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Publication number WO2017013498 A2
Publication type Application
Application number PCT/IB2016/001181
Publication date Jan 26, 2017
Filing date Jul 19, 2016
Priority date Jul 22, 2015
Also published as WO2017013498A3
Inventors Peter York, Lucy Anne LEONARD, Daniel Mark LEDGER, Linda Sharon Daintree
Applicant Anavex Life Sciences Corp.
Export Citation BiBTeX, EndNote, RefMan
Classifications (5), Legal Events (1)
External Links: Patentscope, Espacenet
Crystal forms of tetra-hydro-n, n-dimethyl-2, 2-diphenyl-3-furanmethanamine hydrochloride, processes for making such forms, and their pharmaceutical compositions
WO 2017013498 A2
ABSTRACT
Polymorphic forms of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride (ANAVEX2-73) and a metabolite of tetrahydro-N,N-dimethyl-2,2-diphenyl-3-furanmethanamine hydrochloride (ANAVEX2-73) are disclosed and characterized. Compositions and method for treatment of Alzheimer's disease that includes the polymorphic forms and metabolite of tetrahydro-N,N-dimethyl-2,2- diphenyl-3-furanmethanamine hydrochloride (ANAVEX2-73).
CLAIMS (OCR text may contain errors)
CLAIMS What is claimed is:
1. A crystalline form of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the PXRD pattern shown in FIG. 1, FIG. 4, or FIG. 8.
2. The crystalline form of claim 1, further characterized by the FTIR spectrum shown in FIG. 5 or FIG. 9.
3. The crystalline form of claim 1, further characterized by the ^-NMR spectrum shown in FIG. 6 or FIG. 10.
4. The crystalline form of claim 1, further characterized by the particle shapes depicted in FIG. 2, FIG. 3, FIG. 7 or FIG. 11.
5. The crystalline form of claim 1, further characterized by the particle sizes depicted in FIG. 2, FIG. 3, FIG. 7 or FIG. 11.
6. The crystalline form of claim 1, wherein the habit is plate-like.
7. The crystalline form of claim 1, wherein the habit is needle-like.
The crystalline form of claim 1, wherein the habit is lath
9. A method of making the crystalline form of claim 1, wherein the method uses a supercritical fluid (SCF) technique.
10. A dosage form comprising a therapeutically neuroprotective amount of the crystalline form of claim 1.
11. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the crystalline form of any of claims 1-8.
12. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the crystalline form of any of claims 1-8.
13. Crystalline Form I of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the PXRD pattern shown in FIG. 1.
14. The crystalline Form I according to claim 13, characterized by the particle shapes as depicted in FIG. 2.
15. The crystalline Form I according to claim 13, characterized by the particle shapes as depicted in FIG. 3.
16. The crystalline Form I according to claim 13, characterized by the particle sizes as depicted in FIG. 2.
17. The crystalline Form I according to claim 13, characterized by the particle sizes as depicted in FIG. 3.
18. The crystalline form of claim 13, wherein the habit is plate-like.
19. A method of making the crystalline form of any of claims 13-18, wherein the method uses a supercritical fluid (SCF) technique.
20. A dosage form comprising a therapeutically neuroprotective amount of the crystalline form of any of claims 13-18.
21. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the crystalline form of any of claims 13-18.
22. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the crystalline form of any of claims 13-18.
23. Crystalline Form II of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the PXRD pattern shown in FIG. 4.
24. Crystalline Form II of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the FTIR spectrum shown in FIG. 5.
25. Crystalline Form II of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the ^-NMR spectrum shown in FIG. 6.
26. The crystalline Form II according to any of claims 23-25, characterized by particle shapes as depicted in FIG. 7.
27. The crystalline Form II according to any of claims 23-25, characterized by particle sizes as depicted in FIG. 7.
28. The crystalline Form II of any of claims 23-25, wherein the habit is plate-like.
29. A method of making the crystalline Form II of any of claims 23-28, wherein the method uses a supercritical fluid (SCF) technique.
30. A dosage form comprising a therapeutically neuroprotective amount of the crystalline Form II of any of claims 23-28.
31. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the crystalline Form II of any of claims 23-28.
32. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the crystalline Form II of any of claims 23-28.
33. Crystalline Form III of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the PXRD pattern shown in FIG. 8.
34. Crystalline Form III of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the FTIR spectrum shown in FIG. 9.
35. Crystalline Form III of tetrahydro-N,N-dimethyl-2,2-diphenyl-3- furanmethanamine hydrochloride characterized by the ^-NMR spectrum shown in FIG. 10.
36. The crystalline Form III according to any of claims 33-35, characterized by particle shapes as depicted in FIG. 11.
37. The crystalline Form III according to any of claims 33-35, characterized by particle sizes as depicted in FIG. 11.
38. The crystalline Form III of any of claims 33-35, wherein the habit is lath-like.
39. A method of making the crystalline Form III of any of claims 33-38, wherein the method uses a supercritical fluid (SCF) technique.
40. A dosage form comprising a therapeutically neuroprotective amount of the crystalline Form III of any of claims 33-38.
41. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the crystalline Form III of any of claims 33-38.
42. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the crystalline Form III of any of claims 33-38.
43. The metabolite ANAVEX19-144 characterized by the PXRD pattern shown in FIG. 12.
44. The metabolite ANAVEX19-144 characterized by the DSC-TGA data shown in FIG. 13.
45. The metabolite ANAVEX19-144 characterized by the FTIR spectrum shown in FIG. 14.
46. The metabolite ANAVEX19-144 of any of claims 43-45 characterized by particle shapes as depicted in FIG. 15.
47. The metabolite ANAVEX19-144 of any of claims 43-45 characterized by particle sizes as depicted in FIG. 15.
48. The metabolite ANAVEX19-144 of any of claims 43-45, wherein the habit is needle-like.
49. A method of making the metabolite ANAVEX19-144 of any of claims 43-48, wherein the method uses a supercritical fluid (SCF) technique.
50. A dosage form comprising a therapeutically neuroprotective amount of the metabolite ANAVEX19-144 of any of claims 43-48.
51. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the metabolite ANAVEX19-144 of any of claims 43-48.
52. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the metabolite ANAVEX19-144 of any of claims 43-48.
53. The metabolite ANAVEX19-144 characterized by the PXRD pattern shown in FIG. 17.
54. The metabolite ANAVEX19-144 characterized by the DSC-TGA data shown in FIG. 18.
55. The metabolite ANAVEX19-144 of any of claims 53-54 characterized by particle shapes as depicted in FIG. 16.
56. The metabolite ANAVEX19-144 of any of claims 53-54 characterized by particle sizes as depicted in FIG. 16.
57. A method of making the metabolite ANAVEX19-144 of any of claims 53-56, wherein the method uses a supercritical fluid (SCF) technique.
58. A dosage form comprising a therapeutically neuroprotective amount of the metabolite ANAVEX19-144 of any of claims 53-56.
59. A pharmaceutical composition for the treatment of Alzheimer's disease comprising a therapeutically effective amount of the metabolite ANAVEX19-144 of any of claims 53-56.
60. A method of treating Alzheimer's disease in a subject comprising administering to the subject a therapeutically effective amount of the metabolite ANAVEX19-144 of any of claims 53-56.
DESCRIPTION (OCR text may contain errors)
CRYSTAL FORMS OF TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-3- FURANM ETHAN AMINE HYDROCHLORIDE, PROCESSES OF MAKING SUCH
FORMS, AND THEIR PHARMACEUTICAL COMPOSITIONS
FIELD
[0001] The present disclosure is directed to crystalline forms of tetrahydro-N,N-dimethyl-2,2-diphenyl-3-furanmethanamine
hydrochloride, as well as compositions, processes of preparation, and uses thereof.
