EP2003990A2 - Kombination einer öligen substanz mit einer mischung von mindestens zwei cyclodextrinen - Google Patents

Kombination einer öligen substanz mit einer mischung von mindestens zwei cyclodextrinen

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Publication number
EP2003990A2
EP2003990A2 EP07731799A EP07731799A EP2003990A2 EP 2003990 A2 EP2003990 A2 EP 2003990A2 EP 07731799 A EP07731799 A EP 07731799A EP 07731799 A EP07731799 A EP 07731799A EP 2003990 A2 EP2003990 A2 EP 2003990A2
Authority
EP
European Patent Office
Prior art keywords
cyclodextrin
weight
equal
mixture
cyclodextrins
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Withdrawn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
EP07731799A
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English (en)
French (fr)
Inventor
Mohamed Skiba
Malika Lahiani
Frédéric BOUNOURE
Pierre Dechelotte
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IN CYCLO
Original Assignee
IN CYCLO
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Publication date
Application filed by IN CYCLO filed Critical IN CYCLO
Publication of EP2003990A2 publication Critical patent/EP2003990A2/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
    • 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
    • A61K31/201—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 one or two double bonds, e.g. oleic, linoleic acids
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A61K31/724—Cyclodextrins
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/16—Cyclodextrin; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

Definitions

  • the present invention relates to the field of cosmetic, pharmaceutical, food, nutritional, nutraceutical and veterinary compositions.
  • the invention relates to inclusion complexes of oleaginous substance (s), in particular of fatty acids, and a mixture of cyclodextrins, compositions comprising them and a process for the preparation of such complexes.
  • s oleaginous substance
  • the invention also relates to compositions comprising at least two cyclodextrins and at least one oleaginous substance.
  • Oleaginous substances and in particular unsaturated fatty acids, can play a very important role in the body. For example, they may have an influence in: - cellular activity and humoral immunity,
  • the organism in particular human, may have deficiencies in terms of unsaturated fatty acids, it may be useful to provide it.
  • these fatty acids may have a specific taste and / or odor.
  • Patent FR 2 547 829 proposes a composition containing unsaturated fatty acid compounds and a type of cyclodextrin whose role is to stabilize fatty acids and reduce the odor and bitterness associated with polyunsaturated fatty acids.
  • EP 0 470 452 discloses a product comprising gamma-cyclodextrin for complexing an oleaginous substance containing a mixture EPA and DHA, polyunsaturated fatty acids of different structures.
  • US 5189149 and US 6878696 disclose a method of encapsulating polyunsaturated fatty acid-rich animal or plant oils and their derivatives using a type of cyclodextrin. However, the protection of oils composed of a mixture of different polyunsaturated fatty acids may be insufficient.
  • Patent FR 2,850,040 for its part describes an acid complex with alpha-cyclodextrin alone.
  • inclusion complexes described above may have insufficient stability, or insufficiently mask the taste and / or odor of certain types of oleaginous substances, such as fatty acids.
  • the subject of the invention is a mixture of inclusion complexes comprising, or consisting of:
  • cyclodextrins chosen from alpha-, beta- and gamma-cyclodextrin and / or their derivatives, in particular their modified derivatives on the primary and / or secondary hydroxyl groups, and
  • At least one oleaginous substance chosen especially from oils of animal, plant and synthetic origin.
  • the mixture of complexes according to the invention may comprise an oleaginous substance content greater than or equal to 40% by weight, in particular greater than or equal to 50% by weight, in particular greater than or equal to 60% by weight, or even greater than or equal to 70% by weight relative to the total weight of complexes.
  • the oleaginous substance may especially comprise or consist of at least one fatty acid, especially saturated and / or unsaturated fatty acid, a corresponding ester or triglyceride, in particular a mono- or poly-unsaturated fatty acid.
  • fatty acids is intended to mean carboxylic acids comprising from 6 to 50 carbon atoms, in particular from 10 to 30 carbon atoms, and in particular from 12 to 22 carbon atoms.
  • the name of this class of compounds recalls their natural origin, the fatty substances, which are esters of long-chain carboxylic acids, in particular fats of animal or vegetable origin which can be triesters of glycerol.
  • unsaturated fatty acids means monounsaturated or polyunsaturated fatty acids.
  • the fatty acid may come from a vegetable, animal or synthetic oil or a mixture thereof, in particular from fish oil, linseed oil and / or camelina oil, and in particular the fatty acid may be from an oil selected from the group consisting of:
  • linseed oil which may comprise an alpha-linolenic acid content of about 56%
  • nut, rapeseed and soybean oil which may comprise an alpha-linolenic acid content ranging from 8% to 14%
  • - blackcurrant seed oil which may comprise about 12 to 24% linoleic acid, 15 to 19% gamma-linolenic acid but also 30 to 40% alpha-linolenic acid and 3 to 4 % of stearidonic acid (omega 3),
  • camelina oil which may contain 12 to 24% linoleic acid, but also 30 to 40% alpha-linolenic acid, 10 to 24% oleic acid and 500 to 800 mg / kg of tocopherol and tocorienol,
  • - Corn, sunflower and grapeseed oils which can be very rich, especially in linoleic acid, and - fish oils, which may contain large proportions of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • the oleaginous substance may comprise an unsaturated fatty acid content greater than or equal to 30% by weight, in particular greater than or equal to 50% by weight, in particular greater than or equal to 70% by particular weight, more particularly greater than or equal to 90% by weight.
  • % by weight or even greater than or equal to 95% by weight, relative to the total weight of oleaginous substance.
  • Unsaturated fatty acids include fatty acids selected from the group consisting of:
  • docosene-13-oic acid 22: 1, omega-9
  • the oleaginous substance may comprise a content of omega fatty acid (s), in particular omega-3, omega-6 and / or omega-9, greater than or equal to 50% by weight, in particular greater than or equal to 75% by weight. weight, in particular greater than or equal to 90% weight, or even greater than or equal to 99% by weight relative to the total weight of oleaginous substance.
  • omega fatty acid s
  • omega-3, omega-6 and / or omega-9 greater than or equal to 50% by weight, in particular greater than or equal to 75% by weight.
  • weight in particular greater than or equal to 90% weight, or even greater than or equal to 99% by weight relative to the total weight of oleaginous substance.
  • Natural cyclodextrins (alpha, beta and gamma) are most often derived from the bioconversion of maize starch by a bacterial enzyme, cycloglycosyltransferase (CGTase).
  • cyclic oligosaccharides having respectively, for alpha, beta and gamma: 6, 7 or 8 alpha-D-glucopyranose units, the bonds connecting these units are of the alpha- (1 4) glucosidic type.
  • Aqueous solubility (g / 100 14.5 1.85 23.2 mL, 25 ° C)
  • the cyclodextrin derivatives can be obtained by substitution of primary or secondary hydroxyl groups, for example by alkyl radicals, in particular comprising from 1 to 12 carbon atoms, for example methyl (-CH 3 ) or propyl (-C 3 H 9 ) . These substitutions may make it possible to increase the lipophilicity of the cavity and increase the aqueous solubility of the cyclodextrin.
  • the structure of cyclodextrins can be represented as a conical trunk with a hydrophobic cavity.
  • the exterior of the cyclodextrin molecule is generally hydrophilic, they are pseudo-amphiphilic molecules.
  • This pseudo-amphiphilic structure can allow the formation of inclusion complexes.
  • the inclusion complex may have physicochemical properties independent of the guest molecule and thus improve the apparent solubility in water of this molecule.
  • This improvement in solubility may allow, for example, an improvement in the bioavailability of the molecule, in particular by improving the dissolution rate of the molecule.
  • the mixture of complexes according to the invention comprises at least two different cyclodextrins, which may each be present in a content greater than or equal to 1% by weight, especially at a content greater than or equal to 10% by weight, or even a higher content. or equal to 20% by weight, or even a content greater than or equal to 30% relative to the total weight of cyclodextrin.
  • the mixture of complexes comprises two cyclodextrins, in particular: an alpha-cyclodextrin / beta-cyclodextrin mixture, in particular in a ratio ranging from 10/1 to 1/10, or even from 4/1 to 1/4,
  • an alpha-cyclodextrin / gamma-cyclodextrin mixture in particular in a ratio ranging from 10/1 to 1/10, or even from 4/1 to 1/4, or a beta-cyclodextrin / gamma-cyclodextrin mixture, in particular in a ratio ranging from 10/1 to 1/10, or even from 4/1 to 1/4.
  • the mixture of complexes comprises three cyclodextrins, in particular an alpha-cyclodextrin / beta-cyclodextrin / gamma-cyclodextrin mixture, in particular with an alpha-cyclodextrin / beta-cyclodextrin ratio ranging from 10/1 to 1/10, or even from 4/1 to 1/4, with an alpha-cyclodextrin / gamma-cyclodextrin ratio ranging from 10/1 to 1/10, or even from 4/1 to 1/4, and / or with a beta-cyclodextrin / gamma-cyclodextrin ratio ranging from 10/1 to 1/10, or even 4/1 to 1/4.
  • the subject of the invention is also a composition
  • a composition comprising or consisting of a mixture of at least two cyclodextrins chosen from alpha-, beta- and gamma-cyclodextrin and / or their derivatives, and at least one oleaginous substance.
  • This composition may have an oleaginous substance / cyclodextrin weight ratio greater than or equal to 0.5, in particular greater than or equal to 1, or even greater than or equal to 2.
  • the composition comprises an oleaginous substance content greater than or equal to 10% by weight, in particular greater than or equal to 20% by weight, advantageously greater than or equal to 30% by weight, in particular greater than or equal to 40% by weight, more especially greater than or equal to 50% by weight, especially greater than or equal to 60% by weight, or even greater than or equal to 70% by weight relative to the total weight of the composition.
  • the composition may comprise at least two different cyclodextrins, each present in a content greater than or equal to 1% by weight, especially at a content greater than or equal to 10% by weight, or even a content greater than or equal to 20% by weight, even at a content greater than or equal to 30% relative to the total weight of cyclodextrin.
  • the composition comprises inclusion complexes according to the invention, especially in a content ranging from 1 to 99.9% by weight, in particular ranging from 15 to 99% by weight, or even from 25 to at 95% by weight relative to the total weight of the composition.
  • composition according to the invention may be in the form of a liquid, in particular aqueous, a semi-solid, a solid. It may especially be in the form of a powder, tablets, capsules, a cream, an emulsion, especially oil-in-water or water-in-oil, or even a multiple emulsion, liposomes, nanoparticles, microparticles or a suspension.
  • compositions according to the invention may be pharmaceutical, nutritional, veterinary, nutraceutical, food or cosmetic compositions comprising a mixture of inclusion complexes according to the invention.
  • inclusion of oleaginous substance, and in particular of fatty acids, in particular polyunsaturated fatty acids, or of their triglycerides, salts and / or esters in mixtures of cyclodextrins, according to the invention may make it possible to obtain aqueous, solid formulations or semi-solid, at 20 ° C.
  • this oleaginous substance and in particular these polyunsaturated fatty acids and / or their triglycerides, salts and esters while suppressing or greatly reducing the problems related to their oxidability and their instability as well as reducing or eliminating their taste and / or smell.
  • the subject of the invention is also the use of a mixture of at least two cyclodextrins as an agent for stabilizing and / or masking the taste and / or odor of oleaginous substance, in particular of acid unsaturated fats, in a composition, especially food, nutraceutical, cosmetic, pharmaceutical, veterinary, further comprising at least one oleaginous substance.
  • the subject of the invention is also the use of a mixture of at least two cyclodextrins and an oleaginous substance, in particular at least one unsaturated fatty acid, for the preparation of a medicinal product, in particular intended to treat or to prevent cardiovascular diseases.
  • the subject of the invention is a method for preparing inclusion complexes comprising at least the steps of: solubilizing at least two cyclodextrins chosen from alpha-, beta- and gamma-cyclodextrin and / or their derivatives, in particular in degassed water
  • the mixture is agitated, in particular under an inert atmosphere and / or absence of light, in particular at a temperature ranging from 10 to 40 ° C.,
  • the complexes can be recovered directly in emulsion form, or in powder form, in particular by lyophilization of the emulsion or by spray drying.
  • Example 1 Inclusion complexes of 60% camelina oil with a binary mixture of 40% cyclodextrins composed of 50% alpha-cyclodextrin and 50% ⁇ -cyclodextrin.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 2 Inclusion complexes of 60% camelina oil with a binary mixture of 40% cyclodextrins composed of 30% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.75 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved. 1.5 g of camelina oil are then added, and stirring is maintained constant at 300 rpm in the absence of light on a turntable for 24 hours at room temperature. A stable white suspension consisting of 40% binary mixture of cyclodextrin and 60% camelina oil is formed.
  • Example 3 Inclusion complexes of 70% camelina oil with a binary mixture of 30% cyclodextrins composed of 15% ⁇ -cyclodextrin and 15% ⁇ -cyclodextrin.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 4 Inclusion complexes of 70% camelina oil with a binary mixture of 30% cyclodextrins composed of 20% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.5 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved. 1.75 g of camelina oil are then added, and stirring is kept constant at 300 rpm in the absence of light on a turntable for 24 hours at room temperature. A stable white suspension consisting of 30% binary mixture of cyclodextrin and 70% camelina oil is formed.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 5 Inclusion complexes of 80% of camelina oil with a binary mixture of 20% cyclodextrins composed of 10% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.25 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • Example 6 Inclusion complexes of 80% of camelina oil with a binary mixture of 20% of cyclodextrins composed of 15% of ⁇ -cyclodextrin and 5% of ⁇ -cyclodextrin.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 7 Inclusion complexes of 60% camelina oil with a binary mixture of 40% cyclodextrins composed of 20% ⁇ -cyclodextrin and 20% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.5 g of ⁇ -cyclodextrin and 0.5 g is introduced into a container.
  • ⁇ -cyclodextrin and 30 ml degassed water The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 8 60% inclusion complexes of camelina oil with a binary mixture of 40% cyclodextrins composed of 30% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.75 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 9 Inclusion complexes of 70% camelina oil with a binary mixture of 30% cyclodextrins composed of 15% ⁇ -cyclodextrin and 15% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.375 g of ⁇ -cyclodextrin and 0.375 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • Example 10 Inclusion complexes of 70% camelina oil with a binary mixture of 30% cyclodextrins composed of 20% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin. 0.75 g of the cyclodextrin mixture composed of 0.5 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • Example 11 Inclusion complexes of 80% camelina oil with a binary mixture of 20% cyclodextrins composed of 10% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.25 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • Example 12 Inclusion complexes of 80% of camelina oil with a binary mixture of 20% cyclodextrins composed of 15% ⁇ -cyclodextrin and 5% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.375 g of ⁇ -cyclodextrin and 0.125 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a vessel. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 13 Inclusion Complexes of 60% camelina oil with a ternary mixture of 40% of cyclodextrins composed of 15% ⁇ -cyclodextrin, 10% ⁇ -cyclodextrin and 15% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.375 g of ⁇ -cyclodextrin, 0.25 g of ⁇ -cyclodextrin and 0.375 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved. 1.5 g of camelina oil are then added, and stirring is maintained constant at 300 rpm in the absence of light on a turntable for 24 hours at room temperature. A stable white suspension consisting of 40% binary mixture of cyclodextrin and 60% camelina oil is formed.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 14 Inclusion complexes of 70% camelina oil with a ternary mixture of 30% cyclodextrins composed of 10% ⁇ -cyclodextrin, 10% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.25 g of ⁇ -cyclodextrin, 0.25 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. . The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 15 Inclusion complexes of 79% of camelina oil by a ternary mixture of 21% of cyclodextrins composed of 7% ⁇ -cyclodextrin, 7% ⁇ -cyclodextrin and 7% ⁇ -cyclodextrin.
  • cyclodextrin mixture consisting of 0.175 g of ⁇ -cyclodextrin, 0.175 g of ⁇ -cyclodextrin and 0.175 g of ⁇ -cyclodextrin are introduced into a container and 30 ml of degassed water. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 16 60% inclusion complexes of argan oil with a binary mixture of 40% cyclodextrins composed of 30% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.75 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 17 Inclusion complexes of 70% argan oil with a binary mixture of 30% cyclodextrins composed of 15% ⁇ -cyclodextrin and 15% ⁇ -cyclodextrin.
  • Example 18 Inclusion complexes of 70% argan oil with a binary mixture of 30% cyclodextrins composed of 20% ⁇ -cyclodextrin and 10% ⁇ -cyclodextrin. 0.75 g of the cyclodextrin mixture composed of 0.5 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • a stable white suspension is formed consisting of 30% binary mixture of cyclodextrin and 70% argan oil.
  • Example 19 60% inclusion complexes of argan oil with a ternary mixture of 40% of cyclodextrins composed of 15% of ⁇ -cyclodextrin, 10% of ⁇ -cyclodextrin and 15% of ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.375 g of ⁇ -cyclodextrin, 0.25 g of ⁇ -cyclodextrin and 0.375 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved. 1.5 g of argan oil are then added, and stirring is kept constant at 300 rpm in the absence of light on a turntable during 24 hours. hours, at room temperature. A stable white suspension is formed consisting of 40% binary mixture of cyclodextrin and 60% argan oil.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.
  • Example 20 Inclusion complexes of 70% of argan oil by a ternary mixture of 30% of cyclodextrins composed of 10% of ⁇ -cyclodextrin, 10% of ⁇ -cyclodextrin and 10% of ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.25 g of ⁇ -cyclodextrin, 0.25 g of ⁇ -cyclodextrin and 0.25 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • a stable white suspension is formed consisting of 30% binary mixture of cyclodextrin and 70% argan oil.
  • Example 21 Inclusion complexes of 79% of argan oil by a ternary mixture of 21% of cyclodextrins composed of 7% of ⁇ -cyclodextrin, 7% of ⁇ -cyclodextrin and 7% of ⁇ -cyclodextrin.
  • cyclodextrin mixture composed of 0.175 g of ⁇ -cyclodextrin, 0.175 g of ⁇ -cyclodextrin and 0.175 g of ⁇ -cyclodextrin and 30 ml of degassed water are introduced into a container. The whole is stirred on a turntable at 300 rpm until the mixture of cyclodextrins has completely dissolved.
  • solubility of the lyophilized complexes is then examined, by dissolving in water, it leads to an opalescent solution.

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EP07731799A 2006-03-23 2007-03-22 Kombination einer öligen substanz mit einer mischung von mindestens zwei cyclodextrinen Withdrawn EP2003990A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0602526A FR2898817B1 (fr) 2006-03-23 2006-03-23 Association de substance oleagineuse avec un melange d'au moins deux cyclodextrines
PCT/FR2007/050986 WO2007107679A2 (fr) 2006-03-23 2007-03-22 Association de substance oleagineuse avec un melange d'au moins deux cyclodextrines

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GB0710439D0 (en) * 2007-05-31 2007-07-11 Uni I Oslo Oral dosage form
WO2009078030A1 (en) * 2007-12-17 2009-06-25 Alkem Laboratories Limited Fat substitute
US10328152B2 (en) 2011-06-16 2019-06-25 Nayan Patel Method for stabilization and delivery of therapeutic molecules
FR2999924B1 (fr) * 2012-12-21 2015-07-17 Oreal Association d'actifs comprenant au moins une huile essentielle, une cyclodextrine et un corps gras liquide et composition la contenant.
FR3009504B1 (fr) * 2013-08-12 2025-10-24 In Cyclo Nouveau systeme solide instantane auto-emulsionnant a base de cyclodextrines et d'huile pour l'administration orale
AR105019A1 (es) * 2015-06-25 2017-08-30 Acraf COMPOSICIÓN DESODORANTE QUE COMPRENDE DE UNA MEZCLA DE CICLODEXTRINA a, b Y g
JP6855001B2 (ja) * 2016-11-24 2021-04-07 池田食研株式会社 油溶性物質含浸食品の製造方法

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JPS5423966B2 (de) * 1972-11-11 1979-08-17
HU176217B (en) * 1978-11-20 1981-01-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing a cyclodextrin-chamomille inclusion complex and compositions containing thereof
JPS5921613A (ja) * 1982-07-28 1984-02-03 Takeda Chem Ind Ltd 直腸投与製剤
GB2140806B (en) * 1983-05-28 1987-10-28 Sekimoto Hiroshi Stabilisation of unsaturated fatty acids, fish oils or fish
JPS6058973A (ja) * 1983-09-13 1985-04-05 Mitsubishi Yuka Yakuhin Kk γ−プチロラクトン誘導体及びそれを有効成分とする免疫調節剤
US4727064A (en) * 1984-04-25 1988-02-23 The United States Of America As Represented By The Department Of Health And Human Services Pharmaceutical preparations containing cyclodextrin derivatives
JPS636196A (ja) * 1986-06-26 1988-01-12 柴内　裕子 紙の製造方法
IT1243192B (it) * 1990-08-09 1994-05-24 Staroil Ltd Complessi di acidi grassi polinsaturi a lunga catena e di loro derivati, con ciclodestrine
FR2692168B1 (fr) * 1992-06-16 1995-03-24 Centre Nat Rech Scient Préparation et utilisation de nouveaux systèmes colloïdaux dispersibles à base de cyclodextrine, sous forme de nanosphères.
US7799365B2 (en) * 2001-04-06 2010-09-21 Burnbrae Farms Limited Liquid egg composition including fish oil with omega-3 fatty acid
US7105195B2 (en) * 2003-07-25 2006-09-12 General Mills, Inc. Reduced trans fat product
CA2523390A1 (en) * 2004-10-15 2006-04-15 General Mills, Inc. Microwave popcorn with thaumatin and method of preparation

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JP2009530357A (ja) 2009-08-27
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US20090130218A1 (en) 2009-05-21
CA2647089A1 (fr) 2007-09-27
WO2007107679A3 (fr) 2007-11-15

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