Oxazolidine-based compound and selective androgen receptor agonist comprising same

A method of preparing a compound of Chemical Formula 1a comprising the steps of:

• preparing a compound of Chemical Formula 5 from a fluorobenzene compound of Chemical Formula 4 by substitution reaction, and
• preparing the compound of Chemical Formula 1a from the compound of Chemical Formula 5 by cyclodehydration reaction with aldehyde, ketone, or a precursor thereof:
• in Chemical Formula 1a , R1 is a substituent represented by the following Chemical Formula 2,
• R2 is hydrogen,
• —X(CH2)nR8 [Chemical Formula 2]
• in Chemical Formula 2, X is O, n is 0, R8 is hydrogen,
• R3 and R4 each independently is a substituent selected from the group consisting of hydrogen and C1-C6 alkyl,
• R5 and R6 each independently is a substituent selected from the group consisting of hydrogen, halogen and C1-C6 alkyl,
• R7 is halogen, cyano, or nitro, and
• the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, and halogen.

A method of preparing a compound of Chemical Formula 1d comprising the steps of:

• preparing a compound of Chemical Formula 7 from the fluorobenzene compound of Chemical Formula 4 by substitution reaction,
• preparing a compound of Chemical Formula 8 from the compound of Chemical Formula 7 by cyclodehydration reaction with aldehyde, ketone, or a precursor thereof, and
• preparing a compound of Chemical Formula 1d from the compound of Chemical Formula 8 by amide formation reaction with amine,
• in Chemical Formula 1d, R1 is a substituent represented by the following Chemical Formula 2 or Chemical Formula 3,
• R2 is an oxo group,
• R3 and R4 each independently is a substituent selected from the group consisting of hydrogen and C1-C6 alkyl,
• R5 and R6 each independently is a substituent selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl,
• R7 is halogen, cyano, or nitro, and
• the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, and halogen;
• —X(CH2)nR8 [Chemical Formula 2]
• in Chemical Formula 2, X is N(R), n is an integer of 0 or 1,
• R is hydrogen,
• R8 is hydrogen, C3-C7 heterocycle having a nitrogen atom, aryl, or heteroaryl having a nitrogen atom which has one or more rings,
• the heterocycle, aryl, or heteroaryl each independently is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, a cyano group, a nitro group, a hydroxyimino group, a C1-C6 alkoxyimino group, (CH2)pNR10R11, (CH2)pNC(O)R10, (CH2)pNC(O)OR10, (CH2)pNC(O)NR10R11, (CH2)pNS(O)2R10, (CH2)S(O)2R10(CH2)pC(O)OR10,
• p is an integer of 0 or 1,
• R10 and R11 each independently is a substituent selected from the group consisting of hydrogen, C1-C6 alkyl, pyrrolidinyl, and phenyl, and
• the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, amino, cyano and halogen,
• in Chemical Formula 3, Y is C or N,
• m is an integer of 0, 1 or 2,
• R9 is a substituent selected from the group consisting of hydrogen, oxo, hydroxy, C1-C6 alkyl, cyano, C(O)R12, C(O)OR12, C(O)NR12R13, S(O)2R12, NC(O)R13, and NC(O)OR12,
• R12 and R13 each independently is a substituent selected from the group consisting of hydrogen, hydroxy, and C1-C6 alkyl, and
• the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, halogen and cyano.