Imidazoquinoline derivatives and their use in therapy

Abstract

This invention relates inter alia to novel imidazoquinoline derivatives and their use in therapy, particularly as vaccine adjuvants.

1 . A compound of formula (VI) 
       
         
           
           
               
               
           
         
         R 1a  represents —O—Z—H; 
         Z represents (C 2 -C 6  alkyleneO) q ; 
         q represents an integer 1 to 6; 
         R 2  represents H, C 1 -C 6 alkyl, C 1 -C 6 alkylamino, C 1 -C 6 alkoxy, C 3 -C 6  cycloalkylC 1 -C 6  alkyl, C 3 -C 6  cycloalkylC 1 -C 6  alkylamino, C 3 -C 6 cycloalkylC 1 -C 6 alkoxy, C 1 -C 6  alkoxyC 1 -C 6  alkyl, C 1 -C 6  alkoxyC 1 -C 6  alkylamino, C 1 -C 6  alkoxyC 1 -C 6  alkoxy; and 
         optionally terminally substituted with a hydroxyl, amino, —NHNH 2 , N 3 , —C≡CH, —COOH, or maleimido group; 
         R 3  represents C 2 -C 6  alkylene-OH, C 2 -C 6  alkylene-NH 2 , C 2 -C 5  alkenyl-CH 2 —OH or C 2 -C 5  alkenyl-CH 2 —NH 2 ; 
         or pharmaceutically acceptable salt thereof or a protected derivative either thereof. 
       
     
     
         2 . The compound according to  claim 1  wherein R 2  represents H, C 1 -C 6 alkyl or C 1 -C 6  alkoxyC 1 -C 6  alkyl. 
     
     
         3 . The compound according to  claim 2  wherein R 2  represents H, C 1 -C 6 alkyl or C 1 -C 3  alkoxyC 1 -C 3  alkyl; 
     
     
         4 . The compound according to  claim 3  wherein R 2  represents H, n-butyl or CH 3 CH 2 OCH 2 —. 
     
     
         5 . The compound according to  claim 4  wherein R 2  represents H. 
     
     
         6 . The compound according to  claim 4  wherein R 2  represents n-butyl. 
     
     
         7 . The compound according to  claim 4  wherein R 2  represents CH 3 CH 2 OCH 2 —. 
     
     
         8 . The compound according to  claim 1  wherein R 3  represents C 2 -C 6  alkylene-OH. 
     
     
         9 . The compound according to  claim 8  wherein R 3  represents —CH 2 CH 2 OH. 
     
     
         10 . The compound according to  claim 4  wherein R 3  represents C 2 -C 6  alkylene-OH. 
     
     
         11 . The compound according to  claim 10  wherein R 3  represents —CH 2 CH 2 OH. 
     
     
         12 . The compound according to  claim 1  wherein q represents an integer 1 to 3. 
     
     
         13 . The compound according to  claim 12  wherein q represents 1. 
     
     
         14 . The compound according to  claim 12  wherein q represents 3. 
     
     
         15 . The compound according to  claim 4  wherein q represents an integer 1 to 3. 
     
     
         16 . The compound according to  claim 15  wherein q represents 1. 
     
     
         17 . The compound according to  claim 15  wherein q represents 3. 
     
     
         18 . The compound according to  claim 10  wherein q represents an integer 1 to 3. 
     
     
         19 . The compound according to  claim 18  wherein q represents 1. 
     
     
         20 . The compound according to  claim 18  wherein q represents 3.