Classifications

• • 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
  • A61Q5/006—Antidandruff preparations
• • 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
  • A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
  • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9783—Angiosperms [Magnoliophyta]
  • A61K8/9789—Magnoliopsida [dicotyledons]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/10—Anti-acne agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • 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
• • 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
  • A61Q5/02—Preparations for cleaning 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
  • A61Q19/002—Aftershave preparations
• • 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
  • A61Q19/005—Preparations for sensitive 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
  • A61Q19/008—Preparations for oily skin

Definitions

• the present invention relates to a new cosmetic composition of compounds with a lipoamino acid structure, with germicidal activity.
• acne which is a frequent skin condition affecting, as of the filing date of this patent application, approximately five million people in this country; the most common form is juvenile polymorphic acne, which appears at puberty.
• Acne is triggered in the pilosebaceous follicle by simultaneously causing hyper keratinization of the pilosebaceous canal, sebaceous hypersecretion as well as bacterial proliferation in the pilosebaceous follicle
• the hyper keratinization of the pilosebaceous canal leads to its obstruction, which in turn favors the implantation of a germ frequently found in this pathology: Propionibacterium acnes.
• Sebaceous hypersecretion is a constant factor during acne; it comes from an increased sensitivity of the sebaceous gland to androgens, which leads to greater secretion of sebum. Due to the hyper keratinization of the pilosebaceous canal, the elimination of sebum is hindered, even prevented, and this induces the formation of closed comedones and microcysts. The sebum thus accumulated in a follicle then becomes a place of bacterial proliferation. The sebum, rich in triglycerides, is then very quickly degraded into free fatty acids (GLA) by lipases from bacterial germs.
• GLA free fatty acids
• the free fatty acids thus formed oxidize on contact with oxygen in the air, in particular into peroxides, which maintain, or even aggravate, local inflammation.
• the bacterial flora found on the surface or inside the comedones is qualitatively the same: they are yeasts such as Pityrosporum ovale and Pityrosporum orbiculare , staphylococci such as Staphylococus epidermis, Staphylococus capitis or Staphylococus hominis or of propionibacteria such as Propionibacterium acnes.
• Propionibacterium acnes produces lipases which are capable of hydrolyzing the triglycerides of sebum into free fatty acids. Free fatty acids are known to be comedogenic, that is, they can cause follicular hyperkeratosis. Thus, colonization of the follicle by these bacteria determines another source of comedogenic material which, subsequently, will cause the development of micro-comedones. Propionibacterium acnes is also responsible for the accumulation of neutrophilic leukocytes and indirectly of mononuclear lymphocytes, thus leading to the development of inflammation and the activation of an immune response.
• staphylococci colonize both healthy skin and acne lesions, in which they are encountered with a frequency comparable to that of Propionibacterium acnes: 70 to 75% of comedones are colonized, either by staphyloccocci, or by propionibacteria with average 10 4 to 10 5 bacteria per blackhead.
• comedones are open (black dots) or closed (microcysts) does not seem to have a qualitative influence on the proliferation of these two types of bacteria.
• Staphylococus epidermis secretes Pelastase, responsible for lesions of perifollicular elastolysis.
• Pityrosporum such as those previously named, are present in quantities of the same order as staphylococci or as propionibacteria; although aerobic, they can be found in the deep layers of the follicle as well as in closed comedones.
• the Applicant has therefore sought to develop a composition effective against the harmful effects caused by the germs present on the skin and in particular against the harmful effects caused by the enzymes which maintain and develop the inflammatory process.
• compositions comprising as active principles, the association of lipoaminacids with certain natural plant extracts, possessed both a germicidal and antimicrobial activity on the one hand and an anti-microbial activity on the other hand inflammatory by inhibiting lipases, 5-alpha-reductase, responsible in particular for the production of sebum and by inhibiting elastase.
• this activity is the result of the synergy between these two families of active principles.
• composition characterized in that it comprises, as active principle, at least one compound of formula (I):
• topically acceptable salts in which R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, Ri represents a characterizing chain of an amino acid and m is included between 1 and 5, and the constituents of at least one extract and / or at least one tincture of vegetable raw materials rich in tannins (II).
• topically acceptable salt means any salt of the acid of formula (I) which is biologically acceptable for the skin and / or the mucous membranes, ie any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin
• alkaline salts such as the sodium, potassium or lithium salts, alkaline earth salts such as the calcium, magnesium or strontium salts; it can also be metallic salts such as divalent zinc or manganese salts or also trivalent salts of iron, lanthanum, cerium or aluminum.
• the compound of formula (I) present in the composition which is the subject of the present invention may be in the form of free acid or in the form of partially or totally salified.
• characterizing chain used within the framework of the present application designates the non-functional main chain of the fatty acid or of the amino acid considered.
• the characterizing chain will be the chain represented by R.
• the radical R represents in particular a radical comprising from 5 to 22 carbon atoms chosen from the pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl radicals , unicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou strictlynyle.
• a more particular subject of the invention is the composition as described above for which, in formula (I), the R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl and octanoyl radicals (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyle), octadecanoyl (stearyl), eicosanoyle (arachidoyle), docosanoyle (behenoyoy) (behenoyl) , docosènoyl (erucyle), octadécadiènoyl (linolènoyl).
• the R-CO fragment (I) contains from 7 to 22 carbon atoms and represents in particular
• Ri represents in particular the characterizing chain of one of the amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine.
• amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine.
• R 1 represents the characterizing chain of glycine, alanine, glutamic acid or aspartic acid.
• composition according to the invention can contain one or more of these compounds.
• extracts are concentrated preparations, liquids, solids or of intermediate consistency, generally obtained from dried vegetable or animal raw materials.
• Tinctures preparations generally obtained from dried vegetable or animal raw materials.
• extracts or tinctures of vegetable raw materials rich in tannins is meant in particular extracts or tinctures of rathania, tea, cinnamon, willow or witch hazel. These extracts or tinctures are commercially available. Some are registered in the French and / or European pharmacopoeias.
• a more particular subject of the invention is the composition as described above in which the extract or tincture of vegetable raw materials rich in tannins is a cinnamon extract;
• the compounds of formula (I) are generally obtained by acylation of compounds of formula (F)
• proteins of all origins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of vegetable origin, such as, for example , those from soy, sunflower, oats, wheat, corn, barley, potato, lupine, horse bean, sweet almond, silk, or obtained from chorelles (unicellular algae), pink algae or yeast.
• animal origin such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein
• vegetable origin such as, for example , those from soy, sunflower, oats, wheat, corn, barley, potato, lupine, horse bean, sweet almond, silk, or obtained from chorelles (unicellular algae), pink algae or yeast.
• This hydrolysis can be carried out, for example, by heating at a temperature between 60 and 130 ° C. a protein placed in an acidic or alkaline medium.
• This hydrolysis can also be carried out enzymatically with a protease, optionally coupled to an alkaline or acid post-hydrolysis.
• Ri represents several of the characterizing chains of amino acids, depending on the hydrolyzed protein and the degree of hydrolysis.
• Ri represents several of the characterizing chains of amino acids, depending on the hydrolyzed protein and the degree of hydrolysis.
• m is equal to 1 and when the composition comprises a mixture of compounds of formula (I), the average degree of condensation of N-acylated amino acids in this mixture is less than 2.
• the acylation reaction allowing the abovementioned compounds of formula (I) to be obtained can be carried out chemically in an alkaline medium (pH 8 to 10) according to the reaction of
• the currently preferred embodiment for the preparation of the lipoamino acid compounds of formula (I) comprises the following steps: a) Acylation in an alkaline medium (pH 8 to 10) of an excess mixture of amino acids (mixture extemporaneous or obtained by complete hydrolysis of a protein) with a fatty acid (or a mixture of fatty acids), in the form of acid chloride or anhydride.
• the amino acid / acid chloride ratio is preferably 1.05 to 1.30 equivalents.
• the optimal acylation temperature is around 80 ° C but varies from one amino acid to another between 60 and 110 ° C.
• the duration of acylation depends on the equipment used (size, stirring); it is approximately 2 hours for an acylated mass of 500 kg and approximately 5 hours for an acylated mass of 5,000 kg.
• composition according to the invention comprises mineral or organic vehicles commonly used in the manufacture of compositions intended to be formulated in preparations for cosmetic and / or pharmaceutical use; mention may, for example, be made of water, propylene glycol, butylene glycol, hexylene glycol or glycerin.
• composition - according to the invention can also comprise one or more neutralization bases commonly used in the manufacture of cosmetic products; these are for example tris (tri shydroxyamino methane), triethylamine, lysine or methyl glycine.
• neutralization bases commonly used in the manufacture of cosmetic products; these are for example tris (tri shydroxyamino methane), triethylamine, lysine or methyl glycine.
• the composition as described above comprises from 15% to 60% and, more particularly, from 20% to 40% by weight of at least one compound of formula (I) in which the fragment R -CO includes 7 to 12 carbon atoms, or its topically acceptable salts, and from 0.1% to 10% by weight and, more particularly, from 0.5% to 5% by weight of constituents of at least one extract and / or a tincture of vegetable raw materials rich in tannins.
• the extracts can be in the form of fluid extracts, soft or firm extracts or dry extracts.
• the percentages by weight of constituents of the extract or of the dye correspond to the percentages by weight of dry residue, said dry residue being obtained by evaporation of the solvent and drying of said extract or of said dye under operating conditions in which the alteration of the constituents is minimal.
• composition as defined above especially comprises from 20% to 40% by weight of a compound of formula (I) in which Rj. represents a hydrogen atom, the R-CO fragment represents an octanoyl radical and m is equal to 1 and from 0.50% to 5% by weight of constituents of a cinnamon extract.
• cinnamon there is for example cinnamon from Ceylon cinnamon
• composition according to the invention can also comprise from 0.1% to 10% by weight of magnesium and potassium aspartate.
• the composition as described above comprises from 4% to 20% of lauroyl glutamic acid, from 4% to 20% of lauroyl aspartic acid, from 2% to 8% of lauroyl glycine and from 2% to 8% of lauroyl alanine, from 0.5% to 5% by weight of constituents of a cinnamon extract and from 0.5% to 5% of mixed magnesium and potassium aspartate.
• the composition as described above further comprises from 0.1% to 10% by weight of zinc gluconate.
• composition which is the subject of the present invention is prepared by methods known to those skilled in the art. In general, there is introduced with stirring, into a composition comprising at least one compound of formula (I), at least one extract and / or one tincture of vegetable raw materials rich in tannins, in an amount suitable for reaching the desired concentration in the solution final component of said extract and / or said tincture. If necessary, or if desired, said extract and / or said tincture are diluted before mixing.
• the composition according to the invention is used in cosmetics. As the following examples show, the composition according to the invention is unexpectedly characterized by a quadruple activity, anti-elastase, anti-lipase, anti-bacterial and anti-5- ⁇ -reductase.
• composition according to the invention can be used as a complementary treatment to medical treatment of acne.
• composition according to the invention is also used for disinfecting the skin and mucous membranes. In this case it can be a simple act of personal hygiene or a complementary treatment to the medical treatment of an infection.
• composition according to the invention is also used in the treatment of the scalp, in particular as an anti-dandruff active.
• the composition as described above is used at different concentrations and in a formulation suitable for this use; such cosmetic compositions are usually in the form of aqueous solutions, dilute alcoholic solutions, or single or multiple emulsions, such as water in oil (W / O), oil in water (HE) or water in oil in emulsion. water (W / O / W).
• aqueous solutions such as water in oil (W / O), oil in water (HE) or water in oil in emulsion. water (W / O / W).
• HE oil in water
• W / O / W water in oil in emulsion. water (W / O / W).
• cosmetic formulation mention may be made of creams, milks, lotions, wipes, shower gels, soaps, liquid soaps, probes, intimate hygiene products or shampoos.
• the invention therefore also relates to a cosmetic formulation capable of being obtained by dilution from 1/10 to 1/20000 of the composition as described above, in one or more cosmetically acceptable excipients, and in particular a cosmetic formulation under form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than lPa.s. comprising as emulsifier a self-emulsifiable composition based on fatty alcohols.
• compositions include MONTANOV 68 ® marketed by Seppic.
• dilution used in the foregoing includes, in its broadest sense, all the steps making it possible to pass from the composition as defined above to the cosmetic formulation intended to be marketed.
• the cosmetic formulation is a lotion for treating skin prone to acne.
• the cosmetic formulation is a foaming formula or an anti-dandruff shampoo.
• the invention particularly relates to a cosmetic formulation
• a cosmetic formulation comprising, as active principle, from 0.001% to 6% by weight of at least one compound of formula (I) and from 0.00005%) to 1% by weight of constituents d '' at least one extract (H) and / or at least one tincture of vegetable raw materials rich in tannins chosen from cinnamon, rathania, tea, willow or witch hazel extracts. and if desired up to 1% zinc gluconate.
• the invention particularly relates to a cosmetic formulation comprising as active principle from 0.5% to 2% by weight of a compound of formula (I) ⁇ CH 3 - (CH 2 ) 6 -CO-NH-CH 2 -COOH (I) ⁇ from 0.05% to 0.2% by weight of constituents of an extract of vegetable raw material chosen from cinnamon, rathania, tea, willow or witch hazel extracts. and if desired from 0.025% to 0.2% zinc gluconate, and a cosmetic formulation comprising as active ingredient from 0.001% to
• Lipacide ® C8G marketed by SEPPIC, the active ingredient of which is octanoyl glycine
• Tris Tris hydroxymethyl aminomethane or tromethamine: sufficient quantity to obtain a pH of approximately 5.0 to 6.0;
• composition A containing approximately:
• composition B a) To a mixture consisting of 27.4 kg of L-aspartic acid, 35.3 kg of L-glutamic acid, 7.9 kg of L-alanine, 7.9 kg of glycine and 112 , 5 kg of water are added 96 kg of potassium hydroxide solution (50%) in order to obtain a pH of approximately 10. A co-solvent facilitating subsequent acylation can also be added to this mixture.
• the temperature of the mixture thus obtained is brought to 80 ° C., then 110 kg of lauroyl chloride are poured simultaneously with stirring. The reaction lasts 2 hours.
• the “acylated mass” of 465 kg thus obtained comprises a mixture of lauroylated amino acids, free amino acids and lauric acid, these compounds being in the form of potassium salt.
• the mixture of compounds with a lipoamino acid structure can be extracted from this acylated mass in a very acid medium (pH of approximately 1) and under hot conditions (90 ° C.) for example by implementing the following protocol: - adjustment of the pH to a value of 1 by adding an appropriate quantity (approximately
• Lauroyl glycine acid 6%. 8% lauroyl alanine acid as well as reaction residues, in particular:. Lauric acid 15%. Water 10%
• Tris Tris hydroxymethyl aminomethane or tromethamine: sufficient quantity to obtain a pH of approximately 5.0 to 6.0; . Sepicide® HB: 2 kg; . Water: 200 kg. . Mixed potassium and magnesium aspartate: 5 kg;
• composition B containing approximately: - 25% by weight of the mixture of products of formula (I)
• EHL human leukocyte elastase
• This enzyme is in particular capable of degrading many macromolecules such as fibrous elastin, certain types of collagen, proteoglycans, glycoproteins.
• human leukocyte elastase is one of the links in the chain of reactions accompanying an inflammation phenomenon.
• the blocking of this enzyme by an anti-elastase effect therefore makes it possible to prevent the degradation of the aforementioned molecules and therefore to inhibit the process of inflammation.
• the anti-elastatic properties of a given product can be demonstrated by an in vitro test, carried out with a spectrophotometer, using a support substance capable of degrading by coloring, in contact with human leukocyte elastase.
• Such a substance can be for example N-methoxysuccinyl-alanine-proline-valine-para-nitroanilide, normally colorless substance which releases, by hydrolysis by human leukocyte elastase, a colored product, para-nitroaniline, whose kinetics d appearance can be followed by spectrophotometry at 410 nm.
• the reaction is carried out in a spectrophotometer thermostatically controlled at 25 ° C., having a sample changer. All the kinetics are carried out at least three times, the mean and the standard deviation then being calculated for the three values obtained.
• the presence of a molecule with anti-elastatic activity results in a limitation of the appearance of the colored product and the anti-elastatic effect can then be calculated relative to a control curve obtained in the absence of said molecule.
• compositions A and H are diluted in water to get Ai compositions, A. , A 3 , Hi, H 2 and H 3 having the following active ingredient concentrations:
• the elastase inhibition percentages are as follows
• Enzymes of the 5-alpha-reductase type transform testosterone into 5-dehydrotestosterone (5-HT).
• the activity of 5-alpha-reductase is important on the skin, in the perineal areas. It is present in the sebaceous glands and the apocrine glands (sweat), in keratinocytes and fibroblasts.
• the carbon-14 testosterone is incubated in the presence of microsomes of human skin, prepared according to the method described by VOIGT et al. (1970) J. Biol. Chem., 245, 5594-5599, in the absence and in the presence of the test compound or in the presence of finasteride, used as a reference inhibitor molecule.
• a known quantity of triglycerides (“Lipase Substrate” sold by the company SIGMA), a known quantity of lipase (“Enzyme Control 2E” sold by the company SIGMA) are brought into contact with the composition to be tested. After an incubation period of three hours at 37 ° C., the enzymatic reaction is stopped and the free fatty acids formed are assayed by titration with 0.05 M sodium hydroxide. The results are expressed as a percentage of inhibition of the enzyme by the composition considered by comparing it with a control test. b results
• composition A was diluted 1/15 in water to obtain composition A 4 having the following active ingredient concentrations:. octanoyl glycine: 1.6%. cinnamon extract: 0.19%. While 1.6% octanoyl glycine leads to a 44% inhibition percentage
• composition A4 leads to a percentage inhibition of 71%, while the simple addition of the effects would give 60% inhibition.
• Example 3 Purifying cleanser for oily skin prone to acne FORMULA
• Composition A 2.00% CAPIGEL ® 98 2.00%
• Composition A 2 to 4%
• Composition A 2 to 4%
• LANOL 99 is isononyl isononanoate marketed by the company SEPPIC
• Composition A 2% > magnesium and potassium aspartate 0.002% to 0.5%

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• 1997
  • 1997-06-25 FR FR9707943A patent/FR2765109B1/fr not_active Expired - Lifetime
• 1998
  • 1998-06-23 WO PCT/FR1998/001313 patent/WO1999000109A1/fr not_active Application Discontinuation
  • 1998-06-23 JP JP50531999A patent/JP2002507207A/ja active Pending
  • 1998-06-23 EP EP98933685A patent/EP0998264A1/fr not_active Withdrawn
• 2001
  • 2001-01-05 US US09/754,209 patent/US20010002257A1/en not_active Abandoned

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