US 11,905,301 B2
Nitrogen-containing macrocyclic conjugates as radiopharmaceuticals
Paul Stephen Donnelly, Victoria (AU); Michelle Therese Ma, Victoria (AU); and Denis Bernard Scanlon, Meadows (AU)
Assigned to Clarity Pharmaceuticals Ltd., Eveleigh (AU)
Filed by Clarity Pharmaceuticals Ltd., Eveleigh (AU)
Filed on Aug. 4, 2021, as Appl. No. 17/393,837.
Application 17/393,837 is a continuation of application No. 16/712,485, filed on Dec. 12, 2019.
Application 16/712,485 is a continuation of application No. 15/612,009, filed on Jun. 2, 2017, granted, now 10,544,164, issued on Jan. 28, 2020.
Application 15/612,009 is a continuation of application No. 13/132,194, granted, now 9,701,694, issued on Jul. 11, 2017, previously published as PCT/AU2009/001572, filed on Dec. 2, 2009.
Claims priority of application No. 2008906239 (AU), filed on Dec. 2, 2008.
Prior Publication US 2021/0363161 A1, Nov. 25, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 8/72 (2006.01); C07D 521/00 (2006.01); A61K 51/04 (2006.01); A61K 51/08 (2006.01); A61K 49/10 (2006.01); A61K 49/08 (2006.01); A61K 49/06 (2006.01); A61K 51/00 (2006.01); A61K 51/02 (2006.01); A61K 51/10 (2006.01)
CPC C07D 521/00 (2013.01) [A61K 51/0482 (2013.01); A61K 51/082 (2013.01); A61K 51/088 (2013.01); A61K 49/06 (2013.01); A61K 49/08 (2013.01); A61K 49/10 (2013.01); A61K 49/101 (2013.01); A61K 51/00 (2013.01); A61K 51/02 (2013.01); A61K 51/04 (2013.01); A61K 51/08 (2013.01); A61K 51/10 (2013.01); A61K 51/106 (2013.01)] 11 Claims
 
1. A compound of formula (I),

OG Complex Work Unit Chemistry
wherein:
L is a nitrogen containing macrocyclic metal ligand of the formula

OG Complex Work Unit Chemistry
V is selected from the group consisting of N and CR4;
each Rx and Ry are independently selected from the group consisting of H, CH3, CO2H, NO2, CH2OH, H2PO4, HSO3, CN, CONH2 and CHO;
each p is independently an integer selected from the group consisting of 2, 3, and 4; R4 is selected from the group consisting of H, OH, halogen, NO2, NH2, optionally substituted C1-C12alkyl, optionally substituted C6-C18aryl, cyano, CO2R5, NHR5, N(R5)2 and a group of the formula:

OG Complex Work Unit Chemistry
wherein
X1 is a linking moiety;
Y1 is selected from the group consisting of OR6,SR7, N(R8)2 and a molecular recognition moiety;
wherein R5 is H or C1-C12alkyl;
R6 is selected from the group consisting of H, halogen, an oxygen protecting group, optionally substituted C1-C12alkyl, optionally substituted C2-C12alkenyl, optionally substituted C2-C12alkynyl and optionally substituted C2-C12 heteroalkyl;
R7 is selected from the group consisting of H, halogen, a sulfur protecting group, optionally substituted C1-C12alkyl, optionally substituted C2-C-12alkenyl, optionally substituted C2-C12alkynyl and optionally substituted C2-C12 heteroalkyl;
each R8 is independently selected from the group consisting of H, a nitrogen protecting group, optionally substituted C1-C12alkyl, optionally substituted C2-C12alkenyl, optionally substituted C2-C12alkynyl and optionally substituted C2-C12 heteroalkyl;
X is a linking moiety;
Y is a molecular recognition moiety, wherein the molecular recognition moiety is a cyclic RGD or a portion thereof; or
a pharmaceutically acceptable salt or complex thereof.