US 12,435,067 B2
Truncated itraconazole analogues and methods of use thereof
Matthew Kyle Hadden, Ellington, CT (US)
Assigned to UNIVERSITY OF CONNECTICUT, Farmington, CT (US)
Appl. No. 17/633,679
Filed by University of Connecticut, Farmington, CT (US)
PCT Filed Aug. 7, 2020, PCT No. PCT/US2020/045341
§ 371(c)(1), (2) Date Feb. 8, 2022,
PCT Pub. No. WO2021/030174, PCT Pub. Date Feb. 18, 2021.
Claims priority of provisional application 62/884,988, filed on Aug. 9, 2019.
Prior Publication US 2022/0324849 A1, Oct. 13, 2022
Int. Cl. C07D 405/12 (2006.01); A61P 35/00 (2006.01); C07D 317/22 (2006.01)
CPC C07D 405/12 (2013.01) [A61P 35/00 (2018.01); C07D 317/22 (2013.01)] 15 Claims
 
1. A compound having the structure of Formula (Ia-1), (Ia-2), (Ia-3), or (Ia-4)

OG Complex Work Unit Chemistry
wherein
Q is O;
R1 is methyl;
R4 is chloro;
n is 2; and
one of a), b), or c):
a) J1 and J2 are absent and R3 is H;
b) J1 is —C(═O)— or —C(═O)NH—N═CH—;
J2 is absent, C1-4 alkyl, or C2-4 alkenyl; and
R3 is unsubstituted or substituted phenyl or pyridyl; or
c) J1 is absent; J2 is C3-4 alkyl; and R3 is unsubstituted or substituted phenyl;
wherein each substituted phenyl or pyridyl individually is substituted with 1, 2, or 3 substituents, each substituent is independently C1-6 alkyl, halo, —OH, —COOH, cyano, nitro, amino, C1-6 monoalkylamine, C1-6 dialkylamine, C1-6 haloalkyl, or C1-6 haloalkoxy; or
a pharmaceutically acceptable salt, a stereoisomeric form thereof, or a combination thereof.