EP1620185A2 - Kosmetische oder pharmazeutische zusammensetzung enthaltend säureamide und deren dermatologische verwendung - Google Patents

Kosmetische oder pharmazeutische zusammensetzung enthaltend säureamide und deren dermatologische verwendung

Info

Publication number
EP1620185A2
EP1620185A2 EP04742373A EP04742373A EP1620185A2 EP 1620185 A2 EP1620185 A2 EP 1620185A2 EP 04742373 A EP04742373 A EP 04742373A EP 04742373 A EP04742373 A EP 04742373A EP 1620185 A2 EP1620185 A2 EP 1620185A2
Authority
EP
European Patent Office
Prior art keywords
skin
active agent
composition
cosmetic
amino acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04742373A
Other languages
English (en)
French (fr)
Inventor
Claude Dal Farra
Nouha Domloge
Dominique Peyronel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vincience SA
Original Assignee
Societe dExtraction des Principes Actifs SA
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 Societe dExtraction des Principes Actifs SA filed Critical Societe dExtraction des Principes Actifs SA
Publication of EP1620185A2 publication Critical patent/EP1620185A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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

  • Cosmetic or pharmaceutical composition comprising amino acids, uses and methods of treatment.
  • the invention relates to the field of cosmetics and pharmaceuticals, in particular the field of dermatology.
  • the subject of the present invention is the use of at least one isoleucine amino acid, mono or polyhydroxylated, and / or one of these derivatives, as active agent, alone or in combination with at least one other active agent , in or for the preparation of a cosmetic or dermo-pharmaceutical or dermatological composition.
  • the skin is a covering organ covering the entire surface of the body. It is a vital organ ensuring multiple functions such as sensory functions, protective vis-à-vis multiple external aggressions, immune, metabolic or thermoregulatory. These roles are made possible thanks to a complex structure which combines various tissue structures.
  • the skin, as well as the integuments, are constantly subjected to nuisances of external origin which manifest themselves in different aspects. These attacks can be significant and they can threaten their balance and appearance.
  • the search for means in order to preserve the skin and the integuments, or even to protect them against all manifestations liable to affect their proper functioning or their appearance, such as aging, mobilizes a very large number of researchers, in particular in the field of cosmetics .
  • the inventors have succeeded in selecting particular substances having remarkable properties when these are applied to the skin.
  • the inventors of the present invention have unexpectedly and surprisingly found that particular amino acids exhibit specific biological activities which make them directly usable in cosmetic, dermatological or pharmaceutical preparations or compositions.
  • isoleucine and / or its derivatives, mono or polyhydroxylated, in the pharmaceutical field is known in particular for its effective action in the treatment of non-insulin dependent diabetes as described in patent EP 0 587 476.
  • the active agent can be defined as being a molecule or a set of molecules capable of bringing modifications or modulations to the functioning of a biological system.
  • the amino acid is 4-hydroxyisoleucine of formula:
  • the compounds according to the invention relate to the isoleucine derivatives and to the 4-hydroxyisoleucine derivatives.
  • isoleucine derivatives is meant both these chemical derivatives and these biological derivatives.
  • derivative is meant all the amino acid derivatives leucine or isoleucine to which a group would have been added. This group being capable of bringing better properties to the active agent defined according to the invention.
  • the groups can be added in order to facilitate better penetration into the skin, these derivatives being for example radicals of the "oleyl”, “stearyl”, “palmityl” type, etc.
  • the amino acid is modified on its carboxylic acid functions and / or on its amino functions.
  • the amino acids according to the invention can be modified by acylation or acetylation on their amino function, and / or they can be modified by amidation or esterification on their carboxylic function.
  • amino acids may be in the form of lactone.
  • amino acids according to the present invention can be found in any existing isometric form.
  • 4-hydroxyisoleucine will preferably be used in the form of its isomers (2S, 3R, 4S) and / or (2R, 3R, 4S). These particular isomers being the isomers which are mainly obtained from the process for obtaining 4-hydroxyisoleucine used to obtain the active agent according to the invention. More particularly according to the invention, 4-hydroxyisoleucine is in the form of the (2S, 3R, 4S) isomer.
  • the active agent is of plant origin.
  • the active principle according to the invention is obtained from plants belonging to the genus Trigonella.
  • the amino acid can be obtained from at least any one of the numerous varieties and species belonging to the genus Trigonella.
  • the active substance is obtained from at least one plant of the species Trigonella foenum graecum, commonly called fenugreek.
  • Fenugreek is an annual herb, it belongs to the sub-order of legumes, to the family of Papilionaceae and to the genus Trigonella. It is a plant cultivated mainly in the Mediterranean regions and known since antiquity for its therapeutic virtues. This plant has the distinction of having a high content of protein material in the seed and especially of having a particular free amino acid, hydroxisoleucine. This amino acid was first identified in 1973 by Fowden et al., It represents more than 60% of the free amino acids present in the seed. Hydroxyisoleucine is also present but in smaller quantities in the leaves and stems of fenugreek. Thus, according to a preferred embodiment of the invention, the active principles will be extracted from the seeds of plants of the genus Trigonella, and more particularly from seeds of the plant of the species Trigonella foenum graecum.
  • 4-hydroxyisoleucine is also present in some other plant species; thus Raffholz et al. (1984) have shown the presence of this particular amino acid in Quararibea funebris, a tree in the Bombacaceae family.
  • the presence of 4-hydroxyisoleucine has also been reported in species such as Lactarius camphoraius (Dardenne et al., 1986), Dioscoreae delto ⁇ dea and Balanites aegyplia (Hardman and Abu-Al-Futuh, 1976). It is understood that the active compound according to the invention, in particular 4-hydroxyisoleucine, can be obtained from any of the plant species containing it.
  • amino acids which are the subject of this patent can be obtained either by conventional chemical synthesis or by extraction or purification from a substance of natural or synthetic origin.
  • the active principle is obtained by extraction and / or purification from a natural raw material, in particular vegetable.
  • a first step it is possible to grind the seeds, using a plant grinder for example. Then the fenugreek seeds are "defatted” by extraction of fatty substances with conventional organic solvents for this use such as, for example, hexane, chloroform, an alcohol or acetone. According to a variant of the process of the invention, it is possible to use seeds during germination, or even to use only part of the seed containing the embryo and / or the cotyledons.
  • the actual extraction is carried out with stirring, at a temperature between 4 and 100 ° C, in an aqueous solution, that is to say composed of water, or by a solution comprising a mixture of water and d 'An organic solvent miscible with water, preferably an alcohol (methanol, ethanol or isopropanol).
  • aqueous solution that is to say composed of water
  • d 'An organic solvent miscible with water preferably an alcohol (methanol, ethanol or isopropanol).
  • the proportion of water in the mixture can vary between 10 and 100%.
  • the extraction is carried out at a pH between 2 and 12. According to a variant of the extraction process, this can be made in a mixture of water and polyol; that is to say propylene, dipropylene, butylene or hexylene glycol, or also glycerol.
  • the extraction can be carried out using a hydroalcoholic mixture, preferably in a mixture containing approximately 70% of ethanol.
  • the alcoholic extract being a first usable form of the extract containing the active agent.
  • An alcohol evaporation step can easily be envisaged.
  • the soluble fraction is subsequently recovered by centrifugation and by filtration.
  • Low molecular weight components, i.e. free amino acids, are separated by dialysis from other higher molecular weight compounds.
  • This treatment can consist of bringing our solution into contact with various absorbents such as activated carbon, bleaching earth or silica; then, thereafter, to carry out a filtration step.
  • the extract obtained can be further purified by fractionation, in particular by a conventional method of chromatography on ion exchange resin, such as for example by the technique of Moore, Syein and Spackman (1958).
  • the extract can also be purified and concentrated by a dialysis process. Any one of the more or less purified forms of the extract is then dissolved in water or in any mixture containing water, then sterilized by ultrafiltration. It is thus possible to easily obtain an extract containing 4-hydroxyisoleucine at a very high degree of purity.
  • the invention further relates to the use of at least one amino acid isoleucine and / or an isoleucine derivative, mono or polyhydroxylated, as defined above, in or for the preparation of a composition ; the active agent or the composition being intended to treat in a curative and / or preventive manner the cutaneous manifestations of aging, and / or to improve the appearance of the skin and / or integuments. More generally, the active compound according to the invention will have an effective activity in all skin care and / or integuments. By the care of the skin and / or appendages, is meant all the actions intended to preserve or restore a good functioning of the skin and / or appendages or still any means which is used to preserve or improve their appearance and / or their appearance.
  • the treatment includes hydration, soothing, protection against all types of aggression, in particular sun protection, the fight and the prevention of the manifestations of aging, in particular the cutaneous manifestations of aging.
  • the expression “cutaneous manifestations of aging” means any modification of the external appearance of the skin due to aging, such as, for example, wrinkles and fine lines, withered skin, soft skin, thinned skin, lack of elasticity and / or skin tone, dull and dull skin but also all internal skin modifications which do not systematically result in a modified external appearance such as, for example, all internal degradations of the skin following exposure to ultraviolet radiation.
  • improving the appearance of the skin is meant all the phenomena which are likely to result in a visual improvement in the condition of the skin. The skin will look better; it will, for example, be much more beautiful, firm and / or smooth. All small imperfections will be diminished or removed. The papery appearance of the skin will, for example, be reduced.
  • the active agent according to the invention has a particularly effective action on the metabolism of skin cells.
  • the active ingredient according to the invention makes it possible in particular to increase the synthesis of proteins essential to its functioning, very particularly by increasing the synthesis of proteins constituting the extracellular matrix.
  • proteins constituting the extracellular matrix and particularly effective in the proper functioning of the skin, mention may be made of laminin, fibronectin, elastin or even collagen.
  • laminin, fibronectin, elastin or even collagen As proteins constituting the extracellular matrix, and particularly effective in the proper functioning of the skin, mention may be made of laminin, fibronectin, elastin or even collagen.
  • the increased expression of these proteins has been demonstrated by numerous tests using immunolabeling methods.
  • the active agent according to the invention, or the composition containing it has a truly positive action on the tissue regeneration of the skin as well as on scarring.
  • the active agent according to the invention has beneficial effects in terms of protein synthesis of keratinocytes.
  • Another subject of the invention therefore is the use of at least one active ingredient as defined above, or of a cosmetic composition comprising it, in order to increase the synthesis of keratins.
  • This active ingredient in particular promotes cell differentiation of keratinocytes, the latter therefore migrate more rapidly towards the surface of the epidermis and ensure better resistance of the stratum corneum. While progressing towards the higher layers, the keratinocytes flatten and pour into the extracellular space a cement made up of lipids, cholesterol, free saturated fatty acids and ceramides which increase the cohesion between cells and thus contribute to the barrier role of the epidemic.
  • the active ingredient according to the invention therefore has an effective action on the skin barrier, this active ingredient therefore increases this barrier function.
  • the active principle or the composition according to the invention can be intended to protect keratinous substrates, and more particularly to protect the skin and / or the integuments against all types of external aggressions.
  • This active agent, or of a composition containing it will allow the keratinous substrates to be protected and to better resist the stress that the environment produces on them.
  • the term "external aggression” means the aggressions that the environment can produce. These attacks can be of chemical, physical, biological or thermal origin. By way of example, mention may be made of aggressions such as pollution, UV, friction, water with a high concentration of limestone, temperature variations or even products with an irritant nature such as surfactants, preservatives or the perfumes.
  • the active agent, or the composition containing it has anti-inflammatory and anti-irritant effects. The use of the properties of this cosmetic agent therefore makes it possible to have a more protected skin and clearly less sensitive to the various aggressions it may encounter. The skin is soothed.
  • the subject of the invention is a cosmetic and / or dermatological and / or dermo-pharmaceutical composition containing, as active ingredient, in a cosmetically or pharmaceutically acceptable medium, at least one compound as defined above; that is to say an amino acid isoleucine, mono or polyhydroxylated, and / or one of its derivatives.
  • the amino acid of the composition is 4-hydroxyisoleucine.
  • the active substance is obtained from at least one plant of the species Trigonella foenum graecum.
  • the part used for the preparation of the active agent is the plant seed.
  • the composition according to the invention may be a cosmetic and / or dermatological and / or dermo-pharmaceutical composition.
  • the composition is a cosmetic composition, because it is intended to improve the appearance and the general cutaneous performance of the individual who uses it.
  • the composition according to the invention is preferably a composition suitable for administration by the route external topical, mainly on the skin, mucous membranes and / or integuments, comprising a cosmetically or dermatologically acceptable medium.
  • the invention is intended for mammals in general and more particularly for human beings.
  • the effective amount of active ingredient corresponds to the amount necessary to obtain the desired result.
  • the abovementioned active principle is present, in the compositions of the invention, at a concentration of between 0.00001% and 20% approximately, and preferably at a concentration of between 0.001 % and approximately 10% by weight relative to the total weight of the final composition.
  • the abovementioned active agent is dissolved beforehand in one or more cosmetically or pharmaceutically acceptable solvents such as water, ethanol, propanol or isopropanol, propylene glycol, butylene glycol, dipropylene glycol, ethoxylated or propoxylated diglycols or any mixture of these solvents.
  • one or more cosmetically or pharmaceutically acceptable solvents such as water, ethanol, propanol or isopropanol, propylene glycol, butylene glycol, dipropylene glycol, ethoxylated or propoxylated diglycols or any mixture of these solvents.
  • the abovementioned active agent is dissolved beforehand in a cosmetic or pharmaceutical carrier such as liposomes or adsorbed on powdery organic polymers, mineral supports such as talcs and bentonites, and more generally solubilized in or attached to any cosmetically or pharmaceutically acceptable carrier.
  • a cosmetic or pharmaceutical carrier such as liposomes or adsorbed on powdery organic polymers, mineral supports such as talcs and bentonites, and more generally solubilized in or attached to any cosmetically or pharmaceutically acceptable carrier.
  • the composition according to the invention can be ingested, injected or applied to the skin (on any cutaneous zone of the body), the hair, the nails or the mucous membranes.
  • the composition according to the invention can be in all the galenical forms normally used.
  • the compositions according to the present invention will be in a dosage form suitable for administration by the topical skin route. They cover all cosmetic and dermatological forms. These compositions must therefore contain a cosmetically acceptable medium, that is to say compatible with the skin, hair or hair.
  • compositions can in particular be in the form of an aqueous, hydroalcoholic or oily solution; an oil-in-water, water-in-oil or multiple emulsion; they can also be in the form of creams, suspensions or even powders, suitable for application to the skin, mucous membranes, lips and / or the hair.
  • These compositions can be more or less fluid and have the appearance of a cream, a lotion, a milk, a serum, an ointment, a shampoo, a gel, a paste or foam. They can also be in solid form, such as a stick or be applied to the skin in the form of an aerosol. They can be used as a care product and / or as a make-up product for the skin.
  • the composition according to the invention can be in the form of an aqueous, oily lotion or in the form of serum.
  • the composition can be in the form of drops and for ingestion, it can be in the form of capsules, granules, syrups or tablets.
  • These compositions also include any additive commonly used in the intended field of application as well as the adjuvants necessary for their formulation, such as solvents, thickeners, diluents, antioxidants, dyes, sunscreens, self-tanning agents, pigments, fillers, preservatives, perfumes, odor absorbers, cosmetic or pharmaceutical active ingredients, essential oils, vitamins, essential fatty acids, surfactants, film-forming polymers, etc. .
  • these adjuvants are chosen so as not to harm the desired advantageous properties of the composition according to the invention.
  • These adjuvants can, for example, correspond from 0.01 to 20% of the total weight of the composition.
  • the fatty phase can represent from 5 to 80% by weight and preferably from 5 to 50% by weight relative to the total weight of the composition.
  • the emulsifiers and co-emulsifiers used in the composition will be chosen from those conventionally used in the field under consideration. For example, they can be used in a proportion ranging from 0.3 to 30% by weight, relative to the total weight of the composition.
  • those skilled in the art will take care to choose any additional compounds, active or non-active, and / or their quantities, so that the advantageous properties of the mixture are not, or not substantially, altered by the addition considered.
  • compositions according to the invention find application in particular as a cosmetic or pharmaceutical composition for the skin, mucous membranes and / or semi-mucous membranes, but also as a cosmetic composition for the hair and / or body hair. They find a very particular application as a product for protecting and / or caring for the skin.
  • compositions which are the subject of the invention find their application in a large number of treatments, in particular cosmetic or dermatological treatments, and they can constitute a cosmetic composition, in particular for the treatment, protection, care, make-up removal and / or cleaning of the skin, lips and / or hair, and / or for making up the skin, lips, eyelashes and / or body.
  • the composition according to the invention may also consist of solid preparations also comprising soaps or cleaning bars.
  • the composition can also be packaged in the form of an aerosol composition also comprising a propellant under pressure.
  • the composition can also be for oral use, such as for example a toothpaste paste.
  • the composition of the invention can also be a cosmetic composition intended for oral administration.
  • the composition according to the invention can be in any suitable form, particularly in the form of an oral solution, a syrup, a tablet, a dragee, a capsule or still a food or nutritional supplement.
  • the present invention relates to a cosmetic treatment method for caring for the skin and / or integuments comprising applying to the surface of the skin an effective amount of active agent as defined above, in order to obtain the desired action.
  • These methods can in particular be used in order to preventively and / or curatively treat the manifestations of skin aging, but also in order to protect the skin and / or the integuments against external aggressions, or also in order to combat the manifestations of the skin inflammation and irritation.
  • Particular embodiments of this cosmetic treatment process also result from the preceding description.
  • the cosmetic treatment method of the invention can be implemented in particular by applying the cosmetic compositions as defined above, according to the usual technique for using these compositions, for example: application of creams, gels, serums , lotions, milks, shampoos or sunscreen compositions, on the skin or on the hair, or else application of toothpaste on the gums.
  • application of creams, gels, serums , lotions, milks, shampoos or sunscreen compositions for example: application of creams, gels, serums , lotions, milks, shampoos or sunscreen compositions, on the skin or on the hair, or else application of toothpaste on the gums.
  • Example 1 Preparation of 4-hydroxyisoleucine. A quantity of 100 grams of defatted seeds of the plant of the species Trigonella foenum graecum is ground in a knife mill, at a particle size of 200mm.
  • the concentrate is passed through a column containing a cation exchange resin so as to retain the amino acid 4-hydroxyisoleucine, which is then eluted using, for example, an ammonia solution.
  • the solution thus obtained is concentrated in 70% ethanol, then a new purification step is carried out by passing the mixture over an adsorption chromatography on silica gel.
  • the column is eluted with 70% ethanol.
  • the recovered mixture is concentrated so as to obtain a solution containing an optimal level of 4-hydroxyisoleucine.
  • phase A and phase B are heated separately to a temperature between 65 ° C and 70 ° C, phase C is incorporated, then phase A is emulsified in phase B.
  • the Carbomer is neutralized with the phase D at a temperature around 45 ° C.
  • Phase E is then added with stirring and the cooling is continued to 25 ° C.
  • phase A and phase B are heated separately to a temperature between 70 ° C and 75 ° C.
  • Phase B is emulsified in A with “Staro” stirring. After cooling to 50 ° C, the mixture is neutralized with phase C.
  • Phase D is then added when the temperature is below 40 ° C. Cooling is continued to 25 ° C with slow stirring.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP04742373A 2003-03-28 2004-03-26 Kosmetische oder pharmazeutische zusammensetzung enthaltend säureamide und deren dermatologische verwendung Withdrawn EP1620185A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0303886A FR2852841B1 (fr) 2003-03-28 2003-03-28 Composition cosmetique ou pharmaceutique comprenant des acides amines, utilisations et procedes de traitement
PCT/FR2004/000769 WO2004087091A2 (fr) 2003-03-28 2004-03-26 Composition cosmetique ou pharmaceutique comprenant des acides amines, utilisation et procede de traitement dermatologique

Publications (1)

Publication Number Publication Date
EP1620185A2 true EP1620185A2 (de) 2006-02-01

Family

ID=32947268

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04742373A Withdrawn EP1620185A2 (de) 2003-03-28 2004-03-26 Kosmetische oder pharmazeutische zusammensetzung enthaltend säureamide und deren dermatologische verwendung

Country Status (3)

Country Link
EP (1) EP1620185A2 (de)
FR (1) FR2852841B1 (de)
WO (1) WO2004087091A2 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2887773B1 (fr) * 2005-07-01 2008-05-30 Soc Extraction Principes Actif Utilisation d'un acide amine en tant qu'agent actif inducteur de la synthese des proteines sirt dans les cellules de la peau.
WO2008102671A1 (ja) 2007-02-22 2008-08-28 Ajinomoto Co., Inc. ４－ヒドロキシイソロイシンの精製方法
CN104027266A (zh) * 2014-05-26 2014-09-10 邓林生 高效生发乳液的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2695317B1 (fr) * 1992-09-07 1995-03-10 Monal Lab Composition apte à stimuler la sécrétion d'insuline destinée au traitement du diabète non insulino-dépendant.
IL108583A (en) * 1994-02-07 1997-06-10 Yissum Res Dev Co Galactomannan emulsions and comestible products containing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004087091A3 *

Also Published As

Publication number Publication date
FR2852841A1 (fr) 2004-10-01
WO2004087091A3 (fr) 2004-11-11
FR2852841B1 (fr) 2006-08-04
WO2004087091A2 (fr) 2004-10-14

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