Derivatives of substituted morpholines and uses thereof
A compound of Formula I includes a stereoisomer thereof and/or a salt thereof; wherein R 1 is a substituted alkane group, a heterocylic group, or a pyridine group; X is hydrogen, a halogen, an amino acid residue, a substituted amino acid residue, an alkyl group, or an ester. Such compounds may be used in pharmaceutical compositions and for the treatment of central nervous system (CNS) disorders:
1. A compound of Formula I, a stereoisomer thereof, or a salt thereof:
wherein:
R 1 is alkyl, heterocyclyl, or a pyridyl;
R 2 is alkyl, aryl, heteroaryl, or heterocyclyl;
R 3 -R 14 are each independently H, F, Cl, Br, I, CN, NO 2 , alkyl, aryl, heteroaryl, or heterocyclyl; and
X is halogen, an amino acid residue with a hydrophobic side chain, or ester, wherein X may also be H only when R 1 is pyridyl.
2. The compound of claim 1 , wherein R 1 is CH 2 , CH 2 CH 2 , CH 3 CH, CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , (CH 3 ) 2 C, (CH 3 ) 2 CHCH, or (CH 3 ) 3 CCH.
3. The compound of claim 1 , wherein the amino acid residue with a hydrophobic side chain is unsubstituted.
4. The compound of claim 3 , wherein the amino acid residue with a hydrophobic side chain is valine.
5. The compound of claim 4 , wherein R 1 is CH 2 , CH 3 CH, or (CH 3 ) 2 CHCH.
6. The compound of claim 5 that is:
7. The compound of claim 3 , wherein the amino acid residue with a hydrophobic side chain is phenylalanine.
8. The compound of claim 7 , wherein R 1 is CH 3 CH.
9. The compound of claim 8 having the structure
10. The compound of claim 3 , wherein each of R 3 -R 14 is independently H, F, Cl, Br, I, or alkyl.
11. The compound of claim 10 , wherein each of R 3 -R 14 are each independently H or C 1 -C 6 alkyl.
12. The compound of claim 11 , wherein R 3 -R 14 are all H.
13. The compound of claim 12 , wherein R 1 is CH 2 , CH 2 CH 2 , CH 3 CH, CH 2 CH 2 CH 2 CH 2 , or CH 3 CH 2 CH 2 CH, or (CH 3 ) 3 CCH.
14. A compound of formula:
wherein:
R 15 is H, alkyl, —C(O)OR 17 , or —C(O)R 17 , wherein R 17 is H or alkyl; and
R 16 is H, alkyl, —C(O)OR 17 , or —C(O)R 17 , wherein R 17 is H or alkyl.
15. The compound of claim 14 , wherein R 15 is alkyl and R 16 is H or alkyl.
16. The compound of claim 15 , wherein R 15 is methyl and R 16 is H or methyl.
17. The compound of claim 16 having the structure:
18. The compound of claim 16 , wherein R 15 and R 16 are methyl.
19. The compound of claim 18 having the structure:
20. The compound of claim 14 , wherein R 15 is —C(O)R 17 in which R 17 is methyl, and R 16 is H.
21. The compound of claim 20 having the structure:
22. The compound of claim 1 , wherein R 1 is CH 2 or CH 3 CH.
23. The compound of claim 22 , wherein X is an ester.
24. The compound of claim 23 which is:
25. The compound of claim 1 which is:
26. The compound of claim 1 , wherein R 1 is a pyridyl group and X is H.
27. The compound of claim 26 that is:
28. The compound of claim 1 , wherein R 1 is a pyridyl group and X is F, Cl, Br, or I.
29. The compound of claim 28 that is: