US 7,501,419 B2
4-Squarylpiperazine derivatives as antiviral agents
Carol Bachand, Candiac (Canada); Daniel H. Deon, Brossard (Canada); and Edward H. Ruediger, Greenfield Park (Canada)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on Apr. 19, 2007, as Appl. No. 11/737,354.
Claims priority of provisional application 60/794699, filed on Apr. 25, 2006.
Prior Publication US 2007/0249624 A1, Oct. 25, 2007
Int. Cl. A61K 31/496 (2006.01); C07D 295/192 (2006.01); C07D 403/12 (2006.01); C07D 405/12 (2006.01); C07D 487/04 (2006.01)
U.S. Cl. 514—253.04  [514/254.09; 544/230; 544/362; 544/373] 7 Claims
 
1. A compound of Formula I, or pharmaceutically acceptable salts thereof,

OG Complex Work Unit Drawing
wherein: X is CH or N;
R1 is F or methoxy;
R2 is methoxy, Cl, Br, or heteroaryl wherein said heteroaryl is optionally substituted with one or two of the same or different members selected from the group consisting of amino, nitro, cyano, hydroxy, C1-6 alkoxy, —C(O)NH2, C1-6 alkyl, —NHC(O)CH3, halogen, and trifluoromethyl;
R3 is H or methyl;
R4 is H or methyl;
R5 is alkyl, aryl, heteroaryl, OR6, or NR6R7;
R6 and R7 are each independently selected from the group consisting of H, C1-C6 alkyl and C3-C6 cycloalkyl, wherein said C3-C6 cycloalkyl can fuse with phenyl or pyridine; R6 and R7 can optionally be joined by C, O, N or S atom, among which the junctioning C and N atom can be substituted with C1-C6 alkyl, C3-C6 cycloalkyl group or junctioning C atom can be a part of C3-C6 cycloalkyl group.