WO2002069927A1 - Compositions comprising melatonin and vitamin a - Google Patents

Compositions comprising melatonin and vitamin a Download PDF

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Publication number
WO2002069927A1
WO2002069927A1 PCT/EP2002/002355 EP0202355W WO02069927A1 WO 2002069927 A1 WO2002069927 A1 WO 2002069927A1 EP 0202355 W EP0202355 W EP 0202355W WO 02069927 A1 WO02069927 A1 WO 02069927A1
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Prior art keywords
vitamin
composition according
melatonin
acid
derivative
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PCT/EP2002/002355
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German (de)
French (fr)
Inventor
Hans W. Schmid
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Asat Ag Applied Science & Technology
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Publication of WO2002069927A1 publication Critical patent/WO2002069927A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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

Definitions

  • the present invention relates to a composition which contains a combination of melatonin and vitamin A as active ingredients.
  • the composition is particularly suitable for the production of formulations for topical use on the skin and in the hair.
  • vitamin A in particular in the form of vitamin A acid
  • side effects include dermal irritation, which can cause reddening of the skin to various degrees. With sensitive skin, even edema or blisters can occur.
  • sunscreens After using a vitamin A preparation, exposure to sunlight or UV radiation should also be avoided. It is therefore strongly recommended to use sunscreens with a protection factor of 1 5 or more.
  • the present invention thus relates to a composition which comprises as active ingredients (a) melatonin or a derivative thereof and (b) vitamin A or a derivative thereof, in particular vitamin A acid or a derivative thereof.
  • the composition is preferred a topical formulation suitable for pharmaceutical or cosmetic applications.
  • the composition according to the invention contains a combination of active ingredients.
  • the first component of this combination is melatonin or a melatonin derivative, wherein melatonin derivatives are preferably selected from 5-methoxytryptamine, 5-M ethoxytryptophan, 5-methoxytryptophol, 5-methoxyindole-3-acetic acid and 6-hydroxymelatonin.
  • physiologically acceptable salts, esters and complex compounds thereof can also be used.
  • the second component of the composition is vitamin A or a vitamin A derivative, in particular selected from vitamin A acetate and vitamin A palmitate and in particular vitamin A acid (retinoic acid) or a derivative thereof, such as an ester, Salt or a complex compound of retinoic acid.
  • vitamin A acid retinoic acid
  • Physiologically acceptable salts, esters and complex compounds are preferably used.
  • composition according to the invention can contain the active ingredients dissolved or / and dispersed in a liquid, semi-solid or solid carrier system.
  • suitable carrier systems are liquids such as water, physiologically acceptable organic solvents such as ethanol or combinations thereof, oil-water emulsions, water-oil emulsions, fats, polyethylene glycols, propylene glycols, glycerol, emulsifiers or combinations thereof, and others in pharmaceutical and cosmetic formulations Carriers or auxiliaries used.
  • compositions can be obtained which allow a controlled release of at least one of the active ingredients, in particular of both active ingredients.
  • concentration of the active ingredients in the composition - depending on the application - can be varied within a wide range. Conveniently, the concentrations of the active ingredients are each independently in the range between 0.001% (weight) to 1% (weight) based on the total weight of the composition.
  • compositions according to the invention are particularly suitable for pharmaceutical or / and cosmetic applications, for example on the skin and / or in the hair.
  • the transdermal absorption of at least one of the active ingredients is preferably controllable.
  • compositions can be in the form of a solution, suspension, emulsion, microemulsion, nanosystem, cream, gel, lotion, spray, foam or ointment or in any other form suitable for topical applications. They are usually used in a packaging or application system selected from tubes, bottles, spray bottles, plasters, sponges and textile or plastic carriers and other systems suitable for application to the skin and / or in the hair.
  • the combination preparations according to the invention are particularly recommended for use in the evening and are particularly effective during the night.
  • the reduction in the side effects of vitamin A acid caused by melatonin is particularly strong.
  • compositions according to the invention are suitable for reducing or preventing the side effects of vitamin A, vitamin A acid or their derivatives due to the addition of melatonin. Furthermore, an increase in the physiological effect, in particular the wrinkle-reducing effect of vitamin A is found due to the addition of melatonin.
  • Vitamin A acid and melatonin were integrated in concentrations of 0.001% to 1% (wt.) In stable pharmaceutically and cosmetically applicable liposomal carriers to control the delivery of effects.
  • the Bangha et al. (Dermatology 1 95 (1 997), 248-252) described nanocarriers were used to produce the combination preparations according to the invention in order to achieve a targeted release of the active ingredient.
  • solid carrier systems such as agarose in various particle sizes, which contain vitamin A acid and melatonin distributed in the carrier system, have been successfully used for targeted drug delivery.
  • Combination preparations of vitamin A acid and melatonin have also been produced and successfully applied in emulsions, such as the Retin A formulation by Ortho Dermatological.

Abstract

The invention relates to compositions containing, as active substances, a combination of melatonin and vitamin A or vitamin A acid. The composition is particularly suited for producing formulations for topical use on skin and in hair.

Description

elatonin-Vitamin-A-Präparate elatonin vitamin A supplements
Beschreibungdescription
Die vorliegende Erfindung betrifft eine Zusammensetzung, die als Wirkstoffe eine Kombination von Melatonin und Vitamin A enthält. Die Zusammensetzung eignet sich insbesondere zur Herstellung von Formulierungen für die topische Anwendung auf der Haut und im Haar.The present invention relates to a composition which contains a combination of melatonin and vitamin A as active ingredients. The composition is particularly suitable for the production of formulations for topical use on the skin and in the hair.
Der Einsatz von Vitamin A, insbesondere in Form von Vitamin-A-Säure, für topische Applikationen ist bekannt. Als Nebenwirkungen findet man jedoch dermale Irritationen, die Rötungen der Haut in verschiedenen Graden erzeugen können. Bei empfindlicher Haut können sogar Ödeme oder Blasen auftreten. Nach Anwendung eines Vitamin-A-Präparats ist weiterhin die Exposition gegenüber Sonnenlicht oder UV-Strahlung zu vermeiden. Es wird daher dringend die Verwendung von Sonnenschutzmitteln mit dem Schutzfaktor 1 5 oder mehr empfohlen. Diese Nebenwirkungen von Vitamin A in topischen Applikationen begrenzen erheblich den Einsatz solcher Präparate.The use of vitamin A, in particular in the form of vitamin A acid, for topical applications is known. However, side effects include dermal irritation, which can cause reddening of the skin to various degrees. With sensitive skin, even edema or blisters can occur. After using a vitamin A preparation, exposure to sunlight or UV radiation should also be avoided. It is therefore strongly recommended to use sunscreens with a protection factor of 1 5 or more. These side effects of vitamin A in topical applications considerably limit the use of such preparations.
Überraschenderweise wurde im Rahmen der zur vorliegenden Erfindung führenden Untersuchungen festgestellt, dass der Zusatz von Melatonin in topischen Formulierungen bei gleichzeitiger Anwendung mit Vitamin A, insbesondere in Form von Vitamin-A-Säure oder deren Derivate, die unerwünschten Nebenwirkungen verhindert oder reduziert, ohne die Wirkung des Präparats zu verringern.Surprisingly, it was found in the course of the investigations leading to the present invention that the addition of melatonin in topical formulations when used simultaneously with vitamin A, in particular in the form of vitamin A acid or its derivatives, prevents or reduces the undesirable side effects without the effect to reduce the drug.
Ein Gegenstand der vorliegenden Erfindung ist somit eine Zusammensetzung, die als Wirkstoffe (a) Melatonin oder ein Derivat davon und (b) Vitamin A oder ein Derivat davon, insbesondere Vitamin-A-Säure oder ein Derivat davon, enthält. Die Zusammensetzung ist vorzugsweise eine topische Formulierung, die für pharmazeutische oder und kosmetische Anwendungen geeignet ist.The present invention thus relates to a composition which comprises as active ingredients (a) melatonin or a derivative thereof and (b) vitamin A or a derivative thereof, in particular vitamin A acid or a derivative thereof. The composition is preferred a topical formulation suitable for pharmaceutical or cosmetic applications.
Die erfindungsgemäße Zusammensetzung enthält eine Kombination von Wirkstoffen. Die erste Komponente dieser Kombination ist Melatonin oder ein Melatoninderivat, wobei Melatoninderivate vorzugweise ausgewählt werden a us 5-Methoxytryptamin , 5-M ethoxytryptophan, 5- Methoxytryptophol, 5-Methoxyindol-3-essigsäure und 6-Hydroxy- melatonin. Neben diesen Substanzen können auch physiologisch akzeptable Salze, Ester und Komplexverbindungen davon eingesetzt werden.The composition according to the invention contains a combination of active ingredients. The first component of this combination is melatonin or a melatonin derivative, wherein melatonin derivatives are preferably selected from 5-methoxytryptamine, 5-M ethoxytryptophan, 5-methoxytryptophol, 5-methoxyindole-3-acetic acid and 6-hydroxymelatonin. In addition to these substances, physiologically acceptable salts, esters and complex compounds thereof can also be used.
Die zweite Komponente der Zusammensetzung ist Vitamin A oder ein Vitamin-A-Derivat, insbesondere ausgewählt aus Vitamin-A-Acetat und Vitamin-A-Palmitat und insbesondere Vitamin-A-Säure (Retinoesäure) oder ein Derivat davon, wie etwa ein Ester, Salz oder eine Komplexverbindung der Retinoesäure. Bevorzugt werden physiologisch akzeptable Salze, Ester und Komplexverbindungen eingesetzt.The second component of the composition is vitamin A or a vitamin A derivative, in particular selected from vitamin A acetate and vitamin A palmitate and in particular vitamin A acid (retinoic acid) or a derivative thereof, such as an ester, Salt or a complex compound of retinoic acid. Physiologically acceptable salts, esters and complex compounds are preferably used.
Die erfindungsmäße Zusammensetzung kann die Wirkstoffe gelöst oder/und dispergiert in einem flüssigen, halbfesten oder festen Trägersystem enthalten. Beispiele für geeignete Trägersysteme sind Flüssigkeiten wie Wasser, physiologisch verträgliche organische Lösungsmittel wie Ethanol oder Kombinationen davon, Öl-Wasser-Emulsionen, Wasser-Öl-Emulsionen, Fette, Polyethylenglykole, Propylenglykole, Glycerin, Emulgatoren oder Kombinationen davon sowie andere in pharmazeutischen und kosmetischen Formulierungen verwendete Träger- oder Hilfsstoffe.The composition according to the invention can contain the active ingredients dissolved or / and dispersed in a liquid, semi-solid or solid carrier system. Examples of suitable carrier systems are liquids such as water, physiologically acceptable organic solvents such as ethanol or combinations thereof, oil-water emulsions, water-oil emulsions, fats, polyethylene glycols, propylene glycols, glycerol, emulsifiers or combinations thereof, and others in pharmaceutical and cosmetic formulations Carriers or auxiliaries used.
Bei Verwendung von spezifischen Formulierungssystemen wie Liposomen, Nanosomen oder festen Einschlussträgern wie Agarose können Zusammensetzungen erhalten werden, die eine kontrollierte Abgabe von zumindest einem der Wirkstoffe, insbesondere von beiden Wirkstoffen, erlauben. Die Konzentration der Wirkstoffe in der Zusammensetzung kann - je nach Anwendung - in breiten Bereichen variiert werden. Günstigerweise liegen die Konzentrationen der Wirkstoffe jeweils unabhängig im Bereich zwischen 0,001 % (Gewicht) bis 1 % (Gewicht) bezogen auf das Gesamtgewicht der Zusammensetzung.When using specific formulation systems such as liposomes, nanosomes or solid inclusion carriers such as agarose, compositions can be obtained which allow a controlled release of at least one of the active ingredients, in particular of both active ingredients. The concentration of the active ingredients in the composition - depending on the application - can be varied within a wide range. Conveniently, the concentrations of the active ingredients are each independently in the range between 0.001% (weight) to 1% (weight) based on the total weight of the composition.
Die erfindungsgemäßen Zusammensetzungen eignen sich insbesondere für pharmazeutische oder/und kosmetische Anwendungen beispielsweise auf der Haut oder/und im Haar. Dabei ist vorzugsweise die transdermale Absorption von zumindest einem der Wirkstoffe steuerbar.The compositions according to the invention are particularly suitable for pharmaceutical or / and cosmetic applications, for example on the skin and / or in the hair. The transdermal absorption of at least one of the active ingredients is preferably controllable.
Die Zusammensetzungen können als Lösung, Suspension, Emulsion, Mikroemulsion, Nanosystem, Creme, Gel, Lotion, Spray, Schaum oder Salbe oder in jeder anderen für topische Anwendungen geeigneten Form vorliegen. Sie werden überlicherweise in einem Verpackungs- oder Anwendungssystem ausgewählt aus Tuben, Flaschen, Sprayflaschen, Pflastern, Schwämmen und Textil- oder Kunststoffträgern und anderen für die Applikation auf der Haut oder/und im Haar geeigneten Systemen eingesetzt.The compositions can be in the form of a solution, suspension, emulsion, microemulsion, nanosystem, cream, gel, lotion, spray, foam or ointment or in any other form suitable for topical applications. They are usually used in a packaging or application system selected from tubes, bottles, spray bottles, plasters, sponges and textile or plastic carriers and other systems suitable for application to the skin and / or in the hair.
Die erfindungsgemäßen Kombinationspräparate werden insbesondere zur Anwendung am Abend empfohlen und entfalten ihre Wirkung insbesondere während der Nachtstunden. Bei dieser Art von Anwendung ist die durch Melatonin bewirkte Verringerung der Nebenwirkungen von Vitamin-A-Säure besonders stark.The combination preparations according to the invention are particularly recommended for use in the evening and are particularly effective during the night. In this type of application, the reduction in the side effects of vitamin A acid caused by melatonin is particularly strong.
Die Behandlung erfolgt in topischen, für die Anwendung auf der Haut oder/und im Haar geeigneten Applikationen, welche die entsprechenden, für den jeweiligen Verwendungszweck geeigneten Konzentrationen der Wirkstoffe enthalten. Die erfindungsgemäßen Zusammensetzungen eignen sich zur Verringerung bzw. Verhinderung der Nebenwirkungen von Vitamin A, Vitamin-A-Säure oder deren Derivaten auf Grund des Zusatzes von Melatonin. Weiterhin wird eine Verstärkung der physiologischen Wirkung, insbesondere der faltenreduzierenden Wirkung von Vitamin A auf Grund des Zusatzes von Melatonin gefunden.The treatment is carried out in topical applications which are suitable for use on the skin and / or in the hair and which contain the appropriate concentrations of the active compounds which are suitable for the particular intended use. The compositions according to the invention are suitable for reducing or preventing the side effects of vitamin A, vitamin A acid or their derivatives due to the addition of melatonin. Furthermore, an increase in the physiological effect, in particular the wrinkle-reducing effect of vitamin A is found due to the addition of melatonin.
Die Erfindung soll weiterhin durch die folgenden Beispiele erläutert werden.The invention is further illustrated by the following examples.
Beispiel 1example 1
Es wurden Lösungen von Vitamin-A-Säure in jeweils verschiedenen Konzentrationen zwischen 0,001 % und 1 % (Gew.) und Melatonin in jeweils verschiedenen Konzentrationen von 0,001 % und 1 % (Gew.) in Trägergemischen, bestehend aus Ethylalkohol, Propylenglycol und Wasser in jeweils verschiedenen Konzentrationen hergestellt.There were solutions of vitamin A acid in different concentrations between 0.001% and 1% (wt.) And melatonin in different concentrations of 0.001% and 1% (wt.) In carrier mixtures consisting of ethyl alcohol, propylene glycol and water in different concentrations produced.
Beispiel 2Example 2
Vitamin-A-Säure und Melatonin wurden in Konzentrationen von jeweils 0,001 % bis 1 % (Gew.) in stabilen pharmazeutisch und kosmetisch anwendbaren liposomalen Trägern zur Steuerung der Wirkungsabgabe integriert.Vitamin A acid and melatonin were integrated in concentrations of 0.001% to 1% (wt.) In stable pharmaceutically and cosmetically applicable liposomal carriers to control the delivery of effects.
Auch die bei Bangha et al. (Dermatology 1 95 ( 1 997), 248-252) beschriebenen Nanoträger wurden zur Herstellung der erfindungsgemäßen Kombinationspräparate verwendet, um eine gezielte Wirkstoffabgabe zu erreichen.The Bangha et al. (Dermatology 1 95 (1 997), 248-252) described nanocarriers were used to produce the combination preparations according to the invention in order to achieve a targeted release of the active ingredient.
Außerdem wurden feste Trägersysteme wie Agarose in verschiedenen Partikelgrößen, die Vitamin-A-Säure und Melatonin im Trägersystem verteilt enthalten, erfolgreich zur gezielten Wirkstoffabgabe eingesetzt. Kombinationspräparate von Vitamin-A-Säure und Melatonin wurden auch in Emulsionen, wie z.B der Retin-A-Formulierung von Ortho Dermatological hergestellt und erfolgreich zur Anwendung gebracht. In addition, solid carrier systems such as agarose in various particle sizes, which contain vitamin A acid and melatonin distributed in the carrier system, have been successfully used for targeted drug delivery. Combination preparations of vitamin A acid and melatonin have also been produced and successfully applied in emulsions, such as the Retin A formulation by Ortho Dermatological.

Claims

Ansprüche Expectations
1 . Zusammensetzung, dadurch gekennzeichnet, dass sie als Wirkstoffe1 . Composition, characterized in that they are active ingredients
(a) Melatonin oder ein Derivat davon und(a) melatonin or a derivative thereof and
(b) Vitamin A oder ein Derivat davon oder Vitamin-A-Säure oder ein Derivat davon enthält.(b) contains vitamin A or a derivative thereof or vitamin A acid or a derivative thereof.
2. Zusammensetzung nach Anspruch 1 , dadurch gekennzeichnet, dass sie Melatonin oder ein Melatonin-Derivat ausgewählt aus 5- Methoxytryptamin, 5-Methoxytryptophan, 5-Methoxytryptophol, 5- Methoxyindol-3-essigsäure und 6-Hydroxy-melatonin sowie physiologisch akzeptablen Salzen, Estern u nd Komplexverbindungen davon enthält.2. Composition according to claim 1, characterized in that it contains melatonin or a melatonin derivative selected from 5-methoxytryptamine, 5-methoxytryptophan, 5-methoxytryptophol, 5-methoxyindole-3-acetic acid and 6-hydroxy-melatonin and physiologically acceptable salts, Contains esters and complex compounds thereof.
3. Zusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass sie Vitamin A oder ein Vitamin-A-Derivat ausgewählt aus Vitamin-A-Acetat und Vitamin-A-Palmitat enthält.3. Composition according to claim 1 or 2, characterized in that it contains vitamin A or a vitamin A derivative selected from vitamin A acetate and vitamin A palmitate.
4. Zusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass sie Vitamin-A-Säure oder/und physiologisch akzeptabel Salze, Ester oder/und Komplexverbindungen davon enthält.4. Composition according to claim 1 or 2, characterized in that it contains vitamin A acid and / or physiologically acceptable salts, esters or / and complex compounds thereof.
5. Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass die Wirkstoffe gelöst oder/und dispergiert in einem flüssigen, halbfesten oder festen Trägersystem vorliegen. 5. Composition according to one of claims 1 to 4, characterized in that the active ingredients are dissolved or / and dispersed in a liquid, semi-solid or solid carrier system.
6. Zusammensetzung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass die Konzentration oder Wirkstoffe jeweils im Bereich zwischen 0,001 % (Gewicht) und 1 % (Gewicht) bezogen auf das Gesamtgewicht der Zusammensetzung ist.6. Composition according to one of the preceding claims, characterized in that the concentration or active ingredients in each case in the range between 0.001% (weight) and 1% (weight) based on the total weight of the composition.
7. Zusammensetzung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass sie eine kontrollierte Abgabe von zumindest einem der Wirkstoffe erlaubt.7. Composition according to one of the preceding claims, characterized in that it allows a controlled release of at least one of the active ingredients.
8. Zusammensetzung nach einem der vorhergehenden Ansprüche für pharmazeutische oder/und kosmetische Anwendungen.8. Composition according to one of the preceding claims for pharmaceutical and / or cosmetic applications.
9. Zusammensetzung nach Anspruch 7 zur Anwendung auf der Haut oder/und im Haar.9. The composition according to claim 7 for use on the skin and / or in the hair.
1 0. Zusammensetzung nach Anspruch 9, dadurch gekennzeichnet, dass die transdermale Absorption von zumindest einem der1 0. Composition according to claim 9, characterized in that the transdermal absorption of at least one of the
Wirkstoffe steuerbar ist.Active substances is controllable.
1 1 . Zusammensetzung nach einem der vorhergehenden Ansprüche als Lösung, Suspension, Emulsion, Mikroemulsion, Nanosystem, Creme, Gel, Lotion, Spray, Schaum oder Salbe.1 1. Composition according to one of the preceding claims as a solution, suspension, emulsion, microemulsion, nanosystem, cream, gel, lotion, spray, foam or ointment.
1 2. Zusammensetzung nach einem der vorhergehenden Ansprüche in einem Verpackungs- oder Anwendungssystem ausgewählt aus Tuben, Flaschen, Sprayflaschen, Pflastern, Schwämmen und Textil- oder Kunststoffträgern. 1 2. Composition according to one of the preceding claims in a packaging or application system selected from tubes, bottles, spray bottles, plasters, sponges and textile or plastic carriers.
3. Zusammensetzung nach einem der vorhergehenden Ansprüche zur Verringerung bzw. Verhinderung der Nebenwirkungen von Vitamin A oder Vitamin-A-Säure durch den Zusatz von Melatonin.3. Composition according to one of the preceding claims for reducing or preventing the side effects of vitamin A or vitamin A acid by the addition of melatonin.
4. Zusammensetzung nach einem der vorhergehenden Ansprüche zur Verstärkung der faltenreduzierenden Wirkung von Vitamin A, Vitamin-A-Säure oder/und Derivaten davon durch den Zusatz von Melatonin. 4. Composition according to one of the preceding claims for enhancing the wrinkle-reducing effect of vitamin A, vitamin A acid or / and derivatives thereof by the addition of melatonin.
PCT/EP2002/002355 2001-03-05 2002-03-04 Compositions comprising melatonin and vitamin a WO2002069927A1 (en)

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DE2001110418 DE10110418A1 (en) 2001-03-05 2001-03-05 Melatonin Vitamin A supplements
DE10110418.9 2001-03-05

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WO2009024361A1 (en) * 2007-08-22 2009-02-26 Henkel Ag & Co. Kgaa Hair treatment compositions with alcohol(s) and melatonin/agomelatine
WO2009024359A1 (en) * 2007-08-22 2009-02-26 Henkel Ag & Co. Kgaa Hair treatment agent with conditioner(s) and melatonin/agomelatin
US8017645B2 (en) 2002-10-30 2011-09-13 Asat Ag Applied Science & Technology Melatonin daily dosage units
KR101675062B1 (en) 2016-03-24 2016-11-11 김삼 Double coated Vitamin C using melatonin and cosmetic composition containing the same

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CN1294909C (en) * 2004-03-19 2007-01-17 谭敦宁 Novel anti-biological cell free redical oxidation injury mixture
ITRM20060108A1 (en) 2006-03-03 2007-09-04 Colella Gino MELATONIN-BASED COMPOSITIONS AND IMMUNOSTIMULATING SUBSTANCES
JP5895303B2 (en) * 2011-04-01 2016-03-30 イアソマイ エービー Novel combinations comprising N-acetyl-L-cysteine and uses thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8017645B2 (en) 2002-10-30 2011-09-13 Asat Ag Applied Science & Technology Melatonin daily dosage units
US8062648B2 (en) 2002-10-30 2011-11-22 Asat Ag Applied Science & Technology Formulations containing melatonin, ginkgo biloba, and biotin
WO2009024361A1 (en) * 2007-08-22 2009-02-26 Henkel Ag & Co. Kgaa Hair treatment compositions with alcohol(s) and melatonin/agomelatine
WO2009024359A1 (en) * 2007-08-22 2009-02-26 Henkel Ag & Co. Kgaa Hair treatment agent with conditioner(s) and melatonin/agomelatin
KR101675062B1 (en) 2016-03-24 2016-11-11 김삼 Double coated Vitamin C using melatonin and cosmetic composition containing the same

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