US 12,478,628 B2
Germ cell nuclear factor ligands and methods of use thereof
Ian Mitchelle Sayo De Vera, St. Louis, MO (US); Udayanga Sumith Wanninayake, Valley Park, MO (US); Tom Burriss, St. Louis, MO (US); and Kristine Griffett, St. Louis, MO (US)
Assigned to Saint Louis University, St. Louis, MO (US); and University of Health Sciences and Pharmacy in St. Louis, St. Louis, MO (US)
Filed by Saint Louis University, St. Louis, MO (US); and UNIVERSITY OF HEALTH SCIENCES AND PHARMACY IN ST. LOUIS, St. Louis, MO (US)
Filed on Sep. 27, 2021, as Appl. No. 17/486,695.
Claims priority of provisional application 63/083,227, filed on Sep. 25, 2020.
Prior Publication US 2022/0110942 A1, Apr. 14, 2022
Int. Cl. A61K 31/5377 (2006.01); A61K 31/352 (2006.01); A61K 31/404 (2006.01); A61K 31/438 (2006.01); A61K 31/472 (2006.01); A61K 31/517 (2006.01); C12N 5/074 (2010.01)
CPC A61K 31/5377 (2013.01) [A61K 31/352 (2013.01); A61K 31/404 (2013.01); A61K 31/438 (2013.01); A61K 31/472 (2013.01); A61K 31/517 (2013.01); C12N 5/0696 (2013.01); C12N 2501/38 (2013.01)] 18 Claims
 
1. A pharmaceutical composition comprising:
(A) a compound of the formula:

OG Complex Work Unit Chemistry
wherein:
n is 0, 1, or 2;
R1 is hydrogen or -L-Ra, wherein:
L1 is a covalent bond, —C(O)—, —S(O)2—, -alkanediyl(C≤6)—C(O)—, -alkanediyl(C≤6)—C(O)—, -alkanediyl(C≤6)—S(O)2—, or substituted -alkanediyl(C≤6)—S(O)2—;
Ra is aryl(C≤12), heteroaryl(C≤12), or a substituted version of any of these groups; or
a group of the formula:

OG Complex Work Unit Chemistry
wherein:
 n is 1 or 2;
 Rb is amino, halo, hydrogen, or hydroxy; or
 alkyl(C≤12), alkylamino(C≤12), dialkylamino(C≤12), alkoxy(C≤12), or a substituted version of any of these groups;
R2 is hydrogen or -L1-Ra, wherein:
L1 is a covalent bond, —C(O)—, —S(O)2—, -alkanediyl(C=6)—C(O)—, substituted-alkanediyl(C≤6)—C(O)—, -alkanediyl(C≤6)—S(O)2″, or substituted -alkanediyl(C≤6)—S(O)2—;
Ra is alkyl(C≤12), acyl(C≤12), amido(C≤12), or a substituted version of any of these groups;
R3 is alkyl(C≤12), cycloalkyl(C≤12), heterocycloalkyl(C≤12), or a substituted version of any of these groups;
R4 is amino, halo, hydrogen, or hydroxy; or alkyl(C≤12), alkylamino(C≤12), dialkylamino(C≤12), alkoxy(C≤12), —NH-aralkyl(C≤12), —NH-heteroaralkyl(C≤12), —O-aralkyl(C≤12), —O-heteroaralkyl(C≤12), or a substituted version of any of these groups;
R5 is, in each instance independently, amino, halo, or hydroxy; or alkyl(C≤12), alkylamino(C≤12), dialkylamino(C≤12), alkoxy(C≤12), or a substituted version of any of these groups; and
X1, X2, X3, X4, and X5 are each independently N or CH;
or a pharmaceutically acceptable salt thereof; and
(B) an excipient.