Novel hydrogen sulfate salt

Abstract

The present invention relates to Compound 1 hydrogen sulfate salt and solvates, crystalline forms and amorphous forms thereof, and to processes for their preparation.

1 . A hydrogen sulfate salt of Compound 1: 
       
         
           
           
               
               
           
         
       
     
     
         2 . A hydrogen sulfate salt of Compound 1 according to  claim 1  in anhydrous form. 
     
     
         3 . A hydrogen sulfate salt of Compound 1 according to  claim 1  in the form of a solvate. 
     
     
         4 . A hydrogen sulfate salt of Compound 1 according to  claim 1  which is crystalline. 
     
     
         5 . A hydrogen sulfate salt of Compound 1 according to  claim 4 , wherein said hydrogen sulfate salt of Compound 1 has an X-ray powder diffraction pattern with at least one specific peak at about 24.59°. 
     
     
         6 . A hydrogen sulfate salt of Compound 1 according to  claim 5 , wherein said hydrogen sulfate salt of Compound 1 has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59°, 20.97°, 23.99°, 27.65°, 12.24°, 23.49°, 24.30°, 17.02°, 25.91° and 22.50°. 
     
     
         7 . A hydrogen sulfate salt of Compound 1 according to  claim 1  which has a powder X-ray diffraction pattern substantially the same as the X-ray powder diffraction pattern shown in  FIG. 1 . 
     
     
         8 . A hydrogen sulfate salt of Compound 1 according to  claim 1  in amorphous form. 
     
     
         9 . A method for preparing a hydrogen sulfate salt of Compound 1 according to  claim 1 , said method comprising
 (i) reacting a slurry of Compound 1 in an organic liquid with at least a stoichiometric amount of sulfuric acid and water;   (ii) recovering the salt from the resultant solution; and   (iii) thereafter, if desired or necessary, forming a solvate thereof.   
     
     
         10 . The method according to  claim 9  wherein the amount of water added in step (i) is restricted to that amount necessary to ensure that the salt is formed. 
     
     
         11 . The method according to  claim 9  wherein step (i) is carried out at a temperature of from 40-80° C. 
     
     
         12 . The method according to  claim 9 , wherein the organic liquid is a C 1-6  alkyl ketone. 
     
     
         13 . The method according to  claim 9 , wherein the hydrogen sulfate salt is recovered in step (ii) by cooling the reaction mixture, optionally with the addition of further organic liquid, so that the hydrogen sulfate salt is precipitated. 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . A method for treating disease states mediated through the MEK in a warm-blooded mammal need of such treatment, which comprises administering to said mammal an effective amount of a hydrogen sulfate salt of Compound 1 according to  claim 1 .