Anti-wrinkle and Anti-inflammatory composition comprising isoquinoline derivative as active ingredient

Abstract

The present invention relates to a novel isoquinoline derivative and a use thereof. The novel isoquinoline derivative of the present invention exhibits effects of improving the function of wrinkle reduction factors and inhibiting the function of factors related to inflammation, and thus is expected to be utilized in the development of an anti-wrinkle or anti-inflammatory cosmetic composition, a medical device, a quasi-drug composition, and a health functional food composition.

Description

Anti-wrinkle and anti-inflammatory composition containing an isoquinoline derivative as an active ingredient

[0001] The present invention relates to an anti-wrinkle and anti-inflammatory composition comprising a novel isoquinoline derivative as an active ingredient.

[0002] The present invention claims priority based on Korean Patent Application No. 10-2024-0202964 filed on December 31, 2024 and Korean Patent Application No. 10-2025-0215310 filed on December 30, 2025, and all contents disclosed in the specifications and drawings of said applications are incorporated by reference into the present application.

[0003] The skin is an important organ located on the outermost part of the body that has various functions and significantly influences appearance and image. It accounts for approximately 3 to 5 kg of total weight depending on the individual and is composed of various cells and a unique structure that covers the outer surface of the body. It can be said to be an organ that serves as the body's primary defense barrier, preventing moisture evaporation, regulating body temperature, protecting the body from external stimuli such as ultraviolet rays, and preventing the intrusion of harmful microorganisms.

[0004] Furthermore, the skin protects the human body from physical and chemical injuries, infections by microorganisms such as bacteria and fungi, parasitic infections, damage caused by ultraviolet rays, and dryness. At the same time, it acts as a nerve receptor for various external stimuli and plays a role in recognizing external antigens to provide immune cells. This skin can be damaged by various external factors, including sunlight. Sunlight consists of visible light, ultraviolet rays, and infrared rays. Among these, ultraviolet rays perform beneficial roles, such as synthesizing Vitamin D in the body and sterilizing, but they can also cause skin aging, skin cancer, dryness, dermatitis, fine lines, melasma, and freckles. Ultraviolet rays are divided into three types—A, B, and C—based on wavelength; among these, UVC is blocked by the ozone layer, while UVA and UVB affect the skin. In particular, UVB (290–320 nm), a medium-wavelength ultraviolet ray, causes many side effects, including the development of skin cancer, suppression of the immune system, and photoaging.

[0005] Interest in skin health is rising among modern people who are increasingly exposed to environmental stressors such as global warming, exhaust fumes, and UV rays. Collagen is the most abundant protein in the dermis of the skin, with over 90% existing in the form of collagen type I, which is generated from procollagen. Long-term exposure to ultraviolet rays causes skin damage through photoaging, resulting in rough and dry skin, wrinkle formation, and weakened immunity. This damage extends not only to the epidermis but also to the dermis and is known to increase the activity of matrix metalloproteinases (MMPs), which act to break down other components bound to collagen that govern dermal elasticity.

[0006] Meanwhile, TNF-α is a representative cytokine primarily secreted by inflammatory or immune cells in response to external stimuli or infectious agents. Along with interleukin-1 (IL-1), it is a proinflammatory cytokine that plays a central role in mediating infections, inflammation, autoimmune and allergic diseases. Chronic inflammatory skin diseases mediated by TNF-α include psoriasis, eczema, and seborrheic dermatitis, while acute inflammatory diseases include contact dermatitis (Mache E Descapms V, Ann. Dermatol. Venereol. 129(12):1374-9, 2002). Additionally, atopic dermatitis can be cited as a TNF-α-mediated allergic disease.

[0007] To inhibit TNF-α activity, major targets for TNF-α inhibition are being studied, including blocking the production, processing, and secretion processes of TNF-α, tumor necrosis factor-alpha converting enzyme (TACE) which catalyzes the degradation of TNF-α into soluble TNF-α, phosphodiesterase 4 or adenosine receptors which alter intracellular cAMP levels causing changes in TNF-α gene expression, various kinases (NIK, IKK, PKB) related to the activity of NF-kB, a major signaling pathway that induces TNF-α expression, and MAPKs (mitogen-activated protein kinases) such as p38 and JNK (c-jun N-terminal kinase).

[0008] Meanwhile, the anti-wrinkle and anti-inflammatory effects of isoquinoline derivatives are not known. Based on this, there is a need for the development of cosmetic compositions, medical devices, quasi-drugs, and food products.

[0009] Accordingly, the inventors of the present invention made efforts to find a substance capable of exhibiting anti-wrinkle or anti-inflammatory effects, and confirmed that the isoquinoline derivative of the present invention possesses significant anti-wrinkle or anti-inflammatory effects, thereby completing the present invention.

[0010] Accordingly, one object of the present invention is to provide a cosmetic composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by the following Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof:

[0011] [Chemical Formula 1]

[0012]

[0013]

[0014] [Chemical Formula 2]

[0015]

[0016] In the above chemical formula 1,

[0017] X is F, Cl, Br, I, or OH.

[0018] Another object of the present invention is to provide a medical device selected from functional wound dressings, fillers, or composite fillers having anti-wrinkle or anti-inflammatory functions, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0019] Another objective of the present invention is to provide a quasi-drug composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0020] Another objective of the present invention is to provide a health functional food composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof.

[0021]

[0022] 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.

[0023] The present invention provides a cosmetic composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by the following Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof:

[0024] [Chemical Formula 1]

[0025]

[0026] [Chemical Formula 2]

[0027]

[0028] In the above chemical formula 1,

[0029] X is F, Cl, Br, I, or OH.

[0030] The present invention provides a medical device selected from functional wound dressings, fillers, or composite fillers having anti-wrinkle or anti-inflammatory functions, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0031] The present invention provides a quasi-drug composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0032] The present invention provides a health functional food composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof.

[0033] The present invention provides a cosmetic composition for improving inflammation, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof.

[0034]

[0035] In one embodiment of the present invention, the compound represented by Formula 1 may be one or more selected from the group consisting of compounds listed in Table 1 below, but is not limited thereto.

[0036] [Table 1]

[0037]

[0038] In another embodiment of the present invention, the compound represented by Formula 1 may be one or more selected from the group consisting of the following compounds, but is not limited thereto.

[0039] (1) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide;

[0040] (2) 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium hydroxide; and

[0041] (3) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride.

[0042] Specifically, in another embodiment of the present invention, the compound represented by Formula 1 may be 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide, but is not limited thereto.

[0043] In another embodiment of the present invention, the wrinkles may be skin wrinkles caused by one or more selected from the group consisting of ultraviolet rays and skin inflammation, but are not limited thereto.

[0044] In another embodiment of the present invention, the wrinkles may be wrinkles resulting from the expression or reduced activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins, but are not limited thereto.

[0045] In another embodiment of the present invention, the inflammation may be inflammation caused by increased expression or activity of one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α), or genes encoding such proteins, but is not limited thereto.

[0046] In another embodiment of the present invention, the composition may be processed in one or more ways selected from the group consisting of Microneedle Therapy System (MTS) methods and Auto Microneedle Therapy System (AMTS) methods, but is not limited thereto.

[0047] In another embodiment of the present invention, the quasi-drug composition may be formulated into one or more selected from the group consisting of external preparations, powders, antiseptics, toothpastes, ointments, lotions, oral preparations, wet wipes, sprays, patches, bandages, patches, and combinations thereof, but is not limited thereto.

[0048] According to another embodiment of the present invention, the isoquinoline derivative according to the present invention may reduce the expression of inflammatory factors, but is not limited thereto.

[0049] According to another embodiment of the present invention, the reduction in the expression of the inflammatory factor may be achieved by reducing the expression of one or more selected from the group consisting of TNF-α, IL-1β, and IL-6 to improve immune function, but is not limited thereto.

[0050]

[0051] In addition, the present invention provides a method for anti-wrinkle or anti-inflammatory effects, comprising the step of administering a composition containing a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof as an active ingredient to an individual in need thereof in a cosmetically effective amount.

[0052] In addition, the present invention provides a non-therapeutic method for anti-wrinkle or anti-inflammation, comprising the step of administering a composition containing a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof as an active ingredient to an individual in need thereof in a cosmetically effective amount.

[0053] In addition, the present invention provides an anti-wrinkle or anti-inflammatory use of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof.

[0054] In addition, the present invention provides a use for preparing anti-wrinkle or anti-inflammatory agents of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof.

[0055] In addition, the present invention provides a cosmetic method for anti-wrinkle or anti-inflammatory effects comprising the step of administering to an individual a composition comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof.

[0056] In addition, the present invention provides an anti-wrinkle or anti-inflammatory method comprising the step of administering a composition containing a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient to an individual in need thereof in a pharmaceutically effective amount.

[0057] In addition, the present invention provides an anti-wrinkle or anti-inflammatory use of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0058] In addition, the present invention provides a use for preparing anti-wrinkle or anti-inflammatory agents of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0059]

[0060] In addition, the present invention provides an anti-wrinkle or anti-inflammatory method comprising the step of administering a composition containing a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof as an active ingredient to an individual in need thereof in a food-grade effective amount.

[0061] In addition, the present invention provides a non-therapeutic method for anti-wrinkle or anti-inflammation, comprising the step of administering a composition containing a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof as an active ingredient to an individual in need thereof in a food-grade effective amount.

[0062] In addition, the present invention provides an anti-wrinkle or anti-inflammatory use of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof.

[0063] In addition, the present invention provides a use for preparing anti-wrinkle or anti-inflammatory agents of a composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof.

[0064]

[0065] The novel isoquinoline derivative of the present invention exhibits the effect of enhancing the function of wrinkle improvement factors and inhibiting the function of factors related to the occurrence of inflammation, and is expected to be utilized in the development of anti-wrinkle or anti-inflammatory cosmetic compositions, medical devices, quasi-drug compositions, and health functional food compositions.

[0066]

[0067] Figure 1 confirms the wrinkle-improving effect of ALT 001, a novel isoquinoline derivative of the present invention. Specifically, “NC” refers to a normal control group that was not irradiated with UV, “C” refers to a control group that was irradiated with only UV, L-AA is a positive control group that was treated with 100 μg / mL of L-ascorbic acid while irradiating with UV, and the test samples represent groups treated with the isoquinoline derivative ALT 001 at concentrations of 15, 30, and 50 μM, respectively.

[0068] Figures 2a and 2b show the changes in the expression of proteins involved in skin wrinkles 24 hours after treatment with ALT 001. Figure 2a shows the Western blot band results, and Figure 2b shows the quantitative expression levels of p-Smad3 / Smad3, type I collagen, and elastin. Specifically, “NC” represents the normal control group that was not irradiated with UV, “C” represents the control group that was irradiated with UV only, and PC represents the positive control group that was treated with 100 μg / mL of L-ascorbic acid while irradiating with UV. The test samples represent the groups treated with the isoquinoline derivative ALT 001 at concentrations of 4, 12, and 24 μM, respectively, and treated with UV light. The results are expressed as mean ± standard deviation (n = 3), and different superscripts indicate significance at P < 0.05.

[0069] Figures 3a and 3b show the changes in the expression of proteins involved in skin wrinkles 48 hours after treatment with ALT 001. Figure 3a shows the Western blot band results, and Figure 3b shows the quantitative expression levels of p-Smad3 / Smad3, type I collagen, and elastin. Specifically, “NC” represents the normal control group that was not irradiated with UV, “C” represents the control group that was irradiated with UV only, and PC represents the positive control group that was treated with 100 μg / mL of L-ascorbic acid while irradiating with UV. The test samples represent the groups treated with the isoquinoline derivative ALT 001 at concentrations of 4, 12, and 24 μM, respectively, and UV-treated. The results are expressed as mean ± standard deviation (n = 3), and different superscripts indicate significance at P < 0.05.

[0070] Figure 4a shows representative images of hematoxylin and eosin (H&E) staining confirming adverse reactions in ex vivo human-derived skin tissue (F / 49 / Korean, scale bar=50μm).

[0071] Figure 4b shows the results of the analysis of collagen expression levels in ex vivo human-derived skin tissue, 1 This indicates that improvement occurs as the average value increases, and 2 The rate of change represents the rate of change (%) compared to the negative control group (N=5 points).

[0072] Figure 4c shows the results of MT staining confirming collagen density in a cross-section of ex vivo human-derived skin tissue (Mean±SEM).

[0073] Figure 4d shows a representative image of MT staining confirming collagen density of ex vivo human-derived skin tissue (F / 49 / Korean, scale bar=50μm).

[0074] Figure 4e shows the results of the analysis of elastin expression levels in ex vivo human-derived skin tissue, 1 This indicates that improvement occurs as the average value increases, and 2 The rate of change represents the rate of change (%) compared to the negative control group (N=3 points).

[0075] Figure 4f shows the results of Victoria Blue staining confirming elastin density in cross-sections of ex vivo human-derived skin tissue (Mean±SEM).

[0076] Figure 4g shows a representative image of Victoria blue staining confirming the elastin density of ex vivo human-derived skin tissue (F / 49 / Korean, scale bar=50μm).

[0077] Figure 5 confirms the anti-inflammatory effect of ALT 001 of the present invention.

[0078] Embodiments of the present invention will be described in detail below with reference to the attached drawings. In the following description, detailed descriptions of technologies well known to those skilled in the art may be omitted. Furthermore, in describing the present invention, detailed descriptions of related known functions or configurations may be omitted if it is determined that such descriptions would unnecessarily obscure the essence of the present invention. Additionally, the terminology used in this specification is used to appropriately express preferred embodiments of the present invention, and may vary depending on the intent of the user or operator, or the conventions of the field to which the present invention belongs.

[0079] Therefore, the definitions of these terms should be based on the content throughout this specification. Throughout the specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0080]

[0081] The present invention provides a cosmetic composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by the following Formula 1 or Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof:

[0082] [Chemical Formula 1]

[0083]

[0084] [Chemical Formula 2]

[0085]

[0086] In the above chemical formula 1,

[0087] X is F, Cl, Br, I, or OH.

[0088] The present invention provides an anti-wrinkle or anti-inflammatory composition comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a salt thereof.

[0089] Including all claims below, the composition may be one or more selected from the group consisting of, for example, cosmetic compositions, quasi-drug compositions, and health functional food compositions, but is not limited thereto.

[0090] Including all claims below, the salt may be one or more selected from the group consisting of, for example, cosmetically acceptable salts, pharmaceutically acceptable salts, and food-acceptable salts, but is not limited thereto.

[0091] In the entire specification including the following claims, the compound represented by the following Formula 1 or Formula 2 may be an isoquinoline derivative, but is not limited thereto.

[0092] In one embodiment of the present invention, it was confirmed that the isoquinoline derivative according to the present invention improves the function of a gene related to skin wrinkle improvement (see Example 2 and Fig. 1).

[0093] In another embodiment of the present invention, it was confirmed that the isoquinoline derivative according to the present invention enhances the function of a protein regarding the improvement of skin wrinkles (see Example 3, FIG. 2a, FIG. 2b, FIG. 3a, and FIG. 3b).

[0094] In another embodiment of the present invention, it was confirmed that the isoquinoline derivative according to the present invention not only ensures safety but also exhibits effects of improving skin elasticity and anti-wrinkle (see Example 4 and FIGS. 4a to 4g).

[0095] In another embodiment of the present invention, it was confirmed that the isoquinoline derivative according to the present invention promotes immune activity and inhibits the function of factors related to the occurrence of inflammation (see Example 5 and Fig. 5).

[0096] Including the entire claims below, the scope of the compounds of the present invention may include cosmetically acceptable salts, pharmaceutically acceptable salts, and food-acceptable salts, as well as all isomers, hydrates, and solvates that can be prepared by conventional methods.

[0097] In this specification, including all claims below, "isomer" refers to a compound having the same molecular formula but different arrangements of constituent atoms within the molecule. Isomers include, for example, structural isomers and stereoisomers. The stereoisomers may be diastereomers or enantiomers. Enantiomers are isomers that do not overlap with their mirror images, like the relationship between a left hand and a right hand, and are also called optical isomers. Enantiomers are distinguished as R (Rectus: clockwise) and S (Sinister: counterclockwise) when four or more substituents on the chiral central carbon differ. Diastereomers are stereoisomers that are not mirror images of each other and can be divided into cis and trans isomers, which are formed by differences in the spatial arrangement of atoms.

[0098] Including all claims below, the form of the isoquinoline derivative, its cosmetically acceptable salt, pharmaceutically acceptable salt, or food-grade acceptable salt may be a derivative in which a hydrophobic substituent (methoxy group) of the core structure of palmatin or berberine is substituted with a hydrophilic substituent or a functional group (hydroxyl group) capable of providing intermolecular hydrogen bonding. For example, the isoquinoline derivatives according to the present invention are 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide, 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium hydroxide, and are respectively represented by the following chemical formulas 1a to 1c. It may be one or more selected from the group consisting of 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride. In the present invention, the 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide may be referred to as "ALT 001".

[0099] [Chemical Formula 1a]

[0100]

[0101] [Chemical Formula 1b]

[0102]

[0103] [Chemical Formula 1c]

[0104]

[0105]

[0106] Including all claims below, “ALT 001” can improve mitochondrial abnormalities by specifically and excellently promoting the activity of mitophagy without inducing mitochondrial damage like conventional mitochondrial toxins such as CCCP, and may be useful for treating diseases caused by mitochondrial dysfunction, but is not limited thereto.

[0107] In the present specification, including all claims below, the isoquinoline derivative may be produced through a method comprising the step (step 1) of adding a Lewis acid catalyst to palmatine represented by Formula 3 or berberine represented by Formula 4 and reacting them with an organic solvent as shown in Reaction Scheme 1 below to produce an isoquinoline derivative compound represented by Formula 2.

[0108] [Reaction Equation 1]

[0109]

[0110] Including all claims below, the method for preparing an isoquinoline derivative compound of the present invention is,

[0111] The method may include a step of reacting palmatin represented by Chemical Formula 3 with a Lewis acid catalyst in an organic solvent; or a step of reacting berberine represented by Chemical Formula 4 with a Lewis acid catalyst in an organic solvent, which may be represented as in Reaction Formula 1, but is not limited thereto.

[0112] Including all claims below, the Lewis acid catalyst herein is one or more metal halides selected from the group consisting of BF3, BBr3, AlF3, AlCl3, AlBr3, TiCl4, TiBr4, TiI4, FeCl3, FeCl2, SnCl2, SnCl4, WCl6, MoCl5, SbCl5, TeCl2, and ZnCl2; one or more metal alkyl compounds selected from the group consisting of Et3Al, Et2AlCl, EtAlCl2, Et3Al2Cl3, (i-Bu)3Al, (i-Bu)2AlCl, (i-Bu)AlCl2, Me4Sn, Et4Sn, Bu4Sn, and Bu3SnCl; or Al (OR) 3-x Cl x and Ti (OR) 4-y Cl y (wherein R represents an alkyl group or an aryl group, x is 1 or 2, and y is an integer from 1 to 3) may be one or more metal alkoxy compounds selected from the group consisting of, specifically, the Lewis acid catalyst may be a metal halide, and more specifically, the luyric acid catalyst may be BBr3, but is not limited thereto.

[0113] Including all claims below, the organic solvent may be one or more selected from the group consisting of dimethyl sulfoxide, dimethyl formamide, acetone, tetrahydrofuran, benzene, toluene, ether, methanol, hexane, cyclohexane, pyridine, acetic acid, carbon tetrachloride, chloroform, dichloromethane, and water, and specifically, the organic solvent may be dichloromethane, but is not limited thereto.

[0114] Including all claims below, the Lewis acid catalyst may be added in an inert gas. Specifically, the Lewis acid catalyst may be added dropwise to palmatin or berberine dissolved in the organic solvent at about 0°C in an inert gas atmosphere, for example, under a nitrogen stream.

[0115] Including all claims below, the reaction may be carried out by stirring at room temperature, for example, 20°C to 28°C, for example, 24°C to 26°C, for 10 to 14 hours, for example, 11 to 13 hours, for example, 12 hours after adding the Lewis acid catalyst, and the termination of the reaction may be confirmed using, for example, thin-layer chromatography (TLC), but is not limited thereto.

[0116] Including all claims below, the composition of the present invention may be intended to improve skin condition, but is not limited thereto.

[0117] In the entire specification including the following claims, “skin condition” may be, but is not limited to, skin aging caused by ultraviolet rays, melasma, freckles, skin wounds, dermatitis, atopic dermatitis, pruritus, eczematous skin disease, dry eczema, erythema, urticaria, psoriasis, drug rash, or acne condition.

[0118] In the entire specification including the following claims, “skin aging caused by ultraviolet rays” may mean that premature skin aging occurs when there is excessive exposure to ultraviolet rays for a long time, affecting skin elasticity, barrier function, and wound healing, and causing structural and functional changes in both the epidermis and dermis, and the main mechanisms include reduced fibroblast activity, reduced production of collagen and elastin, and degradation of the extracellular matrix (ECM) through enzymes such as matrix metalloproteinases (MMPs), which may mean that the skin becomes thinner, wrinkles form, and elasticity decreases, but is not limited thereto.

[0119] In the entirety of the following claims, the term “improvement of skin condition” may mean one or more selected from the group consisting of: prevention or improvement of skin wrinkles; prevention or improvement of skin aging; prevention or improvement of skin inflammation; shrinkage or reduction of pores; improvement of skin barrier function; alleviation of skin irritation; and improvement of skin cell proliferation, regenerative ability, antioxidant ability, or collagen synthesis enhancement ability, but is not limited thereto.

[0120] In all claims below, the term “anti-inflammatory” or “anti-inflammatory” may mean soothing, resisting, or inhibiting inflammation, and the anti-inflammatory function in skin tissue may mean protecting and stabilizing the skin and performing disinfection and sterilization actions, but is not limited thereto.

[0121] In this specification, including the entire claims below, “inflammation” refers to a complex lesion involving the concomitant occurrence of three conditions: tissue degeneration, circulatory disturbance and exudation, and tissue proliferation, as one of the defensive responses of biological tissues to a stimulus, but is not limited thereto. More specifically, inflammation is part of innate immunity, and as in other animals, human innate immunity can recognize patterns on the cell surface that are specifically present on pathogens. Phagocytes recognize cells with such surfaces as non-self and attack the pathogens. If pathogens break through the body's physical barriers and enter, an inflammatory response occurs. The inflammatory response is a non-specific defense mechanism that creates a hostile environment for microorganisms that have invaded the wound site. In an inflammatory response, when a wound occurs or an external infectious agent enters the body, leukocytes responsible for the initial stage of the immune response gather and express cytokines. Therefore, the expression level of intracellular cytokines serves as an indicator of the activation of the inflammatory response. In one embodiment of the present invention, inflammation may be one or more selected from the group consisting of skin inflammation and oral mucosal inflammation, but is not limited thereto.

[0122] In the entire specification including the following claims, “skin inflammation” may cause chronic inflammatory diseases of the skin such as psoriasis, eczema, or seborrheic dermatitis, and may cause acute inflammatory diseases such as contact dermatitis, but is not limited thereto.

[0123] In all claims below, the term “wrinkle” means a wrinkle occurring on any part of the body including the face, and may include both static rhytides and dynamic rhytides, but is not limited thereto. In one embodiment of the present invention, the wrinkle may include skin wrinkles, mucosal wrinkles, muscle wrinkles, and aging wrinkles, but is not limited thereto.

[0124] In this specification, including all claims below, “anti-wrinkle” means preventing the formation of wrinkles or alleviating existing wrinkles by promoting the expression of factors that improve wrinkles occurring in a body part; or inhibiting or suppressing the formation of wrinkles or alleviating existing wrinkles by promoting the expression of factors that improve wrinkles occurring in a body part.

[0125] In the present specification, including all claims below, the term “prevention of skin wrinkles” means preventing the formation of wrinkles on the skin or alleviating wrinkles that have already formed by promoting the expression of factors that improve skin wrinkles.

[0126] In the present specification, including all claims below, the term “improvement of skin wrinkles” means promoting the expression of factors that improve skin wrinkles to suppress or inhibit the formation of wrinkles on the skin, or to alleviate wrinkles that have already formed.

[0127] Including all claims below, “improvement” in this specification means any act that at least reduces parameters related to the condition being treated, e.g., the degree of symptoms.

[0128] In this specification, including all claims below, “prevention” means any act of suppressing or delaying the onset of a target disease, and “treatment” means any act of improving or beneficially altering a target disease and associated metabolic abnormality symptoms by administering a composition according to the present invention.

[0129] In the present specification, including all claims below, the meaning of “containing as an active ingredient” may mean containing an effective amount to the extent that it can exhibit anti-inflammatory or skin improvement effects, such as improvement of inflammation, improvement of wrinkles, improvement of atopic dermatitis, skin regeneration, or strengthening of the skin barrier, and may mean containing an effective amount to the extent that it can exhibit anti-wrinkle or anti-inflammatory effects.

[0130] The present invention provides a cosmetic composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by the following chemical formula 5, an isomer thereof, or a cosmetically acceptable salt thereof.

[0131] [Chemical Formula 5]

[0132]

[0133] (In the above chemical formula 5,

[0134] X is F, Cl, Br, I, or OH;

[0135] R is H, C 1-20 alkyl of, C 1-20 alkenyl or C 1-20 It is an alkynyl, and here the above C 1-20 The alkenyl of is characterized by having a double bond at the terminal, and the above C 1-20 The alkynyl group is characterized by having a triple bond at the terminal;

[0136] R 1 and R 2 can independently form OH, C1-3 alkyloxy, or linked together to form 1,3-dioxolane;

[0137] R 3 and R 4 It can independently form OH, C1-3 alkyloxy groups, or link with each other to form 1,3-dioxolane).

[0138] Including all claims below, the compound represented by Formula 1 may be one or more selected from the group consisting of compounds listed in Table 1 below, but is not limited thereto:

[0139] [Table 1]

[0140]

[0141] Including the entire claims below, the compound represented by Formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:

[0142] (1) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide;

[0143] (2) 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium hydroxide; and

[0144] (3) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride.

[0145] Including all claims below, in this specification, wrinkles may be skin wrinkles, but are not limited thereto.

[0146] Including all claims below, the wrinkles in this specification may be skin wrinkles caused by one or more selected from the group consisting of ultraviolet rays and skin inflammation, but are not limited thereto.

[0147] Including all claims below, the ultraviolet rays may be one or more selected from the group consisting of ultraviolet A (UVA), ultraviolet B (UVB), and ultraviolet C (UVC), but are not limited thereto.

[0148] Including all claims below, the inflammation may be acute inflammation, specifically acute inflammation induced by LPS (lipopolysaccharide), but is not limited thereto.

[0149]

[0150] Including all claims below, the wrinkles of the present invention may be wrinkles resulting from a decrease in the expression or activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins, but are not limited thereto.

[0151] Including all claims below, the composition may increase the expression or activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins, but is not limited thereto. Specifically, the composition can increase the expression of a gene encoding one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, and collagen type 1, and the composition can increase the expression of one or more proteins selected from the group consisting of collagen, collagen type 1, and elastin, and the composition can increase the activity of Smad3 protein, but is not limited thereto.

[0152] Including all claims below, the composition of the present invention may increase the expression or activity of a protein of a procollagen C-endopeptidase enhancer (PCOLCE) or a gene encoding the same, but is not limited thereto.

[0153] Including all claims below, one or more selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, elastin, and procollagen C-endopeptidase enhancer (PCOLCE) may be skin wrinkle improvement factors, but are not limited thereto.

[0154] Including all claims below, the composition may promote activity for collagen synthesis, but is not limited thereto. Furthermore, in the present invention, the promotion of activity for collagen synthesis may be the promotion of the expression or activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins, but is not limited thereto.

[0155] Including the entire claims below, inflammation may be inflammation caused by increased expression or activity of one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α), or genes encoding such proteins, but is not limited thereto.

[0156] Including all claims below, the composition may reduce, but is not limited to, the expression or activity of one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α), or genes encoding such proteins. Specifically, the composition may reduce, but is not limited to, the expression of genes encoding one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α).

[0157] Including all claims below, one or more selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α) may be inflammatory factors, but are not limited thereto.

[0158] In the entirety of the following claims, “increase” is included without limitation and means, for example, that the level of the experimental group is at least 1%, 2%, 3%, 4%, 5%, 10% or higher, for example, 5%, 10%, 20%, 30%, 40%, or 50%, 60%, 70%, 80%, 90% or higher, and / or 0.5 times, 1.1 times, 1.2 times, 1.4 times, 1.6 times, 1.8 times or higher. Specifically, it may mean an increase of 1 to 1.5 times, 1.5 to 2 times, 2 to 2.5 times, 2.5 to 3 times, 3 to 3.5 times, 3.5 to 4 times, 4 to 4.5 times, 4.5 to 5 times, 5 to 5.5 times, 5.5 to 6 times, 6 to 6.5 times, 6.5 to 7 times, 7 to 7.5 times, 7.5 to 8 times, 8 to 8.5 times, 8.5 to 9 times, 9 to 9.5 times, 9.5 to 10 times, or 10 times or more compared to that of the control group, but is not limited thereto.

[0159] In the entire specification including the following claims, “increase” means that the amount of protein expression, protein activity, or mRNA expression of a gene encoding the same is increased in an individual treated with the compound represented by Formula 1 or Formula 2 of the present invention, its isomer, its cosmetically acceptable salt, pharmaceutically acceptable salt, or food-acceptable salt compared to an individual not treated with the compound.

[0160] In the entirety of the following claims, “reduction” is included without limitation and means, for example, that the level of the experimental group is at least 1%, 2%, 3%, 4%, 5%, 10% or lower than that of the control group, for example, 5%, 10%, 20%, 30%, 40%, or 50%, 60%, 70%, 80%, 90% or lower than that of the control group, and / or is lower than 0.9 times, 0.8 times, 0.6 times, 0.4 times, 0.2 times, 0.1 times or less. Specifically, a decrease in level may mean a decrease of 1 to 1.5 times, 1.5 to 2 times, 2 to 2.5 times, 2.5 to 3 times, 3 to 3.5 times, 3.5 to 4 times, 4 to 4.5 times, 4.5 to 5 times, 5 to 5.5 times, 5.5 to 6 times, 6 to 6.5 times, 6.5 to 7 times, 7 to 7.5 times, 7.5 to 8 times, 8 to 8.5 times, 8.5 to 9 times, 9 to 9.5 times, 9.5 to 10 times, or 10 times or more compared to the control group, but is not limited thereto.

[0161] In the entirety of the following claims, “reduction” means that the amount of protein expression, protein activity, or mRNA expression of a gene encoding the same is reduced in an individual treated with the compound represented by Formula 1 or Formula 2 of the present invention, its isomer, its cosmetically acceptable salt, pharmaceutically acceptable salt, or food-acceptable salt compared to an individual not treated with the compound.

[0162] In the entirety of the following claims, the “experimental group” may be an individual having developed wrinkles or inflammation, specifically an individual having developed skin wrinkles or inflammation, but is not limited thereto.

[0163] In the entirety of the following claims, the “control group” may be a normal individual, an individual without wrinkles or inflammation, specifically an individual without skin wrinkles or inflammation, but is not limited thereto.

[0164] Including all claims below, as described in this specification, TNF-α is a representative cytokine primarily secreted by inflammatory cells or immune cells in response to external stimuli or infectious agents, and is a proinflammatory cytokine that plays a central role in mediating infections, inflammation, autoimmune and allergic diseases together with interleukin-1 (IL-1). Chronic inflammatory diseases of the skin mediated by TNF-α include psoriasis, eczema, or seborrheic dermatitis, while acute inflammatory diseases include contact dermatitis. Additionally, atopic dermatitis can be cited as a TNF-α-mediated allergic disease.

[0165] Including all claims below, the composition may increase the expression or activity of one or more selected from the group consisting of collagen and elastin, but is not limited thereto. In one embodiment of the present invention, it was confirmed that the composition of the present invention may help improve skin elasticity and reduce wrinkles by aiding the production of collagen and elastin, but is not limited thereto.

[0166] In all claims below, collagen is a major protein in the extracellular matrix of connective tissues of many animals, found in cartilage, bone, tendons, ligaments, and skin, and may be one or more selected from the group consisting of type I collagen, type II collagen, type III collagen, type IV collagen, and type V collagen, but is not limited thereto.

[0167] In the entire specification including the following claims, elastin is a protein with high elasticity within connective tissue and enables numerous body tissues to maintain their shape after expansion or contraction, and elastin may enable the skin to return to its original position when compressed or tightened, but is not limited thereto.

[0168] Including all claims below, in this specification, an increase in expression or activity may mean an increase in the expression or activity of a protein or a gene encoding it. Specifically, in one embodiment of the present invention, the present invention has confirmed an increase in the expression of a protein or a gene encoding it, but is not limited thereto.

[0169] Including all claims below, the composition may be processed in one or more ways selected from the group consisting of Microneedle Therapy System (MTS) method, Auto Microneedle Therapy System (AMTS) method, application method, injection method, iontophoresis, sonophoresis, electroporation, and tape stripping. Specifically, in the present invention, the composition may be processed in one or more ways selected from the group consisting of Microneedle Therapy System (MTS) method and Auto Microneedle Therapy System (AMTS) method, but is not limited thereto.

[0170] Including all claims below, the Microneedle Therapy System (MTS) method or Auto Microneedle Therapy System (AMTS) method is 0.05 to 2 mm, 0.1 to 2 mm, 0.15 to 2 mm, 0.2 to 2 mm, 0.25 to 2 mm, 0.3 to 2 mm, 0.5 to 2 mm, 1 to 2 mm, 1.5 to 2 mm, 0.05 to 2 mm, 0.1 to 2 mm, 0.15 to 2 mm, 0.2 to 2 mm, 0.25 to 2 mm, 0.3 to 2 mm, 0.5 to 2 mm, 1 to 2 mm, 1.5 to 2 mm, 0.05 to 1.5 mm, 0.1 to 1.5 mm, 0.15 to 1.5 mm, 0.2 to 1.5 mm, 0.25 to 1.5 mm, 0.3 to 1.5 mm, 0.5 to 1.5 mm, 1 to 1.5 mm, 0.05 to 1 mm, 0.1 to 1 mm, 0.15 to 1 mm, 0.2 to 1 mm, 0.25 to 1 mm, 0.3 to 1 mm, 0.5 to 1 mm, 0.05 to 0.5 mm, 0.1 to 0.5 mm, 0.15 to 0.5 mm, 0.2 to 0.5 mm, 0.25 to 0.5 mm, 0.3 to 0.5 mm, 0.05 to 0.3 mm, 0.1 to 0.3 mm, 0.15 to 0.3 mm, 0.2 to 0.3 mm, 0.25 to 0.3 mm, 0.05 to The method may use a needle with a length of 0.25 mm, 0.1 to 0.25 mm, 0.15 to 0.25 mm, 0.2 to 0.25 mm, or 0.2 mm, but is not limited thereto.

[0171] In the entirety of the following claims, the term "cosmetically acceptable salt" includes salts derived from cosmetically acceptable inorganic acids, organic acids, or bases. Specific examples include the salts described above, and additionally include hydrobromide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, acetate, succinate, citrate, tartrate, lactate, mandelate, methanesulfonate (mesylate), and p-toluenesulfonate (tosylate) salts.

[0172] In all claims below, the cosmetically effective amount is 0.0001 to 100 mg / kg, preferably 0.001 to 10 mg / kg, but is not limited thereto. The treatment or dosage may be adjusted according to the specific patient's body weight, age, gender, health condition, diet, duration of administration, method of administration, elimination rate, severity of disease, etc. The treatment or administration may be performed once a day or divided into several times.

[0173] Including all claims below, the formulation of the cosmetic composition according to the present invention may be one or more forms selected from the group consisting of shampoo, skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nourishing lotion, massage cream, nourishing cream, mist, moisture cream, hand cream, hand lotion, foundation, essence, nourishing essence, pack, soap, cleansing foam, cleansing lotion, cleansing cream, cleansing oil, cleansing balm, body lotion, and body cleanser, but is not limited thereto.

[0174] Including all claims below, the cosmetic composition of the present invention may be prepared in the form of a shampoo, but is not limited thereto. Specifically, when the cosmetic composition of the present invention is prepared in the form of a shampoo, the cosmetic composition may not only improve or prevent scalp wrinkles, but may also improve and alleviate scalp inflammation by reducing inflammatory factors, but is not limited thereto.

[0175] Including the entire claims below, the cosmetic composition of the present invention may further comprise a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, high molecular weight polysaccharides, and sphingolipids.

[0176] In the present specification, including all claims below, any water-soluble vitamin that can be incorporated into cosmetics may be used, but examples include vitamin B1, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinamide, folic acid, vitamin C, vitamin H, etc., and their salts (thiamine hydrochloride, sodium ascorbate, etc.) or derivatives (sodium ascorbate-2-phosphate, magnesium ascorbate-2-phosphate, etc.) are also included in the water-soluble vitamins that can be used in the present invention. Water-soluble vitamins can be obtained by conventional methods such as microbial conversion, purification from microbial cultures, enzymatic methods, or chemical synthesis methods.

[0177] In the entire specification including the following claims, any useful vitamin that can be incorporated into cosmetics may be used, but examples include vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol), and their derivatives (ascorbin palmitate, ascorbin stearate, ascorbin dipalmitate, dl-alpha tocopherol acetate, dl-alpha tocopherol nicotinate, vitamin E, DL-pantotenyl alcohol, D-pantotenyl alcohol, pantotenyl ethyl ether, etc.) are also included in the useful vitamins used in the present invention. The useful vitamins may be obtained by conventional methods such as microbial conversion, purification from microbial cultures, enzymes, or chemical synthesis.

[0178] In the present specification, including all claims below, any polymeric peptide that can be incorporated into cosmetics may be used, but examples include collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, keratin, etc. Polymeric peptides may be obtained by purification through conventional methods such as purification from a culture medium of microorganisms, enzymatic methods, or chemical synthesis methods, or they may be used by purifying from natural materials such as the dermis of pigs or cattle, or silk fibers of silkworms.

[0179] In the present specification, including all claims below, any polymeric polysaccharide that can be incorporated into cosmetics may be used, but examples include hydroxyethylcellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate or its salt (sodium salt, etc.). For example, chondroitin sulfate or its salt, etc., can be used after purifying it from mammals or fish.

[0180] In the present specification, including all claims below, any sphingolipid that can be incorporated into cosmetics may be used, such as ceramide, phytosphingosine, sphingoglycolipid, etc. Sphingolipids can be obtained by purifying them by conventional methods or by chemical synthesis from mammals, fish, shellfish, yeast, plants, etc.

[0181] Including all claims below, the cosmetic composition of the present invention may include other ingredients conventionally used in cosmetics in addition to the essential ingredients as needed.

[0182] Including all claims below, the formulation ingredients that may be added in addition include oil ingredients, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, UV absorbers, preservatives, disinfectants, antioxidants, plant extracts, pH adjusters, alcohols, dyes, fragrances, blood circulation promoters, cooling agents, antiperspirants, purified water, etc.

[0183] In the present specification, including all claims below, oil components may include ester-based oils, hydrocarbon-based oils, silicone-based oils, fluorine-based oils, animal oils, plant oils, etc.

[0184] In this specification, including all claims below, the ester-based oils include tri2-ethylhexanoate glyceryl, 2-ethylhexanoate cetyl, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isocetyl isocetyl isostearate, butyl stearate, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, diisopropyl adipate, isoalkyl neopentanoate, tri(capryl, capric acid)glyceryl, tri2-ethylhexanoate trimethylolpropane, triisostearate trimethylolpropane, tetra2-ethylhexanoate pentaelislitol, cetyl caprylate, Decyl lauric acid, hexyl lauric acid, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleic acid, cetyl lisinooleic acid, isostearyl lauric acid, isotridecyl myristate, isocetyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleic acid, octyldodecyl oleic acid, octyldodecyl linoleic acid, isopropyl isostearate, 2-cetostearyl ethylhexanoate, 2-stearyl ethylhexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicaprine, di(capryl, capric acid)propylene glycol, propylene glycol dicaprylate, neopentyl glycol dicaprine, neopentyl glycol dioctanoate, Glyceryl tricaprylate, Glyceryl triundecylate, Glyceryl triisopalmitate, Glyceryl triisostearate, Octyldodecyl neopentanoate, Isostearyl octanoate, Octyl isononanoate, Hexyldecyl neodecanoate, Octyldodecyl neodecanoate, Isocetyl isostearate, Isostearyl isostearate, Octyldecyl isostearate, Polyglycerin oleic acid ester, Polyglycerin isostearic acid ester, Triisocetyl citrate, Triisoalkyl citrate, Triisooctyl citrate, Lauryl lactate, Myristyl lactate, Cetyl lactate, Octyldecyl lactate, Triethyl citrate, Acetyltriethyl citrate, Acetyltributyl citrate, Trioctyl citrate, Diisostearyl malate, 2-ethylhexyl hydroxystearic acid, di2-ethylhexyl succinate,Examples include ester compounds such as diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholesteryl oleate, pitsteryl isostearate, pitsteryl oleate, isocetyl 12-stealloylhydroxystearate, stearyl 12-stealloylhydroxystearate, and isostearyl 12-stealloylhydroxystearate.

[0185] In the present specification, including all claims below, hydrocarbon oils may include squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybutene, microcrystalline wax, Vaseline, etc.

[0186] In the present specification, including all claims below, silicone-based oils may include polymethylsilicon, methylphenylsilicon, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane-methylcetyloxysiloxane copolymer, dimethylsiloxane-methylstealoxysiloxane copolymer, alkyl-modified silicone oil, amino-modified silicone oil, etc.

[0187] In the present specification, including all claims below, fluorinated oils may include perfluoropolyethers, etc.

[0188] In the present specification, including all claims below, animal or plant oils may include avocado oil, almond oil, olive oil, sesame oil, rice bran oil, safflower oil, soybean oil, corn oil, rapeseed oil, apricot kernel oil, palm kernel oil, palm oil, castor oil, sunflower oil, grapeseed oil, cottonseed oil, coconut oil, cucui nut oil, wheat germ oil, rice germ oil, shea butter, laurel oil, macadamia nut oil, meadowsweet oil, egg yolk oil, beef tallow, horse oil, mink oil, orange raffia oil, jojoba oil, candelilla wax, carnaba wax, liquid lanolin, hydrogenated castor oil, etc.

[0189] In the present specification, including all claims below, examples of moisturizers include water-soluble low molecular weight moisturizers, oil-soluble molecular moisturizers, water-soluble polymers, oil-soluble polymers, etc.

[0190] In the present specification, including all claims below, examples of water-soluble low molecular weight moisturizers include serine, glutamine, sorbitol, mannitol, pyrrolidone-sodium carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B (degree of polymerization n = 2 or more), polypropylene glycol (degree of polymerization n = 2 or more), polyglycerin B (degree of polymerization n = 2 or more), lactic acid, lactate, etc.

[0191] In the present specification, including all claims below, examples of fat-soluble low molecular weight moisturizers include cholesterol, cholesterol esters, etc.

[0192] In the present specification, including all claims below, examples of water-soluble polymers include carboxyvinyl polymer, polyaspartate, tragacanth, xanthan gum, methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, water-soluble chitin, chitosan, dextrin, etc.

[0193] In the present specification, including all claims below, examples of fat-soluble polymers include polyvinylpyrrolidone-eicocene copolymer, polyvinylpyrrolidone-hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, polymeric silicone, etc.

[0194] In the present specification, including all claims below, examples of emollient agents include long-chain acylglutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid, lanolin fatty acid cholesteryl ester, etc.

[0195] In the present specification, including all claims below, surfactants may include nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc.

[0196] Including all claims below, nonionic surfactants may include self-emulsifying monostearate glycerin, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE hydrogenated castor oil, POE castor oil, POE·POP (polyoxyethylene·polyoxypropylene) copolymer, POE·POP alkyl ether, polyether-modified silicone, lauric acid alkanolamide, alkylamine oxide, hydrogenated soybean phospholipid, etc.

[0197] In the present specification, including all claims below, examples of anionic surfactants include fatty acid soap, alpha-acylsulfonate, alkylsulfonate, alkylallylsulfonate, alkylnaphthalenesulfonate, alkyl sulfate, POE alkyl ether sulfate, alkylamide sulfate, alkyl phosphate, POE alkyl phosphate, alkylamide phosphate, alkylloylalkyl taurine salt, N-acylamino acid, POE alkyl ether carboxylate, alkyl sulfosuccinate, sodium alkyl sulfoacetate, acylated hydrolyzed collagen peptide salt, perfluoroalkyl phosphate ester, etc.

[0198] In the present specification, including all claims below, cationic surfactants may include alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, benzalkonium chloride, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, lanolin derivative quaternary ammonium salts, etc.

[0199] In the present specification, including all claims below, examples of amphoteric surfactants include carboxybetaine type, amidebetaine type, sulfobetaine type, hydroxysulfobetaine type, amidesulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amideamine type, etc.

[0200] Including all claims below, the organic and inorganic pigments comprises inorganic pigments such as silica, anhydrous silica, magnesium silicate, talc, sericite, mica, kaolin, bengala, clay, bentonite, titanium-coated mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide, calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, ultramarine, chromium oxide, chromium hydroxide, calamine, and complexes thereof; Examples include organic pigments such as polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenolic resin, fluoropolymer, silicone resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene-styrene copolymer, silk powder, cellulose, CI pigment yellow, CI pigment orange, etc., and composite pigments of inorganic pigments and organic pigments thereof.

[0201] In this specification, including all claims below, the organic powder comprises: a metal soap such as calcium stearate; metal alkyl phosphate salts such as sodium zinc cetylphosphate, zinc laurylphosphate, calcium laurylphosphate; polyvalent acyl amino acid salts such as calcium lauroyl-beta-alanine, zinc lauroyl-beta-alanine, and calcium lauroylglycine; polyvalent amide sulfonic acid salts such as calcium lauroyl-taurine and calcium palmitoyl-taurine; N-acyl basic amino acids such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoyllysine, N-alpha-paritoylolnitine, N-alpha-lauroylarginine, and N-alpha-hydrogenated beef tallow fatty acid acylarginine; and N-acyl polypeptides such as N-lauroylglycylglycine. Alpha-amino fatty acids such as alpha-aminocaprilic acid and alpha-aminolauric acid; examples include polyethylene, polypropylene, nylon, polymethyl methacrylate, polystyrene, divinylbenzene-styrene copolymer, tetrafluoroethylene, etc.

[0202] Including all claims below, the ultraviolet absorber comprises para-aminobenzoic acid, ethyl para-aminobenzoate, amyl para-aminobenzoate, octyl para-aminobenzoate, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butylphenyl salicylate, homomentyl salicylate, benzyl cinnamonate, paramethoxycinnamic acid-2-ethoxyethyl paramethoxycinnamic acid, octyl paramethoxycinnamic acid, diparamethoxycinnamic acid mono-2-ethylhexaneglyceryl, isopropyl paramethoxycinnamic acid, a mixture of diisopropyl and diisopropyl cinnamonic acid esters, urocanic acid, ethyl urocanic acid, hydroxymethoxybenzophenone, hydroxymethoxybenzophenonesulfonic acid and its salts, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenonedisulfonate, dihydroxybenzophenone, Examples include tetrahydroxybenzophenone, 4-tert-butyl-4'-methoxydibenzoylmethane, 2,4,6-trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine, 2-(2-hydroxy-5-methylphenyl)benzotriazole, etc.

[0203] Including all claims below, examples of disinfectants in this specification include hinokitiol, triclosan, trichlorohydroxydiphenyl ether, chlorhexidine gluconate, phenoxyethanol, resorcinol, isopropylmethylphenol, azulene, salicylic acid, zincphyllithion, benzalkonium chloride, photosensitive agent 301, mononitroguaiacol sodium, undecylenic acid, etc.

[0204] In the present specification, including the entire claims below, examples of antioxidants include butylhydroxyanisole, propyl gallic acid, elisorbic acid, etc.

[0205] In the present specification, including all claims below, pH adjusting agents may include citric acid, sodium citrate, malic acid, sodium malate, fumaric acid, sodium fumarate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogen phosphate, etc.

[0206] In the present specification, including all claims below, alcohols may include higher alcohols such as cetyl alcohol.

[0207] In addition, the formulation components that may be added in addition to the above claims, including the entire claim below, are not limited thereto, and any of the above components may be formulated within a range that does not impair the purpose and effect of the present invention, but may be formulated in an amount of 0.01-5% by weight or 0.01-3% by weight with respect to the total weight.

[0208] In the entire specification including the following claims, when the formulation of the present invention is a lotion, paste, cream, or gel, animal fiber, plant fiber, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, or zinc oxide, etc. may be used as a carrier component.

[0209] Including all claims below, in the specification, when the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, or polyamide powder may be used as a carrier component, and particularly in the case of a spray, may additionally include a propellant such as chlorofluorohydrocarbon, propane / butane, or dimethyl ether.

[0210] In the entire specification including the following claims, when the formulation of the present invention is a solution or emulsion, a solvent, a solvating agent, or an emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol, or fatty acid ester of sorbitan.

[0211] In the entire specification including the following claims, when the formulation of the present invention is a suspension, a liquid diluent such as water, ethanol, or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester, and polyoxyethylene sorbitan ester, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, or tracanthera may be used as a carrier component.

[0212] In the present specification, including all claims below, when the formulation of the present invention is a surfactant-containing cleansing agent, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcosinate, fatty acid amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolin derivative, or ethoxylated glycerol fatty acid ester, etc. may be used as a carrier component.

[0213]

[0214] The present invention provides a medical device selected from functional wound dressings, fillers, or composite fillers having anti-wrinkle or anti-inflammatory functions, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0215] In addition, the present invention provides a composition for a dermal filler comprising, as an active ingredient, a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0216] In all claims below, the “wound dressing” may create a moist environment on a wound, but is not limited thereto. In one embodiment of the present invention, the functional wound dressing of the present invention not only creates a moist environment on a wound, but may also improve skin wrinkles on the wound by increasing skin wrinkle improvement factors, and may alleviate inflammation by reducing inflammatory factors on the wound to which it is applied, but is not limited thereto.

[0217] In all claims below, the term “filler” in this specification may be a biomaterial capable of filling skin tissue, but is not limited thereto. In one embodiment of the present invention, the filler of the present invention, by being filled into skin tissue, may exhibit an effect of improving skin wrinkles by increasing skin wrinkle improvement factors and thereby improving the cause of wrinkle formation, and may exhibit an anti-inflammatory effect and a side effect reduction effect by reducing inflammatory factors in the filled area, but is not limited thereto.

[0218] In all claims below, the “composite filler” in this specification may be a biomaterial composed of a plurality of functional components capable of filling skin tissue, but is not limited thereto. In one embodiment of the present invention, the composite filler of the present invention may include the compound of the present invention and hyaluronic acid, etc., and may include, without limitation, any component having an anti-wrinkle or anti-inflammatory function, but is not limited thereto.

[0219] In all claims below, “hyaluronic acid (hereinafter also referred to as “HA”)” is a biopolymer material in which disaccharide repeating units composed of N-acetyl-D-glucosamine and D-glucuronic acid are linearly linked. It is abundant in the vitreous fluid of the eye, synovial fluid of joints, and chicken combs, and because it possesses excellent biocompatibility, it is widely used for medical and medical devices or cosmetics, such as ophthalmic surgical aids, joint function enhancers, drug delivery systems, eye drops, and anti-wrinkle agents. Furthermore, the filler or composite filler according to the present invention may further comprise water, an anesthetic, or a combination thereof in addition to the hyaluronic acid.

[0220] Including all claims below, the compound represented by Formula 1 or Formula 2, its isomer, or its pharmaceutically acceptable salt may be used as a composition for fillers for cosmetic or therapeutic purposes due to the skin condition-improving activity, and more specifically, may be very useful as a composition for filler injection, and as specific examples, may be useful as a composition for filling or replacing biological tissue, a composition for filling wrinkles, remodeling of the face or increasing lip volume, a composition for use in the treatment of skin rehydration by mesotherapy, but is not limited thereto.

[0221] In this specification, including all claims below, medical devices may be, but are not limited to, consultation and diagnosis equipment, clinical examination equipment, radiation equipment, surgical apparatus and equipment, cure apparatus and equipment, rehabilitation medicine and physiotherapy apparatus, ophthalmic apparatus, dental apparatus, central supply equipment, hospital accommodation and emergency equipment, Oriental medicine and equipment, pharmaceutical equipment, obesity and health equipment, medical supplies, consumables, etc.

[0222] Including all claims below, the medical device may increase the expression or activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins, but is not limited thereto.

[0223] Including all claims below, the medical device may reduce the expression or activity of one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α), or genes encoding such proteins, but is not limited thereto.

[0224]

[0225] The present invention provides a quasi-drug composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0226] In this specification, including the entire claim below, the term “quasi-drug” refers to articles used for the purpose of treating, improving, alleviating, managing, or preventing diseases of humans or animals, among which the effect is milder than that of pharmaceuticals. For example, quasi-drugs under the Pharmaceutical Affairs Act exclude articles used for pharmaceutical purposes and include products used for the treatment or prevention of diseases in humans / animals, products that have a mild effect on the human body or do not act directly on it, etc.

[0227] Including all claims below, the quasi-drug composition of the present invention may be used by adding the active ingredient as is or together with other quasi-drug ingredients, and may be used appropriately according to conventional methods. The amount of the mixture of the active ingredient may be appropriately determined according to the purpose of use (prevention, improvement, health, or therapeutic treatment).

[0228] Including all claims below, the quasi-drug composition may be formulated into one or more selected from the group consisting of external preparations, powders, antiseptics and disinfectants, toothpastes, ointments, lotions, oral preparations, wet wipes, sprays, patches, bandages, patches, and combinations thereof, but is not limited thereto. Additionally, the quasi-drug of the present invention may be a quasi-drug composition for the prevention or improvement of periodontitis or peri-implantitis characterized by being one of toothpaste, oral rinse, oral spray, oral ointment, oral patch, and gum, but is not limited thereto.

[0229] Including all claims below, when a quasi-drug composition is utilized as a toothpaste or toothpaste, it may not only have disinfecting, tartar-dissolving, odor-reducing, and tooth decay-improving or preventive effects, but may also maintain elasticity in the oral cavity and surrounding skin, and reduce inflammatory factors to restore inflamed oral mucosa, but is not limited thereto.

[0230] In all claims below, the term “pharmaceuticalally acceptable” means a compound or composition that is suitable for use in contact with tissues of a subject (e.g., human) and is within the scope of sound medical judgment, having a reasonable benefit / risk ratio without excessive toxicity, irritation, allergic reaction, or other problems or complications.

[0231] Including all claims below, examples of suitable acids in this specification include hydrochloric acid, bromic acid, sulfuric acid, nitric acid, perchloric acid, hydroiodic acid, fumaric acid, maleic acid, phosphoric acid, glycolic acid, lactic acid, salicylic acid, succinic acid, toluene-p-sulfonic acid, tartaric acid, (+)-L-tartar acid, acetic acid, trichloroacetic acid or trifluoroacetic acid, 2,2-dichloroacetic acid, acylated amino acids, adipic acid, alginic acid, ascorbic acid, L-aspartic acid, 4-acetamidobenzoic acid, (+)-camponic acid, camphosulfonic acid, (+)-(1S)-camphosulfonic acid, capric acid, caproic acid, caprylic acid, cinnamic acid, cyclamic acid, dodecylsulferic acid, ethane-1,2-disulfonic acid, ethanesulfonic acid, 2-Hydroxyethanesulfonic acid, galactar acid, gentizin acid, glucoheptanoic acid, D-gluconic acid, D-glucuronic acid, L-glutamic acid, α-oxo-glutaric acid, hipfuric acid, (+)-L-lactic acid, (+-)-DL-lactic acid, lactobionic acid, (-)-L-malic acid, (+-)-DL-mandelic acid, citric acid, methanesulfonic acid, formic acid, benzoic acid, malonic acid, gluconic acid, naphthalene-2-sulfonic acid, naphthalene-1,5-disulfonic acid, benzenesulfonic acid, 1-hydroxy-2-naphthoic acid, nicotinic acid, oleic acid, orotic acid, oxalic acid, palmitic acid, palm acid, L-pyroglutamic acid, salicylic acid, 4-amino-salicylic acid, sebacic acid, stearic acid, Examples include tannic acid, thiocyanate, camsylic acid, and undecylic acid. Acid addition salts can be prepared by conventional methods, for example, by dissolving a compound in an excess amount of an aqueous acid solution and precipitating the salt using a water-miscible organic solvent such as methanol, ethanol, acetone, or acetonitrile. Alternatively, they can be prepared by heating an equal molar amount of the compound and an acid or alcohol in water, followed by evaporating and drying the mixture, or by suction filtration of the precipitated salt.

[0232] In the entire specification including the following claims, salts derived from suitable bases may include, but are not limited to, alkali metals such as sodium and potassium, alkaline earth metals such as magnesium, and ammonium. Alkali metal or alkaline earth metal salts can be obtained, for example, by dissolving a compound in an excess amount of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the undissolved compound salt, and then evaporating and drying the filtrate. In this case, it is particularly suitable for pharmaceutical purposes to produce sodium, potassium, or calcium salts as metal salts, and the corresponding silver salts can be obtained by reacting the alkali metal or alkaline earth metal salt with a suitable silver salt (e.g., silver nitrate).

[0233] Including the entire claims below, the scope of the compounds of the present invention may include not only pharmaceutically acceptable salts but also all isomers, hydrates, and solvates that can be prepared by conventional methods.

[0234] In the entire specification including the following claims, the content of the compound of the present invention in the composition of the present invention can be appropriately adjusted according to the symptoms of the disease, the degree of progression of the symptoms, the condition of the patient, etc., and, for example, may be 0.0001 to 99.9% by weight or 0.001 to 50% by weight based on the total weight of the composition, but is not limited thereto. The above content ratio is a value based on the dry weight after removing the solvent.

[0235] Including all claims below, the composition according to the present invention may further comprise a suitable carrier, excipient, and diluent commonly used in the manufacture of the composition. The excipient may be one or more selected from the group consisting of, for example, diluents, binders, disintegrants, lubricants, adsorbents, humectants, film-coating materials, and controlled-release additives.

[0236] Including all claims below, the composition according to the present invention is, each according to a conventional method, a tablet, sustained-release tablet, enteric-coated tablet, sublingual tablet, lozenge, pill, capsule, hard capsule, soft capsule, sustained-release capsule, enteric-coated capsule, granule, sustained-release granule, enteric-coated granule, powder, dry liquid, liquid, suspension, soft liquid, fluid liquid, limonade, fragrance, emulsion, ethanol, tincture, inhalant, ellipsis, injection, irrigation solution, sterile injection solution, eye drops, warning agent. It can be formulated and used in the form of external preparations such as lotions, pastes, sprays, patches, or aerosols, and the external preparation may have a formulation such as a cream, gel, patch, spray, ointment, ointment, lotion, liniment, paste, or cataplasma.

[0237] Including all claims below, carriers, excipients, and diluents that may be included in the composition according to the present invention may include lactose, dextrose, sucrose, oligosaccharides, 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.

[0238] Including all claims below, the formulation is prepared using diluents or excipients such as commonly used fillers, extenders, binders, wetting agents, disintegrants, and surfactants.

[0239] Including all claims below, the composition according to the present invention is administered in a pharmaceutically effective amount. In the present invention, "pharmaceutically effective amount" means an amount sufficient to treat a disease with a reasonable benefit / risk ratio applicable to medical treatment, and the effective dose level may be determined based on factors including the type and severity of the patient's disease, drug activity, sensitivity to the drug, time of administration, route of administration and elimination rate, duration of treatment, concurrently used drugs, and other factors well known in the medical field.

[0240] Including all claims below, the composition according to the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, may be administered sequentially or simultaneously with conventional therapeutic agents, and may be administered as a single or multiple doses. It is important to administer an amount that obtains maximum effect with a minimum amount without side effects, taking all of the above factors into consideration, and this can be easily determined by a person skilled in the art to which the present invention pertains.

[0241] Including the entire claims below, the composition of the present invention may be administered to an individual by various routes. All modes of administration may be anticipated, for example, by oral administration, subcutaneous injection, intraperitoneal administration, intramuscular injection, intrathecal (intradural) injection, sublingual administration, buccal mucosal administration, rectal insertion, vaginal insertion, ocular administration, ear administration, nasal administration, inhalation, spray through the mouth or nose, skin administration, transdermal administration, etc.

[0242] Including the full claims below, the composition of the present invention is determined according to the type of drug as the active ingredient, along with various relevant factors such as the disease to be treated, the route of administration, the age, gender, weight, and severity of the disease of the patient.

[0243] In the entirety of the following claims, the term “individual” means an object requiring prevention, improvement, or treatment of wrinkles or inflammation, and more specifically means mammals such as human or non-human primates, mice, rats, dogs, cats, horses, and cattle.

[0244]

[0245] The present invention provides a health functional food composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by Formula 1 or Formula 2, an isomer thereof, or a food-grade acceptable salt thereof.

[0246] In all claims below, when a compound represented by Formula 1 or Formula 2 of the present invention, or an isomer thereof, is used as a food additive, said compound represented by Formula 1 or Formula 2, or an isomer thereof, may be added as is or used together with other food or food ingredients, or may be used appropriately according to conventional methods. The amount of the active ingredient may be appropriately determined according to the purpose of use (prevention, improvement, health, or therapeutic treatment). Generally, when manufacturing food or beverages, the compound represented by Formula 1 or Formula 2 of the present invention, or an isomer thereof, may be added in an amount of 15% by weight or less, or 10% by weight or less, relative to the raw material. However, in the case of long-term consumption for the purpose of health and hygiene or health control, the above amount may be less than the above range, and since there are no issues regarding safety, the active ingredient may be used in an amount greater than the above range.

[0247] In all claims below, the term “food-acceptable salt” in this specification includes a salt derived from a food-acceptable organic acid, inorganic acid, or base.

[0248] In the present specification, including all claims below, there are no special limitations on the types of food. Examples of foods to which the substance may be added include meat, sausage, bread, chocolate, candies, snacks, confectionery, pizza, ramen, other noodles, chewing gum, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages, and vitamin complexes, and include all health functional foods in the conventional sense.

[0249] Including all claims below, the health beverage composition according to the present invention may contain various flavoring agents or natural carbohydrates, etc., as additional ingredients, as in conventional beverages. The natural carbohydrates described above are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. As sweeteners, natural sweeteners such as taumatin and stevia extract, or synthetic sweeteners such as saccharin and aspartame may be used. The proportion of the natural carbohydrates is generally about 0.01-0.20 g or about 0.04-0.10 g per 100 mL of the composition of the present invention.

[0250] Including the full claims below, the composition of the present invention may contain, in addition to the above, various nutrients, vitamins, electrolytes, 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. Furthermore, the composition of the present invention may contain fruit pulp for the production of natural fruit juices, fruit juice beverages, and vegetable beverages. These ingredients may be used independently or in combination. Although the proportion of these additives is not critical, it is generally selected in the range of 0.01 to 0.20 parts by weight per 100 parts by weight of the composition of the present invention.

[0251] In this specification, including all claims below, the term “health functional food” is synonymous with “food for special health use (FoSHU)” and refers to a food with high medical or therapeutic effects that is processed to efficiently exhibit bio-regulatory functions in addition to nutritional supply, and said food may be manufactured in various forms such as tablets, capsules, powders, granules, liquids, and pills to obtain useful effects for anti-wrinkle or anti-inflammation.

[0252] Including all claims below, the health functional food of the present invention can be manufactured by methods commonly used in the art, and can be manufactured by adding raw materials and ingredients commonly added in the art. In addition, unlike general pharmaceuticals, it has the advantage of being made from food, thus avoiding side effects that may occur during long-term use of pharmaceuticals, and can be highly portable.

[0253] Including all claims below, the health functional food has the advantage of having a superior effect when consumed in the form of an inner beauty food. The inner beauty refers to a food referred to as "edible cosmetics or beauty food," which is a food that changes the skin constitution to a healthy state by absorbing various skin-beneficial ingredients into the body. Just as one chooses cosmetics suitable for a skin type, one can select and consume an inner beauty food suitable for an individual by considering skin condition and lifestyle. For example, when a cosmetic containing the above cosmetic composition is combined with an inner beauty food containing a compound represented by Chemical Formula 1 or Chemical Formula 2 of the present invention, an isomer thereof, or a food-grade acceptable salt thereof, the effect is significantly higher compared to using only the cosmetic or pharmaceutical, thereby providing the advantage of more effective anti-wrinkle or anti-inflammatory effects on the skin.

[0254]

[0255] Including the entire claims below, the above descriptions regarding cosmetic compositions, medical devices, quasi-drug compositions, and health functional food compositions in the present invention may be used interchangeably without limitation where interchangeable.

[0256] In this specification, including the entire claims below, terms such as “about,” “substantially,” etc., are used to mean at or near the stated value when inherent manufacturing and material tolerances are presented in the said meaning, and are used to prevent unscrupulous infringers from unfairly exploiting the disclosed content in which precise or absolute values ​​are mentioned to aid in understanding the invention.

[0257] In all claims below, the term “combination thereof” included in the Markush-type expression means one or more mixtures or combinations selected from the group consisting of the components described in the Markush-type expression, and means including one or more selected from the group consisting of said components.

[0258]

[0259] The present invention will be explained in more detail below through examples. These examples are merely for the purpose of explaining 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 to these examples.

[0260]

[0261] Example 1-1. Synthesis of Isoquinoline Derivative Compound ALT 001

[0262] The isoquinoline derivative compound 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide (2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide; ALT 001) according to the present invention was synthesized through the following process: palmatine (1.0 g, 2.92 mmol) was dissolved in 40 mL of anhydrous CH2Cl2 in a dried 250 mL round-bottom flask, and a BBr3 solution (12.80 mL, 12.80 mmol) was added under a nitrogen stream at 0°C to prepare a reaction solution, and the reaction solution was stirred at room temperature for 12 hours, after which the reaction was confirmed to be complete using TLC. 10 mL of MeOH was added to the reaction solution after the above reaction was completed and stirred for 30 minutes. After concentrating using a vacuum concentrator, the solution was washed with CH2Cl2 (100 mL x 5) and dried under reduced pressure to obtain a solid isoquinoline derivative compound (2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide; ALT 001) with a yield of 99% (1.09 g, 2.98 mmol), and the reaction is illustrated in Reaction Scheme 1a below:

[0263] 1 H-NMR (400 MHz, DMSO-d6) δ10.71 (s, 1H), 10.62 (s, 1H) 9.98 (br, 1H), 9.74 (s, 1H), 9.23 (br, 1H), 8.58 (s, 1H), 7.75 (d, J = 8.8 Hz, 1H) 7.61 (d, J = 8.8 Hz 1H), 7.46 (s, 1H), 6.77 (s, 1H), 4.82 (t, J = 6.0 Hz, 2H), 3.06 (t, J = 6.0 Hz, 2H)

[0264] [Reaction Equation 1a]

[0265]

[0266]

[0267] Example 1-2. Palmatine

[0268] Palmatine (CAS Number: 3486-67-7), represented by Chemical Formula 3, is shown below.

[0269] [Chemical Formula 3]

[0270]

[0271]

[0272] Examples 1-3. Berberine

[0273] Berberine represented by chemical formula 4 (Berberine, CAS Number: 633-65-8 (Berberine·HCl) or CAS Number: 2086-83-1 (Berberine·HCl·2H2O)) is shown below.

[0274] [Chemical Formula 4]

[0275]

[0276]

[0277] Example 2. Confirmation of the effect of enhancing the function of genes related to skin wrinkle improvement

[0278] In this embodiment, it was confirmed whether the isoquinoline derivative of the present invention improves the function of genes related to skin wrinkle improvement. Specifically, living HS27 cells were used to identify wrinkle factors caused by ultraviolet (UV) stress, using fibroblasts isolated from the wool of Black men.

[0279] 5×10⁶ HS27 cells in a 6-well plate 5Cells were seeded at wells and cultured overnight to stabilize, after which they were washed with DPBS (Dulbecco's Phosphate-Buffered Saline). Subsequently, a UV lamp (5 Sankyo Denki G5T5 lamps, Sankyo Denki Co., Yokohama, Japan) was used at 50 mJ / cm². 2The study investigated the results. L-ascorbic acid 100 μg / mL was used as a positive control, and ALT 001, the isoquinoline derivative of the present invention, was treated at concentrations of 15 μM, 30 μM, and 50 μM. After 24 hours, cells were collected with 0.25% trypsin-EDTA, RNA was extracted using the RNasyMini Kit (QIAGEN, Hilden, Germany), and then synthesized into cDNA using the iScript™ cDNA Synthesis Kit (Bio-Rad). To measure gene expression, real-time quantitative PCR was performed using SYBR Green (iQSYBR Green Supermix, Bio-Rad Laboratories Inc.), and the instrument used was the CFX Connect™ real-time PCR detection system (Bio-Rad Laboratories Headquarters, Hercules, CA, USA). The nucleotide sequences of each primer used for the gene amplification reaction are shown in Table 2. Specifically, Table 2 shows the base sequences of the skin wrinkle improvement factor primers. After a hot start at 95°C for 10 minutes, PCR analysis was performed for 40 cycles at 95°C for 15 seconds, 57°C for 15 seconds, and 72°C for 30 seconds. After all cycles were completed, a melting curve analysis was performed to confirm the specificity of the primers. The results were analyzed using CFX Maestro™ Analysis Software provided by BioRad (Bio-Rad Laboratories Headquarters, Hercules, CA, USA).

[0280] As a result, as shown in Figure 1, it was confirmed that the ALT 001 of the present invention significantly increases TGFβR1 (Transforming Growth Factor beta-receptor 1), procollagen, and collagen type 1 (COL1), which are skin wrinkle improvement factors, in a concentration-dependent manner.

[0281] [Table 2]

[0282]

[0283]

[0284] Example 3. Confirmation of the effect of enhancing the function of proteins related to skin wrinkle improvement

[0285] In this example, it was confirmed whether the isoquinoline derivative of the present invention improves the function of a protein regarding skin wrinkle improvement. Specifically, the same HS27 cells as in Example 2 were used.

[0286] 5×10⁶ HS27 cells in a 6-well plate 5 Cells were seeded at wells, cultured overnight to stabilize, and then washed with DPBS. Subsequently, a UV lamp (5 Sankyo Denki G5T5 lamps, Sankyo Denki Co., Yokohama, Japan) at 50 mJ / cm² was used. 2UV irradiation was performed. L-ascorbic acid 100 μg / mL was used as a positive control, and ALT 001, the isoquinoline derivative of the present invention, was treated at concentrations of 4 μM, 12 μM, and 24 μM. After 24 and 48 hours, the respective media were removed, and the cells were homogenized using lysis buffer containing a protease inhibitor and maintained on ice for a certain period. Subsequently, proteins were separated by centrifugation (12,000 rpm, 20 min, 4°C). Protein quantification was performed using the Bradford method with BSA and Bio-Rad protein assay Dye Reagent Concentrate (Bio-Rad, Hercules, CA USA). Twenty μL of each protein sample was loaded onto a 10% SDS-PAGE (Sodium dodecyl sulfate-polyacrylamide gel) and separated by electrophoresis, after which the proteins were transferred to a nitrocellulose membrane. The transferred membrane was blocked for one hour with 5% skim milk (TBS containing 0.5% Tween 20) dissolved in TBST buffer. Subsequently, primary antibodies against collagen type I, Smad3, elastin, and β-actin (Cell Signaling Technology, Beverly, MA, USA) were reacted at room temperature for three hours, followed by a secondary antibody polymerized with HRP (horseradish peroxidase) (Cell Signaling Technology, Beverly, MA, USA) for 60 minutes.

[0287] After developing color using an enhanced chemiluminescent (ECL) reagent (Amersham pharmacia Biotech, UK), images were captured using Easy Photo. The band densities of the captured Western blot band images were measured using Image J software (NIH, Bethesda, MD).

[0288] The results of this example were analyzed using the statistical program SPSS (Statistical package for social science version 25.0, SPSS Inc., Chicago, IL, USA), and the measurement results of each item were expressed as mean ± standard deviation (mean ± SD). Mean differences between groups were confirmed using one-way ANOVA, and statistical significance was tested at the P<0.05 level using Duncan's test.

[0289]

[0290] It is known that ultraviolet (UV) irradiation inhibits TGF-β, a major regulator of procollagen synthesis in dermal fibroblasts, and the Smad pathway activated by it, thereby reducing the production of procollagen type I and consequently causing collagen loss. Additionally, Collagen type I constitutes the largest portion of skin tissue and is a major protein responsible for maintaining skin elasticity; it is characterized by its degradation and inhibition of production by matrix metalloproteinases (MMPs) known as collagenases. Smad3 is known to promote the synthesis of collagen and extracellular matrix (ECM) proteins by mediating TGF-β signaling. Therefore, in this embodiment, after treating UV-irradiated HS27 human fibroblasts with ALT 001, the protein expression of wrinkle-related factors p-Smad3 / Smad3, Collagen type I, and Elastin was measured at 24 and 48 hours, as shown in Figures 2a, 2b, 3a, and 3b below.

[0291] First, in the analysis after 24 hours, the protein expression levels of p-Smad3 / Smad3, Collagen type I, and Elastin were examined, and it was confirmed that they were expressed at the lowest levels in the UV-irradiated group (C). On the other hand, it was confirmed that the protein expression in the ALT 001-treated group was significantly increased compared to the UV-irradiated group (C). In particular, when the ALT 001 24 μM-treated group was compared to the normal control group (NC) that was not treated with UV light, no significant difference was observed in the protein expression levels of Collagen type I and Elastin (Figs. 2a and 2b). This result suggests that protein expression reduced by UV damage was protected by treatment with ALT 001.

[0292] In the analysis after 48 hours, the protein expression levels of p-Smad3 / Smad3, Collagen type I, and Elastin were confirmed to be lowest in the UV-irradiated group (C). On the other hand, it was confirmed that the ALT 001 12 μM and ALT 001 24 μM treatment groups showed a significant increase compared to the UV-irradiated group (C) (Figs. 3a and 3b).

[0293] As a result, it was confirmed that ALT 001 exhibits an anti-wrinkle effect that restores the reduced expression of wrinkle-improving proteins caused by UV-induced damage, and that the effect increases in a concentration-dependent and time-dependent manner.

[0294]

[0295] Example 4. Confirmation of skin wrinkle improvement effect in ex vivo human-derived skin tissue

[0296] In this embodiment, it was confirmed whether the isoquinoline derivative of the present invention exerts a skin wrinkle improvement effect in ex vivo human-derived skin tissue.

[0297]

[0298] Example 4.1. Obtaining Human-Derived Skin Tissue and Test Group

[0299] Skin tissue discarded after surgery was used in the example with IRB approval (IRB approval number: E-2025-016-01). After washing the human-derived skin tissue twice with PBS inside a clean bench, it was transferred to a sterile Petri dish, and holes were punched in the human-derived skin tissue using a Biopsy Punch (KAI Medical, Japan).

[0300] In this example, the skin wrinkle improvement effect was confirmed under conditions for the untreated group, negative control group, PDRN (Polydeoxyribonucleotide) treated group (control group), and ALT 001 treated group (test group) (Table 3).

[0301] [Table 3]

[0302]

[0303]

[0304] Specifically, to evaluate the anti-wrinkle effect on the ALT 001 treatment group, UVB (300 mJ / cm²) was applied to the negative control group, control group, and test group (excluding the untreated group). Subsequently, a Microneedle Therapy System (MTS) was applied once (LARCO-AMTS-08, 2.5 Round 16 Pins, 0.2 mm) to the skin tissue of the test group (excluding the untreated group, negative control group, and control group), and processed using an 8 mm biopsy punch according to the number of groups. Afterward, 7 μL of the test product was applied and incubated for 48 hours, and safety and anti-wrinkle related factors in the skin were confirmed through histological staining.

[0305]

[0306] Example 4.2. Confirmation of the safety of isoquinoline derivatives in skin tissue

[0307] In this embodiment, through the results of hematoxylin and eosin (H&E) staining, it was confirmed that no adverse reactions were observed and safety was ensured when the isoquinoline derivative of the present invention was treated with human-derived skin tissue. Specifically, paraffin blocks were prepared using tissue fixed with a 10% formalin solution, and tissue slides were prepared by sectioning the tissue to a thickness of 3 μm. Subsequently, after a hydration process, staining was performed with hematoxylin and eosin solutions, and the epidermis and dermis were observed at 200x magnification using an optical microscope to check for structural changes.

[0308] As a result, adverse reactions in ex vivo human skin tissue cross-sections were observed through hematoxylin and eosin (H&E) staining, and it was confirmed that no adverse reactions were observed when ALT 001 was treated (Fig. 4a). The fact that no adverse reactions were observed when the isoquinoline derivative of the present invention was treated suggests that the isoquinoline derivative of the present invention has secured safety.

[0309]

[0310] Example 4.3. Confirmation of the collagen expression-promoting effect of isoquinoline derivatives

[0311] In this embodiment, through the results of Masson's trichrome staining (MT staining), it was confirmed that collagen expression is promoted when the isoquinoline derivative of the present invention is treated to human-derived skin tissue, and consequently, the elasticity of the skin tissue is improved. Specifically, a paraffin block was prepared using tissue fixed with a 10% formalin solution, and tissue slides were prepared by sectioning the tissue to a thickness of 3 μm. Subsequently, after a hydration process, the tissue was stained with Biebrich Scarlet-Acid Fuchsin solution for 5 minutes and washed, then stained again with Phosphotungstic / Phosphomolybdic Acid for 5 minutes, and finally stained with Aniline blue and Acetic Acid solution. In addition, stained tissue slides were photographed using a slide scanner (Digital pathology 5 Slides Scanner, KF-PRO-005, Zhejiang), images were extracted using a slide viewer (Slide Viewer, 3DHISTECH, Hungary), and the ratio of the area occupied by blue-stained collagen to the total area of ​​the photograph was analyzed using Image J (The National Institutes of Health, USA).

[0312] As a result, collagen density was evaluated by MT staining on ex vivo human skin tissue cross-sections, and it was confirmed that collagen expression increased by 14.46% (improved) in the ALT 001-treated group compared to the negative control group (Figs. 4b to 4d).

[0313]

[0314] Example 4.4. Confirmation of the elastin expression-promoting effect of isoquinoline derivatives

[0315] In this embodiment, through the results of Victoria blue staining (VB staining), it was confirmed that elastin expression is promoted when the isoquinoline derivative of the present invention is treated to human-derived skin tissue, and consequently, the elasticity of the skin tissue is improved. Specifically, a paraffin block was prepared using tissue fixed with a 10% formalin solution, and tissue slides were prepared by sectioning the tissue to a thickness of 3 μm. Subsequently, the tissue was stained with Victoria Blue B after a hydration process. In addition, the stained tissue slides were photographed using a slide scanner (Digital pathology 5 Slides Scanner, KF-PRO-005, Zhejiang), images were extracted using a slide viewer program (Slide Viewer, 3DHISTECH, Hungary), and the ratio of the area occupied by blue-stained elastin (elastic fiber) to the total area of ​​the captured photographs was analyzed using Image J (The National Institutes of Health, USA).

[0316] As a result, when elastin density was evaluated by Victoria blue staining on cross-sections of ex vivo human-derived skin tissue, it was confirmed that the expression of elastin (elastic fiber) in the ALT 001-treated group increased (improved) by 41.15% compared to the negative control group (Figs. 4e to 4g).

[0317]

[0318] The isoquinoline derivative of the present invention did not exhibit adverse reactions upon treatment, and the expression levels of collagen and elastin increased (improved). Therefore, it was confirmed that the isoquinoline derivative of the present invention is not only a compound with assured safety, but also significantly improves the structural elasticity indicators of the skin and exhibits effects of improving skin elasticity and anti-wrinkle properties in human-derived skin tissues induced by photoaging.

[0319]

[0320] Example 5. Confirmation of the effect of inhibiting the function of factors related to the occurrence of inflammation

[0321] In this embodiment, it was confirmed whether the isoquinoline derivative of the present invention promotes immune activity and inhibits the function of factors related to the occurrence of inflammation. Specifically, experiments were conducted using Raw264.7 cells, which are derived from mouse bone marrow tissue and are an important tool for immunological and inflammatory research due to their relatively easy culture and manipulation. In this embodiment, inflammation was induced with LPS (lipopolysaccharide) to confirm the anti-inflammatory efficacy of the samples. For the in vitro test, the groups were tested as NC (Normal Control), a group treated with the inflammatory factor LPS at 5 μg / mL, and an ALT 001 test sample group (groups treated with ALT 001 at concentrations of 15 μM, 30 μM, and 50 μM, respectively).

[0322] 1×10⁶ Raw264.7 cells in a 6-well plate 6Cells were seeded per well and stabilized overnight. After washing with DPBS, the cells were treated with ALT 001 at concentrations of 15 μM, 30 μM, and 50 μM. After 22 hours, 5 μg / mL of LPS was added. Two hours after LPS treatment, the cells were washed with DPBS. Subsequently, cells were collected using a scraper, RNA was extracted using the RnasyMini Kit (QIAGEN, Hilden, Germany), and then synthesized into cDNA using the iScript™ cDNA Synthesis Kit (Bio-Rad). To measure gene expression, real-time quantitative PCR was performed using SYBR Green (IqSYBR Green Supermix, Bio-Rad Laboratories Inc.), utilizing the CFX Connect™ real-time PCR detection system (Bio-Rad Laboratories Headquarters, Hercules, CA, USA). The nucleotide sequences of each primer used for the gene amplification reaction are shown in Table 4. Specifically, Table 4 presents the nucleotide sequences of the inflammatory factor primers. After a hot start at 95°C for 10 minutes, PCR analysis was performed for 40 cycles at 95°C for 15 seconds, 55°C for 15 seconds, and 72°C for 30 seconds. After all cycles were completed, a melting curve analysis was performed to confirm the specificity of the primers. The results were analyzed using the CFX Maestro™ Analysis Software provided by BioRad (Bio-Rad Laboratories Headquarters, Hercules, CA, USA).

[0323] As a result, as shown in Figure 5, it was confirmed that when the ALT 001 of the present invention was treated, the amounts of inflammatory factors IL-1β, IL-6, and TNF-α were reduced, and based on the above results, it was confirmed that the ALT 001 of the present invention promotes immune activity and reduces inflammatory factors.

[0324] [Table 4]

[0325]

[0326]

[0327] The foregoing description of the present invention is for illustrative purposes only, and those skilled in the art will understand that other specific forms can be easily modified without altering the technical spirit or essential features of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

[0328] The present invention relates to a novel isoquinoline derivative and its use. The novel isoquinoline derivative of the present invention exhibits the effect of enhancing the function of wrinkle improvement factors and inhibiting the function of factors related to the occurrence of inflammation. As such, it is expected to be utilized in the development of cosmetic compositions, medical devices, quasi-drug compositions, and health functional food compositions for anti-wrinkle or anti-inflammatory purposes, and thus industrial applicability exists.

Claims

1. A cosmetic composition for anti-wrinkle or anti-inflammatory purposes comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

2. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory purposes, characterized in that the compound represented by the above chemical formula 1 is one or more selected from the group consisting of compounds listed in Table 1 below: [Table 1] 3. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory purposes, characterized in that the compound represented by Chemical Formula 1 above is one or more selected from the group consisting of the following compounds: (1) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium bromide; (2) 2,3,9,10-tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium hydroxide; and (3) 2,3,9,10-Tetrahydroxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride.

4. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory purposes, characterized in that the wrinkles are skin wrinkles caused by one or more selected from the group consisting of ultraviolet rays and skin inflammation.

5. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory properties, characterized in that the wrinkles are wrinkles resulting from a decrease in the expression or activity of one or more proteins selected from the group consisting of Transforming Growth Factor beta-receptor 1 (TGFβR1), procollagen, collagen, collagen type 1, Smad3, and elastin, or genes encoding such proteins.

6. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory properties, characterized in that the inflammation is inflammation caused by increased expression or activity of one or more proteins selected from the group consisting of Interleukin-1 beta (IL-1β), Interleukin 6 (IL-6), and tumor necrosis factor-α (TNF-α), or genes encoding such proteins.

7. In Paragraph 1, A cosmetic composition for anti-wrinkle or anti-inflammatory purposes, characterized in that the above composition is processed by one or more methods selected from the group consisting of the MTS (Microneedle Therapy System) method and the AMTS (Auto Microneedle Therapy System) method.

8. A medical device selected from functional wound dressings, fillers, or composite fillers having anti-wrinkle or anti-inflammatory functions, comprising as an active ingredient a compound represented by Chemical Formula 1 or Chemical Formula 2 below, an isomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

9. An anti-wrinkle or anti-inflammatory quasi-drug composition comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

10. In Paragraph 9, The above-mentioned quasi-drug composition is characterized by being formulated into one or more selected from the group consisting of external preparations, powders, antiseptics and disinfectants, toothpastes, ointments, lotions, oral preparations, wet wipes, sprays, patches, bandages, patches, and combinations thereof, for anti-wrinkle or anti-inflammatory purposes.

11. A health functional food composition for anti-wrinkle or anti-inflammatory purposes, comprising as an active ingredient a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a food-grade acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

12. A non-therapeutic method for anti-wrinkle or anti-inflammation, comprising the step of administering a composition comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof, to an individual in need thereof in a cosmetically effective amount: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

13. Anti-wrinkle or anti-inflammatory use of a composition comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

14. Use for preparing anti-wrinkle or anti-inflammatory agents comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a cosmetically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

15. An anti-wrinkle or anti-inflammatory method comprising the step of administering a composition comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof, to an individual in need thereof in a pharmaceutically effective amount: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

16. Anti-wrinkle or anti-inflammatory use of a composition comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

17. Use for preparing anti-wrinkle or anti-inflammatory agents comprising, as an active ingredient, a compound represented by the following Chemical Formula 1 or Chemical Formula 2, an isomer thereof, or a pharmaceutically acceptable salt thereof: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X is F, Cl, Br, I, or OH.

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