WO2001082878A1 - Traitement de lesions cutanees au moyen d'acetyl-carnitine et de phosphatidylcholine et/ou d'esters d'acide gras d'ascorbyle - Google Patents

Traitement de lesions cutanees au moyen d'acetyl-carnitine et de phosphatidylcholine et/ou d'esters d'acide gras d'ascorbyle Download PDF

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Publication number
WO2001082878A1
WO2001082878A1 PCT/US2001/013401 US0113401W WO0182878A1 WO 2001082878 A1 WO2001082878 A1 WO 2001082878A1 US 0113401 W US0113401 W US 0113401W WO 0182878 A1 WO0182878 A1 WO 0182878A1
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Prior art keywords
acetyl carnitine
skin
ascorbyl
fatty acid
carnitine
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PCT/US2001/013401
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English (en)
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Nicholas V. Perricone
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Perricone Nicholas V
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Publication date
Application filed by Perricone Nicholas V filed Critical Perricone Nicholas V
Priority to AU2001259158A priority Critical patent/AU2001259158A1/en
Publication of WO2001082878A1 publication Critical patent/WO2001082878A1/fr

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    • 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
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • This invention relates to the topical application of acetyl-carnitine and phosphatidylcholine and/or fatty acid esters of ascorbic acid for the treatment of acute and chronic skin damage.
  • Therapies according to the invention are particularly efficacious for treating a variety of skin conditions including contact dermatitis, atopic dermatitis, xerosis, eczema, rosacea, sebor- rhea, psoriasis, thermal and radiation burns, other types of skin inflammation, and the tissue degerative effects of aging.
  • Acute inflammation is also characterized by mast cell degranula- tion wherein serotonin is produced, which acts as a signal transduction factor. Following that, excited oxygen species are generated, e.g. , superoxide anion, and these damage the lipid-rich membranes and activate the chemical mediators of proinflammation and mflammation.
  • NFKB transcription factors
  • API proiriflammation mediators
  • TF ⁇ TF ⁇ and various interleukins
  • cytokines cytokines
  • Arachadonic acid is released, which is oxidized to biologically active mediators.
  • arachadonic acid is oxidized via the cyclooxygenase or lipoxygenase pathways, for example, prostaglandins, leukotrines, and hyroxyeicosatetraenoic acid (HETE) are produced, which cause erythma, edema, and free radical production.
  • Transcription factors such as NF/cB and API alter DNA expression in the cell and produce cytokines and proteinases such as collagenase.
  • the body contains an endogenous antioxidant defense system made up of antioxidants such as vitamins C and E, glutathione, and enzymes, e.g., superoxide dismutase.
  • antioxidants such as vitamins C and E, glutathione, and enzymes, e.g., superoxide dismutase.
  • enzymes e.g., superoxide dismutase.
  • the endogenous antioxidant systems are overwhelmed, and free radical damage takes place.
  • the cell membrane continually receives damage from reactive oxygen species and other free radicals, resulting in cross-linkage or cleavage or proteins and lipoprotins, and oxidation of membrane lipids and lipoproteins.
  • Damage to the cell membrane can result in myriad changes including loss of cell permeability, increased intercellular ionic concentration, and decreased cellular capacity to excrete or detoxify waste products.
  • intercellular ionic concentration of potassium increases, colloid density increases and m-RNA and protein synthesis are hampered, resulting in decreased cellular repair. Some cells become so dehydrated they cannot function at all.
  • Acetyl carnitine has been shown to have a scavenging effect on free superoxide anions. This antioxidant activity, coupled by acetyl carnitine 's effect of reducing an increase in reduced glutathione and reduced ubiquinone levels, provides a stabilizing effect on membranes by decreasing membrane lipid peroxidation.
  • Carnitine is a molecule that can be derived from the diet or, in the presence of ascorbic acid, be synthesized in the human body. L-carnitine, 3-carboxy-2-hydroxy- ⁇ , ⁇ , ⁇ -trimethyl-l-propanaminium hydroxide (see the Merck Index, 11th ed.
  • jS-hydroxy- ⁇ -trimethyl amino butyric acid is a molecule that is essential for the transportation of fatty acids across the mitochon- drial membrane to be oxidized. If L-carnitine is not present in adequate amounts, fatty acid metabolism is impaired, and there is a marked decrease in energy production. The fatigue associated with scurvy may be associated with carnitine deficiency.
  • carnitine enhances mitochondrial energy production, probably by increasing cytochrome oxidase activity, the final enzyme in the cellular respiratory chain. This results in a more efficient cellular maintenance and repair.
  • carnitine given as an oral supplement may enhance muscular and cellular function and increase energy levels and repair.
  • Carnitine does not pass the blood-brain barrier.
  • biologically equivalent derivatives such as acetyl carnitine, can pass the barrier.
  • Acetyl carnitine has been used in cognitive enhancement and has been shown to slow damage to the mitochondria with age, as well as to enhance mitochondrial function.
  • Acetyl carnitine has been suggested for the treatment of viral infections, including skin infections such as those caused by Herpes, including lesions that occur after sunlight or UN exposure (U.S. Pat. No. 5,314,689 to Scandurra and Aurelian).
  • Acetyl carnitine was suggested as an optional ingredient in a composition containing glutathione and selenoamino acid for reducing and repairing x-ray radiation-induced skin damage (U.S. Pat. No. 5,667,791 to Hersh and Warshaw).
  • Oral administration of acetyl carnitine has also been suggested for the treatment of AIDS symptoms, including skin inflammation (U.S. Pat. No. 5,667,791 to Weil and Scandurra).
  • Oral or parenteral acetyl carnitine has also been disclosed as useful in stimulating the immune system of patients with an impaired immune system (U.S. Pat. No. 4,415,588 to Cavazza), and in the therapeutical treatment of impaired cardiac function, myocardial anoxia and cardiac arrhythmias ⁇ ibid.).
  • skin damage such as atopic dermatitis, contact dermatitis, xerosis, eczema, rosacea, seborrhea, psoriasis, thermal and radiation burns, other types of skin inflammation, and aging.
  • the amount of acetyl carnitine and phosphatidylcholine and/or fatty acid esters of ascorbic acid necessary to treat damaged skin is not fixed per se, and necessarily is dependent upon the acetyl carnitine preparation employed, the amount of acetyl carnitine, the amount and identity of the ascorbyl esters where employed, the amount and type of any adjunct ingredients employed in the composition, the user's skin type, and the severity, extent, and nature of the dermatological problem treated.
  • the composition contains from about 0.025% to about 5 weight %, more narrowly from about 0.5% to about 2%, by weight acetyl carnitine, and, where employed, from about 0.5% to about 7%, more narrowly from about 1 % to about 5% by weight saturated fatty acid esters of ascorbic acid such as ascorbyl palmitate.
  • Adjunct ingredients such as an ⁇ -hydroxy acid may be added to compositions of the invention in some embodiments.
  • acetyl carnitine and phosphatidylcholine are used and/or fatty acid esters of ascorbic acid to treat skin damage when topically applied in effective amounts.
  • L-acetyl carnitine and/or biologically equivalent derivatives of acetyl carnitine such as D-acetyl cartinine, DL-acetyl carnitine, DL-acetyl cartinine hydrochloride, DL-acetyl carnitine chloride, acetyl D,L carnitine hydrochloride, acetyl L-carnitine hydrochloride
  • acetyl carnitine and/or biologically equivalent derivatives of acetyl carnitine such as D-acetyl cartinine, DL-acetyl carnitine, DL-acetyl cartinine hydrochloride, DL-acetyl carnitine chloride, acetyl D,L carnitine hydrochloride, acetyl L-carnitine hydrochloride
  • phosphatidylcholine and/or ascorbyl fatty acid esters penetrate skin and cause enhanced function of
  • Advantageous embodiments deliver carnitine directly into skin cells through the use of acetyl carnitine and/or a biologically active derivative, to enhance mito- chondrial function. This, in turn, leads to high energy production in the cell, which then can maintain the integrity of cellular membranes and increase exchange of nutrients and wastes across these membranes.
  • Use of effective amounts of acetyl carnitine gives skin a softer, smoother appearance, and decreases epidermal age pigments.
  • acetyl carnitine Any synthetic or natural acetyl carnitine preparation may be employed in compositions of the invention.
  • acetyl carnitine encompasses D-, L-, or DL- acetyl carnitine, and biologically active derivatives such as those listed above. L-acetyl cartine is preferred because it is the most active form. Preferred concentrations of acetyl carnitine in compositions of the invention vary from about 0.025% to about 5%, more narrowly from about 0.5% to about 2%, by weight.
  • Phosphatidylcholine (sometimes hereafter abbreviated "PC"), commonly called lecithin, is a mixture of diglycerides of stearic, palmitic, and oleic acids, linked to the choline ester of phosphoric acid. It can be isolated from eggs, soybeans, and other biological materials rich in PC, chemically synthesized, or obtained commercially from many sources. Food grade lecithin is preferred. Some commercial grades, for example, contain about 2.2% PC. It is an advantage of the invention that both acetyl carnitine and phosphatidylcholine are natural products that have been shown to have no toxicity to mammals, and ascorbyl fatty acid esters are similarly nontoxic.
  • PC Phosphatidylcholine
  • phosphatidylcholine is edible and digestible, and used in margarine, chocolate, and the food industry in general. Moreover, since acetyl carnitine penetrates poorly when topically administered, it is a particular advantage of the invention that combining it with phosphatidyl choline considerably enhances penetration of this active ingredient.
  • fatty acid esters of ascorbic acid are employed with acetyl carnitine in the practice of the invention.
  • Fat-soluble fatty acid esters of ascorbic acid (vitamin C) is employed as an adjunct ingredient in other embodiments, alone or in combination with c -hydroxy acids.
  • the more oxidation-resistant saturated fatty acid esters of ascorbic acid are preferred, including, but not limited to, ascorbyl laurate, ascorbyl myristate, ascorbyl palmitate, ascorbyl stearate, and ascorbyl behenate.
  • Ascorbyl palmitate is used in one embodiment.
  • fatty acid esters are described, e.g.
  • ascorbyl stearate compositions having predominantly that ester, e.g. , predominantly stearate, are included.
  • the esters may be prepared using hydrogenated oils or fats, or fractions thereof, and contain small amounts of another ester.
  • Ascorbyl stearate prepared using canola for example, commonly contain about 4% ascorbyl palmitate.
  • Typical concentrations of ascorbyl esters in compositions of the invention are from about 0.5% to about 7% by weight, more narrowly from about 1 % to about 7% to 10% by weight. It is an advantage of the invention that where fatty acid esters of ascorbic acid are employed in compositions of the invention, they help stabilize the compositions of the invention and enhance the radical scavenging properties of acetyl carnitine.
  • the active ingredient combination is topically applied to exposed or affected skin areas in amounts effective to treat skin damage.
  • effective amount is meant an amount of both active ingredients sufficient to stabilize the cell plasma membrane by scavenging and neutralizing free radicals and exhibiting antioxidant activity, thereby inhibiting the arachidonic acid cascade which leads to the activation of transcription factors that direct the cell nucleus into producing pro-inflammatory chemicals such as arachidonic acid.
  • active ingredients are typically delivered to lipid-rich layers of the skin in amounts effective to prevent inflammation and accelerate collagen synthesis.
  • Acetyl carnitine, fatty acid esters of ascorbic acid, and PC are fat-soluble. Therefore, compositions of the invention can be applied neat to skin tissue, and this is preferred in some embodiments.
  • One embodiment comprises acetyl carnitine in food grade lecithin; another comprises acetyl carnitine and ascorbyl palmitate in food grade lecithin.
  • PC is fatty so that compositions of the invention physically contribute to the lubrication of affected skin areas to which it is applied.
  • Active ingredients may also be administered in association with a carrier, which is particularly useful where lower amounts are needed to treat skin damage
  • the carrier is inert in the sense of not bringing about a deactivation or oxidation of the acetyl carnitine or ascorbyl fatty acid esters and in the sense of not bringing about any adverse effect on the skin areas to which it is applied.
  • carriers or vehicles e.g. , lotions, creams, ointments, soaps, sticks, or the like
  • they are formulated as to facilitate topical application and, in some cases, provide additional therapeutic effects as might be brought about, e.g. , by moisturizing of the affected skin or mucosal areas.
  • the carrier for dermatological compositions can consist of a relatively simple solvent or dispersant such as water
  • the carrier comprise a composition more conducive to topical application, and particularly one which will form a film or layer on the skin to which it is applied so as to localize the application and provide some resistance to washing off by immer- sion in water or by perspiration and/or aid in the percutaneous delivery of the active agent.
  • oils and/or alcohols and emollients such as hydrocarbon oils and waxes, silicone oils, vegetable, animal or marine fats or oils, glyceride derivatives, fatty acids or fatty acid esters or alcohols or alcohol ethers, lanolin and derivatives, polyhydric alcohols or esters, wax esters, sterols, phospholipids and the like, as well as lecithin, and generally also emulsifiers (nonionic, cationic or anionic), although some such as lecithini inherently possess emulsifying properties.
  • oils and/or alcohols and emollients such as hydrocarbon oils and waxes, silicone oils, vegetable, animal or marine fats or oils, glyceride derivatives, fatty acids or fatty acid esters or alcohols or alcohol ethers, lanolin and derivatives, polyhydric alcohols or esters, wax esters, sterols, phospholipids and the like, as well as lecithin, and generally also e
  • compositions can be formulated into a cream rather than a lotion, or into gels, or into solid sticks by utilization of different proportions of the ingredients and/or by inclusion of thickening agents such as gums or other forms of hydrophilic colloids.
  • Such compositions are referred to herein as dermally or dermatologically acceptable carriers.
  • Suitable carriers include water, alcohols, oils and the like, chosen for their ability to dissolve or disperse acetyl carnitine and any other ingredients used in the treatment. Generally, even low concentrations of active ingredients in a carrier are suitable, depending upon the application regimen and adjunct ingredients employed. Chronic conditions typically require a lower concentration of active acetyl carnitine ingredient than to acute conditions. As a practical matter, however, to avoid the need for repeated application, it is desirable that the topically applied composition (i.e. , acetyl carnitine plus PC and/or ascorbyl esters, and, in some cases, carrier) be formulated to contain at least about 0.01 % by weight, preferably at least about 0.025% acetyl carnitine.
  • the topically applied composition i.e. , acetyl carnitine plus PC and/or ascorbyl esters, and, in some cases, carrier
  • compositions of the invention contain from about 0.5% to about 2% acetyl carnitine and about 1 % to about 5% ascorbyl palmitate or other saturated ester.
  • the composition is topically applied to the affected skin areas in a predetermined or as-needed regimen either at intervals by application of a lotion or the like, it generally being the case that gradual improvement is noted with each successive application. Insofar as has been determined based upon clinical studies to date, no adverse side effects are encountered.
  • ⁇ -hydroxy acid has reference to and encompasses the general class of organic compounds containing at least one hydroxy group and at least one carboxyl group, and wherein at least one hydroxyl group is located on the ⁇ -carbon atom.
  • the compounds are organic acids having at least one carboxylic acid group and at least one hydroxyl group on the ⁇ -carbon atom, and may contain other functional groups including additional hydroxyl and carboxylic acid moieties.
  • Preferred ⁇ -hydroxy acids and/or ⁇ -hydroxy acid derivatives are less bulky structurally so that they penetrate the skin well, and thus have a backbone of from one to three carbon atoms such as those set out in U.S. Pat. No. 5,965,618 at column 6 lines 4 to 29.
  • glycolic and/or lactic acid or their derivatives are preferred; glycolic acid is especially efficacious.
  • acetyl carnitine in PC and/or ascorbyl fatty acid esters is efficacious in the treatment of skin damage because it is fat-soluble and readily disperses in cell membranes and other cellular components. In the presence of PC and/or ascorbyl fatty acid esters, acetyl carnitine readily penetrates skin. As mentioned above, it also is an active antioxidant that has been shown to protect against lipid peroxidation. Acetyl carnitine acts as a free radical scavenger and neutralizer, and prevents the cross-linking of cell membranes that is often seen in its post-inflammatory phases.
  • acetyl carnitine modulation of free radicals and other oxidative species appears to affect gene expression, including expression of nuclear factor ⁇ -B (NF- ⁇ B), nitric oxide synthe- tase and other mediators at all stages of proinflammation and inflammation.
  • NF- ⁇ B nuclear factor ⁇ -B
  • Acetyl carnitine's alteration of lipid peroxidation, protein cross-linking, growth factor stimulation, and membrane permeability may explain its negative effect on the symptoms of damaged skin.
  • the effects of acetyl carnitine are enhanced by using it in combination with ascorbyl fatty acid esters such as ascorbyl palmitate, because these compounds also act as antioxidants and scavenge free radicals.
  • phospholipase-A-2 produces arachidonic acid from the phospholipid- rich membranes of the cell, resulting in the production of metabolites.
  • stabilization of the cell membrane can inhibit the inflammatory cascade, therefore preventing the inflammatory response.
  • arachidonic acid has a direct toxic effect on the mitochondria, resulting in the uncoupling of oxidative phosphorylation, resulting in free radical damage to the mitochondrial membrane.
  • Acetyl carnitine with PC and/or fatty acid esters of ascorbic acid appear to intersperse in the cell membrane, stabilizing the membrane, and, at the same time, providing antioxidant capability.
  • the delivery of acetyl carnitine into the cell membrane appears to enhance membrane activity, such as exchange of nutrients and wastes of the cellular environment. This also enhances cellular function and repair.
  • Methods and compositions of the present invention are particularly useful for treating damaged skin tissue, particularly various types of dermatitis, skin conditions such as rosacea, seborrhea, eczema, xerosis (dry skin), psoriasis, thermal and radiation burns, and other types of inflammation.
  • Acetyl carnitine compositions of the invention are useful in treating both contact dermatitis and atopic dermatitis.
  • Topical application of acetyl carnitine according to the invention can also be effective to prevent symptoms in aging persons for the inhibition of microscarring of the dermis and to promote collagen production. It is an advantage of the invention that that treatment or preventive measures employ, as an active ingredient, natural compounds.
  • topical application of acetyl carnitine with phosphatidylcholine and/or ascorbyl fatty acid esters provides a simple, non-invasive, nontoxic, over-the-counter topical method for treating all kinds of skin damage.
  • composition contains fromtion. It is intended, however, that all such obvious modifications and variations be included within the scope of the invention in any sequence which is effective to meet the objectives there intended, unless the context specifically indicates the contrary.

Abstract

Selon l'invention, de l'acétyl-carnitine et de la phosphatidylcholine et/ou des esters d'acide gras d'ascorbyle sont appliqués de manière topique en vue de traiter des lésions cutanées, telles que l'eczéma de contact, la dermite atopique, le xérosis, l'eczéma, l'acné rosacée, la séborrhée, le psoriasis, les brûlures thermiques et celles causées par des radiations et d'autres types d'inflammations cutanées, ainsi que le vieillissement cutané. Les compositions typiques renferment entre environ 0,025 % et environ 5 %, plus restrictivement entre environ 0,5 % et environ 2 % d'acétyl-carnitine. Lorsque les esters d'acide gras d'ascorbyle sont utilisés, leurs concentrations sont comprises entre environ 0,5 % et environ 7 %, plus restrictivement entre environ 1 % et 5 % en poids, et les esters sont, de préférence, gras-solubles et saturés. Un mode de réalisation préféré renferme de l'acétyl L-carnitine, de la palmitate d'ascorbyle et de la lécithine alimentaire.
PCT/US2001/013401 2000-05-02 2001-04-25 Traitement de lesions cutanees au moyen d'acetyl-carnitine et de phosphatidylcholine et/ou d'esters d'acide gras d'ascorbyle WO2001082878A1 (fr)

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US56310800A 2000-05-02 2000-05-02
US09/563,108 2000-05-02

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Cited By (9)

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WO2002102340A2 (fr) * 2001-06-19 2002-12-27 Beiersdorf Ag Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide
WO2003005980A2 (fr) * 2001-07-07 2003-01-23 Beiersdorf Ag Preparations cosmetiques et dermatologiques contenant de la carnitine pour le traitement et la prevention active de la peau seche et autres alterations negatives de l'homeostasie physiologique de la peau saine
WO2003066573A1 (fr) * 2002-02-04 2003-08-14 Aldo Fassi Sels metalliques de carnitines, supplements dietetiques contenant ces sels et necessaires dietetiques destines a traiter des troubles sexuels chez l'homme
KR20040015533A (ko) * 2002-08-13 2004-02-19 주식회사 웰스킨 포스페티딜콜린을 포함하는 섬유화 유도용 조성물 및 상기조성물을 이용한 섬유화 유도방법
EP1610760A2 (fr) * 2003-03-28 2006-01-04 Lonza Inc. Compositions topiques de l-carnitine
WO2011024354A1 (fr) * 2009-08-25 2011-03-03 株式会社メドレックス Composition transdermique de la phosphatidylcholine et son procédé de production
DE102012214038A1 (de) * 2012-08-08 2014-02-13 Beiersdorf Ag Verwendung von Wirkstoffkombinationen aus Harnstoff und Car-ni-tin und/oder einem oder mehreren Acyl-Carnitinen zur Behandlung und Prophylaxe von Neurodermitis sowie des diabetischen Fußes
US20150094292A1 (en) * 2008-12-31 2015-04-02 Nitromega Corp. Topical compositions containing nitro fatty acids
IT201700054488A1 (it) * 2017-05-19 2018-11-19 Giancarlo Muscas Composizione per il trattamento di forme infiammatorie cutanee

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US5376361A (en) * 1993-01-13 1994-12-27 Perricone; Nicholas V. Method and compositions for topical application to the skin for prevention and/or treatment of radiation-induced skin damage
US5554647A (en) * 1989-10-12 1996-09-10 Perricone; Nicholas V. Method and compositions for treatment and/or prevention of skin damage and aging
US5667791A (en) * 1996-05-31 1997-09-16 Thione International, Inc. X-ray induced skin damage protective composition

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US5554647A (en) * 1989-10-12 1996-09-10 Perricone; Nicholas V. Method and compositions for treatment and/or prevention of skin damage and aging
US5376361A (en) * 1993-01-13 1994-12-27 Perricone; Nicholas V. Method and compositions for topical application to the skin for prevention and/or treatment of radiation-induced skin damage
US5667791A (en) * 1996-05-31 1997-09-16 Thione International, Inc. X-ray induced skin damage protective composition

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002102340A3 (fr) * 2001-06-19 2003-07-17 Beiersdorf Ag Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide
WO2002102340A2 (fr) * 2001-06-19 2002-12-27 Beiersdorf Ag Utilisation de carnitine et/ou d'une ou de plusieurs acyl-carnitines pour realiser des preparations cosmetiques ou dermatologiques destinees a accroitre la biosynthese de ceramide
WO2003005980A2 (fr) * 2001-07-07 2003-01-23 Beiersdorf Ag Preparations cosmetiques et dermatologiques contenant de la carnitine pour le traitement et la prevention active de la peau seche et autres alterations negatives de l'homeostasie physiologique de la peau saine
WO2003005980A3 (fr) * 2001-07-07 2003-09-18 Beiersdorf Ag Preparations cosmetiques et dermatologiques contenant de la carnitine pour le traitement et la prevention active de la peau seche et autres alterations negatives de l'homeostasie physiologique de la peau saine
US9744382B2 (en) 2001-07-07 2017-08-29 Beiersdorf Ag Cosmetic and dermatological preparations containing carnitine for treating and actively preventing dry skin and other negative alterations in the physiological homeostasis of healthy skin
WO2003066573A1 (fr) * 2002-02-04 2003-08-14 Aldo Fassi Sels metalliques de carnitines, supplements dietetiques contenant ces sels et necessaires dietetiques destines a traiter des troubles sexuels chez l'homme
KR20040015533A (ko) * 2002-08-13 2004-02-19 주식회사 웰스킨 포스페티딜콜린을 포함하는 섬유화 유도용 조성물 및 상기조성물을 이용한 섬유화 유도방법
EP1610760A2 (fr) * 2003-03-28 2006-01-04 Lonza Inc. Compositions topiques de l-carnitine
EP1610760A4 (fr) * 2003-03-28 2008-01-09 Lonza Ag Compositions topiques de l-carnitine
US20150094292A1 (en) * 2008-12-31 2015-04-02 Nitromega Corp. Topical compositions containing nitro fatty acids
WO2011024354A1 (fr) * 2009-08-25 2011-03-03 株式会社メドレックス Composition transdermique de la phosphatidylcholine et son procédé de production
JP5747820B2 (ja) * 2009-08-25 2015-07-15 株式会社 メドレックス ホスファチジルコリンの経皮投与組成物とその製造方法
US8568746B2 (en) 2009-08-25 2013-10-29 Medrx Co., Ltd. Transdermal composition of phosphatidylcholine and method for producing same
DE102012214038A1 (de) * 2012-08-08 2014-02-13 Beiersdorf Ag Verwendung von Wirkstoffkombinationen aus Harnstoff und Car-ni-tin und/oder einem oder mehreren Acyl-Carnitinen zur Behandlung und Prophylaxe von Neurodermitis sowie des diabetischen Fußes
IT201700054488A1 (it) * 2017-05-19 2018-11-19 Giancarlo Muscas Composizione per il trattamento di forme infiammatorie cutanee
WO2018211445A1 (fr) * 2017-05-19 2018-11-22 Muscas Giancarlo Composition pour le traitement de formes d'inflammation cutanée

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