Glycomimetic replacements for hexoses and n-acetyl hexosamines

Abstract

Compounds and methods are provided for obtaining oligosaccharide mimics. More specifically, compounds and methods are described wherein oligosaccharide mimics are obtained by incorporating or substituting in a cyclohexane derivative.

1 .- 3 . (canceled) 
     
     
         4 . A compound comprising: 
       
         
           
           
               
               
           
         
         R 1 ═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, OH, or NHX where X═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; C(═O)OX, alkanyl substituted with C(═O)OX, C(═O)NHX, alkanyl substituted with C(═O)NHX, where X═C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; NHX, where X═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; 
         R 2 ═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, OH, or NHX where X═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; —C(═O)OX where X is C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; —C(═O)NH(CH 2 ) n NH 2  where n=0-30, C(═O)NHX or CX 2 OH, where X═C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; OX, NHX, NH(═O)X, where X═H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH; with the proviso that R 1  and R 2  are not both H; 
         R 3 ═—OH, 
       
       
         
           
           
               
               
           
         
          —O—C(═O)—X, —NH 2 , —NH—C(═O)—NHX, or —NH—C(═O)—X where n=0-2 and X is independently selected from C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, 
       
       
         
           
           
               
               
           
         
          where Q is H or a physiologically acceptable cation, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, aryl, heteroaryl, (CH 2 ) m -aryl or (CH 2 ) m -heteroaryl where m is 1-10, and where n=0-10, and any of the above ring compounds may be substituted with one to three independently selected of Cl, F, CF 3 , C 1 -C 8  alkoxy, NO 2 , C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, C 1 -C 14  aryl, or OY, C(═O)OY, NY 2  or C(═O)NHY where Y is H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, or C 1 -C 14  aryl; 
       
       
         
           
           
               
               
           
         
          where R 9  is aryl, heteroaryl, cyclohexane, t-butane, adamantane, or triazole, and any of R 9  may be substituted with one to three independently selected of Cl, F CF 3 , C 1 -C 8  alkoxy, NO 2 , C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8 alkynyl or OY, C(═O)OY, NY 2  or C(═O)NHY where Y is H, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, and C 1 -C 8  alkynyl or C 1 -C 14  aryl; and where R 10  is one of 
       
       
         
           
           
               
               
           
         
          where Q is H or a physiologically acceptable cation, C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, aryl, heteroaryl, (CH 2 ) m -aryl or (CH 2 ) m -heteroaryl where m is 1-10, n=1-4, Z and Y═C 1 -C 8  alkanyl, C 1 -C 8  alkenyl, C 1 -C 8  alkynyl, halogenated C 1 -C 8  alkanyl, aryl and heteroaryl substituted with Me, OMe, halide, OH; and 
         R 5 ═H, D-mannose, L-galactose, D-arabinose, L-fucose, polyols. 
       
     
     
         5 . A compound consisting of the compound of  claim 4 . 
     
     
         6 .- 17 . (canceled) 
     
     
         18 . The compound according to  claim 5  having the formula: 
       
         
           
           
               
               
           
         
       
       where Me is methyl, Et is ethyl and Bz is benzoyl. 
     
     
         19 . The compound according to  claim 5  having the formula: 
       
         
           
           
               
               
           
         
       
       where Me is methyl and Bz is benzoyl. 
     
     
         20 . The compound according to  claim 5  having the formula: 
       
         
           
           
               
               
           
         
       
       where Me is methyl, Et is ethyl and Bz is benzoyl. 
     
     
         21 . The compound according to  claim 5  having the formula: 
       
         
           
           
               
               
           
         
       
       where Me is methyl and Bz is benzoyl. 
     
     
         22 . The compound according to  claim 4  with polyethylene glycol attached thereto. 
     
     
         23 . The compound according to  claim 4  attached to another of the compound according to  claim 4  by polyethylene glycol. 
     
     
         24 . The compound according to  claim 5  with polyethylene glycol attached thereto. 
     
     
         25 . The compound according to  claim 5  attached to another of the compound according to  claim 5  by polyethylene glycol.