"3-Carbamoyloxy cephalosporins"

Details "3-Carbamoyloxy cephalosporins" "3-Carbamoyloxy cephalosporins"

1983-08-19

1985-05-21

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 22, 2602391, C07D50114, A61K 31545

Patent

active

045187738

ABSTRACT:
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.

REFERENCES:
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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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