Amide derivative
AssigneeDaiichi Sankyo Company, Limited
InventorsShigeo Yamanoi, Hidenori Namiki, Takahiro Katagiri, Mayuko Akiu, Katsuji Kagechika, Takeshi Honda, Koji Matsumoto, Ryutaro Nakashima
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Abstract
Provided are a compound having an excellent hypoglycemic action, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition having an excellent therapeutic effect and/or prophylactic effect on type 1 diabetes, type 2 diabetes, and the like, which cause an increase in the blood sugar level due to abnormal sugar metabolism. A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof, is disclosed.
Claims22
A compound represented by formula (I):
- wherein R1 represents a hydrogen atom, or the C1-C6 alkyl group substituted with one or two substituents selected from a substituent subgroup α;
- the substituent subgroup α is the group consisting of a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, a hydroxyl group which may be substituted with a substituent selected from a substituent subgroup β, and a carboxyl group;
- the substituent subgroup β is the group consisting of a C1-C6 alkylcarbonyl group substituted with one or two substituents selected from a substituent subgroup γ, and a 4- to 6-membered heterocyclic carbonyl group which may be substituted with one C1-C6 alkyl group;
- the substituent subgroup γ is the group consisting of a hydroxyl group, an amino group, a (C1-C6 alkyl)amino group, a di(C1-C6 alkyl)amino group, a carbamoyl group, a phenyl group and a 4- to 6-membered heterocyclic group;
- R2 represents a hydrogen atom, or a C1-C6 alkyl group which may be substituted with one hydroxyl group;
- or R1 and R2, together with the nitrogen atom to which R1 and R2 are bonded, may be joined to form an azetidino group, a pyrrolidino group or a morpholino group, wherein the azetidino group, pyrrolidino group or morpholino group may be substituted with one hydroxyl group or one hydroxy-C1-C6 alkyl group;
- R3 and R4 each independently represent a C1-C6 alkyl group;
- R5 represents a halogen atom or a C1-C6 alkyl group;
- R6 represents a halogen atom;
- m and n each independently represent an integer from 0 to 4;
- and
- V, W, X, Y and Z each independently represent CH or N, or a pharmaceutically acceptable salt thereof.
A compound selected from the group consisting of the following compounds:
- 2-fluoro-N-(2-hydroxyethyl)-4-(5-{1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzamide,
- 2-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4-(5-1{-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzamide,
- 2-fluoro-N-(2-hydroxy-1,1-dimethylethyl)-4-(5-{1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzamide,
- (2R)-2-{[2-fluoro-4-(5-{1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzoyl]amino}propyl glycinate hydrochloride,
- 2-{[2-fluoro-4-(5-{1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2-methylpropyl glycinate hydrochloride,
- 2-fluoro-N-[(1S)-2-hydroxy-1-methylethyl]-4 (2-{1-[4 (5 isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,3-oxazol-4-yl)benzamide,
- (2S)-2-{[2-fluoro-4 (2-{1-[4 (5 isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,3-oxazol-4-yl)benzoyl]amino}propyl glycinate hydrochloride,
- 4-(5-{1-[4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(1S)-2-hydroxy-1-methylethyl]benzamide,
- (2S)-2-{[4-(5-{1-[4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoyl]amino}propyl glycinate hydrochloride,
- 2-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4-(5-{(1R)-1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzamide, and
- N-(cyclopropylmethyl)-2-fluoro-4-(5-{(1R)-1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzamide.
Dependencies are inferred from the claim text.