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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
• • 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
  • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
  • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
  • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
  • A23L33/12—Fatty acids or derivatives thereof
• • 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
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
  • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
  • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
  • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
  • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
  • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
  • A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
  • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
  • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
  • A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
• • 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
• • 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
  • A61K8/738—Cyclodextrins
• • 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
  • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
• • 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
  • A61P17/06—Antipsoriatics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P19/00—Drugs for skeletal disorders
  • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
  • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P9/00—Drugs for disorders of the cardiovascular system
• • 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
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B82—NANOTECHNOLOGY
  • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
  • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
  • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
  • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
  • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
  • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
• • 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
  • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

• the invention relates to solubilization
• Polyunsaturated fatty acids such as arachidonic or eicosatetraenoic (AA) eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids are long chain polyunsaturated fatty acids
• DHA Docosahexaenoic acid
• Triglycerides RR 2 , R 3 represent the fatty acid hydrocarbon group such as EPA, DHA or the like. These n-3 series polyunsaturated fatty acids (PUFA) have very interesting properties in the prevention of certain inflammatory pathologies (psoriasis, arthritis) and cardiovascular diseases.
• PUFA polyunsaturated fatty acids
• n-3 PUFAs exert their beneficial effect by intervening at two levels:
• the period of perinatal development is special in that it corresponds to the most active phase of incorporation of long chain PUFAs (22: 6 n-3; i.e. 22 carbon atoms, 6 ethylenic unsaturations , the first being on carbon n-3) in the structural lipids of the central nervous system, but also the most sensitive to dietary intake of PUFAs.
• this period of rapid growth extends from the last three months of fetal life until the age of two. During the first year, the newborn's brain will take two grams per day mainly due to the phenomenon of myelinization. This implies that dietary intake of PUFA must be quantitatively and qualitatively correct.
• document FR-A-2 547 829 [1] provides a stable composition containing compounds of unsaturated fatty acids and a stabilizing organic compound corresponding to the formula:
• R 1 and R 2 represent Ls respectively fatty acid residues while R represents H 3 or
• Document EP-A-0 470 452 [3] also describes the production of a product comprising ⁇ -cyclodextrin and an oleaginous substance containing EPA or DHA, by precipitation from a solution.
• the present invention specifically relates to formulations in the form of aqueous solutions containing in solution at least one oleaginous substance belonging to the group of polyunsaturated fatty acids and their derivatives (salts, esters and triglycerides), which are suitable for such incorporation.
• the subject of the invention is an aqueous solution comprising at least one oleaginous substance chosen from polyunsaturated fatty acids and the salts, esters and triglycerides of polyunsaturated fatty acids, in which the said substance (s) are in the form of an inclusion complex in ⁇ -cyclodextrin.
• natural cyclodextrins are cyclic oligosaccharides consisting of D-glucopyranosyl units linked in ⁇ -1,4.
• ⁇ -cyclodextrin which is a natural cyclodextrin, comprises eight D-glycopyranosyl units.
• the oleaginous substances used in the invention can be of different types and from various origins, for example from fish or plants.
• the polyunsaturated fatty acids AA, EPA and DHA mentioned above are used, in particular in the form of triglycerides. It is possible to use a mixture of one or more of these acids with other saturated or unsaturated fatty acids, for example a fish oil.
• the solution comprises several oleaginous substances, these being constituted by a fish oil.
• the fish oil can in particular be a sardine oil or a tuna oil.
• Such an oil comprises unsaturated fatty acids having from 1 to 6 ethylenic unsaturations as well as fatty acids without ethylenic unsaturation.
• the invention also relates to a process for the preparation of an aqueous solution comprising at least one oleaginous substance chosen from polyunsaturated fatty acids and the salts, esters and triglycerides of polyunsaturated fatty acids.
• ⁇ -cyclodextrin is used to dissolve these substances and the process comprises the following steps: a) dissolving ⁇ -cyclodextrin in water, b) adding to the solution obtained in a) oleaginous substance (s) to be dissolved, and c) separating the precipitated complex of ⁇ -cyclodextrin and of oleaginous substance (s)
• the precipitated complex can also be recovered, dried, then put back into an aqueous solution.
• the complex obtained can be recovered and dried in the supernatant and then put back into an aqueous solution.
• the method may further comprise a step of recovering and drying at least one of the complexes obtained in step c) followed by the re-solution in aqueous solution of the dried complex (s). .
• one begins by dissolving the ⁇ -cyclodextrin in water with stirring using an amount of ⁇ -cyclodextrin which can go to the saturation of the. solution, i.e. 230 g / 1.
• step b) which follows, the oleaginous substance (s) are added in an amount such that it corresponds to a slight excess relative to the amount of ⁇ -cyclodextrin necessary to form the equimolar complex. It is also subjected to agitation.
• step c) the supernatant is separated from the precipitate, for example by centrifugation.
• oleaginous substances in ⁇ -cyclodextrin overcomes the following problems: the polymerization of polyunsaturated fatty acids, the migration of cis double bonds in trans, and peroxidation.
• Such aqueous formulations can be used to include these polyunsaturated fatty acids and / or their triglycerides, salts and esters in food compositions and in cosmetic compositions.
• the subject of the invention is also pharmaceutical, food or cosmetic compositions comprising an aqueous solution of at least one oleaginous substance chosen from polyunsaturated fatty acids and the salts, esters and triglycerides of polyunsaturated fatty acids, in which the (said) substance (s) are in the form of an inclusion complex in ⁇ -cyclodextrin.
• FIG. 1 is the spectrum obtained by nuclear magnetic resonance of the proton, in pyridine, of the ⁇ -cyclodextrin-fish oil complex, precipitated in the example given below.
• the following example illustrates the solubilization of fish oil using ⁇ -cyclodextrin.
• 9.9931 g of ⁇ -cyclodextrin and 87 ml of water are introduced into a container to obtain a solution of 114.86 g / 1 of ⁇ -cyclodextrin, which corresponds substantially to half of the maximum solubility (230 g / 1) ⁇ -cyclodextrin.
• the mixture is stirred on a turntable at 300 revolutions / minute until the ⁇ -cyclodextrin is completely dissolved, which is obtained in a few minutes.
• TGL (noted TGL in the figure) which are unambiguously attributed to triglycerides from fish oil.
• the amount of triglycerides included in the supernatant is quite large and the amount included in the precipitate is even greater.
• the solubility of the lyophilized complexes is then examined by re-solution in water. To this end, the quantity of water necessary to obtain the dissolution of 0.0846 g of lyophilized complex is added; this is 47.08 ml and it leads to an opalescent solution, the complex concentration of which is 1.79 g / l.
• the lyophilized complex obtained from the supernatant and the lyophilized complex obtained from the precipitate are dissolved in a minimum volume of dimethylformamide DMF, which denatures the complex by separating the two species which constitute it. Having taken a mass of 1 g of complex, a volume of DMF of 4 ml is necessary to dissolve everything. About 60 ml of ether are added to each sample because the triglycerides are soluble therein but not the cyclodextrin which precipitates instantly.
• the fraction of the triglycerides which have been included in the ⁇ -cyclodextrin is thus recovered.
• the fluid obtained is oily in appearance.
• the mass of triglycerides recovered is 0.1178 g per 1 g of the complex from the supernatant and 0.2164 g for 1 g of the complex from the precipitate.
• the samples are stored under argon to avoid any degradation in air, before their analysis by gas chromatography, which will give their characteristic fatty acid profile.
• fatty acids are identified by their number of carbon atoms, followed by the number of ethylenic unsaturations and the location in the chain of the first unsaturation.
• EPA corresponds to 20: 5 n-3.

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• 1999
  • 1999-03-09 FR FR9902881A patent/FR2790758A1/fr active Pending
• 2000
  • 2000-03-07 EP EP00909441A patent/EP1165620A1/fr not_active Withdrawn
  • 2000-03-07 JP JP2000604072A patent/JP2002539138A/ja not_active Withdrawn
  • 2000-03-07 CA CA002366719A patent/CA2366719A1/fr not_active Abandoned
  • 2000-03-07 WO PCT/FR2000/000560 patent/WO2000053637A1/fr not_active Application Discontinuation
• 2001
  • 2001-09-06 NO NO20014341A patent/NO20014341L/no unknown

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