US 9,809,583 B2
Oxazolidine-based compound and selective androgen receptor agonist comprising same
Sung Pil Choi, Gyeonggi-do (KR); Seul Min Choi, Gyeonggi-do (KR); Byoung Hwa Son, Gyeonggi-do (KR); Hyun Jung Kim, Gyeonggi-do (KR); Ju Mi Kim, Gyeonggi-do (KR); Byung Jun Jang, Seoul (KR); Ji Hyun Sung, Seoul (KR); Ji Hye Lee, Gyeonggi-do (KR); Eunjin Kim, Gyeonggi-do (KR); Kyung Koo Kang, Gyeonggi-do (KR); and Soon-Hoe Kim, Gyeonggi-do (KR)
Assigned to DONG-A ST CO., LTD., (KR)
Appl. No. 15/305,929
Filed by DONG-A ST CO., LTD., Seoul (KR)
PCT Filed Apr. 7, 2015, PCT No. PCT/KR2015/003477
§ 371(c)(1), (2) Date Oct. 21, 2016,
PCT Pub. No. WO2015/163604, PCT Pub. Date Oct. 29, 2015.
Claims priority of application No. 10-2014-0049277 (KR), filed on Apr. 24, 2014.
Prior Publication US 2017/0050955 A1, Feb. 23, 2017
Int. Cl. C07D 413/12 (2006.01); C07D 413/06 (2006.01); C07D 263/04 (2006.01); C07D 263/06 (2006.01); A61K 31/421 (2006.01)
CPC C07D 413/12 (2013.01) [A61K 31/421 (2013.01); C07D 263/04 (2013.01); C07D 263/06 (2013.01); C07D 413/06 (2013.01)] 14 Claims
 
1. A compound represented by the following Chemical Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Drawing
in Chemical Formula 1,
R1 is a substituent represented by the following Chemical Formula 2 or Chemical Formula 3,
R2 is hydrogen, oxo, or C1-C6 alkyl,
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,
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 O, N(R), S or S(O)2,
R is hydrogen,
R8 is hydrogen, C3-C7 heterocycle having a nitrogen atom, aryl, or heteroaryl having a nitrogen atom which has one or two 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)pC(O)NR10R11, (CH2)pNS(O)2R10, (CH2)pS(O)2R10(CH2)pC(O)OR10,

OG Complex Work Unit Drawing
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,
the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, amino, cyano and halogen,
n is 0 or 1;

OG Complex Work Unit Drawing
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, NR12R13, 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.