Granted Patent B2

US 12,589,155 · App. 17/625,066 · Granted Mar 31, 2026

Inventors: Philip Stewart Low (West Lafayette, IN); Madduri Srinivasarao (West Lafayette, IN)

A61K47/544A61K41/0042A61K47/545

Abstract

Claims (32)

1 . A compound of Formula (I) or (II):

or a pharmaceutically acceptable salt thereof;

wherein:

R 1 is independently H, or a protecting group that is deprotected in tumor extracellular matrix, wherein at least one R 1 group is a protecting group;

Y is absent, —N(H)C(S)N(H)—, —N(H)C(O)N(H)—, —N(H)C(O)—, —N(H)C(S)—, —C(O)—N(H)—, —C(S)N(H)—, —C(O)O—, —N(H)—, —S(O)N(H)—, —S(O) 2 N(H)—, —S(O) 3 —, —P(O) 2 N(H)—, or —P(O) 3 —;

L is a linker; and

Lipid is a cancer-cell targeting lipid; and

at least one R 1 is a protecting group;

wherein the protecting group is:

or a pharmaceutically acceptable salt thereof.

2 . The compound of claim 1 , wherein both R 1 groups in the compound of Formula (I) are protecting groups.

3 . The compound of claim 1 , wherein Lis an ultraviolet (UV)-active linker.

4 . The compound of claim 1 , wherein L is a chromophore.

5 . A compound of Formula (I) or (II):

or a pharmaceutically acceptable salt thereof,

wherein:

R 1 is independently H, or a protecting group that is deprotected in tumor extracellular matrix, wherein at least one R 1 group is a protecting group;

Y is absent, —N(H)C(S)N(H)—, —N(H)C(O)N(H)—, —N(H)C(O)—, —N(H)C(S)—, —C(O)—N(H)—, —C(S)N(H)—, —C(O)O—, —N(H)—, —S(O)N(H)—, —S(O) 2 N(H)—, —S(O)—, —P(O) 2 N(H)—, or —P(O) 3 —;

L is:

and

Lipid is a cancer-cell targeting lipid.

6 . The compound of claim 1 , wherein Lipid is:

7 . The compound of claim 5 , wherein Lipid is:

8 . The compound of claim 1 , wherein the compound is:

9 . The compound of claim 5 , wherein the compound is:

10 . The compound of claim 1 , wherein the compound is:

11 . A pharmaceutical composition comprising a compound of claim 1 , and a pharmaceutical acceptable carrier.

12 . The compound of claim 5 , wherein the protecting group is a reactive oxygen species (ROS)-cleavable group.

13 . The compound of claim 5 , wherein the protecting group is:

14 . The compound of claim 5 , wherein the compound is:

15 . The compound of claim 5 , wherein the compound is:

16 . A pharmaceutical composition comprising a compound of claim 5 , and a pharmaceutical acceptable carrier.

Assignments (2)

Continuity (2)

References Cited (61)