Compounds and compositions for treating chemical warfare agent-induced injuries

Abstract

Compounds and compositions for treating injuries caused by exposure to chemical warfare agents are described herein.

1 . A method of treating an injury to the skin or respiratory tract resulting from exposure to a chemical warfare agent, the method comprising administering to a subject an effective amount of a compound of Formula (I) or a salt thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H; 
         R 2  is H or C 1 -C 6  alkyl; 
         L is C(O)NR 6 ; 
         R 3  is nitrogen-containing heteroaryl substituted with R 7 ; 
         R 6  is H; 
         R 7  is heteroaryl substituted with 1-3 R 8 ; 
         each R 8  is independently cyclyl or heterocyclyl; 
         wherein said cyclyl or heterocyclyl can be substituted at one or more positions with halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphate, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, —CF 3 , or —CN; 
         R 9  is H; 
         R 11  is H; 
         R 12  is C 1 -C 6  alkyl; 
         m is 1; and 
         n is 0. 
       
     
     
         2 . A method of treating an injury to the skin or respiratory tract resulting from exposure to a chemical warfare agent, the method comprising administering to a subject an effective amount of a compound of Formula (I) or a salt thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H or C 1 -C 6  alkyl; 
         R 2  is H; 
         L is C(O)NR 6 ; 
         R 3  is nitrogen-containing heteroaryl substituted with R 7 ; 
         R 6  is H; 
         R 7  is heteroaryl substituted with 1-3 R 8 ; 
         each R 8  is independently cyclyl or heterocyclyl; 
         wherein said cyclyl or heterocyclyl can be substituted at one or more positions with halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphate, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, —CF 3 , or —CN; 
         R 9  is H; 
         R 11  is H; 
         R 12  is C 1 -C 6  alkyl; 
         m is 1; and 
         n is 0. 
       
     
     
         3 . The method of  claim 1 , wherein the compound is administered orally, via intramuscular injection, or topically. 
     
     
         4 . The method of  claim 1 , wherein the chemical warfare agent is tear gas. 
     
     
         5 . The method of  claim 1 , wherein the chemical warfare agent is chlorine. 
     
     
         6 . The method of  claim 1 , wherein the chemical warfare agent is mustard gas. 
     
     
         7 . The method of  claim 1 , wherein the subject is a human. 
     
     
         8 . The method of  claim 2 , wherein the compound is administered orally, via intramuscular injection, or topically. 
     
     
         9 . The method of  claim 2 , wherein the chemical warfare agent is tear gas. 
     
     
         10 . The method of  claim 2 , wherein the chemical warfare agent is chlorine. 
     
     
         11 . The method of  claim 2 , wherein the chemical warfare agent is mustard gas. 
     
     
         12 . The method of  claim 2 , wherein the subject is a human.