US 12,410,168 B2
Pyrazolopyridine derivative having GLP-1 receptor agonist effect
Hitoshi Yoshino, Shizuoka (JP); Satoshi Tsuchiya, Shizuoka (JP); Atsushi Matsuo, Shizuoka (JP); Tsutomu Sato, Shizuoka (JP); Masahiro Nishimoto, Shizuoka (JP); Kyoko Oguri, Shizuoka (JP); Hiroko Ogawa, Shizuoka (JP); Yoshikazu Nishimura, Shizuoka (JP); Yoshiyuki Furuta, Kanagawa (JP); Hirotaka Kashiwagi, Shizuoka (JP); Nobuyuki Hori, Shizuoka (JP); Takuma Kamon, Shizuoka (JP); Takuya Shiraishi, Shizuoka (JP); Shoshin Yoshida, Shizuoka (JP); Takahiro Kawai, Shizuoka (JP); Satoshi Tanida, Shizuoka (JP); and Masahide Aoki, Shizuoka (JP)
Assigned to CHUGAI SEIYAKU KABUSHIKI KAISHA, Tokyo (JP)
Filed by Chugai Seiyaku Kabushiki Kaisha, Tokyo (JP)
Filed on Feb. 22, 2024, as Appl. No. 18/584,177.
Application 18/584,177 is a continuation of application No. 18/448,497, filed on Aug. 11, 2023.
Application 18/448,497 is a continuation of application No. 17/065,122, filed on Oct. 7, 2020, granted, now 11,814,381, issued on Nov. 14, 2023.
Application 17/065,122 is a continuation of application No. 15/759,872, granted, now 10,858,356, issued on Dec. 8, 2020, previously published as PCT/JP2017/034620, filed on Sep. 26, 2017.
Claims priority of application No. 2016-187605 (JP), filed on Sep. 26, 2016.
Prior Publication US 2024/0262824 A1, Aug. 8, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01); A61K 31/437 (2006.01); A61K 31/444 (2006.01); A61K 31/4709 (2006.01); A61K 31/4725 (2006.01); A61K 31/496 (2006.01); A61K 31/506 (2006.01); A61K 31/5377 (2006.01); A61K 31/5386 (2006.01); A61P 1/16 (2006.01); A61P 3/04 (2006.01); A61P 3/06 (2006.01); A61P 3/10 (2006.01); A61P 9/10 (2006.01); A61P 9/12 (2006.01); A61P 25/16 (2006.01); A61P 25/28 (2006.01); C07D 519/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 31/437 (2013.01); A61K 31/444 (2013.01); A61K 31/4709 (2013.01); A61K 31/4725 (2013.01); A61K 31/496 (2013.01); A61K 31/506 (2013.01); A61K 31/5377 (2013.01); A61K 31/5386 (2013.01); A61P 1/16 (2018.01); A61P 3/04 (2018.01); A61P 3/06 (2018.01); A61P 3/10 (2018.01); A61P 9/10 (2018.01); A61P 25/16 (2018.01); A61P 25/28 (2018.01); C07D 519/00 (2013.01)] 11 Claims
 
1. A compound represented by Formula (I):

OG Complex Work Unit Chemistry
wherein:
X is —N═ or —CRa═; Ra is selected from a hydrogen atom and a halogen atom;
Y is selected from —C(═O)— and —CHR—; wherein R is a hydrogen atom or C1-6 alkyl;
R1 is selected from a hydrogen atom and C1-6 alkyl;
R2 is selected from a hydrogen atom and C1-6 alkyl;
R3 is selected from a hydrogen atom and C1-6 alkyl;
R4 is selected from a hydrogen atom and C1-6 alkyl;
R5 is selected from a hydrogen atom and C1-6 alkyl;
R6 is selected from a hydrogen atom and C1-6 alkyl;
R7 and R8 together with the carbon atom to which they are attached form a C3-15 cycloalkane ring, optionally substituted with 1 to 3 C1-6 alkyl;
R9 is selected from a group represented by Formula (IIa), (IIb), (IIc), and (IId):

OG Complex Work Unit Chemistry
R9a, R9b, R9c, R9d, and R9e are each independently selected from a hydrogen atom and C1-6 alkyl;
n1 is an integer of 0 to 3;
n2 is an integer of 0 to 5;
Q1 is C1-10 aryl, optionally substituted with 1 to 5 substituents independently selected from a halogen atom and C1-6 alkyl;
Q2 is a 3 to 12 membered heterocyclyl, optionally substituted with 1 to 3 substituents independently selected from a halogen atom and C1-6 alkyl;
Z1 is a group represented by Formula (IIIa);

OG Complex Work Unit Chemistry
and
Z2 is 5 to 10 membered heteroaryl, optionally substituted with 1 to 5 substituents independently selected from a halogen atom and C1-6 alkyl;
or a salt thereof.