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

A method for producing a compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt of the compound, the method comprising:

• reacting an amine compound represented by the following Chemical Formula 5 with formic acid to produce a formamide compound represented by the following Chemical Formula 6;
• reacting the formamide compound with selenium (Se) under a condition containing one or more selected from the group consisting of triphosgene, dichloromethane, and triethylamine to produce an isoselenocyanate compound represented by the following Chemical Formula 7;
• reacting the isoselenocyanate compound with an amino acid compound represented by the following Chemical Formula 8 in a solvent to produce a 1-alkyl-2-selenoxoimidazolidine-4-on compound represented by the following Chemical Formula 9;
• and
• reacting the 1-alkyl-2-selenoxoimidazolidine-4-on compound with an aldehyde-based compound represented by the following Chemical Formula 10 to produce the compound represented by Chemical Formula 1:
• where,
• R1 and R1′ are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, an aryl group, heteroaryl, benzyl, and a phenethyl group, or R1 and R1′ may bond to each other to form a single ring;
• R2 and R3 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.