Solid forms of (Z)-4-(5-((3-benzyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid

1. A crystalline form of a choline salt of a compound of Formula (I):

which is crystalline form G characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 5.6, 7.9, 11.2, 13.3, 15.0, 15.7, 16.1, 16.2, 16.5, 16.6, 17.8, 18.1, 18.5, 19.1, 19.8, 20.0, 21.1, 23.0, 24.6, 25.0, 25.6, 26.6, 26.8, 26.9, 29.3, 29.7, 30.6, 30.7, and 34.4 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

2. A crystalline form of a choline salt of a compound of Formula (I):

which is crystalline form O characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 8.4, 8.8, 9.3, 13.3, 14.3, 16.7, 17.0, 18.1, 19.4, 19.6, 19.9, 20.7, 20.9, 21.4, 21.7, 22.5, 23.4, 24.1, and 25.5 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

3. A crystalline form of a choline salt of a compound of Formula (I):

which is crystalline form Q characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 5.0, 5.2, 8.4, 9.6, 9.9, 11.5, 12.6, 12.8, 13.3, 14.4, 15.8, 16.1, 16.6, 17.5, 18.0, 19.3, 20.6, 20.7, 21.5, 21.7, 22.9, 23.7, 24.8, 25.1, 25.3, 25.3, 25.5, 26.3, 26.9, 27.0, 28.1, 28.8, 30.4, 31.2, 32.0, 35.7, and 37.4 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

4. A crystalline form of a choline salt of a compound of Formula (I):

which is crystalline form R characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 5.1, 5.6, 8.0, 8.2, 8.4, 9.8, 11.2, 12.7, 13.4, 14.6, 15.1, 15.7, 16.1, 16.3, 16.7, 17.1, 17.8, 18.2, 18.5, 19.1, 19.9, 20.1, 21.1, 22.6, 23.0, 23.4, 24.0, 24.5, 24.7, 25.0, 25.6, 26.0, 26.6, 26.8, 27.1, 27.4, 27.7, 28.1, 29.3, 29.7, 30.6, 31.1, 31.7, 32.2, 32.8, 33.2, 33.5, 34.5, 34.8, 35.1, 35.4, 36.5, 37.6, 38.5, 39.5, 40.4, 41.3, 42.7, and 44.4 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

5. A crystalline form of a choline salt of a compound of Formula (I):

which is crystalline form S characterized by an X-ray powder diffraction (XRPD) pattern including at least three peaks selected from 5.1, 8.4, 9.6, 10.0, 11.6, 12.9, 13.3, 14.4, 14.9, 15.8, 16.6, 17.4, 18.0, 19.2, 19.3, 20.6, 21.4, 21.7, 22.7, 23.7, 24.8, 25.4, 26.3, 26.8, 28.1, 28.7, 29.6, 30.3, 31.0, 31.9, 33.0, 34.0, 35.7, 37.4, 39.2, 40.5, and 41.7 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

6. The crystalline form of claim 4 , which is crystalline form R characterized by an X-ray powder diffraction (XRPD) pattern including at least six peaks selected from 5.6, 11.2, 15.1, 16.3, 16.7, 19.1, 20.1, 21.1, 23.0, 24.5, 25.0, 25.6, 26.0, 31.1, 32.8, and 33.5±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

7. The crystalline form of claim 4 , which is crystalline form R characterized by an X-ray powder diffraction (XRPD) pattern including at least nine peaks selected from 5.6, 11.2, 15.1, 16.3, 16.7, 19.1, 20.1, 21.1, 23.0, 24.5, 25.0, 25.6, 26.0, 31.1, 32.8, and 33.5±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

8. The crystalline form of claim 4 , which is crystalline form R characterized by an X-ray powder diffraction (XRPD) pattern in accordance with FIG. 7 , as determined on a diffractometer using Cu-Kα radiation.

9. A crystalline form of a meglumine salt of a compound of Formula (I):

which is crystalline form H characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 5.3, 7.1, 10.7, 10.9, 16.1, 16.5, 17.7, 18.5, 20.3, 23.6, 24.9, and 27.2 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

10. A crystalline form of a meglumine salt of a compound of Formula (I):

which is crystalline form L characterized by an X-ray powder diffraction (XRPD) pattern including at least three peaks selected from 5.3, 7.9, 8.5, 9.0, 9.9, 10.6, 10.9, 11.6, 12.0, 12.6, 13.1, 14.5, 14.8, 15.0, 15.3, 15.9, 16.2, 16.9, 17.4, 17.8, 18.0, 18.4, 18.8, 19.2, 20.2, 20.8, 21.3, 21.7, 22.1, 23.2, 23.8, 24.5, 25.2, 25.5, 26.3, 26.9, 27.3, 27.9, 28.4, 28.9, 29.2, 29.8, 30.3, 30.6, 31.1, 32.1, 32.8, 34.1, 34.5, 34.9, 35.1, 36.0, 36.5, 37.5, 38.0, 38.9, 39.6, 40.7, 41.7, 42.5, and 42.9 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

11. A crystalline form of a meglumine salt of a compound of Formula (I):

which is crystalline form M characterized by an X-ray powder diffraction (XRPD) pattern including at least three peaks selected from 6.5, 8.5, 9.0, 9.9, 10.6, 11.6, 14.4, 14.8, 15.0, 15.3, 15.9, 16.1, 16.9, 17.8, 18.0, 19.0, 20.4, 20.8, 21.3, 21.7, 23.6, 24.5, 25.2, 26.3, 26.9, 27.5, 27.9, 28.5, 28.9, 29.8, 30.6, 32.1, 32.8, 33.8, 34.5, 36.0, 36.4, 37.1, 38.0, 39.7, 40.7, 41.7, 43.0, and 44.0 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

12. A crystalline form of a meglumine salt of a compound of Formula (I):

which is crystalline form N characterized by an X-ray powder diffraction (XRPD) pattern including at least three peaks selected from 4.3, 5.0, 5.4, 6.1, 7.5, 7.9, 8.9, 9.5, 10.0, 10.8, 11.4, 12.1, 12.5, 13.8, 14.3, 14.8, 15.6, 16.1, 16.7, 17.4, 18.1, 19.2, 19.5, 20.1, 20.9, 21.4, 21.5, 22.1, 22.5, 23.9, 24.6, 25.3, 26.3, 26.7, 27.1, 27.6, 28.2, 29.0, 30.4, 30.9, 32.0, 32.9, 33.9, 34.7, 36.9, 38.3, 39.1, 39.6, 40.2, and 41.4 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

13. A crystalline form of a meglumine salt of a compound of Formula (I):

which is crystalline form T characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three peaks selected from the group consisting of 6.9, 8.2, 8.4, 9.4, 11.6, 15.0, 15.1, 15.5, 17.2, 17.8, 18.1, 20.5, 21.3, 21.9, 22.3, 23.5, 25.0, and 26.7 °2θ, ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

14. The crystalline form of claim 9 , which is crystalline form H characterized by an X-ray powder diffraction (XRPD) pattern comprising at least six peaks selected from the group consisting of 5.3, 7.1, 10.7, 10.9, 16.1, 16.5, 17.7, 18.5, 20.3, 23.6, 24.9, and 27.2±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

15. The crystalline form of claim 9 , which is crystalline form H characterized by an X-ray powder diffraction (XRPD) pattern comprising at least ten peaks selected from the group consisting of 5.3, 7.1, 10.7, 10.9, 16.1, 16.5, 17.7, 18.5, 20.3, 23.6, 24.9, and 27.2±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation.

16. The crystalline form of claim 9 , which is crystalline form H characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 6B , as determined on a diffractometer using Cu-Kα radiation.

17. A crystalline form of a tromethamine salt of a compound of Formula (I):

which is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 6C , as determined on a diffractometer using Cu-Kα radiation.

18. A crystalline form of a tromethamine salt of a compound of Formula (I):

which is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 6D , as determined on a diffractometer using Cu-Kα radiation.

19. A pharmaceutical formulation comprising a pharmaceutically acceptable excipient and a crystalline form of a choline salt of a compound of Formula (I) as recited in any one of claims 1 , 2 , 3 , 4 , 5 , 6 , 7 or 8 .

20. A pharmaceutical formulation comprising a pharmaceutically acceptable excipient and a crystalline form of a meglumine salt of a compound of Formula (I) as recited in any one of claim 9 , 10 , 11 , 12 , 13 , 14 , 15 or 16 .

21. A method for treating a β2 integrin-mediated condition comprising administering to a patient having said condition a pharmaceutical formulation 19 .

22. A method for treating a β2 integrin-mediated condition comprising administering to a patient having said condition a pharmaceutical composition of claim 20 .

23. The method of claim 21 , wherein the β2 integrin-mediated condition is selected from the group consisting of acute inflammation, chronic inflammation, chronic kidney disease, neointimal thickening associated with vascular injury, tissue injury, peritonitis, diabetic nephropathy, an autoimmune disease, cancer, glaucoma, graft versus host disease, macular degeneration, and uveitis.

24. The method of claim 21 , wherein the β2 integrin-mediated condition is cancer.

25. The method of claim 22 , wherein the β2 integrin-mediated condition is selected from the group consisting of acute inflammation, chronic inflammation, chronic kidney disease, neointimal thickening associated with vascular injury, tissue injury, peritonitis, diabetic nephropathy, an autoimmune disease, cancer, glaucoma, graft versus host disease, macular degeneration, and uveitis.

26. The method of claim 22 , wherein the β2 integrin-mediated condition is cancer.