US 6,982,267 B2 | ||
Heteroaryl urea neuropeptide Y Y5 receptor antagonists | ||
Andrew Stamford, Chatham, N.J. (US); Youhao Dong, Keasbey, N.J. (US); Stuart W. McCombie, Caldwell, N.J. (US); and Yusheng Wu, New York, N.Y. (US) | ||
Assigned to Schering Corporation, Kenilworth, N.J. (US) | ||
Filed on Dec. 18, 2001, as Appl. No. 10/26,651. | ||
Claims priority of provisional application 60/257308, filed on Dec. 21, 2000. | ||
Prior Publication US 2003/0055062 A1, Mar. 20, 2003 | ||
Int. Cl. C07D 241/26 (2006.01); C07D 409/04 (2006.01); A61K 31/4965 (2006.01); A61K 31/497 (2006.01); A61K 3/04 (2006.01) |
U.S. Cl. 514—255.05 | 16 Claims |
1. A compound of Formula I: ![]() or a pharmaceutically acceptable salt of said compound, or where applicable, a geometric or optical isomer or racemic mixture
thereof,
wherein
=A-B= is ═C(R4)—N═ and —X═Y— is —N═C(R6)—,
or =A-B= is —N—C(R6)—, and —X═Y— is —C(R4)═N—
Z is
![]() R1 is H or —(C1-C6)alkyl;
R2 is H, —(C1-C6)alkyl, —(C3-C7)cycloalkyl or —(C1-C6)alkyl(C3-C7)cycloalkyl;
![]() Q is —OR13, or —NR13R14;
j is 1 or 2;
k is 0, 1 or 2;
l is 0, 1 or 2;
m is 0, 1 or 2;
R4, R5, R6 and R7 may be the same or different, and are independently selected from the group consisting of H, —OH, halogen, polyhaloalkyl,
—(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C1-C6)alkyl(C3-C7)cycloalkyl, —CN, NR10R11, NR13R14, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C1-C6)alkyl(C3-C7)cycolalkyl, —S(C1-C6)alkyl, —S(C3-C7)cycloalkyl and —S(C1-C6)alkyl(C3-C7)cycloalkyl;
R8 is 1 to 3 substituents, which may be the same or different, and are independently selected from the group consisting of H,
halogen, —OH, polyhaloalkyl, polyhaloalkoxy, —CN, —NO2, —(C1-C6)alkyl, —(C3-C7)cycloalkyl,—(C1-C6)alkyl(C3-C7)cycloalkyl, NR10R11, NR13R14, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C1-C6)alkyl(C3-C7)cycloalkyl and —CONR13R14;
R9 is —SO2(C1-C6)alkyl, —SO2(C3-C7)cycloalkyl, —SO2(C1-C6)alkyl (C3-C7)cycloalkyl, —SO2(C1-C6)polyhaloalkyl, —SO2[hydroxy(C2-C6)alkyl], —SO2[amino(C2-C6)alkyl], —SO2[alkoxy(C2-C6)alkyl], —SO2[alkylamino(C2-C6)alkyl], —SO2[dialkylamino(C2-C6)alkyl], —SO2(aryl), —SO2(heteroaryl), —SO2[aryl(C1-C6) alkyl], —SO2NR13R14, —CO(C1-C6)alkyl, —CO(C3-C7)cycloalkyl, —CO(C1-C6)alkyl(C3-C7)cycloalkyl, CO(C1-C6)polyhaloalkyl, —C(O)aryl, —C(O)heteroaryl, —CONR13R14, —C(S)NR13R14, aryl, heteroaryl, —(CH2)CONR13R14, —C(═NCN)alkylthio, —C(═NCN)NR13R14, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C1-C6)alkyl(C3-C7)cycloalkyl, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl or —COOR12;
R10 is H or alkyl;
R11 is H, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C1-C6)alkyl(C3-C7)cycloalkyl, aryl, heteroaryl, —SO2(C1-C6)alkyl, —SO2(C3-C7)cycloalkyl, —SO2(C1-C6)alkyl(C3-C7)cycloalkyl, —SO2(C1-C6)polyhaloalkyl, —SO2(aryl), —SO2(heteroaryl), —CO(C1-C6)alkyl, —CO(C3-C7)cycloalkyl, —CO(C1-C6)alkyl(C3-C7)cycloalkyl, —C(O)aryl, —C(O)heteroaryl, —CONR13R14 or —COOR12;
R12 is (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)alkyl(C3-C7)cycloalkyl, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl, aryl or heteroaryl;
R13 and R14 may be the same or different and are independently H, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C1-C6)alkyl(C3-C7)cycloalkyl, —(C1-C6)alkylaryl, aryl or heteroaryl; and,
R15 is one or two substituents, which may be the same or different, and are independently H, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C1-C6)alkyl(C3-C7)cycloalkyl, aryl, heteroaryl, —CN, —CONR13R14, —COOR13, —OH, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C1-C6)alkyl(C3-C7)cycloalkyl, —NR10R11, —NR13R14, or a —(C1-C6)alkyl group substituted by an aryl, heteroaryl, hydroxy, alkoxy, —NR10R11, —NR13R14, —CONR13R14, or —COOR13 group, provided that a chemically stable compound results from substitution by R15.
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