US 12,071,430 B2
Itraconazole analogs and use thereof
Jun Liu, Baltimore, MD (US); Yingjun Li, Baltimore, MD (US); Kalyan Kumar Pasunooti, Baltimore, MD (US); Wukun Liu, Baltimore, MD (US); Wei Shi, Baltimore, MD (US); Ruojing Li, Baltimore, MD (US); and Sarah Head, Baltimore, MD (US)
Assigned to The Johns Hopkins University, Baltimore, MD (US)
Appl. No. 17/282,378
Filed by The Johns Hopkins University, Baltimore, MD (US)
PCT Filed Oct. 3, 2019, PCT No. PCT/US2019/054583
§ 371(c)(1), (2) Date Apr. 1, 2021,
PCT Pub. No. WO2020/072830, PCT Pub. Date Apr. 9, 2020.
Application 17/282,378 is a continuation in part of application No. 16/152,008, filed on Oct. 4, 2018, granted, now 11,028,078.
Application 16/152,008 is a continuation in part of application No. 15/162,524, filed on May 23, 2016, abandoned.
Application 15/162,524 is a continuation of application No. 14/343,040, granted, now 9,346,791, issued on May 24, 2016, previously published as PCT/US2012/054306, filed on Sep. 7, 2012.
Claims priority of provisional application 62/742,046, filed on Oct. 5, 2018.
Claims priority of provisional application 61/531,819, filed on Sep. 7, 2011.
Prior Publication US 2022/0106302 A1, Apr. 7, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/14 (2006.01); A61K 31/496 (2006.01); A61K 31/506 (2006.01); A61P 35/00 (2006.01)
CPC C07D 405/14 (2013.01) [A61P 35/00 (2018.01); A61K 31/496 (2013.01); A61K 31/506 (2013.01)] 13 Claims
OG exemplary drawing
 
1. A compound having a structure according to Formula (I):

OG Complex Work Unit Chemistry
or an optically pure stereoisomer or pharmaceutically acceptable salt thereof,
wherein,
U is

OG Complex Work Unit Chemistry
R1, R2, R3, and R4 are each independently selected from the group consisting of alkoxy, alkyl, alkynyl, amino, amido, halogen, hydroxyl, haloalkyl, perhaloalkyl, perhaloalkoxy, nitro, and cyano, wherein alkoxy, alkyl, and alkynyl are optionally substituted with halogen, hydroxyl, or nitro group;
A is CR5 or N;
B is CR6 or N;
E is CR7 or N;
L is CR8 or N;
R5, R6, R7, and R8 are each independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkynyl, amino, halogen, hydroxyl, haloalkyl, perhaloalkyl, perhaloalkoxy, nitro, and cyano, wherein alkoxy, alkyl, and alkynyl are optionally substituted with halogen, hydroxyl, or nitro group;
G, Q, and T together with the atom(s) to which they are attached joined together to form dioxolane

OG Complex Work Unit Chemistry
m is an integer between 0 and 5;
n and q are each independently an integer between 0 and 2;
p is an integer between 0 and 4;
D is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein,
custom character is a single or double bond;
R10 is selected from the group consisting of hydrogen, alkyl, arylalkyl, alkoxyalkyl, arylalkoxy, alkynylalkyl, alkylalkynylalkyl, alkenylalkyl, alkylalkenylalkyl, cycloalkyl, cyanoalkyl, cycloalkylalkyl, heteroalkyl, heterocycloalkyl, heteroaryl, heteroarylalkyl, heterocycloalkylalkyl, and alkylsulfonyl, any of which can be optionally substituted with halogen, hydroxyl, or nitro group;
I is (CH2)r or NH;
J is (CH2)s or NH;
K is (CH2)t or NH; and
r, s, and t are each independently an integer between 0 and 4.