IP Library › Granted Patent US 8,877,729
Granted Patent B2
US 8,877,729 · App. 13/933,110 · Granted Nov 4, 2014

Amino acid lipids and uses thereof

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Quick Facts
Patent No.
US 8,877,729
App. No.
13/933,110
Granted
Nov 4, 2014
Kind
B2
Abstract

This disclosure provides a range of amino acid lipid compounds and compositions useful for drug delivery, therapeutics, and the diagnosis and treatment of diseases and conditions. The amino acid lipid compounds and compositions can be used for delivery of various agents such as nucleic acid therapeutics to cells, tissues, organs, and subjects.

Claims (27)

1. A compound comprising the structure shown in Formula I:

R 3 —(C═O)—Xaa-Z—R 4   Formula I

wherein

Xaa is pyridylalanine or side chain N-methylated pyridylalanine;

R 3 is independently a substituted or unsubstituted C(12-22)alkyl or C(12-22)alkenyl;

R 4 is independently a substituted or unsubstituted C(12-22)alkyl or C(12-22)alkenyl;

Z is NH;

and salts thereof.

2. The compound of claim 1 , wherein R 3 and R 4 are C(12-22)alkyl and are the same or different.

3. The compound of claim 1 , wherein R 3 and R 4 are C(12-22)alkenyl and are the same or different.

4. The compound of claim 1 , wherein R 3 is C(12-22)alkyl and R 4 is C(12-22)alkenyl.

5. The compound of claim 1 , wherein R 4 is C(12-22)alkyl and R 3 is C(12-22)alkenyl.

6. The compound of claim 1 , selected from (C12acyl)-4-Pal-NH-(C12alkyl), (C14acyl)-4-Pal-NH-(C14alkyl), (C16acyl)-4-Pal-NH-(C16alkyl), (C18acyl)-4-Pal-NH-(C18alkyl), (C12acyl)-4-Pal(Me)-NH-(C12alkyl), (C14acyl)-4-Pal(Me)-NH-(C14alkyl), (C16acyl)-4-Pal(Me)-NH-(C16alkyl), and (C18acyl)-4-Pal(Me)-NH-(C18alkyl).

7. The compound N-(1-oxo-3-(pyridin-4-yl)-1-(hexadecylamino)propan-2-yl)octadec-9-enamide.

8. A composition comprising one or more compounds according to claim 1 and one or more therapeutic nucleic acids.

9. The composition of claim 8 , wherein the therapeutic nucleic acid is a gene silencing agent.

10. The composition of claim 8 , wherein the therapeutic nucleic acid is a RNAi-inducing agent.

11. The composition of claim 8 , wherein the therapeutic nucleic acid is a double-stranded RNA.

12. The composition of claim 8 , wherein the therapeutic nucleic acid is an mdRNA.

13. The composition of claim 8 , wherein the therapeutic nucleic acid contains a modified nucleoside.

14. The composition of claim 8 , further comprising cholesteryl hemisuccinate.

15. The composition of claim 8 , further comprising one or more cationic lipids.

16. The composition of claim 8 , wherein the composition contains liposomes.

17. The composition of claim 8 , wherein the composition is an emulsion.

18. A pharmaceutical composition comprising one or more compounds according to claim 1 and one or more drug agents or biologically active agents.

19. A method for inhibiting expression of a gene in a mammal comprising preparing a composition according to claim 8 and administering the composition to the mammal.

20. A method for treating a disease in a human, the disease being selected from rheumatoid arthritis, liver disease, encephalitis, bone fracture, heart disease, viral disease, hepatitis, influenza, sepsis, and cancer, the method comprising preparing a composition according to claim 8 and administering the composition to the human.