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US 4,272,439 AGranted
6-(Substituted-hydroxymethylene penams)
AssigneeSchering Corporation
InventorsAshit K. Ganguly, Viyyoor M. Girijavallabhan, Patricia Cavender, Olga Sarre, Stuart W. McCombie
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Abstract
.beta.-Lactams having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group are prepared by reaction of an .alpha.-halo-.beta.-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone. Also described are noval penicillins and cephalosporins having useful antibacterial activity.
Claims4
A compound of the formula:
- ##STR44## wherein Y is sulfur or sulfoxide;
- R.sub.1 together with the carbon atom to which it is attached, is the carbon residue of an aldehyde or ketone which contains no functional group that would preferentially react with a zinc halo-.beta.-lactam intermediate over the oxo functionality;
- R.sub.2 is a group of the formula
- --(CH.sub.2).sub.m --(X).sub.p --(CH.sub.2).sub.n --
- wherein
- X is O or S;
- m is 0-3;
- p is 0-1;
- n is 0-3;
- and
- m+p+n is 3-5;
- and
- R.sub.4 is cyano, or --COOR.sub.11 wherein R.sub.11 is a readily removable ester-forming moiety, and the pharmaceutically acceptable acid addition salts thereof.
10 more elements
A compound of the formula:
- ##STR45## wherein R.sub.1, together with the carbon atom to which it is attached, is the carbon residue of an aldehyde or ketone which contains no functional group that would preferentially react with a zinc halo-.beta.-lactam intermediate over the oxo functionality;
- R.sub.2 is a group of the formula:
- --(CH.sub.2).sub.m --(X).sub.p --(CH.sub.2).sub.n --
- wherein X is O or S;
- m is 0-3;
- p is 0-1;
- n is 0-3;
- and
- m+p+n is 3-5;
- R.sub.3 is hydrogen or lower alkoxy;
- Y is sulfur or sulfoxide;
- R.sub.12 is hydroxy, lower alkoxy, formyloxy, lower alkanoyloxy, lower alkylsulfonyloxy, or a halogen atom;
- and R.sub.13 is hydrogen, an alkali metal cation, acetoxymethyl, or a readily removable ester-forming moiety with the proviso that when R.sub.12 is hydroxy, then R.sub.13 is not a readily removable ester-forming moiety, and the pharmaceutically acceptable acid addition salts thereof.
10 more elements
Dependencies are inferred from the claim text.