Novel compound as NLRP3 inhibitor and pharmaceutical compositions comprising same

Abstract

The present invention relates to a novel compound as an NLRP3 inhibitor and pharmaceutical compositions comprising same and, more specifically, to: a novel NLRP3 inhibitor compound having good activity as an NLPR3 inhibitor and thus being useful for neurodegenerative diseases or chronic inflammatory diseases; and pharmaceutical compositions comprising the novel compound.

Description

Novel compound as an NLRP3 inhibitor and pharmaceutical composition containing the same The present invention relates to a novel compound as an NLRP3 inhibitor and a pharmaceutical composition containing the same, and more specifically, to a novel NLRP3 inhibitor compound having good activity as an NLRP3 inhibitor and having useful efficacy for inflammatory diseases such as neurodegenerative diseases or chronic inflammation, and a pharmaceutical composition containing the same. NOD-like receptor 3 (NLRP3) is a protein-coding gene and an intracellular signaling molecule that detects multiple pathogen-derived, environmental, and host-derived factors. In response to sterile inflammation danger signals, NLRP3 binds to apoptosis-associated speck-like protein (ASC), which contains caspase-activating and supplementary domains. Subsequently, the ASC polymerizes to form large aggregates known as ASC specks, and the polymerized ASC then interacts with the cysteine ​​protease caspase-1 to form a complex called the NLRP3 inflammasome. This leads to the activation of caspase-1, which activates these cytokines by cleaving their precursor forms (referred to as pro-IL-1β and pro-IL-18, respectively). Caspase 1 activation can mediate cell death directly (through a process known as pyroptosis) or indirectly (through apoptosis) (V. Sagulenko et al., Cell Death Differ 20, 1149-1160 (2013)). ASC spots can also replenish and activate caspase-8, which can trigger apoptosis by processing pro-IL-1β and pro-IL-18. In other words, NLRP3 inflammasome activation can cause a number of related diseases by resulting in the release of inflammatory cytokines IL-1β and IL-18. It is known that NLRP3 inflammasome activation can contribute to the onset and progression of various inflammasome-related diseases / disorders, immune diseases, inflammatory diseases, autoimmune diseases, and autoinflammatory diseases. Furthermore, it has been shown that the involvement of increased production of IL-1β and IL-18 by the NLRP3 inflammasome can contribute to the onset and progression of various diseases, such as neuroinflammation-related disorders (e.g., brain infections, acute injury), neurodegenerative diseases including Alzheimer's disease, multiple sclerosis, and Parkinson's disease, cardiovascular / metabolic disorders / disorders, inflammatory skin diseases, and cancer-related diseases / disorders. Recent studies have shown that mitochondrial dysfunction and NLRP3 activation are associated in neuroinflammation-related diseases such as Parkinson's disease (Zhou et al., Nature, 2011, 469, 221). One of the major problems associated with mitochondrial regulators is their poor metabolic stability, so selective and stable inhibitors are needed for neuroinflammation of this nature (Lee et al., Eur J. Org. Chem.2017, 141, 240). Meanwhile, current treatments for NLRP3-related diseases include biological agents that target IL-1β. These include the recombinant IL-1β receptor antagonist anakinra, the neutralizing IL-1β antibody canakinumab, and the soluble decoy IL-1β receptor rilonacept. These approaches have proven successful in the treatment of CAPS, and these biological agents have been used in clinical trials for other IL-1β-associated diseases. Several biological therapies, including the antibodies canakinumab, anakinra, and rilonacept, target inflammasome-induced IL-1β, IL-1RA, and IL-18 for the treatment of NLRP3-related diseases (CA Dinarello et al., Semin Immunol 25, 469-484 (2013)). Although several small molecule inhibitors of the NLRP3 inflammasome, including glyburide, parthenolide, Bay11-708, auranofin, CRID3, and β-hydroxybutyrate (BHB), have been reported, some of these inhibitors have non-specific and limited efficacy (E. Isakov, P et al., Biochim Biophys Acta 1840, 3153-3161 (2014)). Therefore, there is a need for inhibitors of the NLRP3 inflammasome pathway to provide new and alternative therapies for these inflammasome-related diseases / disorders. Accordingly, the inventors made diligent efforts to develop a new NLRP3 inflammasome inhibitor, synthesized NLRP3 inhibitor compounds, and through in vitro experiments, found that these compounds inhibit the NLRP3 inflammasome and prevent the expression of caspase 1 and IL-1β, thereby completing the present invention. [No prior art] [Patent Literature] Republic of Korea Published Patent No. 10-2020-0041919 Republic of Korea Published Patent No. 10-2023-0066899 Republic of Korea Published Patent No. 10-2023-0002652 Republic of Korea Published Patent No. 10-2023-0157535 [Non-patent literature] V. Sagulenko et al., Cell Death Differ 20, 1149-1160 (2013) Zhou et al., Nature, 2011, 469, 221 Lee et al., Eur J. Org. Chem.2017, 141, 240 C. A. Dinarello et al., Semin Immunol 25, 469-484 (2013) E. Isakov, P et al., Biochim Biophys Acta 1840, 3153-3161 (2014) The object of the present invention is to provide a novel compound and a pharmaceutical composition thereof that inhibits the NLRP3 inflammasome and prevents the expression of caspase 1 and IL-1β for inflammatory diseases such as neurodegenerative diseases or chronic inflammatory diseases. To achieve the above objective, the present invention provides a compound represented by Formula 1, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof. The present invention also provides a pharmaceutical composition for treating or preventing inflammatory diseases comprising the compound, its salt, or its stereoisomer as an active ingredient. The present invention also provides a health functional food for preventing or improving inflammatory diseases, comprising the compound, its salt, or its stereoisomer as an active ingredient. The present invention also provides a pharmaceutical formulation comprising the above-mentioned pharmaceutical composition for the treatment or prevention of inflammatory diseases. A composition comprising a compound of Formula 1 according to the present invention, a salt or isomer thereof as an active ingredient inhibits the NLRP3 inflammasome and prevents the expression of caspase 1 and IL-1β, thereby having an excellent improvement effect in the treatment of inflammatory diseases. FIG. 1 is a diagram illustrating the results of a Western blot analysis according to an embodiment of the present invention. Specific details for implementing the invention Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by a skilled expert in the art to which this invention pertains. In general, the nomenclature used herein is well known and commonly used in the art. It has been confirmed that a composition comprising the compound of Formula 1 according to the present invention, its salt, or its isomer as an active ingredient has good NLRP3 inhibitory activity and is effective against inflammatory diseases such as neurodegenerative diseases or chronic inflammatory diseases. Accordingly, in one aspect, the present invention relates to a compound represented by Formula 1, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 1] In Chemical Formula 1 R 1 , R 2 and R 3 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl; -CONR 10 R 11 ; -NR 10 CO-R 11 ; R 12 CO- and, here, R 10 and R 11 Each is independently a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A and, Here, A is i) a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and R 12 ... is a C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, or C5-C20 alkylheteroaryl, wherein the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4, and; R 4 is a hydrogen atom or a C1-C6 alkyl. In another aspect, the present invention relates to a pharmaceutical composition for treating or preventing inflammatory diseases comprising the above-mentioned compound, its salt, or its stereoisomer as an active ingredient. In another aspect, the present invention relates to a health functional food for preventing or improving inflammatory diseases, comprising the above compound, its salt, or its stereoisomer as an active ingredient. The present invention will be described in detail below. The compound according to the present invention can be represented by Chemical Formula 1. Compounds represented by Chemical Formula 1, pharmaceutically acceptable salts thereof, or stereoisomers thereof: [Chemical Formula 1] In Chemical Formula 1 R 1 , R 2 and R 3 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl; -CONR 10 R 11 ; -NR 10 CO-R11 ; R 12 CO- and, here, R 10 and R 11 Each is independently a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A and, Here, A is i) a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and R 12 ... is a C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, or C5-C20 alkylheteroaryl, wherein the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4, and; R 4 is a hydrogen atom or a C1-C6 alkyl. In this case, in the present invention, preferably, Formula 1 can be represented by Formula 2. [Chemical Formula 2] In Chemical Formula 2 R 5 and R 6 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl, and R 13 and R 14 Each independently consists of a hydrogen atom, C1-C12 alkyl, hydroxy, -(CH2) n -A or R 13 and R 14 Together, they can form a saturated or unsaturated heterocycloalkyl or heteroaryl ring having 2 to 20 carbon atoms and 1 to 7 heteroatoms, and Here, A is i) a C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4, and; R 7 is a hydrogen atom or a C1-C6 alkyl. In the present invention, more preferably, Formula 1 can be represented by Formula 3. [Chemical Formula 3] In chemical formula 3 R 8 is a hydrogen atom, halogen, amino, C1-C6 alkyl halide, hydroxy, and R 9 is a C1-C6 alkyl, and R 13 and R 14 Each independently consists of a hydrogen atom, C1-C12 alkyl, hydroxy, -(CH2) n -A or R 13 and R 14 Together, they can form a saturated or unsaturated heterocycloalkyl or heteroaryl ring having 2 to 20 carbon atoms and 1 to 7 heteroatoms, and Here, A is i) a C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl, and n is 1, 2, 3, or 4. In the present invention, more preferably, Formula 1 can be represented by Formula 4. [Chemical Formula 4] In chemical formula 4 R 5 and R 6 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl, and ⓐ is a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n-A, where A is i) C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain a heteroatom selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4; R 7 is a hydrogen atom or a C1-C6 alkyl. In the present invention, more preferably, Formula 1 can be represented by Formula 5. [Chemical Formula 5] In chemical formula 5 R 8 is a hydrogen atom, a halogen, an amino, and a C1-C6 alkyl halide, and R 9 is a C1-C6 alkyl, and ⓐ is a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n-A, where A is i) C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain a heteroatom selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, or 3. In the present invention, in Formula 1, the above A is i) one of Chemical Formulas 6 to 11 or ii) unsubstituted or C1-C6 alkoxy or methylsulfonyl substituted naphthalenyl or benzofuran, indole, indazole, or iii) -(CH2) n -A or, where A is a C1-C6 alkyl, cyano, halogen, or hydroxyl, and n is 1 or 2, and iv) C3-C6 cycloalkyl or iv) A compound characterized as being unsubstituted or substituted with a C1-C6 alkyl or alkyl ester peperidinyl or piperazinyl, a pharmaceutically acceptable salt thereof or a stereoisomer thereof: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] R 18 and R 19 are each independently hydrogen atoms, C1-C6 alkyl, hydroxy, carboxyl, ester, C1-C6 alkoxy, halogen, C1-C6 alkyl halide, R 20 CONH, carbonyl, halogenated carbonyl, R 15 SO2- and, where, R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 is a hydrogen atom or a C1-C6 alkyl; R 20 is a hydrogen atom, a C1-C6 alkyl, or a C2-C6 alkenyl, and W is a single bond or -NH or -CH2O- and R 21 and R 22 Each is independently hydrogen or a C1-C6 alkyl, and X and Y are heteroatoms selected from carbon or oxygen, sulfur and nitrogen, wherein X and Y cannot be carbon simultaneously, and hydrogen or a C1-C6 alkyl group is bonded to the heteroatom to satisfy the normal valence of the said atom, and Z is a heteroatom selected from oxygen, sulfur, and nitrogen, wherein hydrogen or a C1-C6 alkyl group is bonded to the heteroatom to satisfy the normal valence of the atom. In the present invention, A in Chemical Formula 1 may be one of the following functional groups, but is not limited thereto. In the present invention, it may be selected from the following group. In a preferred embodiment of the present invention, compounds 1 to 18 may be selected from the group consisting of compounds 1 to 18. In the present invention, the term “cycloalkyl” refers to a saturated or partially unsaturated monocyclic or polycyclic (e.g., condensed, cross-linked, or spiro-ring) hydrocarbon system having 3 to 30 carbon atoms (e.g., C3-C12, C3-C10, or C3-C8). Examples of cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexeniyl, cycloheptenyl, 1,2,3,4-tetrahydronaphthalenyl, and adamantyl. In the present invention, the term “heterocycloalkyl” refers to one or more heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur (e.g., O, N, or S), for example, 1 or 1 to 2 or 1 to 3 or 1 to 4 or 1 to 5 or 1 to 6 heteroatoms, or, for example, a saturated or partially unsaturated 3 to 8-membered monocyclic or dicyclic, 7 to 12-membered dicyclic (condensed, cross-linked, or spiro ring), or 11 to 14-membered tricyclic ring system (condensed, cross-linked, or spiro ring) having 1, 2, 3, 4, 5, or 6 heteroatoms. Examples of heterocycloalkyl groups include piperidine-yl, piperazine-yl, pyrrolidine-yl, dioxane-yl, tetrahydrofuran-yl, isoindoline-yl, indoline-yl, imidazolidine-yl, pyrazolidine-yl, oxazolidine-yl, isooxazolidine-yl, triazolidine-yl, oxiran-yl, azetidine-yl, oxetane-yl, thietane-yl, 1,2,3,6-tetrahydropyridine-yl, tetrahydropyran-yl, dihydropyran-yl, pyran-yl, morpholine-yl, tetrahydrothiopyran-yl, 1,4-diazepan-yl, 1,4-oxazepan-yl, 2-oxa-5-azabicyclo[2.2.1]heptan-yl, 2,5-diazabicyclo[2.2.1]heptan-yl, 2-oxa-6-azaspiro[3.3]heptanyl, 2,6-diazaspiro[3.3]heptanyl, 1,4-dioxa-8-azaspiro[4.5]decaneyl, 1,4-dioxaspiro[4.5]decaneyl, 1-oxaspiro[4.5]decaneyl, 1-azaspiro[4.5]decaneyl, 3'H-spiro[cyclohexane-1,1'-isobenzofuran]-yl, 7'H-spiro[cyclohexane-1,5'-furo[3,4-b]pyridine]-yl, 3'H-spiro[cyclohexane-1,1'-furo[3,4-c]pyridine]-yl, 3-azabicyclo[3.1.0]hexaneyl, 3-Azabicycle[3.1.0]Hexane-3-yl, 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazolyl, 3,4,5,6,7,8-hexahydropyridodo[4,3-d]pyrimidinyl, 4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridinyl, 5,6,7,8-tetrahydropyridodo[4,3-d]pyrimidinyl, 2-azaspiro[3.3]heptanyl, 2-methyl-2-azaspiro[3.3]heptanyl, 2-azaspiro[3.5]nonanyl, 2-methyl-2-azaspiro[3.5]nonanyl, 2-azaspiro[4.5]decaneyl, 2-methyl-2-azaspiro[4.5]decaneyl, Includes, but is not limited to, 2-oxa-azaspiro[3,4]octanyl, 2-oxa-azaspiro[3,4]octanyl-6-yl, 5,6-dihydro-4H-cyclopenta[b]thiophenyl, etc. In the present invention, the term "aryl" refers to a monocyclic or bicyclic group, e.g.,

[0128] It refers to a cyclic, aromatic hydrocarbon group having one to three aromatic rings, including phenyl, biphenyl, or naphthyl. In the case of containing two aromatic rings (e.g., bicyclic), the aromatic rings of the aryl group may be bonded at a single point (e.g., biphenyl) or condensed (e.g., naphthyl). The aryl group may be optionally substituted at any attachment site by one or more substituents, e.g., one to five substituents. In the present invention, the term "heteroaryl" means a monocyclic or polycyclic aromatic group having 5 to 24 ring atoms, containing one or more ring heteroatoms selected from N, O, or S, and the remaining ring atoms being C. Examples include furyl, thienyl, pyrrolyl, pyridyl, pyrazolyl, pyrimidinyl, imidazolyl, isooxazolyl, oxazolyl, oxadiazolyl, pyrazinyl, indolyl, thiophene-2-yl, quinolineyl, benzopyranyl, isothiazolyl, thiazolyl, thiadiazole, indazole, benzimidazolyl, thieno[3,2-b]thiophene, triazolyl, triazinyl, imidazo[1,2-b]pyrazolyl, furo[2,3-c]pyridinyl, imidazo[1,2-a]pyridinyl, indazolyl, pyrrolo[2,3-c]pyridinyl, pyrrolo[3,2-c]pyridinyl, pyrazolo[3,4-c]pyridinyl, Thieno[3,2-c]pyridinyl, Thieno[2,3-c]pyridinyl, Thieno[2,3-b]pyridinyl, benzothiazolyl, indolyl, indolinyl, indolinonyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, benzofuran, chromanyl, thiochromanyl, tetrahydroquinolineyl, dihydrobenzothiazine, quinolineyl, isoquinolineyl, 1,6-naphthiridinyl, benzo[de]isoquinolineyl, pyrido[4,3-b][1,6]naphthiridinyl, Thieno[2,3-b]pyrazineyl, quinazolinyl, tetrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, isoindolyl, Pyrrolo[2,3-b]pyridinyl, pyrrolo[3,4-b]pyridinyl, pyrrolo[3,2-b]pyridinyl, imidazo[5,4-b]pyridinyl, pyrrolo[1,2-a]pyrimidinyl, dibenzo[b,d]thiophene, pyridin-2-one, furo[3,2-c]pyridinyl, furo[2,3-c]pyridinyl, 1H-pyrido[3,4-b][1,4]thiazineyl, benzoxazolyl, benzisooxazolyl, furo[2,3-b]pyridinyl, benzothiophenyl, 1,5-naphthiridinyl, furo[3,2-b]pyridine, [1,2,4]triazolo[1,5-a]pyridinyl, benzo [1,2,3]triazolyl, imidazo[1,2-a]pyrimidinyl, [1,2,4]triazolo[4,3-b]pyridazinyl,Benzo[c][1,2,5]thiadiazolyl, benzo[c][1,2,5]oxadiazole, 1,3-dihydro-2H-benzo[d]imidazol-2-one, 3,4-dihydro-2H-pyrazolo[1,5-b][1,2]oxazinyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, thiazolo[5,4-d]thiazolyl, imidazo[2,1-b][1,3,4]thiadiazolyl, thieno[2,3-b]pyrroli, 3H-indolyl, and derivatives thereof, but are not limited thereto. In the present invention, the pharmaceutically acceptable salt may be selected from one or more of the group consisting of hydrochloride, p-toluenesulfonate, fumarate, citrate, succinate, salicylate, oxalate, bromate, phosphate, methanesulfonate, tartrate, sulfate, and mandelate, and preferably the pharmaceutically acceptable salt is hydrochloride, but is not limited thereto. In the present invention, the term “halogen” refers to fluoro, chloro, bromo, and iodo. In the present invention, the terms "alkyl halide" or "carbonyl halide" refer to an alkyl or carbonyl substituted with one or more halogen atoms. In the present invention, the term "alkoxy" includes substituted and unsubstituted alkyl, alkenyl, and alkynyl groups covalently connected to an oxygen atom. As used herein, the term “treatment” refers to any act of improving or beneficially altering the symptoms of a disease through the administration of a composition according to the present invention. As used herein, the term “prevention” refers to any act of suppressing or delaying a disease through the administration of a composition according to the present invention. As used herein, the term “improvement” refers to any act of improving a poor condition of a disease by administering or ingesting a composition of the present invention to an individual. The pharmaceutical composition of the present invention can be administered to mammals, including humans, by any route of administration, and can be administered orally or parenterally. Parenteral administration methods may include, for example, intravenous, intramuscular, intra-arterial, intramedullary, intrathecal, intracardiac, transdermal, subcutaneous, intraperitoneal, intranasal, intestinal, local, sublingual, or rectal administration, but are not limited thereto. The inflammatory disease in the present invention is an NLRP3 inflammasome-related inflammatory disease, and preferably, the inflammatory disease may be any one selected from the group consisting of neurodegenerative diseases, cardiovascular diseases, metabolic diseases, immune diseases and inflammatory skin diseases, but is not limited thereto. In the present invention, the inflammatory disease is a neurodegenerative disease (Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis (ALS), Creutzfeldt-Jakob disease, multiple sclerosis, Lewy body dementia, leukocytosis, temporal lobe epilepsy, frontotemporal dementia, viral encephalitis, epilepsy, stroke), cardiovascular disease (heart failure, ischemic heart disease), metabolic disease (type 2 diabetes, arteriosclerosis, obesity, hyperlipidemia, hypercholesterolemia, non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH)), and immune disease (Muckle-Wells syndrome (MWS), Sjögren's syndrome, adult-onset delayed autoimmune diabetes (LADA), familial cold autoinflammatory syndrome (FCAS), cryopyrin-associated periodic syndrome (CAPS), neonatal multisystem inflammatory syndrome (NOMID), chronic It may be any one selected from the group consisting of infantile neurocutaneous joint syndrome (CINCA), familial Mediterranean fever (FMF), specific forms of juvenile arthritis such as systemic onset juvenile idiopathic arthritis (SJIA), specific forms of juvenile rheumatoid arthritis such as systemic onset juvenile idiopathic rheumatoid arthritis or specific forms of adult rheumatoid arthritis, gout and gouty arthritis), and inflammatory skin diseases (psoriasis, eczema, acne, pustulosis, actinic keratosis), but is not limited thereto. The present specification includes a composition comprising a compound or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. For example, the above-mentioned pharmaceutically acceptable carrier may be used as an oral administration carrier or a parenteral administration carrier. The oral administration carrier may include lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, etc. Additionally, the parenteral administration carrier may include water, suitable oil, saline solution, aqueous glucose and glycol, etc., and may further include stabilizers and preservatives, etc. Suitable stabilizers include antioxidants such as sodium bisulfite, sodium sulfite, or ascorbic acid. Suitable preservatives include benzalkonium chloride, methyl- or propyl-paraben, and chlorobutanol, etc. For other pharmaceutically acceptable carriers, reference may be made to the literature well known in the field to which the present invention belongs. In another aspect, the present invention relates to a pharmaceutical formulation comprising a pharmaceutical composition for the treatment or prevention of inflammatory diseases. In the present invention, the pharmaceutical formulation may be an oral administration, transdermal administration, subcutaneous injection, or topical application formulation. In the case of an oral administration formulation, the composition of the present invention may be formulated using methods known in the art, such as powder, granules, tablets, pills, coated tablets, capsules, liquids, gels, syrups, slurries, and suspensions. For example, an oral formulation may be obtained by combining an active ingredient with a solid excipient, grinding the mixture, adding a suitable additive, and processing it into a granular mixture. Examples of suitable excipients may include sugars such as lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, and maltitol; starches such as corn starch, wheat starch, rice starch, and potato starch; celluloses such as cellulose, methylcellulose, sodium carboxymethylcellulose, and hydroxypropylmethylcellulose; and fillers such as gelatin and polyvinylpyrrolidone. Additionally, cross-linked polyvinylpyrrolidone, agar, alginic acid, or sodium alginate may be added as disintegrants. Furthermore, the pharmaceutical composition of the present invention may additionally include anticoagulants, lubricants, humectants, flavorings, emulsifiers, and preservatives. Additionally, to alleviate gastrointestinal irritation, the drug may be subjected to an enteric coating or microencapsulation intended to be released as it passes through the intestinal tract rather than being released in the stomach. The above external skin formulation can be formulated in a form selected from the group consisting of creams, lotions, topical ointments, oils, moisturizers, gels, aerosols, and nasal inhalants using methods known in the art. The pharmaceutical composition of the present invention may additionally include a lubricant, a wetting agent, a sweetener, a flavoring agent, an emulsifier, a suspending agent, a preservative, etc., in addition to the above components. The quasi-drug composition or cosmetic composition of the present invention may be prepared by combining various known ingredients to be incorporated into a composition applied to the skin or mucous membrane, and may be prepared by mixing each ingredient well with a suitable base as needed according to a well-known method for preparing a topical skin preparation or cosmetic composition, and the preparation thus prepared is applied to a lesion as needed. The formulation according to the present invention is included in an amount of 0.01 to 30 weight%, more preferably 1 to 10 weight%, based on the total weight of the quasi-drug composition or cosmetic composition of the present invention. If the content is less than 0.01 weight%, therapeutic and preventive effects cannot be achieved, and if it exceeds 30 weight%, formulation is difficult and the user experience may be reduced. The administration route and method of administration of the pharmaceutical composition of the present invention may each be independent and are not particularly limited in such manner, and may follow any administration route and method as long as the pharmaceutical composition can reach the intended site. The effective dosage is generally about 0.01 to about 300 mg / kg / day, preferably about 0.1 to about 100 mg / kg / day, and most preferably 1 to 50 mg / kg / day, as a single or divided dose. Depending on age, gender, and the disease or condition to be treated, a dosage level below the lower limit of this range may be suitable. In other cases, a larger dosage may still be used without harmful side effects. A larger dosage may be divided into several smaller doses for administration over a day. Methods for determining an appropriate dosage are well known in the field to which the present invention belongs. The health functional food according to the present invention may be used in combination with other foods or food additives in addition to the active ingredient of the compound of Formula 1 or a pharmaceutically acceptable salt thereof, and may be used appropriately according to conventional methods. The amount of the active ingredient may be appropriately determined according to the purpose of use, for example, prevention, health, or therapeutic treatment. The effective dose of the compound contained in the above health food may be used in accordance with the effective dose of the above therapeutic agent, but in the case of long-term consumption for the purpose of health and hygiene or health control, it may be less than the above range, and it is certain that the active ingredient may be used in an amount greater than the above range because there is no problem in terms of safety. There are no special restrictions on the types of health foods mentioned above, and examples include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, chewing gum, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages, and vitamin complexes. Hereinafter, preferred embodiments are presented to aid in understanding the present invention; however, the following embodiments are merely illustrative of the invention, and it is obvious to those skilled in the art that various changes and modifications are possible within the scope and spirit of the invention, and that such variations and modifications fall within the scope of the appended claims. [Example] [Reaction Equation 1] Preparation Example 1: 5-Bromo-N-(3,4-dimethoxyphenethyl)-2-(methylthio)pyrimidine-4-carboxamide 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (250 mg, 1.0 mmol) and 2-(3,4-dimethoxyphenyl)ethane-1-amine (0.2 ml, 1.2 mmol) were dissolved in dichloromethane (6 ml), after which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (289 mg, 1.5 mmol), hydroxybenzotriazole (203 mg, 1.5 mmol), and N,N-diisopropylethylamine (0.5 ml, 3.0 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was solidified with 1N hydrochloric acid and water, and the precipitated solid was filtered and purified by column chromatography to obtain the title compound (231 mg, yield: 55%, white solid). 1 H NMR (400 MHz, CDCl3) δ8.75 (s, 1H), 7.68 (br s, NH), 6.82-6.76 (m, 3H), 3.87 (s, 6H), 3.69 (q,J= 7.2 Hz, 2H), 2.88 (t,J= 7.2 Hz, 2H) 2.47 (s, 3H); MS (ESI)m / z412.0 [M+H] + Example 1 Example 1-1: 5-Bromo-N-(3,4-dimethoxyphenetyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 1 (175 mg, 0.4 mmol) was dissolved in methanol (3.9 ml), potassium peroxymonosulfate (459 mg, 1.4 mmol) dissolved in water (3.9 ml) was added, and the mixture was stirred at room temperature for 1 day. The solidified reaction mixture was filtered while washing with water and purified by column chromatography to obtain the title compound (94 mg, yield: 50%, white solid). 1H NMR (400 MHz, CDCl3) δ9.15 (s, 1H), 7.76 (br s, NH), 6.86-6.77 (m, 3H), 3.88 (s, 3H), 3.87 (s, 3H), 3.70 (q,J= 6.4 Hz, 2H), 3.33 (s, 3H), 2.91 (t,J= 6.8 Hz, 2H); MS (ESI)m / z444.0 [M+H] + Examples 1-2 to 1-278 used a compound obtained through the same reaction as Preparation Example 1 according to Reaction Scheme 1 and carried out the same reaction as Example 1-1 to obtain the corresponding compound, respectively. Example 1-2: 5-chloro-2-(methylsulfonyl)-N-(3-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-3: N-(4-hydroxy-3-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 1-4: 2-(methylsulfonyl)-N-(3-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Examples 1-5: 5-bromo-N-(3,4-dihydroxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 1-6: 5-bromo-N-(3,4-dimethoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 1-7: 5-bromo-N-(4-ethoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 1-8: 5-bromo-N-(5-fluoro-2-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 1-9: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-10: 5-bromo-N-(2,4-dimethylphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-11: 5-bromo-N-(3-methylphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-12: 5-bromo-N-(2,3-dichlorophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-13: 5-bromo-N-(5-chloro-2-propoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-14: 5-bromo-N-(5-chloro-2-propoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-15: 5-bromo-N-(3-methylbenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-16: 5-bromo-N-(2,3-dichlorobenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-17: 5-bromo-N-(2,5-dimethylbenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-18: 5-bromo-N-(2,5-dichlorobenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-19: 5-bromo-N-(3,4-dimethoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-20: 5-bromo-N-(3,4-dimethoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-21: 5-bromo-N-(5-chloro-2-propoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-22: 5-bromo-N-(5-chloro-2-propoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-23: 5-bromo-N-(3-(3,4-dimethoxyphenyl)propyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-24: 5-bromo-N-(5-fluoro-2-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-25: 5-bromo-N-(5-bromo-2-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-26: 5-bromo-N-(5-chloro-2-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-27: 5-amino-N-(3,4-dimethoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-28: N-(4-acetamidophenethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-29: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-30: 5-bromo-2-(methylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-31: 5-bromo-N-(4-hydroxy-3-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-32: 5-bromo-N-(3-hydroxy-4-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-33: 5-bromo-N-(5-chloro-2-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-34: 5-bromo-N-(5-fluoro-2-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-35: 5-bromo-N-(4-chlorophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-36: 5-bromo-N-(3-hydroxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-37: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxy-3-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-38: 5-bromo-N-(4-ethoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-39: 5-bromo-N-(4-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-40: 5-bromo-N-(3-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-41: 5-bromo-2-(ethylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-42: 5-bromo-N-phenethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-43: 5-bromo-2-(ethylsulfonyl)-N-(3-hydroxy-4-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-44: 5-bromo-2-(ethylsulfonyl)-N-(3-hydroxy-4-methoxybenzyl)pyrimidine-4-carboxamide Example 1-45: 5-bromo-N-(3-hydroxy-4-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-46: 5-bromo-N-(4-hydroxy-3-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-47: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxy-3-methoxybenzyl)pyrimidine-4-carboxamide Example 1-48: 5-bromo-N-(4-hydroxy-3-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-49: 5-bromo-2-(ethylsulfonyl)-N-(5-fluoro-2-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-50: 5-bromo-2-(ethylsulfonyl)-N-(3-methylbenzyl)pyrimidine-4-carboxamide Example 1-51: 5-bromo-2-(ethylsulfonyl)-N-(3-methylphenethyl)pyrimidine-4-carboxamide Example 1-52: 5-bromo-N-(3-methylbenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-53: 5-bromo-N-(3-methylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-54: 5-bromo-2-(methylsulfonyl)-N-propylpyrimidine-4-carboxamide Example 1-55: 5-bromo-N-(4-ethoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-56: 5-bromo-N-(4-ethoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-57: 5-bromo-N-(4-chlorophenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-58: 5-bromo-2-(ethylsulfonyl)-N-(4-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-59: 5-bromo-2-(ethylsulfonyl)-N-(3-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-60: 5-bromo-2-(ethylsulfonyl)-N-(4-methoxybenzyl)pyrimidine-4-carboxamide Example 1-61: 5-bromo-2-(ethylsulfonyl)-N-(3-methoxybenzyl)pyrimidine-4-carboxamide Example 1-62: 5-bromo-2-(ethylsulfonyl)-N-(3-hydroxyphenethyl)pyrimidine-4-carboxamide Example 1-63: 5-bromo-N-(3-hydroxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-64: 5-bromo-N-(2,4-dimethylbenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-65: 5-bromo-N-(2,4-dimethylphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-66: 5-bromo-N-(2,5-dimethylbenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-67: 5-bromo-N-(2,5-dimethylphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-68: 5-bromo-N-(3-(4-hydroxy-3-methoxyphenyl)propyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-69: 5-bromo-2-(ethylsulfonyl)-N-(3-(4-hydroxy-3-methoxyphenyl)propyl)pyrimidine-4-carboxamide Example 1-70: 5-bromo-N-(3-(4-hydroxy-3-methoxyphenyl)propyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-71: 5-bromo-2-(methylsulfonyl)-N-(3-phenylpropyl)pyrimidine-4-carboxamide Example 1-72: 5-bromo-2-(ethylsulfonyl)-N-(3-phenylpropyl)pyrimidine-4-carboxamide Example 1-73: 5-bromo-N-(3-phenylpropyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-74: 5-bromo-N-(2,4-dimethylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-75: 5-bromo-N-(2,5-dimethylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-76: N-(4-acetamidophenethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-77: 5-bromo-2-(methylsulfonyl)-N-(naphthalen-1-ylmethyl)pyrimidine-4-carboxamide Example 1-78: 5-bromo-N-(2-cyclohexylethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-79: 5-chloro-N-(5-chloro-2-methoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-80: 5-bromo-N-(2-cyclohexylethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-81: N-(4-acetamidophenethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-82: 5-bromo-2-(ethylsulfonyl)-N-(naphthalen-1-ylmethyl)pyrimidine-4-carboxamide Example 1-83: 5-bromo-2-(ethylsulfonyl)-N-(naphthalen-2-ylmethyl)pyrimidine-4-carboxamide Example 1-84: 5-bromo-2-(methylsulfonyl)-N-(2-(naphthalen-1-yl)ethyl)pyrimidine-4-carboxamide Example 1-85: 5-bromo-2-(methylsulfonyl)-N-(2-(naphthalen-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-86: 5-bromo-2-(methylsulfonyl)-N-(naphthalen-2-ylmethyl)pyrimidine-4-carboxamide Example 1-87: N-(3,4-dimethoxyphenethyl)-3-(methylsulfonyl)benzamide Example 1-88: 3-(methylsulfonyl)-N-phenethylbenzamide Example 1-89: 2-(methylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-90: 5-chloro-2-(ethylsulfonyl)-N-(5-fluoro-2-methoxyphenethyl)pyrimidine-4-carboxamide Example 1-91: 5-bromo-N-ethyl-2-(methylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-92: 5-bromo-N-ethyl-N-phenethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-93: 5-bromo-N-(2,5-dimethoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-94: 5-bromo-N-(2,5-dimethoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-95: 5-bromo-N-(2,5-dimethoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-96: 2-chloro-N-(3,4-dimethoxyphenethyl)-5-(methylsulfonyl)benzamide Example 1-97: 5-chloro-1-(1-(5-chloro-2-(methylsulfonyl)pyrimidine-4-carbonyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one Example 1-98: (5-chloro-2-(methylsulfonyl)pyrimidin-4-yl)(4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazin-1-yl)methanone) Example 1-99: 5-chloro-2-(methylsulfonyl)-N-(4-(methylsulfonyl)phenethyl)pyrimidine-4-carboxamide Example 1-100: N-(3,4-dimethoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-101: 5-chloro-N-(4-hydroxy-3-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-102: 5-chloro-N-(5-chloro-2-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-103: 5-bromo-2-(methylsulfonyl)-N-(3-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-104: 5-bromo-N-(4-hydroxy-3-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-105: 5-bromo-N-(5-chloro-2-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-106: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-107: 5-bromo-2-(methylsulfonyl)-N-(4-(methylsulfonyl)phenethyl)pyrimidine-4-carboxamide Example 1-108: 5-bromo-2-(methylsulfonyl)-N-(4-sulfamoylphenethyl)pyrimidine-4-carboxamide Example 1-109: (5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)(4-(3,4-dimethoxyphenyl)piperazin-1-yl)methanone Example 1-110: 5-bromo-N-(3-(3,4-dimethoxyphenyl)propyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-111: 5-bromo-N-(2,4-dichlorophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-112: 5-bromo-N-(2,5-dimethylphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-113: 5-bromo-N-(3,4-dimethoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-114: 5-bromo-N-(5-chloro-2-methoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-115: 5-bromo-N-(3,4-dimethoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-116: 5-bromo-N-(3-(3,4-dimethoxyphenyl)propyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-117: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-118: 5-bromo-2-(ethylsulfonyl)-N-(3-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-119: 5-bromo-N-(4-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-120: 5-bromo-N-(3-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-121: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-122: N-(4-acetylphenethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-123: 5-bromo-N-(2-cyclohexylethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-124: 5-bromo-N-(3-hydroxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-125: 5-bromo-N-(4-ethoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-126: 5-bromo-N-(4-ethoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-127: 5-bromo-N-(4-chlorophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-128: 5-bromo-N-(4-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-129: 5-bromo-N-(3-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-130: 5-bromo-N-(4-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-131: 5-bromo-N-(3-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-132: 5-chloro-2-(methylsulfonyl)-N-(4-sulfamoylphenethyl)pyrimidine-4-carboxamide Example 1-133: 5-bromo-2-(ethylsulfonyl)-N-(3-hydroxybenzyl)pyrimidine-4-carboxamide Example 1-134: 5-bromo-N-(3-hydroxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-135: 5-bromo-N-(2,4-dichlorobenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-136: 5-bromo-N-(2,4-dichlorophenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-137: 5-bromo-N-(2,3-dichlorobenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-138: 5-bromo-N-(2,3-dichlorophenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-139: N-benzyl-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-140: N-benzyl-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-141: N-benzyl-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-142: 5-bromo-N-(3,4-dihydroxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-143: 5-bromo-N-(3,4-dihydroxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-144: 5-bromo-N-(3-(3-hydroxy-4-methoxyphenyl)propyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-145: 5-bromo-2-(ethylsulfonyl)-N-(3-(3-hydroxy-4-methoxyphenyl)propyl)pyrimidine-4-carboxamide Example 1-146: 5-bromo-N-(3-(3-hydroxy-4-methoxyphenyl)propyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-147: 5-bromo-N-(2,4-dimethylbenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-148: 5-bromo-N-(2,4-dimethylbenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-149: 5-bromo-N-(2,5-dimethylbenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-150: N-(4-acetylphenethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-151: N-(4-acetylphenethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-152: 5-bromo-N-(2,4-dichlorobenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-153: 5-bromo-N-(2,4-dichlorophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-154: 5-bromo-N-(2,3-dichlorobenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-155: 5-bromo-N-(2,3-dichlorophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-156: 5-bromo-2-(methylsulfonyl)-N-(2-(thiazol-4-yl)ethyl)pyrimidine-4-carboxamide Example 1-157: 5-bromo-2-(ethylsulfonyl)-N-(2-(thiazol-4-yl)ethyl)pyrimidine-4-carboxamide Example 1-158: 5-bromo-2-(propylsulfonyl)-N-(2-(thiazol-4-yl)ethyl)pyrimidine-4-carboxamide Example 1-159: N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-160: N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-161: 5-bromo-N-(2-bromoethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-162: 5-bromo-2-((2-hydroxyethyl)sulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-163: 5-bromo-N-(2-cyanoethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-164: N-((1H-indol-2-yl)methyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-165: N-((1H-indol-2-yl)methyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-166: methyl 4-(2-(5-bromo-2-(propylsulfonyl) pyrimidine-4-carboxamido)ethyl)benzenesulfonate Example 1-167: 5-bromo-N-(4-(methylsulfonyl)phenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-168: 5-bromo-N-(4-(N-methylsulfamoyl)phenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-169: 5-bromo-2-(propylsulfonyl)-N-(4-sulfamoylphenethyl)pyrimidine-4-carboxamide Example 1-170: 5-bromo-N-(2-(5-methylfuran-2-yl)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-171: 5-bromo-2-(ethylsulfonyl)-N-(2-(5-methylfuran-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-172: 5-bromo-N-(2-(5-methylfuran-2-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-173: 5-chloro-2-(methylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 1-174: 2-chloro-5-(methylsulfonyl)-N-phenethylbenzamide Example 1-175: 5-bromo-2-(ethylsulfonyl)-N-((tetrahydrofuran-2-yl)methyl)pyrimidine-4-carboxamide Example 1-176: 5-bromo-2-(ethylsulfonyl)-N-(2-(tetrahydrofuran-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-177: 5-bromo-N-(3-ethoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-178: 5-bromo-N-(3-ethoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-179: 5-bromo-N-(5-chloro-2-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-180: 5-bromo-N-(5-fluoro-2-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-181: 5-bromo-N-(5-bromo-2-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-182: 5-bromo-N-(5-bromo-2-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-183: 5-bromo-N-(5-chloro-2-propoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-184: 5-bromo-N-(5-chloro-2-propoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-185: N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-186: N-(benzo[d][1,3]dioxol-5-ylethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-187: 5-bromo-N-(2-methoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-188: 5-bromo-N-(3-ethoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-189: 5-bromo-N-(3-ethoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-190: 5-bromo-N-(3-ethoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-191: 5-bromo-N-(3-ethoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-192: 2-bromo-N-(3,4-dimethoxyphenethyl)-5-(methylsulfonyl)benzimide Example 1-193: 2-bromo-N-(3,4-dimethoxyphenethyl)-5-(propylsulfonyl)benzimide (2-bromo-5-(methylsulfonyl)-N-phenethylbenzamide) Example 1-194: 5-bromo-2-(ethylsulfonyl)-N-(4-(trifluoromethoxy)phenethyl)pyrimidine-4-carboxamide Example 1-195: 5-bromo-2-(ethylsulfonyl)-N-(4-trifluoromethoxy)benzyl)pyrimidine-4-carboxamide Example 1-196: 5-bromo-2-(methylsulfonyl)-N-(4-(trifluoromethoxy)phenethyl)pyrimidine-4-carboxamide Example 1-197: 5-bromo-2-(methylsulfonyl)-N-(4-(trifluoromethoxy)benzyl)pyrimidine-4-carboxamide Example 1-198: 5-bromo-2-(propylsulfonyl)-N-(4-(trifluoromethoxy)phenethyl)pyrimidine-4-carboxamide Example 1-199: 5-bromo-2-(propylsulfonyl)-N-(4-trifluoromethoxy)benzyl)pyrimidine-4-carboxamide Example 1-200: 5-bromo-N-(4-fluorophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-201: 5-bromo-N-(4-bromophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-202: 5-bromo-N-(4-iodophenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-203: 5-bromo-2-(methylsulfonyl)-N-(4-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-204: 5-bromo-2-(propylsulfonyl)-N-(3-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-205: N-(4-acetylbenzyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-206: N-(4-acetylbenzyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-207: N-(4-acetylbenzyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-208: N-(4-acrylamidobenzyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-209: N-(4-acrylamidobenzyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-210: N-(4-acrylamidobenzyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-211: N-(4-acrylamidobenzyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-212: 5-bromo-2-(methylsulfonyl)-N-(3-(trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-213: 5-bromo-2-(ethylsulfonyl)-N-(3-(trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-214: 5-bromo-2-(propylsulfonyl)-N-(3-(trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-215: 5-bromo-2-(methylsulfonyl)-N-(4-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 1-216: 5-bromo-2-(ethylsulfonyl)-N-(4-trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-217: 5-bromo-2-(ethylsulfonyl)-N-(4-(trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-218: 5-bromo-2-(propylsulfonyl)-N-(4-(trifluoromethyl)benzyl)pyrimidine-4-carboxamide Example 1-219: 5-bromo-N-(4-hydroxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-220: 5-bromo-N-(4-hydroxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-221: 5-bromo-N-(2-hydroxy-4-(trifluoromethyl)phenyl-2-(methylsulfonyl)pyrimidine-4-carboxamide) Example 1-222: 5-bromo-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-223: 5-bromo-N-(4-methylbenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-224: N-(2-benzyloxy)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-225: 5-bromo-N-(2-hydroxyethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-226: N-(2-(benzyloxy)ethyl-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-227: 5-bromo-N-(4-bromo-2,5-dimethoxybenzyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-228: 5-bromo-N-(4-bromo-2,5-dimethoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-229: N-(2-(1H-indol-2-yl)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-230: N-(2-(1H-indol-2-yl)methyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-231: 5-bromo-N-((5-methoxy-1H-indol-3-yl)methyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-232: 5-bromo-N-((5-methoxy-1H-indol-3-yl)methyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-233: 5-bromo-N-((5-methoxy-1H-indol-3-yl)methyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-234: N-(benzofuran-3-ylmethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-235: N-((1H-indazol-7-yl)methyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-236: N-((1H-indazol-7-yl)methyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-237: N-(2-(1H-indol-5-yl)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-238: 5-bromo-2-(methylsulfonyl)-N-((tetrahydrofuran-2-yl)methyl)pyrimidine-4-carboxamide Example 1-239: 5-bromo-2-(propylsulfonyl)-N-((tetrahydrofuran-2-yl)methyl)pyrimidine-4-carboxamide Example 1-240: 5-bromo-2-(propylsulfonyl)-N-((tetrahydrofuran-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-241: 5-bromo-2-(propylsulfonyl)-N-((tetrahydrofuran-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-242: 5-bromo-N-((1-methyl-1H-pyrazol-4-yl)methyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-243: 5-bromo-N-((1-methyl-1H-pyrazol-4-yl)methyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-244: 5-bromo-N-((1-methyl-1H-pyrazol-4-yl)methyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-245: methyl 2-(4-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamido)-6-methoxybenzoate Example 1-246: N-(2-(benzo[d]thiazol-2-yl)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-247: N-(2-(benzo[d]thiazol-2-ylmethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-248: 5-bromo-N-isopentyl-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-249: 5-bromo-N-(2-cyanoethyl)-2-methylsulfonyl)pyrimidine-4-carboxamide Example 1-250: 5-bromo-N-(2-bromoethyl)-2-methylsulfonyl)pyrimidine-4-carboxamide Example 1-251: methyl 2-(5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamido)-6-methoxybenzoate Example 1-252: N-(2-(benzo[d]thiazol-2-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-253: N-(2-(benzo[d]thiazol-2-ylmethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-254: 5-bromo-N-(2-(naphthalen-1-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-255: 5-bromo-N-(2-(naphthalen-2-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-256: 5-bromo-N-propyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-257: 5-bromo-N-propyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-258: 5-bromo-N-(2-cyanoethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-259: 5-bromo-N-(2-bromoethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-260: 5-bromo-N-(2,5-dimethoxyphenylethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-261: 5-bromo-N-(2,5-dimethoxyphenylethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-262: 5-(5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamido)-2-hydroxybenzoic acid Example 1-263: 5-(5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamido)-2-hydroxybenzoic acid Example 1-264: 5-bromo-2-(ethylsulfonyl)-N-(2-pyridin-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-265: 5-bromo-2-(ethylsulfonyl)-N-(pyridin-2-ylmethyl)pyrimidine-4-carboxamide Example 1-266: 5-bromo-2-(ethylsulfonyl)-N-(2-(pyridin-3-yl)ethyl)pyrimidine-4-carboxamide Example 1-267: 5-bromo-2-(methylsulfonyl)-N-(2-(pyridin-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-268: 5-bromo-2-(methylsulfonyl)-N-(2-pyridin-2-ylmethyl)pyrimidine-4-carboxamide Example 1-269: 5-bromo-2-(methylsulfonyl)-N-(2-(pyridin-3-yl)ethyl)pyrimidine-4-carboxamide Example 1-270: 5-bromo-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-271: 5-bromo-2-(propylsulfonyl)-N-(2-(pyridin-2-yl)ethyl)pyrimidine-4-carboxamide Example 1-272: 5-bromo-2-(propylsulfonyl)-N-(pyridin-2-ylmethyl)pyrimidine-4-carboxamide Example 1-273: 5-bromo-2-(propylsulfonyl)-N-(2-(pyridin-3-yl)ethyl)pyrimidine-4-carboxamide Example 1-274: 5-bromo-N-(2,6-diisopropylphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 1-275: 5-bromo-N-(2,6-diisopropylphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 1-276: 5-bromo-N-(2,6-diisopropylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-277: 5-bromo-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 1-278: 5-bromo-2-(ethylsulfonyl)-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)pyrimidine-4-carboxamide Preparation Example 2: 5-chloro-N-(4-chlorophenetyl)-2-(methylthio)pyrimidine-4-carboxamide 5-chloro-2-(methylthio)pyrimidine-4-carboxylic acid (350 mg, 1.71 mmol) was dissolved in dichloromethane (5.6 ml), after which 2-(4-chlorophenyl)ethane-1-amine (0.24 ml, 1.71 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (492 mg, 2.56 mmol), hydroxybenzotriazole (347 mg, 2.56 mmol), and N,N-diisopropylethylamine (0.66 ml, 5.13 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (350 mg, yield: 59.8%). Example 2 Example 2-1: 5-chloro-N-(4-chlorophenetyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 2 (345 mg, 1.01 mmol) was dissolved in dichloromethane (10 ml), then metachloroperoxybenzoic acid (522 mg, 2.12 mmol) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with an aqueous sodium bicarbonate solution and dichloromethane, and purified by column chromatography to obtain the title compound (257 mg, yield: 67.9%, white solid). 1 H NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 7.60 (br s, NH), 7.27-7.23 (m, 2H), 7.15-7.13 (m, 2H), 3.95 (s, 3H), 3.64 (q,J= 7.2 Hz, 2H), 2.88 (t,J= 7.2 Hz, 2H); MS (ESI)m / z373.7 [M+H] + Examples 2-2 to 2-3 used a compound obtained through the same reaction as Preparation Example 2 according to Reaction Scheme 1, and carried out the same reaction as Example 2-1 to obtain the corresponding compound, respectively. Example 2-2: 5-chloro-N-(3,4-dimethoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 2-3: N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-5-chloro-2-(methylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 2] Example 3 Example 3-1: 5-Bromo-N-(2-(5-methoxy-1H-indole-3-yl)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide 5-Bromo-2-(methylsulfonyl)pyrimidine-4-carboxylic acid (200 mg, 0.71 mmol) was dissolved in dimethylformamide (2.5 ml), after which 5-methyltryptamine hydrochloride (160.9 mg, 0.71 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (162.9 mg, 0.85 mmol), hydroxybenzotriazole (105.3 mg, 0.78 mmol), and N,N-diisopropylethylamine (0.19 ml, 1.42 mmol) were added and stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, extracted with water and dichloromethane, and purified by column chromatography to obtain the title compound (75 mg, yield: 23%, yellow solid). 1 H NMR (400MHz, DMSO-d6) δ10.69 (br s, NH), 9.42 (s, 1H), 9.04 (t,J= 5.6 Hz, NH), 7.23 (d,J= 8.8 Hz, 1H), 7.18 (d,J= 4.8 Hz, 1H), 7.06 (d,J=2.4 Hz, 1H), 6.72 (dd,J= 8.8, 2.4 Hz, 1H), 3.76 (s, 3H), 3.58 (q,J= 7.2 Hz, 2H), 3.44 (s, 3H), 2.94 (t,J= 7.6 Hz, 2H); MS (ESI) m / z 452.9 [M+H] + Examples 3-2 to 3-8 each obtained the corresponding compound by carrying out the same reaction as Example 3-1 according to Reaction Scheme 2. Example 3-2: N-(5-chloro-2-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 3-3: N-(2-(1H-indol-3-yl)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 3-4: N-((1H-indol-3-yl)methyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 3-5: N-((1H-indol-3-yl)methyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 3-6: N-((1H-indol-3-yl)methyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 3-7: 5-bromo-2-(ethylsulfonyl)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)pyrimidine-4-carboxamide Examples 3-8: 5-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4 Example 4-1: 5-Bromo-N-(4-Bromophenetyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (79 mg, 0.41 mmol), and N-hydroxysuccinimide (47 mg, 0.41 mmol) were dissolved in dimethylformamide (1 ml) and stirred at room temperature for 10 minutes. Subsequently, 2-(4-bromophenyl)ethylamine (68 mg, 0.34 mmol) dissolved in dimethylformamide (1 ml) was added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (99 mg, yield: 61%, white solid). 1 H NMR (400 MHz, CDCl3) δ9.18 (s, 1H), 7.79 (br s, NH), 7.48 (d,J= 8.4 Hz, 2H), 7.16 (d,J= 8.4 Hz, 2H), 3.72 (q,J= 7.2 Hz, 2H), 3.54 (q,J= 7.6 Hz, 2H) 2.94 (t,J= 7.2 Hz, 2H) 1.45 (t,J= 7.2 Hz, 3H); MS (ESI) m / z 475.9 [M+H] + Examples 4-2 to 4-49 each obtained the corresponding compound by carrying out the same reaction as Example 4-1. Example 4-2: N-((1H-indol-6-yl)methyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-3: N-(2-(benzofuran-3-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-4: 5-bromo-2-(ethylsulfonyl)-N-(4-sulfamoylphenethyl)pyrimidine-4-carboxamide Examples 4-5: 5-bromo-2-(ethylsulfonyl)-N-(4-(methylsulfonyl)phenethyl)pyrimidine-4-carboxamide Examples 4-6: 5-bromo-2-(ethylsulfonyl)-N-(2-(naphthalen-1-yl)ethyl)pyrimidine-4-carboxamide Examples 4-7: 5-bromo-2-(ethylsulfonyl)-N-(2-(naphthalen-2-yl)ethyl)pyrimidine-4-carboxamide Examples 4-8: 5-bromo-N-(naphthalen-1-ylmethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Examples 4-9: 5-bromo-N-(naphthalen-2-ylmethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-10: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxyphenethyl)pyrimidine-4-carboxamide Example 4-11: 5-bromo-N-(4-hydroxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-12: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxybenzyl)pyrimidine-4-carboxamide Example 4-13: 5-bromo-N-(4-hydroxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-14: 5-bromo-2-(ethylsulfonyl)-N-(2-methoxyphenethyl)pyrimidine-4-carboxamide Example 4-15: 5-bromo-N-(2-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-16: 5-bromo-2-(ethylsulfonyl)-N-(2-methoxybenzyl)pyrimidine-4-carboxamide Example 4-17: 5-bromo-N-(2-methoxybenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-18: N-((1H-indazol-7-yl)methyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-19: 5-bromo-N-(2,5-dimethoxyphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-20: 5-bromo-N-methyl-2-(methylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 4-21: 5-bromo-N-methyl-N-phenethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-22: 5-bromo-N-(2-hydroxy-4-methylphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 4-23: 5-bromo-N-(2-hydroxy-4-methylphenethyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-24: 5-bromo-N-(2-hydroxy-4-methylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-25: 5-bromo-2-(methylsulfonyl)-N-(2-(piperidin-1-yl)ethyl)pyrimidine-4-carboxamide Example 4-26: 5-bromo-2-(ethylsulfonyl)-N-(2-(piperidin-1-yl)ethyl)pyrimidine-4-carboxamide Example 4-27: 5-bromo-2-(ethylsulfonyl)-N-(2-(4-methylpiperidin-1-yl)ethyl)pyrimidine-4-carboxamide Example 4-28: 5-bromo-2-(ethylsulfonyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)pyrimidine-4-carboxamide Example 4-29: 5-bromo-2-(ethylsulfonyl)-N-(4-(trifluoromethyl10l)phenethyl)pyrimidine-4-carboxamide Example 4-30: tert-butyl 4-(2-(5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamido)ethyl)piperazine-1-carboxylate Example 4-31: N-(2-(benzo[d]thiazol-2-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-32: N-(benzo[d]thiazol-2-ylmethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-33: N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-34: N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-35: 5-bromo-2-(ethylsulfonyl)-N-(4-fluorophenethyl)pyrimidine-4-carboxamide Example 4-36: 5-bromo-N-(4-fluorophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-37: 5-bromo-N-(4-bromophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-38: 5-bromo-2-(propylsulfonyl)-N-(4-(trifluoromethyl)phenethyl)pyrimidine-4-carboxamide Example 4-39: 5-bromo-N-(5-chloro-2-methoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-40: 5-bromo-2-(ethylsulfonyl)-N-(5-fluoro-2-methoxybenzyl)pyrimidine-4-carboxamide Example 4-41: 5-bromo-N-(5-bromo-2-methoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-42: 5-bromo-2-(ethylsulfonyl)-N-(4-iodophenethyl)pyrimidine-4-carboxamide Example 4-43: 5-bromo-N-(4-iodophenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-44: 5-bromo-2-(ethylsulfonyl)-N-propylpyrimidine-4-carboxamide Example 4-45: 5-bromo-2-(ethylsulfonyl)-N-isopentylpyrimidine-4-carboxamide Example 4-46: 5-bromo-2-(ethylsulfonyl)-N-(4-methylbenzyl)pyrimidine-4-carboxamide Example 4-47: 5-bromo-N-(4-methylbenzyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 4-48: N-(2-(1H-indol-2-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 4-49: N-(2-(1H-indol-2-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 5 Example 5-1: 5-Bromo-N-(2-(furan-2-yl)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxylic acid (200 mg, 0.7 mmol) was dissolved in dichloromethane (30 ml), then 2.0 M oxalyl chloride dichloromethane solution (0.71 ml) and dimethylformamide (4 drops) were added and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, dissolved in dichloromethane (20 ml), and then 2-furan-2-yl-ethylamine (78.8 mg, 0.7 mmol) and triethylamine (0.2 ml, 1.4 mmol) were added and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, extracted with water and dichloromethane, and purified by column chromatography to obtain the title compound (152 mg, yield: 57%, white solid). 1H NMR (400MHz, CDCl3) δ9.18 (s, 1H), 7.97 (br s, NH), 7.40-7.39 (m, 1H), 6.34-6.33 (m, 1H), 6.16-6.15 (m, 1H), 3.77 (q,J= 6.8 Hz, 2H), 3.38 (s, 3H), 3.01 (t,J= 6.8 Hz, 2H); MS (ESI) m / z373.90 [M+H] + Examples 5-2 to 5-3 each obtained the corresponding compound by carrying out the same reaction as in Example 5-1. Example 5-2: N-((1H-indol-6-yl)methyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 5-3: 5-bromo-N-(furan-2-ylmethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 6 Example 6-1: 5-Bromo-2-(methylsulfonyl)-N-((5-methylthiophene-2-yl)methyl)pyrimidine-4-carboxamide 5-Bromo-2-(methylsulfonyl)pyrimidine-4-carboxylic acid (150 mg, 0.53 mmol) was dissolved in dichloromethane (3 ml), after which thionyl chloride (1.5 ml) and dimethylformamide (3 drops) were added and stirred at room temperature for 2 hours and 30 minutes. The reaction mixture was concentrated under reduced pressure, and after dissolving in dichloromethane (3 ml), (5-methylthiene-2-yl)methylamine hydrochloride (86.7 mg, 0.53 mmol) and N,N-diisopropylethylamine (0.46 ml, 2.67 mmol) were added and stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (38 mg, yield: 18.3%, white solid). 1 H NMR (400MHz, CDCl3) δ9.18 (s, 1H), 8.00 (br s, NH), 6.86 (d,J= 3.2Hz, 1H), 6.63-6.62 (m, 1H), 4.75 (d,J= 6.0Hz, 2H), 3.39 (s, 3H), 3.47 (s, 3H); MS (ESI) m / z389.9 [M+H] + Examples 6-2 to 6-27 each obtained the corresponding compound by carrying out the same reaction as in Example 6-1. Example 6-2: 5-bromo-2-(methylsulfonyl)-N-(2-(5-methylthiophen-2-yl)ethyl)pyrimidine-4-carboxamide Example 6-3: 5-bromo-N-((1-isopropyl-1H-pyrazol-4-yl)methyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 6-4: N-(2-(1H-indol-3-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 6-5: 5-bromo-2-(ethylsulfonyl)-N-(2-(furan-2-yl)ethyl)pyrimidine-4-carboxamide Example 6-6: 5-bromo-N-(2-(furan-2-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Examples 6-7: 5-bromo-2-(ethylsulfonyl)-N-((5-methylthiophen-2-yl)methyl)pyrimidine-4-carboxamide Examples 6-8: 5-bromo-2-(ethylsulfonyl)-N-(2-(5-methylthiophen-2-yl)ethyl)pyrimidine-4-carboxamide Examples 6-9: 5-bromo-N-((5-methylthiophen-2-yl)methyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Examples 6-10: 5-bromo-N-(2-(5-methylthiophen-2-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 6-11: 5-bromo-2-(ethylsulfonyl)-N-((1-isopropyl-1H-pyrazol-4-yl)methyl)pyrimidine-4-carboxamide Example 6-12: 5-bromo-N-((1-isopropyl-1H-pyrazol-4-yl)methyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 6-13: N-(2-(1H-indol-3-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 6-14: N-(2-(benzofuran-3-yl)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 6-15: N-(2-(benzofuran-3-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 6-16: N-((1H-indol-6-yl)methyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 6-17: 5-bromo-N-((5-methylfuran-2-yl)methyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 6-18: 5-bromo-2-(methylsulfonyl)-N-(thiophen-2-ylmethyl)pyrimidine-4-carboxamide Example 6-19: 5-bromo-2-(methylsulfonyl)-N-(2-(thiophen-2-yl)ethyl)pyrimidine-4-carboxamide Example 6-20: 5-bromo-2-(ethylsulfonyl)-N-(furan-2-ylmethyl)pyrimidine-4-carboxamide Example 6-21: 5-bromo-N-(furan-2-ylmethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 6-22: 5-bromo-2-(ethylsulfonyl)-N-((5-methylfuran-2-yl)methyl)pyrimidine-4-carboxamide Example 6-23: 5-bromo-N-((5-methylfuran-2-yl)methyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 6-24: 5-bromo-2-(ethylsulfonyl)-N-(thiophen-2-ylmethyl)pyrimidine-4-carboxamide Example 6-25: 5-bromo-2-(propylsulfonyl)-N-(thiophen-2-ylmethyl)pyrimidine-4-carboxamide Example 6-26: 5-bromo-2-(ethylsulfonyl)-N-(2-(thiophen-2-yl)ethyl)pyrimidine-4-carboxamide Example 6-27: 5-bromo-2-(propylsulfonyl)-N-(2-(thiophen-2-yl)ethyl)pyrimidine-4-carboxamide [Reaction Equation 3] Preparation Example 3: 5-Bromo-N-ethyl-2-(ethylthio)-N-phenethylpyrimidine-4-carboxamide 5-Bromo-2-(ethylthio)pyrimidine-4-carboxylic acid (200 mg, 0.76 mmol) was dissolved in dimethylformamide (2 ml), after which N-ethylbenzeneethanolamine hydrochloride (141.1 mg, 0.76 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (218.5 mg, 1.14 mmol), hydroxybenzotriazole (154 mg, 1.14 mmol), and N,N-diisopropylethylamine (0.39 ml, 2.28 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (237 mg, yield: 79%, clear liquid). Example 7 Example 7-1: 5-Bromo-N-ethyl-2-(ethylsulfonyl)-N-phenethylpyrimidine-4-carboxamide The compound obtained in Preparation Example 3 (110 mg, 0.27 mmol) was dissolved in methanol (4 ml), potassium peroxymonosulfate (292 mg, 0.95 mmol) dissolved in water (4 ml) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (85 mg, yield: 73.8%, white solid). 1 H NMR (400 MHz, CDCl3) major diastereomer: δ9.08 (s, 1H), 7.37-7.19 (m, 4H), 7.06-7.02 (m, 1H), 3.81-3.77 (m, 2H), 3.63 (q,J= 7.2 Hz, 2H), 3.59-3.53 (m, 2H), 3.08-3.02 (m, 2H), 1.46 (t,J= 7.2 Hz, 3H), 1.16 (t,J= 7.2 Hz, 3H) minor diastereomer: δ9.05 (s, 1H), 7.37-7.19 (m, 4H), 7.06-7.02 (m, 1H), 3.59-3.53 (m, 2H), 3.36-3.32 (m, 2H), 3.08-3.02 (m, 2H), 2.96-2.92 (m, 2H), 1.46 (t,J= 7.2 Hz, 3H), 1.34 (t,J= 7.2 Hz, 3H); major : minor = 1 : 0.66; MS (ESI)m / z426.0 [M+H] + Examples 7-2 to 7-15 used a compound obtained through the same reaction as Preparation Example 3 according to Reaction Scheme 3, and each compound was obtained by carrying out the same reaction as Example 7-1. Example 7-2: 5-bromo-N-(3,4-dimethoxyphenethyl)-N-methyl-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 7-3: 5-bromo-N-(3-ethoxy-4-methoxyphenethyl)-N-ethyl-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 7-4: 5-bromo-N-ethyl-N-(3-hydroxy-4-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 7-5: 5-bromo-N-(3-ethoxy-4-methoxyphenethyl)-N-ethyl-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 7-6: 5-bromo-N-ethyl-2-(ethylsulfonyl)-N-(3-hydroxy-4-methoxyphenethyl)pyrimidine-4-carboxamide Example 7-7: 5-bromo-N-ethyl-3-(3-ethoxy-4-methoxyphenethyl)-N-ethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Examples 7-8: 5-bromo-N-ethyl-N-(3-hydroxy-4-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Examples 7-9: 5-bromo-N-(4-ethoxy-3-methoxyphenethyl)-N-ethyl-2-(methylsulfonyl)pyrimidine-4-carboxamide Examples 7-10: 5-bromo-N-ethyl-N-(4-hydroxy-3-methoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 7-11: 5-bromo-N-(4-ethoxy-3-methoxyphenethyl)-N-ethyl-2-(ethylsulfonyl)pyrimidine-4-carboxamide Example 7-12: 5-bromo-N-ethyl-2-(ethylsulfonyl)-N-(4-hydroxy-3-methoxyphenethyl)pyrimidine-4-carboxamide Example 7-13: 5-bromo-N-(4-ethoxy-3-methoxyphenethyl)-N-ethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 7-14: 5-bromo-N-ethyl-N-(4-hydroxy-3-methoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 7-15: 5-bromo-N-(3,4-dimethoxyphenethyl)-N-ethyl-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 4] Example 8 Example 8-1: 5-Bromo-N-(3,4-dimethoxyphenethyl)-2-(ethylsulfonyl)-N-methylpyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (74.7 mg, 0.39 mmol), and N-hydroxysuccinimide (44.8 mg, 0.39 mmol) were dissolved in dimethylformamide (1 ml) and stirred at room temperature for 10 minutes. Subsequently, N-methylhomoveratrilamine (64.4 mg, 0.33 mmol) dissolved in dimethylformamide (1 ml) was added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (90 mg, yield: 57.7%, white solid). 1H NMR (400 MHz, CDCl3) major diastereomer: δ9.07 (s, 1H), 6.86-6.76 (m, 2H), 6.63-6.59 (m, 1H), 3.93 (s, 3H), 3.85-3.81 (m, 5H), 3.58-3.52 (m, 2H), 3.00 (t,J= 7.6 Hz, 2H), 2.81 (s, 3H), 1.47-1.43 (m, 3H) minor diastereomer: δ9.06 (s, 1H), 6.86-6.76 (m, 2H), 6.63-6.59 (m, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.58-3.52 (m, 2H), 3.37 (t,J= 7.6 Hz, 2H), 3.20 (s, 3H), 2.91 (t,J= 8.0 Hz, 2H), 1.47-1.43 (m, 3H); major : minor = 1 : 0.87; MS (ESI)m / z472.0 [M+H] + Examples 8-2 to 8-7 each obtained the corresponding compound by carrying out the same reaction as in Example 8-1. Example 8-2: 5-bromo-2-(ethylsulfonyl)-N-methyl-N-phenethylpyrimidine-4-carboxamide Example 8-3: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxy-3-methoxyphenethyl)-N-methylpyrimidine-4-carboxamide Example 8-4: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-N-methyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 8-5: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-N-methyl-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 8-6: 5-bromo-N-(4-hydroxy-3-methoxyphenethyl)-N-methyl-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 8-7: 5-bromo-N-(3,4-dimethoxyphenethyl)-N-methyl-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 5] Preparation Example 4: 5-Bromo-N-(3,4-dimethoxyphenethyl)-2-(methylthio)pyrimidine-4-carboxamide 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (300 mg, 1.2 mmol) was dissolved in dimethylformamide (4 ml), after which 2-(3,4-dimethoxyphenyl)ethane-1-amine (217.4 mg, 1.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (345 mg, 1.8 mmol), hydroxybenzotriazole (243.2 mg, 1.8 mmol), and N,N-diisopropylethylamine (0.63 ml, 3.6 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (200 mg, yield: 40.4%, white solid). Preparation Example 5: 5-Bromo-N-(3,4-dimethoxyphenethyl)-N-ethyl-2-(methylthio)pyrimidine-4-carboxamide The compound obtained in Preparation Example 4 (145 mg, 0.35 mmol) was dissolved in dimethylformamide (4 ml), sodium hydride (28 mg, 0.7 mmol) was added, and the mixture was stirred for 30 minutes. The temperature was lowered to 0°C, bromoethane (0.03 ml, 0.46 mmol) was added, and the mixture was stirred again at room temperature for 3 hours and 30 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the mixed title compound (80 mg, yield: 51.9%, clear white liquid). Example 9 Example 9-1: 5-Bromo-N-(3,4-dimethoxyphenethyl)-N-ethyl-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 5 (110 mg, 0.25 mmol) was dissolved in methanol (2 ml), potassium peroxymonosulfate (270.3 mg, 0.88 mmol) dissolved in water (2 ml) was added, and the mixture was stirred at room temperature for 1 day. The solidified reaction mixture was filtered while washing with water and purified by column chromatography to obtain the title compound (80 mg, yield: 67%, white solid). 1 H NMR (400MHz, CDCl3) major diastereomer: δ 9.08 (s, 1H), 6.85-6.75 (m, 2H), 6.60-6.55 (m, 1H), 3.93 (s, 3H), 3.85 (s, 3H), 3.77 (t,J= 7.2, 2H), 3.64 (q,J= 7.2, 2H), 3.37 (s, 3H), 3.01 (t,J= 8.0 Hz, 2H), 1.18 (t,J= 6.8 Hz, 3H) minor diastereomer: δ 9.05 (s, 1H), 6.85-6.75 (m, 2H), 6.60-6.55 (m, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.37 (s, 3H), 3.31 (t,J= 8.0 Hz, 2H), 3.07 (q,J= 6.8 Hz, 2H), 2.89 (t,J= 8.0 Hz, 2H), 1.35 (t,J= 7.2 Hz, 3H); major : minor = 1 : 0.74 ; MS (ESI) m / z472.0 [M+H] + Example 9-2 used a compound obtained through the same reaction as Preparation Examples 4 and 5 and carried out the same reaction as Example 9-1 to obtain the corresponding compound. Example 9-2: 5-bromo-N-(3,4-dimethoxyphenethyl)-N-ethyl-2-(ethylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 6] Preparation Example 6: Methyl(4-hydroxy-3-methoxyphenethyl)carbamate mixture 3-methoxycytiramine hydrochloride (500 mg, 2.46 mmol) was dissolved in dimethylformamide (4 ml), triethylamine (1.03 ml, 7.38 mmol) was added, and the temperature was lowered to 0°C. At 0°C, methylchloroformate (0.19 ml, 2.46 mmol) was slowly added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (280 mg, mixture, clear liquid). Preparation Example 7: Methyl(4-hydroxy-3-methoxyphenetyl)carbamate The compound obtained in Preparation Example 6 (280 mg, 1.24 mmol) and potassium hydroxide (69.6 mg, 1.24 mmol) were dissolved in methanol (20 ml) and stirred at reflux temperature for 2 hours and 30 minutes. After the reaction was complete, 1N-HCl was added to neutralize the potassium hydroxide, and the methanol was concentrated under reduced pressure. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (270 mg, yield: 96.7%, clear liquid). Preparation Example 8: 2-Methoxy-4-(2-(methylamino)ethyl)phenol The compound obtained in Preparation Example 7 (140 mg, 0.62 mmol) was dissolved in tetrahydrofuran (4 ml) under argon purging, and then lithium aluminum hydride (94.1 mg, 2.48 mmol) dissolved in tetrahydrofuran (4 ml) was slowly added at 0°C and stirred at reflux temperature for 4 hours. After the reaction was finished, the temperature of the reaction mixture was lowered to 0°C, and water was slowly added to quench the lithium aluminum hydride. The mixture was then extracted with an aqueous sodium bicarbonate solution and dichloromethane and concentrated to obtain the title compound (88.5 mg, yield: 78.8%, yellow liquid). Preparation Example 9: 5-Bromo-N-(4-hydroxy-3-methoxyphenethyl)-N-methyl-2-(methylthio)pyrimidine-4-carboxamide 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid (117 mg, 0.47 mmol) was dissolved in dimethylformamide (4 ml), and then the compound obtained in Preparation Example 8 (86 mg, 0.47 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (134.2 mg, 0.7 mmol), hydroxybenzotriazole (94.6 mg, 0.7 mmol), and N,N-diisopropylethylamine (0.24 ml, 1.4 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (71 mg, yield: 36%, clear liquid). Example 10 Example 10-1: 5-Bromo-N-(4-hydroxy-3-methoxyphenethyl)-N-methyl-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound (67 mg, 0.16 mmol) obtained in Preparation Example 9 was dissolved in methanol (2 ml), potassium peroxymonosulfate (172.1 mg, 0.56 mmol) dissolved in water (2 ml) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (43 mg, yield: 60.4%, white solid). 1 H NMR (400MHz, CDCl3) major diastereomer: δ 9.06 (s, 1H), 6.89-6.85 (m, 1H), 6.82-6.78 (m, 1H), 6.57-6.55 (m, 1H), 5.55 (s, OH), 3.94 (s, 3H), 3.83 (t,J= 8.8 Hz, 2H), 3.36 (s, 3H), 2.98 (t,J= 7.6 Hz, 2H), 2.81 (s, 3H) minor diastereomer: δ9.05 (s, 1H), 6.89-6.85 (m, 1H), 6.82-6.78 (m, 1H), 6.57- 6.55 (m, 1H), 5.53 (s, OH), 3.85 (s, 3H), 3.37-3.33 (m, 5H), 3.20 (s, 3H), 2.89 (t,J= 8.0 Hz, 2H); major : minor = 1 : 0.93; MS (ESI) m / z444.0 [M+H] + [Reaction Equation 7] Example 10-2 used a compound obtained through the same reaction as Preparation Examples 6, 7, 8, and 9, and carried out the same reaction as Example 10-1 to obtain the corresponding compound. Example 10-2: 5-bromo-2-(ethylsulfonyl)-N-(3-hydroxy-4-methoxyphenethyl)-N-methylpyrimidine-4-carboxamide [Reaction Equation 8] Preparation Example 10: 1-(1H-indazole-7-yl)-N-methylmethaneamine 1H-indazole-7-carbaldehyde (300 mg, 2.0 mmol) was dissolved in methanol (1.5 ml), followed by the addition of acetic acid (0.012 ml, 0.20 mmol) and 2M methylamine (in methanol) (3.08 ml, 6.16 mmol), and the mixture was stirred at room temperature for 3 hours. After the starting material was consumed, sodium borohydride (85.44 mg, 2.25 mmol) was added at 0 ℃ and the mixture was stirred at room temperature for 1 day. After the reaction was complete, the mixture was extracted using 1N HCl, 1M NaOH, water, and ethyl acetate to obtain the title compound (295 mg, mixture, white solid) containing a small amount of impurities. Example 11: N-((1H-indazole-7-yl)methyl)-5-bromo-2-(ethylsulfonyl)-N-methylpyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (77.9 mg, 0.41 mmol), and N-hydroxysuccinate (46.7 mg, 0.41 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 10 (54.5 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (62 mg, yield: 42%, white solid). 1 H NMR (400 MHz, CDCl3) major diastereomer: δ11.38 (br s, NH), 9.08 (s, 1H), 8.13 (s, 1H), 7.83-7.81 (m, 1H), 7.33-7.31 (m, 1H), 7.19-7.14 (m, 1H), 5.00 (s, 2H), 3.56 (q,J= 9.2 Hz, 2H), 2.87 (s, 3H), 1.46 (t,J= 7.6 Hz, 3H) minor diastereomer: δ11.38 (br s, NH), 9.17 (s, 1H), 8.18 (s, 1H), 7.83-7.81 (m, 1H), 7.33-7.31 (m, 1H), 7.19-7.14 (m, 1H), 4.68 (s, 2H), 3.56 (q,J= 9.2 Hz, 2H), 2.97 (s, 3H), 1.47 (t,J= 7.2 Hz, 3H); major:minor=1:0.07; MS (ESI)m / z438.0 [M+H] + [Reaction Equation 9] Preparation Example 11: 4-(2-bromoethyl)-1,2-dimethoxybenzene 2-(3,4-dimethoxyphenyl)ethanol (3 g, 16.5 mmol) and tetrabromocarbon (7.1 g, 21.4 mmol) were dissolved in dichloromethane (50 ml), and then a solution of triphenylphosphine (5.6 g, 21.4 mmol) dissolved in dichloromethane (50 ml) was slowly added at 0°C, followed by stirring at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure and purified by column chromatography to obtain the title compound (4.38 g, yield: 108%, yellow liquid). Preparation Example 12: Tert-butyl ((tert-butoxycarbonyl)oxy)(3,4-dimethoxyphenetyl)carbamate The compound obtained in Preparation Example 11 (2.4 g, 9.8 mmol), tert-butyl(tert-butoxycarbonyl)oxycarbamate (2.28 g, 9.8 mmol), and potassium carbonate (4 g, 29.4 mmol) were dissolved in dimethylformamide (50 ml) and stirred at 60 °C for 1 day. The reaction mixture was extracted with water and ethyl acetate, and then purified by column chromatography to obtain the title compound (3.53 g, yield: 90%, colorless oil). Preparation Example 13: N-(3,4-dimethoxyphenethyl)hydroxyamine hydrochloride The compound obtained in Preparation Example 12 (1.1 g, 2.77 mmol) was dissolved in a 4M hydrochloric acid (in dioxane) solution (8.31 ml, 33.24 mmol) and stirred at room temperature for 1 day. A dichloromethane / hexane (1:1) mixed solution was poured into the reaction mixture, and the solid was filtered to obtain the title compound (505 mg, yield: 78%, pale yellow solid). Preparation Example 14: 5-Bromo-N-(3,4-dimethoxyphenetyl)-N-hydroxy-2-(methylthio)pyrimidine-4-carboxamide The compound obtained in Preparation Example 13 (235 mg, 1.0 mmol), 5-bromo-2-(methylthio)pyrimidine-4-carboxyside (250 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (288 mg, 1.5 mmol), and hydroxybenzotriazole (203 mg, 1.5 mmol) were dissolved in dimethylformamide (3 ml), after which N,N-diisopropylethylamine (0.6 ml, 3.0 mmol) was added and stirred at room temperature for 1 day. Extraction was performed by adding 1N hydrochloric acid solution and ethyl acetate to the reaction mixture, and the mixture was purified by column chromatography to obtain the title compound (130 mg, yield: 30%, white solid). Example 12: 5-Bromo-N-(3,4-Dimethoxyphenetyl)-N-Hydroxy-2-(methylsulfonyl)pyrimidine-4-Carboxamide The compound obtained in Preparation Example 14 (150 mg, 0.35 mmol) was dissolved in methanol (2 ml), and potassium peroxymonosulfate (377 mg, 1.22 mmol) dissolved in water (2 ml) was added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with dichloromethane and water, and purified by column chromatography to obtain the title compound (70 mg, yield: 43%, yellow solid). 1H NMR (400 MHz, CDCl3) major diastereomer: δ 9.03 (s, 1H), 7.20 (s, 1H), 6.91 - 6.55 (m, 3H), 4.12 (t,J= 7.2 Hz, 2H), 3.92 (s, 3H), 3.89 (s, 3H), 3.34 (s, 3H), 3.08 (t,J= 7.6 Hz, 2H) minor diastereomer: δ 9.01 (s, 1H), 8.37 (s, 1H), 6.93 - 6.47 (m, 3H), 3.99 (t,J= 6.7 Hz, 2H), 3.86 (s, 3H), 3.82 (s, 3H), 3.35 (s, 3H), 3.03 (t,J= 6.7 Hz, 2H); major : minor = 1 : 0.88; MS (ESI) 459.9m / z[M+H] + [Reaction Equation 10] Preparation Example 15: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(methylthio)pyrimidine-4-carboxamide Bromo-2-(methylthio)pyrimidine-4-carboxyside (1 g, 4.01 mmol), 3,4-dimethoxyphenylethylamine (727 mg, 4.01 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.154 g, 6.02 mmol), and hydroxybenzotriazole (813 mg, 6.02 mmol) were dissolved in dimethylformamide (10 ml) and stirred at room temperature for 10 minutes. Subsequently, N,N-diisopropylethylamine (2.1 ml, 12.03 mmol) was added and stirred at room temperature for 1 day. After the reaction was complete, ethyl acetate, a 1 normal hydrochloric acid solution, and water were added for extraction, followed by purification by column chromatography to obtain the title compound (1.55 g, yield: 94%, white solid). Preparation Example 16: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound (1.55 g, 3.76 mmol) obtained in Preparation Example 15 was dissolved in methanol (50 ml), and then potassium peroxymonosulfate (4.044 g, 13.2 mmol) dissolved in water (50 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (1.3 g, yield: 78%, white solid). Preparation Example 17: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(isopropylthio)pyrimidine-4-carboxamide The compound obtained in Preparation Example 16 (200 mg, 0.45 mmol) was dissolved in dimethylformamide (2 ml) and cooled to 0 °C. Subsequently, a solution of sodium 2-propanethiolate (53 mg, 0.54 mmol) dissolved in dimethylformamide (2 ml) was slowly added, and the mixture was stirred for 1 hour while slowly raising the temperature to room temperature. The reaction mixture was extracted with ethyl acetate and water, and then purified by column chromatography to obtain the title compound (174 mg, yield: 88%, colorless oil). Example 13: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(isopropylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 17 (170 mg, 0.39 mmol) was dissolved in methanol (2 ml), and potassium peroxymonosulfate (415 mg, 1.35 mmol) dissolved in water (2 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (129 mg, yield: 70%, yellow solid). 1H NMR (400 MHz, CDCl3): δ9.19 (s, 1H), 7.86 (br s, NH), 6.88-6.79 (m, 3H), 3.90 (s, 3H), 3.89 (s, 3H), 3.87-3.82 (m, 1H), 3.73 (q,J= 6.8 Hz, 2H), 2.93 (t,J= 7.2 Hz, 2H), 1.43 (s, 3H), 1.41 (s, 3H); MS (ESI) 472.0m / z[M+H] + Preparation Example 18: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(isobutylthio)pyrimidine-4-carboxamide The compound obtained in Preparation Example 16 (200 mg, 0.45 mmol) and potassium carbonate (187 mg, 1.35 mmol) were dissolved in dimethylformamide (2 ml), and then isobutyl mercaptan (122 mg, 1.35 mmol) dissolved in dimethylformamide (2 ml) was added to the reaction mixture and stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate and water, and then purified by column chromatography to obtain the title compound (157 mg, yield: 78%, white solid). Example 14 Example 14-1: 5-Bromo-N-(3,4-dimethoxyphenylethyl)-2-(isobutylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 18 (153 mg, 0.34 mmol) was dissolved in methanol (2 ml), and then potassium peroxymonosulfate (362 mg, 1.18 mmol) dissolved in water (2 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (143 mg, yield: 86%, yellow solid). 1H NMR (400 MHz, CDCl3): δ9.18 (s, 1H), 7.87 (br s, NH), 6.88-6.79 (m, 3H), 3.91 (s, 3H), 3.89 (s, 3H), 3.72 (q,J= 7.2 Hz, 2H), 3.42 (d,J= 6.4 Hz, 2H), 2.93 (t,J= 7.6 Hz, 2H), 2.44-2.34 (m, 1H), 1.14 (s, 3H), 1.13 (s, 3H); MS (ESI) 486.0m / z[M+H] + Examples 14-2 to 14-14 used a compound obtained through the same reaction as Preparation Example 18 according to Reaction Scheme 10, and each obtained the corresponding compound by carrying out the same reaction as Example 14-1. Example 14-2: 5-bromo-2-(tert-butylsulfonyl)-N-(3,4-dimethoxyphenethyl)pyrimidine-4-carboxamide Example 14-3: 5-bromo-N-(4-hydroxy-3-methoxyphenethyl)-2-(isobutylsulfonyl)pyrimidine-4-carboxamide Example 14-4: 5-bromo-2-(tert-butylsulfonyl)-N-(4-hydroxy-3-methoxyphenethyl)pyrimidine-4-carboxamide Example 14-5: 5-bromo-2-(isobutylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 14-6: 5-bromo-2-(tert-butylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 14-7: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-2-(isobutylsulfonyl)pyrimidine-4-carboxamide Example 14-8: 5-bromo-2-(tert-butylsulfonyl)-N-(3-hydroxy-4-methoxyphenethyl)pyrimidine-4-carboxamide Example 14-9: 5-bromo-2-(isopropylsulfonyl)-N-phenethylpyrimidine-4-carboxamide Example 14-10: 5-bromo-N-(3-hydroxy-4-methoxyphenethyl)-2-(isopropylsulfonyl)pyrimidine-4-carboxamide Example 14-11: 5-bromo-N-(4-hydroxy-3-methoxyphenethyl)-2-(isopropylsulfonyl)pyrimidine-4-carboxamide Example 14-12: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(isobutylsulfonyl)pyrimidine-4-carboxamide Examples 14-13: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(isopropylsulfonyl)pyrimidine-4-carboxamide Example 14-14: 5-bromo-N-(5-bromo-2-methoxyphenethyl)-2-(tert-butylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 11] Preparation Example 19: N-(2-(benzyloxy)ethyl)-5-bromo-2-(methylthio)pyrimidine-4-carboxamide 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (400 mg, 1.6 mmol) and 2-(benzyloxyl)-1-ethanolamine (0.24 ml, 1.6 mmol) were dissolved in dimethylformamide (5 ml), after which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (460 mg, 2.4 mmol), hydroxybenzotriazole (324.2 mg, 2.4 mmol), and N,N-diisopropylethylamine (0.84 ml, 4.8 mmol) were added and stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (372 mg, yield: 60.8%, clear oil). Example 15: N-(2-(benzyloxy)ethyl)-5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 19 (367 mg, 0.96 mmol) was dissolved in methanol (7.0 ml), potassium peroxymonosulfate (1000 mg, 3.36 mmol) dissolved in water (7.0 ml) was added, and the mixture was stirred at room temperature for 1 day. The solidified reaction mixture was filtered while washing with water and purified by column chromatography to obtain the title compound (260 mg, yield: 65.3%, white solid). 1 H NMR (400MHz, CDCl3) δ9.18 (s, 1H), 8.02 (br s, NH), 7.37 (d,J= 4.4 Hz, 4H), 7.31-7.28 (m, 1H), 4.58 (s, 2H), 3.71-3.70 (m, 4H), 3.35 (s, 3H); MS (ESI) m / z 414.0 [M+H] + Example 16: N-(2-(benzyloxy)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound (150 mg, 0.3 mmol) obtained by the synthesis method of Example 15 was dissolved in ethanol (3 ml), 10% palladium / carbon was added, and the mixture was replaced with H2 gas and stirred at room temperature for 4 hours. N-(2-(benzyloxy)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide and N-(2-hydroxyethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide were formed in a ratio of approximately 1:1. The reaction mixture was filtered to remove Pd, and the residue obtained after vacuum concentration was purified by column chromatography to obtain the title compound (39 mg, yield: 44%, white solid). 1 H NMR (400MHz, CDCl3) δ9.14 (d,J= 5.2 Hz, 1H), 8.46 (br s, NH), 8.36 (d,J= 4.8 Hz, 1H), 3.90 (t,J= 5.2 Hz, 2H), 3.71 (q,J= 6.0 Hz, 2H), 3.43 (s, 3H), 2.58 (br s, OH); MS (ESI) m / z 246.0 [M+H] + Example 17: N-(2-hydroxyethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound (150 mg, 0.3 mmol) obtained by the synthesis method of Example 15 was dissolved in ethanol (3 ml), 10% palladium / carbon was added, and the mixture was replaced with H2 gas and stirred at room temperature for 4 hours. N-(2-(benzyloxy)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide and N-(2-hydroxyethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide were formed in a ratio of approximately 1:1. The reaction mixture was filtered to remove Pd, and the residue obtained after vacuum concentration was purified by column chromatography to obtain the title compound (43 mg, yield: 35%, clear oil). 1H NMR (400MHz, CDCl3) δ9.14 (d,J= 4.8 Hz, 1H), 8.35 (d,J= 5.2 Hz, 1H), 8.26 (br s, NH), 7.37 (d,J= 4.4 Hz, 4H), 7.33-7.28 (m, 1H), 4.58 (s, 2H), 3.76-3.68 (m, 4H), 3.39 (s, 3H); MS (ESI) m / z 336.0 [M+H] + [Reaction Equation 12] Preparation Example 20: 2-((tert-butyldimethylsilyl)oxy)ethane-1-amine Ethanolamine (386 mg, 6.3 mmol) and imidazole (757 mg, 12.6 mmol) were dissolved in dichloromethane (7 ml), and then tert-butyldimethylchlorosilane (1 g, 6.6 mmol) dissolved in dichloromethane (8 ml) was added to the reaction mixture and stirred at room temperature for 3 hours. The reaction mixture was extracted with dichloromethane and water, and then vacuum dried to obtain the title compound (954 mg, yield: 86%, yellow oil). Preparation Example 21: 5-Bromo-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(ethylthio)pyrimidine-4-carboxyamide 5-bromo-2-(ethylthio)pyrimidine-4-carboxylic acid (200 mg, 0.76 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (219 mg, 1.14 mmol), and hydroxybenzotriazole (154 mg, 1.14 mmol) were dissolved in dimethylformamide (1 ml), and then the compound obtained in Preparation Example 20 (134 mg, 0.76 mmol) dissolved in dimethylformamide (1 ml) and N,N-diisopropylethylamine (0.4 ml, 2.28 mmol) were added and stirred at room temperature for 4 hours. The reaction mixture was extracted with ethyl acetate and 1-normal hydrochloric acid solution and purified by column chromatography to obtain the title compound (165 mg, yield: 52%, colorless oil). Example 18 Example 18-1: 5-Bromo-2-(ethylsulfonyl)-N-(2-hydroxyethyl)pyrimidine-4-carboxyamide The compound obtained in Preparation Example 21 (150 mg, 0.36 mmol) was dissolved in methanol (2 ml), and potassium peroxymonosulfate (548 mg, 1.78 mmol) dissolved in water (2 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (74 mg, yield: 61%, white solid). 1 H NMR (400 MHz, CDCl3): δ 9.18 (s, 1H), 8.23 ​​(br s, NH), 3.89 (q,J= 5.2 Hz, 2H), 3.68 (q,J= 5.6 Hz, 2H), 3.58 (q,J= 7.6 Hz, 2H), 2.58 (t,J= 5.2 Hz, 1H), 1.45 (t,J= 7.6 Hz, 3H); MS (ESI) 337.9m / z[M+H] + Example 18-2 used a compound obtained through the same reaction as Preparation Examples 20 and 21 according to Reaction Scheme 12, and carried out the same reaction as Example 18-1 to obtain the corresponding compound. Example 18-2: 5-bromo-N-(2-hydroxyethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 13] Preparation Example 22: Tert-butyl 4-(3,4-dimethoxybenzoyl)piperazine-1-carboxylate 1-Boc-piperazine (50 mg, 0.26 mmol) was dissolved in dichloromethane (4 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (25 mg, 0.13 mmol) and 3,4-dimethoxybenzoic acid (34.6 mg, 0.19 mmol) were added and stirred at room temperature for 10 minutes. Subsequently, 4-dimethylaminopyridine was added and stirred at room temperature for 3 hours and 50 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water, 1 normal hydrochloric acid, and ethyl acetate, and purified by column chromatography to obtain the title compound (40 mg, yield: 44.3%, white solid). Preparation Example 23: (3,4-Dimethoxyphenyl)(Piperazine-1-yl)methanone The compound obtained in Preparation Example 22 (100 mg, 0.28 mmol) was dissolved in dichloromethane (2 ml), then trifluoroacetic acid (0.84 ml) was added at 0°C and stirred at room temperature for 1 hour. The reaction mixture was extracted with an aqueous solution of sodium hexanormal hydroxide and dichloromethane, and then concentrated under reduced pressure to obtain the title compound (65.0 mg, yield: 92.8%, clear liquid). Example 19: (5-Bromo-2-(methylsulfonyl)pyrimidine-4-yl)(4-(3,4-dimethoxybenzoyl)piperazine-1-yl)methanone 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid (100 mg, 0.35 mmol) was dissolved in dichloromethane (1 ml), then thionyl chloride (0.25 ml, 3.5 mmol) and dimethylformamide (3 drops) were added and stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and dissolved in dichloromethane (2 ml), then the compound obtained in Preparation Example 23 (87 mg, 0.35 mmol) and N,N-disopropylethylamine (0.4 ml, 2.1 mmol) were added and stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (63 mg, yield: 35%, light ochre solid). 1 H NMR (400MHz, CDCl3) δ9.09 (s, 1H), 7.01 (d,J= 2.0 Hz, 1H), 6.99 (dd,J=8.0, 2.0 Hz, 1H), 6.87 (d,J= 8.0 Hz, 1H), 3.91 (s, 3H), 3.90 (s, 3H), 3.84 (br s, 2H), 3.81 (br s, 2H), 3.73 (br s, 2H), 3.36 (s, 3H), 3.30 (br s, 2H); MS (ESI) m / z513.0 [M+H] + Preparation Example 24: Tert-butyl 4-(3,4-dimethoxybenzyl)piperazine-1-carboxylate 1-Boc-piperazine (1 g, 5.4 mmol) and 3,4-dimethoxybenzyl bromide (1.49 g, 6.45 mmol) were dissolved in acetonitrile (20 ml), potassium carbonate (746.2 mg, 5.4 mmol) was added, and the mixture was stirred at 70°C for 5 hours. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (1.4 g, yield: 77.3%, clear viscous liquid). Preparation Example 25: 1-(3,4-dimethoxybenzyl)piperazine The compound (1.4 g, 4.16 mmol) obtained in Preparation Example 24 was dissolved in dichloromethane (28 ml), then trifluoroacetic acid (12.5 ml) was added at 0°C and stirred at room temperature for 1 hour. The reaction mixture was extracted with an aqueous solution of sodium hexanormal hydroxide and dichloromethane, and then concentrated under reduced pressure to obtain the title compound (660.0 mg, yield: 67.1%, white solid). Example 20: (5-Bromo-2-(methylsulfonyl)pyrimidine-4-yl)(4-(3,4-dimethoxybenzyl)piperazine-1-yl)methanone 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (100 mg, 0.35 mmol) was dissolved in dichloromethane (1 ml), then thionyl chloride (0.25 ml, 3.5 mmol) and dimethylformamide (3 drops) were added and stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in dichloromethane (2 ml), and then the compound obtained in Preparation Example 25 (82.7 mg, 0.35 mmol) and N,N-disopropylethylamine (0.4 ml, 2.1 mmol) were added and stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (110 mg, yield: 62.9%, ivory solid). 1 H NMR (400MHz, CDCl3) δ9.06 (s, 1H), 6.86 (s, 1H), 6.81 (s, 2H), 3.89 (s, 3H), 3.87 (s, 3H), 3.82 (t,J= 4.8 Hz, 2H), 3.49 (s, 2H), 3.356 (s, 3H), 3.25 (t,J= 4.8 Hz, 2H), 2.57 (t,J= 5.2 Hz, 2H), 2.47 (t,J= 5.2 Hz, 2H); MS (ESI) m / z499.0 [M+H] + [Reaction Equation 14] Example 21: N-(3,4-dimethoxyphenethyl)-2-(methylsulfonyl)-5-(trifluoromethyl)pyrimidine-4-carboxamide Tert-butyl 4-(2-(5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamido)ethyl)piperazine-1-carboxylate (60 mg, 0.12 mmol) was dissolved in a 20% trifluoroacetic acid / dichloromethane mixed solution (2 ml), water (2 drops) was added, and the mixture was stirred at room temperature for 1 day. After the reaction was complete, the solid was dried under reduced pressure, and then filtered while washing the solid with dichloromethane. Subsequently, the solid compound obtained through the filter was dissolved in a methanol and dichloromethane mixed solution, the undissolved sludge was filtered out, and the filtrate was dried under reduced pressure to obtain the title compound (61 mg, yield: 99%, white solid). 1 H NMR (400 MHz, DMSO-d6): δ9.45 (s, 1H), 8.96 (br s, NH), 8.69 (br s, NH), 3.64 (q,J= 7.2 Hz, 2H), 3.49-3.48 (m, 2H), 3.16 (br s, 4H), 2.82 (br s, 4H), 2.73 (br s, 2H), 1.26 (s, 3H); MS (ESI) 406.0m / z[M+H] + [Reaction Equation 15] Preparation Example 26: 2-tert-butyl (2-bromoethyl)carbamate 2-bromoethylamine was dissolved in dichloromethane (30 ml), and then triethylamine (2.5 ml, 18.2 mmol) was added. Subsequently, a vacuum needle was used to prevent the internal pressure from increasing, and then di-tert-butyl dicarbonate (5 ml, 16.6 mmol) was slowly added and stirred at room temperature for 4 hours. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (2.77 g, yield: 82%, white solid). Preparation Example 27: Tert-butyl (2-((3,4-dimethoxyphenyl)amino)ethyl)carbamate The compound obtained in Preparation Example 26 (2.77 g, 12.4 mmol), 3,4-dimethoxyaniline (2.85 g, 18.6 mmol), and potassium carbonate (5.12 g, 37.1 mmol) were dissolved in acetonitrile (50 ml) and stirred under reflux at 120 °C for 1 day. Afterward, the reaction mixture was concentrated under reduced pressure and dissolved again in dichloromethane; the insoluble sludge was removed by filtering, and the resulting filtrate was extracted by adding dichloromethane and water. Subsequently, the mixture was purified by column chromatography to obtain the title compound (976 mg, yield: 27%, brown oil). Preparation Example 28: (9H-fluore-9-nyl)methyl (2-((tert-butoxycarbonyl)amino)ethyl(3,4-dimethoxyphenyl)carbamate The compound obtained in Preparation Example 27 (970 mg, 3.27 mmol) and 9-fluorenylmethyl chloroformate (1.27 g, 4.91 mmol) were dissolved in dichloromethane (20 ml), followed by the addition of triethylamine (0.6 ml, 3.92 mmol) and stirring at room temperature for 2 hours. Afterward, the mixture was extracted by adding dichloromethane and a 0.5 normal hydrochloric acid solution, and then purified by column chromatography to obtain the title compound (1.43 g, yield: 86%, orange solid). Preparation Example 29: (9H-fluore-9-nyl)methyl (2-aminoethyl)(3,4-dimethoxyphenyl)carbamate hydrochloride The compound obtained in Preparation Example 28 (1.13 g, 2.18 mmol) was dissolved in dioxane (6.5 ml), then 4 molar hydrochloric acid solution (in dioxane) (6.5 ml, 26.16 mmol) was added and stirred at room temperature for 2 hours. Afterward, hexane was poured to produce a solid, and then filtered to obtain the title compound (900 mg, yield: 91%, pale yellow solid). Preparation Example 30: (9H-fluore-9-nyl)methyl (2-(5-bromo-2-(methylthio)pyrimidine-4-carboxamido)ethyl)(3,4-dimethoxyphenyl)carbamate 5-bromo-2-(methylthio)pyrimidine-4-carboxyside (150 mg, 0.6 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (173 mg, 0.9 mmol), and hydroxybenzotriazole (122 mg, 0.9 mmol) were dissolved in dimethylformamide (1 ml), after which N,N-diisopropylethylamine (116 mg, 0.9 mmol) was added and stirred at room temperature for 10 minutes. Then, the compound obtained in Preparation Example 29 (274 mg, 0.6 mmol) dissolved in dimethylformamide (1 ml) was added and stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate and water, and then purified by column chromatography to obtain the title compound (327 mg, yield: 84%, pale yellow solid). Preparation Example 31: (9H-fluore-9-nyl)methyl (2-(5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamido)ethyl)(3,4-dimethoxyphenyl)carbamate The compound obtained in Preparation Example 30 (324 mg, 0.5 mmol) was dissolved in methanol (4 ml), and potassium peroxymonosulfate (537 mg, 1.75 mmol) dissolved in water (4 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography to obtain the title compound (301 mg, yield: 88%, pale yellow solid). Example 22: 5-Bromo-N-(2-((3,4-dimethoxyphenyl)amino)ethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 31 (140 mg, 0.21 mmol) was dissolved in a 50% triethylamine / dimethylformamide solution and stirred at room temperature for 3 hours and 30 minutes. Subsequently, the triethylamine was removed by concentrating under reduced pressure at 40 ℃, and then extracted with ethyl acetate and water. The compound was then purified by column chromatography to obtain the title compound (56 mg, yield: 59%, reddish-brown solid). 1 H NMR (400 MHz, CDCl3): δ9.17 (s, 1H), 8.01 (br s, NH), 6.77-6.75 (m, 1H), 6.32-6.31 (m, 1H), 6.23-6.12 (m, 1H), 3.87 (s, 3H), 3.82 (s, 3H), 3.74 (q,J= 6.4 Hz, 2H), 3.42 (t,J= 6.4 Hz, 2H), 3.37 (s, 3H); MS (ESI) 459.0m / z[M+H] + [Reaction Equation 16] Preparation Example 32: 4-(2-(5-bromo-2-(methylthio)pyrimidine-4-carboxamido)ethyl)benzenesulfonyl chloride 5-bromo-2-(methylthio)-N-phenethylpyrimidine-4-carboxamide (290 mg, 0.82 mmol) was dissolved in chloroform (2.9 ml), then chlorosulfonic acid (0.45 ml, 6.83 mmol) was added at 0 ℃ and stirred at 0 ℃ for 30 minutes. After moving to room temperature and stirring for 6 hours and 30 minutes, water was added to terminate the reaction. The mixture was then extracted with water and ethyl acetate and purified by column chromatography to obtain the title compound (235 mg, yield: 63.3%, white solid). Preparation Example 33: 5-Bromo-N-(4-(N-methylsulfamoyl)phenethyl)-2-(methylthio)pyrimidine-4-carboxamide The compound obtained in Preparation Example 32 (44 mg, 0.09 mmol) was dissolved in dichloromethane (1 ml), then methylamine hydrochloride (7.9 mg, 0.12 mmol) and potassium carbonate (40.35 mg, 0.29 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (34 mg, yield: 78.7%, white solid). Example 23 Example 23-1: 5-Bromo-N-(4-(N-methylsulfamoyl)phenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 33 (30 mg, 0.07 mmol) was dissolved in methanol (2 ml), potassium peroxymonosulfate (72.9 mg, 0.24 mmol) dissolved in water (2 ml) was added, and the mixture was stirred at room temperature for 1 day. The solidified reaction mixture was filtered while washing with water and purified by column chromatography to obtain the title compound (20 mg, yield: 62.5%, white solid). 1 H NMR (400 MHz, DMSO-d6) δ9.41 (s, 1H), 9.03 (t,J= 5.6 Hz, NH), 7.71 (d,J= 8.4 Hz, 2H), 7.52 (d,J= 8.4 Hz, 2H), 7.39 (q,J= 5.2 Hz, NH), 3.59 (q,J= 6.8 Hz, 2H), 3.44 (s, 3H), 2.96 (t,J= 7.2 Hz, 2H), 2.40 (d,J= 5.2 Hz, 3H); MS (ESI)m / z477.0 [M+H] + Example 23-2 used a compound obtained through the same reaction as Preparation Examples 32 and 33 according to Reaction Scheme 16, and carried out the same reaction as Example 23-1 to obtain the corresponding compound. Example 23-2: 5-bromo-2-(ethylsulfonyl)-N-(4-(N-methylsulfamoyl)phenethyl)pyrimidine-4-carboxamide [Reaction Equation 17] Example 24 Example 24-1: Methyl 4-(2-(5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxamide)ethyl)benzenesulfonate The compound (110 mg, 0.24 mmol) obtained in Preparation Example 32 was dissolved in methanol (4 ml), and potassium peroxymonosulfate (258.2 mg, 0.84 mmol) dissolved in water (4 ml) was added and stirred at room temperature for 1 day. The solidified reaction mixture was filtered while washing with water and purified by column chromatography to obtain the title compound (18.7 mg, yield: 16.2%, white solid). 1 H NMR (400 MHz, CDCl3) δ9.18 (s, 1H), 7.90 (d,J= 8.4 Hz, 2H), 7.87 (br s, NH), 7.48 (d,J= 8.4 Hz, 2H), 3.79 (s, 3H), 3.77 (q,J= 6.8 Hz, 2H), 3.38 (s, 3H), 3.09 (t,J= 7.2 Hz, 2H); MS (ESI)m / z477.9 [M+H] + Example 24-2 obtained the corresponding compound by carrying out the same reaction as Example 24-1 according to Reaction Scheme 17. Example 24-2: Methyl 4-(2-(5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamido)ethyl)benzenesulfonate [Reaction Equation 18] Preparation Example 34: N-(4-(2-aminoethyl)phenyl)acrylamide trifluoroacetate Tert-butyl-4-aminophenethyl carbamate (400 mg, 1.69 mmol) was dissolved in dichloromethane (1 ml), and then N,N-diisopropylethylamine (0.4 ml, 2.3 mmol) was added. The temperature of the reaction mixture was lowered to -15 °C, then acryl chloride (0.15 ml, 1.86 mmol) was added, and the reaction was carried out at room temperature for 1 hour. After adding 1 ml of normal hydrochloric acid to terminate the reaction, the reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and then the next reaction was carried out immediately. The concentrated reaction mixture was dissolved in dichloromethane (2 ml), then trifluoroacetic acid (1 ml, 13.6 mmol) was added, and the reaction was carried out at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the solid formed after adding diethyl ether was filtered to obtain the title compound (435 mg, yield: 84.5%, pale ivory solid). Example 25 Example 25-1: N-(4-acrylamidophenethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (77.9 mg, 0.41 mmol), and N-hydroxysuccinate (46.7 mg, 0.41 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 34 (103 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (25.8 mg, yield: 16.3%, white solid). 1 H NMR (400 MHz, DMSO-d6) δ10.08 (s, NH), 9.42 (s, 1H), 8.97 (t,J= 5.2 Hz, NH), 7.60 (d,J= 8.4 Hz, 2H), 7.24 (d,J= 8.4 Hz, 2H), 6.46-6.39 (m, 1H), 6.24 (dd,J= 2.0 Hz, 1H), 5.74 (dd,J= 1.6 Hz, 1H), 3.62 (q,J= 7.2 Hz, 2H), 3.52 (q,J= 6.8 Hz, 2H), 2.82 (t,J= 7.2 Hz, 2H), 1.25 (t,J= 7.2 Hz, 3H); MS (ESI)m / z467.0 [M+H] + Example 25-2 used a compound obtained through the same reaction as Preparation Example 34 according to Reaction Scheme 18 and carried out the same reaction as Example 25-1 to obtain the corresponding compound. Example 25-2: N-(4-acrylamidophenethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 19] Preparation Example 35: (E)-3-(2-nitrovinyl)-1H-indole Indole-3-carboxyaldehyde (1.8 g, 12.4 mmol) was dissolved in nitromethane (14 ml, 261.4 mmol), then ammonium acetate (477.8 mg, 6.2 mmol) and benzene (0.17 ml, 1.86 mmol) were added, and the mixture was stirred at reflux temperature for 5 hours. The temperature of the reaction mixture was lowered to room temperature and concentrated under reduced pressure, resulting in a solid. The mixture was sonicated with dichloromethane and purified by filtration to obtain the title compound (1.75 g, yield: 75%, brown solid). Preparation Example 36: (E)-1-(methylsulfonyl)-3-(2-nitrovinyl)-1H-indole A substance (3.4 g, 18.1 mmol) containing the compound obtained in Preparation Example 35 was dissolved in dichloromethane (60 ml), then methanesulfonyl chloride (1.68 ml, 21.67 mmol) was added, the temperature was lowered to 0°C, N,N-diisopropylethylamine (3.77 ml, 21.67 mmol) was added, and the mixture was stirred at room temperature for 4 hours. When the reaction mixture was concentrated under reduced pressure, a solid was formed, and acetone was added to sonicate the mixture, followed by filtration and purification to obtain the title compound (2.6 g, yield: 54%, yellow solid). Preparation Example 37: (E)-2-(1-(methylsulfonyl)-1H-indole-3-yl)ethene-1-amine The compound obtained in Preparation Example 36 (1.5 g, 5.63 mmol) was added and argon-substituted, then anhydrous tetrahydrofuran (5 ml) was added and stirred at room temperature for 5 minutes. Anhydrous methanol (19 ml) was added to the reaction mixture, the temperature was lowered to 0°C, then sodium borohydride (639.5 mg, 16.9 mmol) was added and stirred again at room temperature for 10 minutes. After that, nickel(II) chlorohexahydrate (2.0 g, 8.41 mmol) was added in methanol (10 ml), then sodium borohydride (954.7 mg, 25.2 mmol) was added at 0°C and stirred for 15 minutes. The resulting NiB2 (crude) and sodium borohydride (2.13 g, 56.3 mmol) were slowly added at 0°C and reacted for 3 hours at room temperature under argon substitution. The reaction mixture was filtered to remove NiB2, and the filtrate was collected and concentrated under reduced pressure, after which water and ethyl acetate were added for extraction. The residue obtained from the extraction was purified by column chromatography to obtain the title compound (330 mg, yield: 24.6%, yellow solid). Example 26 Example 26-1: 5-Bromo-2-(methylsulfonyl)-N-(2-(1-(methylsulfonyl)-1H-indole-3-yl)ethyl)pyrimidine-4-carboxamide 5-Bromo-2-(methylsulfonyl)pyrimidine-4-carboxylic acid (120 mg, 0.4 mmol) was dissolved in dichloromethane (1.2 ml), then thionyl chloride (0.3 ml, 4.2 mmol) and dimethylformamide (3 drops) were added and stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in dichloromethane (3 ml), and then the compound obtained in Preparation Example 37 (102 mg, 0.42 mmol) and N,N-diisopropylethylamine (0.45 ml, 2.5 mmol) were added and stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, concentrated again, and the solid was filtered using dichloromethane and hexane. When filtering, the solid was washed with hexane and finally purified by washing the solid with a small amount of dichloromethane, and the title compound (68 mg, yield: 32%, white solid) was obtained. 1 H NMR (400MHz, CDCl3) δ9.18 (s, 1H), 7.93 (d,J= 8.0 Hz, 1H), 7.90 (br s, NH), 7.68 (d,J= 7.6 Hz, 1H), 7.44-7.34 (m, 3H), 3.84 (q,J= 6.8 Hz, 2H), 3.35 (s, 3H), 3.14 (s, 3H), 3.11 (t,J= 6.8 Hz, 2H); MS (ESI) m / z500.9 [M+H] + Examples 26-2 to 26-3 used compounds obtained through the same reaction as Preparation Examples 35, 36, and 37 according to Reaction Scheme 19, and carried out the same reaction as Example 26-1 to obtain the corresponding compounds, respectively. Example 26-2: 5-bromo-2-(ethylsulfonyl)-N-(2-(1-(methylsulfonyl)-1H-indol-3-yl)ethyl)pyrimidine-4-carboxamide Example 26-3: 5-bromo-N-(2-(1-(methylsulfonyl)-1H-indol-3-yl)ethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 20] Preparation Example 38: (E)-6-(2-nitrovinyl)-1H-indole Indole-6-carboxaldehyde (1.5 g, 10.3 mmol) was dissolved in nitromethane (16.5 ml, 309.9 mmol), followed by the addition of ammonium acetate (318.3 mg, 4.13 mmol) and stirring at 100 °C for 4 hours and 30 minutes. After the reaction was complete, the reaction mixture was concentrated under reduced pressure, and the resulting solid was filtered while washing with a small amount of dichloromethane to obtain the title compound (975 mg, yield: 50.1%, brown solid). Preparation Example 39: 2-(1H-indole-6-yl)ethane-1-amine Tetrahydrofuran (15 ml) was added to lithium aluminum hydride (616 mg, 16.23 mmol) and the temperature was lowered to 0 ℃. The compound obtained in Preparation Example 38 (650 mg, 3.45 mmol), dissolved in tetrahydrofuran (15 ml), was slowly added to this reaction mixture, and then the reaction temperature was raised to 80 ℃ and stirred for 2 hours. After the reaction was completed, the temperature of the reaction mixture was lowered to 0 ℃, and water was slowly added to quench the lithium aluminum hydride. The reaction mixture was then extracted using 1 normal hydrochloric acid, 1 mol sodium hydroxide aqueous solution, and ethyl acetate to obtain the title compound (275 mg, mixture, reddish-yellow solid) mixed with a small amount of impurities. Example 27 Example 27-1: N-(2-(1H-indole-6-yl)ethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (77.9 mg, 0.41 mmol), and N-hydroxysuccinide (46.7 mg, 0.41 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 39 (54.2 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (83 mg, yield: 56.1%, pale yellow solid). 1 H NMR (400 MHz, CDCl3) δ9.15 (s, 1H), 8.72 (br s, NH), 7.77 (br s, NH), 7.63 (d,J= 8.0 Hz, 1H), 7.48 (s, 1H), 7.23 (t,J= 2.8 Hz, 1H), 7.01 (d,J= 8.0 Hz, 1H), 6.53 (br s, 1H), 3.74 (q,J= 6.0 Hz, 2H), 3.45 (q,J= 7.6 Hz, 2H), 3.05 (t,J= 6.4 Hz, 2H), 1.38 (t,J= 7.6 Hz, 3H); MS (ESI)m / z437.0 [M+H] + Examples 27-2 to 27-4 used compounds obtained through the same reaction as Preparation Examples 38 and 39 according to Reaction Scheme 20, and carried out the same reaction as Example 27-1 to obtain the corresponding compounds, respectively. Example 27-2: N-(2-(1H-indol-6-yl)ethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 27-3: 5-bromo-2-(ethylsulfonyl)-N-(4-hydroxy-3,5-dimethylphenethyl)pyrimidine-4-carboxamide Example 27-4: 5-bromo-N-(4-hydroxy-3,5-dimethylphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 21] Preparation Example 40: Benzofuran-3-carbaldehyde oxime 1-benzofuran-3-carbaldehyde (1.2 g, 8.21 mmol) was dissolved in ethyl alcohol (20 ml) and water (20 ml), then hydroxylammonium chloride (855.4 mg, 12.31 mmol) and sodium hydroxide (1.64 g, 41.05 mmol) were added and stirred at room temperature for 1 day. After the reaction was complete, 1 normal hydrochloric acid was added, the resulting solid was filtered, and then purified by column chromatography to obtain the title compound (960 mg, yield: 72.5%, yellow solid). Preparation Example 41: Benzofuran-3-ylmethanamine The compound (710 mg, 4.4 mmol) obtained in Preparation Example 40 was added to acetic acid (10 ml), followed by the addition of zinc (432.1 mg, 6.6 mmol), and the reaction was carried out at 55°C for 7 hours and 30 minutes. Since the starting material remained, an equivalent amount of zinc was added during the reaction. After the reaction was completed, the mixture was extracted using 1 normal hydrochloric acid, 1 mol sodium hydroxide aqueous solution, and ethyl acetate to obtain the title compound (381 mg, mixture, clear liquid) mixed with a small amount of impurities. Example 28 Example 28-1: N-(benzofuran-3-ylmethyl)-5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (77.9 mg, 0.41 mmol), and N-hydroxysuccinate (46.7 mg, 0.41 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 41 (49.8 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (46 mg, yield: 32%, white solid). 1 H NMR (400 MHz, DMSO-d6) δ9.43 (s, 1H), 9.40 (t,J= 5.6 Hz, NH), 7.78 (dd,J= 7.6, 0.8 Hz, 1H), 7.99 (s, 1H), 7.59 (d,J= 8.0 Hz, 1H), 7.37-7.28 (m, 2H), 4.66 (d,J= 5.6 Hz, 2H), 3.61 (q,J= 7.6 Hz, 2H), 1.23 (t,J= 7.6 Hz, 3H); MS (ESI)m / z445.9 [M+Na] + Examples 28-2 to 28-3 used compounds obtained through the same reaction as Preparation Examples 40 and 41 according to Reaction Scheme 21, and carried out the same reaction as Example 28-1 to obtain the corresponding compounds, respectively. Example 28-2: N-(benzofuran-3-ylmethyl)-5-bromo-2-(propylsulfonyl)pyrimidine-4-carboxamide Example 28-3: 5-bromo-N-(4-bromo-2,5-dimethoxybenzyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 22] Preparation Example 42: Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid (5 g, 20.07 mmol) was dissolved in dichloromethane (50 ml), then thionyl chloride (10.2 ml, 140.52 mmol) and dimethylformamide (50 drops) were added and stirred at room temperature for 40 minutes. Afterward, the temperature was lowered to 0 ℃, methanol (30 ml) was added, and the mixture was stirred for 10 minutes. The reaction mixture was extracted with water and dichloromethane and purified by column chromatography to obtain the title compound (1.5 g, yield: 28.4%, white solid). Preparation Example 43: Methyl 2-(methylthio)-5-(trifluoromethyl)pyrimidine-4-carboxylate The compound obtained in Preparation Example 42 (400 mg, 1.52 mmol) and (1,10-phenanthroline)(trifluoromethyl)copper(l) (714 mg, 2.28 mmol) were dissolved in dimethylformamide (4 ml) and stirred at 50 °C for 1 day. Subsequently, water and ethyl acetate were added, and the insoluble sludge was filtered out, after which the organic layer was extracted. The mixture was then purified by column chromatography to obtain the title compound (120 mg, yield: 31%, yellow oil). Preparation Example 44: 2-(methylthio)-5(trifluoromethyl)pyrimidine-4-carboxylic acid The compound (91 mg, 0.47 mmol) obtained in Preparation Example 43 was dissolved in tetrahydrofuran (2 ml), and then lithium hydroxide (60 mg, 1.42 mmol) dissolved in water (1 mL) was added and stirred at room temperature for 1 day. Subsequently, an aqueous layer was obtained by extraction with water and ethyl acetate, and then an aqueous layer was obtained by further extraction with water saturated with sodium bicarbonate and ethyl acetate. Afterward, a small amount of concentrated hydrochloric acid solution at 0 ℃ was added to adjust the pH to 2, and then an organic layer was obtained by extraction with a 10% methanol / dichloromethane solution and water. The organic layer was then dried under reduced pressure to obtain the title compound (91 mg, yield: 81%, white solid). Preparation Example 45: N-(3,4-dimethoxyphenethyl)-2-(methylthio)-5-(trifluoromethyl)pyrimidine-4-carboxyamide The compound obtained in Preparation Example 44 (100 mg, 0.42 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (121 mg, 0.63 mmol), and hydroxybenzotriazole (86 mg, 0.63 mmol) were dissolved in dimethylformamide (1 ml) and stirred at room temperature for 10 minutes. Subsequently, 3,4-dimethoxyphenylethanolamine (76 mg, 0.42 mmol) and N,N-disopropylethylamine (0.2 ml, 1.26 mmol) dissolved in dimethylformamide (1 ml) were added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was extracted with a 1 normal hydrochloric acid solution and ethyl acetate, and purified by column chromatography to obtain the title compound (103 mg, yield: 61%, white solid). Example 29: N-(3,4-dimethoxyphenethyl)-2-(methylsulfonyl)-5-(trifluoromethyl)pyrimidine-4-carboxamide The compound obtained in Preparation Example 45 (100 mg, 0.25 mmol) was dissolved in methanol (2 ml), and then potassium peroxymonosulfate (268 mg, 0.87 mmol) dissolved in water (2 ml) was added and stirred at room temperature for 1 day. The reaction mixture was extracted with water and dichloromethane and then purified by column chromatography to obtain the title compound (62 mg, yield: 57%, white solid). 1 H NMR (400 MHz, CDCl3): δ 9.36 (s, 1H), 7.68 (br s, NH), 6.88-6.79 (m, 3H), 3.90 (s, 3H), 3.89 (s, 3H), 3.76 (q,J= 6.8 Hz, 2H), 6.41 (s, 3H), 2.94 (t,J= 6.8 Hz, 2H) ; MS (ESI) 434.1m / z[M+H] + [Reaction Equation 23] Preparation Example 46: (E)-1-bromo-2,5-dimethoxy-4-(2-nitrovinyl)benzene 4-Bromo-2,5-dimethoxybenzaldehyde (1.6 g, 6.53 mmol) was dissolved in nitromethane (10.32 ml, 195.9 mmol), followed by the addition of ammonium acetate (201.33 mg, 2.61 mmol) and stirring at 100 °C for 5 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure, and the resulting solid was filtered while washing with a small amount of dichloromethane to obtain the title compound (975 mg, yield: 51.8%, yellow solid). Preparation Example 47: 1-Bromo-2,5-dimethoxy-4-(2-nitroethyl)benzene A mixed solution was prepared by adding '1,4-dioxane / ethanol' (2:1) (15 ml) to sodium borohydride (254.3 mg, 6.72 mmol), and then lowering the temperature to 0 ℃. The compound obtained in Preparation Example 46 (970 mg, 3.36 mmol) was dissolved in 1,4-dioxane, slowly added to the reaction mixture at 0 ℃, and stirred for 50 minutes at the above temperature. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (445 mg, yield: 45.6%, yellow solid). Preparation Example 48: 2-(4-bromo-2,5-dimethoxyphenyl)ethane-1-amine The compound obtained in Preparation Example 47 (440 mg, 1.52 mmol) was added to acetic acid (15 ml), followed by the addition of zinc (1.98 g, 30.33 mmol) and the reaction was carried out at room temperature for 30 minutes. After the reaction was complete, the mixture was extracted using 1 normal hydrochloric acid, 1 mol sodium hydroxide aqueous solution, and ethyl acetate to obtain the title compound (232 mg, yield: 58%, pale blue transparent liquid). Example 30 Example 30-1: 5-Bromo-N-(4-Bromo-2,5-Dimethoxyphenetyl)-2-(ethylsulfonyl)pyrimidine-4-Carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (77 mg, 0.26 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (59.4 mg, 0.31 mmol), and N-hydroxysuccinimide (35.7 mg, 0.31 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 48 (70 mg, 0.26 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (54 mg, yield: 38.6%, white solid). 1 H NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 7.97 (br s, 1H), 7.09 (s, 1H), 6.80 (s, 1H), 3.86 (s, 3H), 3.86 (s, 3H), 3.70 (q,J= 6.8Hz, 2H), 3.55 (q,J= 7.6 Hz, 2H), 2.97 (t,J= 7.2 Hz, 2H), 1.45 (t,J= 7.2 Hz, 3H); MS (ESI)m / z535.9 [M+H] + Examples 30-2 to 30-3 used compounds obtained through the same reaction as Preparation Examples 46, 47, and 48 according to Reaction Scheme 23, and carried out the same reaction as Example 30-1 to obtain the corresponding compounds, respectively. Example 30-2: 5-bromo-N-(4-bromo-2,5-dimethoxyphenethyl)-2-(methylsulfonyl)pyrimidine-4-carboxamide Example 30-3: 5-bromo-N-(4-bromo-2,5-dimethoxyphenethyl)-2-(propylsulfonyl)pyrimidine-4-carboxamide [Reaction Equation 24] Preparation Example 49: 3-Ethylpentanitrile Sodium cyanide (133.7 mg, 2.73 mmol) and potassium iodide (5.47 mg, 0.033 mmol) were dissolved in dimethyl sulfoxide (2 ml) and stirred at 40 °C for 10 minutes. At the same temperature, 1-bromo-2-ethylbutane (300 mg, 1.82 mmol) was slowly added to the reaction mixture, and the temperature was raised to 100 °C and stirred for 1 day. The reaction mixture was concentrated under reduced pressure and extracted with water and diethyl ether to obtain the title compound (1.61 g, Mixture, pale yellow transparent liquid). Preparation Example 50: 3-ethylpentane-1-amine Diethyl ether (20 ml) was added to lithium aluminum hydride (1.09 g, 28.76 mmol) and the temperature was lowered to 0 °C. The compound obtained in Preparation Example 49 (1.6 g, 14.38 mmol) was slowly added to this reaction mixture, and then the reaction temperature was raised to 40 °C and stirred for 4 hours. After the reaction was finished, the temperature of the reaction mixture was lowered to 0 °C, and water was slowly added to quench the lithium aluminum hydride. The reaction mixture was then extracted using 1 normal hydrochloric acid, 1 mol sodium hydroxide aqueous solution, and ethyl acetate to obtain the title compound (345 mg, mixture, pale yellow transparent liquid) mixed with a small amount of impurities. Example 31: 5-Bromo-N-(3-ethylpentyl)-2-(ethylsulfonyl)pyrimidine-4-carboxamide 5-bromo-2-(ethylsulfonyl)pyrimidine-4-carboxylic acid (100 mg, 0.34 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (78.6 mg, 0.41 mmol), and N-hydroxysuccinimide (47.2 mg, 0.41 mmol) were dissolved in dimethylformamide (2 ml), then the compound obtained in Preparation Example 50 (39.2 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, extracted with water and ethyl acetate, and purified by column chromatography to obtain the title compound (10 mg, yield: 7.49%, clear viscous liquid). 1 H NMR (400 MHz, CDCl3) δ 9.18 (s, 1H), 7.73 (br s, 1H), 3.59 (q,J= 7.6 Hz, 2H), 3.51-3.46 (m, 2H), 1.65-1.57 (m, 2H), 1.47 (t,J= 7.6 Hz, 3H), 1.42-1.30 (m, 5H), 0.90 (t,J= 7.2 Hz, 6H); MS (ESI) m / z 329.1 [M+H] + cell culture In this study, the THP-1 cell line, a monocyte cell isolated from the peripheral blood of an acute mononuclear leukemia patient, was purchased from ATCC and used. THP-1 cells were cultured in 1X RPMI 1640 medium (Gibco, A1049101) containing 10% fetal bovine serum (Gibco, 1600044) and 1% penicillin streptomycin (Gibco, 00354) at 37°C and 5% CO2. cytotoxicity test To evaluate the cytotoxicity of the synthesized compound, a cell counting kit-8 assay (CCK-8 assay, Dojindo, CK04) was performed. To differentiate THP-1 cell lines into human macrophages, phorbol 12-myristate 13-acetate (PMA) was added at a concentration of 50 ng / mL, and the cells were cultured in a 96-well plate at a density of 5.0 x 10⁴ cells / well. After 24 hours, the culture medium containing PMA was removed, and the synthetic compound was diluted to a concentration of 10 μM and dispensed into fresh growth medium, followed by incubation for 24 hours. After 24 hours, 10 μL of CCK-8 reagent was added to each well and reacted for 2 hours, after which the absorbance was measured at a wavelength of 450 nm. Cell viability was calculated according to the following formula. [Mathematical Formula 1] OD (control) = Absorbance of untreated group OD (blank) = CCK-8 reagent absorbance OD (sample) = Absorbance of compound treatment group Enzyme-linked immunosorbent assay (ELISA) To determine the degree of inhibition of the cytokine IL-1β generated by NLRP3 inflammasome activation, a human IL-1β Quantikine ELISA Kit (R&D System, SLB50) was performed. To differentiate THP-1 cell lines into human macrophages, phorbol 12-myristate 13-acetate (PMA) was added at a concentration of 50 ng / mL, and the cells were cultured in a 96-well plate to a density of 2.5 x 10⁴ cells / well. After 24 hours, the culture medium containing PMA was removed, and the cells were cultured in fresh growth medium for 48 hours. Subsequently, 2 μg / mL of LPS (Sigma-Aldrich, L5424) was added to the differentiated THP-1 cell lines, and the cells were cultured for 4 hours. Afterward, the synthetic compound was diluted to a concentration of 1 μM and reacted for 30 minutes, followed by the addition of 10 μM of nigericin (Invivogen, tlrl-nig) and reacted for an additional 30 minutes. ELISA was performed using 50 μL of the supernatant per well according to the manual protocol enclosed in the kit. Evaluation of the oligomerization inhibitory ability of Apopotosis-associated speck-like protein containing a CARD (ASC) protein ASC is a protein that plays an important role in the inflammatory response signaling pathway and is one of the components of the NLRP3 inflammasome complex. Oligomerized ASC binds to the NLRP3 protein and promotes the activation of the NLRP3 inflammasome. To differentiate THP-1 cell lines into human macrophages, phorbol 12-myristate 13-acetate (PMA) was added at a final concentration of 50 ng / mL, and the cells were cultured in a 6-well plate to a density of 2 x 10⁶ cells / well. After 24 hours, the culture medium containing PMA was removed, and the cells were cultured in fresh growth medium for 48 hours. Subsequently, LPS (Sigma-Aldrich, L5424) at a final concentration of 0.5 μg / mL was added to the differentiated THP-1 cell lines to induce priming for 3 hours. Then, the synthetic compound of the present invention was reacted at a concentration of 1 μM for 30 minutes, followed by an additional reaction with nigericin (Invivogen, tlrl-nig) for 30 minutes to reach a final concentration of 2.5 μM. Cells treated with stimulation were lysed using NP-40 buffer and centrifuged at 13,000 rpm for 15 minutes. The supernatant was removed, and the remaining precipitate was washed once with PBS. After completely removing the PBS, the precipitate was treated with disuccinimidyl suberate (DSS) at a final concentration of 2 mM, and crosslinking was performed using a rotator at room temperature for 30 minutes. After the reaction was complete, the sample was centrifuged at 4,000 rpm for 5 minutes to remove the supernatant, and Laemmli sample buffer was added to the precipitate to form a sample. The sample was heated in a heating block at 95°C for 5 minutes, then completely cooled, and Western blot analysis was performed, as shown in Figure 1. Foregoing, specific parts of the present invention have been described in detail. It will be apparent to those skilled in the art that such specific descriptions are merely preferred embodiments and do not limit the scope of the invention. Accordingly, the actual scope of the invention is defined by the claims and their equivalents.

Claims

1. A compound represented by Chemical Formula 1, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 1] In Chemical Formula 1 R 1 , R 2 and R 3 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl; -CONR 10 R 11 ; -NR 10 CO-R 11 ; R 12 CO- and, here, R 10 and R 11 Each is independently a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A and, Here, A is i) a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and R 12 is a C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, or C5-C20 alkylheteroaryl, wherein the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4, and; R 4 is a hydrogen atom or a C1-C6 alkyl.

2. The compound of claim 1, characterized by being represented by Chemical Formula 2, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 2] In Chemical Formula 2 R 5 and R 6 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl, and R 13 and R 14 Each independently consists of a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A or R 13 and R 14 Together, they can form a saturated or unsaturated heterocycloalkyl or heteroaryl ring having 2 to 20 carbon atoms and 1 to 7 heteroatoms, and Here, A is i) a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4, and; R 7 is a hydrogen atom or a C1-C6 alkyl.

3. The compound of claim 1, characterized by being represented by Chemical Formula 3, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 3] In chemical formula 3 R 8 is a hydrogen atom, halogen, amino, C1-C6 alkyl halide, hydroxy, and R 9 is a C1-C6 alkyl, and R 13 and R 14 Each is independently a hydrogen atom, C1-C12 alkyl, hydroxy, -(CH2) n -A or R 13 and R 14 Together, they can form a saturated or unsaturated heterocycloalkyl or heteroaryl ring having 2 to 20 carbon atoms and 1 to 7 heteroatoms, and Here, A is i) a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4.

4. The compound of claim 1, characterized by being represented by Chemical Formula 4, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 4] In chemical formula 4 R 5 and R 6 Each independently consists of: hydrogen atom; halogen; hydroxy; amino; cyano; nitro; C1-C6 alkyl halide; C1-C12 alkyl; C2-C6 Alkenyl; C2-C6 alkynyl; C1-C6 alkoxy; C1-C6 alkoxyalkyl; C1-C6 aminoalkyl; C1-C6 hydroxyalkyl; C1-C6 haloalkyl; C3-C10 cycloalkyl; C2-C7 heterocycloalkyl; C3-C10 alkylcycloalkyl; C2-C7 alkylheterocycloalkyl; C6-C20 aryl; C6-C20 alkylaryl; C5-C20 heteroaryl; C5-C20 alkylheteroaryl, and ⓐ is a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A, where A is i) C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain a heteroatom selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, 3, or 4; R 7 is a hydrogen atom or a C1-C6 alkyl.

5. The compound of claim 1, characterized by being represented by Chemical Formula 5, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof: [Chemical Formula 5] In chemical formula 5 R 8 is a hydrogen atom, a halogen, an amino, and a C1-C6 alkyl halide, and R 9 is a C1-C6 alkyl, and ⓐ is a hydrogen atom, C1-C12 alkyl, cyano, halogen, hydroxy, -(CH2) n -A, where A is i) C1-C12 alkyl, cyano, halogen, hydroxy, C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl or C5-C20 alkylheteroaryl, or ii) a polycyclic functional group formed by fusing 2 to 4 functional groups selected from the group consisting of C6-C20 aryl, C3-C10 cycloalkyl, C2-C7 heterocycloalkyl, C6-C20 alkylaryl, C5-C20 heteroaryl, and C5-C20 alkylheteroaryl, and Here, the heteroaryl and heterocycloalkyl contain a heteroatom selected from oxygen, sulfur, and nitrogen, and the aryl and heteroaryl are unsubstituted or halogen, hydroxy, amino, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, or R 15 It can be substituted with SO2-, where R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 It is a hydrogen atom or a C1-C6 alkyl; n is 1, 2, or 3.

6. In any one of paragraphs 1 to 5, the above A is i) one of Chemical Formulas 6 to 11 or ii) unsubstituted or C1-C6 alkoxy or methylsulfonyl substituted naphthalenyl or benzofuran, indole, indazole, or iii) -(CH2) n -A or, where A is a C1-C6 alkyl, cyano, halogen, or hydroxyl, and n is 1 or 2, and iv) C3-C6 cycloalkyl or iv) A compound characterized as being unsubstituted or substituted with a C1-C6 alkyl or alkyl ester peperidinyl or piperazinyl, a pharmaceutically acceptable salt thereof or a stereoisomer thereof: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] R 18 and R 19 are each independently hydrogen atoms, C1-C6 alkyl, hydroxy, carboxyl, ester, C1-C6 alkoxy, halogen, C1-C6 alkyl halide, R 20 CONH, carbonyl, halogenated carbonyl, R 15 SO2- and, where, R 15 is a C1-C6 alkyl, C1-C6 alkoxy, or NR 16 R 17 and, the above R 16 and R 17 is a hydrogen atom or a C1-C6 alkyl; R 20 is a hydrogen atom, a C1-C6 alkyl, or a C2-C6 alkenyl, and W is a single bond or -NH or -CH2O- and R 21 and R 22 Each is independently hydrogen or a C1-C6 alkyl, and X and Y are heteroatoms selected from carbon or oxygen, sulfur and nitrogen, wherein X and Y cannot be carbon simultaneously, and hydrogen or a C1-C6 alkyl group is bonded to the heteroatom to satisfy the normal valence of the said atom, and Z is a heteroatom selected from oxygen, sulfur, and nitrogen, wherein hydrogen or a C1-C6 alkyl group is bonded to the heteroatom to satisfy the normal valence of the atom.

7. A compound, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, characterized in that, in any one of claims 1 to 5, A is one of the following functional groups:

8. In paragraph 1, a compound selected from the following group, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof:

9. The compound of claim 1, characterized by being selected from the group consisting of compounds 1 to 18, a pharmaceutically acceptable salt thereof, or a stereoisomer thereof.

10. A pharmaceutical composition for the treatment or prevention of inflammatory diseases comprising, as an active ingredient, a compound according to any one of claims 1 to 9, a salt thereof, or a stereoisomer thereof.

11. A pharmaceutical composition for treating or preventing inflammatory diseases according to claim 10, wherein the inflammatory disease is selected from the group consisting of neurodegenerative diseases, cardiovascular diseases, metabolic diseases, immune diseases, and inflammatory skin diseases.

12. In paragraph 11, the neurodegenerative disease is Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis (ALS), Creutzfeldt-Jakob disease, multiple sclerosis, Lewy body dementia, leukocytosis, temporal lobe epilepsy, frontotemporal dementia, viral encephalitis, epilepsy, or stroke, and The above cardiovascular disease is heart failure or ischemic heart disease, and The above metabolic diseases are type 2 diabetes, arteriosclerosis, obesity, hyperlipidemia, hypercholesterolemia, non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH), and The above immune diseases are Merkle-Wells syndrome (MWS), Sjögren's syndrome, adult-onset delayed autoimmune diabetes mellitus (LADA), familial cold autoinflammatory syndrome (FCAS), cryopyrin-associated periodic syndrome (CAPS), neonatal multisystem inflammatory syndrome (NOMID), chronic infantile neurocutaneous joint syndrome (CINCA), familial Mediterranean fever (FMF), systemic juvenile idiopathic arthritis (SJIA), systemic juvenile idiopathic rheumatoid arthritis, adult rheumatoid arthritis, gout, or gouty arthritis, and A pharmaceutical composition for treating or preventing inflammatory diseases, characterized in that the above-mentioned inflammatory skin disease is psoriasis, eczema, acne, pustulosis, or actinic keratosis.

13. A health functional food for preventing or improving inflammatory diseases comprising, as an active ingredient, a compound according to any one of paragraphs 1 to 9, a salt thereof, or a stereoisomer thereof.

14. A pharmaceutical composition for preventing or improving inflammatory diseases according to claim 13, wherein the inflammatory disease is selected from the group consisting of neurodegenerative diseases, cardiovascular diseases, metabolic diseases, immune diseases, and inflammatory skin diseases.

15. In paragraph 14, the neurodegenerative disease is Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis (ALS), Creutzfeldt-Jakob disease, multiple sclerosis, Lewy body dementia, leukocytosis, temporal lobe epilepsy, frontotemporal dementia, viral encephalitis, epilepsy, or stroke, and The above cardiovascular disease is heart failure or ischemic heart disease, and The above metabolic diseases are type 2 diabetes, arteriosclerosis, obesity, hyperlipidemia, hypercholesterolemia, non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH), and The above immune diseases are Merkle-Wells syndrome (MWS), Sjögren's syndrome, adult-onset delayed autoimmune diabetes mellitus (LADA), familial cold autoinflammatory syndrome (FCAS), cryopyrin-associated periodic syndrome (CAPS), neonatal multisystem inflammatory syndrome (NOMID), chronic infantile neurocutaneous joint syndrome (CINCA), familial Mediterranean fever (FMF), systemic juvenile idiopathic arthritis (SJIA), systemic juvenile idiopathic rheumatoid arthritis, adult rheumatoid arthritis, gout, or gouty arthritis, and A pharmaceutical composition for preventing or improving inflammatory diseases, characterized in that the above-mentioned inflammatory skin disease is psoriasis, eczema, acne, pustulosis, or actinic keratosis.

16. A pharmaceutical formulation comprising the pharmaceutical composition of paragraph 10 for the treatment or prevention of inflammatory diseases.

17. A pharmaceutical formulation according to claim 16, characterized as being an oral administration, transdermal administration, subcutaneous injection, or topical application.

18. A pharmaceutical formulation according to claim 16, wherein the oral administration formulation is selected from the group consisting of powder, granules, tablets, pills, sugar-coated tablets, capsules, liquids, gels, syrups, slurries, and suspensions.

19. A pharmaceutical formulation according to claim 16, wherein the above-mentioned external formulation is selected from the group consisting of creams, lotions, topical ointments, oils, moisturizers, gels, aerosols, and nasal inhalers.

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