US 12,325,678 B2
Anti-fungals compounds targeting the synthesis of fungal sphingolipids
Iwao Ojima, Port Jefferson, NY (US); Maurizio Del Poeta, Mount Sinai, NY (US); Cristina Lazzarini, East Setauket, NY (US); Krupanandan Haranahalli, Setauket, NY (US); and Yi Sun, Mount Sinai, NY (US)
Assigned to THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK, Albany, NY (US)
Filed by THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK, Albany, NY (US)
Filed on Dec. 6, 2023, as Appl. No. 18/530,774.
Application 18/530,774 is a division of application No. 17/837,548, filed on Jun. 10, 2022, granted, now 11,858,880, issued on Jan. 2, 2024.
Application 17/837,548 is a division of application No. 16/622,431, granted, now 11,414,378, issued on Aug. 16, 2022, previously published as PCT/US2018/037846, filed on Jun. 15, 2018.
Claims priority of provisional application 62/521,069, filed on Jun. 16, 2017.
Prior Publication US 2024/0124392 A1, Apr. 18, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 251/86 (2006.01); A01N 37/28 (2006.01); A61K 31/195 (2006.01); A61P 31/10 (2006.01); C07D 213/86 (2006.01); C07D 215/54 (2006.01); C07D 239/30 (2006.01); C07D 307/68 (2006.01); C07D 309/08 (2006.01); C07D 333/38 (2006.01); A61K 45/06 (2006.01)
CPC C07C 251/86 (2013.01) [A01N 37/28 (2013.01); A61K 31/195 (2013.01); A61P 31/10 (2018.01); C07D 213/86 (2013.01); C07D 215/54 (2013.01); C07D 239/30 (2013.01); C07D 307/68 (2013.01); C07D 309/08 (2013.01); C07D 333/38 (2013.01); A61K 45/06 (2013.01)] 20 Claims
 
1. A method of treating a subject afflicted with a fungal infection comprising administering to the subject an effective amount of the compound having the following structure:

OG Complex Work Unit Chemistry
wherein
R1 is —H, alkyl, alkenyl, or alkynyl;
R2 is —H, alkyl, alkenyl, or alkynyl;
R3, R4, R5, and R6 are each independently —H, halogen, C1-C6 alkyl, —OH, —O— (C1-C6 alkyl), —CHF2, —CF3, —OCHF2 or —OCF3, or
R3 and R4 are each independently —H, halogen, C1-C6 alkyl, —OH, —O— (C1-C6 alkyl), —CHF2, —CF3, —OCHF2 or —OCF3, and R5 and R6 combine to form a fused aryl or fused heteroaryl, which are each unsubstituted or substituted, or
R3 and R6 are each independently —H, halogen, C1-C6 alkyl, —OH, —O— (C1-C6 alkyl), —CHF2, —CF3, —OCHF2 or —OCF3, and R4 and R5 combine to form a fused aryl or fused heteroaryl, which are each unsubstituted or substitute, or
R5 and R6 are each independently —H, halogen, C1-C6 alkyl, —OH, —O— (C1-C6 alkyl), —CHF2, —CF3, —OCHF2 or —OCF3, and R3 and R4 combine to form a fused aryl or fused heteroaryl, which are each unsubstituted or substituted; and
A is an aryl or heteroaryl, which are each unsubstituted or substituted,
wherein when R3, R4, and R6 are each —H and R5 is —OH or —OCH3, or R3, R5, and R6 are each —H and R4 is —Br, then A is other than ortho-tolyl or meta-bromophenyl.