Novel salts and polymorphs of scy-078

Abstract

SCY-078 is a glucan synthase inhibitor with antimicrobial activity. Novel salts and polymorph forms of SCY-078 are disclosed herein. The disclosure also relates to pharmaceutical compositions, methods of use, and methods of preparing the novel salts and polymorphs of SCY-078.

1 - 84 . (canceled) 
     
     
         85 . A pharmaceutically acceptable salt of compound 1: 
       
         
           
           
               
               
           
         
         wherein the salt is selected from citrate, hippurate, mesylate, and fumarate, and 
         wherein the pharmaceutically acceptable salt of compound 1 has a chemical purity of at least 98%. 
       
     
     
         86 . The pharmaceutically acceptable salt of  claim 85 , wherein the pharmaceutically acceptable salt has a kinetic solubility of one or more of the following:
 from 2 mg/mL to 5 mg/mL at 4 hours in dextrose buffer at pH 5.5,   from 2 mg/mL to 9 mg/mL at 24 hours in dextrose buffer at pH 5.5,   from 1 mg/mL to 5 mg/mL at 4 hours in phosphate buffer at pH 6.0,   from 4 mg/mL to 8 mg/mL at 24 hours in phosphate buffer at pH 6.0,   from 12 mg/mL to 21 mg/mL at 1 hour in SGF media, or   from 17 mg/mL to 22 mg/mL at 24 hours in FaSSIF media.   
     
     
         87 . The pharmaceutically acceptable salt of  claim 86 , wherein the pharmaceutically acceptable salt has a water sorption of not greater than 7% at 25° C. and 80% relative humidity. 
     
     
         88 . A method of preparing a pharmaceutical composition for injection, comprising dissolving the pharmaceutically acceptable salt of  claim 85  in a pharmaceutically acceptable carrier. 
     
     
         89 . The method of  claim 88 , wherein the step of dissolving the pharmaceutically acceptable salt in the pharmaceutically acceptable carrier takes less than 24 hours. 
     
     
         90 . A method of treating a fungal infection in a patient in need thereof, comprising administering to the patient a pharmaceutical composition comprising an effective amount of the pharmaceutically acceptable salt of  claim 85  and a pharmaceutically acceptable carrier, wherein the pharmaceutical composition is suitable for injection into a human. 
     
     
         91 . The method of  claim 90 , wherein the administering comprises administration by intravenous injection. 
     
     
         92 . The method of  claim 90 , wherein the fungal infection is a  Candida  and/or  Aspergillus  fungal infection. 
     
     
         93 . The method of  claim 90 , wherein the fungal infection is Invasive Candidiasis and/or Invasive Aspergillosis.