US 5,672,332 A · Delta 1,2 bicyclo4,4,0! functional dyes for contrast enhancement in optical imaging

Abstract

This invention provides functional dyes of the general formula: ##STR1## wherein R.sup.1, R.sup.2, 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 allkyl, 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 is 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); R.sup.9 and R.sup.10 are independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 carboxyalkyl, C.sub.1 -C.sub.10 alkoxycarbonyl, and --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7); and A or B may be the same or different and are selected from the group consisting of --(CH.sub.2).sub.m, --C(R.sup.9)(R.sup.10), --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7), --O--, --S--, or --NR.sup.8.

Claims8

Dependent claims

A diagnostic composition comprising a compound of the formula:

##STR6## wherein R.sup.1 is hydrogen;
R.sup.2 is hydrogen;
R.sup.3 is methyl;
R.sup.4 is methyl;
R.sup.5 is methoxycarbonyl;
W.sup.1 is --S--;
W.sup.2 is --S--;
A is --CH.sub.2 --;
and B is --CH.sub.2 --.

6 more elements

A method of imaging a patient comprising the administration of a diagnostically effective amount of a compound of the formula:

##STR9## wherein R.sup.1, R.sup.2, 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 is 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);
R.sup.9 and R.sup.10 are independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 carboxyalkyl, C.sub.1 -C.sub.10 alkoxycarbonyl, and --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7);
and A or B may be the same or different and are selected from the group consisting of --(CH.sub.2).sub.m, --C(R.sup.9)(R.sup.10), --(CH.sub.2).sub.m --N(R.sup.6)(R.sup.7), --O--, --S--, or --NR.sup.8.

4 more elements

Dependencies are inferred from the claim text.

Delta 1,2 bicyclo4,4,0! functional dyes for contrast enhancement in optical imaging

Life of this patent

Delta 1,2 bicyclo4,4,0! functional dyes for contrast enhancement in optical imaging

Life of this patent

Abstract

Claims8