Tricyclic functional dyes for contrast enhancement in optical im

Details Tricyclic functional dyes for contrast enhancement in optical im Tricyclic functional dyes for contrast enhancement in optical im

1996-05-13

1998-01-20

Kight, John

Drug, bio-affecting and body treating compositions

In vivo diagnosis or in vivo testing

Diagnostic or test agent produces in vivo fluorescence

424 944, 424 91, 424 165, 540 1, A61K 4900, G01N 3100, G01N 3348

Patent

active

057098450

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 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 is 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.

REFERENCES:
patent: 3655392 (1972-04-01), Fumia, Jr. et al.
patent: 3855210 (1974-12-01), Keller
Elwood (1973), J. Org. Chem., vol. 38, No. 14, pp. 2425-2430.
"Dyes Containing the Phenalene Ring System. I. Synthesis of Benzothiazole--Containing Dyes".
Elwood (1973), J. Org. Chem., vol. 38, No. 14, pp. 2430-2433.
"Dyes Containing the Phenalene Ring System. II. Electronic Spectra and their Correlations with Hucke 1 Molecular Orbital Theory".

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