US 12,466,812 B2
Pyridinyltriazine derivative having protein kinase inhibitory activity, and pharmaceutical composition for preventing, ameliorating, or treating cancer comprising same
Tae Bo Sim, Seoul (KR); Seong Shick Ryu, Seoul (KR); Yun Ju Nam, Seoul (KR); and Woo Young Hur, Seoul (KR)
Assigned to KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY, Seoul (KR)
Appl. No. 17/770,630
Filed by KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY, Seoul (KR)
PCT Filed Oct. 22, 2020, PCT No. PCT/KR2020/014491
§ 371(c)(1), (2) Date Apr. 21, 2022,
PCT Pub. No. WO2021/080346, PCT Pub. Date Apr. 29, 2021.
Claims priority of application No. 10-2019-0132662 (KR), filed on Oct. 24, 2019.
Prior Publication US 2023/0027716 A1, Jan. 26, 2023
Int. Cl. C07D 403/12 (2006.01); A61P 35/00 (2006.01); C07D 401/04 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 403/12 (2013.01) [A61P 35/00 (2018.01); C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01)] 9 Claims
 
1. A compound selected from a pyridinyl triazine derivative compound represented by the following Formula 1, a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, and a stereoisomer thereof:

OG Complex Work Unit Chemistry
wherein
X1, X2, and X3 are each CH;
X4 is N;
n is 4, wherein the four groups of R1 are Cl at the 2nd position, Cl at the 6th position, OCH3 at the 3rd position, and OCH3 at the 5th position,
R2 is a halogen atom, a C1-C13 alkyl group, a C3-C10 cyclic group, a C3-C10 aryl group, or a C3-C10 heteroaryl group,
wherein the C1-C13 alkyl group or the C3-C10 cyclic group comprises at least one substituent selected from the group consisting of a hydroxy group, a halogen group, a C1-C13 alkyl group, a C1-C6 alkoxy group, an amino group (—NR3R4), a nitro group (—N(O)2), an amide group (−(C═O)NR3R4), a carboxyl group (—C(O)OH), a nitrile group (—CN), a urea group (—NR3(C═O)NR4—), a sulfonamide group (—NHS(O)2—), a sulfide group (—S—), a sulfone group (—S(O)2—), a phosphinyl group (—P(O)R3R4), a C6-C10 aryl group, a C3-C10 heteroaryl group, and a C3-C10 heterocyclic group,
the C3-C10 aryl group or the C3-C10 heteroaryl group comprises at least one substituent selected from the group consisting of hydrogen, a hydroxy group, a halogen group, a carbonyl group (—(C═O)R3R4), a C1-C3 alkyl group substituted or unsubstituted with halogen or a C3-C10 heterocyclic group, a C1-C3 alkoxy group substituted or unsubstituted with halogen or a C3-C10 heterocyclic group, a C6-C10 phenoxy group, an amino group (—NR3R4), a nitro group (—N(O)2), an amide group (—(C═O)NR3R4), a carboxyl group (—C(O)OH), a nitrile group (—CN), a urea group (—NR3(C═O)NR4—), a sulfonamide group (—NHS(O)2—), a sulfide group (—S—), a sulfone group (—S(O)2—), a phosphinyl group (—P(O)R3R4), a C6-C10 aryl group, a C3-C10 heteroaryl group, and a C3-C10 heterocyclic group,
R3 and R4 described above each independently comprise at least one selected from the group consisting of hydrogen, a C1-C6 alkyl group, a C1-C6 alkenyl group, a C1-C6 alkynyl group, a C6-C10 aryl group, a C3-C10 heteroaryl group, and a C3-C10 heterocyclic group,
the C3-C10 heteroaryl group contains at least one heteroatom selected from the group consisting of N, O, and S,
L is —NHC(O)— or —C(O)NH—,
Z comprises one to four substituents selected from C1-C8 alkyl, C1-C8 haloalkyl, 5-membered or 6-membered heteroaryl containing 1 to 3 nitrogen atoms, and 5-membered or 6-membered heterocycloalkyl containing 1 to 3 heteroatoms selected from nitrogen and oxygen atoms, wherein the heteroaryl or heterocycloalkyl is substituted or unsubstituted with C1-C8 alkyl.