Claims
- 1. A compound according to formula (I),
- 2. A compound according to formula (Ia),
- 3. The compound according to claim 2, that is a member selected from the group consisting of
2-(((8-(1,3,3-trimethylbutoxy)quinolin-2-yl)amino)carbonyl)benzyl benzoate; N-(3-((2-aminoquinolin-8-yl)oxy)propyl)-8-(1,3,3-trimethylbutoxy)quinolin-2-amine;
- 4. A compound according to formula (Ib),
- 5. The compound according to claim 4, that is a member selected from the group consisting of
8-(1,3,3-trimethylbutoxy)quinolin-2-amine; 8-(2-ethyl-1-methylbutoxy)quinolin-2-amine; 8-(hexyloxy)quinolin-2-amine; 8-(3,3-dimethylbutoxy)quinolin-2-amine; 8-((1-ethylpentyl)oxy)quinolin-2-amine; 8-(1-ethyl-2-methylpropoxy)quinolin-2-amine; 8-(1,2-diethylbutoxy)quinolin-2-amine; 8-((1,4-diethylhexyl)oxy)quinolin-2-amine; 8-(1,3-dimethylbutoxy)quinolin-2-amine; 8-((1-isopropylpentyl)oxy)quinolin-2-amine; 8-((1-ethyl-4-methylpentyl)oxy)quinolin-2-amine; N-methyl-8-(1,3,3-trimethylbutoxy)quinolin-2-amine; N-propyl-8-(1,3,3-trimethylbutoxy)quinolin-2-amine; 8-(((1R)-1,3,3-trimethylbutyl)oxy)quinolin-2-amine; 8-(((1S)-1,3,3-trimethylbutyl)oxy)quinolin-2-amine; and 3-methyl-8-(1,3,3-trimethylbutoxy)quinolin-2-amine.
- 6. A compound according to formula (Ic),
- 7. The compound according to claim 6, that is a member selected from the group consisting of
8-(2-methoxy-1-methylethoxy)quinolin-2-amine; 8-(2-ethoxy-1-methylethoxy)quinolin-2-amine; 8-(3-methoxy-3-methylbutoxy)quinolin-2-amine; 8-(1-(methoxymethyl)propoxy)quinolin-2-amine; 8-(3-ethoxy-1-ethylpropoxy)quinolin-2-amine; 8-(3-methoxybutoxy)quinolin-2-amine; 8-(3,3,3-trifluoropropoxy)quinolin-2-amine; 8-(2-(methylthio)ethoxy)quinolin-2-amine; 4-((3-((2-aminoquinolin-8-yl)oxy)propyl)amino)-6-methyl-2H-chromen-2-one; and 4-((3-((2-aminoquinolin-8-yl)oxy)propyl)amino)-6-chloro-2H-chromen-2-one.
- 8. A compound according to formula (Id),
- 9. The compound according to claim 8, that is a member selected from the group consisting of
8-(cyclobutyloxy)quinolin-2-amine; 8-(cyclopentyloxy)quinolin-2-amine; 8-(cyclohexyloxy)quinolin-2-amine; 8-((3-methylcyclopentyl)oxy)quinolin-2-amine; 8-((2-methylcyclohexyl)oxy)quinolin-2-amine; 8-((3-methylcyclohexyl)oxy)quinolin-2-amine; 8-((4-methylcyclohexyl)oxy)quinolin-2-amine; 8-(cycloheptyloxy)quinolin-2-amine; 8-(((1R,2S)-2-methylcyclohexyl)oxy)quinolin-2-amine; 8-(((1R,2S)-2-methylcyclopentyl)oxy)quinolin-2-amine; 8-(2,3-dihydro-1H-inden-2-yloxy)quinolin-2-amine; 8-(((1S,5S)-3,3,5-trimethylcyclohexyl)oxy)quinolin-2-amine; 8-(((1R,5S)-3,3,5-trimethylcyclohexyl)oxy)quinolin-2-amine; 8-(((3S)-1-benzylpyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3R)-1-benzylpyrrolidin-3-yl)oxy)quinolin-2-amine; 8-((1-benzylpiperidin-4-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(1,3-benzodioxol-5-ylmethyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(2-fluorobenzyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(1,1′-biphenyl-4-ylmethyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-((3-methyl-1-benzothien-2-yl)methyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-((2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)methyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; tert-butyl (3S)-3-((2-aminoquinolin-8-yl)oxy)pyrrolidine-1-carboxylate; 8-((3S)-pyrrolidin-3-yloxy)quinolin-2-amine; 8-(((3S)-1-(4-tert-butylbenzyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(2,3-difluorobenzyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(3-(trifluoromethyl)benzyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-((2,2-difluoro-1,3-benzodioxol-5-yl)methyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; 8-(((3S)-1-(2,4-dimethylbenzyl)pyrrolidin-3-yl)oxy)quinolin-2-amine; and N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-8-(((3 S)-1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)pyrrolidin-3-yl)oxy)quinolin-2-amine.
- 10. A compound according to formula (Ie),
- 11. The compound according to claim 10, that is a member selected from the group consisting of
8-(((1S)-2-methyl-1-phenylpropyl)oxy)quinolin-2-amine; 8-(1-benzylpropoxy)quinolin-2-amine; 8-(1-(4-fluorophenyl)ethoxy)quinolin-2-amine; 8-(1-methyl-2-phenylethoxy)quinolin-2-amine; 8-(2-(1-naphthyl)ethoxy)quinolin-2-amine; 8-(benzyloxy)quinolin-2-amine; 8-((3-(trifluoromethyl)benzyl)oxy)quinolin-2-amine; 8-((2,4-dimethylbenzyl)oxy)quinolin-2-amine; 8-(((1R)-1-phenylethyl)oxy)quinolin-2-amine; 8-(1-(4-(trifluoromethyl)phenyl)ethoxy)quinolin-2-amine; 8-((4-(((2-aminoquinolin-8-yl)oxy)methyl)benzyl)oxy)-quinolin-2-amine; 8-(3-phenoxypropoxy)quinolin-2-amine; 8-(3-(3,5-dichlorophenoxy)propoxy)quinolin-2-amine; 8-(4-(3,5-dichlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-methoxyphenoxy)-1-methylbutoxy)quinolin-2-amine; N-(4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenyl)acetamide; methyl 3-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)berizoate; 8-(1-methyl-4-(3,4,5-trimethylphenoxy)butoxy)quinolin-2-amine; methyl O-(4-((2-aminoquinolin-8-yl)oxy)pentyl)-L-tyrosinate; 8-(1-methyl-4-(2-naphthyloxy)butoxy)quinolin-2-amine; 1-(4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-3-methylphenyl)ethanone; 8-(1-methyl-4-(4-propylphenoxy)butoxy)quinolin-2-amine; 8-(4-(3-isopropylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-chloro-3-fluorophenoxy)-1-methylbutoxy)quinolin-2-amine; 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzonitrile; 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzamide; 8-(1-methyl-4-(2-methyl-5-nitrophenoxy)butoxy)quinolin-2-amine; 8-(4-((5-amino-1-naphthyl)oxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3-anilinophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-chloro-4-methoxyphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-((4-methoxy-1-naphthyl)oxy)-1-methylbutoxy)quinolin-2-amine; methyl (4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenyl)acetate; ethyl 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-5-methylbenzoate; 8-(4-(4-bromo-2-fluorophenoxy)-1-methylbutoxy)quinolin-2-amine; N-(3-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenyl)urea; 4-(4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenyl)butan-2-one; ethyl 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzoate; methyl 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-5-methoxybenzoate; 8-(4-(4-amino-2-chlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 1-(4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenyl)propan-1-one; 8-(4-(3-(diethylamino)phenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(1,1′-biphenyl-3-yloxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-fluoro-5-methylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-ethoxy-5-((1E)-prop-1-enyl)phenoxy)-1-methylbutoxy)quinolin-2-amine; methyl 2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-4-methoxybenzoate; 8-(4-(2-benzylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-fluoro-4-nitrophenoxy)-1-methylbutoxy)quinolin-2-amine; 5-acetyl-2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzamide; 8-(4-(2,3-dihydro-1 H-inden-5-yloxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-(1H-imidazol-1-yl)phenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-isoxazol-5-ylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-methoxy-4-propylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-chloro-3-(trifluoromethyl)phenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(1-methyl-4-(2-methylphenoxy)butoxy)quinolin-2-amine; 8-(1-methyl-4-(3-methylphenoxy)butoxy)quinolin-2-amine; 8-(1-methyl-4-(4-methylphenoxy)butoxy)quinolin-2-amine; 8-(4-(2-chloro-5-methylphenoxy)-1-methylbutoxy)quinolin-2-amine; 4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)phenol; 8-(4-(3-methoxyphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-methoxyphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-fluorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3-fluorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-fluorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-chlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3-chlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-chlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-bromophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3-bromophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(4-bromophenoxy)-1-methylbutoxy)quinolin-2-amine; 3-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzonitrile; 4-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzonitrile; 8-(1-methyl-4-(3-(trifluoromethyl)phenoxy)butoxy)quinolin-2-amine; 8-(1-methyl-4-(4-(trifluoromethyl)phenoxy)butoxy)quinolin-2-amine; 8-(1-methyl-4-(3-(trifluoromethoxy)phenoxy)butoxy)quinolin-2-amine; 8-(4-(2,3-dimethylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2,4-dimethylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2,5-dimethylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3,4-dimethylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3,5-dimethylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2,3-dichlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2,4-dichlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2,5-dichlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3-isopropyl-5-methylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(3,4-dichlorophenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-chloro-4-methylphenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(2-(benzyloxy)phenoxy)-1-methylbutoxy)quinolin-2-amine; 8-(cyclobutylmethoxy)quinolin-2-amine; 8-(2-cyclopropylethoxy)quinolin-2-amine; 8-(cyclopentylmethoxy)quinolin-2-amine; 8-(cyclohexylmethoxy)quinolin-2-amine; 8-(2-cyclohexylethoxy)quinolin-2-amine; 8-((1S,4R)-bicyclo[2.2.1]hept-2-ylmethoxy)quinolin-2-amine; 8-(1-cyclohexylpropoxy)quinolin-2-amine; 8-(((1R,2R)-2-methylcyclohexyl)oxy)quinolin-2-amine; 8-(1-cyclohexylethoxy)quinolin-2-amine; 8-(tetrahydrofuran-3-ylmethoxy)quinolin-2-amine; 8-(2-(1-methylpyrrolidin-2-yl)ethoxy)quinolin-2-amine; 8-(3-((2-methylquinolin-8-yl)oxy)propoxy)quinolin-2-amine; 8-(3-(quinolin-8-yloxy)propoxy)quinolin-2-amine; 8-(3-((2-aminoquinolin-8-yl)oxy)propoxy)quinolin-2-ol; 6-(3-((2-aminoquinolin-8-yl)oxy)propoxy)quinolin-2-ol; 4-(3-((2-aminoquinolin-8-yl)oxy)propoxy)quinolin-2-amine; 8-(1-methyl-4-((2-methylquinolin-8-yl)oxy)butoxy)quinolin-2-amine; 8-(4-((2-aminoquinolin-8-yl)oxy)-1-methylbutoxy)quinolin-2-amine; 8-(1-methyl-4-(quinolin-7-yloxy)butoxy)quinolin-2-amine; 8-(4-(isoquinolin-5-yloxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-(dibenzo[b,d]furan-2-yloxy)-1-methylbutoxy)quinolin-2-amine; 8-(4-((2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy)-1-methylbutoxy)quinolin-2-amine; 6-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-1,3-benzoxathiol-2-one; 8-(4-(1,3-benzodioxol-5-yloxy)-1-methylbutoxy)quinolin-2-amine; N-((5-(2-(trifluoromethyl)phenyl)-2-furyl)methyl)-8-(1,3,3-trimethylbutoxy)quinolin-2-amine; N-((5-(2-nitrophenyl)-2-furyl)methyl)-8-(1,3,3-trimethylbutoxy)quinolin-2-amine; N-((5-(2-chlorophenyl)-2-furyl)methyl)-8-(1,3,3-trimethylbutoxy)quinolin-2-amine; 8-((5-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)-quinolin-2-amine; 8-(3-((2-aminoquinolin-8-yl)oxy)butoxy)quinolin-2-amine; 8-(3-((2-aminoquinolin-8-yl)oxy)propoxy)-N-methylquinolin-2-amine; and 8-(2-(2-((2-aminoquinolin-8-yl)oxy)ethoxy)ethoxy)-quinolin-2-amine.
- 12. The following additional compounds
8-isopropoxyquinolin-2-amine; 8-sec-butoxyquinolin-2-amine; 8-(1-methylbutoxy)quinolin-2-amine; 8-(1,2-dimethylpropoxy)quinolin-2-amine; 8-(1-ethylpropoxy)quinolin-2-amine; 8-ethoxyquinolin-2-amine; 8-propoxyquinolin-2-amine; 8-butoxyquinolin-2-amine; 8-isobutoxyquinolin-2-amine; 8-(pentyloxy)quinolin-2-amine; 8-(2-methylbutoxy)quinolin-2-amine; 8-(3-methylbutoxy)quinolin-2-amine; 8-(((1R)-1-methylpropyl)oxy)quinolin-2-amine; 8-(((1S)-1,2-dimethylpropyl)oxy)quinolin-2-amine; 8-(((1R)-1,2-dimethylpropyl)oxy)quinolin-2-amine; 8-(((1S)-1-methylpropyl)oxy)quinolin-2-amine; 8-((1-isopropylbut-3-enyl)oxy)quinolin-2-amine; 8-((1,5-dimethylhex-4-enyl)oxy)quinolin-2-amine; 8-((2E)-but-2-enyloxy)quinolin-2-amine; 8-hexylquinolin-2-amine; 8-(1-methylpentyl)quinolin-2-amine; 8-(1-ethylbutyl)quinolin-2-amine; 8-(1-ethylpentyl)quinolin-2-amine; 3-((2-aminoquinolin-8-yl)oxy)propan-1-ol; and 4-((2-aminoquinolin-8-yl)oxy)pentan-1-ol.
- 13. A method of treating disorders mediated by MCH through the MCH receptor comprising administering a therapeutically effective amount of a compound of formula (I).
- 14. A method for treating eating disorders, weight gain and obesity comprising administering a therapeutically effective amount of a compound of formula (I).
- 15. A method for treating abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders comprising administering a therapeutically effective amount of a compound of formula (I).
- 16. A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) in combination with a pharmaceutically suitable carrier.
Parent Case Info
[0001] This application claims priority to the U.S. Provisional Application Serial No. 60/389,558 filed on Jun. 18, 2002, incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60389558 |
Jun 2002 |
US |