US 12,324,845 B2
Ligands for imaging cardiac innervation
Ajay Purohit, Sudbury, MA (US); Thomas D. Harris, Salem, NH (US); Heike S. Radeke, South Grafton, MA (US); Simon P. Robinson, Stow, MA (US); Ming Yu, Chelmsford, MA (US); David S. Casebier, Carlisle, MA (US); and Michael T. Azure, Renlop, AL (US)
Assigned to Lantheus Medical Imaging, Inc., Bedford, MA (US)
Filed by Lantheus Medical Imaging, Inc., North Billerica, MA (US)
Filed on Jan. 28, 2022, as Appl. No. 17/587,454.
Application 17/587,454 is a continuation of application No. 15/986,680, filed on May 22, 2018, granted, now 11,241,509.
Application 15/986,680 is a continuation of application No. 13/916,205, filed on Jun. 12, 2013, granted, now 10,010,631.
Application 13/916,205 is a continuation of application No. 12/448,575, granted, now 8,491,868, previously published as PCT/US2007/088500, filed on Dec. 21, 2007.
Claims priority of provisional application 60/877,211, filed on Dec. 26, 2006.
Prior Publication US 2022/0288243 A1, Sep. 15, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 51/04 (2006.01); C07B 59/00 (2006.01); C07C 215/60 (2006.01); C07C 217/70 (2006.01); C07C 279/06 (2006.01); C07C 279/08 (2006.01)
CPC A61K 51/04 (2013.01) [A61K 51/0453 (2013.01); A61K 51/0459 (2013.01); C07B 59/001 (2013.01); C07C 215/60 (2013.01); C07C 217/70 (2013.01); C07C 279/06 (2013.01); C07C 279/08 (2013.01); C07B 2200/05 (2013.01)] 11 Claims
 
1. A method of imaging, the method comprising administering, to a subject, a compound of Structure Alpha, of the formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
n is 0;
R, R1, and R3 are independently selected from the group consisting of H, OR4, F, Cl, Br, I, CF3, alkyl (C1-C4), aryl, heteroaryl, C(═O)R4, CO2R4, N(R4)2, CN, C(═NR4)OR5, NR4C(═NR5)NHR6, C(═NR4)NHR5, C(═O)NHR4, NR4C(═O)NR5, NR4NR5, SO2OR4, and imaging moiety Im;
R2 is absent;
R4, R5, and R6 are independently selected from the group consisting of H, alkyl, aryl and heteroaryl substituents; wherein the alkyl, aryl, or heteroaryl may be substituted with imaging moiety Im, wherein optionally any two of R4, R5, and R6 form a cyclic structure selected from the group consisting of —CH2—CH2—, —CH2—CH2—CH2, —CH═CH—, —X═CH—, and —X—CH═CH—, wherein X is selected from the group consisting of O, NH, and NR7, and wherein R7 is selected from the group consisting of alkyl, aryl, and heteroaryl substituents;
W, X, Y and Z are independently selected from the group consisting of H, OR4, N(R4)2, F, Cl, Br, I, CF3, imaging moiety Im, aryl, and heteroaryl;
A is O or absent; and
selected from the group consisting of 18F, 76Br, 124I, 131I, 99mTc, 153Gd, and 111In;
and acquiring at least one image of the subject.