US 12,391,674 B2
Heterocyclic compounds for the treatment of epilepsy
Tomoichi Shinohara, Osaka (JP); Shin Iwata, Osaka (JP); Masaki Suzuki, Osaka (JP); Kenta Arai, Osaka (JP); Nobuaki Ito, Osaka (JP); and Takuya Chiba, Osaka (JP)
Assigned to OTSUKA PHARMACEUTICAL CO., LTD., Tokyo (JP)
Appl. No. 17/292,528
Filed by OTSUKA PHARMACEUTICAL CO., LTD., Tokyo (JP)
PCT Filed Nov. 29, 2019, PCT No. PCT/JP2019/046879
§ 371(c)(1), (2) Date May 10, 2021,
PCT Pub. No. WO2020/111263, PCT Pub. Date Jun. 4, 2020.
Claims priority of application No. 2018-224724 (JP), filed on Nov. 30, 2018.
Prior Publication US 2021/0403456 A1, Dec. 30, 2021
Int. Cl. C07D 403/04 (2006.01); A61P 25/08 (2006.01); C07D 239/34 (2006.01); C07D 239/47 (2006.01); C07D 239/54 (2006.01); C07D 401/04 (2006.01); C07D 401/12 (2006.01); C07D 405/04 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01); C07D 471/04 (2006.01); C07D 487/04 (2006.01)
CPC C07D 403/04 (2013.01) [A61P 25/08 (2018.01); C07D 239/34 (2013.01); C07D 239/47 (2013.01); C07D 239/54 (2013.01); C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 405/04 (2013.01); C07D 413/04 (2013.01); C07D 417/04 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01)] 17 Claims
 
1. A compound represented by Formula I:

OG Complex Work Unit Chemistry
wherein
D is

OG Complex Work Unit Chemistry
ring A is benzene;
ring B is pyrimidine;
ring C is the following unsaturated rings, oxides thereof, dioxides thereof, provided that pyrimidine-2,4-dione and dihydropyrimidine-2,4-dione are excluded, or those in which a part or all of unsaturated bonds in the unsaturated rings are reduced with hydrogen:
pyridazine,
pyrimidine,
indole,
pyrrolopyridine,
indazole,
pyrazolopyridine,
imidazopyridine,
imidazopyrazine,
imidazopyridazine,
triazolopyridine,
pyrazolopyrimidine,
imidazopyrimidine,
triazolopyrimidine,
isoquinoline,
naphthyridine,
quinazoline,
quinoxaline,
benzodioxole,
oxazine,
oxazepine,
benzothiazole, and
triazolopyridazine;
wherein ring C is bonded to a 5-position of ring B,
R1 is halogen, C1-6 alkyl optionally substituted with halogen, —O—C1-6 alkyl optionally substituted with halogen or —CN;
R2 is —O—C1-6 alkyl;
R3 is halogen, C1-6 alkyl optionally substituted with halogen or —O—C1-6 alkyl, —O— C1-6 alkyl optionally substituted with halogen, —C1-6 alkyl-OH, —OH, —CN, —CONH2 or —NH2;
L is —O—, which is bonded at a 2-position of ring B; and
k is 0, 1 or 2, and when k is 2, each R1 independently represents the same or different substituent;
m is 0 or 1;
n is 0, 1 or 2, and when n is 2, each R3 independently represents the same or different substituent;
or a salt thereof.