Azepine compounds, their compositions and uses

Abstract

Compounds represented by general formula I, compositions and their uses. Compounds represented by general formula I have the following structures, and their pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates and deuterated compounds. TIFF2026519809000321.tif40170

Description

[Technical Field]

[0001] This application claims priority to a Chinese patent application filed with the China National Patent Office on 9 June 2023, application number 202310682400.4, title of invention "Benzodiazepine compounds, compositions and uses thereof," which is incorporated herein by reference in its entirety.

[0002] This invention belongs to the field of pharmaceutical technology and specifically relates to azepine compounds, their compositions, and their use. [Background technology]

[0003] Benzodiazepines are a type of sedative and hypnotic drug developed in the late 1950s. Because they have fewer toxic side effects compared to barbiturates, they are the first-line treatment for sedation, hypnosis, and anxiety in clinical practice.

[0004] The mechanism of action of benzodiazepine drugs is as follows: Benzodiazepine receptors, which have a high affinity for diazepam, are present in the brain, most abundantly distributed in the cerebral cortex, followed by the limbic system, midbrain, and then the brainstem and spinal cord. This distribution pattern is similar to that of gamma-aminobutyric acid (GABA), a central inhibitory neurotransmitter. A This closely matches the distribution of receptors. Benzodiazepine drugs enhance agonistic neurotransmission and synaptic inhibitory effects, affecting GABA and GABAGABA. A By strengthening receptor binding, it exerts anti-anxiety, sedative, and hypnotic effects. [Overview of the Initiative]

[0005] The object of the present invention is to provide azepine compounds, pharmaceutical compositions of the azepine compounds, and uses of the azepine compounds.

[0006] In a first embodiment, the present invention provides compounds represented by general formula I, pharmaceutically acceptable salts thereof, stereoisomers, prodrugs, solvates, and deuterated compounds.

[0007] TIFF2026519809000002.tif33170Here, Y is selected from N or -CF, A is selected from N or CH, M is absent or forms a condensed ring with an adjacent carbon to jointly form a saturated / unsaturated alicyclic ring, a saturated / unsaturated heterocyclic ring, an aromatic ring or a heteroaromatic ring, When M is absent, R X is -H, halogen, -NO 2、 -CN, -CF3, C 2-8 an alkenyl group, C 2-8 an alkynyl group, C 1-10 a straight-chain / branched alkyl group, -N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -OC 0-10 an alkyl group, C 3-10 a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, an S heterocycloalkyl group, and when M forms a condensed ring with an adjacent carbon, R X is absent, n1 is 0, 1 or 2, The H in the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring or heteroaromatic ring is halogen, -NO2, -CN, -CF3, C 2-8 an alkenyl group, C 2-8 an alkynyl group, C 1-10 a straight-chain / branched alkyl group, -N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -OC 0-10 an alkyl group, C 3-10 a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, an S heterocycloalkyl group, -NHCO(C 0-10 an alkyl group) and can be substituted, Q is O, S-Rxx, N or TIFF2026519809000003.tif12170selected from, R3 is -H, C 1-5 a straight-chain / branched alkyl group selected from, and the H in the alkyl group is -N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -OC0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. When Q is N, R3, Q, together with the N and C atoms between them, form a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms, optionally the 5-membered aromatic heterocycle being an imidazole group, and optionally the 6-membered aromatic heterocycle being a pyridyl group. L does not exist, or L is C 2-8 Olefin bond or C l-8 Selected from alkylene groups, where H in the group is halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 Alkyl group )(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. Q is N or TIFF2026519809000004.tif12170, and when A is N, Q, A, and L, together with the atoms in between, form a 5-membered or 6-membered nitrogen-containing heterocycle. n is either 0 or 1, and when n is 0, it indicates that there is no -CO- group. If X is absent or n is 1, X is O; if n is 0, X is selected from O, substituted / unsubstituted N alkyl groups, and substituted / unsubstituted N heterocycloalkyl groups. R4 is -H, halogen, CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C3-10 Cycloalkyl groups, heterocycloalkyl groups, aryl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, -SO2(C 0-10 Alkyl(alkyl group), -SO(C 0-10 Alkyl(alkyl group), -SO2O(C 0-10 Alkyl(alkyl group), -SO2N(C 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -SO2(C 3-10 Cycloalkyl group), -SO2-aryl group, -CON(C 0-10 (Alkyl group)(C 0-10 Alkyl(C)(-CO(C)) 0-10 Alkyl(C)(-CO(C)) 3-10 Cycloalkyl groups), -CO (3-6 member heterocycloalkyl groups), (C 0-10 Alkyl(COO)(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, -NO2, -CF3, or C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C 3-6 Heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C), -CON(C 0-10 (Alkyl group)(C 0-10 Alkyl(C)), -OCOO(C 0-10 It can be substituted with alkyl groups, phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, and alkynyl groups.

[0008] Preferably, Y is N.

[0009] In equation I, "TIFF2026519809000005.tif5170" indicates a single bond or a double bond.

[0010] In this invention, the formation of a fused ring between M and an adjacent carbon atom means that M forms a ring with an adjacent carbon atom and also condenses with the seven-membered ring of the core structure to form a fused ring. The ring that M forms with an adjacent carbon atom may be a monoring or a fused ring.

[0011] When Q is O, it bonds to the nucleus via a double bond. When Q is S, it bonds to the nucleus via a single bond. It bonds to the nucleus via a single bond or a double bond. When Q is N or If the data type is TIFF2026519809000006.tif10170, it binds to the nucleus via single or double bonds.

[0012] To more clearly indicate the positions of M and adjacent carbon atoms, the nuclear atoms represented by formula I are numbered as follows: If TIFF2026519809000007.tif34170M does not exist, the structure of the compound represented by formula I is as follows: TIFF2026519809000008.tif30170M forming a fused ring with an adjacent carbon means that M forms a ring with the carbon at position 6 and the carbon at position 7, forming a saturated / unsaturated alicyclic ring, a saturated / unsaturated heterocyclic ring, an aromatic ring, or a heteroaromatic ring.

[0013] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000009.tif30170 Here, Y is selected from N or -CF, R1 and R2 are independently -H, halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is selected from .N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, or R1 and R2 are such that the C atom between R1 and R2 forms a 5-membered aromatic heterocycle, a 6-membered aromatic heterocycle, or an aromatic ring, and the 5-membered aromatic heterocycle is selected from furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, and thiazole, and the 6-membered aromatic heterocycle is selected from pyridine, pyridazine, pyrimidine, and pyrazine. Optionally, the H in the 5-membered aromatic heterocycle, 6-membered aromatic heterocycle, or aromatic ring is a halogen, -CN, -CF3, or C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -OOC 1-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, or an S heterocycloalkyl group, and optionally the aromatic ring is selected from a 6-membered aromatic ring. Q is selected from O, S, or N, and R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. When Q is N, R3, Q, together with the N and C atoms between them, form a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms, and optionally the 5-membered aromatic heterocycle is an imidazole group. L does not exist, or L is C 2-8 Olefin bond or Cl-8 Selected from an alkylene group, where H in said group is halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 a straight-chain / branched alkyl group, -N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -OC 0-10 an alkyl group, C 3-10 a cycloalkyl group, -CO(C 0-10 an alkyl group), -COO(C 0-10 an alkyl group) and may be substituted by When Q is N and A is N, Q, A, and L, together with the atoms between them, form a 5- or 6-membered nitrogen-containing heterocyclic ring, n is 0 or 1, and when n is 0, it indicates that the -CO- group does not exist, X does not exist, or when n is 1, X is O, and when n is 0, X is selected from O, a substituted / unsubstituted N-alkyl group, and a substituted / unsubstituted N-heterocycloalkyl group, R4 is -H, halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 a straight-chain / branched alkyl group, -N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -OC 0-10 an alkyl group, C 3-10 a cycloalkyl group, a heterocycloalkyl group, an aryl group, an N-heterocycloaryl group, an O-heterocycloaryl group, an S-heterocycloaryl group, -SO2(C 0-10 an alkyl group), -SO(C 0-10 an alkyl group), -SO2O(C 0-10 an alkyl group), -SO2N(C 0-10 an alkyl group)(C 0-10 an alkyl group), -SO2(C 3-10 a cycloalkyl group), -SO2-aryl group, -CON(C 0-10 an alkyl group)(C 0-10 an alkyl group), -CO(C 0-10 an alkyl group), -CO(C 3-10 a cycloalkyl group), -CO(3-6 membered heterocycloalkyl group), -(C 0-10Alkyl(COO)(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, -NO2, -CF3, or C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C 3-6 Heterocycloalkyl groups, -N( 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C), -CON(C 0-10 (Alkyl group)(C 0-10 Alkyl(C)), -OCOO(C 0-10 It can be substituted with alkyl groups, phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, and alkynyl groups.

[0014] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000010.tif32170

[0015] Here, Y is selected from N or -CF, R1 and R2 are independently -H, -F, -Cl, -Br, -NO2, -CN, -CF3, and C. 2-4 Alkenyl group, C 2-4 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10R1 and R2 are selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, or R1 and R2, together with the C atom between R1 and R2, form a 5-membered aromatic heterocycle, a 6-membered aromatic heterocycle, or a benzene ring, wherein the 5-membered aromatic heterocycle is selected from furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, and thiazole, and the 6-membered aromatic heterocycle is selected from pyridine, pyridazine, pyrimidine, and pyrazine. Optionally, the H in the 5-membered aromatic heterocycle, 6-membered aromatic heterocycle, or benzene ring may be halogen, -CN, -CF3, or C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 1-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, or an S heterocycloalkyl group. Q is chosen from O or N, and R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group or a 3- to 8-membered heterocycloalkyl group, the heterocycloalkyl group containing at least one N, O, or S as a ring atom. When Q is N, R3, Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. L does not exist, or L is C 2-4 Olefin bond or C 1-8 Selected from alkylene groups, where H in the group is halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C n-10 (alkyl group), -OC 0-10Alkyl alkyl groups, 3-10 membered cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. R a is -H, C 1-10 Linear / branched alkyl groups, OR b Selected from, R b C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3- to 8-membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, -CN, -CH3, -C2H5, or -OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R c is -H, -Cl -10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH2CO(C 0-10 Alkyl(alkyl group), -CH2COO(C 0-6 Alkyl(alkyl group), -CH2COO(C 3-6 Cycloalkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO2, C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 (Alkyl alkyl group), C 2-8It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or R c teeth, TIFF2026519809000011.tif12170, TIFF2026519809000012.tif14170, Selected from TIFF2026519809000013.tif11170, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, and vinyl groups may be substituted with y, wherein the alkyl group is -CN, -OCF3, -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R d1 and R d2 These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(C)(-CO(C)) 0-10 Selected from alkyl groups, 3-6 membered cycloalkyl groups, 3-6 membered heterocycloalkyl groups, or aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3-6 member heterocycloalkyl group, and the H in the group is a halogen, -CN, -NO2, C 1-3 Linear / branched alkyl groups, -OC1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-10 Alkyl(COO)(C 0-10 Alkyl(C)(-CO(C)) 0-10 Alkyl group), aryl group, -N(C 1-3 (Alkyl group)(C 1-3 The alkyl group may be substituted with -CN, -OCF3, -OC 0-10 , -CO(C 0-10 (Alkyl alkyl group), C 3-4 It may be substituted with a cycloalkyl group or an aryl group. R e1 and R e2 These are H and C, respectively, independently. 1-3 Selected from linear / branched alkyl groups.

[0016] In certain embodiments of the present invention, the compound, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound have the following structural formula: TIFF2026519809000014.tif31170

[0017] Here, the substitutions of Y, Q, R1, R2, and R3 are as described above.

[0018] m is an integer between 0 and 4. R5 is -H, halogen, -CN, -CF3, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R6 is -H, C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3-6 membered heterocycloalkyl groups, and aryl groups, where H in the group is a halogen, -CN, -CH3, -C2H5, -OCH3, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted with a cycloalkyl group.

[0019] Furthermore, the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000015.tif30170 Here, Y is selected from N or -CF, and P is N or CH, m is an integer between 0 and 4. R7 consists of -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R8 is -H, -CN, -CF3, C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R9 consists of -H, -F, -Cl, -Br, I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 10 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group)(C 1-3It may be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group, R5 is -H, halogen, -CN, -CF3, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R 6’ and R 6” Each of these is independently -H, CL-10 linear / branched alkyl group, C 3-10 Selected from cycloalkyl groups, 3-6 membered heterocycloalkyl groups, and aryl groups, where H in the group is a halogen, -CN, -CH3, -C2H5, -OCH3, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted with a cycloalkyl group.

[0020] Furthermore, the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000016.tif29170 Here, Y is selected from N or -CF, and P is N or CH, m1 is an integer between 0 and 2. R 11 -F, -Cl, -Br, -I, -NO2, ethynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 6a teeth, TIFF2026519809000017.tif14170, TIFF2026519809000018.tif12170, TIFF2026519809000019.tif14170 or C 1-4 Selected from alkyl groups, the H in the alkyl group is -F, -OCH3, C 3-6 Can be substituted with a cycloalkyl group, R 6a1 R is selected from -H, -CN, -CH3, -C2H5, vinyl group, propadienyl group, and ethynyl group. 6a2 R is selected from vinyl group, ethynyl group, -COCH3, -COC2H5, and 3-4 member epoxy alkyl groups. 6a3 It is selected from -CH3, -C2H5, -OCH3, and -OC2H5.

[0021] R 12 These are selected from -F, -Cl, -Br, -I, -, ethynyl group, and -CF3. R 13 , R 13’ , R 13” These are, independently, -H and C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group)(C 1-3 It may be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group, R 6b The group is selected from -H, -CH3, -C2H5, propyl group, isopropyl group, butyl group, tert-butyl group, and 3-4 membered saturated ring O alkyl group, and the H in the group is -F, -CI, -CN, -CH3, -C2H5, -OCH3, C 3-4 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 1-3 Alkyl(alkyl group), -OCO(C 1-3 It may be substituted with alkyl groups, vinyl groups, or ethynyl groups, and furthermore, the alkyl group may be substituted with -OCH3 or -OC2H5.

[0022] R 14 -H, halogen, -NO2, -CN, -CF3, C1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, R 6C is -H, C 1-5 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and -O heterocycloalkyl groups, the H in the group may be substituted with -F, -Cl, -CN, -CH3, -C 2H5, -OCH3, C3-4 cycloalkyl groups, vinyl groups, or ethynyl groups.

[0023] T is C, N, O, or S. R 15 -H, halogen, -NO2, -CN, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, R 6d is -H, C 1-5 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and -O heterocycloalkyl groups, the H in the group is -F, -Cl, -CN, -CH3, -C2H5, -OCH3, C 3-4 It can be substituted with cycloalkyl groups, vinyl groups, or ethynyl groups.

[0024] In certain embodiments of the present invention, the compound, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound have the following structural formula: TIFF2026519809000020.tif33170

[0025] Here, the substitutions of Y, Q, L, R1, R2, and R3 are as described above.

[0026] R 16 C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O(C 3-4 (heterocycloalkyl group), -C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group )(C 0-10 Selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted with a cycloalkyl group.

[0027] Furthermore, the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000021.tif66170

[0028] Here, Y is selected from N or -CF, and P is N or CH. m is an integer between 0 and 4. R7 consists of -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 Alkyl group )(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R8 is -H, -CN, -CF3, C 1-4 Linear / branched alkyl groups, C3-10 Selected from member cycloalkyl groups, R9 is -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, CL-10 linear / branched alkyl group, -N(C 0-10 Alkyl group )(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 10 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 Alkyl group )(C 1-3 It can be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group.

[0029] R 16’ , R 16” , R 16* , R 16** R 16# and R 16## Each of them is independent of C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O(C 3-4 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group )(C 0-16 Selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 Alkyl group )(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted with a cycloalkyl group.

[0030] Furthermore, the compounds, their pharmaceutically acceptable salts, stereoisomers, esters, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000022.tif101170

[0031] Here, Y is selected from N or -CF, m1 is an integer between 0 and 2. R 17 and R 18 These are independently selected from -F, -Cl, -Br, -I, -NO2, ethynyl group, and -CF3. R 16a1 and R 16a2 Each of them is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O(C 3-4 Heterocycloalkyl groups), C 3-6 Cycloalkyl group, 3-6 member N heterocycloalkyl group, 3-6 member O heterocycloalkyl group, -N(C 0-10 Alkyl group )(C 0-10 Selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 Alkyl group )(C 1-3 Alkyl groups can be substituted with vinyl groups.

[0032] R 16b1 and R 16b2 Each of them is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, aryl group, -N(C 1-3 Alkyl group )(C 1-3 A alkyl group is selected from the alkyl groups, and the H in the group may be substituted with a halogen, -CN, -CH3, -C2H5, or -OCH3.

[0033] R 16 c1 and R 16 c2 is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and aryl groups.

[0034] In certain embodiments of the present invention, the compound, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound have the following structural formula: TIFF2026519809000023.tif32170

[0035] Here, the substitutions of Y, Q, R1, R2, and R3 are as described above.

[0036] m is an integer between 0 and 4. R 19 -H, -C 1-10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH2CO(C 1-5 Alkyl(C1-5), -CH2COO(C) 3-6 Cycloalkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 1-3 Alkyl group )(C 1-3 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -C3H7, 3-6 member heterocycloalkyl groups, -OC 1-3 Alkyl, -N(C 1-3 Alkyl group )(C 1-3 It can be substituted with alkyl groups, vinyl groups, imidazolyl groups, oxazolyl groups, thiazolyl groups, or pyridinyl groups.

[0037] Furthermore, the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000024.tif42170

[0038] Here, Y is selected from N or -CF, and P is N or CH. m is an integer between 0 and 4. R7 consists of -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R8 is -H, -CN, -CF3, C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R9 consists of -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, -CF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 10 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 Alkyl group )(C 1-3 It can be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group.

[0039] R 19’ and R 19” These are -H and -C, respectively, independently. 1-10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH2CO(C 1-5 Alkyl(alkyl group), -CH2COO(C 1-5 Alkyl(alkyl group), -CH2COO(C 3-6Cycloalkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 1-3 (Alkyl group)(C 1-3 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -C3H7, 3-6 member heterocycloalkyl groups, -OC 1-3 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 It can be substituted with alkyl groups, vinyl groups, imidazolyl groups, oxazolyl groups, thiazolyl groups, or pyridinyl groups.

[0040] Furthermore, the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000025.tif38170

[0041] Here, Y is selected from N or -CF, and P is N or CH. m1 is an integer between 0 and 2. R 17 and R 18 These are independently selected from -F, -Cl, -Br, -I, -NO2, ethynyl group, and -CF3. R 19a1 and R 19a2 These are, independently, -H and C 1-3 Linear / branched alkyl groups, C 3-6 Cycloalkyl groups, -CH2CO(C 1-3 Alkyl(alkyl group), -CH2COO(C 1-3 Alkyl(alkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 1-3 (Alkyl group)(C 1-3 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -C3H7, -OC 1-3 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3It can be substituted with alkyl groups, vinyl groups, imidazolyl groups, thiazolyl groups, or pyridinyl groups.

[0042] In certain embodiments of the present invention, the compound, its pharmaceutically acceptable salt, stereoisomer, ester, prodrug, solvate, and deuterated compound have the following structural formula: TIFF2026519809000026.tif38170

[0043] Here, the substitutions of Y, Q, R1, R2, and R3 are as described above.

[0044] m is an integer between 0 and 4. R 20a and R 20b These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(C)(-CO(C)) 0-10 (Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3-6 member heterocycloalkyl groups, aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3-6 member N heterocycloalkyl group, and the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3 Alkyl(COO)(C 0-5 Alkyl(C)(-CO(C)) 0-5 Alkyl(alkyl group), -N(C) 1-3 (Alkyl group)(C 1-3 Alkyl group), may be substituted with an aryl group, the alkyl group portion being -CN, -OCF3, -OC 0-3 Alkyl group, -CO(C 0-5 (Alkyl alkyl group), C 3-4 It can be substituted with cycloalkyl groups or aryl groups.

[0045] Furthermore, the compounds, their pharmaceutically acceptable salts, stereoisomers, esters, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000027.tif42170

[0046] Here, Y is selected from N or -CF, and P is N or CH. m is an integer between 0 and 4. R7 is selected from -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, and -CF3. R8 is -H, -CN, -CF3, C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R9 is selected from -H, -F, -Cl, -Br, -I, -NO2, -CN, alkenyl group, alkynyl group, and -CF3. R 10 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 Alkyl group )(C 1-3 It can be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group.

[0047] R 20a’ , R 20a”、 R 20b’ and R 20b” These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(C)(-CO(C)) 0-10 (Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3-6 member heterocycloalkyl groups, aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3-6 member N heterocycloalkyl group, and the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3Alkyl(COO)(C 0-5 Alkyl(C)(-CO(C)) 0-5 Alkyl(alkyl group), -N(C) 1-3 Alkyl group )(C 1-3 Alkyl group), may be substituted with an aryl group, the alkyl group portion being -CN, -OCF3, -OC 0-3 Alkyl group, -CO(C 0-5 (Alkyl alkyl group), C 3-4 It can be substituted with cycloalkyl groups or aryl groups.

[0048] Furthermore, the compounds, their pharmaceutically acceptable salts, stereoisomers, esters, prodrugs, solvates, and deuterated compounds have the following structural formulas: TIFF2026519809000028.tif35170

[0049] Here, Y is selected from N or -CF, m1 is an integer between 0 and 2. R 21 These are selected from -F, -Cl, -Br, -I, -NO2, ethynyl group, and -CF3. R 22a and R 22b These are, independently, -H and C 1-3 Linear / branched alkyl groups, -COO(C 1-3 Alkyl(C)(-CO(C)) 1-3 (Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3-6 membered heterocycloalkyl groups, and aryl groups, wherein the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -OCH3, -(C 0-3 Alkyl group )COO(C 1-3 It can be substituted with an alkyl group.

[0050] m2 is an integer between 1 and 3. R 23 is -H, C 1-3 Linear / branched alkyl groups, -COO(C 1-3 Alkyl(C)(-CO(C)) 1-3 (Alkyl alkyl group), C 3-5Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-3 (Alkyl group)(C 0-3 Selected from alkyl groups and aryl groups, the H in the group is -F, -Cl, -CN, -NO2, -CH3, -C2H5, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3 Alkyl group )COO(C 0-5 Alkyl(C)(-CO(C)) 0-5 It can be substituted with an alkyl group or an aryl group.

[0051] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000029.tif34170 Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The components are a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, and an S heterocycloalkyl group, preferably R x -H, halogen, -NO2, -CN, -CF3, C23 alkenyl group, C 2-3 Alkynyl group, C 1-6 Linear / branched alkyl groups, -N(C 0-6 Alkyl group )(C 0-6 (alkyl group), -OC 0-6 Alkyl alkyl group, C 3-6A cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, an S heterocycloalkyl group, and more preferably R x -H, halogen, -NO2, -CN, -CF3, C 2-3 Alkenyl group, C 2-3 Alkynyl group, C 1-3 Linear / branched alkyl groups, -N(C 0-3 Alkyl group )(C 0-3 (alkyl group), -OC 0-3 Alkyl alkyl group, C 3-6 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n1 is 0, 1, or 2. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 Alkyl group )(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 H may be substituted with alkyl groups, preferably H in the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring is a halogen, -NO2, -CN, -CF3, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 1-6 Linear / branched alkyl groups, -N(C 0-6 Alkyl group )(C 0-6 (alkyl group), -OC 0-6 Alkyl alkyl group, C 3-6 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10H may be substituted with alkyl groups, more preferably H in the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring or heteroaromatic ring is a halogen, -NO2, -CN, -CF3, C 2-3 Alkenyl group, C 2-3 Alkynyl group, C 1-3 Linear / branched alkyl groups, -N(C 0-3 (Alkyl group)(C 0-3 (alkyl group), -OC 0-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is O, S-Rxx, N or Selected from TIFF2026519809000030.tif12170, R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 H in the alkyl group may be substituted with -N(C 1-6 (Alkyl group)(C 1-6 (alkyl group), -OC 1-6 Alkyl alkyl group, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -COO(C 1-6 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, preferably selected from H or a methyl group, wherein the H in the alkyl group is a halogen, nitro group, cyano group, or -OC. 0-10 It may be substituted with an alkyl group. When Q is N, R3, Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms with the N and C atoms between them, optionally the 5-membered aromatic heterocycle being an imidazole group, and the H in the imidazole group being a halogen, a cyano group, or -C 0-10 Alkyl, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 It may be substituted with an alkyl group, preferably the H of the imidazole group is a halogen, a cyano group, or -Cl -6 Alkyl, -N(C 1-6 (Alkyl group)(C 1-6 (alkyl group), -OC 1-6 The six-membered aromatic heterocycle may be substituted with an alkyl group, and optionally the six-membered aromatic heterocycle is a pyridyl group, and the H in the pyridyl group may be a halogen, a cyano group, or -C 0-10 Alkyl, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 It may be substituted with an alkyl group, preferably the H of the pyridyl group is a halogen, a cyano group, or -Cl -6 Alkyl, -N(C 1-6 (Alkyl group)(C 1-6 (alkyl group), -OC 1-6 It may be substituted with an alkyl group. L does not exist, or L is C 2-8 Olefin bond or C l-8 Selected from alkylene groups, where H in the group is halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 Alkyl group )(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. Q is N or In the case of TIFF2026519809000031.tif12170, Q and L form a 5-membered or 6-membered nitrogen-containing heterocycle with the atoms between them. n is either 0 or 1, and when n is 0, it indicates that there is no -CO- group. If X is absent or n is 1, X is O; if n is 0, X is selected from O, substituted / unsubstituted N alkyl groups, and substituted / unsubstituted N heterocycloalkyl groups. R4 is -H, halogen, CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, heterocycloalkyl groups, aryl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, -SO2(C 0-10 Alkyl(alkyl group), -SO(C 0-10 Alkyl(alkyl group), -SO2O(C 0-10 Alkyl(alkyl group), -SO2N(C 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -SO2(C 3-10 Cycloalkyl group), -SO2-aryl group, -CON(C 0-10 (Alkyl group)(C 0-10 Alkyl(C)(-CO(C)) 0-10 Alkyl(C)(-CO(C)) 3-10 Cycloalkyl groups), -CO (3-6 member heterocycloalkyl groups), (C 0-10 Alkyl(COO)(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, -NO2, -CF3, or C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C3-6 Heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C), -CON(C 0-10 (Alkyl group)(C 0-10 Alkyl(C)), -OCOO(C 0-10 It can be substituted with alkyl groups, phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, and alkynyl groups.

[0052] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000032.tif32170 Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C1-10 linear / branched alkyl group, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 H may be substituted with alkyl groups, preferably the H in the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring is a halogen, -CN, -NO2, -NHCO(C 0-10 Alkyl()), CF3, C 1-10 Linear alkyl groups, -OC0-10 It may be substituted with an alkyl group. Q is N or Selected from TIFF2026519809000033.tif13170, R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 H in the alkyl group may be substituted with -N(C 1-6 (Alkyl group)(C 1-6 (alkyl group), -OC 1-6 Alkyl alkyl group, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -COO(C 1-6 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. When Q is N, R3, Q, together with the N and C atoms between them, form a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms, optionally the 5-membered aromatic heterocycle being an imidazole group, and optionally the 6-membered aromatic heterocycle being a pyridyl group. Preferably, Q is N, and R3, together with its adjacent N atom of the triazolobenzodiazepine and Q, forms an imidazole structure.

[0053] Preferably, R3 and Q do not form a ring, and Q is N or -NCO(C 0-10 It is an alkyl group. When Q is N, Q is attached to the nucleus via a double bond, and Q is -NCO(C 0-10 If it is an alkyl group, Q is attached to the nucleus via a single bond.

[0054] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000034.tif32170(Ib-1-1) (Ib-1-2) (Ib-1-3)

[0055] Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. n1 is 0, 1, or 2. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 H may be substituted with alkyl groups, preferably the H in the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring is a halogen, -CN, -NO2, -NHCO(C 0-10 Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-10 It may be substituted with an alkyl group. R y1 -H, -CN, -CF3, C 1-4 Linear / branched alkyl groups, C 3-10 Selected from a cycloalkyl group, preferably selected from a methyl group, R y2 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group)(C 1-3 Alkyl(alkyl group), -COO(C 0-5 It may be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group, preferably the H in the alkyl group is N(C1-3 (Alkyl group)(C 1-3 Alkyl(alkyl group), -COO(C 1-3 It can be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group.

[0056] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000035.tif42170

[0057] Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R X -H, halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R X It does not exist, n1 is 0, 1, or 2. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10It may be substituted with an alkyl group. Q is selected from O, S-Rxx or N, and R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 membered heterocyclic alkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocyclic alkyl group contains at least one N, O, or S as a ring atom. When Q is N, R3, Q, together with the N and C atoms between them, forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, preferably H or a methyl group, wherein the H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. L does not exist, or L is C 2-4 Olefin bond or C 1-8 Selected from alkylene groups, where H in the group is halogen, -CN, -CF3, -OCH2F, -OCHF2, -OCF3, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl groups, 3-10 membered cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. R f is -H, C 1-10 Linear / branched alkyl groups, OR j Selected from, R j C 1-10 Linear / branched alkyl groups, C 3-10Selected from cycloalkyl groups, 3-8 membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, -CN, -CH3, -C2H5, or -OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R g -H, -C 1-10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH2CO(C 0-10 Alkyl(alkyl group), -CH2COO(C 0-6 Alkyl(alkyl group), -CH2COO(C 3-6 Cycloalkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, where H in the group is -F, -Cl, -CN, -NO2, C10, linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 (Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or R g teeth, TIFF2026519809000036.tif12170, TIFF2026519809000037.tif15170, Selected from TIFF2026519809000038.tif11170, R c1 , R c2 , R c3 Independently, C 1-10Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R h1 and sum R h2 These are H and C, which are independent of each other. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(C)(-CO(C)) 0-10 Selected from alkyl groups, 3-6 membered cycloalkyl groups, 3-6 membered heterocycloalkyl groups, or aryl groups, h1 and R h2 These, together with the N atoms between them, form a 3- to 6-membered heterocycloalkyl group, and the H in the group is a halogen, -CN, -NO2,C 1-3 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-10 Alkyl(COO)(C 0-10 Alkyl(C)(-CO(C)) 0-10 Alkyl group), aryl group, -N(C 1-3 (Alkyl group)(C 1-3 The alkyl group may be substituted with -CN, -OCF3, -OC 0-10 , -CO(C 0-10 It may be substituted with an alkyl group, a C3-4 cycloalkyl group, or an aryl group. Rj The group is selected from halogens, cyano groups, aryl groups, heteroaryl groups, 3-6 membered cycloalkyl groups, or 3-6 membered heterocycloalkyl groups, and the H in the group is halogen, -CN, -NO2, C 1-10 Linear / branched alkyl groups, -OC 1-10 It can be substituted with an alkyl group.

[0058] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000039.tif45170 Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n1 is 0, 1, or 2. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is selected from O, S-Rxx or N, and R3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 membered heterocyclic alkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocyclic alkyl group contains at least one N, O, or S as a ring atom. When Q is N, R3, Q, together with the N and C atoms between them, forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, preferably a methyl group, wherein the H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. m1, m2, and m3 are independent integers selected from 0 to 5, preferably from 1 to 5, and more preferably from 1 to 3. R5', R5'', and R5''' are independently -H, halogen, -CN, -CF3, and -Cl. -10 Alkyl group, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, preferably -H, halogen, -CN, -CF3, -Cl -6 Alkyl group, -CO(C 0-6 Alkyl(alkyl group), -COO(C 0-6 Selected from alkyl groups, R f ' is -H, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (Alkyl alkyl group), OR j Selected from, Rj ' is C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3-8 membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, CN, -CH3, -C2H5, or -OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. Preferably, R f ' is -H, C 1-6 Linear / branched alkyl groups, -N(C 1-6 (Alkyl group)(C 1-6 (Alkyl alkyl group), OR j Selected from, R j ' is C 1-6 Linear / branched alkyl groups, C 3-5 Selected from cycloalkyl groups, 3-6 membered heterocycloalkyl groups, phenyl groups, 3-5 membered N, O and / or S-containing heterocyclic groups, and 3-5 membered N, O and / or S-containing heteroaryl groups, where H in the group is a halogen, -CN, -CH3, -C2H5, or -OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH2F, -OCHF2, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R g ' is -H, -C 1-10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH2CO(C 0-10Alkyl(alkyl group), -CH2COO(C 0-6 Alkyl(alkyl group), -CH2COO(C 3-6 Cycloalkyl group), -CH2COO(C 3-6 Heterocycloalkyl groups), -CH2CON(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO2, C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 (Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or R g 'teeth, TIFF2026519809000040.tif12170, TIFF2026519809000041.tif16170, Selected from TIFF2026519809000042.tif11170, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C3-4 It may be substituted with a cycloalkyl group. Preferably, R g ' is -H, -C 1-6 Linear / branched alkyl groups, -C 3-6 Selected from cycloalkyl groups, the H in the group is F, -CI, -CN, -NO2, C 1-6 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 (Alkyl alkyl group), C 2-8 It may be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or Rg' is Selected from TIFF2026519809000043.tif12170, R c1 C 1-6 Linear / branched alkyl groups, -OC 1-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 1-6 (Alkyl group)(C 1-6 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R i ' is selected from halogens, cyano groups, phenyl groups, 5-6 member N, O and / or S-containing heteroaryl groups, 3-6 member cycloalkyl groups or 3-6 member heterocycloalkyl groups, preferably R i' is selected from halogen, cyano group, phenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, thiazolyl group, triazolyl group, isoxazolyl group, oxazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group or the following groups: TIFF2026519809000044.tif17170 The above R i In the base of ', H is a halogen, -CN, -NO2, C 1-6 Linear / branched alkyl groups, -OC 1-6 It may be substituted with an alkyl group. TIFF2026519809000045.tif4170 indicates the bond location.

[0059] Preferably, the structural formulas of the compound, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds are as follows: TIFF2026519809000046.tif106170 Here, Y is selected from N or -CF, and P' is N or CH, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n1 is 0, 1, or 2. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. R8' stands for -H, Halogen, -CN, -NO2, -CF3, C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R 10 ' is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group)(C 1-3 Alkyl(C)(-CO(C)) 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group, Q' is chosen from =O or -S-Rxx, where Rxx is H, C 1-3 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. m1, m2, and m3 are independently chosen from integers between 0 and 4. R5', R5'', R5''' are independently -H, halogen, -CN, -CF3, and -C 1-10 Alkyl group, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R f ' is -H, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (Alkyl alkyl group), ORj selected from ‘, R j ’ is C 1-10 linear / branched alkyl group, C 3-10 cycloalkyl group, 3-8 member heterocycloalkyl group, aryl group, heteroaryl group, wherein H in said group is halogen, -CN, -CH3, -C2H5, -OC 1-5 , C 3-6 cycloalkyl group, 3-6 member heterocycloalkyl group, -CO(C 0-10 alkyl group), -OCO(C 0-10 alkyl group), vinyl group, propadienyl group, ethynyl group, and further, the alkyl group moiety may be substituted by -CN, -OCH2F, -OCHF2, -OCF3, -OC 0-10 alkyl group, C 3-4 cycloalkyl group, R g ’ is -H, -C 1-10 linear / branched alkyl group, -C 3-10 cycloalkyl group, -CH2CO(C 0-10 alkyl group), -CH2COO(C 0-6 alkyl group), -CH2COO(C 3-6 cycloalkyl group), -CH2COO(C 3-6 heterocycloalkyl group), -CH2CON(C 0-10 alkyl group)(C 0-10 alkyl group), benzyl group, aryl group, wherein H in said group is -F, -Cl, -CN, -NO2, C 1-10 linear / branched alkyl group, 3-6 member heterocycloalkyl group, -OC 1-5 alkyl group, -N(C 1-3 alkyl group)(C 1-3 alkyl group), C 2-8 alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, phenyl group, or R g ’ is TIFF2026519809000047.tif12170、 TIFF2026519809000048.tif16170、 Selected from TIFF2026519809000049.tif11170, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R i ' is selected from halogens, cyano groups, phenyl groups, 5-6 member N, O and / or S-containing heteroaryl groups, 3-6 member cycloalkyl groups or 3-6 member heterocycloalkyl groups, wherein H in the group is halogen, -CN, -NO2, C 1-6 Linear / branched alkyl groups, -OC 1-6 It can be substituted with an alkyl group.

[0060] The aforementioned Y is N or -CF, and is preferably N.

[0061] The P' is N or CH, preferably CH.

[0062] Preferably, the R g ' is -H, halogen, -CN, -NO2, -CF3, C 1-3 Linear / branched alkyl groups, C 3~6It is a cycloalkyl group, more preferably H or a methyl group.

[0063] R 10 ' is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group)(C 1-3 Alkyl(C)(-CO(C)) 1-3 Alkyl(alkyl group), -COO(C 1-3 It can be substituted with an alkyl group, a piperazinyl group, an N-methylpiperazinyl group, or an N-ethylpiperazinyl group.

[0064] Q' is selected from =O or -S-Rxx, preferably Rxx is H or a methyl group.

[0065] The m1, m2, and m3 are independently selected integers from 0 to 4, preferably integers from 0 to 2, and in some embodiments of the present invention, the m1, m2, and m3 are independently selected from 0, 1, 2, 3, or 4.

[0066] R5', R5'', and R5''' are independently -H, halogen, -CN, -CF3, and -Cl -6 Alkyl group, -CO(C 1-6 Alkyl(alkyl group), -COO(C 1-6 Selected from alkyl groups, preferably -H, halogen, -CN, -CF3, -Cl -3 Alkyl group, -CO(C 1-3 Alkyl(alkyl group), -COO(C 1-3 Selected from alkyl groups.

[0067] Preferably, R f ' is -H, C 1-6 Linear / branched alkyl groups, -N(C 0-6 (Alkyl group)(C 0-6 (Alkyl alkyl group), OR j 'and, more preferably, -H, C 1-5 Linear / branched alkyl groups, -N(C 0-3 (Alkyl group)(C 0-3(alkyl group), OR j ’ and preferably, R j ’ is a C 1-6 linear / branched alkyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, thiophenyl group, furanyl group, pyrrolyl group, pyridinyl group or the following group, TIFF2026519809000050.tif16170 Here, R j1 ’, R j2 ’, R j3 ’, R j4 ’, R j5 ’, R j6 ’ are independently H, halogen, -CN, -C 1-6 linear / branched alkyl group, -C 2-6 linear / branched alkenyl group, -OC 1-6 linear / branched alkyl group, C 3-6 cycloalkyl group, 3-6 member heterocycloalkyl group, -CO(C 0-10 alkyl group), -OCO(C 0-10 alkyl group), ethynyl group, and are selected from Here, the H in the group of the said R f ’ can be substituted by halogen, -CN, -CH3, -C2H5, -OC 1-5 , C 3-6 cycloalkyl group, 3-6 member heterocycloalkyl group, -CO(C 0-10 alkyl group), -OCO(C 0-10 alkyl group), vinyl group, propadienyl group, ethynyl group, and further, the alkyl group portion can be substituted by -CN, -OCH2F, -OCHF2, -OCF3, -OC 0-10 alkyl group, C 3-4 cycloalkyl group.

[0068] R g ’ is -H, -Cl -6 linear / branched alkyl group, -C 3-6 cycloalkyl group, -CH2CO(C 1-6 alkyl group), -CH2COO(C 0-6 alkyl group), -CH2COO(C 3-6 cycloalkyl group), -CH2COO(C3-6 Heterocycloalkyl groups), -CH2CON(C 0-6 (Alkyl group)(C 0-6 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO2, C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OH, -OC 1-5 Alkyl, -N(C 1-3 (Alkyl group)(C 1-3 (Alkyl alkyl group), C 2-8 The groups may be substituted with alkenyl groups, imidazolyl groups, oxazolyl groups, thiazolyl groups, pyridinyl groups, pyrimidinyl groups, or phenyl groups, preferably with H being -F, -Cl, -CN, -NO2, or C 1-6 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OH, -OC 1-5 Alkyl, -N(C 1-3 Alkyl group )(C 1-3 (Alkyl alkyl group), C 2-3 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group. or R g 'teeth, TIFF2026519809000051.tif12170, TIFF2026519809000052.tif16170, Selected from TIFF2026519809000053.tif11170, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, preferably R c1 , R c2, R c3 Independently, C 1-6 Linear / branched alkyl groups, -OC 1-6 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-6 (Alkyl group)(C 0-6 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, more preferably R c1 , R c2 , R c3 Independently, C 1-3 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O(C 3-6 Heterocycloalkyl groups), cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 3-membered N or O-containing heterocycloalkyl group, 4-membered N or O-containing heterocycloalkyl group, 5-membered N or O-containing heterocycloalkyl group, 6-membered N or O-containing heterocycloalkyl group, -N(C 1-3 (Alkyl group)(C 1-3 Selected from alkyl groups, vinyl groups, ethynyl groups, phenyl groups, pyridinyl groups, thiophenyl groups, furanyl groups, pyrrolyl groups, imidazolyl groups, thiazolyl groups, and oxazolyl groups, Preferably, the R g H in the base of ' is halogen, -CN, -CH3, -C2H5, -OCH3, -N(C 1-3 (Alkyl group)(C 1-3 (alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted with a cycloalkyl group.

[0069] Preferably, R i' is a halogen, cyano group, phenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, thiazolyl group, triazolyl group, isoxazolyl group, oxazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, or one of the following groups: TIFF2026519809000054.tif17170 The above R i In the base of ', H is a halogen, -CN, -NO2, C 1-6 Linear / branched alkyl groups, -OC 1-6 It may be substituted with an alkyl group. TIFF2026519809000055.tif4170 indicates the join location.

[0070] Preferably, M, together with adjacent carbons, forms a 3-8 member saturated / unsaturated alicyclic ring, a 3-8 member saturated / unsaturated heterocyclic ring, a benzene ring, a 5- or 6-membered monocyclic heteroaromatic ring, a heteroaromatic ring formed by the condensation of a benzene ring with 1-2 5- or 6-membered monocyclic heteroaryl groups, or a heteroaromatic ring formed by the condensation of 2-3 5- and / or 6-membered monocyclic heteroaryl groups, where H in the group is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 It may be substituted with alkyl groups, preferably H in the group being a halogen, -CN, -NO2, -NHCO(C 0-10 Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-10 It may be substituted with an alkyl group, more preferably, the H in the group is a halogen, -CN, -NO2, -NHCO(C 1-6 Alkyl()), CF3, C1-3 Linear alkyl groups, -OC 1-6 It can be substituted with an alkyl group.

[0071] Preferably, the heteroatoms of the 3-8 member saturated / unsaturated alicyclic ring and the 3-8 member saturated / unsaturated heterocyclic ring are selected from one or more of N, O, and S.

[0072] Preferably, M, together with adjacent carbon atoms, forms a 3-6 member saturated / unsaturated alicyclic ring, a 3-6 member saturated / unsaturated heterocyclic ring, a phenyl group, a pyrroloyl group, a thiophenolyl group, a furanyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, a benzofuranyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenolyl group, a benzothiazolyl group, an indolyl group, or an imidazopyridyl group, where H in the group is a halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 It may be substituted with alkyl groups, preferably H in the group being a halogen, -CN, -NO2, -NHCO(C 0-10 Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-10 It can be substituted with an alkyl group.

[0073] Preferably, the 3-6 membered saturated / unsaturated alicyclic ring is selected from a saturated / unsaturated cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0074] Preferably, the 3- to 6-membered saturated / unsaturated heterocycle is a saturated / unsaturated 3-membered heterocycle, 4-membered heterocycle, 5-membered heterocycle, or 6-membered heterocycle containing one or more of N, O, or S atoms. Preferably, the heterocycle is a monocyclic heterocycle.

[0075] When M forms a heteroaromatic ring with adjacent carbon atoms, it can condense with the nucleus via the phenyl side or the heterocyclic group side of the heteroaromatic ring.

[0076] Preferably, M, together with adjacent carbon atoms, forms one of the following structures: TIFF2026519809000056.tif40170R 1x , R 2x , R 3x , R 4x These are H, halogen, -NO2, -CN, -CF3, and C, respectively, independently. 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 Selected from alkyl groups, preferably H, halogen, -CN, -NO2, -NHCO(C 0-10 Alkyl()), CF3, C11-3 linear alkyl group, -OC 0-10 Selected from alkyl groups, preferably H, halogen, -CN, -NO2, -NHCO(C 0-6 Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-6 Selected from alkyl groups, T1, T2, T3, T4, and T5 are independently CR 24 Selected from N, O, or S, T6 is selected from C, N, O, or S. R 24 H, halogen, -CN, -NO2, -NHCO(C 0-10Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-10 Selected from alkyl groups, preferably H, halogen, -CN, -NO2, -NHCO(C 0-6 Alkyl()), CF3, C 1-3 Linear alkyl groups, -OC 0-6 Selected from alkyl groups, TIFF2026519809000057.tif4170 indicates the bond location.

[0077] More preferably, M, together with adjacent carbon atoms, forms one of the following structures: TIFF2026519809000058.tif107170R 5x -R 23x These are independently H. halogen, -NO2, -CN, -CF3, C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C 0-10 (Alkyl group)(C 0-10 (alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 Selected from alkyl groups, preferably H, halogen, -Cl -3 Linear / branched alkyl groups, -OC 0-3 Selected from linear / branched alkyl groups, -CF3, -CN, and -NO2, TIFF2026519809000059.tif4170 indicates the bond location.

[0078] In specific embodiments of the present invention, the following specific compounds are provided: TIFF2026519809000060.tif248170TIFF2026519809000061.tif208170TIFF2026519809000062.tif231170TIFF202 6519809000063.tif197170TIFF2026519809000064.tif213170TIFF2026519809000065.tif229170TIFF20265198090 00066.tif248170TIFF2026519809000067.tif238170TIFF2026519809000068.tif227170TIFF2026519809000069.ti f240170TIFF2026519809000070.tif130170TIFF2026519809000071.tif248170TIFF2026519809000072.tif181170.

[0079] In a second embodiment, the present invention provides pharmaceutical compositions comprising compounds provided in the present invention, pharmaceutically acceptable salts thereof, stereoisomers, prodrugs, solvates, and deuterated compounds.

[0080] Preferably, the pharmaceutical composition further includes, but is not limited to, carriers, diluents, binders, lubricants, and wetting agents, which are pharmaceutically acceptable additives.

[0081] In some embodiments, the pharmaceutical composition may be administered alone or in combination with other active ingredients having anesthetic and / or analgesic effects.

[0082] The aforementioned pharmaceutical composition can be administered to humans and / or animals.

[0083] The pharmaceutical composition is suitable for gastrointestinal or non-gastrointestinal administration via intravenous, intramuscular, intradermal, and subcutaneous routes. Accordingly, the pharmaceutical composition further comprises antioxidants, buffers, antibacterial agents, and solutes, suspensions, solubilizers, thickeners, stabilizers, and preservatives that make the formulation isotonic with the recipient's blood.

[0084] The pharmaceutical composition of the present invention can be incorporated into pharmaceutical preparations in the form of syrups, elixirs, suspensions, powders, granules, tablets, capsules, ingots, aqueous solutions, creams, ointments, lotions, gels, emulsions, and the like.

[0085] Preferably, the pharmaceutical preparation is a unit-dose preparation comprising a therapeutically effective amount of a compound represented by general formula I, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound. The unit-dose preparation may be in the form of a capsule, tablet, or any other dosage form. Furthermore, the unit-dose preparation may also be in the form of a packaged preparation such as a tablet, capsule, or powder packaged in a vial or ampoule.

[0086] The amount of the active ingredient in the aforementioned unit-dose formulation can be varied or adjusted from 0.001 mg to 1000 mg, depending on the specific use and efficacy of the active ingredient. Other suitable active ingredients may be included as needed.

[0087] In a third aspect, the present invention provides the use of compounds provided herein, their pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates and deuterated compounds or the pharmaceutical compositions thereof in the preparation of agents capable of analgesic, and / or anesthetic, sedative, hypnotic, and / or status epilepticus control.

[0088] The pharmaceutically acceptable salts described in this invention include acetate, adipine, aspartate, benzoate, benzenesulfonate, bicarbonate, carbonate, bisulfate, sulfate, borate, camphorsulfonate, citrate, cyclohexanesulfonate, ethylenedisulfonate, ethylsulfonate, formate, fumarate, glucoheptulosinate, gluconate, glucuronate, hexafluorophosphate, hydrochloride, hydrobromide, hydroiodide, isethionate, lactate, malate, These are maleate, malonate, methanesulfonate, methylsulfate, naphthalenecarboxylate, naphthalenesulfonate, nicotinate, nitrate, wheyate, oxalate, palmitate, dihydroxychlorate, phosphate, hydrogen phosphate, dihydrogen phosphate, pyroglutamate, glyoxylate, stearate, butanediate, tannate, tartrate, toluenesulfonate, trifluoroacetate, xinafoate, methanesulfonate, or p-toluenesulfonate.

[0089] Preferably, the pharmaceutically acceptable salts described in the present invention are selected from benzenesulfonates, p-toluenesulfonates, hydroxyethylsulfonates, sulfates, hydrochlorides, methanesulfonates, hydrobroms, and naphthalenesulfonates.

[0090] C according to the present invention 0-10 Regarding the term alkyl group, C0 alkyl group refers to H, so C 0-10 Alkyl groups include H, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, and C 10 Contains alkyl groups.

[0091] C according to the present invention 1-10 The term linear / branched alkyl group refers to a methyl group, an ethyl group, a C3 linear / branched alkyl group, a C4 linear / branched alkyl group, a C5 linear / branched alkyl group, a C6 linear / branched alkyl group, a C7 linear / branched alkyl group, a C8 linear / branched alkyl group, a C9 linear / branched alkyl group, and a C 10Includes linear / branched alkyl groups.

[0092] C according to the present invention 3-10 The term cycloalkyl group includes C3 cycloalkyl groups, C4 cycloalkyl groups, C5 cycloalkyl groups, C6 cycloalkyl groups, C7 cycloalkyl groups, C8 cycloalkyl groups, C9 cycloalkyl groups, and C 10 Contains cycloalkyl groups.

[0093] The term halogen as used in this invention includes fluorine, chlorine, bromine, and iodine. The term heterocycloalkyl group as described in the present invention refers to a cycloalkyl group containing a heteroatom, wherein the heteroatom contains N, O, and S, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom, or contains one N, O, or S as a ring atom, or contains two or more N, O, or S as a ring atom, or contains N and O, N and S, O and S, or N, O, and S as a ring atom.

[0094] The term aryl group as used in this invention includes, but is not limited to, phenyl groups, benzyl groups, and other aromatic compounds formed by the condensation of 2 to 4 phenyl groups.

[0095] In the present invention, the term "heteroaryl" refers to an aromatic heterocyclic compound containing one or more heteroatoms selected from N, O, and S, and includes, but is not limited to, monocyclic aromatic heterocyclic compounds, aromatic heterocyclic compounds formed by the condensation of multiple monocyclic aromatic heterocyclic compounds, aromatic heterocyclic compounds formed by the condensation of one or more phenyl groups with one or more monocyclic aromatic heterocyclic compounds.

[0096] Structure described in the present invention In "TIFF2026519809000073.tif14170", when m≧2, the R5 substituents in each alkylene group are independently substituted, and the R5 substituents may be the same or different.

[0097] Embodiments of the Invention The following describes the technical solutions in embodiments of the present invention clearly and completely. However, it should be noted that the embodiments described are only a part of the embodiments of the present invention, not all embodiments. All other embodiments that can be obtained by those skilled in the art without requiring creative effort based on the embodiments of the present invention are within the scope of protection of the present invention.

[0098] Embodiments of the Invention: The raw materials and apparatus used in the specific embodiments of the present invention are all known products and were purchased commercially.

[0099] The structure of the compound was confirmed by nuclear magnetic resonance (NMR) and / or mass spectrometry (MS). The NMR shift (δ) was 10 -6 The values ​​are expressed in units of ppm. NMR measurements were performed using a Bruker Avance III 400 nuclear magnetic resonance spectrometer, with deuterated dimethyl sulfoxide (d6-DMSO) or deuterated methanol (CD3OD) as the measurement solvent, and tetramethylsilane (TMS) as the internal standard solution.

[0100] LCMS measurements were performed using an Agilent LCMS 1260-6110 (ESID) column and a Waters X-Bridge C18 column (50 mm x 4.6 mm x 3.5 μm). Column temperature: 40°C; Flow rate: 2.0 mL / min; Mobile phase: A gradient was created over 3 minutes from 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA] to 0% [water + 0.05% TFA] and 100% [CH3CN + 0.05% TFA], maintained for 1 minute, then a gradient was created over 0.05 minutes from 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA], maintained for 0.7 minutes.

[0101] 1) Medicinal materials and reagents The thin-layer chromatography silica gel plate used is HSGF254 silica gel plate from Yantai Xinnuo Chemical Co., Ltd., with a thickness of 1 mm.

[0102] Thin-layer chromatography (TLC) was performed using a product from Yantai Jiangyou Silica Gel Development Co., Ltd., with a specification of 0.2 ± 0.03 mm.

[0103] Column chromatography typically uses silica gel of 100-200 mesh or 200-300 mesh from Rushan Sun Desiccant Co., Ltd. (Weihai, Shandong) as the support material.

[0104] 2) Main equipment Sartorius BSA124S electronic balance scale (Sartorius Scientific Instruments Beijing Co., Ltd.), 98-2 magnetic stirrer (Shanghai Sartorius Instruments Co., Ltd.), MS-H-PRO + Digitally controlled heating magnetic stirrer (Dalong Xingchuo Experimental Instruments Beijing Co., Ltd.), TDGC2-1 type contact voltage regulator (Zhejiang Tianzheng Electric Co., Ltd.), WMNK-01 type temperature controller (Shanghai Lulin Electric Co., Ltd.), ZF-I three-way UV device (Shanghai Anting Electronic Instruments Manufacturer), R-201 Rotary evaporator (Shanghai Shensun Biological Technology Co., Ltd.), W201D constant temperature water bath (Shanghai Shensun Biological Technology Co., Ltd.), SHB-III circulating water vacuum pump (Zhengzhou Huicheng Technology Co., Ltd.), SHB-B95 mobile water pump (Zhengzhou Huicheng Technology Co., Ltd.), DLSB-5 / 20℃ Low-temperature cooling circulation pump (Guinyi Yuhua Yi Equipment Co., Ltd.), 2XZ-2 Rotary vacuum pump (Linhai Yonghao Vacuum Equipment Co., Ltd.).

[0105] Example 1: Preparation of Compounds 1 and 1D TIFF2026519809000074.tif63170

[0106] 1. Preparation of Compound 1-1 At -40°C, n-butyllithium (305 mL, 2.5 mol / L in hexane, 762.5 mmol) was added to tetrahydrofuran (280 mL), and 2-bromopyridine (132.6 g, 839.2 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred for 1 hour. A solution of 2-amino-5-bromobenzoic acid (41.2 g, 190.7 mmol) in THF (280 mL) was added dropwise to the reaction system. After the addition was complete, the temperature was allowed to rise naturally to 0°C and the mixture was reacted for 3 hours. After confirming the completion of the reaction by TLC, saturated ammonium chloride aqueous solution (67 mL) and water (318 mL) were added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 200 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100 to 1 / 5), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.5 to 0.6 was recovered to obtain yellow solid compound 1-1 (34.7 g, yield 65.7%). EST[M+H] + = 277.1.

[0107] 2. Preparation of Compounds 1-2 1-1 (20.0 g, 72.2 mmol) and Boc-L-glutamic acid-5-methyl ester (20.8 g, 79.6 mmol) were dissolved in dichloromethane (100 mL), and a solution of DCC (16.4 g, 79.5 mmol) in dichloromethane (40 mL) was added dropwise at -10°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (140 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compounds 1-2 (35.5 g, yield 94.5%). ESI[M +H] + = 520.1.

[0108] 3. Preparation of Compounds 1-3 At 0°C, methanol hydrochloride (170.7 mL, 4 mol / L, 682.8 mmol) was added dropwise to a methanol solution (300 mL) containing 1-2 (35.5 g, 68.2 mmol). After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 20 hours. After confirming the completion of the reaction by TLC, the reaction mixture was added dropwise to a sodium bicarbonate (172.1 g, 2.05 mol) solution in acetonitrile (300 mL) and stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 1-3 (24.1 g, yield 87.8%). ESI[M+ H] + = 402.1.

[0109] 4. Preparation of Compounds 1-4 Under nitrogen protection, phosphorus oxychloride (40 g, 260.9 mmol) was dissolved in toluene (200 mL), cooled to 5°C, and morpholine (89.7 g, 1.025 mol) was slowly added dropwise, while maintaining the temperature below 20°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. Insoluble matter was filtered off, and the filtrate was washed three times with toluene (3 × 35 mL). The filtrates were combined and concentrated into an oily substance under reduced pressure. Toluene (64 mL) was added to the oily substance, and it was heated until uniformly dissolved. Petroleum ether (29 mL) was added while stirring, followed by petroleum ether (116 mL), cooled to room temperature, and filtered. The filtered cake was washed with petroleum ether and dried under reduced pressure to obtain a white solid of dimorpholinyl phosphinochloride (40 g, yield 60.2%).

[0110] At -30°C, lithium bis(trimethylsilyl)amide (72 mL, 1 mol / L, 72 mmol) was slowly added dropwise to 1-3 (24.1 g, 59.9 mmol) of tetrahydrofuran (280 mL) and the mixture was stirred for 1 hour. Dimorpholinyl phosphinochloride (36.1 g, 141.8 mmol) was added in small amounts, and the mixture was stirred at -10°C for 4 hours. Isopropanolamine (20.3 g, 270.3 mmol) was added dropwise to the reaction system, the temperature was allowed to rise naturally to room temperature, and the mixture was stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (100 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 100 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compounds 1-4 (20 g, yield 72.7%). ESI[M+H] + = 459.1.

[0111] 5. Preparation of Compounds 1-5 Dess-Martin reagent (45.8 g, 108.0 mmol) was added to 1-4 (20 g, 43.5 mmol) in acetone (200 mL) solution and stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (300 mL), washed with saturated sodium bicarbonate solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / ) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 1-5 (12.7 g, yield 66.4%). ESI[M+H] + = 439.1.

[0112] 6. Preparation of Compounds 1-6 At -10°C, LiOH / H2O (619 mg, 14.8 mmol) and NaOH (536 mg, 13.4 mmol) were sequentially added to 1-5 (5.9 g, 13.4 mmol) of MeOH / H2O (50 mL, v / v=1 / 1) solution, and the mixture was allowed to rise naturally to room temperature and stirred for 5 hours. After confirming the completion of the reaction by TLC, the reaction system was adjusted to pH=6-7 with 1 mol / L hydrochloric acid under an ice bath and extracted with ethyl acetate (3 × 70 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compounds 1-6 (4.7g, yield 82.3%). ESI[M+H] + = 425.1.

[0113] 7. Preparation of target compound 1 At 0°C, vinylmagnesium bromide (13.9 mL, 1.3 mol / L in THF, 18.1 mmol) was slowly added dropwise to a solution of 3-oxetanone (1 g, 13.9 mmol) in anhydrous tetrahydrofuran (20 mL), and the mixture was stirred for 30 minutes. After confirming the completion of the reaction by TLC, saturated ammonium chloride solution (15 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain 3-vinyloxetan-3-ol (1.36 g, yield 97.9%).

[0114] 1-6 (634 mg, 1.49 mmol), DCC (463 mg, 2.24 mmol), and DMAP (274 mg, 2.24 mmol) were dissolved in dichloromethane (10 mL) and stirred at room temperature for 15 minutes. 3-vinyloxetan-3-ol (227.6 mg, 2.27 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (10 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain gray solid compound 1 (290 mg, yield 38.3%). ESI[M+H] + = 507.1.

[0115] 1 H NMR (400 MHz, DMSO-d6) δ8.55 (d, J=4.0 Hz, 1H), 8.11 (d, J=7.9Hz, 1H), 7.95 (td, J=7.8, 1.7 Hz, 1H), 7.89 (dd, J=8.7, 2.3Hz, 1H), 7.66 (d, J=8.7Hz, 1H), 7.60 (d, J=2.3Hz, 1H), 7.54-7.46 (m, 1H), 6.82 (d, J=1.0 Hz, 1H), 6.23 (dd, J=17.4, 10.9Hz, 1H), 5.26 (dd, J=25.2, 14.2 Hz, 2H), 4.70 (d, J=6.0 Hz, 2H), 4.60 (dJ=7.5 Hz, 2H), 4.07-4.02 (m, 1H), 2.87-2.68 (m, 2H), 2.63-2.50 (m, 2H), 2.30 (s, 3H). 8. Preparation of target compound 1D Compound 1 (192.7 mg, 0.38 mmol) was dissolved in ethyl acetate (15 mL), and a solution of benzenesulfonic acid (60.1 mg, 0.38 mmol) in ethanol (0.6 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a white solid compound 1D (196.8 mg, yield 77.9%). ESI[M+H] + = 507.1.

[0116] 1 H NMR (400 MHz, DMSO-d6) δ8.61-8.56 (m, 1H), 8.15 (d, J=7.9 Hz, 1H), 8.05-7.94 (m, 2H), 7.84 (d, J=8.8 Hz, 1H), 7.74 (d, J=2.3 Hz, 1H), 7.62-7.58 (m, 2H), 7.57-7.53 (m, 1H), 7.44 (s, 1H), 7.36 -7.25 (m, 3H), 6.25 (dd, J=17.4, 10.9 Hz, 1H), 5.35-5.25 (m, 2H), 4.71 (dd, J=7.4, 2.4 Hz, 2H), 4.62 (dd, J=7.3, 3.1 Hz, 2H), 4.33 (dd, J=8.3, 5.2 Hz, 1H), 2.90-2.79 (m, 1H), 2.77-2.64 (m, 2H), 2.54-2.50 (m, 1H), 2.39 (d, J=0.8 Hz, 3H). Example 2 Preparation of Compounds 2 and 2D TIFF2026519809000075.tif32170

[0117] 1. Preparation of Compound 2-1 At 0°C, methylmagnesium bromide (23 mL, 3 mol / Lin THF, 69 mmol) was slowly added dropwise to a solution of 3-oxetanone (4 g, 55.5 mmol) in anhydrous tetrahydrofuran (40 mL), and the mixture was stirred for 30 minutes. After confirming the completion of the reaction by TLC, saturated ammonium chloride solution (20 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain 3-methyloxetan-3-ol (2.91 g, yield 59.5%).

[0118] 2. Preparation of target compound 2 1-6 (350 mg, 0.823 mmol), DCC (255 mg, 1.24 mmol), and DMAP (151 mg, 1.24 mmol) were dissolved in dichloromethane (10 mL) and stirred at room temperature for 15 minutes. 3-Methyloxetan-3-ol (148 mg, 1.68 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (10 mL) was added to the reaction system and stirred for 5 minutes. The filtrate was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 2 (148 mg, yield 36.3%). ESI[M+H] + = 495.1.

[0119] 1H NMR (400 MHz, CDCl3) δ8.58 (d, J=3.9 Hz, 1H), 8.21 (d, J=7.9 Hz, 1H), 7.88-7.77 (m, 2H), 7.73 (d, J=1.9Hz, 1H), 7.44-7.34 (m, 2H), 7.08 (s, 1H), 4.71 (dd, J=7.1, 3.9Hz, 2H), 4.46 (d, J=7.6 Hz, 2H), 4.20 (brs, 1H), 3.00 (brs, 1H), 2.85-2.81 (m, 3H), 2.39 (s, 3H), 1.66 (s, 3H). 8. Preparation of target compound 2D Compound 2 (148 mg, 0.30 mmol) was dissolved in ethyl acetate (35 mL), and a solution of benzenesulfonic acid (47.3 mg, 0.30 mmol) in ethanol (0.5 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain solid compound 2D (162.1 mg, yield 83.0%). ESI[M+H] + = 495.1.

[0120] 1 H NMR (400 MHz, DMSO-d6) δ8.60-8.56 (m, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.04-7.95 (m, 2H), 7.84 (d, J=8.7 Hz, 1H), 7.74 (dJ=2.3 Hz, 1H), 7.62-7.57 (m, 2H), 7.55 (ddd, J=7.6, 4.8, 1.1 Hz, 1H), 7.43 (s, 1H), 7.35-7.26 (m, 3H), 4.62 (d, J=6.1 Hz, 2H), 4.43 (d, J=7.7 Hz, 2H), 4.34 (dd, J=8.6, 5.1 Hz, 1H), 2.84-2.71 (m, 1H), 2.71-2.58 (m, 2H), 2.52-2.50 (m, 1H), 2.39 (d, J=0.8 Hz, 3H), 1.62 (s, 3H). Example 3 Preparation of Compound 3 TIFF2026519809000076.tif34170

[0121] 1. Preparation of Compound 3-1 At 0°C, ethynylmagnesium bromide (72.2 mL, 0.5 mol / L in THF, 36.1 mmol) was slowly added dropwise to a solution of 3-oxetanone (2 g, 27.8 mmol) in anhydrous tetrahydrofuran (30 mL), and the mixture was stirred for 30 minutes. After confirming the completion of the reaction by TLC, saturated ammonium chloride solution (20 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain a colorless oily compound 3-1 (1.32 g, yield 48.5%). ESI[M+H] + = 99.1.

[0122] 2. Preparation of Compound 3-2 3-1 (1.07 g, 10.9 mmol) was added to dioxane (30 mL), polyacetal (811 mg, 27.0 mmol), diisopropylamine (1.965 g, 19.4 mmol), and cuprous bromide (770 mg, 5.37 mmol) were added, and the mixture was stirred at 90°C for 1 hour. After confirming the completion of the reaction by TLC, the reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3~0.4 was recovered to obtain a colorless oily compound 3-2 (72 mg, yield 5.9%). ESI[M+H] + = 113.1.

[0123] 3. Preparation of target compound 3 1-6 (100 mg, 0.235 mmol), DCC (73 mg, 0.354 mmol), and DMAP (43.2 mg, 0.354 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 3-2 (26.6 mg, 0.237 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 3 (57.4 mg, yield 47.0%). ESI[M+H] + = 519.1.

[0124] 1 H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.6 Hz, 1H), 8.20 (d, J=7.9 Hz, 1H), 7.88-7.76 (m, 2H), 7.73 (s, 1H), 7.42-7.31 (m, 2H), 7.06 (s, 1H), 5.57 (t, J=6.6Hz, 1H), 4.99-4.94 (m, 2H), 4.78-4.75 (m, 2H), 4.72-4.68 (m, 2H), 4.20-4.18 (m, 1H), 3.02-3.00 (m, 1H), 2.88-2.86 (m, 3H), 2.39 (s, 3H) Example 4 Preparation of Compound 4 TIFF2026519809000077.tif31170

[0125] 1-6 (80 mg, 0.188 mmol), DCC (58.3 mg, 0.283 mmol), and DMAP (34.5 mg, 0.282 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. Oxetan-3-ol (28 mg, 0.378 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The filtrate was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 4 (42.5 mg, yield 46.9%). ESI[M +H] + = 481.0.

[0126] 1 H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.0 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.82 (td, J=7.8, 1.7Hz, 1H), 7.76 (dd, J=8.6, 2.1 Hz, 1H), 7.70 (d, J=2.1 Hz, 1H), 7.40-7.35 (m, 1H), 7.34 (d, J=8.6 Hz, 1H), 6.99 (s, 1H), 5.48-5.38 (m, 1H), 4.85 (dd, J=11.6, 6.8 Hz, 2H), 4.67-4.55 (m, 2H), 4.13 (s, 1H), 2.97- 2.95 (m, 1H), 2.91-2.76 (m, 3H), 2.37 (s, 3H). Example 5 Preparation of compounds 5, 6, 6D, 7 and 7D TIFF2026519809000078.tif45170

[0127] 1. Preparation of target compound 5 1-6 (3 g, 7.05 mmol), DCC (2.89 g, 14.0 mmol), and DMAP (1.71 g, 14.0 mmol) were dissolved in dichloromethane (30 mL) and stirred at room temperature for 15 minutes. 2-methyl-3-buty-2-ol (1.18 g, 14.0 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (30 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 5 (1.8 g, yield 51.9%). ESI[M+H] + = 491.0.

[0128] 1 H NMR (400 MHz, DMSO-d6) δ8.54 (d, J=4.0 Hz, 1H), 8.11 (d, J=7.9Hz, 1H), 7.94 (td, J=7.8, 1.7 Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7Hz, 1H), 7.60 (d, J=2.3Hz, 1H), 7.54-7.47 (m, 1H), 6.81 (d, J=1.1 Hz, 1H), 4.05 (t, J=6.6Hz, 1H), 3.47 (s, 1H), 2.73-2.52 (m, 4H), 2.30 (s, 3H), 1.58 (s, 6H) 2. Preparation of target compound 6 Compound 5 (600 mg, 1.22 mmol) was dissolved in dichloromethane (10 mL), mercury(II) sulfate / sulfuric acid / silica gel (600 mg) was added, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction system was neutralized with saturated sodium bicarbonate aqueous solution and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.4-0.5 was recovered to obtain white solid compound 6 (267.1 mg, yield 42.9%). ESI[M+H] + =509.2. 1 H NMR (400 MHz, DMSO-d6) δ8.54 (d, J=4.0 Hz, 1H), 8.11 (d, J=7.9Hz, 1H), 7.95 (td, J=7.8, 1.7Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7Hz, 1H), 7.60 (d, J=2.3Hz, 1H), 7.54-7.46 (m, 1H), 6.83 (s, 1H), 4.11-4.02 (m, 1H), 2.86-2.51 (m, 4H), 2.30 (s, 3H), 2.01 (s, 3H), 1.37 (s, 3H), 1.36 (s, 3H) 3. Preparation of target compound 6D Compound 6 (199 mg, 0.391 mmol) was dissolved in ethyl acetate (10 mL), and a solution of benzenesulfonic acid (61.9 mg, 0.391 mmol) in ethanol (0.6 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a white solid compound 6D (236.4 mg, yield 90.6%). ESI[M+H] + = 509.1.

[0129] 1H NMR (400 MHz, DMSO-d6) δ8.57 (d, J=4.1 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.02-7.94 (m, 2H), 7.82 (d, J=8.8 Hz, 1H), 7.72 (d, J=2.3 Hz, 1H), 7.62-7.57 (m, 2H), 7.57-7.51 (m, 1H), 7.37 (s, 1H), 7.34 -7.25 (m, 3H), 4.29-4.28 (m, 1H), 2.86-2.75 (m, 1H), 2.71-2.59 (m, 2H), 2.51-2.50 (m, 1H), 2.38 (s, 3H), 2.04 (s, 3H), 1.40 (s, 3H), 1.38 (s, 3H). 4. Preparation of target compound 7 At room temperature, compound 5 (600 mg, 1.22 mmol) was dissolved in tetrahydrofuran (10 mL), and Lindler catalyst (600 mg, 5% Pd) was added. The mixture was stirred under a hydrogen atmosphere for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product residue was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 7 (369.8 mg, yield 61.4%). ESI[M+H] + = 493.2.

[0130] 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=3.7 Hz, 1H), 8.21 (d, J=7.9 Hz, 1H), 7.84-7.80 (m, 1H), 7.78-7.76 (m, 1H), 7.69 (s, 1H), 7.37 (dd, J=7.1, 4.8 Hz, 2H), 7.01 (s, 1H), 6.01 (dd, J=17.5, 10.8 Hz, 1H), 5.09 (d, J=17.5 Hz, 1H), 4.99 (d, J=10.8 Hz, 1H), 4.22-4.19 (m, 1H), 2.95-2.94 (m, 1H), 2.77-2.75 (m, 3H), 2.38 (s, 3H), 1.46 (s, 6H). 5. Preparation of target compound 7D Compound 7 (220 mg, 0.446 mmol) was dissolved in ethyl acetate (2.2 mL), and a solution of benzenesulfonic acid (70.7 mg, 0.446 mmol) in ethanol (0.7 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a white solid compound 7D (251.5 mg, yield 86.6%). ESI[M+H] + = 493.1.

[0131] 1 H NMR (400 MHz, DMSO-d6) δ8.57 (d, J=4.1 Hz, 1H), 8.13 (d, J=7.9 Hz, 1H), 8.03-7.94 (m, 2H), 7.81 (d, J=8.9Hz, 1H), 7.71 (s, 1H), 7.62-7.57 (m, 2H), 7.56-7.51 (m, 1H), 7.38-7.26 (m, 4H), 6.04 (dd, J=17.5, 10.9Hz, 1H), 5.13 (d, J=17.5 Hz, 1H), 5.01 (dd, J=10.9, 0.9Hz, 1H), 4.26 (s, 1H), 2.62-2.50 (m, 4H), 2.37 (s, 3H), 1.45 (s, 6H). Example 6 Preparation of Compound 9 TIFF2026519809000079.tif32170

[0132] 1. Preparation of Compound 9-2 At 0°C, NaH (26.7 mg, 60%, 0.667 mmol) was slowly added to a solution of 9-1 (197 mg, 0.556 mmol) in dry tetrahydrofuran (5 mL), and the mixture was stirred for 30 minutes. Iodomethane (118.3 mg, 0.833 mmol) was added to the reaction system, and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 10), and the portion with Rf = 0.4 to 0.5 was recovered to obtain white solid compound 9-2 (124 mg, yield 60.5%). ESI[M+H] + = 369.2.

[0133] 2. Preparation of Compound 9-3 At 0°C, TBAF (176 mg, 0.673 mmol) was added to a solution of 9-2 (124 mg, 0.336 mmol) in tetrahydrofuran (5 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3~0.4 was recovered to obtain the colorless oily compound 9-3 (38.0 mg, yield 86.8%). ESI[M+H] + = 131.2.

[0134] 3. Preparation of target compound 9 1-6 (100 mg, 0.235 mmol), DCC (73.0 mg, 0.354 mmol), and DMAP (43.2 mg, 0.353 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 9-3 (30.6 mg, 0.235 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 2 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 3 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 9 (81.7 mg, yield 64.6%). EST[M+H] + = 537.2.

[0135] 1 H NMR (400 MHz, CDCl3) δ 8.57 (d, J=4.0 Hz, 1H), 8.22-8.20 (m, 1H), 7.85-7.83 (m, 2H), 7.76- 7.65 (m, 1H), 7.54-7.29 (m, 2H), 7.26-7.13 (m, 1H), 4.47-4.44 (m, 1H), 4.17-3.91 (m, 2H), 3.30 (s, 5H), 3.17-2.63 (m, 4H), 2.39 (s, 3H), 1.85-1.71 (m, 6H). Example 7 Preparation of Compound 10 TIFF2026519809000080.tif29170

[0136] 1-6 (100 mg, 0.235 mmol), DCC (73 mg, 0.354 mmol), and DMAP (43.2 mg, 0.354 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 2,2-difluoroethanol (21.3 mg, 0.260 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.4-0.5 was recovered to obtain a colorless oily compound 10 (90.1 mg, yield 78.3%). ESI[M+H] + = 489.0.

[0137] 1 H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.0Hz, 1H), 8.22-8.19 (m, 1H), 7.86 (t, J=7.8 Hz, 2H), 7.80 (s, 1H), 7.42 (dd, J=7.3, 5.0 Hz, 2H), 7.28-7.26 (m, 1H), 6.10-5.70 (m, 1H), 4.40-4.37 (m, 1H), 4.32- 4.16 (m, 2H), 3.22-3.17 (m, 1H), 3.09-2.80 (m, 3H), 2.44 (s, 3H). Example 8 Preparation of Compound 11 TIFF2026519809000081.tif29170

[0138] 1-6 (81 mg, 0.190 mmol), bromomethyl acetate (35.1 mg, 0.229 mmol), and cesium carbonate (93 mg, 0.285 mmol) were dissolved in DMF (2 mL) and stirred at 60°C for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 11 (39.1 mg, yield 41.3%). ESI[M+H] + = 497.2.

[0139] 1 H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.7 Hz, 1H), 8.19 (d, J=7.9 Hz, 1H), 7.87-7.77 (m, 2H), 7.75 (s, 1H), 7.43-7.33 (m, 2H), 7.12 (s, 1H), 5.75-5.66 (m, 2H), 4.28-4.26 (m, 1H), 3.06-3.04 (m, 1H), 2.92-2.88 (m, 3H), 2.40 (s, 3H), 2.06 (s, 3H). Example 9 Preparation of Compound 12 TIFF2026519809000082.tif42170

[0140] 1. Preparation of Compound 12-1 1-5 (632 mg, 1.44 mmol), trimethylsilylacetylene (2.82 g, 28.7 mmol), and PdCl2(PPh3)2 (101.1 mg, 0.144 mmol) were dissolved in a mixed solvent of triethylamine (20 mL) and acetonitrile (30 mL) and stirred at 70°C for 4 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The residual solution was dissolved in ethyl acetate (50 mL), washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 12-1 (627 mg, yield 95.4%). ESI[M+ H] + = 457.2.

[0141] 2. Preparation of Compound 12-2 At 0°C, TBAF (538.5 mg, 2.06 mmol) was added to 12-1 (627 mg, 1.37 mmol) in tetrahydrofuran (5 mL) solution, and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain the yellow solid compound 12-2 (287.5 mg, yield 54.5%). ESI[M+H] + = 385.2.

[0142] 3. Preparation of Compound 12-3 At -20°C, LiOH / H2O (34.5 mg, 0.822 mmol) and NaOH (29.9 mg, 0.747 mmol) were sequentially added to 12-2 (287.5 mg, 0.748 mmol) of MeOH / THF / H2O (10 mL, v / v / v=1 / 1 / 1), and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction system was adjusted to pH=6-7 using 1 mol / L hydrochloric acid under an ice bath and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated saline solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 8), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 12-3 (267.9 mg, yield 96.7%). ESI[M+H] + = 371.1.

[0143] 4. Preparation of target compound 12 At 0°C, 12-3 (146.5 mg, 0.396 mmol), chloromethylmethyl carbonate (148.4 mg, 1.19 mmol), and potassium carbonate (129.5 mg, 0.937 mmol) were dissolved in DMF (3 mL), allowed to rise naturally to room temperature, and stirred for 4 hours. After confirming the completion of the reaction by TLC, water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain the white solid compound 12 (49.4 mg, yield 27.2%). ESI[M+H₂] + = 459.1.

[0144] 1H NMR (400 MHz, DMSO-d6) δ8.53 (d, J=4.0 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.98-7.90 (m, 1H), 7.77 (dd, J=8.4, 1.9 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.51-7.48 (m, 2H), 6.82 (d, J=1.0 Hz, 1H), 5.71 (s, 2H), 4.32 (s, 1H), 4.06-4.02 (m, 1H), 3.73 (s, 3H), 2.85-2.73 (m, 2H), 2.66-2.50 (m, 2H), 2.31 (s, 3H). Example 10 Preparation of Compound 13 TIFF2026519809000083.tif19170

[0145] 1. Preparation of Compound 13-1 At 0°C, NaH (175 mg, 60%, 4.37 mmol) was slowly added to 1-3 (1.6 g, 3.98 mmol) of dry DMF (15 mL) solution and stirred for 30 minutes. Iodomethane (623 mg, 4.39 mmol) was added to the reaction system and stirred for 1 hour. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (30 mL) and extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 11), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 13-1 (1.603 g, yield 96.8%). ESI[M+H] + = 416.1.

[0146] 2. Preparation of Compound 13-2 At -20°C, LiOH / H2O (177.7 mg, 4.23 mmol) and NaOH (154 mg, 3.85 mmol) were sequentially added to 13-1 (1.603 g, 3.85 mmol) of MeOH / THF / H2O (20 mL, v / v / v=1 / 1 / 1), and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction system was adjusted to pH=6-7 using 1 mol / L hydrochloric acid under an ice bath and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 30~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2~0.3 was recovered to obtain white solid compound 13-2 (1.54 g, yield 99.4%). ESI[M+H] + = 402.1.

[0147] 3. Preparation of target compound 13 13-2 (100 mg, 0.249 mmol), DCC (77 mg, 0.373 mmol), and DMAP (46 mg, 0.377 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 3-Vinyloxetan-3-ol (50 mg, 0.499 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 3 / 1), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 13 (39.0 mg, yield 32.4%). ESI[M+H] + =484.1. 1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 8.19 (d, J=7.9 Hz, 1H), 8.04-8.02 (m, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.59-7.57 (m, 1H), 7.44 (s, 1H), 7.28-7.26 (m, 1H), 6.17 (dd, J=17.4, 10.9Hz, 1H), 5.29 (d, J=17.4Hz, 1H), 5.23 (d, J=11.0Hz, 1H), 4.78 (d, J=7.1 Hz, 2H), 4.66 (dd, J=7.4, 3.2 Hz, 2H), 3.76 (t, J=6.8 Hz, 1H), 3.43 (s, 3H), 2.74 (t, J=6.9Hz, 2H), 2.69-2.59 (m, 1H), 2.56-2.47 (m, 1H). Example 11 Preparation of Compounds 14-16 TIFF2026519809000084.tif27170

[0148] The preparation method for target compounds 14-16 was the same as for compound 13 in Example 10, using 13-2 and the corresponding alcohol as starting materials to obtain the corresponding esters.

[0149] Compound 14:80 mg,ESI[M+H] + = 472.1.

[0150] 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J=4.1 Hz, 1H), 8.18 (d, J=7.8 Hz, 1H), 7.94 (t, J=7.2 Hz, 1H), 7.68 (dd, J=8.8, 2.1 Hz, 1H), 7.49 (d, J=2.0Hz, 2H), 7.24 (s, 1H), 4.71 (d, J=7.1 Hz, 2H), 4.46 (d, J=7.6 Hz, 2H), 3.74-3.72 (m, 1H), 3.42 (s, 3H), 2.71-2.43 (m, 4H), 1.65 (s, 3H). Compound 15: 102.7 mg, ESI [M+H] + =496.0.

[0151] 1 H NMR (400 MHz, CDCl3) δ 8.65 (d, J=4.2 Hz, 1H), 8.17 (d, J=7.9 Hz, 1H), 7.86 (t, J=7.3 Hz, 1H), 7.66 (dd, J=8.8, 2.2Hz, 1H), 7.52 (d, J=2.2 Hz, 1H), 7.46-7.38 (m, 1H), 7.24 (d, J=8.8Hz, 1H), 5.58 (t, J=6.6 Hz, 1H), 4.97 (d, J=6.6 Hz, 2H), 4.76 (t, J=7.0 Hz, 2H), 4.71 (t, J=6.6 Hz, 2H), 3.73-3.68 (m, 1H), 3.40 (s, 3H), 2.72-2.65 (m, 2H), 2.63-2.55 (m, 1H), 2.53-2.45 (m, 1H). Compound 16: 65.6 mg, ESI [M+H] + =458.1.

[0152] 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J=4.4 Hz, 1H), 8.16 (d, J=7.8 Hz, 1H), 7.93 (t, J=7.5 Hz, 1H), 7.67 (dd, J=8.8, 2.0 Hz, 1H), 7.49-7.47 (m, 2H), 7.26-7.25 (m, 1H), 5.52-5.36 (m, 1H), 4.85 (dd, J= 11.9, 6.7Hz, 2H), 4.60 (t, J=6.4 Hz, 2H), 3.75-3.72 (m, 1H), 3.41 (s, 3H), 2.71 (t, J=7.1 Hz, 2H), 2.66- 2.55 (m, 1H), 2.54-2.44 (m, 1H). Example 12 Preparation of compounds 17, 17E, 18, 19 and および19E TIFF2026519809000085.tif52170

[0153] 1. Preparation of target compound 17 13-2 (1.0 g, 2.49 mmol), DCC (1.03 g, 4.99 mmol), and DMAP (610 mg, 4.99 mmol) were dissolved in dichloromethane (10 mL) and stirred at room temperature for 15 minutes. 2-methyl-3-buty-2-ol (420 mg, 4.99 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After monitoring for complete reaction by TLC, methyl tert-butyl ether (10 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 17 (621.0 mg, yield 53.3%). ESI[M + H] + = 468.0.

[0154] 1 H NMR (400 MHz, CDCl3) δ 8.66 (d, J=3.9 Hz, 1H), 8.20 (d, J=7.7 Hz, 1H), 7.91 (t, J=7.1Hz, 1H), 7.65 (dd, J=8.8, 2.1 Hz, 1H), 7.48-7.42 (m, 2H), 7.24 (d, J=8.8 Hz, 1H), 3.75 (t, J=6.5Hz, 1H), 3.41 (s, 3H), 2.66-2.57 (m, 3H), 2.53-2.44 (m, 1H), 2.40 (s, 1H), 1.61 (s, 3H), 1.61 (s, 3H). 2. Preparation of target compound 17E Compound 17 (218 mg, 0.465 mmol) was dissolved in diethyl ether (10 mL), and a solution of p-toluenesulfonic acid monohydrate (88.3 mg, 0.464 mmol) in acetone (0.5 mL) was added dropwise at -70°C, and the mixture was stirred for 20 minutes. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a yellow solid compound 17E (258.3 mg, yield 86.6%). ESI[M+H] + = 468.2.

[0155] 1 H NMR (400 MHz, DMSO-d6) δ8.62 (d, J=4.1 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H), 8.03 (td, J=7.7, 1.6 Hz, 1H), 7.82 (dd, J=8.8, 2.4Hz, 1H), 7.62-7.56 (m, 1H), 7.53 (t, J=5.8 Hz, 2H), 7.47 (d, J=8.1 Hz, 2H), 7.11 (d, J=7.9 Hz, 2H), 3.71 (dd, J=8.0, 5.5 Hz, 1H), 3.45 (s, 1H), 3.31 (s, 3H), 2.55-2.50 (m, 1H), 2.47- 2.30 (m, 2H), 2.29 (s, 3H), 2.26-2.16 (m, 1H), 1.55 (s, 3H), 1.55 (s, 3H). 3. Preparation of target compound 18 Compound 17 (310 mg, 0.662 mmol) was dissolved in dichloromethane (10 mL), mercury(II) sulfate / sulfuric acid / silica gel (310 mg) was added, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction system was neutralized with saturated sodium bicarbonate aqueous solution and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 18 (284 mg, yield 88.2%). ESI[M+H] + = 486.2.

[0156] 1 H NMR (400 MHz, DMSO-d6) δ8.61-8.56 (m, 1H), 8.12 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.8, 1.7Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.57-7.50 (m, 2H), 7.48 (d, J=2.4 Hz, 1H), 3.71 (dd, J=8.3, 5.5 Hz, 1H), 3.31 (s, 3H), 2.66-2.51 (m, 2H), 2.39-2.30 (m, 1H), 2.28-2.14 (m, 1H), 1.96 (s, 3H), 1.34 (s, 3H), 1.32 (s, 3H). 4. Preparation of target compound 19 At room temperature, compound 17 (300 mg, 0.641 mmol) was dissolved in tetrahydrofuran (10 mL), and Lindler catalyst (300 mg, 5% Pd) was added. The mixture was stirred under a hydrogen atmosphere for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 19 (296 mg, yield 98.2%). ESI[M+H] + = 470.2.

[0157] 1H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.0 Hz, 1H), 8.11 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.8, 1.8 Hz, 1H), 7.81 (dd, J=8.8, 2.4 Hz, 1H), 7.54-7.51 (m, 2H), 7.48 (d, J=2.4 Hz, 1H), 5.97 (dd, J=17.5, 10.9 Hz, 1H), 5.08 (d, J=17.5Hz, 1H), 4.97 (dd, J=10.9, 0.9Hz, 1H), 3.67 (dd, J=8.2, 5.6Hz, 1H), 3.30 (s, 3H), 2.44-2.14 (m, 4H), 1.39 (s, 6H). 5. Preparation of target compound 19E The preparation method for compound 19E was the same as for compound 17E in Example 12, and it was obtained by preparation using 19 and p-toluenesulfonic acid monohydrate as raw materials.

[0158] Compound 19E:265.1mg,ESI[M+H] + = 470.2.

[0159] 1 H NMR (400 MHz, DMSO-d6) δ 8.62 (d, J=4.3 Hz, 1H), 8.11 (d, J=7.9 Hz, 1H), 8.05-8.02 (m, 1H), 7.83 (dd, J=8.9, 2.4 Hz, 1H), 7.63-7.57 (m, 1H), 7.55-7.51 (m, 2H), 7.47 (d, J=8.1 Hz, 2H), 7.11 (d, J= 7.8 Hz, 2H), 5.97 (dd, J=17.5, 10.9Hz, 1H), 5.12-5.05 (m, 1H), 4.97 (dd, J=10.9, 0.9Hz, 1H), 3.69 (dd, J =7.9, 5.6 Hz, 1H), 3.30 (s, 3H), 2.48-2.30 (m, 3H), 2.29 (s, 3H), 2.24-2.19 (m, 1H), 1.39 (s, 6H). Example 13 Preparation of Compound 20 TIFF2026519809000086.tif27170

[0160] m-CPBA (56 mg, 0.325 mmol) was divided and added to 19 (100 mg, 0.213 mmol) of dichloromethane (5 mL) solution, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1) to obtain white solid compound 20 (84.3 mg, yield 81.5%). ESI[M + H] + = 486.2.

[0161] 1 H NMR (400 MHz, DMSO-d6) δ8.19 (d, J=5.8 Hz, 1H), 7.79-7.73 (m, 2H), 7.63-7.49 (m, 3H), 7.22 (d, J=2.3 Hz, 1H), 6.02-5.93 (m, 1H), 5.11-5.04 (m, 1H), 4.96 (dd, J=10.9, 0.9Hz, 1H), 3.66 (dd, J =8.3, 5.5Hz, 1H), 3.32 (s, 3H), 2.43-2.35 (m, 2H), 2.32-2.25 (m, 1H), 2.20-2.15 (m, 1H), 1.39 (s, 6H) Example 14 Preparation of Compounds 21-23 TIFF2026519809000087.tif47170

[0162] 1. Preparation of Compound 23-1 1-1 (630 mg, 2.27 mmol) and (S)-2-fluorenylmethoxycarbonylaminohexanoic acid-6-tert-butyl ester (1 g, 2.28 mmol) were dissolved in dichloromethane (10 mL), and a solution of DCC (705 mg, 3.42 mmol) in dichloromethane (2 mL) was added dropwise at -10°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (12 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product, which was used directly in the next step without purification. ESI[M+H] + = 642.1.

[0163] 2. Preparation of target compound 21 The crude product from the previous step was dissolved in a mixed solvent of morpholine and dichloromethane (10 mL, v / v=1 / 1) and stirred at room temperature for 24 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography (methanol / dichloromethane (v / v)=1 / 100~1 / 10) and confirmed by TLC (methanol / dichloromethane (v / v)=1 / 10). The portion with Rf=0.2~0.3 was recovered to obtain white solid compound 21 (294 mg, 2-step yield 28.2%). ESI[M+H] + =458.2. 1 H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.13 (brs, 1H), 8.11 (d, J=7.7 Hz, 1H), 7.91 (t, J=7.3 Hz, 1H), 7.62 (d, J=8.5Hz, 1H), 7.52-7.50 (m, 1H), 7.48-7.46 (m, 1H), 7.05 (d, J=7.7Hz, 1H), 3.63 (s, 1H), 2.33-2.17 (m, 2H), 1.93-1.80 (m, 2H), 1.76-1.58 (m, 2H), 1.44 (s, 9H). 3. Preparation of target compound 22 At -10°C, NaH (25.2 mg, 60%, 0.63 mmol) was slowly added to 21 (264 mg, 0.576 mmol) in 3 mL of dry DMF solution, and the mixture was stirred for 30 minutes. Iodomethane (89.6 mg, 0.631 mmol) was added to the reaction system, and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, the reaction mixture was poured into 10 mL of ice water and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 22 (152 mg, yield 55.9%). ESI[M+H] + = 472.2.

[0164] 1 H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.23-8.17 (m, 1H), 7.95-7.85 (m, 1H), 7.66 (d, J=8.8Hz, 1H), 7.52-7.40 (m, 2H), 7.24 (d, J=9.0 Hz, 1H), 3.62-3.58 (m, 1H), 3.41 (s, 3H), 2.40-2.27 (m, 3H), 2.25 -2.15 (m, 1H), 1.84-1.80 (m, 2H), 1.44 (s, 9H). 4. Preparation of Compound 23-2 At 0°C, trifluoroacetic acid (0.55 mL) was added to a solution of 22 (130 mg, 0.275 mmol) of dichloromethane (3.25 mL) and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, and the reaction system was adjusted to pH 8-9 using saturated sodium bicarbonate aqueous solution, and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 8), and the portion with Rf = 0.3-0.4 was recovered to obtain the white solid compound 23-2 (95 mg, yield 82.9%). ESI[M+H] + = 416.1.

[0165] 5. Preparation of target compound 23 23-2 (52 mg, 0.125 mmol), DCC (50.5 mg, 0.245 mmol), and DMAP (29.9 mg, 0.245 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 3-methyloxetan-3-ol (22.0 mg, 0.250 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 23 (26.7 mg, yield 43.9%). ESI[M +H] + = 486.2.

[0166] 1 H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.5 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.8, 1.7 Hz, 1H), 7.80 (dd, J=8.8, 2.4 Hz, 1H), 7.53-7.50 (m, 3H), 4.60 (d, J=6.9Hz, 2H), 4.40 (d, J=7.5Hz, 2H), 3.63 (dd, J=8.2, 5.3 Hz, 1H), 3.30 (s, 3H), 2.39 (t, J=7.4 Hz, 2H), 2.17-1.98 (m, 2H), 1.74-1.70 (m, 1H), 1.62-1.56 (m, 4H). Example 15 Preparation of Compound 24 TIFF2026519809000088.tif32170

[0167] The method for preparing compound 24 was the same as for compound 23 in Example 14, using 23-2 and oxetan-3-ol as raw materials and obtaining it by purification.

[0168] Compound 24:14.5mg,ESI[M+H] + =472.2. 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=4.0Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.7, 1.7 Hz, 1H), 7.80 (dd, J=8.8, 2.4Hz, 1H), 7.55-7.49 (m, 3H), 5.37-5.30 (m, 1H), 4.77 (t, J=7.3 Hz, 2H), 4.51 -4.41 (m, 2H), 3.63 (dd, J=8.3, 5.5Hz, 1H), 3.30 (s, 3H), 2.44 (t, J=7.5 Hz, 2H), 2.12-2.00 (m, 2H), 1.80 -1.70 (m, 1H), 1.65-1.55 (m, 1H) Example 16 Preparation of Compounds 26-28 TIFF2026519809000089.tif69170

[0169] 1. Preparation of Compound 28-1 At -70°C, n-butyllithium (179 mL, 2.5 mol / L in hexane, 447.5 mmol) was added dropwise to a solution of 2-bromopyridine (71.95 g, 455.4 mmol) in toluene (492 mL). After the addition was complete, the mixture was stirred for 30 minutes. Anthranironitrile (23.5 g, 198.9 mmol) in toluene (163 mL) was added dropwise to the reaction system, and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3 × 200 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 50~1 / 5), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.4~0.6 was recovered to obtain white solid compound 28-1 (12.4 g, yield 31.4%). ESI[M+H] + =199.1.

[0170] 2. Preparation of Compound 28-2 Trifluoroacetic anhydride (16.1 g, 76.7 mmol) was added to a solution of 28-1 (12.73 g, 64.2 mmol) in chloroform (408 mL) and stirred at 42°C for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, and the reaction system was adjusted to pH 8-9 using saturated sodium bicarbonate aqueous solution, and extracted with ethyl acetate (3 × 100 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 50-1 / 5), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.4-0.6 was recovered to obtain the white solid compound 28-2 (10.8 g, yield 57.2%). ESI[M+H] + =295.1.

[0171] 3. Preparation of Compound 28-3 Potassium nitrate (5.565 g, 55.0 mmol) was dissolved in concentrated sulfuric acid (50 mL) and added dropwise to a solution of 28-2 (10.6 g, 36.0 mmol) in concentrated sulfuric acid (50 mL) at 0°C, while maintaining the temperature below 10°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 4 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water, the reaction system was adjusted to H=8-9 using a 25% sodium hydroxide aqueous solution, and extracted with ethyl acetate (3 × 60 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 50~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.4~0.6 was recovered to obtain yellow solid compound 28-3 (9.5g, yield 77.7%). ESI[M+H] + =340.1.

[0172] 4. Preparation of Compound 28-4 28-3 (9.5 g, 28.0 mmol) and potassium carbonate (7.71 g, 55.8 mmol) were added to a mixed solvent of methanol and water (100 mL, v / v=1 / 1) and stirred at 70°C for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. Ice water was added to the residue and filtered by suction. The filtered cake was washed three times with water and vacuum dried to obtain the yellow solid compound 28-4 (6.8 g, yield 99.8%). ESI[M+H] + =244.1.

[0173] 5. Preparation of Compound 28-5 Thionyl chloride (30 mL) was added to a solution of Fmoc-L-methyl glutamate (13.3 g, 34.7 mmol) in chloroform (100 mL) and stirred at 50°C for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in chloroform (50 mL), and this was added dropwise to a solution of 28-4 (4.21 g, 17.3 mmol) and pyridine (1.35 g, 17.1 mmol) in chloroform (40 mL), and stirred at 60°C for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 50~1 / 5), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 5), and the portion with Rf = 0.4~0.5 was recovered to obtain the white solid compound 28-5 (7.7 g, yield 73.1%). ESI[M+ H] + = 609.2.

[0174] 6. Preparation of target compound 26 Compound 28-5 (7.67 g, 12.6 mmol) was added to a mixed solvent of morpholine (13 mL) and dichloromethane (67 mL) and stirred at room temperature for 24 hours. After confirming the completion of the reaction by TLC, ice water (30 mL) was added to the reaction system. Extraction was performed with dichloromethane (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 26 (2.2 g, yield 47.4%). ESI[M+H] + = 369.2.

[0175] 1 H NMR (400 MHz, CDCl3) δ 9.05-8.90 (m, 1H), 8.60-8.57 (m, 1H), 8.39-8.27 (m, 2H), 8.20 (d, J=7.9 Hz, 1H), 7.90-7.86 (m, 1H), 7.46-7.41 (m, 1H), 7.25-7.14 (m, 1H), 3.83-3.78 (m, 1H), 3.67-3.66 (m, 3H), 2.75-2.65 (m, 2H), 2.65-2.44 (m, 2H). 7. Preparation of target compound 27 At -10°C, NaH (215 mg, 60%, 5.37 mmol) was slowly added to 26 (1.8 g, 4.89 mmol) in a 20 mL solution of dry DMF, and the mixture was stirred for 30 minutes. Iodomethane (764 mg, 5.38 mmol) was added to the reaction system, and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, the reaction mixture was poured into 40 mL of ice water and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4 to 0.5 was recovered to obtain white solid compound 27 (1.505 g, yield 80.5%). ESI[M+H] + = 383.2.

[0176] 1 H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.41 (d, J=9.0 Hz, 1H), 8.34-8.21 (m, 2H), 7.96-7.94 (m, 1H), 7.50 (d, J=9.0 Hz, 2H), 3.79-3.77 (m, 1H), 3.65 (s, 3H), 3.49 (s, 3H), 2.71-2.58 (m, 3H), 2.57-2.46 (m, 1H). 8. Preparation of target compound 28 At 0°C, sodium ethoxide (219.5 mg, 3.23 mmol) was added to 27 (857 mg, 2.24 mmol) of EtOH / THF (18 mL, v / v=1 / 1) mixed solution, and the mixture was allowed to rise naturally to room temperature and stirred for 8 hours. After confirming the completion of the reaction by TLC, ice water (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v)=1 / 1), and the portion with Rf=0.2~0.3 was recovered to obtain white solid compound 28 (242.9 mg, yield 27.3%). ESI[M+H] + =397.2. 1 H NMR (400 MHz, DMSO-d6) δ8.57 (d, J=4.7 Hz, 1H), 8.45 (dd, J=9.2, 2.8 Hz, 1H), 8.22 (d, J=2.7 Hz, 1H), 8.19 (d, J=7.9 Hz, 1H), 8.00 (td, J=7.8, 1.7Hz, 1H), 7.79 (d, J=9.2 Hz, 1H), 7.57-7.54 (m, 1H), 4.04 (q, J=7.1 Hz, 2H), 3.8 0-3 .74 (m, 1H), 3.38 (s, 3H), 2.59-2.53 (m, 1H), 2.45-2.35 (m, 2H), 2.31-2.21 (m, 1H), 1.14 (t, J=7.1 Hz, 3H) Example 17 Preparation of Compound 29 TIFF2026519809000090.tif24170

[0177] 1. Preparation of Compound 29-1 At -10°C, LiOH / H2O (64.3 mg, 1.53 mmol) and NaOH (55.7 mg, 1.39 mmol) were sequentially added to 27 (532 mg, 1.39 mmol) of MeOH / THF / H2O (7 mL, v / v / v=1 / 1 / 1) solution, and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming completion of the reaction, the reaction system was adjusted to pH=6-7 using 1 mol / L dilute hydrochloric acid and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 29-1 (254 mg, yield 49.6%). ESI[M+H] + =369.1.

[0178] 2. Preparation of target compound 29 29-1 (50 mg, 0.136 mmol), DCC (39.6 mg, 0.192 mmol), and DMAP (23.5 mg, 0.192 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 3-Methyloxetan-3-ol (12.5 mg, 0.142 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain white solid compound 29 (15.4 mg, yield 25.9%). ESI[M+H] + =439.2. 1 H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.44 (d, J=8.9Hz, 1H), 8.34-8.28 (m, 1H), 8.27-8.23 (m, 1H), 8.10-8.06 (m, 1H), 7.64-7.58 (m, 1H), 7.54-7.52 (m, 1H), 4.71 (d, J=6.7 Hz, 2H), 4.47 (d, J=7.5 Hz, 2H), 3.80-3.73 (m, 1H), 3.52 (s, 3H), 2.70-2.58 (m, 3H), 2.55-2.46 (m, 1H), 1.66 (s, 3H) Example 18 Preparation of compounds 30-32 TIFF2026519809000091.tif27170

[0179] The preparation method for target compounds 30-32 was the same as for compound 29 in Example 17, using 29-1 and the corresponding alcohol as starting materials to obtain the corresponding esters.

[0180] Compound 30:18.8mg,ESI[M+H] + = 451.2.

[0181] 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 8.42 (d, J=8.7 Hz, 1H), 8.33-8.27 (m, 2H), 8.01-7.95 (m, 1H), 7.55-7.50 (m, 2H), 6.18 (dd, , 2.73-2.60 (m, 3H), 2.55-2.45 (m, 1H). Compound 31: 23.1 mg, ESI [M+H] + =425.2. 1 H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.41 (d, J=9.0 Hz, 1H), 8.34 (s, 1H), 8.27 (d, J=7.5 Hz, 1H), 7.96-7.90 (m, 1H), 7.54-7.42 (m, 2H), 5.46-5.38 (m, 1H), 4.86 (dd, J=11.2, 6.6 Hz, 2H), 4.62- 4.59 (m, 2H), 3.78-3.74 (m, 1H), 3.49 (s, 3H), 2.76-2.57 (m, 3H), 2.55-2.45 (m, 1H) . Compound 32: 41.4 mg, ESI [M+H] + =435.1.

[0182] 1H NMR (400 MHz, DMSO-d6) δ 8.57 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.44 (dd, J=9.2, 2.8 Hz, 1H), 8.22-8.20 (m, 2H), 8.00 (td, J=7.7, 1.8Hz, 1H), 7.80 (d, J=9.2 Hz, 1H), 7.55 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 3.76 (dd, J=7.8, 5.5 Hz, 1H), 3.44 (s, 1H), 3.39 (s, 3H), 2.49-2.29 (m, 3H), 2.27-2.21 (m, 1H), 1.56 (s, 3H), 1.55 (s, 3H). Example 19 Preparation of Compounds 34-37 TIFF2026519809000092.tif59170

[0183] 1. Preparation of Compound 37-1 BOC-L-serine (18.0 g, 87.7 mmol) was added to dichloromethane (180 mL) with DIEA (13.6 g, 105.2 mmol) and anhydride acetate (9.78 g, 95.8 mmol), and the mixture was stirred at room temperature for 18 hours. After confirming the completion of the reaction by TLC, water (50 mL) was added to the reaction system and extracted with dichloromethane (3 × 100 mL). The organic phase was washed with 1% dilute hydrochloric acid, then with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain a colorless oily compound 37-1 (16.7 g, yield 77.0%). ESI[M+H] + = 248.1.

[0184] 2. Preparation of Compound 37-2 1-1 (12.4 g, 44.7 mmol) and 37-1 (16.7 g, 67.5 mmol) were dissolved in dichloromethane (100 mL), and a solution of DCC (18.5 g, 89.7 mmol) in dichloromethane (40 mL) was added dropwise at -10°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (140 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (V / v) = 1 / 20~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 37-2 (10.5 g, yield 46.3%). ESI[M+H] + = 506.1.

[0185] 3. Preparation of Compound 37-3 At 0°C, 10 mL of trifluoroacetic acid was added to a 20 mL solution of 37-2 (10.5 g, 20.7 mmol) of dichloromethane, and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step without purification.

[0186] 4. Preparation of target compound 34 The crude product from the previous step was dissolved in acetonitrile (100 mL), sodium bicarbonate (52.0 g, 619 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2~0.3 was recovered to obtain white solid compound 34 (6.3 g, 2-step yield 78.3%). ESI[M+H] + = 388.2.

[0187] 1H NMR (400MHz, DMSO-d6) δ10.85 (s, 1H), 8.57 (dd, J=4.0, 0.8 Hz, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.7 Hz, 1H), 7.75 (dd, J=8.7, 2.3 Hz, 1H), 7.55-7.49 (m, 2H), 7.19 (d, J=8.8 Hz, 1H), 4.72-4.58 (m, 2H), 3.93 (t, J=6.4 Hz, 1H), 2.03 (s, 3H). 5. Preparation of Compound 37-4 and Target Compound 35 At -20°C, NaH (716 mg, 60%, 17.9 mmol) was slowly added to 34 (6.3 g, 16.2 mmol) dry DMF (60 mL) solution and stirred for 30 minutes. Iodomethane (2.54 g, 17.9 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (120 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1) and confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), yielding white solid compound 37-4 (2.86 g, yield 43.8%) and yellow solid compound 35 (62.8 mg, yield 1.2%).

[0188] Compound 37-4:ESI[M+H] + = 402.1.

[0189] Compound 35: ESI[M+H] + = 328.2.

[0190] 1H NMR (400 MHz, DMSO-d6) δ 10.77 (s, 1H), 8.69-8.58 (m, 1H), 8.13 (d, J=7.9 Hz, 1H), 8.01 (td, J =7.8, 1.7 Hz, 1H), 7.71 (dd, J=8.7, 2.3 Hz, 1H), 7.56 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 7.42 (d, J=2.3 Hz, 1H), 7.19 (d, J=8.7 Hz, 1H), 5.19 (s, 1H), 4.99 (s, 1H). 6. Preparation of target compounds 36 and 37 At 0°C, LiOH / H2O (450 mg, 10.7 mmol) was added to 37-4 (2.86 g, 7.11 mmol) in a THF / H2O (25 mL, v / v = 1 / 1) solution, and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1) and confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1) to obtain yellow solid compound 36 (1.2 g, yield 49.3%) and colorless oily compound 37 (1.01 g, yield 39.4%).

[0191] Compound 36:ESI[M+H] + = 342.2.

[0192] 1H NMR (400 MHz, DMSO-d6) δ 8.63 (d, J=4.7Hz, 1H), 8.19 (d, J=7.9 Hz, 1H), 8.01 (td, J=7.8, 1.7 Hz, 1H), 7.78 (dd, J=8.8, 2.4 Hz, 1H), 7.61-7.55 (m, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.48 (d, J=8.9Hz, 1H), 5.10 (s, 1H), 4.92 (s, 1H), 3.32 (s, 3H). Compound 37: ESI[M+H] + =360.2.

[0193] 1 H NMR (400MHz, DMSO-d6) δ 8.58 (d, J=4.0Hz, 1H), 8.15 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.8, 1.7 Hz, 1H), 7.82 (dd, J=8.8, 2.4 Hz, 1H), 7.55 (d, J=8.9Hz, 1H), 7.53-7.50 (m, 2H), 4.71 (t, J=5.8 Hz, 1H), 4.21-4.15 (m, 1H), 4.03-3.94 (m, 1H), 3.65 (t, J=6.5 Hz, 1H), 3.30 (s, 3H) . Example 20 Preparation of Compound 40 TIFF2026519809000093.tif27170

[0194] At -10°C, propionyl chloride (38.7 mg, 0.418 mmol) was added dropwise to a solution of 37 (100 mg, 0.278 mmol) and triethylamine (56.3 mg, 0.556 mmol) in dichloromethane (2 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4~0.5 was recovered to obtain white solid compound 40 (73.5 mg, yield 63.6%). ESI[M+H] + =416.0. 1 H NMR (400 MHz, DMSO-d6) δ8.59 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.58-7.49 (m, 3H), 4.72-4.59 (m, 2H), 3.97 (tJ=6.5Hz, 1H), 3.32 (s, 3H), 2.31 (q, J=7.5 Hz, 2H), 1.02 (t, J=7.5 Hz, 3H). Example 21 Preparation of Compounds 41-43 TIFF2026519809000094.tif28170

[0195] The preparation method for target compounds 41-43 was the same as for compound 40 in Example 20, using compound 37 and the corresponding asyl chloride as starting materials, and the corresponding esters were obtained by preparation.

[0196] Compound 41:72.4 mg,ESI[M+H] + = 430.0.

[0197] 1H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=4.1 Hz, 1H), 8.06 (d, J=7.9Hz, 1H), 7.97 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=8.9, 2.4 Hz, 1H), 7.59-7.50 (m, 3H), 4.71-4.59 (m, 2H), 3.99 (t, J=6.5Hz, 1H), 3.32 (s, 3H), 2.57-2.51 (m, 1H), 1.09-1.04 (m, 6H). Compound 42: 19.7 mg, ESI [M+H] + =464.0.

[0198] 1 H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=4.0 Hz, 1H), 8.07 (d, J=7.9 Hz, 1H), 7.99-7.91 (m, 3H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.65 (t, J=7.4 Hz, 1H), 7.58-7.50 (m, 5H), 4.97-4.87 (m, 2H), 4.19 (t, J= 6.4 Hz, 1H), 3.34 (s, 3H). Compound 43: 54.1 mg, ESI [M+H] + =436.0.

[0199] 1 H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=4.0 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.7Hz, 1H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.60-7.49 (m, 3H), 4.78 (d, J=6.5 Hz, 2H), 4.40 (s, 2H), 4.05-4.00 (m, 1H), 3.32 (s, 3H). Example 22 Preparation of compound 44 and 45 TIFF2026519809000095.tif29170

[0200] At -10°C, 53.1 mg, 0.418 mmol of 3-chloropropionyl chloride was added dropwise to a solution of 37 (100 mg, 0.278 mmol) and triethylamine (56.3 mg, 0.556 mmol) in 2 mL of dichloromethane, and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, 10 mL of ice water was added to the reaction system, and the mixture was extracted with 3 × 10 mL of dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20) and confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10) to obtain white solid compound 44 (9.5 mg, yield 7.6%) and white solid compound 45 (19.5 mg, yield 17.0%).

[0201] Compound 44:ESI[M+H] + =450.0. 1 H NMR (400 MHz, DMSO-d6) δ 8.62-8.57 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.83 (dd, J=8.9, 2.4 Hz, 1H), 7.59-7.49 (m, 3H), 4.77-4.70 (m, 2H), 3.99 (t, J=6.4 Hz, 1H), 3.79 (t, J=6.2 Hz, 2H), 3.32 (s, 3H), 2.83 (dd, J=6.5, 5.8Hz, 2H). Compound 45:ESI[M+H] + = 414.0.

[0202] 1H NMR (400 MHz, DMSO-d6) δ 8.59 (ddd, J=4.8, 1.6, 0.9 Hz, 1H), 8.07 (d, J=7.9Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.60-7.49 (m, 3H), 6.35 (dd, J=17.3, 1.6Hz, 1H), 6.19 (dd, J=17.3, 10.3 Hz, 1H), 5.95 (dd, J=10.3, 1.6 Hz, 1H), 4.80-4.71 (m, 2H), 4.04 (t, J=6.5 Hz, 1H), 3.32 (s, 3H). Example 23 Preparation of Compound 46 TIFF2026519809000096.tif31170

[0203] 2-Picolinic acid (51.4 mg, 0.418 mmol), DCC (86.1 mg, 0.417 mmol), and DMAP (68 mg, 0.557 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 37 (100 mg, 0.278 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 46 (39.1 mg, yield 30.3%). ESI[M+H] + = 465.0.

[0204] H NMR (400 MHz, DMSO-d6) δ8.72-8.70 (m, 1H), 8.63-8.58 (m, 1H), 8.10-8.03 (m, 2H), 7.99-7.93 (m, 2H), 7.85 (dd, J=8.9, 2.4 Hz, 1H), 7.64 (ddd, J=7.5, 4.7, 1.3 Hz, 1H), 7.59-7.56 (m, 2H), 7.53 (ddd, J=7.5, 4.8, 1.2Hz, 1H), 5.02-4.91 (m, 2H), 4.19 (t, J=6.4 Hz, 1H), 3.33 (s, 3H). Example 24 Preparation of compounds 47-49, 51 TIFF2026519809000097.tif27170

[0205] The preparation method for compounds 47-49 and 51 was the same as for compound 46 in Example 23, using compound 37 and the corresponding carboxylic acid as starting materials to obtain the corresponding esters.

[0206] Compound 47:48.3mg,ESI[M+H] + = 465.1.

[0207] 1 H NMR (400 MHz, DMSO-d6) δ 8.80-8.79 (m, 2H), 8.62-8.57 (m, 1H), 8.07 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8 Hz, 1H), 7.86-7.82 (m, 3H), 7.59-7.49 (m, 3H), 5.01-4.92 (m, 2H), 4.22 (t, J=6.3 Hz, 1H), 3.34 (m, 3H). Compound 48:72.3mg,ESI[M+H] + = 465.1.

[0208] H NMR (400 MHz, DMSO-d6) δ 9.03 (s, 1H), 8.75 (d, J=4.7Hz, 1H), 8.53 (d, J=4.1 Hz, 1H), 8.23 ​​(d, J=8.0 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.89 (t, J=7.7 Hz, 1H), 7.81-7.75 (m, 1H), 7.52-7.45 (m, 4H), 4.96-4.83 (m, 2H), 4.16 (t, J=6.3 Hz, 1H), 3.28 (s, 3H). Compound 49: 32.3 mg, ESI [M+H] + =434.0.

[0209] 1 H NMR (400 MHz, DMSO-d6) δ 8.61-8.57 (m, 1H), 8.09-8.02 (m, 1H), 8.02-7.94 (m, 1H), 7.84 (dd, J=8.9, 2.4Hz, 1H), 7.57-7.52 (m, 3H), 5.31-5.25 (m, 1H), 4.88-4.68 (m, 2H), 4.06 (dd, J=9.6, 3.2Hz, 1H), 3.32 (s, 3H), 1.51-1.42 (m, 3H). Compound 51: 22.7 mg, ESI [M+H] + =426.1.

[0210] 1 H NMR (400 MHz, DMSO-d6) δ 8.62 (d, J=4.2 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 8.00 (td, J=7.7, 1.7 Hz, 1H), 7.86 (dd, J=8.9, 2.3Hz, 1H), 7.63-7.50 (m, 3H), 4.83-4.71 (m, 2H), 4.06 (t, J=6.3 Hz, 1H), 3.34 (s, 3H), 2.04 (s, 3H). Example 25 Preparation of Compound 53 TIFF2026519809000098.tif34170

[0211] 1. Preparation of Compound 53-1 NaOH (232 mg, 5.8 mmol) was added to a solution of ethyl fluoroethyl (530 mg, 5.0 mmol) in EtOH / H2O (7 mL, v / v=1 / 1) and stirred at room temperature for 16 hours. After confirming the completion of the reaction by TLC, the reaction system was adjusted to pH=6-7 using 1 mol / L hydrochloric acid and extracted with diethyl ether (3 × 30 mL). The organic phase was washed with saturated saline solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain a colorless oily compound 53-1 (150 mg, yield 38.5%).

[0212] 2. Preparation of Compound 53 53-1 (116.1 mg, 1.49 mmol), DCC (592.4 mg, 2.87 mmol), and DMAP (526.0 mg, 4.31 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 37 (50 mg, 0.139 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system, stirred for 5 minutes, filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 53 (5.6 mg, yield 9.6%). ESI[M + H] + = 420.0.

[0213] 1H NMR (400 MHz, DMSO-d6) δ8.62 (d, J= 4.0 Hz, 1H), 8.11 (d, J= 7.9 Hz, 1H), 8.00 (td, J= 7.7, 1.7Hz, 1H), 7.86 (dd, J = 8.9, 2.4 Hz, 1H), 7.59 - 7.56 (m, 3H), 5.06 (d, J= 46.2 Hz, 2H), 4.84 - 4.81 (m, 2H),4.06 (t, J= 6.4 Hz, 1H), 3.34 (s, 3H). Example 26 Preparation of Compound 54 TIFF2026519809000099.tif27170

[0214] At 0°C, ethyl chloroformate (272.1 mg, 2.51 mmol) was added dropwise to a solution of 37 (300 mg, 0.833 mmol), pyridine (198.3 mg, 2.51 mmol), and DMAP (101.9 mg, 0.834 mmol) in dichloromethane (5 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain off-white solid compound 54 (170.3 mg, yield 47.3%). ESI[M + H] + = 432.2.

[0215] 1H NMR (400 MHz, DMSO-d6) δ8.59 (d, J=4.0Hz, 1H), 8.07 (d, J=7.9 Hz, 1H), 8.00-7.93 (m, 1H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.58-7.51 (m, 3H), 4.77-4.73 (m, 1H), 4.70-4.65 (m, 1H), 4.13 (q, J=7.1 Hz, 2H), 4.02 (t, J=6.4 Hz, 1H), 3.31 (s, 3H), 1.20 (t, J=7.1 Hz, 3H). Example 27 Preparation of Compound 55 TIFF2026519809000100.tif29170

[0216] The method for preparing target compound 55 was the same as for compound 54 in Example 26, using compound 37 and isopropyl chloroformate as raw materials and obtaining it by purification.

[0217] Compound 55:279.7mg,ESI[M+H] + = 446.0.

[0218] 1 H NMR (400 MHz, DMSO-d6) δ 8.60-8.58 (m, 1H), 8.09-8.03 (m, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.58-7.50 (m, 3H), 4.81-4.63 (m, 3H), 4.01 (t, J=6.4 Hz, 1H), 3.31 (s, 3H), 1.28-1.20 (m, 6H). Example 28 Preparation of compounds 56 and 57 TIFF2026519809000101.tif44170

[0219] 1. Preparation of Compound 56-1 At 0°C, 4-nitrophenyl chloroformate (505.3 mg, 2.51 mmol) was added to a 5 mL solution of dichloromethane containing 37 (300 mg, 0.833 mmol), pyridine (193.1 mg, 2.44 mmol), and DMAP (102 mg, 0.835 mmol). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, 10 mL of ice water was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 56-1 (272.8 mg, yield 62.4%). ESI[M+H] + =525.1. 2. Preparation of target compound 56 Dimethylamine (0.095 mL, 2 mol / Lin THF, 0.19 mmol) was added to a solution of 56-1 (100 mg, 0.19 mmol) and DIEA (24.6 mg, 0.19 mmol) in dichloromethane (2 mL), and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 56 (34.8 mg, yield 42.4%). ESI[M+H] + = 431.1.

[0220] 1H NMR (400 MHz, DMSO-d6) δ8.61 (d, J=4.1 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.99 (td, J=7.7, 1.7 Hz, 1H), 7.85 (dd, J=8.8, 2.4 Hz, 1H), 7.58 (d, J=8.9Hz, 1H), 7.56-7.54 (m, 2H), 4.69 (dd, J=10.9, 5.9 Hz, 1H), 4.60 (dd, J=10.8, 7.1 Hz, 1H), 3.97 (t, J=6.5 Hz, 1H), 3.34 (s, 3H), 2.82 (s, 6H). 3. Preparation of target compound 57 The method for preparing target compound 57 was the same as for compound 56 in Example 28, using compound 56-1 and N-ethylmethylamine as starting materials and obtaining it by purification.

[0221] Compound 57:62.1 mg,ESI[M+H] + = 445.1.

[0222] 1 H NMR (400 MHz, DMSO-d6) δ 8.61-8.56 (m, 1H), 8.07 (d, J=7.9 Hz, 1H), 8.00-7.93 (m, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.56 (d, J=8.9Hz, 1H), 7.53-7.52 (m, 2H), 4.67-4.60 (m, 2H), 3.95 (t, J= 6.5 Hz, 1H), 3.32 (s, 3H), 3.25-3.15 (m, 2H), 2.78 (s, 3H), 1.00 (t, J=7.0 Hz, 3H). Example 29 Preparation of Compounds 58 and 61 TIFF2026519809000102.tif24170

[0223] 1. Preparation of target compound 58 At 0°C, methanesulfonyl chloride (572.5 mg, 5.0 mmol) was added dropwise to a solution of 37 (359 mg, 0.997 mmol), pyridine (395 mg, 4.99 mmol), and DMAP (122 mg, 0.999 mmol) in dichloromethane (10 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 58 (190 mg, yield 43.5%). ESI[M+H] + = 438.0.

[0224] 1 H NMR (400 MHz, CDCl3) δ 8.65 (d, J=3.8 Hz, 1H), 8.16 (d, J=7.9 Hz, 1H), 7.88-7.84 (m, 1H), 7.69 (dd, J=8.8, 2.2 Hz, 1H), 7.54 (d, J=2.3 Hz, 1H), 7.42 (dd, J=6.9, 4.9Hz, 1H), 7.28-7.25 (m, 1H), 5.08 (dd, J=10.1, 7.0 Hz, 1H), 4.88 (dd, J=10.1, 6.1 Hz, 1H), 4.05 (t, J=6.5Hz, 1H), 3.42 (s, 3H), 3.16 (s, 3H). 2. Preparation of target compound 61 At 0°C, NaH (47.2 mg, 60%, 1.18 mmol) was slowly added to a solution of hydroxyacetone (88.6 mg, 1.20 mmol) in dry DMF (3 mL) and stirred for 30 minutes. Compound 58 (172 mg, 0.392 mmol) was added to the reaction system and stirred for a further 5 hours at 0°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 61 (8.2 mg, yield 5.0%). ESI[M+H] + =416.0. 1 H NMR (400 MHz, DMSO-d6) δ8.60-8.56 (m, 1H), 7.98-7.97 (m, 2H), 7.82 (dd, J=8.8, 2.4 Hz, 1H), 7.56-7.50 (m, 2H), 7.46 (d, J=2.4 Hz, 1H), 5.26 (d, J=5.3 Hz, 1H), 4.17 (dd, J=11.5, 5.7 Hz, 1H), 3.86 (t, J=6.9 Hz, 1H), 3.31 (s, 3H), 2.55-2.50 (m, 1H), 2.43-2.38 (m, 1H), 2.19 (s, 3H). Example 30 Preparation of compounds 62, 63, 66-69 TIFF2026519809000103.tif30170

[0225] The preparation method for compounds 62, 63, and 66-69 was the same as for compound 58 in Example 29, using compound 37 and the corresponding sulfuryl chloride as starting materials, and obtaining them by purification.

[0226] Compound 62:18 .5mg,ESI[M+H] + = 452.0.

[0227] 1H NMR (400 MHz, DMSO-d6) δ 8.62-8.58 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.99 (td, J=7.7, 1.7Hz, 1H), 7.84 (dd, J=8.8, 2.4 Hz, 1H), 7.59-7.50 (m, 3H), 4.82-4.73 (m, 2H), 4.11 (dd, J=7.0, 5.7 Hz, 1H), 3.47-3.41 (m, 2H), 3.32 (s, 3H), 1.27 (t, J=7.3 Hz, 3H). Compound 63: 15.8 mg, ESI [M+H] + =466.0.

[0228] 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=4.0Hz, 1H), 8.07 (d, J=7.9Hz, 1H), 7.97 (td, J=7.7, 1.7 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.59-7.47 (m, 3H), 4.83-4.69 (m, 2H), 4.09 (t, J=6.3 Hz, 1H), 3.78 -3.65 (m, 1H), 3.30 (s, 3H), 1.32-1.28 (m, 6H). Compound 66: 17.1 mg, ESI [M+H] + =500.0.

[0229] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.1Hz, 1H), 8.02-7.96 (m, 3H), 7.92 (d, J=7.9 Hz, 1H), 7.88-7.79 (m, 2H), 7.71 (t, J=7.7 Hz, 2H), 7.58-7.50 (m, 3H), 4.73-4.60 (m, 2H), 4.02 (dd, J=7.2, 5.4 Hz, 1H), 3.29 (s, 3H). Compound 67: 26.6 mg, ESI [M+H] + =534.0.

[0230] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.2 Hz, 1H), 7.98-7.96 (m, 3H), 7.90 (d, J=7.9Hz, 1H), 7.85 (dd, J=8.9, 2.4 Hz, 1H), 7.79-7.77 (m, 2H), 7.60-7.51 (m, 3H), 4.73-4.63 (m, 2H), 4.08-3.98 (m, 1H), 3.29 (s, 3H). Compound 68: 80.3 mg, ESI [M+H] + =534.1.

[0231] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.6 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.85 (dd, J=8.9, 2.4 Hz, 1H), 7.79-7.78 (m, 2H), 7.66-7.59 (m, 1H), 7.58-7.53 (m, 2H), 7.51 (d, J=2.3 Hz, 1H), 4.79-4.69 (m, 2H), 4.04 (dd, J=7.7, 4.9 Hz, 1H), 3.28 (s, 3H) . Compound 69: 106.0 mg, ESI [M+H] + =534.2. 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.3 Hz, 1H), 8.03-8.00 (m, 1H), 7.98-7.96 (m, 2H), 7.94-7.88 (m, 2H), 7.85 (dd, J=8.9, 2.4Hz, 1H), 7.73 (t, J=8.0 Hz, 1H), 7.57-7.52 (m, 2H), 7.51 (d, J= 2.4 Hz, 1H), 4.77-4.66 (m, 2H), 4.04 (dd, J=7.3, 5.2 Hz, 1H), 3.29 (s, 3H). Example 31 Preparation of Compound 71 TIFF2026519809000104.tif27170

[0232] Methyl acetoacetate (68 mg, 0.586 mmol) was added to a methanol (3 mL) solution of sodium methoxide (32 mg, 0.592 mmol) and stirred at room temperature for 30 minutes. 36 (200 mg, 0.584 mmol) was added to the reaction system and stirred for a further 16 hours at room temperature. After confirming the completion of the reaction by TLC, the reaction system was adjusted to pH 6-7 using 1 mol / L hydrochloric acid under an ice bath and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20-1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain the white solid compound 71 (113.0 mg, yield 42.2%). ESI[M+H] + = 458.2.

[0233] 1 H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.6 Hz, 1H), 8.05-7.96 (m, 2H), 7.81 (dd, J=8.6, 2.2 Hz, 1H), 7.56-7.50 (m, 2H), 7.48 (dd, J=9.5, 2.4 Hz, 1H), 3.95-3.91 (m, 1H), 3.76-3.71 (m, 1H), 3.67 (s, 1.5H), 3.61 (s, 1.5H), 3.30 (s, 3H), 2.68-2.57 (m, 1H), 2.45-2.40 (m, 1H), 2.27 (s, 1.5H), 2.20 (s, 1.5H) Example 32 Preparation of Compound 72 TIFF2026519809000105.tif29170

[0234] The preparation method for compound 72 was the same as for compound 71 in Example 31, using compound 36 and dimethyl malonate as raw materials and obtaining it by purification.

[0235] Compound 72:165.4 mg,ESI[M+H] + = 474.2.

[0236] 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=4.4 Hz, 1H), 8.04 (d, J=7.8 Hz, 1H), 8.00-7.97 (m, 1H), 7.82 (dd, J=8.8, 2.4 Hz, 1H), 7.56-7.50 (m, 2H), 7.49 (d, J=2.4Hz, 1H), 3.85-3.73 (m, 2H), 3.67 (s, 3H), 3.60 (s, 3H), 3.30 (s, 3H), 2.71-2.62 (m, 1H), 2.50-2.45 (m, 1H). Example 33 Preparation of Compound 73 TIFF2026519809000106.tif29170

[0237] Compound 36 (95 mg, 0.278 mmol), azacyclobutane-3-carboxylate methyl hydrochloride (63.3 mg, 0.418 mmol), DBU (46.5 mg, 0.305 mmol), and sodium bicarbonate (44.3 mg, 0.527 mmol) were dissolved in methanol (2 mL) and stirred at 50°C for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 73 (71.5 mg, yield 56.3%). ESI[M+H] + =457.1. 1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.04-7.98 (m, 2H), 7.81 (d, J=8.3Hz, 1H), 7.53-7.49 (m, 3H), 3.62 (s, 3H), 3.60-3.37 (m, 4H), 3.31-3.29 (m, 1H), 3.28 (s, 3H), 3.22-3.05 (m, 3H). Example 34 Preparation of compounds 74 and 75 TIFF2026519809000107.tif60170

[0238] The preparation methods for compounds 74 and 75 were the same as for compound 73 in Example 33, using compound 36 and the corresponding amines (or their salts) as starting materials, and obtaining them by purification.

[0239] Compound 74:121.2 mg,ESI[M+H] + = 574.2.

[0240] 1 H NMR (400 MHz, DMSO-d6) δ8.80-8.20 (m, 1H), 8.01-7.71 (m, 3H), 7.65-7.29 (m, 6H), 7.21- 7.10 (m, 2H), 4.57-4.37 (m, 1H), 3.32-3.30 (m, 1H), 3.28 (s, 3H), 3.20-2.80 (m, 4H), 2.48-2.37 (m, 1H), 2.30-1.97 (m, 1H), 1.81-1.79 (m, 2H), 1.69-1.51 (m, 2H), 1.50-1.28 (m, 1H), 1.20-1.04 (m, 1H), 0.86 (t, J=7.4 Hz, 3H). Compound 75:70.3mg,ESI[M+H] + = 485.1.

[0241] 1H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=4.6 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.99-7.95 (m, 1H), 7.85-7.78 (m, 1H), 7.59-7.49 (m, 3H), 3.78-3.75 (m, 1H), 3.58 (s, 3H), 3.30 (s, 3H), 3.10-2.95 (m, 1H), 2.92-2.75 (m, 2H), 2.42-2.23 (m, 2H), 2.22-1.95 (m, 2H), 1.82-1.62 (m, 2H), 1.57-1.38 (m, 2H) Example 35 Preparation of Compounds 76 and 77 TIFF2026519809000108.tif52170

[0242] 1. Preparation of Compound 76-1 Compound 36 (170 mg, 0.497 mmol), benzeneamine (69.75 mg, 0.749 mmol), and DBU (83.6 mg, 0.549 mmol) were dissolved in methanol (2 mL) and stirred at 50°C for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 76-1 (198.6 mg, yield 91.8%). ESI[M+H] + = 435.1.

[0243] 2. Preparation of target compound 76 Ethyl chloroformate (45 mg, 0.415 mmol) was added to a solution of 76-1 (90.1 mg, 0.207 mmol) and cesium carbonate (135 mg, 0.414 mmol) in acetonitrile (2 mL), and the mixture was stirred at room temperature for 30 minutes. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 30), and the portion with Rf = 0.3-0.4 was recovered to obtain the white solid compound 76 (35.66 mg, yield 34.0%). ESI[M + H] + = 507.1.

[0244] 1 H NMR (400 MHz, DMSO-d6) δ8.59-8.53 (m, 1H), 7.90 (td, J=7.8, 1.8 Hz, 1H), 7.80 (dd, J=8.8, 2.4 Hz, 1H), 7.71 (d, J=7.9 Hz, 1H), 7.53-7.49 (m, 2H), 7.48 (d, J=2.3 Hz, 1H), 7.38-7.32 (m, 2H), 7.31 -7.29 (m, 2H), 7.25-7.21 (m, 1H), 4.48-4.34 (m, 1H), 4.29 (dd, J=14.2, 3.8 Hz, 1H), 4.07-3.95 (m, 2H), 3.90 (dd, J=9.3, 3.8 Hz, 1H), 3.28 (s, 3H), 1.04 (t, J=7.1 Hz, 3H). 3. Preparation of target compound 77 At 0°C, propionyl chloride (28.2 mg, 0.305 mmol) was added dropwise to a solution of 76-1 (88.5 mg, 0.203 mmol) and triethylamine (41.1 mg, 0.406 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 1 hour. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 50), and the portion with Rf = 0.3-0.4 was recovered to obtain the white solid compound 77 (34.48 mg, yield 34.5%). ESI[M+H] + = 491.1.

[0245] 1 H NMR (400 MHz, DMSO-d6) δ8.56 (d, J=4.7 Hz, 1H), 7.89 (t, J=7.8 Hz, 1H), 7.81 (dd, J=8.8, 2.1 Hz, 1H), 7.69 (d, J=7.7 Hz, 1H), 7.55-7.47 (m, 3H), 7.46-7.42 (m, 2H), 7.38-7.34 (m, 3H), 4.46 (d, J= 11.2 Hz, 1H), 4.27-4.20 (m, 1H), 3.96 (d, J=6.8 Hz, 1H), 3.27 (s, 3H), 1.99-1.85 (m, 2H), 0.85 (t, J=7.1 Hz, 3H). Example 36 Preparation of Compounds 79 and 80 TIFF2026519809000109.tif29170

[0246] The preparation methods for compounds 79 and 80 were the same as for compound 76 in Example 35. Compounds 79 and 80 were reacted with compound 36 and the corresponding amine to obtain intermediate 79-1, which was then reacted with ethyl chloroformate to obtain the target compound.

[0247] Compound 79:68.0 mg,ESI[M+H] + = 471.1.

[0248] 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=4.7Hz, 1H), 8.05-7.94 (m, 2H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.55-7.51 (m, 3H), 4.15-3.90 (m, 4H), 3.80-3.77 (m, 1H), 3.31 (s, 3H), 2.59-2.55 (m, 1H), 1.10-1.06 (m, 3H), 0.81-0.78 (m, 2H), 0.68-0.64 (m, 2H). Compound 80: 68.0 mg, ESI [M+H] + =445.0. 1 H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=4.1Hz, 1H), 8.08-8.05 (m, 1H), 7.97 (td, J=7.7, 1.7Hz, 1H), 7.83 (dd, J=8.9, 2.4Hz, 1H), 7.57-7.50 (m, 3H), 4.06-3.81 (m, 5H), 3.31 (s, 3H), 3.03-2.93 (m, 3H), 1.16-0.99 (m, 3H). Example 37 Preparation of Compound 81 TIFF2026519809000110.tif44170

[0249] 1. Preparation of compound 81-1 Compound 36 (376.2 mg, 1.10 mmol), 1-Boc-4-aminopiperidine (440 mg, 2.20 mmol), and DBU (183.7 mg, 1.21 mmol) were dissolved in methanol (4 mL) and stirred at 50°C for 1 hour. After confirming the completion of the reaction by TLC, ice water (15 mL) was added to the reaction system and extracted with ethyl acetate (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain white solid compound 81-1 (408 mg, yield 68.4%). EST[M+H] + = 542.2.

[0250] 2. Preparation of Compound 81-2 At 0°C, propionyl chloride (83.25 mg, 0.90 mmol) was added dropwise to a solution of 81-1 (408 mg, 0.752 mmol) and DIEA (193.9 mg, 1.50 mmol) in THF (4 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 1 hour. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100~1 / 10), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 5), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 81-2 (438 mg, yield 97.3%). ESI[M + H] + = 598.3 3. Preparation of Compound 81-3 Trifluoroacetic acid (5 mL) was added to a solution of 81-2 (438 mg, 0.732 mmol) in dichloromethane (10 mL) and stirred at room temperature for 30 minutes. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, the pH was adjusted to 8-9 with saturated sodium bicarbonate aqueous solution, and extracted with dichloromethane (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain the white solid compound 81-3 (348 mg, yield 95.4%). ESI[M + H] + = 498.2.

[0251] 4. Preparation of target compound 81 At 0°C, methyl 3-bromopropionate (100.8 mg, 0.604 mmol) was added to a solution of 81-3 (200 mg, 0.401 mmol) and DIEA (156 mg, 1.21 mmol) in dichloromethane (3 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain the white solid compound 81 (46.8 mg, yield 20.0%). ESI[M + H] + = 584.1.

[0252] 1H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.6 Hz, 1H), 8.08 (d, J=7.7Hz, 0.5H), 7.98 (t, J=7.9 Hz, 1H), 7.91 (dJ=8.0 Hz, 0.5H), 7.82 (td, , 3.79-3.70 (m, 1H), 3.63-3.60 (m, 0.5H), 3.60 (s, 1.5H), 3.54 (s, 1.5H), 3.31 (s, 3H), 2.97-2.90 (m, 1H), 2.85-2.66 (m, 2H), 2.62-2.55 (m, 1H), 2.41-2.30 (m, 3H), 2.09-2.00 (m, 1H), 1.98-1.69 (m, 3H), 1.65-1.50 (m, 1H), 1.45-1.31 (m, 2H), 0.99 (t, J=8.0 Hz, 1.5H), 0.88 (t, J=8.0Hz, 1.5H). Example 38 Preparation of Compound 82 TIFF2026519809000111.tif49170

[0253] 1. Preparation of compound 82-1 N-tert-butoxycarbonyl-4-piperidone (10.0 g, 50.2 mmol) and cyclopropylamine (5.73 g, 100.4 mmol) were dissolved in dichloromethane (150 mL) and stirred at room temperature for 2 hours. NaBH(OAc)3 (31.9 g, 150.5 mmol) was added to the reaction system and stirred for a further 10 hours at room temperature. After confirming the completion of the reaction by TLC, saturated sodium bicarbonate aqueous solution (100 mL) was added to the reaction system and extracted with ethyl acetate (3 × 100 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 82-1 (9.9g, yield 82.1%). ESI[M + H] + = 241.1.

[0254] 2. Preparation of Compound 82-2 Propionyl chloride (920 mg, 9.94 mmol) was added to a solution of 82-1 (1.20 g, 5.0 mmol) and DIEA (1.94 g, 15.0 mmol) in dried tetrahydrofuran (25 mL) and stirred at room temperature for 2 hours. After confirming the completion of the reaction by TLC, ice water (50 mL) was added to the reaction system and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100~1 / 3), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.3~0.4 was recovered to obtain a colorless oily compound 82-2 (1.33 g, yield 89.9%). ESI[M+H] + =297.2. 3. Preparation of Compound 82-3 Trifluoroacetic acid (2.57 g, 22.5 mmol) was added to a solution of 82-2 (1.33 g, 4.49 mmol) in dichloromethane (10 mL) and stirred at room temperature for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, the pH was adjusted to 8-9 using saturated sodium bicarbonate aqueous solution, and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100-1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3-0.4 was recovered to obtain a colorless oily compound 82-3 (684 mg, yield 77.7%). ESI[M +H] + = 197.1.

[0255] 4. Preparation of target compound 82 Compounds 36 (100 mg, 0.292 mmol), 82-3 (86.0 mg, 0.438 mmol), and DBU (49.0 mg, 0.322 mmol) were dissolved in methanol (2 mL) and stirred at 50°C for 1 hour. After confirming the completion of the reaction by TLC, ice water (15 mL) was added to the reaction system and extracted with ethyl acetate (3 × 15 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 2 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain the white solid compound 82 (77.7 mg, yield 49.4%). ESI[M+H] + =538.2. 1H NMR (400 MHz, DMSO-d6) δ8.97-8.52 (m, 1H), 8.33-7.79 (m, 4H), 7.71-7.46 (m, 2H), 3.90-3.71 (m, 1H), 3.60-3.46 (m, 1H), 3.31 (s, 3H), 3.30-3.28 (m, 1H), 3.25-2.75 (m, 3H), 2.60-2.52 (m, 1H), 2.49-2.33 (m, 3H), 2.35-1.75 (m, 3H), 1.52-1.25 (m, 2H), 1.02-0.90 (m, 3H), 0.81-0.71 (m, 4H) Example 39 Preparation of Compounds 83 and 88 TIFF2026519809000112.tif69170

[0256] 1. Preparation of Compound 88-1 At 0°C, NaH (2.146 g, 60%, 53.6 mmol) was slowly added to a solution of BOC-L-serine (5.0 g, 24.4 mmol) in dry DMF (60 mL), and the mixture was stirred for 30 minutes. Benzyl bromide (4.67 g, 27.3 mmol) was added to the reaction system, and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (100 mL), the pH was adjusted to 6-7 with 1 mol / L dilute hydrochloric acid, and the mixture was extracted with ethyl acetate (3 × 100 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2~0.3 was recovered to obtain a colorless oily compound 88-1 (6.8 g, yield 94.5%). ESI[M +H] + = 296.2.

[0257] 2. Preparation of Compound 88-2 1-1 (2.76 g, 9.96 mmol) and 88-1 (4.42 g, 15.0 mmol) were dissolved in dichloromethane (30 mL), and a solution of DCC (3.09 g, 15.0 mmol) in dichloromethane (10 mL) was added dropwise at -10°C. After the addition was complete, the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (40 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 88-2 (4.857 g, yield 88.0%). ESI[M+H] + = 554.1.

[0258] 3. Preparation of Compound 88-3 At 0°C, trifluoroacetic acid (20 mL) was added to a solution of 88-2 (4.857 g, 8.76 mmol) of dichloromethane (40 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step without purification.

[0259] 4. Preparation of Compound 88-4 The crude product from the previous step was dissolved in acetonitrile (50 mL), sodium bicarbonate (22.1 g, 263.1 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 88-4 (2.491 g, 2-step yield 65.2%). ESI[M + H] + = 436.1.

[0260] 5. Preparation of target compound 83 At -20°C, NaH (275 mg, 60%, 6.87 mmol) was added to 88-4 (2.49 g, 5.71 mmol) in a 30 mL solution of dry DMF and stirred for 30 minutes. Iodomethane (975 mg, 6.87 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / ) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 83 (2.47 g, yield 96.1%). ESI[M+H] + = 450.4.

[0261] 1 H NMR (400 MHz, DMSO-d6) δ8.61 (d, J=4.6 Hz, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.99 (td, J=7.8, 1.7 Hz, 1H), 7.84 (dd, J=8.8, 2.4 Hz, 1H), 7.56-7.53 (m, 3H), 7.37-7.34 (m, 4H), 7.32-7.26 (m, 1H), 4.62 (s, 2H), 4.25 (dd, J=9.6, 6.0 Hz, 1H), 4.08 (dd, J=9.6, 6.9Hz, 1H), 3.87 (t, J=6.3 Hz, 1H), 3.32 (s, 3H) 6. Preparation of Compound 37 At 0°C, aluminum chloride (7.19 g, 53.9 mmol) was slowly added to a solution of 83 (2.43 g, 5.40 mmol) of dichloromethane (50 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 60 mL). The organic phase was washed with 5% sodium bicarbonate aqueous solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain a colorless oily compound 37 (1.15 g, yield 59.2%). ESI[M+H] + = 360.2.

[0262] 7. Preparation of target compound 88 At 0°C, NaH (67 mg, 60%, 1.67 mmol) was slowly added to 37 (200 mg, 0.555 mmol) dry DMF (3 mL) solution and stirred for 30 minutes. Acetyl bromoethyl (186 mg, 1.11 mmol) was added to the reaction system, heated to 50°C, and stirred for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain white solid compound 88 (11.5 mg, yield 4.6%). ESI[M+H] + = 446.2.

[0263] 1H NMR (400 MHz, DMSO-d6) δ8.59 (d, J=4.2 Hz, 1H), 8.08 (d, J=7.6Hz, 1H), 7.99-7.95 (m, 1H), 7.83 (dd, J=8.8, 2.5Hz, 1H), 7.56-7.51 (m, 3H), 4.27 (dd, J=10.3, 6.0Hz, 1H), 4.23 (s, 2H), 4.15-4.14 (m, 1H), 4.10 (q, J=7.3 Hz, 2H), 3.88 (t, J=6.4 Hz, 1H), 3.30 (s, 3H), 1.18 (t, J=7.1 Hz, 3H). Example 40 Preparation of compounds 84-87 TIFF2026519809000113.tif50170

[0264] The preparation method for compounds 84-87 was the same as for compound 83 in Example 39, and they were reacted with BOC-L-serine and benzyl bromide having different substituents to obtain the corresponding carboxylic acids. The obtained carboxylic acids were condensed with compound 1-1, and the target compounds were obtained by deBoc, ring closure, and N-methylation reactions.

[0265] Compound 84:18.9mg,ESI[M+H] + = 464.1.

[0266] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.2 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.99 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.57-7.50 (m, 3H), 7.24 (d, J=7.9 Hz, 2H), 7.16 (d, J=7.8 Hz, 2H), 4.56 (s, 2H), 4.22 (dd, J=9.7, 6.0Hz, 1H), 4.05 (dd, J=9.7, 6.8Hz, 1H), 3.83 (t, J=6.4 Hz, 1H), 3.31 (s, 3H), 2.30 (s, 3H). Compound 85: 13.5 mg, ESI [M+H] + =484.0.

[0267] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.1 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.99 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.56-7.53 (m, 3H), 7.49-7.34 (m, 4H), 4.61 (s, 2H), 4.25 (dd, J= 9.7, 6.0Hz, 1H), 4.07 (dd, J=9.6, 6.8 Hz, 1H), 3.87 (t, J=6.4 Hz, 1H), 3.32 (s, 3H) . Compound 86: 24.2 mg, ESI [M+H] + =480.1.

[0268] 1 H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.2 Hz, 1H), 8.09 (d, J=7.9Hz, 1H), 7.99 (td, J=7.8, 1.7 Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.55-7.52 (m, 3H), 7.28 (d, J=8.6Hz, 2H), 6.91 (d, J=8.6Hz, 2H), 4.53 (s, 2H), 4.21 (dd, J=9.6, 6.1 Hz, 1H), 4.03 (dd, J=9.6, 6.8Hz, 1H), 3.82 (t, J=6.4 Hz, 1H), 3.75 (s, 3H), 3.31 (s, 3H). Compound 87: 51.2 mg, ESI [M+H] + =492.2.

[0269] 1H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.3 Hz, 1H), 8.09 (d, J=7.9Hz, 1H), 7.98 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=8.8, 2.4 Hz, 1H), 7.57-7.50 (m, 3H), 7.27 (d, J=8.1 Hz, 2H), 7.22 (d, J=8.1 Hz, 2H), 4.56 (s, 2H), 4.21 (dd, J=9.6, 6.0Hz, 1H), 4.05 (dd, J=9.6, 6.9Hz, 1H), 3.85 (t, J=6.4 Hz, 1H), 3.31 (s, 3H), 2.94-2.83 (m, 1H), 1.21 (s, 3H), 1.19 (s, 3H). Example 41 Preparation of Compound 91 TIFF2026519809000114.tif29170

[0270] 37 (300 mg, 0.833 mmol), 4-nitrobenzyl bromide (198.6 mg, 0.919 mmol), and silver oxide (232.4 mg, 1.00 mmol) were dissolved in dichloromethane (5 mL) and stirred at room temperature for 18 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain the white solid compound 91 (21.7 mg, yield 5.3%). ESI[M+H] + = 495.1.

[0271] 1H NMR (400 MHz, DMSO-d6) δ8.61 (d, J=4.2 Hz, 1H), 8.23 ​​(d, J=8.7 Hz, 2H), 8.11 (d, J=7.9 Hz, 1H), 8.01-7.98 (m, 1H), 7.84 (dd, J=8.9, 2.3Hz, 1H), 7.65 (d, J=8.7Hz, 2H), 7.57-7.54 (m, 3H), 4.79 (s, 2H), 4.30 (dd, J=9.7, 5.9Hz, 1H), 4.14 (dd, J=9.7, 6.9Hz, 1H), 3.93 (t, J=6.4Hz, 1H), 3.33 (s, 3H) . Example 42 Preparation of Compound 95 TIFF2026519809000115.tif29170

[0272] 1. Preparation of Compound 95-1 At -30°C, lithium bis(trimethylsilyl)amide (5.98 mL, 1 mol / L, 5.98 mmol) was slowly added dropwise to 88-4 (2.24 g, 5.13 mmol) tetrahydrofuran (20 mL) and stirred for 1 hour. Dimorpholinyl phosphinochloride (2.99 g, 11.7 mmol) was added in small amounts, and the mixture was stirred at -10°C for 4 hours. Isopropanolamine (1.68 g, 22.4 mmol) was added dropwise to the reaction system, allowed to rise naturally to room temperature, and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (20 mL) was added to the reaction system and extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 95-1 (1.6 g, yield 63.2%). ESI[M+H + = 493.1.

[0273] 2. Preparation of target compound 95 Dess-Martin reagent (3.5 g, 8.25 mmol) was added to a solution of 95-1 (1.6 g, 3.24 mmol) in acetone (20 mL) and stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (300 mL), washed with saturated sodium bicarbonate aqueous solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 95 (1.164 g, yield 75.8%). ESI[M+H] + = 473.1.

[0274] 1 H NMR (400 MHz, DMSO-d6) δ8.56-8.52 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8 Hz, 1H), 7.88 (dd, J=8.7, 2.3Hz, 1H), 7.66-7.63 (m, 2H), 7.51-7.48 (m, 1H), 7.43-7.32 (m, 4H), 7.30-7.26 (m, 1H), 6.80 (d, J=0.9Hz, 1H), 4.68 (s, 2H), 4.40-4.32 (m, 2H), 4.23 (dd, J=7.5, 5.3 Hz, 1H), 2.30 (d, J= 0.8 Hz, 3H). Example 43 Preparation of Compound 96 TIFF2026519809000116.tif28170

[0275] 1. Preparation of Compound 96-1 At -30°C, lithium bis(trimethylsilyl)amide (2.7 mL, 1 mol / L, 2.7 mmol) was slowly added dropwise to 84-4 (1.0 g, 2.22 mmol) tetrahydrofuran (10 mL) and the mixture was stirred for 1 hour. Dimorpholinyl phosphinochloride (1.34 g, 5.26 mmol) was added in small amounts, and the mixture was stirred at -10°C for 4 hours. Isopropanolamine (752 mg, 10.0 mmol) was added dropwise to the reaction system, the temperature was allowed to rise naturally to room temperature, and the mixture was stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (20 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 96-1 (811 mg, yield 72.0%). ESI[M+H] + =507.1. 2. Preparation of target compound 96 Dess-Martin reagent (1.698 g, 4.0 mmol) was added to a solution of 96-1 (811 mg, 1.60 mmol) in acetone (20 mL) and stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (30 mL), washed with saturated sodium bicarbonate aqueous solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 96 (228.7 mg, yield 29.4%). ESI[M +H] + =487.2. 1H NMR (400 MHz, DMSO-d6) δ8.56 (d, J=4.2 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.8, 1.7 Hz, 1H), 7.90 (dd, J=8.7, 2.3Hz, 1H), 7.67 (d, J=8.7Hz, 1H), 7.64 (d, J=2.3 Hz, 1H), 7.51 (dd, J=6.5, 4.9Hz, 1H), 7.28 (d, J=7.9 Hz, 2H), 7.17 (d, J=7.8 Hz, 2H), 6.81 (s, 1H), 4.64 (s, 2H), 4.44-4.31 (m, 2H), 4.22 (dd, J=7.3, 5.4 Hz, 1H), 2.31 (s, 3H), 2.30 (s, 3H). Example 44 Preparation of compounds 97,97B and 97D TIFF2026519809000117.tif44170

[0276] 1. Preparation of Compound 97-1 At 0°C, aluminum chloride (2.44 g, 18.3 mmol) was slowly added to a solution of 95 (866 mg, 1.83 mmol) of dichloromethane (50 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 60 mL). The organic phase was washed with 5% sodium bicarbonate aqueous solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 97-1 (620 mg, yield 88.4%). ESI[M+H] + = 383.1.

[0277] 2. Preparation of target compound 97 At -10°C, isobutyryl chloride (125 mg, 1.17 mmol) was added dropwise to a solution of 97-1 (300 mg, 0.783 mmol) and triethylamine (159 mg, 1.57 mmol) in dichloromethane (3 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4~0.5 was recovered to obtain the white solid compound 97 (208 mg, yield 58.6%). ESI[M+H] + =453.1. 1 H NMR (400 MHz, DMSO-d6) δ8.57-8.53 (m, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.7Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.64 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.83 (d, J=1.1Hz, 1H), 4.93 (dd, J=10.9, 8.0Hz, 1H), 4.84 (dd, J=11.0, 5.4Hz, 1H), 4.36 (dd, J=7.9, 5.4 Hz, 1H), 2.60-2.53 (m, 1H), 2.31 (d, J=0.7Hz, 3H), 1.11 (d, J=7.0Hz, 3H), 1.09 (d, J=7.0 Hz, 3H). 3. Preparation of target compound 97B Compound 97 (109.8 mg, 0.242 mmol) was dissolved in acetone (10 mL), and a solution of sulfuric acid (23.7 mg, 0.242 mmol) in acetone (1 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 hours. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain the white solid compound 97B (85.5 mg, yield 64.0%). ESI[M + H] + = 453.1.

[0278] 1 H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=4.7Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 8.04-7.96 (m, 2H), 7.80 (d, J=8.7 Hz, 1H), 7.75 (d, J=2.2 Hz, 1H), 7.55 (dd, J=6.3, 4.9Hz, 1H), 7.20 (s, 1H), 4.95 (dd, J= 11.0, 7.3 Hz, 1H), 4.87 (dd, J=11.1, 6.0 Hz, 1H), 4.58 (t, J=6.7 Hz, 1H), 2.60-2.52 (m, 1H), 2.38 (s, 3H), 1.14 (d, J=5.2 Hz, 3H), 1.12 (d, J=5.2 Hz, 3H). 4. Preparation of target compound 97D Compound 97 (27.2 mg, 0.06 mmol) was dissolved in ethyl acetate (1 mL), and a solution of benzenesulfonic acid (9.47 mg, 0.06 mmol) in ethanol (0.1 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain the white solid compound 97D (10.3 mg, yield 28.1%). ESI[M + H] + = 453.1.

[0279] 1H NMR (400 MHz, DMSO-d6) δ8.57 (d, J=4.6 Hz, 1H), 8.06 (d, J=7.8 Hz, 1H), 8.01-7.93 (m, 2H), 7.77 (d, J=8.7 Hz, 1H), 7.72 (d, J=2.2 Hz, 1H), 7.60-7.58 (m, 2H), 7.56-7.51 (m, 1H), 7.35-7.28 (m, 3H), 7.14 (s, 1H), 4.93 (dd, J=11.1, 7.4 Hz, 1H), 4.85 (dd, J=11.1, 6.0 Hz, 1H), 4.54 (t, J=6.6 Hz, 1H), 2.61-2.54 (m, 1H), 2.35 (s, 3H), 1.11 (d, J=5.6 Hz, 3H), 1.10 (d, J=5.6 Hz, 3H). Example 45 Preparation of Compounds 98 and 98D TIFF2026519809000118.tif27170

[0280] The preparation method for compounds 98 and 98D was the same as for compounds 97 and 97D in Example 44. Compound 97-1 and propionyl chloride were used as starting materials, and 98 was obtained by purification. This was then reacted with benzenesulfonic acid to obtain 98D.

[0281] Compound 98:73.1 mg,ESI[M+H] + = 439.0.

[0282] 1H NMR (400 MHz, DMSO-d6) δ 8.55 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.06 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8 Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.68 (d, J=8.7Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.83 (d, J=1.1 Hz, 1H), 4.98-4.82 (m, 2H), 4.34 (dd, J=7.5, 5.7 Hz, 1H), 2.38-2.32 (m, 2H), 2.31 (d, J=0.8 Hz, 3H), 1.05 (t, J=7.5 Hz, 3H). Compound 98D: 9.3 mg, ESI [M+H] + =439.1.

[0283] 1 H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=4.0 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.77 (d, J=8.7 Hz, 1H), 7.73 (d, J=2.3 Hz, 1H), 7.62-7.57 (m, 2H), 7.56-7.50 (m, 1H), 7.34-7.26 (m, 3H), 7.16 (s, 1H), 4.94-4.85 (m, 2H), 4.53 (t, J=6.3 Hz, 1H), 2.39-2.32 (m, 5H), 1.05 (t, J=7.5Hz, 3H). Example 46 Preparation of Compound 99 TIFF2026519809000119.tif31170

[0284] The method for preparing the target compound 99 was obtained by using the same method as the compound 97 in Example 44 and the compound 97-1 as a raw material and a purified compound.

[0285] Compound 99:42.8mg,ESI[M+H] + = 425.0.

[0286] 1 H NMR (400 MHz, DMSO-d6) δ 8.55 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.08-8.06 (m, 1H), 7.95 (td, J= 7.7, 1.8 Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.83 (d, J=1.1 Hz, 1H), 4.95-4.84 (m, 2H), 4.34 (t, J=6.6 Hz, 1H), 2.31 (d, J=0.8 Hz, 3H), 2.05 (s, 3H). Example 47 Preparation of Compound 100 TIFF2026519809000120.tif27170

[0287] At 0°C, benzenesulfonyl chloride (691.1 mg, 3.91 mmol) was added to a solution of 97-1 (300 mg, 0.783 mmol), pyridine (302.3 mg, 3.82 mmol), and DMAP (287.4 mg, 2.35 mmol) in dichloromethane (5 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain 100 units of pale yellow solid compound (126.4 mg, yield 30.9%). ESI[M+H] + = 523.1.

[0288] 1 H NMR (400 MHz, DMSO-d6) δ8.55 (d, J=4.2 Hz, 1H), 8.03 (d, J=7.5 Hz, 2H), 7.97 (t, J=7.0 Hz, 1H), 7.92-7.88 (m, 2H), 7.83 (t, J=7.4 Hz, 1H), 7.73 (t, J=7.7 Hz, 2H), 7.66 (d, J=8.7 Hz, 1H), 7.63 (d, J =2.2 Hz, 1H), 7.55-7.49 (m, 1H), 6.81 (s, 1H), 4.94-4.79 (m, 2H), 4.42 (dd, J=7.8, 5.0Hz, 1H), 2.30 (s, 3H) Example 48 Preparation of Compounds 101 and 101D TIFF2026519809000121.tif27170

[0289] 1. Preparation of target compound 101 3-Oxetanecarboxylic acid (80 mg, 0.784 mmol), DCC (162 mg, 0.785 mmol), and DMAP (192 mg, 1.57 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 97-1 (200 mg, 0.522 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 101 (81.5 mg, yield 33.4%). ESI[M+H] + =467.1. 1H NMR (400 MHz, DMSO-d6) δ8.55 (d, J=4.0 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8 Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.65 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.84 (d, J=1.1 Hz, 1H), 5.04-4.91 (m, 2H), 4.74-4.69 (m, 2H), 4.67-4.62 (m, 2H), 4.40 (dd, J=7.4, 5.7Hz, 1H), 3.96-3.90 (m, 1H), 2.31 (d, J=0.8 Hz, 3H). 2. Preparation of target compound 101D Compound 101 (81.5 mg, 0.174 mmol) was dissolved in ethyl acetate (1 mL), and a solution of benzenesulfonic acid (27.8 mg, 0.176 mmol) in ethanol (0.1 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a white solid compound 101D (60.8 mg, yield 55.7%). ESI[M + H] + = 467.0.

[0290] 1 H NMR (400 MHz, DMSO-d6) δ8.56 (d, J=4.0Hz, 1H), 8.06 (d, J=7.9 Hz, 1H), 8.00-7.91 (m, 2H), 7.75 (d, J=8.7 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.62-7.56 (m, 2H), 7.56-7.47 (m, 1H), 7.35-7.25 (m, 3H), 7.08 (s, 1H), 5.04-4.91 (m, 2H), 4.74-4.69 (m, 2H), 4.68-4.63 (m, 2H), 4.53 (t, J=6.5 Hz, 1H), 3.96 -3.90 (m, 1H), 2.34 (s, 3H). Example 49 Preparation of Compound 102 TIFF2026519809000122.tif29170

[0291] The preparation method for compound 102 was the same as for compound 101 in Example 48, using compound 97-1 and 2-fluoropropionic acid as starting materials and obtaining it by purification.

[0292] Compound 102:61.6mg,ESI[M+H] + = 457.3.

[0293] 1 H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=4.1 Hz, 1H), 8.07 (dd, J=7.9, 3.9 Hz, 1H), 8.00-7.96 (m, 1H), 7.93 (dd, J=8.7, 2.3 Hz, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.67 (d, J=2.2 Hz, 1H), 7.56-7.48 (m, 1H), 6.86 (d, J=1.0 Hz, 1H), 5.38-5.16 (m, 1H), 5.12-4.94 (m, 2H), 4.45 (dd, J=7.3, 5.7Hz, 1H), 2.34 (s, 3H), 1.57-1.47 (m, 3H). Example 50 Preparation of compounds 103 and 103D TIFF2026519809000123.tif29170

[0294] 1. Preparation of target compound 103 At 0°C, ethyl chloroformate (128 mg, 1.18 mmol) was added dropwise to a solution of 97-1 (150 mg, 0.391 mmol), pyridine (90.7 mg, 1.15 mmol), and DMAP (48 mg, 0.393 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 103 (138 mg, yield 77.4%). ESI[M + H] + = 455.0.

[0295] 1 H NMR (400 MHz, DMSO-d6) δ8.55 (dd, J=3.9, 0.8 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.95 (td, J= 7.7, 1.7Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.69-7.66 (m, 2H), 7.51 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.83 (d, J=1.1 Hz, 1H), 4.97-4.92 (m, 2H), 4.39 (t, J=6.6Hz, 1H), 4.15 (q, J=7.0 Hz, 2H), 2.31 (d, J=0.8 Hz, 3H), 1.23 (t, J=7.1 Hz, 3H). 2. Preparation of target compound 103D Compound 103 (125 mg, 0.275 mmol) was dissolved in ethyl acetate (4 mL), and a solution of benzenesulfonic acid (43.6 mg, 0.276 mmol) in ethyl acetate (0.5 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain a white solid compound 103D (120 mg, yield 71.2%). ESI[M + H] + = 455.0.

[0296] 1 H NMR (400 MHz, DMSO-d6) δ8.61-8.56 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 8.03-7.94 (m, 2H), 7.80 (d, J=8.7 Hz, 1H), 7.76 (d, J=2.3 Hz, 1H), 7.62-7.49 (m, 3H), 7.36-7.26 (m, 4H), 4.95 (d, J=6.7 Hz, 2H), 4.64 (t, J=6.5 Hz, 1H), 4.17 (q, J=7.1 Hz, 2H), 2.37 (d, J=0.7 Hz, 3H), 1.23 (t, J=7.1 Hz, 3H) . Example 51 Preparation of Compound 104 TIFF2026519809000124.tif31170

[0297] The preparation method for compound 104 was the same as for compound 103 in Example 50, and it was obtained by preparing compound 97-1 and isopropyl chloroformate.

[0298] Compound 104:68.8mg,ESI[M+H] + =469.0 1H NMR (400 MHz, DMSO-d6) δ 8.55 (dd, J=3.9, 0.8 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.95 (td, J= 7.7, 1.7Hz, 1H), 7.90 (dd, J=8.7, 2.3 Hz, 1H), 7.69-7.66 (m, 2H), 7.51 (ddd, J=7.5, 4.8, 1.2Hz, 1H), 6.83 (d, J=1.1 Hz, 1H), 5.00-4.88 (m, 2H), 4.86-4.75 (m, 1H), 4.39 (dd, J=7.4, 5.7 Hz, 1H), 2.31 (d, J=0.7 Hz, 3H), 1.25 (d, J=6.2 Hz, 3H), 1.23 (d, J=6.2 Hz, 3H). Example 52 Preparation of Compound 105 TIFF2026519809000125.tif31170

[0299] At 0°C, 4-nitrophenyl chloroformate (157 mg, 0.779 mmol) was added to a solution of 97-1 (100 mg, 0.261 mmol), pyridine (61.7 mg, 0.780 mmol), and DMAP (63.6 mg, 0.521 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, dimethylamine (0.4 mL, 2 mol / L in THF, 0.8 mmol) and DIEA (33.6 mg, 0.26 mmol) were added to the reaction system, and the mixture was stirred for a further 2 hours at room temperature. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 105 (47.2 mg, yield 39.8%). ESI[M + H] + = 454.3.

[0300] 1 H NMR (400 MHz, DMSO-d6) δ8.57 (d, J=4.0 Hz, 1H), 8.08 (d, J=7.8 Hz, 1H), 7.99-7.96 (m, 1H), 7.92 (dd, J=8.7, 2.3 Hz, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.67 (d, J=2.3 Hz, 1H), 7.56-7.48 (m, 1H), 6.86 (s, 1H), 4.91-4.83 (m, 2H) .4.34 (t,J=6.5 Hz, 1H), 2.85 (s, 6H), 2.33 (s, 3H). Example 53 Preparation of Compounds 109 and 110 TIFF2026519809000126.tif30170

[0301] 1. Preparation of target compound 109 At 0°C, NaH (60.6 mg, 60%, 1.51 mmol) was added to 88-4 (300 mg, 0.688 mmol) in a 5 mL solution of dry DMF, and the mixture was stirred for 30 minutes. 2-Diethylamino-1-bromoethane hydrobromide (216 mg, 0.828 mmol) was added to the reaction system, and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / ) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 109 (161 mg, yield 43.7%). ESI[M +H] + = 535.4.

[0302] 1H NMR (400 MHz, DMSO-d6) δ8.62 (d, J=4.3 Hz, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.97 (t, J=7.8 Hz, 1H), 7.81 (dd, J=8.8, 2.2 Hz, 1H), 7.71 (d, J=9.0 Hz, 1H), 7.60 (d, J=2.2 Hz, 1H), 7.55-7.50 (m, 1H), 7.36-7.35 (m, 4H), 7.31-7.28 (m, 1H), 4.61 (s, 2H), 4.32-4.14 (m, 2H), 4.05 (dd, J=9.5, 6.6 Hz, 1H), 3.84 (t, J=6.5 Hz, 1H), 3.74-3.71 (m, 1H), 2.37-2.35 (m, 2H), 2.25-2.22 (m, 4H), 0.67 (t, J=6.9 Hz, 6H). 2. Preparation of Compound 110-1 At 0°C, aluminum chloride (401 mg, 3.01 mmol) was slowly added to a solution of 10⁹ (161 mg, 0.301 mmol) of dichloromethane (10 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (10 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 20 mL). The organic phase was washed with 5% sodium bicarbonate aqueous solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2~0.3 was recovered to obtain the white solid compound 110-1 (84 mg, yield 62.7%). ESI[M + H] + = 445.1.

[0303] 3. Preparation of target compound 110 At 0°C, propionyl chloride (13.0 mg, 0.141 mmol) was added dropwise to a solution of 110-1 (42 mg, 0.094 mmol) and triethylamine (19.1 mg, 0.189 mmol) in dichloromethane (2 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the syrup-like solid compound 110 (10.6 mg, yield 22.4%). ESI[M+H] + =501.1. 1 H NMR (400 MHz, DMSO-d6) δ8.63 (d, J=4.7Hz, 1H), 8.10 (d, J=7.9Hz, 1H), 7.97 (t, J=7.0 Hz, 1H), 7.83 (dd, J=8.8, 2.3 Hz, 1H), 7.76 (d, J=8.9Hz, 1H), 7.63 (d, J=2.2 Hz, 1H), 7.57-7.51 (m, 1H), 4.73 (dd, J=10.7, 6.4Hz, 1H), 4.65 (dd, J=10.8, 6.7Hz, 1H), 4.20 (dd, J=14.0, 6.9Hz, 1H), 3.96 (t, J=6.6Hz, 1H), 3.80-3.70 (m, 1H), 2.38 (t, J=6.0 Hz, 2H), 2.35-2.17 (m, 6H), 1.03 (t, J=7.5 Hz, 3H), 0.66 (t, J=7.1 Hz, 6H). Example 54 Preparation of Compound 111 TIFF2026519809000127.tif39170

[0304] The method for preparing target compound 111 was the same as for compound 110 in Example 53, using 110-1 and isobutyryl chloride as starting materials and obtaining it by purification.

[0305] Compound 111: 26.2 mg, ESI [M+H] + =515.2.

[0306] 1 H NMR (400 MHz, DMSO-d6) δ 8.63 (d, J=4.7 Hz, 1H), 8.10 (d, J=7.8 Hz, 1H), 7.98 (t, J=7.2 Hz, 1H), 7.83 (dd, J=8.9, 2.2 Hz, 1H), 7.77 (d, J=8.9 Hz, 1H), 7.62 (d, J=2.1 Hz, 1H), 7.57-7.48 (m, 1H), 4.73-4.64 (m, 2H), 4.23-4.16 (m, 1H), 3.99 (t, J=6.6 Hz, 1H), 3.84-3.64 (m, 1H), 2.57-2.52 (m, 1H), 2.42-2.38 (m, 2H), 2.32-2.13 (m, 4H), 1.09 (d, J=2.4 Hz, 3H), 1.08 (d, J=2.4Hz, 3H), 0.68 (t, J=7.0 Hz, 6H). Example 55 Preparation of compound 113 and 114 TIFF2026519809000128.tif44170

[0307] 1. Preparation of compound 114-1 1-1 (2.76 g, 9.96 mmol) and Boc-L-4-methyl aspartate (3.70 g, 15.0 mmol) were dissolved in dichloromethane (30 mL), and a solution of DCC (3.09 g, 15.0 mmol) in dichloromethane (10 mL) was added dropwise at -10°C. The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming completion of the reaction by TLC, methyl tert-butyl ether (40 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 3), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 114-1 (3.356 g, yield 66.5%). ESI [M + H]+ = 506.1.

[0308] 2. Preparation of Compound 114-2 At 0°C, 15 mL of trifluoroacetic acid was added to a 30 mL solution of 114-1 (3.356 g, 6.63 mmol) of dichloromethane, and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step without purification.

[0309] 3. Preparation of Compound 114-3 The crude product from the previous step was dissolved in acetonitrile (40 mL), sodium bicarbonate (31.8 g, 378.5 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v)) = 1 / 10 to 1 / 2, confirmed by TLC (ethyl acetate / petroleum ether (v / v)) = 1 / 1, and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 114-3 (2.48 g, 2-step yield 96.4%). ESI[M + H] + = 388.1.

[0310] 4. Preparation of target compound 113 At -20°C, NaH (320 mg, 60%, 8.0 mmol) was slowly added to a solution of 114-3 (2.48 g, 6.39 mmol) in dry DMF (30 mL) and stirred for 30 minutes. Iodomethane (1.136 g, 8.0 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (60 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1) and confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1) to obtain the white solid compound 113 (2.459 g, yield 95.7%). ESI[M + H] + = 402.0.

[0311] 1 H NMR (400 MHz, DMSO-d6) δ8.62-8.58 (m, 1H), 8.03 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.7, 1.7Hz, 1H), 7.85 (dd, J=8.9, 2.4 Hz, 1H), 7.58 (d, J=8.9Hz, 1H), 7.55-7.49 (m, 2H), 4.09 (t, J=7.1 Hz, 1H), 3.61 (s, 3H), 3.32 (s, 3H), 3.25 (dd, J=16.6, 7.5 Hz, 1H), 3.09 (dd, J=16.6, 6.6 Hz, 1H). 5. Preparation of target compound 114 At 0°C, sodium isopropoxide (307 mg, 20% in THF, 0.748 mmol) was added dropwise to 113 (200 mg, 0.497 mmol) of 2-propanol (2 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 1 hour. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2-0.3 was recovered to obtain the white solid compound 114 (71.0 mg, yield 33.2%). ESI[M + H] + = 430.0.

[0312] 1 H NMR (400 MHz, DMSO-d6) δ8.59 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.05-8.00 (m, 1H), 7.99-7.93 (m, 1H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.58 (d, J=8.9 Hz, 1H), 7.55-7.49 (m, 2H), 4.92-4.86 (m, 1H), 4.08 (t, J=7.1 Hz, 1H), 3.31 (s, 3H), 3.18 (dd, J=16.5, 7.5 Hz, 1H), 3.04 (dd, J=16.5, 6.8 Hz, 1H), 1.24 - 1.14 (m, 6H) Example 56 Preparation of Compound 115 TIFF2026519809000129.tif42170

[0313] 1. Preparation of Compound 115-1 N-Boc-L-homoserine (9.0 g, 41.1 mmol) was dissolved in ethanol (70 mL), and a solution of sodium hydroxide (1.769 g, 44.2 mmol) in water (21 mL) was added. The mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the resulting white solid was dissolved in DMF (42 mL). Benzyl bromide (14 g, 81.9 mmol) was added to the reaction system, and the mixture was stirred at room temperature for a further 46 hours. After confirming the completion of the reaction by TLC, ice water (50 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3 to 0.4 was recovered to obtain a colorless oily compound 115-1 (2.34 g, yield 18.4%). ESI[M + H] + = 310.1.

[0314] 2. Preparation of Compound 115-2 115-1 (2.34 g, 7.56 mmol) was dissolved in dichloromethane (31 mL), and DIEA (2.14 g, 16.6 mmol) and anhydride acetate (1.53 g, 15.0 mmol) were added. The mixture was stirred at room temperature for 18 hours. After confirming the completion of the reaction by TLC, ice water (50 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 30 mL). The organic phase was washed with 1% dilute hydrochloric acid, then washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain a colorless oily compound 115-2 (1.2 g, yield 45.1%). ESI[M + H] + = 352.2.

[0315] 3. Preparation of Compound 115-3 At room temperature, 115-2 (1.2 g, 3.41 mmol) was dissolved in methanol (10 mL), and palladium hydroxide (carbon-supported) (200 mg, 10%) was added. The mixture was stirred under a hydrogen atmosphere at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 115-3 (769 mg, yield 86.2%). ESI[M + H] + = 262.1.

[0316] 4. Preparation of Compound 115-4 1-1 (1.2 g, 4.33 mmol) and 115-3 (769 mg, 2.94 mmol) were dissolved in dichloromethane (12 mL), and a solution of DCC (910 mg, 4.41 mmol) in dichloromethane (2 mL) was added dropwise at -10°C. The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (14 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20~1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 115-4 (1.42 g, yield 92.7%). ESI[M + H] + = 520.1.

[0317] 5. Preparation of Compound 115-5 At 0°C, trifluoroacetic acid (7.3 mL) was added to a solution of 115-4 (1.42 g, 2.73 mmol) of dichloromethane (14.6 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step without purification.

[0318] 6. Preparation of Compound 115-6 The crude product from the previous step was dissolved in acetonitrile (30 mL), sodium bicarbonate (8.62 g, 102.6 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 115-6 (525 mg, 2-step yield 47.8%). ESI[M + H] + = 402.1.

[0319] 7. Preparation of target compound 115 At -20°C, NaH (78.5 mg, 60%, 1.96 mmol) was slowly added to a solution of 115-6 (525 mg, 1.31 mmol) in dry DMF (10 mL) and stirred for 30 minutes. Iodomethane (279 mg, 1.97 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (20 mL) and extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 115 (395 mg, yield 72.7%). ESI[M+H] + =416.0. 1H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.0Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4Hz, 1H), 7.59-7.47 (m, 3H), 4.26-4.16 (m, 2H), 3.76 (dd, J=7.9, 5.7Hz, 1H), 3.31 (s, 3H), 2.41-2.27 (m, 2H), 1.94 (s, 3H). Example 57 Preparation of Compound 116 TIFF2026519809000130.tif39170

[0320] 1. Preparation of compound 116-1 1-1 (4.46 g, 16.1 mmol) and BOC-O-benzyl-L-homoserine (5.0 g, 16.2 mmol) were dissolved in dichloromethane (45 mL), and a solution of DCC (5.0 g, 24.2 mmol) in dichloromethane (15 mL) was added dropwise at -10°C. The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (60 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 116-1 (4.037 g, yield 44.1%). ESI[M + H] + = 568.1.

[0321] 2. Preparation of Compound 116-2 At 0°C, 10.1 mL of trifluoroacetic acid was added to a solution of 116-1 (4.037 g, 7.10 mmol) of dichloromethane (30.3 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step without purification.

[0322] 3. Preparation of Compound 116-3 The crude product from the previous step was dissolved in acetonitrile (50 mL), sodium bicarbonate (22.0 g, 261.9 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 116-3 (3.029 g, 2-step yield 94.7%). ESI[M + H] + = 450.1.

[0323] 4. Preparation of target compound 116 At -20°C, NaH (385.7 mg, 60%, 9.64 mmol) was added to a solution of 116-3 (3.029 g, 6.73 mmol) in dry DMF (30 mL) and stirred for 30 minutes. Iodomethane (1.053 g, 7.42 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 116 (2.903 g, yield 92.9%). ESI[M+H] + = 464.3.

[0324] 1H NMR (400 MHz, DMSO-d6) δ8.60 (d, J=4.7 Hz, 1H), 8.00-7.93 (m, 2H), 7.84 (dd, J=8.9, 2.2 Hz, 1H), 7.56-7.52 (m, 2H), 7.49 (d, J=2.2 Hz, 1H), 7.29-7.22 (m, 3H), 7.17 (d, J=7.4 Hz, 2H), 4.46 (d, J= 12.3 Hz, 1H), 4.38 (d, J=12.4Hz, 1H), 3.85-3.77 (m, 1H), 3.65-3.64 (m, 2H), 3.31 (s, 3H), 2.40-2.28 (m, 2H) Example 58 Preparation of Compound 117 Method A: TIFF2026519809000131.tif24170

[0325] Method B: TIFF2026519809000132.tif24170

[0326] Method C: TIFF2026519809000133.tif24170

[0327] Method A: Sodium borohydride (581 mg, 15.4 mmol) was added in small amounts to a methanol (30 mL) solution of 113 (2.045 g, 5.08 mmol), and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL) and extracted with ethyl acetate (3 × 40 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 117 (439 mg, yield 23.1%).

[0328] Method B: At 0°C, LiOH / H2O (49 mg, 1.17 mmol) was added to 115 (323 mg, 0.776 mmol) of THF / H2O (5 mL, v / v=1 / 1) solution and stirred for 30 minutes. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 117 (249 mg, yield 85.7%).

[0329] Method C: At 0°C, aluminum chloride (5.83 g, 43.7 mmol) was slowly added to a solution of 116 (2.903 g, 6.25 mmol) in dichloromethane (70 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (70 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 70 mL). The organic phase was washed with 5% sodium bicarbonate aqueous solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2~0.3 was recovered to obtain the white solid compound 117 (2.08 g, yield 88.9%). ESI[M+H] + =374.0. 1H NMR (400MHz, DMSO-d6) δ 8.58 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.7, 1.8 Hz, 1H), 7.81 (dd, J=8.8, 2.4 Hz, 1H), 7.57-7.48 (m, 3H), 4.40 (t, J=5.2 Hz, 1H), 3.79 (t, J= 6.9 Hz, 1H), 3.59 (q, J=6.0 Hz, 2H), 3.30 (s, 3H), 2.21 (q, J=6.7 Hz, 2H). Example 59 Preparation of Compound 118 TIFF2026519809000134.tif29170

[0330] At 0°C, difluoroacetic anhydride (112 mg, 0.643 mmol) was added dropwise to a solution of 117 (120 mg, 0.321 mmol), triethylamine (65.0 mg, 0.642 mmol), and DMAP (78.5 mg, 0.643 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (5 mL) was added to the reaction system and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 118 (24.0 mg, yield 16.5%). ESI[M + H] + = 452.0.

[0331] 1H NMR (400 MHz, DMSO-d6) δ 8.58 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.11 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.56-7.50 (m, 2H), 7.49 (d, J=2.4 Hz, 1H), 6.37 (t, J=52.7 Hz, 1H), 4.51-4.46 (m, 2H), 3.82 (dd, J=8.0, 5.6 Hz, 1H), 3.31 (s, 3H), 2.48-2.37 (m, 2H) Example 60 Preparation of Compound 120 TIFF2026519809000135.tif29170

[0332] 3-Oxetanecarboxylic acid (41 mg, 0.402 mmol), DCC (82.8 mg, 0.401 mmol), and DMAP (49.1 mg, 0.402 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 117 (100 mg, 0.267 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 120 (46.1 mg, yield 37.6%). ESI[M + H] + = 458.0.

[0333] 1H NMR (400 MHz, DMSO-d6) δ8.58 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.10-8.08 (m, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.56-7.48 (m, 3H), 4.65-4.61 (m, 2H), 4.53-4.48 (m, 2H), 4.39-4.25 (m, 2H), 3.87-3.81 (m, 1H), 3.8 0-3 .71 (m, 1H), 3.31 (s, 3H), 2.45-2.32 (m, 2H). Example 61 Preparation of Compounds 121-123 TIFF2026519809000136.tif29170

[0334] The preparation method for compounds 121-123 was the same as for compound 120 in Example 60, using compound 117 and the corresponding carboxylic acid as starting materials to obtain the corresponding esters.

[0335] Compound 121:80 .5mg,ESI[M+H] + = 442.0.

[0336] 1 H NMR (400 MHz, DMSO-d6) δ 8.61-8.56 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.96 (td, J=7.7, 1.8Hz, 1H), 7.82 (dd, J=8.8, 2.4Hz, 1H), 7.56-7.47 (m, 3H), 4.24 (t, J=6.8 Hz, 2H), 3.73 (dd, J=8.1, 5.5Hz, 1H), 3.31 (s, 3H), 2.45-2.28 (m, 2H), 1.58-1.51 (m, 1H), 0.85-0.76 (m, 2H), 0.75-0.65 (m, 2H) . Compound 122:22.7mg,ESI[M+H] + = 448.0.

[0337] 1 H NMR (400 MHz, DMSO-d6) δ 8.62-8.56 (m, 1H), 8.13-8.08 (m, 1H), 8.01-7.92 (m, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.54-7.51 (m, 2H), 7.49 (t, J=2.4 Hz, 1H), 5.23-5.03 (m, 1H), 4.40-4.33 (m, 2H), 3.82-3.72 (m, 1H), 3.31 (s, 3H), 2.47-2.34 (m, 2H), 1.40-1.30 (m, 3H) . Compound 123: 18.0 mg, ESI [M+H] + =484.0.

[0338] 1 H NMR (400 MHz, DMSO-d6) δ 8.62-8.55 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.55-7.50 (m, 2H), 7.48 (d, J=2.4 Hz, 1H), 4.37-4.33 (m, 2H), 3.78 (dd, J=8.3, 5.4 Hz, 1H), 3.62 (q, J=11.0 Hz, 2H), 3.31 (s, 3H), 2.45-2.33 (m, 2H) . Example 62 Preparation of Compound 124 TIFF2026519809000137.tif29170

[0339] - At 10°C, propionyl chloride (21 mg, 0.227 mmol) was added dropwise to a solution of 117 (56.7 mg, 0.152 mmol) and triethylamine (30.7 mg, 0.303 mmol) in dichloromethane (2 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (50 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain off-white solid compound 124 (37.3 mg, yield 57.2%). ESI[M + H] + = 430.0.

[0340] 1 H NMR (400 MHz, DMSO-d6) δ8.61-8.56 (m, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.81 (dd, J=8.9, 2.4Hz, 1H), 7.55-7.45 (m, 3H), 4.30-4.16 (m, 2H), 3.75 (dd, J=8.0, 5.7 Hz, 1H), 3.31 (s, 3H), 2.42-2.29 (m, 2H), 2.23 (q, J=7.5 Hz, 2H), 0.93 (t, J=7.5 Hz, 3H). Example 63 Preparation of Compounds 125-129 TIFF2026519809000138.tif28170

[0341] The preparation method for target compounds 125-129 was the same as for compound 124 in Example 62, using compound 117 and the corresponding acyl chloride as starting materials, and the corresponding esters were obtained by preparation.

[0342] Compound 125:49.1mg,ESI[M+H] + =444.1. 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.56-7.50 (m, 2H), 7.48 (d, J=2.4Hz, 1H), 4.34-4.16 (m, 2H), 3.73 (dd, J=8.2, 5.6 Hz, 1H), 3.31 (s, 3H), 2.45-2.31 (m, 3H), 0.95 (d, J=7.1 Hz, 3H), 0.93 (d, J = 7.1 Hz, 3H). Compound 126: 17.6 mg, ESI [M+H] + =484.0.

[0343] 1 H NMR (400 MHz, DMSO-d6) δ 8.59-8.58 (m, 1H), 8.12 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.54-7.52 (m, 2H), 7.46 (d, J=2.4 Hz, 1H), 6.81 (s, 1H), 4.58-4.41 (m, 2H), 3.81 (dd, J=8.4, 5.4 Hz, 1H), 3.31 (s, 3H), 2.48-2.32 (m, 2H) . Compound 127: 33.1 mg, ESI [M+H] + =450.0.

[0344] 1H NMR (400 MHz, DMSO-d6) δ 8.59 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.55-7.51 (m, 2H), 7.49 (d, J=2.4 Hz, 1H), 4.41-4.33 (m, 2H), 4.32 (s, 2H), 3.81 (dd, J=8.0, 5.6 Hz, 1H), 3.31 (s, 3H), 2.46-2.35 (m, 2H) . Compound 128: 21.4 mg, ESI [M+H] + =492.0.

[0345] 1 H NMR (400 MHz, DMSO-d6) δ 8.61-8.56 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.80 (dd, J=8.9, 2.4 Hz, 1H), 7.57-7.49 (m, 2H), 7.44 (d, J=2.4 Hz, 1H), 4.39-4.33 (m, 1H), 4.28- 4.22 (m, 1H), 3.79 (dd, J=8.3, 5.5 Hz, 1H), 3.54 (s, 2H), 3.31 (s, 3H), 2.46-2.29 (m, 2H), 1.07 (s, 3H), 1.06 (s, 3H). Compound 129: 24.5 mg, ESI [M+H] + =517.9.

[0346] 1H NMR (400 MHz, DMSO-d6) δ 8.61-8.57 (m, 1H), 8.14 (d, J=7.9 Hz, 1H), 7.98 (td, J=7.7, 1.8 Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.54-7.52 (m, 2H), 7.46 (d, J=2.4 Hz, 1H), 4.74-4.57 (m, 2H), 3.84 (dd, J=8.2, 5.4 Hz, 1H), 3.31 (s, 3H), 2.55-2.44 (m, 2H). Example 64 Preparation of Compound 130 TIFF2026519809000139.tif29170

[0347] At 0°C, 3-chloropropionyl chloride (26.0 mg, 0.205 mmol) was added dropwise to a solution of 117 (50 mg, 0.134 mmol) and triethylamine (27.0 mg, 0.267 mmol) in dichloromethane (2 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (5 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 130 (22.1 mg, yield 38.6%). ESI[M+H] + =428.0. 1H NMR (400 MHz, DMSO-d6) δ 8.61-8.57 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.81 (dd, J=8.9, 2.4 Hz, 1H), 7.55-7.50 (m, 2H), 7.49 (d, J=2.4 Hz, 1H), 6.26 (dd, J=17.3, 1.7Hz, 1H), 6.12 (dd, J=17.3, 10.2 Hz, 1H), 5.89 (dd, J=10.2, 1.7 Hz, 1H), 4.39-4.23 (m, 2H), 3.79 (dd, J=8.1, 5.5 Hz, 1H), 3.31 (s, 3H), 2.48-2.36 (m, 2H). Example 65 Preparation of Compound 131 TIFF2026519809000140.tif29170

[0348] At 0°C, ethyl chloroformate (87.3 mg, 0.804 mmol) was added dropwise to a solution of 117 (100 mg, 0.267 mmol), pyridine (61.9 mg, 0.783 mmol), and DMAP (32.7 mg, 0.268 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 131 (90.0 mg, yield 75.5%). EST[M+H] + = 446.0.

[0349] 1H NMR (400 MHz, DMSO-d6) δ8.58 (d, J=4.7 Hz, 1H), 8.11 (d, J=7.8 Hz, 1H), 7.97 (t, J=7.8 Hz, 1H), 7.82 (dd, J=8.9, 2.2 Hz, 1H), 7.57-7.46 (m, 3H), 4.31 (t, J=6.5 Hz, 2H), 4.05 (q, J=7.0 Hz, 2H), 3.75 (dd, J=8.2, 5.4 Hz, 1H), 3.31 (s, 3H), 2.44-2.27 (m, 2H), 1.14 (t, J=7.1 Hz, 3H). Example 66 Preparation of Compound 132 TIFF2026519809000141.tif29170

[0350] The method for preparing compound 132 was the same as for compound 131 in Example 65, using compound 117 and isopropyl chloroformate as raw materials and obtaining it by purification.

[0351] Compound 132:84.5 mg,ESI[M+H] + = 460.1.

[0352] 1 H NMR (400 MHz, DMSO-d6) δ 8.61-8.55 (m, 1H), 8.11 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.55-7.50 (m, 2H), 7.48 (d, J=2.4 Hz, 1H), 4.76-4.61 (m, 1H), 4.32- 4.29 (m, 2H), 3.73 (dd, J=8.3, 5.4 Hz, 1H), 3.31 (s, 3H), 2.45-2.24 (m, 2H), 1.15 (d, J=5.0 Hz, 3H), 1.14 (d, J=5.0 Hz, 3H). Example 67 Preparation of Compounds 133-135 TIFF2026519809000142.tif61170

[0353] 1. Preparation of Compound 133-1 At 0°C, 4-nitrophenyl chloroformate (810 mg, 4.02 mmol) was added to a solution of 117 (500 mg, 1.34 mmol), pyridine (310 mg, 3.92 mmol), and DMAP (163.5 mg, 1.34 mmol) in dichloromethane (5 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 133-1 (369.9 mg, yield 51.3%). ESI[M + H] + = 539.1.

[0354] 2. Preparation of target compound 133 Cyclopropanol (10.8 mg, 0.186 mmol) was added to a solution of 133-1 (100 mg, 0.185 mmol) and DMAP (22.6 mg, 0.185 mmol) in dichloromethane (2 mL), and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 133 (56.1 mg, yield 66.0%). ESI[M+H] + =458.0. 1H NMR (400 MHz, DMSO-d6) δ8.58 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.11 (d, J=7.9 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.56-7.50 (m, 2H), 7.49 (d, J=2.4 Hz, 1H), 4.32 (t, J= 6.6 Hz, 2H), 4.04-3.94 (m, 1H), 3.74 (dd, J=8.2, 5.4 Hz, 1H), 3.31 (s, 3H), 2.46-2.32 (m, 2H), 0.67-0.54 (m, 4H). 3. Preparation of target compound 134 The method for preparing compound 134 was the same as for compound 133 in Example 67, using compound 133-1 and oxetan-3-ol as raw materials and obtaining it by purification.

[0355] Compound 134:56.7mg,ESI[M+H] + = 474.0.

[0356] 1 H NMR (400 MHz, DMSO-d6) δ 8.58 (ddd, J=4.8, 1.7, 0.9 Hz, 1H), 8.14-8.09 (m, 1H), 7.97 (td, J= 7.7, 1.8 Hz, 1H), 7.82 (dd, J=8.9, 2.4 Hz, 1H), 7.56-7.48 (m, 3H), 5.34-5.24 (m, 1H), 4.76-4.67 (m, 2H), 4.50-4.39 (m, 2H), 4.36-4.32 (m, 2H), 3.77 (dd, J=8.2, 5.4 Hz, 1H), 3.31 (s, 3H), 2.44-2.34 (m, 2H). 4. Preparation of target compound 135 133-1 (100 mg, 0.185 mmol) and DIEA (24.0 mg, 0.186 mmol) were dissolved in dichloromethane (2 mL), dimethylamine (0.1 mL, 2 mol / L in THF, 0.2 mmol) was added, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 135 (54.5 mg, yield 66.0%). ESI[M + H] + = 445.0.

[0357] 1 H NMR (400 MHz, DMSO-d6) δ8.59-8.57 (m, 1H), 8.09 (dd, J=7.9, 1.0 Hz, 1H), 7.97 (td, J=7.7, 1.8 Hz, 1H), 7.81 (dd, J=8.8, 2.4 Hz, 1H), 7.55-7.48 (m, 3H), 4.21-4.12 (m, 2H), 3.76 (dd, J=7.8, 5.8 Hz, 1H), 3.30 (s, 3H), 2.74 (s, 3H), 2.70 (s, 3H), 2.40-2.32 (m, 2H) . Example 68 Preparation of Compounds 136 and 137 TIFF2026519809000143.tif27170

[0358] Isopropylsulfonyl chloride (268 mg, 1.88 mmol) was added to a solution of 117 (70.0 mg, 0.187 mmol), pyridine (72.3 mg, 0.914 mmol), and DMAP (137.4 mg, 1.12 mmol) in dichloromethane (2 mL), and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated saline, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20) and confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20) to obtain yellow solid compound 136 (7.6 mg, yield 8.5%) and off-white solid compound 137 (10.7 mg, yield 11.5%).

[0359] Compound 136:ESI[M + H] + = 480.1.

[0360] 1 H NMR (400 MHz, DMSO-d6) δ 8.61 (d, J=4.2Hz, 1H), 8.16 (d, J=7.9 Hz, 1H), 8.00 (td, J=7.8, 1.7 Hz, 1H), 7.84 (dd, J=8.9, 2.4 Hz, 1H), 7.59-7.52 (m, 2H), 7.48 (d, J=2.4 Hz, 1H), 4.59-4.39 (m, 2H), 3.82 (dd, J=8.6, 5.1 Hz, 1H), 3.55-3.49 (m, 1H), 3.34 (s, 3H), 2.51-2.36 (m, 2H), 1.22 (d, J=6.8 Hz, 3H), 1.19 (d, J=6.8 Hz, 3H). Compound 137:ESI[M + H] + = 498.0.

[0361] 1H NMR (400 MHz, DMSO-d6) δ 8.60 (d, J=4.6 Hz, 1H), 8.15 (d, J=7.9 Hz, 1H), 7.99 (t, J=7.7Hz, 1H), 7.82 (d, J=8.9Hz, 1H), 7.56-7.53 (m, 2H), 7.47 (dd, J=6.1, 2.2 Hz, 1H), 4.48-4.25 (m, 2H), 3.86- 3.83 (m, 1H), 3.33 (s, 3H), 2.50-2.34 (m, 2H), 1.58-1.51 (m, 6H). Example 69 Preparation of Compounds 138 and 140 TIFF2026519809000144.tif27170

[0362] 1. Preparation of target compound 138 At 0°C, methanesulfonyl chloride (62.9 mg, 0.549 mmol) was added dropwise to a solution of 117 (165 mg, 0.441 mmol) and triethylamine (106.8 mg, 1.06 mmol) in dichloromethane (2 mL), and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain yellow solid compound 138 (57.0 mg, yield 28.6%). ESI[M + H] + = 452.2.

[0363] 1 H NMR (400 MHz, DMSO-d6) δ8.61 (d, J=4.7Hz, 1H), 8.16 (d, J=7.9 Hz, 1H), 8.02-7.96 (m, 1H), 7.86-7.81 (m, 1H), 7.58-7.50 (m, 3H), 4.55-4.44 (m, 2H), 3.85-3.80 (m, 1H), 3.34 (s, 3H), 3.16 (s, 3H), 2.60-2.38 (m, 2H). 2. Preparation of target compound 140 N-phenyl-N-(4-piperidinyl)propanamide (43.5 mg, 0.187 mmol) was added to 138 (57 mg, 0.126 mmol) and DIEA (32.6 mg, 0.253 mmol) in dichloromethane (2 mL), and the mixture was stirred at room temperature for 48 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 140 (13.2 mg, yield 17.8%). ESI[M +H] + = 588.2.

[0364] 1 H NMR (400 MHz, DMSO-d6) δ8.56 (d, J=4.1 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.96-7.93 (m, 1H), 7.78 (dd, J=8.9, 2.4 Hz, 1H), 7.54-7.49 (m, 1H), 7.46-7.43 (m, 5H), 7.20-7.16 (m, 2H), 4.49-4.47 (m, 1H), 3.64-3.60 (m, 1H), 3.25 (s, 3H), 3.12-2.73 (m, 2H), 2.44-2.34 (m, 2H), 2.30-1.90 (m, 4H), 1.82-1.80 (m, 2H), 1.75-1.60 (m, 2H), 1.23-1.01 (m, 2H), 0.87 (t, J=7.4 Hz, 3H). Example 70 Preparation of compounds 144, 145, and 145D TIFF2026519809000145.tif44170

[0365] 1. Preparation of Compound 145-1 At -30°C, lithium bis(trimethylsilyl)amide (9.08 mL, 1 mol / L, 9.08 mmol) was slowly added to a solution of 116-3 (3.4 g, 7.55 mmol) in THF (40 mL) and stirred for 1 hour. Dimorpholinyl phosphinochloride (4.54 g, 17.8 mmol) was added in small amounts, and the mixture was stirred at -10°C for 4 hours. Isopropanolamine (2.56 g, 34.1 mmol) was added dropwise to the reaction system, allowed to rise naturally to room temperature, and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (40 mL) was added to the reaction system and extracted with ethyl acetate (3 × 40 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 145-1 (3.254 g, yield 84.9%). ESI[M + H] + = 507.1.

[0366] 2. Preparation of target compound 144 Dess-Martin reagent (6.817 g, 16.1 mmol) was added to 145-1 (3.254 g, 6.41 mmol) in acetone (40 mL) and stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (50 mL), washed with saturated sodium bicarbonate solution, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 144 (2.312 g, yield 74.0%). ESI[M +H] + =487.1. 1H NMR (400 MHz, DMSO-d6) δ 8.54-8.53 (m, 1H), 7.96 (d, J=7.7Hz, 1H), 7.94-7.86 (m, 2H), 7.66 (d, J=8.7Hz, 1H), 7.58 (d, J=2.3 Hz, 1H), 7.52-7.42 (m, 1H), 7.29-7.19 (m, 5H), 6.80 (d, J=1.1Hz, 1H), 4.48 (d, J=12.3 Hz, 1H), 4.41 (d, J=12.3Hz, 1H), 4.10 (t, J=7.1Hz, 1H), 3.82-3.69 (m, 2H), 2.59-2.54 (m, 2H), 2.29 (d, J=0.8Hz, 3H). 3. Preparation of Compound 145-2 At 0°C, aluminum chloride (6.326 g, 47.4 mmol) was slowly added to a solution of 144 (2.312 g, 4.74 mmol) in dichloromethane (50 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 60 mL). The organic phase was washed with 5% sodium bicarbonate aqueous solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 145-2 (1.7 g, yield 90.2%). ESI[M + H] + = 397.1.

[0367] 4. Preparation of target compound 145 At -10°C, acetyl chloride (55.1 mg, 0.702 mmol) was added dropwise to a solution of 145-2 (300 mg, 0.755 mmol) and triethylamine (153 mg, 1.512 mmol) in dichloromethane (3 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4~0.5 was recovered to obtain the white solid compound 145 (248 mg, yield 74.8%). ESI[M+H] + = 439.1.

[0368] 1 H NMR (400 MHz, DMSO-d6) δ8.54 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7Hz, 1H), 7.62 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.35-4.31 (m, 2H), 4.12 (t, J=7.0 Hz, 1H), 2.65- 2.59 (m, 2H), 2.30 (d, J=0.8 Hz, 3H), 1.97 (s, 3H). 5. Preparation of target compound 145D Compound 145 (248 mg, 0.565 mmol) was dissolved in ethyl acetate (20 mL), and a solution of benzenesulfonic acid (89.6 mg, 0.566 mmol) in ethyl acetate (1 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain the white solid compound 145D (281.2 mg, yield 83.4%). ESI[M + H]+ = 439.1.

[0369] 1 H NMR (400 MHz, CD3OD) δ 9.42 (d, J=4.6 Hz, 1H), 8.95 (d, J=7.9 Hz, 1H), 8.84 (ddd, J=9.3, 8.3, 1.8 Hz, 2H), 8.70 (d, J=8.7Hz, 1H), 8.61 (d, J=2.2 Hz, 1H), 8.47-8.33 (m, 4H), 8.18-8.10 (m, 3H), 5.28 -5.21 (m, 2H), 5.17-5.10 (m, 1H), 3.63-3.39 (m, 2H), 3.23 (s, 3H), 2.81 (s, 3H). Example 71 Preparation of compounds 146-149 TIFF2026519809000146.tif29170

[0370] The preparation method for compounds 146-149 was the same as for compound 145 in Example 70, using compound 145-2 and the corresponding asyl chloride as starting materials, and obtaining them by purification.

[0371] Compound 146:38.8 mg,ESI[M+H] + =467.1 11H NMR (400 MHz, DMSO-d6) δ 8.54 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.08 (d, J=7.9Hz, 1H), 7.95 (td, J=7.7, 1.8 Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.60 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.44-4.33 (m, 2H), 4.09 (dd, J=8.2, 5.9Hz, 1H), 2.72-2.52 (m, 2H), 2.49-2.43 (m, 1H), 2.30 (d, J=0.8 Hz, 3H), 1.00 (d, J=4.4Hz, 3H), 0.98 (d, J=4.4 Hz, 3H). Compound 147: 51.7 mg, ESI [M+H] + = 453.1 1 1H NMR (400 MHz, DMSO-d6) δ 8.56-8.51 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.47-4.28 (m, 2H), 4.11 (t, J=7.0Hz, 1H), 2.65-2.59 (m, 2H), 2.30 (d, J=0.8 Hz, 3H), 2.29-2.24 (m, 2H), 0.96 (t, J=7.5 Hz, 3H). Compound 148: 90.1 mg, ESI [M+H] + = 473.0 1H NMR (400 MHz, DMSO-d6) δ 8.58-8.50 (m, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.8, 1.7Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.82 (d, J=1.0 Hz, 1H), 4.56-4.44 (m, 2H), 4.35 (s, 2H), 4.16 (t, J=7.0 Hz, 1H), 2.69-2.62 (m, 2H), 2.30 (d, J=0.7 Hz, 3H). Compound 149: 101.7 mg, ESI [M+H] + =515.4 1 H NMR (400 MHz, DMSO-d6) δ 8.56 (d, J=4.2Hz, 1H), 8.10 (d, J=7.9Hz, 1H), 7.97 (td, J=7.8, 1.6 Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.57 (d, J=2.3 Hz, 1H), 7.51 (dd, J=6.9, 5.3 Hz, 1H), 6.84 (s, 1H), 4.55-4.48 (m, 1H), 4.47-4.33 (m, 1H), 4.17 (dd, J=8.5, 5.7 Hz, 1H), 3.60 (s, 2H), 2.73-2.60 (m, 2H), 2.32 (s, 3H), 1.13 (s, 6H). Example 72 Preparation of compound 150 and 151 TIFF2026519809000147.tif26170

[0372] At 0°C, 58.7 mg, 0.462 mmol of 3-chloropropionyl chloride was added dropwise to a solution of 145-2 (100 mg, 0.252 mmol) and triethylamine (51 mg, 0.504 mmol) in 2 mL of dichloromethane, and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, 10 mL of ice water was added to the reaction system, and the mixture was extracted with 3 × 10 mL of dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20) and confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10) to obtain white solid compound 150 (21.1 mg, yield 17.2%) and white solid compound 151 (19.0 mg, yield 16.7%).

[0373] Compound 150:ESI[M+H] + = 487.0.

[0374] 1 H NMR (400 MHz, DMSO-d6) δ 8.58-8.51 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H), 7.58 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.52-4.38 (m, 2H), 4.19-4.11 (m, 1H), 3.71 (t, J=6.1 Hz, 2H), 2.77 (t, J=6.1 Hz, 2H), 2.71-2.59 (m, 2H), 2.30 (d, J=0.7Hz, 3H). Compound 151: ESI[M+H] + = 451.1.

[0375] 1H NMR (400 MHz, DMSO-d6) δ 8.54 (d, J=3.9Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.7 Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (dd, J=6.4, 4.9Hz, 1H), 6.82 (d, J=1.0Hz, 1H), 6.29 (dd, J=17.3, 1.6Hz, 1H), 6.15 (dd, J=17.3, 10.2 Hz, 1H), 5.90 (dd, J =10.2, 1.7Hz, 1H), 4.49-4.44 (m, 2H), 4.21-4.10 (m, 1H), 2.73-2.60 (m, 2H), 2.30 (s, 3H). Example 73 Preparation of Compound 152 TIFF2026519809000148.tif29170

[0376] Benzoic acid (46.2 mg, 0.378 mmol), DCC (78 mg, 0.378 mmol), and DMAP (61.6 mg, 0.504 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 145-2 (100 mg, 0.252 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 152 (58.8 mg, yield 46.6%). ESI[M +H] + = 501.1.

[0377] 1H NMR (400 MHz, DMSO-d6) δ8.56-8.51 (m, 1H), 8.07 (d, J=7.9 Hz, 1H), 7.92-7.90 (m, 3H), 7.89-7.86 (m, 1H), 7.68-7.60 (m, 2H), 7.58 (d, J=2.3 Hz, 1H), 7.51-7.45 (m, 3H), 6.83 (d, J=1.1 Hz, 1H), 4.64 (t, J=6.8 Hz, 2H), 4.24 (dd, J=8.2, 5.7 Hz, 1H), 2.85-2.73 (m, 2H), 2.31 (d, J=0.7Hz, 3H). Example 74 Preparation of Compound 153 TIFF2026519809000149.tif29170

[0378] The preparation method for compound 153 was the same as for compound 152 in Example 73, using compound 145-2 and 3-oxetanecarboxylic acid as starting materials and obtaining it by purification.

[0379] Compound 153:17.6 mg,ESI[M+H] + =481.1 1 H NMR (400 MHz, DMSO-d6) δ8.58-8.53 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.65 (dd, J=8.7, 5.9Hz, 2H), 4.54 (dd, J=12.1, 5.8 Hz, 2H), 4.50- 4.40 (m, 2H), 4.13 (t, J=7.0 Hz, 1H), 3.9 0-3 .82 (m, 1H), 2.68-2.62 (m, 2H), 2.30 (d, J=0.8 Hz, 3H). Example 75 Preparation of Compound 154 TIFF2026519809000150.tif31170

[0380] At 0°C, ethyl chloroformate (66 mg, 0.608 mmol) was added dropwise to a solution of 145-2 (80 mg, 0.201 mmol), pyridine (47 mg, 0.594 mmol), and DMAP (25 mg, 0.205 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 154 (42.3 mg, yield 44.8%). ESI[M + H] + = 469.1.

[0381] 1 H NMR (400 MHz, DMSO-d6) δ8.54 (ddd, J=4.8, 1.6, 0.8Hz, 1H), 8.09 (d, J=7.9Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.91-7.87 (m, 1H), 7.68-7.64 (m, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.44 (t, J=6.6 Hz, 2H), 4.15-4.00 (m, 3H), 2.72-2.57 (m, 2H), 2.30 (d, J=0.8 Hz, 3H), 1.16 (t, J=7.1 Hz, 3H). Example 76 Preparation of Compound 155 TIFF2026519809000151.tif31170

[0382] The preparation method for compound 155 was the same as for compound 154 in Example 75, using compound 145-2 and isopropyl chloroformate as raw materials and obtaining it by purification.

[0383] Compound 155:45.7 mg,ESI[M+H] + =483.1 1 H NMR (400 MHz, DMSO-d6) δ 8.57-8.51 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.89 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.60 (d, J=2.3 Hz, 1H), 7.50 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.80-4.66 (m, 1H), 4.43 (t, J=6.6Hz, 2H), 4.09 (dd, J=8.1, 6.0 Hz, 1H), 2.69-2.59 (m, 2H), 2.30 (d, J=0.8 Hz, 3H), 1.18 (d, J=2.7Hz, 3H), 1.16 (d, J=2.7 Hz, 3H). Example 77 Preparation of compounds 156, 156D, 157, 158, 159 and 159D TIFF2026519809000152.tif77170

[0384] 1. Preparation of Compound 156-1 At 0°C, 4-nitrophenyl chloroformate (487 mg, 2.42 mmol) was added to a solution of 145-2 (320 mg, 0.805 mmol), pyridine (186.2 mg, 2.35 mmol), and DMAP (98 mg, 0.802 mmol) in dichloromethane (5 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 156-1 (404 mg, yield 89.2%). ESI[M + H] + = 562.1.

[0385] 2. Preparation of target compound 156 156-1 (200 mg, 0.356 mmol) and DIEA (46.0 mg, 0.356 mmol) were dissolved in dichloromethane (2 mL), dimethylamine (0.356 mL, 2 mol / L in THF, 0.712 mmol) was added, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 156 (144.7 mg, yield 86.9%). ESI[M + H] + = 468.1.

[0386] 1H NMR (400 MHz, DMSO-d6) δ8.54 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.88 (dd, J=8.7, 2.3Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.62 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.81 (d, J=1.1 Hz, 1H), 4.39-4.25 (m, 2H), 4.11 (dd, J=7.9, 6.1 Hz, 1H), 2.76 (s, 3H), 2.75 (s, 3H), 2.69-2.56 (m, 2H), 2.30 (d, J=0.8 Hz, 3H). 3. Preparation of target compound 156D Compound 156 (144.7 mg, 0.309 mmol) was dissolved in ethyl acetate (10 mL), and a solution of benzenesulfonic acid (49.0 mg, 0.31 mmol) in ethyl acetate (0.5 mL) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction system was filtered, and the filter cake was dried under reduced pressure to obtain the white solid compound 156 D (117.4 mg, yield 60.7%). ESI[M + H] + = 468.1.

[0387] 1 H NMR (400 MHz, DMSO-d6) δ8.60 (d, J=4.1 Hz, 1H), 8.13 (d, J=7.9 Hz, 1H), 8.06-7.95 (m, 2H), 7.86 (d, J=8.7 Hz, 1H), 7.78 (d, J=1.3Hz, 1H), 7.63-7.59 (m, 2H), 7.57 (dd, J=6.6, 5.0 Hz, 1H), 7.46 (s, 1H), 7.36-7.24 (m, 3H), 4.45-4.34 (m, 2H), 4.32-4.23 (m, 1H), 2.79 (s, 3H), 2.77 (s, 3H), 2.74-2.59 (m, 2H), 241 (s, 3H). 4. Preparation of target compound 157 The preparation method for compound 157 was the same as for compound 156 in Example 77, using compound 156-1 and N-ethylmethylamine as starting materials and obtaining it by purification.

[0388] Compound 157:45.5mg,ESI[M+H] + = 482.1.

[0389] 1 H NMR (400 MHz, DMSO-d6) δ8.57-8.51 (m, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.81 (d, J=1.1 Hz, 1H), 4.32 (t, J=6.4Hz, 2H), 4.10 (dd, J=8.0, 6.0Hz, 1H), 3.15-3.10 (m, 2H), 2.73 (s, 3H), 2.68-2.54 (m, 2H), 2.30 (d, J=0.8 Hz, 3H), 0.95-0.82 (m, 3H). 5. Preparation of target compound 158 The preparation method for compound 158 was the same as for compound 156 in Example 77, using compound 156-1 and N-isopropylmethylamine as starting materials and obtaining it by purification.

[0390] Compound 158:44.6 mg,ESI[M+H] + =496.1. 1H NMR (400 MHz, DMSO-d6) δ 8.57-8.53 (m, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.60 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.81 (d, J=1.1 Hz, 1H), 4.33 (t, J=6.6 Hz, 2H), 4.27-3.94 (m, 2H), 2.68-2.60 (m, 2H), 2.59 (s, 3H), 2.30 (d, J=0.8 Hz, 3H), 0.96-0.91 (m, 6H). 6. Preparation of target compounds 159 and 159D The preparation methods for compounds 159 and 159D were the same as those for compounds 156 and 156D in Example 77, respectively. Compound 156-1 and dimethylhydroxylamine were used as starting materials, and 159 was purified to obtain compound 159. This compound was then reacted with benzenesulfonic acid and purified to obtain compound 159D.

[0391] Compound 159:144.7 mg,ESI[M+H] + =484.1 1 H NMR (400 MHz, DMSO-d6) δ8.59-8.51 (m, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.95 (td, J=7.7, 1.8Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.62 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.82 (d, J=1.1 Hz, 1H), 4.49-4.34 (m, 2H), 4.13 (dd, J=8.1, 5.9 Hz, 1H), 3.47 (s, 3H), 3.01 (s, 3H), 2.71-2.60 (m, 2H), 2.30 (d, J=0.7 Hz, 3H). Compound 159D:63.3 mg,ESI[M+H] + =484.1 1 H NMR (400 MHz, DMSO-d6) δ 8.59-8.58 (m, 1H), 8.15 (d, J=7.6 Hz, 1H), 8.01-7.98 (m, 2H), 7.79-7.74 (m, 2H), 7.64-7.59 (m, 2H), 7.57-7.52 (m, 1H), 7.37-7.23 (m, 4H), 4.46-4.41 (m, 3H), 3.50 (s, 3H), 3.03 (s, 3H), 2.79-2.62 (m, 2H), 2.38-2.35 (m, 3H). Example 78 Preparation of Compound 160 TIFF2026519809000153.tif49170

[0392] 1. Preparation of Compound 160-1 1-1 (2.341 g, 8.45 mmol) and BOC-glycine (2.23 g, 12.7 mmol) were dissolved in dichloromethane (30 mL), and a solution of DCC (2.62 g, 12.7 mmol) in dichloromethane (10 mL) was added dropwise at -10°C. The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (40 mL) was added to the reaction system and stirred for 5 minutes. The reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 160-1 (2.5 g, yield 68.1%). ESI[M+H] + = 434.1.

[0393] 2. Preparation of Compound 160-2 At 0°C, 10 mL of trifluoroacetic acid was added to a solution of 160-1 (2.5 g, 5.76 mmol) of dichloromethane (30 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was used directly in the next step of the reaction without purification.

[0394] 3. Preparation of Compound 160-3 The crude product from the previous step was dissolved in acetonitrile (30 mL), sodium bicarbonate (18.9 g, 225 mmol) was added, and the mixture was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 160-3 (672 mg, 2-step yield 36.9%). ESI[M + H] + = 316.0.

[0395] 4. Preparation of Compound 160-4 - At -20°C, NaH (110.6 mg, 60%, 2.76 mmol) was slowly added to 160-3 (672 mg, 2.13 mmol) in a 6 mL solution of dry DMF, and the mixture was stirred for 30 minutes. Iodomethane (392.6 mg, 2.77 mmol) was added to the reaction system, and the mixture was stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into 20 mL of ice water and extracted with ethyl acetate (3 × 20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 160-4 (450 mg, yield 64.1%). ESI[M + H] + = 330.1.

[0396] 5. Preparation of Compound 160-5 At -60°C, LDA (0.926 mL, 2 mol / L in THF, 1.85 mmol) was slowly added dropwise to 160-4 (450 mg, 1.36 mmol) in a solution of dry tetrahydrofuran (8 mL), and the mixture was stirred for 15 minutes. Acetaldehyde (0.85 mL, 5 mol / L in THF, 4.25 mmol) was added to the reaction system, and the mixture was stirred for a further 1 hour at -60°C. After confirming the completion of the reaction by TLC, saturated ammonium chloride aqueous solution (10 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (CH₂Cl₂ / MTBE / MeOH / Et₃N = 50 / 50 / 2.5 / 0.5) to obtain the white solid compound 160-5 (180 mg, yield 35.3%). ESI[M + H] + = 374.1.

[0397] 6. Preparation of target compound 160 2-Fluoropropionic acid (18.5 mg, 0.201 mmol), DCC (41.4 mg, 0.201 mmol), and DMAP (32.7 mg, 0.268 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 160-5 (50 mg, 0.134 mmol) was added to the reaction system and stirred for a further 12 hours at room temperature. After confirming the completion of the reaction by TLC, methyl tert-butyl ether (2 mL) was added to the reaction system and stirred for 5 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain the white solid compound 160 (9.9 mg, yield 16.5%). ESI[M + H] + = 448.1.

[0398] 1H NMR (400MHz, DMSO-d6) δ8.62 (d, J=4.6 Hz, 1H), 8.15 (d, J=7.7Hz, 1H), 8.01 (t, J=7.7Hz, 1H), 7.86 (dd, J=8.8, 2.2 Hz, 1H), 7.61 (d, J=8.9Hz, 1H), 7.58-7.55 (m, 2H), 5.8 0-5 .64 (m, 1H), 5.22- 5.08 (m, 1H), 3.83 (t, J=8.8Hz, 1H), 3.33 (s, 3H), 1.48-1.28 (m, 6H). Example 79 Preparation of Compound 162 TIFF2026519809000154.tif24170

[0399] 1. Preparation of compound 162-1 At 0°C, 4-nitrophenyl chloroformate (80.8 mg, 0.401 mmol) was added to a solution of 160-5 (50 mg, 0.134 mmol), pyridine (31 mg, 0.392 mmol), and DMAP (32.7 mg, 0.268 mmol) in dichloromethane (2 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 2), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 2), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 162-1 (60 mg, yield 83.3%). ESI[M+H] + =539.1. 2. Preparation of target compound 162 162-1 (60 mg, 0.111 mmol) and DIEA (14.4 mg, 0.111 mmol) were dissolved in dichloromethane (2 mL), dimethylamine (0.17 mL, 2 mol / L in THF, 0.34 mmol) was added, and the mixture was stirred at room temperature for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 162 (16.9 mg, yield 34.1%). ESI[M +H] + = 445.1.

[0400] 1 H NMR (400 MHz, DMSO-d6) δ8.61 (d, J=4.4 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.00 (td, J=7.7, 1.5Hz, 1H), 7.85 (dd, J=8.8, 2.3 Hz, 1H), 7.59 (d, J=8.9 Hz, 1H), 7.58-7.53 (m, 2H), 5.49-5.43 (m, 1H), 3.76 (d, J=7.6 Hz, 1H), 3.33 (s, 3H), 2.81 (s, 3H), 2.76 (s, 3H), 1.44 (d, J=6.3 Hz, 3H). Example 80 Preparation of compounds 164 and 165 TIFF2026519809000155.tif44170

[0401] 1. Preparation of Compound 165-1 160-3 (1.616 g, 5.11 mmol) was dissolved in acetic acid (20 mL), potassium acetate (1.004 g, 10.23 mmol), iodine (1.303 g, 5.13 mmol), and manganese dioxide (1.454 g, 16.7 mmol) were added, and the mixture was stirred at 80°C for 2 hours. After confirming the completion of the reaction by TLC, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (30 mL). The organic phase was washed with 10% aqueous sodium thiosulfate solution, washed with saturated brine, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 10 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.2 to 0.3 was recovered to obtain white solid compound 165-1 (1.03 g, yield 53.9%). ESI[M + H] + = 374.1.

[0402] 2. Preparation of target compound 164 At -20°C, NaH (141 mg, 60%, 3.52 mmol) was slowly added to 165-1 (1.013 g, 2.71 mmol) in dry DMF (10 mL) solution and stirred for 30 minutes. Iodomethane (385 mg, 2.71 mmol) was added to the reaction system and stirred for a further 1 hour at -20°C. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (30 mL) and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 100 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain off-white solid compound 164 (550 mg, yield 52.3%). ESI[M+H] + =388.0. 1H NMR (400 MHz, DMSO-d6) δ8.64 (d, J=4.0 Hz, 1H), 8.13 (d, J=7.9 Hz, 1H), 8.02 (td, J=7.8, 1.7 Hz, 1H), 7.90 (dd, J=8.9, 2.4 Hz, 1H), 7.65 (d, J=8.9Hz, 1H), 7.61-7.55 (m, 2H), 5.93 (s, 1H), 3.37 (s, 3H), 2.23 (s, 3H). 3. Preparation of Compound 165-2 At 5°C, a solution of sodium hydroxide (102.3 mg, 2.56 mmol) in water (5 mL) was added to a solution of 164 (450 mg, 1.16 mmol) in ethanol (10 mL), and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, the reaction mixture was concentrated under reduced pressure. The remaining solution was dissolved in ethyl acetate (20 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 20), and the portion with Rf = 0.3~0.4 was recovered to obtain the white solid compound 165-2 (350 mg, yield 87.2%). ESI[M + H] + = 346.1.

[0403] 4. Preparation of target compound 165 At 0°C, 4-nitrophenyl chloroformate (175 mg, 0.868 mmol) was added to a solution of 165-2 (100 mg, 0.289 mmol), pyridine (67 mg, 0.847 mmol), and DMAP (35.5 mg, 0.291 mmol) in dichloromethane (3 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, dimethylamine (0.87 mL, 2 mol / L in THF, 1.74 mmol) and DIEA (37 mg, 0.286 mmol) were added to the reaction system, and the mixture was stirred for a further 2 hours at room temperature. After confirming the completion of the reaction by TLC, water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain off-white solid compound 165 (2.5 mg, yield 2.1%). ESI[M+H] + = 417.1.

[0404] 1 H NMR (400 MHz, DMSO-d6) δ8.63 (d, J=4.6 Hz, 1H), 8.11 (d, J=7.9Hz, 1H), 8.00 (td, J=7.7, 1.6Hz, 1H), 7.89 (dd, J=8.9, 2.4 Hz, 1H), 7.62 (d, J=8.9Hz, 1H), 7.59-7.56 (m, 2H), 5.84 (s, 1H), 3.35 (s, 3H), 3.09 (s, 3H), 2.86 (s, 3H). Example 81 Preparation of Compound 166 TIFF2026519809000156.tif29170

[0405] At 0°C, isopropyl chloroformate (52.3 mg, 0.427 mmol) was added dropwise to a solution of 165-2 (80 mg, 0.231 mmol) and DIEA (94.1 mg, 0.728 mmol) in dichloromethane (2 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain pale yellow solid compound 166 (21.4 mg, yield 21.4%). ESI[M + H] + = 432.1.

[0406] 1 H NMR (400 MHz, DMSO-d6) δ8.51 (d, J=4.7Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.84-7.79 (m, 2H), 7.54 (d, J=8.6 Hz, 1H), 7.41-7.30 (m, 1H), 7.17 (d, J=8.0Hz, 1H), 6.89 (s, 1H), 5.11-5.05 (m, 1H), 2.80 (s, 3H), 1.36 (d, J=6.2Hz, 3H), 1.32 (d, J=6.2 Hz, 3H). Example 82 Preparation of Compound 167 TIFF2026519809000157.tif29170

[0407] At 0°C, isobutyryl chloride (32.3 mg, 0.303 mmol) was added dropwise to a solution of 165-2 (70 mg, 0.202 mmol) and triethylamine (41 mg, 0.405 mmol) in dichloromethane (2 mL), and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 167 (42.7 mg, yield 50.7%). ESI[M + H] + = 416.1.

[0408] 1 H NMR (400 MHz, DMSO-d6) δ8.49 (d, J=4.3 Hz, 1H), 8.01 (d, J=2.2 Hz, 1H), 7.85-7.76 (m, 2H), 7.55 (d, J=8.6 Hz, 1H), 7.38-7.31 (m, 1H), 7.16-7.08 (m, 2H), 3.58-3.51 (m, 1H), 2.83 (s, 3H), 1.26 (d, J =6.8 Hz, 3H), 1.16 (d, J=6.7 Hz, 3H). Example 83 Preparation of Compounds 169-172 TIFF2026519809000158.tif72170

[0409] 1. Preparation of Compound 169-1 At 0°C, sodium borohydride (1.3 g, 34.4 mmol) was added in small amounts to 1-5 (1.0 g, 2.28 mmol) methanol (15 mL) solutions and stirred for 8 hours. After confirming the completion of the reaction by TLC, ice water (30 mL) was added to the reaction system and extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain white solid compound 169-1 (266 mg, yield 28.4%). ESI[M + H] + = 411.1.

[0410] 2. Preparation of target compound 169 At 0°C, propionyl chloride (20.2 mg, 0.218 mmol) was added dropwise to a solution of 169-1 (60 mg, 0.146 mmol) and triethylamine (30 mg, 0.296 mmol) in dichloromethane (2 mL), and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4~0.5 was recovered to obtain the white solid compound 169 (29.6 mg, yield 43.4%). ESI[M + H] + = 467.1.

[0411] 1H NMR (400 MHz, DMSO-d6) δ8.54 (ddd, J=4.8, 1.7, 0.9Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8 Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.80 (d, J=1.1 Hz, 1H), 4.19-4.09 (m, 2H), 4.02 (dd, J=8.2, 6.0 Hz, 1H), 2.42-2.32 (m, 2H), 2.31-2.24 (m, 5H), 2.03-1.90 (m, 1H), 1.88-1.80 (m, 1H), 1.00 (t, J=7.5Hz, 3H). 3. Preparation of Compound 170 The method for preparing target compound 170 was the same as for compound 169 in Example 83, using compound 169-1 and isobutyryl chloride as starting materials and purifying them to obtain the compound.

[0412] Compound 170:37.3mg,ESI[M+H] + =481.1. 1H NMR (400 MHz, DMSO-d6) δ 8.57-8.51 (m, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.94 (td, J=7.7, 1.8Hz, 1H), 7.87 (dd, J=8.7, 2.3 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.2 Hz, 1H), 6.80 (d, J=1.1 Hz, 1H), 4.13 (t, J=6.5 Hz, 2H), 4.02 (dd, J=8.0, 6.1 Hz, 1H), 2.48-2.43 (m, 1H), 2.42-2.31 (m, 2H), 2.29 (d, J=0.8 Hz, 3H), 1.94-1.91 (m, 1H), 1.89-1.80 (m, 1H), 1.06 (d, J=1.2Hz, 3H), 1.04 (d, J=1.2 Hz, 3H). 4. Preparation of Compound 171-1 At 0°C, 4-nitrophenyl chloroformate (215 mg, 1.07 mmol) was added to a solution of 169-1 (146 mg, 0.355 mmol), pyridine (55 mg, 0.695 mmol), and DMAP (87 mg, 0.712 mmol) in dichloromethane (5 mL). The mixture was allowed to rise naturally to room temperature and stirred for 12 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether (v / v) = 1 / 20 to 1 / 1), confirmed by TLC (ethyl acetate / petroleum ether (v / v) = 1 / 1), and the portion with Rf = 0.3 to 0.4 was recovered to obtain white solid compound 171-1 (120 mg, yield 58.6%). ESI[M +H] + = 576.1.

[0413] 5. Preparation of target compound 171 171-1 (60 mg, 0.104 mmol) and DIEA (13 mg, 0.101 mmol) were dissolved in dichloromethane (2 mL), dimethylamine (0.1 mL, 2 mol / L in THF, 0.2 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system and extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 171 (13.7 mg, yield 27.3%). ESI[M + H] + = 482.1.

[0414] 1 H NMR (400 MHz, DMSO-d6) δ8.54 (d, J=4.0 Hz, 1H), 8.08 (d, J=8.0Hz, 1H), 7.94 (td, J=7.7, 1.7 Hz, 1H), 7.87 (dd, J=8.7, 2.3 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H), 7.60 (d, J=2.3 Hz, 1H), 7.49 (dd, J=6.4, 4.8 Hz, 1H), 6.80 (d, J=1.0Hz, 1H), 4.10-4.07 (m, 2H), 4.04-3.98 (m, 1H), 2.78 (s, 6H), 2.41-2.32 (m, 2H), 2.30 (s, 3H), 1.98-1.79 (m, 2H). 6. Preparation of target compound 172 The method for preparing target compound 172 was the same as for compound 171 in Example 83, using compound 171-1 and N-isopropylmethylamine as starting materials and obtaining it by purification.

[0415] Compound 172:22.9 mg,ESI[M+H] + = 510.2.

[0416] 1 H NMR (400 MHz, DMSO-d6) δ 8.54 (d, J=4.0 Hz, 1H), 8.08 (d, J=7.9Hz, 1H), 7.94 (td, J=7.7, 1.7 Hz, 1H), 7.88 (dd, J=8.7, 2.3Hz, 1H), 7.65 (d, J=8.7Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.49 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 6.81 (s, 1H), 4.22 (s, 1H), 4.10-4.08 (m, 2H), 4.05-3.98 (m, 1H), 2.64 (s, 3H), 2.40-2.33 (m, 2H), 2.30 (s, 3H), 1.99-1.89 (m, 1H), 1.85-1.81 (m, 1H), 1.03 (d, J=6.7Hz, 6H). Example 84 Preparation of Compounds 173 and 174 TIFF2026519809000159.tif49170

[0417] 1. Preparation of Compound 174-1 At -30°C, lithium bis(trimethylsilyl)amide (8.3 mL, 1 mol / L, 8.3 mmol) was slowly added dropwise to 88-4 (3.0 g, 6.88 mmol) tetrahydrofuran (30 mL) and the mixture was stirred for 1 hour. Dimorpholinyl phosphinochloride (4.14 g, 16.3 mmol) was added in small amounts, and the mixture was stirred at -10°C for 4 hours. After confirming the completion of the reaction by TLC, ice water (40 mL) was added to the reaction system and extracted with ethyl acetate (3 × 40 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was used directly in the next step without purification.

[0418] 2. Preparation of target compound 173 The crude product from the previous step was dissolved in dioxane (30 mL), acethydrazide (2.7 g, 36.4 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Then, it was heated to 100°C and stirred for a further 5 hours. The reaction mixture was poured into ice water (40 mL) and extracted with ethyl acetate (3 × 40 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3~0.4 was recovered to obtain pale yellow solid compound 173 (1.395 g, 2-step yield 42.8%). ESI[M + H] + = 474.1.

[0419] 1 H NMR (400 MHz, DMSO-d6) δ8.56 (d, J=4.3 Hz, 1H), 8.10 (d, J=7.8 Hz, 1H), 8.00-7.96 (m, 2H), 7.79 (d, J=8.8 Hz, 1H), 7.68 (d, J=2.1 Hz, 1H), 7.57-7.48 (m, 1H), 7.45-7.35 (m, 4H), 7.32-7.29 (m, 1H), 4.72 (s, 2H), 4.52-4.43 (m, 2H), 4.41-4.36 (m, 1H), 2.55 (s, 3H). 3. Preparation of Compound 174-2 At 0°C, aluminum chloride (3.79 g, 28.4 mmol) was slowly added to a solution of 173 (1.345 g, 2.84 mmol) in dichloromethane (30 mL), and the mixture was allowed to rise naturally to room temperature and stirred for 3 hours. After confirming the completion of the reaction by TLC, the reaction mixture was poured into ice water (50 mL), filtered by suction, and the filtrate was extracted with dichloromethane (3 × 60 mL). The organic phase was washed with 5% aqueous sodium bicarbonate solution, washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100 to 1 / 10), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.3 to 0.4 was recovered to obtain the white solid compound 174-2 (650 mg, yield 59.7%). ESI[M + H] + = 384.1.

[0420] 4. Preparation of target compound 174 At -10°C, isobutyryl chloride (22.1 mg, 0.207 mmol) was added dropwise to a solution of 174-2 (80 mg, 0.208 mmol) and triethylamine (52.7 mg, 0.521 mmol) in dichloromethane (3 mL), and the mixture was stirred for 2 hours. After confirming the completion of the reaction by TLC, ice water (10 mL) was added to the reaction system, and the mixture was extracted with dichloromethane (3 × 10 mL). The organic phase was washed with saturated brine, dried over anhydrous Na₂SO₄, filtered by suction, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (methanol / dichloromethane (v / v) = 1 / 100~1 / 20), confirmed by TLC (methanol / dichloromethane (v / v) = 1 / 10), and the portion with Rf = 0.4~0.5 was recovered to obtain the white solid compound 174 (46.8 mg, yield 49.5%). ESI[M+H] + = 454.1.

[0421] 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=4.5 Hz, 1H), 8.07 (d, J=7.9 Hz, 1H), 8.02-7.94 (m, 2H), 7.82 (d, J=8.7 Hz, 1H), 7.71 (d, J=2.2 Hz, 1H), 7.54 (dd, J=6.5, 4.9Hz, 1H), 4.98 (dd, J=11.0, 7.7 Hz, 1H), 4.90 (dd, J=11.0, 5.6 Hz, 1H), 4.63 (dd, J=7.5, 5.7 Hz, 1H), 2.63-2.58 (m, 1H), 2.57 (s, 3H), 1.15-1.12 (m, 6H) Example 85 Preparation of Compound 175 TIFF2026519809000160.tif29170

[0422] 3-Oxetanecarboxylic acid (39.9 mg, 0.391 mmol), DCC (80.7 mg, 0.391 mmol), and DMAP (95.6 mg, 0.783 mmol) were dissolved in dichloromethane (2 mL) and stirred at room temperature for 15 minutes. 174-2 (100 mg, 0.260 mmol) was added to the reaction system and stirred for a further 12 hours at room...

Claims

1. Compounds represented by general formula I, pharmaceutically acceptable salts thereof, stereoisomers, prodrugs, solvates, and deuterated compounds, Here, Y is selected from N or -CF, A is selected from N or CH. M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. When M does not exist, R X is -H, halogen, -NO 2 , -CN, -CF 3 , C 2-8 alkenyl group, C 2-8 alkynyl group, C 1-10 linear / branched alkyl group, -N(C 0-10 alkyl group)(C 0-10 alkyl group), -OC 0-10 alkyl group, C 3-10 cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, and when M forms a condensed ring with the adjacent carbon, R X does not exist, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is O, S-Rxx, N or Selected from, R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3- to 8-membered heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. If Q is N, then R 3 Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. L does not exist, or L is C 2-8 Olefin bond or C l-8 Selected from alkylene groups, where H in the group is a halogen, -CN, or -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. Q is N or When A is N, Q, A, and L, together with the atoms in between, form a 5-membered or 6-membered nitrogen-containing heterocycle. n is either 0 or 1, and when n is 0, it indicates that there is no -CO- group. If X is absent or n is 1, X is O; if n is 0, X is selected from O, substituted / unsubstituted N alkyl groups, and substituted / unsubstituted N heterocycloalkyl groups. R 4 -H, Halogen, -CN, -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, heterocycloalkyl groups, aryl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, -SO 2 (C 0-10 Alkyl alkyl group), -SO(C 0-10 Alkyl(alkyl group), -SO 2 O(C) 0-10 Alkyl(alkyl group), -SO 2 N(C) 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -SO 2 (C 3-10 Cycloalkyl groups), -SO 2 - Aryl group, -CON(C 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl(alkyl group), -CO(C 3-10 Cycloalkyl group), -CO (3-6 member heterocycloalkyl group), -(C 0-10 Alkyl(COO) 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, or -NO 2 -CF 3 , C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C 3-6 Heterocycloalkyl groups, -N(C 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO (C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C)(-CON(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OCOO(C 0-10 It can be substituted with alkyl groups, phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, and alkynyl groups. Compounds, their pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds.

2. It has the following structural formula, Here, Y is selected from N or -CF, R 1 、R 2 are each independently -H, halogen, -NO 2 、-CN, -CF 3 、C 2-8 alkenyl group, C 2-8 alkynyl group, C 1-10 linear / branched alkyl group, -N(C 0-10 alkyl group)(C 0-10 alkyl group), -OC 0-10 alkyl group, C 3-10 cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, or R 1 、R 2 is R 1 and R 2 together with the C atom between them form a 5-membered aromatic heterocycle, 6-membered aromatic heterocycle or aromatic ring, wherein the 5-membered aromatic heterocycle is selected from furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, the 6-membered aromatic heterocycle is selected from pyridine, pyridazine, pyrimidine, pyrazine, and optionally, H in the 5-membered aromatic heterocycle, 6-membered aromatic heterocycle or aromatic ring is substituted by halogen, -CN, -CF 3 ,C 1-10 linear / branched alkyl group, -N(C 0-10 alkyl group)(C 0-10 alkyl group), -OC 0-10 alkyl group, C 3-10 cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group. Q is chosen from O or N, and R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group or a 3- to 8-membered heterocycloalkyl group, the heterocycloalkyl group containing at least one N, O, or S as a ring atom. If Q is N, then R 3 Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. L does not exist, or L is C 2-8 Olefin bond or C l-8 Selected from alkylene groups, where H in the group is a halogen, -CN, or -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. n is either 0 or 1, and when n is 0, it indicates that there is no -CO- group. If X is absent or n is 1, X is O; if n is 0, X is selected from O, substituted / unsubstituted N alkyl groups, and substituted / unsubstituted N heterocycloalkyl groups. R 4 -H, halogen, CN, -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, heterocycloalkyl groups, aryl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, -SO 2 (C 0-10 Alkyl alkyl group), -SO(C 0-10 Alkyl(alkyl group), -SO 2 O(C) 0-10 Alkyl(alkyl group), -SO 2 N(C) 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -SO 2 (C 3-10 Cycloalkyl groups), -SO 2 -aryl group, -CON(C) 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl(alkyl group), -CO(C 3-10 Cycloalkyl groups), -CO (3-6 member heterocycloalkyl groups), (C 0-10 Alkyl(COO) 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, or -NO 2 -CF 3 , C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C 3-6 Heterocycloalkyl groups, -N(C 0-10 (Alkyl group) (C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO (C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C)(-CON(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OCOO(C 0-10 It can be substituted with alkyl groups, phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, and alkynyl groups. The compound according to claim 1, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds.

3. It has the following structural formula, Here, Y is selected from N or -CF, R 1 , R 2 These are, independently, -H, -F, -Cl, -Br, and -NO. 2 -CN, -CF 3 , C 2-4 Alkenyl group, C 2-4 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl group), - OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, S heterocycloalkyl groups, or R 1 , R 2 is R and R 2 Together with the C atom between them, they form a 5-membered aromatic heterocycle, a 6-membered aromatic heterocycle, or a benzene ring. The 5-membered aromatic heterocycle is selected from furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, and thiazole. The 6-membered aromatic heterocycle is selected from pyridine, pyridazine, pyrimidine, and pyrazine. Optionally, the H atoms in the 5-membered aromatic heterocycle, 6-membered aromatic heterocycle, or benzene ring are halogens, -CN, and -CF. 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group, an N heterocycloalkyl group, an O heterocycloalkyl group, or an S heterocycloalkyl group. Q is chosen from O or N, and R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 It may be substituted with a cycloalkyl group or a 3- to 8-membered heterocycloalkyl group, the heterocycloalkyl group containing at least one N, O, or S as a ring atom. If Q is N, then R 3 Q, together with the N and C atoms in between, forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms. L does not exist, or L is C 2-4 Olefin bond or C 1-8 Selected from alkylene groups, where H in the group is a halogen, -CN, or -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl groups, 3-10 membered cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. R a is -H, C 1-10 Linear / branched alkyl groups, -OR b Selected from, R b C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3- to 8-membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R c is -H, C 1-10 Linear / branched alkyl groups, Cc 3-10 Cycloalkyl groups, -CH 2 CO(C 0-10 Alkyl(alkyl group), -CH 2 COO (C 0-6 Alkyl(alkyl group), -CH 2 COO (C 3-6 Cycloalkyl groups), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 0-10 Alkyl group) (C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -CI, -CN, -NO 2 , C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, or R c teeth, 、 、 Selected from, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O (C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group) (C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the said groups is a halogen, -CN,-CH 3 , -C 2 H 5 ,- OCH 3 , -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF3, or -OC 0-10 It may be substituted with an alkyl group or a C34 cycloalkyl group. R d1 and R d2 These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(alkyl group), -CO(C 0-10 Selected from alkyl groups, 3-6 membered cycloalkyl groups, 3-6 membered heterocycloalkyl groups, or aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3- to 6-membered heterocycloalkyl group, and the H in the group is a halogen, -CN, -NO 2 , C 1-3 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-10 Alkyl group ) COO (C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl group), aryl group, -N (C 1-3 Alkyl group) (C 1-3 The alkyl group may be substituted with -CN, -OCF 3 ,-OC 0-10 Alkyl, -CO(C 0-10 Alkyl groups), C34 cycloalkyl groups, and aryl groups may be substituted. R e1 and R e2 These are H and C, respectively, independently. 1-3 A compound according to claim 2, selected from linear / branched alkyl groups, a pharmaceutically acceptable salt thereof, a stereoisomer thereof, a prodrug, a solvate, and a deuterated compound thereof.

4. It has the following structural formula, m is an integer from 0 to 4, and R 5 -H, halogen, -CN, -CF 3 , -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R 6 is -H, C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3- to 6-membered heterocycloalkyl groups, and aryl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R 16 C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O (C 3-4 Heterocycloalkyl group), -C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 A group selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 (Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R 19 is -H, -Cl -10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH 2 CO(C 1-5 Alkyl(alkyl group), -CH 2 COO (C 1-5 Alkyl(alkyl group), -CH 2 COO (C 3-6 Cycloalkyl groups), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 1-3 (Alkyl group) (C 1-3 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -CI, -CN, -NO 2 , -CH 3 , -C 2 H 5 , -C 3 H 7 , 3-6 member heterocycloalkyl groups, OC 1-3 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 It may be substituted with an alkyl group, vinyl group, imidazolyl group, oxazolyl group, thiazolyl group, or pyridinyl group. R 20a and R 20b These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3-6 member heterocycloalkyl groups, aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3- to 6-membered N heterocycloalkyl group, and the H in the group is -F, -Cl, -CN, -NO 2 , -CH 3 , -C 2 H 5 ,-OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3 Alkyl(COO) 0-5 Alkyl(alkyl group), -CO(C 0-5 Alkyl(alkyl group), -N(C) 1-3 (Alkyl group) (C 1-3 Alkyl group), may be substituted with an aryl group, and the alkyl group portion may be -CN, -OCF 3 ,-OC 0-3 Alkyl, -CO(C 0-5 Alkyl alkyl group), C 3-4 The compound according to claim 3, which may be substituted with a cycloalkyl group or an aryl group, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

5. It has the following structural formula, Here, Y is selected from N or -CF, and P is N or CH. m is an integer between 0 and 4. R 7 -H, -F, -Cl, -Br, -I, -NO 2 -CN, alkenyl group, alkynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 8 -H, -CN, -CF 3 , C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R 9 -H, -F, -Cl, -Br, -I, -NO 2 -CN, alkenyl group, alkynyl group, -CF 3 ., C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 10 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group) (C 1-3 Alkyl alkyl groups), may be substituted with 5-membered or 6-membered N heterocycloalkyl groups, R 6’ and R 6” These are, independently, -H and C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3- to 6-membered heterocycloalkyl groups, and aryl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R 16’ , R 16” , R 16* , R 16** R 16# and R 16## Each of them is independent of C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O (C 3-4 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3- to 6-membered heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 A group selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3-6 member heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R 19’ and R 19” These are -H and -Cl, respectively, independently. -10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH 2 CO(C 1-5 Alkyl(alkyl group), -CH 2 COO (C 1-5 Alkyl(alkyl group), -CH 2 COO (C 3-6 Cycloalkyl groups), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 1-3 (Alkyl group) (C 1-3 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO 2 , -CH 3 , -C 2 H 5 , -C 3 H 7 , 3-6 member heterocycloalkyl group, -OC 1-3 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 It may be substituted with an alkyl group, vinyl group, imidazolyl group, oxazolyl group, thiazolyl group, or pyridinyl group. R 20a’ , R 20a”、 R 20b’ and R 20b” These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3-6 member heterocycloalkyl groups, aryl groups, or R d1 and R d2 These, together with the N atoms between them, form a 3- to 6-membered N heterocycloalkyl group, and the H in the group is -F, -Cl, -CN, -NO 2 , -CH 3 , -C 2 H 5 ,-OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3 Alkyl(COO) 0-5 Alkyl(alkyl group), -CO(C 0-5 Alkyl(alkyl group), -N(C) 1-3 Alkyl group) (C 1-3 Alkyl group), may be substituted with an aryl group, and the alkyl group portion may be -CN, -OCF 3 ,-OC 0-3 Alkyl, -CO(C 0-5 Alkyl alkyl group), C 3-4 Can be substituted with cycloalkyl groups and aryl groups. The compound according to claim 4, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds.

6. It has the following structural formula, Here, Y is selected from N or -CF, and P is N or CH. m 1 is an integer between 0 and 2, R 11 -F, -Cl, -Br, -I, -NO 2 , ethynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 6a teeth 、 、 or C 1-4 Selected from alkyl groups, the H in the alkyl group is -F, -OCH 3 , C 3-6 Can be substituted with a cycloalkyl group, R 6a1 -H, -CN, -CH 3 , -C 2 H 5 Selected from vinyl group, propadienyl group, and ethynyl group, R 6a2 These are vinyl group, ethynyl group, -COCH 3 ,-COC 2 H 5 , selected from 3-4 member epoxy alkyl groups, R 6a3 is, -CH 3 , -C 2 H 5 ,-OCH 3 ,-OC 2 H 5 Selected from, R 12 -F, -Cl, -Br, -I, -NO 2 , ethynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 13 , R 13’ , R 13” These are, independently, -H and C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group) (C 1-3 Alkyl alkyl groups), may be substituted with 5-membered or 6-membered N heterocycloalkyl groups, R 6b -H, -CH 3 , -C 2 H 5 Selected from propyl group, isopropyl group, butyl group, tert-butyl group, and 3-4 membered saturated ring Oalkyl group, wherein the H in the group is -F, -Cl, -CN, -CH 3 , -C 2 H 5 ,-OCH 3 , C 3-4 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 1-3 Alkyl(alkyl group), -OCO(C 1-3 The alkyl group may be substituted with an alkyl group, a vinyl group, or an ethynyl group, and furthermore, the alkyl group may be -OCH 3 ,-OC 2 H 5 It can be replaced by, R 14 -H, halogen, -NO 2 -CN, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, R 6c is -H, C 1-5 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and -O heterocycloalkyl groups, the H in the group is -F, -Cl, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , C 3-4 It may be substituted with a cycloalkyl group, a vinyl group, or an ethynyl group. T is C, N, O, or S. R 15 -H, halogen, -NO 2 -CN, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, R 6d is -H, C 1-5 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and -O heterocycloalkyl groups, the H in the group is -F, -Cl, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , C 3-4 The compound according to claim 5, which may be substituted with a cycloalkyl group, a vinyl group, or an ethynyl group, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

7. It has the following structural formula, Here, Y is selected from N or -CF, m 1 is an integer between 0 and 2, R 17 , R'17, R"17, R 18 , R' 18 , R" 18 These are, independently, -F, -Cl, -Br, -I, and -NO. 2 , ethynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 16a1 and R 16a2 Each of them is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, -O(C 3-4 Cycloalkyl group), -O (C 3-4 Heterocycloalkyl groups), C 3-6 Cycloalkyl group, 3-6 member N; Heterocycloalkyl group, 3-6 member O; Heterocycloalkyl group, -N (C 0-10 (Alkyl group) (C 0-10 A group selected from alkyl groups, vinyl groups, ethynyl groups, aryl groups, pyridinyl groups, and imidazolyl groups, wherein the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 (Alkyl group) (C 1-3 Alkyl alkyl groups may be substituted with vinyl groups, R 16b1 and R 16b2 Each of them is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, aryl group, -N(C 1-3 (Alkyl group) (C 1-3 Selected from alkyl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 It can be replaced by, R 16c1 and R 16c2 Each of them is independent of C 1-5 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Selected from cycloalkyl groups and aryl groups, The compound according to claim 5, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

8. It has the following structural formula, Here, Y is selected from N or -CF, m 1 is an integer between 0 and 2, R 17 and R 18 These are independently -F, -Cl, -Br, -I, and -NO 2 , ethynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 19a1 and R 19a2 These are, independently, -H and C 1-3 Linear / branched alkyl groups, C 3-6 Cycloalkyl groups, -CH 2 CO(C 1-3 Alkyl(alkyl group), -CH 2 COO (C 1-3 Alkyl(alkyl group), -CH 2 COO (C 3-6 Heterocycloalkyl groups), - CH 2 CON(C 1-3 Selected from alkyl groups (C13 alkyl groups), benzyl groups, and aryl groups, wherein the H in the group is -F, -Cl, -CN, -NO 2 , -CH 3 , -C 2 H 5 , -C 3 H 7 ,-OC 1-3 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 It can be substituted with alkyl groups, vinyl groups, imidazolyl groups, thiazolyl groups, and pyridinyl groups. The compound according to claim 5, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

9. It has the following structural formula, Here, Y is selected from N or -CF, m 1 is an integer between 0 and 2, R 21 and R '21 These are, independently, -F, -Cl, -Br, -I, and -NO. 2 , ethynyl group, -CF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Selected from cycloalkyl groups, N heterocycloalkyl groups, O heterocycloalkyl groups, and S heterocycloalkyl groups, R 22a and R 22b These are, independently, -H and C 1-3 Linear / branched alkyl groups, -COO(C 1-3 Alkyl(alkyl group), -CO(C 1-3 Alkyl alkyl group), C 3-5 Selected from cycloalkyl groups, 3- to 6-membered heterocycloalkyl groups, and aryl groups, wherein the H in the group is F, -Cl, -CN, or -NO 2 , -CH 3 , -C 2 H 5 ,-OCH 3 ,-(C 0-3 Alkyl group ) COO (C 1-3 It may be substituted with an alkyl group. m 2 These are integers from 1 to 3, R 23 is -H, C 1-3 Linear / branched alkyl groups, -COO(C 1-3 Alkyl(alkyl group), -CO(C 1-3 Alkyl alkyl group), C 3-5 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-3 Alkyl group) (C 0-3 Selected from alkyl groups and aryl groups, the H in the group is -F, -Cl, -CN, -NO 2 , -CH 3 , -C 2 H 5 ,-OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-3 Alkyl group ) COO (C 0-5 Alkyl(alkyl group), -CO(C 0-5 The compound according to claim 5, which may be substituted with an alkyl group, an aryl group, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound thereof.

10. It has the following structural formula, Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is O, S-Rxx, N or Selected from, R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3- to 8-membered heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. If Q is N, then R 3 Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. L does not exist, or L is C 2-8 Olefin bond or C 1-8 Selected from alkylene groups, where H in the group is a halogen, -CN, or -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C l-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. Q is N or And when A is N, Q, A, and L, together with the atoms in between, form a 5-membered or 6-membered nitrogen-containing heterocycle. n is either 0 or 1, and when n is 0, it indicates that there is no -CO- group. If X is absent or n is 1, X is O; if n is 0, X is selected from O, substituted / unsubstituted N alkyl groups, and substituted / unsubstituted N heterocycloalkyl groups. R 4 -H, halogen, CN, -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, heterocycloalkyl groups, aryl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, -SO 2 (C 0-10 Alkyl alkyl group), -SO(C 0-10 Alkyl(alkyl group), -SO 2 O(C) 0-10 Alkyl(alkyl group), -SO 2 N(C) 0-10 Alkyl group) (C 0-10 Alkyl(alkyl group), -SO 2 (C 3-10 Cycloalkyl groups), -SO 2 - Aryl group, -CON(C 0-10 Alkyl group) (C 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl(alkyl group), -CO(C 3-10 Cycloalkyl group), -CO (3-6 member heterocycloalkyl group), -(C 0-10 Alkyl group ) COO (C 0-10 Alkyl(alkyl group), -COO(C 3-10 Selected from cycloalkyl groups, -COO (3-6 member heterocycloalkyl groups), alkenyl groups, and alkynyl groups, the heterocycloalkyl group contains at least one N, O, or S as a ring atom, where the H in the group is a halogen, -CN, or -NO 2 -CF 3 , C 1-3 Linear alkyl groups, -OC 0-10 Alkyl alkyl group, C 3-6 Cycloalkyl groups, C 3-6 Heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl(alkyl group), -COO(C 3-10 Cycloalkyl group), -COO (heterocycloalkyl group), -CO (C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Alkyl(C)(-CON(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OCOO(C 0-10 Alkyl groups may be substituted with phenyl groups, N heterocycloaryl groups, O heterocycloaryl groups, S heterocycloaryl groups, alkenyl groups, or alkynyl groups. The compound according to claim 1, its pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates, and deuterated compounds.

11. M, together with adjacent carbon atoms, forms a 3- to 8-membered saturated / unsaturated alicyclic ring, a 3- to 8-membered saturated / unsaturated heterocyclic ring, a benzene ring, a 5- or 6-membered monocyclic heteroaromatic ring, a heteroaromatic ring formed by the condensation of a benzene ring with 1-2 5- or 6-membered monocyclic heteroaryl groups, and a heteroaromatic ring formed by the fusion of 2-3 5- and / or 6-membered monocyclic heteroaryl groups. Here, H in the group is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 The compound according to claim 1 or 10, characterized in that it can be substituted with an alkyl group, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound thereof.

12. M, together with adjacent carbon atoms, forms a 3-6 member saturated / unsaturated alicyclic ring, a 3-6 member saturated / unsaturated heterocyclic ring, a phenyl group, a pyrroloyl group, a thiophenolyl group, a furanyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, a benzofuranyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenolyl group, a benzothiazolyl group, an indolyl group, or an imidazopyridyl group. The heteroatoms of the aforementioned 3- to 8-membered saturated / unsaturated heterocycle are selected from one or more of N, O, and S. Here, H in the group is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 The compound according to claim 11, characterized in that it can be substituted with an alkyl group, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound thereof.

13. It has the following structural formula, Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is N or Selected from, R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 H in the alkyl group may be substituted with -N(C 1-6 (Alkyl group) (C 1-6 Alkyl alkyl group), -OC 1-6 Alkyl alkyl group, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -COO(C 1-6 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. If Q is N, then R 3 The compound according to claim 10, the pharmaceutically acceptable salts, stereoisomers, prodrugs, solvates and deuterated compounds thereof, wherein Q forms a five-membered aromatic heterocycle or a six-membered aromatic heterocycle having at least two heteroatoms together with N and C atoms between them.

14. It has the following structural formula, Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. R y1 -H, -CN, -CF 3 , C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R y2 is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -COO(C 0-5 The compound according to claim 13, which may be substituted with an alkyl group, a 5-membered or 6-membered N heterocycloalkyl group, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound thereof.

15. It has the following structural formula, Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is selected from O, S-Rxx or N, and R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3- to 8-membered heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. If Q is N, then R 3 Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. L does not exist, or L is C 2-4 Olefin bond or C 1-8 Selected from alkylene groups, where H in the group is a halogen, -CN, or -CF 3 ,-OCH 2 F, -OCHF 2 , -OCF 3 , C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl groups, 3-10 membered cycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 It may be substituted with an alkyl group. R f is -H, C 1-10 a linear / branched alkyl group, OR j selected from, R j is C 1-10 a linear / branched alkyl group, C 3-10 a cycloalkyl group, a 3-8 member heterocycloalkyl group, an aryl group, a heteroaryl group, where H in said groups is halogen, -CN, -CH 3 , -C 2 H 5 , -OC 1-5 , C 3-6 a cycloalkyl group, a 3-6 member heterocycloalkyl group, -CO(C 0-10 alkyl group), -OCO(C 0-10 alkyl group), a vinyl group, a propadienyl group, an ethynyl group, and further, the alkyl group portion may be substituted by -CN, -OCH 2 F, -OCHF 2 , -OCF 3 , -OC 0-10 alkyl group, C 3-4 a cycloalkyl group, and may be substituted R g is -H, -Cl -10 a linear / branched alkyl group, -C 3-10 a cycloalkyl group, -CH 2 CO(C 0-10 an alkyl group), -CH 2 COO(C 0-6 an alkyl group), -CH 2 COO(C 3-6 a cycloalkyl group), -CH 2 COO(C 3-6 a heterocycloalkyl group), -CH 2 CON(C 0-10 an alkyl group)(C 0-10 an alkyl group), a benzyl group, an aryl group, and H in the said groups is -F, -Cl, -CN, -NO 2 , C 1-10 a linear / branched alkyl group, a 3- to 6-membered heterocycloalkyl group, -OC 1-5 an alkyl group, -N(C 1-3 an alkyl group)(C 1-3 an alkyl group), C 2-8 an alkenyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyridinyl group, a pyrimidinyl group, a phenyl group, and may be substituted by these, or R g is 、 、 Selected from, R c1 , R c2 , R c3 C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O (C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R h1 and R h2 These are H and C, respectively, independently. 1-10 Linear / branched alkyl groups, -COO(C 0-10 Alkyl(alkyl group), -CO(C 0-10 Selected from alkyl groups, 3-6 membered cycloalkyl groups, 3-6 membered heterocycloalkyl groups, or aryl groups, or R h1 and R h2 These, together with the N atoms between them, form a 3- to 6-membered heterocycloalkyl group, and the H in the group is a halogen, -CN, -NO 2 , C 1-3 Linear / branched alkyl groups, -OC 1-3 Alkyl alkyl group, C 3-6 Cycloalkyl group, -(C 0-10 Alkyl(COO) 0-10 Alkyl(alkyl group), -CO(C 0-10 Alkyl group), aryl group, -N (C 1-3 (Alkyl group) (C 1-3 The alkyl group may be substituted with -CN, -OCF 3 ,-OC 0-10 , -CO(C 0-10 Alkyl alkyl group), C 3-4 It may be substituted with a cycloalkyl group or an aryl group. R j The group is selected from halogens, cyano groups, aryl groups, heteroaryl groups, 3- to 6-membered cycloalkyl groups, or 3- to 6-membered heterocycloalkyl groups, wherein the H in the group is a halogen, -CN, or -NO 2 , C 1-10 Linear / branched alkyl groups, -OC 1-10 The compound according to claim 10, which can be substituted with an alkyl group, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

16. It has the following structural formula, Here, Y is selected from N or -CF, M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. When M is absent, R x is -H, halogen, -NO 2 , -CN, -CF 3 , C 2-8 alkenyl group, C 2-8 alkynyl group, C 1-10 linear / branched alkyl group, -N(C 0-10 alkyl group)(C 0-10 alkyl group), -OC 0-10 alkyl group, C 3-10 cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, and when M forms a condensed ring with the adjacent carbon, R x is absent, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. Q is selected from O, S-Rxx or N, and R 3 is -H, C 1-5 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, 3-8 member heterocycloalkyl groups, -COO(C 0-10 It may be substituted with an alkyl group, and the heterocycloalkyl group contains at least one N, O, or S as a ring atom. If Q is N, then R 3 Q forms a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle having at least two heteroatoms together with the N and C atoms between them. Rxx is H, C 1-5 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. m 1 , m 2 , m 3 These are independently chosen from integers between 0 and 5. R 5 ', R 5 ", R 5 '” independently represents -H, halogen, -CN, and -CF 3 , -Cl -10 Alkyl, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R f ' is -H, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 (Alkyl alkyl group), OR j Selected from, R j ' is C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3-8 membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 A group selected from alkyl groups, vinyl groups, propadienyl groups, and ethynyl groups, and furthermore, the alkyl group portion is -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. Rg' is -H, -Cl -10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH 2 CO(C 0-10 Alkyl(alkyl group), -CH 2 COO (C 0-6 Alkyl(alkyl group), -CH 2 COO (C3-6 cycloalkyl group), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 0-10 (Alkyl group) (C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO 2 , C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or R g 'teeth, 、 、 Selected from, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O (C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 (Alkyl group) (C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 (Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R i ' is selected from halogens, cyano groups, phenyl groups, 5-6 member N, O and / or S-containing heteroaryl groups, 3-6 member cycloalkyl groups or 3-6 member heterocycloalkyl groups, wherein H in the group is a halogen, -CN, -NO 2 , C 1-6 Linear / branched alkyl groups, -OC 1-6 The compound according to claim 15, which can be substituted with an alkyl group, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

17. It has the following structural formula, Here, Y is selected from N or -CF, and P' is N or CH. M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. R 8 ' is -H, halogen, -CN, -NO 2 -CF 3 , C 1-4 Linear / branched alkyl groups, C 3-10 Selected from member cycloalkyl groups, R 10 ' is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group) (C 1-3 Alkyl(alkyl group), -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Alkyl alkyl groups), may be substituted with 5-membered or 6-membered N heterocycloalkyl groups, Q' is chosen from =O or -S-Rxx, where Rxx is H, C 1-3 Selected from linear / branched alkyl groups, wherein H in the alkyl group is a halogen, nitro group, cyano group, -OC 0-10 It may be substituted with an alkyl group. m 1 , m 2 , m 3 These are independently chosen from integers between 0 and 4. R 5 ', R 5 ", R 5 '” independently represents -H, halogen, -CN, and -CF 3 , -C l-10 Alkyl, -CO(C 0-10 Alkyl(alkyl group), -COO(C 0-10 Selected from alkyl groups, R f ' is -H, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 (Alkyl alkyl group), OR j Selected from, R j ' is C 1-10 Linear / branched alkyl groups, C 3-10 Selected from cycloalkyl groups, 3-8 membered heterocycloalkyl groups, aryl groups, and heteroaryl groups, where H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 A group selected from alkyl groups, vinyl groups, propadienyl groups, and ethynyl groups, and furthermore, the alkyl group portion is -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R g ' is -H, -C 1-10 Linear / branched alkyl groups, -C 3-10 Cycloalkyl groups, -CH 2 CO(C 0-10 Alkyl(alkyl group), -CH 2 COO (C 0-6 Alkyl(alkyl group), -CH 2 COO (C 3-6 Cycloalkyl groups), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 0-10 (Alkyl group) (C 0-10 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO 2 , C 1-10 Linear / branched alkyl groups, 3-6 member heterocycloalkyl groups, -OC 1-5 Alkyl alkyl, -N(C) 1-3 (Alkyl group) (C 1-3 Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or R g 'teeth, 、 、 Selected from, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O (C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R i ' is selected from halogens, cyano groups, phenyl groups, 5-6 member N, O and / or S-containing heteroaryl groups, 3-6 member cycloalkyl groups or 3-6 member heterocycloalkyl groups, wherein H in the group is a halogen, -CN, -NO 2 , C 1-6 Linear / branched alkyl groups, -OC 1-6 The compound according to claim 16, which can be substituted with an alkyl group, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

18. Y is selected from N or -CF, and P' is N or CH. M is either absent or forms a fused ring with an adjacent carbon, jointly forming a saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring. If M does not exist, R x -H, halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 The cycloalkyl group is N heterocycloalkyl group, O heterocycloalkyl group, and S heterocycloalkyl group, and when M forms a fused ring with an adjacent carbon, R x It does not exist, n 1 is 0, 1, or 2, In the saturated / unsaturated alicyclic ring, saturated / unsaturated heterocyclic ring, aromatic ring, or heteroaromatic ring, H is a halogen, -NO 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 (Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl groups, N heterocyclic alkyl groups, O heterocyclic alkyl groups, S heterocyclic alkyl groups, -NHCO(C 0-10 It may be substituted with an alkyl group. R 8 ' is selected from H or a methyl group, R 10 ' is -H, C 1-3 Selected from linear / branched alkyl groups, the H in the alkyl group is -N(C 1-3 (Alkyl group) (C 1-3 Alkyl(alkyl group), -CO(C 1-3 Alkyl(alkyl group), -COO(C 1-3 It may be substituted with an alkyl group, a piperazinyl group, an N-methylpiperazinyl group, or an N-ethylpiperazinyl group. Q' is selected from =O or -S-Rxx, and Rxx is selected from H or a methyl group. m 1 , m 2 , m 3 These are independently chosen from integers between 0 and 4. R 5 ', R 5 ", R 5 '” independently represents -H, halogen, -CN, and -CF 3 , -Cl -6 Alkyl, -CO(C 1-6 Alkyl(alkyl group), -COO(C 1-6 Selected from alkyl groups, R f ' is -H, C 1-6 Linear / branched alkyl groups, -N(C) 0-6 Alkyl group) (C 0-6 (Alkyl alkyl group), OR j Selected from, R j ' is C 1-6 Linear / branched alkyl groups, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, phenyl groups, thiophenyl groups, furanyl groups, pyrrolyl groups, pyridinyl groups, or any of the following groups: R j1 ', R j2 ', R j3 ', R j4 ', R j5 ', R j6 ' are independently H, halogen, -CN, and -C 1-6 Linear / branched alkyl groups, -C 2-6 Linear / branched alkenyl groups, -OC 1-6 Linear / branched alkyl groups, C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 Selected from alkyl groups and ethynyl groups, Here, the R f In the base of ', H is halogen, -CN, -CH 3 , -C 2 H 5 ,-OC 1-5 , C 3-6 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -CO(C 0-10 Alkyl(alkyl group), -OCO(C 0-10 The alkyl group may be substituted with an alkyl group, a vinyl group, a propadienyl group, or an ethynyl group, and furthermore, the alkyl group may be -CN, -OCH 2 F, -OCHF 2 , -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It may be substituted with a cycloalkyl group. R g ' is -H, -Cl -6 Linear / branched alkyl groups, -C 3-6 Cycloalkyl groups, -CH 2 CO(C 1-6 Alkyl(alkyl group), -CH 2 COO (C 0-6 Alkyl(alkyl group), -CH 2 COO (C36 cycloalkyl group), -CH 2 COO (C 3-6 Heterocycloalkyl groups), -CH 2 CON(C 0-6 Alkyl group) (C 0-6 Selected from alkyl groups, benzyl groups, and aryl groups, the H in the said group is -F, -Cl, -CN, -NO 2 , C 1-10 Linear / branched alkyl groups, 3- to 6-membered heterocycloalkyl groups, -OH, -OC 1-5 Alkyl alkyl, -N(C) 1-3 Alkyl group) (C 1-3 Alkyl alkyl group), C 2-8 It can be substituted with an alkenyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyridinyl group, pyrimidinyl group, or phenyl group, or R g 'teeth, 、 、 Selected from, R c1 , R c2 , R c3 Independently, C 1-10 Linear / branched alkyl groups, -OC 0-5 Alkyl alkyl group, -O(C 3-6 Cycloalkyl group), -O (C 3-6 Heterocycloalkyl groups), C 3-10 Cycloalkyl groups, 3-6 member heterocycloalkyl groups, -N(C 0-10 Alkyl group) (C 0-10 Selected from alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups, the H in the group is a halogen, -CN, or -CH 3 , -C 2 H 5 ,-OCH 3 , -N(C 1-3 Alkyl group) (C 1-3 Alkyl(alkyl group), -C 3-10 The alkyl group may be substituted with a cycloalkyl group, a 3- to 6-membered heterocycloalkyl group, or a vinyl group, wherein the alkyl group is -CN, -OCF 3 ,-OC 0-10 Alkyl alkyl group, C 3-4 It can be substituted by cycloalkyl grouping, R i ' is selected from the following groups: halogen, cyano group, phenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, thiazolyl group, triazolyl group, isoxazolyl group, oxazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, or the following groups. R i In the group, H is a halogen, -CN, -NO 2 , C 1-6 Linear / branched alkyl groups, -OC 1-6 It may be substituted with an alkyl group. This indicates the bonding position. The compound according to claim 16, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

19. The aforementioned M, together with the adjacent carbon, forms the following arbitrary structure: R 1x , R 2x , R 3x , R 4x These are H, halogen, and -NO, respectively, independently. 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 Selected from alkyl groups, T 1 , T 2 , T 3 , T 4 , T 5 CR is independent. 24 Selected from N, O, or S, T 6 is selected from C, N, O, or S. R 24 H, halogen, -CN, -NO 2 ,-NHCO(C 0-10 Alkyl() ), CF 3 , C 1-3 Linear alkyl groups, -OC 0-10 Selected from alkyl groups, This indicates the bonding position. Compounds according to any one of claims 10 to 18, pharmaceutically acceptable salts thereof, stereoisomers, prodrugs, solvates and deuterated compounds thereof.

20. The aforementioned M, together with the adjacent carbon, forms the following arbitrary structure: R 5x -R 23x These are H, halogen, and -NO, respectively, independently. 2 -CN, -CF 3 , C 2-8 Alkenyl group, C 2-8 Alkynyl group, C 1-10 Linear / branched alkyl groups, -N(C) 0-10 Alkyl group) (C 0-10 Alkyl alkyl group), -OC 0-10 Alkyl alkyl group, C 3-10 Cycloalkyl group, N heterocycloalkyl group, O heterocycloalkyl group, S heterocycloalkyl group, -NHCO(C 0-10 Selected from alkyl groups, This indicates the bonding position. The compound according to claim 19, its pharmaceutically acceptable salt, stereoisomer, prodrug, solvate, and deuterated compound.

21.

22. A pharmaceutical composition comprising a compound according to any one of claims 1 to 21, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, and a deuterated compound.

23. Use of a compound according to any one of claims 1 to 21, a pharmaceutically acceptable salt thereof, a stereoisomer, a prodrug, a solvate, or a deuterated compound thereof, or the pharmaceutical composition according to claim 22, in the preparation of a drug capable of controlling analgesic, and / or anesthetic, sedative, hypnotic, and / or status epilepticus.

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