WO2022014660A1 - 皮脂産生調節剤 - Google Patents

皮脂産生調節剤 Download PDF

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Publication number
WO2022014660A1
WO2022014660A1 PCT/JP2021/026544 JP2021026544W WO2022014660A1 WO 2022014660 A1 WO2022014660 A1 WO 2022014660A1 JP 2021026544 W JP2021026544 W JP 2021026544W WO 2022014660 A1 WO2022014660 A1 WO 2022014660A1
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Prior art keywords
skin
sebum production
acne
sebum
hydrogen atom
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PCT/JP2021/026544
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English (en)
French (fr)
Japanese (ja)
Inventor
隆司 藤田
Original Assignee
学校法人立命館
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Priority to JP2022536434A priority Critical patent/JPWO2022014660A1/ja
Publication of WO2022014660A1 publication Critical patent/WO2022014660A1/ja

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/08—Antiseborrheics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention is based on the formula (I).
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • Sebum has the role of protecting the skin from dryness and external stimuli and keeping the skin soft. Sebum is secreted by the sebaceous glands, which develop most during puberty in the teens and twenties. The developed and enlarged sebaceous glands secrete excess sebum, mix with the old stratum corneum of the pores, and form keratin plugs in the pores to make the pores stand out, which is a cosmetic problem. In addition, excessively secreted sebum can cause acne and skin problems caused by the growth of P. acnes.
  • Isoflavone compounds, matrix metalloproteinase inhibitors and the like are known as compounds having a sebum secretion inhibitory effect.
  • examples of the compound having a sebum secretion promoting action include ⁇ -oryzanol.
  • the part with many sebaceous glands and the part with few sebaceous glands are adjacent to each other, it is necessary to apply an appropriate drug to the appropriate part, which is complicated.
  • Oleanolic acid which is one of the pentacyclic terpenes, is a functional triterpene and has been found to have physiological activities such as anticancer effect, anti-inflammatory effect, antioxidant effect, and antihyperlipidemic effect.
  • oleanolic acid has already been reported as a hair growth or hair growth agent (Patent Document 1), and derivatives of oleanolic acid and ursolic acid have been reported as photoaging inhibitors (Patent Document 2).
  • Patent Document 1 a hair growth or hair growth agent
  • Patent Document 2 derivatives of oleanolic acid and ursolic acid have been reported as photoaging inhibitors
  • no regulatory effect of oleanolic acid on sebum secretion has been reported so far.
  • An object of the present invention is to provide a novel agent for regulating sebum secretion.
  • the present inventor found that when sebaceous gland cells were treated with oleanolic acid or ursolic acid in the absence of C. Acne, lipogenesis increased in a treatment concentration-dependent manner, but DMSO-treated cells in the presence of C. Acne. Although the lipid production was very high, it was confirmed that the cells treated with oleanolic acid or ursolic acid suppressed the increase in the amount of lipid production induced by C. Acne. In addition, when C. Acne was injected into the skin of mice, enlarged sebaceous glands and keratin plugs were observed in the injected skin, but it was found that these were suppressed by treatment with 0.1% oleanolic acid.
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • the compound represented by the compound or a physiologically acceptable salt thereof should be administered to the subject.
  • Methods for regulating sebum production including. [9] Formula (I) for use in the treatment of skin disorders or acne caused by dry skin
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • a compound represented by the compound or a physiologically acceptable salt thereof is used as a sebum production regulator. Can be provided.
  • the present invention is based on the formula (I).
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • a sebum production regulator containing a salt is provided.
  • the combination of R 1 and R 2 may be any combination, but when R 1 is a hydrogen atom, R 2 is a methyl group, and when R 1 is a methyl group, R 2 is preferably a hydrogen atom.
  • R 1 is a hydrogen atom and R 2 is a methyl group
  • the compound of the present invention has the formula (II).
  • the compound of the present invention may be a physiologically acceptable salt thereof.
  • the physiologically acceptable salt of the compound represented by the formula (I) is not particularly limited as long as it is a salt usually used in a pharmaceutical composition, and is, for example, an alkali metal salt such as sodium or potassium.
  • Alkaline earth metal salts such as calcium and magnesium; organic amine salts such as triethylamine, piperazine, piperidine and triethanolamine; basic amino acid salts such as lysine and arginine; and the like can be exemplified.
  • the compounds of the present invention or physiologically acceptable salts thereof are provided as sebum production regulators.
  • the regulation of sebum production includes, but is not limited to, suppression of sebum production in oily skin or promotion of sebum production in dry skin. Therefore, in one embodiment, the sebum production regulator of the present invention is provided as a sebum production inhibitor in oily skin.
  • Suppression of sebum production in oily skin means that when sebum is produced from the sebaceous glands in excess of normal sebum production, the production of sebum is suppressed by the compound of the present invention or a physiologically acceptable salt thereof.
  • causes of sebum production from the sebaceous glands in excess of normal sebum production include sebaceous gland irritation by Cutibacterium acnes, stress, and overexpression of hormones (eg, testosterone, 5 ⁇ -dihydrotestosterone).
  • hormones eg, testosterone, 5 ⁇ -dihydrotestosterone
  • the amount of sebum produced may be reduced, and it is preferable that the amount of sebum produced is reduced to a normal level.
  • the sebum production regulator of the present invention is provided as a sebum production promoter in dry skin.
  • promotion of sebum production in dry skin means that when sebum is produced from the sebaceous glands below the normal amount of sebum produced, the compound of the present invention or a physiologically acceptable salt thereof promotes sebum production.
  • causes of sebum production from the sebaceous glands below the normal production amount include insufficient secretion of sebum from the sebaceous glands due to aging and insufficient secretion of sebum due to a decrease in temperature in winter.
  • the promotion may be as long as the amount of sebum produced is increased, and it is preferable that the amount of sebum produced is increased to a normal level.
  • the skin oil production regulator of the present invention is used for humans, non-human animals (for example, mammals other than humans (livestock such as pigs, cows, horses, dogs, cats), birds (poultry such as turkeys, chickens), etc.). It can be applied, preferably to humans.
  • non-human animals for example, mammals other than humans (livestock such as pigs, cows, horses, dogs, cats), birds (poultry such as turkeys, chickens), etc.
  • the compound of the present invention or a physiologically acceptable salt thereof can be dissolved in ethanol, oils and fats such as tea seed oil, cream and the like, and used as a sebum production regulator.
  • the compounding amount of the compound of the present invention is 0.001% (w / w) or more, preferably 0.01% (w / w) or more, and more preferably 0.1% (w / w) or more of the total weight of the sebum production regulator. It is preferable to mix in a ratio. If the blending amount is too small, the sebum production regulating effect cannot be sufficiently obtained, which is not preferable.
  • As the upper limit for example, 10% (w / w) or less, preferably 5% (w / w) or less, more preferably 2% (w / w) or less can be mentioned.
  • raw material components to be blended in the sebum production regulator those applied to a normal sebum production regulator can be used.
  • hydrocarbons, waxes, fats and oils, esters, higher fatty acids, higher alcohols, surfactants, fragrances, pigments, preservatives, preservatives, excipients, cooling agents, wetting agents, antioxidants. , UV protection agents, alcohols, pH adjusters, etc. can be blended.
  • the sebum production regulator of the present invention may be in any form as long as it can be applied externally to the skin.
  • it can be in the form of a cream, ointment, lotion or the like as a drug or quasi-drug.
  • the present invention is a therapeutic agent for sebum, which comprises a sebum production inhibitor in oily skin.
  • the sebum production inhibitor of the present invention is a therapeutic agent for sebum, which comprises a sebum production inhibitor in oily skin.
  • Acne is a chronic inflammatory disease of the sebaceous glands, and examples thereof include acne vulgaris (acne, especially adolescent acne) and seborrheic dermatitis.
  • the therapeutic agent for acne of the present invention may contain, as other auxiliary agents, a keratolytic agent, a bactericidal agent, an anti-inflammatory agent, an antiseborrheic agent, an antipruritic agent and the like.
  • the sebum production regulator of the present invention is provided as a sebum production promoter in dry skin (the sebum production promoter of the present invention)
  • the present invention is derived from dry skin, which comprises a sebum production promoter in dry skin.
  • Skin diseases caused by dry skin are diseases caused by the loss of the protective function of the skin due to sebum, such as xeroderma, adult acne, redness of adult acne, itching of adult acne, and roughness of the skin. Examples include dry skin or rough skin.
  • adolescent acne differs from acne that mainly affects teenagers, so-called “adolescent acne", in various respects.
  • adult acne is known to have problems such as easy recurrence, acne scars and spots.
  • adolescent acne is mainly caused by increased sebum secretion, whereas adult acne is not limited to them, but is dry, hormonal imbalance, irregular life, and lack of sleep. , Disordered eating habits, overwork, stress, etc. are cited as causes.
  • the preferred applicable disease thereof is adult acne due to dryness or imbalance of hormones, which is more preferable.
  • examples include adult acne due to dryness.
  • Patients with dry skin include patients with a water content of 72 or less when the water content of the cheeks of the face is measured with a corneometer (trade name: Comeometer CM825, manufacturer Courage + Khazaka).
  • Patients with a facial cheek moisture content of 64 or less, preferably 60 or less, can be expected to be more effective as a target for applying the sebum production promoter of the present invention.
  • the therapeutic agent for skin diseases caused by dry skin of the present invention may contain a moisturizer, a bactericidal agent, an anti-inflammatory agent, an antipruritic agent and the like as other auxiliary agents.
  • C. acnes JCM6425, Riken Bioresource Center, Tsukuba, Japan
  • GMG culture Nissui, Tokyo, Japan
  • sebum production was more efficient than live C. acnes, so homogenates were used in the following examples.
  • C. acnes of 5 ⁇ 10 7 CFU was sonicated with Branson Sonifier model 150 (Danbury, CT, USA) and aliquots were stored at 4 ° C until use.
  • protein quantification was performed and aliquots dissolved in the medium were added at 100 ⁇ g / ml.
  • SZ95 Immortalized human sebaceous gland cells SZ95 are derived from human facial sebaceous glands, 10% bovine fetal serum (Thermo Fisher Scientific Inc., Waltham, MA, USA), 5 ng / ml human epidermal growth factor (hEGF) (PeproTech GmbH,). It was cultured in Sebomed® Basal Medium (Millipore, Billerica, MA, USA) supplemented with Hamburg, Germany), 50 IU / ml penicillin, and 50 ⁇ g / ml streptomycin (Nacalai Tesque, Kyoto, Japan). Medium was changed every other day and cells were secondarily cultured at 60-70% confluence.
  • Intracellular lipid concentration For semi-quantitative detection of sebaceous lipids, 10 ⁇ g / ml BODIPY TM 493/503 (4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a) , 4a-Diaza-s-Indasen) (Thermo Fisher Scientific) stain v applied, while 55 ⁇ l lysis buffer of cells stained with fluorescent BODIPY TM in a 48-well plate for quantitative measurement. Lysis with (25 mM Triton phosphate [pH 7.8], 2 mM DTT, 2 mM EDTA, 10% glycerol, and 1% Triton X-100).
  • Tissues were stained with BODIPY, macroscopic images were obtained from the back of the skin with a fluorescent stereomicroscope LEICA MZ10F / DFC7000 T, and analyzed with software LAS V4.12 (Leica mycrosystems, Wetzlar, German). The results are shown in FIG. As a result, by applying oleanolic acid for external use, the enlargement of the sebaceous glands due to P. acnes injection was suppressed, and the stainability by BODIPY was reduced at the beginning compared to the solvent control. The tissue was fixed with 10% formalin and embedded. Paraffin sections were then prepared and stained with HE. The results are shown in FIG.
  • HE staining of paraffin sections showed enlarged sebaceous glands (arrows) and keratin plugs (arrowheads) in C. Acne-injected skin (CRL), which were suppressed by treatment with 0.1% oleanolic acid.
  • Example 3 Test method for suppressing the inhibitory effect of oleanolic acid on the promotion of sebum secretion by n-tetradecane 1. Rabbit grouping Rabbits were grouped as shown in Table 1.
  • n-tetradecane and test substance The administration schedule of n-tetradecane and test substance is shown in FIG. Before administration of n-tetradecane, the approximate area inside the auricle of both ears of each rabbit was determined, the dose was determined to be 0.2 mL / 3x3 cm, and the dose was administered to the entire inside of the auricle. Administration was performed between 8:00 and 18:00, and test days 1 to 14 were performed once / day in both ears of all groups. On test days 15-21, group I was performed once / day on both ears. Group II was not administered to both ears. In group III, only the right ear was performed once a day, and the left ear was not performed.
  • a plant extract containing oleanolic acid (test substance A) and 0.1% oleanolic acid (test substance) was provided at the site where petrolatum was sufficiently formed inside the auricle of rabbits treated with n-tetradecane.
  • B) or Vaseline (base) was administered in an amount of 0.5 g.
  • a 3x3 cm site for diameter measurement and excision was also set in the right ear of group III, which received no administration.
  • Administration was performed to both ears of groups I and II and the left ear of group III for 7 days (once / day, 8: 00-18: 00) on test days 15 to 21, and the right ear of group III was administered. I didn't.
  • Pore diameter measurement Pore diameter was measured before administration of n-tetradecane (TD) on test days 14 and 15, and the average value was used as the pre-value. On test days 16, 18, 20 and 22, optionally 10 pores at the administration site of oleanolic acid (test substance A), plant extract containing 0.1% oleanolic acid (test substance B) or petrolatum (base). The pore size was measured using a microscope (Dino-Lite Digital Microscope, model number: DILOTEPL, sold by Sanko). The average value and standard deviation of the pore diameter were calculated.
  • TD n-tetradecane
  • the significance test was performed by the F-test for homoscedasticity, the Student's t-test for homoscedasticity, and the Aspin-Welch's t-test for unequal dispersion.
  • the significance level was set to a risk rate of 5%
  • the significance level was set to a risk rate of 5% and 1%. The results are shown in Table 2 and FIG.
  • Test 1 when only petrolatum (base) was administered after administration of n-tetradecane for 14 days, the pore diameter on the 22nd day was even larger than the pore diameter on the 14th day (301 left ear). However, when oleanolic acid (test substance A) or a plant extract containing 0.1% oleanolic acid (test substance B) was administered after administration of n-tetradecane for 14 days, the pore diameter on the 22nd day was larger than the pore diameter on the 14th day. It was getting smaller (201 right ear, 201 left ear).
  • Test 2 when n-tetradecane was continuously administered for 22 days, the pore diameter on the 22nd day was even larger than the pore diameter on the 14th day (301 right ear). However, when oleanolic acid (test substance A) or a plant extract containing 0.1% oleanolic acid (test substance B) was administered together with n-tetradecane from the 15th day, the pore diameter on the 22nd day was the pore diameter on the 14th day. Although it was even larger, the degree could be suppressed (101 right ear, 101 left ear).
  • Paraffin sections at the excised site were prepared, stained with hematoxylin and eosin, and observed using a binocular microscope BHS.
  • a representative example of the findings is shown in FIG. In the ear canal tissue on day 22 in the 301 right ear, dilation of the pore diameter was confirmed. On the other hand, in the stained images of the external auditory canal tissue of the 101st right ear and the 201st right ear, no dilation of the pore diameter could be observed.
  • Example 4 Test method for treating adult acne using oleanolic acid Test method Setyl ethylcaproate (trade name: NIKKOL) so that oleanolic acid (trade name: Oleanolic Acid, manufactured by Wako Pure Chemical Industries, Ltd.) is 1% (w / w). CI0, Nikko Chemicals) was used as a solvent to prepare the solutions shown in Table 3.
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or a methyl group.
  • a compound represented by the compound or a physiologically acceptable salt thereof is used as a sebum production regulator. Can be provided. This application is based on Japanese Patent Application No. 2020-122251 (Filing date: July 16, 2nd year of Reiwa), the entire contents of which are incorporated herein by reference.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
PCT/JP2021/026544 2020-07-16 2021-07-15 皮脂産生調節剤 WO2022014660A1 (ja)

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JP2022536434A JPWO2022014660A1 (zh) 2020-07-16 2021-07-15

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JP2020-122251 2020-07-16

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6293215A (ja) * 1985-10-18 1987-04-28 Shiseido Co Ltd 養毛料
JP2003508486A (ja) * 1999-09-10 2003-03-04 アプライド・ジェネティクス・インコーポレーテッド・ダーマティクス 皮膚脂質含量の改良のための組成物及び方法
JP2003113069A (ja) * 2001-10-03 2003-04-18 Sederma Sa ざ瘡傾向肌用の皮膚外用剤組成物
CN103222999A (zh) * 2012-01-31 2013-07-31 财团法人工业技术研究院 金银花萃取物及其制备方法与应用
JP2016132625A (ja) * 2015-01-16 2016-07-25 株式会社マンダム 美容方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6293215A (ja) * 1985-10-18 1987-04-28 Shiseido Co Ltd 養毛料
JP2003508486A (ja) * 1999-09-10 2003-03-04 アプライド・ジェネティクス・インコーポレーテッド・ダーマティクス 皮膚脂質含量の改良のための組成物及び方法
JP2003113069A (ja) * 2001-10-03 2003-04-18 Sederma Sa ざ瘡傾向肌用の皮膚外用剤組成物
CN103222999A (zh) * 2012-01-31 2013-07-31 财团法人工业技术研究院 金银花萃取物及其制备方法与应用
JP2016132625A (ja) * 2015-01-16 2016-07-25 株式会社マンダム 美容方法

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