FR2857581A1 - Use of a combination of an ultraviolet (UV-B) filter and an antiinflammatory agent to retard hair loss - Google Patents

Use of a combination of an ultraviolet (UV-B) filter and an antiinflammatory agent to retard hair loss Download PDF

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FR2857581A1
FR2857581A1 FR0308798A FR0308798A FR2857581A1 FR 2857581 A1 FR2857581 A1 FR 2857581A1 FR 0308798 A FR0308798 A FR 0308798A FR 0308798 A FR0308798 A FR 0308798A FR 2857581 A1 FR2857581 A1 FR 2857581A1
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trp
arg
acid
ala
dphe
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FR2857581B1 (en
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Anne Marie Pinel
Michel Hocquaux
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INST EUROP BIOLOG CELLULAIRE
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INST EUROP BIOLOG CELLULAIRE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
    • 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
    • A61K8/63—Steroids; 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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

Abstract

Combination of a UV-B filter and an antiinflammatory agent is used to retard hair loss. Independent claims are also included for: (1) cosmetic or dermatological composition comprising a combination as above; (2) cosmetic treatment to retard hair loss by applying a cosmetic composition as above to the scalp. ACTIVITY : Antiinflammatory. MECHANISM OF ACTION : Prostaglandin inhibitor; Lipoxygenase inhibitor.

Description

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ASSOCIATION UTILE DANS LE TRAITEMENT PREVENTIF ET CURATIF DE L'ALOPECIE D'UN AGENT ANTI-INFLAMMATOIRE ET D'UN FILTRE UVB 5 L'invention se rapporte à une association d'un filtre UV et d'un agent anti-inflammatoire pour freiner la chute des cheveux. The invention relates to a combination of a UV filter and an anti-inflammatory agent to slow down Hair loss.

Chez un être humain, on recense sur la tête plus de 10 120 000 cheveux d'un diamètre de 80 pm environ.  In a human being, more than 120,000 hairs with a diameter of about 80 microns are counted on the head.

Chez un adulte, une douzaine de kilomètres de cheveux pousse par an pour une perte quotidienne de 60 à 100 cheveux environ.  In an adult, a dozen kilometers of hair grows per year for a daily loss of about 60 to 100 hairs.

15 Durant toute la vie d'un individu, la croissance des cheveux et leur renouvellement sont déterminés par l'activité des follicules pileux. Throughout an individual's life, hair growth and renewal is determined by the activity of the hair follicles.

A l'inverse de certaines espèces animales, l'homme possède des follicules pileux non synchrones. Nos cheveux 20 se renouvellent cycliquement, indépendamment les uns des autres.  Unlike some animal species, humans have non-synchronous hair follicles. Our hair 20 is renewed cyclically, independently of each other.

La durée de ces cycles pilaires génétiquement programmés est normalement de 2 à 4 ans chez l'homme et de 4 à 6 chez la femme.  The duration of these genetically programmed hair cycles is normally 2 to 4 years for men and 4 to 6 for women.

25
Notre programme génétique nous permet de réaliser 24 à 25 cycles pilaires qui comportent chacun 3 phases : # Phase anagène qui correspond à une phase de croissance du cheveu. La durée de cette phase est de 4 à 6 ans 30 chez la femme et de 2 à 4 ans en moyenne chez l'homme. 25
Our genetic program allows us to perform 24 to 25 hair cycles which each have 3 phases: # Anagen phase which corresponds to a phase of growth of the hair. The duration of this phase is 4-6 years in women and 2-4 years in men.

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# Phase catagène qui correspond à un arrêt de la croissance et à un début d'involution du bulbe pilaire. La durée de cette phase est très brève, de l'ordre de 3 semaines.  # Catagenic phase which corresponds to a stop of the growth and a beginning of involution of the hair bulb. The duration of this phase is very short, of the order of 3 weeks.

5 # Phase télogène qui correspond à la phase de chute du cheveu. 5 # Telogen phase which corresponds to the phase of hair loss.

Le bulbe pilaire involué devient plus superficiel et le cheveu tombe en 2 à 4 mois.  The involute hair bulb becomes more superficial and the hair falls in 2 to 4 months.

10 L'ensemble des connaissances actuelles concernant la biologie du cheveu et du cuir chevelu, les alopécies et les affections du cuir chevelu, les traitements sont rassemblés dans "Pathologie du cheveu et du cuir chevelu"
P. Bouhana et P. Reygagne - Editions Masson. 10 The body of current knowledge concerning the biology of hair and scalp, alopecia and scalp disorders, the treatments are gathered in "Hair and scalp pathology"
P. Bouhana and P. Reygagne - Editions Masson.

15
Plus qu'une véritable pathologie, l'alopécie androgénétique est un état au cours duquel on assiste à une raréfaction de la chevelure. 15
More than a true pathology, androgenetic alopecia is a state in which there is a rarefaction of the hair.

Le terme alopécie recouvre diverses actions sur le 20 follicule pileux, ayant pour conséquence la perte définitive ou partielle des cheveux.  The term alopecia covers various actions on the hair follicle, resulting in permanent or partial loss of hair.

On sait que si les rayonnements UV de longueurs d'ondes comprises entre 280 et 400 nm qui se partagent en UVB de 25 280 à 320 nm et en UVA de 320 - 400 nm permettent le brunissement de l'épiderme humain, ils sont également la cause d'effets indésirables nombreux.  It is known that if the UV radiations of wavelengths between 280 and 400 nm which share in UVB from 280 to 320 nm and UVA from 320 to 400 nm allow the browning of the human epidermis, they are also the cause of many adverse effects.

L'ensemble des connaissances actuelles est rassemblé dans "Rayonnement Ultra violet et Peau" Publication 2001 de la 30 Fédération des industries de la parfumerie - John
Libbey/Eurotext. The body of current knowledge is gathered in "Ultra Violet Radiation and Skin" 2001 Publication of the 30th Federation of Fragrance Industries - John
Libbey / Eurotext.

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Les UVB de longueur d'ondes comprises entre 280 et 320 nm provoquent des érythèmes et des brûlures cutanées. Les UVA de longueur d'ondes comprises entre 320 et 400 nm sont susceptibles d'induire une altération de la peau, provoquant perte d'élasticité et vieillissement cutané prématuré. Ils favorisent le déclenchement de la réaction érythémateuse ou amplifient cette dernière.  UVB wavelengths between 280 and 320 nm cause erythema and skin burns. UVA wavelengths between 320 and 400 nm are likely to induce an alteration of the skin, causing loss of elasticity and premature skin aging. They promote the triggering of the erythematous reaction or amplify the latter.

10 Dans le chapitre rédigé par Patrice Molieri, p.34 du livre "Rayonnement Ultraviolet et Peau" on relève : "Les spectres d'action (spectre d'efficacité en fonction de la longueur d'ondes) érythématogène et pigmentogène de l' UV montrent qu'il existe un rapport d' environ 103 à 104 15 entre l'efficacité des UVB et celle des UVA". 10 In the chapter written by Patrice Molieri, p.34 of the book "Ultraviolet Radiation and Skin" we note: "The spectra of action (spectrum of effectiveness as a function of wavelength) erythematogenic and pigmentogenic UV show that there is a ratio of about 103 to 104 between the efficacy of UVB and that of UVA ".

En terme d'effets biologiques exprimés en dose erythémale minimale, il faut environ 1000 fois plus d'UVA que d'UVB solaires pour induire un érythème.  In terms of biological effects expressed in minimum erythemal dose, it takes about 1000 times more UVA than solar UVB to induce erythema.

La contribution de l'UVA dans l'expression de l'érythème 20 solaire peut être estimée à environ 10 à 20%;
La demanderesse a mis au point une association d'un ou plusieurs filtres UVB et d'un agent anti-inflammatoire utile pour freiner la chute des cheveux. The contribution of AVU in the expression of solar erythema can be estimated at about 10 to 20%;
The Applicant has developed a combination of one or more UVB filters and an anti-inflammatory agent useful for curbing hair loss.

25
Parmi les agents anti-inflammatoires qui peuvent être contenus dans l'association selon la présente invention, on peut notamment citer les composés anti-inflammatoires stéroïdiens (AIS) ou non stéroïdiens (AINS). 25
Among the anti-inflammatory agents that may be contained in the combination according to the present invention, there may be mentioned steroidal anti-inflammatory compounds (AIS) or non-steroidal compounds (NSAIDs).

30
Parmi ces dérivés anti-inflammatoires, on peut citer : 30
Among these anti-inflammatory derivatives, mention may be made of:

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les agents anti-inflammatoires dits "stéroïdiens", tels l'hydrocortisone, valérate de bétaméthasone ou le propionate de clobétasol, ou les autres agents anti- inflammatoires comme 5 diclofénac et ses l'ibuprofène et ses sels, le sels, l'acétaminophène, l'acide glycyrrhizique ou le peptide Lysine-Proline-Valine, les inhibiteurs essentiellement parmi stéroïdiens" (AINS) 10 aminophenols, les hétéroarylacétiques, des prostaglandines, choisis les anti-inflammatoires dits "nontels les salycilates, les p- indoles, les acides l'aspirine, l'indomethacine, l'ibuprofène, le Piroxicam, les inhibiteurs des lipoxygénases (Lox) tels que l'acide hydroxamique et les hydroxamates, les 15 alkylhydroxyaminoacides, les dérivés N-hydroxyurée et l'acide nordihydroguaiarétique (NDGA). L'agent anti-inflammatoire est préférentiellement un peptide de formule (I) 20 X-His-Phe-Arg-Y (I) (SEQ ID N l) ou son conjugué peptidique de formule (II)
A-X-His-Phe-Arg-Y
Dans lesquelles 25
X représente Nle-Ala, (II) (SEQ ID N 2) MeNle-Ala, MeNle-Glu, Nle-Trp, Ala, une liaison, Glu, Lys ou Lys-Glu,
Y représente Trp-Gly-OH, Trp-Gly-NH2, Trp-NH2, Trp-OH, 30 Trp-CH20H, Trp-OMe ou Nal-NH2, the so-called "steroidal" anti-inflammatory agents, such as hydrocortisone, betamethasone valerate or clobetasol propionate, or other anti-inflammatory agents such as diclofenac and its ibuprofen and its salts, salts, acetaminophen, glycyrrhizic acid or the peptide Lysine-Proline-Valine, the inhibitors mainly among steroids (NSAIDs) aminophenols, heteroarylacetics, prostaglandins, chosen the anti-inflammatories known as salicylates, p-indoles, acids, and the like. Aspirin, indomethacin, ibuprofen, piroxicam, lipoxygenase (Lox) inhibitors such as hydroxamic acid and hydroxamates, alkylhydroxyamino acids, N-hydroxyurea derivatives and nordihydroguaiaretic acid (NDGA). The anti-inflammatory agent is preferably a peptide of formula (I) X-His-Phe-Arg-Y (I) (SEQ ID No. 1) or its peptide conjugate of formula (II)
AX-His-Phe-Arg-Y
In which 25
X represents Nle-Ala, (II) (SEQ ID No. 2) MeNle-Ala, MeNle-Glu, Nle-Trp, Ala, a bond, Glu, Lys or Lys-Glu,
Y represents Trp-Gly-OH, Trp-Gly-NH 2, Trp-NH 2, Trp-OH, Trp-CH 2 OH, Trp-OMe or Nal-NH 2,

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- un acide monocarboxylique de formule générale
HOOC-R (III) dans laquelle
R représente un radical aliphatique en C1-C24, linéaire 5 ou ramifié, éventuellement substitué par un groupe hydroxy, pouvant comporter une ou plusieurs insaturations, avantageusement de 1 à 6, l'acide lipoïque ou sa forme réduite, l'acide dihydrolipoïque, la N-lipoyl-lysine ou encore l'acide 10 rétinoïque, où Phe représente la phénylalanine, l'homophénylalanine (HomoPhe) ou encore la p-fluorophénylalanine (p- fluoroPhe). a monocarboxylic acid of general formula
HOOC-R (III) in which
R represents a linear or branched C 1 -C 24 aliphatic radical, optionally substituted by a hydroxyl group, which may comprise one or more unsaturations, advantageously from 1 to 6, lipoic acid or its reduced form, dihydrolipoic acid, N-lipoyl-lysine or retinoic acid, where Phe represents phenylalanine, homophenylalanine (HomoPhe) or even p-fluorophenylalanine (p-fluoroPhe).

15
Les acides aminés dans le peptide de formule (I) ou le conjugué peptidique de formule (II) peuvent avoir une configuration D, L ou DL. 15
The amino acids in the peptide of formula (I) or the peptide conjugate of formula (II) may have a D, L or DL configuration.

Autrement dit, les peptides de formule (I) et les 20 conjugués peptidiques de formule (II) peuvent comporter un ou plusieurs atomes de carbone asymétriques. Ils peuvent donc exister sous forme d'énantiomères ou de diastéréoisomères. Ces énantiomères, diastéréoisomères, ainsi que leurs mélanges, y compris les mélanges 25 racémiques font partie de l'invention.  In other words, the peptides of formula (I) and the peptide conjugates of formula (II) can comprise one or more asymmetric carbon atoms. They can therefore exist as enantiomers or diastereoisomers. These enantiomers, diastereoisomers, as well as mixtures thereof, including racemic mixtures are part of the invention.

Les conjugués peptidiques de formule (II) sont des dérivés de faible poids moléculaire qui sont obtenus sous forme d'amides du composé de formule (III).  Peptide conjugates of formula (II) are low molecular weight derivatives which are obtained as amides of the compound of formula (III).

Les peptides et leurs conjugués peptidiques, ainsi que 30 leur synthèse, sont en partie décrits dans le brevet européen EP 669 938. Leur activité anti-inflammatoire et  The peptides and their peptide conjugates, as well as their synthesis, are in part described in European patent EP 669 938. Their anti-inflammatory and

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anti-allergique mais encore leur rôle d'activateur de la mélanogénèse y sont également décrits.  anti-allergic but also their role of activator of melanogenesis are also described.

Dans le cadre de la présente invention, on entend 5 par : - His, l'histidine, - Gly, la glycine ou un de ses dérivés alkylés, tel que la méthyl-glycine.  In the context of the present invention is meant by: - His, histidine, - Gly, glycine or one of its alkylated derivatives, such as methyl-glycine.

- HomoPhe, l'homophénylalanine, 10- Prop, le propionoyl, - Palm, le palmitoyl, - Hex, l'hexanoyl, - Nal, la naphtylalanine, - MeNle, la méthyl-norleucine, 15- Tpi, la 1,2,3,4 tetrahydronorharman-3carboxylique,
Il est également précisé que les peptides de formule (I) ou les conjugués peptidiques de formule (II) mentionnés ci-dessus et dont l'utilisation est l'objet de la 20 présente invention, peuvent être obtenus sous la forme terminale NH2 (autrement dit présentant une fonction amide) et sous la forme terminale OH (autrement dit présentant une fonction acide carboxylique). HomoPhe, homophenylalanine, 10-Prop, propionoyl, Palm, palmitoyl, Hex, hexanoyl, Nal, naphthylalanine, MeNle, methyl-norleucine, 15-Tpi, 1,2, 3,4-tetrahydronoran-3-carboxylic acid,
It is also specified that the peptides of formula (I) or the peptide conjugates of formula (II) mentioned above and whose use is the subject of the present invention can be obtained in the terminal form NH 2 (otherwise said having an amide function) and in the terminal OH form (that is, having a carboxylic acid function).

25 De préférence, l'acide de formule (III) est un acide gras polyinsaturé, c'est-à-dire comportant de 1 à 6 insaturations. De manière encore plus préférée, il s'agit d'un acide oméga-3. Preferably, the acid of formula (III) is a polyunsaturated fatty acid, i.e. having from 1 to 6 unsaturations. Even more preferably, it is an omega-3 acid.

Parmi ces acides oméga-3 on peut notamment citer l'acide 30 a -linolénique, l'acide cervonique, l'acide timnodonique et l'acide pinolénique. Les acides cervonique, timnodonique et pinolénique sont également connus sous  Among these omega-3 acids there may be mentioned α-linolenic acid, cervonic acid, timnodonic acid and pinolenic acid. The cervonic, timnodonic and pinolenic acids are also known as

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les dénominations respectives d'acide 4,7,10,13,16,19 docosahexaenoïque (DHA), d'acide 5,8,11,14,17 eicosapentaénoïque (EPA) et d'acide 5,9,12 octodécatriénoïque.  the respective denominations of 4,7,10,13,16,19 docosahexaenoic acid (DHA), 5,8,11,14,17 eicosapentaenoic acid (EPA) and 5,9,12-octodecatrienoic acid.

5 Lorsque A représente un acide monocarboxylique de formule générale (III), il peut être avantageusement choisi parmi l'acide acétique, l'acide myristique, l'acide palmitique, les acides hydroxydécénoïques et décénoïliques et notamment, l'acide trans- 10-hydroxy-2-décénoïque et 10 l'acide trans-oxo-9-decene-2-oïque. Parmi les conjugués peptidiques de l'invention on peut citer les conjugués peptidiques suivants : A Ac-Nle-Ala-His-DPhe-Arg-Trp-NH2 B (D,L)Lipoyl-Glu-His-DHomoPhe-Arg-Trp-Gly-NH2 C Palm-His-DPhe-Arg-Trp-OMe D HO-(CH2)7-CH=CH-CO-MeNle-Glu-His-DHomoPhe-Arg-Trp-Gly-NH2 E Ac-MeNle-Ala-His-DHomoPhe-Arg-Trp-NH2 F Ac-Nle-Ala-His-DHomoPhe-Arg-Trp-NH2 G Ac-Nle-Ala-His-DPhe-Arg-Nal-NH2 H Ac-Nle-Ala-His-DPhe-Arg-Tpi-NH2 I Ac-Nle-Trp-His-DPhe-Arg-Trp-NH2 J Prop-Nle-Ala-His-DPhe-Arg-Trp-NH2 K Hex-Ala-His-DPhe-Arg-Trp-NH2 L Palm-His-DPhe-Arg-Trp-NH2 M Palm-Nle-Ala-His-DPhe-Arg-Trp-NH2 N Palm-His-DPhe-Arg-Trp(CH20H)  When A represents a monocarboxylic acid of the general formula (III), it may advantageously be chosen from acetic acid, myristic acid, palmitic acid, hydroxydecenoic and decenoic acids and in particular, trans-acid. 2-hydroxy-decenoic acid and trans-oxo-9-decene-2-oic acid. Among the peptide conjugates of the invention, mention may be made of the following peptide conjugates: ## STR1 ## Gly-NH 2 C Palm-His-DPhe-Arg-Trp-OMe D HO- (CH 2) 7-CH = CH-CO-MeNle-Glu-His-DHomoPhe-Arg-Trp-Gly-NH 2 E Ac-MeNle-Ala -His-DHomoPhe-Arg-Trp-NH 2 F Ac-Nle-Ala-His-DHomoPhe-Arg-Trp-NH 2 G Ac-Nle-Ala-His-DPhe-Arg-Nal-NH 2 H Ac-Nle-Ala-His -Phe-Arg-Tpi-NH 2 I Ac-Nle-Trp-His-DPhe-Arg-Trp-NH 2 J Prop-Nle-Ala-His-DPhe-Arg-Trp-NH 2 K Hex-Ala-His-DPhe-Arg Trp-NH 2 L Palm-His-DPhe-Arg-Trp-NH 2 M Palm-Nle-Ala-His-DPhe-Arg-Trp-NH 2 N Palm-His-DPhe-Arg-Trp (CH 2 OH)

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La composition cosmétique selon l'invention contient un ou plusieurs filtres organiques actifs dans l'UVB solubles dans au moins l'une des phases des compositions. The cosmetic composition according to the invention contains one or more organic filters active in the UVB soluble in at least one of the phases of the compositions.

Avantageusement, la composition contient un ou deux 5 filtres organiques actifs dans l'UVB. Comme exemple de filtres solaires actifs dans l'UVB, on peut citer, sous leur nom INCI : 10 -L'acide p-aminobenzoïque ou PABA et ses esters : *EthylhexyldimethylPABA *PEG-25PABA -Les cinnamates : 15 *Ethylhexyl Methoxycinnamate *Isoamyl p-Methoxycinnamate *Octocrylene -les Salicylates : 20 *Homosalate *Ethylhexyl Salicylate -les benzimidazoles : *Acide Phényl benzimidazole sulfonique 25 (Phenylbenzimidazole Sulfonic Acid) -les dérivés Benzylidène camphres *4- Méthylbenzylidene Camphre (4-Methylbenzylidene
Camphor) 30 *Benzilidene Camphre (Benzilidene Camphor) * Camphre Benzalkonium Méthosulfate (Camphor
Benzalkonium Methosulfate) Advantageously, the composition contains one or two active organic filters in the UVB. As an example of active UVB sunscreens, their INCI name may be: β-aminobenzoic acid or PABA and its esters: * EthylhexyldimethylPABA * PEG-25PABA -Cinnamates: 15 * Ethylhexyl Methoxycinnamate * Isoamyl p-Methoxycinnamate * Octocrylene -Salicylates: 20 * Homosalate * Ethylhexyl Salicylate -benzimidazoles: * Phenylbenzimidazolesulfonic acid 25 (Phenylbenzimidazole Sulfonic Acid) -Benzylidene derivatives camphors * 4- Methylbenzylidene Camphor (4-Methylbenzylidene)
Camphor) 30 * Benzilidene Camphor (Benzilidene Camphor) * Camphor Benzalkonium Methosulfate (Camphor)
Benzalkonium Methosulfate)

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*Polyacrylamidomethyl Benzilidene Camphre (Polyacrylamidomethyl Benzylidene Camphor) -les triazines : 5 *Ethylhexyl Triazone *Diethylhexyl Butamido Triazone.  * Polyacrylamidomethyl Benzilidene Camphor (Polyacrylamidomethyl Benzylidene Camphor) - Triazines: 5 * Ethylhexyl Triazone * Diethylhexyl Butamido Triazone.

L'association peut en outre optionnellement comprendre un filtre absorbant dans l'UVB et dans l'UVA comme : 10 -les Benzophenones : *Benzophenone-3 (Oxybenzone) *Benzophenone-4 (Sulibenzone) 15-les benzotriazoles : *Drometrizole Trisiloxane *Methylene Bis-Benzatriazolyl
Tetramethylbutylphenol 20-les triazines : *anisotriazine ou absorbant uniquement dans l'UVA comme : *Bisimidazylata (Neoheliopan E-1000) 25 *Térephtalyden Dicamphre acide sulfonique (Terephtalylidene Dicamphor Sulfonic Acid) *Butyl-methoxydibenzoyl methane
Ainsi l'association selon la présente invention peut être 30 mise en #uvre dans une composition cosmétique contenant en outre des excipients cosmétiquement acceptables, qui fait également partie de l'invention. The combination may further optionally include an absorbent filter in UVB and UVA such as: Benzophenones: Benzophenone-3 (Oxybenzone) Benzophenone-4 (Sulibenzone) Benzotriazoles: Drometrizole Trisiloxane Methylene Bis-Benzatriazolyl
Tetramethylbutylphenol 20-triazines: * anisotriazine or absorbent only in UVA such as: * Bisimidazylata (Neoheliopan E-1000) 25 * Terephthalene Dicamphor sulfonic acid (Terephthalylidene Dicamphor Sulfonic Acid) * Butyl-methoxydibenzoyl methane
Thus the combination according to the present invention can be implemented in a cosmetic composition further containing cosmetically acceptable excipients, which is also part of the invention.

<Desc/Clms Page number 10> <Desc / Clms Page number 10>

Les compositions cosmétiques peuvent aussi contenir des pigments inorganiques, à savoir des oxydes métalliques tels que TiO2, ZnO, CeÛ2 sous forme de nanoparticules de taille 10 nm à 50 nm. The cosmetic compositions may also contain inorganic pigments, namely metal oxides such as TiO 2, ZnO, CeO 2 in the form of nanoparticles of size 10 nm to 50 nm.

A titre d'exemple, les compositions cosmétiques peuvent contenir : une concentration totale de filtres comprise entre
0,5 et 15% en poids, de préférence de 1 à 10%, 10- une concentration de peptides ou conjugués peptidiques tels que décrits ci-dessus de 10-4 à
10-8 M de préférence de 10-5 à 10-6 M. By way of example, the cosmetic compositions may contain: a total concentration of filters between
0.5 and 15% by weight, preferably 1 to 10%, a concentration of peptides or peptide conjugates as described above from 10-4 to
10-8 M, preferably 10-5 to 10-6 M.

Pour une application topique sur le cuir chevelu, la 15 composition peut prendre la forme d'une solution aqueuse ou huileuse, d'une dispersion, d'une lotion, d'une émulsion ou d'un spray.  For topical application to the scalp, the composition may take the form of an aqueous or oily solution, a dispersion, a lotion, an emulsion or a spray.

Enfin, l'invention se rapporte à une méthode de 20 traitement cosmétique destinée à freiner la chute des cheveux, caractérisée en ce qu'elle consiste à appliquer sur le cuir chevelu une composition cosmétique selon l'invention. 25 Les exemples de formulation suivants illustrent la présente invention.  Finally, the invention relates to a cosmetic treatment method for curbing hair loss, characterized in that it consists in applying to the scalp a cosmetic composition according to the invention. The following formulation examples illustrate the present invention.

<Desc/Clms Page number 11> <Desc / Clms Page number 11>

Lotion 1 associant : 5- octocrylène ou Univul N 539 (BASF) - peptide A
Lotion 2 associant : - octyl methoxycinnamate 10- oxyde de titane nanométrique - peptide E
A ces compositions peuvent être associés : - des agents améliorant l'activité sur la repousse 15 comme le minoxidil, l'acide nicotinique et ses dérivés, l'aminexil. Lotion 1 associating: 5- octocrylene or Univul N 539 (BASF) - peptide A
Lotion 2 combining: - octyl methoxycinnamate 10- nanometric titanium oxide - peptide E
These compositions may be combined with: agents which improve the activity on regrowth such as minoxidil, nicotinic acid and its derivatives, aminexil.

- l'acide rétinoïque, le rétinol et ses esters - les radicaux libres. L'application régulière de la lotion 1 sur le cuir chevelu d'un homme atteint d'une alopécie de type III comme décrite dans la classification de Hamilton, empêche la chute accélérée des cheveux. - retinoic acid, retinol and its esters - free radicals. The regular application of lotion 1 on the scalp of a man with type III alopecia as described in the Hamilton classification prevents the accelerated fall of hair.

Claims (9)

Revendicationsclaims 1. Association d'un ou plusieurs filtres UVB et d'un agent anti-inflammatoire choisi parmi un composé anti- 5 inflammatoire stéroïdien (AIS) et un composé anti- inflammatoire non stéroïdien (AINS) utile pour freiner la chute des cheveux. 1. Combination of one or more UVB filters and an anti-inflammatory agent selected from a steroidal anti-inflammatory compound (AIS) and a nonsteroidal anti-inflammatory compound (NSAID) useful for curbing hair loss. 2. Association selon la revendication 1, caractérisée en 10 ce que le filtre UVB est choisi parmi l'acide p- aminobenzoïque ou PABA et ses esters tels que l'EthylhexyldimethylPABA ou le PEG-25PABA ; les cinnamates tels que l'Ethylhexyl Methoxycinnamate, l'Isoamyl p-Methoxycinnamate, l'Octocrylene ; les 15 Salicylates tels que l'Homosalate, l'Ethylhexyl 2. Association according to claim 1, characterized in that the UVB filter is selected from p-aminobenzoic acid or PABA and its esters such as ethylhexyldimethylPABA or PEG-25PABA; cinnamates such as ethylhexyl methoxycinnamate, isomethyl p-methoxycinnamate, octocrylene; Salicylates such as Homosalate, Ethylhexyl Salicylate ; les benzimidazoles tels que l'acide phényl benzimidazole sulfonique (Phenylbenzimidazole SulfonicSalicylate; benzimidazoles such as phenyl benzimidazole sulfonic acid (Phenylbenzimidazole Sulfonic Acid) ; les dérivés benzylidène camphres tels que le 4-Acid); benzylidene camphor derivatives such as 4- Méthylbenzylidene Camphre (4-Methylbenzylidene Camphor), 20 le Benzilidene Camphre (Benzilidene Camphor), le CamphreMethylbenzylidene Camphor (4-Methylbenzylidene Camphor), Benzilidene Camphor (Benzilidene Camphor), Camphor Benzalkonium Méthosulfate (Camphor BenzalkoniumBenzalkonium Methosulfate (Camphor Benzalkonium Methosulfate) et le Polyacrylamidométhyl BenzilideneMethosulfate) and Polyacrylamidomethyl Benzilidene Camphre (Polyacrylamidomethyl Benzylidene Camphor) ou encore les triazines telles que l'Ethylhexyl Triazone et 25 le Diethylhexyl Butamido Triazone. Camphor (Polyacrylamidomethyl Benzylidene Camphor) or triazines such as Ethylhexyl Triazone and Diethylhexyl Butamido Triazone. 3. Association selon l'une quelconque des revendications 1 ou 2, caractérisée en ce que l'agent anti-inflammatoire est choisi parmi 3. Association according to any one of claims 1 or 2, characterized in that the anti-inflammatory agent is chosen from <Desc/Clms Page number 13><Desc / Clms Page number 13> A-X-His-Phe-Arg-Y 25 Dans lesquelles (II) (SEQ ID N 2) X représente Nle-Ala MeNle-Ala, MeNle-Glu, Nle-Trp, Ala, une liaison, Glu, Lys ou Lys-Glu, 30 Y représente Trp-Gly-OH, Trp-CH20H, Trp-OMe ou Nal-NH2, In which (II) (SEQ ID NO: 2) X is Nle-Ala MeNle-Ala, MeNle-Glu, Nle-Trp, Ala, a bond, Glu, Lys or Lys-Glu Y represents Trp-Gly-OH, Trp-CH 2 OH, Trp-OMe or Nal-NH 2, X-His-Phe-Arg-Y (I) (I) (SEQ ID N 1) ou son conjugué peptidique de formule (II) X-His-Phe-Arg-Y (I) (I) (SEQ ID No. 1) or its peptide conjugate of formula (II) - les agents anti-inflammatoires dits "stéroïdiens", tels que l'hydrocortisone, le valérate de bétaméthasone ou le propionate de clobétasol, ou les autres agents anti- inflammatoires comme 1 ibuprofène et ses sels, le 5 diclofénac et ses sels, l'acétaminophène, l'acide glycyrrhizique ou le peptide Lysine-Proline-Valine, les inhibiteurs des prostaglandines, choisis essentiellement parmi les anti-inflammatoires dits "non- stéroidiens" (AINS) tels les salycilates, les p- 10 aminophenols, les hétéroarylacétiques, indoles, les acides l'aspirine, l'indomethacine, l'ibuprofène, le Piroxicam, les inhibiteurs des l'acide hydroxamique 15 alkylhydroxyaminoacides, lipoxygénases (Lox) tels que et les hydroxamates, les les dérivés N-hydroxyurée et l'acide nordihydroguaiarétique (NDGA), the so-called "steroidal" anti-inflammatory agents, such as hydrocortisone, betamethasone valerate or clobetasol propionate, or the other anti-inflammatory agents such as ibuprofen and its salts, diclofenac and its salts, acetaminophen, glycyrrhizic acid or peptide Lysine-Proline-Valine, prostaglandin inhibitors, chosen essentially from the so-called "non-steroidal" anti-inflammatory drugs (NSAIDs) such as salycilates, p-aminophenols, heteroarylacetics, indoles; aspirin, indomethacin, ibuprofen, piroxicam, hydroxamic acid alkylhydroxyamino acid inhibitors, lipoxygenases (Lox) such as and hydroxamates, N-hydroxyurea derivatives and nordihydroguaiaretic acid ( NDGA) 4. Association selon l'une quelconque des revendications 1 ou 2, caractérisée en ce que l'agent anti-inflammatoire 20 est un peptide de formule4. Association according to any one of claims 1 or 2, characterized in that the anti-inflammatory agent 20 is a peptide of formula <Desc/Clms Page number 14> <Desc / Clms Page number 14> 5. Association selon la revendication 4, caractérisée en ce que le peptide ou le conjugué peptidique est choisi 20 parmi A Ac-Nle-Ala-His-DPhe-Arg-Trp-NH2 B (D,L)Lipoyl-Glu-His-DHomoPhe-Arg-Trp-Gly-NH2 C Palm-His-DPhe-Arg-Trp-OMe D HO-(CH2)7-CH=CH-CO-MeNle-Glu-His-DHomoPhe-Arg-Trp-Gly-NH2 E Ac-MeNle-Ala-His-DHomoPhe-Arg-Trp-NH2 F Ac-Nle-Ala-His-DHomoPhe-Arg-Trp-NH2 G Ac-Nle-Ala-His-DPhe-Arg-Nap-NH2 H Ac-Nle-Ala-His-DPhe-Arg-Tpi-NH2 I Ac-Nle-Trp-His-DPhe-Arg-Trp-NH2 J Prop-Nle-Ala-His-DPhe-Arg-Trp-NH2 5. Combination according to claim 4, characterized in that the peptide or peptide conjugate is selected from A-Nle-Ala-His-DPhe-Arg-Trp-NH2 B (D, L) Lipoyl-Glu-His- DHomoPhe-Arg-Trp-Gly-NH2 C Palm-His-DPhe-Arg-Trp-OMe D HO- (CH2) 7-CH = CH-CO-MeNle-Glu-His-DHomoPhe-Arg-Trp-Gly-NH2 Ac-MeNle-Ala-His-DHomoPhe-Arg-Trp-NH 2 F Ac-Nle-Ala-His-DHomoPhe-Arg-Trp-NH 2 G Ac-Nle-Ala-His-DPhe-Arg-Nap-NH 2 H Ac Ala-His-DPhe-Arg-Tpi-NH 2 I Ac-Nle-Trp-His-DPhe-Arg-Trp-NH 2 J Prop-Nle-Ala-His-DPhe-Arg-Trp-NH 2 HOOC-R (III) dans laquelle 5 R représente un radical aliphatique en C1-C24, linéaire ou ramifié, éventuellement substitué par un groupe hydroxy, pouvant comporter une ou plusieurs insaturations, avantageusement de 1 à 6 insaturations, l'acide lipoïque ou sa forme réduite, l'acide 10 dihydrolipoïque, la N-lipoyl-lysine ou encore l'acide rétinoïque, où Phe représente la phénylalanine, l'homophénylalanine (HomoPhe) ou encore la p-flurophénlalanine (p-fluoroPhe) 15 sous forme d'énantiomères ou de diasteréoisomères, ainsi que leurs mélanges, y compris les mélanges racémiques. HOOC-R (III) in which R 5 represents a C 1 -C 24 aliphatic radical, linear or branched, optionally substituted by a hydroxyl group, which may comprise one or more unsaturations, advantageously from 1 to 6 unsaturations, lipoic acid or its reduced form, dihydrolipoic acid, N-lipoyl-lysine or retinoic acid, where Phe represents phenylalanine, homophenylalanine (HomoPhe) or p-flurophenlalanine (p-fluoroPhe) 15 in the form of enantiomers or diastereoisomers, and mixtures thereof, including racemic mixtures. A représente le radical correspondant à - un acide monocarboxylique de formule généraleA represents the radical corresponding to - a monocarboxylic acid of general formula <Desc/Clms Page number 15><Desc / Clms Page number 15> K Hex-Ala-His-DPhe-Arg-Trp-NH2 L Palm-His-DPhe-Arg-Trp-NH2 M Palm-Nle-Ala-His-DPhe-Arg-Trp-NH2 N Palm-His-DPhe-Arg-Trp(CH20H)  Hex-Ala-His-DPhe-Arg-Trp-NH2 L Palm-His-DPhe-Arg-Trp-NH2 M Palm-Nle-Ala-His-DPhe-Arg-Trp-NH2 N Palm-His-DPhe-Arg -Trp (CH20H) 6. Composition cosmétique ou dermatologique comportant l'association selon l'une quelconque des revendications 1 à 5. Cosmetic or dermatological composition comprising the combination according to any one of claims 1 to 5. 55 7. Composition selon la revendication 6, caractérisée en ce qu'elle est formulée pour être administrée par voie topique. 107. Composition according to claim 6, characterized in that it is formulated to be administered topically. 10 8. Composition selon la revendication 7, caractérisée en ce qu'elle prend la forme d'une solution aqueuse ou huileuse, d'une dispersion, d'une lotion, d'une émulsion ou d'un spray. 8. Composition according to claim 7, characterized in that it takes the form of an aqueous or oily solution, a dispersion, a lotion, an emulsion or a spray. 1515 9. Méthode de traitement cosmétique destinée à freiner la chute des cheveux, caractérisée en ce qu'elle consiste à appliquer sur le cuir chevelu une composition cosmétique selon l'une quelconque des revendications 6 à 8.9. A cosmetic treatment method for curbing hair loss, characterized in that it consists in applying to the scalp a cosmetic composition according to any one of claims 6 to 8.
FR0308798A 2003-07-18 2003-07-18 ASSOCIATION USEFUL IN THE PREVENTIVE AND CURATIVE TREATMENT OF ALOPECIA OF AN ANTI-INFLAMMATORY AGENT AND A UVB FILTER Expired - Fee Related FR2857581B1 (en)

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MX2009014233A (en) 2007-06-29 2010-03-10 Innovactiv Inc Novel compounds, use thereof in cosmetic and cosmeceutic applications, and compositions comprising same.
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