EP3057578A1 - Composition permettant l'administration orale de curcumine - Google Patents

Composition permettant l'administration orale de curcumine

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Publication number
EP3057578A1
EP3057578A1 EP14801919.3A EP14801919A EP3057578A1 EP 3057578 A1 EP3057578 A1 EP 3057578A1 EP 14801919 A EP14801919 A EP 14801919A EP 3057578 A1 EP3057578 A1 EP 3057578A1
Authority
EP
European Patent Office
Prior art keywords
curcumin
oil
composition according
composition
weight
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Withdrawn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
EP14801919.3A
Other languages
German (de)
English (en)
Inventor
Uwe-Bernd Rose
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.)
BRIU GmbH
Original Assignee
BRIU GmbH
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 BRIU GmbH filed Critical BRIU GmbH
Publication of EP3057578A1 publication Critical patent/EP3057578A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/906—Zingiberaceae (Ginger family)
    • A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators

Definitions

  • composition for oral administration of curcumin Composition for oral administration of curcumin
  • the invention relates to a composition for the oral administration of curcumin.
  • the composition of the invention comprises curcumin in an olbas convinced composition.
  • the composition may contain one or more oils and one or more amphiphilic complexing agents.
  • the composition may also contain other additives or adjuvants, such as dispersants, anticaking / lubricants, antioxidants, chelating agents and / or preservatives.
  • the invention also relates to methods for the preparation of the compositions and their use as a medicament in the treatment or prevention of diseases. Background of the invention
  • Curcumin [l, 7-bis (4-hydroxyl-3-methoxyphenyl) -l, 6-heptadiene-3,5-dione] is a natural nutritional ingredient found in turmeric / turmeric, a spice made from Curcuma longa Linn becomes. Curcumin shows an anti-inflammatory effect, as well as an antioxidant effect and can inhibit the expression of cyclooxygenase 2 (COX 2). Curcumin also has anti-neoplastic properties and was able to inhibit cancer cells in vitro and therefore in rodent models to prevent cancer of the intestine, skin, stomach, duodenum, soft palate, tongue, sebaceous glands and breast.
  • curcumin Due to its anti-inflammatory and antineoplastic properties, curcumin has potential as both a therapeutic and prophylactic agent.
  • Curcumin can be extracted from natural sources (such as Javan turmeric) or produced synthetically.
  • curcumin is virtually insoluble in water.
  • the bioavailability of curcumin for therapeutic or prophylactic purposes is therefore difficult to achieve.
  • Various approaches have been pursued to improve the bioavailability of curcumin, including the inclusion of curcumin in liposomes or nanoparticles, the preparation of self-microemulsifying delivery systems, and the synthesis of structural analogues of curcumin. These approaches showed different success.
  • curcumin composition which enhances the bioavailability of curcumin is desirable to realize the performance of curcumin as a pharmaceutical agent.
  • the invention is therefore based on the object to provide a composition of the type mentioned, which is easy to handle and administer and which is therefore also suitable for prophylactic use. Description of the invention
  • the invention relates to an oil-based composition comprising curcumin.
  • composition is oil-based
  • the curcumin content of the composition is at least about 3% by weight.
  • composition of the invention is suitable for oral administration. It can thus be taken orally and utilized in the gastrointestinal tract.
  • the composition is oil-based. This means that it has as carrier liquid one or more oils and thus an oil phase.
  • the stable oil-based composition of the present invention comprises curcumin.
  • oil refers to fats or fatty acid triglycerides which are sufficiently liquid at the application temperature (preferably room temperature). These may be vegetable, animal or synthetic oils. Curcunnin is dissolved in the oil.
  • curcumin refers to curcumin as well as suitable curcumin derivatives in the context of the invention. The term curcumin may include pure curcumin, a metabolite thereof, a derivative thereof or a curcuminoid.
  • the composition of the present invention may include argumerone, methylcurcumin, demethoxycurcumin, bisdemethoxycurcumin, sodium curcuminate, dibenzoylmethane, acetylcurcumin, feruloylmethane, tetrahydrocurcumin, 1,7-bis (4-hydroxy-3-methoxyphenyl) -l, 6-heptadiene-3,5 dione (curcumin 1), 1, 7-bis (piperonyl) -1, 6-heptadiene-3,5-dione (piperonylurcumin), 1, 7-bis (2-hydroxynaphthyl) -1, 6-heptadiene-2, 5-dione (2-hydroxylnaphthylcurcumin), 1, 1-bis (phenyl) -l, 3,8,10-undecatetraene-5,7-dione or combinations thereof.
  • curcumin 1 1, 7-bis (piperonyl) -1, 6-h
  • curcumin derivative in the context of the invention refers to natural and synthetic curcumin derivatives. Examples include naturally occurring curcuminoids. These are secondary phytochemicals found in the rhizomes of various curcuma plants such as Curcuma longa.
  • curcuminoids summarizes the three substances curcumin, demethoxycurcumin and bisdemethoxycurcumin. From a chemical point of view, the curcuminoids are conjugated diarylheptanoids, in other words polyphenols.
  • synthetically modified molecules can be produced which have the same or similar physico-chemical properties but can be more physiologically active.
  • An example of this is EF-24:
  • EF-24 is an IKK inhibitor and synthetic curcumin analogue. EF-24 is more potent than curcumin and has a significantly higher bioavailability, and it has a 10-fold higher potency in cell death induction. In anti-tumor screening, it is more effective than cisplatin with much less side effect potential.
  • the curcumin derivatives are thus preferably selected according to the invention from the group consisting of demethoxycurcumin, bisdemethoxycurcumin and synthetic curcumin analogs, in particular EF-24. It is an essential aspect and advantage of the invention that the one or more oils as carrier liquid can dissolve curcumin to a certain extent and, surprisingly enough, make them sufficiently bioavailable in the gastrointestinal tract.
  • the composition further contains a complex of curcumin and one or more amphiphilic complexing agents.
  • Amphiphilic complexing agents are molecules which have both hydrophilic and lipophilic regions and are thus soluble in preferably polar solvents such as water and non-polar solvents such as oils, preferably readily soluble.
  • the amphiphilic complexing agents complex the curcumin, this complex is dispersed in the oil used as a carrier liquid. In this way, the potential concentration of curcumin in the composition of the invention is increased far beyond the solubility of curcumin in the carrier oil, and the amphiphilia of the complexing agent further improves the bioavailability of the curcumin upon passage through the gastrointestinal tract.
  • the essence of the invention is thus to provide a formulation for the oral administration of curcumin, which contains curcumin in two different ways (dissolved in the oil and dispersed as a complex in the oil by using an oil as a base and the dispersion of a curcumin complex in this carrier liquid Oil) and thus with tolerable volumes large amounts of curcumin fed to the organism and can be made bioavailable via the gastrointestinal tract.
  • the curcumine content of the composition according to the invention is at least about 3% by weight.
  • tolerable quantities of liquid for example with a 200 ml glass
  • large amounts of curcumin can be supplied to the organism. Oral administration is easily possible even outside a clinical environment and is therefore particularly suitable when curcumin is to be used prophylactically.
  • the composition may comprise one or more oils.
  • the one or more oils are selected from soybean oil, corn oil, medium chain triglycerides, olive oil, peanut oil, cottonseed oil, sesame oil, diesel oil, coconut oil, palm kernel oil, glycerol monostearate or glycerol monooleate, and mixtures thereof.
  • the one or more oils are preferably selected from the group consisting of vegetable oils.
  • the one or more oils according to the invention comprises medium-chain triglycerides (MCT).
  • MCT medium-chain triglycerides
  • C6, C8, C10 and C12 medium-chain triglycerides
  • MCTs are obtained industrially, for example, by hydrolysis of coconut oil and palm kernel oil, fractionation of medium-chain fatty acids and subsequent esterification with glycerol.
  • MCT oil is declared as a vegetable oil, is relatively soluble in an aqueous environment due to the relatively short fatty acid chain length and can be metabolized without bile acids. Due to the metabolic characteristics of MCT oils and they are used, inter alia, as part of nutritional therapy in various clinical pictures. Tropical vegetable fats such as coconut oil or palm kernel oil are also usable in this context.
  • a composition according to the invention comprises about 20 to about 80% by weight, more preferably about 30 to about 75% by weight, more preferably about 40 to about 70% by weight, even more preferably about 50 to about 70% by weight. one or more oils.
  • the composition is preferably anhydrous. This also improves the stability of curcumin, which can decompose in an aqueous environment depending on the pH.
  • water-in-oil emulsion preferably as a water-in-oil emulsion.
  • the proportion of water in such an emulsion may be up to 50% by weight, but is preferably 40% by weight or less, more preferably 20% by weight or less, more preferably 10% by weight or less, further preferably 5% Wt% or less.
  • a substantially anhydrous composition is particularly preferred.
  • the fraction of curcumin dissolved in the oil is preferably about 0.1 to about 1% by weight, more preferably about 0.2 to about 0.7% by weight, based on the amount of oil used (that is, not the weight of the total composition). -%, more preferably about 0.3 to about 0.6 wt .-%, more preferably about 0.4 to about 0.5 wt .-%.
  • amphiphilic complexing agent phospholipids are particularly preferred.
  • the phospholipids may be selected from one or more of phosphatidylcholines, phosphatidylethanolamines, phosphatidylserines, phosphatidylsphingomyelins, phosphatidic acids, phosphatidylinositol, phosphatidylglycerol and / or diphosphatidylglycerol (cardiolipin), the two carbon chains typically having between 14-22 carbon atoms in the chain and can vary in their degree of saturation.
  • the two carbon chains of the lipid may be symmetrical or unsymmetrical.
  • Phosphatidylcholine may be selected from Dilauroylphophatidylcholin, Dimyristoylphophatidylcholin, Dipalmitoylphophatidylcholin, Distearoylphophatidylcholin, Diarachidoylphophatidylcholin, Dioleoylphophatidylcholin, Dilinoleoylphophatidylcholin, Dierucoyl- phosphatidylcholine, Palmitoyloleoylphophatidylcholin, phosphatidylcholine of the egg phosphatidylcholine Myristoylpalmitoyl-, Palmitoylmyristoylphosphatidylcholin, Myristoylstearoylphosphatidylcholin, Palmitoylstearoylphosphatidylcholin, Stearoylpalmitoylphosphatidyl
  • Phosphatidylethanolamines may be selected from
  • Phosphatidic acids may be selected from, but are not limited to, dimyristoylphosphatidic acid, dipalmitoylphosphatidic acid, and dioleoylphosphatidic acid.
  • Phosphatidylserines may be selected from dimyristoylphosphatidylserine, dipalmitoylphosphatidylserine, dioleoylphosphatidylserine,
  • Distearoylphosphatidylserine, painnitoyloleylphosphatidylserine and phosphatidylserine of the brain are not limited thereto.
  • Phosphatidylglycerols may be selected from dilauryloylphosphatidylglycerol, dipalmitoylphosphatidylglycerol, distearoylphosphatidylglycerol, dioleoylphosphatidylglycerol, dimyristoylphosphatidylglycerol, Palmitoyloleoylphosphatidylglycerol and phosphatidylglycerol of ice, but are not limited thereto.
  • the phospholipids may be "caged" phospholipids, which are aminophospholipids that can render a liposome pH-sensitive As a result, the entrapped groups are released once endocytosed into the target cells, destabilizing the liposome can and causes the liposomes' non-entrapped lipids to become fusogenic, thereby releasing the active material carried by the liposome into the cell cytosome.
  • amphiphilic complexing agents include lecithin. Often it will be preferred that lecithin be used as a natural source of phosphatidylcholines.
  • amphiphilic complexing agents are in the form of liposomes, micelles, or a combination of both.
  • amphiphilic complexing agent (s) is in a complex with curcumin.
  • Phospholipids may include curcumin in the oil phase in micelles, or more preferably in liposomes, and complex with it.
  • the proportion of amphiphilic complexing agents, in particular phospholipids, in the total amount of the composition according to the invention is preferably about 4 to about 30% by weight, more preferably about 5 to about 25% by weight, more preferably about 10 to about 20% by weight.
  • the curcumine content of the total composition is according to the invention preferably about 3 to about 20 wt .-%, more preferably about 5 to about 18 wt .-%, more preferably about 10 to about 15 wt .-%.
  • a dispersing aid keeps the curcumin complexed in particular in liposomes in dispersion.
  • Waxes for example hydrogenated castor oil, can be used in particular as dispersing aids.
  • other suitable waxes which can be used as dispersion auxiliaries or viscosity regulators.
  • wax is to be understood in the context of the invention as in Ullmann's Encyclopedia of Industrial Chemistry, 6th edition, Volume 39, page 135 ff.
  • composition according to the invention may contain, instead of or in addition to the dispersing aids, further additives or adjuvants, such as anti-caking / lubricating agents, antioxidants, chelating agents, preservatives or combinations thereof.
  • further additives or adjuvants such as anti-caking / lubricating agents, antioxidants, chelating agents, preservatives or combinations thereof.
  • suitable anti-sticking agents or lubricants which are also used, for example, in tablet or granule production.
  • a suitable agent is, for example, magnesium stearate.
  • preservatives include, but are not limited to, benzalkonium chloride, benzoic acid, butylated hydroxyanisole, butyl 4-hydroxybenzoate (butylparaben), chlorobutanol, ethylparaben, methylparaben, propylparaben, phenoxyethanol, and phenylethyl alcohol.
  • the preservative is butyl 4-hydroxybenzoate.
  • antioxidants include, but are not limited to, ⁇ -tocopherol, ascorbic acid, butylated hydroxyanisole, butylated hydroxytoluene, citric acid, fumaric acid, maleic acid, monothioglycerol, propanoic acid, propyl gallate, sodium ascorbate, sodium bisulfite, sodium metabisulfite, potassium metabisulfite, sodium sulfite, tartaric acid and vitamin E.
  • chelating agents include, but are not limited to, ethylenediaminetetraacetic acid / ethylenediaminetetraacetate (EDTA), ethylenediaminetriacetic acid and diethylenetriaminepentacetic acid (DTPA).
  • composition of the invention for use as a medicament. It can be used in particular for the treatment or prophylaxis of inflammatory diseases or various cancers.
  • the present invention relates to methods of administering stable oil-based compositions as described above.
  • the oil-based compositions are orally administered to the patient.
  • Any effective dose of curcumin may be administered, such as doses of about 10-200 mg curcumin per kg body weight, and preferably doses of 40-100 mg / kg.
  • compositions can be administered to treat patients in need of these compositions.
  • the compositions may also be administered to treat a disease in a patient or to prevent the disease.
  • the disease may be a malignant or a non-malignant proliferative disease, an autoimmune or auto-inflammatory disease, or a degenerative disease.
  • malignant disease for the treatment of the present invention are skin cancer, gastrointestinal tract (esophagus, stomach, small and large intestine), lung cancer, liver cancer, pancreatic cancer, brain tumors, breast cancer, prostate cancer, cervix and vaginal cancer, cancer of the head, Neck and parts of the hematopoietic system (leukemias, lymphomas), but are not limited thereto.
  • non-malignant proliferative tissue diseases include, but are not limited to, gastrointestinal polyp formation, multible polyposis, and neurofibromatosis.
  • autoimmune diseases or auto-inflammatory disease include, but are not limited to, anaphylaxis, arthritis, or irritable bowel syndrome.
  • neurodegenerative diseases include, but are not limited to, frontotem porcine dementia (Pick's disease), Alzheimer's, Parkinson's, Huntington's, carpal tunnel syndrome, and amyotrophic lateral sclerosis (ALS).
  • soft tissue / soft tissue degenerative diseases that may be treated by the present invention include, but are not limited to, cataracts, arthritis, neural diseases, muscular diseases, connective tissue diseases, or combinations thereof.
  • compositions of the present invention may be useful in the treatment or prevention of cancer, for example, in gastrointestinal tract, soft tissue, and the like.
  • the present invention also relates to methods for preparing the stable, oil-based compositions as described above.
  • the method comprises mixing one or more oils with one or more amphiphilic complexing agents. Thereafter, curcumin can be added to the mixture whereby curcumin is dissolved in the one or more oils and can complex with the one or more amphiphilic complexing agents.
  • Another object of the invention is a process for the preparation of a composition according to the invention, comprising the steps:
  • curcumin to produce the complex of curcumin and amphiphilic complexing agent.
  • the complex is particularly preferred according to the invention for the complex to be prepared under shear to open phospholipid micelles or liposomes. When phospholipids and the carrier oil are mixed, they form (empty) liposomes or micelles from the outset. In order to be able to include curcumin in them, they must first be opened, this is done physically by suitable shearing.
  • the composition may comprise a formulation as shown in Table 2. Table 2. Curcumin compositions according to embodiments of the invention.
  • the composition may comprise a formulation as shown in Table 3.
  • Cutina® HR is a hydrogenated castor oil available from Cognis (CRS No. 8001 -78-3). The phospholipids and Cutina HR are heated to about 50 ° C with stirring. The medium chain triglycerides are added and stirring is continued until a homogeneous mass is obtained.
  • the curcumin is added and the mixture is whirled through a high speed Ultraturrax for about a minute and sheared until a homogeneous mass is formed again.
  • the antioxidant 4-butyl hydroxybenzoate and the anti-stick / lubricant magnesium stearate are added and stirred.
  • flavorants and other flavorings or sweeteners may then be added.
  • compositions of the present invention are obtained. It is storable and can be taken orally for therapeutic or prophylactic purposes.
  • the stability of the compositions of the present invention is consistent with what is commercially viable and / or commercially feasible for an orally administered product.
  • the compositions of the present invention may have a shelf-life and a post-storage contaminant level which is common for orally administered products.
  • compositions of the invention can be used as a medicament.
  • the compositions of the invention can be used to treat or prevent diseases, including cancer.
  • a stable oil-based composition for oral administration comprising:
  • composition of 1, wherein the curcumin comprises pure curcumin, a metabilotene thereof, a derivative thereof, or a curcuminoid.
  • composition of 1, wherein the curcumin in the composition has a content of about 3 to about 20 wt .-%.
  • composition of 1, wherein the one or more oils are selected from soybean oil, corn oil, medium chain triglycerides (MCT), castor oil, olive oil, peanut oil, cottonseed oil, sesame oil, diesel oil, glycerol monostearate or glycerol monooleate, and mixtures thereof.
  • MCT medium chain triglycerides
  • composition of 4 wherein the one or more oils comprise MCT.
  • composition of 1, wherein the one or more oils in the composition have a level of from about 20% to about 80% by weight.
  • composition of 1 wherein the curcumin in the composition is present in proportion to the one or more oils in the composition, wherein the ratio is about 0.1 to about 1 weight percent.
  • composition of 1, wherein the one or more amphiphilic complexing agents comprise one or more phospholipids.
  • the one or more phospholipids are selected from phosphatidylcholines, phosphatidylethanolamines, phosphatidylserines, phosphatidylsphingomyelins, phosphatidic acids, phosphatidylinositol, phosphatidylglycerol, diphosphatidylglycerol, and combinations thereof.
  • composition of 1, wherein the one or more amphiphilic complexing agents comprise lecithin.
  • composition of 1, wherein the one or more amphiphilic complexing agents are in the form of liposomes, micelles or combinations thereof. 12. The composition of 1, wherein the one or more amphiphilic complexing agents in the composition have a level of from about 4 to about 30 weight percent. 13. The composition of 1, wherein the one or more amphiphilic complexing agents are in complex with the curcumin.
  • composition of 14 wherein the one or more dispersants comprise hydrogenated castor oil. 16. The composition of 14, wherein the one or more anti-caking agents comprises magnesium stearate.
  • composition of claim 14, wherein the one or more preservatives comprise butyl 4-hydroxybenzoate.
  • composition of 1, wherein the composition is used as a medicament.
  • composition of 1, wherein the composition is used to treat or prevent cancer.
  • a method of treating patients comprising administering an assembly according to 1. 21. The method of 20, wherein the method is the treatment of cancer.

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Abstract

L'invention concerne une composition permettant l'administration orale de curcumine et présentant les caractéristiques suivantes : a) la composition est à base d'huile ; b) elle contient de la curcumine dissoute dans l'huile ; c) elle contient un complexe à base de curcumine et d'agents complexants amphiphiles ; d) la teneur en curcumine de la composition s'élève à au moins 3 % en poids.
EP14801919.3A 2013-10-16 2014-09-26 Composition permettant l'administration orale de curcumine Withdrawn EP3057578A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201310220974 DE102013220974A1 (de) 2013-10-16 2013-10-16 Zusammensetzung zur oralen Administration von Curcumin
PCT/DE2014/200508 WO2015055193A1 (fr) 2013-10-16 2014-09-26 Composition permettant l'administration orale de curcumine

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EP3057578A1 true EP3057578A1 (fr) 2016-08-24

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WO2015055193A1 (fr) 2015-04-23

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