US 7,517,893 B2
Bichalcophenes and their prodrugs as antiprotozoal agents
Richard R. Tidwell, Pittsboro, N.C. (US); David W. Boykin, Atlanta, Ga. (US); Chad Stephens, Augusta, Ga. (US); Mohamed A. Ismail, Atlanta, Ga. (US); W. David Wilson, Atlanta, Ga. (US); Reto Brun, Basel (Switzerland); and Karl Werbovetz, Colombus, Ohio (US)
Assigned to The University of North Carolina at Chapel Hill, Chapel Hill, N.C. (US); and Georgia State University Research Foundation, Inc., Atlanta, Ga. (US)
Filed on May 16, 2006, as Appl. No. 11/435,323.
Claims priority of provisional application 60/683177, filed on May 20, 2005.
Prior Publication US 2006/0293540 A1, Dec. 28, 2006
Int. Cl. C07D 401/02 (2006.01); A61K 31/44 (2006.01)
U.S. Cl. 514—336  [514/387; 514/461; 546/268.1; 546/280.4; 546/283.4; 548/304.7; 549/472] 33 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Drawing
wherein:
X1 and X2 are independently selected from the group consisting of O, S, Se, Te, and NR1, wherein R1, is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl;
p is an integer from 0 to 1;
each q is independently an integer from 0 to 2;
each R2 is independently selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, halo, hydroxyl, alkoxyl, aryloxyl, and aralkyloxyl;
Ar1 and Ar2 are independently selected from the group consisting of phenyl, pyridine, and benzimidazole;
Am1 and Am2 are each

OG Complex Work Unit Drawing
wherein:
each R3 is independently selected from the group consisting of H, hydroxyl, acyloxyl, and alkoxyl;
each R4, R5, R6, and R7 is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl; or
R3 and R4 together represent a C2 to C10 alkyl, C2 to C10 hydroxyalkyl, or C2 to C10 alkylene; or
R3 and R4 together are:

OG Complex Work Unit Drawing
wherein s is a number from 1 to 4, and R8 is H or —CONHR9NR10R11, wherein R9 is alkyl, and R10 and R11 are each independently selected from the group consisting of H and alkyl;
or a pharmaceutically acceptable salt thereof.