2-Carbamoyloxymethyl-penicillin derivatives

Details 2-Carbamoyloxymethyl-penicillin derivatives 2-Carbamoyloxymethyl-penicillin derivatives

1978-04-03

1982-03-30

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, 424271, 544 16, 544 18, 544 21, 544 22, 544 23, 544 24, 544 25, 544 30, 548178, C07D49932, A61K 3138, C07D50114

Patent

active

043223478

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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patent: 4010156 (1977-03-01), Nudelman et al.
patent: 4182711 (1980-01-01), Ueda
patent: 4218374 (1980-08-01), Kamiya et al.
patent: 4254029 (1981-03-01), Kaspi et al.
Cooper et al., "Accounts of Chemical Research", vol. 6, 1973, pp. 32-40.
Grant et al., "J. Chem. Soc.", (6), 1965, pp. 3842-3845.

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