US 9,808,448 B2
Pharmaceutical compounds and use of same in cancer and tauopathies
Jason E. Gestwicki, Moss Beach, CA (US); and Chad Dickey, Tampa, FL (US)
Assigned to REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US); and UNIVERSITY OF SOUTH FLORIDA, Tampa, FL (US)
Filed by THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US); and UNIVERSITY OF SOUTH FLORIDA, Tampa, FL (US)
Filed on Apr. 11, 2017, as Appl. No. 15/484,445.
Application 15/484,445 is a division of application No. 14/770,850, granted, now 9,642,843, previously published as PCT/US2014/018843, filed on Feb. 27, 2014.
Claims priority of provisional application 61/769,942, filed on Feb. 27, 2013.
Prior Publication US 2017/0273963 A1, Sep. 28, 2017
Int. Cl. A61K 31/395 (2006.01); A61K 31/428 (2006.01); A61K 31/4439 (2006.01); A61K 38/05 (2006.01); C07D 277/64 (2006.01); C07D 417/14 (2006.01)
CPC A61K 31/4439 (2013.01) [A61K 31/395 (2013.01); A61K 31/428 (2013.01); A61K 38/05 (2013.01); C07D 277/64 (2013.01); C07D 417/14 (2013.01)] 18 Claims
 
1. A method of treating a subject suffering from cancer comprising administering to the subject a compound or salt thereof in an amount effective to treat the cancer, wherein the compound or salt thereof has a structure of Formula (I) or (III):

OG Complex Work Unit Drawing
R1, R2, and R3 are each selected from the group consisting of hydrogen, fluoro, chloro, methoxy, and trifluoromethyl,
R4 and R5 are each selected from the group consisting of hydrogen, fluoro, and chloro,R6 is C1-C4 alkyl or CH2Ar;Ar is aryl;R7 is ethyl, allyl, or benzyl;X is a pharmaceutically acceptable anion, and m is 1, 2, or 3;with the proviso that
(1) if R6 is alkyl, R7 is ethyl, and each of R4 and R5 is hydrogen, then at least one of R1, R2, and R3 is other than hydrogen;
(2) when each of R1, R2, R3, R4, and R5 is hydrogen R6 is CH2Ar; and
(3) when the compound has a structure of Formula (III) and R7 is ethyl, at least one of R4 and R5 is other than hydrogen.