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WO2011039175A1 - Traitement de l'acné vulgaire, de l'acné rosacée et de l'alopécie androgénétique et protection contre le cancer chez les fumeurs, l'obésité et le diabète sucré - Google Patents

Traitement de l'acné vulgaire, de l'acné rosacée et de l'alopécie androgénétique et protection contre le cancer chez les fumeurs, l'obésité et le diabète sucré Download PDF

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Publication number
WO2011039175A1
WO2011039175A1 PCT/EP2010/064346 EP2010064346W WO2011039175A1 WO 2011039175 A1 WO2011039175 A1 WO 2011039175A1 EP 2010064346 W EP2010064346 W EP 2010064346W WO 2011039175 A1 WO2011039175 A1 WO 2011039175A1
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Prior art keywords
treatment
resveratrol
medicament
rosacea
acne
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Application number
PCT/EP2010/064346
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English (en)
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Bodo Melnik
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Bodo Melnik
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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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • 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
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • 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
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts thereof
    • 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
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to treatment of acne vulgaris, rosacea, androge- netic alopecia and protection of cancer, obesity and diabetes mellitus. Background of the invention
  • Acne is a chronic inflammatory disease of the pilosebaceous unit, mostly affecting the sebaceous follicles.
  • Major contributors of acne pathogenesis are abnormal follicular differentiation with increased cornification, enhanced sebaceous gland activity with hyperseborrhea, bacterial hypercolonization, inflam- mation as wells as immunological host reactions.
  • Sebaceous glands function continuously in excreting sebum to the skin surface with an average sebaceous cell transition time of 14 days. Androgens play an essential role for the stimulation of the size of sebocytes and sebum production as well as keratino- cyte proliferation in the ductus seboglandularis and the acroinfundibulum.
  • Exogeneous androgen excess or hyperandrogenism are associated with increased sebum production and the development of severe acne.
  • Acne-prone skin exhibits a higher androgen receptor density and higher 5a-reductase type-I activity than not involved skin.
  • Anti-androgens reduce the synthesis of sebaceous lipids and improve acne, whereas androgen-insensitive subjects who lack functional androgen receptors do not produce sebum and do not develop acne.
  • Rosacea is an inflammatory skin disease appearing in areas with high density of sebaceous glands.
  • the primary clinical features of rosacea include flushing, inflammatory papules, pustules, and teleangiectases.
  • Oxydative stress plays an important role in the pathophysiology of the disease.
  • mesenchymal tissue has an increased tendency of proliferation : sebaceous glands with sebaceous hyperplasia, connective tissue with fibrosis and formation of rhinophyma, and increased angiogenesis with formation of multiple teleangiectases.
  • Disturbed homeostasis of vascular and fibroblast growth factors have been implicated in the pathogenesis of rosacea.
  • Male androgenetic alopecia or male pattern hair loss is another androgen- dependent disease of the pilosebaceous unit. This most common hair loss is characterized by a progressive decline in the duration of anagen, an increase in the duration of telogen, and miniaturization of scalp follicles, indicating a final common pathway of follicular regression.
  • Interleukin-lalpha is regarded as a negative hair growth regulator and is involved in androgen-dependent gene regulation of dermal papilla cells. Multiple FGFs and FGFRs are involved in the ordered regulation of the hair cycle progression.
  • Androgen-dependent expression of dickkopfl from balding dermal papilla cells have been implicated in the apoptosis of follicular keratinocytes.
  • Androgen receptor (AR) transacti- vation is negatively controlled by FoxOl among other AR corepressors.
  • AR transcriptional activity is modulated by acetylation.
  • FoxO-1 forkhead box 0-1
  • FoxO-1 is involved in repression of several nuclear receptors like androgen receptor (AR), peroxisome proliferator-activated receptor gamma (PPARy), retinoid X receptor (RXR) and liver X receptor (LXR) and activation of the promoter of insulin-sensitive glucose transporter 4 (GLUT4).
  • AR androgen receptor
  • PPARy peroxisome proliferator-activated receptor gamma
  • RXR retinoid X receptor
  • LXR liver X receptor
  • IGF-1 insulin/insulin-like growth factor-1
  • PI3K phosphoinositide-3-kinase
  • Akt phosphorylates FoxO-1.
  • Phosphorylated FoxO-1 is translocated from the nucleus into the cytoplasm, where it is sequestered by protein 14.3.3.
  • the nuclear extrusion of FoxO-1 activates AR, PPARy, RXR/LXR heterodimers resulting in transactivation of these receptors.
  • Activation of AR is important in the pathogenesis of acne.
  • Activated AR induces sebocyte proliferation, whe- reas activated PPARY induces terminal differentiation of sebocytes with increased lipogenesis.
  • SREPBlc Sterol regulatory element binding protein lc
  • FoxO- 1 phosphorylation is further increased by FoxO- 1 acetylation .
  • FoxO- 1 is deacylated by a physiologic deacylase sirtuin 1 (SIRTl) .
  • SIRTl physiologic deacylase sirtuin 1
  • FoxO- 1 deacetylation is important to increase the concentration of nuclear FoxO- 1 which is necessary for repression of AR, PPARy, RXR/LXR and activation of GLUT4 at the promoter level . It is the major strategy of this invention to increase nuclear FoxO- 1 levels in androgen-related disorders.
  • AR transcriptional activity is modified by AR acetylation .
  • SIRTl is a corepressor of AR and deacylation of AR by SIRTl decreases AR transcriptional activity.
  • Resveratrol activates Sirtuin 1 (SIRTl) and is thus useful in the attenuation of pathological signaling in acne, rosacea, and androgenetic alopecia, especially AR-mediated growth factor signaling .
  • SIRTl Sirtuin 1
  • These treatments will also be beneficial for hypertrichosis, hirsutism, virilism and polycystic ovary syndrome.
  • One embodiment of the invention is the use of resveratrol for the preparation of a medicament for the treatment of acne, rosacea or androgenetic alopecia .
  • Resveratrol (trans-resveratrol) is trans-3,5,4 ' -trihydroxystilbene and is a natural compound especially present in red wine grapes and red wine.
  • Resveratrol derivatives are compounds of the general formulas shown in figure 4 and include cis-resveratrol and cis-resveratrol derivatives.
  • an amount of 100 to 2000 or 500 to 2000 mg resveratrol per day is preferred .
  • the use in form of capsules or liquids is especially suitable.
  • Daily dosis between 5 and 20 mg resveratrol per kg body weight are useful.
  • the application in a formulation for sublingual or buccal administration is preferred .
  • Such formulations are e.g. available from the company Terraternal .
  • Suitable sublingual preparations are e.g. chewing gums and lozenges.
  • Other useful forms for oral administration are e.g . ampoules and syrups.
  • resveratrol is combined with other hydroxystilbenes like piceatannol in comparable concentrations.
  • the medicament is in a form for topical appli- cation like a cream, a lotion, a gel, a hydrogelor a solution.
  • a suitable amount of resveratrol is 0.1 to 3% or 0.5 to 3% by weight of the topical preparation.
  • Topical application provides the possibility of topical and transdermal delivery.
  • a preferred form for topical application of resveratrol is a hydrogel .
  • a low viscosity hydrogel is preferred. Suitable preparations of hydrogels and solutions are described in Chi-Feng Hung et al., Biol. Pharm. Bull . 31 (5) 955-962 (2008).
  • topical resveratol use is the combination with other hydroxystilbenes.
  • the oral or topical treatment is combined with other topi- cal or oral treatment for the mentioned diseases.
  • the active ingredient resveratrol is combined with a further ingredient selected from
  • a preferred amount of metformin is 250 to 2000 mg per day.
  • a combination with tetracyclines, oral isotretinoin, anti- androgens like cyproterone acetate, metformin, rosiglitazone, pioglitazone and/or other related PPARy agonists (ligands) is especially preferred .
  • the substances could be combined in one pharmaceutical preparation or could be administered as overlapping treatments in separate pharmaceuticals formulations.
  • the medicament of the invention may be used in combination with topical medicaments like adapalene, erythromycin, other topical antibiotics like nadifloxacine, all-trans-retinoic acid, azelaic acid and/or benzoyl peroxide.
  • topical medicaments like adapalene, erythromycin, other topical antibiotics like nadifloxacine, all-trans-retinoic acid, azelaic acid and/or benzoyl peroxide.
  • a combination with tetracycline, oral isotre- tinoin, anti-androgens like cyproterone acetate, metformin, rosiglitazone, pioglitazone and/or other related PPARy agonists (ligands) is suitable.
  • topical metronidazol As an additional topical administration, topical metronidazol, erythromycin, azelaic acid or the like is useful.
  • a treatment with further - known oral or topical administration is useful.
  • suitable medicaments for additional systemic treatments are anti-androgens (women), finasteride (men), dutasteride (men), other 5a-reductase inhibitors, metformin, rosiglitazone, pioglitazone and/or other related PPARY agonists (ligands) .
  • the invention is directed to the use of resveratrol and/or resveratrol derivatives for the preparation of a medicament for oral preventive treatment of individuals with an increased familial risk of cancer, smokers, obese individuals, persons with pre-diabetes mellitus or with diabetes mellitus type 2.
  • a suitable dose is 100 to 2000 or 200 to 2000 mg resveratrol per day
  • the invention is directed to the use of resveratrol for the preparation of a medicament for the treatment of hypertrichosis, hirsutism, virilism and polycystic ovary syndrome.
  • FIGURES Figure 1 shows a 15 year old boy before and 4 weeks after topical 0.1% resveratrol treatment.
  • Figure 2 shows a 12-year-old boy before and 6 weeks after systemic resveratrol treatment.
  • Figure 3 shows a 15-year-old girl before and 8 weeks after systemic and topi- cal resveratrol treatment.
  • Figure 4 shows resveratrol derivatives as described in Mazue et al . , European Journal of Medicinal Chemistry 45 (2010) 2972-2980. Examples for resveratrol use in acne
  • a 15 year old boy with acne vulgaris was treated with a hydrogel comprising resveratol in a concentration of 0.1% (w/w).
  • the hydrogel was applied twice a day to the affected facial skin areas.
  • the acne improved significantly over a period of 4 weeks, see figure 1.
  • a 12-year old boy with acne vulgaris of the face was treated daily for 6 weeks with 3 x 100 mg of sublingual/buccal resveratrol tablets. Acne significantly improved after 6 weeks of systemic resveratrol treatment, see figure 2.
  • a 15-year-old girl with acne papulopustulosa was treated daily with 3 x 100 mg of sublingual/buccal resveratrol tablets as well as twice daily with a 0.1% resveratrol-containing hydrogel .
  • Acne papulopustulosa and seborrhea significantly improved after 8 weeks of systemic and topical resveratrol treatment see figure 3.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne l'utilisation de resvératrol et/ou de dérivés de resvératrol pour la préparation d'un médicament pour le traitement de l'acné, l'acné rosacée, l'alopécie androgénétique ou des maladies hyperprolifératives de la peau.
PCT/EP2010/064346 2009-09-29 2010-09-28 Traitement de l'acné vulgaire, de l'acné rosacée et de l'alopécie androgénétique et protection contre le cancer chez les fumeurs, l'obésité et le diabète sucré WO2011039175A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP09171639.9 2009-09-29
EP09171639 2009-09-29
US24930209P 2009-10-07 2009-10-07
US61/249,302 2009-10-07
EP09173153 2009-10-15
EP09173153.9 2009-10-15

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WO2011039175A1 true WO2011039175A1 (fr) 2011-04-07

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Cited By (12)

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WO2011089168A3 (fr) * 2010-01-21 2011-12-29 INSERM (Institut National de la Santé et de la Recherche Médicale) Composition particuliere pour son application comme medicament
WO2013092269A1 (fr) * 2011-12-19 2013-06-27 Ares Trading S.A. Compositions pharmaceutiques des glitazones et des activateurs de nrf2
DE102013104441A1 (de) * 2013-04-30 2014-10-16 Bodo C. Melnik Akne-Medikament und Verfahren zu seiner Herstellung
WO2015085143A3 (fr) * 2013-12-06 2015-07-30 Stc.Unm Agents thérapeutiques pour maladies et affections cutanées
US9504679B2 (en) 2011-12-19 2016-11-29 Bjoern Colin Kahrs Pharmaceutical compositions comprising glitazones and Nrf2 activators
WO2017004692A1 (fr) 2015-07-08 2017-01-12 Triple Hair Inc. Composition comprenant du resvératrol et de la mélatonine pour réduire la chute des cheveux et/ou améliorer la repousse des cheveux
US9549905B2 (en) 2011-03-23 2017-01-24 The Regents Of The University Of California Treatment of inflammatory and infectious skin disorders
US9889165B2 (en) 2016-04-21 2018-02-13 Naked Biome, Inc. Compositions and methods for treatment of skin disorders
CN110923198A (zh) * 2018-09-19 2020-03-27 中国农业大学 白藜芦醇的用途及原始卵泡的体外激活试剂与方法
WO2021007108A1 (fr) * 2019-07-05 2021-01-14 Icahn School Of Medicine At Mount Sinai Méthode de prévention contre la perte de cheveux
US20210128452A1 (en) * 2019-11-04 2021-05-06 Seed Health Inc. Compositions and methods of improving the skin microbiome
WO2024119694A1 (fr) * 2022-12-08 2024-06-13 苏州大学 Tonique pour la croissance des cheveux de type mousse et son procédé de préparation

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EP0953345A1 (fr) * 1998-04-10 1999-11-03 L'oreal Utilisation d'au moins un hydroxystilbène en tant qu'agent diminuant l'adhésion des micro-organismes
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EP1138323A2 (fr) * 2000-03-24 2001-10-04 D.B.P. (Development Biotechnological Processes) di Rossi Valentina e C. s.n.c. Resveratrol pour le traitement de l'eczéma exfoliative, de l'acné ou du psoriasis
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Cited By (26)

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EP3347009A4 (fr) * 2015-07-08 2019-01-02 Triple Hair Inc. Composition comprenant du resvératrol et de la mélatonine pour réduire la chute des cheveux et/ou améliorer la repousse des cheveux
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WO2021007108A1 (fr) * 2019-07-05 2021-01-14 Icahn School Of Medicine At Mount Sinai Méthode de prévention contre la perte de cheveux
US20210128452A1 (en) * 2019-11-04 2021-05-06 Seed Health Inc. Compositions and methods of improving the skin microbiome
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