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WO2024095793A1 - Composition - Google Patents

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Publication number
WO2024095793A1
WO2024095793A1 PCT/JP2023/037958 JP2023037958W WO2024095793A1 WO 2024095793 A1 WO2024095793 A1 WO 2024095793A1 JP 2023037958 W JP2023037958 W JP 2023037958W WO 2024095793 A1 WO2024095793 A1 WO 2024095793A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
salt
composition
antioxidant cosmetic
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2023/037958
Other languages
English (en)
Japanese (ja)
Inventor
育浩 鈴木
裕介 奥山
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shiseido Co Ltd
Original Assignee
Shiseido Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to JP2024554396A priority Critical patent/JPWO2024095793A1/ja
Publication of WO2024095793A1 publication Critical patent/WO2024095793A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to antioxidant cosmetics and skin topical compositions.
  • Cyclic carboxamide derivatives have the effect of inhibiting heparanase activity, and have been proposed for use, for example, as wrinkle improving agents or as whitening agents effective in preventing or suppressing pigmentation such as blemishes (Patent Document 1).
  • 1-Piperidinepropionic acid has been proposed to act on the mechanism of wrinkle formation and to be used as an anti-wrinkle agent (Patent Document 2).
  • Dipotassium glycyrrhizinate has an anti-wrinkle effect, and its use as an anti-wrinkle agent has been proposed (Patent Document 3).
  • a cyclic carboxamide derivative or a salt thereof, an organic acid having a specific structure such as 1-piperidine carboxylic acid or a salt thereof, and glycyrrhizic acid or a salt thereof each have the ability to effectively remove reactive oxygen species.
  • a composition containing a combination of an organic acid having a specific structure, such as 1-piperidine carboxylic acid, or a salt thereof, and glycyrrhizinic acid or a salt thereof effectively inhibits tyrosinase activity.
  • the present invention is based on these findings.
  • An antioxidant cosmetic preparation comprising at least one member selected from the group consisting of (A) a cyclic carboxamide derivative represented by formula (a) or a salt thereof, (B) an organic acid represented by formula (b) or a salt thereof, and (C) glycyrrhizic acid or a salt thereof.
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom;
  • X is -CH2- or -N( R2 )-, where R2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and na is an integer of 1 to 3.
  • nb is an integer of 2 to 5.
  • R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms;
  • component (C) is dipotassium glycyrrhizinate.
  • a composition for external application to the skin comprising a combination of (B) an organic acid represented by formula (b) or a salt thereof and (C) glycyrrhizinic acid or a salt thereof.
  • nb is an integer of 2 to 5.
  • the present invention can provide an antioxidant cosmetic that has effective removal capabilities against reactive oxygen species.
  • the present invention can also provide a composition for external use on the skin that effectively inhibits tyrosinase activity.
  • One aspect of the present invention relates to an antioxidant cosmetic preparation comprising at least one selected from the group consisting of (A) a cyclic carboxamide derivative having a specific structure or a salt thereof, (B) an organic acid having a specific structure or a salt thereof, and (C) glycyrrhizinic acid or a salt thereof.
  • A a cyclic carboxamide derivative having a specific structure or a salt thereof
  • B an organic acid having a specific structure or a salt thereof
  • C glycyrrhizinic acid or a salt thereof.
  • the antioxidant cosmetic composition according to the present invention can contain a cyclic carboxamide derivative represented by formula (a) or a salt thereof (hereinafter, sometimes referred to as component (A).
  • component (A) Cyclic Carboxamide Derivative or Salt thereof
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • X is —CH 2 — or —N(R 2 )—, where R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • na is an integer of 1 to 3.
  • the above-mentioned hydrocarbon group is not particularly limited and may be, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cycloalkylalkyl group, a haloalkyl group, an alkoxyalkyl group, or an alkoxycarbonylalkyl group, and is preferably an alkyl group.
  • R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms;
  • X is —CH 2 — or —NH—, and
  • na is 1.
  • Specific examples of the cyclic carboxamide derivative represented by formula (a) include the following.
  • the component (A) is most preferably 1-(2-hydroxyethyl)-2-imidazolidinone.
  • the (A) component may be a salt of a cyclic carboxamide derivative represented by formula (a).
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, magnesium salts, and ammonium salts.
  • organic salts include acetates, lactates, maleates, fumarates, tartrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, and amino acid salts.
  • the (A) component may be used in combination with one or more types.
  • the amount of the (A) component is preferably 10 to 200 mg/mL, more preferably 15 to 180 mg/mL, and even more preferably 50 to 150 mg/mL, based on the total amount of the antioxidant cosmetic.
  • the antioxidant cosmetic preparation according to the present invention may contain an organic acid represented by formula (b) or a salt thereof.
  • nb is an integer from 2 to 5.
  • Component (B) may be a salt of an organic acid represented by formula (b).
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, and ammonium salts.
  • organic salts include acetates, lactates, maleates, fumarates, tartrates, citrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, diethanolamine salts, and amino acid salts.
  • the (B) component may be used in combination with one or more types.
  • the amount of the (B) component is preferably 0.5 to 100 mg/mL, more preferably 3 to 95 mg/mL, even more preferably 8 to 90 mg/mL, and particularly preferably 15 to 85 mg/mL, relative to the total amount of the antioxidant cosmetic.
  • the antioxidant cosmetic according to the present invention may contain (C) glycyrrhizic acid or its salt.
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • Examples of glycyrrhizinic acid salts include sodium salts, potassium salts, ammonium salts, basic amino acid salts, and alkanolamine salts, and specific examples include monoammonium glycyrrhizinate, dipotassium glycyrrhizinate, and trisodium glycyrrhizinate.
  • the (C) component is preferably dipotassium glycyrrhizinate.
  • the component (C) may be used alone or in combination with two or more other components.
  • the amount of component (C) to be used is preferably 0.01 to 10 mg/mL, more preferably 0.2 to 8 mg/mL, even more preferably 0.4 to 5 mg/mL, and particularly preferably 1.5 to 4.5 mg/mL, relative to the total amount of the antioxidant cosmetic.
  • the antioxidant cosmetic composition according to the present invention contains one or more of the components (A) to (C), and preferably contains one or two of them. In one embodiment of the present invention, the antioxidant cosmetic composition according to the present invention contains a combination of two or more of the components (A) to (C), and more preferably contains a combination of the component (B) and the component (C).
  • compositions for external application to the skin comprising a combination of (B) an organic acid having a specific structure or a salt thereof and (C) a glycyrrhizinic acid or a salt thereof component.
  • Pigmentation such as age spots, freckles, and dullness is generally caused by melanin accumulation, and it is believed that the accumulation of melanin in the epidermis is greatly influenced by tyrosinase activity in melanocytes.
  • the composition for external use on the skin according to the present invention has tyrosinase inhibitory activity and can effectively inhibit tyrosinase activity.
  • the composition according to the present invention is preferably a whitening cosmetic.
  • whitening mainly means suppressing the production of melanin and preventing age spots, freckles, dullness, etc.
  • the composition for topical application to the skin according to the present invention is a tyrosinase inhibitor active agent.
  • the composition for external application to skin contains an organic acid represented by formula (b) or a salt thereof.
  • nb is an integer from 2 to 5.
  • Component (B) may be a salt of an organic acid represented by formula (b).
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, and ammonium salts.
  • organic salts include acetates, lactates, maleates, fumarates, tartrates, citrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, diethanolamine salts, and amino acid salts.
  • the component (B) may be one or more types.
  • the amount of component (B) is preferably 0.5 to 15 mg/mL, more preferably 0.7 to 5 mg/mL, and even more preferably 1 to 2 mg/mL, based on the total amount of the topical skin composition.
  • the skin external composition according to the present invention comprises (C) glycyrrhizic acid or its salt.
  • Glycyrrhizic acid salts include, for example, sodium salts, potassium salts, ammonium salts, basic amino acids, or alkanolamine salts, and specifically, glycyrrhizinic acid monoammonium, glycyrrhizinic acid dipotassium, and glycyrrhizinic acid trisodium.
  • (C) component is preferably glycyrrhizinic acid dipotassium.
  • the component (C) may be used alone or in combination with two or more other components.
  • the amount of component (C) is preferably 0.01 to 0.8 mg/mL, more preferably 0.02 to 0.5 mg/mL, and even more preferably 0.03 to 0.1 mg/mL, relative to the total amount of the composition for topical skin application.
  • the amount of component (B) relative to the amount of component (C) ((B)/(C)) is preferably 5 to 200 by mass, and more preferably 10 to 50 by mass.
  • the antioxidant cosmetic and topical skin composition according to the present invention may further contain water.
  • water water used in cosmetics, quasi-drugs, etc. may be used, such as purified water, ultrapure water, ion-exchanged water, tap water, etc.
  • the antioxidant cosmetic and topical skin composition according to the present invention can contain optional ingredients that are normally used in cosmetics and pharmaceuticals, in addition to the above-mentioned ingredients.
  • Optional ingredients include, for example, moisturizers, lower alcohols, thickeners, surfactants, sequestering agents, neutralizing agents, pH adjusters, antioxidants, preservatives, medicines, UV absorbers, powdered ingredients, oily ingredients, fragrances, etc., and one or more of these can be contained as long as the effects of the present invention are achieved.
  • the formulation of the antioxidant cosmetic and topical skin composition according to the present invention is not particularly limited, and may take any formulation, such as a solution system, a solubilized system, an emulsion system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, an ointment, a gel, an aerosol, etc.
  • the form of use is also not particularly limited, and may take any form, such as a lotion, milky lotion, cream, essence, jelly, gel, ointment, pack, mask, foundation, etc.
  • the antioxidant cosmetic and topical skin composition according to the present invention can be produced according to a conventional method.
  • antioxidant cosmetic preparation 1-(2-hydroxyethyl)-2-imidazolidinone as component (A), 1-piperidinepropionic acid as component (B), and dipotassium glycyrrhizinate as component (C) were added to ultrapure water in the amounts shown in Table 1, and the mixture was stirred to prepare the antioxidant cosmetics of Examples 101 to 118.
  • antioxidant cosmetic compositions of Examples 101 to 118 were evaluated for their radical scavenging ability against DPPH radicals by the following procedure. 60 ⁇ L of the antioxidant cosmetic of each Example or control (ultrapure water was used for the control), 60 ⁇ L of ethanol (CAS No. 64-17-5, Nippon Alcohol), and 40 ⁇ L of 0.25 M acetic acid buffer (pH 5.5) were added to a 96-well plate and incubated at 37° C. for 5 minutes. Ethanol was used as a blank instead of DPPH. Three wells were used for each treatment group.
  • DPPH 2,2-diphenyl-1-picrylhydrazyl
  • the 96-well plate was shaken at 270 rpm for 30 seconds and then incubated at 37° C. for 30 minutes.
  • the 96-well plate was shaken at 270 rpm for 10 seconds to uniformly disperse the dye in the wells, and then the optical density at 517 nm (OD 517 ) was measured using a microplate reader.
  • the DPPH scavenging rate of the antioxidant cosmetic of the Example was calculated from the OD 517 of the antioxidant cosmetic of the Example and the control according to the following formula.
  • phosphate buffer 100 mM phosphate buffer was used instead of the tyrosinase solution.
  • Three wells were used for one treatment group. After 3 minutes, 50 ⁇ L of 2.5 mM 3,4-L-dihydroxyphenylalanine (L-DOPA, CAS No. 59-92-7, Wako) solution was added, the 96-well plate was shaken at 270 rpm for 10 seconds, and the optical density at 490 nm (OD 490 ) was measured using a microplate reader (SPARK 10M, TECAN). The plate was incubated at 23° C. for 10 minutes, and the optical density at 490 nm (OD 490 ) was measured after 10 minutes.
  • L-DOPA 3,4-L-dihydroxyphenylalanine
  • the tyrosinase inhibitory activity rate of the examples and comparative examples was calculated according to the following formula.
  • Tyrosinase inhibitory activity rate (%) 100 - [ ⁇ (As10 - Ab10) - (As0 - Ab0) ⁇ / (Ac10 - Ac0) x 100]
  • Ac10 OD 490 of control after incubation
  • As0 OD 490 of each of the compositions for external use on the skin of each of the Examples and Comparative Examples before incubation As10: OD 490 of each of the compositions for external use on the skin of the Examples and Comparative Examples after incubation It is.
  • Table 2 The results obtained are shown in Table 2.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Le problème décrit par la présente invention est de fournir un produit cosmétique antioxydant. [Solution] L'invention concerne un produit cosmétique antioxydant contenant au moins un composant choisi dans le groupe constitué par (A) un dérivé de carboxamide cyclique ayant une structure spécifique ou un sel de celui-ci, (B) un acide organique ayant une structure spécifique ou un sel de celui-ci et (C) de l'acide glycyrrhizique ou un sel de celui-ci.
PCT/JP2023/037958 2022-11-02 2023-10-20 Composition Ceased WO2024095793A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2024554396A JPWO2024095793A1 (fr) 2022-11-02 2023-10-20

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022176688 2022-11-02
JP2022-176688 2022-11-02

Publications (1)

Publication Number Publication Date
WO2024095793A1 true WO2024095793A1 (fr) 2024-05-10

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PCT/JP2023/037958 Ceased WO2024095793A1 (fr) 2022-11-02 2023-10-20 Composition

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JP (1) JPWO2024095793A1 (fr)
WO (1) WO2024095793A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017641A (en) * 1975-01-31 1977-04-12 The Procter & Gamble Company Skin moisturizing compositions containing 2-pyrrolidinone
JPS52151738A (en) * 1976-04-06 1977-12-16 Wella Ag Cosmetics
JP2012240911A (ja) * 2011-05-13 2012-12-10 Shiseido Co Ltd １−ピペリジンプロピオン酸からなる、抗シワ剤、マトリックスメタロプロテアーゼ（ｍｍｐ）抑制剤、及び／又はラミニン５産生促進剤
JP2019006697A (ja) * 2017-06-22 2019-01-17 小林製薬株式会社 活性酸素消去剤
WO2020204191A1 (fr) * 2019-04-05 2020-10-08 株式会社 資生堂 Produit cosmétique contenant une substance de conversion de longueur d'onde ultraviolette et agent médicinal
WO2022131108A1 (fr) * 2020-12-15 2022-06-23 株式会社 資生堂 Promoteur de régénération de derme

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017641A (en) * 1975-01-31 1977-04-12 The Procter & Gamble Company Skin moisturizing compositions containing 2-pyrrolidinone
JPS52151738A (en) * 1976-04-06 1977-12-16 Wella Ag Cosmetics
JP2012240911A (ja) * 2011-05-13 2012-12-10 Shiseido Co Ltd １−ピペリジンプロピオン酸からなる、抗シワ剤、マトリックスメタロプロテアーゼ（ｍｍｐ）抑制剤、及び／又はラミニン５産生促進剤
JP2019006697A (ja) * 2017-06-22 2019-01-17 小林製薬株式会社 活性酸素消去剤
WO2020204191A1 (fr) * 2019-04-05 2020-10-08 株式会社 資生堂 Produit cosmétique contenant une substance de conversion de longueur d'onde ultraviolette et agent médicinal
WO2022131108A1 (fr) * 2020-12-15 2022-06-23 株式会社 資生堂 Promoteur de régénération de derme

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