Novel pharmaceutical salts and polymorphs of a factor xa inhibitor

Abstract

The present invention provides for salts comprising a compound of Formula I and an acid that has activity against mammalian factor Xa. The present invention is also directed to methods of making the compound of Formula I.

1 .- 5 . (canceled) 
     
     
         6 . A method of preparing a salt represented by Formula II: 
       
         
           
           
               
               
           
         
         comprising reacting a compound of Formula I with one or more molar equivalents of maleic acid 
       
       
         
           
           
               
               
           
         
       
     
     
         7 . The method of  claim 6  wherein the salt is isolated as a crystalline polymorph form. 
     
     
         8 . The method of  claim 7 , wherein the crystalline polymorph form of the salt has a powder X-ray diffraction pattern having at least four approximate characteristic peak locations selected from 4.9, 9.7, 13.8, 14.1, 15.2, 17.6, 18.5, 20.8, 21.6, 22.7, 24.1, 26.3, and 26.8 degrees 2θ. 
     
     
         9 . The method of  claim 7 , wherein the crystalline polymorph form of the salt has a powder X-ray diffraction pattern having at least eight approximate characteristic peak locations selected from 4.9, 9.7, 11.8, 13.8, 14.1, 15.2, 17.6, 18.5, 19.9, 20.8, 21.6, 22.7, 24.1, 25.0, 26.3, and 26.8 degrees 2θ. 
     
     
         10 .- 28 . (canceled) 
     
     
         29 . The method of  claim 7 , wherein the crystalline polymorph form of the salt has a powder X-ray diffraction pattern having at least four characteristic peak locations selected from 4.9, 9.7, 13.8, 14.1, 15.2, 17.6, 18.5, 20.8, 21.6, 22.7, 24.1, 26.3, and 26.8 degrees 2θ, each ±0.2 degrees 2θ. 
     
     
         30 . The method of  claim 7 , wherein the crystalline polymorph form of the salt has a powder X-ray diffraction pattern having at least eight characteristic peak locations selected from 4.9, 9.7, 11.8, 13.8, 14.1, 15.2, 17.6, 18.5, 19.9, 20.8, 21.6, 22.7, 24.1, 25.0, 26.3, and 26.8 degrees 2θ, each ±0.2 degrees 2θ.