C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/111, 260/101
C07D 501/14 (2006.01) C07D 499/00 (2006.01)
Patent
CA 1140915
ABSTRACT Penicillin sulfoxide esters are reacted with an iso- cyanate to produce the corresponding (substituted)-2-carbamoyl- oxyamethylpenam, the corresponding (substituted)-3-carbamoyl- oxycepham or the corresponding 3-methylcepham. the 6- or 7- side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephams) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephams. The substituent groups may be removed from the (substituted)-2- carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively. Novel penams and cephams provided by the present invention (after removal of the carboxyl-protecting group to produce the free acid) are active against various Gram-positive and Gram-negative organisms and, accordingly, are useful antibacterial agents for the treatment of diseases caused by such organisms in animals, including man.
322307
Cundall Robert L.
Walker Derek
Bristol-Myers Squibb Company
Gowling Lafleur Henderson Llp
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