Carbamates of 2-heterocyclic-1,2-ethanediols

Abstract

Carbamate compounds of 2-heteroaryl-1,2-ethanediol are described. The compounds are effective in the treatment of disorders of the central nervous system, especially as anti-convulsive or anti-epileptic agents.

1 . A compound represented by the formula:  
       
         
           
           
               
               
           
         
       
       wherein A is a heterocyclic moiety selected from the group consisting of  
       
         
           
           
               
               
           
         
       
       wherein each of R 3 , R 4  and R 5  is independently selected from the group consisting of hydrogen, halogen, trihalomethyl, alkyl and aryl, and X is selected from sulfur, oxygen and nitrogen; B 1  and B 2  are independently hydroxy or OCONR 1 , R 2 , provided that B 1  and B 2  are not simultaneously hydroxy; and R 1  and R 2  are independently selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy, alkylaryl, arylalkyl, aryl and aryloxy, and their enantiomers, enantiomeric mixtures thereof, and pharmaceutically acceptable salts thereof.  
     
     
         2 . A compound in accordance with  claim 1 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.  
     
     
         3 . A compound in accordance with  claim 1 , wherein B 1  and B 2  are OCONH 2 .  
     
     
         4 . A compound in accordance with  claim 1 , wherein only one of B 1  and B 2  is OCONH 2 .  
     
     
         5 . Cancelled  
     
     
         6 . A compound in accordance with  claim 1 , wherein A is selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
       wherein each of R 3 , R 4  and R 5  is independently selected from the group consisting of hydrogen, halogen, trihalomethyl, alkyl and aryl, and X is selected from sulfur, oxygen and nitrogen.  
     
     
         7 - 12 . Cancelled.  
     
     
         13 . A pharmaceutical composition comprising an effective amount of a compound of in accordance with  claim 1  for treating disorders of the central nervous system.  
     
     
         14 . A pharmaceutical composition in accordance with  claim 13 , wherein the central nervous systems disorder being treated is selected from the group consisting of convulsions, epilepsy, stroke, neurogenic pain and muscle spasm.  
     
     
         15 . A pharmaceutical composition in accordance with  claim 13 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.  
     
     
         16 . A method for the treatment of a central nervous system disorder which comprises administering to a host requiring such treatment an effective amount of a compound in accordance with  claim 1 .  
     
     
         17 . A method in accordance with  claim 16 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.