US 12,187,729 B2
Compounds having PDE9A inhibitory activity, and pharmaceutical uses thereof
Chae Jo Lim, Daejeon (KR); Kwang-Seok Oh, Daejeon (KR); Jeong Hyun Lee, Daejeon (KR); Kyu Yang Yi, Daejeon (KR); Nack Jeong Kim, Daejeon (KR); Byung Ho Lee, Daejeon (KR); Ho Won Seo, Daejeon (KR); Soo Hee Kim, Daejeon (KR); Junyoung Choi, Daejeon (KR); Mi Young Lee, Daejeon (KR); and Ju Hee Lee, Daejeon (KR)
Assigned to KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
Appl. No. 17/311,293
Filed by KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
PCT Filed Dec. 5, 2019, PCT No. PCT/KR2019/017128
§ 371(c)(1), (2) Date Jun. 4, 2021,
PCT Pub. No. WO2020/116972, PCT Pub. Date Jun. 11, 2020.
Claims priority of application No. 10-2018-0156038 (KR), filed on Dec. 6, 2018.
Prior Publication US 2022/0017528 A1, Jan. 20, 2022
Int. Cl. A61K 31/519 (2006.01); C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) 8 Claims
 
1. A method for or preventing a disease related to Phosphodiesterase 9A, comprising administering a therapeutically effective amount of a compound represented by the following Chemical formula 1 or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
in Chemical Formula 1,
A1 is NH or N-C1-2alkyl,
A2 is H, linear or branched C1-5alkyl, or phenyl,
X is a substituent selected from the group consisting of —H, halogen, —NO2, —CN, -SR1, linear or branched C1-10alkyl unsubstituted or substituted with one or more halogens, linear or branched C1-10alkoxy unsubstituted or substituted with one or more halogens, C6-10aryl unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl, and C6-10aryloxy unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl,
Y is a substituent selected from the group consisting of C1-10 linear or branched alkyl unsubstituted or substituted with one or more halogens, C3-10cycloalkyl unsubstituted or substituted with one or more halogens, 6-10 membered heterocycloalkyl comprising O or S heteroatom unsubstituted or substituted with one or more halogens, C1-10 linear or branched alkoxy unsubstituted or substituted with one or more halogens, C6-10aryl unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl, and C6-10aryloxy unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl, and
R1 is a substituent selected from the group consisting of C1-10 linear or branched alkyl unsubstituted or substituted with one or more halogens, C1-10 linear or branched alkoxy unsubstituted or substituted with one or more halogens, C6-10aryl unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl, C1-2alkyl-C6-10aryl unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl, and C6-10aryloxy unsubstituted or substituted with one or more halogen or C1-10 linear or branched alkyl.