US 12,065,430 B2
Indazole compound or salt thereof
Toshihiro Sakamoto, Ibaraki (JP); Hideki Kazuno, Ibaraki (JP); Tetsuya Sugimoto, Ibaraki (JP); Hitomi Kondo, Ibaraki (JP); and Tomohiro Yamamoto, Ibaraki (JP)
Assigned to TAIHO PHARMACEUTICAL CO., LTD., Tokyo (JP)
Appl. No. 17/288,780
Filed by TAIHO PHARMACEUTICAL CO., LTD., Tokyo (JP)
PCT Filed Oct. 25, 2019, PCT No. PCT/JP2019/041942
§ 371(c)(1), (2) Date Apr. 26, 2021,
PCT Pub. No. WO2020/085493, PCT Pub. Date Apr. 30, 2020.
Claims priority of application No. 2018-202226 (JP), filed on Oct. 26, 2018; and application No. 2019-075118 (JP), filed on Apr. 10, 2019.
Prior Publication US 2021/0395234 A1, Dec. 23, 2021
Int. Cl. C07D 403/14 (2006.01); A61K 9/00 (2006.01); A61K 45/06 (2006.01); A61P 35/00 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 403/14 (2013.01) [A61K 9/0053 (2013.01); A61K 45/06 (2013.01); A61P 35/00 (2018.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01); C07B 2200/05 (2013.01)] 27 Claims
 
1. An indazole compound represented by the following Formula (I) or a salt thereof:

OG Complex Work Unit Chemistry
wherein
X represents nitrogen or CH,
R1 represents hydrogen, halogen, cyano, nitro, amino, hydroxy, carboxy, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C4-C10 cycloalkyl, C6-C10 aromatic hydrocarbon, a 5- to 10-membered saturated heterocyclic group, or a 5- to 10-membered unsaturated heterocyclic group,
R2 represents hydrogen, cyano, nitro, amino, hydroxy, carboxy, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, C6-C10 aromatic hydrocarbon, a 5- to 10-membered saturated heterocyclic group, or a 5- to 10-membered unsaturated heterocyclic group,
L1 represents —NH—C(Ra)2-, wherein Ras are identical or different, and each represents a hydrogen atom, a deuterium atom, or C1-C6 alkyl,
ring A represents a substituted or unsubstituted 5-membered unsaturated heterocyclic group,
one of A1, A2, and A3 represents substituted or unsubstituted nitrogen or sulfur, and the rest of A1, A2, and A3 are identical or different, and represent substituted or unsubstituted carbon, substituted or unsubstituted nitrogen, sulfur, or oxygen, and
when A1 represents substituted carbon or substituted nitrogen, the substituent is at least one member selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, carboxy, C1-C6 alkyl that may have Rb, C2-C6 alkenyl that may have Rb, C2-C6 alkynyl that may have Rb, C3-C10 cycloalkyl that may have Rc, C4-C10 cycloalkenyl that may have Rc, C6-C10 aromatic hydrocarbon that may have Rc, a 4- to 10-membered saturated heterocyclic group that may have Rc, and a 5- to 10-membered unsaturated heterocyclic group that may have Rc,
wherein
Rb represents halogen, cyano, nitro, amino, hydroxy, carboxy, C1-C6 alkoxy, C1-C6 alkylamino, C3-C6 cycloalkyl, substituted or unsubstituted C6-C10 aromatic hydrocarbon, or a substituted or unsubstituted 5- to 10-membered saturated heterocyclic group, and
Re represents halogen, cyano, nitro, amino, hydroxy, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxy-C1-C6 alkyl, C7-C20 aralkyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C6-C10 aromatic hydrocarbon, a 5- to 10-membered saturated heterocyclic group, or a 5- to 10-membered unsaturated heterocyclic group, and
wherein when two or more Rbs are present, the plurality of Rbs may be identical or different, and when two or more Res are present, the plurality of Rcs may be identical or different,
when A2 represents substituted carbon or substituted nitrogen, the substituent is at least one member selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, carboxy, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, and substituted or unsubstituted C2-C6 alkynyl, and
when A3 represents substituted carbon or substituted nitrogen, the substituent is at least one member selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, carboxy, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, and substituted or unsubstituted C2-C6 alkynyl,
L2 represents

OG Complex Work Unit Chemistry
wherein

OG Complex Work Unit Chemistry
represent a 4- to 8-membered saturated heterocyclic group that contains at least one nitrogen atom, and that may contain 1 or 2 heteroatoms selected from sulfur and oxygen, in which N represents nitrogen,
R3 represents hydrogen or C1-C6 alkyl,
R4 represents halogen, cyano, nitro, amino, hydroxy, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 alkylamino-C1-C6 alkyl, cyano-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, or C1-C6 hydroxyalkyl, and wherein
when two or more R4s are present, the plurality of R4s may be identical or different,
when two R4s are attached to the same carbon atom, and these two R4s each represent C1-C6 alkyl, then these two R4s, taken together with the carbon atom to which these groups are attached, may form a ring, and
n represents 0, 1, 2, or 3,
L3 represents —C(═O)— or —S(═O)2—, and
R5 represents substituted or unsubstituted C2-C6 alkenyl or substituted or unsubstituted C2-C6 alkynyl.