Aminoalkylamide derivative compound comprising benzyloxy group and Anti-inflammatory pharmaceutical composition comprising same

Abstract

The present invention provides an anti-inflammatory pharmaceutical composition comprising an aminoalkylamide derivative compound containing a benzyloxy group as an active ingredient. The aminoalkylamide derivative compound containing a benzyloxy group is a compound represented by chemical formulae 1 to 31, and exhibits, on average, high cell viability and high inhibitory activity against the 5-HT2A receptor.

Description

Aminoalkylamide derivative compounds containing a benzyloxyl group and anti-inflammatory pharmaceutical compositions containing the same The present invention relates to an aminoalkalamide derivative compound containing a benzyloxyl group, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof; and a pharmaceutical composition for treating inflammation or pruritus containing the same as an active ingredient. Opportunistic fungal infections are on the rise due to impaired immune function, with representative opportunistic pathogens reported to include *Candida albicans*, *Candida glabrata*, and *Candida krusei*. Conventional techniques for treating these Candida infections primarily involve antifungal-based approaches to suppress or eliminate the infection, including azole, polyene, echinocandi, and allylamine antifungals. However, *Candida albicans*, *Candida glabrata*, and *Candida auris* exhibit high resistance to azole antifungals, leading to an increasing number of cases where treatment is difficult. As existing antifungal agents carry various side effects, such as high resistance or cytotoxicity, research into therapeutic methods based on neuro-immune interactions is necessary to minimize these adverse effects. Throughout the specification, numerous papers and patent documents are referenced and their citations are indicated. The disclosures of the cited papers and patent documents are incorporated by reference into this specification in their entirety to more clearly explain the state of the art to which the present invention pertains and the content of the present invention. The present invention is a result derived as part of the research project titled "Development of a Treatment for Chronic Pain / Itching After Candida Infection Based on Neuro-Immune Interactions" (Project No. 2460000446, Project No. RS-2023-00265913), which was conducted as a Global Research Cooperation Support Project funded by the Ministry of Health and Welfare of the Republic of Korea through the Korea Health Industry Development Institute to Yonsei University Industry-Academic Cooperation Foundation and Amtics Bio. The inventors made diligent efforts to develop novel compounds for preventing or treating pruritus after Candida infection. As a result, the present invention was completed by discovering that aminoalkylamide derivative compounds containing a benzyloxyl group of Chemical Formulas 1 to 30 described below effectively inhibit 5-HT2A receptors. However, the technical problems that the present invention aims to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by those skilled in the art from the description below. Various embodiments of the present invention are described with reference to the drawings. In the following description, for a complete understanding of the present invention, various specific details, such as specific forms, compositions, and processes, are described. However, specific embodiments may be practiced without one or more of these specific details, or in combination with other known methods and forms. In other examples, known processes and manufacturing techniques are not described as specific details so as not to make the present invention unnecessary or obscure. Reference throughout this specification to one embodiment implies that a particular feature, form, composition, or characteristic described in association with the embodiment is included in one or more embodiments of the present invention. Accordingly, the circumstances of an embodiment expressed at various locations throughout this specification do not necessarily represent the same embodiment of the present invention. Additionally, a particular feature, form, composition, or characteristic may be combined in any suitable way in one or more embodiments. The entire contents of Korean Patent Application No. 10-2018-7033364, filed on October 30, 2017, and Korean Patent Application No. 10-2021-7000289, filed on June 25, 2020, are incorporated into the specification of the present invention by reference. In this specification, the term “alkyl” means a straight-chain, pulverized, or cyclic saturated hydrocarbon group, and includes, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, heptyl, and octyl. In this specification, the term “heterocycloalkyl” means a saturated carbon ring containing oxygen, sulfur, or nitrogen as a heteroatom within the ring. “Heterocycloalkyl of a pentagonal-hexagonal ring” means that the sum of the number of carbons and heteroatoms forming the ring is 5 to 6. In this specification, the term “benzyloxy group” refers to a form in which a benzyl group (C6H5CH2-) and a hydroxyl group (-OH) are combined, and is represented by the structural formula C6H5CH2O-. The benzyloxy group is an ether-type protecting group in which a phenyl group (benzene ring, C6H5-) is connected to an oxygen atom through a methylene group (-CH2-). In this specification, the term “Aminoalkylamide” refers to a compound in which an amino group (-NH2) and an alkyl group (-R, hydrocarbon chain) are bonded to an amide structure. It primarily refers to an organic compound containing an aminoalkyl portion along with an amide bond. In this specification, the term “haloalkyl” means an alkyl group substituted with a halogen, for example, C1-C3 haloalkyl means a functional group in which one or more hydrogens of an alkyl having 1 to 3 carbon atoms are substituted with a halogen. In this specification, the term “halogen” refers to a halogen group element and includes, for example, fluoro, chloro, bromo, and iodo. In this specification, the term “aryl” refers to a monocyclic or polycyclic carbon ring that is wholly or partially unsaturated and has aromaticity. For example, C6-C 10 Aryl means a monocyclic or polycyclic carbon ring that is wholly or partially unsaturated and aromatic, composed of 6 to 10 carbon atoms. In this specification, the term “heteroaryl” means a heterocyclic aromatic group containing oxygen, sulfur, or nitrogen within the ring as a heteroatom. The number of heteroatoms included within the ring is 1-3, specifically 1-2. The above aryl and heteroaryl groups may be single rings or fused polycyclic rings. In this specification, the term “alkoxy” means a radical formed by removing hydrogen from an alcohol, for example, C1-C3 alkoxy means a radical formed by removing hydrogen from an alcohol having 1 to 3 carbon atoms. In this specification, the term “haloalkoxy” refers to a radical substituted with a haloalkyl, which is an alkyl group substituted with a halogen on the alkoxy group. For example, C1-C4 haloalkoxy refers to a functional group in which a haloalkyl group is connected to a radical formed by removing hydrogen from an alcohol having 1 to 3 carbon atoms. That is, it refers to a -OR radical in which R is a haloalkyl as defined in this specification. For example, it may be -OCF3, -OCHF2, etc., but is not limited thereto. In this specification, the term "haloalkoxyalkyl" refers to an alkyl group substituted with the haloalkoxy defined above, unless otherwise noted. For example, it may be a haloC1-6 alkoxyalkyl comprising a total of 1 to 6 carbon atoms, but is not limited thereto. In this specification, the term “aryloxy group” means that the alkyl group of the alkoxy group is substituted with an aryl group in the definition of the alkoxy group, and aryloxy groups include, but are not limited to, phenoxy group, p-toryloxy group, m-toryloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthyloxy group, 2-anthyloxy group, 9-anthyloxy group, 1-phenanthyloxy group, 3-phenanthyloxy group, 9-phenanthyloxy group. In this specification, the term “amino group” may be -NH2, -NH(R), -N(R')(R''), and R' and R' may independently be alkyl groups having 1 to 10 carbon atoms, in which case it is called an “alkylamino group”. It is obvious to a person skilled in the art that hydrogen is omitted in accordance with the octet rule in this specification. In this specification, the term “Candida” refers to a genus of fungi that is the most common cause of fungal infections worldwide. The genus Candida includes approximately 200 species, such as Candida albicans, Candida tropicalis, and Candida glabrata, many of which are harmless commensalists or endosymbiotics to hosts, including humans. However, if the mucosal barrier is compromised or the immune system is damaged, they can invade and cause diseases known as opportunistic infections. Candida is found on most mucosal surfaces, such as the mouth, digestive tract, and vagina, as well as on the skin and gastrointestinal tract. While many species of the genus Candida, including Candida albicans, are found in the gut microbiota of mammalian hosts, there are also other species that live as endosymbiotics in insects. Systemic infections of the bloodstream and major organs (candidemia or invasive candidiasis) have a greater impact, especially on patients with compromised immune systems. In this specification, the term “candidiasis” or “Candidas” refers to an infectious disease caused by Candida, a type of fungus. It occurs when one or more parts of the body become infected and exhibit various symptoms and courses depending on the site of infection. Candida commonly causes infections confined to the surface layers of the skin or mucous membranes, and symptoms such as thrush, inflammation of the oropharynx or esophagus, vulvitis, vaginitis, and paronychia may appear. In this specification, the term “pruritus” refers to itching, an unpleasant sensation that makes one want to scratch or rub the skin. Pruritus is felt through a series of processes in which peripheral sensory nerves in the skin perceive specific stimuli and transmit information to the central nervous system, similar to pain. However, unlike stimuli that cause pain and trigger the withdrawal reflex, stimuli that cause pruritus trigger the scratch reflex. Itching originating in the skin is known as “pruritoceptives” and is triggered by various stimuli, including mechanical, chemical, thermal, and electrical stimuli. Pruritus following a Candida infection is a very common symptom of Candida infection, occurring particularly in infected areas such as the vagina, skin, and mouth. This is because the excessive proliferation of Candida bacteria causes an inflammatory response. In this specification, the term “neuro-immune interaction” refers to a method of understanding and approaching the complex mechanisms of the nervous and immune systems. When a Candida infection occurs, immune responses and neurotransmitters are activated, affecting inflammation and the sensory nervous system; these interactions can cause or persist chronic pain and pruritus. In this regard, when inflammatory cytokines such as IL-1β, TNF-α, and IL-6 are secreted due to Candida infection, they activate sensory nerves, causing itching and pain. When nerve growth factor (NGF) is excessively secreted during the inflammatory process, sensory nerves become overactive, and immune cells such as mast cells and neutrophils release histamine and tryptase, causing pruritus, and also neurotransmitters such as prostaglandins amplify the pain response. In this specification, the term “inflammation” refers to a protective response involving immune cells, blood vessels, and inflammatory mediators as one of the biological responses to harmful stimuli. The purpose of inflammation is to inhibit cell damage in the early stages, remove destroyed tissue and necrotic cells at the site of injury, and simultaneously regenerate tissue. Substances that trigger an inflammatory response include pathogens, damaged cells, irritants, and danger signals. Inflammation is a non-specific response mediated by innate immunity; when caused by pathogens, it occurs regardless of the type of pathogen or prior infection, and not only innate immunity but also some local adaptive immunity is involved in inflammation. While inflammation has a protective function of healing infections or promoting tissue regeneration, it can simultaneously result in tissue damage or disease. Inflammation causes redness and a sensation of heat as blood flow increases to the site of inflammation, and edema develops as fluid accumulates in the tissues due to increased vascular permeability. Additionally, the release of histamine and bradycanin, which stimulate nerve endings, leads to the sensation of pain. In this specification, the term “anti-inflammatory” refers to the property of inhibiting the process of inflammation or eliminating inflammation. Inflammation is a protective response, but if it becomes excessive or chronic, it can cause tissue damage, pain, and chronic diseases. Anti-inflammatory action is a process that helps tissue recovery and pain relief by inhibiting such excessive inflammatory responses. In this specification, the term “5-HT 2A The “receptor” is one of the serotonin (5-HT) receptor subgroups and plays a role in receiving and processing chemical signals of serotonin released in the brain. The 5-HT2A receptor is associated with various mental and physical disorders. 5-HT, though not limited to this 2ARelated conditions include depression, anxiety disorders, schizophrenia, insomnia, chronic pain, neuropathic pain, inflammatory diseases, cardiovascular diseases, migraines, drug dependence and addiction, and Parkinson's disease. In this specification, the term “pharmaceutically acceptable salt” includes salts derived from pharmaceutically acceptable inorganic acids, organic acids, or bases. Examples of suitable acids include hydrochloric acid, bromic acid, sulfuric acid, nitric acid, perchloric acid, fumaric acid, maleic acid, phosphoric acid, glycolic acid, lactic acid, salicylic acid, succinic acid, toluene-p-sulfonic acid, tartaric acid, acetic acid, trifluoroacetic acid, citric acid, methanesulfonic acid, formic acid, benzoic acid, malonic acid, naphthalene-2-sulfonic acid, benzenesulfonic acid, etc. Salts derived from suitable bases may include alkali metals such as sodium, alkaline earth metals such as magnesium, and ammonium, etc. In this specification, the term “prevention” means suppressing the occurrence of a disease or illness in a subject who has not been diagnosed with having such a disease or illness but is at risk of developing such a disease or illness. In this specification, the term “treatment” means (a) inhibition of the progression of a disease, illness, or symptom; (b) alleviation of a disease, illness, or symptom; or (c) elimination of a disease, illness, or symptom. When a compound of the present invention is administered to a subject, it serves to inhibit, eliminate, or alleviate the progression of symptoms associated with the overexpression or overactivity of the corresponding pathogenic protein, or other various diseases with this as a pathogenesis, by degrading a specific target protein recognized by a target protein ligand linked to an E3 enzyme ligand. Accordingly, the composition of the present invention may serve as a composition for treating the disease itself, or it may be applied as an adjuvant for treatment of the disease by being administered together with other pharmacological components. Accordingly, in this specification, the terms “treatment” or “therapeutic agent” include the meaning of “therapeutic aid” or “therapeutic adjuvant.” In this specification, the terms “administration” or “to administer” refer to directly administering a therapeutically effective amount of a compound of the present invention to a subject so that an equal amount is formed within the subject’s body. In this specification, the term “therapeutic effective amount” refers to the content of a composition in which the pharmacological component within the composition is contained in an amount sufficient to provide a therapeutic or preventive effect to an individual to whom the compound of the present invention is to be administered, and includes the meaning of “preventive effective amount.” In this specification, the term “object” includes, without limitation, humans, mice, rats, guinea pigs, dogs, cats, horses, cattle, pigs, monkeys, chimpanzees, baboons, or rhesus monkeys. Specifically, the object of the present invention is a human. In this specification, the term “food composition” refers to a food composition used for various purposes to improve specific objectives. A food composition containing the composition of the present invention as an active ingredient may be manufactured in the form of various food products, such as beverages, chewing gum, tea, vitamin complexes, powders, granules, tablets, capsules, confectionery, rice cakes, bread, etc. Since the food composition of the present invention has almost no toxicity or side effects, it can be used with confidence even when taken for a long period for preventive purposes. When the composition of the present invention is included in a food composition, the amount may be added in a ratio of 0.1 to 100% of the total weight. Here, when the food composition is manufactured in the form of a beverage, there are no special limitations other than containing the food composition in the indicated ratio, and it may contain various flavoring agents or natural carbohydrates, etc., as additional ingredients, just like a conventional beverage. That is, as natural carbohydrates, it may include monosaccharides such as glucose, disaccharides such as fructose, polysaccharides such as sucrose, conventional sugars such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. Examples of the above flavoring agents include natural flavoring agents (taumatin, stevia extract (e.g., rebaudioside A, glycyrrhizin, etc.)) and synthetic flavoring agents (saccharin, aspartame, etc.). In addition, the food composition of the present invention may contain various nutritional agents, vitamins, minerals (electrolytes), flavoring agents such as synthetic and natural flavoring agents, coloring agents, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, carbonating agents used in carbonated beverages, etc. These ingredients may be used independently or in combination. Although the proportion of these additives is not particularly important, it is generally selected in the range of 0.1 to 100 parts by weight per 100 parts by weight of the composition of the present invention. In particular, the term “health functional food composition” refers to a food containing ingredients that have a beneficial effect on the structure and function of the human body, and is primarily used to aid in nutrient supplementation, maintaining health, and preventing disease. In the present invention, the health functional food composition is characterized by being one or more formulations selected from powder, tablet, capsule, pill, suspension, emulsion, syrup, aerosol, gum, candy, bar, beverage, and granule. Specifically, the compound may be formulated and used in the form of oral formulations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, and aerosols, external formulations, suppositories, and sterile injectable solutions according to conventional methods, and carriers, excipients, and diluents that may be included in a composition containing the compound may include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oil. When formulating, the product is prepared using diluents or excipients such as commonly used fillers, fillers, binders, humectants, disintegrants, and surfactants. Solid dosage forms for oral administration include tablets, pills, powders, granules, and capsules, and these solid dosage forms are prepared by mixing at least one excipient, such as starch, calcium carbonate, sucrose or lactose, or gelatin, with the extract. In addition to simple excipients, lubricants such as magnesium styrate and talc are also used. Liquid dosage forms for oral administration include suspensions, liquid formulations, emulsions, and syrups, and may contain various excipients, such as humectants, sweeteners, flavorings, and preservatives, in addition to commonly used simple diluents like water and liquid paraffin. Preparations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, and suppositories. As non-aqueous solvents and suspensions, propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate may be used. As bases for suppositories, Witepsol, Macrogol, Tween 61, cocoa oil, laurin oil, glycerogelatin, etc. may be used. The present invention provides compounds represented by the following chemical formulas 1 to 30, stereoisomers thereof, or pharmaceutically acceptable salts thereof: [Chemical Formula 1] In the above chemical formula 1, A and B are directly connected, or X is a C1-C5 alkylene or C1-C5 alkoxy, and The above A is C6-C 10 aryl; or C6-C1 substituted with one or more selected from the group consisting of halogens, trifluoromethyl (-CF3), trifluoromethoxy (-OCF3), difluoromethoxy (-OCF2H), difluoromethyl (-CF2H), cyano (-CN), nitro (-NO2), C1-C3 alkyl, and C1-C3 alkoxy. 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, The above B is C6-C 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, and The above n is an integer between 0 and 8, and The above Y is an unsubstituted or oxo-substituted C1-C5 alkylene, and The above Z is a C1-C3 alkylamine C1-C 10 It is any one selected from the group consisting of alkyl, N-heterocyclic and C5-C9 cycloalkylamines. [Chemical Formula 2] In the above chemical formula 2, The above X is a single bond, or is a C1-C5 alkylene or a C1-C5 alkoxy, and The above n is an integer between 0 and 8. [Chemical Formula 3] In the above chemical formula 3, The above X is a single bond, or is a C1-C5 alkylene or a C1-C5 alkoxy, and The above n is an integer between 0 and 8. [Chemical Formula 4] In the above chemical formula 4, The above X is a single bond, or is a C1-C5 alkylene or a C1-C5 alkoxy, and The above n is an integer between 0 and 8, and The above Y is a C1-C3 alkylamine C1-C 10 It is any one selected from the group consisting of alkyl, N-heterocyclic and C5-C9 cycloalkylamines. [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] Specifically, the compounds of the above chemical formulas 5 to 30 are 5) 2-(methylamino)-N-(4-((4-(trifluoromethyl)oxy)benzyl)butanamide hydrochloride; 6) N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide 7) 2-(methylamino)-N-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)pentanamide hydrochloride; 8) N-((3',4'-dichloro-[1,1'-biphenyl]-4-yl)methyl)-2-(dimethylamino)pentanamide hydrochloride; 9) 2-(dimethylamino)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pentanamide hydrochloride; 10) 2-(methylamino)-N-((4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)methyl)pentanamide hydrochloride; 11) 2-(dimethylamino)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)hexanamide hydrochloride; 12) 2-(dimethylamino)-N-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)hexanamide hydrochloride; 13) N-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)-2-(dimethylamino)pentanamide hydrochloride; 14) N-(2-(3',4'-difluoro-[1,1'-biphenyl]-4-yl)ethyl)-2-(dimethylamino)pentanamide hydrochloride; 15) N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)nicotinamide; 17) 2-(propylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide hydrochloride; 18) N-(4-(benzyloxy)benzyl)-2-(methylamino)heptanamide hydrochloride 19) N-(4-(benzyloxy)benzyl)-2-(propylamino)butanamide hydrochloride; 20) 2-(cyclohexylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide; 21) N-((2-((7-(difluoromethyl)-3-(trifluoromethyl)-1H-indole-4-yl)methoxy)pyrimidine-5-yl)methyl)-2-(methylamino)butanamide 2,2,2-trifluoroacetate; 22) N3-methyl-N2-((6-((4-(trifluoromethyl)benzyl)oxy)pyridine-3-yl)methyl)pentane-2,3-diamine bis(2,2,2-trifluoroacetate); 23) 2-(methylamino)-N-(4-(4-(trifluoromethyl)phenethoxy)benzyl)butanamide; 24) N2-methyl-N1-((5-((4-(trifluoromethyl)benzyl)oxy)pyrimidine-2-yl)methyl)butein-1,2-diamine dihydrochloride; 25) N-(3-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide; 26) N-(4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide; 27) N-(2-(4'-chloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide; 28) N-(3-(4'-chloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide; 29) N-(4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide; 30) N-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)-2-(methylamino)butanamide hydrochloride; is. The pharmaceutical composition according to the present invention may contain, as an active ingredient, a compound represented by Formula 1 to 30, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and may additionally include a pharmaceutically acceptable carrier, diluent, or excipient. For example, it may be formulated and used in various forms according to conventional methods to suit each intended use, such as oral formulations like powders, granules, tablets, capsules, suspensions, emulsions, syrups, and aerosols, or injectable formulations like sterile injection solutions, and may be administered orally or through various routes including intravenous, intraperitoneal, subcutaneous, rectal, and local administration. Examples of suitable carriers, excipients, or diluents that may be included in such compositions include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oil. Additionally, the composition of the present invention may further include fillers, anticoagulants, lubricants, wetting agents, fragrances, emulsifiers, preservatives, etc. Solid dosage forms for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid dosage forms are formulated by mixing at least one excipient, such as starch, calcium carbonate, sucrose, lactose, gelatin, etc., into the above composition. In addition, in addition to simple excipients, lubricants such as magnesium stearate and talc may be used. Examples of oral liquid formulations include suspensions, liquid formulations, emulsions, syrups, etc., and in addition to commonly used simple diluents such as water and liquid paraffin, various excipients, such as humectants, sweeteners, flavorings, and preservatives, may be included. Preparations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, and suppositories. As non-aqueous solvents and suspensions, propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate may be used. As bases for suppositories, Witepsol, Macrogol, Tween 61, cocoa oil, laurin oil, glycerogelatin, etc., may be used. Meanwhile, injectable preparations may contain conventional additives such as solubilizers, isotonic agents, suspending agents, emulsifiers, stabilizers, and preservatives. In one embodiment of the present invention, the first aspect provides a compound represented by the following formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] In the above chemical formula 1, The above A and B are directly connected, or X is a C1-C5 alkylene or a C1-C5 alkoxy, and The above A is C6-C 10 aryl; or C6-C1224 10It is an aryl or a heteroaryl of a 5- to 9-membered ring, and B is C6-C 10 It is an aryl or a heteroaryl having a 5 to 9-membered ring, wherein n is an integer between 0 and 8, wherein Y is an unsubstituted or oxo-substituted C1-C5 alkylene, and Z is a C1-C3 alkylamine C1-C 10 Alkyl, heterocyclic of a pentagonal to ninth-membered ring that is unsubstituted or substituted with C1-C3 alkyls, C6-C 10 It is any one selected from the group consisting of cyclic amines C1-C5 alkyls. In the first embodiment, the second embodiment is that A is C6-C 10 aryl; or C6-C substituted with one or more selected from the group consisting of halogens, trifluoromethyl (-CF3), trifluoromethoxy (-OCF3), difluoromethoxy (-OCF2H) and difluoromethyl (-CF2H). 10 Provides a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, which is an aryl or a heteroaryl having a 5 to 9-membered ring. In the first or second embodiment, the third embodiment provides a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein B is any one selected from the group consisting of a phenyl group, a pyridine group and a pyrimidine group. In any one of the first to third embodiments, the fourth embodiment provides a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein n is an integer between 0 and 4. In any one of the first to fourth embodiments, the fifth embodiment provides that X is a C1-C3 alkylene or C1-C3 alkoxyne, a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. In any one of the first to fifth embodiments, the sixth embodiment provides a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein Y is an unsubstituted or oxo-substituted C1-C3 alkylene. In any one of the first to sixth embodiments, the seventh embodiment is that Z is , , , , , , , Provides a compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof, which is any one selected from the group consisting of piperidine, pyridine, piperazine, and C5-C9 cyclohexylamine. In any one of the first to seventh embodiments, the eighth embodiment provides an anti-inflammatory pharmaceutical composition comprising, as an active ingredient, a compound of any one of claims 1 to 7, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. In any one of the first to eighth embodiments, the ninth embodiment provides an anti-inflammatory pharmaceutical composition wherein the pharmaceutically acceptable salt is an acid addition salt selected from the group consisting of hydrochloride, bromate, sulfate, nitrate, perchlorate, fumarate, maleate, phosphate, glycolate, lactate, salicylate, succinate, toluene-p-sulfonate, tartrate, acetate, trifluoroacetate, citrate, methanesulfonate, formate, benzoate, malonate, naphthalene-2-sulfonate, and benzenesulfonate; or a base addition salt selected from the group consisting of sodium salt, magnesium salt, and ammonium salt. In any one of the first to ninth embodiments, the tenth embodiment provides an anti-inflammatory pharmaceutical composition in which the composition is a formulation for oral administration or parenteral administration. In any one of the first to ten embodiments, the eleventh embodiment provides a pharmaceutical composition for controlling or treating chronic pain and itching, comprising as an active ingredient a stereoisomer of any one of claims 1 to 7 or a pharmaceutically acceptable salt thereof. In any one of the first to eleventh embodiments, the twelfth embodiment provides a pharmaceutical composition for controlling or treating chronic pain and itching, wherein the pharmaceutically acceptable salt is an acid addition salt selected from the group consisting of hydrochloride, bromate, sulfate, nitrate, perchlorate, fumarate, maleate, phosphate, glycolate, lactate, salicylate, succinate, toluene-p-sulfonate, tartrate, acetate, trifluoroacetate, citrate, methanesulfonate, formate, benzoate, malonate, naphthalene-2-sulfonate, and benzenesulfonate; or a base addition salt selected from the group consisting of sodium salt, magnesium salt, and ammonium salt. In any one of the first to twelfth embodiments, the twelfth embodiment provides a pharmaceutical composition for controlling or treating chronic pain and itching, wherein the composition is in a formulation for oral administration or parenteral administration. In one embodiment of the present invention, the 14th aspect provides a health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound represented by the following chemical formula 1, a stereoisomer thereof, or a food-grade acceptable salt thereof. [Chemical Formula 1] In the above chemical formula 1, The above A and B are directly connected, or X is a C1-C5 alkylene or C1-C5 alkoxy, and the above A is a C6-C 10 aryl; or C6-C1224 10 It is an aryl or a heteroaryl of a 5- to 9-membered ring, and B is C6-C 10 It is an aryl or a heteroaryl having a 5 to 9-membered ring, wherein n is an integer between 0 and 8, wherein Y is an unsubstituted or oxo-substituted C1-C5 alkylene, and Z is a C1-C3 alkylamine C1-C 10 Alkyl, heterocyclic of a pentagonal to ninth-membered ring that is unsubstituted or substituted with C1-C3 alkyls, C6-C 10 It is any one selected from the group consisting of cyclic amines C1-C5 alkyls. In the 14th embodiment, the 15th embodiment is that A is C6-C 10 aryl; or C6-C substituted with one or more selected from the group consisting of halogens, trifluoromethyl (-CF3), trifluoromethoxy (-OCF3), difluoromethoxy (-OCF2H) and difluoromethyl (-CF2H). 10 A health functional food composition for relieving or improving chronic pain and itching comprises, as an active ingredient, a compound that is an aryl or a heteroaryl having a 5 to 9-membered ring, a stereoisomer thereof, or a food-grade acceptable salt thereof. In the 14th or 15th embodiment, the 16th embodiment provides a health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, stereoisomer thereof, or a food-grade acceptable salt thereof, wherein B is any one selected from the group consisting of a phenyl group, a pyridine group, and a pyrimidine group. In any one of the 14th to 16th embodiments, the 17th embodiment provides a health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, a stereoisomer thereof, or a food-grade acceptable salt thereof, wherein n is an integer between 0 and 4. In any one of the 14th to 17th embodiments, the 18th embodiment provides a health functional food composition for relieving or improving chronic pain and itching, wherein X comprises a C1-C3 alkylene or C1-C3 alkoxyne, a compound, a stereoisomer thereof, or a food-grade acceptable salt thereof as an active ingredient. In any one of the 14th to 18th embodiments, the 19th embodiment provides a health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, a stereoisomer thereof, or a food-grade acceptable salt thereof, wherein Y is an unsubstituted or oxo-substituted C1-C3 alkylene. In any one of the 14th to 19th embodiments, the 20th embodiment is that Z is , , , , , , , A health functional food composition for relieving or improving chronic pain and itching comprises, as an active ingredient, a compound selected from the group consisting of piperidine, pyridine, piperazine, and C5-C9 cyclohexylamine, a stereoisomer thereof, or a food-grade acceptable salt thereof. In any one of the 14th to 20th embodiments, the 21st embodiment provides a health functional food composition for improving chronic pain or itching, wherein the health functional food composition is in any one formulation selected from the group consisting of powder, granules, tablets, capsules, pills, suspensions, emulsions, syrups, aerosols, gums, candies, bars, and beverages. The features and advantages of the present invention are summarized as follows: (a) The present invention provides an aminoalkylamide derivative compound containing a novel benzyloxyl group. (b) The compound of the present invention has been confirmed to be safe due to its high cell viability, and can be usefully utilized as a pharmaceutical composition for the prevention or treatment of 5-HT2A-related diseases by effectively inhibiting the 5-HT2A receptor. Furthermore, the effects of the present invention are not limited to the effects described above, and should be understood to include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention. Figure 1 is a graph showing the effect on cell viability in RAW264.7 cells and HaCaT cells during the period. Figure 2 is a graph showing the inhibitory effect on 5-HT2A. Figure 3 is a graph showing the inhibitory effect of histamine on the influx of calcium ions into dorsal root ganglion cells. Figure 4 is a graph showing the inhibitory effect of Capsaicin on the influx of calcium ions into dorsal root ganglion cells. Figure 5 is a graph showing the MC903-induced antipruritic effects of Compound 10 (ATS0005) and Compound 23 (ATS0023). Figure 6 is a graph showing the antipruritic effect of MC903 on compound 9 (ATS0004). Figure 7 shows the 1H NMR values ​​for compound 5 (ATB1606). Figure 8 shows the 1H NMR values ​​for compound 6 (ATS0001). Figure 9 shows the 1H NMR values ​​for compound 7 (ATS0002). Figure 10 shows the 1H NMR values ​​for compound 8 (ATS0003). Figure 11 shows the 1H NMR values ​​for compound 9 (ATS0004). Figure 12 shows the 1H NMR values ​​for compound 10 (ATS0005). Figure 13 shows the 1H NMR values ​​for compound 11 (ATS0006). Figure 14 shows the 1H NMR values ​​for compound 12 (ATS0007). Figure 15 shows the 1H NMR values ​​for compound 13 (ATS0008). Figure 16 shows the 1H NMR values ​​for compound 14 (ATS0009). Figure 17 shows the 1H NMR values ​​for compound 15 (ATS0010). Figure 18 shows the 1H NMR values ​​for compound 17 (ATS0014). Figure 19 shows the 1H NMR values ​​for compound 18 (ATS0015). Figure 20 shows the 1H NMR values ​​for compound 19 (ATS0018). Figure 21 shows the 1H NMR values ​​for compound 20 (ATS0020). Figure 22 shows the 1H NMR values ​​for compound 21 (ATS0021). Figure 23 shows the 1H NMR values ​​for compound 22 (ATS0022). Figure 24 shows the 1H NMR values ​​for compound 23 (ATS0023). Figure 25 shows the 1H NMR values ​​for compound 24 (ATS0024). Figure 26 shows the 1H NMR values ​​for compound 25 (ATS0042). Figure 27 shows the 1H NMR values ​​for compound 26 (ATS0043). Figure 28 shows the 1H NMR values ​​for compound 27 (ATS0044). Figure 29 shows the 1H NMR values ​​for compound 28 (ATS0045). Figure 30 shows the 1H NMR values ​​for compound 29 (ATS0046). Figure 31 shows the 1H NMR values ​​for compound 30 (ATS0047). Figure 32 is a graph showing the pKa of compound 9 under aqueous conditions calculated by extrapolating the psKa obtained under different solvent conditions (left) and a graph showing the distribution of ionized / neutral species according to pH change (right). Figure 33 is a graph showing the change in average molecular charge of compound 9 according to the change in pH. Figure 34 shows a graph showing the average molecular charge of compound 9 according to pH change (top left), a graph showing the change in the fraction of ionized species and neutral species according to pH (top right), and a graph showing the change in the distribution coefficient (LogD) according to pH change (bottom). Figure 35 shows a graph showing the average molecular charge of compound 9 according to pH change (top left), a graph showing the pattern of change in the relative fraction of ionized and neutral species according to pH change (top right), a graph showing the change in concentration of neutral species over time during the CheqSol measurement process (bottom left), and a graph showing the change in solubility (logS) according to pH change (bottom right). Figure 36 is a graph showing the pKa of compound 23 under aqueous conditions calculated by extrapolating the psKa obtained under different solvent conditions (left) and a graph showing the distribution of ionized / neutral species according to pH change (right). Figure 37 is a graph showing the change in average molecular charge of compound 23 according to the change in pH. Figure 38 shows a graph showing the average molecular charge of compound 23 according to pH change (top left), a graph showing the change in the fraction of ionized species and neutral species according to pH (top right), and a graph showing the change in the distribution coefficient (LogD) according to pH change (bottom). Figure 39 shows a graph showing the average molecular charge of compound 23 according to pH change (top left), a graph showing the pattern of change in the relative fractions of ionized and neutral species according to pH change (top right), a graph showing the change in concentration of neutral species over time during the CheqSol measurement process (bottom left), and a graph showing the change in solubility (logS) according to pH change (bottom right). Figure 40 is a graph of the plasma concentration-time curve after intravenous administration of compound 9 (ATS0004) in SD rats. Figure 41 is a graph of the plasma concentration-time curve after oral administration of compound 9 (ATS0004) in SD rats. Figure 42 is a graph of the plasma concentration-time curve after intravenous administration of compound 23 (ATS0023) in SD rats. Figure 43 is a graph of the plasma concentration-time curve after oral administration of compound 23 (ATS0023) in SD rats. Figure 44 is a graph of the average plasma concentration-time curve of compound 9 (ATS0004) in SD rats. Figure 45 is a graph of the average plasma concentration-time curve of compound 23 (ATS0023) in SD rats. The present invention will be described in more detail below through examples. These examples are intended solely to explain the present invention more specifically, and it will be obvious to those skilled in the art that the scope of the present invention is not limited by these examples according to the gist of the invention. The reaction scheme for preparing the compounds of the present invention is as follows. In the following reaction schemes 1 to 12, the English alphabet letters and unused numbers represent the compound numbers prepared in each reaction scheme. That is, 1 represents compound 1. [Reaction Equation 1] [Reaction Equation 2] [Reaction Equation 3] [Reaction Equation 4] [Reaction Equation 5] Synthetic examples for preparing the compound of the present invention are as follows: Synthesis Example 1: Protection of amino acid amine group [Reaction Equation 6] Amino acid (1.0 equivalent), Boc anhydride (1.5 equivalents), and sodium bicarbonate (1.5 equivalents) were dissolved in a mixed solvent of distilled water to methanol in a ratio of 1:1 and reacted at room temperature for 36–48 hours. After the reaction was complete, the mixture was washed twice with diethyl ether, the pH of the aqueous layer was adjusted to 2 using 1.0 M hydrochloric acid, and then extracted with ethyl acetate (EA). The resulting organic layer was dehydrated using a drying agent (sodium sulfate) and dried under reduced pressure to obtain the target compound, an amino acid in which the amine group is protected by a protecting group (Boc). Synthesis Example 2: 4-hydroxybenzylamine bond [Reaction Equation 7] At a low temperature of -78 ℃, the compound synthesized in Synthesis Example 1 (0.1 M) and N-methylmorpholine (NMM) (0.15 M, 1.5 equivalents) were added to anhydrous tetrahydrofuran and stirred for 5 minutes. Then, isobutylchloroformate (IBCF) (0.13 M, 1.3 equivalents) was added and stirred for 5 minutes, followed by the addition of a 4-hydroxybenzylamine derivative (0.12 M, 1.2 equivalents) and stirring for 5 minutes. After raising the temperature of the reaction mixture to room temperature, the reaction was monitored while stirring for 30 to 60 minutes. After the reaction was completed, the mixture was filtered, dried under reduced pressure, and purified by silica gel column chromatography. Synthesis Example 3: Benzyl bromide binding reaction [Reaction Equation 8] The compound of Synthesis Example 2 (1.0 equivalent), benzyl bromide (1.0-1.2 equivalents), and potassium carbonate (4.0 equivalents) were dissolved in acetone, and the reaction was monitored while refluxing at 50-60°C for 4 to 12 hours. After the reaction was completed, the reaction mixture was concentrated, extracted with methylene chloride, and the moisture remaining in the organic layer was removed using a drying agent (sodium sulfate). The obtained organic layer was concentrated and then purified by silica gel column chromatography. Synthesis Example 4: Removal of amine protecting group [Reaction Equation 9] The compound obtained in Synthesis Example 3 above was dissolved in methylene chloride, then an excess amount (6-10 equivalents) of 4.0 M hydrochloric acid was added and stirred at room temperature. After the reaction was completed, the resulting solid was washed with ethyl acetate and then dried under vacuum to remove the amine-protecting group (boc), thereby obtaining a benzyloxybenzylaminoyl amino acid derivative containing the desired primary amine structure. Synthesis Example 5.1: Alkylation 1 [Reaction Equation 10] A benzyloxybenzylamininyl amino acid derivative having a primary amine structure was alkylated to form a secondary amine structure. Specifically, the compound of Synthesis Example 4 (1.0 equivalent) and iodomethane (10 equivalents) were dissolved in tetrahydrofuran, and then sodium hydride (10 equivalents) was slowly added dropwise at 0°C, followed by a reaction at room temperature for 24 hours. After the reaction was complete, the reaction mixture was extracted with methylene chloride, moisture was removed using a drying agent (sodium sulfate), and then concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography. The purified compound was dissolved in methylene chloride, and then 6.0 to 10.0 equivalents of 4.0 M hydrochloric acid were added while stirring. After the reaction was complete, the concentrate was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain a benzyloxybenzylamininyl amino acid derivative containing a secondary amine structure. Synthesis Example 5.2: Alkylation 2 [Reaction Equation 11] A benzyloxybenzylaminoyl amino acid derivative having a primary amine structure was alkylated to form a tertiary amine structure. Specifically, the compound of Synthesis Example 4 (1.0 equivalent) was dissolved in methanol, followed by the sequential addition of formalinide (37% by weight solution) and a 10% palladium catalyst, and the reaction was carried out at room temperature for 18 hours. After the reaction, the catalyst was removed by filtration using Celite, and the filtered liquid was evaporated under reduced pressure. The reaction mixture was recrystallized with methanol / diethyl ether to obtain the purified target compound. Synthesis Example 6: General method for ethylation and diethylation of amines [Reaction Equation 12] The compound obtained in Synthesis Example 4 (1.0 equivalent) and iodoethane (0.9 equivalent) were dissolved in tetrahydrofuran solvent, and sodium hydride (10 equivalents) was added very slowly dropwise at 0 °C. The reaction mixture was reacted at room temperature for 24 hours. After the reaction was complete, the mixture was diluted with dimethyl chloride solvent and washed with distilled water; the organic layer was then dried to remove moisture with sodium sulfate and vacuum concentrated. The obtained residue was separated and purified using silica gel chromatography. The purified product was dissolved in dimethyl chloride solvent, 4.0 M hydrochloric acid (6.0-10.0 equivalents) was added while stirring at room temperature, and then vacuum concentrated. The obtained residue was separated and purified using silica gel chromatography. Reaction formulas a to g for preparing the compounds of the present invention are as follows. [Reaction Equation a] Introduction of a butoxycarbonyl protecting group (Boc protecting group) Norusine (1.0 equivalent), Boc anhydride (1.5 equivalents), and sodium bicarbonate (1.5 equivalents) were dissolved in a 1:1 mixed solvent of distilled water and methanol and reacted at room temperature for 36-48 hours. After concentrating the mixture under vacuum, the pH of the water layer was adjusted to 2 with 1.0 M hydrochloric acid. Subsequently, the water in the organic layer obtained by extraction with ethyl acetate was removed with sodium sulfate, and the solvent was evaporated under vacuum to obtain the title compound. [Reaction Equation b] Methylation of the amine group The compound obtained from reaction scheme a (1.0 equivalent) and iodomethane (10 equivalents) were dissolved in tetrahydrofuran solvent, and sodium hydride (10 equivalents) was added dropwise very slowly at 0 °C. The reaction mixture was reacted at room temperature for 24 hours. After the reaction was complete, the mixture was diluted with ether solvent and distilled water was added. The pH of the aqueous layer was adjusted to 2 using a 20% citric acid solution. Subsequently, the water in the organic layer obtained by extraction with ethyl acetate was removed with sodium sulfate, and the solvent was evaporated under vacuum. The resulting residue was separated and purified using silica gel chromatography to obtain the title compound. [Reaction Equation c] Introduction of a Boc protecting group on the primary amine group 4-bromophenethylamine (1.0 equivalent) was dissolved in dimethyl chloride solvent, potassium carbonate (1.5 equivalents) and Boc anhydride (1.05 equivalents) were added, and the reaction was carried out at room temperature for about 12-18 hours. The reaction mixture was diluted with dimethyl chloride and washed twice with distilled water. The organic layer was dried with sodium sulfate and concentrated under vacuum. The obtained residue was washed with hexane and then evaporated under vacuum to obtain the title compound. [Reaction Scheme d] Synthesis of biphenylamine hydrochloride derivatives The compound obtained from reaction scheme c above, tert-butyl (4-bromobenzyl)carbamate or tert-butyl (4-bromophenyl)carbamate (1.0 equivalent), benzeneboronic acid (1.5 equivalents), sodium carbonate (5.0 equivalents), and tetrakis(triphenylphosphine)palladium (0.04 equivalents) were dissolved in a 2:1 to 2.5:1 mixed solvent of degassed toluene and distilled water and reacted under reflux at a temperature of 140 °C for 12 to 18 hours. After the reaction, the catalyst was removed by filtration with Celite, and the solvent was evaporated from the filtered organic layer under vacuum. The obtained residue was separated and purified by chromatography using silica gel. The purified product was dissolved in ethyl acetate solvent and stirred at room temperature while adding 4.0 M hydrochloric acid (6.0-10.0 equivalents). The white solid in the form of a salt obtained was washed with ethyl acetate and then completely dried under vacuum to obtain the title compound. [Reaction Equation e] Mixed Anhydride Coupling (MAC) Reaction In a distilled tetrahydrofuran solvent, the compound synthesized according to reaction scheme a or the compound synthesized according to reaction scheme b (1.0 equivalent) and N-methylmorpholine (NMM, 2.5-2.8 equivalents) were added and stirred for 15 minutes. Then, isobutyl chloroformate (IBCF, 1.3 equivalents) was added and stirred for another 15 minutes, after which the compound obtained from reaction scheme d (1.05 equivalents) was added. The reaction mixture was allowed to proceed at room temperature for about 3-5 hours. The mixture was filtered, and the solvent was evaporated under vacuum. The obtained residue was separated and purified by silica gel chromatography to obtain the title compound. [Reaction Equation f] Removal of Boc protector The compound derivative (1.0 equivalent) obtained from the above reaction scheme e was dissolved in ethyl acetate solvent, and then 4.0 M hydrochloric acid (6.0-10.0 equivalents) was added while stirring at room temperature. The white solid in the form of a salt obtained was washed with ethyl acetate and then completely dried under vacuum to obtain the title compound. [Reaction Equation g] Dimethylation of amine groups The compound (1.0 equivalent) obtained from the above reaction scheme f was dissolved in methanol, and triethylamine (6.0 equivalents) was added, followed by the addition of formaldehyde (37% by weight solution, 1.0-2.5 equivalents) and 10% palladium catalyst (0.1-0.5 equivalents). The reaction mixture was reacted at room temperature for 18 hours. After the reaction, the catalyst was removed by filtering with Celite, and the filtered organic layer was evaporated under vacuum to obtain a white solid. The resulting product was recrystallized with methanol and diethyl ether to obtain the title compound. Preparation Example The process for preparing the compounds of the present invention is as described in Preparation Examples 1 to 27 below. In Preparation Examples 1 to 27, the English alphabet letters and unused numbers represent the compound numbers prepared in each preparation example. That is, 1 represents Compound 1. [Preparation Example 1] Preparation of 2-(methylamino)-N-(4-((4-(trifluoromethyl)oxy)benzyl)butanamide hydrochloride Using the above reaction scheme 6, 2-aminopropanoic acid (alanine, 3.00 g, 29.1 mmol), Boc anhydride (10.00 mL, 43.6 mmol), and NaHCO3 (3.67 g, 43.6 mmol) were reacted to synthesize 2-((tert-butoxycarbonyl)amino)butanoic acid in the form of a white powder (5.89 g, 100%): Rf = 0.50 (DCM 19: methanol 1 and a few drops of acetic acid); 1H NMR (DMSO-d6, 400 MHz) 12.40 (C(O)OH), 7.02 (d, J = 7.9 Hz, NH), 3.74-3.82 (m, NHCHCH2), 1.50-1.73 (m, CH2CH3), 1.38 (s, Boc), 0.87 (t, J = 7.4) Hz, CH2CH3). Using the above reaction scheme 7, 2-((tert-butoxycarbonyl)amino)butanoic acid (1.05 g, 5.2 mmol), NMM (0.85 mL, 7.8 mmol), and IBCF (0.85 mL, 6.6 mmol)

[0173] Tert-butyl(1-((4-hydroxybenzyl)amino)-1-oxobuta-2-nyl)carbamate in the form of a pale pink powder was synthesized by reacting 4-hydroxybenzylamine (0.76 g, 6.2 mmol) with (1.27 g, 80%): Rf = 0.35 (EtOAc 1 : n-hexane 1); 1H NMR (DMSO-d6, 400 MHz) 9.27 (s, Ar-OH), 8.15 (t, J = 5.7 Hz, C(O)NH), 7.03 (d, J = 8.1 Hz, ArH), 6.67 (d, J = 8.0 Hz, ArH), 6.78 (d, J = 8.0 Hz, Boc-NH), 4.08-4.22 (m, NHCH2), 3.79-3.87 (m, NHCHCH2), 1.45-1.67 (m, CH2CH3), 1.38 (s, Boc), 0.82 (t, J = 7.3 Hz, CH2CH3). Using the above Reaction Scheme 8, the above tert-butyl(1-((4-hydroxybenzyl)amino)-1-oxobuta-2-nyl)carbamate (0.30 g, 1.0 mmol), 4-(trifluoromethyl)benzyl bromide (0.17 mL, 1.1 mmol), and K2CO3 (0.54 g, 3.9 mmol) were reacted to synthesize tert-butyl(1-oxo-1-((4-((4-(trifluoromethyl)benzyl)oxy)benzyl)amino)propa-2-nyl)carbamate in the form of a white powder (0.44 g, 96%): R f =0.24 (EtOAc 1 : n-hexane 1); 1H NMR (DMSO-d6, 400 MHz) 8.21 (t, J = 5.8 Hz, C(O)NH), 7.62-7.80 (m, ArH), 7.14-7.21 (m, ArH), 6.91-6.98 (m, ArH), 6.80 (d, J = 7.9 Hz, Boc-NH), 5.21 (s, OCH2), 4.13-4.28 (m, NHCH2), 3.80-3.87 (m, NHCHCH2), 1.46-1.67 (m, CH2CH3), 1.37 (s, Boc), 0.82 (t, J = 7.3 Hz, CH2CH3). Using the above reaction scheme 10, the tert-butyl(1-oxo-1-((4-((4-(trifluoromethyl)benzyl)oxy)benzyl)amino)propa-2-nyl)carbamate (0.40 g, 0.86 mmol), NaH (10 equivalents), and CH3I (10 equivalents) were reacted to obtain a methylation compound, and then 2-(methylamino)-N-(4-((4-(trifluoromethyl)oxy)benzyl)butanamide hydrochloride (Compound 5, ATB1606) was synthesized by removing the Boc group using 4.0 M HCl in dioxane (1.49 mL, 42.8 mmol) (0.30 g); 1H NMR (DMSO-d6, 400 MHz) 8.89 (t, J = 5.7 Hz, C(O)NH), 8.09 (broad, NH3+Cl-), 7.61-7.82 (m, ArH), 7.20-7.25 (m, ArH), 6.98-7.03 (m, ArH), 5.18 (s, OCH2), 4.22-4.34 (m, NHCH2), 3.67-3.72 (m, NHCHCH2), 2.39 (s, NHCH3), 1.70-1.80 (m, CH2CH3), 0.86 (t, J = 7.5 Hz, CH2CH3) (NMR values, see Fig. 7). [Preparation Example 2] Preparation of N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide General manufacturing procedure of Compound 3 of Manufacturing Example 2 above Compound 2 (2.4 g, 10.5 mmol), HATU (380.23 g, 10.5 mmol), and DIEA (2.7 g, 21 mmol) were added to a solution of Compound 1 (2.1 g, 10.5 mmol) dissolved in DMF (30 mL). The mixture was stirred at room temperature for 1 hour, then diluted with water (100 mL). The mixture was extracted with EA (50 mL × 3). The bound organic phase was concentrated and purified by silica gel column chromatography (PE:EA = 5:1) to obtain Compound 3 (2.9 g, 100% yield) as a white solid. LCMS: MS (ESI) m / z: 311.0 [M-100+H] + . General manufacturing procedure of Compound 5 of Preparation Example 2 above Compound 4 (232 mg, 1.21 mmol), Pd(dppf)Cl2 (267 mg, 0.363 mmol), and K2CO3 (504 mg, 3.63 mmol) were added to a solution of Compound 3 (500 mg, 1.21 mmol) dissolved in 1,4-dioxane (10 mL) and H2O (2 mL). The mixture was stirred overnight at 100 °C under a nitrogen atmosphere and then cooled to room temperature. The mixture was diluted with water (100 mL) and extracted with EA (50 mL × 3). The combined organic phase was concentrated and purified by silica gel column chromatography (PE:EA = 5:1) to obtain Compound 5 (460 mg, 92% yield) as a yellow solid. LCMS: MS (ESI) m / z: 377.2 [M+H] + . General manufacturing procedure of N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide TFA (2 mL) was added to a solution of compound 5 (260 mg, 0.54 mmol) dissolved in DCM (6 mL), and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was concentrated to obtain a residue, which was then neutralized with a saturated aqueous NaHCO3 solution (100 mL). The mixture was extracted with EA (50 mL × 3). The combined organic phase was concentrated and purified by reverse-phase Combi-flash (under NH4HCO3 conditions) to obtain compound N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide (138 mg, 53.1% yield) as a white solid. LCMS: MS (ESI) m / z: 377.1 [M+H] + ; 1 H NMR (400 MHz, CDCl3) δ 7.66 (d,J= 2.1 Hz, 1H), 7.51 - 7.45 (m, 3H), 7.40 (dd,J= 8.3, 2.1 Hz, 1H), 7.29 (s, 1H), 7.27 (s, 1H), 6.90 (br, 1H), 3.60 - 3.44 (m, 2H), 3.23 (dd, J = 9.5, 3.4 Hz, 1H), 3.07 - 2.94 (m, 1H), 2.87 (t,J= 7.1 Hz, 2H), 2.68 (dd,J= 15.9, 6.9 Hz, 1H), 1.96 (dd,J= 8.5, 4.0 Hz, 2H), 1.78 (d,J= 4.0 Hz, 1H), 1.63 - 1.53 (m, 1H), 1.45 - 1.35 (m, 3H). [Preparation Example 3] Preparation of 2-(methylamino)-N-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)pentanamide hydrochloride Compound 7 (ATS0002) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 4] Preparation of N-((3',4'-dichloro-[1,1'-biphenyl]-4-yl)methyl)-2-(dimethylamino)pentanamide hydrochloride Compound 8 (ATS0003) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 5] Preparation of 2-(dimethylamino)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pentanamide hydrochloride Compound 9 (ATS0004) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 6] Preparation of 2-(methylamino)-N-((4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)methyl)pentanamide hydrochloride Compound 10 (ATS0005) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 7] Preparation of 2-(dimethylamino)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)hexanamide hydrochloride Compound 11 (ATS0006) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 8] Preparation of 2-(dimethylamino)-N-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)hexanamide hydrochloride Compound 12 (ATS0007) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 9] Preparation of N-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)-2-(dimethylamino)pentanamide hydrochloride Compound 13 (ATS0008) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 10] Preparation of N-(2-(3',4'-difluoro-[1,1'-biphenyl]-4-yl)ethyl)-2-(dimethylamino)pentanamide hydrochloride Compound 14 (ATS0009) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 11] Preparation of N-(2-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)ethyl)nicotinamide Compound 15 (ATS0010) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 12] Preparation of 2-(propylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide hydrochloride Compound 17 (ATS0014) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 13] Preparation of N-(4-(benzyloxy)benzyl)-2-(methylamino)heptanamide hydrochloride Compound 18 (ATS0015) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 14] Preparation of N-(4-(benzyloxy)benzyl)-2-(propylamino)butanamide hydrochloride Compound 19 (ATS0018) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. [Preparation Example 15] Preparation of 2-(cyclohexylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide General manufacturing procedure of Compound 2 of Preparation Example 15 above Compound 1 (15 g, 145.4 mmol) was placed in MeOH (100 mL) and H2O (100 mL), and NaOH (8.7 g, 218.1 mmol) and (Boc)2O (47.6 g, 218.1 mmol) were added. The reaction mixture was stirred overnight at room temperature, after which it was diluted with water (200 mL). The mixture was washed with EA (100 mL × 3). The pH of the aqueous layer was adjusted to 5 with HCl (1 N). Subsequently, it was extracted with EA (100 mL × 3). The organic layer was dried with Na2SO4 and filtered. The filtrate was concentrated and dried under reduced pressure to obtain Compound 2 (29.5 g, 100% yield) as a white solid. 1 H NMR (400 MHz, CDCl3) δ 6.98 (d,J= 25.1 Hz, 1H), 4.68 (dd,J= 316.3, 6.7 Hz, 1H), 1.97 - 1.83 (m, 1H), 1.79 - 1.69 (m, 1H), 1.45 (s, 9H), 0.98 (t,J= 7.4 Hz, 3H). General manufacturing procedure of Compound 4 of Preparation Example 15 above Compound 2 (2.0 g, 9.84 mmol) was dissolved in THF (20 mL), and NMM (1.5 g, 14.76 mmol) was added under a nitrogen atmosphere while maintaining the temperature at -78 °C. The mixture was stirred at -78 °C for 5 minutes, after which IBCF (1.75 g, 12.79 mmol) was added. After stirring again at -78 °C for 5 minutes, Compound 3 (1.45 g, 11.81 mmol) was added. The mixture was heated to room temperature and stirred for 1 hour. The reaction mixture was filtered and concentrated under reduced pressure to obtain the residue. The residue was purified using a silica gel column (PE:EA = 2:1) to obtain Compound 4 (2.6 g, 85.7% yield) as a white solid. LCMS: MS (ESI) M / Z: 309.2 [M+H] + . General manufacturing procedure of Compound 6 of Preparation Example 15 above Compound 4 (1.3 g, 4.2 mmol) was dissolved in DMF (15 mL), and Compound 5 (1.1 g, 4.6 mmol) and K2CO3 (1.7 g, 12.6 mmol) were added. The mixture was stirred overnight at 50 °C and then cooled to room temperature. The reaction mixture was diluted in water (200 mL) and extracted with EA (50 mL × 3). The organic layer was concentrated and purified with silica gel (PE:EA = 2:1) to obtain Compound 6 (1.83 g, 93.4% yield) as a white solid. MS (ESI) M / Z: 411.2 [M+H] + . General manufacturing procedure of Compound 7 of Preparation Example 15 above Compound 6 (1.83 g, 3.92 mmol) was dissolved in DCM (20 mL) and TFA (10 mL) was added. The mixture was stirred at room temperature for 1 hour and then concentrated to obtain the residue. The residue was neutralized with a saturated aqueous NaHCO₃ solution (300 mL) and extracted with EA (50 mL × 3). The organic layer was dried with Na₂SO₄ and filtered. The filtrate was concentrated and dried under reduced pressure to obtain Compound 7 (1.4 g, 97.5% yield) as a yellow solid. Manufacturing procedure of 2-(cyclohexylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide Compound 7 (500 mg, 1.366 mmol) was dissolved in a mixed solvent of DCM (10 mL) and MeOH (1 mL), and Compound 8 (201 mg, 2.049 mmol) and NaOAc (258 mg, 3.142 mmol) were added. After stirring the mixture at 0 °C for 0.5 hours, NaBH(OAc)3 (984 mg, 4.644 mmol) was added. The reaction mixture was stirred overnight at room temperature and then concentrated to obtain the residue. The residue was purified by reverse-phase combi-flash (under NH₄HCO₃ conditions) to obtain 2-(cyclohexylamino)-N-(4-((4-(trifluoromethyl)benzyl)oxy)benzyl)butanamide (409.15 mg, 66.7% yield) as a white solid. LCMS: MS (ESI) M / Z: 449.2 [M+H] + ; 1H NMR (400 MHz, DMSO-d6) δ 8.28 (t,J= 6.0 Hz, 1H), 7.75 (d,J= 8.2 Hz, 2H), 7.65 (d,J= 8.1 Hz, 2H), 7.17 (d,J= 8.6 Hz, 2H), 7.03 - 6.86 (m, 2H), 5.21 (s, 2H), 4.29 - 4.13 (m, 2H), 3.02 (q,J= 6.9 Hz, 1H), 2.28 - 2.13 (m, 1H), 1.83 (d,J= 12.3 Hz, 1H), 1.71 - 1.57 (m, 4H), 1.54 - 1.30 (m, 3H), 1.14 - 0.88 (m, 5H), 0.83 (t,J= 7.4 Hz, 3H). [Preparation Example 16] Preparation of N-((2-((7-(difluoromethyl)-3-(trifluoromethyl)-1H-indole-4-yl)methoxy)pyrimidine-5-yl)methyl)-2-(methylamino)butanamide 2,2,2-trifluoroacetate General preparation procedure for Compound 2 of Preparation Example 16 above (MC24-1242-006) Compound 1 (3 g, 13.9 mmol) was dissolved in anhydrous THF (60 mL) and cooled to -78 °C. Subsequently, vinylmagnesium bromide THF solution (1 M, 42.0 mL, 42.0 mmol) was slowly added over 30 minutes. After addition, the reaction mixture was stirred at -78 °C for 1 hour, and the reaction was stopped with a saturated aqueous NH4Cl solution (80 mL). The mixture was extracted with 3 × 60 mL of EA, the organic layer was concentrated, and then purified with Combiflash (100% PE → PE:EA = 10:1) to obtain Compound 2 (1.5 g, 51.4%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.60 (br, 1H), 7.88 (d,J= 8.0 Hz, 1H), 7.43 (d,J= 4.0 Hz, 1H), 7.27 (d,J= 4.0 Hz, 1H), 7.25 (d,J= 8.0 Hz, 1H), 4.00 (s, 3H). General preparation procedure for Compound 3 of Preparation Example 16 above (MC24-1242-008) Compound 2 (1.0 g, 4.77 mmol) was dissolved in DMF (20 mL), and NIS (11.61 g, 7.16 mmol) was added in several portions. The mixture was stirred at room temperature for 1.5 hours, and the reaction was stopped with brine (50 mL). It was extracted with EA (3 × 50 mL), washed with a saturated Na2S2O3 solution (2 × 50 mL), and dried with Na2SO4. After filtration, the solvent was removed, and the solution was purified with silica gel flash (100% PE → PE:EA=8:1) to obtain Compound 3 (1.5 g, 93.8%) as an off-white solid. 1 H NMR (400 MHz, CDCl3) δ 8.84 (br, 1H), 7.54-7.52 (m, 2H), 7.30 (d, J= 8.0 Hz, 1H), 4.01 (s, 3H). General preparation procedure for Compound 4 of Preparation Example 16 above (MC24-1242-016) Compound 3 (6.0 g, 17.88 mmol) was dissolved in DMF (50 mL), and methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (17.18 g, 89.41 mmol) and CuI (4.09 g, 21.46 mmol) were added. The mixture was stirred at 110 °C for 16 hours and then cooled. The mixture was stopped by adding brine (100 mL) and extracted with EA (3 × 80 mL). The organic layer was dried, filtered, concentrated, and purified by flash (100% PE → PE:EA = 5:1) to obtain Compound 4 (3.3 g, 66.5%). 1 H NMR (400 MHz, CDCl3) δ 8.98 (br, 1H), 7.81 (d, J = 4.0 Hz, 1H), 7.71 (d,J= 8.0 Hz, 1H), 7.38 (d,J= 8.0 Hz, 1H), 3.98 (s, 3H). General preparation procedure for Compound 5 of Preparation Example 16 above (MC24-1242-018) Compound 4 (100 mg, 0.36 mmol) and (tributylstannyl)methanol (127 mg, 0.40 mmol) were dissolved in 1,4-dioxane (10 mL), and Xphos-Pd-G3 (31 mg, 0.04 mmol) was added. The mixture was refluxed for 16 hours and then cooled to room temperature. After concentration, the residue was purified with silica flash (100% PE → PE:EA = 1:1) to obtain Compound 5 (50 mg, 50.8%) as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 12.10 (br, 1H), 8.05 (d,J= 4.0 Hz, 1H), 7.54 (d,J= 8.0 Hz, 1H), 7.34 (d,J= 8.0 Hz, 1H), 5.94 (t,J= 4.0 Hz, 1H), 4.86 (d,J= 8.0 Hz, 2H), 3.82 (s, 3H). General preparation procedure for Compound 6 of Preparation Example 16 above (MC24-1242-021) Compound 5 (720 mg, 2.64 mmol) was dissolved in chloroform (100 mL), and MnO2 (4.58 g, 52.71 mmol) was added. The mixture was stirred at 50 ℃ for 2 hours and then cooled. After filtration and concentration, the solution was purified by flash (100% PE → PE:EA = 4:1) to obtain Compound 6 (560 mg, 78.3%). 1 H NMR (400 MHz, CDCl3) δ 10.68 (br, 1H), 10.22 (s, 1H), 7.88 - 7.28 (m, 3H), 4.02 (s, 3H). General preparation procedure for Compound 7 of Preparation Example 16 above (MC24-1242-022) Compound 6 (100 mg, 0.37 mmol) was dissolved in DCM (5 mL), and DAST (297 mg, 1.84 mmol) was added at 0 °C. The mixture was stirred overnight at room temperature and then neutralized with a saturated NaHCO3 solution. It was extracted with DCM (3 × 20 mL), concentrated, and purified by flash (100% PE → PE:EA = 4:1) to obtain Compound 7 (85 mg, 78.6%). 1 H NMR (400 MHz, CDCl3) δ 9.09 (br, 1H), 7.73 (d,J= 4.0 Hz, 1H), 763 (d,J= 8.0 Hz, 1H), 7.31 (d,J= 4.0 Hz, 1H), 6.86 (t,J= 56.0 Hz, 1H), 3.90 (s, 3H). General preparation procedure for Compound 8 of Preparation Example 16 above (MC24-1242-023) Compound 7 (85 mg, 0.29 mmol) was dissolved in CH3CN (5 mL), and DMAP (3.6 mg, 29 μmol) and Boc2O (76 mg, 0.35 mmol) were added in sequence. The mixture was stirred overnight at room temperature, concentrated, and purified by flash (100% PE → PE:EA = 8:1) to obtain Compound 8 (80 mg, 70.0%). 1 H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.67 (s, 2H), 7.44 (t,J= 56.0 Hz, 1H), 3.88 (s, 3H), 1.60 (s, 9H). General preparation procedure for Compound 9 of Preparation Example 16 above (MC24-1242-027) Compound 8 (80 mg, 0.20 mmol) was dissolved in dry THF (10 mL), and DIBAL-H (1.01 mL, 1.01 mmol) was slowly added at 0 °C. The mixture was then stirred at room temperature for 3 hours and stopped with a saturated NH4Cl solution (10 mL). After extraction with EA (3 × 15 mL), the mixture was dried, filtered, and concentrated, and purified by flash (100% PE → PE:EA = 2:1) to obtain Compound 9 (70 mg, 93%). 1 H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.68 (d,J= 8.0 Hz, 1H), 7.60 (d,J= 8.0 Hz, 1H),7.43 (t,J= 56.0 Hz, 1H), 5.01 (s, 2H), 1.60 (s, 9H). General manufacturing procedure for Compound 10 of Manufacturing Example 16 above (MC24-1242-043) Compound 9 (1.5 g, 4.11 mmol) and 2-chloropyrimidine-5-carbaldehyde (0.88 g, 6.16 mmol) were dissolved in CH3CN (80 mL). K2CO3 (1.70 g, 12.32 mmol) and CuI (1.17 g, 6.16 mmol) were added, and the mixture was refluxed overnight under an N2 atmosphere. After cooling, the mixture was filtered and concentrated, and purified by flash (100% PE → PE:EA=3:1) to obtain Compound 10 (1 g, 51.5%). LC-MS: MS (ESI) m / z 472.3 [M+H] + . General manufacturing procedure for Compound 11 of Preparation Example 16 above (MC24-1242-044) Compound 10 (200 mg, 0.42 mmol) was dissolved in THF (10 mL) and EtOH (10 mL), and NaBH4 (20 mg, 0.51 mmol) was added at 0 °C. After stirring at room temperature for 1 hour, the solution was concentrated and purified by flash (100% PE → PE:EA = 1:1) to obtain Compound 11 (80 mg, 39.8%). LC-MS: MS (ESI) m / z 474.3 [M+H] + . General manufacturing procedure for Compound 12 of Manufacturing Example 16 above (MC24-1242-050) Compound 11 (1 g, 0.533 mmol) was dissolved in dry THF (20 mL), and DIEA (0.82 g, 6.34 mmol) and MsCl (0.36 g, 3.17 mmol) were added sequentially at 0 °C. After stirring the mixture at room temperature for 2 hours, ammonium hydroxide (20 mL) was added, and the mixture was stirred for another 8 hours at 60 °C. After concentration, the solution was purified by flash (100% PE → PE:EA = 1:2) to obtain Compound 12 (240 mg, 30.5%). LC-MS: MS (ESI) m / z 373.1 [M+H] +. General preparation procedure for N-((2-((7-(difluoromethyl)-3-(trifluoromethyl)-1H-indole-4-yl)methoxy)pyrimidine-5-yl)methyl)-2-(methylamino)butanamide 2,2,2-trifluoroacetate Compound 12 (110 mg, 0.30 mmol) and 2-(methylamino)butanoic acid (39 mg, 0.33 mmol) were dissolved in DCM (20 mL), followed by the addition of HATU (169 mg, 0.44 mmol) and then DIEA (115 mg, 0.89 mmol). After stirring at room temperature for 3 hours, the mixture was concentrated and purified by reverse-phase Combiflash (TFA conditions) to obtain the final compound N-((2-((7-(difluoromethyl)-3-(trifluoromethyl)-1H-indole-4-yl)methoxy)pyrimidine-5-yl)methyl)-2-(methylamino)butanamide 2,2,2-trifluoroacetate (21.57 mg, 12.2%) as a white solid. LC-MS: MS (ESI) m / z 472.4 [M+H] + ; 1 H NMR (400 MHz, CD3OD) δ 8.60 (s, 2H), 7.84 (s, 1H), 7.44-7.39 (m, 2H), 7.09 (t,J= 56.0 Hz, 1H), 5.80 (s, 2H), 4.42 (s, 2H), 3.68 (t,J= 4.0 Hz, 1H), 2.64 (s, 3H), 1.94-1.87 (m, 2H), 0.94 (t,J= 8.0 Hz, 3H). [Preparation Example 17] Preparation of N3-methyl-N2-((6-((4-(trifluoromethyl)benzyl)oxy)pyridine-3-yl)methyl)pentane-2,3-diamine bis(2,2,2-trifluoroacetate) General manufacturing procedure of Compound 3 (MC24-1171-049) of Preparation Example 17 above Compound 2 (500 mg, 4.06 mmol) was dissolved in ACN (15 mL), after which Compound 1 (1164 mg, 4.872 mmol) and Ag2CO3 (1679 mg, 6.09 mmol) were added. The mixture was stirred overnight at room temperature and then filtered. Water (100 mL) was added to the filtrate, and it was extracted with EA (50 mL × 3). The combined organic layer was dried with Na2SO4 and filtered. The filtrate was concentrated and purified using a silica gel column (PE:EA = 5:1) to obtain Compound 3 (700 mg, 61.4% yield) as a white solid. LC-MS: MS (ESI) m / z: 282.2 [M+H] + . 1 H NMR (400 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.77 (d,J= 2.2 Hz, 1H), 8.17 (dd,J= 8.6, 2.3 Hz, 1H), 7.76 (d,J= 8.2 Hz, 2H), 7.69 (d,J= 8.1 Hz, 2H), 7.11 (d,J= 8.6 Hz, 1H), 5.59 (s, 2H). General manufacturing procedure of Compound 5 (MC24-1171-049) of Preparation Example 17 above Compound 1 (3.7 g, 17.03 mmol) was added to THF (40 mL), and CDI (3.32 g, 20.44 mmol) was added and stirred at room temperature for 0.5 hours. Subsequently, N,O-dimethylhydroxylamine hydrochloride (1.83 g, 18.73 mmol) and DIEA (2.4 g, 18.73 mmol) were added sequentially. After stirring the mixture at room temperature for 2 hours, H2O (100 mL) was added, and the mixture was extracted with EA (100 mL × 3). The organic layers were combined, dried with Na2SO4, filtered, and concentrated to obtain Compound 5 (3.97 g, 89.6% yield) as a yellow liquid. LC-MS: MS (ESI) m / z: 205.2 [M-55] + . General manufacturing procedure of Compound 6 (MC24-1171-063) of Preparation Example 17 above Compound 5 (4.0 g, 15.37 mmol) was dissolved in THF (40 mL), and LiAlH4 (875 mg, 23.05 mmol) was added under a nitrogen atmosphere at 0 °C. The mixture was heated to room temperature and stirred for 2 hours. Subsequently, H2O (80 mL) was added, and the mixture was extracted with EA (50 mL × 3). The organic layer was concentrated and vacuum dried to obtain Compound 6 (2.8 g, 90.6% yield) as a yellow liquid. LC-MS: MS (ESI) m / z: 146.0 [M-55] + . General manufacturing procedure of Compound 7 (MC24-1171-085) of Preparation Example 17 above Compound 6 (200 mg, 0.99 mmol) was dissolved in DCM (3 mL), and N-benzylhydroxylamine (122 mg, 0.99 mmol) and Molecular Sieves (150 mg) were added. The mixture was stirred at room temperature for 4 hours under a nitrogen atmosphere and filtered. The filtrate was concentrated and purified by Prep-TLC (PE:EA = 2:1) to obtain Compound 7 (118 mg, 40.8% yield) as a yellow liquid. LC-MS: MS (ESI) m / z: 207.2 [M-55] + . General manufacturing procedure of Compound 8 (MC24-1171-091) of Preparation Example 17 above Compound 7 (118 mg, 0.4 mmol) was dissolved in dry THF (3 mL), and MeMgBr (0.5 mL, 1.6 mmol) was added at 0 °C under a nitrogen atmosphere. The mixture was stirred at room temperature for 4 hours, and the reaction was quenched with H2O (50 mL). The mixture was extracted with EA (20 mL × 3), and the organic layer was dried, filtered, and concentrated. After purification by Prep-TLC (PE:EA = 6:1), Compound 8 (100 mg, 81.9% yield) was obtained as a yellow liquid. 1 H NMR (400 MHz, DMSO-d6) δ 7.31 - 7.19 (m, 5H), 3.92 - 3.60 (m, 2H), 3.54 (d,J= 13.7 Hz, 1H), 3.30 (s, 3H), 3.08 - 2.78 (m, 1H), 2.68 (s, 1H), 2.60 (s, 2H), 1.39 (s, 6H), 1.26 (s, 3H), 1.05 (t,J= 5.6 Hz, 3H), 0.78 (dt,J= 11.6, 5.8 Hz, 3H). General manufacturing procedure of Compound 9 (MC24-1171-096) of Preparation Example 17 above Compound 8 (944 mg, 2.9 mmol) was dissolved in THF (15 mL), and Pd / C (400 mg) was added. The mixture was stirred overnight at room temperature under an H2 balloon (1 atm). The reaction mixture was filtered, concentrated, and dried to obtain Compound 9 (627 mg, 100% yield) as a yellow liquid. LC-MS: MS (ESI) m / z: 217.2 [M+H] + . General preparation procedure for Compound 10 (MC24-1171-101) of Preparation Example 17 above Compound 3 (400 mg, 1.42 mmol) was dissolved in DCM (10 mL), and Compound 9 (461 mg, 2.13 mmol) was added. The mixture was stirred overnight at room temperature, after which NaBH(OAc)3 (602 mg, 2.84 mmol) was added and stirred for an additional 5 hours. Water (100 mL) was added, and the mixture was extracted with EA (30 mL × 3). The organic layer was concentrated and purified by reverse-phase combi-flash (under NH₄HCO₃ conditions) to obtain Compound 10 (569 mg, 83.3% yield) as a white liquid. LC-MS: MS (ESI) m / z: 482.2 [M+H] + . Compound N3-methyl-N2-((6-((4-(trifluoromethyl)benzyl)oxy)pyridine-3-yl)methyl)pentane-2,3-diamine bis(2,2,2-trifluoroacetate) (MC24-1171-103) General Manufacturing Procedure Compound 10 (569 mg, 1.18 mmol) was dissolved in DCM (5 mL), and TFA (3 mL) was added. After stirring at room temperature for 4 hours, the mixture was concentrated, and the remaining residue was purified using a reverse-phase column (TFA conditions) to obtain N3-methyl-N2-((6-((4-(trifluoromethyl)benzyl)oxy)pyridine-3-yl)methyl)pentane-2,3-diamine bis(2,2,2-trifluoroacetate) (147.49 mg, 32.8% yield) as a white solid. LC-MS: MS (ESI) m / z: 382.2 [M+H] + ; 1 H NMR (400 MHz, DMSO-d6) δ 8.98 (s, 2H), 8.28 (s, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.74 (d,J= 7.8 Hz, 2H), 7.65 (d,J= 7.8 Hz, 2H), 7.02 (d, J = 8.5 Hz, 1H), 5.50 (s, 2H), 4.21 (d,J= 34.5 Hz, 2H), 3.31 (s, 2H), 2.66 (d,J= 13.0 Hz, 3H), 1.90 - 1.74 (m, 1H), 1.56 (dd,J= 14.9, 7.4 Hz, 1H), 1.27 (d,J= 23.0 Hz, 3H), 1.08 - 0.87 (m, 3H). [Preparation Example 18] Preparation of 2-(methylamino)-N-(4-(4-(trifluoromethyl)phenethoxy)benzyl)butanamide General manufacturing procedure of Compound 2 of Preparation Example 18 above NaH (60%, 4.9 g, 123.15 mmol) was added to a mixture of Compound 1 (5.0 g, 24.63 mmol) in THF (60 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, CH3I (34.9 g, 246.3 mmol) was added at 0 °C, and the reaction mixture was stirred overnight at room temperature. After the reaction was complete, H2O (300 mL) was added and washed with EA (100 mL × 3). The aqueous layer was adjusted to pH = 5 using HCl (1 N) and extracted with EA (100 mL × 3). The organic layer was dried with Na2SO4, filtered, and the filtrate was concentrated and dried under reduced pressure to obtain yellow solid Compound 2 (5.2 g, 97.3% yield). 1 H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 4.67 - 4.35 (m, 1H), 2.83 (d,J= 18.3 Hz, 3H), 2.08 - 1.66 (m, 2H), 1.46 (d,J= 10.4 Hz, 9H), 0.95 (t,J= 7.2 Hz, 3H). General manufacturing procedure of Compound 4 of Manufacturing Example 18 above NMM (698 mg, 6.9 mmol) was added to a solution of Compound 2 (1.0 g, 4.6 mmol) dissolved in THF (15 mL) at -78 °C under a nitrogen atmosphere. After stirring the mixture at -78 °C for 5 minutes, IBCF (817 mg, 5.98 mmol) was added. After stirring again at -78 °C for 5 minutes, Compound 3 (680 mg, 5.52 mmol) was added. The mixture was slowly raised to room temperature and stirred at room temperature for 1 hour. The reaction mixture was filtered, and the residue obtained by concentrating the filtrate was purified using a silica gel column (PE:EA = 2:1) to obtain white solid Compound 4 (1.2 g, 78.5% yield). General manufacturing procedure of Compound 6 of Preparation Example 18 above PPh3 (551 mg, 2.1 mmol) and DIAD (425 mg, 2.1 mmol) were sequentially added to Compound 4 (566 mg, 1.75 mmol) and Compound 5 (400 mg, 2.1 mmol) dissolved in THF (10 mL). The mixture was stirred overnight at room temperature under a nitrogen atmosphere and subsequently diluted by adding water (100 mL). The mixture was extracted with EA (30 mL × 3), the organic layer was dried with Na2SO4, and then filtered. The residue obtained by concentrating the filtrate was purified using a reverse-phase column (under NH4HCO3 conditions) to obtain yellow liquid Compound 6 (176 mg, 20.2% yield). LCMS: MS (ESI) m / z: 395.2 [M-100+H] + . General manufacturing procedure of 2-(methylamino)-N-(4-(4-(trifluoromethyl)phenethoxy)benzyl)butanamide TFA (2 mL) was added to a solution of compound 6 (176 mg, 0.355 mmol) dissolved in DCM (5 mL). The mixture was stirred at room temperature for 1 hour and then concentrated to obtain the residue. This residue was purified using a reverse-phase column (under NH4HCO3 conditions) to obtain the white solid 2-(methylamino)-N-(4-(4-(trifluoromethyl)phenethoxy)benzyl)butanamide (100.23 mg, 71.6% yield). LCMS: MS (ESI) m / z: 395.2 [M+H] + ; 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.67 (d,J= 7.7 Hz, 2H), 7.55 (d,J= 7.8 Hz, 2H), 7.16 (d,J= 8.2 Hz, 2H), 6.87 (d, J = 8.3 Hz, 2H), 4.21 (t, J = 6.7 Hz, 4H), 3.12 (t,J= 6.3 Hz, 2H), 2.77 (s, 1H), 2.17 (s, 3H), 1.82 (s, 1H), 1.56 - 1.38 (m, 2H), 0.82 (t,J= 7.3 Hz, 3H). [Preparation Example 19] Preparation of N2-methyl-N1-((5-((4-(trifluoromethyl)benzyl)oxy)pyrimidine-2-yl)methyl)butein-1,2-diamine dihydrochloride General manufacturing procedure of Compound 2 (MC24-1017-093) of Preparation Example 19 above SM1 (0.5 g, 3.83 mmol) and SM2 (1.0 g, 4.59 mmol) were dissolved in DMF (15 mL), and then K2CO3 (0.795 g, 5.74 mmol) was added. The mixture was stirred overnight at room temperature and then diluted with water (100 mL). The mixture was extracted with EA (100 mL × 3). The bound organic layer was dried with Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to obtain the residue. The residue was purified by silica gel flash chromatography (PE:EA = 1:10) to obtain Compound 2 (1.0 g, 90.9% yield) as a white solid. LC-MS: MS (ESI) m / z: 288.9. General manufacturing procedure of Compound 3 (MC24-1017-097) of Preparation Example 19 above CataCXium A-Pd-G3 (177 mg, 0.244 mmol) and K3PO4 (1.5 g, 7.32 mmol) were added to a solution of Compound 2 (0.706 g, 2.44 mmol) and SM3 (0.870 g, 3.66 mmol) dissolved in 1,4-dioxane (40 mL) and H2O (8 mL). The mixture was stirred at 110 °C under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature and diluted with water (50 mL). The mixture was extracted with EA (100 mL × 3). The bound organic layer was dried with Na2SO4 and filtered. The filtrate was evaporated under reduced pressure and purified by silica gel flash chromatography (PE:EA = 1:2) to obtain Compound 3 (1.3 g, 100% yield) as a white solid. LC-MS: MS (ESI) m / z: 384.6. General preparation procedure for Compound 4 (MC24-1017-107) of Preparation Example 19 above TFA (4 mL) was added to a solution of Compound 3 (700 mg, 1.83 mmol) dissolved in DCM (12 mL), and the mixture was stirred at room temperature for 2 hours. After confirming the completion of the reaction by LC-MS, the reaction mixture was neutralized with a saturated NaHCO3 solution. The mixture was extracted with DCM (80 mL × 3). The bound organic layer was dried with Na2SO4 and filtered. The filtrate was concentrated to obtain Compound 4 (650 mg, 100% yield) as a white solid. LC-MS: MS (ESI) m / z: 284.2. General manufacturing procedure of Compound 5 (MC24-1017-108) of Manufacturing Example 19 above AcOH (0.3 mL) was added to a solution of Compound 4 (0.380 g, 1.34 mmol) and SM4 (0.270 g, 1.34 mmol) dissolved in DCM (30 mL), and the mixture was stirred at room temperature for 2 hours. Subsequently, NaBH(OAc)3 (0.568 g, 2.68 mmol) was added all at once. The mixture was stirred at room temperature for an additional 2 hours. After confirming the completion of the reaction by LC-MS, water (40 mL) was added to dilute the solution. The mixture was extracted with EA (80 mL × 3). The bound organic layer was concentrated under reduced pressure and purified by C18 reverse-phase chromatography (ACN / H2O, 0.05% TFA) to obtain Compound 5 (0.250 g, 39.8% yield) as a colorless oil. LC-MS: MS (ESI) m / z: 469.4. General manufacturing procedure of N2-methyl-N1-((5-((4-(trifluoromethyl)benzyl)oxy)pyrimidine-2-yl)methyl)butein-1,2-diamine dihydrochloride TFA (4 mL) was added to a solution of Compound 5 (250 mg, 0.533 mmol) dissolved in DCM (12 mL), and the mixture was stirred at room temperature for 2 hours. After confirming the completion of the reaction by LC-MS, the reaction mixture was concentrated and neutralized with a saturated NaHCO3 solution. The residue was extracted with DCM (50 mL × 3), the organic layer was dried with Na2SO4, and filtered. The filtrate was concentrated and purified by C18 reverse-phase chromatography (ACN / H2O, 0.05% HCl) to obtain N2-methyl-N1-((5-((4-(trifluoromethyl)benzyl)oxy)pyrimidine-2-yl)methyl)butein-1,2-diamine dihydrochloride (159 mg, 81.1% yield) as a colorless oil. LC-MS: MS (ESI) m / z: 369.4; 1H NMR (400 MHz, DMSO-d6) δ 9.93 (br, 2H), 9.71 (br, 1H), 9.51 (br, 1H), 8.74 (s, 2H), 7.77 (dd,J= 29.4, 8.1 Hz, 4H), 5.46 (s, 2H), 4.48 (q,J= 15.8 Hz, 2H), 3.63 - 3.43 (m, 3H), 2.58 (d,J= 19.9 Hz, 3H), 1.88 -1.81 (m, 1H), 1.76 - 1.67 (m, 1H), 0.99 (t,J= 7.4 Hz, 3H). [Preparation Example 20] Preparation of N-(3-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide General manufacturing procedure of Compound 2 of Preparation Example 20 above To a solution in which Compound 1 (7.5 g, 35.04 mmol), PPh3 (13.6 g, 52.57 mmol), and HN(Boc)2 (7.6 g, 35.04 mmol) were dissolved in THF (100 mL), DEAD (9.1 g, 52.57 mmol) was added under an N2 atmosphere at 0 °C. The mixture was stirred overnight at room temperature and then diluted with water (100 mL). The mixture was extracted with EA (100 mL × 3). The bound organic layer was evaporated under reduced pressure and purified by silica gel flash chromatography (PE:EA = 1:10) to obtain Compound 2 (3.75 g, 25.9% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 7.46 (d,J= 8.4 Hz, 2H), 7.17 (d,J= 8.4 Hz, 2H), 3.55 - 3.43 (m, 2H), 2.54 (dd,J= 13.0, 5.5 Hz, 2H), 1.84 - 1.68 (m, 2H), 1.42 (s, 18H). General manufacturing procedure of Compound 3 of Manufacturing Example 20 above A solution of Compound 2 (4.7 g, 11.37 mmol) dissolved in HCl-dioxane (50 mL) was stirred at room temperature for 1 hour. The solution was evaporated to obtain Compound 3 (2.7 g, 100% yield) as a white solid. LC-MS: MS (ESI) m / z: 214.2 [M+H] + (79 Br). General manufacturing procedure of Compound 4 of Manufacturing Example 20 above HATU (4.4 g, 11.68 mmol) was added to a solution of Compound 3 (2.67 g, 11.68 mmol) dissolved in DMF (30 mL), and the mixture was stirred at room temperature for 5 minutes. Subsequently, SM1 (2.5 g, 11.68 mmol) and DIEA (3.0 g, 23.36 mmol) were added sequentially. After stirring the mixture at room temperature for 1 hour, water (100 mL) was added to dilute it, and it was extracted with EA (100 mL × 3). The bound organic layer was evaporated under reduced pressure, and the solution was purified by silica gel flash chromatography (PE:EA = 1:5) to obtain Compound 4 (3.0 g, 56.7% yield) as a white solid. LC-MS: MS (ESI) m / z: 327.0 [M-100+H] + (81 Br). General manufacturing procedure of Compound 5 of Manufacturing Example 20 above Pd(dppf)Cl2 (358 mg, 0.49 mmol) and K2CO3 (680 mg, 4.92 mmol) were added to a solution of Compound 4 (700 mg, 1.64 mmol) and SM2 (312 mg, 1.64 mmol) dissolved in 1,4-dioxane (15 mL) and H2O (3 mL). The mixture was stirred overnight at 100 °C under an N2 atmosphere and then cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with EA (60 mL × 3). The bound organic layer was evaporated under reduced pressure and purified by silica gel flash chromatography (PE:EA = 1:5) to obtain Compound 5 (0.7 g, 86.6% yield) as a white solid. LC-MS: MS (ESI) m / z: 391.0 [M-100+H] + . General manufacturing procedure of N-(3-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide TFA (3 mL) was added to a solution of Compound 5 (350 mg, 0.71 mmol) dissolved in DCM (12 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to obtain the residue, which was neutralized with a saturated aqueous NaHCO3 solution. The mixture was extracted with EA (100 mL × 3). The bound organic layer was evaporated under reduced pressure and purified by C18 reverse-phase chromatography (ACN / H2O, 10 mmol / L NH4HCO3) to obtain Compound N-(3-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide as a white solid. LC-MS: MS (ESI) m / z: 391.3 [M+H] + ; 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J = 2.1 Hz, 1H), 7.51 - 7.44 (m, 3H), 7.39 (dd, J = 8.3, 2.1 Hz, 1H), 7.28 (s, 1H), 7.26 (s, 1H), 6.86 (s, 1H), 3.31 (dd, J = 13.2, 6.9 Hz, 2H), 3.21 (dd, J = 9.5, 3.1 Hz, 1H), 3.02 (dd, J = 11.6, 2.9 Hz, 1H), 2.76 - 2.59 (m, 3H), 2.02 - 1.94 (m, 1H), 1.88 (m, 3H), 1.79 (d, J = 4.5 Hz, 1H), 1.58 (dd, J = 8.9, 3.2 Hz, 1H), 1.48 - 1.31 (m, 3H). [Preparation Example 21] Preparation of N-(4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide General manufacturing procedure of Compound 1 of Manufacturing Example 21 above DMF (0.1 mL) was added to a solution of 4-(4-bromophenyl)butanoic acid (10.0 g, 41.1 mmol) dissolved in CH2Cl2 (100 mL), and then SOCl2 (9.8 g, 82.2 mmol) was added under an N2 atmosphere at 0 °C. The reaction mixture was stirred at room temperature for 60 minutes. After concentrating the reaction solution, the residue was poured into ammonium hydroxide (100 mL) filled with ice. The resulting mixture was stirred at 0 °C for 10 minutes. The reaction suspension was filtered, and the filter cake was washed with water (20 mL) to obtain 4-(4-bromophenyl)butanamide (8.5 g, 85.3% yield) as a white solid. LC-MS: MS (ESI) m / z: 244.1 [M+H] + . General manufacturing procedure of Compound 2 of Manufacturing Example 21 above To a solution of 4-(4-bromophenyl)butanamide (8.5 g, 35.1 mmol) dissolved in THF (85 mL), a borane-methyl sulfide complex (17.6 mL, 176 mmol) was slowly added at 0 °C under an N2 atmosphere. The reaction mixture was stirred at 70 °C for 60 minutes. After cooling the reaction solution to room temperature, MeOH (100 mL) was added and stirred at room temperature for 30 minutes. The resulting mixture was concentrated, and the residue was purified using a C18 column (H2O:MeCN = 3:1) to obtain 4-(4-bromophenyl)butan-1-amine (3.6 g, 45.0% yield) as a pale yellow oil. LC-MS: MS (ESI) m / z: 230.2 [M+H] + . General manufacturing procedure of Compound 3 of Manufacturing Example 21 above HATU (2.5 g, 6.6 mmol) and DIPEA (1.7 g, 13.2 mmol) were added to a solution of 4-(4-bromophenyl)butan-1-amine (1.0 g, 4.4 mmol) and 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (1.1 g, 4.8 mmol) dissolved in DMF (20 mL). The reaction mixture was stirred at room temperature for 16 hours. The reaction solution was poured into ice water (60 mL), and the mixture was extracted with EtOAc (50 mL × 2). The bound organic layer was washed with salt water, dried with anhydrous Na2SO4, and concentrated. The residue was purified using a silica gel column (petroleum ether:EtOAc = 2:1) to obtain tert-butyl 2-((4-(4-bromophenyl)butyl)carbamoyl)piperidine-1-carboxylate (1.5 g, 77.9% yield) as a white solid. LC-MS: MS (ESI) m / z: 341.3 [M+H]+ . General manufacturing procedure of Compound 4 of Manufacturing Example 21 above K2CO3 (314 mg, 2.28 mmol) and Pd(dppf)Cl2 (67 mg, 0.09 mmol) were added to a solution in which tert-butyl 2-((4-(4-bromophenyl)butyl)carbamoyl)piperidine-1-carboxylate (400 mg, 0.91 mmol) and (3,4-dichlorophenyl)boronic acid (260 mg, 1.37 mmol) were dissolved in 1,4-dioxane (10.0 mL) and water (2.0 mL). The mixture was degassed three times with N2. The reaction mixture was stirred at 90 °C for 3 hours. The reaction solution was poured into ice water (30 mL) and extracted with EtOAc (30 mL × 2). The bound organic layer was washed with salt water, dried with anhydrous Na2SO4, and concentrated. The residue was purified using a silica gel column (petroleum ether:EtOAc=3:1) to obtain tert-butyl 2-((4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)carbamoyl)piperidine-1-carboxylate (280 mg, 60.8% yield) as a pale yellow solid. LC-MS: MS (ESI) m / z: 527.4 [M+Na] + . General manufacturing procedure of N-(4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide tert-butyl 2-((4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)carbamoyl)piperidine-1-carboxylate (280 mg, 0.55 mmol) was dissolved in CH2Cl2 (5.0 mL), and TFA (1.0 mL) was slowly added. The reaction mixture was stirred at room temperature for 60 minutes. The reaction solution was concentrated, diluted with CH2Cl2 (20 mL), and washed sequentially with saturated NaHCO3 (20 mL) and salt water (20 mL). The organic layer was dried with anhydrous Na2SO4 and concentrated. The residue was purified using a silica gel column (CH2Cl2:MeOH=10:1) to obtain the compound N-(4-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide (136 mg, 60.6% yield) as a white solid. LC-MS: MS (ESI) m / z: 405.3 [M+H] + ; 1 H NMR (400 MHz, DMSO-d6) δ 7.92 (d,J= 2.0 Hz, 1H), 7.71 - 7.58 (m, 5H), 7.31 (d,J= 8.0 Hz, 2H), 3.11 - 3.05 (m, 2H), 2.99 - 2.96 (m, 1H), 2.90 - 2.86 (m, 1H), 2.62 (t,J= 7.2 Hz, 2H), 2.49 - 2.44 (m, 1H), 2.13 (s, 1H), 1.70 - 1.68 (m, 2H), 1.61 - 1.53 (m, 2H), 1.46 - 1.39 (m, 3H), 1.33 - 1.24 (m, 3H). [Preparation Example 22] Preparation of N-(2-(4'-chloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide General manufacturing procedure of Compound 3 of Manufacturing Example 22 above Compound 2 (347 mg, 2.43 mmol), Pd(dppf)Cl2 (534 mg, 0.729 mmol), and K2CO3 (1.01 g, 7.29 mmol) were added to a solution of Compound 1 (1 g, 2.43 mmol) dissolved in 1,4-dioxane (20 mL) and H2O (4 mL). The mixture was stirred overnight at 100°C under a nitrogen atmosphere and then cooled to room temperature. The reaction mixture was diluted with water (50 mL) and extracted with EA (50 mL × 3). The organic layer was concentrated and purified by silica gel column chromatography (PE:EA=5:1) to obtain Compound 3 (930 mg, 93% yield) as a white solid. LCMS: MS (ESI) m / z: 343.2 [M+H] + . General manufacturing procedure of N-(2-(4'-chloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide TFA (3 mL) was added to a solution of Compound 3 (300 mg, 0.67 mmol) dissolved in DCM (9 mL), and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was concentrated to obtain a residue, which was neutralized with a saturated aqueous NaHCO3 solution (100 mL). The mixture was extracted with EA (50 mL × 3). After concentrating the organic layer, it was purified by reverse-phase Combi-flash (under NH4HCO3 conditions) to obtain Compound N-(2-(4'-chloro-[1,1'-biphenyl]-4-yl)ethyl)piperidine-2-carboxamide as a white solid. LCMS: MS (ESI) m / z: 343.1 [M+H] + ; 1H NMR (400 MHz, CDCl3) δ 7.50 (dd,J= 8.3, 3.0 Hz, 4H), 7.39 (d,J= 8.5 Hz, 2H), 7.27 (d,J= 6.9 Hz, 2H), 6.86 (s, 1H), 3.61 - 3.49 (m, 2H), 3.18 (dd,J= 9.7, 3.2 Hz, 1H), 2.97 (dd,J= 12.4, 3.6 Hz, 1H), 2.86 (t,J= 7.1 Hz, 2H), 2.65 (dd,J= 15.7, 6.9 Hz, 1H), 1.95 (d,J= 9.2 Hz, 1H), 1.83 - 1.75 (m, 1H), 1.66 (s, 1H), 1.56 (d,J= 7.3 Hz, 1H), 1.47 - 1.32 (m, 3H). [Preparation Example 23] Preparation of N-(3-(4'-chloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide General manufacturing procedure of Compound 2 of Manufacturing Example 23 above Pd(dppf)Cl2 (358 mg, 0.49 mmol) and K2CO3 (679 mg, 4.92 mmol) were added to a solution of Compound 1 (700 mg, 1.64 mmol) and SM1 (256 mg, 1.64 mmol) dissolved in 1,4-dioxane (15 mL) and H2O (3 mL). The mixture was stirred overnight at 100 °C under an N2 atmosphere and then cooled to room temperature. The mixture was diluted with water (60 mL) and extracted with EA (80 mL × 3). The bound organic layer was concentrated under reduced pressure and purified by silica gel flash chromatography (PE:EA=1:5) to obtain Compound 2 (0.8 g, 100% yield) as a white solid. LC-MS: MS (ESI) m / z: 357.1 [M-100+H] + General manufacturing procedure of N-(3-(4'-chloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide TFA (3 mL) was added to a solution of Compound 2 (350 mg, 0.76 mmol) dissolved in DCM (12 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to obtain the residue, which was neutralized with a saturated aqueous NaHCO3 solution. The mixture was extracted with EA (80 mL × 3). The bound organic layer was concentrated under reduced pressure and purified by C18 reverse-phase chromatography (ACN / H2O, 10 mmol / L NH4HCO3) to obtain Compound N-(3-(4'-chloro-[1,1'-biphenyl]-4-yl)propyl)piperidine-2-carboxamide as a white solid. LC-MS: MS (ESI) m / z: 357.1 [M+H] + ; 1 H NMR (400 MHz, CDCl3) δ 7.49 (t,J= 8.2 Hz, 4H), 7.39 (d,J= 8.4 Hz, 2H), 7.27 (s, 1H), 7.25 (s, 1H), 6.81 (s, 1H), 3.32 (dd, J = 13.2, 6.6 Hz, 2H), 3.22 - 3.14 (m, 1H), 2.99 (d,J= 11.7 Hz, 1H), 2.77 - 2.55 (m, 3H), 1.97 (d, J = 9.1 Hz, 1H), 1.89 (dd,J= 14.6, 7.3 Hz, 2H), 1.73 (s, 2H), 1.57 (d,J= 5.4 Hz, 1H), 1.45 - 1.28 (m, 3H). [Preparation Example 24] Preparation of N-(4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide General manufacturing procedure of Compound 2 of Manufacturing Example 24 above K2CO3 (314 mg, 2.28 mmol) and Pd(dppf)Cl2 (67 mg, 0.09 mmol) were added to a solution in which tert-butyl 2-((4-(4-bromophenyl)butyl)carbamoyl)piperidine-1-carboxylate (400 mg, 0.91 mmol) and (4-chlorophenyl)boronic acid (214 mg, 1.37 mmol) were dissolved in 1,4-dioxane (10.0 mL) and water (2.0 mL). The mixture was degassed three times with N2. The reaction mixture was stirred at 90 °C for 3 hours. The reaction solution was poured into ice water (30 mL) and extracted with EtOAc (30 mL × 2). The bound organic layer was washed with salt water, dried with anhydrous Na2SO4, and concentrated. The residue was purified using a silica gel column (petroleum ether:EtOAc=3:1) to obtain tert-butyl 2-((4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)carbamoyl)piperidine-1-carboxylate (360 mg, 84.0% yield) as a pale yellow solid. LC-MS: MS (ESI) m / z: 493.4 [M+Na] + . General manufacturing procedure of N-(4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide TFA (1.0 mL) was slowly added to a solution of tert-butyl 2-((4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)carbamoyl)piperidine-1-carboxylate (360 mg, 0.76 mmol) dissolved in CH2Cl2 (5.0 mL). The mixture was stirred at room temperature for 60 minutes. The reaction solution was concentrated, diluted with CH2Cl2 (20 mL), and washed with saturated NaHCO3 (20 mL) and salt water (20 mL). The organic layer was dried with anhydrous Na2SO4 and then concentrated. The residue was purified using a silica gel column (CH2Cl2:MeOH = 10:1) to obtain N-(4-(4'-chloro-[1,1'-biphenyl]-4-yl)butyl)piperidine-2-carboxamide as a white solid. LC-MS: MS (ESI) m / z: 371.3 [M+H] + ; 1 H NMR (400 MHz, DMSO-d6) δ 7.68 - 7.65 (m, 2H), 7.61 - 7.56 (m, 3H), 7.51 - 7.48 (m, 2H), 7.30 (d,J= 8.4 Hz, 2H), 3.11 - 3.06 (m, 2H), 2.99 - 2.96 (m, 1H), 2.90 - 2.86 (m, 1H), 2.61 (t,J= 7.6 Hz, 2H), 2.50 - 2.45 (m, 1H), 2.21 (s, 1H), 1.70 - 1.68 (m, 2H), 1.61 - 1.53 (m, 2H), 1.46 - 1.39 (m, 3H), 1.35 - 1.24 (m, 3H). [Preparation Example 25] Preparation of N-(3',4'-dichloro-[1,1'-biphenyl]-4-yl)-2-(methylamino)butanamide hydrochloride Compound 30 (ATS0047) was prepared by referring to reaction schemes 1 to 12, reaction schemes a to g, Korean registered patent publication 10-2099980 and Korean registered patent publication 10-2286897. <Physical Properties Investigation> Investigation Example 1: Compound 9 (2-(dimethylamino)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)pentanamide hydrochloride) Investigation of pKa values The pKa of the sample was determined using the pH-metric method. Compound 9 was confirmed to be insoluble in aqueous solution through a pretest. Therefore, the use of organic solvents such as methanol (MeOH) or DMSO was essential to completely dissolve the sample and determine the type of pKa (acidic pKa or basic pKa). Test results for selecting an appropriate solvent showed that MeOH was more suitable for dissolving the sample, and multiple titrations were performed under conditions of approximately 59.7%, 48.9%, and 39.1% MeOH to evaluate the types of ionizable functional groups. As a result of the multiple titrations for Compound 9, a total of three psKa values, rather than pKa values, were derived for each ionizable functional group. Subsequently, a single regression curve was derived by applying the Yasuda-Shedlovsky extrapolation method to the individual titration results, and the pKa value under aqueous conditions was calculated using this. As a result, pKa = 7.68 ± 0.05 (basicity, R 2 = 0.9976) was calculated from the potentiometric data. The fact that a single regression curve was derived means that the compound 9 originally contains only one ionizable functional group, and therefore only one pKa value was measured for this compound. Yasuda-Shedlovsky result Extrapolation typepKaSDInterceptSlopeR 2 Ionic strengthTemperature (℃)Yasuda-Shedlovsky7.68±0.0511.96-198.91900.99760.171M25 Component assay results TitrationMethanol (wt%)DirectionResult typeDielectric constant[H2O] (M)Ionic strength (M)Temperature (℃)psKa125H-30006Points 1-4559.65 %UppH-metric51.819.30.16125.06.8225H-30006Points 46-9248.87 %UppH-metric56.925.00.17225.07.0825H-30006Points 93-14239.08 %UppH-metric61.430.50.17925.07.20 Investigation of LogP values The LogP of the sample was determined using the potentiometric (pH-metric) method. Compound 9 was titrated to cover the pH range of 2–12 under conditions with varying octanol / water ratios, with sample concentrations ranging from 0.74 to 1.53 mM. Using the collected potentiometric data, the LogP value for neutral species was calculated as 4.80 ± 0.02. Since no precipitation or degradation occurred during duplicate titrations, accurate LogP and LogD values ​​could be measured across the entire pH range. The Lipophilicity Profile interprets the change in LogP as a function of pH at pH > 9.0 and LogD as a function of pH in the pH < 9.0 range. Accordingly, based on the LogD table calculated from the Lipophilicity Profile, the LogD value under physiological conditions (pH 7.4, blood) was derived as 4.34. pH-metric Result Type Result logP (XH+) 1.95±0.02 (n=50) logP (neutral X) 4.80±0.02 (n=50) Sample LogD Values ​​logD pH Comment 1.000 1.95 1.200 1.95 Stomach pH 2.000 1.95 3.000 1.95 4.000 2.01 5.000 2.3 4 6.000 3.1 4 7.000 4.04 7.400 4.3 4 Blood pH 8.000 4.6 3 9.000 4.7 8 10.000 4.8 11.000 4.8 12.000 4.8 1 Solubility investigation Solubility tests were performed using the potentiometric (pH-metric) method and the CheqSol technique. Unlike pKa and LogP tests, solubility tests require the use of an excess amount of sample to reach saturation. To this end, all samples were titrated at relatively high concentrations in the pH range of 2 to 12 to induce saturation in aqueous solution. The CheqSol(crossing points) analysis method is designed to induce a supersaturated solution by establishing crossing points to estimate equilibrium solubility based on neutral species (for details, see siriuskorea.com / references). When precipitation occurs at a specific pH point and reaches a supersaturated state, kinetic solubility can be estimated based on the pH point where the first precipitation is observed. The following are the results of the solubility test according to the pH range. According to the CheqSol test results, the equilibrium solubility of sample ATS0004 was determined to be 26.03 μM in the pH > 10.0 range (kinetic solubility was 58.1 μM at pH 5.5). Due to the pH-dependent change in solubility according to the pKa value, solubility changed in the low pH range (pH < 10.0), which is shown in the solubility-pH profile (Solubility vs. pH Profile). Overall ResultItem ValueRefinement methodCrossing point (CheqSol)DMSO11.7 wt%Molarity (Equilibrium solubility)26.03 μMlogS-4.585log(1 / S)4.585Weight / mL10.8 μg / mLIonic strength0.145 MTemperature25.0 ℃Concentration CV31.23 %Kinetic solubility58.1 μMNatural solubility30.62 μMNatural pH8.433 Solubility Versus pH Table [Calculated Values] Molarity pH log S log (1 / S) Weight / mL Comment 1.000----1.200----Stomach pH 2.000----3.000 1.246 μm-0.0954 0.09545 16.9 mg / mL 4.000 124.6 mM-0.9045 0.9045 1.7 mg / mL 5.000 12.48 mM-1.904 1.9045 5.18 mg / mL 6.000 1.272 mM-2.896 2.8965 27.7 μg / mL 7.000 150.6 μm-3.822 3.822 62.49 μg / mL 7.400 75.63 μM-4.1214.12131.38 μg / mLLOOD pH8.00038.49 μM-4.4154.41515.97 μg / mL9.00027.27 μM-4.5644.56411.32 μg / mL10.00026.15 μM-4.5824.58210.85 μg / mL11.00026.04 μM-4.5844.58410.8 μg / mL12.00026.03 μM-4.5854.58510.8 μg / mL Investigation Example 2: Compound 23 (2-(methylamino)-N-(4-(4-(trifluoromethyl)phenethoxy)benzyl)butanamide) Investigation of pKa values The pKa of the sample was measured using the pH-metric (potentiometric titration) method. Pretesting confirmed that Compound 23 is insoluble in aqueous solution. Therefore, the use of organic solvents such as methanol (MeOH) or DMSO was essential to completely dissolve the sample and identify the type of ionization group, such as whether it is acidic or basic. Based on the results of solvent selection tests, methanol was determined to be the most suitable for dissolving the sample and was used in this experiment. Multiple titrations were performed under conditions of approximately 59.6%, 48.8%, and 38.8% MeOH to characterize the ionization group. As a result of the multiple titrations performed on Compound 23, a total of three psKa values ​​were derived for each ionization group, rather than pKa values. Subsequently, a single regression curve was established to calculate the pKa value under aqueous conditions by applying the Yasuda-Shedlovsky extrapolation method to each titration result. As a result, the pKa under aqueous conditions calculated from the potential difference data is 8.04 ± 0.00 (basicity, R 2 = 1.0000). The fact that a single regression curve was derived means that the sample ATS0023 originally contains only one ionizable group, and accordingly, only one pKa value was measured for this compound. Yasuda-Shedlovsky result Extrapolation typepKaSDInterceptSlopeR 2 Ionic strengthTemperature (℃)Yasuda-Shedlovsky8.04±0.0011.48-132.63701.00000.170M25 Component assay resultsTitrationMethanol (wt%)DirectionResult typeDielectric constant[H2O] (M)Ionic strength (M)Temperature (℃)psKa125H-31006 (Points 1-47)59.61UppH-metric51.819.3 M0.16025.07.6325H-31006 (Points 48-96)48.77UppH-metric56.925.1 M0.17125.07.7425H-31006 (Points 97-147)38.75UppH-metric61.530.7 M0.17825.07.80 Investigation of LogP values The LogP of the samples was measured using the pH-metric method. Compound 23 was titrated in the pH range of 2–12 with varying octanol / water ratios, and sample concentrations ranged from 0.57 to 1.18 mM. Using the collected potentiometric data, a LogP value of 4.18 ± 0.02 for neutral species was calculated. Since no precipitation or degradation occurred during duplicate titrations, reliable LogP and LogD values ​​could be measured across the entire pH range. The Lipophilicity Profile interprets changes in LogP at pH > 9.0 and LogD at pH < 9.0. Accordingly, based on the LogD table calculated from the Lipophilicity Profile, the LogD value at pH 7.4 (blood conditions) was derived as 3.47. pH-metric Result Type Result logP (XH+) 1.98±0.03 (n=50) logP (neutral X) 4.18±0.02 (n=50) Sample LogD Values ​​pH logD Comment 1.000 1.98 1.200 1.98 Stomach pH 2.000 1.98 3.000 1.98 4.000 1.98 5.000 2.04 6.000 2.37 7.000 3.13 7.400 3.47 Blood pH 8.000 3.87 9.000 4.14 10.000 4.18 11.000 4.18 12.000 4.18 Solubility investigation Solubility was evaluated using the pH-metric method and the CheqSol method. Unlike pKa and LogP measurements, solubility tests require the use of an excess amount of sample to ensure that the matrix containing the sample reaches a saturation state. To this end, all samples were titrated at relatively high concentrations within the pH range of 2–12 to induce saturation in the aqueous solution. The CheqSol (crossing points) analysis method is designed to form a supersaturated state by inducing precipitation at specific pH points and to estimate the equilibrium solubility of neutral species based on this (see siriuskorea.com / references). Kinetic solubility can be estimated at the pH point where the first precipitation is observed upon reaching supersaturation. This is defined as the pH point where precipitation first occurs. The results of the solubility tests according to pH changes are summarized as Solubility vs. pH Profile. CheqSol analysis revealed that the equilibrium solubility of compound 23 was 488 μM in the pH > 11.0 range, and the kinetic solubility was measured at 512.5 μM at pH 7.8. Since solubility varies with pH as a function of pKa values, the solubility showed a changing pattern in the pH range below 11.0 (pH < 11.0), which can be confirmed in the solubility vs. pH profile. Overall ResultItem ValueRefinement methodCrossing point (CheqSol)DMSO11.7 wt%Molarity (Equilibrium solubility)488 μMlogS-3.312log(1 / S)3.312Weight / mL210.3 μg / mLIonic strength0.145 MTemperature25.0 °CConcentration CV2.17 %Kinetic solubility512.5 μMNatural solubility518 μMNatural pH9.249 Solubility Versus pH Table [Calculated Values] pH Molarity log S log (1 / S) Weight / mL Comment 1.000----1.200----Stomach pH 2.000----3.000----4.0005.351 M 0.7284-0.72842306 mg / mL 5.000535.5 mM-0.27120.2712230.8 mg / mL 6.00053.99 mM-1.2681.26823.27 mg / mL 7.0005.838 mM-2.2342.2342.516 mg / mL 7.4002.618 mM-2.5822.5821.128 mg / mL L Blood pH 8.0001.023 mM-2.9902.990440.8 μg / mL9.000541.5 μM-3.2663.266233.3 μg / mL10.000493.3 μM-3.3073.307212.6 μg / mL11.000488.5 μM-3.3113.311210.5 μg / mL12.000488 μM-3.3123.312210.3 μg / mL <Example> Example 1: Cell line and cell culture RAW 264.7 cell lines and HaCaT cell lines were obtained from the Korean Cell Line Bank (KCLB, Seoul, Korea) and cultured in Dürbecco modified Eagle medium (DMEM, Gibbco, Cat No. 11995073) supplemented with 10% fetal bovine serum (FBS, Gibbco, Cat No. 26140-079) in a CO2 incubator (Thermo Scientific, Cat No. 51023121) under conditions of 5% CO2 and a temperature of 37°C. Example 2: Evaluation of cell viability To evaluate the cell viability of the ATS series drugs (compounds 5 to 30), RAW264.7 cells and HaCaT cells were seeded into 96-well plates at a density of 5 x 10^4 cells / well, respectively, and stabilized by incubating overnight in a 37°C CO2 incubator. After 24 hours, the ATS series drugs were prepared in DMEM to a concentration of 10 μM and treated to the cells for 24 hours. After 24 hours, EZ-CYTOX (DOGEN, Cat No. EZ-3000) was added and reacted for 30 minutes, after which cell viability was measured using a spectrophotometer. Cell viability (%) was calculated as (absorbance value of drug-treated group - absorbance value of solvent only) / (absorbance value of control group - absorbance value of solvent only) x 100. Example 3: 5-HT 2A Antagonist analysis 5-HT 2A A human serotonin GPCR binding antagonist radioligand leadhunter assay (Eurofins, 135) was performed on human 5-HT in HEK-293 cells 2A Radioligand binding assays were used to evaluate the affinity of ATS series drugs by transducing receptors. Cell membrane homogenates (protein 40 μg) were mixed with ATS series drugs (10 μM) and [ 3[H]ketanserin (0.5 nM) was added and incubated at 22°C for 60 minutes. ATS series drugs were dissolved in DMSO and diluted in 50 mM Tris-HCl buffer (pH 7.4) to a concentration of 10 μM. The samples were plated in two replicates to evaluate the displacement of the radioligand from the target receptor, and nonspecific binding was screened using a positive control, ketanserin (1 μM). After incubation, samples were rapidly filtered under vacuum through a glass fiber filter (GF / B, Packard) pre-soaked in 0.3% PEI, and washed multiple times with ice-cold 50 mM Tris-HCl using a 96-sample cell harvester (Unifilter, Packard). After drying the filters, radioactivity was measured using a stintillation cocktail (Microscint O, Packard) and a stintillation counter (Topcount, Packard). The measured value was calculated as the inhibition rate (%) of control group-specific binding = 100 - (measured specific binding / control group-specific binding X 100). Example 4: Cell culture culture Dorsal root ganglions (DRGs) excised from C57BL / 6 mice were separated into single-cell suspensions after enzyme treatment and cultured on culture plates coated with laminin (Gibco, Cat No. 23017-015) and Neurobasal medium (NBM, Gibco Cat No. 21103-049) containing B27 serum-free supplement (Gibco, Cat No. 17504-044) and L-Glutamine (Gibco, Cat No. 25030-164). Example 5: Calcium imaging To investigate the effects on calcium ion regulation, which is important for pain and itching pathways, the effects of candidate drugs on intracellular calcium influx in cultured DRG cells were analyzed. Cells were pretreated with the calcium-specific dye Fluo-3 / AM (5 μM), followed by treatment with 100 μM Histamine or 1 μM Capsaicin to induce calcium ion influx. After treatment, changes in fluorescence intensity over time were measured using a confocal microscope, and intracellular calcium concentration was quantified by calculating the ratio (F / F0) of the fluorescence intensity (F) to the initial value (F0). Example 6: MC903-induced pruritus model An MC903-induced pruritus model was established using BALB / c mice. The animals were fed free food and water for one week during the acclimatization period. After acclimatization, pruritus was induced by dissolving 1.5 nmol or 2 nmol of MC903 in 100% ethanol and applying it to both ears of the mice for 10 days. Starting from day 4 of pruritus induction, 10 mg / kg Ruxolitinib and 1 mg / kg Compound 5 (ATB1606) were used as positive controls, and four ATS series drugs (Compound 9 (ATS0004), Compound 10 (ATS0005), and Compound 23 (ATS0023)) were administered intraperitoneally (ip) at 1, 5, and 10 mg / kg for 7 days. All drugs were dissolved in 100% DMSO and then diluted to an excipient composition of 5% DMSO, 30% PEG300, and 65% Saline (only Compound 23 (ATS0023) had an excipient composition of 10% DMSO, 30% PEG300, and 60% Saline). For the evaluation of itching, mice were separated into individual mini-cages, video recorded for 30 minutes, and the number of times they scratched their ears with their hind legs was recorded and quantified. Example 7: Pharmacokinetic Experiment Test Substance Test Substance Batch Number Storage Conditions Appearance Salt Form or Free Form Molecular Weight (Salt) Molecular Weight (Free Form) Purity ATS 000 4AC 116 25H Store in a sealed container and keep away from light at room temperature (+1 to +30°C) Solid, white powder Free Form Not applicable Not applicable >95% ATS 00 23MC 25-630 32A1 Store in a sealed container and keep away from light at room temperature (+1 to +30°C) Solid, white powder Hydrochloride (HCl salt) 414.9378.4496.7% The test substance was prepared at free-form concentration and adjusted according to purity. (Hydrochloride molecular weight: 402.84, free-form molecular weight: 366.38) Preparation of Test Article The preparation of the test substances was performed by Medicilon Preclinical Research (Shanghai) LLC in accordance with the preparation guidelines provided by the sponsor. The test substance formulations were prepared with purity correction, and all test substance formulations were prepared on the day of administration. Group 1: 3.42 mg of compound 9 (ATS0004) was weighed and dissolved in 0.370 mL of DMSO, vortexed for 1 minute, and then sonicated for 5 minutes. Subsequently, 0.741 mL of Solutol was added and vortexed for 1 minute. Finally, 6.298 mL of water for injection was added and vortexed for 1 minute to obtain a final formulation for intravenous administration at a concentration of 0.4 mg / mL. (pH: approx. 7) The formulation was a colorless, transparent solution. Group 2: 18.44 mg of compound 9 (ATS0004) was dissolved in 0.8 mL of DMSO, vortexed for 1 minute, and sonicated for 5 minutes to prepare a 20 mg / mL DMSO stock solution. Of this, 0.6 mL of the 20 mg / mL ATS0004 DMSO stock was taken, dissolved in 1.2 mL of Solutol, and vortexed for 1 minute. Finally, 10.2 mL of water for injection was added and vortexed for 1 minute to obtain a final oral formulation with a concentration of 1 mg / mL. (pH: approx. 7) The formulation was a colorless, transparent solution. Group 3: 3.28 mg of compound 23 (ATS0023) was dissolved in 0.363 mL of DMSO and vortexed for 1 minute, followed by sonication for 5 minutes. Then, 0.726 mL of Solutol was added and vortexed for 1 minute. Finally, 6.169 mL of water for injection was added and vortexed for 1 minute to obtain a formulation with a final concentration of 0.4 mg / mL for intravenous administration. (pH: approx. 7) The formulation was a colorless, transparent solution. Group 4: 18.03 mg of compound 23 (ATS0023) was dissolved in 0.8 mL of DMSO and vortexed for 1 minute to prepare a 20 mg / mL DMSO stock solution. Of this, 0.6 mL of the 20 mg / mL ATS0023 DMSO stock was taken, dissolved in 1.2 mL of Solutol, and vortexed for 1 minute. Finally, 10.2 mL of water for injection was added and vortexed for 1 minute to obtain a final oral formulation with a concentration of 1 mg / mL. (pH: approx. 7) The formulation was a colorless, transparent solution. Administration The test substance was administered to 24 male SD rats purchased from Zhejiang Vital River Laboratory Animal Technology Co., Ltd. in Zhejiang Province, China, according to Table 19. The oral administration group fasted from the night before administration and resumed feeding 4 hours after administration. Administration Condition Group Number Male Count Test Substance Dose (mg / kg) Formulation Concentration (mg / mL) Administered Volume (mL / kg) Route of Administration Sample 14ATS000420.45 Intravenous (IV) Plasma 24ATS000410110 Oral (PO)* Plasma 34ATS002320.45 Intravenous (IV) Plasma 44ATS002310110 Oral (PO)* Plasma * Before oral administration, the animals fasted overnight. Feeding of the animals administered orally was resumed 4 hours after administration. Sample Collection and Bioanalysis Blood samples (approximately 200 μL per sample) were collected from all groups via the jugular vein before administration (pre-dose) and at 5, 15, 30 minutes, 1 hour, 3 hours, 5 hours, 8 hours, 12 hours, and 24 hours after administration. The collected blood was placed in tubes containing heparin sodium, and plasma was separated by centrifugation at 6800 g / min for 6 minutes under conditions of 2-8 ℃. The plasma obtained after centrifugation was transferred to clean tubes and frozen at -80 ℃ until bioanalysis. Data Analysis Pharmacokinetic analysis and interpretation of results were performed by Medicilon Preclinical Research (Shanghai) LLC. Based on individual concentration-time data obtained from the test species, pharmacokinetic (PK) indices of the test substance were calculated by the Study Director. PK indices were calculated using Phoenix WinNonlin® 8.5 software. Concentration values ​​below the Lower Limit of Quantification (BLQ) were excluded from the PK indices calculation. Bioavailability was calculated using the following formula: Animal Final Disposition After the final blood sample collection, all test animals were euthanized by carbon dioxide inhalation. Animals additionally acquired for the study but not assigned to the experiment were euthanized and used for blank blood collection. Euthanasia was confirmed by cervical dislocation, and the carcasses were disposed of without further evaluation. <Experimental Results> 1. Effects of ATS series drugs on cell viability in RAW264.7 and HaCaT cell lines Figure 1 shows the results of measuring cell viability when treated at different concentrations of 10 μM to determine whether the ATS series drugs exhibit toxicity to cells. Cell viability was measured using a spectrophotometer after reaction using EZ-CYTOX, a technique for measuring cell viability. As a result, in mouse macrophage cell line RAW264.7 cells, cell viability of over 80% was observed for all compounds, and in human skin keratinocyte cell line HaCaT cells, compound 15 (ATS0010) showed a cell viability of 61%, while cell viability of over 80% was confirmed for all other compounds. Subsequent experiments were conducted with the ATS series drugs excluding compound 15 (ATS0010). 2. 5-HT of ATS series drugs 2A Inhibitory effect Figure 2 is 5-HT 2A 5-HT of 10μM ATS series drugs using human serotonin GPCR binding antagonist radioligand leadhunter assay 2A This is the result of evaluating the inhibitory effect. The analysis results showed that all ATS series 5-HT exceeding 50% 2A It showed an inhibitory effect and demonstrated a significant effect, with an average inhibitory effect of 80%. No. Compound Number ATS No. Molecular Weight 5HT-2A%Inh.1 Compound 5ATB1606416.8799.02 Compound 6ATS0001377.3168.53 Compound 7ATS0002386.8486.94 Compound 8ATS0003415.7887.65 Compound 9ATS0004414.9096.76 Compound 10ATS0005416.8799.67 Compound 11ATS0006428.9289.39 Compound 17ATS0014444.9291.210 Compound 18ATS0015390.9572.311 Compound 19ATS0018376.9369.912 Compound 20ATS0020448.5383.313 Compound 21ATS0021585.4650.514 Compound 22ATS0022609.4979.715 Compound 23ATS0023394.4497.916 Compound 24ATS0024441.3252.717 Compound 25ATS0042391.3487.618 Compound 26ATS0043405.4053.919 Compound 27ATS0044342.8779.220 Compound 28ATS0045356.8988.921 Compound 29ATS0046370.9282.422 Compound 30ATS0047373.7091.3 Table 15 above shows the molecular weight of each compound and 5-HT 2A This is a table showing the inhibition efficiency of. 4. Calcium influx inhibitory effect of ATS series drugs Figure 3 verified the inhibitory effects of seven compounds (compound 5 (ATB1606), compound 7 (ATS0002), compound 9 (ATS0004), compound 10 (ATS0005), compound 23 (ATS0023), and compounds 25 (ATS0042) and ATS0048) on histamine-induced calcium influx in mouse DRGs. As a result, the inhibitory effects on calcium influx induced by 100 μM histamine were 77%, 63%, 57%, and 26% for compound 10 (ATS0005), compound 5 (ATB1606), ATS0048, and compound 9 (ATS0004), respectively. Figure 4 shows the inhibitory effects of seven compounds (compound 5 (ATB1606), compound 9 (ATS0004), compound 10 (ATS0005), compound 20 (ATS0020), compound 23 (ATS0023), compound 29 (ATS0046), and ATS0048) on capsaicin-induced calcium influx in mouse DRG. As a result, the inhibitory effects of 1 μM histamine-induced calcium influx were 45%, 35%, and 10% for compound 23 (ATS0023), compound 9 (ATS0004), and compound 5 (ATB1606), respectively. 5. Antipruritic efficacy of ATS series drugs Figure 5 verified the inhibitory effects of compounds 10 and 23 (ATS0005, ATS0023) on calcium influx induced by 2 nmol MC903 in mice. The 10 mg / kg ATS0005 administration group and the 1 mg / kg compound 10 (ATS0005) administration group inhibited itching to a level similar to the control group, and compound 23 (ATS0023) showed superior itching inhibitory efficacy compared to the negative control group in all administration groups. Figure 6 verified the inhibitory effects of Compound 9 (ATS0004) and ATS0048 on calcium influx induced by 1.5 nmol MC903 in mice. The groups administered 10 mg / kg Compound 9 (ATS0004) and 10 mg / kg ATS0048 showed antipruritic efficacy at a level similar to the control group. 6. Results of pharmacokinetic experiments Clinical Observations No distinct abnormal findings were observed before or after administration. Plasma Concentration Plasma concentrations of compound 9 (ATS0004) and compound 23 (ATS0023) measured in individual animals are presented in Tables 16 to 19. Plasma concentration-time curves are presented in Figures 39 to 44, and average plasma concentration curves are presented in Figures 45 to 47. Plasma Pharmacokinetics Plasma pharmacokinetic indicators of individual animals are presented in Tables 22–24. Under the conditions of this study, when compound 9 (ATS0004) was intravenously administered to SD rats at a dose of 2 mg / kg, the mean Cmax was 237.11 ± 25.47 ng / mL, the mean AUC(0-t) was 777.84 ± 80.68 h·ng / mL, and the mean half-life (T 1 / 2 The mean Cmax was 10.79 ± 1.54 h, and when ATS0004 was orally administered to SD rats at 10 mg / kg, the mean Cmax was 192.06 ± 15.03 ng / mL, the mean AUC(0-t) was 2869.10 ± 260.78 h·ng / mL, and the mean half-life (T 1 / 2 ) was 12.18 ± 1.58 h. Therefore, the average bioavailability of compound 9 (ATS0004) in SD rats was 73.77 ± 6.71%. Under the conditions of this study, when compound 23 (ATS0023) was intravenously administered to SD rats at a dose of 2 mg / kg, the mean Cmax was 212.94 ± 26.31 ng / mL, the mean AUC(0-t) was 314.41 ± 61.89 h·ng / mL, and the mean half-life (T 1 / 2 The mean Cmax was 1.51 ± 0.20 h. Meanwhile, when ATS0023 was orally administered to SD rats at 10 mg / kg, the mean Cmax was 79.07 ± 16.03 ng / mL, the mean AUC(0-t) was 530.09 ± 111.82 h·ng / mL, and the mean half-life (T 1 / 2 ) was 2.70 ± 0.62 h. Accordingly, the average bioavailability of compound 23 (ATS0023) in SD rats was calculated to be 33.72 ± 7.11%. Plasma Concentration (ATS0004) After Intravenous Administration of Compound 9 (ATS0004) in SD Rats (ATS0004-IV-2 mg / kg-Rat) Time (hr) ATS0004-Plasma Concentration (ng / mL) Standard Deviation (SD) 10 1 10 2 10 3 10 4 Mean (Mean) 0 BLQ BLQ BLQ BLQ NANA 0.08 3 2 2 8.8 0 2 5 8.6 9 2 0 4.7 5 2 5 6.2 0 2 3 7.1 2 5 4 7 0.2 5 1 49.06 1 6 6.8 1 6 3.1 9 2 4 2.1 9 1 8 0.3 3 4 1.9 5 0.5 1 2 0.8 5 1 49.68 1 3 5.69 1 4 2.4 6 1 3 7.1 7 1 2.2 9 1 9 5.2 2 9 9.08 9 4.2 3 9 0. 2994.703.61345.0247.1656.2558.1651.656.52532.1733.1244.4041.3637.766.05828.4321.6834.5926.7227.855.321222.7316.9427.6719.8721.804.57249.098.5014.088.179.962.77 ※ NA: Not applicable, BLQ: Below limit of quantitation or peak not detected (LLOQ = 0.5 ng / mL) Plasma Concentration (ATS0004-PO-10 mg / kg-Rat) After Oral Administration of Compound 9 (ATS0004) in SD Rats Time (hr) ATS0004-Plasma Concentration (ng / mL) Standard Deviation (SD) 201 202 203 204 Mean 0 8 3 BLQ 1.7 3 0.9 6 1.5 7 1.4 2 0.4 0 0.2 5 18.7 21 1.6 4 3 0.3 6 21.8 7 20.6 5 7.7 6 0.5 9 6.5 7 37.4 17 1.6 4 7 8.4 17 1.0 12 4.7 5 11 5 7.0 2 7 4.9 7 9 3.1 11 12 4 4 10 9.3 8 35.2 5 31 69.7 11 5 6.9 3143.86136.59151.7714.625201.53193.72202.66170.32192.0615.038153.90170.13171.63144.46160.0313.1212122.94130.96142.8893.13122.4821.212453.4470.0866.9461.3262.957.30 ※ NA: Not applicable, BLQ: Below limit of quantitation or peak not detected (LLOQ = 0.5 ng / mL) Plasma Concentration (ng / mL) after Intravenous Administration of Compound 23 (ATS0023) in SD Rats Time (hr) ATS0023-Plasma Concentration (ng / mL) Standard Deviation (SD) 301 302 303 304 Mean 0BLQBLQBLQBLQNANA 0.08 3188.8 924 2.5 5227.5 5192.7 5212.9 426.3 10.2 5138.8 2182.0 1211.6 6164.3 117 4.2 030.6 30.5 103.2 2114.2 0141.5 6188.2 2136.8 037.8 8196.1 876 .0969.51100.0985.4714.96323.9418.8720.3840.8826.0210.1355.806.417.9118.619 .686.0182.001.811.943.912.421.0012BLQBLQ0.501.000.750.3524BLQBLQBLQBLQNANA ※ NA: Not applicable, BLQ: Below limit of quantitation or peak not detected (LLOQ = 0.5 ng / mL) Plasma Concentration (ATS0023-PO-10 mg / kg-Rat) After Oral Administration of Compound 23 (ATS0023) in SD Rats Time (hr) ATS0023-Plasma Concentration (ng / mL) Standard Deviation (SD) 401 402 403 404 Mean 0 BLQ BLQ BLQ BLQ NANA 0.08 30.48 3.19 1.09 4.44 2.30 1.84 0.25 15.43 18.53 11.43 10.22 13.90 3.8 10.53 3.84 59.13 28.69 39.58 40.31 13.31 159.25 92.96 44.00 54.076 2.572 1.22392.8467.6263.4867.0172.7413.52588.3364.8455.5462.5567.8114.24835.151 9.3422.8821.2224.657.15127.435.617.283.826.031.69241.56BLQBLQ0.691.130.62 ※ NA: Not applicable, BLQ: Below limit of quantitation or peak not detected (LLOQ = 0.5 ng / mL) Plasma pharmacokinetic parameters after intravenous administration of Compound 9 (ATS0004) in SD rats Animal No. Route of Administration Dose (mg / kg)T 1 / 2 (h)Tmax (h)Cmax (ng / mL)AUC(0-t) (h·ng / mL)AUC(0-∞) (h·ng / mL)MRT(0-t) (h)MRT(0-∞) (h)C0(ng / mL)Vss (L / kg)Vz (L / kg)Cl (mL / h / kg)101IV29.570.083228.80742.19867.776.8911.36283.1126.1931.8 338.41102IV211.890.083258.69699.95845.836.1712.20321.6628.8540.5839 .41103IV212.330.083204.75888.211138.707.5415.08229.1926.4831.2529.27104IV29.360.083256.20781.01891.416.2110.09263.4622.6430.3037.39Average (Mean) 10.79 0.08 237.117 77.84 935.9 36.70 12.18 274.35 26.04 33.49 36.12 Standard Deviation (SD) 1.54 0.00 25.47 80.68 136.46 0.65 2.12 38.62 2.56 4.77 4.64 Plasma pharmacokinetic parameters after oral administration of Compound 9 (ATS0004) in SD rats Animal Number Route of Administration Dose (mg / kg)T 1 / 2(h)Tmax (h)Cmax (ng / mL)AUC(0-t) (h·ng / mL)AUC(0-∞) (h·ng / mL)MRT(0-t) (h)MRT(0-∞) (h)Bioavailability F (%) 20 1 PO 10 10.3 75.00 20 1.5 3 29 22.4 3 72 1.6 29.4 3 15.7 75.1 4 20 2 PO 10 12.6 85.00 19 3.7 229 72.1 7 4 25 4.3 0 10.3 9 20.01 76.4 22 3 PO 10 11.5 85.00 20 2.6 6 30 89.4 9 4 20 8.1 7 10.2 6 18.3 5 79.4 20 4 PO 10 14.0 85.00 17 0.3 22 4 92.3 0 3 73 7.9 8 10.00 21.4 3 6 4.08 Average (Mean)12.18 5.00 19 2.06 28 69.10 39 80.5 21 0.02 18.8 9 73.77 Standard Deviation (SD)1.58 0.00 15.03 26 0.78 29 0.19 0.43 2.43 6.71 Plasma pharmacokinetic parameters after intravenous administration of Compound 23 (ATS0023) in SD rats Animal No. Route of Administration Dose (mg / kg)T 1 / 2 (h)Tmax (h)Cmax (ng / mL)AUC(0-t) (h·ng / mL)AUC(0-∞) (h·ng / mL)MRT(0-t) (h)MRT(0-∞) (h)C0(ng / mL)Vss (L / kg)Vz (L / kg)Cl (mL / h / kg)301IV21.230.083188.89286.00289.541.361.46220.1310.1012.2 1115.12302IV21.490.083242.55274.31278.211.251.38279.769.9015.4711 9.82303IV21.680.083227.55290.68291.901.431.48235.8910.1416.61114.19304IV21.630.083192.75406.66409.021.922.00208.679.7611.4981.50 Mean 1.510.08212.94314.41317.171.491.58236.119.9813.95107.66 Standard Deviation (SD) 0.200.0026.3161.8961.530.300.2831.160.182.4817.61 Plasma pharmacokinetic parameters after oral administration of Compound 23 (ATS0023) in SD rats Animal No. Route of Administration Dose (mg / kg)T 1 / 2 (h)Tmax (h)Cmax (ng / mL)AUC(0-t) (h·ng / mL)AUC(0-∞) (h·ng / mL)MRT(0-t) (h)MRT(0-∞) (h)Bioavailability F (%) 40 1PO 10 3.3 8 3.00 9 2.8 46 8 8.3 06 9 5.9 1 5.3 2 5.5 8 4 3.7 8 40 2PO 10 1.9 9 1.00 9 2.9 6 51 8.8 553 5.00 3.8 9 4.2 3 3.00 40 3PO 10 2.3 9 3.00 6 3.4 8 42 8.7 2 453.8 44.5 55.1 5 27.2 7 40 4PO 10 3.0 4 3.00 6 7.0 1 48 4.4 8 48 7.5 0 4.7 9 4.9 3 30.8 2.8 2.7 0 2.5 0 7 9.0 7 53 0.0 9 54 3.0 6 4.6 44.9 7 33.7 2.7 2.7 2.8 (SD)0.621.0016.03111.82107.200.590.577.11 Foregoing, specific parts of the present invention have been described in detail. It is evident 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 appended claims and their equivalents.

Claims

1. A compound represented by the following chemical formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] In the above chemical formula 1, The above A and B are directly connected, or X is a C1-C5 alkylene or a C1-C5 alkoxy, and The above A is C6-C 10 aryl; or C6-C1224 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, The above B is C6-C 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, and The above n is an integer between 0 and 8, and The above Y is an unsubstituted or oxo-substituted C1-C5 alkylene, and The above Z is a C1-C3 alkylamine C1-C 10 Alkyl, heterocyclic of a pentagonal to ninth-membered ring that is unsubstituted or substituted with C1-C3 alkyls, C6-C 10 It is any one selected from the group consisting of cyclic amines C1-C5 alkyls.

2. In Paragraph 1, The above A is C6-C 10 aryl; or C6-C substituted with one or more selected from the group consisting of halogens, trifluoromethyl (-CF3), trifluoromethoxy (-OCF3), difluoromethoxy (-OCF2H) and difluoromethyl (-CF2H). 10 A compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof, which is an aryl or a heteroaryl having a 5 to 9-membered ring.

3. In Paragraph 1, The above B is a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, which is any one selected from the group consisting of a phenyl group, a pyridine group, and a pyrimidine group.

4. In Paragraph 1, A compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein n is an integer between 0 and 4.

5. In Paragraph 1, The above X is a C1-C3 alkylene or C1-C3 alkoxyne, a compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.

6. In Paragraph 1, The above Y is a compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof, which is an unsubstituted or oxo-substituted C1-C3 alkylene.

7. In Paragraph 1, The above Z is , , , , , , , A compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof, any one selected from the group consisting of piperidine, pyridine, piperazine, and C5-C9 cyclohexylamine.

8. A pharmaceutical composition for anti-inflammatory purposes comprising, as an active ingredient, a compound of any one of claims 1 to 7, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.

9. In Paragraph 8, The above pharmaceutically acceptable salt is the above pharmaceutically acceptable salt An anti-inflammatory pharmaceutical composition, wherein the acid addition salt selected from the group consisting of hydrochloride, bromate, sulfate, nitrate, perchlorate, fumarate, maleate, phosphate, glycolate, lactate, salicylate, succinate, toluene-p-sulfonate, tartrate, acetate, trifluoroacetate, citrate, methanesulfonate, formate, benzoate, malonate, naphthalene-2-sulfonate, and benzenesulfonate; or the base addition salt selected from the group consisting of sodium salt, magnesium salt, and ammonium salt.

10. In Paragraph 8, The above composition is an anti-inflammatory pharmaceutical composition in the form of an oral or parenteral administration formulation.

11. A pharmaceutical composition for controlling or treating chronic pain and itching, comprising as an active ingredient a stereoisomer of any one of claims 1 to 7, or a pharmaceutically acceptable salt thereof.

12. In Paragraph 11, The above pharmaceutically acceptable salt is the above pharmaceutically acceptable salt A pharmaceutical composition for controlling or treating chronic pain and itching, comprising an acid addition salt selected from the group consisting of hydrochloride, bromate, sulfate, nitrate, perchlorate, fumarate, maleate, phosphate, glycolate, lactate, salicylate, succinate, toluene-p-sulfonate, tartrate, acetate, trifluoroacetate, citrate, methanesulfonate, formate, benzoate, malonate, naphthalene-2-sulfonate, and benzenesulfonate; or a base addition salt selected from the group consisting of sodium salt, magnesium salt, and ammonium salt.

13. In Paragraph 11, The above composition is a pharmaceutical composition for controlling or treating chronic pain and itching, in a formulation for oral or parenteral administration.

14. A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound represented by the following chemical formula 1, a stereoisomer thereof, or a food-grade acceptable salt thereof. [Chemical Formula 1] In the above chemical formula 1, The above A and B are directly connected, or X is a C1-C5 alkylene or a C1-C5 alkoxy, and The above A is C6-C 10 aryl; or C6-C1224 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, The above B is C6-C 10 It is an aryl or a heteroaryl of a 5 to 9-membered ring, and The above n is an integer between 0 and 8, and The above Y is an unsubstituted or oxo-substituted C1-C5 alkylene, and The above Z is a C1-C3 alkylamine C1-C 10 Alkyl, heterocyclic of a pentagonal to ninth-membered ring that is unsubstituted or substituted with C1-C3 alkyls, C6-C 10 It is any one selected from the group consisting of cyclic amines C1-C5 alkyls.

15. In Paragraph 14, The above A is C6-C 10 aryl; or C6-C substituted with one or more selected from the group consisting of halogens, trifluoromethyl (-CF3), trifluoromethoxy (-OCF3), difluoromethoxy (-OCF2H) and difluoromethyl (-CF2H). 10 A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound that is an aryl or a heteroaryl having a 5 to 9-membered ring, a stereoisomer thereof, or a food-grade acceptable salt thereof.

16. In Paragraph 14, A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, stereoisomer thereof, or a food-grade acceptable salt thereof, wherein B is any one selected from the group consisting of a phenyl group, a pyridine group, and a pyrimidine group.

17. In Paragraph 14, A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, a stereoisomer thereof, or a food-grade acceptable salt thereof, wherein n is an integer between 0 and 4.

18. In Paragraph 14, A health functional food composition for relieving or improving chronic pain and itching, wherein X comprises a C1-C3 alkylene or C1-C3 alkoxyne, a compound, a stereoisomer thereof, or a food-grade acceptable salt thereof as an active ingredient.

19. In Paragraph 14, A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound, stereoisomer thereof, or a food-grade acceptable salt thereof, wherein the above Y is an unsubstituted or oxo-substituted C1-C3 alkylene.

20. In Paragraph 14, The above Z is , , , , , , , A health functional food composition for relieving or improving chronic pain and itching, comprising as an active ingredient a compound selected from the group consisting of piperidine, pyridine, piperazine, and C5-C9 cyclohexylamine, a stereoisomer thereof, or a food-grade acceptable salt thereof.

21. In Paragraph 14, The above health functional food composition is a health functional food composition for improving chronic pain or itching, wherein the composition is any one formulation selected from the group consisting of powder, granules, tablets, capsules, pills, suspensions, emulsions, syrups, aerosols, gum, candy, bars, and beverages.

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