US 7,524,878 B2
Phenyl substituted carboxylic acids
Darren Whitehouse, Westbrook, Conn. (US); Shaojing Hu, Hamden, Conn. (US); Haiquan Fang, Madison, Conn. (US); and Michael C. Van Zandt, Guilford, Conn. (US)
Assigned to The Institute for Pharmaceuticals Discovery LLC, Branford, Conn. (US)
Filed on Apr. 30, 2004, as Appl. No. 10/835,924.
Claims priority of provisional application 60/466868, filed on Apr. 30, 2003.
Prior Publication US 2005/0004369 A1, Jan. 06, 2005
Int. Cl. A61K 31/341 (2006.01); A61K 31/404 (2006.01); C07D 209/04 (2006.01); C07D 307/79 (2006.01)
U.S. Cl. 514—419  [514/468; 514/469; 548/490; 549/461; 549/462] 50 Claims
 
1. A compound of the formula:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein,
R1 is H, C1-C6 alkyl, phenyl(C1-C6)alkyl, or C2- C6 alkenyl;
L2 is a bond;
L3 is a bond, —(C1-C4)alkyl-O—, —O—(C1-C4)alkyl, —(C1-C4) alkyl-, -alkenyl-, or -phenyl-;
L5 is —N(R9)C(O)—(C1-C4) alkyl- or —N(R9)SO2—(C1-C4)alkyl-, wherein
R9 is H, C1-C6 alkyl, C1-C6 alkoxycarbonyl, —SO2-aryl, heteroarylalkyl, or arylalkyl, wherein the aryl or heteroaryl groups are optionally substituted with 1, 2, 3, or 4 groups that are independently C1-C4 alkyl, C1-C4 alkoxy, halogen, OH, NO2, NH2, NH(C1-C6)alkyl, N(C1-C6)alkyl(C1-C6)alkyl, haloalkyl, or haloalkoxy;
R20, R21, R22, and R23 are independently selected from H, arylalkoxy, arylalkyl, halogen, alkyl, alkoxy, NO2, NH2, CN, NH(C1-C6)alkyl, N(C1-C6)alkyl (C1-C6)alkyl, NH-aryl, NHC(O)—(C1-C4) alkyl-aryl, N(C1-C4 alkyl)C(O)—(C1-C4) alkyl-aryl, N(C1-C4)alkyl-aryl, —NHSO2-aryl, and —N(C1-C4alkyl)SO2-aryl, wherein the aryl group is optionally substituted with 1, 2, 3, 4, or 5 groups that are independently C1-C6 alkyl, C1-C6 alkoxy, halogen, OH, NO2, haloalkyl, or haloalkoxy;
the A ring is phenyl, which is optionally substituted with 1, 2, or 3 groups that are independently, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, NO2, NH2, NH(C1-C6)alkyl, or N(C1-C6)alkyl(C1-C6)alkyl;
Q is aryl, aryl-carbonyl-aryl, -aryl-O-aryl, -aryl-alkyl-aryl, -aryl-heteroaryl, -aryl-heterocycloalkyl, heteroaryl, or -heteroaryl-alkyl-aryl, wherein the aforementioned cyclic groups are optionally substituted with 1, 2, 3, 4, or 5 groups that are independently alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, halogen, haloalkyl, haloalkoxy, NR6R7, phenyl, phenyl-C1-C6 alkyl-, or phenyloxy-; wherein
R6 and R7 are independently H, C1-C6 alkyl, aryl(C1-C6)alkyl, C2-C6 alkanoyl, aryl C2-C6 alkanoyl, C1-C6 alkoxycarbonyl, aryl C1-C6 alkoxycarbonyl, heteroarylcarbonyl, heteroaryl, heterocycloalkylcarbonyl, —C(O)NH2, —C(O)NH(C1-C6)alkyl, —C(O)N(C1-C6)alkyl(C1-C6)alkyl, or —SO2-aryl, wherein the cyclic groups are optionally substituted with 1, 2, 3, or 4 groups that are independently halogen, C1-C4 alkyl, C1-C4 alkoxy, NO2, OH, NH2, NH(C1-C6)alkyl, N(C1-C6)alkyl(C1-C6)alkyl, haloalkyl or haloalkoxy; and
Z is absent, H, —NHC(O)aryl, —N(C1-C4 alkyl)C(O)aryl, or aryl, wherein the aryl groups are optionally substituted with 1, 2, 3, 4, or 5 groups that are independently C1-C6 alkyl, C1-C6 alkoxy, halogen, haloalkyl, haloalkoxy, or NO2, or
Z is —NHC(O)—(C1-C4)alkyl-(C3-C7)cycloalkyl, or —N(C1-C4)alkyl-C(O)—(C1-C4)alkyl-(C3-C7)cycloalkyl.