IP Library › Granted Patent US 12,583,816
Granted Patent B2
US 12,583,816 · App. 17/286,134 · Granted Mar 24, 2026

Lipids for lipid nanoparticle delivery of active agents

Inventor: Steven M. Hansell (Vancouver, CA)
Assignee: Acuitas Therapeutics, Inc.
C07C237/06A61K9/5123A61K9/5146A61K45/06C07C211/09B82Y5/00
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Quick Facts
Patent No.
US 12,583,816
App. No.
17/286,134
Granted
Mar 24, 2026
Kind
B2
Abstract

Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein G 1 , R 1 , R 2 , L, and n are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

Claims (49)

1 . A compound having the following structure (I):

or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein:

G 1 is —N(R 3 )R 4 or —OR 5 ;

R 1 is branched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl;

R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl when L is —C(═O)—; or R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 4 -C 36 alkyl when L is C 6 -C 12 alkylene, C 6 -C 12 alkenylene, or C 2 -C 6 alkynylene;

R 3 and R 4 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 1 -C 6 alkyl, or R 3 and R 4 , together with the nitrogen to which they are attached, join to form a heterocyclyl;

R 5 is H or optionally substituted C 1 -C 6 alkyl;

L is —C(═O)—, C 6 -C 12 alkylene, C 6 -C 12 alkenylene, or C 2 -C 6 alkynylene; and

n is an integer from 1 to 12.

2 . The compound of claim 1 , or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein:

G 1 is —N(R 3 )R 4 or —OR 5 ;

R 1 is branched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl;

R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl;

R 3 and R 4 are each independently or unbranched, saturated or unsaturated, optionally substituted C 1 -C 6 alkyl; or R 3 and R 4 , together with the nitrogen to which they are attached, join to form a heterocyclyl;

R 5 is H or optionally substituted C 1 -C 6 alkyl;

L is —C(═O)—; and

n is an integer from 1 to 12.

3 . The compound of claim 1 , or a pharmaceutically acceptable salt, or stereoisomer thereof, wherein:

G 1 is —N(R 3 )R 4 or —OR 5 ;

R 1 is branched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl;

R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 4 -C 36 alkyl;

R 3 and R 4 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 1 -C 6 alkyl, or R 3 and R 4 together along with the nitrogen to which they are attached, join to form a heterocyclyl;

R 5 is H or optionally substituted C 1 -C 6 alkyl;

L is a C 6 -C 12 alkylene linker, C 6 -C 12 alkenylene linker, or C 2 -C 6 alkynylene linker; and

n is an integer from 1 to 12.

4 . The compound of claim 1 , having the following structure (IA):

wherein

R 1 and R 9 are each independently H or branched or unbranched, saturated or unsaturated, optionally substituted C 2 -C 12 alkyl, provided that R 1 and R 9 are each independently selected such that R 1 is branched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl; and

R 10 and R 11 are each independently H or branched or unbranched, saturated or unsaturated, optionally substituted C 2 -C 12 alkyl, provided that R 10 and R 11 are each independently selected such that: R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 12 -C 36 alkyl when L is —C(═O)—; and R 2 is branched or unbranched, saturated or unsaturated, optionally substituted C 4 -C 36 alkyl when L is C 6 -C 12 alkylene, C 6 -C 12 alkenylene, or C 2 -C 6 alkynylene.

5 . The compound of claim 4 , wherein R 1 and R 9 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 2 -C 12 alkyl.

6 . The compound of claim 4 , wherein R 8 is optionally substituted: C 2 alkyl, C 4 alkyl, C 6 alkyl, C 8 alkyl, or C 10 alkyl.

7 . The compound of claim 4 , wherein R 9 is optionally substituted: C 4 alkyl, C 6 alkyl, C 8 alkyl, C 10 alkyl, or C 12 alkyl.

8 . The compound of claim 4 , wherein R 10 and R 11 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 2 -C 12 alkyl.

9 . The compound of claim 4 , wherein R 11 is optionally substituted unbranched: C 2 alkyl, C 6 alkyl, or C 10 alkyl.

10 . The compound of claim 4 , wherein R 11 is optionally substituted: C 4 alkyl, C 6 alkyl, C 8 alkyl, C 10 alkyl, or C 12 alkyl.

11 . The compound of claim 4 , wherein R 1 , R 9 , R 10 and R 11 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 6 -C 10 alkyl.

12 . The compound claim 4 , wherein R 8 , R 9 , R 10 , and R 11 are each independently branched or unbranched, saturated or unsaturated, optionally substituted C 6 -C 12 alkyl.

13 . The compound of claim 1 , wherein R 1 and R 2 are each independently branched, saturated or unsaturated, optionally substituted C 12 -C 30 alkyl.

14 . The compound of claim 1 , wherein R 1 and R 2 each have one of the following structures:

15 . The compound of claim 1 , wherein R 2 has one of the following structures:

16 . The compound of claim 1 , wherein L is C 6 -C 12 alkylene.

17 . The compound of claim 1 , wherein G 1 is —N(R 3 )R 4 .

18 . The compound of claim 17 , wherein G 1 is —N(CH 3 ) 2 .

19 . The compound of claim 17 , wherein R 3 and R 4 , together with the nitrogen to which they are attached, join to form a heterocyclyl.

20 . The compound of claim 1 , wherein G 1 has one of the following structures:

21 . The compound of claim 1 , having one of the following structures:

22 . A composition comprising the compound of claim 1 and a therapeutic agent.

23 . A lipid nanoparticle comprising the compound of claim 1 and a therapeutic agent.

24 . A method for administering a therapeutic agent to a patient in need thereof, the method comprising preparing or providing the lipid nanoparticle of claim 23 , and administering the nanoparticle to the patient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2026
From: ANSELL, STEVEN M.
To: ACUITAS THERAPEUTICS, INC.
Reel/Frame 073673/0413 →
Continuity (3)
Provisional Application 62747521 · Oct 18, 2018
Provisional Application 62747557 · Oct 18, 2018
Related Publication 20210395188A1 · Dec 23, 2021
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