Solid forms of(Z)-4-(5-((3-benzyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl) benzoic acid
The present invention provides new salts and crystalline forms of leukadherin LA1 [(Z)-4-(5-((3-benzyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid] according to Formula I. Methods for preparation of the salts and crystalline forms are also described, as well as methods for treating β2 integrin-mediated diseases and conditions using the salts and crystalline forms.
1. A method for treating a cancer comprising administering to a patient having cancer:
(a) an immune checkpoint inhibitor; and
(b) a choline or meglumine salt of a compound according to Formula (I)
or a crystalline form thereof.
2. The method of claim 1 , wherein the immune checkpoint inhibitor inhibits the activity of an immune checkpoint protein selected from the group consisting of PD1, PD-L1, PD-L2, CTLA-4, TIM3, B7-H3, B7-H4, BTLA, HVEM, GAL9, LAG3, VISTA, KIR, 2B4, CD160, and IDO1/IDO2.
3. The method of claim 2 , wherein the immune checkpoint inhibitor inhibits the activity of PD1.
4. The method of claim 3 , wherein the immune checkpoint inhibitor is MK-3475 (pembrolizumab).
5. The method of claim 3 , wherein the immune checkpoint inhibitor is nivolumab.
6. The method of claim 2 , wherein the immune checkpoint inhibitor inhibits the activity of PD-L1.
7. The method of claim 6 , wherein the immune checkpoint inhibitor is MEDI4736 (durvalumab), MSB0010718C (avelumab), MPLD3280A (atezolizumab), or BMS-936559.
8. The method of claim 2 , wherein the immune checkpoint inhibitor inhibits the activity of CTLA-4.
9. The method of claim 8 , wherein the immune checkpoint inhibitor is ipilimumab or tremelimumab.
10. The method of claim 1 , wherein the immune checkpoint inhibitor is a protein.
11. The method of claim 10 , wherein the protein is an antibody or antigen binding fragment thereof.
12. The method of claim 1 , wherein the immune checkpoint inhibitor inhibits the activity of PD1 and the cancer is melanoma, pancreatic cancer, esophageal cancer, colon cancer, prostate cancer, breast cancer, or stomach cancer.
13. The method of claim 12 , wherein the immune checkpoint inhibitor is MK-3475 (pembrolizumab).
14. The method of claim 12 , wherein the immune checkpoint inhibitor is nivolumab.
15. The method of claim 1 , wherein the immune checkpoint inhibitor inhibits the activity of CTLA4 and the cancer is melanoma.
16. The method of claim 15 , wherein the immune checkpoint inhibitor is ipilimumab or tremelimumab.
17. The method of claim 1 , wherein the salt is a choline salt according to Formula (I) or a crystalline form thereof.
18. The method of claim 1 , wherein the salt is a meglumine salt according to Formula (I) or a crystalline form thereof.