WO2012164061A2 - Préparations cosmétiques antipelliculaires - Google Patents

Préparations cosmétiques antipelliculaires Download PDF

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Publication number
WO2012164061A2
WO2012164061A2 PCT/EP2012/060343 EP2012060343W WO2012164061A2 WO 2012164061 A2 WO2012164061 A2 WO 2012164061A2 EP 2012060343 W EP2012060343 W EP 2012060343W WO 2012164061 A2 WO2012164061 A2 WO 2012164061A2
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WIPO (PCT)
Prior art keywords
dandruff
lae
weight
combination
cosmetic preparation
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PCT/EP2012/060343
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English (en)
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WO2012164061A3 (fr
Inventor
Pina Maria Teresa BELTRÁN
Xavier Rocabayera Bonvila
Maria MINGUET BONVEHÍ
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Laboratorios Miret SA
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Laboratorios Miret SA
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Application filed by Laboratorios Miret SA filed Critical Laboratorios Miret SA
Publication of WO2012164061A2 publication Critical patent/WO2012164061A2/fr
Anticipated expiration legal-status Critical
Publication of WO2012164061A3 publication Critical patent/WO2012164061A3/fr
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • 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
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present application relates to novel cosmetic preparations for the treatment of dandruff.
  • Dandruff also called scurf, and historically termed Pityriasis capitis
  • Pityriasis capitis is clinically defined as a light seborrheic dermatitis of the scalp, which affects almost half of the post-pubertal population of both genders of any ethnicity (Saint Leger, D. ; in: The science of hair care, 2 nd edn (Bouillon, C, Wilkinson, J., eds), 2005, 609-631 ).
  • This disorder consists of an exfoliation process of the scalp epidermis caused by several parameters, which leads to an unusual increase of a yeast-like fungus of the genus Malassezia around the comeocyte (McGinley, KJ. et al.; J. Invest.
  • Corneocytes respond to this increase of the Malassezia population releasing a set of pro-inflammatory mediators responsible of the micro-inflammation frequently associated to dandruff.
  • Local deposits of immunoglobulins appear and lymphokines are released that are responsible for the recruitment and local activation of leukocytes, which in turn lead to the eventual amplification of the inflammatory reaction (Pierard-Franchimont, C. et al.; International Journal of Cosmetic Science 2006; 28: 311-318).
  • Several stimuli are known to cause this excess of sebum production on the scalp: stress, lack of adequate hygiene, allergies, vitamin B deficiency, hormonal factors and environmental factors, such as ultraviolet radiation and direct application on the scalp of some irritant chemical products. Dandruff represents an annoying aesthetical disturbance, because of the visible scalp flaking and the itching often associated.
  • Malassezia genus needs for its growth to dispose of an exogenous source of C12-C1 6 fatty acids, since it is not possible for this micro-organism to synthesize these.
  • Malassezia yeasts can usually be found on the skin of humans, however, when a major amount of sebum is produced on the skin because of the aforementioned stimuli, its population increases contributing to the development of dandruff.
  • the species of the genus Malassezia which has mainly been related to dandruff is Malassezia furfur (also known as Pityrosporum ovale), but other species such as M. globosa, M. restricts and .
  • anti-dandruff agents are: zinc pyrithione (see below a), salicylic acid (see below b) and piroctone olamine ( see below c).
  • Zinc pyrithione is a powerful anti-fungal with some keratolytic properties.
  • this compound has the disadvantage of being quite water-insoluble. Therefore, it has to be incorporated as a suspension to anti-dandruff shampoos or lotions. Besides, it is a compound with a certain degree of toxicity and it has been described that it can damage the DMA of keratinocytes (Lamore S. D. et al.; Cell Stress and Chapenones 2010; 15: 309-322).
  • Salicylic acid is a mild anti-fungal and anti-bacterial active with exfoliating properties on the basis of its capacity to soften the keratin filaments of the cornified layer of the epidermis. It is used in anti-acne and anti-dandruff treatments thanks to its keratolytic and comedolytic properties ⁇ Ranganathan S. & Mukhopadhyay T.; Indian J. Dermatol. 2010; 55(2): 130-4; Bunse T. & ahrle G.; Acta Derm. Venereol. 992; 72(1 ): 72-3).
  • Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone. It is primarily used as anti-dandruff active agent due to its anti-bacterial and anti-fungal properties. It is considered to be safer and less irritating than zinc pyrithione (Dubini F. et a!.; Azneim.-Forschung 2005; 55 (8): 478-83) being a good alternative to the latter for skin-sensitive individuals.
  • Ethyl Lauroyl Arginate HCI (LAE ® , trademark registered for Laboratorios iret S.A.) is a cationic surfactant with antimicrobial properties derived from natural building blocks: Erasmus acid and the amino acid L-arginine (see formula below). This compound inhibits the proliferation of several micro-organisms including bacteria, fungi and yeasts by means of disturbance of the membrane potential, altering cell permeability and therefore inducing the loss of cell viability (Infante R. et al.;
  • the MIC (Minimum Inhibitory Concentration) values of LAE for all microorganisms are extremely low, being 12 ppm of active substance the corresponding MIC value for Malassezia furfur (Woods, G.L. & Washington, J.A.; in: Antibacterial susceptibility test: Dilution and disk diffusion methods en Manual of Clinical Microbiology eds. Murray, P.R. et al. ASM Press. Washington, D.C. 1995,1327- 1341 ).
  • LAE has been described as an active ingredient in the treatment of dandruff (see Commission Directive 2010/3/EU of February 1 , 2010).
  • LAE is a cationic surfactant, with a very mild eco-toxicological profile and suitable for Ecocert formulations, it shows many advantages in terms of being aligned with the current market trends compared to the traditional anti-dandruff active agents.
  • the use of LAE in shampoos has been described before. For instance such a shampoo is described in EP 0 749 960 B1 ; but in that case the technological need to apply LAE was to preserve the shampoo and this use is different from the anti- dandruff use.
  • cosmetic preparations which are used to treat dandruff are the preferred ones, due to their convenience.
  • Other sorts of cosmetic preparations which can deliver anti-dandruff active agents are lotions, rinse-off conditioners and leave-on treatments.
  • LAE is effective for the treatment of dandruff.
  • This effect of LAE can be observed when the product 0.01 to 1.5 % by weight relative to the total weight of the preparation. This is within the normal range of the concentration of LAE which is normally adjusted to achieve a preservative effect. It is preferred to maintain the concentration of LAE within the range of 0.05 to 1.0 % by weight and more preferred to maintain this concentration within the range of 0.1 to 0.8 % by weight.
  • the treatment with LAE may be conducted on the basis of a conventional preparation.
  • This conventional preparation may be an aqueous solution containing further ingredients which are usual in the art. It is also possible to provide the preparation as a shampoo, whereby LAE as the active ingredient is added to any type of shampoo preparation which has been described in the state of the art.
  • the at least one further active ingredient may be selected from the group consisting of Aminopropyl Menthyl Phosphate, Artemisia annua Leaf Extract, Asarum heterotropoides Extract , Betula ermanii Stem Extract, Boesenbergia pandurata Rhizome Extract, Brassica campestris (Rapeseed) Flower Extract, Capsicum annuum Fruit Extract, Cardiospermum halicacabum Seed Extract, Carpinus tschonoskii Leaf Extract, Citronellic Acid, * Coal Tar, Coptis japonica Extract, Fragaha ananassa (Strawberry) Seed Oil, Hedera helix (Ivy) Stem Extract, Hexamidine Diisethionate, Hydrolyzed Saccharo yces/Sodm ' m Selenate Ferment Extract, Hydroxypropyl Bisstearamide MEA, Juniperus communis Sprout Extract, Kiwi Fruit Extract Beta-Glucan, Ketoconazole, Lac
  • the cosmetic preparations according to the invention contain at least one active ingredient selected from zinc pyrithione, salicylic acid and piroctone olamine besides LAE.
  • the cosmetic preparation may be any preparation which is known in the state of the art for the treatment of dandruff.
  • the concentration of LAE and the at least one other active ingredient may be lower in comparison with the concentration in compositions containing LAE and the at least one other ingredient alone.
  • the concentration of LAE may be between 0.01 and 1.5 % by weight, preferably between 0.05 and 1 % weight and more preferably between 0.1 to 0,8 % by weight relative to the total composition.
  • LAE ability of LAE to disturb the membrane of micro-organisms can help the other anti-dandruff active ingredient to penetrate more easily and therefore, lower concentrations of them might be necessary. This is particularly important when those active ingredients have an irritating effect, such as zinc pyrithione. Selenium sulphide presents a certain toxicity as well.
  • the incorporation of LAE into the anti-dandruff cosmetic preparations may allow a considerable reduction in the amount of the ingredients necessary to reach an effect in the elimination of Malassezia furfur, and as a consequence, in the improvement of the problem in patients.
  • the concentration of the at least one further active ingredient may be regularly adjusted in the range of 0.01 to 3 % by weight, depending on the activity of the active ingredient which is selected for the combined preparation.
  • the concentration of this compound in the total composition will be between 0.01 and 3 % by weight, preferably between 0.3 and 2 % by weight and more preferably between 0.5 and 1 % by weight relative to the total composition.
  • the concentration of this compound in the total composition will be between 0.01 and 3 % by weight, preferably between 0.3 and 2 % by weight and more preferably between 0.5 and 1 % by weight relative to the total composition.
  • piroctone olamine is selected as the at least one further active
  • the concentration of this compound in the total composition will be between 0.01 and 3 % by weight, preferably between 0.3 and 2 % by weight and more preferably between 0.5 and 1 % by weight relative to the total composition.
  • the anti-dandruff activity of LAE and the other active ingredients alone or in combination is compared by means of in vitro tests, such as inhibition halo determination or suspension " test for the specific micro-organism (in this case, Malassezia furfur), In vivo studies were carried out to compare the anti-dandruff activity of LAE with other shampoos that contain different anti-dandruff agents,
  • a diffusion plate procedure was used for the screening of anti-fungal activity of the different anti-dandruff active agents.
  • Malassezia furfur DSM 6170 / ATCC 14521
  • Potato Dextrose Broth up to 10 8 CFU (Colony Forming Units) per mL
  • 200 mL of liquid Potato Dextrose Agar were inoculated with 2 mL of the yeast suspension (approximately 10 e spores), mixed homogeneously and poured onto Petri dishes (20 mL/pIate).
  • DSM 6170 / ATCC 14521 Malassezia furfur was grown in Potato Dextrose Agar (PDA) up to 10 8 CFU (Colony Forming Units) per mL. Each test sample was inoculated with this culture at 1 % (time zero) and an aliquot of 1 mL of each solution was removed at different times (0, 10 minutes, 30 minutes and 2 hours).
  • PDA Potato Dextrose Agar
  • the dandruff condition was assessed on the basis of the following scorage scale:
  • the volunteers were treated with the preparations A, B or C for a period of 4 weeks. At the beginning and at the end of the treatment period the evaluation of the dandruff condition was conducted by a dermatologist.
  • An anti-dandruff shampoo formula was prepared in order to compare the effectiveness of several anti-dandruff agents. a) Combinations of LAE and salicylic acid were evaluated.
  • An anti-dandruff hair-conditioner formula was prepared in order to evaluate salicylic acid alone or in combination with LAE.
  • An anti-dandruff hair-conditioner formula was prepared in order to evaluate zinc pyrithione alone or in combination with LAE,
  • An anti-dandruff hair-conditioner formula was prepared in order to evaluate piroctone olamine alone or in combination with LAE.
  • Anti-dandruff hydro-alcoholic lotions were prepared in order to evaluate the activity of salicylic acid alone or in combination with LAE.
  • Anti-dandruff hydro-alcoholic lotions were prepared in order to evaluate the activity of zinc pyrithione alone or in combination with LAE.
  • Anti-dandruff hydro-alcoholic lotions were prepared in order to evaluate the activity of piroctone olamine alone or in combination with LAE.
  • Anti-dandruff actives are evaluated in water solution by mean of inhibition halo. The results are the mean value of three replicates. When the diameter of the inhibition halo observed was higher than 7 mm, it was considered positive for anti-fungal activity.
  • LAE is more effective than salicylic acid and similar to zinc pyrithione and piroctone olamine. Nevertheless, the combination of any of the active ingredients with LAE increases significantly the effectiveness compared to the active ingredients alone.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Préparations cosmétiques antipelliculaires contenant du HCl d'arginate d'éthyl-lauroyle (LAE) en association avec un autre principe actif qui est efficace contre les pellicules, ledit autre principe actif pouvant être au moins un principe actif choisi dans le groupe constitué par la pyrithione de zinc, l'acide salicylique et la piroctone olamine.
PCT/EP2012/060343 2011-06-03 2012-06-01 Préparations cosmétiques antipelliculaires Ceased WO2012164061A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP11382185.4 2011-06-03
EP11382185 2011-06-03
US201161515230P 2011-08-04 2011-08-04
US61/515,230 2011-08-04

Publications (2)

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WO2012164061A2 true WO2012164061A2 (fr) 2012-12-06
WO2012164061A3 WO2012164061A3 (fr) 2014-09-12

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3013965A1 (fr) * 2013-11-29 2015-06-05 Oreal Utilisation cosmetique d'au moins un derive de la condensation d'acides gras et d'acides amines dibasiques esterifies a titre d'agent desquamant
WO2021196628A1 (fr) * 2020-03-31 2021-10-07 宁波御坊堂生物科技有限公司 Shampoing naturel comestible et son procédé de préparation
WO2022194860A1 (fr) * 2021-03-15 2022-09-22 Pierre Fabre Dermo-Cosmetique Nouvelle composition topique exempte de tensioactifs dérivés de sulfate
CN118340710A (zh) * 2024-04-01 2024-07-16 广州慕可生物科技有限公司 一种去屑控油组合物在制备洗护发产品中的应用及洗护发产品

Citations (4)

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EP0749960A1 (fr) 1995-01-10 1996-12-27 Laboratorios Miret, S.A. Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies, et leur application en tant qu'agents antimicrobiens
EP1414395A1 (fr) 2001-08-09 2004-05-06 Laboratorios Miret, S.A. Utilisation de tensioactifs cationiques dans des preparations cosmetiques
EP1414394A1 (fr) 2001-08-09 2004-05-06 Laboratorios Miret, S.A. Nouveaux systemes conservateurs et utilisation de ceux-ci dans des preparations cosmetiques
ES2234757T3 (es) 2001-03-09 2005-07-01 Wella Aktiengesellschaft Composicion anticaspa.

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EP1443892B1 (fr) * 2001-11-15 2009-06-10 Laboratorios Miret, S.A. Utilisation d'un tensioactif cationique en tant qu'amplificateur de l'activite antimicrobienne dans des deodorants et preparations d'hygiene bucco-dentaire
US8278478B2 (en) * 2009-09-30 2012-10-02 Vishwas Sadhu Ghare Process for the synthesis of hydrochloride salt of N-fatty acylsubstituted amino acid ethyl esters
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EP0749960B1 (fr) 1995-01-10 2001-06-27 Laboratorios Miret, S.A. Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies
ES2234757T3 (es) 2001-03-09 2005-07-01 Wella Aktiengesellschaft Composicion anticaspa.
EP1414395A1 (fr) 2001-08-09 2004-05-06 Laboratorios Miret, S.A. Utilisation de tensioactifs cationiques dans des preparations cosmetiques
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3013965A1 (fr) * 2013-11-29 2015-06-05 Oreal Utilisation cosmetique d'au moins un derive de la condensation d'acides gras et d'acides amines dibasiques esterifies a titre d'agent desquamant
WO2021196628A1 (fr) * 2020-03-31 2021-10-07 宁波御坊堂生物科技有限公司 Shampoing naturel comestible et son procédé de préparation
WO2022194860A1 (fr) * 2021-03-15 2022-09-22 Pierre Fabre Dermo-Cosmetique Nouvelle composition topique exempte de tensioactifs dérivés de sulfate
CN117083051A (zh) * 2021-03-15 2023-11-17 皮埃尔·法布尔皮肤化妆品公司 不含硫酸盐衍生型表面活性剂的新型局部用组合物
CN118340710A (zh) * 2024-04-01 2024-07-16 广州慕可生物科技有限公司 一种去屑控油组合物在制备洗护发产品中的应用及洗护发产品

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