Amine prodrugs of pharmaceutical compounds

A prodrug consisting of a drug molecule and at least one or more prodrug appendage moieties, the prodrug is formed as:

• wherein the drug molecule is riluzole, and
• wherein R is a prodrug appendage moiety, wherein the prodrug appendage moiety is coupled to amine of the drug molecule and is independently selected from the group of consisting of:
• where R1 is H or alkyl;
• R2 is alkyl, cycloalkyl, aryl, or heteroaryl, or halo alkyl, which is substituted or unsubstituted,
• R3 is H, metal, R2 or a substituted or unsubstituted primary, secondary or tertiary amine;
• R4 is H, metal, ammonium salt or alkyl;
• R5 is a substituted or unsubstituted natural amino acid;
• Ra or Rb is H, alkyl or aryl;
• or NRa or NRb is an amino acid;
• X is CH2 or O;
• k is 1 or 2, m is 2-22, or (CHk)m is saturated, unsaturated or conjugated hydrocarbon;
• n is 0-2;
• the metal is Na, K, Li, Ca, Mg, Ag or Zn, and
• wherein i is 1 or 2 and j is 0 or 1,
• wherein “substituted” refers to one or more substituents, which are the same or different, each replacing a hydrogen atom, wherein the one or more substituents are selected from the group consisting of F, Cl, Br, I, hydroxyl, amino, alkylamino, arylamino, dialkylamino, diarylamino, cyano, nitro, mercapto, oxo, thio, imino, formyl, carbamido, carbamyl, carboxyl, thioureido, thiocyanato, sulfoamido, sulfonylalkyl, sulfonylaryl, alkyl, alkenyl, alkoxy, mercaptoalkoxy, aryl, heteroaryl, and cyclyl, wherein alkyl, alkenyl, alkyloxy, aryl, heteroaryl, and cyclyl are optionally substituted with alkyl, aryl, heteroaryl, halogen, hydroxyl, amino, mercapto, cyano, nitro, oxo, thioxo, or imino.