US 11,987,586 B1
Pyrrolo[1,2-c]imidazole derivatives as orexin type 2 receptor agonists
Yasushi Hattori, Kanagawa (JP); Marilena Pira, Kanagawa (JP); Yoshiteru Ito, Kanagawa (JP); Kohei Takeuchi, Kanagawa (JP); Eiji Kimura, Kanagawa (JP); Norihito Tokunaga, Kanagawa (JP); Shuhei Ikeda, Kanagawa (JP); Martin Alexander Pawliczek, Kanagawa (JP); Noriyuki Tezuka, Kanagawa (JP); Yasutaka Hoashi, Kanagawa (JP); Yuhei Miyanohana, Kanagawa (JP); Yuichi Kajita, Kanagawa (JP); and Tatsuki Koike, Kanagawa (JP)
Assigned to Takeda Pharmaceutical Company Limited, (JP)
Filed by TAKEDA PHARMACEUTICAL COMPANY LIMITED, Osaka (JP)
Filed on Oct. 30, 2023, as Appl. No. 18/497,602.
Claims priority of provisional application 63/381,736, filed on Oct. 31, 2022.
Int. Cl. C07D 487/04 (2006.01); A61P 25/00 (2006.01); C07D 413/04 (2006.01); C07D 519/00 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 25/00 (2018.01); C07D 413/04 (2013.01); C07D 519/00 (2013.01)] 16 Claims
 
1. A compound represented by the formula (Ia):

OG Complex Work Unit Chemistry
wherein
R1 is a C1-6 alkyl group, a C3-10 cycloalkyl group, or a mono-C1-6 alkylamino group;
r is 0 or 1;
R2 and R3 are each independently a hydrogen atom, or
when r is 0, then R2 and R3 may be taken together to form a bond;
R4 is a hydrogen atom;
R5 is a phenyl group optionally substituted by 1 to 3 halogen atoms;
R6 and R7 are each independently a hydrogen atom, or a halogen atom;
X5 is CH or N; and
R12 and R13 are each independently a hydrogen atom, a C1-6 alkyl group, or a halogen atom;
or a salt thereof.