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US 12,624,011 B2Granted
Oxadiazole derivative
AssigneeSumitomo Pharma Co., Ltd.
InventorsYoshiaki Isobe, Tomoyuki Tanaka, Hirotaka Miyachi
Life of this patent
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Abstract
The present invention relates to a compound of formula (1) wherein Q1 is halogen atom, Q2 is hydrogen atom, etc., X, Y, and Z are nitrogen atom or oxygen atom, and R1 has a given structure, or a pharmaceutically acceptable salt thereof, and a medicament comprising the compound for treating and/or preventing a disease such as epilepsy.
Claims16
A compound of formula (1):
- or a pharmaceutically acceptable salt thereof, wherein
- Q1 is halogen,
- Q2 is hydrogen, fluorine, cyano, C1-3 alkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C3-6 cycloalkyl, and C1-3 alkoxy, or C1-3 alkoxy which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C3-6 cycloalkyl, and C1-3 alkoxy,
- X, Y, and Z are the same or different and are nitrogen atom or oxygen atom, provided that the ring containing X, Y, and Z is a heteroaryl wherein any two of X, Y, and Z are nitrogen atom and the other is oxygen atom,
- R1 is any one of the following formulae (2) to (4):
- R2 and R3 are the same or different and are C1-6 alkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C3-6 cycloalkyl, and C1-3 alkoxy or C3-6 cycloalkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C1-3 alkyl, and C1-3 alkoxy,
- R4 and R5 are the same or different and are hydrogen, halogen, hydroxy, C1-6 alkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C3-6 cycloalkyl, and C1-3 alkoxy, or C3-6 cycloalkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C1-3 alkyl, and C1-3 alkoxy;
- or when R4 and R5 are attached to the same carbon atom or to two adjacent carbon atoms respectively, R4 and R5 may be taken together with the carbon atom(s) to which they are attached to form C3-6 cycloalkyl which may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C1-3 alkyl, and C1-3 alkoxy, or C4-6 saturated hetero ring containing one or two heteroatoms selected independently from nitrogen atom and oxygen atom, said saturated hetero ring may be substituted with 1 to 3 substituents selected independently from the group consisting of halogen, hydroxy, C1-3 alkyl, and C1-3 alkoxy, and
- n is 0 or 1.
6 more elements
A compound which is selected from the following compounds, or a pharmaceutically acceptable salt thereof:
- 2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-2-methylpropanamide,
- 2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-2-methylpropanamide,
- 2-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-2-methylpropanamide,
- 1-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxamide,
- 1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxamide,
- 1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-fluorocyclobutane-1-carboxamide,
- 1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3,3-difluorocyclobutane-1-carboxamide,
- 1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]cyclobutane-1-carboxamide,
- 1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]cyclopentane-1-carboxamide,
- 4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]tetrahydro-2H-pyran-4-carboxamide,
- 2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-2-ethylbutanamide,
- 2-[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]-2-methylpropanamide,
- 2-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]-2-methylpropanamide,
- 2-[5-(4-bromophenyl)-1,2,4-oxadiazol-3-yl]-2-methylpropanamide,
- 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-2-methylpropanamide,
- 2-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-2-methylpropanamide,
- 2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]propane-2-sulfonamide,
- 2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propane-2-sulfonamide,
- 2-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]propane-2-sulfonamide,
- 2-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]propane-2-sulfonamide,
- 2-[5-(4-bromophenyl)-1,2,4-oxadiazol-3-yl]propane-2-sulfonamide,
- 2-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]propane-2-sulfonamide,
- 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]propane-2-sulfonamide,
- 2-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]propane-2-sulfonamide,
- 5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one,
- 5-[3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one,
- 5-[3-(3,4-difluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one,
- 5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-1,5-dimethylpyrrolidin-2-one,
- 5-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one,
- 5-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one,
- (S)-5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one, and
- (R)-5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-2-one.
29 more elements
Dependencies are inferred from the claim text.