Cyclopentylacrylamide derivative
AssigneesKyorin Pharmaceutical Co., Ltd., Teijin Pharma Limited
InventorsYasumichi Fukuda, Yoshikazu Asahina, Masanori Takadoi, Masanori Yamamoto
Life of this patent
Estimating the term…
Abstract
A compound having a hypoglycemic effect is provided. The compound and a pharmaceutically acceptable salt thereof are useful for the treatment or prevention of diabetes, obesity, and the like. The compound is represented by the general formula (1): (wherein R1 and R2 are each independently a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a hydroxyamino group, a nitro group, a cyano group, a sulfamoyl group, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C1 to C6 alkylsulfanyl group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group, or a C1 to C6 alkoxy-C1 to C6 alkylsulfonyl group, and A is a substituted or unsubstituted heteroaryl group).
Claims23
A compound represented by the general formula (1) or a pharmaceutically acceptable salt thereof:
- wherein:
- R1 and R2 are each independently a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a hydroxyamino group, a nitro group, a cyano group, a sulfamoyl group, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C1 to C6 alkylsulfanyl group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group, or a C1 to C6 alkoxy-C1 to C6 alkylsulfonyl group, and
- A is a substituted or unsubstituted heteroaryl group).
A compound selected from the group consisting of:
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclpentyl)-2-(4-(methylsulfonyl)phenyl)-N-(thiazol-2- yl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-2-(4-(methylsulfonyl)phenyl)-N-(pyrazin-2-yl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-methylpyazin-2-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-methoxyethoxy)pyrazin-2-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1-methyl-1H-pyrazol-3-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1-(difluoromethyl)- 1H-pyrazol-3-yl)-2-(4-methylsulfonyl)phenyl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-methoxyethoxy)thiazolo[5,4-b]pyridin-2-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-(dimethylamino)ethoxy)thiazolo[5,4-b]pyridin-2-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(thiazol-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-fluorothiazol-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(4-methylthiazol-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1,2,4-thiadiazol-5-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(3-methyl-1,2,4-thiadiazol-5-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-methylpyazin-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-methoxyethoxy)pyrazin-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-hydroxyethoxy)pyrazin-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1-methyl -1H-pyrazol-3-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1-(2-hydroxyethyl)-1H-pyrazol-3-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(thiazolo[5,4-b]pyridin-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-2-(piperidin-1-yl)ethyl)thio)thiaz01-2-yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-hydroxy-2-methylpropoxy)pyrazin-2 -yl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(2-(dimethylamino)ethoxy)thiazolo[5,4-]pyridin-2-yl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-2-(4-(methylsulfonyl)phenyl)-N-(4-(2-hydroxyethyl)thiazol-2-yl)acrylamide,
- (E)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(1-(2-hydroxyethyl)-1H-pyrazol-3-yl)-2-(4-(methylsulfonyl)phenyl)acrylamide,
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-(hydroxymethyl)pyridin-2-yl)acrylamide,
- Diethyl ((2-((E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-(((1r,3R,4S)-3 ,4-difluorocyclopentyl) acrylamido)thiazol-5-yl)methyl)phosphonate, and
- (E)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((1α, 3α, 4α)-3,4-difluorocyclopentyl)-N-(5-((2-aminoethyl)thio)thiazol-2-yl)acrylamide,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.