WO2019230990A1 - Feuille à micro-aiguilles - Google Patents

Feuille à micro-aiguilles Download PDF

Info

Publication number
WO2019230990A1
WO2019230990A1 PCT/JP2019/022247 JP2019022247W WO2019230990A1 WO 2019230990 A1 WO2019230990 A1 WO 2019230990A1 JP 2019022247 W JP2019022247 W JP 2019022247W WO 2019230990 A1 WO2019230990 A1 WO 2019230990A1
Authority
WO
WIPO (PCT)
Prior art keywords
microneedle
skin
sheet according
microns
microneedle sheet
Prior art date
Application number
PCT/JP2019/022247
Other languages
English (en)
Inventor
Shu Liu
Gaurav Agarwal
Original Assignee
L'oreal
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 L'oreal filed Critical L'oreal
Publication of WO2019230990A1 publication Critical patent/WO2019230990A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M37/00—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin
    • A61M37/0015—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin by using microneedles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0021—Intradermal administration, e.g. through microneedle arrays, needleless injectors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M37/00—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin
    • A61M37/0015—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin by using microneedles
    • A61M2037/0046—Solid microneedles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M37/00—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin
    • A61M37/0015—Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin by using microneedles
    • A61M2037/0061—Methods for using microneedles

Definitions

  • the present invention relates to a microneedle sheet comprising a plurality of microneedles which can be used for cosmetic treatments of skin.
  • C-xyloside is a covalent product of proxylane and vanillin. Similarly to proxylane, C- xyloside stimulates the synthesis of glycosaminoglycans and heparan sulphate proteoglycans which happens at the dermo-epidermal junction.
  • C-xyloside Anti-ageing and de-pigmentation efficacy of C-xyloside have been shown in several patent applications.
  • WO 2011/157746 and W02010/067036 describe the cosmetics application of C-xyloside for the treatment of keratin materials, more specifically the use of this compound as an anti-oxidant. It was demonstrated that this compound can be used in cosmetic products to prevent and/or treat the cutaneous signs of ageing.
  • C-Xyloside was prepared and tested as an anti-aging agent to show its effect on glycosaminoglycan sulfates on fibroblasts and keratinocytes.
  • WO 2014/096699 shows the application of this compound in cosmetics for depigmentation efficacy.
  • WO 2015/097029 discloses a cosmetic topical composition
  • a cosmetic topical composition comprising an oil, a specific nonionic surfactant, C-glycoside, and water.
  • C- xyloside poorly permeates across skin and highly cumulates in the outmost skin layer, i.e., stratum comeum, so that it is difficult to expect anti-aging and de-pigmentation efficacy. This is mainly due to the hydrophilic nature of C-xyloside.
  • An objective of the present invention is to effectively deliver C-glycoside such as C-xyloside to below the stratum comeum of the skin, i.e., the epidermis and/or dermis of the skin, preferably the dermo-epidermal junction of the skin.
  • microneedle sheet comprising a substrate sheet and a plurality of microneedles on the substrate sheet, wherein
  • the microneedle has a height of from 50 to 1000 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns,
  • the microneedle comprises at least one water-soluble or water-dispersible polymer, and the microneedle comprises at least one C-glycoside.
  • the microneedle sheet according to the present invention is capable of providing C-glycoside more in the dermis and/or epidermins of the skin, preferably the dermo-epidermal junction of the skin, than in the stratum comeum of the skin.
  • the microneedle of the microneedle sheet according to the present invention may be in the shape of a cone.
  • the base of the cone of the microneedle of the microneedle sheet according to the present invention may have a diameter of from 50 to 350 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns.
  • the ratio of (the height of the cone)/(the diameter of the base of the cone) of the microneedle of the microneedle sheet according to the present invention may be 1 or more.
  • the microneedle sheet according to the present invention may have a Young modulus of 50 N/mm or more, preferably 55 N/mm or more, and more preferably 60 N/mm or more.
  • the microneedle of the microneedle sheet according to the present invention is capable of penetrating into the skin in a depth of 200 microns or less, preferably 190 microns or less, and more preferably 180 microns or less.
  • the water-soluble or water-dispersible polymer in the microneedle of the microneedle sheet according to the present invention may be selected from hyaluronic acids, monosaccharides, disaccharides, oligosaccharides, polysaccharides, dextrins, dextrans, polyethylene glycols, polyvinyl alcohols, poly(methyvinylether/maleic anhydride), polyvinylpyrrolidone, poly(methyl/vinyl ether/maleic acid) (PMVE/MA) and esters thereof, poly(methyl/vinyl ether/maleic anhydride) (PMVE/MAH), and mixtures thereof.
  • the water-soluble or water-dispersible polymer in the microneedle of the microneedle sheet according to the present invention has a molecular weight of from 10,000 to 400,000 Dalton, preferably from 30,000 to 300,000 Dalton and more preferably from 50,000 to 200,000 Dalton.
  • the C-glycoside in the microneedle of the microneedle sheet according to the present invention may be selected from C-xylosides.
  • the amount of the C-glycoside in the microneedle of the microneedle sheet according to the present invention may range from 0.01 to 50% by weight, preferably from 0.1 to 40% by weight, and more preferably from 1 to 30% by weight relative to the total weight of the microneedle.
  • Another aspect of the present invention relates to a cosmetic process for skin comprising the step of applying onto the skin the microneedle sheet according to the present invention to insert the microneedles of the microneedle sheet into the skin.
  • the cosmetic process for skin according to the present invention may be intended for preventing and/or treating skin aging, in particular skin aging induced by oxidative stress.
  • the cosmetic process for skin according to the present invention may be intended for delivering C-glycoside more in the dermis and/or epidermins of the skin, preferably the dermo-epidermal junction of the skin, than in the stratum comeum of the skin.
  • Another aspect of the present invention relates to a cosmetic use of the microneedle sheet according to the present invention for delivering C-glycoside more in the dermis and/or epidermins of the skin, preferably the dermo-epidermal junction of the skin, than in the stratum comeum of the skin.
  • the cosmetic use according to the present invention may be intended for preventing and/or treating skin aging, in particular skin aging induced by oxidative stress.
  • C-glycoside such as C-xyloside
  • the epidermis and/or dermis of the skin preferably the dermo-epidermal junction of the skin
  • a microneedle sheet which has specific microneedles.
  • the microneedle sheet according to the present invention comprises a substrate sheet and a plurality of microneedles on the substrate sheet, wherein
  • the microneedle has a height of from 50 to 1000 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns,
  • the microneedle comprises at least one water-soluble or water-dispersible polymer, the microneedle comprises at least one C-glycoside.
  • the microneedles of the microneedle sheet according to the present invention has a limited height which targets upper epidermis layer of skin, the microneedles can shallowly penetrate into the skin.
  • the microneedle sheet according to the present invention can deliver C-glycoside into the epidermins and/or dermis of the skin without pain.
  • the mechanical strength of the microneedle sheet according to the present invention can be further enhanced.
  • hyaluronic acid can reduces stacking interactions between the aromatic rings of C-glycosides, and therefore, it can stabilize C-glycoside during storage and skin penetration.
  • the microneedles of the microneedle sheet according to the present invention can stably release C-glycoside even after storage for a long period of time.
  • microneedle sheet according to the present invention will be described in a detailed manner.
  • the microneedle sheet according to the present invention comprises a substrate sheet and a plurality of microneedles on the substrate sheet, wherein
  • the microneedle has a height of from 50 to 1000 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns,
  • the microneedle comprises at least one water-soluble or water-dispersible polymer, the microneedle comprises at least one C-glycoside.
  • the microneedle sheet according to the present invention comprises a plurality of
  • microneedles are present on the surface of the substrate sheet.
  • the microneedles may be present on the 50% or more, preferably 70% or more, and more preferably 90% or more of the surface of the substrate sheet.
  • microneedles are present on one of the surfaces of the substrate sheet.
  • microneedles in the microneedle sheet according to the present invention are designed to penetrate or insert into the stratum comeum of the skin, in particular the face.
  • microneedles are not limited as long as the shape is a“needle”. It will be apparent to those skilled in the art that the microneedles of the present invention can take any reasonable shape, including, but not limited to, cones, rods and/or pillars. As such, the microneedles may have the same diameter at the tip as at the base or may taper in diameter in the direction from the base to the tip.
  • the shape of the microneedle may be in the form of a triangular pyramid, a square pyramid or a pentagonal pyramid.
  • the microneedle may be in the form of a cylinder preferably with a tip which may be formed by diagonally cutting the cylinder.
  • microneedles as the type of microprotrusion or microprojection which is being employed. It will be understood by persons of skill in the art that in many cases the same inventive principles apply to the use of other microprotrusions or
  • microprojections to penetrate skin may include, for example, microblades as described in U.S. Patent No. 6,219,574 and Canadian Patent Application No. 2,226,718, and edged microneedles as described in U.S. Patent No.
  • the microneedle is in the form of a cone.
  • the cone may comprise a distal end such as a tip and a base.
  • the shape of the base may be a circle or oval.
  • a microneedle can be any suitable size and shape to puncture the stratum comeum.
  • the microneedles are designed to pierce and cross the stratum comeum.
  • the height of the microneedles can be altered so as to allow penetration into the epidermis and/or dermis of the skin, preferably to upper dermis, and more preferably to lower dermis.
  • the apical separation distance between each of the individual microneedles on a substrate sheet can be modified to ensure the penetration of the skin by the microneedles while having a sufficiently small separation distance to provide high transdermal transport rates.
  • the range of apical separation distances between microneedles can be in the range of 50-1000 pm, such as 100-400 pm or 200-300 pm. This may allow a compromise to be achieved between efficient penetration of the stratum comeum by the microneedles as many as possible and necessary margin for possible swelling of the microneedles if they are swellable.
  • the height or length of the microneedle of the microneedle sheet according to the present invention is 50 to 1000 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns.
  • the base of the cone of the microneedle of the microneedle sheet according to the present invention may have a diameter or width of from 50 to 350 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns. If the base of the cone of the microneedle of the microneedle sheet according to the present invention is in the shape of an oval or ellipse, the length of major axis or width of the oval may be from 50 to 350 microns, preferably from 100 to 300 microns, and more preferably from 150 to 250 microns.
  • the microneedle may have an aspect ratio (length/width at base) of at least about 3:1, at least about 2: 1 , or at least about 1 : 1. However, it is preferable that the the ratio of (the height of the cone)/(the diameter of the base of the cone) of the microneedle is 1 or more.
  • the microneedles are used for transdermal delivery, in order to be used in transdermal delivery, the microneedles should be capable of creating openings in the stratum comeum.
  • the microneedles do not fracture by force when a pressure of insertion of less than 50.0 N/cm 2 , for example less than 20.0 N/cm 2 , such as less than 10 N/cm 2 is exerted on microneedles along their length.
  • the microneedle sheet according to the present invention in particular the microneedle of the microneedle sheet, have a Young modulus of 50 N/mm or more, preferably 55 N/mm or more, and more preferably 60 N/mm or more.
  • the microneedle is capable of penetrating into the skin in a depth of 200 microns or less, preferably 190 microns or less, and more preferably 180 microns or less.
  • the microneedle of the microneedle sheet according to the present invention comprises at least one water-soluble or water-dispersible polymer.
  • water-soluble and“water-dispersible” mean soluble and dispersible, respectively, when being contact with water.
  • a single water-soluble or water-dispersible polymer may be used.
  • Two or more water-soluble or water-dispersible polymers may be used in combination.
  • the water-soluble or water-dispersible polymer be soluble or dispersible in the skin.
  • the water-soluble or water- dispersible polymer is capable of being dissolved or dispersed after insertion into the skin.
  • the microneedle of the microneedle sheet according to the present invention can effectively release the cosmetic active ingredient, i.e., C-glycoside, in the microneedle.
  • Optional external water combined with the application of the microneedle sheet according to the present invention can be used to accelerate the dissolution or dispersion of the microneedle.
  • the water-soluble or water-dispersible polymer may be selected from hyaluronic acids (in particular lower molecular weight hyaluronic acid), monosaccharides, disaccharides, oligosaccharides, polysaccharides (including derivatives thereof such as
  • hydroxymethylcellulose dextrins, dextrans, polyethylene glycols, polyvinyl alcohols, poly(methyvinylether/maleic anhydride), polyvinylpyrrolidone, poly(methyl/vinyl ether/maleic acid) (PMVE/MA) and esters thereof, poly(methyl/vinyl ether/maleic anhydride) (PMVE/MAH), and mixtures thereof.
  • the water-soluble or water-dispersible polymer may have a molecular weight of from 10,000 to 400,000 Dalton, preferably from 30,000 to 300,000 Dalton, and more preferably from 50,000 to 200,000 Dalton.
  • the low molecular weight hyaluronic acid may have a molecular weight 100 kDa or less, preferably 50 kDa or less, and more preferably 10 kDa or less.
  • the polyvinylpyrrolidone may have a molecular weight between 1 kDa and 300 kDa, preferably between 5 kDa and 200 kDa, and more preferably between 7 kDa and 100 kDa.
  • PMVE/MAH poly(methyl/vinyl ether/maleic anhydride)
  • the amount (solid basis) of the water-soluble or water-dispersible polymer(s) in the microneedle of the microneedle sheet according to the present invention may be 50% by weight or more, preferably 60% by weight or more, and more preferably 70% by weight or more, relative to the total weight of the microneedle.
  • the amount (solid basis) of the water- soluble or water-dispersible polymer(s) in the microneedle of the microneedle sheet according to the present invention may be 100% by weight or less, preferably 90% by weight or less, and more preferably 80% by weight or less, relative to the total weight of the microneedle.
  • the amount (solid basis) of the water-soluble or water-dispersible polymer(s) in the microneedle of the microneedle sheet according to the present invention may be from 50% to 100% by weight, preferably from 60% to 90% by weight, and more preferably from 70% to 80% by weight, relative to the total weight of the microneedle.
  • the microneedle of the microneedle sheet according to the present invention comprises at least one material which is swellable, more preferably water-swellable, and even more preferably swellable in the skin.
  • the above material may be a polymer which is swellable, more preferably water-swellable, and even more preferably swellable in the skin.
  • water-swellable means swellable when being contact with water.
  • the above swellable material or polymer may have a high swellability such that it can swell at least over 10 times in a l-hour in vitro incubation in a physiological saline solution or phosphate buffered saline, preferably at least 20 times in l-hour incubation, more preferably at least 30 times in l-hour incubation, even more preferably at least 40 times in l-hour incubation, and most preferably about 45-55 times in l-hour incubation.
  • the distal end portion of the microneedle swells upon insertion into the skin, more preferably within less than 1 hour, and even more preferably at least 2 times within 24 hour after insertion into the skin.
  • the above swellable material preferably the above swellable polymer, may have a high viscoelasticity such that it can form a gel after the in vitro incubation in a physiological saline solution or phosphate buffered saline.
  • the above swellable material preferably the swellable polymer, is not water-soluble or not water-dispersible.
  • the above swellable material preferably the swellable polymer, may be a hydrogel-forming polymer.
  • the above swellable polymer may be selected from high molecular weight hyaluronic acids, cross-linked hyaluronic acids, cross-linked polyethylene glycol, polyethylene glycol cross- linked poly-lactic acid or poly-glycolic acid or poly-lactic-co-glycolic acid or poly dioxanone, poly(styrene)-block-poly(acrylic acid), polyethylene glycol cross-linked PMVE/MA, cross- linked polyvinylpyrrolidone, sodium starch glycolate; cellulose; natural and synthetic gums; alginates; sodium polyacrylate PEG-crosslinked poly(methyl/vinyl ether/maleic acid)
  • the high molecular weight hyaluronic acid may have a molecular weight more than 500 kDa, preferably more than 1000 kDa, and more preferably more than 2100 kDa, and preferably less than 10000 kDa.
  • the molecular weight here means a number average molecular weight.
  • PMVE/MAH poly(methyl/vinyl ether/maleic anhydride)
  • the amount (solid basis) of the swellable material(s) in the microneedle of the microneedle sheet according to the present invention may be 1% by weight or more, preferably 5% by weight or more, and more preferably 10% by weight or more, relative to the total weight of the microneedle.
  • the amount (solid basis) of the swellable material(s) in the microneedle of the microneedle sheet according to the present invention may be 30% by weight or less, preferably 25% by weight or less, and more preferably 20% by weight or less, relative to the total weight of the microneedle.
  • the amount (solid basis) of the swellable material(s) in the microneedle of the microneedle sheet according to the present invention may be from 1% to 30% by weight, preferably from 5% to 25% by weight, and more preferably from 10% to 20% by weight, relative to the total weight of the microneedle.
  • a reduction in the amount of matrix, such as epidermis, in the skin tends to lead to a decrease in skin thickness and deterioration of skin elasticity, causing the formation of wrinkles.
  • the microneedle of the microneedle sheet according to the present invention comprises at least one swellable material, preferably at least one swellable polymer
  • the microneedle may be swellable such that it can improve the aesthetic appearance of the skin, in particular the face, by reducing the appearance of wrinkles.
  • the microneedle if it is swellable, it can swell in the skin to further increase the volume of the microneedle along with its absorption of, for example, water in the skin.
  • Such volume expansion beneath the skin surface of a wrinkle site can effectively push the wrinkles from inside the skin and makes the wrinkles become shallower and wider.
  • the wrinkles can be reduced or less noticeable.
  • the swellable microneedles may increase the amount of matrix in the skin to cause the increase of skin elasticity which results in the reduction of wrinkles on the skin.
  • the microneedle of the microneedle sheet according to the present invention comprises at least one C-glycoside.
  • a single type of C-glycoside may be used.
  • two or more C-glycosides may be used in combination.
  • the C-glycosides may be represented by the general formula (I) below:
  • R represents a saturated or unsaturated Ci-Cio and in particular Ci-C 4 alkyl radical, which may be optionally substituted with at least one radical chosen from OH, COOH, Y and COOR" 2 with R" 2 being a saturated C ! -C 4 alkyl radical
  • Y denotes a phenyl radical or a heterocycle, optionally substituted with 1 to 5 (OR a ) groups
  • S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for said monosaccharide or polysaccharide to be substituted with a hydroxyl group which must be free, and optionally with one or more optionally protected amine functions, and
  • X represents a radical chosen from the following groups: -CO-, -CH(OR')-, -CH(NH 2 )-, - CHNRbRc, -CHNHORd, -C(OR , -C(NH 2 )-, -CNR b Rc, -CNHORa-, - CH(NHCH 2 CH 2 CH 2 OH)-, -CH(NHPh)- and -CH(CH 3 )- and in particular a radical -CO-, - CH(OH)- or -CH(NH 2 )- and more particularly a radical -CH(OH)-,
  • R' denotes: a hydrogen atom; a saturated linear Ci-Ci 8 alkyl radical, an unsaturated linear C 2 -Ci 8 alkyl radical, a saturated or unsaturated branched C 3 -Ci 8 alkyl radical, a saturated or unsaturated C 5 or C 6 cyclic radical, a linear or branched, saturated or unsaturated C 2 -Ci 8 , or saturated or unsaturated C 5 or C 6 cyclic acyl radical,
  • R a denotes: a hydrogen atom; a linear or branched Ci-C 4 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical; a linear or branched C 2 -Ci 8 acyl or linear or branched C 2 -C l8 alkenylcarbonyl radical,
  • R b denotes: a hydrogen atom; a linear C 2 -Ci 8 or branched C 3 -C l8 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical or a radical - CH(Z l )-C0 2 Z 2 in which Zi denotes a hydrogen atom or a linear or branched Ci-C 6 , or saturated or unsaturated cyclic C 3 -C 6 alkyl radical, the said radical being optionally substituted with at least one group chosen from -NH
  • R o denotes: a hydrogen atom; a linear Ci-C 4 or branched C 3 -C 4 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical, the said radical being optionally substituted with a phenyl group, and
  • R d denotes: a hydrogen atom; a linear Ci-Ci 8 or branched C 3 -Ci 8 alkyl radical, or a linear or branched unsaturated C 3 -Ci 8 hydrocarbon-based radical, the said radical being optionally substituted with a phenyl group, and
  • the bond S-CHh-X represents a bond of C-anomeric nature, which may be a or b,
  • the C-glycosides of formula (I) that are useful for performing the present invention are in particular those for which R denotes a saturated linear Ci-C 6 , in particular Ci-C 4 and preferentially Ci-C 2 alkyl radical and more preferentially a methyl radical.
  • R denotes a saturated linear Ci-C 6 , in particular Ci-C 4 and preferentially Ci-C 2 alkyl radical and more preferentially a methyl radical.
  • alkyl groups that are suitable for use in the present invention, mention may be made especially of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl and cyclohexyl groups.
  • a C-glycoside compound may be used corresponding to formula (I) for which S may represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, the said mono- or polysaccharide containing at least one mandatorily free hydroxyl function and/or optionally one or more mandatorily protected amine functions, X and R otherwise conserving all the definitions given previously.
  • a monosaccharide of the present invention may be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D- lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D- iduronic acid, N-acetyl-D-glucosamine and N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D- xylose.
  • a polysaccharide of the present invention containing up to 6 sugar units may be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid and D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine and N- acetyl-D-glucosamine, an oligosaccharide containing at least one xylose which may be advantageously chosen from xylobiose, methyl-P-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and especially xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
  • S may represent a monosaccharide chosen from D-glucose, D-xylose, L- fucose, D-galactose and D-maltose, and especially D-xylose.
  • the acceptable salts of the compounds described in the present invention include
  • salts of mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid.
  • salts of organic acids may comprise one or more carboxylic, sulfonic or phosphonic acid groups. They may be linear, branched or cyclic aliphatic acids, or alternatively aromatic acids. These acids may also include one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. Mention may be made especially of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
  • neutralization of the acid group(s) may be performed with a mineral base, such as LiOH, NaOH, KOH, Ca(OH) 2 , NH 4 OH, Mg(OH) 2 or Zn(OH) 2; or with an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • a mineral base such as LiOH, NaOH, KOH, Ca(OH) 2 , NH 4 OH, Mg(OH) 2 or Zn(OH) 2
  • organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made especially of 2-amino-2- methylpropanol, triethanolamine, 2-dimethylaminopropanol and 2-amino-2-(hydroxymethyl)- 1, 3-propanediol. Mention may also be made of lysine or 3-(dimethylam ino)propylamine.
  • solvates that are acceptable for the compounds described in the present invention comprise conventional solvates such as those formed during the final step of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol. According to a first embodiment, preferentially, use is made of a C-glycoside derivative of formula (I) in which:
  • R denotes an unsubstituted linear C1-C4 alkyl radical, especially Ci-C 2 , in particular methyl;
  • S represents a monosaccharide as described previously, chosen in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine and L-fucose, and in particular D-xylose;
  • X represents a group chosen from -CO-, -CH(OH)- and -CH(NH 2 )- and preferentially a group -CH(OH)-.
  • C-P-D-xylopyranoside-2-hydroxypropane or C-a-D- xylopyranoside-2-hydroxypropane, and preferably C-P-D-xylopyranoside-2-hydroxypropane may be advantageously used for the preparation of a composition according to the present invention.
  • the C-glycoside compound may be C-b- ⁇ - xylopyranoside-2-hydroxypropane (or hydroxypropyltetrahydropyrantriol) in the form of a solution containing 30% by weight of active material in a water/propylene glycol mixture (60%/40% by weight).
  • a C-glycoside derivative that is suitable for use in the present invention may especially be obtained via the synthetic method described in document WO 02/051828.
  • the C-glycoside is selected from C-xylosides.
  • the C-glycosides are preferably chosen from the C-glycosides of general formula (I) in which S is xylose and R represents a saturated or unsaturated C2 alkyl radical substituted with a radical Y which denotes a phenyl radical or a heterocycle, optionally substituted with 1 to 5 groups (OR a ) and represented by formula (II) below:
  • Y denotes a phenyl radical or a heterocycle, optionally substituted with 1 to 5 groups (ORa), W— OR'; (-0); NR b R c ; NHORd,
  • R' denotes: a hydrogen atom; a saturated linear Ci-C l8 alkyl radical; an unsaturated linear C 2 - Ci 8 alkyl radical; a saturated or unsaturated branched C 3 -C l8 alkyl radical; a saturated or unsaturated C 5 or C 6 cyclic radical; a linear or branched, saturated or unsaturated C 2 -Ci 8 , or saturated or unsaturated C or C 6 cyclic acyl radical,
  • R a denotes: a hydrogen atom; a linear or branched Ci-C 4 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical; a linear or branched C 2 -Ci 8 acyl or linear or branched C 2 -Ci 8 alkenylcarbonyl radical,
  • OR a when Y denotes a phenyl radical or a heterocycle substituted with 2 to 5 groups (OR a ), two adjacent groups OR a may together form a divalent radical -0-CH 2 -0- with the proviso that when W-OH, the compound does not comprise an ethylenic double bond alpha to the carbon bearing this OH,
  • R b denotes: a hydrogen atom; a linear C 2 -Ci 8 or branched C 3 -Ci 8 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical or a radical - CH(Zi)-C0 2 Z 2 in which Zi denotes a hydrogen atom or a linear or branched Ci-C 6 , or saturated or unsaturated C 3 -C 6 cyclic alkyl radical, the said radical being optionally substituted with at least one group chosen from -NH, -NH 2 , -N(T) 2 , -O, - OH, -OT, -SH, -ST, -C0 2 T, phenyl, phenyl substituted with -OH or -OT,
  • R c denotes: a hydrogen atom; a linear C1-C4 or branched C 3 -C 4 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical, the said radical being optionally substituted with a phenyl group, and
  • R d denotes: a hydrogen atom; a linear Ci-Ci 8 or branched C 3 -Ci 8 alkyl radical, or a linear or branched unsaturated C 3 -C l8 hydrocarbon-based radical, the said radical being optionally substituted with a phenyl group,
  • heterocycle denotes a saturated or unsaturated 5- to lO-membered cyclic hydrocarbon-based radical, including an aromatic radical, comprising at least one heteroatom chosen from O, S and N.
  • heterocycle denotes a pyridine, pyrimidine or indole radical and more preferentially pyridine or indole.
  • Y denotes a phenyl radical or a heterocycle, optionally substituted with 1 to 5 groups (OR a ) W— OR'; (-O); NR b Rc; NHOR d
  • R' denotes: a hydrogen atom; a linear or branched, saturated or unsaturated C1-C12, or saturated cyclic C 5 or C 6 alkyl radical; a linear or branched, saturated or unsaturated Ci-C 6 , or saturated cyclic C 5 or C 6 acyl radical,
  • R a denotes: a hydrogen atom; a linear or branched C1-C4 alkyl radical, a linear or branched Ci-C 6 acyl radical, when Y denotes a phenyl radical or a heterocycle substituted with 2 to 5 groups (OR a ), two adjacent groups OR a may together form a divalent radical -0-CH 2 -0- with the proviso that when W-OH, the compound does not comprise an ethylenic double bond alpha to the carbon bearing this OH,
  • R b denotes: a hydrogen atom; a linear C 2 -C l2 or branched C 3 -C l2 alkyl radical, or a radical— CH(Zi)-C0 2 Z 2 in which Zi denotes a hydrogen atom or a linear or branched Ci-C 6 , or saturated or unsaturated cyclic C 3 -C 6 alkyl radical, the said radical being
  • R c denotes: a hydrogen atom; a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical, or a linear or branched unsaturated C 3 -C 4 hydrocarbon-based radical, the said radical being optionally substituted with a phenyl group, and
  • R d denotes: a hydrogen atom; a linear Ci-C l2 or branched C 3 -C ]2 alkyl radical, the said radical being optionally substituted with a phenyl group,
  • heterocycle denotes a saturated or unsaturated 5- to lO-membered cyclic hydrocarbon-based radical, including an aromatic radical, comprising at least one heteroatom chosen from O, S and N.
  • heterocycle denotes a pyridine, pyrimidine or indole radical and more preferentially pyridine or indole.
  • Y denotes a phenyl radical or a heterocycle, optionally substituted with 1 to 3 groups (OR a ), W--OR'; (-O); NR b Rc; NHOR d ,
  • R 1 denotes: a hydrogen atom, a linear or branched, saturated or unsaturated C 1 -C 4 alkyl radical, a linear or branched Ci-C 6 acyl radical,
  • R a denotes: a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical, a linear or branched Cj-C 6 acyl radical, when Y denotes a phenyl radical or a heterocycle substituted with 2 or 3 groups (OR a ), two adjacent groups ORa may together form a divalent radical -O-CH2-O- with the proviso that when W-OH, the compound does not comprise an ethylenic double bond alpha to the carbon bearing this OH,
  • R b denotes: a hydrogen atom; a linear C 2 -C 8 or branched C 3 -C 8 alkyl radical, or a radical -CH(Z l )-C0 2 Z 2 in which Zi denotes a hydrogen atom or a linear or branched Ci-C 6 , or saturated or unsaturated cyclic C 3 -C 6 alkyl radical, the said radical being optionally substituted with at least one group chosen from -NH, -NH2, -N(T) 2 , -O, - OH, -OT, -SH, -ST, -C0 2 T, phenyl, phenyl substituted with -OH or -OT,
  • R c denotes: a hydrogen atom; a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical, optionally substituted with a phenyl group,
  • R d denotes: a hydrogen atom; a linear C1-C4 or branched C 3 -C 4 alkyl radical, the said radical being optionally substituted with a phenyl group,
  • heterocycle denotes a saturated or unsaturated 5- to lO-membered cyclic hydrocarbon-based radical, including an aromatic radical, comprising at least one heteroatom chosen from O, S and N.
  • heterocycle denotes a pyridine, pyrimidine or indole radical and more
  • the C-xyloside of formula (II) is preferably chosen from compounds (1) and (1 1).
  • the C-xyloside is preferably chosen from C-b- ⁇ - xylopyranoside-2-hydroxypropane, a-D-xylopyranoside-2-hydroxypropane, compounds (1) and (11) and more particularly from C- -D-xylopyranoside-2-hydroxypropane and compound 1.
  • the compounds of formula (I) and/or (II) may be synthesized according to the general procedure given in patent application EP 376 5l0 or according to patent application FR 1 262 731.
  • a C-glycoside derivative corresponding to formula (I) and/or (II) may be used alone or as a mixture with other C-glycoside derivatives and in any proportion.
  • the amount (solid basis) of the C-glycoside(s) in the microneedle of the microneedle sheet according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1 % by weight or more, relative to the total weight of the microneedle.
  • the amount (solid basis) of the C-glycoside(s) in the microneedle of the microneedle sheet according to the present invention may be 50% by weight or less, preferably 40% by weight or less, and more preferably 30% by weight or less, relative to the total weight of the microneedle.
  • the amount (solid basis) of the C-Glycoside (s) in the microneedle of the microneedle sheet according to the present invention may be from 0.01% to 50% by weight, preferably from 0.1% to 40% by weight, and more preferably from 1% to 30% by weight, relative to the total weight of the microneedle.
  • the microneedle of the microneedle sheet according to the present invention may further comprise at least one additional cosmetic active ingredient.
  • a single additional cosmetic active ingredient may be used.
  • Two or more additional cosmetic active ingredients may be used in combination.
  • the type of the additional cosmetic active ingredient is not limited.
  • an anti- aging agent other than C-glycoside may be used as the additional cosmetic active ingredient.
  • anti-oxidant other than C- glycoside
  • moisturizers free-radical scavengers
  • kerato lytic agents vitamins, anti-elastase and anti-collagenase agents, protides, fatty acid derivatives, steroids, trace elements, bleaching agents, extracts of algae and of planktons, enzymes and coenzymes, flavonoids and ceramides, and mixtures thereof.
  • the amount of the additional cosmetic active ingredient(s) in the microneedle of the microneedle sheet according to the present invention is not limited, and may be from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferably from 0.1% to 1% by weight, relative to the total weight of the composition.
  • the microneedle sheet according to the present invention comprises a substrate sheet on which the microneedles are present or placed.
  • the substrate sheet may comprise at least one water-soluble or water dispersible polymer.
  • the substrate sheet and the microneedles can be integrated.
  • the substrate sheet and the microneedles can be a single element comprising the water-soluble or water-dispersible polymer.
  • the single element can be prepared by using the water- soluble or water-dispersible polymer.
  • the substrate sheet may be different or distinct from the microneedles.
  • the substrate sheet may be, for example, chosen from masks, wipes, patches, and in general all types of porous substrate sheets.
  • these substrate sheets have an oblong structure, namely with a thickness smaller than the dimensions of the plane in which they are defined.
  • the substrate sheet may be cut so as to be in the form of a disc, a mask, a towel, a glove, a precut roll, or any other form suitable for a cosmetic use.
  • microneedle sheet according to the present invention there is no limitation regarding how to prepare the microneedle sheet according to the present invention. It is possible to prepare the microneedle sheet according to the present invention based on the conventional technology such as molding or 3D printing.
  • the microneedle sheet according to the present invention can be prepared, for example, by a process comprising the steps of molding a composition comprising at least one water-soluble or water-dispersible polymer and at least one C-glycoside, as explained above.
  • the microneedle sheet according to the present invention can be prepared by a process comprising the step of
  • the above composition may include at least one additional polymer such as the above-explained swellable polymer and/or at least one additional cosmetic active ingredient as explained above.
  • At least one evaporable liquid ingredient may be added to the above composition, if necessary, in order to enhance fluidity of the composition.
  • the evaporable liquid ingredient are not limited, but preferably water and alcohol such as ethanol.
  • the amount of the evaporable liquid ingredient(s) may be 10% by weight or more, preferably 20% by weight or more, and more preferably 30% by weight or more, relative to the total weight of the mixture of the evaporable liquid ingredient(s) and the composition.
  • the amount of the evaporable liquid ingredient(s) may be 90% by weight or less, preferably 80% by weight or less, and more preferably 70% by weight or less, relative to the total weight of the mixture of the evaporable liquid ingredient(s) and the composition.
  • the amount of the evaporable liquid ingredient(s) may be from 10% to 90% by weight, preferably from 20% to 80% by weight, and more preferably from 30% to 70% by weight, relative to the total weight of the mixture of the evaporable liquid ingredient(s) and the composition.
  • the microneedle sheet according to the present invention may be a cosmetic device, preferably a cosmetic device for skin, and more preferably a cosmetic device for delivering C- glycoside more in the dermis and/or epidermins of the skin, preferably the dermo-epidermal junction of the skin, than in the stratum comeum of the skin, in particular the face.
  • the microneedle sheet according to the present invention can be used for (non-therapeutic) cosmetic treatments, preferably cosmetic treatments for skin, and more preferably cosmetic treatments for preventing and/or treating skin aging, in particular skin aging induced by oxidative stress.
  • the cosmetic process according to the present invention may comprise the step of applying onto the skin the microneedle sheet according to the present invention to insert the microneedles of the microneedle sheet into the skin.
  • the cosmetic process for skin according to the present invention may be intended for preventing and/or treating skin aging, in particular skin aging induced by oxidative stress.
  • Another aspect of the present invention relates to a cosmetic process for skin comprising the step of applying onto the skin the microneedle sheet according to the present invention to deliver C-glycoside more in the dermis and/or epidermins of the skin, preferably the dermo- epidermal junction of the skin, than in the stratum comeum of the skin.
  • the present invention also relates to a cosmetic use of the microneedle sheet according to the present invention for delivering C-glycoside more in the dermis and/or epidermins of the skin, preferably the dermo-epidermal junction of the skin, than in the stratum comeum of the skin.
  • the cosmetic use according to the present invention may be intended for preventing and/or treating skin aging, in particular skin aging induced by oxidative stress.
  • Example 1 The ingredients for each of Examples 1 and 2 shown in Table 1 were mixed with water to obtain a mixture. Immediately after mixing, the mixture was poured into the cavities of a mold which correspond to the shape of microneedles. After drying at room temperature to remove water, microneedles in the cavities were demolded as a microneedle sheet having a plurality of microneedles.
  • each of the microneedles was a cone and the dimension of the cone is shown in Table 2.
  • the pitch between two cones on the microneedle sheet was 600 pm.
  • the microneedle sheet has a plurality of microneedles in the shape of cones at a density of 324 needles/cm 2 .
  • C-Xyloside was extracted from the microneedle sheet according to Example 1 or Example 2 by dissolving the microneedle sheet with 5 mL (for Example 1) or 15 mL (for Example 2) of purified water with sonication for 10 minutes and vibration shaking for 10 minutes. After centrifuged at 12,000 rpm for 3 minutes, C-Xyloside in the solution was measured by HPLC. The weight percentage content of C-Xyloside was calculated as a measured value divided by the weight of microneedle sheet.
  • the microneedle sheets according to Examples 1 and 2 were very stable to release almost all amount of C-Xyloside from the microneedle sheets even after two months’ storage at 4°C and 40 °C with 75% humidity, respectively.
  • Each of the microneedle sheets according to Examples 1 and 2 was compressed by using two flat stainless steel plates with the compression speed of 1.0 mm/min to get the Stress-Strain Curve (S-S Curve).
  • S-S Curve Stress-Strain Curve
  • the penetration depth of the microneedles according to Examples 1 and 2 was determined using optical coherence tomography as explained below.
  • Porcine skin was excised and trimmed to a thickness of 500.0 pm using an electric dermatome (Integra Life SciencesTM, Padgett Instruments, Plainsboro, NJ, USA).
  • an electric dermatome Integra Life SciencesTM, Padgett Instruments, Plainsboro, NJ, USA.
  • two sections of 500 pm thick skin were placed together, with the dermal side contacting each other, such that the stratum comeum surface was exposed at either side. This gave a total skin thickness of 1000 pm and this was then utilized for the OCT assessment of the penetration of microneedles.
  • the skin was then placed onto a sheet of dental wax for support.
  • the microneedles on the microneedle sheet according to Example 1 were inserted into the skin by gentle hand pressure or at a pre-determined force, and immediately viewed using an EX1301 OCT Microscope (Michelson Diagnostics Ltd, Kent, UK).
  • the swept-source Fourier domain OCT system has a laser center wavelength of 1305.0 ⁇ 15.0 nm, facilitating real time high resolution imaging of the upper skin layers (7.5 pm laterals and 10.0 pm vertical resolutions).
  • the 2D images were analyzed using the imaging software Image J® (National Institute of Health, USA).
  • To allow differentiation between the microneedles and the skin, false colors were applied using Ability Photopaint® Version 4.14 (Ability Plus Software Ltd, Crawley, UK). The above measurements were repeated 10 times.
  • the penetration depth was 117.89 ⁇ 12.67pm, which corresponds to the skin layer of upper epidermis in vivo.
  • Human dermatome skin with a filter paper was mounted between the receptor and donor chambers of the cells such that the stratum comeum of the skin faces the donor chamber.
  • the receptor chamber was filled with 2.4 ml of physiological saline solution as a receptor solution, and the temperature was maintained at 32 °C over the 24 hour permeation study.
  • the receptor solution (500 ml) was withdrawn at a certain timing and replaced with an equal volume of a fresh receptor solution automatically.
  • the amount of C-Xyloside penetrated into the stratum comeum was determined after the permeation of the above-applied microneedle sheet.
  • the microneedle sheet remained on the surface of the skin was carefully removed by wiping with cotton.
  • an adhesive tape was used for stripping the S.C. by peeling twenty times.
  • C-Xyloside was extracted from these stripped S.C. with methanol After the filtration, the amount of C-Xyloside in the supernatant liquid was analyzed with LC/MS/MS.
  • the amount of C-Xyloside penetrated into the epidermis and dermis was also determined. After the above-tape stripping, skin pieces were cut into smaller pieces and homogenized in 4 ml of distilled water for 20 minutes. Subsequently, ethanol was added to the skin homogenate and was shaken for 16 hours. The suspended solution was centrifuged After the filtration, the amount of C-Xyloside in the supernatant liquid was analyzed with LC/MS/MS.
  • the application of the aqueous solution including C-Xyloside provides C-Xyloside mainly into the outmost layer of the skin, while it provides only a low level of C-Xyloside into deeper layers of the skin.
  • both microneedle sheets according to Examples 1 and 2 well modified skin distribution profile of C-Xyloside, enabling much higher permeation of the active ingredient into deeper layers of the skin.
  • the microneedle sheets according to Examples 1 and 2 can effectively provide C-Xyloside into the deeper level of the skin.

Landscapes

  • Health & Medical Sciences (AREA)
  • Dermatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Medical Informatics (AREA)
  • Anesthesiology (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Media Introduction/Drainage Providing Device (AREA)

Abstract

La présente invention concerne une feuille à micro-aiguilles comprenant une feuille de substrat et une pluralité de micro-aiguilles sur la feuille de substrat, la micro-aiguille possédant une hauteur de 50 à 1000 microns, de préférence de 100 à 300 microns, et de manière davantage préférée de 150 à 250 microns, la micro-aiguille comprenant au moins un polymère hydrosoluble ou hydrodispersable, et la micro-aiguille comprenant au moins un C-glycoside. La présente invention permet d'administrer efficacement du C-glycoside tel que le C-xyloside au-dessous de la couche cornée de la peau, c'est-à-dire l'épiderme et/ou le derme de la peau, de préférence la jonction dermo-épidermique de la peau.
PCT/JP2019/022247 2018-05-30 2019-05-29 Feuille à micro-aiguilles WO2019230990A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018103259A JP7305311B2 (ja) 2018-05-30 2018-05-30 マイクロニードルシート
JP2018-103259 2018-05-30

Publications (1)

Publication Number Publication Date
WO2019230990A1 true WO2019230990A1 (fr) 2019-12-05

Family

ID=67139780

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/022247 WO2019230990A1 (fr) 2018-05-30 2019-05-29 Feuille à micro-aiguilles

Country Status (2)

Country Link
JP (1) JP7305311B2 (fr)
WO (1) WO2019230990A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021143146A (ja) 2020-03-11 2021-09-24 コスメディ製薬株式会社 天然保湿因子含有貼付型化粧料

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1262731A (fr) 1960-04-22 1961-06-05 Renault Commande électrique à commutateur pas-à-pas
CA2226718A1 (fr) 1995-07-14 1997-02-06 Boehringer Ingelheim Kg Systeme transcorneen de liberation de medicament
US6219574B1 (en) 1996-06-18 2001-04-17 Alza Corporation Device and method for enchancing transdermal sampling
WO2002051828A2 (fr) 2000-12-22 2002-07-04 L'oreal Nouveau derives c-glycosides et utilisation
US6652478B1 (en) 1999-06-09 2003-11-25 The Procter & Gamble Company Intracutaneous edged microneedle apparatus
US20080003191A1 (en) * 2006-07-03 2008-01-03 L'oreal Composition combining a C-glycoside derivative and an emulsifying polymer
WO2009040548A1 (fr) * 2007-09-28 2009-04-02 The Queen's University Of Belfast Méthode et dispositif d'administration
US20090182306A1 (en) * 2006-07-21 2009-07-16 Georgia Tech Research Corporation Microneedle Devices and Methods of Drug Delivery or Fluid Withdrawal
WO2010067036A1 (fr) 2008-12-12 2010-06-17 L'oreal Nouveaux composés c-xylosides aryle et utilisation en cosmétique
WO2011157746A1 (fr) 2010-06-16 2011-12-22 L'oreal C‑glycosides aromatiques antioxydants cosmétiques
WO2014096699A1 (fr) 2012-12-21 2014-06-26 L'oreal Composés c-xylosides,compositions et leur utilisation pour dépigmenter la peau
US20140276378A1 (en) * 2013-03-15 2014-09-18 Corium International, Inc. Microstructure array for delivery of active agents
WO2015097029A1 (fr) 2013-12-24 2015-07-02 L'oreal Composition cosmétique comprenant une huile, un tensioactif non ionique et un composé c-glycosidique
WO2016076442A1 (fr) * 2014-11-14 2016-05-19 L'oreal Feuille de micro-aiguille pour réduire les rides et procédé de formation associé
US20170296465A1 (en) * 2016-04-15 2017-10-19 Fujifilm Corporation Microneedle array
WO2017209774A1 (fr) * 2016-06-03 2017-12-07 Sanova Bioscience Inc Timbre à micro-aiguilles contenant de l'acide hyaluronique à usage cosmétique

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2903003B1 (fr) * 2006-07-03 2012-08-17 Oreal Utilisation d'un derive c-glycoside pour ameliorer la fonction barriere de la peau
FR2902998B1 (fr) * 2006-07-03 2012-09-21 Oreal Utilisation d'au moins un derive c-glycoside a titre d'agent apaisant
FR2973237A1 (fr) * 2011-03-31 2012-10-05 Oreal Procede de traitement cosmetique fractionne utilisant un laser ou des micro-aiguilles

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1262731A (fr) 1960-04-22 1961-06-05 Renault Commande électrique à commutateur pas-à-pas
CA2226718A1 (fr) 1995-07-14 1997-02-06 Boehringer Ingelheim Kg Systeme transcorneen de liberation de medicament
US6219574B1 (en) 1996-06-18 2001-04-17 Alza Corporation Device and method for enchancing transdermal sampling
US6652478B1 (en) 1999-06-09 2003-11-25 The Procter & Gamble Company Intracutaneous edged microneedle apparatus
WO2002051828A2 (fr) 2000-12-22 2002-07-04 L'oreal Nouveau derives c-glycosides et utilisation
US20040048785A1 (en) * 2000-12-22 2004-03-11 Societe L'oreal S.A. C-glycoside compounds for stimulating the synthesis of glycosaminoglycans
US20080003191A1 (en) * 2006-07-03 2008-01-03 L'oreal Composition combining a C-glycoside derivative and an emulsifying polymer
US20090182306A1 (en) * 2006-07-21 2009-07-16 Georgia Tech Research Corporation Microneedle Devices and Methods of Drug Delivery or Fluid Withdrawal
WO2009040548A1 (fr) * 2007-09-28 2009-04-02 The Queen's University Of Belfast Méthode et dispositif d'administration
WO2010067036A1 (fr) 2008-12-12 2010-06-17 L'oreal Nouveaux composés c-xylosides aryle et utilisation en cosmétique
EP2376510A1 (fr) 2008-12-12 2011-10-19 L'Oréal Nouveaux composés c-xylosides aryle et utilisation en cosmétique
WO2011157746A1 (fr) 2010-06-16 2011-12-22 L'oreal C‑glycosides aromatiques antioxydants cosmétiques
WO2014096699A1 (fr) 2012-12-21 2014-06-26 L'oreal Composés c-xylosides,compositions et leur utilisation pour dépigmenter la peau
US20140276378A1 (en) * 2013-03-15 2014-09-18 Corium International, Inc. Microstructure array for delivery of active agents
WO2015097029A1 (fr) 2013-12-24 2015-07-02 L'oreal Composition cosmétique comprenant une huile, un tensioactif non ionique et un composé c-glycosidique
WO2016076442A1 (fr) * 2014-11-14 2016-05-19 L'oreal Feuille de micro-aiguille pour réduire les rides et procédé de formation associé
US20170296465A1 (en) * 2016-04-15 2017-10-19 Fujifilm Corporation Microneedle array
WO2017209774A1 (fr) * 2016-06-03 2017-12-07 Sanova Bioscience Inc Timbre à micro-aiguilles contenant de l'acide hyaluronique à usage cosmétique

Also Published As

Publication number Publication date
JP7305311B2 (ja) 2023-07-10
JP2019206500A (ja) 2019-12-05

Similar Documents

Publication Publication Date Title
Fonseca et al. Bacterial nanocellulose-hyaluronic acid microneedle patches for skin applications: In vitro and in vivo evaluation
EP3220997B1 (fr) Usage cosmétique pour réduire les rides d'une micro-aiguille
CN107375008B (zh) 用于美白的可溶性微针贴片及其制备方法
KR20190080549A (ko) 미백용 용해성 마이크로니들 및 그 제조방법
KR102333037B1 (ko) 입술용 마이크로니들 어레이
KR102070466B1 (ko) 화장료의 평가 방법
FR2920968A1 (fr) Procede cosmetique de traitement esthetique et/ou reparateur de la peau
WO2015136198A1 (fr) Utilisations cosmétiques de la swertiamarine
KR20040043194A (ko) 피부 수렴효과를 가지는 미용 조성물
WO2019230990A1 (fr) Feuille à micro-aiguilles
EP2833124B1 (fr) Méthode d'évaluation de l'efficacité d'un produit cosmétique en matière d'atténuation des rides
JP7543611B2 (ja) スキンケア用シート
CN116763716B (zh) 一种载人参皂苷Rg3的白及多糖微针及其制备方法和用途
CN115024997B (zh) 具有抗皮肤衰老功效的化妆品组合物
KR20090056300A (ko) 피부탄력 증진용 화장료 조성물
JP7378927B2 (ja) マイクロニードルシート
CN113116745B (zh) 一种透明质酸无创可溶性微针贴片及其制备方法
Tadini et al. In vivo skin effects of a dimethylaminoethanol (DMAE) based formulation
EP3501494A1 (fr) Composition cosmétique anti-rides, utilisation de cette composition et méthode de traitement anti-rides
JP7429458B2 (ja) 抗シワ組成物、抗シワマイクロニードルパッチおよびその製造方法
JP2006298808A (ja) 痛覚刺激緩和剤
US20230130124A1 (en) Cosmetic microneedle
US20230398040A1 (en) A multi-layered sheet mask
KR20230067127A (ko) 화장품용 마이크로니들
Sousa N-acetyl-d-glucosamine Delivery From Gels and 3D Printed Matrices: a Comparative Study

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19735414

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19735414

Country of ref document: EP

Kind code of ref document: A1