US 10,889,550 B2
Contrast agents for myocardial perfusion imaging
David S. Casebier, Carlisle, MA (US); Simon P. Robinson, Stow, MA (US); Ajay Purohit, Sudbury, MA (US); Heike S. Radeke, South Grafton, MA (US); Michael T. Azure, Renlop, AL (US); and Douglas D. Dischino, Middlefield, CT (US)
Assigned to Lantheus Medical Imaging, Inc., North Billerica, MA (US)
Filed by Lantheus Medical Imaging, Inc., North Billerica, MA (US)
Filed on Sep. 27, 2018, as Appl. No. 16/143,748.
Application 12/014,161 is a division of application No. 11/055,498, filed on Feb. 10, 2005, granted, now 7,344,702.
Application 16/143,748 is a continuation of application No. 15/629,068, filed on Jun. 21, 2017, granted, now 10,125,106.
Application 15/629,068 is a continuation of application No. 14/845,320, filed on Sep. 4, 2015, granted, now 9,718,786.
Application 14/845,320 is a continuation of application No. 13/529,756, filed on Jun. 21, 2012, granted, now 9,161,997.
Application 13/529,756 is a continuation of application No. 12/014,161, filed on Jan. 15, 2008, granted, now 8,226,929.
Claims priority of provisional application 60/544,861, filed on Feb. 13, 2004.
Prior Publication US 2019/0127333 A1, May 2, 2019
Int. Cl. C07D 237/16 (2006.01); A61K 49/00 (2006.01); A61K 49/10 (2006.01); A61K 49/22 (2006.01); A61K 51/04 (2006.01); C07B 59/00 (2006.01); C07D 239/88 (2006.01)
CPC C07D 237/16 (2013.01) [A61K 49/00 (2013.01); A61K 49/0002 (2013.01); A61K 49/0052 (2013.01); A61K 49/10 (2013.01); A61K 49/22 (2013.01); A61K 51/04 (2013.01); A61K 51/0421 (2013.01); A61K 51/0453 (2013.01); A61K 51/0459 (2013.01); C07B 59/002 (2013.01); C07D 239/88 (2013.01)] 5 Claims
 
1. A contrast agent comprising an imaging moiety, and a fenazaquin analog having the structure of formula (II),

OG Complex Work Unit Drawing
wherein:
G is

OG Complex Work Unit Drawing
wherein:
R30, R31, R32, and R3 are independently selected from hydrogen, C1-C6 alkyl optionally substituted with an imaging moiety, and an imaging moiety;
R34 is selected from hydrogen and an imaging moiety;
J is selected from N(R27), S, O, C(═O), C(═O)O, NHCH2CH2O, a bond, and C(═O)N(R27), with each group being drawn with its left end attached to G and its right end attached to the carbon substituted with R21 and R22;
wherein R27 is selected from hydrogen, C1-C6 alkyl optionally substituted with an imaging moiety, and an imaging moiety;
when present, K is selected from hydrogen, alkoxyalkyl, alkyloxy, aryl, C1-C6 alkyl optionally substituted with an imaging moiety, heteroaryl, and an imaging moiety;
when present, L is selected from hydrogen, alkoxyalkyl, alkyloxy, aryl, C1-C6 alkyl optionally substituted with an imaging moiety, heteroaryl, and an imaging moiety;
M is selected from hydrogen, alkoxyalkyl, alkyloxy, aryl, C1-C6 alkyl optionally substituted with an imaging moiety, heteroaryl, and an imaging moiety; or
L and M, together with the atom to which they are attached, form a three- or four-membered carbocyclic ring;
n is 0, 1, 2, or 3;
Y is selected from a bond, carbon, and oxygen; provided that when Y is a bond, K and L are absent and M is selected from aryl and heteroaryl; and provided that when Y is oxygen, K and L are absent and M is selected from hydrogen, alkoxyalkyl, aryl, C1-C6 alkyl optionally substituted with an imaging moiety, and heteroaryl;
provided that at least one imaging moiety is present in formula (II),
wherein the imaging moiety is 11C, 13N, 18F, 123I, 125I, 99mTc, 95Tc, 111In, 62Cu, 64Cu, 67Ga, or 68Ga.