Crystalline forms of an S1P receptor modulator
AssigneeOppilan Pharma Ltd.
InventorsJohn Nuss, Jason Harris, Shendong Yuan, Scott Alan Wolckenhauer
Life of this patent
Estimating the term…
Abstract
Described herein are crystalline forms of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one, or a salt or solvate thereof.
Claims20
A crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one, wherein the crystalline form is Form 1 having at least one of the following properties:
- (a) an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 1;
- (b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 16.5° 2-Theta, 18.5° 2-Theta, 21.0° 2-Theta, 22.1° 2-Theta, 22.8° 2-Theta, 26.6° 2-Theta, 27.8° 2-Theta, and 28.9° 2-Theta;
- (c) a thermo-gravimetric analysis (TGA) substantially similar to the one set forth in FIG. 2;
- (d) a DSC thermogram substantially similar to the one set forth in FIG. 2;
- (e) a DSC thermogram with an endotherm having an onset at about 282° C.;
- or
- (f) combinations thereof.
A crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one, wherein the crystalline form is Form 2 having at least one of the following properties:
- (a) an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 3;
- (b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 6.9° 2-Theta, 17.1° 2-Theta, 18.1° 2-Theta, 22.0° 2-Theta, 24.0° 2-Theta, 24.8° 2-Theta, 25.5° 2-Theta, 26.2° 2-Theta, and 28.2° 2-Theta;
- (c) a thermo-gravimetric analysis (TGA) substantially similar to the one set forth in FIG. 4;
- (d) a DSC thermogram substantially similar to the one set forth in FIG. 4;
- (e) a DSC thermogram with a first endotherm having an onset at about 145° C. and a second endotherm having an onset at about 280° C.;
- or
- (f) combinations thereof.
A crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one para-toluenesulfonic acid salt, wherein the crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one para-toluenesulfonic acid salt is Form 3 having at least one of the following properties:
- (a) an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 5;
- (b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 4.9° 2-Theta, 8.4° 2-Theta, 17.5° 2-Theta, 19.8° 2-Theta, 20.5° 2-Theta, 24.8° 2-Theta, 25.6° 2-Theta, and 26.4° 2-Theta;
- (c) a thermo-gravimetric analysis (TGA) substantially similar to the one set forth in FIG. 6;
- (d) a DSC thermogram substantially similar to the one set forth in FIG. 6;
- (e) a DSC thermogram with a first endotherm at about 41° C., a second endotherm having an onset at about 93° C., and a third endotherm having an onset at about 156° C.;
- or
- (f) combinations thereof.
A crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one is a methanesulfonic acid salt, wherein the crystalline form of (R)-5-(2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-2-one methanesulfonic acid salt is Form 4 having at least one of the following properties:
- (a) an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 7;
- (b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 10.8° 2-Theta, 15.4° 2-Theta, 17.3° 2-Theta, 18.2° 2-Theta, 19.2° 2-Theta, 20.1° 2-Theta, 21.6° 2-Theta, 22.8° 2-Theta, 23.4° 2-Theta, 24.8° 2-Theta, 25.3° 2-Theta, 26.7° 2-Theta, and 30.9° 2-Theta;
- (c) a thermo-gravimetric analysis (TGA) substantially similar to the one set forth in FIG. 8;
- (d) a DSC thermogram substantially similar to the one set forth in FIG. 8;
- (e) a DSC thermogram with a first endotherm at about 60° C. and a second endotherm having an onset at about 128° C.;
- or
- (f) combinations thereof.
Dependencies are inferred from the claim text.