WO2008018683A1 - Dérivés d'acide hydroxycinnamique et leur procédé de préparation et composition cosmétique les contenant - Google Patents

Dérivés d'acide hydroxycinnamique et leur procédé de préparation et composition cosmétique les contenant Download PDF

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Publication number
WO2008018683A1
WO2008018683A1 PCT/KR2007/002847 KR2007002847W WO2008018683A1 WO 2008018683 A1 WO2008018683 A1 WO 2008018683A1 KR 2007002847 W KR2007002847 W KR 2007002847W WO 2008018683 A1 WO2008018683 A1 WO 2008018683A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
hydroxycinnamic acid
acid derivatives
cosmetic composition
adamantylamide
Prior art date
Application number
PCT/KR2007/002847
Other languages
English (en)
Inventor
Heung Soo Baek
Jae Won You
Gae Won Nam
Soo Mi Ahn
Boo Min Kim
Ho Sik Rho
Duck Hee Kim
Original Assignee
Amorepacific Corporation
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 Amorepacific Corporation filed Critical Amorepacific Corporation
Publication of WO2008018683A1 publication Critical patent/WO2008018683A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/10—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring

Definitions

  • the present invention relates to hydroxycinnamic acid derivatives conjugated with adamantylamide represented by the following formula 1 and a preparation method thereof and a cosmetic composition containing the same as an active ingredient .
  • UV irradiation causes skin troubles such as pigmentation or wrinkles.
  • Recent studies report that the active oxygen acts as a key factor to cause such skin troubles .
  • melanin is a very stable substance that is not easily gotten rid of until keratinization once it is generated by internal or outer stress stimulus.
  • Endogenous melanin is produced by polymerizing oxidation using tyrosine or DOPA as a substrate and tyrosinase as a catalyst and this melanin is increased with the increase of free radical, inflammation or UV.
  • UV increases the generation of endogenous active oxygen and this active oxygen increases melanin generation. And then, the increased local melanin becomes skin stain which might spoil the beauty and further cause serious problems such as wrinkles and skin cancer with threatening our lives.
  • active oxygen inhibitors such as ascorbic acid and its derivatives, Mori Cotex Radicis extract, green tea extract, aloe extract, Scutellariae Radix extract, which are so called natural polyphenol extracts, have been tried. But, these natural polyphenol extracts are so unstable that their effects cannot be constant during mixing procedure and percutaneous absorption is difficult, resulting in doubt in whitening and anti-wrinkle effects. [Disclosure]
  • the present inventors completed this invention by confirming that hydroxycinnamic acid derivatives conjugated with adamantylamide had melanin generation inhibitory activity or procollagen synthesis inducing effect, and therefore it can be an excellent cosmetic composition to bring whitening effect or anti-wrinkle effect. It is an object of the present invention to provide hydroxycinnamic acid derivatives conjugated with adamantylamide having a novel chemical structure and a preparation method thereof.
  • the present invention relates to hydroxycinnamic acid derivatives conjugated with adamantylamide represented by formula 1 and a preparation method thereof as well as an antioxidant, a whitening or an anti-wrinkle cosmetic composition containing the same as an active ingredient.
  • the hydroxycinnamic acid derivatives conjugated with adamantylamide of the present invention represented by formula 1 are generated by the following reaction formula, in which the following steps are included, 1) preparing the acetylated compound of formula III by converting H of hydroxy1 group to acetyl group by using hydroxycinnamic acid of formula II, acetic anhydride, base and a catalyst; 2) preparing the amide compound of formula IV by reacting the acetylated compound of formula III prepared in the above step 1) with adamantaneamine having hydrophobic group and ethylchloroformate; and
  • Ri is H or C1-C7 alkyl ;
  • Ri is C1-C7 alkyl
  • Ri is the same as R 2 but when Ri is H , R 2 is acetyl .
  • step 1) hydrogen atom of hydroxyl group is converted to acetyl group by the reaction of hydroxycinnamic acid, acetic anhydride and base in the presence of a catalyst.
  • base is pyridine or triethylamine
  • a reaction solvent is selected from the group consisting of dichloromethane, chloroform and tetrahydrofuran.
  • dimethylaminopyridine is used as a catalyst, and if not, the reaction is not smoothly carried out and yield is not high.
  • the reaction temperature is preferably 10 - 80 ° C and more preferably 40°C .
  • step 2) the reaction of the acetylated compound (III) with adamantylamine having hydrophobic group and ethylchloroformate is induced to give an adamantylamide compound (IV) .
  • This reaction can be induced by acid halogenation, active ester method, or acid anhydride method, but it is preferred to convert the compound to adamantylamine having hydrophobic group under anhydrous condition to produce adamantylamide compound (IV) .
  • the equivalence ratio of adamantylamine having hydrophobic group to be reacted with the acetylated compound (III) is preferably 1.1 - 1.3. If the equivalence ratio is under 1:1, the level of adamantylamide compound (IV) is reduced.
  • the base herein is pyridine or triethylamine but preferably triethylamine .
  • a reaction solvent is selected from the group consisting of dichloromethane, acetone, N, N- dimethylformatnide, acetonitrile and tetrahydrofuran, but N, N- dimethylformaraide and tetrahydrofuran are preferred.
  • the preferable reaction temperature is 10 - 60°C and 30 ° C is more preferred.
  • step 3) hydroxycinnamic acid derivatives conjugated with adamantylamide represented by formula I is obtained.
  • the hydrolysis of acetyl group of adamantylamide compound (IV) is induced in the presence of a base selected among alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • a reaction solvent is selected from the group consisting of water, methanol, ethanol, propanol, tetrahydrofuran and dichloromrthane . It is preferred to mix tetrahydrofuran and methanol at the volume ratio of 1 : 1 - 1 : 5, and more preferably 1 : 1 for desirable reaction in a short period of time.
  • hydroxycinnamic acid derivatives conjugated with adamantylamide represented by formula I which can be generated by the above preparation method are as follows .
  • the hydroxycinnamic acid derivatives conjugated with adamantylamide (I) prepared by the method of the present invention can be included in an anti-oxidant, a whitening or an anti-wrinkle cosmetic composition as an active ingredient, and at this time, the concentration can be determined considering the maximum effect of anti-oxidant, whitening or anti-wrinkle activity.
  • the compound can be contained in an amount of 0.01 - 20.0 weight%, based on the total cosmetic composition and formulation form can be cream, lotion, toner, massage cream or essence but not always limited
  • the hydroxycinnamic acid derivatives conjugated with adamantylamide (I) prepared by the method of the present invention can be included in an anti-oxidant, a whitening or an anti-wrinkle cosmetic composition as an active ingredient, and at this time, the concentration can be determined considering the maximum effect of anti-oxidant, whitening or anti-wrinkle activity.
  • the compound can be contained in an amount of 0.01 - 20.0 weight%, based on the total cosmetic composition and formulation form can be cream, lotion, toner, massage cream or essence but not always limited thereto.
  • the composition of the present invention can include other general ingredients according to its formulation and the kinds, and contents of such ingredients can be generally- determined by those in the art.
  • the composition of the present invention can include any other anti-oxidant, whitening or anti-wrinkle agent in addition to the hydroxycinnamic acid derivatives conjugated with adamantylamide (I) of the present invention in order to increase the anti-oxidative, whitening or anti-wrinkle effect.
  • adamantylamide (I) of the present invention in order to increase the anti-oxidative, whitening or anti-wrinkle effect.
  • the kind and concentration of an acceptable conventional anti-oxidant, whitening or anti-wrinkle agents are well informed to those in the art.
  • the target compound 3- (3-hydroxy-4-methoxyphenyl) -N- adamantyl-propeneamide (Formula I-c) was prepared as 75g of a 13
  • Examples 1 - 4 the most representative conventional anti-oxidant tocopherol (as a positive control) , EGCG (Epigallocatechin Gallate) and BHT (t- butyl hydroperoxide) were treated thereto at the concentration of 10 "4 mol, followed by culture in a 37 ° C, 5% CO 2 incubator. Cells were obtained 4 hours later. The cells were lysed by freeze/thawing. The following experiments were performed according to the instructions of the assay kit.
  • 4- hydroxyalkenal i.e. 4-hydroxy-2 (E) -nonenal, 4-HNE
  • MDA and HNE shown in Table 1 are the products from the peroxidation of saturated fatty acid associated ester. So, measuring such aldehydes leads to the understanding of the level of lipid peroxidation. And the lower the value, the greater the lipid peroxidation inhibitory effect will be. From the results of investigation of anti-oxidation shown in Table 1, it was confirmed that hydroxycinnamic acid derivatives prepared in Examples 1 - 4 had excellent anti-oxidative effect, compared with the representative conventional anti-oxidants such as t-BHP, tocopherol and EGEG.
  • MeI-Ab cell line derived from cutaneous pigment cells of C57BL/6 was used. Cell culture was carried out in DEME supplemented with 10% FBS, 100 nM 12-OI-tetradecanoyl phobol- 13-acetate, 1 nM cholera toxin in a 37 ° C, 5% CO 2 incubator. Cultured MeI-Ab cells were recovered using 0.25% trypsin- EDTA and then re-distributed in a 24 -well plate at the equal concentration (IxIO 5 cells/well) . For the three consecutive days from the second day of distribution, media each containing 10 ppm of sample were replaced.
  • UVB was irradiated 1.5 - 2 times the minimal erythema dose to induce darkening of skin.
  • the hydroxycinnamic acid derivatives conjugated with adamantylamide of Examples 1 - 4 were confirmed to have excellent whitening effect, compared with lipoic acid that has been known as a whitening agent, which was also similar or even improved, compared with the whitening effect of hydroquinone (HQ) .
  • Collagen biosynthesis promoting effects of hydroxycinnamic acid derivatives conjugated with adamantylamide of Examples 1 - 4 were compared with those of retinol and retinoic acid.
  • Fibroblasts were seeded in a 24 well plate at the concentration of 10 5 cells per well and cultured until they grew 90%. After culturing in serum-free DMEM for 24 hours, the cells were treated with 10 "4 mol of hydroxycinnamic acid derivatives of Examples 1 - 4, retinol and retinoic acid, 19
  • hydroxycinnamic acid derivatives prepared in Examples 1 - 4 were confirmed to have similar or greater collagen biosynthesis inducing effect in skin, compared with retinol and retinoic acid.
  • hydroxycinnamic acid derivatives prepared in Examples 1 - 4 were tested for the inhibitory effect on collagenase expression, by comparing those of retinol and retinoic acid.
  • Human fibroblasts were seeded in a 96 well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) 20
  • the cells were treated with the hydroxycinnamic acid derivatives of Examples 1 - 4, retinol and retinoic acid by 10 "4 mol each for 24 hours and then the cell culture medium was obtained.
  • Collagenase generation in the cell culture medium was measured by collagenase measuring kit (Amersham Pharmacia, USA) .
  • the cell culture medium was loaded in a 96 well plate supplemented evenly with the primary collagenase antibody to induce antigen-antibody reaction for 3 hours.
  • the chromophore-conjugated secondary collagen antibody was loaded in the 96 well plate again and reaction was induced for 15 minutes.
  • a coloring material was added 15 minutes later to induce color development for 15 minutes and then 1 M sulfuric acid was added to terminate color development.
  • the color of the reaction solution was yellow and the degree of yellow varied from the degree of reaction.
  • OD 405 of the yellow 96 -well plate was measured and collagenase synthesis was calculated by the following mathematical formula 1.
  • the optical density of the cell culture medium that had not been treated with any composition was considered as the control. 21
  • compositions for whitening and anti-wrinkles were prepared with the hydroxycinnamic acid derivatives of 22
  • Examples 1 - 4 having excellent melanin generation inhibitory- effect and collagen biosynthesis promoting effect by the conventional cosmetic composition preparation method according to the following constitution and ratio.
  • Palmitic acid 10% Palmitic acid 5%
  • hydroxycinnamic acid derivatives conjugated with adamantylamide of the present invention have the activities of inhibiting active oxygen and melanin generation, promoting procollagen biosynthesis and inhibiting collagenase expression. So, the compositions containing the hydroxycinnamic acid derivatives as an active ingredient can be effectively used as an anti-oxidative cosmetic composition with inhibiting effect of active oxygen, a cosmetic composition for whitening with improvement of skin pigmentation, or an anti-wrinkle cosmetic composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des dérivés d'acide hydroxycinnamique conjugués avec de l'adamantylamide, leur procédé de préparation et des compositions cosmétiques les contenant. Les dérivés d'acide hydroxycinnamique de la présente invention présentent des activités d'inhibition de la génération de mélanine par anti-oxydation et de renforcement de la synthèse de collagène. C'est pourquoi les compositions contenant les dérivés de l'invention peuvent être efficacement utilisées en tant que compositions cosmétiques à effet anti-oxydant, effet améliorant sur la pigmentation cutanée et effet anti-rides par renforcement de la synthèse de collagène.
PCT/KR2007/002847 2006-08-10 2007-06-13 Dérivés d'acide hydroxycinnamique et leur procédé de préparation et composition cosmétique les contenant WO2008018683A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2006-0075755 2006-08-10
KR1020060075755A KR100957465B1 (ko) 2006-08-10 2006-08-10 히드록시신남산 유도체 화합물과 그 제조방법 및 이를함유하는 화장료 조성물

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103702977A (zh) * 2011-08-05 2014-04-02 株式会社爱茉莉太平洋 新型苯甲酸酰胺化合物

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101557646B1 (ko) 2013-04-29 2015-10-06 (주)삼경코스텍 피부미백용 조성물
KR102649608B1 (ko) * 2022-02-17 2024-03-21 에코리엔트샤인 (주) 축광 탄성칩 조성물, 이를 함유하는 탄성바닥재 및 이를 이용한 시공방법

Citations (6)

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Publication number Priority date Publication date Assignee Title
EP0333522A2 (fr) * 1988-03-18 1989-09-20 MITSUI TOATSU CHEMICALS, Inc. Dérivés du catéchol et préparations pharmaceutiques les contenant
EP0399814A2 (fr) * 1989-05-23 1990-11-28 Sankyo Company Limited Dérivés de phénol stimulant le facteur de croissance du nerf humain
JPH049355A (ja) * 1990-04-02 1992-01-14 Shiseido Co Ltd 桂皮酸誘導体、紫外線吸収剤およびそれを配合した皮膚外用剤
JPH05105643A (ja) * 1991-10-15 1993-04-27 Kao Corp 桂皮酸誘導体およびこれを有効成分とする美白化粧料
JPH05246949A (ja) * 1992-03-06 1993-09-24 Kao Corp 新規桂皮酸誘導体、その製造方法及び該化合物からなる紫外線吸収剤
US5426210A (en) * 1991-05-09 1995-06-20 Shiseido Co., Ltd. Adduct of cinnamic acid and glycerin, ultraviolet absorbent and external preparation for skin

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0333522A2 (fr) * 1988-03-18 1989-09-20 MITSUI TOATSU CHEMICALS, Inc. Dérivés du catéchol et préparations pharmaceutiques les contenant
EP0399814A2 (fr) * 1989-05-23 1990-11-28 Sankyo Company Limited Dérivés de phénol stimulant le facteur de croissance du nerf humain
JPH049355A (ja) * 1990-04-02 1992-01-14 Shiseido Co Ltd 桂皮酸誘導体、紫外線吸収剤およびそれを配合した皮膚外用剤
US5426210A (en) * 1991-05-09 1995-06-20 Shiseido Co., Ltd. Adduct of cinnamic acid and glycerin, ultraviolet absorbent and external preparation for skin
JPH05105643A (ja) * 1991-10-15 1993-04-27 Kao Corp 桂皮酸誘導体およびこれを有効成分とする美白化粧料
JPH05246949A (ja) * 1992-03-06 1993-09-24 Kao Corp 新規桂皮酸誘導体、その製造方法及び該化合物からなる紫外線吸収剤

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103702977A (zh) * 2011-08-05 2014-04-02 株式会社爱茉莉太平洋 新型苯甲酸酰胺化合物
EP2740721A2 (fr) * 2011-08-05 2014-06-11 Amorepacific Corporation Nouveau composé d'amide d'acide benzoïque
JP2014529583A (ja) * 2011-08-05 2014-11-13 株式会社アモーレパシフィックＡｍｏｒｅｐａｃｉｆｉｃ Ｃｏｒｐｏｒａｔｉｏｎ 新規安息香酸アミド化合物
EP2740721A4 (fr) * 2011-08-05 2015-03-18 Amorepacific Corp Nouveau composé d'amide d'acide benzoïque
CN103702977B (zh) * 2011-08-05 2016-08-17 株式会社爱茉莉太平洋 苯甲酸酰胺化合物

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KR20080014279A (ko) 2008-02-14
KR100957465B1 (ko) 2010-05-14

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