| US 7,465,809 B2 | ||
| Heterocycle derivatives useful as selective androgen receptor modulators (SARMs) | ||
| Xuqing Zhang, Raritan, N.J. (US); Xiaojie Li, Raritan, N.J. (US); and Zhihua Sui, Raritan, N.J. (US) | ||
| Assigned to Janssen Pharmaceutica N.V., Beerse (Bulgaria) | ||
| Filed on Oct. 25, 2005, as Appl. No. 11/258,448. | ||
| Claims priority of provisional application 60/628337, filed on Nov. 16, 2004. | ||
| Prior Publication US 2006/0211756 A1, Sep. 21, 2006 | ||
| Int. Cl. C07D 231/04 (2006.01); C07D 231/06 (2006.01) | ||
| U.S. Cl. 548—379.4 | 10 Claims |
1. A compound of formula (I)
 W is selected from the group consisting of O, S and NRF; wherein RF is selected from the group consisting of hydrogen, hydroxy, C1-4alkyl, C1-4alkoxy, cyano and —SO2—C1-4alkyl;
R1 is selected from the group consisting of C1-4alkyl and halogenated C1-4alkyl;
R2 is selected from the group consisting of hydrogen, C1-4alkyl, halogenated C1-4alkyl, —C(O)O—C1-4alkyl, —C(O)—C1-4alkyl and —C(O)-(halogenated C1-4alkyl);
a is an integer from 0 to 1;
 is phenyl;
R3 is selected from the group consisting of hydrogen, halogen, C1-4alkyl, halogenated C1-4alkyl, cyano, nitro, amino, benzyl, —O-phenyl, —C(O)-phenyl, —S(O)0-2—C1-4alkyl, C1-4alkylamino, di C1-4alkylamino, —O—C1-4alkyl, —NRA—C(O)—C1-4alkyl and —S(O)0-2-phenyl, wherein RA is either hydrogen or C1-4alkyl;
R4 is selected from the group consisting of hydrogen, halogen, C1-4alkyl, halogenated C1-4alkyl, cyano, nitro, amino, benzyl, —O-phenyl, —C(O)-phenyl, —S(O)0-2—C1-4alkyl, C1-4alkylamino, di C1-4alkylamino, —O—C1-4alkyl, —NRB—C(O)—C1-4alkyl and —S(O)0-2-phenyl, wherein RB is either hydrogen or C1-4alkyl;
provided that at least one of R3 of R4 other than hydrogen;
R6 and R7 are each independently selected from the group consisting of hydrogen, halogen, C1-4alkyl, C2-4alkenyl, C1-4alkoxy, cyano, —C(O)O—C1-4alkyl and —S(O)0-2—C1-4alkyl;
 is selected from the group consisting of
 wherein R5′ is selected from the group consisting of halogen and C1-4alkyl; and wherein R10 is selected from hydrogen, C1-4alkyl, benzyl or —C(O)—CF3;
R5 is selected from the group consisting of hydrogen, carboxy, alkyl, halogenated C1-4alkyl, hydroxy substituted C1-4alkyl, cycloalkyl, aryl, aralkyl, —C(O)—C1-4alkyl, —C(O)-(halogenated C1-4alkyl), —C(O)O—C1-4alkyl, —C(O)O-aryl, —C1-4alkyl-S(O)0-2—C1-4alkyl, t-butyl-dimethyl-silyl and trimethylsilyl;
wherein the aryl, whether alone or as part of a substituent group is optionally substituted with one or more substituents
independently selected from the group consisting of halogen, hydroxy, C1-4alkyl, C1-4alkoxy, halogenated C1-4alkyl, cyano, nitro, —NRC—C(O)—C1-4alkyl, NRC—C(O)-(halogenated C1-4alkyl), —C(O)O—C1-4alkyl, trimethyl-silyl and t-butyl-dimethyl-silyloxy; wherein RC and RD are each independently selected from hydrogen or C1-4alkyl;
or a pharmaceutically acceptable salt thereof.
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