Cationic lipids for therapeutic agent delivery formulations
Here described are compounds of formula I: wherein R 1 and R 2 is independently selected from a group consisting of C 10 to C 18 alkyl, C 12 to C 18 alkenyl, and oleyl group; wherein R 3 and R 4 are independently selected from a group consisting of C 1 to C 6 alkyl, and C 2 to C 6 alkanol; wherein X is selected from a group consisting of —CH 2 —, —S—, and —O— or absent; wherein Y is selected from —(CH 2 ) n , —S(CH 2 ) n , —O(CH 2 ) n —, thiophene, —SO 2 (CH 2 ) n —, and ester, wherein n=1-4; wherein a=1-4; wherein b=1-4; wherein c=1-4; and wherein Z is a counterion; as well as compositions and pharmaceutical formulations including compounds of formula I which are useful for the delivery of therapeutic agents; and methods of using these compositions and formulations.
1. A compound of formula I
wherein R 1 and R 2 are independently selected from the group consisting of C 12 to C 18 alkyl, and C 12 to C 18 alkenyl; wherein R 3 and R 4 are independently selected from the group consisting of C 1 to C 6 alkyl, and C 2 to C 6 alkanol; wherein X is selected from the group consisting of —CH 2 —, —S—, and —O— or X is absent; wherein Y is selected from —(CH 2 ) n —, —S(CH 2 ) n —O(CH 2 ) n —, thiophene, —SO 2 (CH 2 ) n —, and ester, wherein n=1-4; wherein a=1-4; wherein b=1-4; wherein c=1-4; and wherein Z is a counterion.
2. The compound of claim 1 , wherein Z is a halogen or mesylate.
3. The compound of claim 1 that is selected from the group consisting of
4. The compound of claim 1 , wherein R 1 and R 2 are independently C 13 to C 17 alkyl.
5. The compound of claim 1 , wherein R 1 and R 2 are independently C 13 to C 17 alkenyl.
6. The compound of claim 1 , wherein R 1 and R 2 are each C 13 alkyl or C 17 alkenyl.
7. The compound of claim 1 , wherein R 1 and R 2 are each an oleoyl or a linoleoyl group.
8. The compound of claim 1 , wherein R 1 is C 18 monoalkenyl and R 2 is C 16 alkyl or alkenyl.
9. The compound of claim 1 , wherein a=1 or 2 and b=1 or 2.
10. The compound of claim 1 , wherein X is —CH 2 —.
11. The compound of claim 1 , wherein X is —S—.
12. The compound of claim 1 , wherein X is absent.
13. The compound of claim 1 , wherein Y is —(CH 2 ) n —.
14. The compound of claim 13 , wherein n=1-3.
15. The compound of claim 1 , wherein Y is —S(CH 2 ) n —.
16. The compound of claim 15 , wherein n=1.
17. The compound of claim 1 , wherein R 3 is C 1 alkyl.
18. The compound of claim 1 , wherein R 4 is C 1 alkyl.
19. The compound of claim 1 , wherein R 4 is C 1 or C 2 alkanol.
20. The compound of claim 1 , wherein c=1.
21. The compound of claim 2 , wherein Z is a halogen.
22. The compound of claim 21 , wherein Z is a bromide.
23. The compound of claim 21 , wherein Z is a chloride.