US 12,466,814 B2
Sterically shielded heptamethine cyanine dyes
Bradley D. Smith, Granger, IN (US); and Donghao Li, South Bend, IN (US)
Assigned to UNIVERSITY OF NOTRE DAME DU LAC, South Bend, IN (US)
Appl. No. 17/996,420
Filed by UNIVERSITY OF NOTRE DAME DU LAC, South Bend, IN (US)
PCT Filed Feb. 22, 2021, PCT No. PCT/US2021/018994
§ 371(c)(1), (2) Date Oct. 17, 2022,
PCT Pub. No. WO2021/216183, PCT Pub. Date Oct. 28, 2021.
Claims priority of provisional application 63/148,067, filed on Feb. 10, 2021.
Claims priority of provisional application 63/013,756, filed on Apr. 22, 2020.
Prior Publication US 2023/0219933 A1, Jul. 13, 2023
Int. Cl. C07D 403/14 (2006.01); G01N 33/58 (2006.01)
CPC C07D 403/14 (2013.01) [G01N 33/582 (2013.01)] 20 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
or a salt thereof;
wherein
G1 and G2 are each independently-(C1-C4)alkyl-(Z)—RW;
each Z is independently 5- or 6-membered heterocycle;
each RW is independently —X1(C1-C4)alkyl-(O(C2-C4)alkyl)m-O(C1-C4)alkyl, or H;
each X1 is independently absent, O, S, or NH;
each m is independently 0-500;
G3 is —(C═O)RA wherein RA is ORB, NRBRC, H, or halo;
RB and RC are each independently H, N-succinimidyl, drug, or biologic;
J1 and J2 are each independently SO3H or CO2H;
Q1 and Q2 are each independently —(C2-C6)alkyl-X2;
each X2 is independently N+(RD)3, N(RD)2, CO2H, SO3H, or —O(C1-C6)alkyl;
each RD is independently-(C1-C6)alkyl;
R1, R2, R3 and R4 are each independently —(C1-C4)alkyl or H;
R5 and R6 are each independently H or —(C1-C4)alkyl; or
R5 and R5 taken together form a 5- or 6-membered carbocycle; and
x and y are each independently 0-3;
wherein the moieties (C2-C4)alkyl or (C2-C6)alkyl are optionally branched, and charged moieties present in the compound are counterbalanced with counterions.