US 11,858,880 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 Hanarahalli, 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 Jun. 10, 2022, as Appl. No. 17/837,548.
Application 17/837,548 is a division of application No. 16/622,431, granted, now 11,414,378, 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 2022/0394973 A1, Dec. 15, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 251/86 (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); A01N 37/28 (2006.01); A61K 31/195 (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 inhibiting the growth of a fungus comprising contacting the fungus with an effective amount of the compound having the 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,
or a pharmaceutically acceptable salt or ester thereof, so as to thereby inhibit the growth of the fungus.