Crystalline compounds
The present invention relates to crystalline forms of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and compositions comprising the same and methods of making and using the same.
1. A process for making Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises seeding a solution or slurry of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride with Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 5.7, 5.4, 5.2, 4.8, 4.6, 4.3, 3.9, and 3.5.
2. The process of claim 1 , wherein the solution or slurry is seeded while the temperature of the solution or slurry is above room temperature.
3. The process of claim 1 , wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 1, 35, 37, and 47 .
4. The process of claim 2 , wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 1, 35, 37, and 47 .
5. The process of claim 1 further comprising isolating the Crystalline Form A.
6. The process of claim 2 further comprising isolating the Crystalline Form A.
7. The process of claim 3 further comprising isolating the Crystalline Form A.
8. The process of claim 4 further comprising isolating the Crystalline Form A.
9. A process for making Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises dissolving (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride in ethanol with heating, optionally filtering, concentrating, seeding with Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride before or after concentrating, and optionally filtering, wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 5.7, 5.4, 5.2, 4.8, 4.6, 4.3, 3.9, and 3.5.
10. The process of claim 9 , wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 1, 35, 37, and 47 .
11. The process of claim 9 further comprising isolating the Crystalline Form A.
12. The process of claim 10 further comprising isolating the Crystalline Form A.
13. A process for making a pharmaceutical composition comprising Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises isolating Crystalline Form A of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and admixing the isolated Crystalline Form A with a pharmaceutically acceptable diluent or carrier, wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 5.7, 5.4, 5.2, 4.8, 4.6, 4.3, 3.9, and 3.5.
14. The process of claim 13 , wherein the Crystalline Form A exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 1, 35, 37, and 47 .