2-pyridone compound
This 2-pyridone compound represented by formula [1] or a tautomer of said compound, or a pharmaceutically acceptable salt of said compound or said tautomer, or a solvate of said compound or the like has a superior GK-activating effect and is useful as a pharmaceutical.
1. A compound represented by formula [1]:
a tautomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate of the compound, the tautomer thereof, or the salt thereof.
2. The compound according to claim 1 , which is a crystal of 3-cyclopropyl-6-{(1R)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}pyridin-2(1H)-onehaving
an X-ray powder diffraction pattern (Cu—Kα) showing peaks at diffraction angles 2θ of 8.5, 13.4, 19.1 and 24.5°.
3. The compound according to claim 1 , which is a crystal of 3-cyclopropyl-6-{(1R)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}pyridin-2(1H)-one having physical properties of the following (a) to (c):
(a) an X-ray powder diffraction pattern (Cu—Kα) showing peaks at diffraction angles 2θ of 8.5, 13.4, 19.1 and 24.5°;
(b) an infrared absorption spectrum showing characteristic absorption bands at 916, 1146, 1167, 1295, 1651, 1664, 2909, 2955, 3003 and 3146 cm −1 ; and
(c) a melting point of 199 to 201° C.
4. A method for producing a crystal of 3-cyclopropyl-6-{(1R)-1-[4-(1,1 -difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}pyridin-2(1H)-one having the physical properties of the following (a) to (c):
(a) an X-ray powder diffraction pattern (Cu—Kα) showing peaks at diffraction angles 2θ of 8.5, 13.4, 19.1 and 24.5°;
(b) an infrared absorption spectrum showing characteristic absorption bands at 916, 1146, 1167, 1295, 1651, 1664, 2909, 2955, 3003 and 3146 cm −1 ; and
(c) a melting point of 199 to 201° C.,
the method comprising: dissolving 3-cyclopropyl-6-{(1R)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}pyridin-2(1H)-one represented by formula [1] in an alcohol solvent while heating, to provide a solution; thereafter, adding a water solvent to the solution; cooling the resultant solution to 5° C. or lower to yield a crystal; and
drying the obtained crystal at 60° C. or lower:
5. A pharmaceutical composition comprising, as an active ingredient, the compound, a tautomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate of the compound, the tautomer thereof, or the salt thereof of claim 1 , and pharmacologically acceptable carriers or diluents.
6. A method for activating glucokinase, comprising administering an effective amount of the compound according to claim 1 to a subject in need thereof.
7. The pharmaceutical composition according to claim 5 , which is a hypoglycemic agent.
8. A method for treating diabetes comprising administering an effective amount of the compound according to claim 1 to a subject in need thereof.