Claims for Patent: 11,186,584

Summary for Patent: 11,186,584

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, Jayanthy Jayanth, Mohamed-Eslam F. Mohamed, Mathew Mulhern, Fredrik Lars NORDSTROM, Ahmed A. Othman, Michael J. Rozema, Lakshmi Bhagavatula, Patrick J. Marroum, Peter T. Mayer, Ahmad Y. Sheikh, Thomas B. Borchardt, Ben Klünder
Assignee:	AbbVie Inc
Application Number:	US17/230,288
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 11,186,584
Patent Claims:	1. Crystalline (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 (Compound 1) selected from the group consisting of: a. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 15.5±0.2, 17.0±0.2 and 21.7±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation; b. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation; and c. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 2. A process for preparing a pharmaceutical composition comprising amorphous 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 (Compound 1), the process comprising contacting a crystalline freebase Compound 1 with a pharmaceutically acceptable carrier, wherein the crystalline freebase Compound 1 is selected from the group consisting of: a. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation; and b. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation; wherein the crystalline freebase Compound 1 is converted into amorphous freebase of Compound 1. 3. The crystalline freebase Compound 1 of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 4. The crystalline freebase Compound 1 of claim 3, further characterized by at least one additional peak selected from the group consisting of 5.4±0.2, 12.1±0.2 and 19.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 5. The crystalline freebase Compound 1 of claim 3, which is an isopropyl acetate/water solvate. 6. The crystalline freebase Compound 1 of claim 1, having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 7. The crystalline freebase Compound 1 of claim 6, further characterized by at least one additional peak selected from the group consisting of 12.0±0.2 and 25.0±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 8. The crystalline freebase Compound 1 of claim 6, which is a hydrate. 9. The process of claim 2, wherein the contacting comprises dispersing the crystalline freebase Compound 1 in the pharmaceutically acceptable carrier. 10. The process of claim 2, wherein the pharmaceutically acceptable carrier is a hydrophilic polymer. 11. The process of claim 2, wherein at least about 80% by weight of the crystalline freebase Compound 1 is converted into the amorphous freebase Compound 1. 12. The process of claim 2, wherein at least about 98% by weight of the crystalline freebase Compound 1 is converted into the amorphous freebase Compound 1. 13. The process of claim 2, wherein the crystalline freebase Compound 1 has an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 14. The process of claim 13, wherein the crystalline freebase Compound 1 is further characterized by at least one additional peak selected from the group consisting of 5.4±0.2, 19.1±0.2 and 12.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 15. The process of claim 13, wherein the crystalline freebase Compound 1 is an isopropyl acetate/water solvate. 16. The process of claim 2, wherein the crystalline freebase Compound 1 has an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 17. The process of claim 16, wherein the crystalline freebase Compound 1 is further characterized by at least one additional peak selected from the group consisting of 12.0±0.2 and 25.0±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 18. The process of claim 16, wherein the crystalline freebase Compound 1 is a hydrate. 19. A process for preparing a pharmaceutical composition comprising 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 (Compound 1), the process comprising contacting a crystalline freebase Compound 1 with a pharmaceutically acceptable carrier, wherein the crystalline freebase Compound 1 is selected from the group consisting of: a. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation; and b. crystalline freebase Compound 1 having an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 20. The process of claim 19, wherein the crystalline freebase Compound 1 has an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.4±0.2 and 21.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 21. The process of claim 20, wherein the crystalline freebase Compound 1 is further characterized by at least one additional peak selected from the group consisting of 5.4±0.2, 12.1±0.2 and 19.1±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 22. The process of claim 20, wherein the crystalline freebase Compound 1 has an X-ray powder diffraction pattern characterized by peaks at 3.1±0.2, 9.3±0.2 and 20.8±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation. 23. The process of claim 22, wherein the crystalline freebase Compound 1 is further characterized by at least one additional peak selected from the group consisting of 12.0±0.2 and 25.0±0.2 degrees two theta when measured at about 25° C. with monochromatic Kα1 radiation.