Solid Forms of (E)-1-(4-((1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone Oxime

Abstract

Solid forms of (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone oxime, compositions comprising them, and methods of their use are disclosed.

1 - 8 . (canceled) 
     
     
         9 . Crystalline anhydrous (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime. 
     
     
         10 . The crystalline anhydrous (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime of  claim 9 , which has a X-ray powder diffraction pattern comprising peaks at about 4.7, 8.2 and/or 12.5 degrees 2θ. 
     
     
         11 . The crystalline anhydrous (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime of  claim 9 , which has a X-ray powder diffraction pattern comprising peaks at about 17.1, 19.9 and/or 20.8 degrees 2θ. 
     
     
         12 . The crystalline anhydrous (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime of  claim 9 , which has a X-ray powder diffraction pattern comprising peaks at about 29.3, 32.0 and/or 33.1 degrees 2θ. 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . Crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime monohydrate. 
     
     
         16 . Crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime dihydrate. 
     
     
         17 . The crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime dihydrate of  claim 16 , which has a X-ray powder diffraction pattern comprising peaks at about 12.5, 14.1 and/or 16.9 degrees 2θ. 
     
     
         18 . The crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime dihydrate of  claim 16 , which has a X-ray powder diffraction pattern comprising peaks at about 20.4, 25.2 and/or 27.0 degrees 2θ. 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime dihydrate crystallized in a P1 space group. 
     
     
         22 . (canceled) 
     
     
         23 . A composition comprising crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime or a hydrate thereof and a pharmaceutically acceptable excipient. 
     
     
         24 - 30 . (canceled) 
     
     
         31 . A method of reducing the number of circulating lymphocytes in a patient, which comprises administering to the patient an effective amount of crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime or a hydrate thereof. 
     
     
         32 - 38 . (canceled) 
     
     
         39 . A method of suppressing immune response in a patient, which comprises administering to the patient an effective amount of crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime or a hydrate thereof. 
     
     
         40 - 42 . (canceled) 
     
     
         43 . A method of treating, managing or preventing an autoimmune or inflammatory disease or disorder, which comprises administering to a patient in need thereof a therapeutically or prophylactically effective amount of crystalline (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-ethanone oxime or a hydrate thereof. 
     
     
         44 - 46 . (canceled) 
     
     
         47 . The method of  claim 43 , wherein the disease or disorder is rheumatoid arthritis. 
     
     
         48 . The method of  claim 43 , wherein the disease or disorder is multiple sclerosis.