Heteroaromatic and heterobicyclic compound acting as pkmyt1 inhibitor and use thereof

Abstract

Provided in the present invention are a heteroaromatic and heterobicyclic compound acting as a PKMYT1 inhibitor and the use thereof. Specifically, provided in the present invention are a compound of formula I, and a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or a pharmaceutically acceptable salt thereof, or a mixture thereof, wherein each group in the formula is as described herein. The compound of the present invention is a PKMYT1 kinase inhibitor, which can treat or prevent diseases or conditions caused by PKMYT1 activity abnormality, or is used for preparing a drug for treating or preventing diseases or conditions caused by PKMYT1 activity abnormality.

Description

Heteroaromatic and heterobicyclic compounds as PKMYT1 inhibitors and their applications Technical Field

[0001] The present invention relates to heteroaromatic and heterobicyclic compounds as PKMYT1 inhibitors and their uses. Background Art

[0002] Accurate and complete DNA replication is crucial for cell survival and division. In order to ensure that DNA replication is completed accurately, multiple cell cycle checkpoints monitor the entire process of DNA replication in real time during cell division (Zeman MK et al., Nature cell biology, 2014, 16(1): 2-9; Barnum KJ et al., Cell cycle control: mechanisms and protocols, 2014: 29-40). Mammalian cell cycle checkpoints rely on cell cycle kinase (CDKs) family proteins for regulation (Malumbres M et al., Nature reviews cancer, 2009, 9(3): 153-166). The WEE1 family kinase is an important component of the cell cycle G2 / M checkpoint, which controls the progression of the cell cycle G2 phase to the mitotic phase by regulating the activity of downstream CDK1. WEE1 is mainly distributed in the cell nucleus and maintains a relatively high concentration. It prevents cells from entering mitosis by phosphorylating CDK1. Protein kinase membrane associated tyrosine / threonine 1 (PKMYT1 / MYT1) belongs to the WEE1 kinase family, which inhibits PKMYT1 by regulating the activity of CDK1 and CDK2 through phosphorylation, resulting in the activation of CDK1 and causing cells to enter mitosis. This allows tumor cells carrying DNA mutations and chromosomal instability to enter mitosis directly and eventually die (Ghelli Luserna di Rorà A et al., Journal of Hematology & Oncology, 2020, 13 (1): 1-17). In addition, inhibiting PKMYT1 is an effective strategy for treating CCNE1 amplified cancers (Gallo D, Young JTF et al., Nature, 2022, 604 (7907): 749-756).

[0003] Studies have shown that PKMYT1 is overexpressed to varying degrees in a variety of cancer cells and has a significant impact on tumor growth (Shao C et al., Translational Lung Cancer Research, 2021, 10(12): 4600). The PKMYT1 gene is expected to become a new drug target for the treatment of these tumors.

[0004] In recent years, a variety of PKMYT1 inhibitors have been reported and disclosed, such as WO2021195781, WO2023155870, WO2023155871, WO2023155892, WO2023174329, WO2023174397, WO2023177356, WO2023198199, WO2023220831, WO2024012409, WO2024061343, CN117510503 and WO2024084450. Among them, Lunresertib (RP6306) is a first-in-class selective PKMYT1 inhibitor that has a selective killing effect on CCNE1-amplified tumor cells and can inhibit tumor growth in CCNE1-amplified xenograft models (David G et al., Nature, 2022, 604(7907): 749-756). In addition, PKMYT1 inhibitors can be combined with other targeted drugs, including ATR inhibitors and WEE1 inhibitors. For example, at the AACR-NCI-EORTC International Conference on Molecular Targets and Cancer Therapy in October 2023, preclinical data on the combination of Lunresertib with ATR inhibitors and WEE1 inhibitors were reported, showing encouraging synergistic effects and efficacy of Lunrsertib + ATR inhibitors and Lunsertib + WEE1 inhibitors. Lunresertib is currently undergoing multiple clinical trials, including monotherapy and combination with ATR inhibitors, as well as combination with chemotherapy for the treatment of solid tumors. The results of the first-in-human Phase I clinical trial showed preliminary monotherapy anti-tumor activity of Lunresertib, and its combination with the ATR inhibitor Camonsertib (RP3500) showed higher anti-tumor activity than monotherapy (ClinicalTrials.gov ID: NCT04855656). Summary of the Invention

[0005] The present invention provides compounds represented by formula I, formula II (including formula IIa, IIb, IIc, IId, IIe, IIf, IIg and IIh) and formula III (including formula IIIa and IIIb), which can be used as PKMYT1 inhibitors.

[0006] The present invention also provides a pharmaceutical composition comprising an effective amount of a compound of Formula I, Formula II (including Formula IIa, IIb, IIc, IId, IIe, IIf and IIh) or Formula III (including Formula IIIa and IIIb), which can be used to treat cancer.

[0007] In one embodiment, the pharmaceutical composition may further contain one or more pharmaceutically acceptable carriers or diluents.

[0008] In one embodiment, the pharmaceutical composition may further contain at least one known anticancer drug or a pharmaceutically acceptable salt of the anticancer drug.

[0009] The present invention also relates to methods for preparing compounds of Formula I, Formula II (including Formula IIa, IIb, IIc, IId, IIe, IIf and IIh) and Formula III (including Formula IIIa and IIIb). DETAILED DESCRIPTION

[0010] It should be understood that the features of the various embodiments described herein can be arbitrarily combined to form the technical solutions of this invention; the definition of each group herein is applicable to any embodiment described herein, for example, the definition of the substituent of the alkyl group herein is applicable to any embodiment described herein, unless the embodiment has clearly defined the substituent of the alkyl group.

[0011] As used herein, "hydrogen (H)" includes its isotopes deuterium (D) and tritium (T).

[0012] The heteroatoms described herein include oxygen (O), sulfur (S) and nitrogen (N).

[0013] As used herein, "alkyl" refers to a straight or branched chain group containing up to ten carbon atoms. The number of carbon atoms in an alkyl group can be 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, or within a range formed by any two of the above values. Useful alkyl groups include straight or branched chain C 1-10 Alkyl, preferably C 1-6 In certain embodiments, the alkyl group is C 1-4 Alkyl. Typical C 1-10 Alkyl groups include optionally substituted methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, 3-pentyl, hexyl and octyl groups.

[0014] As used herein, "alkenyl" refers to a straight or branched chain containing 2 to 10 carbon atoms, unless the carbon chain length is otherwise limited, wherein at least one double bond is present between two carbon atoms in the chain. The number of carbon atoms in an alkenyl group can be 2, 3, 4, 5, 6, 7, 8, 9 or 10, or within the range formed by any two of the above values. Alkenyl is preferably C 2-6Typical alkenyl groups include ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl and 2-butenyl.

[0015] As used herein, "alkynyl" refers to a straight or branched chain containing 2 to 10 carbon atoms, unless the carbon chain length is otherwise limited, wherein at least one of the carbon atoms in the chain contains a triple bond. The number of carbon atoms in an alkynyl group can be 2, 3, 4, 5, 6, 7, 8, 9 or 10, or within the range formed by any two of the above values. Alkynyl is preferably C 2-6 Typical alkynyl groups include ethynyl, 1-propynyl, 1-methyl-2-propynyl, 2-propynyl, 1-butynyl, and 2-butynyl.

[0016] As used herein, "alkoxy" refers to an oxy group substituted with an alkyl group as described herein. Preferred alkoxy groups are C 1-6 Alkoxy or C 1-4 Alkoxy. Exemplary alkoxy groups include methoxy, ethoxy, etc. The alkyl group in the alkoxy group may be optionally substituted. Substituents of the alkoxy group include, but are not limited to, halogen, amino, and carboxyl (including ester groups thereof), wherein the amino group includes alkylamino and dialkylamino.

[0017] The "amino group" herein may be represented by -NR'R", wherein R' and R" are each independently hydrogen, optionally substituted C 1-10 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, preferably, R' and R" are each independently H, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 cycloalkyl or an optionally substituted 5-membered heteroaryl; or R′ and R″ together with the N to which they are attached form an optionally substituted nitrogen-containing heterocyclic group or nitrogen-containing heteroaryl, such as a 4- to 7-membered nitrogen-containing heterocyclic group or nitrogen-containing heteroaryl, wherein the nitrogen-containing heterocyclic group or nitrogen-containing heteroaryl optionally contains one or more (such as 2, 3) additional heteroatoms selected from O, N and S. Preferred amino groups include —NH2, —NHR′ and —NHR″, wherein R′ and R″ are each independently an optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 cycloalkyl and optionally substituted 3- to 6-membered heterocyclic groups.

[0018] As used herein, "oxo" refers to =0.

[0019] As used herein, "aryl" refers to an aromatic group, by itself or as part of another group, a monocyclic, bicyclic, or tricyclic aromatic group containing 6 to 14 carbon atoms. Aryl groups may be substituted with one or more substituents as described herein.

[0020] Useful aryl groups include C6-14 Aryl, preferably C 6-10 Aryl. Typical C 6-14 Aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, indenyl, azulenyl, biphenyl, biphenylene, and fluorenyl.

[0021] As used herein, "carbocyclic group" includes cycloalkyl and partially saturated carbocyclic groups. Useful cycloalkyl groups are C3-8 cycloalkyl groups, such as C 3-6 Cycloalkyl or C 3-4 Cycloalkyl. Typical cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Useful partially saturated carbocyclic groups include cycloalkenyl, such as C 3-8 Cycloalkenyl, C 3-6 Cycloalkenyl or C 3-4 Cycloalkenyl groups, such as cyclopentenyl, cycloheptenyl, and cyclooctenyl. Carbocyclic groups may be substituted with one or more substituents as described herein.

[0022] Useful halogens or halogen groups include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0023] An acyl group is a functional group containing a carbonyl group (carbon-oxygen double bond) and can be represented by RC(O)-, where R is an alkyl group as described herein. Useful acyl groups include C 1-6 Acyl, or C 1-3 Acyl, such as acetyl. The acyl group may be optionally substituted by a group selected from halogen, amino and aryl, wherein amino and aryl may be optionally substituted. When substituted by halogen, the number of halogen substituents may be in the range of 1-5. Examples of acyl substituted by halogen include chloroacetyl and pentafluorobenzoyl, etc. When substituted by amino, the amino group may be substituted by one or two substituents described herein. In some embodiments, aminoacyl is -C(O)-NR'R", wherein R' and R" are each independently hydrogen, optionally substituted C 1-10 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, preferably, R' and R" are each independently H, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 cycloalkyl and optionally substituted 3- to 6-membered heterocyclic group.

[0024] Herein, acylamino is -NH- substituted with an acyl group, which can be represented by RC(O)-NH-, wherein R is an alkyl group as described herein. Exemplary acylamino groups include acylamino groups where R is methyl, ethyl, propyl, tert-butyl, and the like.

[0025] Herein, sulfonyl refers to RS(=O)2-, wherein R can be, for example, an alkyl group as described herein. 1-4 Sulfonyl refers to R is C1-4 Alkyl sulfonyl group.

[0026] As used herein, "heteroaryl" refers to a group containing 5 to 14, preferably 5 to 10, ring atoms, with 6, 10, or 14 pi electrons shared throughout the ring system. The ring atoms of a heteroaryl group are carbon atoms and 13 heteroatoms selected from oxygen, nitrogen, and sulfur. A heteroaryl group may be substituted with one or more substituents described herein.

[0027] Useful heteroaryl groups include thienyl (phenylthio), benzo[d]isothiazol-3-yl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thianthrenyl, furanyl, pyranyl, isobenzofuranyl, chromenyl, xanthrenyl, phenoxanthiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl (including but not limited to 2-pyridyl, 3-pyridyl and 4-pyridyl), pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, 3H-indolyl, indolyl, indazolyl, purinyl, 4H-quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, azathiophene, benzophenone ... pyridinyl, perylene diazaphenyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, phenoxazinyl, tetrahydropyridopyrimidinyl, tetrahydrofive-membered [c]pyrazol-3-yl, benzisoxazolyl such as 1,2-benzisoxazol-3-yl, benzimidazolyl, 2-hydroxyindolyl, thiadiazide, 2-oxobenzimidazolyl, imidazopyridazinyl, imidazopyridinyl, triazolopyridazinyl, tetrahydropyridopyrimidinyl, pyrazolopyrimidinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, pyrrolopyrazinyl, triazolopyrazinyl, thienoquinolyl, furanoquinolyl, thiazoquinolyl, pyrazoloquinolyl, pyrroloquinolyl, imidazoquinolyl, oxazoloquinolyl, etc. When the heteroaryl group contains a nitrogen atom in a ring, such nitrogen atom may be in the form of an N-oxide, such as pyridyl N-oxide, pyrazinyl N-oxide and pyrimidinyl N-oxide.

[0028] As used herein, "heterocyclyl" refers to a saturated or partially saturated 3-7 membered monocyclic group, a 7-10 membered bicyclic group, an 11-14 membered tricyclic group, a spirocyclic group, or a bridged cyclic group, which is composed of carbon atoms and 1-4 heteroatoms selected from O, N, and S. In some embodiments, the heteroatoms nitrogen and sulfur in the heterocyclyl may be oxidized, and the nitrogen may be quaternized. The heterocyclyl also includes a fused heterocycle formed by condensing any of the heterocycles defined above with a benzene ring in the bicyclic system. If the resulting compound is stable, the carbon atoms or nitrogen atoms of the heterocycle may be substituted. The heterocyclyl may be substituted with one or more substituents described herein.

[0029] Useful saturated or partially saturated heterocyclic groups include tetrahydrofuranyl, pyranyl, piperidinyl, piperazinyl, 1,4-diazepanyl, azetidinyl, oxetanyl, pyrrolidinyl, imidazolidinyl, imidazolinyl, indolinyl, isoindolinyl, quinuclidinyl, morpholinyl, isochromanyl, chromanyl, pyrazolidinyl, pyrazolinyl, tetrahydroisoquinolinyl, dihydropyrrolopyrazolyl, tetronoyl, and tetramoyl, which may be substituted with one or more substituents as described herein.

[0030] As used herein, unless otherwise indicated, when substituted, the alkyl, alkenyl, alkynyl, alkoxy, amino, acyl, carbocyclyl, aryl, heterocyclyl, and heteroaryl groups described in any embodiment herein may each be substituted with one or more (e.g., 1, 2, 3, 4, or 5) substituents selected from the group consisting of halogen, hydroxy, carboxyl, amino, nitro, cyano, C 1-6 Acylamino, C 1-6 Alkoxy, C 1-6 Alkyl, C 1-6 Acyl, C 6-10 Aryl, C 3-8 Cycloalkyl, heteroaryl, heterocyclic and carbonyl etc. wherein the substituent itself can also be optionally substituted. More preferred substituents include but are not limited to halogen, hydroxyl, cyano, amino, C 1-6 Alkoxy, C 1-6 Alkyl, -NR'R" and C 1-6 acyl group.

[0031] It should be understood that in each embodiment herein, when the substituent is a carbocyclyl, heterocyclyl, aryl or heteroaryl group, the number of the carbocyclyl, heterocyclyl, aryl or heteroaryl group as a substituent is generally one.

[0032] Specifically, the present invention provides a compound represented by the following formula I, its stereoisomers, tautomers, N-oxides, hydrates, solvates, isotope-labeled compounds or pharmaceutically acceptable salts, or mixtures thereof: wherein A0, A1 and A2 are each independently C or N; R1 is an optionally substituted aryl or an optionally substituted heteroaryl; R5 is hydrogen, halogen, cyano, hydroxyl, an optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or -NR 5a R 5b ; Among them, R 5a and R 5b are each independently hydrogen, optionally substituted C 1-6 Alkyl or optionally substituted C 3-8 Cycloalkyl; R6 is -C(O)NR 6a R 6b , -SO2R6c or -C(O)R 6d ; Among them, R 6a and R 6b are each independently hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, or R 6a and R 6b Together with the attached N, it forms an optionally substituted heterocyclic group; R 6c is optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted aryl or -NR 6a R 6b ; R 6d is optionally substituted C 1-6 Alkyl, optionally substituted C 2-6 Alkenyl or optionally substituted C 2-6 R7, R8 and R9 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 2-6 Alkenyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 3-8 R7 and R8, together with the connected A1 and A0, form an optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl; or R8 and R9, together with the connected A0 and A2, form an optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl.

[0033] It should be understood that each structural formula and each group defined herein satisfies the bond valence theory. For example, when one of R7, R8 or R9 is a ═O group, the corresponding A0, A1 or A2 should be C.

[0034] In Formula I and various structural formulas of the present invention, when each alkyl, alkoxy, or acyl group in the definitions of the various groups is substituted, the substituents may be independently selected from cyano, hydroxyl, nitro, amino (-NR'R"), aryl, heteroaryl, and halogen, and the number of substituents may be independently 1, 2, 3, 4, or 5. R' and R" are as defined herein, and are preferably each independently H or C 1-4Alkyl. For example, the substituted alkyl group can be a hydroxyalkyl, dihydroxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, arylalkyl, heteroarylalkyl, and haloalkyl. It should be understood that when the substituent is an aryl, heteroaryl, cyano, and nitro group, the number of substituents is generally 1; when the substituent is, for example, a halogen, the number of substituents can be up to 5 halogen groups depending on the carbon chain length of the alkyl and alkoxy groups; exemplary substituents of this type include trifluoromethyl and pentafluoroethyl. In some embodiments, in Formula I and various structural formulas described herein, each alkyl, alkoxy, and acyl group in the definitions of the various groups is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from hydroxy, nitro, amino, and halogen.

[0035] In the formula I and various structural formulas of the present invention, when each cycloalkyl, heterocyclic, aryl and heteroaryl in the group definition is substituted, the number of substituents can be 1, 2, 3, 4 or 5 independently, and each substituent can be independently selected from halogen, hydroxyl, carboxyl, amino, nitro, cyano, C 1-6 Acylamino, C 1-6 Alkoxy, C 1-6 Alkyl, C 1-6 Acyl, C 6-10 Aryl, C 3-8 Cycloalkyl, heteroaryl, heterocyclyl and carbonyl, preferably selected from halogen, hydroxy, cyano, amino, C 1-6 Alkoxy, C 1-6 Alkyl and C 1-6 Acyl. 1-6 Acylamino, C 1-6 Alkoxy, C 1-6 Alkyl, C 1-6 Each acyl group may also be optionally substituted with 1, 2, 3, 4 or 5 substituents selected from cyano, hydroxy, nitro, amino, aryl, heteroaryl and halogen. 6-10 Aryl, C 3-8 Cycloalkyl, heteroaryl, heterocyclyl may also be optionally substituted by 1, 2, 3, 4 or 5 groups selected from halogen, hydroxy, carboxyl, amino, nitro, cyano, C 1-6 Acylamino, C 1-6 Alkoxy, C 1-6 Alkyl, C 1-6 The acyl and carbonyl groups are substituted with substituents.

[0036] In one or more embodiments of the compound of Formula I, A0, A1 and A2 are all C, or one of them is N and the remaining two are C. In one or more embodiments, A0 is N, and A1 and A2 are all C. In one or more embodiments, A1 is N, A0 is C, and A2 is C. In one or more embodiments, A1 is C, A0 is C, and A2 is N.

[0037] In one or more embodiments of the compound of formula I, R1 is an optionally substituted 6-14 membered aryl, such as phenyl; or an optionally substituted 5-10 membered heteroaryl, preferably a nitrogen-containing heteroaryl, such as pyridyl or indazolyl.

[0038] In one or more embodiments of the compound of formula I, R1 is replaced by 1, 2, 3, 4 or 5 groups selected from hydroxy, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 In some embodiments, when R1 is an aryl group, such as a phenyl group, it is substituted with at least one hydroxyl group or one C 1-6 In some embodiments, the heteroaryl group described in R1 is a bicyclic heteroaryl group, preferably containing at least one nitrogen atom among the heteroatoms. In some embodiments, the heteroaryl group is a 5- or 6-membered heteroaryl group or a 9-membered fused bicyclic heteroaryl group.

[0039] In one or more embodiments of the compound of formula I, R1 is: Where W is N or CR w ; Z1 and Z2 are each independently N or CR w , and at least one of Z1 and Z2 is N; n is 0, 1 or 2; R w , R2 and R3 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; each R4 is independently halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; * indicates the position where R1 is attached to the rest of the compound of formula I. Preferably, the optionally substituted C 1-6 Alkyl and optionally substituted C 1-6 Each alkoxy group may be independently substituted with 1, 2 or 3 substituents selected from halogen and deuterium; the optionally substituted C 3-8 The alkyl group may be optionally substituted by 1, 2 or 3 groups selected from halogen and C 1- 4 alkyl substituents are substituted.

[0040] In one or more embodiments of the compound of formula I, W is N. In one or more embodiments, W is CR w , R w For hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8Cycloalkyl; preferably hydrogen, halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 More preferably, W is hydrogen, halogen, methyl or deuterated methyl. In some embodiments, W is CH.

[0041] In one or more embodiments of the compound of formula I, Z1 is N and Z2 is CH. In some embodiments, Z1 is CH and Z2 is N.

[0042] In one or more embodiments of the compound of formula I, R2 and R3 are each independently hydrogen, halogen, C 1- 6-alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 In some embodiments, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 Cycloalkyl, preferably hydrogen, chlorine, methyl, deuterated methyl or cyclopropyl. In some embodiments, R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 The cycloalkyl group is preferably methyl, deuterated methyl, bromine, chlorine or cyclopropyl.

[0043] In one or more embodiments of the compound of formula I, n is 0 or 1.

[0044] In one or more embodiments of the compound of formula I, each R4 is independently halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 Alkyl; more preferably each independently hydrogen, methyl, deuterated methyl, chlorine or fluorine.

[0045] In one or more embodiments of the compound of formula I, R1 is: Wherein, R2, R3 and R4 are as described in any of the above embodiments; preferably, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably hydrogen, methyl, deuterated methyl or chlorine; R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably methyl, deuterated methyl, bromine or chlorine; R4 is halogen.

[0046] In one or more embodiments of the compound of formula I, R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0047] In one or more embodiments of the compound of formula I, R5 is hydrogen, halogen, cyano, halo 1-3 Alkyl or -NR 5a R 5b ; Preferably, R5 is -NR 5a R 5b Preferably, R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0048] In one or more embodiments of the compound of formula I, R6a and R 6b Each independently is an optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclic, optionally substituted aryl or optionally substituted heteroaryl, said C 1-6 The alkyl group is optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxyl and aryl, heteroaryl or heterocyclic groups as described in any embodiment of the present invention; preferably, the C 1-6 The alkyl group is optionally substituted by 1 heteroaryl group; preferably, the heteroaryl group is a 5-6 membered heteroaryl group containing 1 or 2 nitrogen atoms; preferably, the aryl, heteroaryl or heterocyclic group is optionally substituted by 1, 2 or 3 groups selected from halogen, C 1-4 The alkyl and hydroxy groups are substituted. 3-8 Cycloalkyl, heterocyclyl, aryl and heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, C 1-4 The alkyl and hydroxy groups are substituted with substituents.

[0049] In one or more embodiments of the compound of formula I, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 In some embodiments, R 6a and R 6b Together with the attached N, it forms a 5-10 membered heterocyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxy and optionally substituted C 1-4 In some preferred embodiments, R 6a and R 6b Together with the attached N, it forms a 9-10 heterobicyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally 1, 2 or 3 selected from halogen, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl and hydroxy substituted C 1-4 The alkyl group is substituted with a substituent.

[0050] In one or more embodiments of the compound of formula I, R6 is -C(O)NR 6a R 6b , R 6a and R 6b As described in any of the above embodiments; preferably, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 cycloalkyl, more preferably all hydrogen; in some embodiments, R 6a and R 6b Together with the attached N, it forms an optionally substituted heterocyclyl as described herein. In a preferred embodiment, R6 is -C(O)NH2.

[0051] In one or more embodiments of the compound of formula I, the optionally substituted C 3- 8 cycloalkyl, optionally substituted C 3-8 The cycloalkenyl, optionally substituted heterocyclyl, optionally substituted aryl and optionally substituted heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, cyano, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 In some embodiments, R7, R8 and R9 are each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C 2-4 Alkenyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkenyl, 4-10 membered heterocyclic group, C 6-14 Aryl, 5-10 membered heteroaryl or =O, the C 3-6 Cycloalkyl, C 3-6 Cycloalkenyl, 4-10 membered heterocyclic group, C 6-14 Aryl and 5-10 membered heteroaryl are each optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy and halogenated C 1-4 The substituents of the alkoxy group are substituted.

[0052] In one or more embodiments of the compound of formula I, A0 is N, R7 or R9 is =O, R8 is an optionally substituted 4-10 membered heterocyclyl, an optionally substituted C 6-14 Preferably, the optionally substituted 4-10 membered heterocyclic group, the optionally substituted C 6-14 The aryl and optionally substituted 5-10 membered heteroaryl groups may each be optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, cyano, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4Preferably, the 5-10 membered heteroaryl group is a 5- or 6-membered heteroaryl group, and preferably the heteroatoms contained therein include at least a nitrogen atom, such as pyridyl, thiazolyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl and pyridazinyl. Preferably, the 4-10 membered heterocyclic group is a 4-6 membered heterocyclic group, and preferably the heteroatoms contained therein include at least a nitrogen atom, such as azetidinyl, pyrrolidinyl, imidazolidinyl and morpholinyl.

[0053] In one or more embodiments of the compound of formula I, R7 and R8 together with the attached A1 and A0 form an optionally substituted 5-6 membered heterocyclyl, an optionally substituted 6 membered aryl or an optionally substituted 5-6 membered heteroaryl; A2 is C, and R9 is as described in any of the above embodiments, preferably hydrogen or =O. Preferably, each of the 5-6 membered heterocyclyl, 6 membered aryl and 5-6 membered heteroaryl can be optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C1-4 alkyl (such as halo C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, -CONR'R" substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 Alkyl, wherein R' and R" are each independently H or C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, optionally substituted 5-10-membered heteroaryl-O-; preferably, the optionally substituted C 3-6 The cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl and optionally substituted 5-10-membered heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxy, C1-4 Alkyl, halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, and 5-6 membered heterocyclic (preferably nitrogen-containing heterocyclic) substituents, preferably each optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, C 1-4 Alkoxy and halogenated C 1-4 More preferably, the 5-6 membered heterocyclic group, 6 membered aryl group and 5-6 membered heteroaryl group formed together with the connected A1 and A0 are unsubstituted, or may be optionally substituted with 1, 2 or 3 groups selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl substituted C 1-4 Alkyl, C 3-6 Cycloalkyl, halogenated C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 The present invention is substituted by a substituent selected from the group consisting of an alkyl, an optionally substituted phenyl, an optionally substituted 5-6 membered heterocyclic group, and an optionally substituted 5-10 membered heteroaryl. Preferably, the heteroatoms in the 5-6 membered heterocyclic group and the 5-6 membered heteroaryl formed together with the connected A1 and A0 include at least one nitrogen atom, and optionally further contain one or two heteroatoms selected from N, S, and O; preferably, the heteroaryl includes but is not limited to imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, indazolyl, pyridyl, benzothiazolyl, and pyrimidinyl, and the heterocyclic group includes but is not limited to pyrrolidinyl, imidazolidinyl, morpholinyl, piperidinyl, and piperazinyl; further preferably, A0 is the at least one nitrogen atom. In some embodiments, the 5-6 membered heterocyclic group as a substituent includes but is not limited to azetidinyl, pyrrolidinyl, imidazolidinyl, morpholinyl, piperidinyl and piperazinyl, etc.; the 5-10 membered heteroaryl as a substituent includes but is not limited to imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, indazolyl, pyridinyl, benzothiazolyl and pyrimidinyl, etc.

[0054] In some embodiments, R7 and R8 together with the attached A1 and A0 form an optionally substituted 5-membered heteroaryl; A2 is C, R9 is hydrogen; the 5-membered heteroaryl may be optionally substituted with 1 or 2 optionally substituted C 1-4 Alkyl, optionally substituted C 3-6The substituents of cycloalkyl, optionally substituted 6-membered aryl and optionally substituted 5-10 membered heteroaryl are substituted. In some embodiments, A0 is N, R7 and R8 together with the connected A1 and A0 form the aforementioned optionally substituted 5-6 membered heterocyclyl or the optionally substituted 5-6 membered heteroaryl, except the N on the A0 position, the 5-6 membered heterocyclyl and the 5-6 membered heteroaryl may also contain 1, 2 or 3 heteroatoms selected from O, N and S; preferably, A0 is N, A1 is C, R7 and R8 together with the connected A1 and A0 form the aforementioned optionally substituted 5-membered heteroaryl, except the N on the A0 position, the 5-6 membered heteroaryl may also contain 1, 2 or 3 heteroatoms selected from N. In some embodiments, A0 and A1 are both C, and R7 and R8 together with the linked A0 and A1 form an optionally substituted 5-membered heteroaryl as described above, which contains 1, 2 or 3 heteroatoms selected from O, N and S.

[0055] In one or more embodiments of the compound of formula I, the heteroaromatic ring or heterobicyclic ring formed by A0, A1, A2, R7 and R8 is: Among them, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; R 13 is hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted aryl or optionally substituted 5-6 membered heteroaryl, preferably C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 3-4 Cycloalkyl or optionally 1-2 selected C 1-3 The heteroaromatic ring or heterobicyclic ring may be optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 Preferably, the heteroaryl or heterobicyclic ring may be optionally substituted with 1, 2 or 3 halogens, optionally substituted C 1-4 Alkyl, optionally substituted C 1-4 Alkoxy, optionally substituted C 3-6 More preferably, the heteroaryl or heterobicyclic ring may be optionally 1, 2, 3 or 4 selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 In some embodiments, the 5-6 membered heterocyclic group as a substituent includes but is not limited to azetidinyl, pyrrolidinyl, imidazolidinyl, morpholinyl, piperidinyl and piperazinyl; the 5-10 membered heteroaryl as a substituent includes but is not limited to imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, indazolyl, pyridinyl, benzothiazolyl and pyrimidinyl.

[0056] In one or more embodiments of the compound of formula I, R8 and R9 together with the attached A0 and A2 form an optionally substituted 5-6 membered heterocyclyl, an optionally substituted 6 membered aryl, or an optionally substituted 5-6 membered heteroaryl; A1 is C, and R7 is as described in any of the above embodiments, preferably hydrogen or =O. Preferably, the 5-6 membered heterocyclyl, 6 membered aryl, and 5-6 membered heteroaryl may be optionally substituted by 1, 2, or 3 groups selected from halogen, hydroxy, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 More preferably, the 5-6 membered heterocyclyl, 6 membered aryl and 5-6 membered heteroaryl are unsubstituted or may be optionally substituted with 1, 2 or 3 groups selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 alkyl and optionally substituted 5-10 membered heteroaryl. Preferably, the heteroatoms in the 5-6 membered heterocyclic group and 5-6 membered heteroaryl formed by R8 and R9 together with the connected A0 and A2 include at least one nitrogen atom, and optionally further contain one or two heteroatoms selected from N, S and O; preferably, the heteroaryl includes but is not limited to imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, indazolyl, pyridyl, benzothiazolyl and pyrimidinyl, and the heterocyclic group includes but is not limited to pyrrolidinyl, imidazolidinyl, morpholinyl, piperidinyl and piperazinyl; further preferably, A0 is the at least one nitrogen atom. In some embodiments, the 5-6 membered heterocyclic group as a substituent includes but is not limited to azetidinyl, pyrrolidinyl, imidazolidinyl, morpholinyl, piperidinyl and piperazinyl, etc.; the 5-10 membered heteroaryl as a substituent includes but is not limited to imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, indazolyl, pyridinyl, benzothiazolyl and pyrimidinyl, etc.

[0057] In some embodiments, R8 and R9 together with the linked A0 and A2 form an optionally substituted 5-membered heteroaryl; A1 is C, R7 is hydrogen; the 5-membered heteroaryl may be optionally substituted with 1 or 2 members selected from optionally substituted C 1-4 Alkyl, optionally substituted C 3-6Preferably, A0 is N, R8 and R9 together with the connected A0 and A2 form the above-mentioned optionally substituted 5-6 membered heterocyclic group, optionally substituted 5-6 membered heteroaryl, except for the N at the A0 position, the 5-6 membered heterocyclic group and the 5-6 membered heteroaryl may further contain 1, 2 or 3 heteroatoms selected from O, N and S; preferably, A0 is N, A2 is C, R8 and R9 together with the connected A0 and A2 form the above-mentioned optionally substituted 5-membered heteroaryl, except for the N at the A0 position, the 5-6 membered heteroaryl may further contain 1, 2 or 3 heteroatoms selected from N. In some embodiments, A0 and A2 are both C, and R8 and R9 together with the linked A0 and A2 form an optionally substituted 5-membered heteroaryl as described above, which contains 1, 2 or 3 heteroatoms selected from O, N and S.

[0058] In one or more embodiments of the compound of formula I, the heteroaromatic ring or heterobicyclic ring formed by A0, A1, A2, R8 and R9 is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively. The heteroaromatic ring or heterobicyclic ring may be optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6Preferably, the 5-6 membered heterocyclyl, 6 membered aryl and 5-6 membered heteroaryl may be optionally substituted by 1, 2 or 3 substituents selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 The substituents of the alkyl group and the optionally substituted 5- to 10-membered heteroaryl group are substituted.

[0059] One group of preferred compounds of formula I of the present invention is represented by compounds represented by formula II (including formula IIa, IIb, IIc, IId, IIe and IIf) or stereoisomers, tautomers, N-oxides, hydrates, solvates, isotope-labeled compounds or pharmaceutically acceptable salts thereof, or mixtures thereof: wherein R1, R5, R6, R7 and R9 are each as described in any embodiment of Formula I; A3, A4, A5, A6, A7, A8, D1, D2, D3, D4, B1, B2 and B3 are each independently CR 10 , CR 11 R 12 NR 13 , N, O or S; R 1o is hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or =O; R 11 and R 12 are independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl; R 13 is hydrogen, optionally substituted C 1-6 Alkyl or optionally substituted C 3-8 Cycloalkyl.

[0060] In one or more embodiments of the compound of formula II, R1 is an optionally substituted 6-14 membered aryl, such as phenyl; or an optionally substituted 5-10 membered heteroaryl, preferably a nitrogen-containing heteroaryl, such as pyridyl or indazolyl. In some embodiments, R1 is replaced by 1, 2, 3, 4 or 5 groups selected from hydroxy, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8In some embodiments, when R1 is an aryl group, such as a phenyl group, it is substituted with at least one hydroxyl group or one C 1-6 In some embodiments, the heteroaryl group described in R1 is a bicyclic heteroaryl group, preferably containing at least one nitrogen atom among the heteroatoms. In some embodiments, the heteroaryl group is a 5- or 6-membered heteroaryl group or a 9-membered benzo-fused bicyclic heteroaryl group.

[0061] In one or more embodiments of the compound of formula II, R1 is: Where W is N or CR w ; Z1 and Z2 are each independently N or CR w , and at least one of Z1 and Z2 is N; n is 0, 1 or 2; R w , R2 and R3 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; each R4 is independently halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; * indicates the position where R1 is attached to the rest of the compound of formula I. Preferably, the optionally substituted C 1-6 Alkyl and optionally substituted C 1-6 Each alkoxy group may be independently substituted with 1, 2 or 3 substituents selected from halogen and deuterium; the optionally substituted C 3-8 The alkyl group may be optionally substituted by 1, 2 or 3 groups selected from halogen and C 1- 4 alkyl substituents are substituted.

[0062] In one or more embodiments of the compound of formula II, W is N. In one or more embodiments, W is CR w , R w For hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably hydrogen, halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 More preferably, W is hydrogen, halogen, methyl or deuterated methyl. In some embodiments, W is CH.

[0063] In one or more embodiments of the compound of formula II, Z1 is N and Z2 is CH. In some embodiments, Z1 is CH and Z2 is N.

[0064] In one or more embodiments of the compound of formula II, R2 and R3 are each independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 In some embodiments, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 Cycloalkyl, preferably hydrogen, chlorine, methyl, deuterated methyl or cyclopropyl. In some embodiments, R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 The cycloalkyl group is preferably methyl, deuterated methyl, bromine, chlorine or cyclopropyl.

[0065] In one or more embodiments of the compound of Formula II, n is 0 or 1.

[0066] In one or more embodiments of the compound of formula II, each R4 is independently halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3Alkyl or deuterated C 1-3 Alkyl; more preferably each independently hydrogen, methyl, deuterated methyl, chlorine or fluorine.

[0067] In one or more embodiments of the compound of formula II, R1 is: Wherein, R2, R3 and R4 are as described in any of the above embodiments; preferably, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably hydrogen, methyl, deuterated methyl or chlorine; R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably methyl, deuterated methyl, bromine or chlorine; R4 is halogen.

[0068] In one or more embodiments of the compound of Formula II, R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0069] In one or more embodiments of the compound of formula II, R5 is hydrogen, halogen, cyano, halo 1-3 Alkyl or -NR 5a R 5b ; Preferably, R5 is -NR 5a R 5b Preferably, R 5a and R 3b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0070] In one or more embodiments of the compound of Formula II, R 6a and R 6b Each independently is an optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclic, optionally substituted aryl or optionally substituted heteroaryl, said C 1-6 The alkyl group is optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxyl and aryl, heteroaryl or heterocyclic groups as described in any embodiment of the present invention; preferably, the C 1-6The alkyl group is optionally substituted by 1 heteroaryl group; preferably, the heteroaryl group is a 5-6 membered heteroaryl group containing 1 or 2 nitrogen atoms; preferably, the aryl, heteroaryl or heterocyclic group is optionally substituted by 1, 2 or 3 groups selected from halogen, C 1-4 The alkyl and hydroxy groups are substituted. 3-8 Cycloalkyl, heterocyclyl, aryl and heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, C 1-4 The alkyl and hydroxy groups are substituted with substituents.

[0071] In one or more embodiments of the compound of Formula II, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 In some embodiments, R 6a and R 6b Together with the attached N, it forms a 5-10 membered heterocyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxy and optionally substituted C 1-4 In some preferred embodiments, R 6a and R 6b Together with the attached N, it forms a 9-10 heterobicyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally 1, 2 or 3 selected from halogen, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl and hydroxy substituted C 1-4 The alkyl group is substituted with a substituent.

[0072] In one or more embodiments of the compound of formula II, R6 is -C(O)NR 6a R 6b , R 6a and R 6b As described in any of the above embodiments; preferably, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 cycloalkyl, more preferably all hydrogen; in some embodiments, R 6a and R 6b Together with the attached N, it forms an optionally substituted heterocyclyl as described herein. In a preferred embodiment, R6 is -C(O)NH2.

[0073] In one or more embodiments of the compound of Formula II, R 10 is hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 In some embodiments, R 10 For hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 3-8 Cycloalkyl substituted C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl. 3-8 Cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl and optionally substituted 5-10 membered heteroaryl are each optionally substituted by 1 or 2 members selected from halogen, C 1-4 Alkyl, C 1-4 Alkoxy and optionally substituted (e.g., optionally with 1, 2 or 3 groups selected from halogen and C 1-4 alkyl) is substituted by a substituent of a 4-7 membered heterocyclic group; preferably, the optionally substituted C 3-8 Cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl and optionally substituted 5-10 membered heteroaryl are each optionally substituted by 1 or 2 members selected from halogen and C 1-4 In some embodiments, the 6-14 membered aryl group is a phenyl group; preferably, the 5-10 membered heteroaryl group is selected from imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, indazolyl, pyridinyl and pyrimidinyl; preferably, the 4-7 membered heterocyclic group is a nitrogen-containing heterocyclic group, preferably an azetidinyl, pyrrolidinyl, morpholinyl, piperidinyl or piperazinyl.

[0074] In one or more embodiments of the compound of Formula II, R 11 and R 12 Each is independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl or halogenated C 1-4 Preferably, R 11 and R 12 For hydrogen.

[0075] In one or more embodiments of the compound of Formula II, R13 is hydrogen, optionally substituted C 1-4 Alkyl, halogenated C 1-4 Alkyl, optionally substituted C 3-6 alkyl, optionally substituted 6-membered aryl or optionally substituted 5-10-membered heteroaryl, preferably hydrogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C substituted by 5-membered heteroaryl 1-4 Alkyl, C 3-6 alkyl or an optionally substituted 5-6 membered heteroaryl.

[0076] In one or more embodiments of the compound of formula II, A3, A4 and A5 are each independently CR 10 , CR 11 R 12 NR 13 , N, O or S. In some embodiments, A3, A4 and A5 are each independently CR 10 or N.

[0077] In one or more embodiments of the compounds of Formula IIa and IId, the heteroaromatic bicyclic ring formed by A3, A4, A5 and the pyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively. The heteroaromatic bicyclic ring may be optionally substituted, and its substituents may be as described in any of the above embodiments (such as paragraph 0053 herein). In some embodiments, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, -CONR'R" substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 Alkyl, wherein R' and R" are each independently H or C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 Preferably, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2 or 3 substituents selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 The substituents of the alkyl group and the optionally substituted 5- to 10-membered heteroaryl group are substituted.

[0078] In one or more embodiments of the compounds of Formula IIb and IIe, the heteroaromatic ring or heterobicyclic ring formed by A3, A4, A5 and the oxopyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively. The heteroaromatic ring or heterobicyclic ring may be optionally substituted with 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halo C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 Preferably, the heteroaryl ring or heterobicyclic ring may be optionally substituted with 1, 2 or 3 substituents selected from C 1-4 Alkyl, halogenated C1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 More preferably, the heteroaromatic bicyclic ring may optionally have 1, 2, 3 or 4 C 1-4 Alkyl substitution.

[0079] In one or more embodiments of the compound of Formula II, D1, D2, D3 and D4 are each independently CR 10 , CR 11 R 12 NR 13 , N or O.

[0080] In one or more embodiments of the compounds of Formula IIc and IIf, the heteroaromatic ring or heterobicyclic ring formed by D1, D2, D3, D4 and the oxopyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively. The heteroaromatic ring or heterobicyclic ring may be optionally substituted with 1, 2 or 3 groups selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 Preferably, the heteroaryl ring or heterobicyclic ring may be optionally substituted with 1, 2 or 3 substituents selected from halogen, C 1-6 Alkyl, C 1-6 Alkoxy and C 2-6 More preferably, the heteroaromatic bicyclic ring may optionally have 1, 2 or 3 C 1-4 Alkyl substitution.

[0081] In one or more embodiments of the compound of formula IIg, B1, B2 and B3 are each independently N or CR 10 , where each R 10 are independently hydrogen, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclic group or optionally substituted 5-10-membered heteroaryl, preferably C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 In one or more embodiments, B1 and B3 are each independently N or CH, and B2 is CR 10 , where R 10 is optionally substituted C 1-4Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclic group or optionally substituted 5-10-membered heteroaryl, preferably C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 alkyl or an optionally substituted 5-6 membered heteroaryl.

[0082] In one or more embodiments of the compound represented by formula IIg, the heteroaromatic bicyclic ring formed by B1, B2, B3 and the pyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively. The heteroaromatic bicyclic ring may be optionally substituted with 1, 2 or 3 groups selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 Preferably, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2 or 3 substituents selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 substituted by a cycloalkyl, an optionally substituted 6-membered aryl, an optionally substituted 5-6-membered heterocyclyl, and an optionally substituted 5-10-membered heteroaryl; more preferably, the heteroaromatic bicyclic ring may be optionally 1, 2, 3 or 4 selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 The substituents are substituted by alkyl, optionally substituted 6-membered aryl, or optionally substituted 5- to 6-membered heteroaryl.

[0083] In one or more embodiments of the compound of formula IIh, B1, B2 and B3 are each independently N, O, S, CR 10 or NR 13 , where each R 10 are independently hydrogen, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclic group or optionally substituted 5-10-membered heteroaryl, preferably C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 alkyl or optionally substituted 5-6 membered heteroaryl; each R 13 are independently hydrogen, optionally substituted C 1-4 Alkyl, optionally substituted C3-6 alkyl, optionally substituted 6-membered aryl or optionally substituted 5-10-membered heteroaryl, preferably hydrogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C substituted by 5-membered heteroaryl 1-4 Alkyl, C 3-6 In one or more embodiments, B1 and B3 are each independently N, O, S, CH or NH, and B2 is CR 10 , where R 10 is hydrogen, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclic group or optionally substituted 5-10-membered heteroaryl, preferably C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 In one or more embodiments, B1 is N, B3 is CH, B2 is NR 13 , where R 13 is hydrogen, optionally substituted C 1-4 Alkyl, optionally substituted C 3-6 alkyl, optionally substituted 6-membered aryl or optionally substituted 5-10-membered heteroaryl, preferably hydrogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C substituted by 5-membered heteroaryl 1-4 Alkyl, C 3-6 5-6 membered heteroaryl optionally substituted by alkyl.

[0084] In one or more embodiments of the compound represented by Formula IIh, the heteroaromatic bicyclic ring formed by B1, B2, B3 and the benzene ring is: Among them, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; R 13 is hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted aryl or optionally substituted 5-6 membered heteroaryl, preferably C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 3-4 Cycloalkyl or optionally 1-2 selected C 1-3 The heteroaromatic bicyclic ring may be optionally substituted with 1, 2, 3 or 4 groups selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8Preferably, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2, 3 or 4 substituents selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 substituted by a cycloalkyl, an optionally substituted 6-membered aryl, an optionally substituted 5-6-membered heterocyclyl, and an optionally substituted 5-10-membered heteroaryl; more preferably, the heteroaromatic bicyclic ring may be optionally 1, 2, 3 or 4 selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 The substituents are substituted by alkyl, optionally substituted 6-membered aryl, or optionally substituted 5- to 6-membered heteroaryl.

[0085] One group of preferred compounds of formula I of the present invention represents a compound represented by formula IIa or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt thereof, or a mixture thereof: Where: R1 is: Where R2 is C 1-4 Alkyl, preferably methyl or ethyl; R3 is C 1-4 Alkyl, halogen, C 3-6 Cycloalkyl or halogenated C 1- 4 alkyl, preferably C 1-4 Alkyl, such as methyl or ethyl; n is 0 or 1; R4 is H, C 1-4 Alkyl or halogen, preferably halogen; Z1 and Z2 are each independently N or CH, and at least one of Z1 and Z2 is N; R5 is -NR 5a R 5b , where R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably each independently hydrogen or C 1-3 Alkyl, more preferably all hydrogen; R6 is -C(O)NR 6a R 6b , where R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl, C 3-8 Cycloalkyl, optionally substituted 5 or 6 membered heteroaryl substituted C 1-6 alkyl or optionally substituted 5-10 membered heteroaryl, preferably each independently hydrogen, C 1-6 Alkyl or C 3-8 cycloalkyl, more preferably each independently hydrogen or C 1-3alkyl, more preferably all hydrogen; preferably, the optionally substituted 5 or 6 membered heteroaryl is optionally substituted by 1 or 2 groups selected from halogen and C 1-4 A 5- or 6-membered nitrogen-containing heteroaryl group substituted with an alkyl substituent; R9 is hydrogen; A3 is N or CR 10 ; A4 is N or CR 10 ; A5 is N or CR 10 , and at least one of A3, A4 and A5 is N; R 10 are independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, R 10 Each is independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, NR'R"CO-substituted C 1-4 Alkyl, C 3-6 Cycloalkyl substituted C 1-4 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 Cycloalkyl, halogenated C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl, wherein R' and R" are each independently H or C 1-4 Alkyl; More preferably, R 10 Each is independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, the optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl is optionally substituted by 1 or 2 selected from halogen, C 1-4 Alkyl, C 1-4 The substituents of the alkoxy group and the optionally substituted 4-7 membered heterocyclic group are substituted; preferably, the 6-14 membered aryl group is phenyl; preferably, the 5-10 membered heteroaryl group is selected from imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, indazolyl, pyridinyl and pyrimidinyl; preferably, the 4-7 membered heterocyclic group is a nitrogen-containing heterocyclic group, preferably azetidinyl, pyrrolidinyl, morpholinyl, piperidinyl and piperazinyl.

[0086] One group of preferred compounds of formula I of the present invention represents a compound represented by formula IIa or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt thereof, or a mixture thereof: Where: R1 is: Wherein, W is N; R2 is hydrogen or C 1-4 Alkyl, preferably hydrogen; R3 is hydrogen or C 1-4 Alkyl, preferably hydrogen; n is 0 or 1; R4 is H, C 1-4 Alkyl or halogen; R5 is -NR 5a R 5b , where R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably each independently hydrogen or C 1-3 Alkyl, more preferably all hydrogen; R6 is -C(O)NR 6a R 6b , where R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl, C 3-8 Cycloalkyl or optionally substituted 5-10 membered heteroaryl, preferably each independently hydrogen or C 1-3 alkyl, more preferably all hydrogen; R9 is hydrogen; A3 is N or CR 10 ; A4 is N or CR 10 ; A5 is N or CR 10 , and at least one of A3, A4 and A5 is N; R 10 are independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, R 10 Each is independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 Cycloalkyl, halogenated C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; more preferably, R 10 Each is independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C1-6 Alkoxy, C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, the optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl is optionally substituted by 1 or 2 selected from halogen, C 1-4 Alkyl, C 1-4 The substituents of the alkoxy group and the optionally substituted 4-7 membered heterocyclic group are substituted; preferably, the 6-14 membered aryl group is phenyl; preferably, the 5-10 membered heteroaryl group is selected from imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, indazolyl, pyridinyl and pyrimidinyl; preferably, the 4-7 membered heterocyclic group is a nitrogen-containing heterocyclic group, preferably azetidinyl, pyrrolidinyl, morpholinyl, piperidinyl and piperazinyl.

[0087] One group of preferred compounds of formula I of the present invention is represented by compounds represented by formula III (including formula IIIa and IIIb) or stereoisomers, tautomers, N-oxides, hydrates, solvates, isotope-labeled compounds or pharmaceutically acceptable salts thereof, or mixtures thereof: wherein R1, R5 and R6 are as described in any embodiment of Formula I; R7, R8 and R9 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 2-6 Alkenyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 3-8 cycloalkenyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl.

[0088] In one or more embodiments of the compound of formula III, R1 is: Where W is N or CR w ; Z1 and Z2 are each independently N or CR w , and at least one of Z1 and Z2 is N; n is 0, 1 or 2; R w , R2 and R3 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; each R4 is independently halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; * indicates the position where R1 is attached to the rest of the compound of formula I. Preferably, the optionally substituted C 1-6 Alkyl and optionally substituted C 1-6Each alkoxy group may be independently substituted with 1, 2 or 3 substituents selected from halogen and deuterium; the optionally substituted C 3-8 The alkyl group may be optionally substituted by 1, 2 or 3 groups selected from halogen and C 1-4 The alkyl group is substituted with a substituent.

[0089] In one or more embodiments of the compound of formula III, W is N. In one or more embodiments, W is CR w , R w For hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 More preferably, W is hydrogen, halogen, methyl or deuterated methyl. In some embodiments, W is CH.

[0090] In one or more embodiments of the compound of formula III, Z1 is N and Z2 is CH. In some embodiments, Z1 is CH and Z2 is N.

[0091] In one or more embodiments of the compound of formula III, R2 and R3 are each independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 alkyl; more preferably each independently hydrogen, methyl, deuterated methyl or chlorine. In some embodiments, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 In some embodiments, R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 The alkyl group is preferably methyl, deuterated methyl, bromine or chlorine.

[0092] In one or more embodiments of the compound of formula III, n is 0 or 1.

[0093] In one or more embodiments of the compound of formula III, each R4 is independently halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 Alkyl; more preferably each independently hydrogen, methyl, deuterated methyl or chlorine.

[0094] In one or more embodiments of the compound of formula III, R1 is: Wherein, R2, R3 and W are as described in any of the above embodiments; preferably, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably hydrogen, methyl, deuterated methyl or chlorine; R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 The cycloalkyl group is preferably methyl, deuterated methyl, bromine or chlorine.

[0095] In one or more embodiments of the compound of formula III, R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0096] In one or more embodiments of the compound of formula III, R5 is hydrogen, halogen, cyano, halo 1-3 Alkyl or -NR 5a R 5b ; Preferably, R5 is -NR 5a R 5b Preferably, R 5a and R5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 The cycloalkyl groups are more preferably all hydrogen.

[0097] In one or more embodiments of the compound of formula III, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 In some embodiments, R 6a and R 6b Together with the attached N, it forms a 5-10 membered heterocyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxy and optionally substituted C 1-4 In some preferred embodiments, R 6a and R 6b Together with the attached N, it forms a 9-10 heterobicyclic group containing 1, 2, 3 or 4 heteroatoms selected from N and O, optionally 1, 2 or 3 selected from halogen, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl and hydroxy substituted C 1-4 The alkyl group is substituted with a substituent.

[0098] In one or more embodiments of the compound of formula III, R6 is -C(O)NR 6a R 6b , R 6a and R 6b As described in any of the above embodiments; preferably, R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 cycloalkyl, more preferably all hydrogen; in some embodiments, R 6a and R 6b Together with the attached N, it forms an optionally substituted heterocyclyl as described herein. In a preferred embodiment, R6 is -C(O)NH2.

[0099] In one or more embodiments of the compound of formula III, R7 and R9 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C2-6 Alkenyl or optionally substituted C 3-8 Preferably, R7 and R9 are each independently hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, deuterated C 1-6 Alkoxy or C 3-6 More preferably, R7 and R9 are each independently hydrogen, halogen or C 1-3 alkyl.

[0100] In one or more embodiments of the compound of formula III, R8 is an optionally substituted 4-10 membered heterocyclyl, an optionally substituted C 6-14 Preferably, the optionally substituted 4-10 membered heterocyclic group, the optionally substituted C 6-14 The aryl and optionally substituted 5-10 membered heteroaryl groups may each be optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, cyano, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 In some embodiments, the 4-10 membered heterocyclyl, C 6-14 The aryl and 5-10 membered heteroaryl are unsubstituted or each is optionally substituted with one acylamino group.

[0101] It should be understood that although the above description of R1, R5, R6, R7, R8, R9, A0, A1, A2, A3, A4, A5, A6, A7, A 8、 B1, B2, B3, D1, D2, D3 and D4 are described separately, but each of the described features can be combined in any way to form different scopes of compounds of Formula I (including Formula II and Formula III) of the present invention. For example, in some embodiments of the compounds of Formula I (including Formula II and Formula III) of the present invention.

[0102] Preferred examples of compounds of Formula I include, but are not limited to: or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt thereof, or a mixture thereof.

[0103] Some of the compounds of the present invention may exist as stereoisomers, including optical isomers. The present invention includes all stereoisomers and racemic mixtures of such stereoisomers, as well as individual enantiomers that can be separated according to methods well known to those skilled in the art.

[0104] Examples of pharmaceutically acceptable salts include inorganic and organic acid salts, such as hydrochloride, hydrobromide, phosphate, sulfate, citrate, lactate, tartrate, maleate, fumarate, mandelate, and oxalate; and inorganic and organic base salts formed with bases such as sodium hydroxide, tris(hydroxymethyl)aminomethane (TRIS, tromethamine), and N-methylglucamine.

[0105] Examples of prodrugs of the compounds of the invention include simple esters of carboxylic acid-containing compounds (e.g., by reacting with C 1-4 esters of compounds containing hydroxyl groups (for example, by reacting with C 1-4 Carboxylic acid, C 3-6 esters obtained by condensation of diacids or their anhydrides, such as succinic anhydride and fumaric anhydride); imines of compounds containing amino groups (for example, by reacting with C 1-4 imines obtained by condensation of aldehydes or ketones); carbamates of compounds containing amino groups, such as those described by Leu et al. (J. Med. Chem. 42: 3623-3628 (1999)) and Greenwald et al. (J. Med. Chem. 42: 3657-3667 (1999)); acetals or ketals of compounds containing alcohols (such as those obtained by condensation with chloromethyl methyl ether or chloromethyl ethyl ether according to methods known in the art).

[0106] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using methods similar to those shown in the reaction examples in Reaction Scheme 1 shown below. Pyridine-2,4-diamine, I2, and HIO4 react to produce 3-iodopyridine-2,4-diamine. 3-iodopyridine-2,4-diamine reacts with a Pd catalyst (such as Pd(dppf)Cl2) and TEA to produce 2,4-diaminonicotinate methyl ester. 2,4-diaminonicotinate methyl ester reacts with NIS to produce 2,4-diamino-5-iodonicotinate methyl ester. Methyl 2,4-diamino-5-iodonicotinate and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol react in the presence of a Pd catalyst (e.g., cataCXium A Pd G3) and K3PO4 to produce methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate. Methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate reacts with 2-chloroacetaldehyde to produce methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylate. 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester reacts with sodium methoxide and ammonia methanol to obtain the target compound 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Reaction Scheme 1

[0107] Other related compounds can be prepared using similar methods. For example, replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (5-methyl-1H-indazol-4-yl)boronic acid can produce 7-amino-6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide. Replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (1H-indazol-4-yl)boronic acid can produce 7-amino-6-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide. Replacing 2-chloroacetaldehyde with 2-bromoacetic acid can produce 7-amino-2-hydroxy-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Replacing 2-chloroacetaldehyde with 2-bromo-1-cyclopropylethane-1-one can produce 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide.

[0108] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme similar to that shown in Reaction Scheme 2. 4-Amino-6-chloronicotinic acid is reacted with NBS to produce 4-amino-5-bromo-6-chloronicotinic acid. 4-Amino-5-bromo-6-chloronicotinic acid is reacted with TMSCH2N2 to produce 4-amino-5-bromo-6-chloronicotinic acid methyl ester. 4-Amino-5-bromo-6-chloronicotinic acid methyl ester is reacted with Boc2O in the presence of a base (such as triethylamine) to produce 5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinic acid methyl ester. 5-Bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinic acid methyl ester is reacted with NaN3 to produce 6-azido-5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinic acid methyl ester. The reaction of methyl 6-azido-5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinate with PPh3 gives methyl 6-amino-5-bromo-4-((tert-butoxycarbonyl)amino)nicotinate. The reaction of methyl 6-amino-5-bromo-4-((tert-butoxycarbonyl)amino)nicotinate with 3-chlorobutan-2-one gives methyl 8-bromo-7-((tert-butoxycarbonyl)amino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate. 8-Bromo-7-((tert-butoxycarbonyl)amino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol react under the catalysis of Pd catalyst (such as Pd(PPh3)4) and NaOH to obtain 7-((tert-butoxycarbonyl)amino)-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid. 7-((tert-Butoxycarbonyl)amino)-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid reacts with NH4Cl and HATU to give tert-butyl (6-carbamoyl-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)carbamate. Tert-butyl (6-carbamoyl-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)carbamate is deprotected under acidic conditions to give the target compound, 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide. Reaction Scheme 2

[0109] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme similar to that shown below. 2,4-Dichloronicotinic acid reacts with methyl iodide to produce methyl 2,4-dichloronicotinate. 2,4-Dichloronicotinate reacts with sodium azide to produce methyl 4-azido-2-chloronicotinate. 4-Azido-2-chloronicotinate reacts with HI to produce methyl 4-amino-2-chloronicotinate. 4-Amino-2-chloronicotinate reacts with Pd (e.g., Pd(dba)) and Zn(CN) to produce methyl 4-amino-2-cyanonicotinate. 4-Amino-2-cyanonicotinate reacts with bromine to produce methyl 4-amino-5-bromo-2-cyanonicotinate. Methyl 4-amino-5-bromo-2-cyanonicotinate and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol react under the catalysis of Pd (such as catalytic Pd G3) and K3PO4 to produce methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate. Methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate reacts with di-tert-butyl dicarbonate to produce methyl 4-((tert-butyloxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate. Methyl 4-((tert-butoxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate reacts with Raney nickel to give methyl 2-(acetamidomethyl)-4-((tert-butoxycarbonyl)amino)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate. Methyl 2-(acetamidomethyl)-4-((tert-butoxycarbonyl)amino)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate reacts with Burgess reagent to give methyl 7-((tert-butoxycarbonyl)amino)-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylate. Methyl 7-((tert-butoxycarbonyl)amino)-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylate is reacted with TFA to give methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylate. Methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylate is hydrolyzed with NaOH and acidified to give 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylic acid.7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide is obtained by reacting HATU / DIEA with 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide. Reaction Scheme 3.

[0110] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme similar to that shown below in Reaction Scheme 4. 2-Amino-4-chloronicotinic acid is reacted with TMS-CH2N2 to produce 2-amino-4-chloronicotinic acid methyl ester. 2-Amino-4-chloronicotinic acid methyl ester is reacted with 1,1-dimethoxy-N,N-dimethylmethanamine to produce (Z)-4-chloro-2-(((dimethylamino)methylene)amino)nicotinic acid methyl ester. (Z)-4-chloro-2-(((dimethylamino)methylene)amino)nicotinic acid methyl ester is reacted with hydroxylamine hydrochloride to produce (Z)-4-chloro-2-(N'-hydroxycarboxamido)nicotinic acid methyl ester. Methyl (Z)-4-chloro-2-(N'-hydroxycarboxamido)nicotinate reacts with TFAA to give methyl 7-chloro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate. Methyl 7-chloro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate reacts with ammonia methanol to give 7-amino-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. 7-amino-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide reacts with bromine to give 7-amino-6-bromo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. 7-amino-6-bromo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol are catalyzed by Pd (such as Catalytic Pd G3) and K3PO4 to obtain the target compound 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Reaction Scheme 4

[0111] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme similar to that shown below in Reaction Scheme 5. 4-Amino-3-(5-hydroxy-2-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide is reacted with NBS to produce 4-amino-3-(2-bromo-3-hydroxy-6-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide. 4-amino-3-(2-bromo-3-hydroxy-6-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriazolinone react under Pd (such as Pd(OAc)2) and K2CO3 to obtain the target compound 4-amino-3-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide. Reaction Scheme 5

[0112] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme similar to that shown below. 1H-indazole-6-amine reacts with NBS to produce 7-bromo-1H-indazole-6-amine. 7-bromo-1H-indazole-6-amine is reacted with Pd (e.g., Pd(dppf)Cl2) to produce methyl 6-amino-1H-indazole-7-carboxylate. 6-amino-1H-indazole-7-carboxylate is reacted with NIS to produce methyl 6-amino-5-iodo-1H-indazole-7-carboxylate. Methyl 6-amino-5-iodo-1H-indazole-7-carboxylate and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol react under Pd (e.g., CataCXium A Pd G3) catalysis to yield methyl 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylate. Methyl 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylate is hydrolyzed with NaOH to yield 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylic acid. 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylic acid and NH4Cl react under HATU and DIEA conditions to obtain the target compound 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxamide. Reaction Scheme 6

[0113] The compounds of the present invention can be prepared using methods known to those skilled in the art or the novel methods of the present invention. Specifically, the compounds of the present invention having Formula I (including Formula II and Formula III) can be synthesized using a reaction scheme 7 similar to that shown below. 2,4-Diamino-5-iodonicotinic acid methyl ester and 3-bromobutan-2-one react to obtain 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid methyl ester. 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid methyl ester is hydrolyzed and acidified under NaOH conditions to obtain 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid. 7-Amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid and NH4Cl react under HATU and DIEA conditions to give 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide. 7-Amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide and 2-chloro-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol react under Pd (e.g., catalytic Cxium-Pd-G3) to give the target compound 7-amino-6-(2-chloro-3-hydroxy-6-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide. Reaction Scheme 7

[0114] An important aspect of the present invention is the discovery that compounds of Formula I (including Formula II and Formula III) are PKMYT1 kinase inhibitors. Therefore, compounds of Formula I (including Formula II and Formula III) or their stereoisomers, tautomers, N-oxides, hydrates, solvates, isotopically labeled compounds, or pharmaceutically acceptable salts, or mixtures thereof, can be used to treat or prevent PKMYT1-related diseases or to prepare medicaments for treating or preventing PKMYT1-related diseases. As used herein, "PKMYT1-related diseases" refer to diseases mediated by PKMYT1, such as cancer. As used herein, "PKMYT1-mediated diseases" refer to diseases in the occurrence and development of which PKMYT1 is involved. Herein, the PKMYT1-mediated diseases include, but are not limited to, liver cancer, melanoma, Hodgkin's disease, non-Hodgkin's lymphoma, acute lymphocytic leukemia, chronic lymphocytic leukemia, multiple myeloma, neuroblastoma, breast cancer, ovarian cancer, lung cancer (such as small cell lung cancer), Wilms' tumor, cervical cancer, testicular cancer, soft tissue sarcoma, primary macroglobulinemia, bladder cancer, chronic myeloid leukemia, primary brain cancer, gastric cancer, colon cancer, malignant pancreatic insulinoma, malignant carcinoid cancer, choriocarcinoma, mycosis fungoides, head and neck cancer, osteogenic sarcoma, pancreatic cancer, acute myeloid leukemia, hairy cell leukemia, rhabdomyosarcoma, Kaposi's sarcoma, genitourinary neoplasia, thyroid cancer, esophageal cancer, cervical hyperplasia, renal cell carcinoma, endometrial cancer, polycythemia vera, essential thrombocythemia, adrenocortical carcinoma, skin cancer and prostate cancer.

[0115] Therefore, the present invention provides a method for treating or preventing a disease or condition caused by abnormal PKMYT1 kinase activity, comprising administering to a subject in need thereof an effective amount of a compound of Formula I (including Formula II and Formula III) or its stereoisomers, tautomers, N-oxides, hydrates, solvates, isotope-labeled compounds, or pharmaceutically acceptable salts, or a mixture thereof, or a pharmaceutical composition comprising an effective amount of a compound of Formula I (including Formula II and Formula III) or its stereoisomers, tautomers, N-oxides, hydrates, solvates, isotope-labeled compounds, or pharmaceutically acceptable salts, or a mixture thereof. In the present invention, the subject includes a mammal, such as a human.

[0116] When practicing the treatment method of the present invention, an effective amount of a pharmaceutical preparation is administered to a patient with one or more of these symptoms. The pharmaceutical preparation contains a compound of Formula I (including Formula II and Formula III) at an effective therapeutic concentration and is formulated for oral, intravenous, local or external administration for the treatment of cancer and other diseases. The dosage is the amount that effectively improves or eliminates one or more symptoms. For the treatment of a specific disease, an effective amount is an amount that is sufficient to improve or alleviate in some way the symptoms associated with the disease. Such a dosage can be administered as a single dose or can be administered according to an effective treatment regimen. The dosage may cure the disease, but administration is generally intended to improve the symptoms of the disease. Repeated administration is generally required to achieve the desired symptom improvement.

[0117] In another embodiment, provided herein is a pharmaceutical composition comprising a compound of Formula I (including Formula II and Formula III) as described in any embodiment herein or its stereoisomers, tautomers, N-oxides, hydrates, solvates, isotopically labeled compounds or pharmaceutically acceptable salts, or mixtures thereof, as an active ingredient.

[0118] Another embodiment of the present invention relates to a pharmaceutical composition that is effective for treating or preventing cancer, comprising a compound of Formula I (including Formula II and Formula III) as described in any embodiment herein, or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt thereof, or a mixture thereof, and at least one known anticancer drug or a pharmaceutically acceptable salt of an anticancer drug. Herein, the at least one known anticancer drug includes: (1) anticancer drugs related to DNA damage and repair mechanisms, including but not limited to PARP inhibitors Olaparib, Niraparib, Rucaparib, Talazoparib, Senaparib and Saruparib; HDAC inhibitors Vorinostat, Romidepsin, Panobinostat and Belinostat; (2) anticancer drugs related to cell division checkpoints, including but not limited to Chk1 / 2 inhibitors, CDK4 / 6 inhibitors such as Palbociclib, WEE1 inhibitors, ATM inhibitors, ATR inhibitors; (3) alkylating agents, such as busulfan, melphalan, chlorambucil, cyclophosphamide, ifosfamide, temozolomide, bendamustine, cisplatin, mitomycin C, bleomycin and carboplatin; (4) topoisomerase I inhibitors, such as camptothecin, irinotecan and topotecan; topoisomerase II inhibitors, such as doxorubicin, epirubicin, aclarubicin, mitoxantrone, methyl (5) RNA / DNA antimetabolites, such as 5-azacytidine, gemcitabine, 5-fluorouracil and methotrexate; (6) DNA antimetabolites, such as 5-fluoro-2′-deoxyuridine, fludarabine, nelarabine, cytarabine, pralatrexate, pemetrexed, hydroxyurea and thioguanine; (7) antimitotic agents, such as colchicine, vinblastine, vincristine, vinorelbine, paclitaxel, ixabepilone, cabazitaxel and docetaxel; (8) antibodies, For example, monoclonal antibodies, such as panitumumab, neltuzumab, nivolumab, pembrolizumab, ramucirumab, bevacizumab, pertuzumab, trastuzumab, cetuximab, obinutuzumab, ofatumumab, rituximab, alemtuzumab, ibritumomab tiuxetan, tositumomab, brentuximab, daratumumab, elotuzumab, ofatumumab, dinutuximab, blinatumomab, ipilimumab, Avastin, Herceptin, and rituximab;(9) Antibody-drug conjugates (ADCs), such as trastuzumab-emtansine conjugate T-DM1, humanized anti-HER2 antibody-drug conjugates Trastuzumab Deruxtecan, Trastuzumab Emtansine, humanized anti-TROP2 monoclonal antibody-drug conjugates Datopotamab Deruxtecan, Gemtuzumab Ozogamicin, CD30-directed antibody-drug conjugates Brentuximab Vedotin, Inotuzumab Ozogamicin, Sacituzumab govitecan, Enfortumab Vedotin, and Belantamab Mafodotin; (10) Kinase inhibitors, such as imatinib, gefitinib, erlotinib, osimertinib, afatinib, ceritinib, alectinib, crizotinib, erlotinib, lapatinib, sorafenib, regorafenib, vemurafenib, dabrafenib, aflibercept, sunitinib, nilotinib, dasatinib, bosutinib, pralsetinib, ibrutinib, cabozantinib, lenvatinib, vandetanib, trametinib, cobimetinib, axitinib, temsirolimus, idelalisib, Pazopanib, Tecansi and Everolimus; and (11) other known anticancer drugs that can be used for anticancer combination therapy, including tamoxifen, letrozole, fulvestrant, mitoguanidine, octreotide, retinoic acid, arsenic, zoledronic acid, bortezomib, carfilzomib, ixazomib, vismodegib, sonidegi, denosumab, thalidomide, lenalidomide, venetoclax, Aldesleukin (recombinant human interleukin-2) and Sipueucel-T (prostate cancer therapeutic vaccine).

[0119] When practicing the methods of the present invention, the compounds of the present invention and at least one known anticancer drug can be administered together as a single pharmaceutical composition. Alternatively, the compounds of the present invention and at least one known anticancer drug can be administered separately. In one embodiment, the compounds of the present invention and at least one known anticancer drug are administered approximately simultaneously, i.e., all drugs are administered simultaneously or sequentially, as long as therapeutic blood concentrations of the compounds are achieved simultaneously. In another embodiment, the compounds of the present invention and at least one known anticancer drug are administered according to separate dosage regimens, as long as therapeutic blood concentrations of the compounds are achieved.

[0120] Another embodiment of the present invention is a bioconjugate comprising the compound described above that is effective as a kinase inhibitor and capable of inhibiting tumors. This bioconjugate comprises the compound described above combined with at least one known therapeutic antibody, such as Herceptin or Rituximab, or a growth factor, such as EGF or FGF, or a cytokine, such as interleukin-2 or -4, or any other molecule capable of binding to a cell surface. This antibody or other molecule can deliver the compound to its target, making it an effective anticancer agent. This bioconjugate can also enhance the anticancer efficacy of therapeutic antibodies, such as Herceptin or Rituximab.

[0121] Another embodiment of the present invention relates to a pharmaceutical composition that effectively inhibits tumors, comprising a PKMYT1 kinase inhibitor represented by Formula I (including Formula II), or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotopically labeled compound, or pharmaceutically acceptable salt thereof, or a mixture thereof, in combination with radiotherapy. In this embodiment, the compound of the present invention and the radiotherapy may be administered at the same time or at different times.

[0122] Another embodiment of the present invention relates to a pharmaceutical composition effective for postoperative cancer treatment, comprising a PKMYT1 kinase inhibitor represented by Formula I (including Formula II and Formula III), or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound, or pharmaceutically acceptable salt thereof, or a mixture thereof. The present invention also relates to a method of treating cancer in a mammal by surgically resecting a tumor and then treating the mammal with the pharmaceutical composition of the present invention.

[0123] The pharmaceutical compositions of the present invention include pharmaceutical formulations containing all of the compounds of the present invention in an amount effective to achieve their intended purpose. While individual needs vary, those skilled in the art can determine the optimal dosage of each component of the pharmaceutical formulation. Generally, the compounds, or pharmaceutically acceptable salts thereof, are administered orally to mammals daily in an amount of about 0.0025 to 50 mg / kg body weight. However, an oral dosage of about 0.01 to 10 mg / kg is preferred. If a known anticancer drug is also administered, its dosage should be effective to achieve its intended purpose. The optimal dosages of these known anticancer drugs are well known to those skilled in the art.

[0124] The unit oral dose may comprise about 0.01 to 50 mg, preferably about 0.1 to 10 mg, of a compound of this invention. The unit dose may be administered once or multiple times, in one or more tablets per day, each tablet containing about 0.1 to 50 mg, conveniently about 0.25 to 10 mg, of a compound of this invention or a solvate thereof.

[0125] In external preparations, the concentration of the compound of the present invention may be about 0.01 to 100 mg per gram of carrier.

[0126] The compounds of the present invention can be administered as raw pharmaceuticals. They can also be administered as part of a suitable pharmaceutical formulation containing a pharmaceutically acceptable carrier (including excipients and adjuvants). These pharmaceutically acceptable carriers facilitate processing of the compound into pharmaceutical formulations for pharmaceutical use. Preferred pharmaceutical formulations, particularly those for oral administration and preferred modes of administration, such as tablets, lozenges, and capsules, as well as solutions suitable for injection or oral administration, contain from about 0.01% to 99%, preferably from about 0.25% to 75%, of the active compound and excipients.

[0127] The present invention also encompasses the non-toxic pharmaceutically acceptable salts of the compounds of this invention. Acid addition salts are formed by mixing a solution of a non-toxic pharmaceutically acceptable acid with a solution of the compound of this invention. Examples of such acids are hydrochloric acid, fumaric acid, maleic acid, succinic acid, acetic acid, citric acid, tartaric acid, carbonic acid, phosphoric acid, and oxalic acid. Base addition salts are formed by mixing a solution of a non-toxic pharmaceutically acceptable base with a solution of the compound of this invention. Examples of such bases are sodium hydroxide, potassium hydroxide, choline hydroxide, sodium carbonate, tris(hydroxymethyl)aminomethane, and N-methyl-glucamine.

[0128] The pharmaceutical preparations of the present invention can be administered to any mammal, provided they can obtain the therapeutic effect of the compounds of the present invention. Among these mammals, the most important are humans and veterinary animals, although the present invention is not intended to be so limited.

[0129] The pharmaceutical preparations of the present invention may be administered by any route to achieve their intended purpose. For example, they may be administered parenterally, subcutaneously, intravenously, intramuscularly, intraperitoneally, transdermally, orally, intrathecally, intracranially, nasally, or topically. Alternatively or concurrently, they may be administered orally. The dosage will be determined based on the patient's age, health, and weight, the type of concurrent treatment, the frequency of treatment, and the desired therapeutic benefit.

[0130] The pharmaceutical preparations of the present invention can be manufactured in known manners. For example, they can be manufactured by conventional mixing, granulation, tableting, dissolution, or freeze-drying processes. For oral preparations, solid excipients and the active compound can be combined and the mixture can be optionally ground. After adding appropriate amounts of adjuvants, if desired or necessary, the granular mixture can be processed to obtain tablets or lozenge cores.

[0131] Suitable excipients are, in particular, fillers, for example, sugars such as lactose or sucrose, mannitol or sorbitol; cellulose preparations and / or calcium phosphates, for example, tricalcium phosphate or calcium hydrogen phosphate; and binders, for example, starch pastes, including corn starch, wheat starch, rice starch, potato starch, gelatin, tragacanth, methylcellulose, hydroxypropyl methylcellulose, sodium carboxymethylcellulose, and / or polyvinylpyrrolidone. If necessary, disintegrants such as the starches mentioned above, as well as carboxymethyl starch, cross-linked polyvinylpyrrolidone, agar, or alginic acid or salts thereof, such as sodium alginate, can be added. Auxiliary agents are, in particular, flow regulators and lubricants, for example, silica, talc, stearic acid or salts thereof, such as magnesium stearate or calcium stearate, and / or polyethylene glycol. If necessary, the tablet cores can be provided with a suitable coating that is resistant to gastric juices. For this purpose, concentrated sugar solutions can be used. This solution may contain gum arabic, talc, polyvinyl pyrrolidone, polyethylene glycol and / or titanium dioxide, a lacquer solution and a suitable organic solvent or solvent mixture. To prepare a coating resistant to gastric juices, a suitable cellulose solution may be used, for example, cellulose acetate phthalate or hydroxypropyl methylcellulose phthalate. Dyes or pigments may be added to the coating of the tablet or lozenge core, for example, for identification or to characterize the combination of active ingredient doses.

[0132] Other pharmaceutical formulations for oral administration include press-fit capsules made of gelatin and sealed soft capsules made of gelatin and a plasticizer such as glycerol or sorbitol. These press-fit capsules may contain the active compound in granular form, mixed with a filler such as lactose; a binder such as starch; and / or a lubricant such as talc or magnesium stearate; and a stabilizer. In soft capsules, the active compound is preferably dissolved or suspended in a suitable liquid such as a fat or liquid paraffin, to which a stabilizer may be added.

[0133] Formulations suitable for parenteral administration include aqueous solutions of the active compound, such as solutions of water-soluble salts and alkaline solutions. In addition, oily injection suspensions of the appropriate active compound may be administered. Suitable lipophilic solvents or carriers include oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate or triglycerides or polyethylene glycol 400, or hydrogenated castor oil, or cyclodextrins. Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethylcellulose, sorbitol, and / or dextran. They may also contain suspension stabilizers.

[0134] According to one aspect of the present invention, the compounds of the present invention are used in topical and parenteral formulations for the treatment of skin cancer.

[0135] The topical preparation of the present invention can be prepared into oils, creams, emulsions, ointments, etc. by preferably using suitable carriers. Suitable carriers include plant or mineral oils, white mineral oil (white soft paraffin), branched fats or greases, animal fats and high molecular weight alcohols (greater than C 12Preferred carriers are those in which the active ingredient can be dissolved. Emulsifiers, stabilizers, humectants, and antioxidants may also be included, as well as agents that impart color or fragrance, if desired. Furthermore, these topical formulations may contain transdermal penetration enhancers. Examples of such enhancers can be found in U.S. Patent Nos. 3,989,816 and 4,444,762.

[0136] Creams are preferably formulated with a mixture of mineral oil, self-emulsifying beeswax and water, mixed with the active ingredient dissolved in a small amount of oil, such as almond oil. A typical cream example comprises about 40 parts water, 20 parts beeswax, 40 parts mineral oil and 1 part almond oil.

[0137] Ointment can be prepared like this, the vegetable oil that contains active ingredient is for example almond oil and warm soft paraffin are mixed, then make this mixture cool.A typical ointment example comprises about 30% weight almond oil and 70% weight white soft paraffin.

[0138] The present invention also relates to the use of the compounds of the present invention to prepare drugs for treating clinical conditions that are effective in inhibiting PKMYT1 kinase. These drugs may include the above-mentioned pharmaceutical composition.

[0139] The following examples are illustrative, but not limiting, of the methods and formulations of the present invention. Other modifications and improvements to various conditions and parameters that are obvious to those skilled in the art and that are commonly encountered in clinical treatment are within the spirit and scope of the present invention. General description of the examples All reagents used were of commercial quality, and solvents were dried and purified according to standard methods. Mass spectrometry samples were analyzed using a single quadrupole mass spectrometer (Shimadzu 2020) with electrospray. Data were recorded using a Varian 400 MHz nuclear magnetic spectrometer. 1H NMR spectra, chemical shifts are reported in ppm from downfield with TMS as the internal standard (0.00 ppm), and coupling constants J are reported in Hz. Example 1 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 3-iodopyridine-2,4-diamine: Pyridine-2,4-diamine (1.0 g, 9.2 mmol, 1.0 eq) was placed in a mixed solution of acetic acid (9 mL), water (1 mL), and concentrated sulfuric acid (0.2 mL) and reacted at 50°C for 30 minutes. After cooling to room temperature, iodine (1.2 g, 4.6 mmol, 0.5 eq) and iodic acid dihydrate (365 mg, 1.6 mmol, 0.17 eq) were added, and the reaction was continued at 55°C for 6 hours. After completion of the reaction, the reaction solution was poured into a 10% aqueous solution of Na2S2O3 to quench the mixture and concentrated. Water (50 mL) was added and the pH was adjusted to 7 with NaHCO 3 , filtered, and the filtrate was extracted with EtOAc (50 mL×3). The organic layers were combined and concentrated to give a yellow solid (1.6 g, 73% yield). LCMS: 235.95 [M+H] + b) Preparation of methyl 2,4-diaminonicotinate: 3-iodopyridine-2,4-diamine (1.6 g, 6.8 mmol, 1.0 eq) was placed in MeOH (20 mL), and Pd(dppf)Cl2 (512 mg, 0.7 mmol, 0.1 eq) and TEA (2.1 g, 20.4 mmol, 3.0 eq) were added. The reaction was allowed to proceed at 70°C under CO conditions for 20 hours. After completion of the reaction, the product was concentrated and the residue was purified by column chromatography (DCM:MeOH = 10:1) to obtain a crude red solid (1.1 g). LCMS: 167.95 [M+H] +c) Preparation of 2,4-diamino-5-iodonicotinic acid methyl ester: 2,4-diaminonicotinic acid methyl ester (1.1 g, 6.6 mmol, 1.0 eq) was placed in DMF (20 mL) and NIS (1.6 g, 7.3 mmol, 1.1 eq) was added. The reaction was allowed to react at room temperature under nitrogen for 1 hour. After the reaction was completed, water (20 mL) was added and extracted with EA (20 mL × 5). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (PE / EA = 2 / 1) gave a yellow solid (1.6 g, 80% yield). d) Preparation of methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: Methyl 2,4-diamino-5-iodonicotinate (215 mg, 0.7 mmol, 1.0 eq) was placed in a mixture of dioxane (10 mL) and H₂O (2 mL) at room temperature. 2,4-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (273 mg, 1.1 mmol, 1.5 eq), cataCXium A Pd G₃ (73 mg, 0.1 mmol, 0.1 eq), and K₃PO₄ (445 mg, 2.1 mmol, 3.0 eq) were added. The mixture was reacted at 100°C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, water (10 mL) was added, and extraction was performed with EA (10 mL x 3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (DCM / MeOH=20 / 1) gave a yellow solid (120 mg, 57% yield). LC-MS: 288.00 [M+H] + e) Preparation of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylate: Methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (120 mg, 0.4 mmol, 1.0 eq) was placed in DMF (10 mL) at room temperature, and 2-chloroacetaldehyde (312 mg, 4.0 mmol, 10.0 eq) was added. The mixture was reacted at 80°C for 12 hours. After completion of the reaction, the mixture was concentrated to give a black solid crude product (120 mg). LC-MS: 312.10 [M+H] + , 310.05[MH] -f) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (120 mg, crude product) was placed in NH3-MeOH (7M, 30 mL) solution at room temperature, and NaOMe (216 mg, 4.0 mmol, 10.0 eq) was added. The reaction was carried out at 80°C for 72 hours. After completion of the reaction, the mixture was concentrated and the residue was purified by preparative HPLC (C 18, ACN in H2O, 5-55%, 0.1% HCOOH) was purified to give a white solid (6.7 mg, 5% yield). Example 2 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide 4-amino-6-chloronicotinic acid reacts with NBS to give 4-amino-5-bromo-6-chloronicotinic acid. 4-amino-5-bromo-6-chloronicotinic acid reacts with TMSCH2N2 to give 4-amino-5-bromo-6-chloronicotinic acid methyl ester. Methyl 4-amino-5-bromo-6-chloronicotinate reacts with Boc2O in the presence of a base (such as triethylamine) to give methyl 5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinate. Methyl 5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinate reacts with NaN3 to give methyl 6-azido-5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinate. Methyl 6-azido-5-bromo-4-((tert-butoxycarbonyl)amino)-6-chloronicotinate reacts with PPh3 to give methyl 6-amino-5-bromo-4-((tert-butoxycarbonyl)amino)nicotinate. Methyl 6-amino-5-bromo-4-((tert-butoxycarbonyl)amino)nicotinate reacts with 3-chlorobutan-2-one to produce methyl 8-bromo-7-((tert-butoxycarbonyl)amino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate. Methyl 8-bromo-7-((tert-butoxycarbonyl)amino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate reacts with 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol in the presence of a Pd catalyst (e.g., Pd(PPh3)4) and NaOH to produce 7-((tert-butoxycarbonyl)amino)-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid. 7-((tert-Butoxycarbonyl)amino)-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid reacts with NH4Cl and HATU to give tert-butyl (6-carbamoyl-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)carbamate. Tert-butyl (6-carbamoyl-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)carbamate is deprotected under acidic conditions to give the target compound, 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide.Example 3 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide a) Preparation of methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: 5-methoxy-3,4-dihydro-2H-pyrrole (10.0 g, 101 mmol, 1.0 eq) was placed in dimethyl 3-oxoglutarate (17.6 g, 101 ml, 1.0 eq) at room temperature, and TEA (510.0 mg, 5.0 mmol, 0.05 eq) was added. The reaction was allowed to react at room temperature for 48 hours. The mixture was filtered and the solid was washed with MTBE (5 mL × 3). The residue was concentrated to give a white solid (15.9 g, 75% yield). LC-MS: 210.0 [M+H]. + . b) Preparation of 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester: Under nitrogen conditions, 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (4.87 g, 23.3 mmol, 1.0 eq) was placed in POCl3 (50 mL) and reacted at 100°C for 16 hours. The reaction solution was concentrated, quenched with water (30 mL), extracted with EA (30 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate and concentrated to obtain a crude product. Purification by column chromatography (PE / EA=10 / 1 to 2 / 1) gave a yellow solid (3.7 g, 70% yield). LC-MS: 228.0 [M+H] + . c) Preparation of methyl 6-bromo-7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: Under nitrogen, methyl 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (3.7 g, 16.3 mmol, 1.0 eq) was placed in DMF (40 mL) and NBS (3.5 g, 19.5 mmol, 1.2 eq) was added. The reaction was carried out at room temperature for 16 hours. Water (30 mL) was added and extracted with EA (30 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0~40 / 1) to give a yellow solid (4.9 g, 98% yield). LC-MS: 307.90 [M+H] +d) Preparation of methyl 7-amino-6-bromo-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: methyl 6-bromo-7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (1.0 g, 3.3 mmol, 1.0 eq) was placed in NH3 / MeOH (30 mL) and reacted at 60°C for 16 hours. After completion of the reaction, the reaction solution was concentrated. Purification by column chromatography (DCM / MeOH = 1 / 0 to 30 / 1) gave a white solid (368 mg, 39% yield). LC-MS: 288.90 [M+H] + e) Preparation of methyl 7-amino-6-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: Under nitrogen, methyl 7-amino-6-bromo-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (400 mg, 1.4 mmol, 1.0 eq) was placed in a mixed solution of dioxane (10 mL) and H2O (2 mL), and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (652 mg, 2.8 mmol, 2.0 eq), SPhos-Pd-G3 (218 mg, 0.3 mmol, 0.2 eq), and K3PO4 (593 mg, 2.8 mmol, 2.0 eq) were added. The mixture was reacted at 100°C for 16 hours. The reaction mixture was cooled to room temperature, added with water (20 mL), and extracted with EA (30 mL × 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH = 10 / 1) to give a yellow solid (360 mg, 82% yield). LC-MS: 315.05 [M+H] + . f) Preparation of 7-amino-6-(2-bromo-3-hydroxy-6-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester: Under nitrogen protection, 7-amino-6-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (310 mg, 1.0 mmol, 1.0 eq) was placed in DMF (40 mL), and NBS (178 mg, 1.0 mmol, 1.0 eq) was added. The reaction was allowed to react at room temperature for 16 hours. Water (30 mL) was added, and the mixture was extracted with EA (30 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=10 / 1) to give a yellow solid (110 mg, 28% yield). LC-MS: 395.00[M+H] +g) Preparation of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: Under nitrogen, methyl 7-amino-6-(2-bromo-3-hydroxy-6-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (110 mg, 0.3 mmol, 1.0 eq) was placed in a mixture of dioxane (10 mL) and H₂O (2 mL). 2,4,6-trimethyl-1,3,5,2,4-6-trioxatriazine (187 mg, 1.5 mmol, 5.0 eq), Pd(OAc)₂ (14 mg, 0.06 mmol, 0.2 eq), PCy₃ (17 mg, 0.06 mmol, 0.2 eq), and K₂CO₃ (124 mg, 0.9 mmol, 3.0 eq) were added. The mixture was reacted at 100°C for 16 hours. The reaction mixture was cooled to room temperature, added with water (20 mL), and extracted with EA (30 mL x 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=10 / 1) to obtain a yellow solid (50 mg, 51% yield). LC-MS: 329.05 [M+H] + . h) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide: Under nitrogen, 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (50 mg, 0.15 mmol, 1.0 eq) was placed in toluene (8 mL), and NH4Cl (40 mg, 0.75 mmol, 5.0 eq) and AlMe3 (56 mg, 0.75 mmol, 5.0 eq) were added. The reaction was carried out at 80°C for 16 hours. The reaction solution was cooled to room temperature, added with water (10 mL), and extracted with EA (10 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate and concentrated to give a crude product. The crude product was purified by preparative HPLC (C 18,ACN in H2O 5-55%, 0.1% HCOOH) to give a yellow solid (2.2 mg, 5% yield). Example 4 (7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-8-yl)(6,7-dihydropyrazolo[1,5-a]pyrazine- Preparation of methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: Methyl 2,4-diamino-5-iodonicotinate (320 mg, 1.09 mmol, 1.0 eq) was placed in a mixture of dioxane / H₂O (4 mL / 1 mL). 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (407 mg, 1.64 mmol, 1.5 eq), catacxium-Pd-G₃ (79 mg, 0.109 mmol, 0.1 eq), and K₃PO₄ (693 mg, 3.27 mmol, 3.0 eq) were added. The mixture was reacted at 100°C for 16 hours. After completion, the reaction was quenched by addition of water (10 mL) and extracted with EA (10 mL x 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (DCM:MeOH=20:1) to give a yellow solid (110 mg, 35% yield). LC-MS: 288.05 [M+H] + b) Preparation of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylate: methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (35 mg, 0.122 mmol, 1.0 eq) was placed in DMF (2 mL), and 2-chloroacetaldehyde (48 mg, 0.61 mmol, 5.0 eq) and NaHCO3 (21 mg, 0.244 mmol, 2.0 eq) were added. The reaction was carried out at 80°C for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water (5 mL) was added, and EA (5 mL × 3) was extracted. The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC: (DCM:MeOH=12:1) to give a white solid (20 mg, 53% yield). LC-MS: 312.10 [M+H] +. c) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (20 mg, 0.064 mmol, 1.0 eq) was placed in a mixed solution of MeOH / H2O (2 mL / 1 mL) and NaOH (26 mg, 0.64 mmol, 10 eq) was added. The reaction was carried out at 85°C for 1 hour. After the reaction was completed, the reaction solution was cooled to room temperature and concentrated. Water (1 mL) was added and 1.0 M HCl was added to adjust the pH to 4. Filter and dry under reduced pressure to obtain a yellow solid crude product. LC-MS: 398.10[M+1] + . Preparation of d)(7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-8-yl)(6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-yl)methanone: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid (20 mg, crude product) was placed in a DMF (2 mL) solution, and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (12 mg, 0.1 mmol), HATU (38 mg, 0.1 mol), and DIEA (26 mg, 0.2 mmol) were added. The reaction was carried out at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated to obtain a crude product. The residue was purified by preparative HPLC (C 18 , ACN in H2O, 5-55%, 0.1% HCOOH) was purified to give a white solid (3.7 mg, 14% yield). Example 5 7-amino-6-(3-hydroxy-2,6-dimethylphenyl) indolizine-8-carboxamide Example 6 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 5-amino-4-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester: To a solution of 5-aminopyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (2.0 g, 9.746 mmol, 1.0 eq) in DMF (10 mL) was added NBS (1.735 g, 7.746 mmol, 1.0 eq) at 0°C. The reaction mixture was stirred at room temperature under nitrogen for 1 hour. After the reaction was complete, water (20 mL) was added and extracted with EA (20 mL x 5). The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified on silica gel (PE / EA = 3 / 1) to give a yellow solid (2.3 g, 82% yield). LCMS: 284.00 [M+H] +. b) Preparation of 4-bromopyrazolo[1,5-a]pyridine-5-amine: 5-amino-4-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (2.3 g, 8.09 mmol, 1.0 eq) was placed in a 48% HBr aqueous solution (20 mL). The reaction was carried out at 100°C under nitrogen for 1 hour. After the reaction was completed, the solvent was removed under reduced pressure. The reaction mixture was added to ice water (20 mL), saturated sodium bicarbonate was added to adjust the pH to 8-9, and the mixture was extracted with EA (20 mL×5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel (PE / EA=3 / 1) to give a black solid (1.22 g, 68% yield). c) Preparation of methyl 5-aminopyrazolo[1,5-a]pyridine-4-carboxylate: 4-Bromopyrazolo[1,5-a]pyridin-5-amine (1.22 g, 5.75 mmol, 1.0 eq) was placed in MeOH (20 mL), and Pd(OAc)2 (258 mg, 1.15 mmol, 0.2 eq), XantPhos (1.33 g, 2.30 mmol, 0.4 eq), and TEA (5.81 g, 57.53 mmol, 10.0 eq) were added. The reaction mixture was reacted at 70°C under CO2 for 12 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was purified on silica gel (PE:EA = 2:1) to give a yellow oil (400 mg, 53% yield). LCMS: 192.05 [M+H] +. d) Preparation of 5-amino-3-iodopyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester: 5-aminopyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester (246 mg, 2.23 mmol, 1.0 eq) was placed in DMF (10 mL) and NIS (504 mg, 2.23 mmol, 1.0 eq) was added. The reaction solution was reacted at room temperature under nitrogen for 1 hour. After the reaction was completed, water (20 mL) was added and extracted with EA (20 mL×5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel (PE / EA=3 / 1) to give a yellow solid (393 mg, 55.6% yield). e) Preparation of 5-amino-3,6-dibromopyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester: 5-amino-3-iodopyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester (393 mg, 1.24 mmol, 1.0 eq) was placed in AcOH (5.0 mL) and Br2 (992 mg, 6.2 mmol, 5.0 eq) was added. The reaction solution was reacted at 50° C. under nitrogen for 12 hours. After completion of the reaction, the solvent was removed under reduced pressure. The reaction solution was added to ice water, the pH was adjusted to 8-9 with saturated sodium bicarbonate, and extracted with EA (20 mL×5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel (PE / EA=3 / 1) to give a yellow solid (188.0 g, 43.5% yield). LCMS: 351.65 [M+H] + f) Preparation of methyl 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-4-carboxylate: To a mixture of methyl 5-amino-3,6-dibromopyrazolo[1,5-a]pyridine-4-carboxylate (100 mg, 0.2865 mmol, 1.0 eq) in dioxane (4 mL) and H2O (2 mL) were added 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (57 mg, 0.2292 mmol, 0.8 eq), CataCXium A Pd G3 (43 mg, 0.0573 mmol, 0.2 eq), and K3PO4 (182 mg, 0.8595 mmol, 3.0 eq) at room temperature. The reaction mixture was reacted at 100°C for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water (10 mL) was added, and extracted with EA (10 mL × 3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparative TLC to obtain a white solid (10 mg, 11.2% yield). LC-MS: 312.00 [M+H] +. g) Preparation of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxylic acid methyl ester: 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester (10 mg, 0.032 mmol, 1.0 eq) was placed in MeOH (2 mL) at room temperature, and an aqueous solution of NaOH (38 mg, 0.96 mmol, 30.0 eq) was added. The reaction solution was reacted at room temperature for 3 hours. After completion of the reaction, it was concentrated under reduced pressure. The residue was dissolved in H2O (2 mL) and the pH was adjusted to 2 with 2N HCl. The mixture was then concentrated under reduced pressure to obtain an unpurified crude product for the next step. LC-MS: 298.00 [M+H] +h) Preparation of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxamide: Under nitrogen, 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-4-carboxylic acid methyl ester (10.0 mg, 0.034 mmol, 1.0 eq) was placed in DMF (1 mL), and NH4Cl (3.5 mg, 0.068 mmol, 2.0 eq), HATU (25.6 mg, 0.068 mmol, 2.0 eq) and DIEA (13.0 mg, 0.101 mmol, 3.0 eq) were added. The reaction was carried out at room temperature for 16 hours. After completion of the reaction, water (10 mL) was added and EA (10 mL×3) was added. The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by preparative HPLC (ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (1.1 mg, 11.0% yield). Example 7 5-Amino-6-(1H-indol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide Example 8 5-Amino-6-(1H-indazol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide Example 9 5-Amino-6-(5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide Example 10 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide a) Preparation of methyl 2,4-dichloronicotinate: 2,4-Dichloronicotinic acid (15.0 g, 78.5 mmol, 1.0 eq) was placed in ACN (200 mL) at 0°C, and DBU (23.9 g, 157.1 mmol, 2.0 eq) and MeI (16.6 g, 117.8 mmol, 1.5 eq) were added. The reaction was allowed to proceed under nitrogen at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel chromatography (PE:EA = 2:1) to give a colorless oil (13.5 g, 84% yield). LC-MS: 206.15 [M+1] + b) Preparation of methyl 4-azido-2-chloronicotinate: Methyl 2,4-dichloronicotinate (10.0 g, 48.78 mmol, 1.0 eq) was placed in DMF (120 mL) and NaN3 (3.8 g, 58.54 mmol, 1.2 eq) was added. The mixture was reacted at 50°C for 6 hours. After the reaction was completed, water (80 mL) was added and the mixture was extracted with EA (150 mL × 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain a yellow solid (11.8 g, crude product). LC-MS: 213.00 [M+H] +c) Preparation of methyl 4-amino-2-chloronicotinate: methyl 4-azido-2-chloronicotinate (25.0 g, crude product) was placed in a round-bottom flask and HI (55%, 40 mL) was slowly added at 0°C. The reaction was allowed to proceed at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated, quenched with a saturated sodium bicarbonate solution (100 mL), and extracted with EA (150 mL×3). The organic phases were combined and washed with sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated to give a white solid (15.0 g, 78% yield). LC-MS: 187.20 [M+H] + . d) Preparation of methyl 4-amino-2-cyanonicotinate: methyl 4-amino-2-chloronicotinate (4.0 g, 21.5 mmol, 1.0 eq) was placed in DMF (40 mL), and Zn(CN)2 (2.8 g, 23.7 mmol, 1.1 eq), Pd2(dba)3 (89.0 mg, 0.2 mmol, 0.01 eq), and dppf (238.0 mg, 0.4 mmol, 0.02 eq) were added. The reaction was carried out at 120 ° C for 6 hours under nitrogen. After the reaction was completed, water (40 mL) was added and extracted with EA (50 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (PE:EA=2:1) ​​to give a yellow solid (2.5 g, 66% yield). LC-MS: 178.30 [M+H] + e) Preparation of methyl 4-amino-5-bromo-2-cyanonicotinate: methyl 4-amino-2-cyanonicotinate (1.5 g, 8.5 mmol, 1.0 eq) was placed in AcOH (200 mL) and Br2 (13.6 g, 84.7 mmol, 10.0 eq) was added. The reaction was carried out at 60°C for 2 hours under nitrogen. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel chromatography (PE:EA=5:1) to give a white solid (1.5 g, 68% yield). LC-MS: 258.10 [M+H] +f) Preparation of methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: Methyl 4-amino-5-bromo-2-cyanonicotinate (1.8 g, 7.1 mmol, 1.0 eq) was placed in a mixture of dioxane / H₂O (15 mL / 5 mL), and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.8 g, 7.1 mmol, 1.0 eq), catacxium-Pd-G₃ (1.0 g, 1.4 mmol, 0.2 eq), and K₃PO₄ (4.5 g, 21.2 mmol, 3.0 eq) were added. The mixture was reacted at 110°C under nitrogen for 16 hours. After completion of the reaction, water (20 mL) was added and the mixture was extracted with EA (30 mL x 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by reverse phase column (C 18 , ACN in H2O, 5-50%) to give a white solid (490 mg, 23% yield). LC-MS: 298.25 [M+H] + . g) 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (490 mg, 1.6 mmol, 1.0 eq) was placed in a mixed solution of THE:H2O (5 mL / 1 mL), and (Boc)2O (719 mg, 3.3 mmol, 2.0 eq) and DMAP (101 mg, 0.8 mmol, 0.5 eq) were added at 0°C. The reaction was allowed to proceed at room temperature for 16 hours under nitrogen. After completion of the reaction, the product was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (PE:EA=2:1) ​​to give a colorless oil (300 mg, 46% yield). LC-MS: 398.3 [M+H] + . h) Preparation of methyl 2-(acetamidomethyl)-4-((tert-butoxycarbonyl)amino)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: methyl 4-((tert-butoxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (280 mg, 0.7 mmol, 1.0 eq) was placed in MeOH (5 mL), and Ac2O (1 mL) and Raney Ni (280 mg) were added. The reaction was allowed to react at room temperature under H2 for 16 hours. After completion of the reaction, the reaction was concentrated under reduced pressure. The residue was purified by preparative chromatography (PE:EA=3:1) to give a white solid (280 mg, 89% yield). LC-MS: 444.35 [M+H] +i) Preparation of methyl 7-((tert-butoxycarbonyl)amino)-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylate: 2-(acetylaminomethyl)-4-((tert-butoxycarbonyl)amino)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (280 mg, 0.6 mmol, 1.0 eq) was placed in ACN (3 mL) and Burgess reagent (451 mg, 1.9 mmol, 3.0 eq) was added at 0°C. The reaction was carried out at 90°C for 3 hours under nitrogen. After completion of the reaction, the reaction solution was concentrated. The residue was purified by preparative chromatography (DCM:MeOH=15:1) to give a yellow oil (130 mg, 48% yield). LC-MS: 426.15 [M+H] + . j) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylic acid methyl ester: 7-((tert-butoxycarbonyl)amino)-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylic acid methyl ester (130 mg, 0.3 mmol, 1.0 eq) was placed in DCM (5 mL) and CF3COOH (4 mL) was added. The reaction was allowed to react at room temperature for 1 hour. After completion of the reaction, it was concentrated under reduced pressure. The residue was purified by Prep-TLC (DCM:MeOH=12:1) to give a yellow oil (130 mg, 90% yield). LC-MS: 326.05[M+H] + . k) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylic acid: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxylic acid methyl ester (90 mg, 0.3 mmol, 1.0 eq) was placed in a mixed solution of MeOH / H2O (4 mL / 1 mL), and NaOH (111 mg, 27.7 mmol, 10.0 eq) was added. The reaction was carried out at 80°C for 4 hours under nitrogen. After the reaction was completed, the reaction was concentrated under reduced pressure. Water (1 mL) was added, and 2.0 M HCl was added to adjust the pH to 4. The reaction was concentrated under reduced pressure to give a yellow solid (90 mg, crude product). LC-MS: 312.00 [M+H] +. 1) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide (90 mg, crude product) was placed in DMF (2 mL), and NH4Cl (23.0 mg, 0.4 mmol), HATU (164.0 mg, 0.4 mmol) and DIEA (112.0 mg, 0.9 mmol) were added. The reaction was carried out at 40°C for 16 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to obtain a crude product. The residue was purified by Prep-HPLC (C 18 , CH3CN:H2O=5%~55%, 0.1% HCOOH) to obtain a white solid (11.6 mg, 9% yield). Example 11 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a) Preparation of 2-amino-4-chloronicotinic acid methyl ester: At room temperature, 2-amino-4-chloronicotinic acid (800 mg, 4.64 mmol, 1.0 eq) was placed in a mixed solution of MeOH (10 mL) and toluene (1 mL), and TMS-CH2N2 (2M, 4.65 mL, 9.3 mmol, 2.0 eq) was added. The reaction was allowed to react at room temperature for 1 hour. After completion of the reaction, the reaction solution was concentrated to obtain a crude product. The residue was purified by silica gel column (DCM / MeOH=10 / 1) to obtain a yellow solid (709 mg, 82% yield). LC-MS: 187.00 [M+H] + b) Preparation of methyl 4-chloro-2-(((dimethylamino)methylene)amino)nicotinate: Under nitrogen, methyl 2-amino-4-chloronicotinate (709 mg, 3.8 mmol, 1.0 eq) was placed in 1,1-dimethoxy-N,N-dimethylformamide (5 mL) and reacted at 100°C for 2 hours. After completion of the reaction, the reaction solution was concentrated to obtain a yellow solid (869 mg, 94% yield). LC-MS: 241.95 [M+H] + c) Preparation of methyl 4-chloro-2-(N′-hydroxycarboximido)nicotinate: Under nitrogen, methyl 4-chloro-2-(((dimethylamino)methylene)amino)nicotinate (869 mg, 3.6 mmol, 1.0 eq) was placed in DMF (40 mL) and NH2OH-HCl (328 mg, 4.7 mmol, 1.3 eq) was added. The reaction was carried out at 80°C for 3 hours. After completion of the reaction, the reaction solution was concentrated to obtain a yellow solid (762 mg, 92% yield). LC-MS: 230.20 [M+H] + , 228.15[MH] -d) Preparation of methyl 7-chloro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate: Under nitrogen at 0°C, (Z)-4-chloro-2-(N′-hydroxycarbamimidoyl)nicotinate (762 mg, 3.3 mmol, 1.0 eq) was placed in THF (20 mL), and TFAA (2.1 g, 9.9 mmol, 3.0 eq) was added. The mixture was stirred at 0°C for 30 minutes, then the temperature was raised to 70°C, and after reacting for 3 hours, it was concentrated under reduced pressure. The residue was purified by silica gel column (DCM / MeOH=1 / 0 to 30 / 1) to give a white solid (600 mg, 86% yield). LC-MS: 212.20 [M+H] + e) Preparation of 7-amino-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: 7-chloro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester (500 mg, 2.4 mmol, 1.0 eq) was placed in an ammonia methanol solution (7 M, 30 mL) and reacted at 80° C. for 16 hours. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0 to 20 / 1) to give a white solid (140 mg, 33% yield). LC-MS: 178.00 [M+H] + . f) Preparation of 7-amino-6-bromo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: Under nitrogen conditions, 7-amino-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (140 mg, 0.8 mmol, 1.0 eq) was placed in AcOH (8 mL) and Br2 (126 mg, 0.8 mmol, 1.0 eq) was added. The reaction was allowed to react at room temperature for 16 hours. The reaction solution was quenched with aqueous sodium thiosulfate solution (10%, 20 mL) and extracted with EA (10 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product. The residue was purified by silica gel column (DCM / MeOH=10 / 1) to give a yellow solid (60 mg, 30% yield). LC-MS: 255.95, 257.95 [M+H] +g) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: Under nitrogen, 7-amino-6-bromo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (60 mg, 0.2 mmol, 1.0 eq) was placed in a mixed solution of dioxane (10 mL) and H2O (2 mL), and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (99 mg, 0.4 mmol, 2.0 eq), Cataxium Pd G3 (29 mg, 0.04 mmol, 0.2 eq) and K3PO4 (127 mg, 0.6 mmol, 3.0 eq) were added. The reaction was carried out at 100°C for 16 hours, and the reaction solution was cooled to room temperature, and water (20 mL) was added and extracted with EA (30 mL × 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by Prep-HPLC (C 18, aqueous acetonitrile 5-50%, 0.1% HCOOH) to give a white solid (3.1 mg, 5% yield). Example 12 8-Amino-7-(3-hydroxy-2,6-dimethylphenyl)-4-oxo-4H-quinolizine-9-carboxamide Example 13 7-Amino-6-(1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide was prepared using a synthetic method similar to that of Example 3, replacing 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol to prepare 7-amino-6-(1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide. Example 14 8-Amino-7-(7-methyl-1H-indazol-6-yl)-6-oxo-1,3,4,6-tetrahydro-2H-quinoline-9-carboxamide was prepared using a synthetic method similar to that of Example 3, replacing 5-methoxy-3,4-dihydro-2H-pyrrole with 6-methoxy-2,3,4,5-tetrahydropyridine, and replacing 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole to obtain 8-amino-7-(5-methyl-1H-indazol-4-yl)-6-oxo-1,3,4,6-tetrahydro-2H-quinoline-9-carboxamide.Example 15 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-oxazolo[3,2-a]pyridine-8-carboxamide Example 16 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-8-carboxamide Example 17 2-amino-3-(3-hydroxy-2,6-dimethylphenyl)-4-oxo-4H-quinolizine-1-carboxamide Example 18 5-amino-4-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-6-carboxamide Example 19 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-6-carboxamide Example 20 7-Amino-2,3-dimethyl-8-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide Example 21 7-Amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylindolizine-6-carboxamide Example 22 7-Amino-8-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Example 23 7-Amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxamide a) Preparation of methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: 5-Methoxy-3,4-dihydro-2H-pyrrole (15.0 g, 151.3 mmol, 1.0 eq) was placed in dimethyl 3-oxoglutarate (26.4 g, 151.3 mmol, 1.0 eq) at room temperature. TEA (978 mg, 7.6 mmol, 0.05 eq) was added and the mixture was allowed to react at room temperature for 48 hours. The reaction mixture was filtered and the filter cake was washed with MTBE (5 mL x 3). The filter cake was dried under reduced pressure to give a white solid (14 g, 93% yield). LC-MS: 209.95 [M+H]. + , 207.90[MH] - . b) Preparation of 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester: 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (11.4 g, 54.5 mmol, 1.0 eq) was placed in POCl3 (114 mL) and reacted at 100 ° C overnight under nitrogen. The reaction solution was concentrated under reduced pressure, quenched with water (100 mL), extracted with EA (100 mL×3), and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (PE / EA=10 / 1~2 / 1) to give a yellow solid (9.8 g, 79% yield). LC-MS: 227.95 [M+H] +. c) Preparation of methyl 6-bromo-7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: Under nitrogen, methyl 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (9.8 g, 43.1 mmol, 1.0 eq) was placed in DMF (100 mL), NBS (9.2 g, 51.7 mmol, 1.2 eq) was added, and the reaction was allowed to react at room temperature overnight. Water (30 mL) was added and extracted with EA (120 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0~40 / 1) to give a yellow solid (10.5 g, 80% yield). LC-MS: 307.90 [M+H] + d) Preparation of methyl 7-azido-6-bromo-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate: Under nitrogen, methyl 6-bromo-7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (10.5 g, 34.3 mmol, 1.0 eq) was placed in a DMF (100 mL) solution, and NaN3 (4.5 g, 68.6 mmol, 1.2 eq) was added. The mixture was reacted at room temperature overnight. Water (30 mL) was added and extracted with EA (120 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a brown solid (12.0 g, crude product). LC-MS: 312.95, 314.95 [M+H] + e) Preparation of 7-amino-2,3-dihydroindolizine-5(1H)-one: 7-azido-6-bromo-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (7.8 g, crude product) was placed in HI (160 mL, 50%) and reacted at 130°C overnight. Saturated aqueous sodium bicarbonate solution (250 mL) was added and adjusted to pH = 8. Prepared by medium and low pressure (C 18 , CH3CN:H2O=5%~30%, 0.1% HCOOH) to obtain a white solid (4.6 g, crude product). LC-MS: 151.00 [M+H] + , 310.00[2M+H] +. f) Preparation of 7-amino-6-iodo-2,3-dihydroindolizine-5(1H)-one: 7-amino-2,3-dihydroindolizine-5(1H)-one (2.8 g, crude product) was placed in DMF (30 mL) under nitrogen, and NIS (4.6 g, 18.6 mmol) was added. React at 0°C for 1 hour. Water (30 mL) was added and extracted with EA (50 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0~40 / 1) to give a yellow solid (1.7 g, 13% yield). LC-MS: 276.90[M+H] + . g) Preparation of methyl 7-amino-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate: Under nitrogen, 7-amino-6-iodo-2,3-dihydroindolizine-5(1H)-one (1.4 g, 5.1 mmol, 1.0 eq) was placed in MeOH (140 mL), and Pd(OAc)2 (229 mg, 1.0 mmol, 0.2 eq), xantphos (590 mg, 1.0 mmol, 0.2 eq), and TEA (5.2 g, 51.0 mmol, 10 eq) were added. Under CO conditions, the reaction was carried out at 70°C for 16 hours. Filter and concentrate the filtrate. The residue was purified by silica gel column (DCM / MeOH=1 / 0~20 / 1) to give a white solid (1.0 g, 96% yield). LC-MS: 208.90 [M+H] + . h) Preparation of methyl 7-amino-8-iodo-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate: Under nitrogen, methyl 7-amino-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate (611 mg, 2.93 mmol, 1.0 eq) was placed in a DMF (100 mL) solution, NIS (1.1 g, 4.4 mmol, 1.5 eq) was added, and the reaction was allowed to proceed overnight at room temperature. Water (30 mL) was added, and the mixture was extracted with EA (20 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0~40 / 1) to give a yellow solid (805 mg, 79% yield). LC-MS: 334.90 [M+H] +i) Preparation of methyl 7-amino-8-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate: Under nitrogen, methyl 7-amino-8-iodo-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate (256 mg, 0.77 mmol, 1.0 eq) was placed in a mixed solution of dioxane (10 mL) and H2O (2 mL), and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269 mg, 1.15 mmol, 1.5 eq), SPhos-Pd-G3 (120 mg, 0.15 mmol, 0.2 eq) and K3PO4 (488 mg, 2.3 mmol, 3.0 eq) were added. The reaction was sealed at 100°C for 12 hours, cooled to room temperature, and water (20 mL) was added. The mixture was extracted with EA (30 mL x 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC (DCM / MeOH = 10 / 1) to give a white solid (163 mg, 68% yield). LC-MS: 315.00 [M+H] + , 313.00[MH] - j) Preparation of methyl 7-amino-8-(2-bromo-3-hydroxy-6-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate: Under nitrogen, methyl 7-amino-8-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate (163 mg, 0.52 mmol, 1.0 eq) was placed in a DMF (10 mL) solution, NBS (93 mg, 0.52 mol, 1.0 eq) was added, and the mixture was reacted at room temperature overnight. Water (30 mL) was added and extracted with EA (20 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC (DCM / MeOH=10 / 1) to give a yellow solid (46 mg, 23% yield). LC-MS: 395.10 [M+H] +k) Preparation of methyl 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate: Under nitrogen, methyl 7-amino-8-(2-bromo-3-hydroxy-6-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxylate (46 mg, 0.12 mmol, 1.0 eq) was placed in a mixed solution of dioxane (8 mL) and H2O (2 mL), and 2,4,6-trimethyl-1,3,5,2,4,6-trimethoxytriazolinone (3.5 M, 0.1 mL, 0.35 mmol, 3.0 eq), Pd(OAc)2 (5 mg, 0.02 mmol, 0.2 eq), Cy3P (6 mg, 0.02 mmol, 0.2 eq) and K2CO3 (33 mg, 0.24 mmol, 2.0 eq) were added, and the reaction was carried out at 100°C in a sealed tube for 2 days. The mixture was cooled to room temperature, and water (20 mL) was added. The mixture was extracted with EA (30 mL × 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC (DCM / MeOH = 10 / 1) to give a white solid (12 mg, 31% yield). LC-MS: 329.30 [M+H] +, 327.25 [MH] - . l) Preparation of 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxamide: 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxamide (12 mg, 0.04 mmol, 1.0 eq) was placed in anhydrous toluene (1 mL), and NH4Cl (10.6 mg, 0.2 mmol, 5.0 eq) and AlMe3 (0.1 mL, 2 M, 0.2 mmol, 5.0 eq) were added at 80 ° C under nitrogen, and the reaction was continued at 100 ° C overnight. Cool to room temperature, add water (10 mL), EA (10 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by preparative HPLC (C 18, CH3CN:H2O=5%~50%, 0.1% HCOOH) to give a white solid (1.8 mg, 15% yield). Example 24 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-oxazolo[3,2-a]pyridine-6-carboxamide Example 25 8-amino-9-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,3,4,6-tetrahydro-2H-quinolizine-7-carboxamide Example 26 8-amino-9-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-6H-pyrido[1,2-a]pyrazine-7-carboxamide Example 27 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(thiazol-2-yl)-1,6-dihydropyridine-3-carboxamide Example 28 4-Amino-3-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide a) Preparation of 4-amino-3-(2-bromo-3-hydroxy-6-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide: Under nitrogen, 4-amino-3-(5-hydroxy-2-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide (23.0 mg, 0.068 mmol, 1.0 eq) was placed in DMF (5 mL) and NBS (14.6 mg, 0.082 mmol, 1.2 eq) was added. The mixture was reacted at room temperature for 12 hours. Water (30 mL) was added and the mixture was extracted with EA (30 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by liquid chromatography (DCM / MeOH=20 / 1) to give a yellow solid (10 mg, 35% yield). LC-MS: 417.00 [M+H] +b) Preparation of 4-amino-3-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide: Amino-3-(2-bromo-3-hydroxy-6-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide (10 mg, 0.024 mmol, 1.0 eq) was placed in a mixed solution of dioxane (5 mL) and H2O (1 mL), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborane (30 mg, 0.24 mmol, 10.0 eq), Pd(OAc)2 (1.1 mg, 0.005 mmol, 0.2 eq), Cy3P (1.4 mg, 0.005 mmol, 0.2 eq), and K2CO3 (6.6 mg, 0.048 mmol, 2.0 eq) were added. After reacting at 100°C for 12 hours, the reaction solution was cooled to room temperature, water (20 mL) was added, and EA (30 mL × 3) was used for extraction. The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by Prep-HPLC to obtain a white solid (0.5 mg, 5.9% yield). Example 29 4-Amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-1-(thiazol-2-yl)-1,2-dihydropyridine-3-carboxamide Example 30 4-Amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide a) Preparation of ethyl 4-ethoxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxylate: Ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (2.0 g, 9.48 mmol, 1.0 eq) was placed in DMF (15 mL), and 2-fluoropyridine (1.84 g, 18.96 mmol, 2.0 eq), CuI (180 mg, 0.95 mmol, 0.1 eq), and Cs2CO3 (4.64 g, 14.22 mmol, 1.5 eq) were added. The mixture was microwaved at 150° C. for 3 hours. After the reaction was complete, water (15 mL) was added, and the mixture was extracted with EA (15 mL x 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM:MeOH = 20:1) to give a yellow oil (1.0 g, 37% yield). LC-MS: 289.10 [M+H] +. b) Preparation of 4-ethoxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxylic acid: 4-ethoxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxylic acid ethyl ester (1.6 g, 5.56 mmol, 1.0 eq) was placed in a mixed solution of MeOH / H2O (15 mL / 5 mL), and NaOH (2.22 g, 55.6 mmol, 10 eq) was added. The reaction was carried out at 80°C for 2 hours. After the reaction was completed, the reaction solution was cooled to room temperature and concentrated under reduced pressure. Water (5 mL) was added and 2.0 M HCl was added to adjust the pH to 4, and EA (15 mL×3) was used for extraction. The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (DCM:MeOH=20:1) to give a white solid (600 mg, 42% yield). LC-MS: 261.00 [M+H] + c) Preparation of 4-hydroxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxylic acid: 4-ethoxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxylic acid (300 mg, 1.15 mmol, 1.0 eq) was placed in a DCE (8 mL) solution and BBr3 (3.1 mL, 34.5 mmol, 30.0 eq) was added. The reaction was carried out at 90°C for 16 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to obtain a crude product. The residue was purified by a reverse phase column (C 18 , acetonitrile in water content 5% to 50%, 0.1% HCOOH) to obtain a white solid (40 mg, 15% yield). LC-MS: 233.00 [M+H] + d) Preparation of 4-chloro-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide: 4-hydroxy-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide (200 mg, 0.862 mmol, 1.0 eq) was placed in a POCl3 (6 mL) solution and reacted at 105°C for 16 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM:MeOH=15:1) to give a yellow solid (150 mg, 70% yield). LCMS: 249.95 [M+H] +e) Preparation of 4-amino-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide: 4-chloro-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide (100 mg, 0.4 mmol, 1.0 eq) was placed in NH3-MeOH (7 M, 3 mL) and CaCl2 (45 mg, 0.4 mmol, 1.0 eq) was added. The mixture was reacted at 80°C for 2 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was purified by preparative TLC (DCM:MeOH=15:1) to give a white solid (90 mg, 97% yield). LCMS: 231.00 [M+H] + . f) Preparation of 4-amino-5-bromo-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide: 4-amino-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide (150 mg, 0.65 mmol, 1.0 eq) was placed in a DMF (5 mL) solution and NBS (139 mg, 0.78 mmol, 1.2 eq) was added. The reaction was carried out at 50°C under nitrogen for 16 hours. After the reaction was completed, water (20 mL) was added and extracted with EA (10 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH=10:1) to give a white solid (50 mg, 25% yield). LC-MS: 310.90 [M+H] + g) Preparation of 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide: 4-amino-5-bromo-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide (60 mg, 0.195 mmol, 1.0 eq) was placed in a mixed solution of dioxane / H₂O (2 mL / 0.5 mL), and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (73 mg, 0.293 mmol, 1.5 eq), catacxium-Pd-G₃ (14 mg, 0.02 mmol, 0.1 eq), and K₃PO₄ (124 mg, 0.585 mmol, 3.0 eq) were added. The mixture was microwaved at 110° C. for 1 hour. After the reaction was completed, water (10 mL) was added and extracted with EA (5 mL × 3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative TLC (DCM: MeOH = 20: 1) to obtain a crude product. The crude product was purified by preparative HPLC (C 18, acetonitrile content in water 5% to 50%, 0.1% HCOOH) was purified to give a white solid (15.4 mg, 23% yield). Example 31 7-Amino-6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 1, replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (5-methyl-1H-indazol-4-yl)boronic acid to give 7-amino-6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 32 Preparation of 4-amino-3-(5-methyl-1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide (a) (Z)-methyl 2-((dimethylamino)methylene)-3-oxoglutarate: Dimethyl 3-oxoglutarate (5 g, 28.7 mmol, 1.0 eq) was placed in DMF-DMA (50 mL) and refluxed for 12 hours. The reaction solution was concentrated to give a yellow oil (5.3 g, 80% yield). LC-MS: 210 [M+H] + b) Preparation of methyl 4-hydroxy-2-oxo-2H-[1,2′-bipyridine]-5-carboxylate: Dimethyl 2-((dimethylamino)methylene)-3-oxoglutarate (2.0 g, 8.7 mmol, 1.0 eq) was placed in EtOH (20 mL) and pyridin-2-amine (900 mg, 9.6 mmol, 1.1 eq) was added. The reaction was refluxed for 12 hours. The reaction solution was concentrated to obtain a crude product. The residue was washed with EA to obtain a white solid (1.7 g, 79% yield). LC-MS: 247.00 [M+H] + , 244.95[MH] - . c) Preparation of methyl 4-chloro-2-oxo-2H-[1,2′-bipyridine]-5-carboxylate: methyl 4-hydroxy-2-oxo-2H-[1,2′-bipyridine]-5-carboxylate (1.7 g, 6.9 mmol, 1.0 eq) was placed in POCl3 (50 mL) and reacted at 80°C for 12 hours under nitrogen. The reaction solution was concentrated. Water (30 mL) was added and extracted with EA (30 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate and concentrated to give a crude product. The residue was purified by silica gel column (PE / EA=10 / 1~2 / 1) to give a yellow solid (1.5 g, 82% yield). LC-MS: 264.95[M+H] +. d) Preparation of 3-bromo-4-chloro-2-oxo-2H-[1,2′-bipyridine]-5-carboxylic acid methyl ester: Under nitrogen conditions, 4-chloro-2-oxo-2H-[1,2′-bipyridine]-5-carboxylic acid methyl ester (500 mg, 1.9 mmol, 1.0 eq) was placed in a DMF (5 mL) solution, and NBS (406 mg, 2.3 mmol, 1.2 eq) was added. The reaction was allowed to react at room temperature for 4 hours. Water (30 mL) was added and extracted with EA (30 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column (DCM / MeOH=1 / 0~40 / 1) to give a yellow solid (450 mg, 69% yield). LC-MS: 344.95[M+H] + . e) Preparation of 4-amino-3-bromo-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide: 3-bromo-4-chloro-2-oxo-2H-[1,2′-bipyridine]-5-carboxylic acid methyl ester (100 mg, 0.29 mmol, 1.0 eq) was placed in NH3 / MeOH (4 M, 5 mL) and reacted at 70°C for 12 hours. After completion of the reaction, it was concentrated under reduced pressure. The residue was purified by preparative TLC (DCM / MeOH=20 / 1) to give a white solid (60 mg, 67% yield). LC-MS: 310.95 [M+H] +f) Preparation of 4-amino-3-(5-methyl-1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide: Under nitrogen, 4-amino-3-bromo-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide (30 mg L, 0.1 mmol, 1.0 eq) was placed in a mixed solution of dioxane (5 mL) and H2O (1 mL), and (5-methyl-1H-indazol-4-yl)boric acid (35 mg, 0.2 mmol, 2.0 eq), SPhos-Pd-G3 (15 mg, 0.02 mmol, 0.2 eq) and K3PO4 (42 mg, 0.2 mol, 2.0 eq) were added, and the mixture was reacted at 100°C for 12 hours. The reaction solution was cooled to room temperature, water (20 mL) was added, and EA (30 mL × 3) was used for extraction. The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative HPLC to give a white solid (2.3 mg, 6.6% yield). Example 33 7-amino-8-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide was prepared using a synthetic method similar to that of Example 2, replacing 3-chlorobutan-2-one with 2-chloroacetaldehyde and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (5-methyl-1H-indazol-4-yl)boric acid to give 7-amino-8-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide. Example 34 7-Amino-8-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide was prepared by a synthetic method similar to that of Example 2, replacing 3-chlorobutan-2-one with 2-chloroacetaldehyde and replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (1H-indazol-4-yl)boric acid to prepare 7-amino-8-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide. Example 35 7-Amino-6-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 1, replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (1H-indazol-4-yl)boronic acid to obtain 7-amino-6-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide.Example 36 4-Amino-3-(1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide Using a synthetic method similar to that of Example 31, substituting (1H-indazol-4-yl)boronic acid for (5-methyl-1H-indazol-4-yl)boronic acid, 4-amino-3-(1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide was prepared. Example 37 7-Amino-6-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide Using a synthetic method similar to that of Example 3, 7-amino-6-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide was prepared. Example 38 7-Amino-6-(5-methyl-1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide was prepared using a synthetic method similar to that of Example 3, replacing 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole to obtain 7-amino-6-(5-methyl-1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide. Example 39 4-Amino-3-(5-hydroxy-2-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide A synthetic method similar to that of Example 31 was used, replacing (5-methyl-1H-indazol-4-yl)boric acid with (5-hydroxy-2-methylphenyl)boric acid to prepare 4-amino-3-(5-hydroxy-2-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide. Example 40 7-Amino-6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridine-8-carboxamide was prepared by a synthetic method similar to that of Example 1, replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol to obtain 7-amino-6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 41 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 4 was used, replacing 2-chloroacetaldehyde with 3-bromobutan-2-one and replacing 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine with NH4Cl to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide.Example 42 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 4 was used, replacing 2-chloroacetaldehyde with 1-bromo-1-cyclopropylpropan-2-one, and replacing 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine with NH4Cl to prepare 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxamide. Example 43 3-Amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carboxamide a) Preparation of 2-oxocyclohexanecarboxylic acid: Ethyl 2-oxocyclohexanecarboxylate (5.0 g, 29.4 mmol, 1.0 eq) was placed in THF (50 mL) at 0°C, and NaOH (1.3 g, 32.3 mmol, 1.1 eq) and H2O (10 mL) were added. After reacting at 0°C for 3 hours, the mixture was warmed to room temperature and the reaction was continued for 12 hours. The aqueous phase was extracted with diethyl ether, and the pH was adjusted to 4 with 1M HCl in an ice bath. Stirring was continued for 45 minutes. The precipitate was filtered and dried to obtain a white solid (2.98 g, 71% yield). b) Preparation of 2,2-dimethyl-5,6,7,8-tetrahydro-4H-benzo[d][1,3]dioxan-4-one: To a solution of 2-oxocyclohexanecarboxylic acid (1.0 g, 7.0 mmol, 1.0 eq), acetone (818 mg, 14.1 mmol, 2.0 eq) and acetic anhydride (1.6 g, 15.4 mmol, 2.2 eq) was added concentrated sulfuric acid (173 mg, 1.8 mmol, 0.25 eq) at -5°C. The mixture was reacted at 0°C for 4 hours, poured into 10% Na2CO3 solution (20 mL), and extracted with diethyl ether (20 mL x 3). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a colorless solid (1.2 g, 94% yield). c) Preparation of N-(3-methoxy-2,6-dimethylphenyl)-2-oxocyclohexanecarboxamide: 2,2-Dimethyl-5,6,7,8-tetrahydro-4H-benzo[d][1,3]dioxane-4-one (800 mg, 4.4 mmol, 1.0 eq) was placed in xylene (20 mL) under nitrogen, and 3-methoxy-2,6-dimethylaniline (730 mg, 4.8 mmol, 1.1 eq) was added. The mixture was microwaved at 150°C for 5 minutes, and the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (DCM / MeOH = 1 / 0 to 30 / 1) to give a white solid (390 mg, 33% yield). LC-MS: 376.1 [M+H]. + , 374.1[MH] -. d) Preparation of 3-amino-2-(3-methoxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carbonitrile: Under nitrogen conditions, N-(3-methoxy-2,6-dimethylphenyl)-2-oxocyclohexanecarboxamide (300 mg, 1.1 mmol, 1.0 eq) was placed in an EtOH (30 mL) solution, and malononitrile (132 mg, 2.2 mmol, 2.0 eq) and piperidine (60 mg, 0.7 mmol, 0.6 eq) were added, and the reaction was carried out at 100° C. for 2 hours. The reaction solution was cooled and filtered, and the filter cake was dried to obtain a white solid (230 mg, 65% yield). LC-MS: 324.1 [M+H] + , 322.1[MH] - e) Preparation of 3-amino-2-(3-methoxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carboxamide: Under nitrogen conditions, 3-amino-2-(3-methoxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (230 mg, 0.7 mmol, 1.0 eq) was placed in 84% sulfuric acid (10 mL). After reacting at room temperature for 0.5 hours, the reaction was continued at 95°C for 2 hours. The reaction solution was cooled to room temperature and quenched with ice water. The mixture was adjusted to alkalinity with ammonia solution, extracted with EA (30 mL×3), the organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column (DCM / MeOH=10 / 1) to give a yellow solid (75 mg, 31% yield). LC-MS: 342.1[M+H] + , 340.1[MH] -f) Preparation of 3-amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carboxamide: 3-amino-2-(3-methoxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carboxamide (75 mg, 0.2 mmol, 1.0 eq) was placed in a DCM (8 mL) solution at 0°C, BBr3 (150 mg, 0.6 mmol, 3.0 eq) was added, and the mixture was reacted at 0°C for 16 hours. Water (10 mL) was added and the mixture was extracted with EA (10 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give a crude product. The crude product was purified by preparative HPLC (water / acetonitrile = 42 / 58%, 0.1% HCOOH) to give a white solid (8.8 mg, 13% yield). Example 44 7-Amino-2-hydroxy-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide is prepared using a synthetic method similar to that of Example 1, replacing 2-chloroacetaldehyde with 2-bromoacetic acid to obtain 7-amino-2-hydroxy-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 45 3-Amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopentadiene[c]pyridine-4-carboxamide was prepared using a synthetic method similar to that of Example 41, replacing N-(3-methoxy-2,6-dimethylphenyl)-2-oxocyclopentane-1-carboxamide with N-(3-methoxy-2,6-dimethylphenyl)-2-oxocyclohexane-1-carboxamide to obtain 3-amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopentadiene[c]pyridine-4-carboxamide. Example 46 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Preparation of 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide: 2,4-diaminonicotinic acid methyl ester (30 mg, 0.1 mmol, 1.0 eq) was placed in DMF (2.5 mL) and NCS (13 mg, 0.1 mol, 1.0 eq) was added. The reaction was carried out at room temperature under nitrogen for 1 hour. After the reaction was completed, water (10 mL) was added and extracted with EA (10 mL×5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (C 18, ACN in H2O, 5-55%, 0.1% HCOOH) was purified to give a white solid (11.2 mg, 34% yield). Example 47 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylthiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 1, replacing 2-chloroacetaldehyde with 2-bromo-1-(4-methylthiazol-2-yl)ethan-1-one, 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylthiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide was prepared. Example 48 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-cyclopropylethane-1-one to prepare 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 49 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 1, 2-chloroacetaldehyde was replaced with 2-bromo-1-(thiazol-2-yl)ethane-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 50 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 46, 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide was prepared. Example 51 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-phenylimidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-phenylethanol-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-phenylimidazo[1,2-a]pyridine-8-carboxamide. Example 52 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethane-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide.Example 53 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 1-bromo-3-methylbutan-2-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide. Example 54 7-amino-2-(benzo[d]thiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 1-(benzo[d]thiazol-2-yl)-2-bromoethane-1-one to prepare 7-amino-2-(benzo[d]thiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 55 7-amino-6-(6-chloro-3-hydroxy-2-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 58, 3-bromo-4-methylphenol was substituted with 3-bromo-2-methylphenol to prepare 7-amino-6-(6-chloro-3-hydroxy-2-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide. Example 56 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxamide a) Preparation of 7-bromo-1H-indazole-6-amine: 1H-indazole-6-amine (0.5 g, 3.8 mmol, 1.0 eq) was placed in THF (10 mL) and NBS (676 mg, 3.8 mmol, 1.0 eq) was added. The reaction was carried out at room temperature under nitrogen for 4 hours. After the reaction was complete, saturated NaHCO3 (20 mL) was added and extracted with EA (20 mL x 5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a yellow solid (620 mg, 78% yield). LCMS: 213.85 [M+H]. + b) Preparation of methyl 6-amino-1H-indazole-7-carboxylate: 7-bromo-1H-indazole-6-amine (620 mg, 2.9 mmol, 1.0 eq) was placed in MeOH (20 mL), and Pd(dppf)Cl2 (219 mg, 0.3 mmol, 0.1 eq) and TEA (879 mg, 8.7 mmol, 3.0 eq) were added. The mixture was reacted at 70°C under CO2 for 20 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was purified with silica gel (PE:EA=1:1) to give a yellow solid (610 mg, crude product). LCMS: 191.95 [M+H] +. c) Preparation of methyl 6-amino-5-iodo-1H-indazole-7-carboxylate: methyl 6-amino-1H-indazole-7-carboxylate (160 mg, crude product) was placed in DMF (10 mL) and NIS (787 mg, 3.5 mmol) was added. The reaction was allowed to react at room temperature under nitrogen for 16 hours. After the reaction was completed, water (20 mL) was added and extracted with EA (20 mL×5). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel (PE / EA=4 / 1) to give a yellow solid (330 mg, 35% yield). LC-MS: 317.90 [M+H] + d) Preparation of methyl 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylate: Methyl 6-amino-5-iodo-1H-indazole-7-carboxylate (330 mg, 1.0 mmol, 1.0 eq) was placed in a mixed solution of dioxane (15 mL) and H₂O (3 mL) at room temperature. 2,4-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (372 mg, 1.5 mmol, 1.5 eq), CataCXium A Pd G₃ (73 mg, 0.1 mmol, 0.1 eq), and K₃PO₄ (636 mg, 3.0 mmol, 3.0 eq) were added. The mixture was reacted at 100°C under nitrogen for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, water (10 mL) was added, and extraction was performed with EA (10 mL x 3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (DCM / MeOH=20 / 1) to give a yellow solid (130 mg, 40% yield). LC-MS: 312.05 [M+H] + , 309.95[MH] - . e) Preparation of 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylic acid: At room temperature, 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylic acid methyl ester (130 mg, 0.4 mmol, 1.0 eq) was placed in a mixed solution of EtOH (10 mL) and H2O (10 mL), and NaOH (160 mg, 4.0 mmol, 10.0 eq) was added. The reaction was carried out at 60 ° C under nitrogen for 16 hours. After the reaction was completed, 1 M dilute hydrochloric acid solution was added to adjust the pH to 7. The precipitate was filtered off and dried under reduced pressure to obtain a yellow solid (110 mg, crude product). LC-MS: 298.00 [M+H] + , 295.90[MH] -f) Preparation of 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxamide: 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxylic acid (110 mg, crude product) was placed in DMF (10 mL) at room temperature, and NH4Cl (108 mg, 2.0 mmol, 5.0 eq), HATU (228 mg, 0.6 mmol, 1.5 eq) and DIEA (518 mg, 4.0 mmol, 10.0 eq) were added. The reaction was carried out at room temperature under nitrogen for 16 hours. After completion of the reaction, the reaction was concentrated and the residue was purified by preparative HPLC (C 18,ACN in H2O, 5-55%, 0.1% HCOOH) was purified to give a white solid (15.2 mg, 12% yield). Example 57 7-Amino-6-(2-chloro-3-hydroxy-6-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol: 3-Bromo-4-methylphenol (6.0 g, 32.26 mmol, 1.0 eq) was placed in dioxane (80 mL), and B2P2 (16.4 g, 64.52 mmol, 2.0 eq), Pd(dppf)Cl2 (253 mg, 0.323 mmol, 0.1 eq) and KOAc (9.5 g, 96.78 mmol, 3.0 eq) were added. The reaction was carried out at 110°C for 16 hours. After completion of the reaction, water (50 mL) was added and extracted with EA (100 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (PE:EA = 10:1) to obtain a white solid (4.5 g, 60% yield). b) Preparation of 2-chloro-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol: 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.0 g, 4.27 mmol, 1.0 eq) was placed in ACN (10 mL) at 0°C, and NCS (570 mg, 4.27 mmol, 1.0 eq) was added. The reaction was carried out at 40°C under nitrogen for 16 hours. After completion of the reaction, the mixture was concentrated. The residue was purified by silica gel chromatography (PE:EA = 10:1) to give a white solid (480 mg, 42% yield). c) Preparation of methyl 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylate: Methyl 2,4-diamino-5-iodonicotinate (1.5 g, 5.1 mmol, 1.0 eq) was placed in EtOH (15 mL) and 3-bromobutan-2-one (3.84 g, 25.6 mmol, 5.0 eq) was added. The mixture was reacted at 100°C for 16 hours. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel chromatography (DCM:MeOH = 10:1) to give a yellow solid (1.5 g, 84% yield). LC-MS: 345.95 [M+H] +. d) Preparation of 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid: 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (1.5 g, 4.35 mmol, 1.0 eq) was placed in a mixed solution of MeOH / H2O (20 mL / 8 mL) and NaOH (1.74 g, 43.5 mmol, 10 eq) was added. The reaction was carried out at 50°C for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature and concentrated. Water (5 mL) was added and 2.0 M HCl was added to adjust the pH to 4. The reaction solution was concentrated to obtain a yellow oil (1.5 g, crude product). LC-MS: 332.00 [M+H] + . e) Preparation of 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide (1.50 g, crude product) was placed in DMF (20 mL), and NH4Cl (364 mg, 6.80 mmol), HATU (2.58 g, 6.80 mmol), and DIEA (1.75 g, 13.6 mmol) were added. The mixture was reacted at 45°C for 16 hours. After the reaction was completed, water (10 mL) and EA (20 mL × 3) were added, and the organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (DCM:MeOH=15:1) to give a yellow solid (1.0 g, 70% yield). LC-MS: 330.95 [M+H] + f) Preparation of 7-amino-6-(2-chloro-3-hydroxy-6-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-iodo-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide (82 mg, 0.248 mmol, 1.0 eq) was placed in a mixed solution of dioxane / H2O (3 mL / 1 mL), and 2-chloro-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (80 mg, 0.298 mmol, 1.2 eq), cataCxium-Pd-G3 (9.0 mg, 0.0124 mmol, 0.05 eq) and K3PO4 (158 mg, 0.744 mmol, 3.0 eq) were added. The mixture was reacted at 110°C for 16 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by preparative HPLC (C 18 Purification with acetonitrile in H2O, 5% to 50%, 0.1% HCOOH) gave a white solid (4.4 mg, 5.2% yield). LC-MS: 345.10 [M+H] + , 343.05[MH] -. Example 58 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-morpholinoyl azo[1,2-a]pyridine-8-carboxamide 7-amino-2-bromo-6-(3-hydroxy-2,6-dimethylphenyl) imidazo[1,2-a]pyridine-8-carboxamide (50 mg) was placed in a DIEA (5 mL) solution and morpholine (1.0 mL) was added. Microwave reaction was carried out at 160°C for 2 hours. After the reaction was completed, water (40 mL) was added and extracted with EtOAc (30 mL×3). The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC (C 18The reaction mixture was purified by adding 5-55% ACN in H2O, 0.1% HCOOH) to afford the title compound as a white solid (2.1 mg, 4% yield). Example 59 6-Amino-5-(3-hydroxy-2,6-dimethylphenyl)-1-methyl-1H-indazole-7-carboxamide Using a synthetic method similar to that of Example 57, substituting 1H-indazole-6-amine with 1-methyl-1H-indazole-6-amine, 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1-methyl-1H-indazole-7-carboxamide was prepared. Example 60 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(5-methylpyridin-2-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-(5-methylpyridin-2-yl)ethane-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(5-methylpyridin-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 61 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 1, replacing 2-chloroacetaldehyde with 1-bromobutan-2-one, 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide was prepared. Example 62 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 1, replacing 2-chloroacetaldehyde with 3-bromo-1,1,1-trifluoropropane-2-one, 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide was prepared. Example 63 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxamide A synthetic method similar to that of Example 28 was used, replacing pyridin-2-amine with aniline to prepare 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxamide. Example 64 7-amino-2-cyano-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 65 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-5-carboxamide A synthesis method similar to that of Example 2 was used, replacing 3-chlorobutan-2-one with 2-chloroacetaldehyde to prepare 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-5-carboxamide.Example 66 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methoxyimidazo[1,2-a]pyridine-8-carboxamide Example 67 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-4-carboxamide a) Preparation of benzo[d]thiazole-5-amine: 5-nitrobenzo[d]thiazole (2.0 g, 11.1 mmol, 1.0 eq) was placed in a mixed solution of EtOH / H2O (15 mL / 15 mL), and Fe (6.2 g, 111.1 mmol, 10.0 eq) and NH4Cl (5.9 g, 111.11 mmol, 10.0 eq) were added. The mixture was stirred at 85°C under N2 for 2 hours. After the reaction was completed, the reaction solution was filtered and washed with EtOH, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (PE:EA=10:1) to give a yellow solid (1.5 g, 90% yield). LC-MS: 151.10 [M+H]. + b) Preparation of 4,6-dibromobenzo[d]thiazol-5-amine: Benzo[d]thiazol-5-amine (1.5 g, 10.0 mmol, 1.0 eq) was placed in CHCl₃ (20 mL) and Br₂ (1.7 g, 10.3 mmol, 1.0 eq) was added. The mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (PE:EA = 5:1) to give the compound as a white solid (410 mg, 13% yield). c) Preparation of 3-(5-amino-4-bromobenzo[d]thiazol-6-yl)-2,4-dimethylphenol: 4,6-Dibromobenzo[d]thiazol-5-amine (310 mg, 1.0 mmol, 1.0 eq) was placed in a mixture of dioxane / H₂O (5 mL / 2 mL). 2,4-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (377 mg, 1.5 mmol, 1.5 eq), catacxium-Pd-G₃ (146 mg, 0.2 mmol, 0.2 eq), and K₃PO₄ (624 mg, 3.0 mmol, 3.0 eq) were added. The reaction mixture was stirred at 110°C under nitrogen for 16 hours. After completion of the reaction, the mixture was quenched with water (10 mL) and extracted with EA (15 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC (PE:EA=3:1) to give a yellow solid compound (130.0 mg, 37% yield). LC-MS: 349.00, 351.00 [M+H] +. d) Preparation of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-4-carbonitrile: 3-(5-amino-4-bromobenzo[d]thiazole-6-yl)-2,4-dimethylphenol (130 mg, 0.37 mmol, 1.0 eq) was placed in NMP (3 mL) solution and CuCN (43.0 mg, 0.484 mmol, 1.3 eq) was added. The reaction was carried out at 200 ° C for 1.5 hours under microwave conditions. After the reaction was completed, water (10 mL) was added and extracted with EA (5 mL×3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a yellow oily compound (0.1 g, 92% yield). LC-MS: 296.05 [M+H] +e) Preparation of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-4-carboxamide: 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-4-carbonitrile (0.1 g, 0.34 mmol) was placed in DMSO (2 mL), and K2CO3 (141 mg, 1.02 mmol, 3.0 eq) and H2O2 (3 mL) were added. Stir at room temperature for 6 hours. After completion of the reaction, the mixture was purified by preparative HPLC (C18, ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (6.0 mg, 6% yield). Example 68 5-Amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]oxazole-4-carboxamide 5-Amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]oxazole-4-carboxamide was prepared using a synthetic method similar to Reaction Scheme 1, replacing pyridine-2,4-diamine with benzo[d]oxazole-5-amine. Examples 69-70 Separation of Atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Racemic 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide (Example 49, 225 mg) was subjected to SFC chiral column separation (OX-3, CO2:EtOH=60:40, 0.05% DEA) to obtain two fractions. The first fraction was lyophilized to obtain Example 69 (8.4 mg, 4% yield), and the second fraction was lyophilized to obtain Example 70 (9.0 mg, 4% yield). Example 71 7-amino-2-(4-chlorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-chloro-1-(4-chlorothiazol-2-yl)ethane-1-one to prepare 7-amino-2-(4-chlorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 72 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxamide a) Preparation of 7-bromo-1-methyl-1H-indazole-6-amine: To a solution of 1H-indazole-6-amine (0.5 g, 3.8 mmol, 1.0 eq) in THF (10 mL) was added NBS (676 mg, 3.8 mmol, 1 eq). The mixture was stirred at room temperature under nitrogen for 4 hours. After completion of the reaction, it was quenched with saturated NaHCO3 (20 mL) and extracted with EA (20 mL×5).The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a yellow solid (620 mg, 78% yield). LCMS: 211.85, 213.85 [M+H]. + . b) Preparation of methyl 6-amino-1H-indazole-7-carboxylate: 7-bromo-1H-indazole-6-amine (620 mg, 2.9 mmol, 1.0 eq) was placed in MeOH (20 mL), and Pd(dppf)Cl2 (219 mg, 0.3 mmol, 0.1 eq) and TEA (879 mg, 8.7 mmol, 3.0 eq) were added. The reaction solution was stirred at 70°C and CO for 20 hours. After the reaction was completed, the reaction solution was concentrated. The residue was purified with silica gel (PE:EA=1:1) to obtain a yellow solid crude product (610 mg). LCMS: 191.95 [M+H] + . c) Preparation of methyl 6-amino-5-iodo-1H-indazole-7-carboxylate: methyl 6-amino-1H-indazole-7-carboxylate (610 mg, crude product) was placed in DMF (10 mL) and NIS (787 mg, 3.5 mmol) was added. Stir at room temperature for 16 hours under nitrogen protection. After the reaction was completed, water (20 mL) was added and extracted with EA (20 mL×5). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel (PE / EA=4 / 1) to give a yellow solid (330 mg, 35% 2-step yield). LC-MS: 317.90 [M+H] + . d) Preparation of methyl 6-amino-2-(difluoromethyl)-5-iodo-2H-indazole-7-carboxylate: methyl 6-amino-5-iodo-2H-indazole-7-carboxylate (100 mg, 0.3 mmol, 1.0 eq) and diethyl (bromodifluoromethyl)phosphonate (120 mg, 0.45 mmol, 1.5 eq) were placed in ACN (10 mL) and KF (35 mg, 0.6 mmol, 2.0 eq) was added. The reaction solution was stirred at 100 ° C. under nitrogen protection for 3 hours. After the reaction was completed, water (20 mL) was added and extracted with DCM (20 mL×3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel (PE / EA=2 / 1) to give a white solid (90 mg, 78% yield). LC-MS: 367.85[M+H] +e) Preparation of methyl 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxylate: Methyl 6-amino-2-(difluoromethyl)-5-iodo-2H-indazole-7-carboxylate (90 mg, 0.3 mmol, 1.0 eq) was placed in a mixed solution of dioxane (15 mL) and H2O (3 mL), and 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (99 mg, 0.4 mmol, 1.2 eq), CataCXium A Pd G3 (73 mg, 0.1 mmol, 0.1 eq), and K3PO4 (191 mg, 0.9 mmol, 3.0 eq) were added. The reaction mixture was reacted at 100°C under nitrogen for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, diluted with water (10 mL), and extracted with EA (10 mL × 3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparative TLC (DCM / MeOH = 20 / 1) to give a yellow solid (800 mg, 90% yield). LC-MS: 362.05 [M+H] +, 359.95 [MH] -. f) Preparation of 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxylic acid: 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxylic acid methyl ester (80 mg, 0.2 mmol, 1.0 eq) was placed in a mixed solution of EtOH (10 mL) and H2O (10 ml), and NaOH (80 mg, 2.0 mmol, 10.0 eq) was added. The reaction solution was reacted at 60°C under nitrogen protection for 16 hours. After the reaction was completed, 1 M aqueous hydrochloric acid solution was added to the reaction solution to adjust the pH to 7. The precipitate was filtered off and dried under reduced pressure to obtain a white solid (80 mg, crude product). LC-MS: 347.95 [M+H] + , 345.90[MH] -. g) Preparation of 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxamide: 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxylic acid (80 mg, crude) was placed in a DMF (10 mL) solution, and NH4Cl (54 mg, 1.0 mmol), HATU (114 mg, 0.3 mmol) and DIEA (258 mg, 2.0 mmol) were added. The reaction solution was reacted at room temperature under nitrogen for 16 hours. After completion of the reaction, the reaction solution was concentrated and the residue was purified by preparative HPLC (C18, ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (15.2 mg, 20% yield over 2 steps). LC-MS: 347.00 [M+H]+, 344.85 [MH]-. Example 73 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide: 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide (40 mg, 0 0.1 mmol, 1.0 eq) was placed in a mixed solution of dioxane (5 mL) and H2O (1 mL). Under nitrogen protection, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (129 mg, 0.53 mmol, 5.0 eq), Pd(dppf)Cl2 (16 mg, 0.02 mmol, 0.2 eq), and Cs2CO3 (174 mg, 0.53 mmol, 5.0 eq) were added. The reaction solution was reacted at 100°C for 16 hours. After completion of the reaction, water (30 mL) was added, and the mixture was extracted with EtOAc (30 mL × 3). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH=10:1) to give a yellow solid (42 mg, 80% yield). LC-MS: 493.20 [M+H]+, 491.10 [MH] -. b) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide (34 mg) was placed in a THF (4 mL) solution and TBAF (1 M THF, 10 mL) was added. The reaction solution was reacted at room temperature for 16 hours. After the reaction was complete, water (30 mL) was added and extracted with EtOAc (30 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative HPLC to give a yellow solid (1.0 mg, 4% yield). LC-MS: 362.95[M+H] + , 360.90[MH] -Example 74 7-amino-6-(5-methylbenzo[d]thiazol-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 1, replacing 2-chloroacetaldehyde with 2-bromo-1-(thiazol-2-yl)ethane-1-one to prepare 7-amino-6-(5-methylbenzo[d]thiazol-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Examples 75-76 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide Racemic 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide (Example 53) was separated by SFC chiral column using a method similar to that of Examples 69-70 to obtain two components, namely Examples 75 and 76. Example 77 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used, 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol was replaced with (5-methyl-1H-indazol-4-yl)boric acid, and 2-chloroacetaldehyde was replaced with 2-chloro-1-(thiazol-2-yl)ethane-1-one to prepare 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 78 7-amino-2-(4-fluorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 79 7-amino-2-(5-fluorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 80 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-(thiazol-5-yl)ethan-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide.Example 81 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(isothiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthesis method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-(isothiazol-5-yl)ethane-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(isothiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 82 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(oxazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 1,1,3-trichloropropane-2-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(oxazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 83 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used, and 2-bromo-1-(1-methyl-1H-pyrazol-3-yl)ethane-1-one was used to replace 2-chloroacetaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 84 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-hydroxypropyl-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 85 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-ylmethyl)imidazo[1,2-a]pyridine-8-carboxamide Example 86 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yloxy)imidazo[1,2-a]pyridine-8-carboxamide Example 87 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 2-(chloromethyl)thiazole: Thiazol-2-ylmethanol (1.0 g, 8.7 mmol, 1.0 eq) was placed in DCM (10 mL) and SOCl2 (2.1 g, 17.4 mmol, 2.0 eq) was added. The reaction was carried out at 40°C under nitrogen for 2 hours. After the reaction was completed, ice water (10 mL) was added and the pH was adjusted to 2 with saturated sodium bicarbonate aqueous solution. The mixture was extracted with DCM (15 mL x 3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (PE / EA = 2 / 1) to give a yellow oil (0.9 g, yield: 78%).b) Preparation of triphenyl(thiazol-2-ylmethyl)phosphonium chloride: Under nitrogen, 2-(chloromethyl)thiazole (0.9 g, 6.8 mmol, 1.0 eq) was placed in toluene (10 mL) and PPh3 (2.0 g, 7.5 mmol, 1.1 eq). The reaction mixture was reacted at 125°C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered to obtain a white solid (2.0 g, 99% yield). c) Preparation of (E)-7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)vinyl)imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester: At room temperature and nitrogen, triphenyl(thiazol-2-ylmethyl)phosphonium chloride (2.0 g, 5.1 mmol, 1.0 eq) was placed in THF (20 mL), and 7-amino-2-formyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (0.23 g, 5.1 mmol, 1.0 eq) and t-BuOK (0.65 g, 5.1 mmol, 1.0 eq) were added. The reaction solution was stirred at room temperature for 12 hours. After the reaction was completed, water (20 mL) was added and the mixture was extracted with EA (20 mL × 3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel (PE / EA=5 / 1) to give a yellow solid (57 mg, 20% yield). LC-MS: 421.00 [M+H]. + . d) Preparation of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxylate: (E)-methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)vinyl)imidazo[1,2-a]pyridine-8-carboxylate (57 mg, 0.14 mmol, 1.0 eq) was placed in MeOH (5 mL), Pd / C (12 mg, 20 wt%) was added, and the reaction solution was stirred at room temperature under H2 for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (C 18 Purification with 5% ACN in H2O, 5-50%, 0.1% HCOOH) gave a colorless oil (50 mg, 87% yield). LCMS: 422.95 [M+H] +. e) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxylic acid: Methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxylate (50 mg, 0.1 mmol, 1.0 eq) was placed in MeOH (2 mL) at room temperature, and NaOH solution (142 mg dissolved in 1.8 mL of water) was added. The reaction solution was stirred at 40° C. for 12 hours. After completion of the reaction, it was concentrated under reduced pressure. The residue was dissolved in H2O (2 mL) and the pH was adjusted to 2 with 2N HCl. The mixture was then concentrated under reduced pressure to give a crude product (55 mg), which was used in the next step without purification. LC-MS: 409.25 [M+H] + . f) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide: Under nitrogen conditions, 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxylic acid (55 mg, crude product) was placed in DMF (2.0 mL), and NH4Cl (15 mg, 0.2 mmol), HATU (103 mg, 0.2 mol) and DIEA (52 mg, 0.4 mmol) were added. The reaction solution was stirred at 40 ° C for 12 hours. After the reaction was completed, water (5 mL) was added and extracted with EA (5 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product. The crude product was purified by preparative HPLC (C 18 , ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (1.1 mg, 2% yield). LC-MS: 408.00 [M+H] +Example 88 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylpyrazolo[1,5-a]pyridine-4-carboxamide Example 89 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)pyrazolo[1,5-a]pyridine-4-carboxamide Example 90 6-Amino-7-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-5-carboxamide was prepared using a synthetic method similar to that of Example 1, replacing 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate with methyl 3,6-diamino-4-(3-hydroxy-2,6-dimethylphenyl)picolinate and 2-chloroacetaldehyde with 1-bromo-3-methylbutan-2-one. Example 91 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-5-carboxamide Example 92 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylbenzo[d]thiazole-4-carboxamide Example 93 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)benzo[d]thiazole-4-carboxamide A synthetic method similar to that of Example 1 was used to replace 2,4-diamino-5-iodonicotinic acid methyl ester with 5-amino-6-bromo-2-(thiazol-2-yl)benzo[d]thiazole-4-carboxamide to prepare 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)benzo[d]thiazole-4-carboxamide.Example 94 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)benzo[d]thiazole-7-carboxamide Example 95 7-amino-6-(4-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 96 7-amino-6-(5-hydroxy-2,4-dimethylpyridin-3-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 97 7-amino-6-(2-ethyl-3-hydroxy-6-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 98 7-Amino-6-(6-ethyl-3-hydroxy-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 99 7-Amino-6-(3-hydroxy-6-isopropyl-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 100 7-Amino-6-(6-cyclopropyl-3-hydroxy-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used with 7-amino-6-iodo-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Formamide replaced 2,4-diamino-5-iodonicotinate methyl ester, and 4,6-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol replaced 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol to prepare 7-amino-6-(6-cyclopropyl-3-hydroxy-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 101 7-amino-6-(3-hydroxy-2-methyl-6-(trifluoromethyl)phenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 102 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-2H-indazole-7-carboxamide A synthetic method similar to that of Example 1 was used, replacing 2,4-diamino-5-iodonicotinic acid methyl ester with 6-amino-5-bromo-2-isopropyl-2H-indazole-7-carboxylic acid methyl ester to prepare 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-2H-indazole-7-carboxamide.Example 103 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-2H-indazole-7-carboxamide Example 104 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)indolizine-5-carboxamide Example 105 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-7-carboxamide Example 106 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-5-carboxamide Example 107 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-1H-benzo[d]imidazole-4-carboxamide Example 108 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-7-carboxamide Example 109 5-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-1H-indole-4-carboxamide Example 110 5-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-1H-indole-4-carboxamide a) Preparation of 4,6-dibromobenzothiophene-5-amine: To a solution of benzo[b]thiophene-5-amine (100 mg, 0.67 mmol, 1.0 eq) in DMSO (3 mL) was added HBr (48% wt, 230 mg, 1.3 mmol, 2.0 eq). Stir at room temperature for 16 hours. Then, HBr (48% wt, 230 mg, 1.3 mmol, 2.0 eq) was added. The mixture was stirred at 100°C for 2 hours. After the reaction was complete, the solution was cooled to room temperature and the reaction was poured into ice water. Concentrated ammonium hydroxide was added to the mixture until the pH reached 9 and a solid precipitated from the solution. The precipitate was collected on a filter, washed with water, and dried under reduced pressure to give 4,6-dibromobenzothiophene-5-amine as a gray solid (0.2 g, 97% yield). LC-MS: 307.85 [M+H]. +b) Preparation of 3-(5-amino-4-bromobenzothiophen-6-yl)-2,4-dimethylphenol: To a solution of 4,6-dibromobenzo[b]thiophen-5-amine (150 mg, 0.49 mmol, 1.0 eq) in dioxane / water (3 mL / 1 mL) were added 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (182 mg, 0.734 mmol, 1.5 eq), [n-butyldi(1-adamantyl)phosphine](2-amino-1,1′-biphenyl-2-yl)palladium(II) methanesulfonate (catacxium-Pd-G3, 36 mg, 0.049 mmol, 0.1 eq), and K3PO4 (311 mg, 1.467 mmol, 3.0 eq). The mixture was stirred at 110° C. for 16 hours. After the reaction was complete, the mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH = 15:1) to give 3-(5-amino-4-bromobenzothiophen-6-yl)-2,4-dimethylphenol as a gray solid (65 mg, 38% yield). LC-MS: 348.00 [M+H] + c) Preparation of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzothiophene-4-carbonitrile: To a solution of 3-(5-amino-4-bromobenzo[b]thiophen-6-yl)-2,4-dimethylphenol (60 mg, 0.187 mmol, 1.0 eq) in NMP (3 mL) was added CuCN (22 mg, 0.243 mmol, 1.3 eq). The mixture was stirred at 200° C. under microwave for 1.5 hours. After completion of the reaction, the mixture was quenched with water (20 mL) and extracted with EA (10 mL×3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH=12:1) to give 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzothiophene-4-carbonitrile (40 mg, 73% yield) as a white solid. LC-MS: 295.05 [M+H] + d) Preparation of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzothiophene-4-carboxamide: To a solution of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[b]thiophene-4-carbonitrile (40 mg, 0.136 mmol, 1.0 eq) in DMSO (1.5 mL) were added K2CO3 (56 mg, 0.408 mmol, 3.0 eq) and H2O2 (1.5 ml). The mixture was stirred at room temperature for 6 hours. After completion of the reaction, the product was separated by preparative high performance liquid chromatography (C 18The mixture was purified by 5-50% ACN in H2O, 0.1% HCOOH) to afford the preparation of 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzothiophene-4-carboxamide as a white solid (3.7 mg, 8.7% yield). LC-MS: 313.00 [M+H] + , 310.90[MH] -Example 111 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[b]thiophene-4-carboxamide Example 112 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)benzo[b]thiophene-7-carboxamide Example 113 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(2-neoamidophenyl)-1,6-dihydropyridine-3-carboxamide Example 114 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 115 7-Amino-6-(2-hydroxy-3,5-dimethylpyridin-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 1, replacing 2,4-diamino-5-iodonicotinic acid methyl ester with 7-amino-6-iodo-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide, and replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (2-methoxy-3,5-dimethylpyridin-4-yl)boric acid. Example 116 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-morpholinylimidazo[1,2-a]pyridine-8-carboxamide Example 117 7-Amino-2-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 118 7-Amino-2-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 119 7-Amino-2-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 73, replacing 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole to obtain 7-amino-2-bromo-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide.Example 120 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 73 was used to replace 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-1H-pyrazole with 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 121 Preparation of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a)-(methylsulfonyl)hydroxylamine: At 0°C, tert-butyl ((methylsulfonyl)oxy)carbamate (5.0 g, 15.87 mmol, 1.0 eq) was placed in a TFA (20 mL) solution. The mixture was stirred at 0°C under N2 for 2 hours. After the reaction was completed, the reaction solution was poured into ice water, and a white solid precipitated. The solid was filtered to obtain a white solid (3.4 g, 100% yield). b) Preparation of 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium: Methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (130 mg, 0.45 mmol, 1.0 eq) was placed in DCM (3 mL) and O-(methylsulfonyl)hydroxylamine (292 mg, 1.4 mmol, 3.0 eq) was added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to give a yellow oil (0.1 g, crude product). LC-MS: 303.05 [M+H]. + . c) Preparation of methyl 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate: 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium (0.1 g, crude product) was placed in dioxane (2 mL), and cyclopropanecarboxaldehyde (46 mg, 0.66 mmol) and DBU (150 mg, 1.0 mmol) were added. The reaction solution was stirred at 90°C for 16 hours. After the reaction was completed, water (5 mL) was added and extracted with EA (10 mL×3). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative TLC (PE:EA=1:1) to give a yellow solid (35 mg, 9% yield). LC-MS: 353.10 [M+H]+ . d) Preparation of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid: 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester (35 mg, 0.1 mmol, 1.0 eq) was placed in MeOH / H2O (2 mL / 0.5 mL) and NaOH (40 mg, 1.0 mmol, 10.0 eq) was added. Under nitrogen, the reaction solution was stirred at 80°C for 2 hours. After the reaction was completed, it was concentrated under reduced pressure. Water (1 mL) was added and 2N HCl was added to adjust the pH to 4. The reaction solution was concentrated under reduced pressure to give a yellow oil (35 mg, crude product). LC-MS: 339.35 [M+H] + e) Preparation of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (35.0 mg, crude product) was placed in DMF (2 mL), and NH4Cl (8.0 mg, 0.16 mmol, 1.0 eq), HATU (59.0 mg, 0.16 mmol, 1.0 eq), DIEA (40.0 mg, 0.3 mmol, 2.0 eq) were added. Stir at room temperature for 16 hours. After completion of the reaction, the product was purified by preparative HPLC (C 18 The mixture was purified by HPLC (5% HCl, ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (22.2 mg, 66% yield). Example 122 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-phenylimidazo[1,2-a]pyridine-8-carboxamide To a mixed solution of 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide (10 mg, 0.03 mmol, 1.0 eq) in dioxane (2.5 mL) and H2O (0.5 mL) were added phenylboronic acid (13 mg, 0.11 mmol, 4.0 eq) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (Pd(dppf)Cl2, 4 mg, 0.01 mmol, 0.2 eq) and Cs2CO3 (44 mg, 0.13 mmol, 5.0 eq). The mixture was stirred at 100°C for 16 hours. LCMS showed that the reaction was complete, water (30 mL) was added, and the mixture was extracted with EtOAc (30 mL×3). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC (C 18, ACN in H2O, 5-55%, 0.1% HCOOH) to give 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-phenylimidazo[1,2-a]pyridine-8-carboxamide (1.4 mg, 14% yield) as a white solid. Example 123 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide Example 124 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Example 125 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methoxyimidazo[1,2-a]pyridine-8-carboxamide 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide (30 mg, 0.08 mmol, 1.0eq) was placed in MeOH (10 mL), and DBU (24.5 mg, 0.16 mmol, 2.0eq), Cs2CO3 (52.5 mg, 0.16 mmol, 2.0eq) and CuI (3.0 mg, 0.016 mmol, 0.2eq) were added. The reaction solution was stirred at 80°C for 16 hours. After the reaction was completed, water (10 mL) was added and extracted with EtOAc (10 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative HPLC (C18, ACN in H2O, 5-55%, 0.1% HCOOH) to give a yellow solid (1.4 mg, 5% yield). LC-MS: 327.05 [M+H] + , 324.95[MH] -Example 126 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylbenzo[d]thiazole-7-carboxamide Example 127 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 2-bromo-1-(1H-pyrazol-4-yl)ethan-1-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide. Example 128 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide a) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-iodoimidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide (50 mg, 0.17 mmol, 1.0 eq) was placed in DMF (2 mL) and NIS (38 mg, 0.17 mmol, 1.0 eq) was added. The reaction solution was stirred under nitrogen at room temperature for 1 hour. After completion of the reaction, water (10 mL) was added and extracted with EA (15 mL×3). The organic layers were combined and washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (DCM:MeOH = 10:1) to give a yellow solid (45 mg, 63% yield). b) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-2-ylethynyl)imidazo[1,2-a]pyridine-8-carboxamide: Under nitrogen, 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-iodoimidazo[1,2-a]pyridine-8-carboxamide (45 mg, 0.1 mmol, 1.0 eq) was placed in TEA (5 mL), and 2-ethynylthiazole (18 mg, 0.16 mmol, 1.5 eq), Pd(Ph3P)2Cl2 (7.5 mg, 0.01 mmol, 0.1 eq), and CuI (2 mg, 0.01% mmol, 0.1 eq) were added. The reaction mixture was stirred at 100°C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and ice water (20 mL) was added. The mixture was extracted with EA (10 mL × 3). The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM / MeOH = 20 / 1) to give a yellow solid (15.0 mg, 35% yield). LC-MS: 403.95 [M+H] +. c) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-2-ylethynyl)imidazo[1,2-a]pyridine-8-carboxamide (15 mg, 0.04 mmol, 1.0 eq) was placed in MeOH (5 mL) and Pd / C (3 mg, 20% wt) was added. The reaction solution was stirred at room temperature under H2 for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (C 18 , ACN in H2O, 5-55%, 0.1% HCOOH) to give a white solid (1.4 mg, 9% yield). LCMS: 408.00 [M+H] +. Examples 129-130 Separation of atropisomers of 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide Example 61 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 129, and component 2 being Example 130. Examples 131-132 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide Example 61 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 131, and component 2 being Example 132. Examples 133-134 Separation of atropisomers of 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 121 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 133 and component 2 being Example 134. Example 135 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used, substituting 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium for 2,4-diamino-5-iodonicotinic acid methyl ester, and replacing 2-chloroacetaldehyde with 2,2,2-trifluoroacetaldehyde to obtain 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 136-137 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 135 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 136 and component 2 being Example 137.Example 138 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 1 was used, substituting 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium for 2,4-diamino-5-iodonicotinic acid methyl ester, and replacing 2-chloroacetaldehyde with thiazole-2-carboxaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 139-140 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 138 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 139 and component 2 being Example 140. Example 141 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(pyridazin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 142 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide A synthesis method similar to that of Example 1 was used to replace 2-chloroacetaldehyde with 3-bromo-1,1,1-trifluorobutan-2-one to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide. Example 143 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a) Preparation of 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium: To a solution of methyl 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (500 mg, 1.74 mmol, 1.0 eq) in DCM (10 mL) was added O-(mesitylenesulfonyl)hydroxylamine (1.31 g, 6.10 mmol, 3.5 eq) at 0° C. The mixture was reacted at 0° C. for 2 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to obtain 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium as a yellow solid (1.1 g, crude product), which was used directly in the next step. LC-MS: 303.00 [M+H]. +b) Preparation of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate: To a solution of 1,2,4-triamino-5-(3-hydroxy-2,6-dimethylphenyl)-3-(methoxycarbonyl)pyridin-1-ium (0.64 g, crude product, 1.04 mmol, 1.0 eq) in AcOH (10 mL) was added isobutyraldehyde (226 mg, 3.13 mmol, 3.0 eq) and copper (II) acetate (64 mg, 0.52 mmol, 3.0 eq). The mixture was stirred at 70° C. for 16 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH=15:1) to give methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (115 mg, 2 steps, 31% yield) as a yellow solid. LC-MS: 355.05 [M+H] + , 352.95[MH] - c) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid: To a solution of methyl 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (150 mg, 0.42 mmol, 1.0 eq) in MeOH / H2O (15 mL / 5 mL) was added NaOH (85 mg, 2.12 mmol, 5.0 eq). Under N2, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. Water (3 mL) was added, and 2.0 M dilute hydrochloric acid was added to adjust the pH to 4. The mixture was concentrated under reduced pressure to give 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid (166 mg, crude) as a yellow solid, which was used directly in the next step. LC-MS: 341.00 [M+H] + , 338.95[MH] -d) Preparation of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: To a solution of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (166 mg, crude) in DMF (20 mL) were added NH4Cl (113 mg, 2.12 mmol, 5.0 eq), HATU (242 mg, 0.64 mmol, 1.5 eq) and DIEA (328 mg, 2.54 mmol, 6.0 eq). The mixture was stirred at room temperature for 16 hours. After the reaction was completed, the mixture was purified by preparative TLC (DCM:MeOH=10:1) to give 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (112 mg, 2 steps, 78% yield) as a white solid. LC-MS: 340.05 [M+H] + , 337.95[MH] -. Examples 144-145 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 143 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 144 and component 2 being Example 145. Example 146 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143, except that isobutyraldehyde was replaced by acetaldehyde to obtain 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 147-148 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 146 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 147 and component 2 being Example 148. Example 149 7-amino-2-cyclopropyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a) Preparation of 2-(benzyloxy)-1,5-dibromo-3-fluorobenzene: To a solution of 2,4-dibromo-6-fluorophenol (3.0 g, 11.1 mmol, 1.0 eq) in ACN (30 mL) were added (bromomethyl)benzene (2.3 g, 13.3 mmol, 1.2 eq) and K2CO3 (3.1 g, 22.2 mmol, 2.0 eq). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was diluted with water (10 mL) and extracted with EA (10 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel (PE:EA=1:0) to give 2-(benzyloxy)-1,5-dibromo-3-fluorobenzene (3.1 g, 78% yield) as a colorless oil.b) Preparation of 2-(benzyloxy)-1-fluoro-3,5-dimethylbenzene: To a mixed solution of 2-(benzyloxy)-1,5-dibromo-3-fluorobenzene (3.1 g, 8.6 mmol, 1.0 eq) in dioxane (30 mL) and H₂O (6.0 mL) were added 2,4,6-trimethyl-1,3,5,2,4,6-trimethoxyriboborane (2.5 M, 10.3 mL, 25.8 mmol, 3.0 eq), K₂CO₃ (3.6 g, 25.8 mmol, 3.0 eq), Pd(OAc)₂ (380 mg, 1.7 mmol, 0.2 eq), and tricyclohexylphosphine (Cy₃P, 476 mg, 1.7 mmol, 0.2 eq). The reaction mixture was stirred at 100° C. under nitrogen for 20 hours. After the reaction was complete, the mixture was diluted with water (10 mL) and extracted with EA (10 mL × 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with silica gel (PE:EA = 1:0) to give 2-(benzyloxy)-1-fluoro-3,5-dimethylbenzene (1.2 g, 61% yield) as a colorless oil. c) Preparation of 2-(benzyloxy)-4-bromo-1-fluoro-3,5-dimethylbenzene: To a solution of 2-(benzyloxy)-1-fluoro-3,5-dimethylbenzene (1.2 g, 5.2 mmol, 1.0 eq) in acetonitrile (20.0 mL) was added NBS (929 mg, 5.2 mmol, 1.0 eq). Under nitrogen, the reaction mixture was stirred at 50°C for 48 hours. After the reaction was complete, the mixture was diluted with water (20 mL) and extracted with EA (20 mL × 5). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel (PE / EA=1 / 0) to give 2-(benzyloxy)-4-bromo-1-fluoro-3,5-dimethylbenzene (825 mg, 52% yield) as a colorless oil. d) Preparation of 2-(3-(benzyloxy)-4-fluoro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: To a solution of 2-(benzyloxy)-4-bromo-1-fluoro-3,5-dimethylbenzene (825 mg, 2.7 mmol, 1.0 eq) in dioxane (10 mL) were added 4,4,4′,4′,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane) (2.0 g, 8.1 mmol, 3.0 eq), Pd(dppf)Cl2 (423 mg, 0.5 mmol, 0.2 eq) and KOAc (794 mg, 8.1 mmol) at room temperature. The resulting mixture was stirred at 100° C. under nitrogen for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, diluted with water (10 mL), extracted with EA (10 mL×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated.The residue was purified by silica gel (PE / EA=1 / 0) to give 2-(3-(benzyloxy)-4-fluoro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 mg, 10% yield) as a colorless oil. e) Preparation of 7-amino-6-(3-(benzyloxy)-4-fluoro-2,6-dimethylphenyl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: To a mixed solution of 2-(3-(benzyloxyoxy)-4-fluoro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,3,2-dioxaborolane (100 mg, 0.3 mmol, 0.3 mmol, 2.0 eq) in dioxane (10 mL) and H2O (2 mL) were added 7-amino-2-cyclopropyl-6-iodo-[1,2,4,4]triazolo[1,5-a]pyridine-8-carboxamide (50 mg, 0.15 mmol, 1.0 eq), catalytic CXium A Pd G3 (22 mg, 0.03 mmol, 0.2 eq) and K3PO4 (106 mg, 0.5 mmol, 3.0 eq). The resulting mixture was stirred at 100 ° C for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, diluted with water (10 mL) and extracted with EA (10 mL × 3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by pre-TLC (DCM / MeOH=15 / 1) to give a yellow solid 7-amino-6-(3-(benzyloxy)-4-fluoro-2,6-dimethylphenyl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (35 mg, 52% yield). LC-MS: 446.20 [M+H]. + . f) Preparation of 7-amino-2-cyclopropyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: To a solution of 7-amino-6-(3-(benzyloxy)-4-fluoro-2,6-dimethylphenyl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (35 mg, 0.1 mmol, 1.0 eq) in MeOH (10 mL) was added Pd / C (10 mg, 10%) at room temperature. The reaction mixture was stirred at room temperature for 1 hour under hydrogen. Filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (C 18 Purification with 5% ACN in H2O (5-55%, 0.1% HCOOH) gave 7-amino-2-cyclopropyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (4.8 mg, 14% yield) as a white solid. LC-MS: 335.95 [M+H]+ ,353.90[M-H] -Examples 150-151 Separation of atropisomers of 7-amino-2-cyclopropyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 149 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 150 and component 2 being Example 151. Example 152 7-amino-2-cyclopropyl-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Examples 153-154 Separation of atropisomers of 7-amino-2-cyclopropyl-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 152 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 153 and component 2 being Example 154. Example 155 7-amino-2-cyclopropyl-6-(3,4-difluoro-5-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 156 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A similar synthesis method to that of Example 143 was used, substituting cyclopropanecarboxaldehyde for isobutyraldehyde, (5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide By replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)boronic acid, 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide can be prepared.Example 157 7-amino-2-chloro-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 158 7-amino-2-bromo-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 159 7-amino-2-fluoro-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 160 7-Amino-2-cyclopropyl-6-(2-hydroxy-3,5-dimethylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143, replacing isobutyraldehyde with cyclopropanecarboxaldehyde and replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (2-methoxy-3,5-dimethylpyridin-4-yl)boric acid to obtain 7-amino-2-cyclopropyl-6-(2-hydroxy-3,5-dimethylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 161 7-amino-2-cyclopropyl-6-(5-hydroxy-2,4-dimethylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, replacing isobutyraldehyde with cyclopropanecarboxaldehyde, and replacing 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with (5-methoxy-2,4-dimethylpyridin-3-yl)boric acid to obtain 7-amino-2-cyclopropyl-6-(5-hydroxy-2,4-dimethylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 162 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide At room temperature, to a solution of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide (18 mg, 0.05 mmol, 1.0 eq) in DMF (5 mL) was added NCS (6.0 mg, 0.05 mol, 1.0 eq.). The reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, water (10 mL) was added to the mixture and extracted with EA (10 mLx3). The organic phase was concentrated under reduced pressure and the residue was purified by preparative HPLC (C. 18, ACN in H2O, 5-55%, 0.1% HCOOH) to give 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide (5.9 mg, 30% yield) as a white solid. LC-MS: 373.00 [M+H] + , 370.85[MH] -. Example 163 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with propionaldehyde to prepare 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 164-165 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 163 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 164 and component 2 being Example 165. Example 166 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 1H-pyrazole-4-carboxaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 167 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(methyl-d3)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 168 7-amino-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-2-(methyl-d3)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 169 7-amino-2-(furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with furan-2-carboxaldehyde to prepare 7-amino-2- (Furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Example 170 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 171 7-amino-2-(4-bromofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 4-bromofuran-2-carboxaldehyde to prepare 7-amino-2-(4-bromofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 172 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-(pyridin-3-yl)furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 4-(pyridin-3-yl)furan-2-carboxaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-(pyridin-3-yl)furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 173 7-amino-2-(benzofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with benzofuran-2-carboxaldehyde to prepare 7-amino-2-(benzofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 174 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a) Preparation of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine: To a solution of 7-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-amine (1.0 g, 4.694 mmol, 1.0 eq) in acetonitrile (20 mL) were added CuBr2 (1.57 g, 7.042 mmol, 1.5 eq) and isoamyl nitrite (825 mg, 7.042 mol, 1.5 eq.). Under nitrogen, the reaction mixture was stirred at 75°C for 3 hours. After completion of the reaction, the mixture was diluted with water (30 mL) and extracted with EA (30 mL×5). The combined layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel (PE / EA=5 / 1) to give 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1.1 g, 84.8% yield) as a yellow solid.LCMS: 277.80 [M+H]. + . b) Preparation of 7-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine: To a solution of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (0.765 g, 2.78 mmol, 1.0 eq) in i-PrOH (10 mL) was added 4,4-difluoropiperidine (4.38 g, 36.18 mmol, 13.0 eq). Under nitrogen, the reaction mixture was stirred at 120 ° C in a microwave for 60 hours. After completion of the reaction, the mixture was concentrated and purified with silica gel (PE / EA=4 / 1) to give 7-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine (637 mg, 72.4% yield) as a yellow solid. LCMS: 318.85 [M+H] + c) Preparation of tert-butyl (2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)carbamate: To a solution of 7-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine (727 mg, 2.3 mmol, 1.0 eq), NH2Boc (324 mg, 2.76 mmol, 1.2 eq) and Cs2CO3 (1.49 g, 4.6 mmol, 2.0 eq) in dioxane (10 mL) was added Pd(dba)3 (210 mg, 0.23 mmol, 0.1 eq) and 4,5-bis(diphenylphosphino-9,9-dimethylxanthene) (Xphos, 0.266 g, 0.46 mmol, 0.2 eq). The mixture was reacted under nitrogen at 100 ° C for 18 hours. After completion of the reaction, it was diluted with water (10 mL) and extracted with EA (10 mL × 3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (PE / EA = 3 / 1) to give tert-butyl (2- (4,4-difluoropiperidin-1-yl) -[1,2,4] triazolo [1,5-a] pyridin-7-yl) carbamate (554 mg, 68% yield) as a white solid. LCMS: 354.00 [M + H] +. d) Preparation of 2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine: To a solution of tert-butyl (2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)carbamate (650 mg, 1.84 mmol, 1.0 eq) in DCM (10 mL) was added TFA (2.09 g, 18.4 mmol, 10 eq). Under nitrogen, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was diluted with NaHCO3 aqueous solution (10 mL) and extracted with DCM (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (PE / EA=1 / 1) to give 2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (400 mg, 86% yield) as a yellow solid. LCMS: 254.00 [M+H] + . e) Preparation of 8-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-amine: To a solution of 2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-amine (400 mg, 1.58 mmol, 1.0 eq) in DMF (6 mL) was added NBS (280 mg, 1.58 mmol, 1.0 eq) at 0 ° C. Under nitrogen, the reaction mixture was stirred at 0 ° C for 3 hours. After completion of the reaction, the mixture was diluted with water (10 mL) and extracted with EA (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (PE / EA=2 / 1) to give 8-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (500 mg, 95.6% yield) as a yellow solid. LCMS: 332.00, 334 [M+H] +f) Preparation of methyl 7-amino-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate: To a solution of 8-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (500 mg, 1.51 mmol, 1.0 eq) in methanol (10.0 mL) was added Pd(dppf)Cl2 (110 mg, 0.151 mmol, 0.1 eq) and TEA (458 mg, 4.53 mmol, 3.0 eq). The reaction mixture was stirred under CO and 100° C. for 12 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was purified by preparative TLC (PE / EA=2 / 1) to give methyl 7-amino-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (177 mg, 38% yield) as a white solid. LCMS: 312.00 [M+H] + . g) Preparation of 7-amino-6-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester: To a solution of 7-amino-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester (177 mg, 0.569 mmol, 1.0 eq) in AcOH (3.0 mL) was added Br2 (455 mg, 2.84 mmol, 5.0 eq). Under nitrogen, the reaction mixture was stirred at 50° C. for 2 hours. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was poured into ice water, the reaction solution was adjusted to pH=8-9 with saturated sodium bicarbonate, and extracted with EA (20 mL×5). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (PE / EA=1 / 1) to give methyl 7-amino-6-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (166 mg, 75% yield) as a white solid. LCMS: 391.75 [M+H] +h) Preparation of methyl 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate: To a mixed solution of methyl 7-amino-6-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (166 mg, 0.427 mmol, 1.0 eq) in dioxane (5 mL) and H2O (1 mL) were added 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (209 mg, 0.853 mmol, 2.0 eq), CataCXium A Pd G3 (62 mg, 0.085 mmol, 0.2 eq) and K3PO4 (271 mg, 1.28 mmol, 3.0 eq). The resulting mixture was stirred at 100 ° C in a sealed tube for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, diluted with water (10 mL), and extracted with EA (20 mL × 3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (PE / EA = 1 / 2) to give 7-amino-2- (4,4-difluoropiperidin-1-yl) -6- (3-hydroxy-2,6-dimethylphenyl) - [1,2,4] triazolo [1,5-a] pyridine-8-carboxylic acid methyl ester (60 mg, 32.6% yield) as a white solid. LC-MS: 432.00 [M + H] + i) Preparation of 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: To a solution of 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (60 mg, 0.139 mmol, 1.0 eq) in NH3 / MeOH (7N, 5 mL) was added CaCl2 (15.4 mg, 0.139 mmol, 1.0 eq). The resulting mixture was stirred at 70°C in a tube for 16 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (MeCN / H2O = 20% to 30%) to give 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (24 mg, 41.4% yield) as a white solid. LC-MS: 416.95 [M+H] +. Example 175 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxamide a) Preparation of 2,4-dichloronicotinate: To a solution of 2,4-dichloronicotinic acid (15.0 g, 78.5 mmol, 1.0 eq) in ACN (200 mL) were added 1,8-diazacyclo[5,4,0]undecene-7 (DBU, 23.9 g, 157.1 mmol, 2.0 eq) and MeI (16.6 g, 117.8 mmol, 1.5 eq) at 0°C. Under a N2 atmosphere, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EA=2:1) ​​to give 2,4-dichloronicotinate (13.5 g, 84% yield) as a colorless oil. LC-MS: 206.15[M+1] + . b) Preparation of 4-azido-2-chloronicotinic acid methyl ester: To a solution of 2,4-dichloronicotinic acid methyl ester (10.0 g, 48.78 mmol, 1.0 eq) in DMF (120 mL) was added NaN3 (3.8 g, 58.54 mmol, 1.2 eq). The mixture was reacted at 50 ° C for 6 hours. After the reaction was completed, water (80 mL) was added to quench it and extracted with EA (150 mLx3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a yellow solid 4-azido-2-chloronicotinic acid methyl ester (11.8 g, crude product), which was used directly in the next step. LC-MS: 213.00 [M+H] + . c) Preparation of 4-amino-2-chloronicotinic acid methyl ester: 4-azido-2-chloronicotinic acid methyl ester (25.0 g, crude product) was placed in a round-bottom flask and hydroiodic acid (HI, 55%, 40 mL) was slowly added at 0°C. The mixture was stirred at room temperature for 1 hour. After the reaction was completed, the solution was concentrated under reduced pressure, quenched with a saturated solution of sodium bicarbonate (100 mL), and extracted with EA (150 mLx3). The combined organic phases were washed with sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 4-amino-2-chloronicotinic acid methyl ester (15.0 g, 2 steps, 78% yield) as a white solid. LC-MS: 187.20 [M+H] +d) Preparation of methyl 4-amino-2-cyanonicotinate: To a solution of methyl 4-amino-2-chloronicotinate (4.0 g, 21.5 mmol, 1.0 eq) in DMF (40 mL) were added Zn(CN)2 (2.8 g, 23.7 mmol, 1.1 eq), Pd2(dba)3 (89.0 mg, 0.2 mmol, 0.01 eq) and 1,1′-bis(diphenylphosphino)ferrocene (dppf, 238.0 mg, 0.4 mmol, 0.02 eq). Under a nitrogen atmosphere, the reaction mixture was stirred at 120° C. for 6 hours. After completion of the reaction, the mixture was diluted with water (40 mL) and extracted with EA (50 mL×3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EA=2:1) ​​to give methyl 4-amino-2-cyanonicotinate (2.5 g, 66% yield) as a yellow solid. LC-MS: 178.30 [M+H] + . e) Preparation of methyl 4-amino-5-bromo-2-cyanonicotinate: To a solution of methyl 4-amino-2-cyanonicotinate (1.5 g, 8.5 mmol, 1.0 eq) in AcOH (200 mL) was added Br2 (13.6 g, 84.7 mmol, 10.0 eq). Under a nitrogen atmosphere, the mixture was stirred at 60°C for 2 hours. After the reaction was completed, the solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EA=5:1) to give methyl 4-amino-5-bromo-2-cyanonicotinate (1.5 g, 68% yield) as a white solid. LC-MS: 256.10, 258.10 [M+H] + f) Preparation of methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: To a solution of methyl 4-amino-5-bromo-2-cyanonicotinate (1.8 g, 7.1 mmol, 1.0 eq) in dioxane / H2O (15 mL / 5 mL) was added 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.8 g, 7.1 mmol, 1.0 eq), catacxium-Pd-G3 (1.0 g, 1.4 mmol, 0.2 eq), and K3PO4 (4.5 g, 21.2 mmol, 3.0 eq). The mixture was stirred at 110°C for 16 hours under nitrogen. After completion of the reaction, the mixture was quenched with water (20 mL) and extracted with EA (30 mL × 3). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by reverse phase column (C 18, ACN solution in H2O, 5-50%) to give methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (490 mg, 23% yield) as a white solid. LC-MS: 298.25 [M+H] + . g) Preparation of methyl 4-(tert-butoxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: To a mixed solution of methyl 4-amino-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (490 mg, 1.6 mmol, 1.0 eq) in THE / H2O (5 mL / 1 mL) were added (Boc)2O (719.0 mg, 3.3 mmol, 2.0 eq) and DMAP (101 mg, 0.8 mmol, 0.5 eq). Under N2 atmosphere, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EA=2:1) ​​to give methyl 4-(tert-butoxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (300 mg, 46% yield) as a colorless oil. LC-MS: 398.3 [M+H] + h) Preparation of methyl 4-((tert-butoxycarbonyl)amino)-2-(cyclopropanecarboxamidomethyl)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate: To a solution of methyl 4-((tert-butoxycarbonyl)amino)-2-cyano-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (160 mg, 0.4 mmol, 1.0 eq) in MeOH (5 mL) were added cyclopropanecarboxylic anhydride (1 mL) and Raney nickel (Raney Ni, 160 mg). The mixture was stirred at room temperature under a H2 atmosphere for 16 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The residue was purified by preparative TLC (PE:EA=1:1) to give methyl 4-((tert-butoxycarbonyl)amino)-2-(cyclopropanecarboxamidomethyl)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (120 mg, 63% yield) as a colorless oil. LC-MS: 470.10 [M+H] +i) Preparation of methyl 7-((tert-butoxycarbonyl)amino)-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylate: To a solution of methyl 4-((tert-butoxycarbonyl)amino)-2-(cyclopropanecarboxamidomethyl)-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate (120 mg, 0.3 mmol, 1.0 eq) in ACN (10 mL) was added Burgess reagent (214 mg, 0.9 mmol, 3.0 eq) at 0° C. Under a N2 atmosphere, the mixture was stirred at 90° C. for 16 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The residue was purified by preparative TLC (PE:EA=2:1) ​​to give methyl 7-((tert-butoxycarbonyl)amino)-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylate (90 mg, 78% yield) as a yellow solid. LC-MS: 452.15 [M+H] + . j) Preparation of 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylic acid methyl ester: To a solution of 7-((tert-butoxycarbonyl)amino)-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylic acid methyl ester (90 mg, 0.2 mmol, 1.0 eq) in DCM (5 mL) was added TFA (5 mL). The mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (DCM:MeOH=10:1) to give 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylic acid methyl ester (50 mg, 71% yield) as a yellow solid. LC-MS: 352.00 [M+H] + k) Preparation of 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylic acid: To a solution of methyl 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylate (50 mg, 0.1 mmol, 1.0 eq) in MeOH / H2O (4 mL / 1 mL) was added NaOH (40 mg, 1.0 mmol, 10.0 eq). Under an N2 atmosphere, the mixture was stirred at 90°C for 1 hour. After the reaction was complete, the mixture was concentrated under reduced pressure. Water (1 mL) was added, and 2.0 M dilute hydrochloric acid was added to adjust the pH to 4. The mixture was concentrated under reduced pressure to give 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxylic acid (50 mg, crude) as a yellow solid, which was used directly in the next step. LC-MS: 338.00 [M+H]+ . 1) Preparation of 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxamide: To a DMF (5 mL) solution of 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxamide (50 mg, crude) were added NH4Cl (22 mg, 0.4 mmol, 3.0 eq), HATU (76 mg, 0.2 mmol, 1.5 eq) and DIEA (148 mg, 1.5 mmol, 10.0 eq). The mixture was stirred at 40 ° C for 16 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to give a crude product. The residue was purified by preparative HPLC (C 18 , CH3CN:H2O=5%~55%, 0.1% HCOOH) to give 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxamide (7.2 mg, 2 steps, 15% yield) as a white solid. LC-MS: 336.95 [M+H] + , 334.85[MH] -Example 176 4-amino-1-(furan-2-yl)-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide Example 177 4-amino-1-(benzofuran-2-yl)-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide Example 178 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(4-phenylfuran-2-yl)-1,6-dihydropyridine-3-carboxamide Example 179 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(4-(pyridin-3-yl)furan-2-yl)-1,6-dihydropyridine-3-carboxamide Example 180 7-Amino-6-(5-chloro-4-methylpyridin-3-yl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide a) Preparation of 3-chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine: To a solution of 3-bromo-5-chloro-4-methylpyridine (50 mg, 0.242 mmol, 1.0 eq) in dioxane (2 mL) was added B2P2 (123 mg, 0.484 mmol, 2.0 eq), Pd(dppf)Cl2 (18 mg, 0.0242 mmol, 0.1 eq) and KOAc (71 mg, 0.726 mmol, 3.0 eq). The mixture was stirred at 110° C. for 16 hours. After completion of the reaction, the solution was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (PE:EA=2:1) ​​to give 3-chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (40 mg, 65% yield) as a white solid. LC-MS: 172.05 [M+H] + b) Preparation of 7-amino-6-(5-chloro-4-methylpyridin-3-yl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide: To a solution of 3-chloro-4-methyl-5-(4,4,5,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (40 mg, 0.234 mmol, 1.0 eq) in dioxane / water (3 mL / 1 mL) were added 7-amino-2-cyclopropyl-6-iodo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (80 mg, 0.234 mmol, 1.0 eq), catacxium-Pd-G3 (34 mg, 0.0468 mmol, 0.2 eq) and K3PO4 (149 mg, 0.702 mmol, 3.0 eq). The mixture was stirred at 110°C for 16 hours. After the reaction was complete, the product was analyzed by preparative HPLC (C18 Purification with 5% ACN in H2O (5-55%, 0.1% HCOOH) gave 7-amino-6-(5-chloro-4-methylpyridin-3-yl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (18.6 mg, 23% yield) as a white solid. LC-MS: 343.10 [M+H] + , 341.05[MH] -Example 181 7-amino-2-(3-fluoropyridin-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting 3-fluoropyridinecarboxaldehyde for isobutyraldehyde to prepare 7-amino-2-(3-fluoropyridin-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 182 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(3-methoxypyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(3-methoxypyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 181. Examples 183-184 Separation of atropisomers of 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide The racemic 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (Example 156) was separated by SFC chiral column using a method similar to that of Examples 69-70 to obtain two components, namely Examples 183 and 184. Example 185 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 3,3,3-trifluoropropionaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 186 7-Amino-2-(2-amino-2-oxoethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-2-(2-amino-2-oxoethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 185.Example 187 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace (3-hydroxy-2,6-dimethylphenyl)boric acid with (5-methyl-1H-indazol-4-yl)boric acid to prepare 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 188-189 Separation of Atropisomers of 7-amino-2-ethyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-amino-2-ethyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 188 and component 2 being Example 189. Example 190 7-Amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 174 was used, substituting 7-amino-6-iodo-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester for 7-amino-6-bromo-2-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Pyridine-8-carboxylic acid methyl ester, 6-fluoro-2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol replaces 2,4-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol to prepare 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 191 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting 4-methylfuran-2-carboxaldehyde for isobutyraldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Examples 192-193 Separation of atropisomers of 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 187 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 192 and component 2 being Example 193. Example 194 7-amino-6-(3-fluoro-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, replacing (3-hydroxy-2,6-dimethylphenyl)boric acid with (3-fluoro-2,6-dimethylphenyl)boric acid to prepare 7-amino-6-(3-fluoro-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 195 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace NH4Cl with 1-methyl-1H-pyrrol-2-amine to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 196 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace NH4Cl with (1-methyl-1H-pyrrol-3-yl)methanamine to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 197 7-amino-2-(3,3-difluorocyclobutyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 3,3-difluorocyclobutane-1-carboxaldehyde to prepare 7-amino-2-(3,3-difluorocyclobutyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Example 198 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with 1-methyl-1H-pyrrole-2-carboxaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 199-200 Separation of atropisomers of 7-amino-2-(furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 169 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 199 and component 2 being Example 200. Examples 201-202 Separation of atropisomers of 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 190 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 201 and component 2 being Example 202. Example 203 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide is prepared using a synthetic method similar to that of Example 143, replacing isobutyraldehyde with 1-(1-methylpiperidin-4-yl)-1H-pyrazole-4-carboxaldehyde to obtain 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Examples 204-205 Separation of atropisomers of 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 166 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 204 and component 2 being Example 205.Examples 206-207 Separation of Atropisomers of 7-amino-2-ethyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 143, replacing isobutyraldehyde with propionaldehyde and (3-hydroxy-2,6-dimethylphenyl)boric acid with (4-fluoro-3-hydroxy-2,6-dimethylphenyl)boric acid, 7-amino-2-ethyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared. SFC chiral separation was performed using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 206 and component 2 being Example 207. Example 208 7-amino-2-(cyclopropylmethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 143, replacing isobutyraldehyde with 2-cyclopropylacetaldehyde, 7-amino-2-(cyclopropylmethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide can be prepared. Example 209 7-amino-2-cyclopentyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting cyclopentanecarboxaldehyde for isobutyraldehyde to prepare 7-amino-2-cyclopentyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 210 7-amino-2-cyclohexyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting cyclohexanecarboxaldehyde for isobutyraldehyde to prepare 7-amino-2-cyclohexyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 211 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with tetrahydro-2H-pyran-4-carboxaldehyde to prepare 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Example 212 7-Amino-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthesis method similar to that of Example 143 was used, replacing (3-hydroxy-2,6-dimethylphenyl)boric acid with (3-fluoro-5-hydroxy-2,6-dimethylphenyl)boric acid to prepare 7-amino-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 213 7-amino-2-(tert-butyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace isobutyraldehyde with pivalaldehyde to prepare 7-amino-2-(tert-butyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 214 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting 1H-pyrazole-4-carboxaldehyde for isobutyraldehyde to prepare 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 215 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8- Formamide was synthesized using a method similar to that of Example 143, replacing 2,4-diamino-5-(5-methyl-1H-indazol-4-yl)nicotinic acid methyl ester with 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinic acid methyl ester and replacing isobutyraldehyde with 1-methyl-1H-pyrazole-4-carboxaldehyde to obtain 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Example 216 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 143, replacing 2,4-diamino-5-(5-methyl-1H-indazol-4-yl)nicotinamide with 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate, and replacing isobutyraldehyde with 1-methyl-1H-pyrazole-5-carboxaldehyde, 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared. Example 217 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Using a synthetic method similar to that of Example 143, replacing 2,4-diamino-5-(5-methyl-1H-indazol-4-yl)nicotinamide with 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate, and replacing isobutyraldehyde with tetrahydro-2H-pyran-4-carboxaldehyde, 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide can be prepared. Example 218 7-amino-2-(cyclopropylmethyl)-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, substituting 2,4-diamino-5-(5-methyl-1H-indazol-4-yl)nicotinamide for 2,4-diamino-5-(3-hydroxy-2,6-dimethylphenyl)nicotinate, and 2-cyclopropylacetaldehyde for isobutyraldehyde to prepare 7-amino-2-(cyclopropylmethyl)-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 219 7-amino-6-(3,5-dihydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used to replace (3-hydroxy-2,6-dimethylphenyl)boric acid with 2-(3,5-dimethoxy-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane to prepare 7-amino-6-(3,5-dihydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.Example 220 7-Amino-6-(7-fluoro-1H-indazol-4-yl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-6-(7-fluoro-1H-indazol-4-yl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared by a synthetic method similar to that of Example 143. Example 221 7-amino-6-(2,6-difluoro-3-hydroxyphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide A synthetic method similar to that of Example 143 was used, replacing (3-hydroxy-2,6-dimethylphenyl)boric acid with (2,6-difluoro-3-methoxyphenyl)boric acid to prepare 7-amino-6-(2,6-difluoro-3-hydroxyphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide. Example 222 7-Amino-6-(7-fluoro-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl″)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-6-(7-fluoro-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl″)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143. Examples 223-224 Separation of atropisomers of 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl″)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide Example 214 was subjected to SFC chiral separation using a method similar to that of Examples 69-70 to obtain two components, component 1 being Example 223 and component 2 being Example 224. Example 225 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143. Example 226 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143.Example 227 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143. Example 228 7-Amino-6-(6-hydroxy-2,3-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-Amino-6-(6-hydroxy-2,3-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide was prepared using a synthetic method similar to that of Example 143. The compounds of each Example (Examples 1-228) are as follows: Note: ND means not tested. Example 229 Inhibitory effect of the compounds of the present invention on PKMYT1 enzyme activity PKMYT1 enzyme activity was detected using recombinant human PKMYT1 kinase and the commercial reagent ADP-Glo ​​assay (Promega's ADP-Glo TMKinase assay, #V9101) measures ATP hydrolysis. Compounds were serially diluted with DMSO in a compound dilution plate, and 0.1 μL of compound was transferred to a 384-reaction microplate (duplicate wells) using an automated nanoliter pipetting system (Beckman Coulter, Echo655). 5 μL of 2×PKMYT1 enzyme solution was added to each well of the 384-reaction microplate and incubated at 25°C for 10 minutes. 5 μL of 2×ATP (40 μM) and inactive CDK1 solution (final DMSO content of 1%) were then added to each well and incubated at 25°C for 180 minutes. Wells containing 1% DMSO and enzyme were considered high signals, and wells containing 1% DMSO and buffer containing ATP were considered low signals. 5 μL of ADP-Glo ​​reagent was then added to each well and centrifuged at 1000 rpm for 1 minute. Incubate at 25°C for 40 minutes. 10 μL of ADP-Glo ​​assay buffer (final concentration: 5 nM PKMYT1 enzyme reaction solution, 10 nM inactive CDK1, 20 μM ATP) was added to each well and centrifuged at 1000 rpm for 1 minute. Incubate at 25°C for 40 minutes. The relative luminescence unit (RLU) signal was read on a BMG (PHERAstar FSX) microplate reader. The percentage of inhibition of the compound-treated wells was normalized between high and low signals (% inhibition = (RLU)). 高信号 -RLU 化合 (RLU) / (RLU 高信号 -RLU 低信号 )*100). Then, the four-parameter IC was fitted by XLfit 5.5.0. 50 Curve and analysis, IC 50 The inhibitory effect of the compounds of the present invention on PKMYT1 enzyme activity was determined by the above test method, and the measured IC 50 The values ​​are shown in Table 1 below. Among them, +++++ represents IC 50 ≤10nM; ++++ means 10nM <IC 50 ≤100nM; +++ means 100nM <IC 50 ≤500nM; ++ means 500nM <IC 50 ≤1μM; + indicates IC 50 >1μM. Table 1: IC values ​​of Example compounds for inhibition of PKMYT1 enzyme activity 50 The results showed that the compounds of the present invention exhibited potent inhibitory effects on PKMYT1 enzyme activity. Example 230: Inhibition of Wee1 Enzyme Activity by Compounds of the Present Invention ADP-Glo ​​Kinase Reagent (Promega, #V9103) was used in a reaction buffer consisting of 50 mM HEPES, 1 mM EGTA, 10 mM MgCl2, 0.01% Brij 35, and 2 mM DTT (pH 7.5). The stock solution of the test compound was serially diluted with DMSO at a 1:3 ratio to 10 concentrations. Then, using an Echo 665 instrument, 0.05 μL of the diluted compound was added to a 384-well plate (Greiner, #784075). 2.5 μL of Wee1 enzyme (Carna, #05-177) solution was added, and the plate was centrifuged at 1000 rpm for 1 minute. After incubation at 25°C for 10 minutes, the reaction was initiated by adding 2.5 μL of the ATP / substrate mixture and allowed to react at 25°C for 60 minutes. Then, 4 μL of ADP-Glo ​​reagent was added and incubated at 25°C for 40 minutes. Then, 8 μL of kinase detection reagent was added and incubated at 25°C for another 40 minutes. Finally, the chemiluminescence value was detected on a BMG PHERAstar FSX instrument. The inhibition rate was calculated as % = (chemiluminescence value of the well without compound added - chemiluminescence value of the well with test compound) / (chemiluminescence value of the well without compound added - chemiluminescence value of the negative control well) × 100, using the nonlinear regression equation: Y = Bottom + (Top - Bottom) / (1 + 10^((LogIC 50 The curve was fitted with the HillSlope curve, and the IC was calculated using the XLfit 5.5.0 software. 50 The inhibitory effect of the compounds of the present application on Wee1 enzyme activity was determined by the above test method, and the measured IC 50 The values ​​are shown in Table 2 below. Among them, +++++ represents IC 50 ≤10nM; +++ means 10nM <IC 50 ≤100nM; +++ means 100nM <IC 50 ≤500nM; ++ means 500nM <IC 50 ≤1μM; + indicates IC 50 >1μM. Table 2: IC values ​​of Example compounds for inhibition of Wee1 enzyme activity 50 The results showed that the compounds of the present invention had a weak inhibitory effect on Wee1 enzyme activity and had good selectivity for inhibiting PKMYT1 enzyme activity. Example 231 Inhibitory effect of the compounds of the present invention on HCC1569 cell growth The cytotoxicity of the compounds of the present invention on human breast cancer cells HCC1569 was detected by luminescence cell viability assay. HCC1569 cells were seeded into 96-well cell culture plates at an appropriate plating density. The culture plates were placed in a humidified incubator at 37°C and 5% CO2 overnight. The next day, after removing the stock solution, 95 μL of fresh culture medium was added to each well of the cell culture plate. The test compound was serially diluted 3-fold and 10-fold using 100% DMSO to a total of 8 concentration points. In another plate, 245 μL of culture medium and 5 μL of the serially diluted test compound were mixed (50-fold dilution). 5 μL of the diluted test compound (20-fold dilution) was added to each well of the 96-well cell culture plate containing 95 μL of fresh culture medium. The cell culture plate was then returned to a 37°C and 5% CO2 incubator for 7 days. On the 4th day, the culture medium was replenished and the concentration of the test compound remained unchanged. On the 7th day, 100 μL of Cell Counting-Lite 2.0 reagent (Vazyme, DD1101-02) was added to each well. The cell plate was then shaken at 350 rpm for 2 minutes and incubated at room temperature for 30 minutes. The chemiluminescent signal was read using a microplate reader. Using cell survival rate and compound concentration as coordinates, a curve of the inhibitory activity of the compound on cell proliferation was drawn. Cell survival rate % = (RLU 化合物 -RLU 背 景 ) / (RLU DMSO -RLU 背景 )×100. IC 50 The values ​​were fitted by the sigmoidal dose-response curve equation: Y = 100 / (1 + 10^(log C - log IC 50 )), C is the concentration of the compound. The compounds of the present application have an inhibitory effect on the growth of HCC1569 cells. The IC50 values ​​measured by the above test method are shown in Table 3 below. Wherein, ++++ represents IC 50 ≤500nM;+++ means 500nM <IC 50 ≤1000nM; ++ means 1000nM <IC 50 ≤5μM; + indicates IC 50 >5μM. Table 3: IC values ​​of Example compounds for inhibition of HCC1569 cell proliferation 50 The results showed that the compounds of the present invention had a significant inhibitory effect on the proliferation activity of HCC1569 cells. Example 232 Inhibitory Effect of Compounds of the Present Invention on OVCAR-3 Cell Growth A luminescent cell viability assay was used to test the cytotoxicity of the patented MYT1 inhibitor against the human breast cancer OVCAR-3 cell line. OVCAR-3 cells were seeded into 96-well cell culture plates at an appropriate plating density. The culture plates were placed in a humidified incubator at 37°C and 5% CO2 overnight. The next day, after removing the stock solution, 95 μL of fresh culture medium was added to each well of the cell culture plate. The PKMYT1 inhibitor was serially diluted 3-fold and 10-fold using 100% DMSO, for a total of 8 dilutions. In a separate plate, 245 μL of culture medium and 5 μL of the serially diluted test compound were mixed (50-fold dilution). 5 μL of the diluted test compound (20-fold dilution) was added to each well of the 96-well cell culture plate containing 95 μL of fresh culture medium. The cell culture plate was then returned to a 37°C and 5% CO2 incubator and cultured for 7 days. On the 4th day, the culture medium was replenished, and the concentration of the test compound remained unchanged. On the 7th day, 100 μL of Cell Counting-Lite 2.0 reagent (Vazyme, DD1101-02) was added to each well. The cell plate was then shaken at 350 rpm for 2 minutes and incubated at room temperature for 30 minutes. The chemiluminescence signal was read using a microplate reader. Using cell viability and compound concentration as coordinates, a curve of the inhibitory activity of the compound on cell proliferation was drawn. Cell viability % = (RLU compound - RLU background) / (RLUDMSO - RIU background) × 100. The IC50 value was fitted by the s-type dose-response curve equation: Y = 100 / (1+10^(logC-logic50)), where C is the compound concentration. The compounds of the present application have an inhibitory effect on the growth of OVCAR-3 cells, as determined by the above test method, and the measured IC 50 The values ​​are shown in Table 4 below. ++++ indicates IC 50 ≤500nM;+++ means 500nM <IC 50 ≤1000nM; +- indicates 1000nM <IC 50 ≤5μM; + indicates IC 50 >5μM. Table 4: IC values ​​of Example compounds for inhibition of OVCAR-3 cell proliferation 50 The results showed that the compound of the present invention had a good inhibitory effect on the proliferation activity of OVCAR-3 cells.

[0140] Although the present invention has been fully described, it will be understood by those skilled in the art that the same implementation can be carried out within a wide range of and equivalent conditions, formulations, and other parameters without affecting the scope of the present invention or any embodiment thereof. All patents, patent applications, and publications cited herein are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the following formula I, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof: in: A0, A1 and A2 are each independently C or N; R1 is optionally substituted aryl or optionally substituted heteroaryl; R5 is hydrogen, halogen, cyano, hydroxy, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or -NR 5a R 5b ; Among them, R 5a and R 5b are each independently hydrogen, optionally substituted C 1-6 Alkyl or optionally substituted C 3-8 Cycloalkyl; R6 is -C(O)NR 6a R 6b , -SO2R 6c or -C(O)R 6d ; Among them, R 6a and R 6b are each independently hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, or R 6a and R 6b Together with the attached N, it forms an optionally substituted heterocyclic group; R 6c is an optionally substituted C 1-6 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted aryl or -NR 6a R 6b ; R 6d is an optionally substituted C 1-6 Alkyl, optionally substituted C 2-6 Alkenyl or optionally substituted C 2-6 Alkynyl; R7, R8 and R9 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 2-6 Alkenyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 3-8 R7 and R8, together with the connected A1 and A0, form an optionally substituted heterocyclyl, an optionally substituted aryl or an optionally substituted heteroaryl; or R8 and R9, together with the connected A0 and A2, form an optionally substituted heterocyclyl, an optionally substituted aryl or an optionally substituted heteroaryl.

2. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: A0, A1 and A2 are all C, or one of them is N and the remaining two are C; preferably, A0 is N, A1 and A2 are all C, A1 is N, A0 is C and A2 is C, or A1 is C, A0 is C and A2 is N.

3. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: The optionally substituted aryl and optionally substituted heteroaryl described in R1 are optionally substituted 6-14 membered aryl or optionally substituted 5-10 membered heteroaryl; preferably, R1 is optionally substituted by 1, 2, 3, 4 or 5 groups selected from hydroxyl, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Preferably, the aryl group is substituted with at least one hydroxyl group or one C 1-6 Alkyl substitution; preferably, the heteroaryl group described in R1 is a bicyclic heteroaryl group, preferably the heteroatom contains at least one nitrogen atom, and more preferably, the heteroaryl group is a 5- or 6-membered heteroaryl group or a 9-membered fused bicyclic heteroaryl group; Preferably, R1 is: Where W is N or CR w ; Z1 and Z2 are independently N or CR w , and at least one of Z1 and Z2 is N; n is 0, 1 or 2; R w , R2 and R3 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; each R4 is independently halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy or optionally substituted C 3-8 Cycloalkyl; * indicates the position where R1 is attached to the rest of the compound of formula I.

4. The compound according to claim 3, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: W is N; or W is CR w , R w For hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl, preferably hydrogen, halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl, more preferably hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 Alkyl, more preferably hydrogen, halogen, methyl or deuterated methyl; preferably, W is CH; Z1 is N, Z2 is CH, or Z1 is CH, Z2 is N; R2 and R3 are each independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl or C 3-6 Cycloalkyl; more preferably each independently is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1- 3 alkyl or C 3-4 cycloalkyl; more preferably each independently is hydrogen, chlorine, methyl, deuterated methyl or cyclopropyl; preferably, R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 Cycloalkyl, preferably hydrogen, chlorine, methyl, deuterated methyl or cyclopropyl, R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-4 Cycloalkyl, preferably methyl, deuterated methyl, bromine, chlorine or cyclopropyl; n is 0 or 1; and / or Each R4 is independently halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, deuterated C 1-6 Alkyl, C 1-6 Alkoxy or C 3-8 Cycloalkyl; preferably each independently halogen, C 1-4 Alkyl, halogenated C 1-4 Alkyl, deuterated C 1-4 Alkyl, C 1-4 Alkoxy or C 3-6 Cycloalkyl; more preferably each independently is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl or deuterated C 1-3 Alkyl; more preferably each independently is hydrogen, methyl, deuterated methyl, chlorine or fluorine.

5. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: R1 is: Wherein R2 is hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl, preferably hydrogen, methyl, deuterated methyl or chlorine; R3 is halogen, C 1-3 Alkyl, halogenated C 1-3 Alkyl, deuterated C 1-3 Alkyl or C 3-6 Cycloalkyl is preferably methyl, deuterated methyl, bromine or chlorine; R4 is halogen.

6. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: R5 is hydrogen, halogen, cyano, halogenated C 1-3 Alkyl or -NR 5a R 5b ; Preferably, R5 is -NR 5a R 5b Preferably, R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl or C 3-6 Cycloalkyl, more preferably all hydrogen; and / or R6 is -C(O)NR 6a R 6b Preferably, R 6a and R 6b are each independently hydrogen, optionally substituted by a 5- or 6-membered heteroaryl 1-6 Alkyl, or C 3-8 Cycloalkyl, preferably hydrogen, C 1-3 Alkyl, C substituted by 5 or 6-membered nitrogen-containing heteroaryl 1-3 Alkyl, or C 3-6 Cycloalkyl, more preferably all hydrogen; and / or R7, R8 and R9 are optionally substituted C 3-8 Cycloalkyl, optionally substituted C 3-8 The cycloalkenyl, optionally substituted heterocyclyl, optionally substituted aryl and optionally substituted heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, cyano, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 substituted by alkoxy and 4-10 membered heterocyclic groups; preferably, R7, R8 and R9 are each independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C 2-4 Alkenyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkenyl, 4-10 membered heterocyclic group, C 6-14 aryl, 5-10 membered heteroaryl or =O, the C 3-6 Cycloalkyl, C 3-6 Cycloalkenyl, 4-10 membered heterocyclic group, C 6-14 The aryl and 5-10 membered heteroaryl groups are each optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxyl, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy and halogenated C 1-4 The substituents of the alkoxy group are substituted.

7. The compound according to any one of claims 1 to 6, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: A0 is N, R7 or R9 is =O, R8 is an optionally substituted 4-10 membered heterocyclic group, an optionally substituted C 6-14 aryl or optionally substituted 5-10 membered heteroaryl; preferably, the optionally substituted 4-10 membered heterocyclyl, optionally substituted C 6-14 The aryl and optionally substituted 5-10 membered heteroaryl groups may each be optionally substituted by 1, 2 or 3 groups selected from halogen, amino, amido, hydroxy, cyano, C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkoxy and 4-10 membered heterocyclic group are substituted; or R7 and R8 together with the connected A1 and A0 form an optionally substituted 5-6 membered heterocyclyl, an optionally substituted 6 membered aryl or an optionally substituted 5-6 membered heteroaryl, A2 is C; preferably, the 5-6 membered heterocyclyl, 6 membered aryl and 5-6 membered heteroaryl are each optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, -CONR'R" substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 Alkyl, wherein R' and R" are each independently H or C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halogenated C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, optionally substituted 5-10-membered heteroaryl-O-; preferably, the optionally substituted C 3-6 The cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl and optionally substituted 5-10-membered heteroaryl may each be optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxy, C 1-4 Alkyl, halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 substituted with a substituent of an alkoxy group and a 5- or 6-membered heterocyclic group (preferably a nitrogen-containing heterocyclic group); or R8 and R9 together with the connected A0 and A2 form an optionally substituted 5-6 membered heterocyclyl, an optionally substituted 6 membered aryl, an optionally substituted 5-6 membered heteroaryl, A1 is C; preferably, the 5-6 membered heterocyclyl, 6 membered aryl and 5-6 membered heteroaryl can be optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halogenated C 1-4 Alkoxy, hydroxy substituted C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 The cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, optionally substituted 5-10-membered heteroaryl-O-; more preferably, the 5-6-membered heterocyclyl, 6-membered aryl and 5-6-membered heteroaryl are unsubstituted or may be optionally substituted by 1, 2 or 3 substituents selected from C 1-4 Alkyl, halogenated C 1-4 Alkyl, C 3-6 Cycloalkyl, C substituted by 5-membered heteroaryl 1-4 The substituents of the alkyl and optionally substituted 5-10 membered heteroaryl groups are substituted.

8. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: A0, A1, A2, R7 and R8 form the following heteroaromatic ring or heterobicyclic ring: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; R 13 is hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted aryl or optionally substituted 5-6 membered heteroaryl, preferably C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 3-4 Cycloalkyl or optionally 1-2 selected C 1-3 wherein the heteroaromatic ring or heterobicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halogenated C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, or optionally substituted 5-10-membered heteroaryl-O-; or A0, A1, A2, R8 and R9 form the following heteroaromatic ring or heterobicyclic ring: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; wherein the heteroaromatic ring or heterobicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1- 4 Alkoxy (such as halogenated C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 The substituents are cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, or optionally substituted 5-10-membered heteroaryl-O-.

9. The compound according to any one of claims 1 to 8, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: The compound of formula I is a compound represented by the following formula IIa, IIb, IIc, IId, IIe, IIf, IIIa or IIIb, or a stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt thereof, or a mixture thereof: in: In the formulae IIa, IIb, IIc, IId, IIe and IIf, R1, R5, R6, R7 and R9 are each as described in any one of claims 1 to 7; A3, A4, A5, A6, A7, A8, D1, D2, D3, D4, B1, B2 and B3 are each independently CR 10 , CR 11 R 12 NR 13 , N, O or S; R 10 is hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or =O; R 11 and R 12 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl; and R 13 is hydrogen, optionally substituted C 1-6 Alkyl or optionally substituted C 3-8 Cycloalkyl; In the formula IIIa and IIIb, R1, R5 and R6 are each as described in any one of claims 1 to 7; R7, R8 and R9 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 2-6 Alkenyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 3-8 cycloalkenyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl.

10. The compound according to claim 8, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: (1) In formula IIa and IId, the heteroaromatic bicyclic ring formed by A3, A4, A5 and the pyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; preferably, the heteroaromatic bicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, -CONR'R" substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 Alkyl, wherein R' and R" are each independently H or C 1-4 alkyl), optionally substituted C 1-4 Alkoxy (such as halogenated C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 substituted by a substituent selected from cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, or optionally substituted 5-10-membered heteroaryl-O-; (2) In formula IIb and IIe, the heteroaromatic ring or heterobicyclic ring formed by A3, A4, A5 and the oxopyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; preferably, the heteroaromatic ring or heterobicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, hydroxyl, cyano, =O, optionally substituted C 1-4 Alkyl (such as halogenated C 1-4 Alkyl, hydroxy substituted C 1-4 Alkyl, 5-7 membered heteroaryl substituted C 1-4 Alkyl, 6-14 membered aryl substituted C 1-4 Alkyl, C 3-8 Cycloalkyl substituted C 1-4 Alkyl, 4-10 membered heterocyclic substituted C 1-4 alkyl), optionally substituted C 1- 4 Alkoxy (such as halogenated C 1-4 Alkoxy, 5-7 membered heteroaryl substituted C 1-4 Alkoxy, 6-14 membered aryl substituted C 1-4 Alkoxy, C 3-8 Cycloalkyl substituted C 1-4 Alkoxy, 4-10 membered heterocyclic substituted C 1-4 alkoxy), optionally substituted C 3-6 cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, optionally substituted 5-10-membered heteroaryl, optionally substituted C 3-6 substituted by a substituent selected from cycloalkyl-O-, optionally substituted 6-membered aryl-O-, optionally substituted 5-6-membered heterocyclyl-O-, or optionally substituted 5-10-membered heteroaryl-O-; (3) In formula IIc and IIf, the heteroaromatic ring or heterobicyclic ring formed by D1, D2, D3, D4 and the oxopyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; preferably, the heteroaromatic ring or heterobicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 substituted by a substituent selected from the group consisting of cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl or =O; (4) In formula IIg, the heteroaromatic bicyclic ring formed by B1, B2, B3 and the pyridine ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; preferably, the heteroaromatic bicyclic ring is optionally substituted by 1, 2 or 3 groups selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 Preferably, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2 or 3 substituents selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 substituted by a substituent selected from cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl, and optionally substituted 5-10-membered heteroaryl; (5) In formula IIh, the heteroaromatic bicyclic ring formed by B1, B2, B3 and the benzene ring is: Wherein, *1, *2 and *3 are the connection positions with R1, R5 and R6 in the compound structure respectively; R 13 is hydrogen, optionally substituted C 1-6 Alkyl, optionally substituted C 3-6 Cycloalkyl, optionally substituted aryl or optionally substituted 5-6 membered heteroaryl, preferably C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 3-4 Cycloalkyl or optionally 1-2 selected C 1-3 alkyl or halogen substituted 5-6 membered heteroaryl; preferably, the heteroaromatic bicyclic ring may be optionally substituted by 1, 2, 3 or 4 selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 Preferably, the heteroaromatic bicyclic ring may be optionally substituted with 1, 2, 3 or 4 substituents selected from halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 The substituents are substituted by cycloalkyl, optionally substituted 6-membered aryl, optionally substituted 5-6-membered heterocyclyl and optionally substituted 5-10-membered heteroaryl.

11. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: The compound of formula I has the structure shown in the following formula IIa: Where: R1 is: Where R2 is C 1-4 Alkyl, preferably methyl or ethyl; R3 is C 1-4 Alkyl, halogen, C 3-6 Cycloalkyl or halogenated C 1- 4 alkyl, preferably C 1-4 Alkyl, such as methyl or ethyl; n is 0 or 1; R4 is H, C 1-4 Alkyl or halogen, preferably halogen; Z1 and Z2 are each independently N or CH, and at least one of Z1 and Z2 is N; R5 is -NR 5a R 5b , where R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably each independently hydrogen or C 1-3 Alkyl, more preferably all hydrogen; R6 is -C(O)NR 6a R 6b , where R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl, C 3-8 Cycloalkyl, optionally substituted 5 or 6 membered heteroaryl substituted C 1-6 alkyl or optionally substituted 5-10 membered heteroaryl, preferably each independently hydrogen, C 1-6 Alkyl or C 3-8 cycloalkyl, more preferably each independently hydrogen or C 1-3 alkyl, more preferably all hydrogen; preferably, the optionally substituted 5- or 6-membered heteroaryl is optionally substituted by 1 or 2 groups selected from halogen and C 1-4 A 5- or 6-membered nitrogen-containing heteroaryl group substituted with an alkyl substituent; R9 is hydrogen; A3 is N or CR 10 ; A4 is N or CR 10 ; A5 is N or CR 10 , and at least one of A3, A4 and A5 is N; R 10 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, R 10 are independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, NR'R"CO-substituted C 1-4 Alkyl, C 3-6 Cycloalkyl substituted C 1-4 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 Cycloalkyl, halogenated C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl, wherein R' and R" are each independently H or C 1-4 More preferably, R 10 are independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, the optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl is optionally substituted by 1 or 2 selected from halogen, C 1-4 Alkyl, C 1-4 The substituents of the alkoxy group and the optionally substituted 4- to 7-membered heterocyclic group are substituted.

12. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: The compound of formula I has the structure shown in the following formula IIa: Where: R1 is: Wherein, W is N; R2 is hydrogen or C 1-4 Alkyl, preferably hydrogen; R3 is hydrogen or C 1-4 Alkyl, preferably hydrogen; n is 0 or 1; R4 is H, C 1-4 Alkyl or halogen; R5 is -NR 5a R 5b , where R 5a and R 5b Each is independently hydrogen, C 1-6 Alkyl or C 3-8 Cycloalkyl, preferably each independently hydrogen or C 1-3 Alkyl, more preferably all hydrogen; R6 is -C(O)NR 6a R 6b , where R 6a and R 6b Each is independently hydrogen, C 1-6 Alkyl, C 3-8 cycloalkyl or optionally substituted 5-10 membered heteroaryl, preferably each independently hydrogen or C 1-3 Alkyl, more preferably all hydrogen; R9 is hydrogen; A3 is N or CR 10 ; A4 is N or CR 10 ; A5 is N or CR 10 , and at least one of A3, A4 and A5 is N; R 10 are each independently hydrogen, halogen, optionally substituted C 1-6 Alkyl, optionally substituted C 1-6 Alkoxy, optionally substituted C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, R 10 are independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 Cycloalkyl, halogenated C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; more preferably, R 10 are independently hydrogen, halogen, C 1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy, C 3-8 cycloalkyl, optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl; preferably, the optionally substituted 6-14 membered aryl, optionally substituted 4-7 membered heterocyclyl or optionally substituted 5-10 membered heteroaryl is optionally substituted by 1 or 2 selected from halogen, C 1-4 Alkyl, C 1-4 The substituents of the alkoxy group and the optionally substituted 4- to 7-membered heterocyclic group are substituted.

13. The compound according to claim 1, its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof, characterized in that: The compound of formula I is selected from: 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide; (7-amino-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridin-8-yl)(6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)methanone; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)indolizine-8-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-4-carboxamide; 5-amino-6-(1H-indol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide; 5-amino-6-(1H-indazol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide; 5-amino-6-(5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridine-4-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 8-amino-7-(3-hydroxy-2,6-dimethylphenyl)-4-oxo-4H-quinolizine-9-carboxamide; 7-amino-6-(1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide; 8-amino-7-(7-methyl-1H-indazol-6-yl)-6-oxo-1,3,4,6-tetrahydro-2H-quinoline-9-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-oxazolo[3,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-8-carboxamide; 2-amino-3-(3-hydroxy-2,6-dimethylphenyl)-4-oxo-4H-quinolizine-1-carboxamide; 5-amino-4-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-6-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,5-a]pyridine-6-carboxamide; 7-amino-2,3-dimethyl-8-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylindolizine-6-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-6-carboxamide; 7-amino-8-(3-hydroxy-2,6-dimethylphenyl)-5-oxo-5H-oxazolo[3,2-a]pyridine-6-carboxamide; 8-amino-9-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,3,4,6-tetrahydro-2H-quinolizine-7-carboxamide; 8-amino-9-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-6H-pyrido[1,2-a]pyrazine-7-carboxamide; 4-amino-5-(3-hydroxy-2,6-xylyl)-6-oxo-1-(thiazol-2-yl)-1,6-dihydropyridine-3-carboxamide; 4-amino-3-(3-hydroxy-2,6-xylyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide; 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-oxo-1-(thiazol-2-yl)-1,2-dihydropyridine-3-carboxamide; 4-amino-5-(3-hydroxy-2,6-xylyl)-2-oxo-2H-[1,2′-bipyridine]-3-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide; 4-amino-3-(5-methyl-1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide; 7-amino-8-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide; 7-amino-8-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-6-carboxamide; 7-amino-6-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide; 4-amino-3-(1H-indazol-4-yl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide; 7-amino-6-(5-hydroxy-2-methylphenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide; 4-amino-3-(5-hydroxy-2-methylphenyl)-2-oxo-2H-[1,2′-bipyridine]-5-carboxamide; 7-amino-6-(5-hydroxy-2-methylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-3-methylimidazo[1,2-a]pyridine-8-carboxamide; 3-amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-1,2,5,6,7,8-hexahydroisoquinoline-4-carboxamide; 7-amino-2-hydroxy-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 3-amino-2-(3-hydroxy-2,6-dimethylphenyl)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopentadienyl[c]pyridine-4-carboxamide; 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylthiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-3-bromo-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-phenylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-(benzo[d]thiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(6-chloro-3-hydroxy-2-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1H-indazole-7-carboxamide; 7-amino-6-(2-chloro-3-hydroxy-6-methylphenyl)-2,3-dimethylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-morpholinimidazole[1,2-a]pyridine-8-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-1-methyl-1H-indazole-7-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(5-methylpyridin-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide; 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxamide; 7-amino-2-cyano-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-5-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methoxyimidazo[1,2-a]pyridine-8-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-4-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[d]oxazole-4-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-(4-chlorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 6-amino-2-(difluoromethyl)-5-(3-hydroxy-2,6-dimethylphenyl)-2H-indazole-7-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(5-methylbenzo[d]thiazol-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-(4-fluorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-(5-fluorothiazol-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(isothiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(oxazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-hydroxypropan-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-ylmethyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yloxy)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylpyrazolo[1,5-a]pyridine-4-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)pyrazolo[1,5-a]pyridine-4-carboxamide; 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-5-carboxamide; 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-5-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylbenzo[d]thiazole-4-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)benzo[d]thiazole-4-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)benzo[d]thiazole-7-carboxamide; 7-amino-6-(4-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(5-hydroxy-2,4-dimethylpyridin-3-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(2-ethyl-3-hydroxy-6-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(6-ethyl-3-hydroxy-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-6-isopropyl-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(6-cyclopropyl-3-hydroxy-2-methylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2-methyl-6-(trifluoromethyl)phenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-2H-indazole-7-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-2H-indazole-7-carboxamide; 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)indolizine-5-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)pyrazolo[1,5-a]pyridine-7-carboxamide; 6-amino-7-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-5-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-1H-benzo[d]imidazole-4-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)benzo[d]thiazole-7-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)-1H-indole-4-carboxamide; 5-amino-6-(3-hydroxy-2,6-dimethylphenyl)benzo[b]thiophene-4-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)benzo[b]thiophene-7-carboxamide; 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(2-neoamidophenyl)-1,6-dihydropyridine-3-carboxamide; 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(2-hydroxy-3,5-dimethylpyridin-4-yl)-2-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-morpholinimidazole[1,2-a]pyridine-8-carboxamide; 7-amino-2-chloro-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-phenylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-(thiazol-2-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methoxyimidazo[1,2-a]pyridine-8-carboxamide; 6-amino-5-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylbenzo[d]thiazole-7-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2-(thiazol-2-yl)ethyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(thiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(pyridazin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-3-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(3,4-difluoro-5-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-chloro-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(2-hydroxy-3,5-dimethylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(5-hydroxy-2,4-dimethylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-3-chloro-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropylimidazo[1,2-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(methyl-d3)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-2-(methyl-d3)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(4-bromofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-(pyridin-3-yl)furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(benzofuran-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(4,4-difluoropiperidin-1-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-3-cyclopropyl-6-(3-hydroxy-2,6-dimethylphenyl)imidazo[1,5-a]pyridine-8-carboxamide; 4-amino-1-(furan-2-yl)-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide; 4-amino-1-(benzofuran-2-yl)-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxamide; 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(4-phenylfuran-2-yl)-1,6-dihydropyridine-3-carboxamide 4-amino-5-(3-hydroxy-2,6-dimethylphenyl)-6-oxo-1-(4-(pyridin-3-yl)furan-2-yl)-1,6-dihydropyridine-3-carboxamide; 7-amino-6-(5-chloro-4-methylpyridin-3-yl)-2-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(3-fluoropyridin-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(3-methoxypyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(2-amino-2-oxoethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(4-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-isopropyl-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-fluoro-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(3,3-difluorocyclobutyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(furan-2-yl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-ethyl-6-(4-fluoro-3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(cyclopropylmethyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclopentyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-cyclohexyl-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-fluoro-5-hydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(tert-butyl)-6-(3-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-4-yl"-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(tetrahydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-2-(cyclopropylmethyl)-6-(5-methyl-1H-indazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3,5-dihydroxy-2,6-dimethylphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(7-fluoro-1H-indazol-4-yl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(2,6-difluoro-3-hydroxyphenyl)-2-isopropyl-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(7-fluoro-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-4-yl")-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(5-methyl-1H-indazol-4-yl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; 7-amino-6-(3-hydroxy-2,6-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide; and 7-amino-6-(6-hydroxy-2,3-dimethylphenyl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide.

14. Use of the compound according to any one of claims 1 to 13, or its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof in the preparation of a medicament for treating or preventing a disease or condition caused by abnormal PKMYT1 activity; Preferably, the disease or disorder is cancer, preferably selected from the group consisting of liver cancer, melanoma, Hodgkin's disease, non-Hodgkin's lymphoma, acute lymphoid leukemia, chronic lymphoid leukemia, multiple myeloma, neuroblastoma, breast cancer, ovarian cancer, Wilms' tumor, cervical cancer, testicular cancer, soft tissue sarcoma, primary macroglobulinemia, bladder cancer, chronic myeloid leukemia, primary brain cancer, malignant melanoma, non-small cell lung cancer, small cell lung cancer, gastric cancer, colon cancer, malignant pancreatic insulinoma, malignant carcinoid cancer, choriocarcinoma, mycosis fungoides, head and neck cancer, osteogenic sarcoma, pancreatic cancer, acute myeloid leukemia, hairy cell leukemia, rhabdomyosarcoma, Kaposi's sarcoma, genitourinary neoplasia, thyroid cancer, esophageal cancer, cervical hyperplasia, renal cell carcinoma, endometrial cancer, polycythemia vera, essential thrombocythemia, adrenocortical carcinoma, skin cancer and prostate cancer; Preferably, the drug further comprises at least one known anticancer drug or a pharmaceutically acceptable salt thereof;Preferably, the anticancer drug is selected from one or more of the following groups: vorinostat, romidepsin, panobinostat, belinostat, palbociclib, busulfan, melphalan, chlorambucil, cyclophosphamide, ifosfamide, temozolomide, bendamustine, cisplatin, mitomycin C, bleomycin, carboplatin, camptothecin, irinotecan, topotecan, doxorubicin, epirubicin, aclarubicin, mitoxantrone, methylhydroxyellipticine, mingtopop, 5-azacytidine, gemcitabine, 5-fluorouracil, methotrexate, 5-fluoro-2′-deoxyuridine, fludarabine, nelarabine, cytarabine, pralatrexate, pemetrexed, hydroxyurea, thioguanine, colchicine, vinblastine, vincristine, long Primordialib, paclitaxel, ixabepilone, cabazitaxel, docetaxel, monoclonal antibody, panitumumab, necrotizumab, nivolumab, pembrolizumab, ramucirumab, bevacizumab, pertuzumab, trastuzumab, cetuximab, obinutuzumab, ofatumumab, rituximab, alemtuzumab, ibritumomab tiuxetan, tositumomab, brentuximab, daratumumab, elotuzumab, ofatumumab, dinutuximab, blinatumomab, ipilimumab, Avastin, Herceptin, rituximab, trastuzumab-emtansine conjugate T-DM1, humanized anti-HER2 antibody-drug conjugate trastuzumab Deruxtecan, Trastuzumab Emtansine, Humanized anti-TROP2 monoclonal antibody-drug conjugate Datopotamab Deruxtecan, Gemtuzumab Ozogamicin, CD30-directed antibody-drug conjugate Brentuximab Vedotin, Inotuzumab Ozogamicin, Sacituzumab govitecan, Enfortumab Vedotin, and Belantamab Mafodotin, imatinib, gefitinib, erlotinib, osimertinib, afatinib, ceritinib, alectinib, crizotinib, erlotinib, lapatinib, sorafenib, regorafenib, vemurafenib, dabrafenib, aflibercept, sunitinib, nilotinib, dasatinib, bosutinib, pralsetinib, ibrutinib, cabozantinib, lenvatinib, vandetanib, trametinib, cobimetinib, axitinib, temsirolimus, Idel alisib, pazopanib, tebuconazole, everolimus, tamoxifen, letrozole, fulvestrant, mitoguanidine, octreotide, retinoic acid, arsenic, zoledronic acid, bortezomib, carfilzomib, ixazomib, vismodegib, sonidegi, denosumab, thalidomide, lenalidomide, venetoclax, aldesleukin (recombinant human interleukin-2), and sipueucel-T (a prostate cancer vaccine); Preferably, the medicament is used in combination with radiation therapy.

15. A pharmaceutical composition comprising the compound according to any one of claims 1 to 13, or its stereoisomer, tautomer, N-oxide, hydrate, solvate, isotope-labeled compound or pharmaceutically acceptable salt, or a mixture thereof and a pharmaceutically acceptable carrier; Preferably, the pharmaceutical composition further contains at least one known anticancer drug or a pharmaceutically acceptable salt thereof; preferably,The at least one known anticancer drug is selected from the group consisting of vorinostat, romidepsin, panobinostat, belinostat, palbociclib, busulfan, melphalan, chlorambucil, cyclophosphamide, ifosfamide, temozolomide, bendamustine, cisplatin, mitomycin C, bleomycin, carboplatin, camptothecin, irinotecan, topotecan, doxorubicin, epirubicin, aclarubicin, mitoxantrone, methylhydroxyellipticine, mingtopop, 5-azacytidine, gemcitabine, 5-fluorouracil, methotrexate, 5-fluoro-2′-deoxyuridine, fludarabine, nelarabine, cytarabine, pralatrexate, pemetrexed, hydroxyurea, thioguanine, colchicine, vinblastine, vincristine, vinorelbine brine, paclitaxel, ixabepilone, cabazitaxel, docetaxel, monoclonal antibody, panitumumab, necrotizumab, nivolumab, pembrolizumab, ramucirumab, bevacizumab, pertuzumab, trastuzumab, cetuximab, obinutuzumab, ofatumumab, rituximab, alemtuzumab, ibritumomab tiuxetan, tositumomab, brentuximab, daratumumab, elotuzumab, ofatumumab, dinutuximab, blinatumomab, ipilimumab, avastin, herceptin, rituximab, trastuzumab-emtansine conjugate T-DM1, humanized anti-HER2 antibody-drug conjugate trastuzumab Deruxtecan, Trastuzumab Emtansine, Humanized anti-TROP2 monoclonal antibody-drug conjugate Datopotamab Deruxtecan, Gemtuzumab Ozogamicin, CD30-directed antibody-drug conjugate Brentuximab Vedotin, Inotuzumab Ozogamicin, Sacituzumab govitecan, Enfortumab Vedotin, and Belantamab Mafodotin, imatinib, gefitinib, erlotinib, osimertinib, afatinib, ceritinib, alectinib, crizotinib, erlotinib, lapatinib, sorafenib, regorafenib, vemurafenib, dabrafenib, aflibercept, sunitinib, nilotinib, dasatinib, bosutinib, pralsetinib, ibrutinib, cabozantinib, lenvatinib, vandetanib, trametinib, cobimetinib, axitinib, temsirolimus, idelalisib, pazopa Ni, Tecansi, Everolimus, Vorinostat, Romidepsin, Panobinostat, Belinostat, Tamoxifen, Letrozole, Fulvestrant, Mitoguanzone, Octreotide, Retinoic acid, Arsenic, Zoledronic acid, Bortezomib, Carfilzomib, Ixazomib, Vismodegib, Sonidegi, Denosumab, Thalidomide, Lenalidomide, Venetoclax, Aldesleukin (recombinant human interleukin-2) and Sipueucel-T (prostate cancer treatment vaccine).

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