2-oxoazetidine derivatives, their production and use

Details 2-oxoazetidine derivatives, their production and use 2-oxoazetidine derivatives, their production and use

C - Chemistry, Metallurgy

07

D

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C07D 205/08 (2006.01) C07D 205/095 (2006.01) C07D 403/04 (2006.01) C07D 403/12 (2006.01) C07D 417/12 (2006.01) C07D 417/14 (2006.01) C07F 7/08 (2006.01) C07F 7/10 (2006.01)

Patent

CA 1206968

ABSTRACT OF THE DISCLOSURE This invention relates to a novel compound of the formula and its production process, Image [I] wherein R1 is an amino group which may be acylated or protected; X is hydrogen or a methoxyl group; R4 is (1) a sulfamoyl group, (2) a group of the formula, -S-Y-Z where Y is alkylene or alkenylene with up to 3 C atoms, and Z is ? alkanoyloxy with 2 to 4 C atoms, ? carbamoyl optionally substituted by sulfo, ? a carbamoyloxy or haloacetyl-carbamoyloxy, ? sulfocarbamoyloxy, or ? amino optionally substituted by sulfo, alkanoyl or aralkyloxycarbonyl, (3) triazolyl which is bonded with the azetidine ring on a nitrogen atom of the triazol ring, optionally substituted by alkoxycarbonyl, or (4) azido, with the proviso that when R4 is azido, R1 is a group, Image where Q is alkylene with 1 to 3 C atoms, and T is optionally esterified carboxyl, the ester residue being lower alkyl optionally substituted by trimethylsilyl, or a pharmaceutically acceptable salt or ester thereof. The compound [I], and a pharmaceutically acceptable salt or ester thereof exhibit excellent antimicrobial activity against gram-positive and gram-negative bacteria, and .beta.-lactamase inhibitory activity, thus being of value as a prophylactic or therapeutic agent for infectious diseases in mammals.

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