"3-Carbamoyloxy cephalosporins"

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...


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544 22, 2602391, C07D50114, A61K 31545




Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. 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.

patent: 3275626 (1966-09-01), Marin et al.
patent: 3714156 (1973-01-01), Rapoport
patent: 3997533 (1976-12-01), Kalbe et al.
patent: 4010156 (1977-03-01), Nudelman et al.
patent: 4182711 (1980-01-01), Veda
patent: 4218374 (1980-08-01), Kamiya et al.
patent: 4254029 (1981-03-01), Kaspi et al.
patent: 4374982 (1983-02-01), Cundall et al.
patent: 4426520 (1984-01-01), Cundall et al.
Cooper et al., Accounts of Chemical Research vol. 6, 32 (1973).
Cephalosporins and Penicillins, Chapter 5, E. H. Flynn ed., Academic Press, 1972.


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