Long chain N-alkyl compounds and oxa-derivatives thereof

Abstract

Long chain N-alkyl amino and imino compounds, oxa-substituted derivatives thereof, and pharmaceutical compositions including such compounds are described. The long chain N-alkyl group is a C 8 -C 16 alkyl group. The long chain N-alkyl compounds and oxa-substituted derivatives thereof can be used in the treatment of viral infections, in particular hepatitis B virus or hepatitis C virus, in a cell or an individual. For example, the long chain N-alkyl compounds or oxa-substituted derivatives thereof can be derived from piperidines, pyrrolidines, phenylamines, pyridines, pyrroles, or amino acids.

1 - 37 . (canceled) 
   
   
       38 . A compound having the formula: 
     
       
         
         
             
             
         
       
     
     or a physiologically acceptable salt thereof, wherein:
 R 1  is a C 8 -C 16  alkyl or an oxa-substituted derivative thereof; 
 each X, independently, is selected from the group consisting of hydrogen, hydroxy, amino, carboxy, C 1 -C 4  alkylcarboxy, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, C 1 -C 4  hydroxyalkyl, C 1 -C 6  acyloxy, and aroyloxy, and each Y, independently, is selected from the group consisting of hydrogen, hydroxy, amino, carboxy, C 1 -C 4  alkylcarboxy, C 1 -C4 alkyl, C 1 -C4 alkoxy, C 1 -C4 hydroxyalkyl, C 1 -C6 acyloxy, aroyloxy, and deleted; 
 R 4  is hydrogen or deleted; and 
 R 5  is selected from the group consisting of hydrogen, hydroxy, amino, substituted amino, carboxy, alkoxycarbonyl, aminocarbonyl, aryl, aralkyl, alkoxy, hydroxyalkyl, acyloxy, and aroyloxy, 
 wherein said oxa-substituted derivative contains 1 to 5 oxygen atoms, wherein the compound is not N-nonyl-1,5-deoxy-1,5-imino-D-glucitol. 
 
   
   
       39 . The compound of  claim 38 , wherein each X is hydroxy and each Y is hydrogen. 
   
   
       40 . The compound of  claim 39 , wherein the compound is a deoxynojirimycin derivative. 
   
   
       41 . The compound of  claim 40 , wherein R 1  is the oxa-substituted derivative of the C 8 -C 16  alkyl. 
   
   
       42 . The compound of  claim 41 , wherein said oxa-substituted derivative contains 1 to 3 oxygen atoms. 
   
   
       43 . The compound of  claim 42 , wherein said oxa-substituted derivative contains 1 to 2 oxygen atoms. 
   
   
       44 . The compound of  claim 41 , wherein R 1  is a C 8 -C 10  oxa-alkyl group. 
   
   
       45 . The compound of  claim 44 , wherein R 1  is (CH 2 ) 6 O(CH 2 ) n CH 3  or (CH 2 ) 2 O(CH 2 ) n+4 CH 3 , n=1, 2 or 3. 
   
   
       46 . The compound of  claim 45 , wherein R 1  is 3-oxanonyl, 3-oxadecyl, 7-oxanonyl or 7-oxadecyl. 
   
   
       47 . The compound of  claim 39 , wherein the compound is a deoxygalactonojirimycin derivative. 
   
   
       48 . The compound of  claim 47 , wherein R 1  is the oxa-substituted derivative of the C 8 -C 16  alkyl. 
   
   
       49 . The compound of  claim 48 , wherein said oxa-substituted derivative contains 1 to 3 oxygen atoms. 
   
   
       50 . The compound of  claim 49 , wherein said oxa-substituted derivative contains 1 to 2 oxygen atoms. 
   
   
       51 . The compound of  claim 50 , wherein R 1  is a C 8 -C 10  oxa-alkyl group. 
   
   
       52 . The compound of  claim 51 , wherein R 1  is (CH 2 ) 6 O(CH 2 ) n CH 3  or (CH 2 ) 2 O(CH 2 ) n+4 CH 3 , n=1, 2 or 3. 
   
   
       53 . The compound of  claim 52 , wherein R 1  is 3-oxanonyl, 3-oxadecyl, 7-oxanonyl or 7-oxadecyl. 
   
   
       54 . The compound of  claim 53 , that is N-7-oxa-nonyl-1,5-dideoxy-1,5-imino-D-galactitol. 
   
   
       55 . A pharmaceutical composition comprising the compound of  claim 38  and a pharmaceutically acceptable carrier.