Crystalline forms of a cannabinoid receptor type 1 (CB1) modulator and methods of use and preparation thereof
AssigneeAnebulo Pharmaceuticals, Inc.
InventorsJoseph Fenton Lawler, Daniel Pawel Schneeberger
Life of this patent
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Abstract
Described herein are polymorphic forms of a CB1 modulator, methods of making such forms, pharmaceutical compositions and medicaments comprising such forms, and methods of using such forms in the treatment of conditions, diseases, or disorders that would benefit from modulation of the CB1 receptor.
Claims18
A method of preparing a crystalline form of (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide (Compound 1):
- Compound 1, wherein the method comprises:
- (a) dissolving the (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide in a solvent to obtain a solution;
- and (b) crystallizing the solution obtained in step (a).
A method of preparing a crystalline form of (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide (Compound 1):
- Compound 1, wherein the method comprises:
- (a) dissolving the (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide in a solvent to obtain a solution;
- and (b) crystallizing the solution obtained in step (a),
- wherein the crystalline (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide is characterized by:
- (a) an X-ray powder diffraction pattern comprising peaks at 10.2±0.2° 2-θ, 18.1±0.2° 2-θ, and 20.7±0.2° 2-θ, as measured by X-ray powder diffraction using an X-ray wavelength of 1.5406 Å;
- (b) an X-ray powder diffraction pattern substantially the same as shown in FIG. 1;
- (c) a differential scanning calorimetry (DSC) thermogram comprising an endotherm in the range of about 80-90° C.;
- (d) a differential scanning calorimetry (DSC) thermogram comprising an endotherm with an onset of about 84° C. and a peak of about 86° C.;
- (e) a differential scanning calorimetry (DSC) thermogram substantially the same as shown in FIG. 2;
- (f) a thermogravimetric analysis (TGA) thermogram substantially the same as shown in FIG. 3;
- (g) a dynamic vapor sorption (DVS) trace substantially the same as shown in FIG. 4;
- (h) a substantially unchanged XPRD after storage at 25° C. and 90% relative humidity (RH);
- (i) a substantially unchanged XPRD after storage at laboratory conditions for at least 5 weeks;
- or
- (j) combinations thereof.
A method of preparing a crystalline form of (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide (Compound 1):
- Compound 1, wherein the method comprises:
- (a) dissolving the (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide in a solvent to obtain a solution;
- and (b) crystallizing the solution obtained in step (a),
- wherein the crystalline (R)—N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide is characterized by:
- (a) an X-ray powder diffraction pattern comprising peaks at 15.2±0.2° 2-θ, 18.2±0.2° 2−θ, and 20.8±0.2° 2-θ as measured by X-ray powder diffraction using an X-ray wavelength of 1.5406 Å;
- (b) an X-ray powder diffraction pattern substantially the same as shown in FIG. 5;
- (c) a differential scanning calorimetry (DSC) thermogram comprising an endotherm in the range of about 80-90° C.;
- (d) a differential scanning calorimetry (DSC) thermogram comprising an endotherm with an onset of about 81° C. and a peak of about 85° C.;
- (e) a differential scanning calorimetry (DSC) thermogram substantially the same as shown in FIG. 6;
- (f) a thermogravimetric analysis (TGA) thermogram substantially the same as shown in FIG. 7;
- (g) a dynamic vapor sorption (DVS) trace substantially the same as shown in FIG. 8;
- (h) a substantially unchanged XPRD after storage at 25° C. and 90% relative humidity (RH);
- (i) a substantially unchanged XPRD after storage at laboratory conditions for at least 5 weeks;
- or
- (j) combinations thereof.
Dependencies are inferred from the claim text.