US 7,402,704 B2
Arylsulfones and uses related thereto
Pingchen Fan, Fremont, Calif. (US); Hiroyuki Goto, Takatsuki (Japan); Xiao He, Foster City, Calif. (US); Makoto Kakutani, Takatsuki (Japan); Marc Labelle, Chatham, N.J. (US); Dustin L. McMinn, Pacifica, Calif. (US); Jay P. Powers, Pacifica, Calif. (US); Yosup Rew, Foster City, Calif. (US); Daqing Sun, Foster City, Calif. (US); and Xuelei Yan, Burlingame, Calif. (US)
Assigned to Amgen Inc., Thousand Oaks, Calif. (US)
Filed on Apr. 14, 2005, as Appl. No. 11/105,583.
Claims priority of provisional application 60/563251, filed on Apr. 14, 2004.
Prior Publication US 2005/0277665 A1, Dec. 15, 2005
Int. Cl. C07C 317/14 (2006.01); A61K 31/255 (2006.01); A61K 31/275 (2006.01)
U.S. Cl. 568—28  [568/34; 558/413; 514/518; 514/520] 18 Claims
 
1. A compound having the formula:

OG Complex Work Unit Drawing
or pharmaceutically acceptable salts, solvates, stereoisomers, or prodrugs thereof, wherein:
R1 is a member selected from the group consisting of —OH, halogen and (C1-C8)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-C8)haloalkyl, (C2-C8)hydroxyalkyl and (C3-C8)cycloalkyl, wherein no more than two of R1, R2 and R3 are halogen;
R4, R5, R6, R7 and R8 are each members independently selected from the group consisting of H, halogen, —CN, —NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(C1-C6)alkyl, (C3-C8)cycloalkyl(C1-C6)alkoxy, 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′, —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′; and optionally two of R4, R5, R6, R7 and R8 when attached to adjacent carbon atoms are combined to form a fused 5-, 6- or 7-membered aryl or cycloalkyl ring, and
any fused ring portion, cycloalkyl portion, or aryl is optionally substituted with from one to four members selected from the group consisting of H, halogen, —CN, —NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C8)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 and —NR′C(O)R′;
wherein 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-C8)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, aryl, (C3-C8)cycloalkyl(C1-C6)alkyl, and aryl(C1-C6)alkyl;
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-C8)haloalkyl, (C2-C8)hydroxyalkyl, (C3-C8)cycloalkyl, aryl, (C3-C8)cycloalkyl(C1-C6)alkyl, and aryl(C1-C6)alkyl; and
R9 is H or halogen
with the proviso that the compound is other than 2-{4-[4-(1-Hydroxy-1-methyl-ethyl)-benzenesulfonyl]-phenyl}-propan-2-ol or 1-(1-chloro-1-methylethyl)-4-(phenylsulfonyl)benzene.