US 12,427,153 B2
1,2,4-triazin-3(2H)-one compounds for the treatment of hyperproliferative diseases
Stefan Nikolaus Gradl, Berlin (DE); Manuel Ellermann, Berlin (DE); Philip Lienau, Berlin (DE); Charlotte Christine Kopitz, Falkensee (DE); Martin Lange, Berlin (DE); Adrian Tersteegen, Wuppertal (DE); Detlev Sülzle, Berlin (DE); Timothy A. Lewis, Cambridge, MA (US); Heidi Greulich, Cambridge, MA (US); and Xiaoyun Wu, Cambridge, MA (US)
Assigned to Bayer Aktiengesellschaft, Leverkusen (DE); and The Broad Institute, Inc., Cambridge, MA (US)
Filed by BAYER AKTIENGESELLSCHAFT, Leverkusen (DE); and THE BROAD INSTITUTE, INC., Cambridge, MA (US)
Filed on Jul. 30, 2021, as Appl. No. 17/389,940.
Application 17/389,940 is a continuation of application No. PCT/EP2020/052287, filed on Jan. 30, 2020.
Claims priority of provisional application 62/800,126, filed on Feb. 1, 2019.
Prior Publication US 2021/0353630 A1, Nov. 18, 2021
Int. Cl. A61K 31/53 (2006.01); A61P 35/00 (2006.01); C07D 253/06 (2006.01); C07D 403/10 (2006.01); C07D 403/12 (2006.01)
CPC A61K 31/53 (2013.01) [A61P 35/00 (2018.01); C07D 253/06 (2013.01); C07D 403/10 (2013.01); C07D 403/12 (2013.01)] 8 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is a hydrogen atom, a halogen atom, a C1-C3-alkyl group, or a C1-C3-haloalkyl group;
R2 is a hydrogen atom, or a halogen atom;
with the proviso that both, R1 and R2, may not be a hydrogen atom at the same time with the exception if R3 is an ortho substituted phenyl group, both, R1 and R2, may also be a hydrogen atom;
R3 is
a C1-C3-alkyl group which is substituted one or more times with a group independently selected from a C1-C3-alkyl group, a C1-C3-alkoxy group, a heterocycloalkyl group, and an amino group which is substituted once or twice with a C1-C3-alkyl group,
a C2-C6-alkenyl group, which is optionally substituted with a C1-C3-alkoxy group,
a C5-C6-cycloalkenyl group,
a phenyl group which is substituted one or more times with a group independently selected from halogen atom, C1-C3-alkyl group, and a C1-C3-haloalkyl group,
a 4- to 6-membered heterocycloalkyl group which is substituted one or more times with a group independently selected from a fluorine atom, a hydroxy group, and a C1-C3-alkyl group,
a

OG Complex Work Unit Chemistry
 group, a

OG Complex Work Unit Chemistry
 group, a

OG Complex Work Unit Chemistry
 group,
a 5- to 10-membered heteroaryl group which is substituted one or more times with a group independently selected from an amino group, a halogen atom, and a C1-C3-haloalkyl group,
a C1-C6-alkoxy group which is optionally substituted with a group independently selected from C1-C3-haloalkyl group, a hydroxy group, a C1-C3-alkyoxy group, a C4-C6-cycloalkyl group, a 4- to 6-membered heterocycloalkyl group, a 5- to 6-membered heteroaryl group, with the proviso that an unsubstituted methoxy group is excluded;
a NR5R6 group, and
a

OG Complex Work Unit Chemistry
 group,
R4 is a hydrogen atom or a C1-C3-alkyl group;
R5 is a hydrogen atom
R6 is selected from
a C1-C3-alkyl group which is substituted one or more times with a group selected from a 5- to 6-membered heteroaryl group, a C1-C3-alkoxy group, a hydroxy group, a C1-C3-haloalkyl group, and a C4-C6-cycloalkyl group which itself is optionally substituted with a C1-C3-hydroxyalkyl group,
and
a C5-C6-cycloalkyl group;
or a stereoisomer, a tautomer, an N-oxide, or a salt thereof, or a salt of a stereoisomer, a salt of a tautomer, a salt of an N-oxide or a mixture of same.