WO2012157587A1 - Agent antirides, inhibiteur des métalloprotéinases matricielles (mmp) et/ou activateur de production de laminine 5 contenant chacun un propionate de 1-pipéridine - Google Patents

Agent antirides, inhibiteur des métalloprotéinases matricielles (mmp) et/ou activateur de production de laminine 5 contenant chacun un propionate de 1-pipéridine Download PDF

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Publication number
WO2012157587A1
WO2012157587A1 PCT/JP2012/062222 JP2012062222W WO2012157587A1 WO 2012157587 A1 WO2012157587 A1 WO 2012157587A1 JP 2012062222 W JP2012062222 W JP 2012062222W WO 2012157587 A1 WO2012157587 A1 WO 2012157587A1
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laminin
mmp
scca1
inhibitor
production promoter
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PCT/JP2012/062222
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English (en)
Japanese (ja)
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片桐　千華
華代 松本
青木　宏文
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株式会社資生堂
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    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to an anti-wrinkle agent comprising 1-piperidinepropionic acid and / or a salt thereof, more specifically, a matrix metalloproteinase (MMP) inhibitor and / or a laminin 5 production promoter.
  • MMP matrix metalloproteinase
  • Skin covering the entire body of various animals including human beings is exposed to external factors such as sunlight, dryness, oxidation, environmental stress and wrinkle formation due to aging, hardening, spots, dullness, reduced elasticity, etc. Exposed to change.
  • the skin is roughly divided into two layers, the epidermis and the dermis. Between the epidermis and the dermis there is a thin and delicate membrane called the basement membrane.
  • Epidermal metabolism depends on factors and blood supply produced by dermal cells through this basement membrane.
  • the proliferation and differentiation of the epidermis in the skin is influenced by the basement membrane and the dermis. Therefore, communication between the epidermis and the dermis via the basement membrane plays an important role in regulating the function of the skin epidermis.
  • the skin basement membrane has a special structure called an anchoring complex that plays a role in stabilizing the adhesion and communication between the two tissues, the epidermis and dermis.
  • the anchoring complex proteins are linked to both keratin cytoskeleton of keratinocytes and connective tissue proteins of the dermal papillary layer.
  • One important component of the anchoring complex is laminin 5 (Rousselle et al., J J Cell Biol. 1991 Aug; 114 (3): 567-76).
  • Laminin 5 is a protein composed of ⁇ 3, ⁇ 3, and ⁇ 2 chains, and not only directly binds to type VII collagen that forms anchoring fibers connected to the dermal papillary layer, but is also complexed with other laminin 6 and 7 It is reported that this complex binds to type IV collagen, which is the basement membrane skeleton, via a nidogen.
  • type IV collagen constituting the complex decreases with aging (Vazquez F et al., Maturitas 1996, 25: 209-215), and type VII collagen to which laminin 5 binds.
  • dermatofibroblasts derived from elderly people the production ability is reduced at the protein level and mRNA level compared to dermal fibroblasts derived from young people (Chen et al., J. Invest. Dermatol., 1994, 102: 205-209).
  • ⁇ Anti-wrinkle is one of the major problems in preventing skin aging.
  • wrinkles are roughly classified into shallow epidermal wrinkles (small wrinkles) and deep dermal wrinkles (large wrinkles).
  • dermal wrinkles are caused by changes in the basement membrane and the dermal layer. It is thought that the maintenance of the basement membrane is important for this reason.
  • ECM extracellular matrix
  • MMP matrix metalloprotease
  • MMP1 degrades type I and type III collagen, which are components of EMC
  • MMP2 and MMP9 belonging to the gelatinase group degrade laminin, type IV collagen, elastin, which is an EMC component, and the like.
  • MMP3 and MMP10 belonging to the stromelysin group are known as enzymes that degrade proteoglycan, type IV collagen, laminin, and the like. It has been reported that when the skin fibroblasts are irradiated with ultraviolet rays (UVB) in the middle wave region, the mRNA expression, enzyme activity and proteolytic level of MMP increase (Fisher G. J. et al., Nature). , 1996, 379, 335-339), which is considered to be one of the causes of the reduced degeneration of EMC by ultraviolet rays.
  • UVB ultraviolet rays
  • the present invention pays attention to the function of MMP and laminin 5 in the wrinkle formation mechanism of skin, particularly basement membrane and dermis, and is a novel and effective anti-wrinkle agent, more specifically, MMP inhibitor and / or laminin 5 production promoter. It is an issue to provide.
  • the present inventor has studied various factors in the epidermis, dermis and basement membrane and the effects caused by them, and as a result, squamous epithelium known to be involved in epidermal damage. Suppression of MMP, which is a factor affecting wrinkle formation in the dermis and basement membrane, and / or promotion of production of laminin 5 can be achieved by suppressing the production of cell cancer-associated antigen (SCCA1: Squamous Cell Carcinoma Antigen 1). I found it for the first time.
  • SCCA1 Squamous Cell Carcinoma Antigen
  • 1-piperidinepropionic acid that suppresses the production of SCCA1 has MMP inhibitory activity and / or laminin 5 production promoting activity, and the present invention has been completed.
  • the present invention includes the following inventions.
  • MMP matrix metalloproteinase
  • An anti-wrinkle agent comprising 1-piperidinepropionic acid and / or a salt thereof.
  • MMP matrix metalloproteinase
  • FIG. 1 shows a graph showing the relationship between female life stage and SCCA1 expression.
  • FIG. 2 shows the means for establishing SCCA1 highly expressing cells.
  • FIG. 3 shows the means for establishing SCCA1 low expressing cells.
  • FIG. 4 schematically shows the experimental method of Example 1.
  • FIG. 5 shows the effect of SCCA1 on MMP2 and MMP9.
  • FIG. 6 shows the effect of SCCA1 on collagen production.
  • FIG. 7 shows the effect of SCCA1 on laminin 5 production.
  • FIG. 8 shows changes in MMP expression due to the addition of rSCCA1 to human fibroblasts.
  • FIG. 9 shows a comparison of the gene expression level of laminin 5 with and without the addition of 1-piperidinepropionic acid in the cell lines.
  • SCCA1 is an antigen originally found in squamous cell carcinoma cells, and has a high blood concentration in squamous cell carcinoma of the cervix, embryo, esophagus, and skin, and is used for diagnosis of squamous cell carcinoma (H. Kato et al., Cancer, 1997, 40; 1621-1628, N. Mno et al., Cancer, 1998, 62; 730-734).
  • SCCA1 is an apoptotic cell
  • JP-A-2005-281140 an anti-apoptotic factor having an inhibitory action
  • SCCA1 expression is increased 16-fold, 90-fold in exposed area skin, 232-fold in hay fever allergic skin, and 466-fold in psoriatic skin (JP 2007-279024).
  • the present inventors have shown that cell growth activation and epidermal thickening are observed in SCCA high-expressing mice, that there is a correlation between cell growth and SCCA1 expression level in SCCA1 high-expressing cell lines, and SCCA knockdown cells. It was found that cell proliferation activity was reduced in the strain. Then, the present inventor has reported that 1-piperidinepropionic acid and / or a salt thereof can significantly suppress SCCA1 production and can prevent and improve epidermal thickening through various drug screenings (specialty). Open 2009-242345).
  • the present inventors have also found that the expression level of SCCA1 changes in the female life stage.
  • women's age was classified into the following five stages: childhood (2-9 years), adolescence (10-19 years: men with menarche), adulthood (20-44 years: regular sexual cycle) And those who are not pregnant or breastfeeding), menopause (45-59 years old: those who have menopausal symptoms and are not pregnant or breastfeeding), and postmenopausal (60-90 years old: menopause)
  • the expression level of SCCA1 was measured, it was found that the SCCA1 expression level significantly increased after menopause (FIG. 1).
  • the MMP inhibitor and / or laminin 5 production promoter comprising the SCCA1 production inhibitor containing 1-piperidinepropionic acid and / or a salt thereof of the present invention includes wrinkles and / or laminin 5 caused by the presence of MPP. It can be used as an anti-wrinkle agent that can prevent and / or improve wrinkles due to lack.
  • the 1-piperidinepropionic acid according to the present invention is a compound of the following general formula (I).
  • the 1-piperidinepropionic acid represented by the general formula (I) according to the present invention is a known substance, and can be easily synthesized by a known method, or a commercially available product can be easily purchased.
  • the 1-piperidinepropionic acid represented by the general formula (I) according to the present invention can be converted into an inorganic salt or an organic salt by a known method.
  • a salt used in this invention for example, as an inorganic salt, hydrochloride, sulfate, phosphate, hydrobromide, sodium salt, potassium salt, magnesium salt, calcium salt, ammonium Examples include salts.
  • Organic salts include acetate, lactate, maleate, fumarate, tartrate, citrate, methanesulfonate, p-toluenesulfonate, triethanolamine salt, diethanolamine salt, amino acid salt, etc. Can be mentioned.
  • the anti-wrinkle agent, MMP inhibitor and / or laminin 5 production promoter of the present invention comprises 1-piperidinepropionic acid and / or a salt thereof.
  • the anti-wrinkle agent, MMP inhibitor, and / or laminin 5 production promoter includes an effective amount of 1-piperidinepropionic acid to exhibit anti-wrinkle activity, MMP inhibitory activity, and / or laminin 5 production promoter activity.
  • And / or a salt thereof, and the content thereof is preferably 0.0001 to 20% by mass in the composition, more preferably 0.0005 to 10% by mass, and particularly preferably 0.001 to 5% by mass. It is. If the amount is less than 0.0001% by mass, the effect is not sufficiently exhibited. On the other hand, if the content exceeds 20% by mass, no significant improvement in the effect is observed, and formulation may be difficult.
  • the anti-wrinkle agent, MMP inhibitor and / or laminin 5 production promoter of the present invention is used as, for example, a wrinkle improving agent
  • the effects of the present invention are not impaired except for 1-piperidinepropionic acid and / or a salt thereof.
  • components usually used in cosmetics and external preparations such as whitening agents, moisturizers, antioxidants, ultraviolet absorbers, surfactants, thickeners, pH adjusters, diluents, various skin nutrients,
  • a pigment, a fragrance, an alcohol, an aqueous component, an oil component, water, a powder, and the like can be appropriately blended as necessary.
  • disodium edetate trisodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, metal chelates such as gluconic acid, caffeine, tannin, verapamil, tranexamic acid and its derivatives, licorice extract, grabrizine , Hot water extract of karin fruit, various herbal medicines, tocopherol acetate, glycyrrhizic acid and its derivatives, or salts thereof, vitamin C, magnesium ascorbate phosphate, glucoside ascorbate, arbutin, kojic acid, etc.
  • metal chelates such as gluconic acid, caffeine, tannin, verapamil, tranexamic acid and its derivatives, licorice extract, grabrizine , Hot water extract of karin fruit, various herbal medicines, tocopherol acetate, glycyrrhizic acid and its derivatives, or salts thereof, vitamin C, magnesium ascorbate phosphate, glucoside ascorbat
  • Glucose, fructose, mannose, sucrose, trehalose, xylitol, sorbitol, erythritol and other saccharides, retinoic acid, retinol, retinol acetic acid, retinol palmitic acid and other vitamin A derivatives can be added as appropriate
  • the dosage form of the external preparation for skin is not particularly limited.
  • solution system solubilization system, emulsification system, powder dispersion system, water-oil two-phase system, water-oil-powder three-phase system, solid, ointment, gel, aerosol, mousse, mist, spray, patch, adhesive gel
  • any dosage form can be applied.
  • the use aspect is also arbitrary, for example, basic cosmetics, such as lotion, milky lotion, cream, a pack, a cosmetic liquid, makeup cosmetics, such as a foundation, functional cosmetics, such as a sunscreen, cosmetics for hair
  • the present invention is not limited to these.
  • SCCA1 high-expressing cells and low-expressing cells are prepared (prepared by the method described in JP-A-2009-242345, see also FIGS. 2 and 3) and cultured in DMEM-10% FBS medium for 24 hours. A medium was added to human fibroblasts (1 ⁇ 10 5 cells / well) and cultured for 24 hours (FIG. 4).
  • Cells Human fibroblasts (# HDF342 P5100709) were used as cells. Cells were seeded in a 6-well plate at 2.0 ⁇ 10 5 cells per well, and a medium obtained by adding 10% FBS to Dulbecco's modified Eagle (DMEM) medium (Nissui Pharmaceutical Co., Ltd.) was used. The cells were cultured at 37 ° C., 5% CO 2 and saturated water vapor atmosphere for 24 hours. Thereafter, the medium was replaced with DMEM medium containing no 10% FBS, and further cultured for 24 hours.
  • DMEM Dulbecco's modified Eagle
  • RNA extraction / cDNA synthesis After washing twice with 2 ml PBS per well, 1 mL of ISOGEN (Nippon Gene) was added and recovered. RNA was extracted according to the manual, and the concentration and 260 nm / 280 nm OD ratio were confirmed by NanoDrop.
  • RNA solution was adjusted to 150 ng / ⁇ L with RNase-free water, 20 ⁇ L (4 ⁇ g) was adjusted to 50 ⁇ M random primer (TAKARA) and 2 mM dNTP Mixture (TOYOBO), 5 ⁇ First strand buffer (Invitrogen), 0.1 M DTT (Invitrogen) , SuperScript II (Invitrogen), and RNase inhibitor (Invitrogen) were used for reverse transcription reaction with a total reaction volume of 80 ⁇ L.
  • TAKARA random primer
  • TOYOBO 2 mM dNTP Mixture
  • Quantitative PCR Using LightCycler FastStart DNA MasterPlus SYBER Green1 (Roche Cat. No. 03 515 885 001), 4 ⁇ L of cDNA prepared in accordance with the above, forward and reverse primers (see below) each 0.8 ⁇ M (final concentration), Master Mix A reaction solution was prepared by adding water to a total volume of 25 ⁇ L, and was prepared using LightCycler Software Ver. Quantitative PCR was performed according to 3.5 (Roche Diagnostics). The reaction was 95 ° C.-15 minutes, (95 ° C.-15 seconds ⁇ 65 ° C.-20 seconds ⁇ 72 ° C.-20 seconds) ⁇ 45 cycles, and then a melting curve analysis from 95 ° C. to 62 ° C. was performed.
  • the primers used are as follows. As the primers, commercially available products are used for MMP1, elastin, and laminin 5 ⁇ 3, and MMP2, MMP3, MMP9, and MMP10 are prepared by the present inventors. The number of gene cycles of each cDNA sample was determined, and the value was calculated using a calibration curve with rSCCA1 (2.0 ⁇ M) as a standard. Moreover, what was corrected with the GAPDH value obtained with the acid of each cDNA specimen was expressed as the mean ⁇ SE of specimens under the same conditions. Significant differences between groups were tested by Student's t test.
  • MMP1, MMP2, MMP3, MMP9, and MMP10 the expression level of MMP2 and MMP9 was significantly increased by the addition of rSCCA1 to human fibroblasts (FIG. 6).
  • GAPDH Forward (hGAP69F) 5'- GGTGAAGGTCGGAGTCAACGGATTTGGCG-3 '(SEQ ID NO: 1) Reverse (hGAP206R) 5'- TATTGGAACATGTAAACCATGTAGTTGAGG -3 '(SEQ ID NO: 2) MMP1 Forward 5'- GACTTCTACCCATTTGATGG -3 '(SEQ ID NO: 3) Reverse 5'- TTAGGGTTGGGGTCTTCATC -3 '(SEQ ID NO: 4) MMP2 Forward 5'- ACTCCTGAGATCTGCAAACAGGA -3 '(SEQ ID NO: 5) Reverse 5'- ACACCTGCAAAGAACACAGCC -3 '(SEQ ID NO: 6) MMP3 Forward 5'- GACTCGGTTCCGCCTGTCT -3 '(SEQ ID NO: 7) Reverse 5'- CGCCTGAAGGAAGAGATGGC -3 '(SEQ ID NO: 8) MMP9 Forward 5'
  • Propylene glycol and caustic potash are added to ion-exchanged water and dissolved, and heated to 70 ° C. (aqueous phase).
  • the other ingredients are mixed, heated and melted, and kept at 70 ° C. (oil phase).
  • the oil phase is gradually added to the aqueous phase, and after the addition is completed, the temperature is maintained for a while to cause the reaction. Thereafter, the mixture is uniformly emulsified with a homomixer and cooled to 30 ° C. while stirring well.
  • Propylene glycol is added to ion-exchanged water and heated to 70 ° C. (aqueous phase).
  • the other ingredients are mixed, heated and melted, and kept at 70 ° C. (oil phase).
  • the oil phase is added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
  • a phase ion-exchanged water
  • Polyethylene glycol 1500 and triethanolamine are added to the remaining ion-exchanged water, dissolved by heating and maintained at 70 ° C. (aqueous phase).
  • the other ingredients are mixed, heated and melted, and kept at 70 ° C. (oil phase).
  • Add the oil phase to the water phase preliminarily emulsify, add the A phase and uniformly emulsify with a homomixer.
  • Propylene glycol is added to ion-exchanged water and heated to 70 ° C. (aqueous phase).
  • the other ingredients are mixed, heated and melted and kept at 70 ° C. (oil phase). While stirring the oil phase, the aqueous phase is gradually added thereto and uniformly emulsified with a homomixer. Cool to 30 ° C. while stirring well after emulsification.
  • Carbopol 940 is uniformly dissolved in ion-exchanged water, while 1-piperidinepropionic acid and polyoxyethylene (50 mol) oleyl alcohol ether are dissolved in 95% ethanol and added to the aqueous phase. Next, after adding other components, the mixture is neutralized with caustic soda and L-arginine and thickened to obtain a jelly.
  • a phase and C phase are uniformly dissolved, and A phase is added to C phase to solubilize.
  • the phase B is then added before filling.
  • a phase, B phase, and C phase are uniformly dissolved, and B phase is added to A phase to solubilize. Next, this is added to phase C and then filled.
  • Glycerin, dipropylene glycol, 1,3-butylene glycol, erythritol, L-ascorbyl magnesium phosphate and sodium carboxymethylcellulose are added to purified water and heated to 70 ° C. (aqueous phase).
  • the other ingredients are mixed, heated and melted, and kept at 70 ° C. (oil phase).
  • the oil phase is added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.

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Abstract

L'objet de cette invention est de pourvoir à un agent antirides qui soit nouveau et efficace. Cette invention concerne un inhibiteur des métalloprotéinases matricielles (MMP) et/ou un activateur de production de laminine 5, ainsi qu'un agent antirides, contenant chacun un propionate de 1-pipéridine et/ou un sel de celui-ci.
PCT/JP2012/062222 2011-05-13 2012-05-11 Agent antirides, inhibiteur des métalloprotéinases matricielles (mmp) et/ou activateur de production de laminine 5 contenant chacun un propionate de 1-pipéridine WO2012157587A1 (fr)

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JP2011108801A JP2012240911A (ja) 2011-05-13 2011-05-13 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
JP2011-108801 2011-05-13

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WO2022128057A1 (fr) 2020-12-14 2022-06-23 Symrise Ag Médicament pour la prévention et le traitement de la dégradation du collagène dans un tissu conjonctif humain
WO2022224380A1 (fr) * 2021-04-21 2022-10-27 株式会社 資生堂 Produit cosmétique
US11628163B2 (en) * 2017-03-10 2023-04-18 Università Degli Studi Di Padova 1-piperidinepropionic acid for treating a fibrosing disease
WO2023149226A1 (fr) * 2022-02-03 2023-08-10 株式会社 資生堂 Composition de soin de la peau

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WO2023095685A1 (fr) * 2021-11-29 2023-06-01 株式会社 資生堂 Produit cosmétique
WO2024095793A1 (fr) * 2022-11-02 2024-05-10 株式会社 資生堂 Composition

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WO2007034750A1 (fr) * 2005-09-22 2007-03-29 Shiseido Company, Ltd. Agent réducteur de rides
JP2009051790A (ja) * 2007-08-29 2009-03-12 Maruzen Pharmaceut Co Ltd 抗酸化剤、抗老化剤、抗炎症剤、育毛剤、抗肥満剤、及び美白剤、並びに化粧料及び美容用飲食品
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JP2011068570A (ja) * 2009-09-24 2011-04-07 Maruzen Pharmaceut Co Ltd ラミニン５産生促進剤、皮膚基底膜正常化剤及び皮膚損傷回復促進剤

Cited By (4)

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US11628163B2 (en) * 2017-03-10 2023-04-18 Università Degli Studi Di Padova 1-piperidinepropionic acid for treating a fibrosing disease
WO2022128057A1 (fr) 2020-12-14 2022-06-23 Symrise Ag Médicament pour la prévention et le traitement de la dégradation du collagène dans un tissu conjonctif humain
WO2022224380A1 (fr) * 2021-04-21 2022-10-27 株式会社 資生堂 Produit cosmétique
WO2023149226A1 (fr) * 2022-02-03 2023-08-10 株式会社 資生堂 Composition de soin de la peau

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