Fatty acid fumarate derivatives and their uses

Abstract

The invention relates to Fatty Acid Fumarate Derivatives; compositions comprising an effective amount of a Fatty Acid Fumarate Derivative; and methods for treating or preventing cancer, a metabolic disorder or neurodegenerative disorder comprising the administration of an effective amount of a Fatty Acid Fumarate Derivative.

1 - 30 . (canceled) 
     
     
         31 . A compound of Formula I: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt, enantiomer, or stereoisomer thereof; 
       wherein
 W 1  and W 2  is each independently NH or NR, or W 1  and W 2  can be taken together to form an optionally substituted imidazolidine or piperazine group; 
 each a, b, c, and d, is independently —H, -D, —CH 3 , —OCH 3 , —OCH 2 CH 3 , —C(O)OR, —O-Z, or benzyl, or two of a, b, c, and d can be taken together, along with the single carbon to which they are bound, to form a cycloalkyl or heterocycle; 
 each n, o, p, and q is independently 0, 1, or 2; 
 each L is independently null, —O—, or 
 
       
         
           
           
               
               
           
         
         wherein the representation of L is not limited directionally left to right as is depicted, rather either the left side or the right side of L can be bound to the W 1  side of the compound of Formula I; 
         each m is independently 0, 1, 2, or 3; if m is more than 1, then L can be the same or different; 
         each R 4  is independently H or optionally substituted C 1 -C 6  alkyl, wherein a methylene unit of the C 1 -C 6  alkyl can be optionally substituted for either O or NR, and in NR 4  R 4 , both R 4  when taken together with the nitrogen to which they are attached can form a heterocyclic ring such as a pyrrolidine, piperidine, morpholine, piperazine or pyrrole; 
         each Z is independently 
       
       
         
           
           
               
               
           
         
         each t is independently 0 or 1; 
         each r is independently 2, 3, or 7; 
         each s is independently 3, 5, or 6; 
         each v is independently 1, 2, or 6; 
         each R 1  and R 2  is independently —H, -D, —C 1 -C 4  alkyl, -halogen, —OH, —C(O)C 1 -C 4  alkyl, —O-aryl, —O-benzyl, —OC(O)C 1 -C 4  alkyl, —C 2 -C 3  alkene, C 2 -C 3  alkyne, —C(O)C 1 -C 4  alkyl, —NH 2 , —NH(C 1 -C 3  alkyl), —N(C 1 -C 3  alkyl) 2 , —NH(C(O)C 1 -C 3  alkyl), —N(C(O)C 1 -C 3 alkyl) 2 , —SH, —S(C 1 -C 3  alkyl), —S(O)C 1 -C 3  alkyl, or —S(O) 2 C 1 -C 3  alkyl; 
         each R 3  is independently H or —C 1 -C 6  alkyl; and 
         each R is independently —H, —C 1 -C 3  alkyl, or straight or branched C 1 -C 4  alkyl optionally substituted with OH, or halogen. 
       
     
     
         32 . The compound of  claim 31 , wherein W 1  and W 2  are each NH. 
     
     
         33 . The compound of  claim 31 , wherein R 3 is CH 3 . 
     
     
         34 . The compound of  claim 31 , wherein Z is 
       
         
           
           
               
               
           
         
       
       and t=1, r=2, and s=6. 
     
     
         35 . The compound of  claim 31 , wherein R 3  is H. 
     
     
         36 . The compound of  claim 31 , wherein L is 
       
         
           
           
               
               
           
         
       
       and R 4  is CH 3 . 
     
     
         37 . The compound of  claim 31 , wherein W 1  and W 2  are each NH and L is null. 
     
     
         38 . The compound of  claim 31 , wherein Z is 
       
         
           
           
               
               
           
         
       
       and t=1, r=3, and s=5. 
     
     
         39 . The compound of  claim 31 , wherein L is —O—. 
     
     
         40 . The compound of  claim 31 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         41 . The compound of  claim 31 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         42 . The compound of  claim 31 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         43 . The compound of  claim 31 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         44 . The compound of  claim 31 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         45 . A compound, wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         46 . A pharmaceutical composition comprising a compound of any one of  claims 31 - 45  and a pharmaceutically acceptable carrier.