US 12,240,855 B2
Pyrrolopyrazole derivative
Hidenori Namiki, Tokyo (JP); Masanori Saitou, Tokyo (JP); Satoshi Matsui, Tokyo (JP); Yoshihiro Shibata, Tokyo (JP); Yoshito Kawamoto, Tokyo (JP); Rie Ichikawa, Tokyo (JP); Yohei Yoshihama, Tokyo (JP); and Akiko Otsuka, Tokyo (JP)
Assigned to DAIICHI SANKYO COMPANY, LIMITED, Tokyo (JP)
Appl. No. 17/436,500
Filed by DAIICHI SANKYO COMPANY, LIMITED, Tokyo (JP)
PCT Filed Mar. 5, 2020, PCT No. PCT/JP2020/009357
§ 371(c)(1), (2) Date Sep. 3, 2021,
PCT Pub. No. WO2020/179859, PCT Pub. Date Sep. 10, 2020.
Claims priority of application No. 2019-040649 (JP), filed on Mar. 6, 2019.
Prior Publication US 2022/0185815 A1, Jun. 16, 2022
Int. Cl. C07D 487/04 (2006.01); A61K 31/4162 (2006.01); A61K 31/423 (2006.01); A61K 31/427 (2006.01); A61P 35/00 (2006.01); A61P 43/00 (2006.01)
CPC C07D 487/04 (2013.01) [C07B 2200/13 (2013.01)] 20 Claims
 
1. A compound represented by general formula (1) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein
R1 represents a halogeno C1-6 alkyl group, a C3-8 cycloalkyl group, or a 5- or 6-membered aromatic heterocyclic group,
ring Q1 represents any one of formulas (2A) to (2C):

OG Complex Work Unit Chemistry
wherein
* represents a bond,
X represents an oxygen atom, a sulfur atom, or —NH—,
R2 represents a hydrogen atom, a halogen atom, or a phenoxy group, and
R3 represents a C1-6 alkanoyl group,
ring Q2 represents a phenylene group which may have 1 or 2 substituents independently selected from substituent group 1, a 6-membered aromatic heterocyclic group which may have 1 or 2 substituents independently selected from substituent group 1, a 5-membered aromatic heterocyclic group which may have a substituent selected from substituent group 1, or a 9-membered bicyclic aromatic heterocyclic group which may have a substituent selected from substituent group 1,
W is any one substituent selected from substituent group 1, or represents formula (3A):

OG Complex Work Unit Chemistry
wherein
* represents a bond,
Y represents an oxygen atom, a single bond, a sulfur atom, —NH—, *—O—R4—**: (wherein * is bonded to ring Q2 and ** is bonded to ring Q3), a C1-6 alkylene group, a C1-6 alkoxy C1-6 alkylene group, or a halogeno C1-6 alkylene group,
R4 represents a C1-6 alkylene group, and
ring Q3 represents a phenyl group which may have 1 to 3 substituents independently selected from substituent group 2, a 6-membered aromatic heterocyclic group which may have 1 or 2 substituents independently selected from substituent group 2, a 5-membered aromatic heterocyclic group which may have 1 or 2 substituents independently selected from substituent group 2, a 3- to 8-membered saturated hydrocarbon ring group which may have 1 or 2 substituents independently selected from substituent group 2, a 6-membered saturated heterocyclic group which may have 1 or 2 substituents independently selected from substituent group 2, a 9-membered bicyclic aromatic heterocyclic group which may have a substituent selected from substituent group 2, or a 10-membered bicyclic partially unsaturated heterocyclic group which may have 1 to 4 substituents independently selected from substituent group 2;
substituent group 1 represents a group consisting of a halogen atom, a C1-6 alkyl group, a halogeno C1-6 alkyl group, a halogeno C1-6 alkoxy group, and a C3-8 cycloalkyl group; and
substituent group 2 represents a group consisting of a halogen atom, a C1-6 alkyl group, a halogeno C1-6 alkyl group, a halogeno C1-6 alkoxy group, a halogeno C1-6 alkylsulfanyl group, and a halogeno C1-6 alkylsulfonyl group;
wherein the compound represented by formula (1):

OG Complex Work Unit Chemistry
wherein R1, Q1, Q2, and W are as defined above,
may include its tautomer, a compound represented by formula (1′):

OG Complex Work Unit Chemistry
wherein R1, Q1, Q2, and W are as defined above,
in any ratio, and
the ratio of the compound represented by formula (1) may be 100%, or the ratio of the compound represented by formula (1′) may be 100%.