Oxadiazole derivative and pharmaceutical containing same
AssigneeNational Center for Geriatrics and Gerontology
InventorsKatsuhiko Yanagisawa, Akiyoshi Kawai
Life of this patent
Estimating the term…
Abstract
An amyloid fibril formation inhibitor comprising a compound represented by the following general formulae (I) to (III): wherein Q is —C(═O)—; X is —C(═O)—, —NH—C(═O)—; Y is —(CH2)m—; Z is —(CH2)n—; R1, R2, and R3 are each independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkylaminoalkyl group; and R4 is an amino group, an alkylamino group or the like; or a pharmaceutically acceptable salt thereof or a solvate thereof.
Claims16
An amyloid fibril formation inhibitor comprising a compound of formula (II):
- wherein:
- Ring A1 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted indolyl group;
- Ring A2 is 1,2,4-oxadiazolyl or 1,3,4-oxadiazolyl;
- Ring A3 is a substituted or unsubstituted phenyl group;
- n is 1;
- R1 is hydrogen and R2 is a C1-10 hydroxyalkyl group;
- and
- X is —NH—C(═O)—;
- or a pharmaceutically acceptable salt thereof or a solvate thereof.
An amyloid fibril formation inhibitor comprising a compound selected from the group consisting of (S)-4-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-3-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, 4-chloro-N-[2-hydroxy-1-{3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl}ethyl]benzamide, (R)-4-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-2-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-3-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl] ethyl)benzamide, (S)-3-chloro-4-hydroxy-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-4-chloro-N-(1-(3-(3-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)-2-hydroxyethyl)benzamide, (S)-4-cyano-N-(1-(3-(3-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(5-(4-(methylsulfonamido)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(methylsulfonamido)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (R)-4-chloro-N-(1-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-fluoro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-fluoro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl ethyl)benzamide, (R)-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)ethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, (S)-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, N-[(1S)-1-[3-(2-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, N-[(1S)-1-[3-(3-fluoro-4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(propan-2-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-{5-[(1S)-1-[(4-fluorophenyl)formamido]-2-hydroxyethyl]-1,2,4-oxadiazol-3-yl}-N-(3-methoxypropyl)benzamide, 4-{5-[(1S)-2-hydroxy-1-(phenylformamido)ethyl]-1,2,4-oxadiazol-3-yl}-N-(3-methoxypropyl)benzamide, N-[(1S)-1-{3-[4-(dimethylamino)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(4-acetylphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(1-hydroxyethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2-hydroxypropan-2-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2-hydroxyethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-(3-{4-[2-morpholin-4-yl)ethoxy]phenyl}-1,2,4-oxadiazol-5-yl)ethyl]benzamide, 4-{(5-[(1S)-2-hydroxy-1-(phenylformamido)ethyl]-1,2,4-oxadiazol-3-yl}phenyl N-ethyl-N-methylcarbamate, 4-fluoro-N-[(1S) 1-{(3-[4-fluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-{3-[4-(fluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(2,2,2-trifluoroacetyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2,2,2-trifluoroacetyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]-4-fluorobenzamide, 4-chloro-N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-(2-ethoxyethoxy)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-(2-ethoxyethoxy)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-[2-(diethylamino)ethoxy]-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-5-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(1H-pyrazol-1-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(1H-pyrazol-1-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{(3-[2-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-(2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl)-4-(trifluoromethyl)benzamide, N-[(1S)-2-hydroxy-1-{3-[2-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-{3-[4-(3-fluorooxetan-3-yl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(3-fluoro-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3,5-difluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 2,6-difluoro-N-[(1S)-2-hydroxy-1-{(3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(trifluoromethoxy)benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(morpholin-4-yl)benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-phenoxybenzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(pyrrolidin-1-yl)benzamide, 4-(dimethylamino)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-fluoro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1R)-2-hydroxy-1-{(3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-chloro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-{3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-{3-[3-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-[3-(3,5-difluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, N-[(1S)-1-[3-(2-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(morpholin-4-yl)benzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(pyrrolidin-1-yl)benzamide, 3-chloro-5-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trimethylsilyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-1-[3-(5-fluoro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 4-chloro-2-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, N-[(1S)-1-[3-(5-bromo-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-6-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-chloro-N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-2-fluorobenzamide, N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-(pyrrolidin-1-yl)benzamide, 5-chloro-N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]pyridine-2-carboxamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(2,2,2-trifluoroacetyl)-1H-indol-6-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(6-fluoro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(5-methoxy-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[5-(trifluoromethyl)-1H-indol-3-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(6-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[1-(2-hydroxyethyl)-1H-indol-3-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide and 4-fluoro-N-[(1S)-1-[3-(5-fluoro-1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide;
- or a pharmaceutically acceptable salt thereof or a solvate thereof.
A compound selected from the group consisting of (S)-4-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-3-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, 4-chloro-N-[2-hydroxy-1-{3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl}ethyl]benzamide, (R)-4-chloro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-2-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-3-fluoro-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-3-chloro-4-hydroxy-N-(2-hydroxy-1-[3-{4-(trifluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]ethyl)benzamide, (S)-4-chloro-N-(1-(3-(3-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)-2-hydroxyethyl)benzamide, (S)-4-cyano-N-(1-(3-(3-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(5-(4-(methylsulfonamido)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl ethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(methylsulfonamido)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (R)-4-chloro-N-(1-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,3,4-oxadiazol-2-yl)ethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-fluoro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(1-(5-(3-fluoro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, (R)-4-chloro-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)ethyl)benzamide, (R)-N-(2-hydroxy-1-(5-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)ethyl)benzamide, (S)-4-chloro-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5 yl)ethyl)benzamide, (S)-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, (S)-4-fluoro-N-(2-hydroxy-1-(3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)benzamide, N-[(1S)-1-[3-(2-fluoro-4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, N-[(1S)-1-[3-(3-fluoro-4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(propan-2-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-{5-[(1S)-1-[(4-fluorophenyl)formamido]-2-hydroxyethyl]-1,2,4-oxadiazol-3-yl}-N-(3-methoxypropyl)benzamide, 4-{5-[(1S)-2-hydroxy-1-(phenylformamido)ethyl]-1,2,4-oxadiazol-3-yl}-N-(3-methoxypropyl)benzamide, N-[(1S)-1-{3-[4-(dimethylamino)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(4-acetylphenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(1-hydroxyethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2-hydroxypropan-2-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2-hydroxyethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S) 2=hydroxy-1-(3-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1,2,4-oxadiazol-5-yl)ethyl]benzamide, 4-{5-[(1S)-2-hydroxy-1-(phenylformamido)ethyl]-1,2,4-oxadiazol-3-yl}phenyl N-ethyl-N-methylcarbamate, 4-fluoro-N-[(1S)-1-{3-[4-(fluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-{3-[4-(fluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S) 2-hydroxy-1-{3-[4-(2,2,2-trifluoroacetyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(2,2,2-trifluoroacetyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]-4-fluorobenzamide, 4-chloro-N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-{3-[4-(difluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-(2-ethoxyethoxy)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-(2-ethoxyethoxy)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-[2-(diethylamino)ethoxy]-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-5-yl)-1,2,4-oxadiazol-5-yl] ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(1H-pyrazol-1-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(1H-pyrazol-1-yl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[2-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-(2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl)-4-(trifluoromethyl)benzamide, N-[(1S)-2-hydroxy-1-{3-[2-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-{3-[4-(3-fluorooxetan-3-yl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(3-fluoro-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3,5-difluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 2,6-difluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(trifluoromethoxy)benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(morpholin-4-yl)benzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-phenoxybenzamide, N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(pyrrolidin-1-yl)benzamide, 4-(dimethylamino)-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-fluoro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-chloro-N-[(1R)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-{3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-{3-[3-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-hydroxyethyl]benzamide, N-[(1S)-1-[3-(3,5-difluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, N-[(1S)-1-[3-(2-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(morpholin-4-yl)benzamide, N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]-4-(pyrrolidin-1-yl)benzamide, 3-chloro-5-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trimethylsilyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-1-[3-(5-fluoro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 2364-chloro-2-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 3-chloro-4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, N-[(1S)-1-[3-(5-bromo-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-6-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-chloro-N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-2-fluorobenzamide, N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-(pyrrolidin-1-yl)benzamide, 5-chloro-N-[(1S)-1-[3-(5-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]pyridine-2-carboxamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[3-(2,2,2-trifluoroacetyl)-1H-indol-6-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-1-[3-(6-fluoro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(5-methoxy-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[5-(trifluoromethyl)-1H-indol-3-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, N-[(1S)-1-[3-(6-chloro-1H-indol-3-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]-4-fluorobenzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-{3-[1-(2-hydroxyethyl)-1H-indol-3-yl]-1,2,4-oxadiazol-5-yl}ethyl]benzamide, 4-fluoro-N-[(1S)-2-hydroxy-1-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]ethyl]benzamide and 4-fluoro-N-[(1S)-1-[3-(5-fluoro-1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]-2-hydroxyethyl]benzamide;
- or a pharmaceutically acceptable salt thereof or a solvate thereof.
Dependencies are inferred from the claim text.