US 11,813,340 B2
PSMA targeted radiohalogenated urea-polyaminocarboxylates for cancer radiotherapy
Martin G. Pomper, Baltimore, MD (US); Ronnie C. Mease, Fairfax, VA (US); Vivek Kumar, Rensselaer, NY (US); Sangeeta Ray, Ellicott City, MD (US); Michael Zalutsky, Chapel Hill, NC (US); and Ganesan Vaidyanathan, Chapel Hill, NC (US)
Assigned to The Johns Hopkins University, Baltimore, MD (US); and Duke University, Durham, NC (US)
Appl. No. 16/967,488
Filed by The Johns Hopkins University, Baltimore, MD (US); and Duke University, Durham, NC (US)
PCT Filed Feb. 6, 2019, PCT No. PCT/US2019/016821
§ 371(c)(1), (2) Date Aug. 5, 2020,
PCT Pub. No. WO2019/157037, PCT Pub. Date Aug. 15, 2019.
Claims priority of provisional application 62/626,993, filed on Feb. 6, 2018.
Prior Publication US 2021/0220493 A1, Jul. 22, 2021
Int. Cl. A61K 51/04 (2006.01); A61P 35/00 (2006.01)
CPC A61K 51/0497 (2013.01) [A61P 35/00 (2018.01)] 31 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein:
Z is tetrazole or CO2Q;
Q is H or a protecting group;
m is an integer selected from the group consisting of 1, 2, 3, 4, and 5;
R is —CH2—R1; wherein R1 is:

OG Complex Work Unit Chemistry
wherein X1 is —CR3 or N, wherein R3 is H or C1-C4 alkyl;
wherein X is selected from the group consisting of a radioisotope of iodine, a radioisotope of bromine, and a radioisotope of astatine;
L is a linker selected from the group consisting of C1, C2, C3, C4, C5, and C6 alkylene, C3, C4, C5, and C6 cycloalkylene, and arylene, each of which can be substituted or unsubstituted;
W is selected from the group consisting of —NR2—(C═O)—, —NR2—(C═S)—, —(C═O)—NR2—, and —(C═S)—NR2—; wherein each occurrence of L and W can be the same or different;
R2 is H or C1-C4 alkyl;
n is an integer selected from the group consisting of 1, 2, and 3;
Ch is a chelating agent that can comprise a metal; and
pharmaceutically acceptable salts thereof.