US 12,077,549 B2
Pentaaza macrocyclic ring complexes possessing oral bioavailability
Jeffery L. Keene, St. Louis, MO (US); Otto F. Schall, Creve Coeur, MO (US); and Dennis P. Riley, Chesterfield, MO (US)
Assigned to Galera Labs, LLC, Malvern, PA (US)
Filed by Galera Labs, LLC, Creve Coeur, MO (US)
Filed on Jul. 19, 2021, as Appl. No. 17/378,852.
Application 17/378,852 is a continuation of application No. 16/812,740, filed on Mar. 9, 2020, granted, now 11,066,433, issued on Jul. 20, 2021.
Application 16/812,740 is a continuation of application No. 15/751,495, granted, now 10,597,415, issued on Mar. 24, 2020, previously published as PCT/US2016/046599, filed on Aug. 11, 2016.
Claims priority of provisional application 62/203,761, filed on Aug. 11, 2015.
Prior Publication US 2021/0347796 A1, Nov. 11, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07F 13/00 (2006.01); A61K 9/00 (2006.01); A61K 9/28 (2006.01); A61K 9/48 (2006.01); A61K 31/28 (2006.01); A61K 31/555 (2006.01); A61K 47/14 (2017.01); A61K 47/38 (2006.01); A61K 47/44 (2017.01); A61P 1/00 (2006.01); A61P 17/00 (2006.01)
CPC C07F 13/005 (2013.01) [A61K 9/0019 (2013.01); A61K 9/2866 (2013.01); A61K 9/4816 (2013.01); A61K 31/28 (2013.01); A61K 31/555 (2013.01); A61K 47/14 (2013.01); A61K 47/38 (2013.01); A61K 47/44 (2013.01); A61P 1/00 (2018.01); A61P 17/00 (2018.01)] 15 Claims
OG exemplary drawing
 
1. A pentaaza macrocyclic ring complex of Formula (IB):

OG Complex Work Unit Chemistry
wherein
M is Mn+2, or Mn+3;
R1A, R1B, R2, R3, R4A, R4B, R5, R6, R7A, R7B, R8, R9, R10A, and R10B are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, an amino acid side chain moiety, or a moiety independently selected from the group consisting of —OR11, —NR11R12, —COR11, —CO2R11, —C(═O)NR11R1 2, —SR11, —SOR11, —SO2R11, —SO2NR11R12, —N(OR11)(R12), —P(═O)(OR11)(OR12), —P(═O)(O R11)(R12), and —OP(═O)(OR11)(OR12),
wherein R11 and R12 are independently hydrogen or alkyl;
W1, W2, and W3 are independently halo, hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl, alkaryl, acyl, acyloxy, alkoxy, an ether, a thioether, or nitro;
each —OC(═O)X1 is propionato; and
the bonds between the transition metal M and the macrocyclic nitrogen atoms and the bonds between the transition metal M and the oxygen atoms of the axial ligands —OC(═O)X1 are coordinate covalent bonds.