US 12,404,268 B2
2-heteroaryl aminoquinazolinone derivative
Kazuto Mori, Osaka (JP); Hiroyuki Kitano, Osaka (JP); Tomoyuki Furuta, Osaka (JP); Hajime Seki, Osaka (JP); and Yohei Kobayashi, Osaka (JP)
Assigned to Sumitomo Pharma Co., Ltd., Osaka (JP)
Appl. No. 17/433,193
Filed by Sumitomo Pharma Co., Ltd., Osaka (JP)
PCT Filed Apr. 23, 2021, PCT No. PCT/JP2021/016498
§ 371(c)(1), (2) Date Aug. 23, 2021,
PCT Pub. No. WO2021/215537, PCT Pub. Date Oct. 28, 2021.
Claims priority of application No. 2020-077487 (JP), filed on Apr. 24, 2020.
Prior Publication US 2022/0340553 A1, Oct. 27, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 413/12 (2006.01); A61K 31/506 (2006.01); A61K 45/06 (2006.01); A61P 25/08 (2006.01); A61P 25/28 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 471/04 (2006.01)
CPC C07D 413/12 (2013.01) [A61K 31/506 (2013.01); A61K 45/06 (2013.01); A61P 25/08 (2018.01); A61P 25/28 (2018.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 471/04 (2013.01)] 27 Claims
 
1. A compound represented by formula (1):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein
X1 represents CR1 or N,
X2 represents CR2 or N,
X3 represents CR3 or N,
X4 represents CR4 or N,
wherein (1) if X1 is N, X2 is CR2, X3 is CR3, and X4 is CR4, (2) if X2 is N, X1 is CR1, X3 is CR3, and X4 is CR4, (3) if X3 is N, X1 is CR1, X2 is CR2, and X4 is CR4, and (4) if X4 is N, X1 is CR1, X2 is CR2, and X3 is CR3,
Y represents optionally substituted C1-6 alkyl, an optionally substituted C3-10 alicyclic group, an optionally substituted 4- to 10-membered non-aryl heterocycle, optionally substituted C6-10 aryl, or optionally substituted 5- to 10-membered heteroaryl,
Z represents optionally substituted 5- to 10-membered heteroaryl, wherein when Z is substituted, it is substituted with 1 to 3 of the same or different substituents selected from the group consisting of halogen, cyano, dimethylamino, C1-6 alkoxy, and C1-6 alkyl (wherein the alkoxy and the alkyl are each independently optionally substituted with 1 to 3 of the same or different substituents selected from the group consisting of halogen, hydroxy, and C1-6 alkoxy),
wherein Z does not attach to a nitrogen atom to which the heteroaryl attaches at a nitrogen atom on a ring of the
heteroaryl group
R1, R2, R3, and R4 each independently represent a hydrogen atom, halogen, cyano, C1-6 alkylsulfonyl, —SO2—NR5R6, —NR7R8, —NR9—C(═O)R10, —NR11—SO2—R12, —C(═O)NR13R14, —C(═O)OR15, optionally substituted C1-6 alkyl, or optionally substituted C1-6 alkoxy,
R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, and R15 are the same or different, each independently, and if there are multiple instances, they each independently represent a hydrogen atom, a C3-6 alicyclic group, or C1-6 alkyl (wherein the alicyclic group and the alkyl are each independently optionally substituted with 1 to 3 of the same or different substituents selected from the group consisting of halogen, a hydroxyl group, a C3-10 alicyclic group, C1-6 alkoxy, and a 4- to 6-membered non-aryl heterocyclic group), wherein R5 and R6, R7 and R8, and R13 and R14, together with the nitrogen atom to which they are attached, may form a 4- to 10-membered nitrogen-containing non-aryl heterocyclic group (wherein the ring is optionally substituted with 1 to 5 of the same or different substituents selected from the group consisting of halogen, hydroxy, C1-6 alkyl, and C1-6 alkoxy),
provided that the compound is not:
a compound represented by formula (W-1):

OG Complex Work Unit Chemistry
wherein
Za is optionally substituted 5- to 10-membered heteroaryl;
a compound represented by formula (W-2):

OG Complex Work Unit Chemistry
wherein
Xa is O or S, and Yb is ethyl, unsubstituted phenyl, 4-chlorophenyl, or 4-methoxyphenyl;
a compound represented by formula (W-3):

OG Complex Work Unit Chemistry
wherein
Xc is —S— or —SO2—, and Yc is unsubstituted phenyl, 4-chlorophenyl, or 4-methoxyphenyl;
a compound represented by formula (W-4):

OG Complex Work Unit Chemistry
wherein
Xd is methoxy, chloro, or dimethylamino, and Yd is ethyl, unsubstituted phenyl, 4-chlorophenyl, or 4-methoxyphenyl;
2-{(4,6-dimethylpyrimidin-2-yl)amino}-3-isopentylquinazolin-4 (3H)-one;
3-(pyridin-2-yl)-2-(pyridin-2-ylamino) quinazolin-4 (3H)-one;
3-methyl-2-{[2-((1-methylpiperidin-4-yl) methoxy)pyridin-3-yl]amino}pyrido[3,4-d]pyrimidin-4 (3H)-one; or
3-methyl-2-{[2-((1-methylpiperidin-4-yl) methoxy)pyridin-3-yl]amino}pyrido[2,3-d]pyrimidin-4 (3H)-one.