IP Library › Granted Patent US 12,378,220
Granted Patent B2
US 12,378,220 · App. 18/320,805 · Granted Aug 5, 2025

WNT signaling pathway inhibitors for treatments of disease

Inventors: Fengtian Xue (Potomac, MD); Yan Shu (Clarksville, MD)
Assignee: University of Maryland, Baltimore
C07D401/12A61K31/353A61K31/4184A61K31/422A61K31/4245A61K31/427A61K31/4439A61K31/4725A61K31/497A61K31/5377A61K31/541A61P1/16A61P3/10A61P35/00C07D207/34C07D207/416C07D231/14C07D249/06C07D401/14C07D403/12C07D405/12C07D413/12C07D413/14C07D417/12C07D417/14
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Quick Facts
Patent No.
US 12,378,220
App. No.
18/320,805
Granted
Aug 5, 2025
Kind
B2
Abstract

Compounds and compositions are provided as inhibitors of the Wnt/β-catenin pathway for the treatment of diseases that implicate the same.

Claims (15)

1. A method of treating or preventing a disease alleviated by inhibiting Wnt/β-catenin signaling in a patient in need of said treatment or prevention, the method comprising administering a therapeutically effective amount of one or more compounds having the formula (II):

wherein R 7 represents a substituent selected from the group consisting of substituted or unsubstituted isoquinolin-3-yl, quinolin-2-yl, quinolin-3-yl, naphthyl, thiazolyl, isooxazolyl, benzothiazolyl, benzimidizolyl, benzopyronyl,

R 8 represents a substituent selected from the group consisting of H, OH, NO 2 , CN, halo, and substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, amino, and alkoxy;

R 9 , R 10 , R 11 , R 12 , and R 13 each can independently represent a substituent selected from the group consisting of H, OH, NO 2 , CN, halo, and substituted or unsubstituted alkyl, alkylcarbonyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycle, heteroaryl, amino, alkoxy, carboxy, carbalkoxy, carboxamido, sulfonyl, sulfonamido, sulfinyl, monoalkylaminosulfinyl, dialkylaminosulfinyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonylamino, hydroxysulfonyloxy, alkoxysulfonyloxy, alkylsulfonyloxy, hydroxysulfonyl, alkoxysulfonyl, alkylsulfonylalkyl, monoalkylaminosulfonylalkyl, dialkylaminosulfonylalkyl, monoalkylaminosulfinylalkyl, and dialkylaminosulfinylalkyl;

X 4 represents N or CR 14 ;

X 5 represents N;

R 14 independently represents a substituent selected from the group consisting of H, OH, NO 2 , CN, halo, and substituted or unsubstituted alkyl, alkylcarbonyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycle, heteroaryl, amino, alkoxy, carboxy, carbalkoxy, carboxamido, sulfonyl, sulfonamido, sulfinyl, monoalkylaminosulfinyl, dialkylaminosulfinyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonylamino, hydroxysulfonyloxy, alkoxysulfonyloxy, alkylsulfonyloxy, hydroxysulfonyl, alkoxysulfonyl, alkylsulfonylalkyl, monoalkylaminosulfonylalkyl, dialkylaminosulfonylalkyl, monoalkylaminosulfinylalkyl, and dialkylaminosulfinylalkyl; or the pharmaceutically acceptable salts of the compound.

2. The method of claim 1 , wherein R 7 is selected from substituted or unsubstituted isoquinolin-3-yl, quinolin-2-yl, quinolin-3-yl.

3. The method of claim 1 , wherein R 7 is selected from

4. The method of claim 1 , wherein R 9 is selected from hydrogen, methyl, ethyl, fluoro, bromo, chloro, CN, methoxy, NO 2 , —C(O)CH 3 , —C(O)NH 2 , phenyl, and morpholinyl.

5. The method of claim 1 , wherein the compound is 1-(2-Methoxyphenyl)-5-methyl-N-(quinolin-2-yl)-1H-1,2,3-triazole-4-carboxamide, or a pharmaceutically acceptable salt thereof.

6. The method of claim 1 , wherein the compound is or 5-Methyl-N-(quinolin-2-yl)-1-(o-tolyl)-1H-1,2,3-triazole-4-carboxamide, or a pharmaceutically acceptable salt thereof.

7. The method of claim 1 , wherein the disease comprises alcoholic fatty liver disease (ALD) or a non-alcoholic fatty liver disease (NAFLD).

8. The method of claim 1 , wherein the disease is selected from the group consisting of simple fatty liver (steatosis), non-alcoholic steatohepatitis (NASH), and cirrhosis.

9. The method of claim 1 , wherein the disease is non-alcoholic steatohepatitis (NASH).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2023
From: XUE, FENGTIAN; SHU, YAN
To: UNIVERSITY OF MARYLAND, BALTIMORE
Reel/Frame 064184/0484 →
Continuity (6)
Continuation 16900616 · Jun 12, 2020
Continuation 16081657
Provisional Application 62352634 · Jun 21, 2016
Provisional Application 62301882 · Mar 1, 2016
Provisional Application 62301863 · Mar 1, 2016
Related Publication 20240208927A1 · Jun 27, 2024
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