US 11,739,047 B2
Alpha-truxillic acid derivatives and pharmaceutical compositions thereof
Iwao Ojima, Port Jefferson, NY (US); Dale Deutsch, Stony Brook, NY (US); Martin Kaczocha, Dix Hills, NY (US); Kongzhen Hu, Port Jefferson, NY (US); Simon Tong, Great Neck, NY (US); Matthew Elmes, Stony Brook, NY (US); and Su Yan, Stony Brook, 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 Feb. 11, 2021, as Appl. No. 17/174,030.
Application 17/174,030 is a division of application No. 16/080,493, granted, now 10,968,163, previously published as PCT/US2017/021711, filed on Mar. 10, 2017.
Claims priority of provisional application 62/307,262, filed on Mar. 11, 2016.
Prior Publication US 2021/0179535 A1, Jun. 17, 2021
Int. Cl. C07C 69/753 (2006.01); C07C 61/04 (2006.01); C07C 69/757 (2006.01); C07C 205/55 (2006.01); C07D 249/06 (2006.01); C07D 309/06 (2006.01); C07C 233/25 (2006.01); C07D 215/06 (2006.01)
CPC C07C 69/753 (2013.01) [C07C 61/04 (2013.01); C07C 69/757 (2013.01); C07C 205/55 (2013.01); C07C 233/25 (2013.01); C07D 215/06 (2013.01); C07D 249/06 (2013.01); C07D 309/06 (2013.01); C07C 2601/04 (2017.05); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05); C07C 2602/10 (2017.05); C07C 2603/18 (2017.05)] 20 Claims
 
1. A method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound having the structure:

OG Complex Work Unit Chemistry
wherein
one of R1 or R2 is —C(═O)OH and the other of R1 or R2 is —C(═O)OR13 or —C(═O)O-alkyl-R14,
wherein
R13 is cycloalkyl, aryl or heteroaryl, and
R14 is CF3, cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and
R3, R4, R5, R6, Ry, R8, R9, R10, R11 and R12 are each independently, H—OR15 or halogen
wherein R15 is H, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, aryl, or heteroaryl,
wherein when one of R1 or R2 is —C(═O)OH and R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each H, then the other of R1 or R2 is other than —C(═O)OR13 where R13 is 1-naphthyl or 2-naphthyl or —C(═O)O-alkyl-R14 where the alkyl is a branched C2 alkyl and the R14 is phenyl,
or an enantiomer or racemate thereof;
or a pharmaceutically acceptable salt thereof.