US 7,524,839 B2
Compounds, their use and preparation
Patrizia Caldirola, Uppsala (Sweden); Björn M. Nilsson, Stockholm (Sweden); and Gary Johansson, Uppsala (Sweden)
Assigned to Biovitrum AM (publ.),
Filed on Feb. 11, 2005, as Appl. No. 11/57,033.
Application 11/057033 is a continuation of application No. 10/037110, filed on Oct. 22, 2001, granted, now 7,087,750.
Claims priority of provisional application 60/243115, filed on Oct. 25, 2000.
Claims priority of application No. 0003810 (SE), filed on Oct. 20, 2000.
Prior Publication US 2005/0256106 A1, Nov. 17, 2005
Int. Cl. A61P 25/00 (2006.01); A61K 31/404 (2006.01); A61K 31/439 (2006.01); A61K 31/496 (2006.01); C07D 209/08 (2006.01); C07D 453/02 (2006.01); C07D 403/04 (2006.01); C07D 487/04 (2006.01)
U.S. Cl. 514—218  [514/249; 514/252.11; 514/253.04; 514/254.09; 514/305; 514/414; 514/415; 540/575; 544/349; 544/362; 544/373; 546/133; 548/453; 548/469] 26 Claims
 
1. A method for the treatment of obesity, the method comprising administering to a patient in need thereof a therapeutically effective amount of a compound of formula (I):

OG Complex Work Unit Drawing
wherein
Ar is
(1) phenyl,
(2) naphthyl,
(3) a 5- to 10-membered monocyclic or bicyclic heterocyclic ring having 1 to 4 heteroatoms selected from the group consisting of oxygen, sulfur, or nitrogen, or
(4) —R9-phenyl;
wherein the phenyl, naphthyl, or heterocyclic ring is optionally substituted with halogen, C1-6 alkyl, CF3, hydroxyl, C1-6 alkoxyl, OCF3, COCF3, CN, NO2, phenyloxy, phenyl, C1-6 alkylsulfonyl, C2-6 alkenyl, —NR7R8, C1-6 alkylcarboxyl, formyl, —C1-6 alkyl-NH—CO-phenyl, —C1-6 alkyl-CO—NH-phenyl, —NH—CO—C1-6 alkyl, —CO—NR7R8, or SR7; wherein each of R7 and R8 is independently H or C1-6 alkyl; and R9 is C1-6 alkylidene or C2-6 alkenylene, either of which is optionally substituted with phenyl or phenyloxy;
R2 is H, phenyl, I, or C1-6 alkyl;
R3 is H or 3-(1-azabicyclo[2.2.2]oct-2-en)yl;
R4 is H or is selected from the group consisting of:

OG Complex Work Unit Drawing
wherein R6 is H, C1-6 alkyl, or benzyl; and
R5 is H, hydroxy, C1-3 alkoxy, F, NO2, CF3, OCF3, or is selected from the group consisting of:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt, hydrate, or stereoisomer thereof,
with the proviso that when R2 is alkyl, R4 is not H.