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Method for synthesizing aztreonam compound

A synthetic method and compound technology, applied in the field of medicine, can solve problems such as unfavorable to environmental protection and unsuitable for large-scale industrial production, and achieve the effects of reducing reaction time, saving production costs, and reducing environmental pollution

Active Publication Date: 2012-08-29
SHANXI PUDE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a highly toxic solvent, which is not conducive to environmental protection and is not suitable for large-scale industrial production.

Method used

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  • Method for synthesizing aztreonam compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 175g of purified water and 140g of methanol to the reaction vessel, add 20g of trans-3(S)-amino-4-methyl-2-oxo-1-azetidinanesulfonic acid, stir and cool down to -20°C . Keeping the temperature, start to add triethylamine dropwise until the pH value of the solution is 6.0. Begin to add (Z)-2-[(2-aminothiazol-4-yl)-(benzothiazol-2-ylthiocarbonyl)methyleneaminooxy]-2-methylpropionic acid tert-butyl ester 60g , During the feeding process, triethylamine is added dropwise, the pH value is always controlled between 5.0 and 9.0, the temperature is between -20 and -10, and the time is controlled within 2 hours. Continue to react for 2 hours. Filter, lower the temperature to -10°C, adjust the pH value to 1.5 with concentrated hydrochloric acid, white crystals are precipitated, keep warm and crystallize for 2 hours, filter to obtain tert-butylaztreonam.

[0031]Add tert-butylaztreonam into 3 times the amount of acetic acid and water mixed solvent (acetic acid: water = 5:5, ...

Embodiment 2

[0033] Add 200g of purified water, 100g of ethanol, and 100g of acetone into the reaction vessel, add 28g of trans-3(S)-amino-4-methyl-2-oxo-1-azetidinanesulfonic acid, stir and cool down to -30°C. Keeping the temperature, start to add triethylamine dropwise until the pH value of the solution is 8.0. Add (Z)-2-[(2-aminothiazol-4-yl)-(benzothiazol-2-ylthiocarbonyl)methyleneaminooxy]-2-methylpropionic acid tert-butyl ester 84g, During the feeding process, the pH value is always controlled between 5.0 and 9.0, and the temperature is between -20 and 0°C. The control is added within two hours. Continue to react for 2 hours, add activated carbon and stir for 0.5 hours. Filter, lower the temperature to -10°C, adjust the pH value to 1.0-1.5 with concentrated hydrochloric acid, white crystals precipitate, keep warm for 2 hours, and filter to obtain tert-butylaztreonam.

[0034] Add tert-butylaztreonam into a mixed solvent of 3 times the amount of acetic acid and water (acetic acid:...

Embodiment 3

[0036] Add 350kg of purified water, 280kg of acetone, and 40kg of trans-3(S)-amino-4-methyl-2-oxo-1-azetidinanesulfonic acid into the reaction vessel, stir and cool down to -20°C . Keeping the temperature, start to add triethylamine dropwise until the pH value of the solution is 5.0. Add (Z)-2-[(2-aminothiazol-4-yl)-(benzothiazol-2-ylthiocarbonyl)methyleneaminooxy]-2-methylpropionic acid tert-butyl ester 120kg, During the feeding process, the pH value is always controlled between 5.0 and 9.0, and the temperature is between -30 and -20°C. The control is added within 6 hours. Continue to react for 2 hours, add activated carbon and stir for 0.5 hours. Filter, lower the temperature to -20°C, adjust the pH value to 1.0-1.5 with concentrated hydrochloric acid, white crystals are precipitated, keep warm and crystallize for 2 hours, filter to obtain tert-butylaztreonam.

[0037] Add tert-butylaztreonam into 3 times the amount of acetic acid and water mixed solvent (acetic acid: wa...

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Abstract

The invention relates to a method for synthesizing an aztreonam compound. The method comprises the following steps of: (1) adding water and a water-soluble non-aqueous solvent into a reaction container, adding trans-3(S)-amino-4-methyl-2-keto-1-azetidine sulfonic acid, triethylamine and (Z)-2-[(2-aminothiazole-4-radical)-(benzothiazole-2-sulfenyl carbonyl) methylamine oxygroup]-2-methylpropanoic acid tert-butyl ester for reacting, and adjusting the pH with acid and separating crystals out to obtain tertiary butyl aztreonam; and (2) subjecting the tertiary butyl aztreonam and acid-water mixed liquor to reaction and performing post-treatment to obtain aztreonam. By adopting the method, the reaction time can be shortened, the reaction speed can be increased, the production cost can be lowered, and environmental pollution can be reduced.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing aztreonam compound. Background technique [0002] Aztreonam was the first monobactam antibiotic for clinical use. Developed by Bristol-Myers Squibb, it was first launched in Italy in 1984. The chemical name is: [2S-[2α, 3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1 -sulfo-3-azetidinyl)amino]-2-oxyethylene]amino]oxo]-2-methylpropanoic acid. Molecular formula: C 13 h 17 N 5 o 8 S. Molecular weight: 435.44. Structural formula: [0003] [0004] Aztreonam has a strong effect on Gram-negative bacteria and is stable to a variety of plasmid-mediated and chromosome-mediated β-lactamases. Some strains resistant to cephalosporin or penicillin antibiotics are still susceptible to aztreonam. Moreover, this product is safe and effective in clinical use, widely used in various infections, and the clinical effective rate is above ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12
Inventor 解晓荣张磊李立忠李润宝王勇胡成伟
Owner SHANXI PUDE PHARMA CO LTD
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