US 12,065,413 B2
PSMA targeted fluorescent agents for image guided surgery
Martin G. Pomper, Baltimore, MD (US); Ronnie C. Mease, Fairfax, VA (US); Ying Chen, Timonium, MD (US); and Sangeeta Ray, Ellicott City, MD (US)
Assigned to THE JOHNS HOPKINS UNIVERSTY, Baltimore, MD (US)
Filed by The Johns Hopkins University, Baltimore, MD (US)
Filed on May 26, 2021, as Appl. No. 17/331,113.
Application 14/243,535 is a division of application No. 13/257,499, granted, now 9,056,841, issued on Jun. 16, 2015, previously published as PCT/US2010/028020, filed on Mar. 19, 2010.
Application 17/331,113 is a continuation of application No. 16/820,052, filed on Mar. 16, 2020, granted, now 11,021,450.
Application 16/820,052 is a continuation of application No. 16/704,137, filed on Dec. 5, 2019, abandoned.
Application 16/704,137 is a continuation of application No. 15/618,788, filed on Jun. 9, 2017, abandoned.
Application 15/618,788 is a continuation in part of application No. 14/243,535, filed on Apr. 2, 2014, granted, now 9,776,977, issued on Oct. 3, 2017.
Claims priority of provisional application 62/324,097, filed on Apr. 18, 2016.
Claims priority of provisional application 61/248,934, filed on Oct. 6, 2009.
Claims priority of provisional application 61/248,067, filed on Oct. 2, 2009.
Claims priority of provisional application 61/161,485, filed on Mar. 19, 2009.
Claims priority of provisional application 61/161,484, filed on Mar. 19, 2009.
Prior Publication US 2022/0048872 A1, Feb. 17, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 51/00 (2006.01); A61K 49/00 (2006.01); A61K 51/04 (2006.01); A61M 36/14 (2006.01); C07D 209/12 (2006.01); C07D 209/14 (2006.01); C07D 209/24 (2006.01); C07D 213/04 (2006.01); C07D 249/04 (2006.01); C07D 255/02 (2006.01); C07D 257/02 (2006.01); C07D 311/14 (2006.01); C07D 311/20 (2006.01); C07D 311/82 (2006.01); C07F 5/02 (2006.01); C07F 13/00 (2006.01); G01N 33/50 (2006.01)
CPC C07D 257/02 (2013.01) [A61K 49/0032 (2013.01); A61K 49/0052 (2013.01); A61K 51/0421 (2013.01); A61K 51/044 (2013.01); A61K 51/0446 (2013.01); A61K 51/0453 (2013.01); A61K 51/0472 (2013.01); C07D 209/12 (2013.01); C07D 209/14 (2013.01); C07D 209/24 (2013.01); C07D 213/04 (2013.01); C07D 249/04 (2013.01); C07D 255/02 (2013.01); C07D 311/14 (2013.01); C07D 311/20 (2013.01); C07D 311/82 (2013.01); C07F 5/027 (2013.01); C07F 13/005 (2013.01); G01N 33/5091 (2013.01); G01N 2800/342 (2013.01)] 19 Claims
 
1. A compound having the structure:

OG Complex Work Unit Chemistry
wherein:
Z is tetrazole or CO2O;
each Q is independently selected from hydrogen or a protecting group;
FG is a fluorescent dye moiety which emits in the visible or near infrared spectrum;
each R is independently H or C1-C4 alkyl;
V is —C(O)—;
a is 1, 2, 3, or 4;
m is 1, 2, 3, 4, 5, or 6;
n is 1, 2, 3, 4, 5 or 6;
R2 and R3 are independently H, CO2H, or CO2R4, where R4 is a C1-C6 alkyl, C6-C12 aryl, or alkylaryl having 1 to 3 separate or fused rings and from 6 to about 18 ring carbon atoms, wherein when one of R2 and R3 is CO2H or CO2R4, the other is H.