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US 2003/0191136 A1Published application
Melanin concentrating hormone receptor ligands
AssigneeNeurogen Corporation
InventorsRajagopal Bakthavatchalam, Andrew Thurkauf, Alan Hutchison
Life of this patent
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Abstract
Disclosed are compounds of the formula: 1 and the pharmaceutically acceptable salts thereof wherein Q, X, Y, Z, and R1 R9, and R12-R19 are defined herein. These compounds are selective modulators of MCH 1 receptors that are, therefore, useful in the treatment of a variety of metabolic, feeding, and sexual disorders. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also disclosed.
Claims47
A compound of the formula:
- 19
- or a pharmaceutically acceptable salt thereof wherein:
- Q represents a group of the Formula:
- 20
- wherein A is C1-C5 alkylene optionally mono-, di, or trisubstituted with substitutuents independently chosen from C1-C3 alkyl, C1-C3 alkoxy, halogen, halo(C1-C3)alkyl, halo(C1-C3)alkoxy, hydroxy, amino, and mono- or di(C1-C3)alkylamino;
- R1, R2, R3, R4, R5, R6, R7, and R8 are the same or different and represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkyl amino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —SO2NH2, mono or dialkylsulfonamido, —C(O)NH2, or mono or di(C1-C6)alkylcarboxamido;
- R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 independently represent hydrogen or C1-C6 alkyl;
- W is nitrogen or C—Ra where Ra represents hydrogen, hydroxy, C1-C6 alkoxy, C1-C6 alkyl or cyano;
- X represents halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkylamino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —CONH2, mono- or di(C1-C6)alkylcarboxamido, —SO2NH2, mono or di(C1-C6)alkylsulfonamido;
- or
- X represents phenyl which may be optionally substituted with up to five substituents, which aree the same or different and are selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkyl amino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —CONH2, mono- or di-(C1-C6)alkylcarboxamido, —SO2NH2, and mono or di(C1-C6)alkylsulfonamido;
- Y is oxygen, sulfur, —S(O)—, or —SO2—;
- and
- Z is C1-C6 alkyl or mono, di or trifluoromethyl.
11 more elements
A compound of the formula:
- 25
- wherein:
- Q represents a group of the Formula:
- 26
- wherein A is C1-C5 alkylene optionally mono-, di, or trisubstituted with substitutuents independently chosen from C1-C3 alkyl, C1-C3 alkoxy, halogen, halo(C1-C3)alkyl, halo(C1-C3)alkoxy, hydroxy, amino, and mono- or di(C1-C3)alkylamino;
- R1, R2, R3, R4, R5, R6, R7, and R8 are the same or different and represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkyl amino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —SO2NH2, mono or dialkylsulfonamido, —C(O)NH2, or mono or di(C1-C6)alkylcarboxamido;
- R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 independently represent hydrogen or C1-C6 alkyl;
- W is nitrogen or C—Ra where Ra represents hydrogen, hydroxy, C1-C6 alkoxy, C1-C6 alkyl or cyano;
- X represents halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkylamino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —CONH2, mono- or di(C1-C6)alkylcarboxamido, —SO2NH2, mono or di(C1-C6)alkylsulfonamido;
- or
- X represents phenyl which may be optionally substituted by up to five substituents, which may be the same or different and are selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy, amino, mono or di(C1-C6)alkyl amino, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, —COOH, —CONH2, mono- or di-(C1-C6)alkylcarboxamido, —SO2NH2, and mono or di(C1-C6)alkylsulfonamido;
- Y is oxygen, sulfur, —S(O)—, or —SO—;
- and
- Z is C1-C6 alkyl or mono, di or trifluoromethyl.
11 more elements
Dependencies are inferred from the claim text.