1,3,5-triazinane-2,4,6-trione derivatives and uses thereof
The present invention provides novel 1,3,5-triazinane-2,4,6-trione derivatives, such as compounds of any one of Formulae (I) and (II), and salts thereof, and methods of preparing the compounds. Also provided are compositions including a compound of the invention and an agent (e.g., an siRNA, mRNA, or plasmid DNA). The present invention also provides methods and kits using the compositions for delivering an agent to a subject (e.g., to the liver, spleen, or lung of the subject) or cell and for treating and/or preventing a range of diseases, such as genetic diseases, proliferative diseases, hematological diseases, neurological diseases, liver diseases, and lung diseases.
1. A compound of Formula (I):
or a salt thereof;
wherein:
each instance of R A is independently substituted or unsubstituted C 6-13 alkyl;
each instance of R B is independently substituted or unsubstituted C 6-13 alkyl; and
each instance of m is independently 1, 2, 3, 4, 5, or 6.
2. The compound of claim 1 , wherein:
all instances of R A are substituted or unsubstituted C 6-13 alkyl;
all instances of R B are substituted or unsubstituted C 6-13 alkyl; and
all instances of m are 1, 2, 3, 4, 5, or 6.
3. The compound of claim 1 , wherein at least one instance of R A is unsubstituted C 6-13 alkyl.
4. The compound of claim 1 , wherein at least two instances of R A are unsubstituted C 6-13 alkyl.
5. The compound of claim 1 , wherein all instances of R A are unsubstituted C 6-13 alkyl.
6. The compound of claim 1 , wherein:
all instances of R A are unsubstituted C 6-13 alkyl; and
all instances of R B are unsubstituted C 6-13 alkyl.
7. The compound of claim 1 , wherein all instances of m are 1.
8. The compound of claim 1 , wherein:
all instances of R A are unsubstituted C 6-13 alkyl;
all instances of R B are unsubstituted C 6-13 alkyl; and
all instances of m are 1.
9. The compound of claim 1 , wherein the compound is of the formula:
or a salt thereof.
10. A compound of Formula (II):
or a salt thereof;
wherein:
each instance of R C is independently substituted or unsubstituted alkyl; and
each instance of n is independently 1, 2, 3, 4, or 5.
11. A method of preparing a compound of claim 1 , or a salt thereof, the method comprising:
reacting a compound of Formula (A) with a compound of Formula (B), or a salt thereof, to provide a compound of claim 1 , or a salt thereof:
12. A method of preparing a compound of claim 10 , or a salt thereof, the method comprising:
reacting a compound of Formula (C), or a salt thereof, with a compound of Formula (D), or a salt thereof, to provide a compound of claim 10 , or a salt thereof:
13. The compound of claim 1 , wherein all instances of R A are unsubstituted C 8-10 alkyl.
14. The compound of claim 1 , wherein:
all instances of R A are unsubstituted C 8-10 alkyl; and
all instances of R B are unsubstituted C 8-10 alkyl.
15. The compound of claim 1 , wherein:
all instances of R A are unsubstituted C 8-10 alkyl; and
all instances of R B are unsubstituted C 8-10 alkyl
all instances of m are 1.
16. The compound of claim 1 , wherein at least one instance of R A is substituted C 6-13 alkyl.
17. The compound of claim 1 , wherein at least two instances of R A are substituted C 6-13 alkyl.
18. The compound of claim 1 , wherein all instances of R A are substituted C 6-13 alkyl.
19. The compound of claim 10 , wherein at least one instance of R C is unsubstituted C 6-18 alkyl.
20. The compound of claim 10 , wherein at least one instance of R C is substituted C 6-18 alkyl.
21. The compound of claim 10 , wherein all instances of R C are unsubstituted C 6-18 alkyl.
22. The compound of claim 10 , wherein all instances of R C are substituted C 6-18 alkyl.
23. The compound of claim 10 , wherein all instances of n are 1.
24. The compound of claim 10 , wherein:
all instances of R C are unsubstituted alkyl; and
all instances of n are 1.
25. The compound of claim 10 , wherein:
all instances of R C are unsubstituted C 6-18 alkyl; and
all instances of n are 1.