US 12,378,224 B2
Heteroaryl compounds and their use as Mer inhibitors
Jin Kwan Kim, Suwon-si (KR); Hadong Kim, Seoul (KR); Ki Moon Ryu, Yongin-si (KR); Seong Jin Park, Seoul (KR); Taeyoung Yoon, Seoul (KR); and Mi Yeon Jang, Yongin-si (KR)
Assigned to DONG-A SOCIO HOLDINGS CO., LTD., Seoul (KR)
Filed by Dong-A Socio Holdings Co., Ltd., Seoul (KR)
Filed on Dec. 30, 2020, as Appl. No. 17/138,534.
Application 17/138,534 is a continuation of application No. 16/341,005, granted, now 10,913,730, previously published as PCT/US2017/055793, filed on Oct. 9, 2017.
Claims priority of provisional application 62/406,015, filed on Oct. 10, 2016.
Prior Publication US 2021/0371398 A1, Dec. 2, 2021
Int. Cl. C07D 401/14 (2006.01); C07D 401/12 (2006.01); C07D 471/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 401/12 (2013.01); C07D 471/04 (2013.01)] 10 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof;
wherein:
Ring A is

OG Complex Work Unit Chemistry
X is —C(═O)N(R8)—, or —N(R8)—;
n is 1 or 2;
p is 1 or 2;
L is none, C1-3 alkyl, —C(═O)—, —C(═O)O—, —C(═O)N(R8);
R2 is aryl, or heteroaryl which aryl, or heteroaryl can optionally be substituted with one or more R18;
R3 is H, aryl or heteroaryl, which can optionally be substituted with one or more R9;
R4, R5, R6, and R7 are the same as or different from each other, and each are independently H, C1-3 alkyl, —OR21, or —OCH2R21;
R8 is H, C1-6 alkyl, C1-3 alkylaryl, or C1-3 alkylheteroaryl which C1-6 alkyl, C1-3 alkylaryl or C1-3 alkylheteroaryl can optionally be substituted with one or more R9;
R9 is halogen, C1-6 alkyl, —NH2, heteroaryl, aryl, -J9-heterocyle, -J9-aryl or

OG Complex Work Unit Chemistry
 which C1-6 alkyl, aryl, heterocycle, heteroaryl, -J9-heterocycle, or -J9-aryl can be substituted with one or more R16;
R16 is halogen, C1-6 alkyl, (═O), or —NH2;
R18 is C1-6 alkyl, —NH2, or heterocycle, which alkyl or heterocycle, can be substituted with one or more R19;
R19 is halogen, hydroxyl, —CN, —CHO, —NR10R11, —NO2, C1-6 alkyl, (═O), C3-10 cycloalkyl, C1-4 hydroxyalkyl, C1-6 alkoxy, C2-6 alkenyl, or aryl;
R21 is aryl which is substituted with one or more halogen, C1-6 alkyl, or —NH2; J9 is C1-3 alkyl, or —O—;
R10 and R11 are H; and
R24 is H.