IP Library Granted Patent US 6,989,392
Granted Patent B2
US 6,989,392 · App. 10/460,139 · Granted Jan 24, 2006

2-Aminoquinolines as melanin concentrating hormone receptor antagonists

Assignee: Abbott Laboratories
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Quick Facts
Patent No.
US 6,989,392
App. No.
10/460,139
Granted
Jan 24, 2006
Kind
B2
Abstract

The present invention is related to compounds of formula (I), or a therapeutically suitable salt or prodrug thereof, which antagonize the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor and are useful for the prevention or treatment of eating disorders, weight gain and obesity.

Claims (272)

1. A compound according to formula (I),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is a bond or is a member selected from the group consisting of —C(O)—, —O—, —S—, —S(O)—, and —S(O) 2 —;

R 1 is a member selected from the group consisting of hydrogen, alkyl, alkoxy, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is a member selected from the group consisting of alkyl, alkoxy, alkenyl, alkoxyalkyl, aryl, arylalkyl, aryloxyalkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocycle, heterocyclealkyl, heterocycleoxyalkyl, heterocycleoxyalkoxyalkyl, R 7 L 2 R 6 —, R A Salkyl, and R A R B Nalkyl;

R 3 is hydrogen;

R 4 , and R 5 are each independently a member selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R 6 and R 7 are each independently a member selected from the group consisting of aryl, cycloalkyl, and heterocycle;

R A and R B are each independently a member selected from the group consisting of hydrogen, alkyl, aryl and heterocycle;

L 2 is —(CH 2 ) m X(CH 2 ) n —,

X is a member selected from the group consisting of —C(O)—, —O—, —S—, —S(O)—, —S(O) 2 — or is a covalent bond,

m is 0, 1, 2, 3, or 4;

n is 0, 1, 2, 3, or 4; and

provided that

if i) any of R 3 , R 4 , or R 5 is alkyl or alkoxy, or

if ii) L is a bond and R 2 is either alkyl or alkoxy; then

R 1 must be other than hydrogen.

2. A compound according to formula (Ia),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is —O—;

R 1 is selected from the group consisting of hydrogen, alkyl, alkoxy, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is selected from the group consisting of alkyl, alkenyl;

R 3 is hydrogen;

R 4 , and R 5 are each independently selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R A and R B are each independently selected from the group consisting of hydrogen, alkyl, aryl and heterocycle;

provided that

if i) any of R 3 , R 4 , or R 5 is alkyl or alkoxy, or

if ii) L is a bond and R 2 is either alkyl or alkoxy; then

R 1 must be other than hydrogen.

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),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is —O—;

R 1 is a member selected from the group consisting of hydrogen, alkyl, alkoxy, aryl, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is alkyl, wherein alkyl is C 6 or larger;

R 3 is a member selected from the group consisting of hydrogen, alkyl, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R 4 , and R 5 are each independently a member selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—; and

R A and R B are each independently a member selected from the group consisting of hydrogen, alkyl, aryl and heterocycle.

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),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is —O—;

R 1 is a member selected from the group consisting of hydrogen, alkyl, alkoxy, aryl, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is a member selected from the group consisting of alkoxyalkyl, haloalkyl, R A Salkyl, and R A R B Nalkyl;

R 3 is a member selected from the group consisting of hydrogen, alkyl, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R 4 , and R 5 are each independently a member selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R A and R B are each independently a member selected from the group consisting of hydrogen, alkyl, aryl and heterocycle.

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),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is —O—;

R 1 is a member selected from the group consisting of hydrogen, alkyl, alkoxy, aryl, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is a member selected from the group consisting of aryl, cycloalkyl and heterocycle;

R 3 is a member selected from the group consisting of hydrogen, alkyl, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R 4 , and R 5 are each independently a member selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R A and R B are each independently a member selected from the group consisting of hydrogen, alkyl, aryl and heterocycle.

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-(((3S)-1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)pyrrolidin-3-yl)oxy)quinolin-2-amine.

10. A compound according to formula (Ie),

or a therapeutically suitable salt or prodrug thereof, wherein

L 1 is —O—;

R 1 is a member selected from the group consisting of hydrogen, alkyl, alkoxy, aryl, arylalkyl, arylalkoxy, arylcarbonyl, heterocycle, heterocyclealkyl, and R A R B Ncarbonyl;

R 2 is a member selected from the group consisting of arylalkyl, aryloxyalkyl, cycloalkylalkyl, heterocyclealkyl, heterocycleoxyalkyl, heterocycleoxyalkoxyalkyl, R 7 L 2 R 6 —;

R 3 is a member selected from the group consisting of hydrogen, alkyl, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R 4 , and R 5 are each independently a member selected from the group consisting of hydrogen, alkyl, alkoxy, hydroxy, cyano, halo, haloalkoxy, R A R B N—, and alkylcarbonylNH—;

R A and R B are each independently a member selected from the group consisting of hydrogen, alkyl, aryl and heterocycle

R 6 and R 7 are each independently a member selected from the group consisting of aryl, cycloalkyl and heterocycle;

L 2 is —(CH 2 ) m X(CH 2 ) n —;

X is a member selected from the group consisting of —C(O)—, —O—, —S—, —S(O)—, —S(O)— or is a covalent bond;

m is 0, 1, 2, 3 or 4;

n is 0, 1, 2, 3 or 4;

provided that if any of R 3 , R 4 or R 5 is alkyl or alkoxy, then R 1 must be other than hydrogen.

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-1H-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. A compound selected from the group consisting of

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 obesity, by antagonizing the MCH receptor comprising administering a therapeutically effective amount of a compound of formula (I) of claim 1 .

14. A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) of claim 1 in combination with a pharmaceutically suitable carrier.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030176/0968 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2003
From: COLLLINS, CHRISTINE A.; GAO, JU; KYM, PHILIP R.; LEWIS, JARED C.; VASUDEVAN, ANIL; SOUERS, ANDREW J.; WODKA, DARIUSZ
To: ABBOTT LABORATORIES
Reel/Frame 014650/0588 →
Continuity (2)
Provisional Application 6038955800 · Jun 18, 2002
Related Publication 20040063756A1 · Apr 1, 2004