US 12,077,531 B2
Imidazopyridinone compound
Akihiro Moriyama, Azumino (JP); and Yasushi Takigawa, Azumino (JP)
Assigned to KISSEI PHARMACEUTICAL CO., LTD., Matsumoto (JP)
Appl. No. 17/268,011
Filed by KISSEI PHARMACEUTICAL CO., LTD., Matsumoto (JP)
PCT Filed Sep. 12, 2019, PCT No. PCT/JP2019/035792
§ 371(c)(1), (2) Date Feb. 11, 2021,
PCT Pub. No. WO2020/054788, PCT Pub. Date Mar. 19, 2020.
Claims priority of application No. 2018-171839 (JP), filed on Sep. 13, 2018.
Prior Publication US 2021/0206765 A1, Jul. 8, 2021
Int. Cl. C07D 471/04 (2006.01); A61K 9/00 (2006.01); A61P 1/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 9/0053 (2013.01); A61P 1/00 (2018.01)] 19 Claims
 
1. A compound represented by the formula (I):

OG Complex Work Unit Chemistry
wherein
ring W is C6-10 aryl, 5- or 6-membered heteroaryl, 9- or 10-membered heteroaryl, C3-8 cycloalkyl or 3- to 8-membered heterocycloalkyl;
ring Z is a group selected from the group consisting of following (a) to (c):

OG Complex Work Unit Chemistry
wherein
Ra, Rb and Rc are each independently a hydrogen atom, a halogen atom, C1-6 alkyl, cyano, hydroxy or carboxy; and
Rd is a hydrogen atom or C1-6 alkyl;
R1 is a hydrogen atom, a halogen atom, C1-6 alkyl, cyano, hydroxy or carboxy, wherein when m is 2 or 3, two or more R1s may be different from each other;
R2 is a hydrogen atom, a halogen atom, C1-6 alkyl, halo C1-6 alkyl, C1-6 alkoxy, hydroxy, —CO2R4 or —CONR5R5′, wherein when n is 2 or 3, two or more R2s may be different from each other;
R4 is a hydrogen atom or C1-6 alkyl; and
R5 and R5′ are each independently a hydrogen atom, C1-6 alkyl, carboxy C1-6 alkyl, hydroxy C1-6 alkyl, halo C1-6 alkyl, C3-8 cycloalkyl or 3- to 8-membered heterocycloalkyl;
R3 is a hydrogen atom, a halogen atom, C1-6 alkyl, halo C1-6 alkyl, C1-6 alkoxy, halo C1-6 alkoxy, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, hydroxy, cyano, nitro, —NR6R6′, —CO2R7, —CONR8R8′ or the following group A, wherein when u is 2 or 3, two or more R3s may be different from each other;
R6 and R6′ are each independently a hydrogen atom or C1-6 alkyl;
R7 is a hydrogen atom or C1-6 alkyl;
R8 and R8′ are each independently a hydrogen atom, C1-6 alkyl, carboxy C1-6 alkyl, hydroxy C1-6 alkyl, halo C1-6 alkyl, C3-8 cycloalkyl or 3- to 8-membered heterocycloalkyl;
group A is a group selected from the group consisting of following (a) to (h):
(a) C6-10 aryl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(b) 5- or 6-membered heteroaryl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(c) C6-10 aryl C1-6 alkyl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(d) C6-10 aryloxy which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(e) 5- or 6-membered heteroaryl C1-6 alkyl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(f) 5- or 6-membered heteroaryloxy which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
(g) C3-8 cycloalkyl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B, and
(h) 3- to 8-membered heterocycloalkyl which is unsubstituted or substituted with 1 to 3 groups selected from substituent group B,
wherein substituent group B is a group consisting of a halogen atom, C1-6 alkyl, halo C1-6 alkyl, C1-6 alkoxy, halo C1-6 alkoxy, hydroxy, cyano, —NR9R9′, —NR9SO2R10, —CO2R10 and —CONR11R11′;
wherein R9 and R9′ are each independently a hydrogen atom or C1-6 alkyl;
R10 is a hydrogen atom or C1-6 alkyl; and
R11 and R11′ are each independently a hydrogen atom, C1-6 alkyl, carboxy C1-6 alkyl, hydroxy C1-6 alkyl, halo C1-6 alkyl, C3-8 cycloalkyl or 3- to 8-membered heterocycloalkyl;
m, n and u are each independently an integer number 1 to 3;
p and q are each independently 1 or 2; and
r is an integer number 0 to 6;
or a pharmaceutically acceptable salt thereof.