Polymorphic, amorphous and hydrated forms of 5-chloro-3-(4-methanesulfonylphenyl)-6'-methyl-[2,3']bipyridinyl

Abstract

Polymorphic, amorphous and hydrated forms of the title compound having the following structure: are disclosed. The compound is a potent and selective cyclooxygenase-2 (COX-2) inhibitor.

What is claimed is:  
     
         1 . A polymorph of Compound A of structural formula:  
       
         
           
           
               
               
           
         
       
       selected from Forms II, III and IV having the physical characteristics described in the following Table:  
       
         
           
                 
                 
                 
                 
                 
               
                     
                     
                 
                     
                     
                 
                     
                   Form 
                   II 
                   III 
                   IV 
                 
                     
                     
                 
                     
                   DSC 
                   134-136° C. 
                   133° C. 
                   134° C. 
                 
                     
                   extrapolated 
                 
                     
                   melting 
                 
                     
                   temperature 
                 
                     
                   onset 
                 
                     
                   XRPD (peak 
                   5.6 
                   10.5 
                   8.7 
                 
                     
                   positions, Cu K 
                   9.4 
                   16.1 
                   15.2 
                 
                     
                   alpha) 
                   10.7 
                   22.4 
                   17.1 
                 
                     
                     
                   17.6 
                     
                   19.5 
                 
                     
                     
                     
                     
                   21.7 
                 
                     
                     
                     
                     
                   23.5 
                 
                     
                     
                     
                     
                   23.6 
                 
                     
                     
                 
                     
                     
                 
             
                
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         2 . A polymorph in accordance with  claim 1  which is Form IV.  
     
     
         3 . A sesquihydrate of Form I having a DSC of about 134-136° C., peak m.p. 138° C., an XRPD pattern of 7.1, 9.7, 11.8, 15.5, 20.1, 22.7 and 24.1, and further containing approximately 1.5 mol water per mol of compound A.  
     
     
         4 . A polymorph in accordance with  claim 1  which is Form IV.  
     
     
         5 . A hemihydrate of Form IV in accordance with  claim 4  containing 0.5 mol water per mol of compound A.  
     
     
         6 . A polymorph in accordance with  claim 1  which is Form III.  
     
     
         7 . An amorphous form of Compound A in accordance with  claim 1  obtained by cooling a molten sample of a crystalline form of Compound A.  
     
     
         8 . A pharmaceutical composition comprised of a polymorph II, III or IV in accordance with  claim 1  in combination with a pharmaceutically acceptable carrier.  
     
     
         9 . A Form II polymorph of Compound A of structural formula:  
       
         
           
           
               
               
           
         
       
       having a DSC extrapolated melting temperature onset of ˜131° C., and XRPD peak positions, Cu K alpha of 5.6, 9.4, 10.7 and 17.6.