IP Library › Granted Patent US 12,054,478
Granted Patent B2
US 12,054,478 · App. 17/944,757 · Granted Aug 6, 2024

Compositions and methods for inhibiting phenyl triazole MLL1-WDR5 protein-protein interaction

Inventors: Qidong You (Nanjing, CN); Xiaoke Guo (Nanjing, CN); Dongdong Li (Nanjing, CN); Weilin Chen (Nanjing, CN); Zhihui Wang (Nanjing, CN)
Assignee: HUYABIO International, LLC
C07D405/12C07D249/06C07D401/12C07D403/10
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Quick Facts
Patent No.
US 12,054,478
App. No.
17/944,757
Granted
Aug 6, 2024
Kind
B2
Abstract

The present disclosure relates to the field of medicinal chemistry, in particular to a phenyl triazole MLL1-WDR5 protein-protein interaction inhibitor (I) and a preparation method thereof, and pharmacodynamics experiments prove that the compound of the present disclosure has relatively strong MLL1-WDR5 protein-protein interaction inhibition activity.

Claims (10)

1. A method of treating acute leukemia in a subject, the method comprising administering to the subject a compound of the formula (I) or a pharmaceutically acceptable salt thereof:

wherein X is hydrogen, methyl, methoxy or halogen;

Y is —CH2-, —O—, —S—, —CO—, —CH2O—, —NR5-, —CONR6- or —NR7CO—, wherein R5, R6, or R7

each independently is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl or substituted phenyl, the substituent is halogen, C1-C4 alkyl, C1-C4 alkoxy, amino, hydroxyl, thiol, carboxyl, cyano, trifluoromethyl or imidazolyl;

M is 0-6;

R1 is hydrogen, amino, hydroxyl, thiol, carboxyl, cyano, —CONH2, C1-C4 alkyl, C1-C4 alkoxy, phenyl, substituted phenyl, substituted or unsubstituted nitrogen- or oxygen-containing 3 to 7 membered heterocyclic ring, —NR8COR9, —CONR10R11 or —NR10R11, wherein R8 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl or substituted phenyl, R9 is amino, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, phenyl or substituted phenyl, substituted or unsubstituted nitrogen- or oxygen-containing 3 to 7 membered heterocyclic ring, R10, R11 independently is hydrogen, C1-C4 alkyl, phenyl or substituted phenyl, substituted or unsubstituted nitrogen- or oxygen-containing 3 to 7 membered heterocyclic ring, or R10 and R11 are bonded to form nitrogen- or oxygen-containing 3 to 7 membered heterocyclic ring, wherein the substituent is halogen, C1-C4 alkyl, C1-C4 alkoxy, amino, hydroxyl, thiol, carboxyl, cyano, trifluoromethyl or imidazolyl;

R2 is disubstituted or trisubstituted halogen, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethyl, nitro or cyano;

R3 is amino, methylamino, aminomethyl, hydroxyl, hydroxymethyl, thiol or —CONH2; R4 is N-methylpiperazine, 1,2-dimethyl piperazine or N-methylhomopiperazine; and a pharmaceutically acceptable carrier.

2. The method of claim 1 , wherein the acute leukemia is an acute leukemia having an MLL1 gene rearrangement type.

3. The method of claim 1 , the compound of the formula (I) or a pharmaceutically is selected from any of the compounds below:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2023
From: YOU, QIDONG; GUO, XIAOKE; LI, DONGDONG; CHEN, WEILIN; WANG, ZHIHUI
To: CHINA PHARMACEUTICAL UNIVERSITY
Reel/Frame 064364/0009 →
Priority Claims (1)
CN 20181036588.0 · Apr 23, 2018 · national
Continuity (3)
Division 17078052 · Oct 22, 2020
Continuation PCTCN2018123500 · Dec 25, 2018
Related Publication 20230098016A1 · Mar 30, 2023
Cited By (1)
US 12,453,731