3-Azidocephalosporins

Details 3-Azidocephalosporins 3-Azidocephalosporins

1983-09-28

1985-06-04

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 22, C07D50114, A61K 31545

Patent

active

045215987

ABSTRACT:
7.beta.-Acylamino-3-azido-3-cephem-4-carboxylic acid esters are obtained with the corresponding 3-halo or 3-sulfonyloxy-3-cephem esters and an alkali metal azide. The 3-azido compounds as the free acids or salts are antibacterial agents while in esterified form react with alcohols and phenols to provide 2-alkoxy (or 2-phenoxy)-3amino-3-cephem esters and isomeric ring expanded 4,7-bicyclo .beta.-lactam compounds, namely [2R-(2.alpha.,7.alpha.,8.beta.)-4-alkoxy (or 4-phenoxy)-9-oxo-8-acylamino-6-thia-1,3-diazabicyclo[5.2.0]non-3-ene-2-car boxylic acids and esters and the corresponding 3-alkoxy (or 3-phenoxy) 1,4-diazabicyclo[5.2.0]non-3-ene-2-carboxylic acids and esters. These reaction products obtained with the azide possess antibacterial properties.

REFERENCES:
patent: 3274186 (1966-09-01), Barker et al.
patent: 3278531 (1966-10-01), Cox et al.
patent: 3360515 (1967-12-01), Takano et al.
patent: 3634418 (1972-01-01), Willner
patent: 3923795 (1975-12-01), Spry
patent: 4001226 (1977-01-01), Spry
patent: 4420478 (1983-12-01), Heymes

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