KR20220033823A - Antifungal composition comprising 6-pentyl-α-pyrone as an active ingredient - Google Patents

Abstract

The present invention relates to an antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient. 6-pentyl-α-pyrone of the present invention has antifungal activity on Candida spp., Cryptococcus spp., Malassezia spp., and Trichophyton spp., thereby being able to be usefully used as the antifungal composition.

Description

Antifungal composition comprising 6-pentyl-α-pyrone as an active ingredient {Antifungal composition comprising 6-pentyl-α-pyrone as an active ingredient}

The present invention relates to an antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient, and the like.

Fungus refers to a group of microorganisms including mold, yeast, and mushrooms. Most of them cannot synthesize nutrients themselves, so they live as parasites on other organisms. In humans, most of the infections occur on the skin, such as the scalp, hair, face, arms, legs, nails or toenails, where a lot of dead and peeling cells are distributed, but it can also be infected with intestinal mucosa or vaginal mucosa, and it can also cause systemic infection by infection with internal organs. also cause On the other hand, fungal infections are caused by immunodeficiency, old age, use of immunosuppressants or steroids, nutritional deficiencies, poor hygiene, and contact with infected patients.

An antifungal agent refers to a substance for preventing or treating symptoms caused by a fungal infection by inhibiting the growth or reproduction of fungi.

On the other hand, cryptococcosis is caused by an infection of Cryptococcus neoformans and infects all parts of the body including the skin in patients with weakened immunity such as AIDS patients, especially the meninges. It causes meningitis, brain abscesses and brain tumors. Candidasis is a mycosis caused by Candida albicans and was first isolated from thrush patients.

In addition, it has been recently known that the bacteria that cause dandruff are fungi, that is, yeast, and in particular, Malassezia sp. It has been reported that when the Malassezia fungus overproliferates due to environmental triggers such as change, sweat, and food, dandruff symptoms such as scale and itching occur, and when the overproliferation is severe, seborrheic dermatitis occurs. In addition, when dandruff occurs a lot, the scalp is excessively rubbed due to itching, etc., thereby causing a wound or, in some cases, inflammation, and may cause hair loss. In the case of a composition for the purpose of treating, preventing or improving dandruff and itching, it is an essential requirement to contain a component capable of inhibiting the proliferation of a fungus of the genus Malassezia , which is the main causative agent of dandruff, Currently commercially available compositions include antifungal agents such as ketoconazole, zinc pyrithion, itraconazole or piroctone Olamine. In addition, tar, sulfur, salicylic acid, etc. have been used to relieve itching and scale, and selenium sulfide, etc. have been used to suppress the hyperproliferation of epidermal cells. However, while the antifungal agents that have been used for the treatment of dandruff have a good effect on the treatment of dandruff, most of them are artificially synthesized, raising questions about human safety. However, long-term use of ketoconazole, an active ingredient of a dandruff treatment such as Nizoral commercially available in Korea, has raised a problem that may cause adverse effects on the endocrine system.

Ringworm's site of occurrence and the characteristics of the lesion are determined by the type of dermatophytes transmitted. Also, the anatomical characteristics of the site of occurrence are involved in symptom development. In the case of transmission from animals, Trichopyton mentagrophytes is the most causative bacterium, and it mainly occurs on exposed areas such as the scalp (tinea capitis), face (tinea face), chest and extremities (tinea corpuscle), and itching is relatively severe. When it is transmitted from other people, Trichophyton rubrum is the most common causative agent, and the lesion starts mainly on the feet (tinea nail) and spreads to other areas, such as the hands (ringworm of the hands), groin (tinea tinea), and nails and toenails (tinea tinea). Symptoms are not severe and tend to progress to chronic condition. According to the site of occurrence, it is classified into ringworm of the head, ringworm of the body, ringworm of the head (tinea genitalia), ringworm of the feet, ringworm of the face, ringworm of the hands, ringworm of the feet, ringworm of the feet, etc. The clinical characteristics are different according to the characteristics of the skin, hair, nails and toenails, the thickness of the stratum corneum according to the anatomical location of the skin, and the physiological characteristics, and thus there is a difference in the treatment method and duration.

Current commercially available antifungal agents have disadvantages in that they are toxic, narrow active range, and have a strong fungistatic rather than fungicidal nature. Some of these also exhibit drug-drug interactions, which results in very complex treatment. According to the recent trend in which a lot of fungal infections occur in immunosuppressed patients and the patient population is steadily increasing, there is an increasing demand for new antifungal agents having broad-spectrum activity and excellent pharmacological properties.

Republic of Korea Patent Registration No. 10-1302678

Accordingly, the present inventors found that 6-pentyl-α-pyrone is a pathogenic fungus that causes thrush, vaginitis, etc. in the human body, Candida albicans , Cryptococcus neoformans that causes meningitis and pneumonia, dandruff, seborrheic dermatitis , Malassezia restricta, Malassezia globosa, Malassezia sympodialis, Malassezia furfur , otitis externa in dogs, Malassezia pachydermatis causing atopic dermatitis, and Trichophyton rubrum causing athlete's foot or psoriasis, Trichophyton mentagrophytes showing strong antifungal effect on strains By confirming, the present invention was completed.

Accordingly, an object of the present invention is to provide an antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient.

Another object of the present invention is to provide a pharmaceutical composition for preventing or treating pathogenic fungal infectious diseases comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient. will do

Another object of the present invention is to provide a cosmetic composition for preventing or improving pathogenic fungal-infectious skin diseases comprising 6-pentyl-α-pyrone or a cosmetically acceptable salt thereof as an active ingredient. will do

However, the technical problem to be achieved by the present invention is not limited to the above-mentioned problems, and other problems not mentioned will be clearly understood by those skilled in the art from the following description.

Accordingly, the present invention provides an antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient.

In addition, the present invention provides a pharmaceutical composition for preventing or treating pathogenic fungal infectious diseases comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient. .

In addition, the present invention provides a cosmetic composition for preventing or improving pathogenic fungal-infectious skin diseases comprising 6-pentyl-α-pyrone or a cosmetically acceptable salt thereof as an active ingredient. .

In one embodiment of the present invention, the 6-pentyl-α-pyrone may be represented by the following Chemical Formula 1, but is not limited thereto.

[Formula 1]

In another embodiment of the present invention, the antifungal composition is composed of Candida spp. , Cryptococcus spp. , Malassezia spp. and Trichophyton sp . It may have antifungal activity against one or more fungi selected from the group, but is not limited thereto.

In another embodiment of the present invention, the infectious disease is Candida spp. , Cryptococcus spp. , Malassezia spp. , and Trichophyton spp. ) consisting of It may be a disease caused by one or more fungi selected from the group, but is not limited thereto.

In another embodiment of the present invention, the infectious disease may be one or more selected from the group consisting of candidiasis, cryptococcus, seborrheic dermatitis, dandruff, atopic dermatitis, otitis externa, athlete's foot and ringworm, but is not limited thereto.

In another embodiment of the present invention, the candidiasis may be at least one selected from the group consisting of thrush, esophageal candidiasis, vaginal candidiasis, candida mycosis, candida endophthalmitis, candida peritonitis, candida osteoarthritis, candida spondylitis and hepatosplenic candidiasis, However, the present invention is not limited thereto.

In another embodiment of the present invention, the pathogenic fungal infectious skin disease may be caused by the genus Malassezia spp. or Trichophyton spp. , but is not limited thereto.

In another embodiment of the present invention, the pathogenic fungal infectious skin disease may be one or more selected from the group consisting of seborrheic dermatitis, dandruff, atopic dermatitis, athlete's foot and ringworm, but is not limited thereto.

In another embodiment of the present invention, the cosmetic composition may be selected from the group consisting of shampoo, conditioner, hair tonic, hair treatment, foot cream, detergent, skin care and soap, but is not limited thereto.

In addition, the present invention provides an antifungal method comprising administering to a subject an effective amount of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof.

In addition, the present invention provides an antifungal use of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof.

In addition, the present invention provides the use of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof for the preparation of an antifungal agent.

In addition, the present invention provides a method for preventing or treating a pathogenic fungal infectious disease, comprising administering to an individual an effective amount of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof do.

In addition, the present invention provides the use of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof for the prevention or treatment of pathogenic fungal infectious diseases.

In addition, the present invention provides the use of 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof for the preparation of a medicament for a pathogenic fungal infectious disease.

6-pentyl-α-pyrone of the present invention has antifungal activity against Candida spp., Cryptococcus spp., Malassezia spp. and Trichophyton spp. It is excellent and can be usefully used as an antifungal composition.

1 shows the structural formula and ¹ H-NMR data of 6-pentyl-α-pyrone isolated and purified from Trichoderma gamsii .

Accordingly, the present invention provides an antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient.

In addition, the present invention provides a pharmaceutical composition for preventing or treating pathogenic fungal infectious diseases comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient. .

In addition, the present invention provides a cosmetic composition for preventing or improving pathogenic fungal-infectious skin diseases comprising 6-pentyl-α-pyrone or a cosmetically acceptable salt thereof as an active ingredient. .

Hereinafter, the present invention will be described in detail.

In the present invention, the 6-pentyl-α-pyrone (6-pentyl-α-pyrone) may also be referred to as 6-Amyl-α-pyrone, 6-pentyl-2-pyrone, or 6PP, and 6-pentylpyran-2 It can have an IUPAC name of -one.

In the present invention, the 6-pentyl-α-pyrone may be represented by the following Chemical Formula 1, but is not limited thereto.

[Formula 1]

In the present invention, the 6-pentyl-α-pyrone may be isolated from Trichoderma gamsii or a culture thereof, but is not limited thereto.

In the present invention, the antifungal composition is one or more selected from the group consisting of Candida spp. , Cryptococcus spp. , Malassezia spp. and Trichophyton spp. It may have antifungal activity against fungi, but is not limited thereto.

In the present invention, the 6-pentyl-α-pyrone may have an antifungal effect, but is not limited thereto.

The 6-pentyl-α-pyrone may have a non-aromatic double bond and one or more asymmetric centers. Thus, they may occur as racemates and racemic mixtures, single enantiomers, individual diastereomers, diastereomeric mixtures and cis- or trans-isomers. All such isomeric forms are contemplated.

6-pentyl-α-pyrone according to the present invention can be isolated from nature or prepared by chemical synthesis of compounds known in the art.

In addition, the compound of the present invention can be isolated and purified from Trichoderma gamsii or a culture thereof.

In the present invention, the infectious disease is one or more selected from the group consisting of Candida spp. , Cryptococcus spp. , Malassezia spp. , and Trichophyton spp. It may be a disease caused by a fungus, but is not limited thereto.

In the present invention, the infectious disease may be one or more selected from the group consisting of candidiasis, cryptococcosis, seborrheic dermatitis, dandruff, atopic dermatitis, otitis externa, athlete's foot and ringworm, but is not limited thereto.

In the present invention, the candidiasis may be at least one selected from the group consisting of thrush, esophageal candidiasis, vaginal candidiasis, candida mycosis, candida endophthalmitis, candida peritonitis, candida osteoarthritis, candida spondylitis and hepatosplenic candidiasis, but is not limited thereto. .

In the present invention, the cryptococcosis is caused by infection of Cryptococcus neoformans and is infected all parts of the body, including the skin, in patients with weakened immunity such as AIDS patients, especially meninges. It causes meningitis, brain abscesses and brain tumors.

In the present invention, the pathogenic fungal infectious skin disease may be caused by the genus Malassezia spp. or Trichophyton spp. , but is not limited thereto.

In the present invention, the pathogenic fungal-infectious skin disease may be one or more selected from the group consisting of seborrheic dermatitis, dandruff, atopic dermatitis, athlete's foot and ringworm, but is not limited thereto.

In the present invention, the Candida genus fungus may be Candida albicans , but is not limited thereto.

In the present invention, the Cryptococcus genus fungus may be Cryptococcus neoformans , but is not limited thereto.

In the present invention, the Malassezia genus fungus is Malassezia restricta ( Malassezia restricta ) , Malassezia globosa ( Malassezia globosa ) , Malassezia sympodialis ( Malassezia sympodialis ) , Malassezia pachydermatis ( Malassezia pachydermatis) , and may be at least one selected from the group consisting of Malassezia furfur, but is not limited thereto.

In the present invention, the Trichophyton genus fungus may be Trichophyton rubrum or Trichophyton mentagrophytes , but is not limited thereto.

In the present invention, the composition may be a pharmaceutical composition, a food composition or a cosmetic composition, but is not limited thereto.

The present invention may also include a pharmaceutically acceptable salt of 6-pentyl-α-pyrone as an active ingredient. As used herein, the term “pharmaceutically acceptable salt” includes salts derived from pharmaceutically acceptable inorganic acids, organic acids, or bases.

Examples of suitable acids include hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, fumaric acid, maleic acid, phosphoric acid, glycolic acid, lactic acid, salicylic acid, succinic acid, toluene-p-sulfonic acid, tartaric acid, acetic acid, citric acid, methanesulfonic acid, formic acid , benzoic acid, malonic acid, gluconic acid, naphthalene-2-sulfonic acid, benzenesulfonic acid, and the like. Acid addition salts can be prepared by conventional methods, for example, by dissolving the compound in an aqueous solution of an excess of acid, and precipitating the salt using a water-miscible organic solvent such as methanol, ethanol, acetone or acetonitrile. It can also be prepared by heating an equimolar amount of the compound and an acid or alcohol in water and then evaporating the mixture to dryness, or by suction filtration of the precipitated salt.

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. The alkali metal or alkaline earth metal salt can be obtained, for example, by dissolving the compound in an excess alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the undissolved compound salt, and then evaporating and drying the filtrate. In this case, as the metal salt, it is pharmaceutically suitable to prepare a sodium, potassium or calcium salt, and the corresponding silver salt can be obtained by reacting an alkali metal or alkaline earth metal salt with a suitable silver salt (eg, silver nitrate).

The content of 6-pentyl-α-pyrone in the composition of the present invention can be appropriately adjusted depending on the symptoms of the disease, the degree of progression of the symptoms, the condition of the patient, etc., for example, 0.0001 to 99.9% by weight, or 0.001 based on the total weight of the composition. to 50% by weight, but is not limited thereto. The content ratio is a value based on the dry amount from which the solvent is removed.

The pharmaceutical composition according to the present invention may further include suitable carriers, excipients and diluents commonly used in the preparation of pharmaceutical compositions. The excipient may be, for example, at least one selected from the group consisting of a diluent, a binder, a disintegrant, a lubricant, an adsorbent, a humectant, a film-coating material, and a controlled-release additive.

The pharmaceutical composition according to the present invention can be prepared according to a conventional method, respectively, in powders, granules, sustained-release granules, enteric granules, liquids, eye drops, elsilic, emulsions, suspensions, alcohols, troches, fragrances, and limonaade. , tablets, sustained release tablets, enteric tablets, sublingual tablets, hard capsules, soft capsules, sustained release capsules, enteric capsules, pills, tinctures, soft extracts, dry extracts, fluid extracts, injections, capsules, perfusates, Warnings, lotions, pasta, sprays, inhalants, patches, sterile injection solutions, or external preparations such as aerosols can be formulated and used, and the external preparations are creams, gels, patches, sprays, ointments, warning agents , lotion, liniment, pasta, or cataplasma.

Carriers, excipients and diluents that may be included in the pharmaceutical composition according to the present invention include lactose, dextrose, sucrose, oligosaccharide, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.

In the case of formulation, it is prepared using commonly used diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrants, and surfactants.

Corn starch, potato starch, wheat starch, lactose, sucrose, glucose, fructose, di-mannitol, precipitated calcium carbonate, synthetic aluminum silicate, phosphoric acid as additives for tablets, powders, granules, capsules, pills, and troches according to the present invention Calcium monohydrogen, calcium sulfate, sodium chloride, sodium hydrogen carbonate, purified lanolin, microcrystalline cellulose, dextrin, sodium alginate, methyl cellulose, sodium carboxymethyl cellulose, kaolin, urea, colloidal silica gel, hydroxypropyl starch, hydroxypropyl methyl Cellulose, (HPMC) 1928, HPMC 2208, HPMC 2906, HPMC 2910, propylene glycol, casein, calcium lactate, excipients such as Primogel; Gelatin, gum arabic, ethanol, agar powder, cellulose acetate phthalate, carboxymethylcellulose, calcium carboxymethylcellulose, glucose, purified water, sodium caseinate, glycerin, stearic acid, sodium carboxymethylcellulose, sodium methylcellulose, methylcellulose, microcrystalline cellulose, dextrin , hydroxycellulose, hydroxypropyl starch, hydroxymethylcellulose, purified shellac, starch powder, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, etc. Hydroxypropyl methylcellulose, corn starch, agar powder, methylcellulose, bentonite, hydroxypropyl starch, sodium carboxymethylcellulose, sodium alginate, calcium carboxymethylcellulose, calcium citrate, sodium lauryl sulfate, silicic anhydride, 1-hydroxy Propyl cellulose, dextran, ion exchange resin, polyvinyl acetate, formaldehyde treated casein and gelatin, alginic acid, amylose, guar gum, sodium bicarbonate, polyvinylpyrrolidone, calcium phosphate, gelled starch, gum arabic, Disintegrants such as amylopectin, pectin, sodium polyphosphate, ethyl cellulose, sucrose, magnesium aluminum silicate, di-sorbitol solution, light anhydrous silicic acid; Calcium stearate, magnesium stearate, stearic acid, hydrogenated vegetable oil, talc, lycopodite, kaolin, petrolatum, sodium stearate, cacao butter, sodium salicylate, magnesium salicylate, polyethylene glycol 4000, 6000, liquid paraffin, hydrogenated soybean oil (Lubri) wax), aluminum stearate, zinc stearate, sodium lauryl sulfate, magnesium oxide, macrogol, synthetic aluminum silicate, silicic anhydride, higher fatty acid, higher alcohol, silicone oil, paraffin oil, polyethylene glycol fatty acid ether, starch, sodium chloride, A lubricant such as sodium acetate, sodium oleate, dl-leucine, light anhydrous silicic acid; may be used.

As additives for the liquid formulation according to the present invention, water, diluted hydrochloric acid, diluted sulfuric acid, sodium citrate, monostearate sucrose, polyoxyethylene sorbitol fatty acid esters (Twinester), polyoxyethylene monoalkyl ethers, lanolin ethers, Lanolin esters, acetic acid, hydrochloric acid, aqueous ammonia, ammonium carbonate, potassium hydroxide, sodium hydroxide, prolamine, polyvinylpyrrolidone, ethyl cellulose, sodium carboxymethyl cellulose, etc. can be used.

In the syrup according to the present invention, a sucrose solution, other sugars or sweeteners may be used, and if necessary, a fragrance, colorant, preservative, stabilizer, suspending agent, emulsifying agent, thickening agent, etc. may be used.

Purified water may be used in the emulsion according to the present invention, and if necessary, an emulsifier, preservative, stabilizer, fragrance, etc. may be used.

Suspending agents such as acacia, tragacantha, methylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, microcrystalline cellulose, sodium alginate, hydroxypropylmethylcellulose, HPMC 1828, HPMC 2906, HPMC 2910 may be used in the suspending agent according to the present invention. and, if necessary, surfactants, preservatives, stabilizers, colorants, and fragrances may be used.

The injection according to the present invention includes distilled water for injection, 0.9% sodium chloride injection solution, ring gel injection solution, dextrose injection solution, dextrose + sodium chloride injection solution, PEG (PEG), lactated ring gel injection solution, ethanol, propylene glycol, non-volatile oil-sesame oil , solvents such as cottonseed oil, peanut oil, soybean oil, corn oil, ethyl oleate, isopropyl myristate, and benzene benzoate; Solubilizing aids such as sodium benzoate, sodium salicylate, sodium acetate, urea, urethane, monoethylacetamide, butazolidine, propylene glycol, tweens, nijeongtinamide, hexamine, and dimethylacetamide; Weak acids and their salts (acetic acid and sodium acetate), weak bases and their salts (ammonia and ammonium acetate), organic compounds, proteins, buffers such as albumin, peptone, gum; isotonic agents such as sodium chloride; sodium bisulfite (NaHSO ₃ ) carbon dioxide gas, sodium metabisulfite (Na ₂ S ₂ O ₃ ), sodium sulfite (Na ₂ SO ₃ ), nitrogen gas (N ₂ ), stabilizers such as ethylenediaminetetraacetic acid; sulphating agents such as sodium bisulfide 0.1%, sodium formaldehyde sulfoxylate, thiourea, disodium ethylenediaminetetraacetate, acetone sodium bisulfite; analgesic agents such as benzyl alcohol, chlorobutanol, procaine hydrochloride, glucose, and calcium gluconate; suspending agents such as SiMC sodium, sodium alginate, Tween 80, or aluminum monostearate.

The suppository according to the present invention includes cacao fat, lanolin, witepsol, polyethylene glycol, glycerogelatin, methyl cellulose, carboxymethyl cellulose, a mixture of stearic acid and oleic acid, Subanal, cottonseed oil, peanut oil, palm oil, cacao butter + Cholesterol, Lecithin, Lanet Wax, Glycerol Monostearate, Tween or Span, Imhausen, Monolene (Propylene Glycol Monostearate), Glycerin, Adeps Solidus, Butyrum Tego -G), Cebes Pharma 16, Hexalide Base 95, Cotomar, Hydroxote SP, S-70-XXA, S-70-XX75 (S-70-XX95), Hydro Hydrokote 25, Hydrokote 711, Idropostal, Massa estrarium, A, AS, B, C, D, E, I, T, Massa-MF, Masupol, Masupol-15, Neosupostal-N, Paramound-B, Suposiro (OSI, OSIX, A, B, C, D, H, L), Suppository IV type (AB, B, A, BC, BBG, E, BGF, C, D, 299), supostal (N, Es), Wecobi (W, R, S, M, Fs), tester triglyceride base (TG-95, MA, 57) and The same mechanism may be used.

Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations include at least one excipient in the extract, for example, starch, calcium carbonate, sucrose ) or lactose, gelatin, etc. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used.

Liquid formulations for oral administration include suspensions, internal solutions, emulsions, syrups, etc. In addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweeteners, fragrances, and preservatives may be included. there is. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Non-aqueous solvents and suspending agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate.

The pharmaceutical 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 at a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level is determined by the type, severity, drug activity, and type of the patient's disease; Sensitivity to the drug, administration time, administration route and excretion rate, treatment period, factors including concurrent drugs and other factors well known in the medical field may be determined.

The pharmaceutical composition according to the present invention may be administered as an individual therapeutic agent or may be administered in combination with other therapeutic agents, may be administered sequentially or simultaneously with conventional therapeutic agents, and may be administered singly or multiple times. In consideration of all of the above factors, it is important to administer an amount capable of obtaining the maximum effect with a minimum amount without side effects, which can be easily determined by a person skilled in the art to which the present invention pertains.

The pharmaceutical composition of the present invention may be administered to an individual by various routes. All modes of administration can be contemplated, for example, oral administration, subcutaneous injection, intraperitoneal administration, intravenous injection, intramuscular injection, paraspinal space (intrathecal) injection, sublingual administration, buccal administration, rectal insertion, vaginal It can be administered according to internal insertion, ocular administration, ear administration, nasal administration, inhalation, spraying through the mouth or nose, skin administration, transdermal administration, and the like.

The pharmaceutical composition of the present invention is determined according to the type of drug as an active ingredient along with several related factors such as the disease to be treated, the route of administration, the patient's age, sex, weight, and the severity of the disease.

In the present invention, "individual" means a subject in need of treatment for a disease, and more specifically, human or non-human primates, mice, rats, dogs, cats, horses, cattle, etc. It may be a mammal of, but is not limited thereto.

In the present invention, "administration" means providing a predetermined composition of the present invention to an individual by any suitable method.

In the present invention, “prevention” means any action that suppresses or delays the onset of a target disease, and “treatment” means that the target disease and its metabolic abnormalities are improved or It means all actions that are beneficially changed, and “improvement” means all actions that reduce the desired disease-related parameters, for example, the degree of symptoms by administration of the composition according to the present invention.

In addition, the composition of the present invention may be provided in the form of a quasi-drug composition.

The quasi-drug composition of the present invention may further include a pharmaceutically acceptable carrier, excipient or diluent if necessary in addition to the above components. The pharmaceutically acceptable carrier, excipient or diluent is not limited as long as it does not affect the effect of the present invention, for example, a filler, an extender, a binder, a wetting agent, a disintegrant, a surfactant, a lubricant, a sweetener, a fragrance, a preservative and the like.

Representative examples of acceptable carriers, excipients or diluents for the quasi-drug composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, maltitol, starch, gelatin, glycerin, acacia gum, alginate, calcium phosphate, calcium Carbonate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, propylene glycol, polyethylene glycol, vegetable oil , injectable esters, Witepsol, Macrogol, Tween 61, cacao butter, laurage, and the like.

The quasi-drug composition of the present invention may include, but is not limited to, disinfectant cleaner, shower foam, ointment, wet tissue, coating agent, etc. may be appropriately selected from among the techniques of

In addition, the composition of the present invention may be provided in the form of a food composition.

When 6-pentyl-α-pyrone of the present invention is used as a food additive, 6-pentyl-α-pyrone may be added as it is or used together with other foods or food ingredients, and may be appropriately used according to a conventional method. The mixed amount of the active ingredient may be appropriately determined according to the purpose of use (prevention, health or therapeutic treatment). In general, in the production of food or beverage, 6-pentyl-α-pyrone of the present invention may be added in an amount of 15% by weight or less, or 10% by weight or less based on the raw material. However, in the case of long-term intake for health and hygiene or health control, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount greater than the above range.

There is no particular limitation on the type of the food. Examples of foods to which the above substances can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, dairy products including ice cream, various soups, beverages, tea, drinks, There are alcoholic beverages and vitamin complexes, and includes all health functional foods in the ordinary sense.

The health beverage composition according to the present invention may contain various flavoring agents or natural carbohydrates as additional ingredients, as in a conventional beverage. The above-mentioned natural carbohydrates 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 the sweetener, natural sweeteners such as taumartin and stevia extract, synthetic sweeteners such as saccharin and aspartame, and the like can be used. The proportion of the natural carbohydrate 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.

In addition to the above, the composition of the present invention includes 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. may be contained. In addition, the composition of the present invention may contain the pulp for the production of natural fruit juice, fruit juice beverage, and vegetable beverage. These components may be used independently or in combination. The proportion of these additives is not critical, but is generally selected in the range of 0.01-0.20 parts by weight per 100 parts by weight of the composition of the present invention.

In addition, the composition of the present invention may be provided in the form of a cosmetic composition.

6-pentyl-α-pyrone of the present invention can be used as a cosmetic additive to prepare a cosmetic composition for keeping hands or feet clean. As an example, soap (solid soap, liquid soap, bouncy soap, body soap, hand soap, etc.), cleansing foam, shampoo (hair shampoo, dry shampoo, etc.) may be mentioned. Among them, soap is preferable, and in particular, it can be used in formulations such as liquid soap and body soap.

The dosage form of the cosmetic composition according to the present invention includes 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, It may be in the form of essence, nutritional essence, pack, soap, cleansing foam, cleansing lotion, cleansing cream, cleansing oil, cleansing balm, body lotion or body cleanser.

The cosmetic composition of the present invention may further include a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, high molecular weight polysaccharides, and sphingolipids.

As water-soluble vitamins, any type of vitamin can be used as long as it can be formulated in cosmetics. Examples include vitamin B1, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, and vitamin H. Also, their salts (thiamine hydrochloride, sodium ascorbate salt, etc.) and derivatives (ascorbic acid-2-phosphate sodium salt, ascorbic acid-2-phosphate magnesium salt, etc.) are also included in the water-soluble vitamins that can be used in the present invention. Included. Water-soluble vitamins can be obtained by conventional methods, such as a microbial transformation method, a purification method from a microbial culture, an enzymatic method, or a chemical synthesis method.

The oil-soluble vitamin may be any type of vitamin that can be formulated in cosmetics, and for example, vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol), etc. , their derivatives (ascorbine palmitate, ascorbine stearate, ascorbine dipalmitate, dl-alpha tocopherol acetate, dl-alpha tocopherol nicotinic acid, vitamin E, DL-pantothenyl alcohol, D-pantothenyl alcohol, pantothenyl ethyl ethers, etc.) are also included in the oil-soluble vitamins used in the present invention. Oil-soluble vitamins can be obtained by conventional methods such as a microbial transformation method, a purification method from a microbial culture, and an enzyme or chemical synthesis method.

The macromolecular peptide may be any compound as long as it can be formulated in cosmetics, and examples thereof include collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, and keratin. Polymeric peptides can be purified and obtained by conventional methods such as purification from a microbial culture solution, enzyme method or chemical synthesis method, or can be purified and used from natural products such as dermis of pigs or cattle, silk fiber of silkworms, etc.

The high molecular weight polysaccharide may be any compound as long as it can be formulated in cosmetics, and examples thereof include hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate, or a salt thereof (sodium salt, etc.). For example, chondroitin sulfate or a salt thereof can be used after purification from mammals or fish.

The sphingolipid may be any as long as it can be formulated in cosmetics, and examples thereof include ceramide, phytosphingosine, and sphingoglycolipid. Sphingo lipids can be purified by conventional methods from mammals, fish, shellfish, yeast or plants, or can be obtained by chemical synthesis.

In the cosmetic composition of the present invention, in addition to the above essential ingredients, other ingredients usually blended in cosmetics may be blended as needed.

Other ingredients that may be added include oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, UV absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjusters, alcohols, colorants, fragrances, A blood circulation promoter, a cooling agent, a restrictive agent, purified water, etc. are mentioned.

Examples of the fats and oils include ester fats and oils, hydrocarbon oils, silicone oils, fluorine oils, animal fats, and vegetable oils.

As ester-based fats and oils, tri2-ethylhexanoate glyceryl, 2-ethylhexanoate cetyl, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isocetyl isostearate, stearic acid Butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine Diisopropyl acid, isoalkyl neopentanoate, tri(caprylic acid, capric acid) glyceryl, trimethylol propane tri-2-ethylhexanoate, trimethylol propane triisostearate, pentaelysitol tetra2-ethylhexanoate , cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinoleate, isostea laurate Lil, isotridecyl myristate, isocetyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleate, octyldodecyl oleate, octyldodecyl linoleate, isostearic acid isopropyl, 2-ethylhexanoate cetoster Aryl, 2-ethyl stearyl hexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicapric acid, di(caprylic acid, capric acid) propylene glycol, dicaprylic acid propylene glycol, dicapric acid Neopentyl glycol phosphate, neopentyl glycol dioctanoate, glyceryl tricaprylate, glyceryl triundecyl, glyceryl triisopalmitate, glyceryl triisostearate, octyldodecyl neopentanoate, isostearyl octanoate , isononanoate octyl, neodecanoate hexyldecyl, neodecanoate octyldodecyl, isostearate isocetyl, isostearyl isostearate, isostearic acid octyldecyl, polyglycerol oleate, polyglycerol isostearate, Triisocetyl citrate, triisoalkyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyldecyl lactate, triethyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, trioctyl citrate, dimalate Isostearyl, 2-ethylhexyl hydroxystearate, di2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, Cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholesteryl oleate, phytsteryl isostearate, phytsteryl oleate, 12-stealoyl Ester type, such as hydroxy stearate isocetyl, 12-stealoyl hydroxy stearyl stearate, and 12-stealoyl hydroxy stearate isostearyl, etc. are mentioned.

Examples of hydrocarbon-based fats and oils include hydrocarbon-based fats and oils such as squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybudene, microcrystalline wax, petrolatum.

Examples of silicone-based oils and fats include polymethyl silicone, methylphenyl silicone, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane/methylcetyloxysiloxane copolymer, dimethylsiloxane/methylstealloxysiloxane copolymer, and alkyl Modified silicone oil, amino modified silicone oil, etc. are mentioned.

Perfluoropolyether etc. are mentioned as fluorine-type fats and oils.

As animal or vegetable oils, avocado oil, almond oil, olive oil, sesame oil, rice bran oil, saffron oil, soybean oil, corn oil, rapeseed oil, passerine oil, palm kernel oil, palm oil, castor oil, sunflower oil, grape seed oil , Cottonseed Oil, Palm Oil, Kukui Nut Oil, Wheat Germ Oil, Rice Germ Oil, Shea Butter, Wormwood Colostrum, Marcus Damien Nut Oil, Meadow Oil, Egg Yolk Oil, Tallow Oil, Horse Oil, Mink Oil, Orange Raffy Oil, Jojoba Oil , animal or plant oils and fats such as candelabra wax, carnauba wax, liquid lanolin, and hydrogenated castor oil.

Examples of the moisturizing agent include a water-soluble low-molecular moisturizer, a fat-soluble molecular moisturizer, a water-soluble polymer, and a fat-soluble polymer.

As water-soluble low molecular weight moisturizers, serine, glutamine, sorbitol, mannitol, pyrrolidone-sodium carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B (polymerization degree n = 2 or more), polypropylene Glycol (polymerization degree n=2 or more), polyglycerol B (polymerization degree n=2 or more), lactic acid, lactic acid salt, etc. are mentioned.

Cholesterol, cholesterol ester, etc. are mentioned as a fat-soluble low molecular weight humectant.

Examples of the water-soluble polymer include carboxyvinyl polymer, polyaspartate, tragacanth, xanthan gum, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, water-soluble chitin, chitosan, and dextrin. can

Examples of the fat-soluble polymer include polyvinylpyrrolidone/eicocene copolymer, polyvinylpyrrolidone/hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and high molecular weight silicone.

Examples of the emollient include long-chain acylglutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid, and lanolin fatty acid cholesteryl ester.

Nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc. are mentioned as surfactant.

Nonionic surfactants include self-emulsifying glycerin monostearate, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerol 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 alkanolamides, alkylamine oxides, hydrogenated soybean phospholipids, and the like.

Examples of the anionic surfactant include fatty acid soap, alpha-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate, alkyl amide sulfate, alkyl phosphate, POE alkyl phosphate, and alkyl amide phosphate. , alkyloylalkyltaurine salts, N-acylamino acid salts, POE alkylethercarboxylate salts, alkylsulfosuccinate salts, alkylsulfoacetate sodium, acylated hydrolyzed collagen peptide salts, perfluoroalkylphosphate esters, and the like. .

Examples of the cationic surfactant include alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, chloride Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salt of lanolin derivative, etc. are mentioned.

Examples of the amphoteric surfactant include carboxybetaine type, amidebetaine type, sulfobetaine type, hydroxysulfobetaine type, amidesulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amidamine type, etc. Amphoteric surfactant etc. are mentioned.

Examples of organic and inorganic pigments include silicic acid, silicic anhydride, magnesium silicate, talc, sericite, mica, kaolin, bengala, clay, bentonite, titanium-coated mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide. inorganic pigments such as calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, ultramarine blue, chromium oxide, chromium hydroxide, calamine, and complexes thereof; Polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluororesin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene/styrene copolymer, and organic pigments such as silk powder, cellulose, CI pigment yellow and CI pigment orange, and composite pigments of these inorganic pigments and organic pigments.

Examples of the organic powder include metal soaps such as calcium stearate; alkyl phosphate metal salts such as sodium cetylate, zinc laurylate, and calcium laurylate; acylamino acid polyvalent metal salts such as calcium N-lauroyl-beta-alanine, zinc N-lauroyl-beta-alanine, and calcium N-lauroyl glycine; amidesulfonic acid polyvalent metal salts such as calcium N-lauroyl-taurine and calcium N-palmitoyl-taurine; N such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoylizine, N-alpha-paritoylolnithine, N-alpha-lauroylarginine, N-alpha-hydrogenated beef fatty acid acylarginine, etc. -Acyl basic amino acid; N-acyl polypeptides, such as N-lauroyl glycyl glycine; alpha-amino fatty acids such as alpha-aminocaprylic acid and alpha-aminolauric acid; Polyethylene, polypropylene, nylon, polymethyl methacrylate, polystyrene, a divinylbenzene-styrene copolymer, ethylene tetrafluoride, etc. are mentioned.

As UV absorbers, para-aminobenzoic acid, para-aminobenzoate ethyl, para-aminobenzoate amyl, para-aminobenzoate octyl, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butyl salicylate, homomentyl salicylate, benzyl cinnamate , para-methoxycinnamic acid-2-ethoxyethyl, para-methoxycinnamic acid octyl, dipara-methoxycinnamic acid mono-2-ethylhexaneglyceryl, para-methoxycinnamic acid isopropyl, diisopropyl diisopropyl cinnamic acid ester mixture, uro Cannic acid, ethyl urokanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenonesulfonic acid and salts thereof, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenonedisulfonate, dihydroxybenzophenone , 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. are mentioned.

Examples of disinfectants include hinokitiol, triclosan, trichlorohydroxydiphenyl ether, chlorhexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc phyllithione, benzalkonium chloride, photosensitizer. So, No. 301, mononitroguaial sodium, undecyrenic acid, etc. are mentioned.

Examples of the antioxidant include butylhydroxyanisole, propyl gallic acid, and ellisorbic acid.

Examples of the pH adjuster include citric acid, sodium citrate, malic acid, sodium malate, fmalic acid, sodium fumarate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogen phosphate, and the like.

As alcohol, higher alcohols, such as cetyl alcohol, are mentioned.

In addition, blending components that may be added other than this are not limited thereto, and any of the above components can be blended within a range that does not impair the object and effect of the present invention, but 0.01-5% by weight or 0.01-3 based on the total weight % by weight.

When the formulation of the present invention is a lotion, paste, cream or gel, animal fiber, vegetable fiber, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide, etc. can be used

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. In particular, in the case of a spray, additional chlorofluorohydrocarbon, propane /may contain propellants such as butane or dimethyl ether.

When the formulation of the present invention is a solution or emulsion, a solvent, solvating agent or emulsifying agent is used as a carrier component, for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3-butylglycol oil, glycerol fatty esters, fatty acid esters of polyethylene glycol or sorbitan.

When the formulation of the present invention is a suspension, as a carrier component, water, a liquid diluent such as 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 tracanth may be used.

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 as carrier components Ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolin derivative or ethoxylated glycerol fatty acid ester and the like may be used.

In addition, in the present specification, the composition is one or more selected from the group consisting of shampoo, conditioner, hair tonic, hair nourishing lotion, hair essence, hair serum scalp treatment, hair treatment, hair conditioner, hair shampoo and hair lotion. may, but is not limited thereto.

The composition according to the present invention may further contain an appropriate component according to the formulation, which will be described in detail as follows.

In the present specification, it further contains any one or more selected from the group consisting of surfactants, preservatives and viscosity modifiers, pH adjusters, fragrances, dyes, hair conditioning agents, and water.

In the present specification, the surfactant is any one or more selected from anionic surfactants, amphoteric surfactants and nonionic surfactants.

In the present specification, the anionic surfactant may be an alkyl sulfate or an alkyl ether sulfate, and specific examples thereof include sodium lauryl sulfate, ammonium lauryl sulfate, triethanolamine lauryl sulfate, sodium polyoxyethylene lauryl sulfate, polyoxyethylene lauryl sulfate. Ammonium uryl sulfate, etc. are mentioned.

In the present specification, the amphoteric surfactant may be alkyl betaine or alkyl amidopropyl betaine, and specific examples thereof include cocodimethyl carboxymethyl betaine, lauryldimethyl carboxymethyl betaine, lauryldimethyl alpha-carboxyethyl betaine. phosphorus, cetyldimethyl carboxymethyl betaine, cocamido propyl betaine, and the like.

In the present specification, the nonionic surfactant may be an alkanol amide or an amine oxide, and specific examples thereof include lauryl diethyl amine oxide, palm oil alkyldimethyl amine oxide, lauric acid diethanolamide, coconut oil fatty acid diethanolamide, and coconut oil fatty acid monoethanolamide.

In the present specification, the preservative is at least one selected from the group consisting of methyl paraoxybenzoate, propyl paraoxybenzoate, sodium benzoate, methylchloroisothiazolinone, methylisothiazolinone, and sodium benzoate.

In the present specification, the viscosity modifier is any one or more consisting of cocamide ME (CME), cocamide DA (CDE) and sodium chloride.

In the present specification, the pH adjusting agent is any one or more consisting of sodium phosphate, disodium phosphate, citric acid and sodium citrate.

As used herein, the hair conditioning agent is a dimethicone base, a cationic polymer, or a combination thereof.

In the present specification, the hair conditioning agent may further include any one or more of a tertiary amidoamine, a quaternary ammonium compound, a high melting point compound, and a silicone compound.

Specific examples of the tertiary amidoamine include cocamidopropyl dimethylamine, stearamidopropyl dimethylamine, beheniramidopropyl dimethylamine, oleamidopropyl dimethylamine, isostearamidopropyl dimethylamine, and the like. can

Specific examples of the quaternary ammonium compound include alkyl (14 to 22 carbon atoms) trimethyl ammonium chloride, dialkyl (14 to 22 carbon atoms) dimethyl ammonium chloride, hydrogenated tallow alkyl trimethyl ammonium chloride, and ditallow alkyl dimethyl ammonium chloride. there is.

Specific examples of the high melting point compound include fatty alcohol, fatty acid, fatty alcohol derivative, hydrocarbon, and the like, and more specifically, cetyl alcohol, stearyl alcohol, and cetostearyl alcohol.

Specific examples of the silicone compound include polyalkylsiloxane-based, polyarylsiloxane-based, polyalkylarylsiloxane-based, and polyethersiloxane copolymers.

In addition, 6-pentyl-α-pyrone can be used in various ways as antifungal building materials, pesticides, household goods additives, etc., and can be mixed with known antifungal agents used in the field. In one example, pesticide-related antifungal agents are described, for example, in the Pesticide Manual (Pesticide Manual, 12th ed., British Crop Protection Council, 2000).

Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples are only provided for easier understanding of the present invention, and the contents of the present invention are not limited by the following examples.

Experimental Example 1: Native strain Trichoderma gamsii Isolation of 6-Pentyl-α-pyrone from

Trichoderma gamsii was cultured in 5 kg of potato dextrose agar medium for 7 days at 25° C. under dark conditions and extracted with 10 L of methanol. The crude extract was fractionated by increasing or decreasing the ratio of hexane and ethyl acetate by 20% by silica gel column chromatography. The fractions showing the activity by measuring the antifungal activity of each extract were re-fractionated again using Sephadex LH-20, ODS-A, and prep-HPLC. Among the refractionated substances, the structure of a single substance showing antibacterial activity was confirmed through ¹ H-NMR.

As shown in FIG. 1 , the identified antifungal material was 6-pentyl-α-pyrone.

Experimental Example 2: Evaluation of antifungal activity of 6-pentyl-α-pyrone

A total of 9 human pathogenic fungi ( Candida albicans , Cryptococcus neoformans , Malassezia restricta , Malassezia globosa , Malassezia ) Sympodialis ( Malassezia sympodialis ) , Malassezia pachydermatis , Malassezia furfur , Trichophyton rubrum , on Trichophyton mentagrophytes ) The antifungal activity of 6-pentyl-α-pyrone was confirmed. MIC values were determined using a standard broth serial dilution method according to the Clinical and Laboratory Standard Institute (CLSI) guidelines. As a positive control, fluconazole and ketoconazole were used.

As shown in Table 1, 6-pentyl-α-pyrone was 31.25-62.50 μg/mL against Candida albicans, 15.62 μg/mL against Cryptococcus neoformans, and 7.81-15.62 against Malassezia restricta. μg/mL, for Malassezia globosa 62.50 μg/mL, for Malassezia sympodialis 31.25-62.50 μg/mL for Malassezia pachydermatis 31.25-62.50 μg/mL for Malassezia puffer It exhibited a minimal inhibitory concentration (MIC) value of 62.50 μg/mL for 125.00 μg/mL Trichophyton rubrum and 31.25 μg/mL Trichophyton mentagrophytes.

These results are comparable to those of Fluconazole and Ketocoanzole, which are already widely used clinically.

Control MIC
(Unit: μg/mL) MIC
(Unit: μg/mL) Candida albicans SC5314 FLZ ^* - 0.5 31.25 - 62.50 Cryptococcus neoformans H99 FLZ - 4 15.62 Malassezia restricta KCTC27527 KTZ ^** - 0.0625 7.81 - 15.62 Malassezia globosa CBS7966 KTZ - 0.125 62.50 Malassezia sympodialis CBS7222 KTZ - 0.0625 31.25 - 62.50 Malassezia pachydermatis CBS1879 KTZ- 0.125 31.25 - 62.50 Malassezia furfur CBS1878 KTZ - 0.25 125.00 Trichophyton rubrum KCTC6375 ITZ - 0.25 31.25 Trichophyton mentagrophytes 636 ITZ - 0.5 62.50 *FLZ: Fluconazole
**KTZ: Keoconazole

From the above results, it is expected that 6-pentyl-α-pyrone can be used as an antifungal composition because it has a significant antifungal effect against Candida genus, Cryptococcus genus, Malassezia genus, and Tricophyton genus bacteria.

The description of the present invention described above is for illustration, and those of ordinary skill in the art to which the present invention pertains can understand that it can be easily modified into other specific forms without changing the technical spirit or essential features of the present invention. will be. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

Claims (11)

An antifungal composition comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient.
According to claim 1,
The 6-pentyl-α-pyrone is an antifungal composition, characterized in that represented by the following formula (1).
[Formula 1]

According to claim 1,
The antifungal composition is an antifungal against one or more fungi selected from the group consisting of Candida spp. , Cryptococcus spp. , Malassezia spp. and Trichophyton spp. An antifungal composition, characterized in that it has activity.
A pharmaceutical composition for preventing or treating pathogenic fungal infectious diseases, comprising 6-pentyl-α-pyrone or a pharmaceutically acceptable salt thereof as an active ingredient.
5. The method of claim 4,
The infectious disease is caused by one or more fungi selected from the group consisting of Candida spp. , Cryptococcus spp. , Malassezia spp. and Trichophyton spp. Characterized in that the disease is, the pharmaceutical composition.
5. The method of claim 4,
The infectious disease is candidiasis, cryptococcosis, seborrheic dermatitis, dandruff, atopic dermatitis, otitis externa, athlete's foot and ringworm, characterized in that at least one selected from the group consisting of, a pharmaceutical composition.
7. The method of claim 6,
The candidiasis is at least one selected from the group consisting of thrush, esophageal candidiasis, vaginal candidiasis, candidiasis mycosis, candida endophthalmitis, candida peritonitis, candida osteoarthritis, candida spondylitis and hepatosplenic candidiasis, a pharmaceutical composition.
A cosmetic composition for preventing or improving pathogenic fungal-infectious skin diseases, comprising 6-pentyl-α-pyrone or a cosmetically acceptable salt thereof as an active ingredient.
9. The method of claim 8,
The pathogenic fungal-infectious skin disease is of the genus Malassezia ( Malassezia spp. ) or Trichophyton spp .
9. The method of claim 8,
The pathogenic fungal-infectious skin disease is a cosmetic composition, characterized in that at least one selected from the group consisting of seborrheic dermatitis, dandruff, atopic dermatitis, athlete's foot and ringworm.
9. The method of claim 8,
The cosmetic composition is characterized in that selected from the group consisting of shampoo, conditioner, hair tonic, hair treatment, foot cream, detergent, skin care and soap, cosmetic composition.

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