# US 11,999,718 B2 · Pyrazole derivatives

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- Number: US 11,999,718 B2
- Document ID: US11999718B2
- Status: Granted
- Kind: B2
- Application number: 18/150,955
- Filed: 2023-01-06
- Published: 2023-07-27
- Granted: 2024-06-04
- Earliest claimed: 2021-02-25
- Assignees: Aptabio Therapeutics Inc.
- Applicants: Aptabio Therapeutics Inc.
- Inventors: Soo Jin Lee; Sung Hwan Moon; Sooho Ban; Eunsil Lee; Eun Jung Shin; Yoo-Kyung Goh
- Web page: https://patentgrep.com/patent/US11999718B2

## CPC

- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C07D 401/14: containing three or more hetero rings
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 39/06: Free radical scavengers or antioxidants
- C07D 231/54: condensed with carbocyclic rings or ring systems
- C07D 231/56: Benzopyrazoles; Hydrogenated benzopyrazoles
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The Present invention provides a novel pyrazole derivative compound represented by Chemical formula 1, a stereoisomer thereof, a solvate thereof, an isotopic variant thereof, a tautomer thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same. (In the above, A, B and R, and the like are the same as defined in the description of the invention.)

## Claims

### Claim 1

A compound of Chemical formula I below, or a stereoisomer thereof, a solvate thereof, an isotopic variant thereof, a tautomer thereof, or a pharmaceutically acceptable salt thereof:
in the formula,
A is a substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted C5-C20 aryl; and
then, the 5-membered to 20-membered heteroaryl or C6-C20 aryl of A are unsubstituted, or are substituted with 1, 2, 3 or 4 kinds of substituents consisting of cyano, halo, C1-C6 haloalkyl, nitro, —C(═O)R1, —C(═O)OR1, —NH—C(═O)R1, C1-C10 alkoxy group, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C5-C20 aryl, substituted or unsubstituted 5-membered to 20-membered heteroaryl and substituted or unsubstituted 5-membered to 20-membered heterocycloalkyl, and then, the R1 is hydrogen, heavy hydrogen, or C1-C10 alkyl,
two or more adjacent substituents of the 5-membered to 20-membered heteroaryl or C6-C20 aryl of A are combined with each other to form an unsubstituted 5-membered to 10-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C5-C10 aryl ring; and
R is hydrogen, heavy hydrogen, cyano, halo, nitro, C1-C6 haloalkyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C5-C20 aryl, substituted or unsubstituted 5-membered to 20-membered heteroaryl, or —C(═O)R2, and then, the R2 is C3-C8 cycloalkyl, C1-C10 alkyl, C2-C10 alkenyl, or C6-C10 aryl; and
B is -N(K)M or substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted 5-membered to 20-membered heterocycloalkyl; and
K is hydrogen, heavy hydrogen, cyano, halo, nitro, C1-C6 haloalkyl, substituted or unsubstituted C1-C10 alkyl, unsubstituted C1-C10 alkoxy, —C(═O)R′, —C(═O)OR′, —SO2—R″, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryl C1-C10 alkyl, substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted 5-membered to 20-membered heteroaryl C1-C10 alkyl;
M is cyano, halo, nitro, C1-C6 haloalkyl, substituted or unsubstituted C1-C10 alkyl, unsubstituted C1-C10 alkoxy, —C(═O)R′, —C(═O)OR′, —SO2-R″, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryl C1-C10 alkyl, substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted 5-membered to 20-membered heteroaryl C1-C10 alkyl;
wherein the C1-C10 alkyl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of substituents selected from the group consisting of heavy hydrogen, halo, hydroxy, cyano, nitro, carboxyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 haloalkyl, substituted or unsubstituted C1-C10 hydroxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsulfonyl, C5-C20 arylsulfonyl, C5-C20 aryloxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-membered to 20-membered heteroaryl and substituted or unsubstituted 5-membered to 20-membered heterocycloalkyl; and
the C3-C8 cycloalkyl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of substituents selected from the group consisting of heavy hydrogen, halogen, cyano, nitro, carboxyl, substituted or unsubstituted amino, substituted or unsubstituted C6-C20 aryl or 5-membered to 20-membered heteroaryl, C1-C10 alkoxy and C1-C10 haloalkyl; and
the 5-membered to 20-membered heteroaryl, 5-membered to 20-membered heterocycloalkyl, or C6-C20 aryl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of substituents selected from the group consisting of heavy hydrogen, halo, cyano, nitro, —C(═O)R′, —C(═O)OR′, —NH—C(═O)R″, substituted or unsubstituted amino, substituted or unsubstituted C1-C10 alkyl, unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 haloalkyl, substituted or unsubstituted C1-C10 hydroxyalkyl, substituted or unsubstituted C1-C10 alkylsulfonyl, substituted or unsubstituted C5-C20 arylsulfonyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 cycloalkyl C1-C10 alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 aryl C1-C10 alkyl, substituted or unsubstituted 5-membered to 12-membered heterocycloalkyl, substituted or unsubstituted C1-C10 alkyl C3-C8 cycloalkyl and substituted or unsubstituted C1-C10 alkyl 5-membered to 20-membered heterocycloalkyl, and
then, the R′ and R″ are each independently hydrogen, heavy hydrogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C3-Cg cycloalkyl, substituted or unsubstituted C6-C10 aryl or substituted or unsubstituted C6-C10 aryl C1-C6 alkyl, and then, the C2-C6 alkenyl or C2-C6 alkynyl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of mono C1-C6 alkylamine or di C1-C6 alkylamine; and
the substituted amino group is substituted with 1 kind or 2 kinds of C1-C10 alkyl, C6-C10 aryl or C6-C10 aryl C1-C6 alkyl groups; and
the heteroatom of the heterocycloalkyl or heteroaryl ring is one or more kinds selected from N, S and O.

### Claim 2 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the A is a unsubstituted, or substituted 5-membered to 12-membered heteroaryl or C6-C10 aryl, and then, the 5-membered to 12-membered heteroaryl or C6-C10 aryl of A is substituted with 1, 2, 3 or 4 kinds of substituents selected from the group consisting of cyano, halo, C1-C6 haloalkyl, nitro, —C(═O)R1, —C(═O)OR1, —NH—C(═O)R1, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, amino, C6-C10 aryl, 5-membered to 12-membered heteroaryl, and 5-membered to 12-membered heterocycloalkyl, and then the R1 is hydrogen, heavy hydrogen or C1-C6 alkyl; and
the two or more adjacent groups of the 5-membered to 12-membered heteroaryl or C6-C10 aryl of A are combined with each other to form an unsubstituted 5-membered to 7-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C6-C9 aryl ring.

### Claim 3 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the R is hydrogen, heavy hydrogen, cyano, halo, nitro, unsubstituted or C3-C6 cycloalkyl-substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C6-C10 aryl, 5-membered to 12-membered heteroaryl, —C(═O)R2, and then, the R2 is C3-C6 cycloalkyl, C1-C6 alkyl, C2-C6 alkenyl, or C6-C10 aryl.

### Claim 4 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the B is -N(K)M or 5-membered to 12-membered heteroaryl or 5-membered to 12-membered heterocycloalkyl, and then, the 5-membered to 12-membered heteroaryl or 5-membered to 12-membered heterocycloalkyl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of heavy hydrogen, halo, cyano, nitro, -NR3R4, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, —C(═O)R5, —SO2-R6, and
then, the C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryloxy, or unsubstituted or C1-C6 alkyl, C6-C10 aryl C1-C6 alkyl or C1-C6 alkylcarbonyl-substituted 4-membered to 12-membered heterocycloalkyl, and
the R3 and R4 are each independently hydrogen, heavy hydrogen, —C(═O)—Ra, C1-C6 alkyl or C6-C10 aryl, and the C1-C6 alkyl or C6-C10 aryl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of halo, hydroxy, C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryloxy, and then the Ra is hydrogen, heavy hydrogen, C1-C6 alkyl or C1-C6 haloalkyl; and
the R5 is —ORb, -NRcRa, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C8 cycloalkyl, and then, the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of mono C1-C6 alkylamine or di C1-C6 alkylamine, and then the Rb, Rc and Rd are each independently hydrogen, heavy hydrogen, C6-C10 aryl or C6-C10 aryl C1-C6 alkyl, and
the R6 is C1-C6 alkyl, unsubstituted or 1, 2, 3 or 4 kinds of C1-C6 alkyl-substituted C6-C10 aryl, and
the K is hydrogen, heavy hydrogen, cyano, halo, nitro, C1-C6 haloalkyl, C1-C6 alkyl, C1-C6 alkoxy, —C(═O)R′, —C(═O)OR′, —SO2-R″, C3-C8 cycloalkyl, C6-C10 aryl, C6-C10 aryl C1-C6 alkyl-, 5-membered to 12-membered heteroaryl, or 5-membered to 12-membered heteroaryl C1-C6 alkyl, and then the C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, C3-C8 cycloalkyl or 5-membered to 12-membered heteroaryl is substituted with 1, 2, 3 or 4 kinds of cyano, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C6-C10 arylsulfonyl, —C(═O)R9, 5-membered to 12-membered heterocyclyl, hydroxy, nitro, or C6-C10 aryl, and then, the 5-membered to 12-membered heterocyclyl or C6-C10 aryl is unsubstituted or substituted with C1-C6 alkyl,
the M is cyano, halo, nitro, C1-C6 haloalkyl, C1-C6 alkyl, C1-C6 alkoxy, —C(═O)R′, —C(═O)OR′, —SO2-R″, C3-C8 cycloalkyl, C6-C10 aryl, C6-C10 aryl C1-C6 alkyl-, 5-membered to 12-membered heteroaryl, or 5-membered to 12-membered heteroaryl C1-C6 alkyl, and then the C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, C3-C8 cycloalkyl or 5-membered to 12-membered heteroaryl is substituted with 1, 2, 3 or 4 kinds of cyano, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C6-C10 arylsulfonyl, —C(═O)R9, 5-membered to 12-membered heterocyclyl, hydroxy, nitro, or C6-C10 aryl, and then, the 5-membered to 12-membered heterocyclyl or C6-C10 aryl is unsubstituted or substituted with C1-C6 alkyl, and
then, the R′ and R″ are each independently hydrogen, heavy hydrogen, substituted or unsubstituted amino, C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, C3-C8 cycloalkyl, substituted or unsubstituted C6-C10 aryl or substituted or unsubstituted C6-C10 aryl C1-C6 alkyl, and then, the C2-C6 alkenyl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of mono C1-C6 alkylamine or di C1-C6 alkylamine, the C6-C10 aryl are substituted with C1-C10 alkyl;
the substituted amino group is substituted with 1 kind or 2 kinds of C1-C10 alkyl, C6-C10 aryl or C6-C10 aryl C1-C6 alkyl groups; and
the R9 is -ORe, -NReRf, unsubstituted or 1, 2, 3 or 4 kinds of -NReRf-substituted C2-C6 alkenyl, or C6-C10 aryl, and then, the Re and Rf are each independently hydrogen, heavy hydrogen, C1-C6 alkyl, C6-C10 aryl, or C1-C6 alkyl.

### Claim 5 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the compound of Chemical formula I is a compound of Chemical formula 1-1 below:
in the formula,
the definition of K, M and R is same as the Chemical formula I; and
D is CR10, N, O or S, or E is CR11, N, O or S, or F is CR12, N, O or S, or G is CR13, N, O or S, or J is CR14, N, O or S, but N, O and S are one or more; and
the R10 to R14 are same or different, and are each dependently substituted with 1, 2, 3 or 4 kinds of substituents consisting cyano, halo, C1-C6 haloalkyl, nitro, —C(═O) R1, —C(═O)OR1, —NH—C(═O)R1, C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-membered to 12-membered heteroaryl and substituted or unsubstituted 5-membered to 12-membered heterocycloalkyl, and then the R1 may be is hydrogen, heavy hydrogen, C1-C10alkyl; and
two or more adjacent groups among R10 to R14 are combined with each other to form an unsubstituted a 5-membered to 10-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C6-C10 aryl ring.

### Claim 6 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the compound of Chemical formula I is a compound of Chemical formula 1-2 below:
in the formula,
the definition of R is same as the Chemical formula I; and
D is CR10, N, O or S, or E is CR11, N, O or S, or F is CR12, N, O or S, or G is CR13, N, O or S, or J is CR14, N, O or S, but N, O and S are one or more; and
the R10 to R14 are same or different, and are each independently substituted with 1, 2, 3 or 4 kinds of substituents consisting of cyano, halo, C1-C6haloalkyl, nitro, —C(═O)R1, —C(═O)OR1, —NH—C(═O)R1, C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-membered to 12-membered heteroaryl and substituted or unsubstituted 5-membered to 12-membered heterocycloalkyl, and then the R1 is hydrogen, heavy hydrogen, or C1-C10 alkyl; and
two or more adjacent groups among R10 to R14 are combined with each other to form an unsubstituted 5-membered to 10-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C6-C10 aryl ring, and
n is an integer of 0, 1 or 2; and
L is CH2, NH or O; and
is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of heavy hydrogen, halo, cyano, nitro, -NR3R4, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, —C(═O)R5, -SO2-R6, and then, when the substituent is 2 kinds or more, two or more adjacent groups among said substituents are combined with each other to form a substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted 5-membered to 20-membered heterocycloalkyl with
and
then the C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryloxy, or unsubstituted or C1-C6 alkyl, C6-C10 aryl C1-C6 alkyl or C1-C6 alkylcarbonyl-substituted 4-membered to 12-membered heterocycloalkyl, and
the R3 and R4 are each independently hydrogen, heavy hydrogen, —C(═O)—Ra, C1-C6 alkyl or C6-C10 aryl, and the C1-C6 alkyl or C6-C10 aryl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of halo, hydroxy, C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryloxy, and then the Ra is hydrogen, heavy hydrogen, C1-C6 alkyl or C1-C6 haloalkyl; and
the R5 is —ORb, -NRcRd, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C8 cycloalkyl, and then, the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of mono C1-C6 alkylamine or di C1-C6 alkylamine, and the Rb, Rc and Ra are each independently hydrogen, heavy hydrogen, C6-C10 aryl or C6-C10 aryl C1-C6 alkyl, and
the R6 is C1-C6 alkyl, unsubstituted or 1, 2, 3 or 4 kinds of C1-C6 alkyl-substituted C6-C10 aryl.

### Claim 7 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the compound of Chemical formula I is a compound of Chemical formula 1-3 below:
in the formula,
the definition of K, M and R is same as the Chemical formula I; and
D is CR10, N, O or S, or E is CR11, N, O or S, or F is CR12, N, O or S, or G is CR13, N, O or S, but N, O and S are one or more; and
the R10 to R13 are same or different, and are each independently substituted with 1, 2, 3 or 4 kinds of substituents consisting of cyano, halo, C1-C6 haloalkyl, nitro, —C(═O)R1, —C(═O)OR1, —NH—C(═O)R1, C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-membered to 12-membered heteroaryl and substituted or unsubstituted 5-membered to 12-membered heterocycloalkyl, and then, the R1 is hydrogen, heavy hydrogen, C1-C10 alkyl; and
two or more adjacent groups among R10 to R13 are combined with each other to form an unsubstituted 5-membered to 10-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C6-C10 aryl ring.

### Claim 8 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the compound of Chemical formula I is a compound of Chemical formula I-4 below:
in the formula,
the definition of R is same as the Chemical formula I; and
D is CR10, N, O or S, or E is CR11, N, O or S, or F is CR12, N, O or S, or G is CR13, N, O or S, but N, O and S are one or more; and
the R10 to R13 are same or different, and are each independently substituted with 1, 2, 3 or 4 kinds of substituents consisting of cyano, halo, C1-C6haloalkyl, nitro, —C(═O)R1, —C(═O)OR1, —NH—C(═O)R1, C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C5-C20 aryl, substituted or unsubstituted 5-membered to 12-membered heteroaryl and substituted or unsubstituted 5-membered to 12-membered heterocycloalkyl, and then the R1 is hydrogen, heavy hydrogen, C1-C10 alkyl; and
two or more adjacent groups among R10 to R13 are combined with each other to form an unsubstituted 5-membered to 10-membered heteroaryl ring comprising 0, 1, 2 or 3 heteroatoms selected from N, O and S or a C6-C10 aryl ring, and
n is an integer of 0, 1 or 2; and
L is CH2, NH or O; and
is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of heavy hydrogen, halo, cyano, nitro, -NR3R4, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, —C(═O)R5, —SO2-R6, and then, when the substituent is 2 kinds or more, two or more adjacent groups among said substituents are combined with each other to form a substituted or unsubstituted 5-membered to 20-membered heteroaryl or substituted or unsubstituted 5-membered to 20-membered heterocycloalkyl with
and
then the C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryl is unsubstituted, or substituted with 1, 2, 3 or 4 kinds of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryloxy, or unsubstituted or C1-C6 alkyl, C6-C10 aryl C1-C6 alkyl or C1-C6 alkylcarbonyl-substituted 4-membered to 12-membered heterocycloalkyl, and
the R3 and R4 are each independently hydrogen, heavy hydrogen, —C(═O)—Ra, C1-C6 alkyl or C6-C10 aryl, and the C1-C6 alkyl or C6-C10 aryl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of halo, hydroxy, C1-C6 alkyl, C1-C6 alkoxy or C6-C10 aryloxy, and then the Ra is hydrogen, heavy hydrogen, C1-C6 alkyl or C1-C6 haloalkyl; and
the R5 is —ORb, -NRcRd, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cg cycloalkyl, and then, the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is unsubstituted or substituted with 1, 2, 3 or 4 kinds of mono C1-C6 alkylamine or di C1-C6 alkylamine, and then the Rb, Rc and Ra are each independently hydrogen, heavy hydrogen, C6-C10 aryl or C6-C10 aryl C1-C6 alkyl, and
the R6 is C1-C6 alkyl, unsubstituted or 1, 2, 3 or 4 kinds of C1-C6 alkyl-substituted C6-C10 aryl.

### Claim 9 (depends on 1)

The compound, or stereoisomer thereof, solvate thereof, isotopic variant thereof, tautomer, or pharmaceutically acceptable salt thereof according to claim 1,
wherein the compound represented by Chemical formula I is selected from the compounds 1) to 161) below:
1.5-(Benzylmethylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
2.5-(Benzylcyclopropylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
3.4-{[(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)methylamino]methyl}benzonitrile;
4.5-[(4-Fluorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
5.5-[(2,4-Difluorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
6) 5-[(2-Chlorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
7) 5-[(3-Chlorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
8) 5-[Methyl-(4-trifluoromethylbenzyl)amino]-2-pyridin-2-yl-4,5,6,7-tetrahydro-2H-indazol-3-ol;
9) 5-[Methyl-(3-methylbenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
10) 5-[Methyl-(3-trifluoromethylbenzyl)-amino]-2-pyridin-2-yl-4,5,6,7-tetrahydro-2H-indazol-3-ol;
11) 5-[Methyl-(2-trifluoromethylbenzyl)-amino]-2-pyridin-2-yl-4,5,6,7-tetrahydro-2H-indazol-3-ol;
12) 5-[(4-Methanesulfonylbenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
13) 5-[(3-Methoxybenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
14) 5-Piperidin-1-yl-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
15) 5-Morpholino-4-yl-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
16) 5-(4-Methylpiperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
17) 5-(4-(2-(2-Hydroxymethoxy)ethyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
18) 5-(3,4-Dihydro-1H-isoquinolin-2-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
19) 5-[(4-Chlorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
20) 5-(Benzylethylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
21) 5-(Benzylpropylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
22) 5-(Benzylbutylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
23) 5-[Methyl(3-methylsulfonylbenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
24) 5-[Methyl-(4-methylbenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
25) 3-{[(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)methylamino methyl}benzonitrile;
26) 5-[(2-Methoxybenzyl)-methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
27) 5-[(3-Fluorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
28) 5-[(4-Methoxybenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
29) 5-[Methyl-(2-methylbenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
30) 5-[(2,4-Dichlorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
31) 5-[(3,4-Dichlorobenzyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
32) 5-(3,4-Difluorophenylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
33) 5-[Methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
34) 5-(((3-(Hydroxymethyl)-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl)methyl)(methyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
35) 5-{[(3-(Hydroxymethyl)-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl)methyl]methylamino}-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
36) 5-{Methyl[3-methyl-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methylamino}-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
37) 5-{Methyl[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methylamino}-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
38) Cyclopropyl[4-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2-indazol-5-yl)piperazin-1-yl]methanone;
39) 5-(Benzylmethylamino)-2-(5-trifluoromethylpyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
40) 5-(Benzylmethylamino)-2-(5-chloropyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
41) 5-(Benzylmethylamino)-2-(6-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
42) 5-(Benzylmethylamino)-2-(6-methylpyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
43) 5-(Benzylmethylamino)-2-(3-fluoropyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
44) 6-(5-(Benzylmethylamino)-3-hydroxy-4,5,6,7-tetrahydro-2H-indazol-2-yl)nicotinonitrile;
45) 5-(Benzylmethylamino)-2-(6-methyl-4-trifluoromethylpyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
46) 5-(Benzylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
47) 2-(Pyridin-2-yl)-5-[(pyridin-2-ylmethyl)amino]-4,5,6,7-tetrahydro-2H-indazol-3-ol;
48) 5-[Methyl(pyridin-2-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
49) 5-[Methyl(pyridin-4-ylmethyl)amino]-2-(5-trifluoromethylpyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
50) 2-(5-Chloropyridin-2-yl)-5-[methyl(pyridin-4-ylmethyl)amino]-4,5,6,7-tetrahydro-2H-indazol-3-ol;
51) 5-[Methyl(pyridin-4-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
52) 2-(4-Bromophenyl)-5-[methyl(pyridin-4-ylmethyl)amino]-4,5,6,7,-tetrahydro-2H-indazol-3-ol;
53) 5-(Benzylmethylamino)-2-(thieno[3,2-c]pyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
54) 2-(6-Aminopyridin-2-yl)-5-(benzylmethylamino)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
55) 5-Phenylamino-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
56) 5-[(2,5-Dimethylphenyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
57) 5-[(4-Nitrophenyl) amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
58) 5-[(4-Methoxyphenyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
59) 5-(Phenylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
60) 2-(Pyridin-2-yl)-5-(quinolin-3-ylamino)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
61) 5-[Methyl(naphathalen-2-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
62) 5-[(Isoquinolin-3-ylmethyl)methylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
63) 5-[Methyl(quinolin-6-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
64) 5-[(Isoquinolin-3-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
65) 5-[Methyl(pyridin-2-ylmethyl)amino]-2-phenyl-4,5,6,7-tetrahydro-2H-indazol-3-ol;
66) 5-[Ethyl(pyridin-4-ylmethyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
67) 5-[(3-Dimethylaminobenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
68) 5-[(4-Dimethylaminobenzyl)amino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-2-ol;
69) 5-[(3-Dimethylaminobenzyl)methylamino)]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
70) 5-[(4-Dimethylamino)benzylmethylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
71) 5-[(2-Dimethylamino)benzylmethylamino]-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
72) 5-(Benzylmethylamino)-2-phenyl-4,5,6,7-tetrahydro-2H-indazol-3-ol;
73) 4-[(5-Benzylmethylamino)-3-hydroxy-4,5,6,7-tetrahydro-2H-indazol-2-yl]benzoic acid;
74) 5-(Benzylmethylamino)-2-(4-bromophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
75) 5-(Benzylmethylamino)-2-(2-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
76) 5-(Benzylmethylamino)-2-(2-methoxyphenyl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
77) 2-(2-Chlorophenyl)-5-[(3-dimethylaminobenzyl)methylamino]-4,5,6,7-tetrahydro-2H-indazol-3-ol;
78) 4-(((3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)(methyl)amino)methyl)bezoic acid;
79) 4-(((3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)(methyl)amino)methyl)benzamide;
80) 4-(((3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)(methyl)amino)methyl)-N-methylbenzamide;
81) 4-(((3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)(methyl)amino)methyl)-N,N-dimethylbenzamide;
82) 5-(4-Methylpiperazin-1-yl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
83) 2-(6-Chloropyridin-2-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
84) 2-(6-Methyl-4-(trifluoromethyl)pyridin-2-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
85) 5-(4-Methylpiperazin-1-yl)-2-(thieno[3,2-c]pyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
86) 2-(3-Fluoropyridin-2-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
87) 2-(Pyridin-2-yl)-5-(4-(pyridin-2-ylmethyl)piperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
88) 5-((4-Methoxybenzyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
89) 1-(4-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-yl)but-2-en-1-one;
90) 2-(Pyridin-2-yl)-5-(4-(quinolin-6-ylmethyl)piperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
91) 5-(4-Ethylpiperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
92) 5-(Phenylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
93) 5-(Penethylamino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
94) 2-(4-Chlorophenyl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
95) 5-(4-Methylpiperazin-1-yl)-2-(4-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
96) 2-(Pyridin-2-yl)-5-(pyrrolidin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
97) 1-(4-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-yl)prop-2-en-1-one;
98. (E)-4-(dimethylamino)-1-(4-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-yl)but-2-en-1-one;
99. (E)-4-(dimethylamino)-N-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)-N-methylbut-2-enamide;
100) 5-(4-Propylpiperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
101) 2-(4-Bromophenyl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
102) 2-(4-Fluorophenyl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
103) 4-(3-Hydroxy-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-2-yl)benzonitrile;
104) 5-(4-Penethylpiperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
105) 5-(4-Benzylpiperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
106) 5-(4-(Cyclohexylmethyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
107) 5-(4-(3-Phenylpropyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
108) 5-(4-Methylpiperazin-1-yl)-2-(pyrimidin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
109) 5-(Piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
110) 5-(4-(Methylsulfonyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
111) 5-(4-(Phenylsulfonyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
112) 2-(Pyridin-2-yl)-5-(4-tosylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
113) 4-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)-N-phenylpiperazin-1-carboxamide;
114. Benzyl 4-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-carboxylate;
115) 2-(1-Methyl-1 H-pyrrol-2-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
116) 5-(4-Methylpiperazin-1-yl)-2-(thiazol-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
117) 5-(4-Methylpiperazin-1-yl)-2-(oxazol-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
118) 2-(1-Methyl-1H-pyrazol-5-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
119) 2-(1-Methyl-1H-imidazol-5-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
120) 2-(1-Methyl-1H-imidazol-5-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
121) 5-(Benzyl(methyl)amino)-2-(pyrimidin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
122) 5-(Benzyl(methyl)amino)-2-(1-methyl-1H-pyrrol-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
123) 5-(Benzyl(methyl)amino)-2-(1-methyl-1H-pyrazol-5-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
124) 5-(Benzyl(methyl)amino)-2-(1-methyl-1H-imidazol-5-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
125) 5-(Benzyl(methyl)amino)-2-(oxazol-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
126) 2-(Pyridin-2-yl)-5-(4-(p-tolyl)piperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
127) 5-(4-(4-Hydroxyphenyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
128) 5-(4-(3,4-Difluorophenyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
129) 5-(4-(4-Methoxyphenyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
130) 1-(4-(4-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-yl)phenyl)ethan-1-one;
131) 5-(4-(4-(Methylsulfonyl)phenyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
132) 5-(4-(4-Phenoxyphenyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
133) 5-(4-(Piperidin-4-ylmethyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
134) 5-(4-((1-Methylpiperidin-4-yl)methyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
135) 5-(4-((1-Benzylpiperidin-4-yl)methyl)piperazin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
136) 1-(4-((4-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)piperazin-1-yl)methyl)piperidin-1-yl)ethan-1-one;
137. N-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)benzamide;
138. N-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)-2-phenylacetamide;
139) 1-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)-3-phenylurea;
140) 1-Benzyl-3-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)urea;
141. N-(3-Hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)benzenesulfonamide;
142. N-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)-4-methyl benzenesulfonamide;
143. Benzyl (3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)carbamate;
144) 2-(5-Fluoro-4-morpholinopyrimidin-2-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
145. N-benzyl-3-methoxy-N-methyl-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-amine;
146. N-benzyl-3-(cyclopropylmethoxy)-N-methyl-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-amine;
147) 5-(Benzyl(methyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-yl cyclopropane carboxylate;
148) 5-(Benzyl(methyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-yl acrylate;
149) 5-(Benzyl(methyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-yl benzoate;
150) 2-(5-(Benzyl(methyl)amino)-3-hydroxy-4,5,6,7-tetrahydro-2H-indazol-2-yl)pyrimidin-5-carboxylic acid;
151. Methyl 2-(5-(benzyl(methyl)amino)-3-hydroxy-4,5,6,7-tetrahydro-2H-indazol-2-yl)nicotinate;
152. N-(6-(5-(benzyl(methyl)amino)-3-hydroxy-4,5,6,7-tetrahydro-2H-indazol-2-yl)pyridin-2-yl)acetamide;
153) 5-(Benzyl(methyl)amino)-2-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
154) 5-(4-Methylpiperazin-1-yl)-2-(pyrimidin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
155) 2-(5-Chloropyridazin-3-yl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
156) 2-(Pyridin-2-yl)-5-(4-(pyrimidin-2-yl)piperazin-1-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
157) 5-(Benzyl(methyl)amino)-2-(5-nitropyrimidin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
158) 5-((4-Hydroxybenzyl)(methyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
159) 5-(Methyl(4-nitrobenzyl)amino)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol;
160) 5-(3-(Ethyl(methyl)amino)pyrrolidin-1-yl)-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-3-ol; and
161) 2,2,2-Trifluoro-N-(1-(3-hydroxy-2-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl)pyrrolidin-3-yl) acetamide.

### Claim 10 (depends on 1)

The compound or salt thereof according to claim 1, wherein the salt is in a form of a salt induced by one or more kinds of acids selected from the group consisting of hydrochloric acid, tartaric acid, hydrobromic acid, sulfuric acid, phosphoric acid, nitric acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid acid, mandelic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid and hydroiodic acid; sodium salt;
potassium salt; calcium salt; silver salt; hydrobromide; hydrogen sulfate; hydrogen phosphate; dihydrogen phosphate; succinate; citrate; mesylate or tosylate.

### Claim 11 (depends on 1, 9)

A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to any one claim of claim 1 to claim 9 and a pharmaceutically acceptable carrier as an active ingredient.

### Claim 12 (depends on 11)

The pharmaceutical composition according to claim 11, wherein the pharmaceutically acceptable carrier is one or more kinds selected from the group consisting of an excipient, a diluent, a disintegrating agent, a binding agent, a glydent, a surfactant, an emulsifier, a suspending agent and a diluent.