Certain aminoalkyl glucosaminide phosphate compounds and their use

Abstract

Compounds that are adjuvants and immunoeffectors are described and claimed. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

1 - 99 . (canceled) 
     
     
         100 . A compound having the formula 
       
         
           
           
               
               
           
         
       
       wherein X is O at the axial or equatorial position; Y is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; R 1 , R 2  and R 3  are the same or different and are straight chain saturated aliphatic groups having from 1 to about 20 carbon atoms and where one of R 1 , R 2  or R 3  is optionally hydrogen; R 4  and R 5  are the same or different and are selected from the group consisting of H and methyl; R 6  and R 7  are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl and carboxy, and esters and amides thereof; R 8  and R 9  are the same or different and are selected from the group consisting of phosphono and H, and at least one of R 8  and R 9  is phosphono; R 10 , R 11  and R 12  are independently selected from straight chain unsubstituted saturated aliphatic groups having from 1 to 11 carbon atoms;
 or a pharmaceutically acceptable salt thereof. 
 
     
     
         101 . A compound according to  claim 100  wherein Y is oxygen. 
     
     
         102 . A compound according to  claim 101  wherein R 1 , R 2  and R 3  are independently selected from C 6 -C 14  saturated aliphatic groups, and R 10 , R 11  and R 12  are independently straight chain unsubstituted saturated aliphatic groups having from 3 to 9 carbon atoms. 
     
     
         103 . A compound according to  claim 102  wherein R 1 , R 2  and R 3  are independently selected from C 6 -C 10  saturated aliphatic groups. 
     
     
         104 . A compound according to  claim 100  wherein R 10 , R 11  and R 12  are independently straight chain unsubstituted aliphatic groups having from 3 to 7 carbon atoms. 
     
     
         105 . A pharmaceutical composition of matter comprising
 (a) a compound having the formula (III):   
       
         
           
           
               
               
           
         
       
       wherein X is O at the axial or equatorial position; Y is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; R 1 , R 2  and R 3  are the same or different and are straight chain saturated aliphatic groups having from 1 to about 20 carbon atoms and where one of R 1 , R 2  or R 3  is optionally hydrogen; R 4  and R 5  are the same or different and are selected from the group consisting of H and methyl; R 6  and R 7  are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl and carboxy, and esters and amides thereof; R 8  and R 9  are the same or different and are selected from the group consisting of phosphono and H, and at least one of R 8  and R 9  is phosphono; R 10 , R 11  and R 12  are independently selected from straight chain unsubstituted saturated aliphatic groups having from 1 to 11 carbon atoms;
 or a pharmaceutically acceptable salt thereof; and 
 (b) a pharmaceutically acceptable carrier. 
 
     
     
         106 . A composition according to  claim 105  wherein Y is oxygen. 
     
     
         107 . A composition according to  claim 106  wherein R 1 , R 2  and R 3  are independently selected from C 6 -C 14  saturated aliphatic groups, and R 10 , R 11  and R 12  are independently straight chain unsubstituted saturated aliphatic groups having from 3 to 9 carbon atoms. 
     
     
         108 . A composition according to  claim 107  wherein R 1 , R 2  and R 3  are independently selected from C 6 -C 10  saturated aliphatic groups. 
     
     
         109 . A composition according to  claim 105  wherein R 10 , R 11  and R 12  are independently straight chain unsubstituted aliphatic groups having from 3 to 7 carbon atoms. 
     
     
         110 . A composition according to  claim 105  suitable for mucosal administration. 
     
     
         111 . A composition according to  claim 105  suitable for intranasal administration. 
     
     
         112 . A composition according to  claim 105  further comprising an antigen, and comprising an adjuvant-effective amount of the compound of formula (III) or salt thereof.