Indazole compound or salt thereof

1. An indazole compound represented by the following Formula (I) or a salt thereof:

wherein

X represents nitrogen or CH,

R 1 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,

R 2 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,

L 1 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,

L 2 represents

wherein

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,

R 3 represents hydrogen or C1-C6 alkyl,

R 4 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 R 4 s are present, the plurality of R 4 s may be identical or different,

when two R 4 s are attached to the same carbon atom, and these two R 4 s each represent C1-C6 alkyl, then these two R 4 s, taken together with the carbon atom to which these groups are attached, may form a ring, and

n represents 0, 1, 2, or 3,

L 3 represents —C(═O)— or —S(═O) 2 —, and

R 5 represents substituted or unsubstituted C2-C6 alkenyl or substituted or unsubstituted C2-C6 alkynyl.

2. The compound or a salt thereof according to claim 1 , wherein R 1 represents hydrogen, halogen, or substituted or unsubstituted C1-C6 alkyl.

3. The compound or a salt thereof according to claim 1 , wherein R 2 represents substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, or substituted or unsubstituted C3-C10 cycloalkyl.

4. The compound or a salt thereof according to claim 1 , wherein two of A1, A2, and A3 are identical or different, and represent substituted or unsubstituted nitrogen or sulfur, and the other one represents substituted or unsubstituted carbon.

5. The compound or a salt thereof according to claim 1 , wherein A1 represents substituted carbon or substituted nitrogen, and the substituent is at least one member selected from the group consisting of hydrogen, halogen, C1-C6 alkyl that may have Rb, C2-C6 alkenyl that may have Rb, C3-C10 cycloalkyl that may have Rc, C4-C10 cycloalkenyl that may have Rc, a 5- 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 and Rc are as defined above.

6. The compound or a salt thereof according to claim 1 , wherein the substituent of A3 is at least one member selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, and C1-C6 haloalkyl.

7. The compound or a salt thereof according to claim 1 , wherein L 2 represents

wherein

represent a 4- to 6-membered saturated heterocyclic group containing 1 or 2 nitrogen atoms as heteroatoms, in which N represents nitrogen,

R 3 represents hydrogen or methyl, and

R 4 represents halogen, cyano, hydroxy, C1-C3 alkyl, methoxy, C1-C3 haloalkyl, dimethylaminomethyl, or ethoxymethyl, and

when two or more R 4 s are present, the plurality of R 4 s may be identical or different, and

n represents 0, 1, or 2.

8. The compound or a salt thereof according to claim 1 , wherein L 3 is —C(═O)—.

9. The compound or a salt thereof according to claim 1 , wherein R 5 represents vinyl or 1-propynyl.

10. The compound or a salt thereof according to claim 1 , wherein R 5 represents vinyl.

11. The compound or a salt thereof according to claim 1 , wherein X is CH.

12. The compound or a salt thereof according to claim 1 , wherein L 1 represents —NH—CH 2 —.

13. The compound or a salt thereof according to claim 2 , wherein R 1 represents chlorine.

14. The compound or a salt thereof according to claim 1 , wherein R 2 represents C1-C6 alkyl.

15. The compound or a salt thereof according to claim 1 , wherein R 2 represents tert-butyl.

16. The compound or a salt thereof according to claim 4 , wherein

A1 represents substituted or unsubstituted nitrogen,

A2 represents substituted or unsubstituted nitrogen, and

A3 represents substituted or unsubstituted carbon.

17. The compound or a salt thereof according to claim 7 , wherein L 2 represents

wherein

represents a 4- to 5-membered saturated heterocyclic group containing one nitrogen atom as a heteroatom, in which N represents nitrogen,

R 3 represents hydrogen,

R 4 represents halogen, C1-C2 alkyl, or methoxy, and

when two or more R 4 s are present, the plurality of R 4 s may be identical or different, and

n represents 0, 1, or 2.

18. The compound or a salt thereof according to claim 1 , wherein the compound is selected from the following group of compounds:

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-1,4-dimethyl-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-1-isopropyl-4-methyl-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-methyl-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-(difluoromethyl)-1-isopropyl-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-isopropyl-1H-imidazole-5-carboxamide;

N-((3S,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-1,4-dimethyl-1H-imidazole-5-carboxamide;

N-((3S,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-fluoro-1-methyl-1H-imidazole-5-carboxamide;

N-((3S,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-methyl-1H-imidazole-5-carboxamide;

N-((3R,4R)-1-acryloyl-4-methylpyrrolidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-methyl-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-(difluoromethyl)-1-(1-isopropylpyrrolidin-3-yl)-1H-imidazole-5-carboxamide;

(S)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(tetrahydrofuran-3-yl)-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-5-carboxamide;

(R)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(tetrahydrofuran-3-yl)-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-methylpiperidin-4-yl)-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(tetrahydro-2H-pyran-3-yl)-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-cyclopentyl-1H-imidazole-5-carboxamide;

tert-butyl 3-(5-((1-acryloylazetidin-3-yl)carbamoyl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1H-imidazol-1-yl)azetidine-1-carboxylate;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-isopropylazetidin-3-yl)-1H-imidazole-5-carboxamide;

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(4-methoxycyclohexyl)-1H-imidazole-5-carboxamide;

(R)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-(2,2-difluoroethyl)pyrrolidin-3-yl)-1H-imidazole-5-carboxamide;

(R)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-isopropylpyrrolidin-3-yl)-1H-imidazole-5-carboxamide;

(S)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-(2,2-difluoroethyl)pyrrolidin-3-yl)-1H-imidazole-5-carboxamide;

(R)—N-(1-acryloylazetidin-3-yl)-1-(1-allylpyrrolidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1H-imidazole-5-carboxamide;

(R)—N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-(1-(pyridin-2-yl)pyrrolidin-3-yl)-1H-imidazole-5-carboxamide; and

N-(1-acryloylazetidin-3-yl)-2-(((5-(tert-butyl)-6-chloro-1H-indazol-3-yl)amino)methyl)-4-chloro-1-((3R,5R)-1-(2,2-difluoroethyl)-5-methylpyrrolidin-3-yl)-1H-imidazole-5-carboxamide.

19. A pharmaceutical preparation comprising the compound or a salt thereof of claim 1 .

20. A pharmaceutical composition comprising the compound or a salt thereof of claim 1 , and a pharmaceutically acceptable carrier.

21. An antitumor agent comprising the compound or a salt thereof of claim 1 as an active ingredient.

22. An antitumor agent for oral administration comprising the compound or a salt thereof of claim 1 as an active ingredient.

23. A commercial package comprising the compound or a salt thereof of claim 1 as an active ingredient and instructions for use of the compound or a salt thereof in the treatment of a tumor in a subject.

24. A method for treating a tumor, the method comprising administering the compound or a salt thereof of claim 1 in an effective amount to a subject in need.

25. An antitumor agent comprising the compound or a salt thereof of claim 1 , and one or more other antitumor agents, as active ingredients.

26. An antitumor agent comprising the compound or a salt thereof of claim 1 as an active ingredient, wherein the agent is for administration in combination with one or more other antitumor agents.

27. A method for treating a tumor, the method comprising administering an effective amount of the compound or a salt thereof of claim 1 , and an effective amount of one or more other antitumor agents to a subject in need.