Salt Forms Of 4-Cyano-N-(4,4-Dimethylcyclohex-1-EN-1-YL)-6-(2,2,6,6-Tetramethyltetrahydro-2H-Pyran-4-YL)Pyridin-3-YL)-1H-Imidazole-2-Carboximide

Abstract

The present disclosure discusses salt forms of 4-cyano-N-[2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl]-1H-imidazole-2-carboxamide.

What is claimed is: 
     
         1 . A pharmaceutically acceptable salt form of 4-cyano-N-[2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl]-1H-imidazole-2-carboxamide (Compound A) 
       
         
           
           
               
               
           
         
         wherein the pharmaceutically acceptable salt is selected from the group consisting of 
         Compound A, sulfate salt; 
         Compound A, phosphate salt; 
         Compound A, mesylate salt; 
         Compound A, tosylate salt; and 
         Compound A, besylate salt. 
       
     
     
         2 . The salt form of  claim 1  that is Compound A, sulfate salt. 
     
     
         3 . The salt form of  claim 2 , in an amorphous form. 
     
     
         4 . The salt form of  claim 2 , characterized by a differential scanning calorimetry thermogram comprising endothermic events with peak temperatures at about 47.4° C., about 207.2° C., and about 232.8° C. 
     
     
         5 . The salt form of  claim 1  that is Compound A, besylate salt. 
     
     
         6 . The salt form of  claim 5 , in a crystalline form. 
     
     
         7 . The salt form of  claim 5 , characterized by an X-ray powder diffraction pattern comprising peaks at 5.8, 6.3, 17.1, 17.4, and 17.6 degrees two theta±0.2 degrees two theta. 
     
     
         8 . The salt form of  claim 7 , wherein the X-ray powder diffraction pattern further comprises one or more of the following peaks: 7.8, 8.6, 8.9, 18.2, 18.9, 19.6 or 23.0 degrees two theta±0.2 degrees two theta. 
     
     
         9 . The salt form of  claim 5 , further characterized by an X-ray powder diffraction pattern substantially as depicted in  FIG. 24 . 
     
     
         10 . The salt form of  claim 5 , characterized by a differential scanning calorimetry thermogram comprising endothermic events with peak temperatures at about 51.5° C., about 164.8° C., and about 212.2° C. 
     
     
         11 . A pharmaceutical composition comprising the salt form of  claim 1  and at least one pharmaceutically acceptable excipient. 
     
     
         12 . A method of inhibiting colony-stimulating factor-1 receptor in a subject, said method comprising administering to said subject at least one salt form of  claim 1  to said subject. 
     
     
         13 . A method of treating a disease that is at least one of osteoporosis, Paget's disease, rheumatoid arthritis and other forms of inflammatory arthritis, osteoarthritis, prosthesis failure, osteolytic sarcoma, myeloma, or tumor metastasis to bone in a subject comprising administering a therapeutically effective amount of at least one salt form of  claim 1  to said subject. 
     
     
         14 . The method of  claim 19 , wherein said disease is rheumatoid arthritis or cancer. 
     
     
         15 . The method of  claim 19 , wherein said disease is cancer metastasis to bone. 
     
     
         16 . A method of treating a disease that is at least one of glomerulonephritis, inflammatory bowel disease, sarcoidosis, congestive obstructive pulmonary disease, idiopathic pulmonary fibrosis, asthma, pancreatitis, HIV infection, psoriasis, diabetes, tumor-related angiogenesis, age-related macular degeneration, diabetic retinopathy, restenosis, schizophrenia, or Alzheimer's dementia in a subject comprising administering a therapeutically effective amount of at least one salt form of  claim 1  to the subject. 
     
     
         17 . A method of treating pain in a subject comprising administering to the subject a therapeutically effective amount of at least one salt form of  claim 1  to the subject. 
     
     
         18 . A method of treating a disease that is at least one of ovarian cancer, uterine cancer, breast cancer, prostate cancer, lung cancer, colon cancer, stomach cancer, or hairy cell leukemia in a subject comprising administering a therapeutically effective amount of at least one salt form of  claim 1  to the subject. 
     
     
         19 . A method of treating or preventing metastasis from ovarian cancer, uterine cancer, breast cancer, prostate cancer, lung cancer, colon cancer, stomach cancer, or hairy cell leukemia in a subject comprising administering a therapeutically effective amount of at least one salt form of  claim 1  to the subject. 
     
     
         20 . A method of treating an autoimmune disease that is at least one of systemic lupus erythematosus, rheumatoid arthritis and other forms of inflammatory arthritis, psoriasis, Sjogren's syndrome, multiple sclerosis, or uveitis in a subject comprising administering a therapeutically effective amount of at least one salt form of  claim 1  to the subject. 
     
     
         21 . The method of claim  23 , wherein the pain is selected from skeletal pain caused by tumor metastasis or osteoarthritis, or visceral, inflammatory, or neurogenic pain.