Claims for Patent: 11,773,105

Summary for Patent: 11,773,105

Title:	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]- pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
Abstract:	The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis), kits, methods of synthesis, and products-by-process.
Inventor(s):	Ayman ALLIAN
Assignee:	AbbVie Inc
Application Number:	US18/094,263
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 11,773,105
Patent Claims:	1. Crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 2. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 3. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 4. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 7.7±0.2, 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 5. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 7.7±0.2, 7.9±0.2, 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 6. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.8±0.2, 20.5±0.2, 20.9±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 7. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.2±0.2, 17.8±0.2, 20.5±0.2, 20.9±0.2, 23.5±0.2, and 24.9±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 8. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 23.5±0.2, and 24.9±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 9. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 21.2±0.2, 23.5±0.2, 24.9±0.2 and 27.4±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 10. The crystalline freebase of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 21.2±0.2, 22.6±0.2, 23.5±0.2, 24.9±0.2 and 27.4±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 11. The crystalline freebase of claim 1, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is an anhydrate. 12. The crystalline freebase of claim 1, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hydrate. 13. The crystalline freebase of claim 12, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hemihydrate. 14. The crystalline freebase of claim 1, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a solvate. 15. A pharmaceutical composition comprising crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide having an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation, and a pharmaceutically acceptable carrier. 16. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 17. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 18. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 7.7±0.2, 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 19. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 7.7±0.2, 7.9±0.2, 10.3±0.2, 12.4±0.2, 15.5±0.2, 17.8±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 20. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.8±0.2, 20.5±0.2, 20.9±0.2, and 23.5±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 21. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 17.2±0.2, 17.8±0.2, 20.5±0.2, 20.9±0.2, 23.5±0.2, and 24.9±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 22. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 23.5±0.2, and 24.9±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 23. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 21.2±0.2, 23.5±0.2, 24.9±0.2 and 27.4±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 24. The pharmaceutical composition of claim 15, wherein the crystalline freebase has an X-ray powder diffraction pattern characterized by peaks at 12.4±0.2, 15.9±0.2, 17.2±0.2, 17.8±0.2, 19.3±0.2, 20.5±0.2, 20.9±0.2, 21.2±0.2, 22.6±0.2, 23.5±0.2, 24.9±0.2 and 27.4±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 25. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is a solid dosage form. 26. The pharmaceutical composition of claim 25, wherein the solid dosage form is a tablet. 27. The pharmaceutical composition of claim 15, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is an anhydrate. 28. The pharmaceutical composition of claim 15, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hydrate. 29. The pharmaceutical composition of claim 28, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hemihydrate. 30. The pharmaceutical composition of claim 15, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a solvate.