1-alkyl-5-arylidene-2-selenoxoimidazolidine-4-on and derivative thereof, preparation method therefor, and composition comprising same for preventing, alleviating or treating neurodegenerative diseases

Patent metadata

Field	Value
Publication number	US-12552779-B2
Application number	US-202118004952-A
Country	US
Kind code	B2
Filing date	Jul 9, 2021
Priority date	Jul 10, 2020
Publication date	Feb 17, 2026
Grant date	Feb 17, 2026

Abstract

The present invention relates to 1-alkyl-5-arylidene-2-selenoxoimidazolidine-4-ons and derivatives thereof, a method for producing the same, and a composition for prevention, improvement or treatment of neurodegenerative disease containing the same. Specifically, 1-alkyl-5-arylidene-2-selenoxoimidazolidine-4-ons and derivatives thereof, which are novel compounds of the present invention, can be used as an excellent composition for prevention, improvement or treatment of neurodegenerative disease.

First claim

The invention claimed is:

1 . A compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt of the compound:

where,
R 1 and R 1 ′ are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, an aryl group, heteroaryl, benzyl, and a phenethyl group, or R 1 and R 1 ′ may bond to each other to form a single ring;
R 2 and R 3 are each independently hydrogen, halo, cyano, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, heterocycloalkyl-alkyl, aryl, aryl-alkyl, or heteroaryl; and
the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, heterocycloalkyl-alkyl, aryl, aryl-alkyl, or heteroaryl may not be substituted or may be substituted with one or more groups selected from the group consisting of hydroxy; halogen; alkyl; -alkyl-hydroxy; -heterocycloalkyl-alkyl-hydroxy; —NH alkyl-O-alkyl-hydroxy; —NH alkyl-O-alkyl-halogen; —NH alkyl-heterocycloalkyl; alkoxy; amino; dialkylamino; nitro; cyano; carbonyl; cycloalkyl;
heterocycloalkyl unsubstituted or substituted with alkyl; aryl; and heteroaryl.

2 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 1 and R 1 ′ are each independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 heterocycloalkyl, C 6 -C 10 aryl, C 5 -C 10 heteroaryl, benzyl and a phenethyl group, or R 1 and R 1 ′ may bond to each other to form a single ring.

3 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein

4 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 2 is hydrogen; C 1 -C 12 alkyl unsubstituted or substituted with halogen; C 3 -C 10 cycloalkyl; —C 1 -C 6 alkyl-C 3 -C 10 heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O; —C 6 -C 10 aryl unsubstituted or substituted with halogen or C 1 -C 12 alkyl; or —C 1 -C 6 alkyl-C 6 -C 10 aryl.

5 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 2 is hydrogen; C 1 -C 12 alkyl; C 1 -C 6 alkyl substituted with halogen; C 3 -C 8 cycloalkyl; —C 1 -C 6 alkyl-C 3 -C 10 heterocycloalkyl containing heteroatoms N and O; —C 6 -C 10 aryl unsubstituted or substituted with halogen or C 1 -C 6 alkyl; or —C 1 -C 6 alkyl-C 6 -C 10 aryl.

6 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 2 is hydrogen; C 1 -C 12 alkyl; C 1 -C 6 alkyl substituted with halogen; C 3 -C 8 cycloalkyl; —C 1 -C 6 alkyl-morpholine; phenyl unsubstituted or substituted with halogen or C 1 -C 6 alkyl; or —C 1 -C 6 alkyl-phenyl.

7 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 3 is C 6 -C 10 heterocycloalkyl, C 6 -C 10 aryl or C 6 -C 10 heteroaryl, and the heterocycloalkyl, aryl or heteroaryl is not substituted or is substituted with one or more groups selected from the group consisting of hydroxy; halogen; C 1 -C 6 alkyl; —C 1 -C 6 alkyl-hydroxy; —C 3 -C 8 heterocycloalkyl-C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-halogen; —NHC 1 -C 6 alkyl-C 3 -C 8 heterocycloalkyl; C 1 -C 6 alkoxy; amino; di-C 1 -C 6 alkylamino; and C 3 -C 8 heterocycloalkyl unsubstituted or substituted with C 1 -C 6 alkyl.

8 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 3 is C 6 -C 10 heterocycloalkyl having a heteroatom N, C 6 -C 10 aryl or C 6 -C 10 heteroaryl having a heteroatom N, and the heterocycloalkyl, aryl or heteroaryl is not substituted or is substituted with one or more groups selected from the group consisting of hydroxy; halogen; C 1 -C 6 alkyl; —C 1 -C 6 alkyl-hydroxy; —C 3 -C 8 heterocycloalkyl-C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-halogen; —NHC 1 -C 6 alkyl-C 3 -C 8 heterocycloalkyl; C 1 -C 6 alkoxy; amino; di-C 1 -C 6 alkylamino; and C 3 -C 8 heterocycloalkyl unsubstituted or substituted with C 1 -C 6 alkyl.

9 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , wherein R 3 is phenyl, naphthyl, pyridine, piperazine, or imidazole, and the phenyl, naphthyl, pyridine, piperazine, or imidazole is not substituted or is substituted with one or more groups selected from the group consisting of hydroxy; halogen; C 1 -C 6 alkyl; —C 1 -C 6 alkyl-hydroxy; -piperazine-C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-hydroxy; —NHC 1 -C 6 alkyl-O—C 1 -C 6 alkyl-halogen; —NHC 1 -C 6 alkyl-morpholine; C 1 -C 6 alkoxy; amino; di-C 1 -C 6 alkylamino; pyrrolidine; piperidine; piperazine unsubstituted or substituted with C 1 -C 6 alkyl; and morpholine.

10 . The compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt of the compound according to claim 1 , which is selected from the group consisting of the following compounds:

Compound
Structural formula

1

2

3

4

5

6

Assignees

• Duksung Womens Univ Industry Academic Cooperation Foundation
• Knu Industry Cooperation Found
• Industry Academic Cooperation Foundation Of Yeungnam Univ
• Univ Ewha Ind Collaboration
• Ewha University—Industry Collaboration Found

Inventors

• Lee Sang Hyup
• Choi Dong Young
• Lee Jungkwan
• Ahn Sung Hoon
• Choi Sun
• Cho Hyun Sung
• Kim Cho Rong
• Lim Yoo Jin
• Kim Ye Eun
• Lee Yoonji

Classifications

• C07D401/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D233/96 Primary

  having three double bonds between ring members or between ring members and non-ring members · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61K31/5377

  not condensed and containing further heterocyclic rings, e.g. timolol · CPC title

• A61K31/496

  Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin · CPC title