4-fluoro-piperidine T-type calcium channel antagonists
View Patent ↗The present invention is directed to 4-fluoro-piperidine compounds which are antagonists of T-type calcium channels, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which T-type calcium channels are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which T-type calcium channels are involved.
1. A compound which is selected from the group consisting of:
N-((1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl)methyl)-3-fluoro-5-(trifluoromethyl)benzamide;
3,5-dichloro-N-((1-((2,2-dimethyl-tetrahydro-2H-pyran-4-yl)methyl)-4-fluoropiperidin-4-yl)methyl)benzamide;
3-chloro-N-{[1-(3,3-dimethyl-2-oxobutyl)-4-fluoropiperidin-4-yl]methyl}-5-methoxybenzamide;
3-chloro-N-({4-fluoro-1-[(2S)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)-5-methoxybenzamide;
3-chloro-N-({4-fluoro-1-[(2R)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)-5-methoxybenzamide;
N-(1-[2-(tert-butylamino)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dichlorobenzamide;
3,5-dichloro-N-{[4-fluoro-1-(1H-imidazol-2-ylmethyl)piperidin-4-yl]methyl}benzamide;
N-{[1-3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxamide;
N-{[1-3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(trifluoromethyl)cyclobutanecarboxamide;
3,5-dichloro-N-{[4-fluoro-1-(1H-pyrazol-5-ylmethyl)piperidin-4-yl]methyl}benzamide;
2-benzyl-N-{[1(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3,3-dimethylbutanamide;
3,5-dichloro-N-[(1-ethyl-4-fluoropiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-{[4-fluoro-1-(isoxazol-3-ylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(1-methyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}methyl)benzamide;
N-{[1-3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}adamantane-1-carboxamide;
3,5-dichloro-N-{[4-fluoro-1-(tetrahydrofuran-3-ylmethyl)piperidin-4-yl]methyl}benzamide;
(1R,4R)-N-{[1(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxamide;
3-(dimethylamino)-N-{[1(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({1-[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(5-nitro-2-furyl)methyl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-{[4-fluoro-1-(pentafluorobenzyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(4-methyl-1H-imidazol-2-yl}methyl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-{[4-fluoro-1-(1,3-thiazol-4-ylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({1-[(3-ethyloxetan-3-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-{[4-fluoro-1-(tetrahydro-2H-pyran-4-ylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-[(4-fluoro-1-propylpiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-{[1-(cyclopropylmethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
1-(2-chloro-4-fluorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclopentane-carboxamide;
3,5-dichloro-N-{[4-fluoro-1-(2-furylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(1-methyl-1H-pyrazol-3-yl)methyl]piperidin-4-yl}methyl)benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-methylbenzamide;
3,5-dichloro-N-[(1-cyclobutyl-4-fluoropiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-{[4-fluoro-1-(3-furylmethyl)piperidin-4-yl]methyl}benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide;
{5-[(4-{[(3,5-dichlorobenzoyl)amino]methyl}-4-fluoropiperidin-1-yl)methyl]-2-furyl}methyl acetate;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3,3-dimethylbutanamide;
3,5-dichloro-N-({1-[(2,5-dimethoxytetrahydrofuran-3-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
N-[(1-butyl-4-fluoropiperidin-4-yl)methyl]-3,5-dichlorobenzamide;
3,5-dichloro-N-({1-[(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2E,4E)-hexa-2,4-dien-1-yl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-[(4-fluoro-1-isobutylpiperidin-4-yl)methyl]benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-fluorophenyl)cyclopentane-carboxamide;
3,5-dichloro-N-{[1-(2,2-dimethylpropyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-{[1-(1-cyclobutylethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3-[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-({1-[(4-bromo-3-thienyl)methyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dichlorobenzamide;
2-[(1S,4R)-bicyclo[2.2.1]hept-2-yl]-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}acetamide;
3-cyano-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-fluorobenzamide;
3,5-dichloro-N-{[4-fluoro-1-(2-thienylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2E,4E)-nona-2,4-dien-1-yl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-{[1-(cyclobutylmethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-({1-[(4-bromo-2-thienyl)methyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dichlorobenzamide;
3-chloro-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-5-fluorobenzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3,5-difluorobenzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(3-fluorophenyl)cyclohexane-carboxamide;
3,5-dichloro-N-[(4-fluoro-1-nonylpiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-({4-fluoro-1-[(5-methyl-2-furyl)methyl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-[(4-fluoro-1-{[5-(methoxymethyl)-2-furyl]methyl}piperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-{[4-fluoro-1-(7-methoxy-3,7-dimethyloctyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({1-[(4E)-dec-4-en-1-yl]-4-fluoropiperidin-4-yl}methyl)benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(trifluoromethyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(5-methyl-2-thienyl)methyl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-{[4-fluoro-1-(4,4,4-trifluorobutyl)piperidin-4-yl]methyl}benzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
2-(1-adamantyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}acetamide;
3,5-dichloro-N-({1-[(5-ethyl-2-furyl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2E,6Z)-nona-2,6-dien-1-yl]piperidin-4-yl}methyl)benzamide;
3-bromo-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-{[4-fluoro-1-(3-thienylmethyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-[(4-fluoro-1-pentylpiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-{[4-fluoro-1-(3-methylbutyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-{[4-fluoro-1-(3-methoxy-3-methylbutyl)piperidin-4-yl]methyl}benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3,5-dimethylbenzamide;
3,5-dichloro-N-({1-[(2E)-2-ethylbut-2-en-1-yl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2E)-2-methylpent-2-en-1-yl]piperidin-4-yl}methyl)benzamide;
ethyl 2-[(4-{[(3,5-dichlorobenzoyl)amino]methyl}-4-fluoropiperidin-1-yl)methyl]cyclopropanecarboxylate;
3,5-dichloro-N-{[1-(cyclopentylmethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(1,1,2,2-tetrafluoroethoxy)benzamide;
3,5-dichloro-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(trifluoromethoxy)benzamide;
3,5-dichloro-N-{[1-(cyclohex-3-en-1-ylmethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2E)-hex-2-en-1-yl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-[(4-fluoro-1-hexylpiperidin-4-yl)methyl]benzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-methylbenzamide;
3,5-dichloro-N-{[1-(2,6-dimethylhept-5-en-1-yl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-{[1-(2-ethylhexyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)adamantane-1-carboxamide;
3,5-dichloro-N-({1-[(2E)-2,4-dimethylhepta-2,6-dien-1-yl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3-tert-butyl-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-methoxybenzamide;
3,5-dichloro-N-{[1-(cyclohexylmethyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-fluorobenzamide;
3,5-dichloro-N-{[4-fluoro-1-(3,5,5-trimethylhexyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-{[4-fluoro-1-(2-methylpentyl)piperidin-4-yl]methyl}benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-fluoro-5-(trifluoromethyl)benzamide;
3,5-dichloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]piperidin-4-yl}methyl)benzamide;
3,5-dibromo-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-{[1-(1-adamantylmethyl)-4-fluoropiperidin-4-yl]methyl}-3,5-dichlorobenzamide;
3-chloro-5-fluoro-N-({4-fluoro-1-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]piperidin-4-yl}methyl)benzamide;
3-chloro-5-fluoro-N-({4-fluoro-1-[(2,6,6-trimethylcyclohex-1-en-1-yl)methyl]piperidin-4-yl}methyl)benzamide;
N-{[1-(1-adamantylmethyl)-4-fluoropiperidin-4-yl]methyl}-3-chloro-5-fluorobenzamide;
3,5-dichloro-N-{[1-(2,3-dimethylpentyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2,6,6-trimethylcyclohex-1-en-1-yl)methyl]piperidin-4-yl}methyl)benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3,5-dimethoxybenzamide;
3,5-dichloro-N-[(1-{[(1R,5S)-6,6-dimethylbicyclo [3.1.1 ]hept-2-en-2-yl]methyl}-4-fluoropiperidin-4-yl)methyl]benzamide;
3-chloro-N-[(1-{[(1R,5S)-6,6-dimethylbicyclo[3.1.1 ]hept-2-en-2-yl]methyl}-4-fluoropiperidin-4-yl)methyl]-5-fluorobenzamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-(4-methylphenyl)cyclopropanecarboxamide;
1-(4-chlorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclopropanecarboxamide;
1-(2,4-dichlorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclopropanecarboxamide;
1-(4-chlorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclobutanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-phenylcyclopentanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-(4-methylphenyl)cyclopentanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-(3-fluorophenyl)cyclopentanecarboxamide;
1-(4-chlorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclopentanecarboxamide;
1-(2-chloro-6-fluorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclopentanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-phenylcyclohexanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-(4-methylphenyl)cyclohexanecarboxamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-1-(4-fluorophenyl)cyclohexanecarboxamide;
1-(4-chlorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclohexanecarboxamide;
1-(2-chloro-4-fluorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclohexanecarboxamide;
1-(2-chloro-6-fluorophenyl)-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)cyclohexanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-methylphenyl)cyclopropanecarboxamide;
1-(4-chlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclopropanecarboxamide;
1-(2,4-dichlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclopropanecarboxamide;
1-(4-chlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclobutanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-phenylcyclopentanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-methylphenyl)cyclopentanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-methoxyphenyl)cyclopentane-carboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(2-fluorophenyl)cyclopentanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(3-fluorophenyl)cyclopentanecarboxamide;
1-(4-chlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclopentanecarboxamide;
trans-1-(4-chlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-fluorocyclobutane-carboxamide;
1-(2-chloro-6-fluorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclopentane-carboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-phenylcyclohexanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-methylphenyl)cyclohexanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-methoxyphenyl)cyclohexane-carboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(2-fluorophenyl)cyclohexanecarboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-1-(4-fluorophenyl)cyclohexanecarboxamide;
1-(4-chlorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclohexanecarboxamide;
1-(2-chloro-4-fluorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclohexane-carboxamide 1-(2-chloro-6-fluorophenyl)-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}cyclohexane-carboxamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-hydroxy-5-methoxybenzamide;
3,5-dichloro-N-{1-[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]ethyl}benzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(2-fluoroethoxy)-5-methoxybenzamide;
N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-3-(fluoromethoxy)-5-methoxybenzamide;
N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dimethoxybenzamide;
N-({1-[(2,2-dimethyltetrahydrofuran-3-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dimethoxybenzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-4-methoxybenzamide;
4-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-2-methoxybenzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-hydroxybenzamide;
3-chloro-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-4-methoxybenzamide;
3-chloro-N-({1-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-5-hydroxybenzamide;
N-({1-[2-(tert-butylsulfonyl)ethyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dichlorobenzamide;
3,5-dichloro-N-[(4-fluoro-1-{2-oxo-2-[2-(trifluoromethyl)pyrrolidin-1-yl]ethyl}piperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-({1-[2-(4,4-dimethyl-1,3-oxazolidin-3-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
N-[(1-{2-[tert-butyl(2-methoxyethyl)amino]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]-3,5-dichlorobenzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-(fluoromethoxy)benzamide;
3-chloro-N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}-5-methoxybenzamide;
3-chloro-N-({4-fluoro-1-[(2R)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)-5-methoxy-benzamide;
3-chloro-N-({4-fluoro-1-[(2S)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)-5-methoxybenzamide;
3-chloro-N-{[4-fluoro-1-(2-hydroxy-3,3-dimethylbutyl)piperidin-4-yl]methyl}-5-methoxybenzamide;
3-chloro-N-{[1-(3,3-dimethyl-2-oxobutyl)-4-fluoropiperidin-4-yl]methyl}-5-methoxybenzamide;
3,5-dichloro-N-({4-fluoro-1-[(2R)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-({4-fluoro-1-[(2S)-2-hydroxy-3,3-dimethylbutyl]piperidin-4-yl}methyl)benzamide;
3-chloro-N-[(4-fluoro-1-{2-oxo-2-[2-(trifluoromethyl)pyrrolidin-1-yl]ethyl}piperidin-4-yl)methyl]-5-methoxybenzamide;
N-[(4-fluoro-1-{2-oxo-2-[2-(trifluoromethyl)pyrrolidin-1-yl]ethyl}piperidin-4-yl)methyl]-3,5-dimethoxybenzamide;
3-chloro-5-fluoro-N-[(4-fluoro-1-{2-oxo-2-[2-(trifluoromethyl)pyrrolidin-1-yl]ethyl}piperidin-4-yl)methyl]benzamide;
3-chloro-N-[(1-{2-[(1-cyclopropyl-1-methylethyl)amino]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]-5-methoxybenzamide;
N-({1-[2-(tert-butylamino)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-3-chloro-5-methoxybenzamide;
3,5-dichloro-N-{[4-fluoro-1-(2-hydroxy-3,3-dimethylbutyl)piperidin-4-yl]methyl}benzamide;
3,5-dichloro-N-({1-[(6,6-dimethyltetrahydro-2H-pyran-2-yl)methyl]-4-fluoropiperidin-4-yl}methyl)-benzamide;
3,5-dichloro-N-{[1-(3,3-dimethyl-2-oxobutyl)-4-fluoropiperidin-4-yl]methyl}benzamide;
N-({1-[2-(tert-butylamino)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-2-(4-tert-butylphenyl)acetamide;
N-({1-[2-(4,4-dimethyl-1,3-oxazolidin-3-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dimethoxy-benzamide;
N-({1-[2-(3,3-dimethylmorpholin-4-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dimethoxy-benzamide;
N-[(4-fluoro-1-{2-[(2-methoxy-1,1-dimethylethyl)amino]-2-oxoethyl}piperidin-4-yl)methyl]-3,5-dimethoxybenzamide;
N-[(1-{2-[(3R,5R)-3,5-dimethylmorpholin-4-yl]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]-3,5-dimethoxybenzamide;
3-chloro-N-({1-[2-(4,4-dimethyl-1,3-oxazolidin-3-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-5-fluorobenzamide;
3-chloro-N-({1-[2-(3,3-dimethylmorpholin-4-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-5-fluorobenzamide;
3-chloro-5-fluoro-N-[(4-fluoro-1-{2-[(2-methoxy-1,1-dimethylethyl)amino]-2-oxoethyl}piperidin-4-yl)methyl]benzamide;
3-chloro-N-[(1-{2-[(3R,5R)-3,5-dimethylmorpholin-4-yl]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]-5-fluorobenzamide;
3-chloro-N-({1-[2-(4,4-dimethyl-1,3-oxazolidin-3-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl) -5-methoxybenzamide;
3-chloro-N-({1-[2-(3,3-dimethylmorpholin-4-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-5-methoxybenzamide;
3-chloro-N-[(4-fluoro-1-{2-[(2-methoxy-1,1-dimethylethyl)amino]-2-oxoethyl}piperidin-4-yl)methyl]-5-methoxybenzamide;
3-chloro-N-[(1-{2-[(3R,5R)-3,5-dimethylmorpholin-4-yl]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]-5-methoxybenzamide3,5-dichloro-N-({4-fluoro-1-[(6-hydroxy-2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)benzamide;
3-[(4-{[(3,5-dichlorobenzoyl)amino]methyl}-4-fluoropiperidin-1-yl)methyl]-5-hydroxy-5-methylhexanoic acid;
3,5-dichloro-N-({1-[(2,2-dimethyl-6-oxotetrahydro-2H-pyran-4-yl)methyl]-4-fluoropiperidin-4-yl}methyl)benzamide;
3,5-dichloro-N-[(1-{2-[(3R,5S)-3,5-dimethylmorpholin-4-yl]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-[(1-{2-[(3R,5R)-3,5-dimethylmorpholin-4-yl]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]benzamide;
3,5-dichloro -N-[(4-fluoro -1-{2-[(2-methoxy-1,1-dimethylethyl)amino]-2-oxoethyl}piperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-[(1-{2-[(1-cyclopropyl-1-methylethyl)amino]-2-oxoethyl}-4-fluoropiperidin-4-yl)methyl]benzamide;
3,5-dichloro-N-({1-[2-(3,3-dimethylmorpholin-4-yl)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)benzamide; and
N-({1-[2-(tert-butylamino)-2-oxoethyl]-4-fluoropiperidin-4-yl}methyl)-3,5-dichlorobenzamide;
or a pharmaceutically acceptable salt thereof.
2. A compound which is:
3,5-dichloro-N-((1-((2,2-dimethyl-tetrahydro-2H-pyran-4-yl)methyl)-4-fluoropiperidin-4-yl)methyl)benzamide;
or a pharmaceutically acceptable salt thereof.
3. The compound of claim 2 which is:
(+)-3,5-dichloro-N-((14(2,2-dimethyl-tetrahydro-2H-pyran-4-yl)methyl)-4-fluoropiperidin-4-yl)methyl)benzamide;
or a pharmaceutically acceptable salt thereof.
4. The compound of claim 2 which is:
(−)-3,5-dichloro-N-((1-((2,2-dimethyl-tetrahydro-2H-pyran-4-yl)methyl)-4-fluoropiperidin-4-yl)methyl)benzamide;
or a pharmaceutically acceptable salt thereof.
5. The compound of claim 1 which is:
3,5-dichloro -N-{[1-(3,3-dimethylbutyl)-4-fluoropiperidin-4-yl]methyl}benzamide ;
or a pharmaceutically acceptable salt thereof.
6. A pharmaceutical composition which comprises an inert carrier and a compound of claim 1 or a pharmaceutically acceptable salt thereof.
7. A pharmaceutical composition which comprises an inert carrier and a compound of claim 2 or a pharmaceutically acceptable salt thereof.
8. A pharmaceutical composition which comprises an inert carrier and a compound of claim 3 or a pharmaceutically acceptable salt thereof.
9. A pharmaceutical composition which comprises an inert carrier and a compound of claim 4 or a pharmaceutically acceptable salt thereof.
10. A pharmaceutical composition which comprises an inert carrier and a compound of claim 5 or a pharmaceutically acceptable salt thereof.