New pharmaceutical compound and composition for the prevention or treatment of cancer or tumors comprising the same

Description

1 / 66 “NEW PHARMACEUTICAL COMPOUND AND COMPOSITION FOR THE PREVENTION OR TREATMENT OF CANCER OR TUMORS COMPRISING THE SAME Field of Technique

[0001] This disclosure relates to a compound with a novel structure that may be used favorably to prevent or treat cancer or tumors. Background of the Technique

[0002] The Hippo signaling pathway affects the size and number of cells that make up an organ and affects organ development and cell growth. In addition, inadequate regulation of the Hippo signaling pathway has been associated with the development of several types of cancer (breast cancer, head and neck cancer, colon cancer, ovarian cancer, liver cancer, brain cancer, prostate cancer, mesothelioma, sarcoma, etc.).

[0003] The Hippo signaling system is composed of several components, such as NF2 (neurofibromatosis type 2), Mst1 / 2 (mammalian Ste20-like kinases 1 and 2), Lats1 / 2 (large tumor suppressor 1 / 2), YAP / TAZ (transcriptional regulatory protein containing WW domain / YES-associated protein), and TEADs (enhanced transcriptional associated domains). Among these, when mutations occur in upstream signaling proteins, such as NF2, MST1 / 2, and LATS1 / 2, which are tumor suppressors, they induce persistent binding of YAP / TAZ and TEAD. This promotes transcription by YAP / TAZ and TEAD to induce gene expression related to cancer cell proliferation and tumor formation.

[0004] When the phosphorylation of Lats1 / 2 by Mst1 / 2 is mediated by the activation of NF2, which is a gene. Petition 870250087334, dated 09 / 26 / 2025, page 85 / 172 2 / 66 tumor suppressor, the phosphorylation of YAP and TAZ present in the cytoplasm is promoted. Phosphorylated YAP and TAZ undergo a ubiquitination process and are then broken down by the proteasome. Therefore, when the Hippo signaling system is activated, YAP and TAZ are deactivated. In contrast, under conditions in which tumor suppressor genes are deactivated, i.e., when Hippo signaling is deactivated, YAP and TAZ are activated and translocated to the nucleus, where they bind to four proteins of the TEAD family (TEAD1 / 2 / 3 / 4) and induce the expression of target genes such as CTGF (connective tissue growth factor), CYR61 (cysteine-rich angiogenic inducer 61), Gli2 (zinc finger 2 of the GLI family), Birc2 / 5 (baculoviral IAP repeat containing 2 / 5), and FGF (fibroblast growth factor). Thus, genes activated by the YAP / TAZ-transcription factor complex regulate cell growth, cell migration, and apoptosis.

[0005] Signaling system abnormalities Hippo signals have been found in several carcinomas, and various research results have been reported to develop anticancer drugs targeting YAP-TEAD. Furthermore, the relevance of the Hippo signaling system has been revealed in the process of acquiring resistance after the application of existing approved anticancer drugs, and several studies are underway to demonstrate the potential of YAP-TEAD anticancer drugs as combination therapies to treat drug resistance. Therefore, there is a need to develop a small molecule inhibitor for the treatment of cancer caused by dysregulation of the Hippo signaling system. Petition 870250087334, dated 09 / 26 / 2025, page 86 / 172 3 / 66

[0006] In this regard, the present inventors studied drugs that can be used favorably for the treatment of cancer in which the regulation of Hippo signaling is switched off and, as a result, discovered that the compound, according to the present disclosure described below, binds to the palmitate binding site that mediates the palmitoylation of TEAD and also inhibits the in vitro growth of a cell line mutated in the Hippo pathway. Through this, it was discovered that the YAP-TEAD inhibitor according to the present disclosure can be used favorably to treat cancer or tumors in which Hippo signaling is switched off, and concluded the present disclosure. Detailed Description of the Invention Technical Problem

[0007] It is an objective of the present disclosure to provide a compound with a novel structure that can be used favorably to prevent or treat cancer or tumors.

[0008] Another objective of this disclosure is to provide a pharmaceutical composition for the prevention or treatment of cancer or tumors comprising the above compound. Technical Solution

[0009] To achieve the above objective, a compound represented by the following Chemical Formula 1, or a pharmaceutically acceptable salt thereof, is provided here: Chemical formula 1 Petition 870250087334, dated 09 / 26 / 2025, page 87 / 172 4 / 66 Ri R3na Chemical formula 1, Ri is an aryl C1-Io; or a 5- or 6-membered heterocycle containing 1 to 4 heteroatoms each independently selected from the group consisting of N, O, and S, wherein Ri is unsubstituted; or substituted with a halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 thioalkoxy, a C1-4 haloalkoxy, a C2-4 alkenyl, a C2-4 alkynyl, a C3-6 cycloalkyl, an amino, nitro, cyano, a (C1-4 alkyl)amino, or a (C1-4 dialkyl)amino; or is fused with a C3-6 cycloalkyl ring. R2 is a C6-10 aryl; a C3-6 cycloalkenyl; or a 5- or 6-membered heterocycle containing 1 to 4 heteroatoms each independently selected from the group consisting of N, O, and S, wherein R2 is unsubstituted; or substituted with 1 to 3 substituents each independently selected from the group consisting of halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 thioalkoxy, a C1-4 haloalkoxy, a C2-4 alkenyl, a C2-4 alkynyl, a C3-6 cycloalkyl, amino, nitro, cyano, a (C1-4 alkyl)amino, and a (C1-4 dialkyl)amino. R3 is hydrogen or halogen. R4 is -NHCO-R', -NHSO2-R', -COO-R', -CONH-R', or 1Hpyrrola-2,5-dione-1-yl, Petition 870250087334, dated 09 / 26 / 2025, p. 88 / 172 5 / 66 where R' is hydrogen, a C1-4 alkyl, a C2-4 alkynyl, or a substituent represented by the following chemical formula 2: Chemical formula 2 in chemical formula 2, R'1 is hydrogen, halogen, or cyano, and R'2 is each independently hydrogen, an aryl C6-10, -CH2-NH2, -CH2-NH(alkyl C1-4), or -CH2-N(alkyl C1-4) 2.

[0010] Preferably, Ri is phenyl, pyridinyl, pyrimidinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyrrolidinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, or isothiazolyl,

[0011] where R1 is unsubstituted; or substituted with a halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 haloalkoxy, an amino, nitro, cyano, a (C1-4 alkyl)amino, or a (C1-4 dialkyl)amino; or is fused with a C3-6 cycloalkyl ring.

[0012] Preferably, R1 is imidazolyl, imidazolyl fused with cyclopentane, pyrazolyl, or pyridinyl,

[0013] where R1 is unsubstituted; or substituted with methyl, ethyl, fluoromethyl, difluoromethyl, or trifluoromethyl.

[0014] Preferably, R2 is phenyl, Petition 870250087334, dated 09 / 26 / 2025, p. 89 / 172 6 / 66 pyridinyl, pyrimidinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyrrolidinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, or isothiazolyl,

[0015] where R2 is unsubstituted; or substituted with a halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 haloalkoxy, an amino, a nitro, a cyano, a (C1-4 alkyl)amino, or a (C1-4 dialkyl)amino.

[0016] Preferably, R2 is phenyl, pyridinyl, or cyclohexenyl,

[0017] where R2 is unsubstituted; or substituted with 1 to 3 substituents each independently selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, and trifluoromethoxy.

[0018] Preferably, R3 is hydrogen, or chlorine.

[0019] Preferably, R4 is -NHCO-R', -NHSO2R', -COO-R', -CONH-R', or 1H-pyrrola-2,5-dione-1-yl;

[0020] wherein R' is hydrogen; a C1-4 alkyl; a C2-4 alkenyl that is unsubstituted, or substituted with 1 or 2 substituents each independently selected from the group consisting of phenyl, fluorine, and cyano; or a C2-4 alkynyl.

[0021] Preferably, R4 is -NHCO-CH=CH2, NHCO-CF=CH2, -NHCO-C(CN)=CH(phenyl), -nHCO-CC-CH , -NHSO2CH3, -NHSO2-CH=CH2, -COOH, -CONH-CH3, or 1H-pyrrola-2,5-dione-1-yl,

[0022] Preferably, chemical formula 1 is represented by chemical formula 3 below: Petition 870250087334, dated 09 / 26 / 2025, page 90 / 172 7 / 66 Chemical formula 3 in chemical formula 3, R is each independently hydrogen, halogen, a C1-4 alkyl, or a C1-4 haloalkyl, n is an integer from 1 to 3, and R4 is -NHCO-CH=CH2, or -COOH.

[0023] Representative examples of the compounds represented by Chemical Formula 1 are as follows: 1) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 2) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide, 3) N-(2-(4-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 4) N-(7-(1-methyl-1H-imidazol-4-yl)-2-phenyl-1H- indol-5-yl)acrylamide, 5) N-(2-(2,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 6) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3,4,5-trifluorophenyl)-1H-indol-5-yl)acrylamide, 7) N-(7-(1-(difluoromethyl)-1H-imidazol-4-yl)-2-(4-fluorophenyl)-1H-indol-5-yl)acrylamide, 8) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, Petition 870250087334, 09 / 26 / 2025, pág. 91 / 172 8 / 66 9) N-(2-(3,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 10) N-(2-(3-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 11) N-(2-(4-chlorophenyl)-7-(1-(difluoromethyl)-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 12) N-(2-(4-chloro-2-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 13) N-(2-(cyclohex-1-en-1-yl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 14) N-(2-(4-fluor-3-methylphenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 15) N-(7-(1-methyl-1H-imidazol-4-yl)-2-p-tolyl-1H- indol-5-yl)acrylamide, 16) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide, 17) N-(7-(6,7-di-hydro-5H-pyrrolo[1,2-a]imidazol2-yl)-2-(4-fluorophenyl)-1H-indol-5-yl)acrylamide, 18) N-(2-(4-chlorophenyl)-7-(6,7-di-hydro-5Hpyrrolo[1,2-a]imidazol-2-yl)-1H-indol-5-yl)acrylamide, 19) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3-(trifluoromethyl)phenyl)-1H-indol-5-yl)methanesulfonamida, 20) N-(2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, 21) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4yl)-1H-indole-5-yl)methanesulfonamide, 22) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4yl)-1H-indole-5-yl)-2-fluoroacrylamida, 23) N-(3-chloro-2-(4-chlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, Petition 870250087334, 09 / 26 / 2025, pág. 92 / 172 9 / 66 24) (E)-N-(2-(4-chlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)-2-cyano-3-phenylacrylamide, 25) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4yl)-1H-indole-5-yl)but-2-inamide, 26) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)ethenesulfonamida, 27) 1-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)-1H-pyrrola-2,5-diona, 28) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-pyrazol-3yl)-1H-indole-5-yl)acrylamida, 29) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Hpyrazol-3-yl)-1H-indole-5-yl)acrylamida, 30) N-(2-(3,4-dichlorophenyl)-7-(pyridin-2-yl)-1Hindol-5-yl)acrylamida, 31) N-(2-(4-fluorophenyl)-7-(pyridin-2-yl)-1Hindol-5-yl)acrylamide, 32) N-(2-(4-fluorophenyl)-7-(1-methyl-1H-pyrazol-3yl)-1H-indole-5-yl)acrylamida, 33) N-(2-(2,4-difluorophenyl)-7-(1-methyl-1Hpyrazol-3-yl)-1H-indol-5-yl)acrylamide, 34) N-(2-(5-chloropyridin-2-yl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, 35) 2-(4-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, 36) 7-(1-methyl-1H-imidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole-5-carboxylic acid, 37) 2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-acid) 4-yl)-1H-indol-5-carboxylic acid, 38) 2-(3,4-dichlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, Petition 870250087334, 09 / 26 / 2025, pág. 93 / 172 10 / 66 39) 2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indole-5-carboxylic acid, 40) 2-(4-chlorophenyl)-N-methyl-7-(1-methyl-1Himidazol-4-yl)-1H-indole-5-carboxamida, 41) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3,4,5trichlorophenyl)-1H-indol-5-yl)acrylamide, 42)N-(2-(3-fluorophenyl)-7-(1-methyl-1H-imidazol4-yl)-1H-indol-5-yl)acrylamide, 43) 2-(3,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, 44) N-(2-(3-chloro-4-fluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, 45) N-(2-(2,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indole-5-yl)acrylamida, 46) N-(2-(4-chloro-3,5-difluorophenyl)-7-(1-methyl1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 47) N-(2-(4-chloro-2,6-difluorophenyl)-7-(1-methyl1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 48) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(4(trifluoromethoxy)phenyl)-1H-indol-5-yl)acrylamide, 49) N-(2-(4-chlorophenyl)-7-(4-methylthiazol-2-yl)- 1H-indole-5-yl)acrylamide, 50) N-(7-(1-ethyl-1H-imidazol-4-yl)-2-(3,4,5trifluorophenyl)-1H-indol-5-yl)acrylamide, 51) N-(7-(1-ethyl-1H-imidazol-4-yl) -2-(4fluorophenyl)-1H-indol-5-yl)acrylamide, and 52) N-(2-(4-bromophenyl)-7-(1-methyl-1H-imidazol-4yl)-1H-indol-5-yl)acrylamide.

[0024] Accordingly, the compounds of the present disclosure may exist in the form of salts, particularly salts Petition 870250087334, dated 09 / 26 / 2025, p. 94 / 172 11 / 66 pharmaceutically acceptable. As salts, salts commonly used in the art may be used without limitation, such as acid addition salts formed by pharmaceutically acceptable free acids. The term pharmaceutically acceptable salt, as used in this document, refers to any organic or inorganic addition salt of the compound represented by Chemical Formula 1, whose concentration is relatively non-toxic and harmless to the patient, is effective, and whose side effects do not degrade the beneficial efficacy of the compound above.

[0025] As a free acid, either an organic acid or an inorganic acid may be used. Examples of inorganic acids include hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, tartaric acid, and the like. Examples of organic acids include methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, and the like, but are not limited to these.

[0026] Furthermore, a pharmaceutically acceptable metallic salt can be obtained by a conventional method using a base. For example, a compound represented by Chemical Formula 1 is dissolved in an excessive amount of an alkali metal hydroxide or an alkaline earth metal hydroxide solution, the salt Petition 870250087334, dated 09 / 26 / 2025, page 95 / 172 The insoluble 12 / 66 is filtered, and then the filtrate is evaporated and dried to obtain a pharmaceutically acceptable metallic salt. At this point, it is particularly preferable to prepare a sodium salt, a potassium salt, or a calcium salt as the metallic salt.

[0027] Furthermore, a pharmaceutically unacceptable salt or solvate of the compound represented by Chemical Formula 1 may be used as an intermediate in the preparation of the compound represented by Chemical Formula 1, or of the pharmaceutically acceptable salt or solvate thereof.

[0028] Meanwhile, the compound represented by Chemical Formula 1 can be prepared as shown in Reaction Scheme 1 or 2 below. Reaction scheme 1 Reaction scheme 2 Petition 870250087334, dated 09 / 26 / 2025, page 96 / 172 13 / 66 r2 o

[0029] In Reaction Schemes 1 and 2, the remaining substituents, except Y, are the same as defined above, and Y is a C1-4 alkyl, more preferably methyl or ethyl.

[0030] Each step 1 of Reaction Schemes 1 and 2 is a Stille coupling reaction, and step 2 is a Sonogashira coupling reaction, where the order of steps 1 and 2 can be altered depending on the reactivity of each reagent (see Example 28). At this point, X' is a substituent for the Stille coupling reaction and can be -SnBu3 or -B(OH)2 for the Suzuki reaction, but is not limited to the same.

[0031] Each step 3 of Reaction Schemes 1 and 2 is a reaction to synthesize indole via a cyclization reaction, which can be carried out under basic conditions, but is not limited to them.

[0032] Step 4 of Reaction Scheme 1 is a reaction to reduce a nitro group, which can be carried out using iron, but is not limited to it.

[0033] Step 5 of Reaction Scheme 1 is a reaction between an amine group and a carbonyl group or a sulfonyl group, according to R4. Petition 870250087334, dated 09 / 26 / 2025, page 97 / 172 14 / 66

[0034] Step 4 of Reaction Scheme 2 is a hydrolysis reaction, which can be carried out under basic conditions, but is not limited to them.

[0035] Step 5 of Reaction Scheme 2 may be a coupling reaction between a nucleophile and a carbonyl group, according to R4, but it is not limited to that.

[0036] Meanwhile, Reaction Schemes 1 and 2 are the cases where R3 in Chemical Formula 1 of the present disclosure is hydrogen, and if R3 is not hydrogen, after step 3 but before step 4, the indole derivative is synthesized by cyclization reactions and then a substitution reaction of R3 is carried out to replace R3.

[0037] The preparation method can be described more specifically in the Examples of the Example described below.

[0038] A pharmaceutical composition comprising the compound represented by Chemical Formula 1, or a pharmaceutically acceptable salt thereof, is further provided. Specifically, a pharmaceutical composition for the prevention or treatment of cancer or tumors is provided, comprising the compound represented by Chemical Formula 1, or a pharmaceutically acceptable salt thereof, as the active ingredient.

[0039] The terms cancer or “tumor” refer to the presence, for example, in an individual, of cells that possess characteristics typical of cancer-causing cells, such as uncontrolled proliferation, immortality, metastatic potential, rapid growth and proliferation rate, decreased cell death / apoptosis. Cancerous cells frequently include solid tumors, Petition 870250087334, dated 09 / 26 / 2025, page 98 / 172 15 / 66 such as sarcomas or carcinomas. Sarcomas include alveolar rhabdomyosarcoma, alveolar soft tissue sarcoma, ameloblastoma, angiosarcoma, chondrosarcoma, chordoma, clear cell sarcoma, undifferentiated liposarcoma, desmoid sarcoma, small round cell connective tissue tumor, embryonal rhabdomyosarcoma, epithelioid fibrosarcoma, epithelioid hemangioendothelioma, epithelioid sarcoma, esthesioneuroblastoma, Ewing's sarcoma, extrarenal rhabdoid tumor, extraskeletal myxoid chondrosarcoma, extraskeletal osteosarcoma, fibrosarcoma, giant cell tumor, hemangiopericytoma, infantile fibrosarcoma, inflammatory myofibroblastic tumor, Kaposi's sarcoma, osteosarcoma, liposarcoma, bone liposarcoma, malignant fibrous histiocytoma. Malignant fibrous histiocytoma of bone, malignant mesenchymoma, malignant peripheral nerve sheath tumor, mesenchymal chondrosarcoma, myxofibrosarcoma;Myxoid liposarcoma, myxoinflammatory fibroblastic sarcoma, osteosarcoma, parosteal osteosarcoma, periosteal osteosarcoma, pleomorphic liposarcoma, pleomorphic rhabdomyosarcoma, extraskeletal Ewing's tumor, rhabdomyosarcoma, round cell liposarcoma, small cell osteosarcoma, solitary fibrous tumor, synovial sarcoma, and telangiectatic osteosarcoma. Carcinomas include adenocarcinoma, squamous cell carcinoma, adenosquamous carcinoma, anaplastic carcinoma, large cell carcinoma, small cell carcinoma, anal cancer, and appendix cancer. Bile duct cancer, bladder cancer, brain tumor, breast cancer, cervical cancer, colon cancer, primary organ cancer; Petition 870250087334, dated 09 / 26 / 2025, page 99 / 172 16 / 66 unknown, esophageal cancer, eye cancer, primary fallopian tube cancer, digestive organ cancer, kidney cancer, liver cancer, lung cancer, medulloblastoma, malignant melanoma, oral cancer, ovarian cancer, pancreatic cancer, parathyroid cancer, penile tumor, pituitary tumor, prostate cancer, rectal cancer, skin cancer, stomach cancer, testicular cancer, throat cancer, thyroid cancer, uterine cancer, vaginal cancer, and vulvar cancer. In some forms, the carcinoma is breast cancer. In some modalities, the cancer used in this application may include uveal melanoma, mesothelioma, esophageal cancer, liver cancer, breast cancer, hepatocellular carcinoma, lung adenocarcinomas, glioma, colorectal cancer, colon cancer, stomach cancer, medulloblastoma, ovarian cancer, esophageal squamous cell carcinoma, sarcoma, Ewing's sarcoma, head and neck cancer, prostate cancer, and meningioma.

[0040] Cancer also includes non-solid tumors, such as blood cancers, in which the cancer cells are derived from the bone marrow. Blood cancer includes leukemia, lymphoma, myeloma, non-Hodgkin lymphoma, Hodgkin lymphoma, T-cell malignancy, or B-cell malignancy. In particular, T-cell malignancy includes mature T-cell lymphoma not elsewhere classified, anaplastic large cell lymphoma, angioimmunoblastic lymphoma, cutaneous T-cell lymphoma, adult T-cell leukemia, blastic natural killer cell lymphoma, platelet gamma-delta T-cell lymphoma, and lymphoblastic lymphoma. B-cell malignancy includes chronic lymphocytic leukemia, lymphoma Petition 870250087334, dated 09 / 26 / 2025, pp. 100 / 172 17 / 66 small lymphocytic lymphoma, follicular lymphoma, diffuse large B-cell lymphoma, mantle cell lymphoma, Waldenstrom's macroglobulinemia, head and neck tumor, marginal lymph node zone B-cell lymphoma, Burkitt's lymphoma, primary mediastinal B-cell lymphoma, immune large cell lymphoma, B-cell lymphoblastic progenitor lymphoma, prolymphocytic leukemia, lymphoplasmacytic lymphoma, peripheral nasal zone lymphoma, plasma cell myeloma, plasmacytoma, intravascular large B-cell lymphoma, primary effusion lymphoma or lymphomatoid granulomatosis, but is not limited to these.

[0041] In some modalities, it includes recurrent or refractory cancer, in which the cancer is a solid tumor. Recurrent or incurable cancer includes adenocarcinoma, squamous cell carcinoma, adenosquamous cell carcinoma, anaplastic carcinoma, large cell carcinoma, small cell carcinoma, biliary tract cancer, bladder cancer, brain tumor, breast cancer, cervical cancer, colorectal cancer, esophageal cancer, ophthalmic tumor, primary fallopian tube cancer, renal cancer, liver cancer, lung cancer, medulloblastoma, malignant melanoma, oral cancer, ovarian cancer, pancreatic cancer, penile cancer, pituitary tumor, prostate cancer, rectal cancer, skin cancer, stomach cancer, testicular cancer, throat cancer, thyroid cancer, uterine cancer, vaginal cancer, and vulvar cancer.

[0042] As used herein, the term prevention refers to any action to delay or inhibit the occurrence, spread, or recurrence of the diseases mentioned above through the administration of the composition of Petition 870250087334, dated 09 / 26 / 2025, pp. 101 / 172 18 / 66 present disclosure, and treatment refers to any action to improve or alter the symptoms of the diseases mentioned above through the administration of the composition of this disclosure.

[0043] The pharmaceutical composition according to this disclosure may be formulated in types for oral or parenteral administration, in accordance with standard pharmaceutical practice. These formulations may contain pharmaceutically acceptable additives, such as carriers, adjuvants or diluents, in addition to the active ingredient.

[0044] Suitable carriers include, for example, physiological saline, polyethylene glycol, ethanol, vegetable oil, and isopropyl myristate and the like. Diluents include, for example, lactose, dextrose, sucrose, mannitol, sorbitol, cellulose and / or glycine and the like, but are not limited to them. In addition, the compounds of this disclosure can be dissolved in oils, propylene glycol, or other solvents commonly used in the preparation of injectable solutions. Furthermore, the compounds of this disclosure can be formulated into ointments or creams for topical application.

[0045] A preferred dose of the compound in this disclosure may vary depending on the patient's condition and weight, the severity of the disease, the type of medication, and the route and duration of administration, but can be appropriately selected by specialists in the field. To achieve the desired effects, however, the compound in this disclosure may be administered daily at a dose of 0.0001 to 100 mg / kg (body weight) and preferably from 0.001 to 100 mg / kg (body weight). Petition 870250087334, dated 09 / 26 / 2025, pp. 102 / 172 19 / 66 administration can be performed once a day or in divided doses each day, orally or parenterally.

[0046] Depending on the method of administration, the pharmaceutical composition may contain the compound of this disclosure in an amount of 0.001 to 99% by weight, preferably 0.01 to 60% by weight.

[0047] The pharmaceutical composition according to this disclosure can be administered to mammals, such as rats, mice, domestic animals and humans, by various routes. Administration can be carried out by all possible methods, for example, oral, rectal, intravenous, intramuscular, subcutaneous, intraendometrial and intracerebroventricular injection. Advantageous Effects

[0048] A compound represented by Chemical Formula 1 of this disclosure, or a pharmaceutically acceptable salt thereof, may be used favorably to prevent or treat cancer or tumors. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] Figure 1 shows the results of Experimental Example 3 and shows the regulatory properties of the expression of two TEAD target genes in Example 1 using real-time PCR. DETAILED DESCRIPTION OF THE MODALITIES

[0050] The following are preferred examples to assist in understanding this disclosure. However, the following examples are for illustrative purposes only and should not be construed as limiting the scope of this disclosure to these examples. Petition 870250087334, dated 09 / 26 / 2025, pp. 103 / 172 20 / 66 Example 1: Preparation of N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide Pd(PPh3)4 Microwave of 1,4-dioxane, 150°C Pd(PPh3)4, Cul Triethylamine THF, 50 °C Acrylic acid EDO triethylamine CH2CI2, rt NaOH Fe, NH4Cl 70% Ethanol Reflux Dimethylacetamide Microwave, 140°C (Step 1)

[0051] In a sealed tube, 2,6-diiodo-4-nitroaniline (2.56 mmol, 1 g, 1.0 eq.) was dissolved in 1,4-dioxane (10 mL). l-Methyl-4-(tributylstanyl)-1-Himidazole (2.56 mmol, 0.95 g, 1.0 eq.) and Pd(PPh3)4 (0.25 mmol, 0.29 g, 0.1 eq.) were added sequentially to the same, and then reacted in a microwave reactor at 150 °C for 1 hour. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous solution of ethyl acetate and ammonium chloride, and then solidified with tert-butyl methyl ether to obtain 2-iodo-6-(1-methyl-1H-imidazol-4-yl)-4-nitroaniline (0.57 g, yield: 64%). (Step 2)

[0052] 2-Iodo-6-(1-methyl-1H-imidazol-4-yl)-4nitroaniline (0.58 mmol, 0.2 g, 1.0 eq.), Pd(PPh3)4 (0.058 mmol, 0.067 g, 0.1 eq.), copper iodide (0.03 mmol, 0.0057 Petition 870250087334, dated 09 / 26 / 2025, pp. 104 / 172 21 / 66 g, 0.05 eq.), triethylamine (1.7 mmol, 0.24 mL, 2.9 eq.), and tetrahydrofuran (2 mL) were added sequentially, and then ultrasonic degassing was performed under a nitrogen atmosphere for 10 minutes. l-Chloro-4-ethynylbenzene (0.69 mmol, 0.094 g, 1.2 eq.) was added to the mixture and reacted at 50°C for 2 hours. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous solution of ethyl acetate and ammonium chloride, and then solidified with tert-butyl methyl ether to obtain 2-((4-chlorophenyl)ethynyl)-6-(l-methyl-lH-imidazol-411)-4-nitroaniline (0.14 g, yield: 68%). (Step 3)

[0053] 2-((4-Chlorophenyl)ethynyl)-6-(1-methyl-1H-imidazol-4-yl)-4-nitroaniline (0.39 mmol, 0.14 g, 1.0 eq.), sodium hydroxide (1.95 mmol, 0.078 g, 5.0 eq.) and dimethylacetamide (10 mL) were added sequentially to a microwave flask and then reacted at 150°C for 15 minutes. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous ethyl acetate and ammonium chloride solution and then solidified with tert-butyl methyl ether to obtain 2-(4-chlorophenyl)-7(1-methyl-1H-imidazol-4-yl)-5-nitro-1H-indole (0.079 g, yield: 57%). (Step 4)

[0054] 2-(4-Chlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-5-nitro-1H-indole (0.22 mmol, 0.079 g, 1.0 eq.), iron (1.0 mmol, 0.055 g, 4.54 eq.), ammonium chloride (0.22 mmol, 0.012 g, 1.0 eq.), and 10 mL of 70% ethanol (ethanol:distilled water = 7:3 (v:v)) were added sequentially, and the reagents were reacted overnight. Petition 870250087334, dated 09 / 26 / 2025, pp. 105 / 172 22 / 66 60°C. After the reaction was complete, iron and ethanol were removed, extracted with an aqueous solution of ammonium chloride, and concentrated, and 2-(4-chlorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-amine was used in the next reaction without separation and purification. (Step 5)

[0055] 2-(4-Chlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-amine (0.1 mmol, 0.032 g, 1.0 eq.), N-(3-dimethylaminopropyl)-Netylcarbodiimide hydrochloride (0.3 mmol, 0.057 g, 3.0 eq.), and 1 mL of dichloromethane were sequentially added to a flask. 0.05 mL of triethylamine and acrylic acid (0.12 mmol, 0.0086 mL, 1.2 eq.) were added to the same, and then reacted overnight at room temperature. After the reaction was complete, the dichloromethane was removed, and purified by column chromatography to obtain the title compound (9.4 mg, yield: 25%).

[0056] 1H NMR (400 MHz, CDC13) δ 11.14 s, 1H), 7.77 (s, 1H), 7.70-7.68 (m, 2H), 7.55-7.54 (m, 2H), 7.447.40 (m, 3H), 7.24-7.25 (m, 1H), 6.76 (d, J = 2.2 Hz, 1H), 6.46 (d, J = 16.0, 1H), 6.33-6.26 (m, 1H), 5.78 (d, J = 12.0, 1H), 3.79 (s, 3H) Example 2: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 106 / 172 23 / 66

[0057] The title compound (8.6 mg, yield: 21%) was obtained in the same manner as in Example 1, except that 1-trifluoromethyl-4-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0058] 1H NMR (400 MHz, CDCL·) δ 11.28 (s, 1H), 7.87-7.85 (m, 2H), 7.80 (s, 1H), 7.70-7.68 (m, 2H), 7,607.58 (m, 2H), 7.41 (s, 1H), 7.25 (s, 1H), 6.88 (s, 1H), 6.46 (d, J = 12.0, 1H), 6.32-6.27 (m, 1H), 5.78 (d, J = 8.0, 1H), 3.80 (s, 3H). Example 3: Preparation of N-(2-(4-fluorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide

[0059] The title compound (8.6 mg, yield: 21%) was obtained in the same manner as in Example 1, except that 1-ethynyl-4-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0060] 1H NMR (500 MHz, DMSO) δ 11.13 (s, 1H), 10.08 (s, 1H), 7.89-7.86 (m, 4H), 7.76 (s, 1H), 7.68 (d, J = 1.6 Hz, 1H), 7.35 (t, J = 8.8 Hz, 2H), 6.92 (d, J = 2.2 Hz, 1H), 6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.26 (dd, J = 17.0, 1.8 Hz, 1H), 5.74 (dd, J = 10.1, 1.8 Hz, 1H), 3.80 (s, 3H). Example 4: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-phenyl-1H-indol-5-yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 107 / 172 24 / 66 H

[0061] The title compound (11.9 mg, yield: 35%) was obtained in the same manner as in Example 1, except that ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0062] 1H NMR (500 MHz, DMSO) δ 11.13 (s, 1H), 10.08 (s, 1H), 7.89-7.86 (m, 4H), 7.76 (s, 1H), 7.68 (d, J = 1.6 Hz, 1H), 7.35 (t, J = 8.8 Hz, 2H), 6.92 (d, J = 2.2 Hz, 1H), 6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.26 (dd, J = 17.0, 1.8 Hz, 1H), 5.74 (dd, J = 10.1, 1.8 Hz, 1H), 3.80 (s, 3H). Example 5: Preparation of N-(2-(2,4-difluorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide H

[0063] The title compound (6.0 mg, yield: 16%) was obtained in the same manner as in Example 1, except that 1-ethynyl-2,4-difluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0064] 1H NMR (500 MHz, DMSO) δ 11.48 (s, 1H), 10.08 (s, 1H), 8.04-7.99 (m, 1H), 7.88 (d, J = 10.0 Hz, 2H), 7.73-7.69 (m, 2H), 7.49-7.44 (m, 1H), 7.27 (td, J = 8.5, 2.0 Hz, 1H), 6.98 (d, J = 1.5 Hz, 1H), 6.50 (dd, J = 17.0, 10.0 Petition 870250087334, dated 09 / 26 / 2025, pp. 108 / 172 25 / 66 Hz, 1H), 6.27 (dd, J = 17.0, 2.0 Hz, 1H), 5.74 (dd, J = 10.0, 2.0 Hz, 1H), 3.79 (s, 3H). Example 6: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-(3,4,5-trifluorophenyl)-1H-indol-5-yl)acrylamide HF

[0065] The title compound (17.8 mg, yield: 45%) was obtained in the same manner as in Example 1, except that 5-ethynyl-1,2,3-trifluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0066] 1H NMR (500 MHz, CDCL·) δ 11.21 (s,1H), 7.82 (s, 1H), 7.61-7.60 (m, 2H), 7.42-7.29 (m, 3H), 7.31(s, 1H), 6.76 (s, 1H), 6.32 (dd, J = 16.6, 10.4 Hz, 1H), 5.80 (d, J = 10.1 Hz, 1H), 3.82 (s, 3H). Example 7: Preparation of N-(7-(1-(difluoromethyl)1H-imidazol-4-yl)-2-(4-fluorophenyl)-1H-indol-5yl)acrylamide F F—( H

[0067] The title compound (9.1 mg, yield: 23%) was obtained in the same manner as in Example 1, except that 1-(difluoromethyl)-4-(tributylstanyl)-1H Petition 870250087334, dated 09 / 26 / 2025, pp. 109 / 172 26 / 66 imidazole was used instead of 1-methyl-4-(tributylstanyl)-1-himidazole in step 1 of Example 1, and 1-ethinyl-4-fluorobenzene was used instead of 1-chloro-4-ethinylbenzene in step 2 of Example 1.

[0068] 1H NMR (500 MHz, DMSO) δ 10.85 (s, 1H), 10.05 (s, 1H), 8.42 (s, 1H), 8.26 (s, 1H), 7.97-7, 88 (m, 3H), 7.94 (CHF2, t, J = 60 Hz, 1H), 7.83 (s, 1H), 7.34 (t, J = 8.7 Hz, 2H), 6.93 (s, 1H), 6.50 (dd, J = 16.9, 10.2 Hz, 1H), 6.27 (d, J = 15.6 Hz, 1H), 5.74 (d, J = 11.3 Hz, 1H). Example 8: Preparation of N-(2-(3,4-dichlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide

[0069] The title compound (3.5 mg, yield: 9%) was obtained in the same way as in Example 1, except that 1,2-dichloro-4-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0070] 1H NMR (500 MHz, DMSO) δ 11.14 (s,1H), 10.07 (s, 1H), 8.14 (s, 1H), 7.91 (s, 1H), 7.89 (s,1H), 7.82 (d, J = 8.5 Hz, 1H), 7.77 (s, 1H), 7.74 (d, J = 8.5 Hz, 1H), 7.71 (s, 1H), 7.10 (s, 1H), 6.49 (dd, J = 17.0,10.0 Hz, 1H), 6.26 (d, J = 17.0 Hz, 1H), 5.73 (d, J = 10.0 Hz, 1H), 3.80 (s,3H). Example 9: Preparation of N-(2-(3,4-difluorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 110 / 172 27 / 66 H

[0071] The title compound (2.0 mg, yield: 5%) was obtained in the same manner as in Example 1, except that 1,2-difluoro-4-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0072] 1H NMR (500 MHz, CD3OD) δ 8.03 (d, J = 2.0 Hz, 1H), 7.82 (dd, J = 9.0, 2.0 Hz, 2H), 7.77 (dd, J = 8.5, 2.0 Hz, 1H), 7.67-7.62 (m, 4H), 6.92 (s, 1H), 6.50 (dd, J = 17.0, 10.0 Hz, 1H), 6.40 (dd, J = 17.0, 2.0 Hz, 1H), 5.79 (dd, J = 10.0, 1.5 Hz, 1H), 3.87 (s, 3H). Example 10: Preparation of N-(2-(3-chlorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide H

[0073] The title compound (11.6 mg, yield: 31%) was obtained in the same manner as in Example 1, except that 1-chloro-3-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0074] 1H NMR (500 MHz, DMSO) δ 11.16 (s, 1H), 10.07 (s, 1H), 7.91-7.90 (m, 3H), 7.80-7.77 (m, 2H), 7.70 (s, 1H), 7.55-7.52 (m, 1H), 7.42-7.41 (m, 1H) 7.06 (s, 1H) 6.49 (dd, J = 17.0, 10.4 Hz, 1H), 6.27 (d, J = 16.8 Hz, 1H), 5.74 (d, J = 11.0 Hz, 1H), 3.80 (s, 3H). Petition 870250087334, dated 09 / 26 / 2025, pp. 111 / 172 28 / 66 Example 11: Preparation of N-(2-(4-chlorophenyl)-7(1-(difluoromethyl)-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide F F—( H

[0075] The title compound (9.0 mg, yield: 22%) was obtained in the same manner as in Example 1, except that 1-(difluoromethyl)-4-(tributylstanyl)-1-Himidazole was used instead of 1-methyl-4-(tributylstanyl)-1-Himidazole in step 1 of Example 1.

[0076] 1H NMR (500 MHz, DMSO) δ 10.90 (s,1H), 10.11 (s, 1H), 8.44 (s, 1H), 8.30 (s, 1H), 7.98 (s,1H), 7.94 (CHF2, t, J = 60.0 Hz, 1H) 7.91-7.89 (m, 2H), 7.83(d, J = 1.5 Hz, 1H), 7.57-7.56 (m, 2H), 7.02 (d, J = 1.9 Hz, 1H), 6.50 (dd, J = 16.9, 10.2 Hz, 1H), 6.27 (dd, J =17.0, 1.7Hz, 1H), 5.83-5.67 (m,1H). Example 12: Preparation of N-(2-(4-chloro-2-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide H

[0077] The title compound (4.5 mg, yield: 11%) was obtained in the same way as in Example Petition 870250087334, dated 09 / 26 / 2025, pp. 112 / 172 29 / 66 1, except where 4-chloro-1-ethynyl-2-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0078] 1H NMR (500 MHz, DMSO) δ 11.52 (s,1H), 10.09 (s, 1H), 8.00 (t, J = 8.5 Hz, 1H), 7.90-7.89 (m,2H), 7.73-7.70 (m, 2H), 7.67 (dd, J = 11.5, 1.5 Hz, 1H),7.44 (dd, J = 8.5, 1.5 Hz, 1H), 7.06 (d, J = 2.0 Hz, 1H),6.50 (dd, J = 17.0, 10.0 Hz, 1H), 6.27 (dd, J = 17.0, 2.0 Hz, 1H), 5.74 (d, J = 10.0, 2.0 Hz, 1H), 3.79 (s,3H). Example 13: Preparation of N-(2-(cyclohex-1-en-1yl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide H

[0079] The title compound (11.0 mg, yield: 32%) was obtained in the same manner as in Example 1, except that 1-ethynylcyclohex-1-ene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0080] 1H NMR (500 MHz, DMSO) δ 10.84 (s,1H), 10.00 (s, 1H), 7.86 (s, 1H), 7.74 (s, 1H), 7.68 (s,1H), 7.62 (s, 1H), 6.53- 6.41 (m, 2H), 6.25 (d, J = 17.2 Hz, 2H), 5.72 (d, J = 10.1 Hz, 1H), 3.78 (s, 3H), 2.44-2.46 (m,2H), 2.25-2.26 (m, 2H), 1.75-1.77 (m, 2H), 1.66-1.68 (m, 2H). Example 14: Preparation of N-(2-(4-fluoro-3-methylphenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 113 / 172 30 / 66 H

[0081] The title compound (6.0 mg, yield: 16%) was obtained in the same manner as in Example 1, except that 4-ethynyl-1-fluoro-2-methylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0082] 1H NMR (500 MHz, DMSO) δ 11.08 (s, 1H), 10.05 (s, 1H), 7.89 (s, 1H), 7.85 (s, 1H), 7.77-7.73 (m, 2H), 7.67-7.64 (m, 2H), 7.28 (t, J = 9.1 Hz, 1H), 6.88 (d, J = 2.2 Hz, 1H), 6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.26 (dd, J = 17.0, 1.8 Hz, 1H), 5.79-5.69 (m, 1H), 3.80 (s, 3H), 2.35 (s, 3H). Example 15: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-p-tolyl-1H-indol-5-yl)acrylamide H

[0083] The title compound (3.3 mg, yield: 9%) was obtained in the same manner as in Example 1, except that 1-ethynyl-4-methylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0084] 1H NMR (500 MHz, DMSO) δ 11.13 (s, 1H), 10.05 (s, 1H), 7.90 (s, 1H), 7.84 (s, 1H), 7.74-7.66 (m, 4H), 7.32 (d, J = 7.5 Hz, 2H), 6.88 (d, J = 2.0 Hz, 1H), 6.49 (d, J = 17.0, 10.0 Hz, 1H), 6.26 (dd, J = 17.0, 1.5 Hz, Petition 870250087334, dated 09 / 26 / 2025, pp. 114 / 172 31 / 66 1H), 5.73 (dd, J = 10.0, 1.5 Hz, 1H), 3.80 (s, 3H), 2.37 (s, 3H). Example 16: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-(3-(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide

[0085] The title compound (3.2 mg, yield: 8%) was obtained in the same way as in Example 1, except where 1-ethynyl-3-(trifluoromethyl)benzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0086] 1H NMR (500 MHz, DMSO) δ 11.23 (s,1H), 10.09 (s, 1H), 8.17 (s, 1H), 8.12 (d, J = 7.5 Hz, 1H), 7.917.90 (m, 2H), 7.77 (s, 1H), 7.76-7.70 (m, 3H), 7.14 (d, J = 2.0 Hz, 1H), 6.49 (dd, J = 17.0, 10.5 Hz, 1H), 6.27 (dd, J = 17.0, 1.5 Hz, 1H), 5.74 (dd, J =10.0, 1.5 Hz, 1H), 3.80 (s, 3H). Example 17: Preparation of N-(7-(6,7-dihydro-5Hpyrrolo[1,2-a]imidazol-2-yl)-2-(4-fluorophenyl)-1H-indol-5yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 115 / 172 32 / 66

[0087] The title compound (6.9 mg, yield: 18%) was obtained in the same manner as in Example 1, except that 1,2-(tributylstanyl)-6,7-dihydro-5Hpyrrola[1,2-a]imidazole was used instead of 1-methyl-4(tributylstanyl)-1H-imidazole in step 1 of Example 1, and 1-ethinyl-4-fluorobenzene was used instead of 1-chloro-4-ethinylbenzene in step 2 of Example 1.

[0088] 1H NMR (500 MHz, DMSO) δ 11.14 (s,1H), 10.03 (s, 1H), 7.92-7.79 (m, 3H), 7.70 (s, 1H), 7.62(s, 1H), 7.43-7.29 (m, 2H), 6.90 (s, 1H), 6.49 (dd, J =17.0, 10.2 Hz, 1H), 6.26 (d, J = 16.6 Hz, 1H), 5.73 (d, J =11.4 Hz, 1H), 4.14-4.02 (m, 2H), 2.98-2.87 (m, 2H), two protons were missing due to overlap. Example 18: Preparation of N-(2-(4-chlorophenyl)-7(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-2-yl)-1H-indol-5yl)acrylamide

[0089] The title compound (6.8 mg, yield: 17%) was obtained in the same manner as in Example 1, except that 2-(tribunylstanyl)-6,7-dihydro-5Hpyrrola[1,2-a]imidazole was used instead of 1-methyl-4(tributylstanyl)-1H-imidazole in step 1 of Example 1.

[0090] 1H NMR (500 MHz, DMSO) δ 11.17 (s,1H), 10.04 (s, 1H), 7.89 (s, 1H), 7.84 (d, J = 8.5 Hz, 2H), 7.71 (s, 1H), 7.63 (s, 1H), 7.56 (d, J = 8.4 Hz, 2H), 6.98 (s, Petition 870250087334, dated 09 / 26 / 2025, pp. 116 / 172 33 / 66 1H), 6.49 (dd, J = 16.9, 10.2 Hz, 1H), 6.26 (d, J = 15.2 Hz, 1H), 5.73 (d, J = 11.9 Hz, 1H), 4.14-4.05 (m, 2H), 2.97-2.88 (m, 2H), two protons were missing due to overlap. Example 19: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-(3-(trifluoromethyl)phenyl)-1H-indol-5-yl)methanesulfonamide MsCl triethylamine ch2ci2

[0091] 7-(1-Methyl-1H-imidazol-4-yl)-2-(3(trifluoromethyl)phenyl)-1H-indol-5-amine (0.1 mmol, 0.035 g, 1.0 eq.) was dissolved in dichloromethane (1 mL) and then cooled to 0°C. Triethylamine (0.15 mmol, 0.015 g, 1.5 eq.) and methanesulfonyl chloride (0.11 mmol, 0.012 g, 1.1 eq.) were added sequentially to the same. The reaction mixture was reacted at room temperature for 2 hours. After the reaction was complete, the dichloromethane was removed, and purified by column chromatography to obtain the title compound (15.0 mg, yield: 35%).

[0092] 1H NMR (500 MHz, DMSO) δ 11.32 (s,1H), 9.36 (s, 1H), 8.16 (s, 1H), 8.12 (d, J = 7.5 Hz, 1H), 7.90 (s, 1H), 7.81 (s, 1H), 7.75-7.21 (m, 2H), 7.40 (d, J =1.5 Hz, 1H), 7.34 (d, J = 1.5 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 3.80 (s, 3H), 2.93 (s, 3H). Example 20: Preparation of N-(2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 117 / 172 34 / 66

[0093] The title compound (16.2 mg, yield: 39%) was obtained in the same manner as in Example 1, except that 1-chloro-4-ethynyl-2-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0094] 1H NMR (500 MHz, DMSO) δ 11.13 (s, 1H), 10.20 (s, 1H), 8.03-7.99 (m, 2H), 7.96-7.94 (m, 1H), 7,837.77 (m, 2H), 7.73-7.70 (m, 2H), 7.15 (s, 1H), 6.50 (dd, J = 17.0, 10.5 Hz, 1H), 6.27 (dd, J = 17.0, 1.5 Hz, 1H), 5.76 (dd, J = 10.0, 1.5 Hz, 1H), 3.93 (s, 3H). Example 21: Preparation of N-(2-(4-chlorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)methanesulfonamide

[0095] 2-(4-Chlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-amine (0.1 mmol, 0.032 g, 1.0 eq.) was dissolved in dichloromethane (1 mL) and then cooled to 0°C. Triethylamine (0.15 mmol, 0.015 g, 1.5 eq.) and methanesulfonyl chloride (0.11 mmol, 0.012 g, 1.1 eq.) were added sequentially. The reaction mixture was reacted at room temperature for 2 hours. After the reaction was complete, the dichloromethane was removed, and the mixture was purified by column chromatography to obtain the title compound (19.8 mg, yield: 49%). Petition 870250087334, dated 09 / 26 / 2025, pp. 118 / 172 35 / 66

[0096] 1H NMR (500 MHz, DMSO) δ 11.25(s,1H), 9.34 (s, 1H), 7.89 (s, 1H), 7.84 (d, J = 8.5 Hz, 2H), 7.79 (s, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.37 (s, 1H), 7.32 (s, 1H), 6.99 (d, J = 1.5 Hz 1H), 3.80 (s, 3H), 2.92 (s,3H). Example 22: Preparation of N-(2-(4-chlorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)-2-fluoroacrylamide

[0097] The title compound (6.1 mg, yield: 15%) was obtained in the same way as in Example 1, except that 2-fluoroacrylic acid was used instead of acrylic acid in step 5 of Example 1.

[0098] 1H NMR (500 MHz, DMSO) δ 11.23 (s,1H), 10.19 (s, 1H), 7.90 (s, 1H), 7.85 (d, J = 8.5 Hz, 2H), 7.82 (s, 1H), 7.75 (m, 2H), 7.57 (d, J = 8.5 Hz, 1H), 7.00(d, J = 2.0 Hz, 1H), 5.72 (dd, J = 48.0, 3.5 Hz, 1H), 5.41 (dd, J = 5.5, 3.5 Hz, 1H), 3.80 (s,3H). Example 23: Preparation of N-(3-chloro-2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 119 / 172 36 / 66 (Step 1)

[0099] 2-(4-Chlorophenyl)-7-(1-methyl-1-imidazol-4-yl)-5-nitro-1H-indol (0.28 mmol, 0.1 g, 1.0 eq.) was dissolved in dimethylformamide (1 mL). N-chlorosuccinimide (0.31 mmol, 0.041 g, 1.1 eq.) was added to the same, and then reacted overnight at room temperature. After the reaction was complete, distilled water was added, and the solid was filtered to obtain 3-chloro-2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4yl)-5-nitro-1H-indol (0.060 g, yield: 55%). (Step 2)

[0100] 3-Chloro-2-(4-chlorophenyl)-7-(1-methyl1H-imidazol-4-yl)-5-nitro-1H-indole (0.15 mmol, 0.060 g, 1.0 eq.), iron (1.5 mmol, 0.083 g, 1.0 eq.), ammonium chloride (0.15 mmol, 0.008 g, 1.0 eq.), and 70% ethanol (10 mL; Ethanol:distilled water = 7:3 (v:v)) were added sequentially, and the reagents were reacted at 80°C for 4 hours. After the reaction was complete, iron and ethanol were removed, extracted with an aqueous ammonium chloride solution, and concentrated, and 3-chloro-2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-amine was used in the next reaction without separation and purification. Petition 870250087334, dated 09 / 26 / 2025, pp. 120 / 172 37 / 66 (Step 3)

[0101] 3-Chloro-2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-amine (0.1 mmol, 0.035 g, 1.0 eq.), N-(3-dimethylaminopropyl)-Netylcarbodiimide hydrochloride (0.2 mmol, 0.038 g, 2.0 eq.), and dichloromethane (1 mL) were sequentially added to a flask. Triethylamine (0.2 mL) and acrylic acid (0.1 mmol, 0.0072 g, 1.0 eq.) were added to the same, and then reacted overnight at room temperature. After the reaction was complete, the dichloromethane was removed, and purified by column chromatography to obtain the title compound (3.7 mg, yield: 9%).

[0102] 1H NMR (500 MHz, DMSO) δ 11.20 (s, 1H), 10.22 (s, 1H), 7.95 (s, 1H), 7.95-7.90 (m, 2H), 7.87 (s, 1H), 7.82-7.80 (m, 2H), 7.67-7.65 (m, 2H), 6.48 (d, J = 10.4 Hz, 1H), 6.28 (d, J = 17.3 Hz, 1H), 5.76 (d, J = 10.0 Hz, 1H), 3.79 (s, 3H). Example 24: Preparation of (E)-N-(2-(4-chlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)-2-cyano-3-phenylacrylamide

[0103] The title compound (19.8 mg, yield: 41%) was obtained in the same manner as in Example 1, except that (E)-2-cyano-3-phenylacrylic acid was used instead of acrylic acid in step 5 of Example 1. Petition 870250087334, dated 09 / 26 / 2025, pp. 121 / 172 38 / 66

[0104] 1H NMR (500 MHz, DMSO) δ 11.25 (s, 1H), 8.67 (s, 1H), 7.99-7.97(m, 2H), 7.73 (d, J = 8.0 Hz, 2H), 7.60 (s, 1H), 7.52-7.51 (m, 3H), 7.46-7.42 (m, 5H), 6.86 (d, J = 2.0 Hz, 1H), 3.81 (s, 3H). Example 25: Preparation of N-(2-(4-chlorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)but-2-inamide

[0105] The title compound (15.4 mg, yield: 39%) was obtained in the same manner as in Example 1, except that but-2-inoic acid was used instead of acrylic acid in step 5 of Example 1.

[0106] 1H NMR (500 MHz, DMSO) δ 11.19 (s, 1H), 10.48 (s, 1H), 7.89 (s, 1H), 7.84 (d, J = 7.0 Hz, 2H), 7.73 (s, 1H), 7.71 (s, 1H), 7.66 (s, 1H), 7.57 (d, J = 7.0 Hz, 2H), 6.97 (s, 1H), 5.77 (s, 3H), 3.80 (s, 3H). Example 26: Preparation of N-(2-(3,4-dichlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)ethanesulfonamide

[0107] 2-(3,4-Dichlorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-amine (0.1 mmol, 0.036 g, 1.0 eq.) was dissolved in dichloromethane (1 mL) and then cooled to 0°C. Triethylamine (0.15 mmol, 0.015 g, 1.5 eq.) and chloride Petition 870250087334, dated 09 / 26 / 2025, pages 122 / 172 39 / 66 ethenesulfonyl (0.11 mmol, 0.014 g, 1.1 eq.) were added sequentially to the same. The reaction mixture was reacted at room temperature for 2 hours. After the reaction was complete, the dichloromethane was removed and purified by column chromatography to obtain the title compound (21.1 mg, yield: 51%).

[0108] 1H NMR (500 MHz, DMSO) δ 11.20 (s, 1H), 9.64 (s, 1H), 8.12 (d, J = 2.0 Hz, 1H), 7.82-7.74 (m, 3H), 7.34 (d, J = 1.5 Hz, 1H), 7.25 (s, 1H), 7.08 (d, J = 2.5 Hz, 1H), 6.75 (dd, J = 16.0, 9.5 Hz, 1H), 6.02-5.95 (m, 2H), 3.80 (s, 3H). Example 27: Preparation of 1-(2-(3,4-dichlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)-1H-pyrrola-2,5diona

[0109] 2-(3,4-Dichlorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-amine (0.1 mmol, 0.036 g, 1.0 eq.), diethyl ether (0.3 mL), and maleic anhydride (0.1 mmol, 0.0098 g, 1.0 eq.) were added sequentially to a sealed tube and then reacted at room temperature for 1 hour. After the reaction was complete, diethyl ether was removed. Sodium acetate (0.05 mmol, 0.0041 g, 0.5 eq.) and acetic anhydride (0.3 mL) were added to the concentrated residue and then reacted at 90°C for 2 hours. After the reaction was complete, the reaction mixture was extracted with an aqueous solution of potassium carbonate and acetate. Petition 870250087334, dated 09 / 26 / 2025, pp. 123 / 172 40 / 66 ethyl, concentrated, and purified by column chromatography to obtain the title compound (8.9 mg, yield: 20%).

[0110] 1H NMR (500 MHz, DMSO) δ 8.17 (d, J = 2.0 Hz, 1H), 7.91 (s, 1H), 7.86-7.84 (m, 2H), 7.78 (d, J = 8.5Hz, 1H), 7.41-7.38 (m, 2H), 7.21 (s, 1H), 7.18 (d, J = 2.0 Hz, 1H), 3.79 (s, 3H). Example 28: Preparation of N-(2-(4-chlorophenyl)-7(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-yl)acrylamide (Step 1)

[0111] 2-Iodo-4-nitroaniline (37.8 mmol, 10 g, A solution of 1.0 eq. was dissolved in dimethylformamide (74 mL) and then cooled to 0°C. N-bromosuccinimide (41.6 mmol, 7.4 g 1.1 eq.) was added to the solution and reacted at room temperature for 5 hours. After the reaction was complete, distilled water (50 mL) was added and stirred for 10 minutes. The yellow solid was filtered to 2-bromo-6-iodo-4-nitroaniline (10 g, yield: 77%). (Step 2)

[0112] 2-Bromo-6-iodo-4-nitroaniline (1.44 Petition 870250087334, dated 09 / 26 / 2025, pp. 124 / 172 41 / 66 mmol, 0.5 g, 1.0 eq.), Pd(PPha)4 (0.072 mmol, 0.083 g, 0.05 eq.), copper iodide (0.14 mmol, 0.026 g, 0.1 eq.), triethylamine (4.32 mmol, 0.6 mL, 3.0 eq.) and tetrahydrofuran (10 mL) were added sequentially, and then ultrasonic degassing was performed under a nitrogen atmosphere for 10 minutes. 1-Chloro-4-ethynylbenzene (1.59 mmol, 0.21 g, 1.1 eq.) was added to the same, and reacted overnight at 40°C. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous solution of ethyl acetate and ammonium chloride, and then solidified with tert-butyl methyl ether to obtain 2-bromo-6-((4-chlorophenyl)ethynyl)-4-nitroaniline (0.3 g, yield: 59%). (Step 3)

[0113] In a sealed tube, 2-bromo-6-((4-chlorophenyl)ethynyl)-4-nitroaniline (0.77 mmol, 0.3 g, 1.0 eq.) was dissolved in 1,4-dioxane (10 mL). 1-Methyl-3(tributylstanyl)-1H-pyrazole (1.0 mmol, 0.37 g, 1.3 eq.), and Pd(PPh3)4 (0.077 mmol, 0.088 g, 0.1 eq.) were added sequentially to the mixture, and then reacted in a microwave reactor at 150°C for 1 hour. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous solutions of ethyl acetate and ammonium chloride, and then solidified with tert-butyl methyl ether to obtain 2((4-chlorophenyl)ethynyl)-6-(1-methyl-1H-pyrazol-3-yl)-4-nitroaniline (0.14 g, yield: 51%). (Step 4)

[0114] 2-((4-Chlorophenyl)ethynyl)-6-(1-methyl1H-pyrazol-3-yl)-4-nitroaniline (0.39 mmol, 0.14 g, 1.0 eq.), sodium hydroxide (1.81 mmol, 0.072 g, 4.6 eq.) and Petition 870250087334, dated 09 / 26 / 2025, pages 125 / 172 42 / 66 dimethylformamide (10 mL) were sequentially added to a microwaveable flask and then reacted at 150°C for 20 minutes. After the reaction was complete, the reaction mixture was extracted with concentrated aqueous ethyl acetate and ammonium chloride solution and then solidified with tert-butyl methyl ether to obtain 2-(4-chlorophenyl)-7(1-methyl-1H-pyrazol-3-yl)-5-nitro-1H-indol (0.1 g, yield: 72%). (Step 5)

[0115] 2-(4-Chlorophenyl)-7-(1-methyl-1H-pyrazole-3-yl)-5-nitro-1H-indole (0.28 mmol, 0.1 g, 1.0 eq.), iron (2.8 mmol, 0.15 g, 1.0 eq.), ammonium chloride (0.28 mmol, 0.014 g, 1.0 eq.), and 70% ethanol (5 mL; ethanol:distilled water = 7:3 (v:v)) were added sequentially. The reagents were reacted at 70°C for 3 hours. After the reaction was complete, iron and ethanol were removed, extracted with an aqueous ammonium chloride solution, and concentrated, and 2-(4-chlorophenyl)-7-(1-methyl-1H-pyrazol-3-yl)-1H-indol-5amine was used in the next reaction without separation and purification. (Step 6)

[0116] 2-(4-Chlorophenyl)-7-(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-amine (0.1 mmol, 0.032 g, 1.0 eq.), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.2 mmol, 0.038 g, 2.0 eq.), and dichloromethane (1 mL) were sequentially added to a flask. Triethylamine (0.1 mL) and acrylic acid (0.11 mmol, 0.0079 g, 1.1 eq.) were added to the same, and then reacted overnight at room temperature. After the reaction was complete, the dichloromethane was removed, and purified by a column of Petition 870250087334, dated 09 / 26 / 2025, pp. 126 / 172 43 / 66 chromatography to obtain the title compound (9.0 mg, yield: 25%).

[0117] 1H NMR (500 MHz, DMSO) δ 10.77 (s,1H), 10.10 (s, 1H), 8.00 (s, 1H), 7.92-7, 88 (m, 3H), 7.71(s, 1H), 7.57-7.55 (m, 2H), 7.03 (d, J = 2.1 Hz, 1H), 6.76(d, J = 2.1 Hz, 1H), 6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.27(d, J = 17.0 Hz, 1H), 5.75 (d, J = 10.1 Hz, 1H), 4.07 (s,3H). Example 29: Preparation of N-(2-(3,4-dichlorophenyl)7-(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-yl)acrylamide H

[0118] The title compound (14.8 mg, yield: 36%) was obtained in the same way as in Example 28, except that 1,2-dichloro-4-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28.

[0119] 1H NMR (500 MHz, DMSO) δ 10.82 (s,1H), 10.11 (s, 1H), 8.20 (s, 1H), 8.02 (s, 1H), 7.89-7.88(m, 2H), 7.78-7.67 (m, 2H), 7.14 (s, 1H), 6.76 (s, 1H),6.48 (dd, J = 17.0, 10.2Hz, 1H), 6.31-6.24 (m, 1H), 5.79-5.72 (m, 1H), 4.06 (s, 3H). Example 30: Preparation of N-(2-(3,4-dichlorophenyl)7-(pyridin-2-yl)-1H-indol-5-yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pages 127 / 172 44 / 66

[0120] The title compound (11.4 mg, yield: 28%) was obtained in the same manner as in Example 28, except that 1,2-dichloro-4-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28, and 2-(tributylstanyl)pyridine was used instead of 1-methyl-3(tributylstanyl)-1H-pyrazole in step 3 of Example 28.

[0121] 1H NMR (500 MHz, DMSO) δ 11.57 (s, 1H), 10.19 (s, 1H), 8.88 (d, J = 4.5 Hz, 1H), 8.25 (br s, 1H), 8.12 (s, 1H), 8.05-8.00 (m, 3H), 7.94 (d, J = 8.2 Hz, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.47-7.43 (m, 1H), 7.18 (s, 1H), 6.50 (dd, J = 16.9, 10.1 Hz, 1H), 6.29 (d, J = 16.9 Hz, 1H), 5.77 (d, J = 10.1 Hz, 1H). Example 31: Preparation of N-(2-(4-fluorophenyl)-7(pyridin-2-yl)-1H-indol-5-yl)acrylamide

[0122] The title compound (9.6 mg, yield: 27%) was obtained in the same manner as in Example 28, except that 1-ethynyl-4-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28, and 2-(tributylstanyl)pyridine was used instead of 1-methyl-3-(tributylstanyl)-1H-pyrazole in step 3 of Example 28.

[0123] 1H NMR (500 MHz, DMSO) δ 11.56 (s, 1H), 10.18 (s, 1H), 8.88 (d, J = 4.6 Hz, 1H), 8.09 (s, 1H), 8.06 - 7.94 (m, 5H), 7.47 - 7.42 (m, 1H), 7.36 - 7.33 (m, 2H), 7.01 (d, J = 2.3 Hz, 1H), 6.50 (dd, J = 16.9, 10.1 Hz, 1H), 6.29 (d, J = 16.9 Hz, 1H), 5.77 (d, J = 11.9 Hz, 1H). Petition 870250087334, dated 09 / 26 / 2025, pp. 128 / 172 45 / 66 Example 32: Preparation of N-(2-(4-fluorophenyl)-7(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-yl)acrylamide

[0124] The title compound (7.9 mg, yield: 22%) was obtained in the same manner as in Example 28, except that 1-ethynyl-4-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28.

[0125] 1H NMR (500 MHz, DMSO) δ 10.73 (s,1H), 10.10 (s, 1H), 7.98 (s, 1H), 7.94-7.91 (m, 2H), 7.89(d, J = 2.2 Hz, 1H), 7.70 (d, J = 1.6 Hz, 1H), 7.37-7.33 (m, 2H), 6.97 (d, J = 2.2 Hz, 1H), 6.76 (d, J = 2.2 Hz, 1H),6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.27 (dd, J = 17.0, 1.8 Hz, 1H), 5.79-5.71 (m, 1H), 4.06 (s,3H). Example 33: Preparation of N-(2-(2,4-difluorophenyl)-7-(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-yl)acrylamide

[0126] The title compound (8.6 mg, yield: 23%) was obtained in the same way as in Example 28, except that 1-ethynyl-2,4-difluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28.

[0127] 1H NMR (500 MHz, DMSO) δ 11.04 (s, 1H), Petition 870250087334, dated 09 / 26 / 2025, pp. 129 / 172 46 / 66 10.13 (s, 1H), 8.09-8.04 (m, 1H), 8.02 (s, 1H), 7.90 (d, J = 2.0 Hz, 1H), 7.74 (d, J = 1.5 Hz, 1H), 7.52-7.47 (m, 1H), 7.27 (td, J = 8.5, 2.5 Hz, 1H), 7.05 (d, J = 2.0 Hz, 1H), 6.76 (d, J = 2.5 Hz, 1H), 6.49 (dd, J = 17.0, 10.0 Hz, 1H), 6.28 (dd, J = 17.0, 2.0 Hz, 1H), 5.75 (dd, J = 10.0, 2.0 Hz, 1H), 4.03 (s, 3H). Example 34: Preparation of N-(2-(5-chloropyridin-2-yl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide (Step 1)

[0128] In a sealed tube, 2-iodo-6-(1-methyl-1H-imidazol-4-yl)-4-nitroaniline (1.5 mmol, 0.52 g, 1.0 eq.) was dissolved in THF (2.5 mL) and TEA (2.5 mL). Pd(PPh3)4 (0.15 mmol, 173.3 mg, 0.1 eq.) and CuI (0.15 mmol, 28.6 mg, 0.1 eq.) were added, and then 5-chloro-2-ethinylpyridine (3.0 mmol, 0.41 g, 2.0 eq.) was added, and reacted overnight at 55°C. After the reaction was complete, the temperature was cooled to room temperature. tert-butyl methyl ether (5 mL) was added, and the solid was filtered to obtain 2-((5-chloropyridin-2-yl)ethinyl)-6-(1-methyl-1H-imidazol-4-yl)-4-nitroaniline (0.49 g, yield: 92%). (Step 2) Petition 870250087334, dated 09 / 26 / 2025, pp. 130 / 172 47 / 66

[0129] In a sealed tube, 2-((5-chloropyridin-2-yl)ethinyl)-6-(1-methyl-1H-imidazol-4-yl)-4-nitroaniline (1.4 mmol, 0.48 g, 1.0 eq.) was dissolved in DMF (7.0 mL), and then CuI (0.14 mmol, 26.7 mg, 0.1 eq.) was added to it, and reacted at 150°C for 1 hour. After the reaction was complete, the temperature was cooled to room temperature. The reaction mixture was extracted with a concentrated aqueous solution of saturated sodium chloride and ethyl acetate, and then separated and purified by column chromatography to obtain 2-(5-chloropyridin-2-yl)-7-(1-methyl-1H-imidazol-4-yl)-5-nitro-1H-indol (0.22 g, yield: 44%). Steps 3 and 4 were performed in the same manner as in Example 1 to obtain the title compound (12.8 mg, yield: 31%).

[0130] 1H NMR (500 MHz, DMSO) δ 9.93 (s, 1H), 8.66 (s, 1H), 8.02 (dd, J = 8.0, 2.5 Hz, 1H), 7.83 (d, J = 8.5 Hz, 1H), 7.79 (s, 1H), 7.76 (d, J = 2.5 Hz, 1H),7.59 (d, J = 2.0 Hz, 1H), 7.40 (s 1H), 6.67 (s, 2H), 6.40 (dd, J = 16.0, 10.0 Hz, 1H), 6.23 (dd, J = 16.0, 1.5 Hz, 1H), 5.72 (dd, J = 10.0, 1.5 Hz, 1H), 3.75 (s, 3H). Example 35: Preparation of 2-(4-fluorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid Pd(PPh3)4x1-ethenyl-4-fluorobenzene । 1-methyl-4-(tributylstanyl) Pd(PPh3)4, Cul -1H-imidazole γN. JJ -------- A^2-----T11,4-dioxane, MW 150°C, TEA, THF, 55°C, during the night 1.5 h J ' Petition 870250087334, dated 09 / 26 / 2025, pp. 131 / 172 48 / 66 (Step 1)

[0131] Ethyl-4-amino-3,5-diiodobenzoate (2.0 mmol, 0.83 g, 1.0 eq.) was dissolved in 1,4-dioxane (10 mL), and then 1-methyl-4-(tributylstanyl)-1H-imidazole (2.1 mmol, 0.78 g, 1.05 eq.), Pd(PPh3)4 (0.4 mmol, 0.46 g, 0.2 eq.) were added sequentially to a sealed tube, and then reacted in a microwave reactor at 140°C for 1.5 hours. After the reaction was complete, the solvent was removed, and the resulting concentrated residue was separated and purified by column chromatography to obtain ethyl 4-amino-3-iodo-5(1-methyl-1H-imidazol-4-yl)benzoate (0.32 g, yield: 44%). (Step 2)

[0132] In a sealed tube, ethyl 4-amino-3-iodo-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.5 mmol, 186 mg, 1.0 eq.) was dissolved in tetrahydrofuran (0.8 mL), and then 1-ethinyl-4-fluorobenzene (0.8 mmol, 96 mg, 1.6 eq.), Pd(PPh3)4 (0.05 mmol, 58 mg, 0.1 eq.), CuI (0.03 mmol, 4.8 mg, 0.05 eq.) and triethylamine (0.8 mL) were added to the mixture, and reacted overnight at 55°C. After the reaction was complete, the temperature was cooled to room temperature. Water (10 mL) and ethyl acetate (5 mL) were added, and the target compound was extracted with the organic layer, dried, and concentrated to obtain ethyl 4-amino-3-((4-fluorophenyl)ethynyl)-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.15 g, yield: 81%). (Step 3)

[0133] In a sealed tube, ethyl 4-amino-3-((4-fluorophenyl)ethynyl)-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.4 mmol, 0.15 g, 1.0 eq.) was added to Petition 870250087334, dated 09 / 26 / 2025, pages 132 / 172 49 / 66 dissolved in dimethylacetamide (2 mL), and then sodium hydroxide (2.0 mmol, 80 mg, 5.0 eq.) was added and reacted in a microwave reactor at 140°C for 15 minutes. Saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (15 mL) were added and extracted, and the resulting organic layer was dried, and then the solvent was removed. The result was separated and purified by column chromatography to obtain ethyl 2-(4-fluorophenyl)-7-(1-methyl-1-himidazol-4-yl)-1H-indol-5-carboxylate (70 mg, yield: 48%). (Step 4)

[0134] 2-(4-fluorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-carboxylate ethyl (0.1 mmol, 0.036 g, 1.0 eq.), 70% ethanol (0.5 mL; ethanol: distilled water = 7:3 (v:v)), and potassium hydroxide (0.2 mmol, 11.2 mg, 2.0 eq.) were added sequentially to a sealed tube, and the mixture was then refluxed for 2 hours. After the reaction was complete, the temperature was cooled to room temperature. Acetic acid (0.2 mL) and purified water (1 mL) were added to the reaction solution, and the resulting solid was filtered to obtain the title compound (21.5 mg, yield: 19%).

[0135] 1H NMR (500 MHz, DMSO) δ 11.30 (s,1H), 8.06 (s, 1H), 8.01 (s, 1H), 7.88 (s, 1H), 7.84 (m, 2H), 7.79 (s, 1H), 7.35 (m, 2H), 6.94 (s, 1H), 3.79 (s, 3H). Example 36: Preparation of 7-(1-methyl-1-Himidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indol-5-carboxylic acid Petition 870250087334, dated 09 / 26 / 2025, pp. 133 / 172 50 / 66 O

[0136] The title compound (21.5 mg, yield: 56%) was obtained in the same manner as in Example 35, except that 1-ethynyl-4-(trifluoromethyl)benzene was used instead of 1-ethynyl-4-fluorobenzene in step 2 of Example 35.

[0137] 1H NMR (500 MHz, DMSO) δ 11.71 (s, 1H), 8.16 (s, 1H), 8.12-8.03 (m, 3H), 7.99 (s, 1H), 7.93 (s, 1H), 7.88 (d, J = 8.2 Hz, 2H), 7.29 (d, J = 1.7 Hz, 1H), 3.80 (s, 3H). Example 37: Preparation of 2-(4-chlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid THE

[0138] The title compound (8.6 mg, yield: 24%) was obtained in the same manner as in Example 35, except that 1-chloro-4-ethynylbenzene was used instead of 1-ethynyl-4-fluorobenzene in step 2 of Example 35.

[0139] 1H NMR (500 MHz, DMSO) δ 12.50 (br, s, 1H), 11.60 (s, 1H), 8.12 (s, 1H), 8.07 (s, 1H), 7.99 (s, 1H), 7.93 (s, 1H), 7.88 (d, J = 8.5 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H), 7.15 (d, J = 1.5 Hz, 1H), 3.80 (s, 3H). Petition 870250087334, dated 09 / 26 / 2025, pages 134 / 172 51 / 66 Example 38: Preparation of 2-(3,4-dichlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid

[0140] The title compound (6.7 mg, yield: 17%) was obtained in the same manner as in Example 35, except that 1,2-dichloro-4-ethynylbenzene was used instead of 1-ethynyl-4-fluorobenzene in step 2 of Example 35.

[0141] 1H NMR (500 MHz, DMSO) δ 12.56 (br, s, 1H), 11.58 (s, 1H), 8.17 (d, J = 1.5 Hz, 1H), 8.13 (s, 1H), 8.09 (s, 1H), 7.98 (s, 1H), 7.92 (s, 1H), 7.84 (dd, J = 8.5, 1.5 Hz, 1H), 7.78 (d, J = 8.5 Hz, 1H), 7.26 (d, J = 2.0 Hz, 1H), 3.80 (s, 3H). Example 39: Preparation of 2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid

[0142] The title compound (22.5 mg, yield: 60%) was obtained in the same manner as in Example 35, except that 1-chloro-4-ethynyl-2-fluorobenzene was used instead of 1-ethynyl-4-fluorobenzene in step 2 of Example 35. Petition 870250087334, dated 09 / 26 / 2025, pp. 135 / 172 52 / 66

[0143] 1H NMR (500 MHz, DMSO) δ 12.59 (br, s, 1H), 11.59 (s, 1H), 8.13 (s, 1H), 8.09 (s, 1H), 7.99-7.97 (m, 2H), 7.92 (s, 1H), 7.76-7.71 (m, 2H), 7.25 (s, 1H), 3.80 (s, 3H). Example 40: Preparation of 2-(4-chlorophenyl)-N-methyl-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylamide TEA, THF, 55°C, overnight 1-ethenyl-4-chlorobenzene Pd(PPh3)4, Cul KOH ,., EtOH, reflux, 3 h (Step 1)

[0144] In a sealed tube, ethyl-4-amino-3,5-diiodobenzoate (2.0 mmol, 0.83 g 1.0 eq.) was dissolved in 1,4-dioxane (10 mL), imidazole (2.1 mmol and then 1-methyl-4-(tributylstanyl)-1H0.78 g, 1.05 eq.), and Pd(PPh3)4 (0.4 mmol 0.46 g, 0.2 eq.) were added sequentially to the same, and then reacted in a microwave reactor at 140°C for 1.5 hours. After the reaction was complete, the solvent was removed, the concentrated residue obtained was separated and purified by column chromatography to obtain 4 Petition 870250087334, dated 09 / 26 / 2025, pp. 136 / 172 53 / 66 ethyl amino-3-iodo-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.32 g, yield: 44%). (Step 2)

[0145] In a sealed tube, ethyl 4-amino-3-iodo-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.5 mmol, 186 mg, 1.0 eq.) was dissolved in tetrahydrofuran (0.8 mL), and then 1-ethinyl-4-chlorobenzene (0.8 mmol, 96 mg, 1.6 eq.), Pd(PPh3)4 (0.05 mmol, 58 mg, 0.1 eq.), CuI (0.03 mmol, 4.8 mg, 0.05 eq.) and triethylamine (0.8 mL) were added to it, and reacted overnight at 55°C. After the reaction was complete, the temperature was cooled to room temperature. Water (10 mL) and ethyl acetate (5 mL) were added, and the target compound was extracted with the organic layer, dried, and concentrated to obtain ethyl 4-amino-3-((4-chlorophenyl)ethynyl)-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.16 g, yield: 84%). (Step 3)

[0146] In a sealed tube, ethyl 4-amino-3-((4-chlorophenyl)ethynyl)-5-(1-methyl-1H-imidazol-4-yl)benzoate (0.4 mmol, 0.15 g, 1.0 eq.) was added and dissolved in dimethylacetamide (2 mL), then sodium hydroxide (2.0 mmol, 80 mg, 5.0 eq.) was added, and reacted in a microwave reactor at 140°C for 15 minutes. Saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (15 mL) were added, extracted, and then the resulting organic layer was dried and the solvent removed. The result was separated and purified by column chromatography to obtain ethyl 2-(4-chlorophenyl)-7-(1-methyl-1-himidazol-4-yl)-1H-indol-5-carboxylate (81 mg, yield: 53%). Petition 870250087334, dated 09 / 26 / 2025, pages 137 / 172 54 / 66 (Step 4)

[0147] 2-(4-chlorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-carboxylate ethyl (0.2 mmol, 0.080 g, 1.0 eq.), 70% ethanol (0.5 mL; ethanol: distilled water = 7:3 (v:v)), and potassium hydroxide (0.2 mmol, 22.4 mg, 2.0 eq.) were added sequentially to a sealed tube, and then the mixture was refluxed for 2 hours. After the reaction was complete, the temperature was cooled to room temperature. Acetic acid (0.2 mL) and purified water (1 mL) were added to the reaction solution, and the resulting solid was filtered to obtain 2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid (36 mg, yield: 51%). (Step 5)

[0148] 2-(4-chlorophenyl)-7-(1-methyl-1-Himidazol-4-yl)-1H-indol-5-carboxylic acid (0.1 mmol, 0.035 g, 1.0 eq.), N-(3-dimethylaminopropyl)-Netylcarbodiimide hydrochloride (0.2 mmol, 0.038 g, 2.0 eq.), and dichloromethane (1 mL) were added sequentially to a flask. Triethylamine (0.1 mL) and acrylic acid (0.11 mmol, 0.0079 g, 1.1 eq.) were added, and then reacted overnight at room temperature. After the reaction was complete, the dichloromethane was removed, and purified by column chromatography to obtain the title compound (10.3 mg, yield: 28%).

[0149] 1H NMR (500 MHz, DMSO) δ 11.47 (s,1H), 8.38-8.35 (m, 1H), 8.00-7.99 (m, 1H), 7.92 (s, 1H), 7.89-7.87 (m, 3H), 7.60-7.58 (m, 2H), 7.11 (s, 1H), 3.81 (s, 3H), 2.83 (s, 3H). Example 41: Preparation of N-(7-(1-methyl-1H)Petition 870250087334, dated 09 / 26 / 2025, page 138 / 172 55 / 66 imidazol-4-yl)-2-(3,4,5-trichlorophenyl)-1H-indol-5yl)acrylamide π Cl

[0150] The title compound (16.8 mg, yield: 19%) was obtained in the same manner as in Example 1, except that 1,2,3-trichloro-5-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0151] 1H NMR (500 MHz, DMSO) δ 11.10 (s,1H), 10.10 (s, 1H), 8.16 (s, 2H), 7.94 (s, 1H), 7.89 (s,1H), 7.79 (s, 1H), 7.72 (s, 1H), 7.20 (d, J = 1.5 Hz, 1H),6.49 (dd, J = 17.0, 10.0 Hz, 1H), 6.26 (d, J = 17.0 Hz, 1H), 5.74 (d, J = 10.0 Hz, 1H), 3.8 (s,3H). Example 42: Preparation of N-(2-(3-fluorophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide

[0152] The title compound (13.5 mg, yield: 36%) was obtained in the same manner as in Example 1, except that 1-ethynyl-3-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0153] 1H NMR (500 MHz, DMSO) δ 11.16 (s,1H), 10.08 (s, 1H), 7.89 (s, 2H), 7.77 (s, 1H), 7.70-7, 65(m, 3H), 7.55 (dd, J = 8.0 Hz 1H), 7.21-7.17 (m, 1H), 7.04(d, Petition 870250087334, dated 09 / 26 / 2025, pages 139 / 172 56 / 66 J =2.5 Hz, 1H), 6.49 (dd, J = 17.0, 10.0 Hz, 1H), 6.27 (dd, J = 17.0, 2.0 Hz, 1H), 5.74 (dd, J = 10.0, 2.0 Hz, 1H), 3.80 (s, 3H). Example 43: Preparation of 2-(3,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid THE

[0154] The title compound (23.4 mg, yield: 74%) was obtained in the same manner as in Example 35, except that 4-ethynyl-1,2-difluorobenzene was used instead of 1-ethynyl-4-fluorobenzene in step 2 of Example 35.

[0155] 1H NMR (500 MHz, DMSO) δ 11.52 (s,1H), 8.11 (s, 1H), 8.08 (s, 1H), 8.01-7.96 (m, 2H), 7.91 (s,1H), 7.70-7.69 (m, 1H), 7.61 (dd, J = 9.0 Hz, 1H), 7.15 (d, J = 2.0 Hz, 1H), 3.80 (s, 3H). Example 44: Preparation of N-(2-(3-chloro-4-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide H

[0156] The title compound (10.8 mg, yield: 27%) was obtained in the same way as in Example Petition 870250087334, dated 09 / 26 / 2025, pages 140 / 172 57 / 66 1, except that 2-chloro-4-ethynyl-1-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0157] 1H NMR (500 MHz, DMSO) δ 11.09 (s, 1H), 10.06 (s, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.88 (d, J =7.0 Hz, 2H), 7.83 (s, 1H), 7.76 (s, 1H), 7.69 (s, 1H), 7.56-7.52 (m, 1H),7.01 (s, 1H), 7.01 (s, 1H), 6.49 (dd, J = 17.0,10.0 Hz, 1H), 6.26 (d, J = 10.0 Hz, 1H), 3.80 (s,3H). Example 45: Preparation of N-(2-(2,4-dichlorophenyl)7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide H

[0158] The title compound (12.0 mg, yield: 27%) was obtained in the same way as in Example 1, except that 2,4-dichloro-1-ethynylbenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0159] 1H NMR (500 MHz, DMSO) δ 1.50 (s,1H), 10.09 (s, 1H), 7.91 (s, 1H), 7.89-7.84 (m, 2H), 7.80(d, J = 2.0 Hz, 1H), 7.72 (d, J = 1.5 Hz, 1H), 7.59-7.57 (m, 1H), 6.94 (d, J = 2.0 Hz, 1H), 6.50 (dd, J = 17.0, 10.0 Hz, 1H), 6.27 (dd, J = 17.0, 2.0 Hz, 1H), 5.74 (dd, J = 10.0, 2.0 Hz, 1H), 3.78 (s,3H). Example 46: Preparation of N-(2-(4-chloro-3,5-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide Petition 870250087334, dated 09 / 26 / 2025, pp. 141 / 172 58 / 66

[0160] The title compound (36.2 mg, yield: 18%) was obtained in the same manner as in Example 1, except that 2-chloro-5-ethynyl-1,3-difluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0161] 1H NMR (500 MHz, DMSO) δ 11.10 (s,1H), 10.11 (s, 1H), 7.94 (s, 1H), 7.89-7, 88 (m, 3H), 7.79(s, 1H), 7.72 (s, 1H), 7.18 (s, 1H), 6.49 (dd, J = 17.0,10.0 Hz, 1H), 6.26 (d, J = 17.0 Hz, 1H), 5.74 (dd, J = 10.0 Hz, 1H), 3.81 (s,3H). Example 47: Preparation of N-(2-(4-chloro-2,6-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5yl)acrylamide

[0162] The title compound (34.7 mg, yield: 10%) was obtained in the same manner as in Example 1, except that 5-chloro-2-ethynyl-1,3-difluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1. 1.

[0163] 1H NMR (500 MHz, DMSO) δ 11.65 (s, 1H), Petition 870250087334, dated 09 / 26 / 2025, pp. 142 / 172 59 / 66 10.11 (s, 1H), 7.90 (s, 2H), 7.74 (dd, J = 7.0, 1.5 Hz, 1H), 7.60 (d, J = 9.5 Hz, 1H), 7.00 (s, 1H), 6.50 (d, J = 17.0, 10.0 Hz, 1H), 6.27 (dd, J = 17.0, 2.0 Hz, 1H), 5.74 (dd, J = 10.0, 2.0 Hz, 1H), 3.79 (s, 3H). Example 48: Preparation of N-(7-(1-methyl-1-Himidazol-4-yl)-2-(4-(trifluoromethoxy)phenyl)-1H-indol-5yl)acrylamide

[0164] The title compound (38.0 mg, yield: 89%) was obtained in the same manner as in Example 1, except that 1-ethynyl-4-(trifluoromethoxy)benzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0165] 1H NMR (500 MHz, DMSO) δ 11.17 (s, 1H), 10.06 (s, 1H), 7.94 (d, J = 8.5 Hz, 1H), 7.88 (s, 2H), 7.76 (s, 1H), 7.70 9s, 1H), 7.49 (d, J = 8.5 Hz, 1H), 6.98 (s, 1H), 6.49 (dd, J = 17.0, 10.0 Hz, 1H), 6.26 (d, J = 17.0 Hz, 1H), 5.73 (d, J = 10.0 Hz, 1H), 3.80 (s, 3H). Example 49: Preparation of N-(2-(4-chlorophenyl)-7(4-methylthiazol-2-yl)-1H-indol-5-yl)acrylamide H

[0166] The title compound (15.1 mg, Petition 870250087334, dated 09 / 26 / 2025, pp. 143 / 172 60 / 66 yield: 38%) was obtained in the same manner as in Example 28, except that 4-methyl-2-(tributylstanyl)thiazole was used instead of 1-methyl-3-(tributylstanyl)-1H-pyrazole in step 3 of Example 28.

[0167] 1H NMR (500 MHz, DMSO) δ 11.08 (s,1H), 10.23 (s, 1H), 8.12 (d, J = 1.7 Hz, 1H), 7.97 (d, J =1.8 Hz, 1H), 7.91 (d, J = 8.5 Hz, 2H), 7.58 (d, J = 8.5 Hz, 2H), 7.40 (s, 1H), 7.10 (d, J = 2.3 Hz, 1H), 6.47 (dd, J =17.0, 10.1 Hz, 1H), 6.36 - 6.23 (m, 1H), 5.81 - 5.71 (m, 1H),2.60 (s,3H). Example 50: Preparation of N-(7-(1-ethyl-1-Himidazol-4-yl)-2-(3,4,5-trifluorophenyl)-1H-indol-5-yl)acrylamide

[0168] The title compound (15.0 mg, yield: 36%) was obtained in the same manner as in Example 28, except that 5-ethynyl-1,2,3-trifluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28, and 1-ethyl-4-(tributylstanyl)-1H-imidazole was used instead of 1-methyl-3-(tributylstanyl)-1H-pyrazole in step 3 of Example 28.

[0169] 1H NMR (500 MHz, CDC13) δ 7.87 (d, J = 1.9 Hz, 1H), 7.65 (s, 1H), 7.57 (s, 1H), 7.46 (s, 1H), 7.42 - 7.33 (m, 4H), 6.74 (d, J = 2.6 Hz, 1H), 6.49 (d, J = 16.8 Hz, 1H), 6.32 (dd, J = 16.8, 10.2 Hz, 1H), 5.80 (d, J = 10.1 Hz, 1H), 4.10 (q, J = 7.3 Hz, 2H), 1.56 (t, J = 7.3 Hz, 3H). Petition 870250087334, dated 09 / 26 / 2025, pages 144 / 172 61 / 66 Example 51: Preparation of N-(7-(1-ethyl-1-Himidazol-4-yl)-2-(4-fluorophenyl)-1H-indol-5-yl)acrylamide H

[0170] The title compound (25.2 mg, yield: 66%) was obtained in the same manner as in Example 28, except that 1-ethynyl-4-fluorobenzene was used instead of 1-chloro-4-ethynylbenzene in step 2 of Example 28, and 1-ethyl-4-(tributylstanyl)-1H-imidazole was used instead of 1-methyl-3-(tributylstanyl)-1H-pyrazole in step 3 of Example 28.

[0171] 1H NMR (500 MHz, DMSO) δ 11.14 (s, 1H), 10.05 (s, 1H), 7.96 (s, 1H), 7.94 - 7.81 (m, 4H), 7.71 (d, J = 1.8 Hz, 1H), 7.35 (t, J = 8.7 Hz, 2H), 6.91 (d, J = 2.3 Hz, 1H), 6.49 (dd, J = 17.0, 10.1 Hz, 1H), 6.26 (dd, J = 17.0, 2.1 Hz, 1H), 5.74 (dd, J = 10.1, 2.1 Hz, 1H), 4.13 (q, J = 7.3 Hz, 2H), 1.46 (t, J = 7.3 Hz, 3H). Example 52: Preparation of N-(2-(4-bromophenyl)-7(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide H

[0172] The title compound (38.0 mg, yield: 89%) was obtained in the same manner as in Example 1, except that 1-bromo-4-ethynylbenzene was used instead of Petition 870250087334, dated 09 / 26 / 2025, pages 145 / 172 62 / 66 1-chloro-4-ethynylbenzene in step 2 of Example 1.

[0173] 1H NMR (500 MHz, DMSO) δ 11.16 (s,1H), 10.07 (s, 1H), 7.92 - 7.86 (m, 2H), 7.83 - 7.75 (m,3H), 7.73 - 7.67 (m, 3H), 6.99 (d, J = 2.4 Hz, 1H), 6.49 (dd, J = 16.9, 10.1 Hz, 1H), 6.35 - 6.12 (m, 1H), 5.74 (dd, J = 10.1, 2.1 Hz, 1H), 3.80 (s,3H). Experimental Example 1: Inhibition Test of TEAD Transcription Factor Activity

[0174] The TEAD transcription factor activity of the compounds prepared in the Examples was measured by the ONE-GloTM luciferase assay method (Promega, Catalog No. E6110) using the recombinant cell line Hippo Pathway TEAD reporter-MCF7 (BPS Bioscience, Catalog No. 60618).

[0175] Specifically, the cell lineage TEAD Reporter-MCF7 contains the firefly luciferase gene, whose expression is regulated under the control of TEAD response elements in MCF7, a human breast cancer cell line. In the cell line, there is an unphosphorylated YAP / TAZ in the nucleus under non-stressed conditions, which continuously induces reporter luciferase expression.

[0176] TEAD Reporter-MCF7 cells were prepared in 100 μL of cell culture medium (MEM medium, 10% FBS, 1% P / S, 400 μg / mL Geneticin, 1% N-ethyl acetate A, 1 mM NA pyruvate, 10 μg / mL Insulin) in a 96-well microplate with a transparent white bottom. The prepared plate was incubated in a 5% CO2 incubator at 37°C for 24 hours, and then the previously prepared compounds from the Examples were finally treated at concentrations of 0.0005, 0.005, 0.05, 0.5, and 5 μN, which were Petition 870250087334, dated 09 / 26 / 2025, pages 146 / 172 63 / 66 repeated three times for all treatment solutions. Plates treated with the compounds from the Examples were incubated in a 5% CO2 incubator at 37°C for 24 hours. 100 μL / well of the aqueous substrate solution containing luciferin was added to a 96-well microplate with a clear, white bottom, thus initiating an enzymatic reaction. The reaction was carried out at room temperature for 5 minutes, and the luminescence (integration time of 1000 ms) was measured using a Flexstation3 multimode microplate reader. According to the instructions for the ONE-Glo™ Luciferase Assay, the luciferase enzyme activity, representing the TEAD transcription factor activity, was measured by a chemiluminescence method, and the inhibitory activity of the compound according to the present disclosure was calculated. The results for each compound were analyzed using Microsoft Excel, and the IC50 values ​​were calculated using GraphPad Prism software.The results are shown in Table 1 below. Experimental Example 2: Cell Growth Inhibition Test

[0177] Cell growth for the compounds prepared in the Examples was measured by the CellTiterGlo® Luminescent Cell Viability method (Promega, Catalog No. G7571) using NCI-H226 (addexbio) and NCI-H28 (Korea Cell Line Bank) cell lines. This evaluation method consists of a method in which, when the luciferase enzyme is activated by ATP flowing from living cells, it reacts with a luciferin substrate, and the enzymatic activity at this time is measured to confirm cell viability. Petition 870250087334, dated 09 / 26 / 2025, pages 147 / 172 64 / 66

[0178] Specifically, the NCI-H226 cells and NCI-H28 compounds were prepared in 100 μL of cell culture medium (RPMI medium, 10% FBS, 1% P / S, 4.5 g / L D-glucose, 2.383 g / L HEPES buffer, L-glutamine, 1.5 g / L sodium bicarbonate, 110 mg / L sodium pyruvate) in a 96-well microplate with a transparent white bottom. The prepared plate was incubated in a 5% CO2 incubator at 37°C for 24 hours, and then the previously prepared compounds from the Examples were finally treated at concentrations of 0.0005, 0.005, 0.05, 0.5, and 5 μM, which was repeated three times for all treatment solutions. Plates treated with the compounds from the Examples were incubated in a 5% CO2 incubator at 37 °C. 100 μL / well of the aqueous substrate solution containing luciferin were added to a 96-well microplate with a clear, white bottom, thus initiating an enzymatic reaction.The reaction was carried out at room temperature, in the dark, for 10 minutes, and luminescence was measured using a Flexstation3 multimode microplate reader. Following the instructions of CellTiter-Glo™ Luminescent Cell Viability, the activity of the luciferase enzyme, which represents the amount of ATP, was measured by a chemiluminescence method, and the inhibitory activity of the compounds according to this disclosure was calculated. The results for each compound were analyzed using Microsoft Excel, and the IC50 values ​​were calculated using GraphPad Prism software. The results are shown in Table 1 below. Table 1 Petition 870250087334, dated 09 / 26 / 2025, pages 148 / 172 65 / 66 Example No. TEAD IC50 (nM) Growth IC50 (μM) H226 Growth IC50 (μM) H2 8 Example No. TEAD IC50 (nM) Growth IC50 (μM) H226 Growth IC50 (μM) H2 8 1 0.0094 0.0210 > 5 30 0.1260 0.3386 0.553 2 0.0390 0.0650 4.140 31 0.0300 0.012 1.767 3 0.0035 0.0025 1.530 32 0.0230 0.0076 1.357 4 0.0300 0.0100 4.400 33 0.0510 0.0243 4.914 5 0.0064 0.0042 > 5 35 0.1000 0.1367 > 5 6 0.0059 0.0044 4.000 37 0.0260 0.1345 0.759 8 0.1100 0.0570 0.950 39 0.0360 0.0219 > 5 9 0.0200 0.0053 2.950 42 0.0970 0.0045 2.080 10 0.0600 0.0200 2.469 43 0.0540 0.0078 > 5 12 0.0790 0.0225 2,800 44 0.0370 0.0217 1,900 13 0.0460 0.0223 3,500 46 0.0900 0.0790 1,360 14 0.0490 0.0251 2,300 50 0.0270 0.0154 > 5 19 0.1900 0.2099 0.438 51 0.0480 0.0076 2,540 21 0.2360 > 5 2,221 52 0.3460 0.0580 0.868 28 0.0150 0.0084 2,300 Experimental Example 3: CTGF Analysis Test, CYR61

[0179] NCI-H226 human mesothelioma cells (AddexBio) were cultured in a 6-well cell culture plate at a density of 5x105 cells per well. After a 24-hour stabilization process, Example 1 was treated at a concentration of 500 nM, and cells treated with the same amount of DMSO were defined as controls. 24 hours after treatment, cells were collected to secure RNA for target gene expression analysis.

[0180] RNA was extracted from cells Petition 870250087334, dated 09 / 26 / 2025, pp. 149 / 172 66 / 66 using a TRIzol solution (Ambion). After cell lysis and digestion were complete, chloroform was added to each sample and the homogenate was separated into aqueous and organic phases by centrifugation.

[0181] The expression of ctgf (connective tissue growth factor) and cyr61 (cysteine-rich angiogenic inducer 61), which are YAP-TEAD regulated genes, and gapdh (glyceraldehyde 3-phosphate dehydrogenase), which is a maintenance gene, were quantified by qRT-PCR analysis using the Maxima SYBR Green / Fluorescein qPCR master mix and primers for each gene. Cycle threshold (Ct) values ​​of ctgf, cyr61, and gapdh from cellular cDNA samples were determined, and the expression of ctgf and cyr61 was normalized to gapdh.

[0182] The expression of each gene in the experimental group treated with Example 1 was normalized relative to the control treated with DMSO. Figure 1 shows the regulatory properties of the expression of two TEAD target genes in Example 1 using real-time PCR. Petition 870250087334, dated 09 / 26 / 2025, pages 150 / 172

Claims

1 / 9 CLAIMS 1. Compound represented by Chemical Formula 1 below, or a pharmaceutically acceptable salt thereof: Chemical Formula 1 R3 in Chemical Formula 1, Ri is a C6-10 aryl; or a 5- or 6-membered heterocycle containing 1 to 4 heteroatoms each independently selected from the group consisting of N, O and S, characterized in that Ri is unsubstituted; or substituted with halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 thioalkoxy, a C1-4 haloalkoxy, a C2-4 alkenyl, a C2-4 alkynyl, a C3-6 cycloalkyl, amino, nitro, cyano, a (C1-4 alkyl)amino, or a (C1-4 dialkyl)amino; or is fused with a C3-6 cycloalkyl ring, R2 being a C6-10 aryl; a C3-6 cycloalkenyl; or a 5- or 6-membered heterocycle containing 1 to 4 heteroatoms each independently selected from the group consisting of N, O, and S,wherein R2 is unsubstituted; or substituted with 1 to 3 substituents each independently selected from the group consisting of halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 thioalkoxy, a C1-4 haloalkoxy, a C2-4 alkenyl, a C2-4 alkynyl, a C3-6 cycloalkyl, amino, nitro, cyano, a Petition 870250087334, dated 09 / 26 / 2025, p. 151 / 172 2 / 9 (alkyl C1-4)amino, and a (dialkyl C1-4)amino, R3 is hydrogen or halogen, R4 is -NHCO-R', -NHSO2-R', -COO-R', -CONH-R', or 1Hpyrrola-2,5-dione-1-yl, wherein R' is hydrogen, a C1-4 alkyl, a C2-4 alkynyl, or a substituent represented by Chemical Formula 2 below: Chemical Formula 2 R'2 R'1 in Chemical Formula 2, R'i is hydrogen, halogen, or cyano, and R'2 is each independently hydrogen, a C6-10 aryl, -CH2-NH2, -CH2-NH(C1-4 alkyl), or -CH2-N(C1-4 alkyl)2.

2. Pharmaceutically acceptable compounds or salts thereof according to claim 1,characterized in that: R1 is phenyl, pyridinyl, pyrimidinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyrrolidinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, or isothiazolyl, wherein R1 is unsubstituted; or substituted with a halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 haloalkoxy, an amino, nitro, cyano, a (C1-4 alkyl)amino, or a (C14 dialkyl)amino, or is fused with a C3-6 cycloalkyl ring. Petition 870250087334, dated 26 / 09 / 2025, p. 152 / 172 3 / 9 3. Pharmaceutically acceptable compounds or salts thereof, according to claim 1, characterized in that: R1 is imidazolyl, imidazolyl fused with cyclopentane, pyrazolyl, or pyridinyl, wherein R1 is unsubstituted; or substituted with methyl, ethyl, fluoromethyl, difluoromethyl, or trifluoromethyl.

4. Pharmaceutically acceptable compounds or salts thereof, according to claim 1,characterized in that: R2 is phenyl, pyridinyl, pyrimidinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyrrolidinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, or isothiazolyl, wherein R2 is unsubstituted; or substituted with a halogen, a C1-4 alkyl, a C1-4 thioalkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 haloalkoxy, an amino, nitro, cyano, a (C1-4 alkyl)amino, or a (C14 dialkyl)amino.

5. Pharmaceutically acceptable compounds or salts thereof, according to claim 1, characterized in that: R2 is phenyl, pyridinyl, or cyclohexenyl, wherein R2 is unsubstituted; or substituted with 1 to 3 substituents each independently selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, and trifluoromethoxy. Petition 870250087334, dated 09 / 26 / 2025, p. 153 / 172 4 / 9 6. Pharmaceutically acceptable compounds or salts thereof according to claim 1,characterized in that: R3 is hydrogen, or chlorine.

7. Pharmaceutically acceptable compounds or salts thereof, according to claim 1, characterized in that: R4 is -NHCO-R', -NHSO2-R', -COO-R', -CONH-R', or 1Hpyrrola-2,5-dione-1-yl; wherein R' is hydrogen; a C1-4 alkyl; a C2-4 alkenyl that is unsubstituted, or substituted with 1 or 2 substituents each independently selected from the group consisting of phenyl, fluorine, and cyano; or a C2-4 alkynyl.

8. Pharmaceutically acceptable compounds or salts thereof, according to claim 1, characterized in that: R4 is -NHCO-CH=CH2, -NHCO-CF=CH2, -NHCOC(CN)=CH(phenyl), -NiCO-C C-CH , -NHSO2-CH3, -NHSO2-CH=CH2, COOH, -CONH-CH3, or 1H-pyrrola-2,5-dione-1-yl, 9. Pharmaceutically acceptable compounds or salts thereof, according to claim 1,characterized in that: Chemical Formula 1 is represented by Chemical Formula 3 as follows: Chemical Formula 3 Petition 870250087334, dated 09 / 26 / 2025, page 154 / 172 5 / 9 in Chemical Formula 3, R is each independently hydrogen, halogen, a C1-4 alkyl, or a C1-4 haloalkyl, n is an integer from 1 to 3, and R4 is -NHCO-CH=CH2, or -COOH.

10. Pharmaceutically acceptable compounds or salts thereof, according to claim 1, characterized in that the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 1) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 2) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide, 3) N-(2-(4-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 4) N-(7-(1-methyl-1H-imidazol-4-yl)-2-phenyl-1H-indol-5-yl)acrylamide, 5) N-(2-(2,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 6) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3,4,5-trifluorophenyl)-1H-indol-5-yl)acrylamide, 7) N-(7-(1-(difluoromethyl)-1H-imidazol-4-yl)-2-(4-fluorophenyl)-1H-indol-5-yl)acrylamida, Petição 870250087334, de 26 / 09 / 2025, pág. 155 / 172 6 / 9 8) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 9) N-(2-(3,4-difluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 10) N-(2-(3-chlorophenyl)-7-(1-methyl-1H-imidazol- 4-yl)-1H-indol-5-yl)acrylamide, 11) N-(2-(4-chlorophenyl)-7-(1-(difluoromethyl)-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 12) N-(2-(4-chloro-2-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 13) N-(2-cyclohexenyl-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 14) N-(2-(4-fluor-3-methylphenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 15) N-(7-(1-methyl-1H-imidazol-4-yl)-2-p-tolyl- 1H-indol-5-yl)acrylamide, 16) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3-(trifluoromethyl)phenyl)-1H-indol-5-yl)acrylamide, 19) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3(trifluoromethyl)phenyl)-1H-indol-5-yl)methanesulfonamida, 20) N-(2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, 21) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol- 4-yl)-1H-indol-5-yl)methanesulfonamida, 22) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol- 4-yl)-1H-indol-5-yl)-2-fluoroacrylamide, 23) N-(3-chloro-2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 24) (E)-N-(2-(4-chlorophenyl)-7-(1-methyl-1H- imidazol-4-yl)-1H-indol-5-yl)-2-cyano-3-phenylacrylamida, Petição 870250087334, de 26 / 09 / 2025, pág. 156 / 172 7 / 9 25) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol- 4-yl)-1H-indol-5-yl)but-2-inamide, 26) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)ethenesulfonamide, 27) 1-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)-1H-pyrrola-2,5-dione, 28) N-(2-(4-chlorophenyl)-7-(1-methyl-1H-pyrazol-3-yl)-1H-indol-5-yl)acrylamide, 29) N-(2-(3,4-dichlorophenyl)-7-(1-methyl-1Hpyrazol-3-yl)-1H-indol-5-yl)acrylamide, 30) N-(2-(3,4-dichlorophenyl)-7-(pyridin-2-yl)-1H- indol-5-yl)acrylamide, 31) N-(2-(4-fluorophenyl)-7-(pyridin-2-yl)-1H- indol-5-yl)acrylamide, 32) N-(2-(4-fluorophenyl)-7-(1-methyl-1H-pyrazol- 3-yl)-1H-indol-5-yl)acrylamide, 33) N-(2-(2,4-difluorophenyl)-7-(1-methyl-1H- pyrazol-3-yl)-1H-indol-5-yl)acrylamide, 34) N-(2-(5-chloropyridine-2-yl)-7-(1-methyl-1H- imidazol-4-yl)-1H-indol-5-yl)acrylamide, 35) 2-(4-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, 36) 7-(1-methyl-1H-imidazol-4-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole-5-carboxylic acid, 37) 2-(4-chlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, 38) 2-(3,4-dichlorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indole-5-carboxylic acid, 39) 2-(4-chloro-3-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxylic acid, Petition 870250087334, dated 09 / 26 / 2025, page 157 / 172 8 / 9 40) 2-(4-chlorophenyl)-N-methyl-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-carboxamide, 41) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(3,4,5-trichlorophenyl)-1H-indol-5-yl)acrylamide, 42) N-(2-(3-fluorophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 43) 2-(3,4-difluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indole-5-carboxylic acid, 44) N-(2-(3-chloro-4-fluorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indol-5-yl)acrylamide, 45) N-(2-(2,4-dichlorophenyl)-7-(1-methyl-1Himidazol-4-yl)-1H-indole-5-yl)acrylamida, 46) N-(2-(4-chloro-3,5-difluorophenyl)-7-(1-methyl- 1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 47) N-(2-(4-chloro-2,6-difluorophenyl)-7-(1-methyl- 1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide, 48) N-(7-(1-methyl-1H-imidazol-4-yl)-2-(4-(trifluoromethoxy)phenyl)-1H-indol-5-yl)acrylamide, 49) N-(2-(4-chlorophenyl)-7-(4-methylthiazol-2-yl)- 1H-indol-5-yl)acrylamide, 50) N-(7-(1-ethyl-1H-imidazol-4-yl)-2-(3,4,5-trifluorophenyl)-1H-indol-5-yl)acrylamide, 51) N-(7-(1-ethyl-1H-imidazol-4-yl)-2-(4-fluorophenyl)-1H-indol-5-yl)acrylamide, and 52) N-(2-(4-bromophenyl)-7-(1-methyl-1H-imidazol-4-yl)-1H-indol-5-yl)acrylamide.

11. Pharmaceutical composition for the prevention or treatment of cancer or tumors, characterized by comprising the compound according to any of claims 1 to 10, or a pharmaceutically acceptable salt thereof as the active ingredient. Petition 870250087334, dated 09 / 26 / 2025, pp. 158 / 172 9 / 9

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