Chiral indole intermediates and their fluorescent cyanine dyes containing functional groups
AssigneesCarnegie Mellon University, Ge Healthcare UK Limited
InventorsRatnaker B. Mujumdar, Richard Martin West
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Abstract
This invention relates to the functionalized cyanine dyes and more particularly, to the synthesis of chiral 3-substituted 2,3′-dimethyl-3H-indole and its derivatives as intermediates for preparation of cyanine dyes, to methods of preparing these dyes and the dyes so prepared.
Claims9
A compound of the following general formula (XIV)
- wherein:
- Ra, Rc, Rd, and Rf are independently selected from V or L-V where
- L is a bond or C1-22 straight or branched alkyl, optionally containing 0, 1 or 2 unsaturations or unsaturated pendent or interchain groups selected from alkenyl, alkynyl and aryl groups;
- V is selected from hydrogen, halogen, —OH, —NH2, —SH, —CN, trifluoromethyl, —SO3−, phosphate, phosphonate, quaternary ammonium, —NO2, mono- or di-nitro-substituted benzyl, —COOH, and —NHCORg, where Rg is C1-20 straight or branched alkyl;
- a target bonding group, reactive group, reactive moiety, or NHRh where Rh is H, C1-20 straight or branched alkyl or COOH;
- T is
- wherein each L and V are independently as defined above;
- Y is selected from the group consisting of O, S, —CH═CH—, >C(CH3)2,
- and —N—(CH2)1-10X, wherein X is selected from —COOH, —NH2, —SO3−, —OH and halogen;
- Za and Zb are independently, fused
- and p, u, v and r are independently an integer from 0-4, and at least one V must be —COOH in at least one of T and Y.
A compound selected from the group consisting of 6-[9-(5-carboxypentyl)-5,7-dimethyl-5,11-disulfo-1,2,9,14,15,16,15a,16a,2a-nonahydroindolo-[2″,1″-1′,2′]isoquinolino[7′,6′-4,3]pyridino[1,2-a]indolin-7-yl/hexanoic acid, and 6,7,9,10-tetrahydro-2,14-disulphonato-16,16,18-trimethyl-7aH,8aH-bisindolinium[3,2-a,3′2′-a]pyrano[3,2-c;5,6-c′]dipyridin-5-ium-18-hexanoic acid.
Dependencies are inferred from the claim text.