Small molecule inhibitors of MYC and uses thereof

Patent metadata

Field	Value
Publication number	US-11214567-B2
Application number	US-201816641130-A
Country	US
Kind code	B2
Filing date	Aug 23, 2018
Priority date	Aug 23, 2017
Publication date	Jan 4, 2022
Grant date	Jan 4, 2022

Abstract

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having an oxadiazole-oxadiazolone structure (e.g., oxadiazole-phenyl-oxadiazolone compounds, oxadiazole-pyridine-oxadiazolone compounds, oxadiazole-indole-oxadiazolone compounds, oxadiazole-quinoline-oxadiazolone compounds, oxadiazole-pyrrole-oxadiazolone compounds, and oxadiazole-vinyl-oxadiazolone compounds), and their use as therapeutics for the treatment of cancer and other diseases.

First claim

What is claimed is:

1. A compound having

including pharmaceutically acceptable salts, solvates, and/or prodrugs thereof;
wherein R 3 and R 4 are each independently a chemical moiety selected from hydrogen, methyl,

wherein R 5 and R 6 are each independently a chemical moiety selected from hydrogen, fluorine, chlorine, and

and wherein if said compound has Formula VIII then:
R 3 and R 4 cannot both be phenyl, and R 5 and R 6 cannot both be hydrogen.

2. The compound of claim 1 , wherein said compound is selected from the group consisting of:

KJA-21

3-methyl-4-(2-(3-(2-1,2,4-oxadiazol-5- yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-22

3-ethyl-4-(2-(3-ethyl-1,2,4-oxadiazol-5- yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-23

3-isopropyl-4-(2-(3-isopropyl-1,2,4-oxadiazol- 5-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-24

3-cyclohexyl-4-(2-(3-cyclohexyl-1,2,4- oxadiazol-5-yl)phenyl)-1,2,4-oxadiazol- 5(4H)-one

KJA-25

3-(tetrahydro-2H-pyran-4-yl)-4-(2-(3- (tetrahydro-2H-pyran-4-yl)-1,2,4-oxadiazol-5- yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-26

3-cyclopentyl-4-(2-(3-cyclopentyl-1,2,4- oxadiazol-5-yl)-5-fluorophenyl)-1,2,4- oxadiazol-5(4H)-one

KJA-27

3-(cyclohex-3-en-1-yl)-4-(2-(3-(cyclohex-3- en-1-yl)-1,2,4-oxadiazol-5-yl)-5- methoxyphenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-28

4-(2-(5-butyl-1l3,2,4-chloraoxazol-3-yl)-4- chlorophenyl)-3-propyl-1,2,4-oxadiazol- 5(4H)-one

KJA-31

3-(pyridin-3-yl)-4-(2-(5-(pyridin-3-yl)-1l3,2,4- chloraoxazol-3-yl)phenyl)-1,2,4-oxadiazol- 5(4H)-one

KJA-32

3-(thiophen-2-yl)-4-(2-(5-(thiophen-2-yl)- 1l3,2,4-chloraoxazol-3-yl)phenyl)-1,2,4- oxadiazol-5(4H)-one

KJA-33

3-(quinolin-8-yl)-4-(2-(5-(quinolin-8-yl)- 1l3,2,4-chloraoxazol-3-yl)phenyl)-1,2,4- oxadiazol-5(4H)-one

KJA-34

4-(2-(5-(1H-indol-2-yl)-1l3,2,4-chloraoxazol- 3-yl)phenyl)-3-(1H-indol-2-yl)-1,2,4- oxadiazol-5(4H)-one

KJA-02

3-(4-chlorophenyl)-4-(2-(3-(4-chlorophenyl)- 1,2,4-oxadiazol-5-yl)phenyl)-1,2,4-oxadiazol- 5(4H)-one

KJA-03

3-(p-tolyl)-4-(2-(3-(p-tolyl)-1,2,4-oxadiazol-5- yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

KJA-04

3-(4-fluorophenyl)-4-(2-(3-(4-fluorophenyl)- 1,2,4-oxadiazol-5-yl)phenyl)-1,2,4-oxadiazol- 5(4H)-one

KJA-05

Assignees

• Univ Michigan Regents
• Univ Yunnan

Inventors

• Neamati Nouri
• Jin Yi
• Lin Jun

Classifications

• A61K45/00

  Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00 · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• A61K31/4245

  Oxadiazoles · CPC title

• C07D271/06 Primary

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title