Novel forms of apremilast

Abstract

The present disclosure is directed to novel forms of apremilast and pharmaceutical compositions comprising any of the novel forms of apremilast. Also provided are processes for the preparation of novel forms of apremilast.

1 - 16 . (canceled) 
     
     
         17 . A form of apremilast selected from apremilast formic acid solvate Form J, or anhydrous apremilast Form K that has an X-ray powder diffraction pattern comprising peaks, in terms of 2-theta, at about 11.40 and about 13.66. 
     
     
         18 . The form of apremilast according to  claim 17  which is apremilast formic acid solvate Form J. 
     
     
         19 . The apremilast formic acid solvate Form J according to  claim 18  that has an X-ray powder diffraction pattern comprising peaks, in terms of 2-theta, at about 10.81 and about 27.26. 
     
     
         20 . The apremilast formic acid solvate Form J according to  claim 19 , further comprising peaks, in terms of 2-theta, at about 21.21, about 13.12 and about 12.72. 
     
     
         21 . The apremilast formic acid solvate Form J according to  claim 18  that is characterized by two endothermic onset events at about 84° C. and about 148° C. 
     
     
         22 . The form of apremilast according to  claim 17  which is anhydrous apremilast Form K that has an X-ray powder diffraction pattern comprising peaks, in terms of 2-theta, at about 11.40 and about 13.66. 
     
     
         23 . The anhydrous apremilast Form K according to  claim 22 , further comprising peaks, in terms of 2-theta, at about 14.83, about 27.13 and about 22.37. 
     
     
         24 . The anhydrous apremilast Form K according to  claim 23  that is characterized by an endothermic event at about 151° C. 
     
     
         25 . A composition comprising at least one form of apremilast according to  claim 17 . 
     
     
         26 . The composition according to  claim 25 , wherein the composition is a pharmaceutical composition further comprising at least one pharmaceutically acceptable excipient. 
     
     
         27 . A method of treating disease comprising administering the pharmaceutical formulation according to  claim 26  to a subject in need thereof. 
     
     
         28 . A method of making apremilast formic acid solvate Form J according to  claim 17 , comprising exposing a starting material comprising apremilast to formic acid and water to yield apremilast formic acid solvate Form J. 
     
     
         29 . A method of making anhydrous apremilast Form K that has an X-ray powder diffraction pattern comprising peaks, in terms of 2-theta, at about 11.40 and about 13.66 according to  claim 17 , comprising drying apremilast formic acid solvate Form J for time sufficient to yield anhydrous apremilast Form K.