin Tromethamine

[0020] Take 1.22g of cis-acrylphosphoric acid and 5mL of absolute ethanol and add it to a 50mL three-necked bottle, stir to completely dissolve. Add 23 mg of the chiral ligand prepared above, and then add 1.70 g of 30% hydrogen peroxide, heat to 40° C. until completely dissolved, and react for 1 hour, and monitor the reaction by high performance liquid phase. After the reaction was completed, it was cooled, and the insoluble matter was filtered off. Under stirring, 1.37g o...

Embodiment 2

[0024] 1. Synthesis of Chiral Ligands

[0025] Dissolve 1.06 g of chiral bispiperidine derivatives in 10 mL of methanol, slowly add 2.49 g of methyl rhenium trioxide dropwise under stirring, and stir overnight at room temperature under nitrogen protection. The pH was adjusted to 4 with 2M methanolic hydrochloric acid, and a large amount of off-white solid was precipitated. After washing with methanol, dry in vacuum at room temperature before use.

[0026] 2. Preparation of Crude Fosfomycin Tromethamine

[0027] Take 1.22g of cis-acrylphosphoric acid and 5mL of absolute ethanol and add it to a 50mL three-necked bottle, stir to completely dissolve. Add 25 mg of the chiral ligand prepared above, and then add 1.80 g of 30% hydrogen peroxide, heat to 40° C. until completely dissolved, and react for 1 hour, and monitor the reaction by high performance liquid phase. After the reaction was completed, it was cooled, and the insoluble matter was filtered off. Under stirring, add 1.3...

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Abstract

The invention relates to a new method for synthesizing fosfomycin trometamol, which comprises the following steps: directly oxidizing under the catalysis of a chiral ligand through maleic phosphoric acid, obtaining optically-pure free fosfomycin acid and adding an equivalent of tromethamine for neutral reaction to obtain fosfomycin trometamol.

Description

technical field [0001] The invention relates to a new method for preparing fosfomycin tromethamine. The invention provides a new method for synthesizing fosfomycin tromethamine salt which is more convenient and low-cost. Background technique [0002] Fosfomycin is a broad-spectrum, low-toxic, non-sensitizing, non-resistance-resistant antibiotic that has a synergistic effect with most antibiotics. It is effective against Staphylococcus, E. , Serratia, Proteus, Pseudomonas aeruginosa, Shigella and Helicobacter pylori are all sensitive and can inhibit the synthesis of bacterial cell walls. Proteus, some Klebsiella pneumoniae and indole-negative proteobacteria have inhibitory effect. Fosfomycin is suitable for infection and sepsis in urinary tract, respiratory tract, digestive tract, gynecology, skin soft tissue and other parts. Oral administration can treat intestinal infection, urinary tract infection, Serratia infection, Helicobacter pylori infection, blepharitis, hordeolum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655C07C215/10C07C213/08
Inventor 燕立波王丽沈兵程思燕立兵
Owner FARMASINO PHARMA ANHUI
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