EP4262727A1 - Selbstbräunungszusammensetzungen - Google Patents

Selbstbräunungszusammensetzungen

Info

Publication number
EP4262727A1
EP4262727A1 EP21836544.3A EP21836544A EP4262727A1 EP 4262727 A1 EP4262727 A1 EP 4262727A1 EP 21836544 A EP21836544 A EP 21836544A EP 4262727 A1 EP4262727 A1 EP 4262727A1
Authority
EP
European Patent Office
Prior art keywords
self
tanning
cosmetic
tyrosine
skin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21836544.3A
Other languages
English (en)
French (fr)
Inventor
Leithe BUDEL
Dominik Imfeld
Joerg KREMP
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Publication of EP4262727A1 publication Critical patent/EP4262727A1/de
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur

Definitions

  • the present invention relates to self-tanning compositions that, through the combination of certain skin-tanning peptides and L-tyrosine or a derivative thereof, provide a synergistic effect on melanogenesis (tanning).
  • Self-tanners are a safe, rapid and effective alternative for obtaining healthful skin coloration. These products have been more and more sought after, chiefly in countries where the presence of sunlight is scarce. By using self-tanners one can obtain the desired tan throughout the year, without skin damage preventing the risks of excessive exposure to sunlight and the use of tanning chambers. Recently, the scientific community alerts for the risks involving artificial tanning on tanning chambers. According to Dermatologists and researchers, irresponsible uses of tanning chambers may contribute to the increase of skin cancer and induce premature skin aging, since the equipment used in artificial tanning emit mainly Ultra Violet radiation Type A (UV-A), which is also responsible for skin cancer and skin photoaging. Premature skin photoaging is characterized by dark, clear or reddish spots, dry, thick and wrinkled skin, making a person look older than she/he really is.
  • UV-A Ultra Violet radiation Type A
  • Skin-tanning peptides are known from WO2018065345. However, there is still a need to further enhance the tanning effect thereof.
  • the invention relates to a cosmetic and/or dermatological self-tanning composition
  • a cosmetic and/or dermatological self-tanning composition comprising L-tyrosine or a derivative thereof and at least one compound of formula wherein
  • R 1 is selected from the group consisting of a C 1 -C 10 alkyl group, a C 3 -C 6 cycloalkyl group, an aryl group or an aryl C 1 -C 6 alkyl group;
  • R 2 is an amino acid side chain of a basic amino acid or an amino acid side chain of a 2-amino C 2-8 alkanoic acid;
  • R 3 and R 3 ’ are selected from the group consisting of H, an arylC 1 -C 6 alkyl group or a heteroarylC 1 -C 6 alkyl group, wherein the aryl respectively the heteroaryl can optionally be substituted,
  • R 4 and R 5 are, independently of each other, H or a C1-C10 alkyl group; and with the proviso that only one of R 3 or R 3 ’ is H and the respective other one of R 3 and R 3 ’ is not H or a salt thereof.
  • Another objective of the present invention is to use L-tyrosine or a derivative thereof in combination with a compound of formula (I) in preparing a self-tanning cosmetic and/or dermatological composition that has performance similar or superior to that of the presently available compositions.
  • a further objective of the present invention is to provide a skin self-tanning method through application of a cosmetic and/or dermatological composition containing L-tyrosine or a derivative thereof and at least one compound of formula (I) to the skin of a subject in need thereof.
  • C x -C y alkyl group refers to unbranched C x -C y alkyl or branched C3-C y alkyl groups such as methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1- ethylpropyl, n-hexyl, 1 ,1 -di methyl propyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -di methyl butyl, 1 ,2-dimethylbutyl, 1 ,3-di
  • C 3 -C 6 cycloalkyl group refers to a saturated, 3 to 6 membered hydrocarbon ring such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the C 3 -C 6 cycloalkyl group is cyclopropyl, cyclopentyl or cyclohexyl, most preferably cyclohexyl.
  • aryl refers to an aromatic substituent containing 5 to 15 carbon atoms and containing a single aromatic ring or multiple aromatic rings which are fused together, directly linked or indirectly linked (such that the different aromatic rings are bound to a common group such as a methylene or ethylene group).
  • Particularly advantageous aryl groups according to the present invention contain 6 to 12 carbon atoms containing a single aromatic ring or multiple aromatic rings which are fused together or directly linked.
  • Most preferred aryl residues in all embodiments of the present invention are phenyl, naphtyl and biphenyl.
  • side chain of an amino acid refers to that portion of the amino acid attached to the common NH 2 -CH -COOH backbone of the respective amino acids.
  • side chain of serine is -CH 2 -OH and the side chain of alanine is -CH 3 .
  • basic amino acid refers to any natural or unnatural amino acid that have basic side chains at neutral pH such as the natural occurring amino acids arginine (Arg), lysine (Lys), and histidine (His) as well as the unnatural amino acids 2,4-diaminobutyric acid, homolysine and ornithine without being limited thereto.
  • Advantageous amino acid side in all embodiments of the present invention are the side chains of arginine, lysine, 2,4-diaminobutyric acid, homolysine and ornithine such as in particular the side chains of arginine and 2,4- diaminobutyaric acid.
  • 2-amino C 2-8 alkanoic acid refers to amino acids having a C 2-8 alkyl side chain, preferably a linear C4-7 alkyl side chain.
  • Most preferred 2-amino C 2-8 alkanoic acids in all embodiments of the present invention are 2-amino butanoic acid, 2-amino pentanoic acid, 2- amino hexanoic acid or 2-amino heptanoic acid such as in particular 2-amino hexanoic acid.
  • arylC 1 -C 6 alkyl group refers to a -C 1 -C 6 alkyl-aryl group, wherein the term “aryl” is as defined above.
  • Advantageous arylC 1 -C 6 alkyl groups are arylC 1 -C 2 alkyl groups such as in particular phenyl(m)ethyl or naphthyl(m)ethyl.
  • heteroarylC 1 -C 6 alkyl group refers to a -C 1 -C 6 alkyl-heteroaryl wherein the term “heteroaryl” refers to a 5- or 6-membered aromatic ring containing one or more heteroatoms, viz., N, O or S; these heteroaromatic rings may be fused to other aromatic systems.
  • heteroaryl refers to a 5- or 6-membered aromatic ring containing one or more heteroatoms, viz., N, O or S; these heteroaromatic rings may be fused to other aromatic systems.
  • Particularly preferred heteroaromatic rings encompass indole, pyridine and quinoline.
  • heteroarylC 1 -C 6 alkyl group are heteroarylC 1 -C 2 alkyl groups such as (1 H-indol-3-yl)(m)ethyl, (pyridin-2-yl)(m)ethyl, (pyridin-3-yl)(m)ethyl, (quinolin-2-yl)(m)ethyl and (quinolin-3-yl)(m)ethyl groups.
  • aromatic aryl respectively heteroaryl residues may, independently of each other, be unsubstituted or substituted with one or more substituents.
  • substituents are preferably selected from halogen, hydroxy, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 alkanoyloxy.
  • the aryl respectively heteroaryl residues are, independently of each other, unsubstituted or substituted with one substituent selected from the group consisting of F, Cl, hydroxy, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkanoyloxy such as in particular unsubstituted or substituted with one substituent selected from the group consisting of F or hydroxy.
  • the aryl and the heteroaryl residues are unsubstituted.
  • heteroarylC 1 -C 2 alkyl groups are (1 H-indol-3-yl)(m)ethyl, 5-fluoro(1 H-indol-3-yl)(m)ethyl, 6-fluoro(1 H-indol-3-yl)(m)ethyl, 5- hydroxy(1 H-indol-3-yl)(m)ethyl, (pyridin-2-yl)(m)ethyl, (pyridin-3-yl)(m)ethyl, (quinolin-2- yl)(m)ethyl and (quinolin-3-yl)(m)ethyl.
  • heteroarylCi alkyl groups (1 H-indol-3-yl)methyl, 5-fluoro(1 H-indol-3-yl)methyl, 6- fluoro(1 H-indol-3-yl)8m)ethyl, 5-hydroxy(1 H-indol-3-yl)methyl, (pyridin-2-yl)methyl, (pyridin-3- yl)methyl, (quinolin-2-yl)methyl and (quinolin-3-yl)methyl and the heteroarylC 2 alkyl groups (1 H- indol-3-yl)ethyl such as in particular (1 H-indol-3-yl)methyl and (1 H-indol-3-yl)ethyl.
  • the term ‘or a salt thereof’ refers to all conventional non-toxic salts of compounds of formula (I), such as those formed from organic or mineral acids, such as for example the respective acetates, trifluoro acetates, mesylates, citrates, oleates, oxalates or gluconates as well as chlorides, sulfates, borates or carbonates.
  • the nature of the salt is not critical, provided that it is cosmetically, dermatologically and/ or pharmaceutically acceptable. Such salts are well known to a person skilled in the art.
  • the cosmetically, dermatologically or pharmaceutically acceptable salts of the compounds of formula (I) can be obtained by conventional methods that are well known in the state of the art.
  • the present invention encompasses the compounds of formula (I) as optically pure isomers such as e.g. as pure enantiomers or stereoisomers as well as mixtures of different isomers such as e.g. as racemates, or mixtures of diastereoisomers.
  • R 3 and R 3 ’ are selected from the group consisting of H, an unsubstituted aryl(m)ethyl group and an unsubstituted heteroaryl(m)ethyl group, most preferably R 3 is selected from the group consisting of H, phenylmethyl, naphthylmethyl and (1 H-indol-3-yl)methyl and R 3 ’ is H or (1 H-indol-3-yl)ethyl;
  • R 4 and R 5 are, independently of each other, H or a C 3 -C 8 alkyl group, most preferably H, propyl or octyl; and with the proviso that only one of R 3 or R 3 ’ is H and the respective other one of R 3 and R 3 ’ is not H (but the respective arylC 1 -C 6 alkyl group or heteroarylC 1 -C 6 alkyl group, with all the definitions and preferences as given herein for R 3 and R 3 ’).
  • Particularly preferred compounds of formula (I) respectively a salt thereof such as in particular the acetate, trifluoroacetate or mesylate salt thereof in all embodiments of the present invention, are compounds of formula (I) wherein
  • R 1 is a C 1 -C 2 alkyl group or a C 6 -C 12 aryl group
  • R 2 is an amino acid side chain of a basic amino acid
  • R 3 and R 3 ’ are selected from the group consisting of H, an unsubstituted aryl(m)ethyl group or an unsubstituted heteroaryl(m)ethyl group;
  • R 4 and R 5 are, independently of each other H or a C 1 -C 10 lkyl group; and with the proviso that only one of R 3 or R 3 ’ is H and the respective other one of R 3 and R 3 ’ is not H.
  • R 1 is phenyl
  • R 2 is the amino acid side chain of arginine or 2,4-diaminobutyric acid
  • R 3 is H, phenylmethyl, naphthylmethyl or (1 H-indol-3-yl)methyl and R 3 ’ is H or (1 H-indol-3- yl)ethyl;
  • R 4 and R 5 are, independently of each other H, propyl or octyl; with the proviso that only one of R 3 or R 3 ’ is H and the respective other one of R 3 and R 3 ’ is not H.
  • R 1 is are selected from the group consisting of a C1-C 10 alkyl group, a C 3 -C 6 cycloalkyl group, an aryl group or an aryl C 1 -C 6 alkyl group; preferably from C 1 -C 2 alkyl group or a C 6 -C 12 aryl group, most preferably phenyl;
  • R 2 is the amino acid side chain of arginine
  • R 3 is (1 H-indol-3-yl)methyl
  • R 1 -Gly-His-D-Phe-Arg-D-Trp- N(R 4 ,R 5 ) with all the definitions and preferences for R 1 and R 4 and R 5 as outlined herein.
  • Most preferred in all embodiments according to the present invention are the compounds as listed in table 1 , respectively the respective (trifluoro)acetate or mesylate salts thereof:
  • the compounds according to the present invention may be prepared by methods standard in peptide chemistry as e.g. illustrated in WO-2018065345.
  • Bz-Gly-His-D-Phe-Arg-D-Trp-N(Pr)2*2MSA [CAS No. 2210277-15-7], which preferably is used in the form of a solution in glycerin/ water, most preferably in a concentration of about 1000 ppm (w/w) which is commercially available under the tradename SYN®-GLOW at DSM Nutritional Products Ltd.
  • L-Tyrosine (4-hydroxyphenylalanine) is one of the 20 standard amino acids that are used by cells to synthesize proteins. L-Tyrosine is e.g. commercially available at Sigma-Aldrich.
  • L-tyrosine derivatives in all embodiments of the present invention are selected from the group of N-Ci-18-acyl-L-tyrosine, preferably from N-acetyl-L-tyrosine, N-capryl-L-tyrosine and N-oleyl-L-tyrosine as well as mixtures thereof.
  • the derivative is N-acetyl-L- tyrosine, which is e.g. commercially available as Unipertan® VEG-2002 (A cety l-tyrosine) from Givaudan Active Beauty.
  • the self-tanning compositions according to the present invention are self-tanning composition further comprising a cosmetically or dermatologically acceptable carrier.
  • Particularly suitable self-tanning compositions are cosmetic composition.
  • compositions which are used to treat, care for or improve the appearance of the affected skin area.
  • Particular advantageous self-tanning compositions according to the present invention are skin care compositions.
  • cosmetically or dermatologically acceptable carrier refers to a physiologically acceptable medium which is compatible with keratinous substances such as the skin. Suitable carriers are well known in the art and are selected based on the end-use application.
  • the carriers of the present invention are particularly suitable for application to skin (e.g., sunscreens, creams, milks, lotions, masks, serums (e.g. in ethanol or acetone), hydrodispersions, foundations, creams, creamgels, or gels etc.).
  • skin e.g., sunscreens, creams, milks, lotions, masks, serums (e.g. in ethanol or acetone), hydrodispersions, foundations, creams, creamgels, or gels etc.
  • Such carriers are well-known to one of ordinary skill in the art and can include one or more compatible liquid or solid filler diluent, excipient, additive or vehicle which are suitable for application to skin.
  • the exact amount of carrier will depend upon the level of the compound of formula (I) and any other optional ingredients that one of ordinary skill in the art would classify as distinct from the carrier (e.g., other active components).
  • compositions of the present invention preferably comprise from about 75% to about 99.999%, more preferably from about 85% to about 99.99%, still more preferably from 90% to about 99%, and most preferably, from about 93% to about 98%, by weight of the composition, of a carrier.
  • the carrier consists furthermore of at least 30 wt. %, more preferably of at least 40 wt.-%, most preferably of at least 45 wt.-% of water, such as in particular of 50 to 90 wt.-% of water.
  • the amount of the compound of formula (I) or a salt thereof in the self-tanning compositions according to the present invention is at least 1 ppm based on the total weight of the self-tanning composition.
  • the amount of the compound of formula (I) or a salt thereof is preferably selected in the range of about 0.00001 to 0.5 wt.-%, more preferably in the range of 0.0001 to 0.25 wt.-%, most preferably in the range of 0.0001 to 0.1 wt.-%, based on the total weight of the self-tanning composition.
  • suitable ranges encompass from 0.0001 to 0.01 wt.-%, from 0.0025 to 0.1 , respectively from 1 ppm to 100 ppm.
  • Other suitable ranges encompass from 0.001 to 0.1 wt.-%, from 0.001 to 0.075 wt.-%, from 0.001 to 0.05 wt.-%, from 0.002 to 0.1 wt.-%, from 0.002 to 0.075 wt.-% and from 0.002 to 0.05 wt.-%.
  • the amount of L-tyrosine or a derivative thereof in the self-tanning compositions according to the present invention is at least 0.01 wt.-% and/ or at most 10 wt.-%, based on the total weight of the self-tanning composition.
  • the amount of L-tyrosine or a derivative thereof is preferably selected in the range of about 0.01 to 5.0 wt.-%, more preferably in the range of 0.1 to 2.0 wt.-%, most preferably in the range of 0.1 to 1.0 wt.-%, based on the total weight of the self-tanning composition.
  • Other suitable ranges encompass from 0.5 to 5 wt.-%, from 1 to 5 wt.-%, from 2 to 5 wt.-%, from 2.5 to 5 wt.-% and from 3 to 5 wt.-%.
  • L-tyrosine or a derivative thereof is used in an excess, such as in an amount of two times, preferably three times, more preferably 10 times, most preferably 100 times such as 1000 times of the amount (weight) of the compound of formula (I).
  • the ratio (w/w) of L-tyrosine or a derivative thereof to the compound of formula (I) is selected in the range from 5000:1 to 1 :1 , preferably from 2500:1 to 1.5:1 , most preferably from 2000:1 to 2:1 , such as in the range from 2000:1 to 3:1 or from 2000:1 to 4:1. Further suitable ranges are from 2500:1 to 50:1 , or from 2000:1 to 100:1.
  • the self-tanning compositions of the present invention can be formulated into a wide variety of product types, including creams, waxes, pastes, lotions, milks, mousses, gels, oils, tonics, and sprays.
  • the compounds of formula (I) are formulated into lotions, creams, gels, and tonics.
  • These product forms may be used for a number of applications, including, but not limited to, hand and body lotions, facial moisturizers, anti-ageing preparations, make-ups including foundations, and the like. Any additional components required to formulate such products vary with product type and can be routinely chosen by one skilled in the art.
  • the composition may also be in the form of a shaving preparation or an aftershave product intended for application to the skin after shaving.
  • compositions of the present invention are formulated as an aerosol and applied to the skin as a spray-on product, a propellant is added to the composition.
  • the self-tanning compositions according to the present invention may be in the form of a suspension or dispersion in solvents or fatty substances, or alternatively in the form of an emulsion or micro emulsion (in particular of oil-in-water (O/W) or water-in-oil (W/O) type, silicone-in-water (Si/W) or water-in-silicone (W/Si) type, PIT-emulsion, multiple emulsion (e.g.
  • oil-in-water-in oil O/W/O
  • water-in-oil-in-water W/O/W
  • pickering emulsion hydrogel, alcoholic gel, lipogel, one- or multiphase solution or vesicular dispersion or other usual forms, which can also be applied by pens, as masks or as sprays.
  • the self-tanning composition according to the present invention is an emulsion, such as in particular an O/W, W/O, Si/W, W/Si, O/W/O, W/O/W multiple or a pickering emulsion
  • the amount of the oily phase present in such cosmetic emulsions is preferably at least 10 wt.-%, such as in the range of 10 to 60 wt.-%, preferably in the range of 15 to 50 wt.-%, most preferably in the range of 15 to 40 wt.-%, based on the total weight of the self-tanning composition.
  • the self-tanning compositions according to the present invention are advantageously in the form of an oil-in-water (O/W) emulsion comprising an oily phase dispersed in an aqueous phase in the presence of an O/W emulsifier.
  • O/W oil-in-water
  • the preparation of such O/W emulsions is well known to a person skilled in the art.
  • the self-tanning compositions according to the present invention are in the form of O/W emulsions comprising an oily phase dispersed in an aqueous phase in the presence of an O/W emulsifier, preferably in the presence of potassium cetyl phosphate.
  • the amount of oily phase in such O/W emulsions is preferably at least 10 wt.-%, more preferably in the range of 10 to 60 wt.-%, most preferably in the range of 15 to 50 wt.-%, such as in the range of 15 to 40 wt.-%.
  • the self-tanning compositions according to the present invention are after-shaves or toners in the form of aqueous solution or aqueous gels further containing at least one gelling and/ or thickening agent such as e.g. selected from the group of acrylate copolymers of sodium/lecithin, copolymer of hydroxyethyl acrylate/sodium acryloyldimethyl taurate, isohexadecane, polysorbate 60, xanthan gum, carrageenan and mixtures thereof.
  • at least one gelling and/ or thickening agent such as e.g. selected from the group of acrylate copolymers of sodium/lecithin, copolymer of hydroxyethyl acrylate/sodium acryloyldimethyl taurate, isohexadecane, polysorbate 60, xanthan gum, carrageenan and mixtures thereof.
  • the self-tanning compositions according to the invention in general have a pH in the range of 3 to 14.
  • Generally self-tanning compositions for skin care preferably exhibit a pH in the range of 4 to 8 and most preferably a pH in the range of 4 to 7.5.
  • the pH of depilatory creams generally is selected in the range of > 12.
  • suitable acids such as e.g. citric acid, or bases, such as sodium hydroxide (e.g. as aqueous solution), triethanolamine (TEA Care), Tromethamine (Trizma Base) and Aminomethyl Propanol (AMP- Ultra PC 2000), according to standard methods in the art.
  • compositions according to the present invention can be prepared by conventional methods in the art such as e.g. by admixing L-tyrosine or a derivative thereof and a compound of formula (I) or a salt thereof with all the definitions and preferences given herein with an appropriate carrier such as a cosmetically or pharmaceutically acceptable carrier.
  • compositionsof the invention may comprise further conventional cosmetic adjuvants and additives, such as preservatives/antioxidants, fatty substances/oils, water, organic solvents, silicones, thickeners, softeners, emulsifiers, antifoaming agents, aesthetic components such as fragrances, surfactants, fillers, anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, propellants, acidifying or basifying agents, dyes, colorings/colorants, abrasives, absorbents, chelating agents and/ or sequestering agents, essential oils, skin sensates, astringents, pigments or any other ingredients usually formulated into such compositions.
  • cosmetic adjuvants and additives such as preservatives/antioxidants, fatty substances/oils, water, organic solvents, silicones, thickeners, softeners, emulsifiers, antifoaming agents, aesthetic components such as fragrances, surfactants, fillers, anionic, cationic, non
  • compositions according to the present invention should be topically applied to a selected area of the body from which it is desired to reduce hair growth.
  • the composition can be applied to the face, particularly to the beard area of the face, i.e., the cheek, neck, upper lip, and chin.
  • the self-tanning composition according to the present invention can also be applied to the legs, groin region (bikini area), arms, torso or armpits.
  • the self-tanning compositions according to the present invention are furthermore particularly suitable for application to normal to pallor skin but can also be applied to darker skin.
  • the amount of the self-tanning composition to be applied to the skin is not critical and can easily be adjusted by a person skilled in the art.
  • the amount is selected in the range of 0.1 to 3 mg/cm 2 skin, such as preferably in the range of 0.1 to 2 mg/cm 2 skin and most preferably in the range of 0.5 to 2 mg/cm 2 skin.
  • the compound of formula (I) or a salt thereof is applied to the skin in an amount of from 0.001 to 10 micrograms of the compound of formula (I) per square centimeter of skin.
  • the present invention is directed to the use of a self-tanning compositions according to the present invention for enhancing the skin tan of a person in need thereof.
  • the present invention relates to the use of L-tyrosine or a derivative thereof in combination with a compound of formula (I) as defined herein in preparing a self-tanning cosmetic and/or dermatological composition.
  • Said composition has a synergistic (over-additive) skin tanning effect compared to a composition comprising either a compound of formula (I) or L- tyrosine or a derivative thereof.
  • the self-tanning composition according to the present invention may further contain organic or inorganic UV-filter substances (light screening agents) which are active in the IIV-A and/or IIV-B regions (absorbers) to protect the skin against the harmful effects of UV- radiation.
  • organic or inorganic UV-filter substances light screening agents
  • IIV-A and/or IIV-B regions absorbers
  • Exemplary UVA, UVB and/ or broadspectrum UV-filter substances encompass dibenzoylmethane derivatives such as e.g. butyl methoxydibenzoylmethane (PARSOL® 1789); acrylates such as e.g. octocrylene (PARSOL® 340); camphor derivatives such as e.g. 4-methyl benzylidene camphor (PARSOL® 5000) or terephthalylidene dicamphor sulfonic acid (Mexoryl® SX); cinnamate derivatives such as e.g.
  • dibenzoylmethane derivatives such as e.g. butyl methoxydibenzoylmethane (PARSOL® 1789); acrylates such as e.g. octocrylene (PARSOL® 340); camphor derivatives such as e.g. 4-methyl benzylidene camphor (PARSOL® 5000) or tere
  • ethylhexyl methoxycinnamate PARSOL® MCX or isoamyl methoxycinnamate
  • p-aminobenzoic acid derivatives such as e.g. p-aminobenzoic acid or 2- ethylhexyl p-dimethylaminobenzoate
  • benzophenones such as e.g. benzophenone-3, benzophenone-4, 2,2',4,4'-tetrahydroxy-benzophenone or 2,2'-dihydroxy-4,4'- dimethoxybenzophenone
  • esters of benzalmalonic acid such as e.g.
  • organosiloxane compounds carrying chromophore groups such as e.g. polysilicone-15 (PARSOL® SLX) or drometrizole trisiloxane (Mexoryl® XL); imidazole derivatives such as e.g. 2-phenyl benzimidazole sulfonic acid and salts thereof such as e.g. its sodium- or potassium salts (PARSOL® HS); salicylate derivatives such as e.g.
  • PARSOL® EHS ethylhexyl salicylate
  • Neo Heliopan® OS isooctyl salicylate or homosalate
  • PARSOL® HMS Neo Heliopan® HMS
  • triazine derivatives such as e.g.
  • ethylhexyl triazone Uvinul® T-150), diethylhexyl butamido triazone (Uvasorb® HEB), bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb® S) or Tris-Biphenyl Triazine (2,4,6-Tris(biphenyl-4-yl)-1 ,3,5-triazin, Tinosorb® A2B); Benzotriazole derivatives such as e.g. methylene bis-benzotriazolyl tetramethylbutylphenol (Tinosorb® M); encapsulated UV-filters such as e.g.
  • encapsulated ethylhexyl methoxycinnamate (Eusolex® UV- pearls); amino substituted hydroxybenzophenones such as e.g. diethylamino hydroxy benzoyl hexyl benzoate (Aminobenzophenon, Uvinul® A Plus); benzoxazol-derivatives such as e.g.
  • disodium phenyl dibenzimidazole tetrasulfonate (2,2-(1 ,4-phenylene)bis-(1 H-benzimidazol-4,6- disulfonic acid, Neoheliopan® AP); 1 ,1’-(1 ,4-piperazinediyl)bis[1-[4-(diethylamino)-2- hydroxybenzoyl]phenyl]-methanone (CAS No. 919803-06-6); as well as Bis(butylbenzoate) diaminotriazine aminopropyltrisiloxane (CAS No. 207562-42-3).
  • Inorganic UV-filter substances encompass pigments such as e.g. microparticulated zinc oxide or titanium dioxide (e.g. commercially available as PARSOL®TX)
  • microparticulated refers to a particle size from about 5 nm to about 200 nm, particularly from about 15 nm to about 100 nm.
  • the particles may also be coated by other metal oxides such as e.g. aluminum or zirconium oxides or by organic coatings such as e.g. polyols, methicone, aluminum stearate, alkyl silane. Such coatings are well known in the art.
  • Preferred UVB-filter substances to be incorporated into the self-tanning compositions according to the invention encompass polysilicone-15, phenylbenzimidazol sulfonic acid, octocrylene, ethylhexyl methoxycinnamate, ethyl hexylsalicylate, tris-biphenyl triazine and/ or homosalate.
  • Preferred broadband UV-filter substances to be incorporated into the self-tanning compositions according to the invention encompass unsymmetrical s-triazine derivatives such as in particular bis-ethylhexyloxyphenol methoxyphenyl triazine, certain benzophenones such as e.g. 2-hydroxy- 4-methoxy-benzophenon, methylene bis-benzotriazolyl tetramethylbutylphenol and/ or titanium dioxide.
  • Preferred UVA-filter substances to be incorporated into the self-tanning compositions according to the invention encompass butyl methoxydibenzoylmethane, diethylamino hydroxybenzoyl hexyl benzoate, 2, 4-bis-[5-1(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imino- 1 ,3,5-triazine and/ or disodium phenyl dibenzimidazole tetrasulfonate, in particular butyl methoxydibenzoylmethane and/ or diethylamino hydroxybenzoyl hexyl benzoate.
  • topical sunscreen emulsions comprise butyl methoxydibenzoylmethane, then they advantageously contain in addition at least one suitable photostabilizer for butyl methoxydibenzoylmethane.
  • suitable photostabilizers encompass Polyester 8 (Polycrylene®); Methoxycrylene (Solastay); diethylhexyl syringylidene malonate (Oxynex ST liquid); diethylhexyl naphthalate (Corapan TQ) as well as Benzotriazolyl Dodecyl p-Cresol (Tinogard® TL) without being limited thereto.
  • photostabilizers are generally used in an amount of 0.05 to 10 wt.-% with respect to the total weigh of the topical sunscreen emulsion.
  • the amount of the UV-filter substances is preferably selected in the range of 0.1 to 40 wt. %, more preferably in the range of 0.2 to 20 wt. % and most preferably in the range of 0.5 to 15 wt.-% based on the total weight of the self-tanning composition.
  • Further particular advantageous self-tanning compositions according to the present invention comprise one or more additional skin-coloring and/or skin-tanning agents. .
  • Such additional skin-coloring and/ or skin-tanning agent are well known to a person skilled in the art and encompass e.g. mono- or polycarbonyl compounds, such as, for example, isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, the pyrazoline- 4, 5-dione derivatives as described in FR-2,466,492 and WO97/35842, di hydroxyacetone (DHA) or the 4,4-dihydroxy-pyrazolin-5-one derivatives as described in EP-903,342.
  • DHA and/or erythrulose in D- or L-form or as the racemate in particular erythrulose.
  • DHA can be used in the free form and/or in the encapsulated form, for example encapsulated in lipid vesicles, such as liposomes, which are described, in particular, in WO 97/25970.
  • compositions according to the present invention may also contain at least one synthetic or natural direct dye and/or at least one indole derivative, such as those described in EP-425,324 and EP-456,545 and/ or at least one synthetic or natural agent for coloring the skin.
  • the additional coloring agents can also be selected, for example, from among plant extracts, such as, for example, extracts of “insoluble” redwoods of the Pzerocarpus genus and of the Baphia genus, such as Pzerocarpus santalinus, Pterocarpus osun, Plerocarpus soyauxii, Plerocarpus erinaceus, Pterocarpus indicus or Baphia nitida, such as those described in EP-971 ,683.
  • plant extracts such as, for example, extracts of “insoluble” redwoods of the Pzerocarpus genus and of the Baphia genus, such as Pzerocarpus santalinus, Pterocarpus osun, Plerocarpus soyauxii, Plerocarpus erinaceus, Pterocarpus indicus or Baphia nitida, such as those described in EP-971 ,683.
  • the coloring agents can also be iron oxide nanopigments for which the mean size of the individual particles is less than 100 nm, such as those described in EP-966,953.
  • the total amount of such additional skin-coloring and/ or skin-tanning agent(s) in the self-tanning compositions according to the invention is generally selected in proportions ranging from 0.1% to 20% by weight with respect to the total weight of the composition and preferably from 0.2% to 8% by weight with respect to the total weight of the self-tanning composition.
  • the self-tanning compositions according to the present invention only comprise L-tyrosine or a derivative thereof and the compound of formula (I) as skin-tanning agent.
  • the invention is further illustrated with reference to the following, non-limiting examples, in which all percentages are by weight based on total weight unless otherwise specified.
  • the melanin content in the cells of the MEL models was measured. This was done by dissolving the cell models and visualize from this mixture the melanin content using a standard with known melanin concentrations.
  • the melanin analysis was performed on day 8 of treatment and showed that the SYN-GLOW® and L-tyrosine combination had the highest increase compared to the untreated control in melanin levels, see Table 2. Compared to the bioactives separately, a clear synergetic effect can be seen when SYN-GLOW® and L-tyrosine are combined.
  • a cream formulation was prepared containing 3% SYN-GLOW® (0.003-0.03 wt.-% active i.e. peptide) and 5% N-acetyl-L- tyrosine (5 wt.-%) (Table 5);
  • the subjects applied the cream in the morning (except the morning application on measuring days) and in the evening by themselves at their home for a total of 14 days.
  • the application site was covered from sunlight/UV (the application period was in November as well in Switzerland).
  • the determination of skin pigmentation was done using a chromameter with three repeated measurements per area.
  • the L*, A*, and B* values were obtained.
  • the AAITA° was calculated.
  • the AITA° was obtained by comparing day 0 and day x (day with highest difference, e.g., day 14) of placebo cream and cream with compounds.
  • the AAITA° was determined directly between placebo and cream with compounds. Based on this, the following formula was applicable: (SG+TY day 0 vs. day x) vs. (Placebo day 0 vs. day x), where x represents the day with the largest difference.
  • a negative AAITA° value represents a darkened skin pigmentation. As can be retrieved from the results depicted in the table 4 below, the combination leads to an improved pigmentation.

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EP21836544.3A 2020-12-16 2021-12-16 Selbstbräunungszusammensetzungen Pending EP4262727A1 (de)

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EP20214508 2020-12-16
PCT/EP2021/086059 WO2022129265A1 (en) 2020-12-16 2021-12-16 Self-tanning compositions

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FR2466492A1 (en) 1979-10-03 1981-04-10 Elf Aquitaine Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid
FR2651126B1 (fr) 1989-08-29 1991-12-06 Oreal Association de dihydroxyacetone et de derives indoliques pour conferer a la peau une coloration similaire au bronzage naturel et procede de mise en óoeuvre.
FR2661673B1 (fr) 1990-05-07 1992-08-21 Oreal Association de dihydroxyacetone et de monohydroxyindoles pour conferer a la peau une coloration similaire au bronzage naturel, dispositif a plusieurs compartiments et procede de mise en óoeuvre.
DE19603018C2 (de) 1996-01-17 1998-02-26 Lancaster Group Gmbh Kosmetisches Selbstbräunungsmittel mit Lichtschutzwirkung
FR2746391B1 (fr) 1996-03-22 1998-04-17 Oreal Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations
FR2761595B1 (fr) 1997-04-04 1999-09-17 Oreal Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau et utilisations
FR2768733B1 (fr) 1997-09-19 1999-10-29 Oreal Nouveaux composes 4,4-dihydroxypyrazolin-5-ones ; leurs procedes de preparation et utilisations cosmetiques
FR2780281B1 (fr) 1998-06-26 2000-08-18 Oreal Compositions comprenant des nanopigments d'oxydes de fer pour la coloration artificielle de la peau et utilisations
US11591367B2 (en) 2016-10-04 2023-02-28 Dsm Ip Assets B.V. Melanocortin-1-receptor agonists
EP3802559A1 (de) * 2018-06-05 2021-04-14 DSM IP Assets B.V. Verfahren zur synthese von argininhaltigen peptiden
DE202020001282U1 (de) * 2020-03-30 2020-06-10 Dsm Ip Assets B.V. Abbildungen kosmetischer Effekte

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