US 12,186,404 B2
Delta-opioid receptor targeted agent for molecular imaging and immunotherapy of cancer
Mark L. McLaughlin, Tampa, FL (US); and David L. Morse, Tampa, FL (US)
Assigned to H. Lee Moffitt Cancer Center and Research Institute, Inc., Tampa, FL (US); and University of South Florida, Tampa, FL (US)
Filed by H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC., Tampa, FL (US); and UNIVERSITY OF SOUTH FLORIDA, Tampa, FL (US)
Filed on Jun. 2, 2022, as Appl. No. 17/830,781.
Application 17/830,781 is a continuation of application No. 16/587,720, filed on Sep. 30, 2019, abandoned.
Application 16/587,720 is a continuation of application No. 16/098,906, granted, now 10,426,843, issued on Oct. 1, 2019, previously published as PCT/US2017/030962, filed on May 4, 2017.
Claims priority of provisional application 62/331,791, filed on May 4, 2016.
Prior Publication US 2023/0144004 A1, May 11, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 47/68 (2017.01); A61K 49/00 (2006.01); A61P 35/00 (2006.01); A61P 35/04 (2006.01)
CPC A61K 47/6857 (2017.08) [A61K 47/6803 (2017.08); A61K 47/6849 (2017.08); A61K 49/0002 (2013.01); A61K 49/0032 (2013.01); A61K 49/0058 (2013.01); A61P 35/00 (2018.01); A61P 35/04 (2018.01)] 6 Claims
OG exemplary drawing
 
1. A compound having Formula I:

OG Complex Work Unit Chemistry
wherein;
n is an integer from 1 to 50;
L2 is a linking moiety selected from the group consisting of R14, C(O) R14C(O), C(O) R14N, NHR14NH, or C(O) NHR14NHC(O); wherein R14 is O, S, C1-C20 alkyl; C1-C20 heteroalkyl; C1-C20 alkylamine; C1-C20 alkoxyl; C1-C20 alkanoyloxyl; or C1-C20 alkylamido, any of which can be optionally substituted with one or more substituents including halogen, alkoxyl, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, heteroaryl, amine, cyano, hydroxyl, carbonyl, acyl, carboxylic acid (—COOH), —C(O) R12, primary amide (e.g., —CONH2), secondary amide (e.g., —CONHR12), —C(O) NR12R13, —NR12R13, —NR12S (O)2R13, —NR12C(O) R13, —S(O)2R12, and —S(O)2NR12R13, sulfinyl group (e.g., —SOR12), and sulfonyl group (e.g., —SOOR12); wherein R12 and R13 can each independently be hydrogen, halogen, hydroxyl, alkyl, haloalkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, carbonyl, cyano, amino, alkylamino, dialkylamino, alkoxyl, aryloxyl, cycloalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl;
Ab is an antibody that targets PD-1, PD-L1, CD137, OX40 or CD40; and
Dmt-Tic is represented by

OG Complex Work Unit Chemistry
wherein Dmt-Tic is linked to Formula I via an amide bond,
where R1 and R2 are independently selected from H and CH3.