WO2011042469A1 - Utilisation d'une composition à base d' érémophilanolides - Google Patents

Utilisation d'une composition à base d' érémophilanolides Download PDF

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Publication number
WO2011042469A1
WO2011042469A1 PCT/EP2010/064929 EP2010064929W WO2011042469A1 WO 2011042469 A1 WO2011042469 A1 WO 2011042469A1 EP 2010064929 W EP2010064929 W EP 2010064929W WO 2011042469 A1 WO2011042469 A1 WO 2011042469A1
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weight
eremophilanolide
composition
extract
composition according
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PCT/EP2010/064929
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German (de)
English (en)
Inventor
Reiner Rittinghausen
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Reiner Rittinghausen
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Priority to EP10773870A priority Critical patent/EP2485718A1/fr
Publication of WO2011042469A1 publication Critical patent/WO2011042469A1/fr

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    • 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
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • 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
    • A61K9/4816—Wall or shell material
    • A61K9/4825—Proteins, e.g. gelatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • 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

Definitions

  • the present invention relates to a composition based on eremophilanolides and their use, in particular for the production of a dietary supplement or dietetic foodstuff and a pharmaceutically active composition for the treatment of disease states.
  • Petasites hybridus or the common butterbur is a medicinal plant known since ancient times. Depending on the type of ingredients, a distinction is made according to recent studies, two chemotypes, namely the petasin type and the furanopetasin type.
  • the furanopetasin type also called furanopetasin variety, contains so-called furanoeremophilans, which are not found in the petasin-type plant.
  • Petasitic extract and nutritional supplements are, in particular, viscous extracts of the petasin type which have an unpleasant, bitter taste.
  • the furanopetasin type has hitherto not been used for dietary supplements or pharmaceutical preparations as an essential ingredient, since it has hitherto been assumed that only the petasin-type petasins have a pharmacologically active action.
  • the furanopetasin type in contrast to the petasin type (Petasin chemovariancy), the furanopetasin type (Furano chemovariancyte) has cytotoxic properties.
  • Branching of the alkyl side chain with at least one of the nucleic acids is branching of the alkyl side chain with at least one of the nucleic acids.
  • the highest toxicity and carcinogenicity are probably due to the cyclic diesters.
  • the Pyrrolizidinalkaloide are rapidly absorbed after peroral absorption, their N-oxides only after reduction by the intestinal flora.
  • the pyrrolizidine alkaloids are converted by mixed-function oxidases into very toxic pyrrole derivatives. These are highly reactive and alkylate under physiological conditions nucleophilic groups of the DNA, such as amino, thiol and hydroxy groups.
  • petasin-type petasites have been shown to have cytotoxic and hepatotoxic potential despite complete removal of pyrrolizide maltoids.
  • the object of the present invention was to provide a composition, the composition comprising a plant extract, obtainable from plant parts of the butterbur, which is free of pyrrolizide maltoids and has no cytotoxic and hepatotoxic potential.
  • Another object of the present invention was to provide a composition which composition has a pharmacologically active plant extract obtainable from plant parts of butterbur, which is free from pyrrolizide maltoids and has no cytotoxic and hepatotoxic potential.
  • Another object of the present invention was to provide a method for producing a composition, which composition comprises a pharmacologically active plant extract obtainable from plant parts of butterbur, which is free from pyrrolizide maltoids and has no cytotoxic and hepatotoxic potential.
  • composition comprising eremophilanolides and free of pyrrolizidine alkaloids has no cytotoxic and hepatotoxic potential.
  • eremophilanolide extracts obtainable by oxidation and / or oxidative rearrangement of Furanoeremophilanen, main components of the plant extract of furanopetasin type, has no cytotoxic and hepatotoxic potential.
  • Eremophilanolide-containing composition of the invention obtainable by oxidation and / or oxidative rearrangement of Furanopetasin-type furanoerophilans expressing synthesis of glutathione peroxidase 2 (GPX2) and suppressing an integrin receptor (ECM receptor).
  • GPX2 glutathione peroxidase 2
  • ECM receptor integrin receptor
  • Eremophilanolide-containing composition of the invention on human hepatocytes does not regulate genes, in particular phase II and phase III metabolism, which can be mechanistically associated with hepatotoxicity.
  • the furanopetasin type includes for the purposes of this invention all petasinuß species of butterbur. Further, all the parent plants of the genus Petasites (P.) which also contain furanopetasine-type compounds can be used in the present invention, including P. albus, P. japonicus, P. paradoxus, P. kablikianus and P. spurius. According to the invention, however, the furanopetasin type is preferred.
  • pyrrolizidinalkaloidauer Pfianzenxschreib means that the content of Pyrrolizidmalkaloiden in the composition, preferably solvent-free Plant extract, ⁇ 10 ppm, especially ⁇ 5 ppm, preferably ⁇ 1 ppm pyrrolizidine alkaloid, and more preferably ⁇ 0.01 ppm pyrrolizidine alkaloid, and most preferably below the detection limit.
  • the content of Pyrrolizidinalkaloiden in the composition based on 100 mg of solvent-free extract, for example, ⁇ 1 ug and preferably ⁇ 0.1 microg.
  • the weights of the composition are based on the total weight of the composition, free from added solvents or extractants.
  • Free of added solvents or extractants means that a possible residual solvent content in the composition is> 0 wt% to ⁇ 1 wt%, preferably less than 0.1 wt%, based on the total weight of the composition ,
  • Solvents may be selected from the group comprising alcohols, such as methanol or ethanol, and / or water.
  • the furanopetasin-type petasites extracts can be obtained from the plant, plant parts and / or plant cells, with leaves, subterranean plant parts such as rhizomes with foothills and / or roots being preferred. Most preferred is the use of the root. If appropriate, individual substances can also be obtained from a transformed plant, plant parts, and / or plant cells, preferably with
  • Agrobacterium rhizogenes transformed cultures thereof, in particular transformed Toohaarkulturen be recovered.
  • the Furanoeremophilane contained in Furanopetasin type can be obtained by oxidation and / or oxidative rearrangement of the Furanoeremophilane in the plant, plant parts and / or plant cells, with leaves, subterranean plant parts, such as rhizomes with foothills and / or roots are preferred converted into Eremophilanolide become.
  • the composition according to the invention may preferably comprise a furanopetasine-type plant extract in which the furano-eremophilanes are converted into eremophilanolides by oxidation and / or oxidative rearrangement.
  • eremophilanolides are also referred to as Eremophilanlactone.
  • the Furanoeremophilane contained in Furanopetasin type can be obtained by oxidation and / or oxidative rearrangement of Furanoeremophilane in the plant, plant parts and / or plant cells, with leaves, subterranean plant parts, such as rhizomes with foothills and / or roots are preferred Eremophilanolide be transferred and / or converted by oxidation and / or oxidative rearrangement of Furanoeremophilane in the corresponding extract or corresponding extract fraction / s in Eremophilanolide or Eremophilanlactone.
  • the Furanopetasmpfianzenex Exercise in which the Furanoeremophilane contained are converted by oxidation and / or oxidative rearrangement in Eremophilanolide or Eremophilanlactone may be a pure plant extract of furanopetasin type and / or a mixture of Furanopetasinessesektktratation.
  • a composition in which the furano-eremophilanes are converted to eremophilanolides or eremophilan lactones by oxidation and / or oxidative rearrangement can be obtained from a mixture of furanopetasin plant extract fractions by, for example, combining at least two furanopetasin plant extract fractions which differ from each other, in particular different components the furanoerophilanes contained by oxidation and / or oxidative rearrangement in
  • Eremophilanolide or Eremophilanlactone are transferred.
  • the furano-eremophilanes may be partially, preferably substantially and preferably fully converted in the composition into the eremophilanolides or eremophilan lactones.
  • the proportion of furano-eremophilanes in the composition is ⁇ 10 ppm, in particular ⁇ 5 ppm, preferably ⁇ 1 ppm and more preferably ⁇ 0.01 ppm, and most preferably below the detection limit.
  • the furano-eremophilanes may be> 50% to ⁇ 100%, preferably>60%>, more preferably>70%>, more preferably>80%>, even more preferably>90%> and even more> 99 % in the inventive composition in Eremophilanolide or Eremophilanlactone be converted.
  • the composition can contain furano-eremophilanes with> 0 wt.% To ⁇ 10 wt.%>, Preferably> 0.0001 wt.% To ⁇ 8 wt.%>, More preferably> 0.001 wt.%> To ⁇ 6% by weight, more preferably> 0.01% by weight> to ⁇ 4% by weight>,%>, more preferably> 0.05% by weight> to ⁇ 2% by weight> , and furthermore preferably> 0.1% by weight to> 1% by weight, based on the total weight of the composition.
  • furano-eremophilanes almost completely and particularly preferably completely in the inventive composition in
  • Eremophilanolide or Eremophilanlactone are transferred.
  • the ratio of the proportions by weight of furanoeremophilanes to eremophilanolides in the composition according to the invention may be in the range from 1: 1,000,000 to 1:10 and preferably in the range from 1: 1: 00,000 to 1: 100.
  • a composition according to the invention which is free of pyrrolizidine alkaloids may contain> 1% by weight to ⁇ 100% by weight, preferably> 5% by weight to ⁇ 90% by weight, more preferably> 10% by weight. % to ⁇ 80% by weight, more preferably> 15% by weight to ⁇ 70% by weight, furthermore preferably> 20% by weight> to ⁇ 60% by weight, more preferably> 30% by weight %> to ⁇ 50% by weight> eremophilanolides, based on the total weight of the composition.
  • composition of the invention free of pyrrolizidine alkaloids may have petasins.
  • the petasins may be selected from the group comprising petasin, neeopetasine and / or isopetasin, iso-S-petasin, neo-S-petasin, S-petasin, 3-deoxy-isopetasol, 3-deoxyneopetasol, isobutyryl-neopetasol, methacryloyl -petasol, methacryloyl-isopetasol, 3-thiomethylacryl neopetasol, 3-thiomethylacrylisopetasol, 3-methylcrotonoyl-neopetasol, 3-methylcrotonoyl-petasol, and / or 3-methylcrotonoyl-isopetasol.
  • the proportion by weight of petasines can be> 0% by weight to ⁇ 20% by weight, preferably> 1% by weight to ⁇ 17% by weight, more preferably> 2% by weight. % to ⁇ 15% by weight, preferably> 5% by weight to ⁇ 10% by weight, with a petasinbuild composition being most preferred.
  • the content of petasins in the composition can be in the range from> 0 wt.% To ⁇ 5 wt.%, In particular ⁇ 1 wt.%, Based on the total weight of the composition.
  • the composition, especially the furan petasin extract can be free of petasins, i. the composition contains essentially eremophilanolides and no petasins.
  • composition according to the invention which is free of pyrrolizidine alkaloids may have the following components:
  • petasines > 0% by weight to ⁇ 40% by weight, preferably> 1% by weight to ⁇ 5% by weight, petasines;
  • the weight proportions of the components comprising eremophilanolides or eremophilanlactones and petasines are each selected so that together they make up a maximum of 100% by weight of the composition.
  • composition of the invention may preferably have the following components:
  • the weight proportions of the eremophilanolides, petasines and Furanoeremophilane are each chosen so that together make up a maximum of 100 wt .-% of the composition.
  • composition free of pyrrolizidine alkaloids in addition to the aforementioned components - for example to ad 100 wt .-% - other unspecified sesquiterpene compounds, essential oil, monoterpenes, aliphatic, low molecular oxygenated compounds and hydrocarbons such as nonene have.
  • the eremophilanolides may be selected from the group comprising 8 ⁇ -H-eremophilanolide, 8 ⁇ -H-eremophilanoid, and / or 2-angeloyl-8 ⁇ -H-eremophilanolide.
  • the eremophilanolides may be selected from the group comprising 8 ⁇ -H-eremophilanolide, 8 ⁇ -H-eremophilanoid, 2-angeloyl-8 ⁇ -H-eremophilanolide, 2-angeloyl-8 ⁇ -H-eremophilanolide, 2-senecioyl-8 ⁇ -H-eremophilanolide , 2-Tigloyl-8a-H-eremophilanolide, 2-tigloyl-8a-H-eremophilanolide, 2-methacroyl-8a-H-eremophilanolide, 2-isobutyryl-8a-H-eremophilanolide, 2-senecioyl-8 ⁇ -H-eremophilanolide , 2-tigloyl-8 ⁇ -H-eremophilanolide, 2-methacroyl-8 ⁇ -H-eremophilanolide, 8 ⁇ -H-9 ⁇ -hydroxy-petasitolide-A, 8 ⁇ -hydroxy-dememanolanolide, 2-methylthioacryloyl
  • Petasitolide-A Petasitolide-B, S-Petasitolide-A, and / or S-Petasitolide-B.
  • the composition according to the invention comprises at least one, preferably at least five, more preferably at least ten and more preferably at least 15 eremophilanolides or eremophilanlactones selected from the group comprising 8 ⁇ -H-eremophilanolide, 8a-H-eremophilanolide, 2-angeloyl 8 ⁇ -H-eremophilanolide, 2-angeloyl-8a-H-eremophilanolide, 2-senecioyl-8a-H-eremophilanolide, 2-tigloyl-8a-H-eremophilanolide, 2-tigloyl- ⁇ H-eremophilanolide, 2-methacroyl-8a -H-eremophilanolide, 2-isobutyryl-8a-H-eremophilanolide, 2-senecioyl-8 ⁇ -H-eremophilanolide, 2- Methacroyl-8 ⁇ -H-eremophilanolide, 8 ⁇ -H-9 ⁇ -hydroxy-petas
  • a further composition suitable according to the invention may comprise at least one component, preferably at least five, more preferably at least ten, and most preferably at least 15 selected from the group of 8a-eremophilanolides, 8 ⁇ -eremophilanolides, 8 ⁇ -H-eremophilanolide, 8a-H-eremophilanolide, 2 Angoyl-8 ⁇ -H-eremophilanolide, 2-angeloyl-8a-H-eremophilanolide, 2-senecioyl-8a-H-eremophilanolide, 2-tigloyl-8a-H-eremophilanolide, 2-tigloyl-8 ⁇ -H-eremophilanolide, 2 -Methacroyl-8a-H-eremophilanolide, 2-isobutyryl-8a-H-eremophilanolide, 2-senecioyl-8 ⁇ -H-eremophilanolide, 2-methacroyl-8 ⁇ -H-eremophilanolide, 8 ⁇ -H-9 ⁇ -hydroxy-petasit
  • composition of the present invention may be a mixture of furanopetasin-type plant extract and petasin-type plant extract. Where compositions free of petasin-type plant extract are most preferred.
  • composition of the invention may have a ratio of furanopetasin-type plant extract to petasin-type plant extract of> 100: 1 to 1: ⁇ 0.1, preferably> 44: 1 to 1: ⁇ 1 and preferably from 50: 1 to 5: 1, with higher plant extract fractions of the furanopetasine type being preferred in order to avoid the risk of hepatotoxic potential of the composition.
  • compositions of the invention which are free of plant extract of the petasin type, in particular free of petasins, are also most preferred.
  • a preferred composition according to the invention may be the following
  • Eremophilanolide compounds based on the total weight of the composition, have:
  • composition may additionally comprise at least one component, preferably at least two components and more preferably at least three components or else several of the following components:
  • Antiphlogistic, analgesic, antipyretic Extracts of Chamomilla recutita, Rhizoma Curcumae longae, Rhizoma Curcumae xanthorrhizae, Curcumae xanthorrhiza, Cortex Salicis, Salicis purpura, Salicis daphenoides and / or Tanacetum parthenium; Rosmarinus officinalis
  • Trace elements preferably salts of chromium, iron, iodine, copper, cobalt, magnesium, manganese, selenium and / or zinc;
  • Secretolytic, secretomotor moiety preferably extracts of liquorice root, thyme herb and / or peppermint oil;
  • Bronchospasmolytic preferably extracts of ivy leaves, calendula and / or viola;
  • Vitamin preferably vitamin A, B, C, D, E and / or K; and / or antioxidant, preferably Q10, lycopene, lutein, zeaxanthin, bioflavonoids, anthocyanidins, grapeseed extract, extracts of various fruits, for example pomegranate, kiwi, cranberry, etc .;
  • Urinary spasmolytic / antiphlogistic preferably extracts of pumpkin seeds and sabal fruits
  • Antimicrobial plant extract or drug preferably sabal leaves, essential oils such as eucalyptus oil.
  • the composition may, but is not preferred, be added to at least one taste-masking substance, the taste-masking substance preferably comprising essential oils, essences, aromatic waters, oily sugar, fruit flavors, aromatic drug extracts, artificial flavorings, sugars, sweetness polyols, neutral-tasting thickening agents, Cyclodextrins and / or mixtures thereof.
  • the taste-masking substance preferably comprising essential oils, essences, aromatic waters, oily sugar, fruit flavors, aromatic drug extracts, artificial flavorings, sugars, sweetness polyols, neutral-tasting thickening agents, Cyclodextrins and / or mixtures thereof.
  • Another object of the present invention relates to an agent containing a composition of the invention.
  • the composition according to the invention can have the composition according to the invention with a weight fraction, based on the total weight of the composition, of> 0% by weight to ⁇ 100% by weight, in particular> 1% by weight to ⁇ 95% by weight, preferably > 5% by weight to ⁇ 90% by weight, more preferably> 10% by weight to ⁇ 80% by weight, even more preferably> 15% by weight to ⁇ 70% by weight, more preferably> 20 % By weight to ⁇ 60% by weight, more preferably> 30% by weight to ⁇ 50% by weight.
  • such agents can also> 0.01 wt .-% to ⁇ 10 wt .-% of the composition according to the invention, preferably up to 5 wt .-%, in particular up to ⁇ 1 wt .-% and optionally up to ⁇ 0.1 wt .-%, based on the total weight of the agent.
  • compositions according to the invention may be selected from the group comprising medicaments, foods, food supplements.
  • the agents may be used for medical and / or non-medical purposes, especially dietary and / or nutritional supplementation.
  • a pharmaceutical composition containing the composition according to the invention may contain the composition with a weight fraction of> 0.01% by weight to ⁇ 90% by weight, preferably> 0.5% by weight to ⁇ 80% by weight, more preferably> 1 % By weight to ⁇ 70% by weight, more preferably> 5% by weight to ⁇ 60% by weight, further preferably> 10% by weight to ⁇ 50% by weight, and also preferably> 20% by weight % to ⁇ 40% by weight, based on the total weight of the drug.
  • Another object of the present invention relates to a dietary supplement or dietetic food, which has the composition of the invention.
  • the dietary supplement or dietary foodstuff may comprise the composition in a proportion by weight of> 0% by weight to ⁇ 100% by weight, based on the total weight of the dietary supplement.
  • the dietary supplement or dietary foodstuff may contain the composition with a weight fraction of> 0.01% by weight to ⁇ 90% by weight, preferably> 0.5% by weight to ⁇ 80% by weight, more preferably> 1% by weight to ⁇ 70% by weight, more preferably> 5% by weight to ⁇ 60% by weight, further preferably> 10% by weight to ⁇ 50% by weight, and also preferably> 20 Wt .-% to ⁇ 40% by weight, based on the total weight of the dietary supplement or dietetic food, have.
  • composition according to the invention, the medicament according to the invention and / or the food supplement or dietary food according to the invention can be used for the treatment of disease states and / or for nutritive supplementation.
  • the composition according to the invention, the medicaments according to the invention and / or the food supplement or dietary food according to the invention can be used for the preparation of a pharmaceutically active composition or for nutritive supplementation in the treatment of diseases and / or prophylaxis of diseases comprising joint and bile tissue diseases, arthritis, osteoarthritis , Osteoarthritis, rheumatoid arthritis, chronic polyarthritis, polyps, adenomas, gastrointestinal diseases, gastrointestinal ulcerations, gastroduodenitis, and gastritis, of all kinds, spasms in the gastrointestinal tract, biliary tract dykinesia, colitis, Crohn's disease, thromboembolic disorders, coronary Diseases, cardiovascular diseases, ischemia, peripheral arterial occlusive diseases, inflammatory coronar
  • composition according to the invention of the medicament according to the invention and / or of the food supplement or dietetic food according to the invention for nutritive supplementation, treatment of diseases and / or prophylaxis of diseases comprising migraine, asthma, hay fever, allergic rhinitis and / or eczema can be particularly preferred be.
  • the pharmaceutically or pharmacologically active composition according to the invention can be foods for use in Alzheimer's, Parkinson's, neurodegenerative diseases, amyotrophic lateral sclerosis, cancer, metastases, chemotherapy, atherosclerosis, diabetes, metabolic syndrome, rheumatoid arthritis, Immunodeficiency, infections, inflammation, cataract prophylaxis and / or thyroid dysfunction may be used.
  • the pharmaceutically or pharmacologically active composition according to the invention, medicaments and / or food supplements or dietary foods may be used for use in atherosclerosis, thrombosis inhibition, cancer, metastases, rheumatoid arthritis and / or Crohn's disease.
  • compositions according to the invention medicaments and / or dietary supplements or dietetic foods for use as spasmolytic and / or analgesic, in particular
  • the pharmaceutical composition according to the invention is suitable for the manufacture of a medicament for the long-term treatment or long-term therapy of patients, in particular newborns, infants and small children. But it is also an acute treatment possible, i. no curative use, but immediately at or after the onset of the disease.
  • a suitable pharmaceutical and / or dietary supplement or foodstuff according to the invention may be formulated such that the administrable daily dose is between 5 mg - 600 mg of the composition of the invention, preferably between 50 mg - 500 mg of the composition, and most preferably 250 mg of the composition.
  • the respective individual dose of the abovementioned dosage forms is from 5 to 100 mg of the composition according to the invention, preferably from 25 mg to 100 mg of the composition according to the invention.
  • the use of the medicament according to the invention and / or dietary supplement or dietetic food preparation for the preparation of a spasmolytic, analgesic and / or spasmoanalgetic agent may be suitable for the treatment and / or prophylaxis of disease states.
  • Agents according to the invention may be in liquid, gel, solid and / or liposomal form.
  • Compositions according to the invention in liquid form may contain alcohol, such as ethanol, as solvent.
  • compositions according to the invention may be in the form of a spray, an aerosol, a foam, an inhalant, a powder, a tablet, a capsule, a soft gelatin capsule, a chewable tablet, an ointment, a cream Gel, a suppository or as an injection solution.
  • compositions according to the invention can also be formulated as a tablet, capsule, in particular gel capsule or chewable tablet.
  • Orally administrable dosage forms may be provided with a gastric juice resistant layer.
  • compositions according to the invention can be prepared by a homeopathic process technique.
  • Another object of the present invention relates to a process for the preparation of the composition according to the invention.
  • Furanoeremophilane be converted by oxidation and / or oxidative rearrangement in Eremophilanolide or Eremophilanlactone.
  • the drug may be derived from Petasites hybridus, the furanopetasin-type or a furanopetasin-type and petasin-type mixture, from the plant, parts of plants and / or plant cells, with leaves, subterranean plant parts and / or roots are preferred.
  • plant-based, plant-derived and / or plant-cell oxidant such as oxygen and / or H 2 O 2 , preferably H 2 0 2 in an aqueous phase
  • Suitable temperatures are in the range of> 30 ° C bar to ⁇ 80 ° C, preferably> 35 ° C bar to ⁇ 70 ° C and more preferably from> 40 ° C bar to ⁇ 60 ° C.
  • the period for the oxidation of the Plant, plant parts and / or plant cells may be 1 hour to 4 weeks, preferably 1 day to 14 days, preferably 3 to 10 days and most preferably 7 days.
  • the powdered drug has a particle diameter D 50 of> 1 ⁇ to ⁇ 3000 ⁇ , preferably from> 10 ⁇ to ⁇ 2500 ⁇ , preferably from> 100 ⁇ to ⁇ 2000 ⁇ , more preferably from> 200 ⁇ to ⁇ 1600 ⁇ , from> 300 ⁇ to ⁇ 1200 ⁇ , from> 400 ⁇ to ⁇ 1000 ⁇ and most preferably from> 500 ⁇ to ⁇ 800 ⁇ .
  • the powdered drug has a particle diameter D 70 of> 1 ⁇ to ⁇ 3000 ⁇ , preferably from> 10 ⁇ to ⁇ 2500 ⁇ , preferably from> 100 ⁇ to ⁇ 2000 ⁇ , more preferably from> 200 ⁇ to ⁇ 1600 ⁇ , from> 300 microns to ⁇ 1200 microns, from> 400 microns to ⁇ 1000 u ⁇ and most preferably from> 500 microns to ⁇ 800 microns.
  • the powdered drug has a particle diameter D90 of> 1 ⁇ to ⁇ 3000 .mu.m, preferably from> 10 ⁇ to ⁇ 2500 ⁇ , preferably from> 100 ⁇ to ⁇ 2000 microns, more preferably from> 200 ⁇ to ⁇ 1600 microns , from> 300 ⁇ m to ⁇ 1200 ⁇ m, from> 400 ⁇ m to ⁇ 1000 ⁇ m, and most preferably from> 500 ⁇ m to ⁇ 800 ⁇ m.
  • the oxidation of the powdered drug with a defined particle size or particle diameter, as indicated above, is advantageous in order to obtain an almost complete oxidation of the furanoerophilanes to eremophilanolides or eremophilan lactones.
  • the Furanoeremophilane can not be satisfactorily converted into the corresponding Eremophilanolide or Eremophilanlactone, since the contact with oxygen, which is necessary for the oxidation, does not sufficiently penetrate the drug.
  • D 50 means that> 50% by weight of the particles have a defined particle diameter or particle size.
  • D 70 means that> 70% by weight of the particles have a defined particle diameter or particle size.
  • D 90 means that> 90% by weight of the particles have a defined particle diameter or particle size.
  • the oxidation can be carried out, for example, by thermal treatment of the drug and / or the extract in the presence of oxygen.
  • oxygen flow can be supplied to the drug and / or the extract under pressure.
  • the term "elevated temperature” in the sense of the present invention means a temperature of> 25 ° C.
  • the drug and / or the extract for the oxidation of Furanoeremophilane a temperature of> 30 ° C bar to ⁇ 80 ° C, preferably> 35 ° C bar to ⁇ 70 ° C and particularly preferably from> 40 ° C bar exposed to ⁇ 60 ° C.
  • the period of oxidation of the drug and / or extract may be 1 hour to 4 weeks, preferably 1 day to 14 days, preferably 3 to 10 days and most preferably 7 days.
  • the drug and / or the extract can be oxidized by the addition of chemical oxidants.
  • H 2 O 2 can be added to the extract.
  • the furano-eremophilanes in the drug and / or the extract can be converted, preferably substantially and preferably completely, into the eremophilanolides or eremophilanlactones.
  • the furano-eremophilanes in the particulate drug can be converted essentially and preferably completely into the eremophilanolides or eremophilanlactones by passing a stream of hot air through them.
  • Suitable temperatures for the hot air stream may be> 30 ° C bar to ⁇ 80 ° C, preferably> 35 ° C bar to ⁇ 70 ° C and more preferably from> 40 ° C bar to ⁇ 60 ° C.
  • the treatment of the particulate drug with a stream of warm air may be 1 hour to 4 weeks, preferably 1 day to 14 days, preferably 3 to 10 days and most preferably 7 days.
  • the treatment time depends on the amount of drug to be treated.
  • the drug can be analyzed by means of customary analytical methods, such as GC-MS, HPLC-MS, NMR, IR and the like.
  • “complete” means that the proportion of furano-eremophilanes in the composition is ⁇ 10 ppm, in particular ⁇ 5 ppm, preferably ⁇ 1 ppm and more preferably ⁇ 0.01 ppm, and most preferably below the detection limit.
  • the furano-eremophilanes can be> 50% to ⁇ 100%), preferably> 60%>, more preferably> 70%>, more preferably> 80%>, even more preferably> 90% and even more be converted to> 99% in the composition according to the invention by means of oxidation in Eremophilanolide or Eremophilanlactone.
  • the furano-eremophilanes in the drug and / or the extract after the oxidation step may contain> 0% by weight to ⁇ 10% by weight, preferably> 0.0001% by weight to ⁇ 8% by weight. >, more preferably> 0.001 wt.%> to ⁇ 6 wt.%>, more preferably> 0.01 wt.%> to ⁇ 4 wt.%>,%>, furthermore preferably> 0.05 wt .%> to ⁇ 2% by weight>, and furthermore preferably> 0.1% by weight> to ⁇ 1% by weight, based on the total weight of the drug or of the extract.
  • furanoeremophilanes are completely converted into eremophilanolides or eremophilanlactones already in the drug.
  • C0 2 extract of the drug still Furanoeremophilane, which are then converted in the post-treatment steps of the primary extract by oxidation in Eremophilanolide or Eremophilanlactone.
  • the process according to the invention may comprise the following process steps:
  • this step can be repeated 1 to 20 times;
  • oxidation of furanoeremophilanes contained in the primary extract and / or in the extract to eremophilanolides at elevated temperature preferably> 30 ° C bar to ⁇ 80 ° C.
  • the primary extract is subjected to a temperature treatment.
  • Suitable temperatures are in the range of> 30 ° C bar to ⁇ 80 ° C, preferably> 35 ° C bar to ⁇ 70 ° C and more preferably from> 40 ° C bar to ⁇ 60 ° C.
  • H 2 0 2 3% 10% and 30% aqueous H 2 0 2 solutions can be used, with 3% and 10% aqueous H 2 0 2 solutions are gentler. Most preferably from 3% to aqueous H 2 0 2 solutions are used.
  • aqueous H 2 0 2 solution for almost complete or complete oxidation of Furanoeremophilane in Eremophilanolide in the primary extract of this can be added during washing, especially in the wash countercurrent process, additionally with an aqueous H 2 0 2 solution, wherein the oxidation preferably at a temperature in the range of> 35 ° C until ⁇ 45 ° C and preferably at 40 ° C ⁇ 2 0 C is performed.
  • the water content of the primary extract can be lowered to less than 1 wt .-%. It may be advantageous, after at least one washing step, preferably each washing step, to reduce the water content of the primary extract to less than 1% by weight, preferably ⁇ 0.1% by weight and preferably ⁇ 0.01% by weight, based on the total weight of the extract, lower.
  • the extract according to the invention can be prepared by known separation processes, such as
  • Chromatographic separation processes can be distinguished on the basis of the chemical-physical properties of the substances to be separated and the technical implementation of the separation process. Except for the gel filtration, which is based on different transport resistances of the components due to the molecular masses and sizes, chromatographic methods use the adsorption properties of the substance combination of separation mixture, mobile phase and adsorbent for separation. Distribution chromatographic methods are also contemplated.
  • Composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • Iron oxide black E 172 1.13-1.33 mg * Other lipids in which the extract dissolves include: olive oil, corn oil, soybean oil. Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • Soft gelatin capsule Composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l. ** Based on the total weight of the extract and a fluctuation of ⁇ 2% by weight.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity active substance
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l. ** Based on the total weight of the extract and a fluctuation of ⁇ 2% by weight.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • enteric-coated soft gelatin capsule Composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l. ** Based on the total weight of the extract and a fluctuation of ⁇ 2% by weight.
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • enteric-coated soft gelatin capsule Composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • composition quality quantity
  • lipids in which the extract dissolves include: olive oil, corn oil, soybean oil.
  • Therapeutic plasma concentration 1 to 1000 ⁇ g / l.
  • the furanopetasin extract with> 60% by weight **,> 70% by weight **,> 80% by weight **,> 90% by weight ** or> 99% by weight ** Eremophilanolides is mixed 1:10 with highly purified soybean oil with the addition of 0.1-2% by weight of egg lecithin as emulsifier, and the mixture emulsified to 0.5-2.0% by weight in water for injections.
  • the liposomes are prepared from glycerophospholipids, cholesterol and stearylamine and at least one lipid derivative, wherein the extract according to the invention with> 60 wt .-% **,> 70 wt .-% **,> 80 wt .-% **,> 90 wt .-% ** or> 99 wt .-% ** Eremophilanoliden in the lipid phase of the liposomes is dissolved.

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Abstract

L'invention concerne une composition à base d'érémophilanolides, comportant un extrait végétal du type furanopétasine, exempt d'alcaloïdes de la pyrrolizidine, et/ou un extrait végétal qui contient des composés furanoérémophilane du type furanopétasine, transformés en érémophilanolides correspondants par oxydation, ladite composition ayant une action pharmacologique et ne présentant pas de potentiel hépatotoxique, contrairement à l'extrait de pétasite du type pétasine et du tpye furane, exempt d'alcaloïdes de la pyrrolizidine.
PCT/EP2010/064929 2009-10-07 2010-10-06 Utilisation d'une composition à base d' érémophilanolides WO2011042469A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3111349A1 (fr) * 2020-06-11 2021-12-17 Robertet Sa Procédé d'extraction/purification des alcaloïdes pyrrolizidiniques
EP4134075A1 (fr) 2021-08-09 2023-02-15 Támogatott Kutatócsoportok Irodája Derives de l'hexahydronaphthalen-2-one à utiliser contre le sars-cov-2
WO2023017288A1 (fr) 2021-08-09 2023-02-16 Támogatott Kutatócsoportok Irodája Dérivés d'hexahydronaphtalén-2-one destinés à être utilisés contre une infection à coronavirus

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3111349A1 (fr) * 2020-06-11 2021-12-17 Robertet Sa Procédé d'extraction/purification des alcaloïdes pyrrolizidiniques
EP4134075A1 (fr) 2021-08-09 2023-02-15 Támogatott Kutatócsoportok Irodája Derives de l'hexahydronaphthalen-2-one à utiliser contre le sars-cov-2
WO2023017288A1 (fr) 2021-08-09 2023-02-16 Támogatott Kutatócsoportok Irodája Dérivés d'hexahydronaphtalén-2-one destinés à être utilisés contre une infection à coronavirus

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