US 7,498,327 B2
Indolylalkylamine metabolites as 5-hydroxytryptamine-6 ligands
Youchu Wang, St. Laurent (Canada); Chia-Cheng Shaw, St. Laurent (Canada); Ronald Charles Bernotas, Royersford, Pa. (US); Chung-Chiee Paul Wang, Plainsboro, N.J. (US); Ping Cai, New City, N.Y. (US); and Zhi Wang, Malvern, Pa. (US)
Assigned to Wyeth, Madison, N.J. (US)
Filed on Jun. 22, 2005, as Appl. No. 11/158,702.
Claims priority of provisional application 60/582290, filed on Jun. 23, 2004.
Prior Publication US 2006/0003945 A1, Jan. 05, 2006
Int. Cl. C07D 513/04 (2006.01); C07D 209/08 (2006.01); C07D 471/04 (2006.01); A61K 31/4162 (2006.01); A61P 25/18 (2006.01)
U.S. Cl. 514—233.2  [514/368; 514/300; 514/360; 514/254.02; 548/154; 548/151; 546/121; 544/318; 544/133] 20 Claims
 
1. A compound of formula I

OG Complex Work Unit Drawing
wherein
Q is CO2R5 or CH2NR6COR7;
R1 is H or C1-C6alkyl;
R2 is an aryl or heteroaryl group each optionally substituted or an optionally substituted 8- to 13-membered bicyclic or tricyclic ring system having a N atom at the bridgehead and optionally containing 1, 2 or 3 additional heteroatoms selected from N, O or S;
R3 and R4 are each independently H, halogen, CN, OCO2R8, CO2R9, CONR10R11, CNR12NR13R14, SOmR15, NR16R17, OR18, COR19 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted;
R5 and R6 are each independently H or C1-C6alkyl;
R7 is C1-C6alkyl or

OG Complex Work Unit Drawing
m is 0 or an integer of 1 or 2;
R8, R9, R15 and R19 are each independently H or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted;
R10, R11 and R18 are each independently H or a C1-C6alkyl, aryl or heteroaryl group each optionally substituted or R10 and R11 may be taken together with the atom to which they are attached to form a 5- to 7-membered ring optionally containing another heteroatom selected from O, N or S; and
R12, R13, R14, R16 and R17 are each independently H or a C1-C4alkyl, aryl or heteroaryl group each optionally substituted; or R13 and R14 or R16 and R17 may be taken together with the atom to which they are attached to form a 5- to 7-membered ring optionally containing another heteroatom selected from O, N or S; or
a stereoisomer thereof or a pharmaceutically acceptable salt thereof.