Gamma-hydroxybutyrate compositions containing carbohydrate, lipid or amino acid carriers

1. A compound of the formula (III):

wherein R 1 is H or a hydroxyl-protecting group, R is H, (C 1 -C 4 )alkyl or benzyl, X is a residue of a naturally occurring hydroxy group-containing α-amino acid or a naturally occurring bis(carboxy) group containing amino acid, Z is the residue of a naturally occurring hydroxy group-containing α-amino acid or a naturally occurring bis(carboxy) group-containing amino acid, Y is a moiety covalently linking X and Z, n is 0-1, m is 0 to the number of available hydroxy groups in amino acid X and Z, p is 1 to the number of available CO 2 H groups on the amino acid X and Z, or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein each of m and p are 2 and n is 1.

3. The compound of claim 1 wherein m is 0, n is 1 and p is 4.

4. The compound of claim 1 wherein n =0, m =0, p =2 and X is the residue of glutamic acid or tyrosine.

5. The compound of claim 1 wherein m=p=1, n is 0 and X is the residue of tyrosine, threonine, or serine.

6. The compound of claim 1 , 2 or 3 wherein Y is C(O)CH 2 CH 2 C(O) or C(O)CH═CH(CO).

7. A compound of formula (IV):

wherein L and L′ are individually H, (C 1 -C 6 )alkyl or a hydroxyl protecting group, wherein at least one of L′ or L is -(A)(Y)(Z) n , wherein A is (C 1 -C 6 )alkyl, Y is H, OH, N(R 1 )(R 2 )(R 3 ) or (O(PO 3 31 )-AN(R 1 )(R 2 )(R 3 ,), wherein R 1 , R 2 and R 3 are each (C 1 -C 4 )alkyl or R 1 and R 2 together with N are a (C 5 -C 7 )heterocyclic ring, optionally substituted with 1 or 2 N(R 3 ), S, non-peroxide O or a combination thereof; n is 1-2 and Z is XR, wherein X is O, S, NH, N(CH 3 ), NHC(O) or OC(O) and R is (C 8 -C 22 )alkyl, optionally substituted with 1-2 double bonds, or a pharmaceutically acceptable salt thereof, with the proviso that when one of L or L′ is 1,3-dihexadecanoyloxyprop-2-yl, the other is not H.

8. The compound of claim 7 wherein L′ is -(A)(Y)(Z) n and L is H, (C 1 -C 6 )alkyl or a hydroxyl protecting group.

9. The compound of claim 7 or 8 wherein X is OC(O).

10. The compound of claim 7 wherein R is (C 10 -C 22 )alkyl.

11. The compound of claim 7 or 8 wherein Y is —O(PO 3 31 )CH 2 CH 2 N(CH 3 ) 3 30 .

12. The compound of claim 8 or 10 wherein -(A)(Y)(Z) n is —CH[CH 2 Y][CH 2 Z].

13. A method for treating a mammal afflicted with a condition or pathology amenable to treatment by gamma-hydroxy butyrate (GHB) comprising administering to said mammal an effective amount of a compound of formula (IV):

wherein L and L′ are individually H, (C 1 -C 6 )alkyl or a hydroxyl protecting group, wherein at least one of L′ or L is -(A)(Y)(Z) n , wherein A is (C 1 -C 6 )alkyl, Y is H, OH, N(R 1 )(R 2 )(R 3 ) or O(PO 3 31 )-AN(R 1 )(R 2 )(R 3 ) , wherein R 1 , R 2 and R 3 are each (C 1 -C 4 )alkyl or R 1 and R 2 together with N are a (C 5 -C 7 )heterocyclic ring, optionally substituted with 1 or 2 N(R 3 ), S, non-peroxide O or a combination thereof; n is 1-2 and Z is XR, wherein X is O, S, NH, N(CH 3 ), NHC(O) or OC(O) and R is (C 8 -C 22 )alkyl, optionally substituted with 1-2 double bonds, or a pharmaceutically acceptable salt thereof, with the proviso that when one of L or L′ is 1,3-dihexdecanoyloxyprop-2-yl, the other is not H.

14. A compound of the formula (I):

(R′O(CH 2 ) 3 CO 2 ) 4 (—(X)—(Y) n —(Z) n —)(CO 2 (CH 2 ) 3 CO 2 R) p

Wherein R′ is H or a hydroxyl-protecting group, R is H, (C 1 -C 4 )alkyl or benzyl, X and Z are each residues of a naturally occurring hydroxy group-containing α-amino acid or a naturally occurring bis(carboxy)amino acid, Y is a moiety covalently linking X and Z, n is 0-1, m is 0 to the number of available hydroxy groups on amino acid X and Z, p is 0 to the number of available CO 2 H groups on amino acids X and Z, with the proviso that both m and p are not zero, or a pharmaceutically acceptable salt thereof.

15. A method for treating a mammal afflicted with a condition or pathology amenable to treatment by gamma-hydroxy butyrate (GHB) comprising administering to said mammal an effective amount of a compound of the formula (I):

(R′O(CH 2 ) 3 CO 2 ) m (—(X)—(Y) n —(Z) n —)(CO 2 (CH 2 ) 3 CO 2 R) p

wherein R′ is H or a hydroxyl-protecting group, R is H, (C 1 -C 4 )alkyl or benzyl, X and Z are each residues of a naturally occurring hydroxy group-containing α-amino acid or a naturally occurring bis(carboxy)amino acid, Y is a moiety covalently linking X and Z, n is 0-1, m is 0 to the number of available hydroxy groups on amino acid X and Z, p is 0 to the number of available CO 2 H groups on amino acids X and Z, with the proviso that both m and p are not zero, or a pharmaceutically acceptable salt thereof.