EP0930937A1 - Aus hydrogel von vernetzten polysacchariden hergestellte mikrokapsel, die zellen oder moleküle von biologischem interesse enthalten - Google Patents

Aus hydrogel von vernetzten polysacchariden hergestellte mikrokapsel, die zellen oder moleküle von biologischem interesse enthalten

Info

Publication number
EP0930937A1
EP0930937A1 EP98935081A EP98935081A EP0930937A1 EP 0930937 A1 EP0930937 A1 EP 0930937A1 EP 98935081 A EP98935081 A EP 98935081A EP 98935081 A EP98935081 A EP 98935081A EP 0930937 A1 EP0930937 A1 EP 0930937A1
Authority
EP
European Patent Office
Prior art keywords
encapsulated
stirring
capsules
cells
dispersion
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Withdrawn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
EP98935081A
Other languages
English (en)
French (fr)
Inventor
Karim Ioualalen
Rosanne Raynal
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP0930937A1 publication Critical patent/EP0930937A1/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Withdrawn legal-status Critical Current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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds 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
    • A61K8/67—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
    • 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
    • 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
    • A61K8/678—Tocopherol, i.e. vitamin E
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • the different nfilff ⁇ technologies all follow the same scheme comprising two stages. The first consists in dispersing the product or the preparation to be encapsulated into fine droplets. The second sees the realization of the encapsulation proper by the solidification of droplets either on the surface or in the mass.
  • the dispersion is a »ft ⁇ key to the success of a good encapsulation because it conditions at the same time the effectiveness of encapsula ⁇ on, the size of the balls, the homogeneity of size and the shape.
  • Extrusion consists in dispersing the solution to be encapsulated by dropping it drop by drop in a medium where the gelification of the drops or the formation of a surface membrane is carried out (Levy and Poncelet, 1994, Biofutur, Mars, 16-21) .
  • the drip is obtained using a needle.
  • this technique can be modulated by the application of a coaxial air current of a potential difference or a vibration. If it is thus possible to better control the size range, it It seems impossible to envisage industrial production for capsules smaller than 500 microns at a time for reasons of yields and size dispersion.
  • This step leads to the - synthesis of the microcapsule containing the structure to be encapsulated, by the establishment of a membrane of varied nature more or less resistant or by complete solidification forming a solid ball by polymerization or gelation.
  • the capsule must be biocompatible, must not modify physiological balances, must not induce side effects, must be biodegradable after having fulfilled its role and above all be stable in its conditions of use. In addition, it must have a high encapsulation capacity and allow effective modulation of the properties of permeability to nutrients, to the compounds produced or encapsulated, as well as to the various compounds or elements of the medium of use or implantation of the capsules. Finally, the encapsulation technique must be easily industrializable.
  • the capsule can therefore have the following criteria:
  • the compound must be compatible with the stability of the compounds to be encapsulated
  • interfacial polymerization To overcome the low chemical stability of the capsules obtained by ionic coating, other techniques have been developed, called interfacial polymerization. All these techniques are based on the same principle.
  • An aqueous suspension of proteins or polymers containing the product to be encapsulated is dispersed in an organic phase with which the crosslinking agent is added, generally a polychloride of acid which reacts with the amino groups at the interface, to give a membrane.
  • nylon type FR 2 642329A1
  • Macroencapsulation on hollow fiber provides very good results in terms of cell survival and in vivo stability (Aebischer et al, 1991, Exp. Neurol., 111, 269).
  • these techniques have certain disadvantages such as:
  • hydrogels from polymers used in hollow fibers such as acrylonitrile and sodium methaUysulfonate (FR 2696755A1), or ethylene gh / col muttiacrylate photopolymers (WO 9631199), or potyacrylamides.
  • polymers used in hollow fibers such as acrylonitrile and sodium methaUysulfonate (FR 2696755A1), or ethylene gh / col muttiacrylate photopolymers (WO 9631199), or potyacrylamides.
  • the capsule is biocompatible and does not cause an organism response in the event that it is implanted
  • the size is controllable - the porosity can be modulated
  • microcapsules according to the invention are characterized in that they consist of a hydrogel prepared by covalent crosslinking of biocompatible polymers preferably chosen from polysaccharides.
  • the present invention relates to a new type of microcapsule useful in particular for the transport of compounds for biological use.
  • microcapsules have a very important stability, a defined size which can be modulated according to the applications. They are capable of encapsulating various synthetic, semi-synthetic, recombinant or natural molecules, bacterial cells, yeasts, mammalian cells, oily compounds, flavors and powders. These microcapsules can be used to allow or increase solubility and aqueous dispersibility, to provide protection against responses of the immune system during implants, to facilitate the handling and recovery of ferments during vinification and fermentation processes in general.
  • microcapsules can also be used to obtain a modulation of the modes of release of the molecules over time, to improve the physicochemical stability over time of sensitive molecules, to protect the encapsulated compounds against mechanical and thermal aggressions, to ensure transport molecules within complex eukaryotic or prokaryotic biological systems intended to ensure chemical, photochemical, enzymatic immunological reactions for pharmaceutical, cosmetological, diagnostic, study and research, fermentation applications.
  • the present invention relates to a new type of biocompatible polymer matrix intended for the encapsulation of various compounds and characterized in that the crosslinking phase of the polymer can be modulated to allow the internal incorporation of water-soluble or hydrophobic molecules. This homogeneous encapsulation is introduced after the first step of crosslinking the polymer and before complete gelation.
  • the compound to be encapsulated is added while maintaining agitation
  • the reaction medium is then dispersed in a hydr ⁇ phobic organic phase until complete polymerization of the capsules
  • Microcapsules are thus obtained after washing, allowing re-encapsulation of numerous compounds.
  • the reaction medium containing the encapsulation product is not dispersed in the hydrophobic organic phase. It is left to stand until solidified in the form of a gel.
  • the microcapsules containing the product to be encapsulated are then obtained by mechanical grinding.
  • the microcapsules obtained are not spherical but this technique makes it possible to obtain very small sizes of microcapsules without the use of surfactants.
  • this technique allows the incorporation of these cells while maintaining excellent viability and functionality, both for bacterial cells, yeasts and mammalian cells, for example glands adrenal or PC12 dopaminergic lines.
  • the present invention relates to a microcapsule characterized in that it comprises in order:
  • hydrogel matrix based on carbohydrates or crosslinked polyols, hydrophilic, non-liquid and biocompatible - inclusions of the compounds to be encapsulated which are dispersed throughout the matrix
  • the matrix can be prepared by various methods well known to those skilled in the art.
  • it is a polysaccharide, preferably biodegradable, linear or branched, for example starch and derivatives, ceUulose, dextran, polysaccharides derived naturally by ionic functions, for example chitosan, hyaluronic acids, alginates, carrageenans, hydrogel or porysaccharide matrix, is obtained by crosslinking, by methods well known to those skilled in the art.
  • Crosslinking methods can be carried out by the use of bifunctional agents capable react with the hydroxyl groups of polysaccharides such as epichlorohydrin, epibromohydrin or difunctionals such as bis-epoxides, ctialdehydes, dicarides of dicarboxylic acids, diisothiocyanates, mixed anhydrides of dicarboxylic acids.
  • the microcapsules are formed during the last step of the process.
  • a first variant of this step consists in mechanically grinding large blocks of matrices obtained by mass polymerization.
  • the second consists in resuscitating the matrix in the form of capsules by the technique of polymerization in dispersion in a liquid immiscible with the reaction phase.
  • the use of surfactants such as Tween or Span is dependent on the size sought.
  • the dispersion in the hydrophobic phase is carried out by stirring in a reactor using a blade or by stirring on a stirring table with circular movement.
  • the physico-chemical and mechanical stability as well as the porosity of the microcapsule thus prepared are a function of the crosslinking operating conditions such as the initial dilution of the polymer and / or the amount of crosslinking agent.
  • These microcapsules can be used for the administration of molecules by oral, per lingual, nasal, vaginal, rectal, cutaneous, ocular but also pulmonary and parenteral routes. They can also be used for topical applications of keratinous tissues such as dander.
  • Hydrophobic compounds such as mineral oils, for example paraffin or silicone, organic oils, for example, olive, calendula, sweet almond, salmon, cod liver, evening primrose, essential oils, flavorings , dyes, mineral powders such as talc, titanium dioxide, zinc oxide, silicates, foundations for insoluble dyes and pigments, oily dispersions of plant extracts, vitamins alone or in oily dispersion , cells for example hepatocytes, streams of Langerhans, pancreatic cells, adrenal meduocells, PC12 dopaminergic cell cells, genetically modified cells, yeasts for example boulardi saccharomyces, saccharomyces cerevisiae, bacteria by example leuconostoc oenos and molecules with therapeutic activity.
  • mineral oils for example paraffin or silicone
  • organic oils for example, olive, calendula, sweet almond, salmon, cod liver, evening primrose, essential oils, flavorings , dyes, mineral powders such as talc, titanium dioxide, zinc oxide, silicates
  • - peptides and their derivatives glucagon, somatostatin, calcitonin, interferon and interleukins, LHRH, rerythropoietin, bradykinin antagonists, polypeptides as well as recombinants from biotechnology
  • oligonucleotide analogs and reverse transcriptase inhibitors in particular oligonucleotide analogs and reverse transcriptase inhibitors
  • vasodilators diuretics and antidiuretics - prostaglandins
  • Example 1 Preparation of microcapsules of silicone hula 400 microns
  • Example 2 Preparation of 40 micron vitamin A propionate microcapsules
  • Example 3 Preparation of microcapsules of vitamin E / vitamin C / sweet almond oil mixture
  • Example 4 Preparation of microcapsules for mixing titanium dioxide powders and magnesium siUcate
  • Example 5 Preparation of microcapsules for mixing titanium dioxide and zinc oxide powders
  • Example 6 Preparation of microcapsules of rose essential oil of 2000 microns
  • the agitation is kept dispersed by slow agitation using an anchor-type blade at a speed between 30 and 50 revolutions / min. After 3 hours of stirring, the capsules are recovered by decantation and then taken up in 16 liters of water and neutralized with 2N HCl. The microcapsules are then washed 3 times by decantation with 8 liters of water. We obtain essential oil capsules of 2000 microns
  • Example 7 Preparation of microcapsules of essential oil of rose of 40 microns
  • the agitation is kept dispersed by slow agitation using an anchor-type blade at a speed between 30 and 50 revolutions min. After 3 hours of stirring, the capsules are recovered by decantation and then taken up in 16 others of water and neutralized with 2N HCl. The microcapsules are then washed 3 times by decantation with 8 liters of water. 40 micron essential oil capsules are obtained.
  • Example 9 Preparation of encapsulated Boulardii saccharomyces yeasts
  • Example 10 Preparation of encapsulated Leuconostoc Oenos bacteria
  • Example 11 Preparation of large-pore capsules containing leuconostoc oenos

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nutrition Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
EP98935081A 1997-07-03 1998-07-02 Aus hydrogel von vernetzten polysacchariden hergestellte mikrokapsel, die zellen oder moleküle von biologischem interesse enthalten Withdrawn EP0930937A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9708402 1997-07-03
FR9708402A FR2765496B1 (fr) 1997-07-03 1997-07-03 Microbilles appelees capsules a coeur polymerique capables de transporter des molecules, des principes actifs et/ou des cellules.
PCT/FR1998/001414 WO1999001213A1 (fr) 1997-07-03 1998-07-02 Microbilles preparees a partir d'hydrogel de polysaccharide reticule pouvant contenir des molecules d'interet biologique ou des cellules

Publications (1)

Publication Number Publication Date
EP0930937A1 true EP0930937A1 (de) 1999-07-28

Family

ID=9508796

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98935081A Withdrawn EP0930937A1 (de) 1997-07-03 1998-07-02 Aus hydrogel von vernetzten polysacchariden hergestellte mikrokapsel, die zellen oder moleküle von biologischem interesse enthalten

Country Status (3)

Country Link
EP (1) EP0930937A1 (de)
FR (1) FR2765496B1 (de)
WO (1) WO1999001213A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2004243536B2 (en) * 2003-05-28 2007-10-11 Unilever Plc Satiety enhancing food products
FR2862980B1 (fr) * 2003-11-28 2006-03-03 Biopredic Internat Moyens pour le transport et la conservation de cellules ou tissus vivants
FR2913884A1 (fr) * 2007-03-21 2008-09-26 Oralance Pharma Sa Systeme galenique hydrophobe non ionisable

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3615043A1 (de) * 1986-05-03 1987-11-05 Hoechst Ag Verfahren zur verkapselung von biologisch aktivem material
FR2677249B1 (fr) * 1991-06-04 1995-03-17 Biovecteurs As Vecteur particulaire biodegradable et procede de synthese.
FR2688422A1 (fr) * 1992-03-11 1993-09-17 Coletica Microcapsules a parois en polysaccharides contenant des fonctions alcools primaires, et compositions en contenant.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9901213A1 *

Also Published As

Publication number Publication date
WO1999001213A9 (fr) 1999-04-15
FR2765496B1 (fr) 1999-09-24
FR2765496A1 (fr) 1999-01-08
WO1999001213A1 (fr) 1999-01-14

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