Isoquinolinium substituted cephalosporins
AssigneeEli Lilly and Company
InventorsWilliam H. W. Lunn, William J. Wheeler
Life of this patent
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Abstract
Broad spectrum cephalosporin antibiotics represented by the formula ##STR1## wherein R is a 3-aminoisoxazol-5-yl, 2-aminooxazol-4-yl, or a 5-amino-1,2,4-oxadiazol-3-yl group; R.sub.1 is isoquinolinium or substituted isoquinolinium; and R' is C.sub.1 -C.sub.4 alkyl, an N-substituted carbamoyl group, or a carboxy-substituted alkyl or cycloalkyl group; and the pharmaceutically acceptable non-toxic salts thereof; are prepared by the reaction of a 3-iodomethyl cephalosporin, having the above 2-(amino-substituted heterocyclic)-2-oximinoacetyl side chain, with isoquinoline or a substituted isoquinoline. Pharmaceutical formulations of the antibiotics and a method for treating bacterial infections with the antibiotics are provided.
Claims13
A compound of the formula ##STR21## wherein R is an amino-substituted heterocyclic of the formula ##STR22## R' is a hydrogen, C.sub.1 -C.sub.4 alkyl, or a carboxy-substituted alkyl or carboxy-substituted cycloalkyl group of the formula ##STR23## wherein a and b when taken separately are independently hydrogen or C.sub.1 -C.sub.3 alkyl, and when taken together with the carbon atom to which they are attached form a C.sub.3 -C.sub.7 carbocyclic ring;
- R" is hydroxy, C.sub.1 -C.sub.4 alkoxy, or amino;
- or R' is a carbamoyl group of the formula ##STR24## wherein R'" is C.sub.1 -C.sub.3 alkyl, phenyl, or C.sub.1 -C.sub.3 alkyl substituted by phenyl;
- R.sub.1 is isoquinolinium or substituted isoquinolinium substituted by amino, C.sub.1 -C.sub.4 alkylamino, di-(C.sub.1 -C.sub.4 alkyl)amino, hydroxy, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkyl, cyano, trifluoromethyl, sulfo(--SO.sub.3 H), aminosulfonyl(--SO.sub.2 NH.sub.2), carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl, hydroxy substituted C.sub.1 -C.sub.3 alkyl, formyl, C.sub.2 -C.sub.4 alkanoyl, thiocarbamoyl, or carbamoyl;
- and the pharmaceutically acceptable non-toxic salts thereof.
Dependencies are inferred from the claim text.