Delta.sup.1,6 bicyclo �4,4,0! functional dyes for contrast enhancement

Abstract

This invention provides functional dyes of the general formula: ##STR1## wherein R1, R2, and R.sup.5 may be the same or different and are selected from the group consisting of hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyl, hydroxyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 aryl, carboxyl, C.sub.1 -C.sub.10 carboxylalkyl, halogen, nitro, C.sub.1 -C.sub.10 alkoxycarbonyl, mercapto, C.sub.1 -C.sub.10 mercaptoalkyl, C.sub.1 -C.sub.10 alkylthio, sulfonate, and --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7) wherein R.sup.6 and R.sup.7 are independently hydrogen or C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 acyl, and R.sup.6 and R.sup.7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR.sup.8, or --S--; R.sup.3 and R.sup.4 may be the same or different and are selected from the group consisting of C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 aryl, C.sub.1 -C.sub.10 carboxylalkyl, C.sub.1 -C.sub.10 alkyl sulfonate, mercapto alkyl and --(CH.sub.2).sub.m N(R.sup.6)(R.sup.7); W.sup.1 and W.sup.2 may be the same or different and are selected from the group consisting of --S--, --O--, --Se--, --Te--, --NR.sup.8 and C(R.sup.9)(R.sup.10); and m is about 0-10; R.sup.8, R.sup.9, and R.sup.10 are independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 mercaptoalkyl, hydroxyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 aryl, C.sub.1 -C.sub.10 carboxylalkyl, C.sub.1 -C.sub.10 alkoxycarbonyl, C.sub.1 -C.sub.10 alkylthio, and --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7); and A is selected from the group consisting of --(CH.sub.2)--, --O--, --S--, or --NR.sup.8. Also provided are methods of using dyes of the invention comprising administering a diagnostically effective amount of the dye to a patient and visualizing the dye.