US 7,524,867 B2
Tetrasubstituted imidazole derivatives as cannabinoid CB1 receptor modulators with a high CB1/CB2 receptor subtype selectivity
Josephus H. M Lange, Weesp (Netherlands); Henderik C. Wals, Weesp (Netherlands); and Cornelis G. Kruse, Weesp (Netherlands)
Assigned to Solvay Pharmaceuticals, B.V., Weesp (Netherlands)
Filed on May 27, 2005, as Appl. No. 11/138,289.
Claims priority of provisional application 60/574939, filed on May 28, 2004.
Prior Publication US 2005/0267161 A1, Dec. 01, 2005
Int. Cl. A61K 31/445 (2006.01); A61K 31/4164 (2006.01); C07D 401/12 (2006.01); C07D 403/12 (2006.01)
U.S. Cl. 514—326  [546/184; 546/192; 546/207; 546/208; 546/210; 548/300.1; 548/311.1; 548/314.7; 514/385; 514/396; 514/397; 514/315] 11 Claims
 
1. An imidazole compound of formula (I), or a tautomer, a prodrug, or a stereoisomer thereof, or a pharmacologically acceptable salt of any of the foregoing:

OG Complex Work Unit Drawing
wherein:
R1 is chosen from a chlorine atom, a bromine atom, a fluorine atom, and a hydrogen atom,
R2 is chosen from a chlorine atom, a bromine atom, and a CF3 group,
A is chosen from a nitrogen atom and a CH group,
X is chosen from a sulphur atom, a sulfoxide (S═O) moiety, and a sulfone (SO2) moiety,
Y is chosen from a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a trifluoromethyl group, a phenyl group, a benzyl group, and a pyridyl group,
Z is chosen from a nitrogen atom and a CH group, and
n is an integer ranging from 1 to 3.