Granted Patent B2

US 12,528,823 · App. 17/489,022 · Granted Jan 20, 2026

Inventor: Andrew Wasmuth (New York, NY)

Assignee: Applied Therapeutics, Inc.

C07D495/04A61P9/00C07H15/26

Abstract

Claims (19)

1 . A compound of Formula (I-4)

wherein,

R 5 through R 8 are independently hydrogen, halogen, or haloalkyl

X 5 is Q-R 10 ;

Q is O, NH, O—(C 1 -C 6 )-alkyl, O—(C 1 -C 6 )-hydroxyalkyl, O—(C 1 -C 6 )-aminoalkyl, O-aryl, O-heteroaryl, O-biaryl, O-benzyl, NH—(C 1 -C 6 )-alkyl, NH—(C 1 -C 6 )-hydroxyalkyl, NH—(C 1 -C 6 )-aminoalkyl, NH-aryl, NH-heteroaryl, NH-biaryl, NH-benzyl, or a bond;

R 10 is

 aryl, heteroaryl, biaryl, benzyl, heterocycle, or C(O)OR 11 , with the proviso that when Q is not a bond, R 10 can be bonded to any substitutable atom in Q, and when Q is NH, R 10 can also be H or OH; and

R 11 and R 12 are independently H or (C 1 -C 6 )-alkyl optionally substituted with one or more substituents selected from the group consisting of OR 13 , NHR 13 , SR 13 , CO 2 R 13 , CONHR 13 , aryl, hydroxyaryl, indolyl, imidazolyl, and NH(CNH)NH 2 ;

or R 11 and R 12 , taken together with the atoms to which they are attached, form a 3-7 membered heterocyclic ring;

R 13 is H or (C 1 -C 6 )-alkyl; and

n is 0, 1, or 2;

or a pharmaceutically acceptable salt thereof.

2 . The compound of claim 1 , wherein X 5 is selected from a group consisting of

3 . The compound of claim 1 , wherein R 5 , R 7 and R 8 are each H; and

R 6 is halogen or haloalkyl.

4 . The compound of claim 3 , wherein R 6 is trifluoromethyl.

5 . A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

6 . The compound of claim 1 , wherein the compound is selected from the group consisting of

and pharmaceutically acceptable salts thereof, wherein R 12 is H or (C 1 -C 6 )-alkyl optionally substituted with one or more substituents selected from the group consisting of OR 13 , NHR 13 , SR 13 , CO 2 R 13 , CONHR 13 , aryl, hydroxyaryl, indolyl, imidazolyl, and NH(CNH)NH 2 , and wherein R 13 is H or (C 1 -C 6 )-alkyl.

Assignments (3)

Continuity (4)

References Cited (207)