US 7,605,289 B2
Benzamide derivatives and uses related thereto
Jay P. Powers, Pacifica, Calif. (US); Michael Degraffenreid, San Francisco, Calif. (US); Xiao He, Foster City, Calif. (US); Lisa Julian, Redwood City, Calif. (US); Dustin L. McMinn, Pacifica, Calif. (US); Daqing Sun, Foster City, Calif. (US); Yosup Rew, Foster City, Calif. (US); and Xuelei Yan, Burlingame, Calif. (US)
Assigned to Amgen, Inc., Thousand Oaks, Calif. (US)
Filed on Jun. 08, 2006, as Appl. No. 11/448,986.
Claims priority of provisional application 60/691244, filed on Jun. 17, 2005.
Prior Publication US 2006/0293392 A1, Dec. 28, 2006
Int. Cl. C07C 233/65 (2006.01); A61K 31/165 (2006.01)
U.S. Cl. 564—177  [564/176; 548/530; 546/225; 544/358; 540/484; 514/617; 514/423; 514/330; 514/247; 514/231.2; 514/212.01] 42 Claims
 
1. A compound having formula (I):

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt, or stereoisomer thereof, wherein:
R1 is a member selected from the group consisting of —OH, halogen and (C1-C6)haloalkyl;
R2 and R3 are members independently selected from the group consisting of halogen, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl and (C3-C8)cycloalkyl, wherein no more than two of R1, R2 and R3 are halogen;
R4 is a member selected from the group consisting of hydrogen, halogen, (C1-C8)alkyl and (C3-C8)cycloalkyl;
R5 is selected from the group consisting of halogen, —CN, —NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, (C3-C8)heterocycloalkyl, (C3-C8)cycloalkyl(C1-C6)alkyl, (C3-C8)cycloalkyl(C1-C6)alkoxy, (C3-C8)heterocycloalkyl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl, aryl, aryl(C1-C6)alkyl, —C(O)R′, —C(O)OR′, —NR′C(O)OR″, —OR″, —OC(O)R′, —C(O)N(R′)2, —S(O)R″, —SO2R″, —SO2N(R′)2, —N(R′)2, —NR′C(O)R′, —NR′SO2R″, —X—C(O)R′, —X—C(O)OR′, —X—NR′C(O)OR″, —X—OR″, —X—OC(O)R′, —X—C(O)N(R′)2, —X—S(O)R″, —X—SO2R″, —X—SO2N(R′)2, —X—N(R′)2 and —X—NR′C(O)R′;
R6 is selected from the group consisting of halogen, —CN, —NO2, methyl, ethyl, straight or branched butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight or branched octyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, (C3-C8)heterocycloalkyl, (C3-C8)cycloalkyl(C1-C6)alkyl, (C3-C8)cycloalkyl(C1-C6)alkoxy, (C3-C8)heterocycloalkyl(C1-C6)alkyl, aryl, heteroaryl(C1-C6)alkyl, aryl(C1-C6)alkyl, —C(O)R′, —C(O)OR′, —NR′C(O)OR″, —OR″, —OC(O)R′, —C(O)N(R′)2, —S(O)R″, —SO2R″, —SO2N(R′)2, —N(R′)2, —NR′C(O)R′, —NR′SO2R″, —X—C(O)R″, —X—C(O)OR″, —X—NR′C(O)OR″, —X—OR″, —X—OC(O)R′, —X—C(O)N(R′)2, —X—S(O)R″, —X—SO2R″, —X—SO2N(R′)2, —X—N(R′)2 and —X—NR′C(O)R′;
any cycloalkyl portion, heterocycloalkyl portion, aryl portion or heteroaryl portion is optionally substituted with from one to four members selected from the group consisting of halogen, —CN, —NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl, —C(O)R′, —C(O)OR′, —NR′C(O)OR″, —OR′, —SR′, —OC(O)R′, —C(O)N(R′)2, —S(O)R″, —SO2R″, —SO2N(R′)2, —N(R′)2, —NR′C(O)R′ and —NR′SO2R″;
X is a branched or straight chain (C1-C8)alkylene group;
each occurrence of R′ is independently H or an unsubstituted member selected from the group consisting of (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)alkoxy(C1-C4)alkyl, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, (C3-C8)heterocycloalkyl, heteroaryl, aryl, (C3-C8)cycloalkyl(C1-C6)alkyl, (C3-C8)heterocycloalkyl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl, aryl(C1-C6)alkyl, or two R′ groups, when attached to the same nitrogen atom, can be combined with the nitrogen atom to which they are attached to form a heterocycle or heteroaryl group; and
each occurrence of R″ is independently an unsubstituted member selected from the group consisting of (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)alkoxy(C1-C4)alkyl, (C1-C6)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, (C3-C8)heterocycloalkyl, heteroaryl, aryl, (C3-C8)cycloalkyl(C1-C6)alkyl, heterocyclyl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl or aryl(C1-C6)alkyl;
with the proviso that when R1 is —OH, then R2 and R3 are not both CF3.