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WO2023242339A1 - Composition comprenant de la pétasine et de l'isopétasine ayant un effet hépatoprotecteur - Google Patents

Composition comprenant de la pétasine et de l'isopétasine ayant un effet hépatoprotecteur Download PDF

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Publication number
WO2023242339A1
WO2023242339A1 PCT/EP2023/066110 EP2023066110W WO2023242339A1 WO 2023242339 A1 WO2023242339 A1 WO 2023242339A1 EP 2023066110 W EP2023066110 W EP 2023066110W WO 2023242339 A1 WO2023242339 A1 WO 2023242339A1
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WIPO (PCT)
Prior art keywords
petasin
composition
isopetasin
composition according
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.)
Ceased
Application number
PCT/EP2023/066110
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German (de)
English (en)
Inventor
Reiner Rittinghausen
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Weber & Weber GmbH
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Weber & Weber GmbH
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Filing date
Publication date
Application filed by Weber & Weber GmbH filed Critical Weber & Weber GmbH
Publication of WO2023242339A1 publication Critical patent/WO2023242339A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to a composition with a hepatoprotective effect comprising petasin and isopetasin, their use as a dietary food, food supplement, medical device, pharmaceutical composition or medicine, and their use for producing a pharmaceutical composition for the treatment of disease states, in particular for the treatment of migraines.
  • Petasites is also known as butterbur.
  • Petasites extracts or butterbur extracts can be obtained from the plant and/or plant parts, with leaves and/or roots being preferred.
  • Petasites extracts are usually isolated from the roots of butterbur and have antispasmodic and analgesic effects. This effect of butterbur was already known to Hippocrates, Galen and Paracelsus.
  • the European patent application EP 281 656 discloses the use of petasites extracts for the production of drugs for the treatment of gastrointestinal diseases, in particular damage to the gastric mucosa caused by endogenous and exogenous noxious substances, gastrointestinal ulcerations, gastritis of any origin as well as ulcerative colitis and Crohn's disease.
  • the production of the extracts and the treatment Medicines suitable for gastrointestinal diseases are produced using the usual methods of natural product chemistry and galenics.
  • EP 1107775 A1 relates to a pharmaceutical composition based on petasites extract, without hepatotoxic, carcinogenic, cytostatic and/or mutagenic effects, its use and a process for its production.
  • the petasites extract currently used are extracts that do not have any hepatoprotective effect.
  • butterbur In addition to sesquiterpenes, eremophilans, butterbur also contains pyrrolizidine alkaloids.
  • the pyrrolizidine alkaloids share the pyrrolizidine skeleton. They are distributed worldwide in higher plants. Pyrrolizidine alkaloids and their N-oxides are found, among other things, in the genera of Petasites.
  • the pyrrolizidine alkaloids contained in the plant parts of the genus Petasites are characterized by significant hepatotoxic, carcinogenic and mutagenic, but also cytostatic properties.
  • the toxicity of pyrrolizidine alkaloids is linked to certain structural groups that have the following structural features:
  • Cyclic diesters have the highest toxicity and carcinogenicity.
  • the pyrrolizidine alkaloids are quickly absorbed after oral intake, their N-oxides only after reduction by the intestinal flora.
  • the pyrrolizidine alkaloids are converted into very toxic pyrrole derivatives by mixed-functional oxidases. These are very reactive and, under physiological conditions, alkylate nucleophilic groups of DNA, such as amino, thiol and hydroxy groups.
  • Medicinal plants containing pyrrolizidine alkaloids have long been used as natural remedies in phytotherapy.
  • a composition comprising petasin and isopetasin, the weight content of isopetasin being higher than the weight content of petasin, based on the total weight of the composition, not only has no hepatotoxic, carcinogenic and/or mutagenic effect, but in comparison to petasin-containing Petasites extracts or non-depleted petasites containing petasites extract fractions of the prior art, additionally have a hepatoprotective effect.
  • the object of the present invention is to provide a composition with a hepatoprotective effect comprising petasin and isopetasin, which also has no hepatotoxic, carcinogenic, cytostatic and/or mutagenic effects.
  • the object of the present invention is achieved by means of a composition, the composition comprising petasin and isopetasin, the weight content of isopetasin being higher than the weight content of petasin, based on the total weight of the composition, this composition having a hepatoprotective effect.
  • composition in which the weight ratio of petasin to isopetasin is 1:1.1 to 1:20, preferably 1:1.1 to 1:10, preferably 1:2 to 1:9, further preferably 1:3 to 1:8, even more preferably 1:4 to 1:7 and particularly preferably 1:5 to 1:6.
  • the composition comprises S-isopetasine.
  • the composition comprises S-isopetasin, wherein the weight content of S-isopetasin is higher than the weight content of petasin, based on the total weight of the composition.
  • the composition has petasin and S-isopetasin, the weight ratio of petasin to S-isopetasin being 1:1.5 to 1:8, preferably 1:2 to 1:7, more preferably 1:2.5 to 1: 6, even more preferably 1:3 to 1:5 and particularly preferably 1:3.5 to 1:4.
  • the composition comprises S-petasin. According to one embodiment, the composition additionally comprises S-petasin and S-isopetasin. According to one embodiment, the composition has petasin and isopetasin and additionally S-petasin. According to one embodiment, the composition has petasin and isopetasin and additionally S-isopetasin. According to one embodiment, the composition has petasin and isopetasin and additionally S-petasin and S-isopetasin.
  • the weight content of petasin is higher than the weight content of S-petasin, based on the total weight of the composition.
  • the composition comprises S-petasin, wherein the weight content of petasin is higher than the weight content of S-petasin, based on the total weight of the composition.
  • the composition additionally comprises S-petasin and S-isopetasin, where the weight content of petasin is higher than the weight content of S-petasin, based on the total weight of the composition.
  • the composition comprises petasin and Isopetasin and additionally S-petasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the composition.
  • the composition has petasin and isopetasin and additionally S-isopetasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the composition.
  • the composition has petasin and isopetasin and additionally S-petasin and S-isopetasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the composition.
  • the weight ratio of S-petasin to petasin is 1:4 to 1:10, preferably 1:4.5 to 1:9, more preferably 1:5 to 1:8, even more preferably 1:3 to 1:5 and particularly preferably 1:6 to 1:7.
  • the composition comprises S-petasin, the weight ratio of S-petasin to petasin being 1:4 to 1:10, preferably 1:4.5 to 1:9, more preferably 1:5 to 1:8, even further preferably 1:3 to 1:5 and particularly preferably 1:6 to 1:7.
  • the composition additionally has S-petasin and S-isopetasin, the weight ratio of S-petasin to petasin being 1:4 to 1:10, preferably 1:4.5 to 1:9, more preferably 1:5 to 1 : 8, even more preferably 1:3 to 1:5 and particularly preferably 1:6 to 1:7.
  • the composition has >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-aH- and/or 8-ß-H-eremophilanilides and S-petasin, the composition having >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably having >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-aH- and / or 8-ß-H-eremophilanilides as well as petasin and isopetasin and additionally S-isopetasin, the composition having > 0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably > 0 ppb and ⁇ 5 ppb of pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-aH- and/or 8-ß-H-eremophilanilides, petasin and isopetasin as well as additionally S-petasin and S-isopetasin, the composition having >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably > 0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition comprises 8-aH- and/or 8-ß-H-eremophilanilides, wherein the weight content of petasin is higher than the weight content of S-petasin, based on the total weight of the composition, and wherein the composition is >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-a-H- and/or 8-ß-H-eremophilanilides and S-petasin, the weight content being Petasin is higher than the weight content of S-petasin, based on the total weight of the composition, and wherein the composition has > 0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably has > 0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of Pyrrolizidine alkaloids.
  • the composition has 8-aH- and/or 8-ß-H-eremophilanilides and additionally S-petasin and S-isopetasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight the composition, and wherein the composition has >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably has >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-aH- and/or 8-ß-H-eremophilanilides as well as petasin and isopetasin and S-petasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the Composition, and wherein the composition has >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably has >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-a-H- and/or 8-ß-H-eremophilanilides as well as petasin and isopetasin and additionally S-isopetasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the composition, and wherein the composition has >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably has >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids.
  • the composition has 8-aH- and/or 8-ß-H-eremophilanilides, petasin and isopetasin and additionally S-petasin and S-isopetasin, the weight content of petasin being higher than the weight content of S-petasin, based on the total weight of the composition, and wherein the composition has >0 ppb and ⁇ 10 ppb pyrrolizidine alkaloids, preferably has >0 ppb and ⁇ 5 ppb pyrrolizidine alkaloids, and preferably the composition is free of pyrrolizidine alkaloids. Most preferred is an extract comprising petasin and isopetasine fraction(s) that has less than 5 ppb of pyrrolizidine alkaloids.
  • a composition according to the invention can be obtained, for example, by combining extract(s) comprising petasin and isopetasin, which differ from one another, in particular which contain different components and/or which contain different proportions by weight.
  • the petasites extract fraction(s) are usually divided into polar and non-polar petasites extract fraction(s).
  • Non-polar petasites extract fraction(s) have a high proportion of lipophilic substances, such as petasins.
  • polar petasites extract fraction(s) are preferably petasin-free or at most have a small proportion of petasins.
  • a petasites extract fraction(s) is particularly preferred, the petasites extract fraction(s) being a non-polar extract.
  • a polar petasites extract fraction(s) is characterized by a reduced content of petasin or petasins.
  • composition according to the invention can be in a liquid, solid or liposomal dosage form.
  • the dosage form is 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, a gel, a suppository or an injection solution .
  • the composition according to the invention is in the form of a tablet, capsule or chewable tablet which comprises the active ingredient in the form of microcapsules.
  • the composition comes as a liquid, a spray, an aerosol, a foam, an inhalant, a powder, a tablet, a capsule, a soft gelatin capsule, a Chewable tablet, ointment, cream, gel, suppository, patch or solution for injection.
  • the composition can be contained as a component or main component of a liquid, 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, a gel, a Suppository, a patch or an injection solution.
  • the composition may be in the form of a dietary food, dietary supplement, medical device, pharmaceutical composition or medicine.
  • composition can be administered for the treatment and/or prophylaxis of diseases.
  • composition may be administered for the treatment of disease states, for the treatment of deficiency conditions and/or for the prophylaxis of disease states, comprising:
  • composition can be administered in particular for the treatment of disease states, for the treatment of deficiency states and/or for prophylaxis against disease states, comprising:
  • the pharmaceutically or pharmacologically active extract comprising petasin and isopetasin and/or the composition containing at least one extract fraction comprising petasin and isopetasin is suitable according to the invention as a spasmolytic and/or analgesic, in particular a spasmoanalgesic.
  • compositions are selected from the group of medicines, foods and nutritional supplements for medical and non-medical purposes.
  • compositions are also referred to as agents in this invention.
  • weight information refers to the total weight of the extract fraction(s) free of added solvents or extractants. Free of added solvents or extractants means that a possible remaining residual content of added solvent in the petasites extract fraction is > 0% by weight to ⁇ 1% by weight, preferably > 0% by weight and less than 0.1% by weight. , based on the total weight of the extract or the extract fraction.
  • the petasites extract fraction contains petasins.
  • Petasites There are 2 chemovarieties of Petasites that differ in the type and composition of the petasins: a) Furanopetasin chemovariety with furanoeremophilans, such as furanoeremophilans, 9-hydroxy-furanoeremophilanes, furanopetasin, 2-senecioyl-furanopetasol, 2-tigloyl-furanopetasol, 2 -Methlythioacryloyl-furanopetasol and/or eremophilan lactones.
  • furanopetasin chemovariety with furanoeremophilans such as furanoeremophilans, 9-hydroxy-furanoeremophilanes, furanopetasin, 2-senecioyl-furanopetasol, 2-tigloyl-furanopetasol, 2 -Methlythioacryloyl
  • Petasin chemovariety with various petasins which consist of esters of different acids, such as esterified acids: including angelica acid, cis-3-methylthioacryloylic acid, methacrylic acid, 3-methylcrotonic acid, isobutyric acid with the 3 isomeric compounds petasol, isopetasol and / or neopetasol.
  • esters of different acids such as esterified acids: including angelica acid, cis-3-methylthioacryloylic acid, methacrylic acid, 3-methylcrotonic acid, isobutyric acid with the 3 isomeric compounds petasol, isopetasol and / or neopetasol.
  • physiologically active substances such as trace elements, can be added to the composition or agent according to the invention.
  • a petasites extract can be separated preparatively using known separation methods, such as chromatography methods: a) via molecular size b) via polarity using adsorption chromatography, such as TLC or HPLC
  • the Petasites extract fraction(s) can preferably be made from plants and/or plant parts of Petasites hybridus, Petasites albus, Petasites japonicus, Petasites paradoxus, Petasites formosanus, Petasites kablikianus, Petasites tricholobus, Petasites niveus, Petasites amplus, Petasites georgicus, Petasites fragrans and/or Petasites spurius can be obtained, preferably using the underground parts of the plant to produce the extract.
  • Furanopetasin may comprise at least one of the following components:
  • composition according to the invention can also be achieved by adding at least one pharmaceutically and/or physiologically active substance, comprising at least one anti-inflammatory or analgesic, preferably extracts of Chamomilla recutita, Rhizoma Curcumae longae, Rhizoma Curcumae xanthorrhizae, Curcumae xanthorrhiza, Cortex Salicis, Salicis purpurea , Salicis daphenoides and/or Tanacetum parthenium; at least one trace element, preferably salts of iron, cobalt, chromium, iodine, copper, manganese, magnesium, zinc and/or selenium; at least one secretolytic or secretomotor agent, preferably extracts of licorice root, thyme herb and/or peppermint oil; at least one bronchospasmolytic, preferably extracts of ivy leaves; and/or vitamin, preferably vitamin A, B, C, D and/or
  • Such a composition has the advantage that a larger amount of the composition according to the invention can be administered, which is then absorbed over a prolonged period of time.
  • This makes it possible to achieve a practically constant active ingredient blood plasma level of the pharmaceutically active main active ingredients of the petasin and isopetasin-containing composition according to the invention over a period of at least 12 - 48 hours, preferably 24 hours, which requires a two-time, preferably one-time administration of the composition or dosage unit allowed per day.
  • Suitable substances for this include, in particular, the generally known substances which delay the absorption in the gastrointestinal tract for the release of lipophilic active ingredients.
  • the substance delaying absorption, selected from the group of paraffins is preferably a paraffin that is solid at room temperature, particularly preferably a hard paraffin.
  • the respective single dose of the aforementioned dosage forms comprising petasin, isopetasin and preferably petasin, isopetasin, S-isopetasin and S-petasin is from 50 to 300 mg of the composition, preferably from 75 mg to 200 mg of the composition, more preferably from 100 mg to 150 mg of the composition, based on the solvent-free petasites extract fraction(s), wherein the petasites extract fraction(s) comprise petasin and isopetasin, the weight content of isopetasin being higher than the weight content of petasin, based on the total weight of the composition.
  • Fig. 1 shows the CGRP expression depending on the petasin content.
  • Fig. 2 shows the CGRP expression depending on the petasin content
  • Figure 2 shows that the level of CGRP gene expression is related to the petasitis content of the composition.
  • composition according to the invention has a significant hepatoprotective effect, so that the composition according to the invention inhibits and/or heals and/or significantly reduces damaging processes of the liver, in particular due to a paracrine effect.
  • the composition according to the invention therefore has an anti-inflammatory or anti-inflammatory effect.

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Abstract

La présente invention concerne une composition ayant un effet hépatoprotecteur et comprenant de la pétasine et de l'isopétasine, son utilisation en tant qu'aliment diététique, complément alimentaire, produit médicinal, composition pharmaceutique ou médicament, et son utilisation pour la production d'une composition pharmaceutique pour le traitement d'états pathologiques, plus particulièrement pour le traitement de la migraine.
PCT/EP2023/066110 2022-06-15 2023-06-15 Composition comprenant de la pétasine et de l'isopétasine ayant un effet hépatoprotecteur Ceased WO2023242339A1 (fr)

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DE102022115137.9A DE102022115137A1 (de) 2022-06-15 2022-06-15 Zusammensetzung mit hepatoprotektiver Wirkung
DE102022115137.9 2022-06-15

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WO2023242339A1 true WO2023242339A1 (fr) 2023-12-21

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH660966A5 (en) * 1984-02-29 1987-06-30 Amo Pharm Ag Process for obtaining a petasites extract with high therapeutic activity from Petasites hybridus, with a content of from 60 to 75% petasin
EP0281656A1 (fr) 1987-03-12 1988-09-14 Plantamed Arzneimittel GmbH Utilisation d'extraits de pétasites pour la préparation d'un médicament pour le traitement de maladies gastro-intestinales
DE3910831C1 (fr) 1989-04-04 1990-12-06 Vogel & Weber Gmbh, 8084 Inning, De
DE4111141A1 (de) 1991-04-06 1992-10-08 Sueddeutsche Kalkstickstoff Verfahren zur herstellung von extrakten aus rhizoma petasitidis
DE4141749A1 (de) 1991-12-14 1993-06-17 Weber & Weber Gmbh Verfahren zur herstellung von extrakten aus rhizoma petasitidis
DE4208300A1 (de) * 1992-03-16 1993-09-23 Plantamed Arzneimittel Gmbh Petasin, isopetasin oder oxopetasin als bestandteil von arzneimitteln
DE19838848A1 (de) 1998-08-26 2000-03-02 Weber & Weber Gmbh & Co Kg Pyrrolizidinalkaloidfreie Petasites enthaltende Zusammensetzung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10311651A1 (de) 2003-03-14 2004-09-23 Weber & Weber Gmbh & Co. Kg Petasites, Petasitesextrakt und/oder Petasitesextraktfraktionen davon zur Akutbehandlung von Krankheitszuständen
WO2011056174A1 (fr) 2009-11-05 2011-05-12 Govindan Gopinathan Composition de soulagement des maux de tête migraineux

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH660966A5 (en) * 1984-02-29 1987-06-30 Amo Pharm Ag Process for obtaining a petasites extract with high therapeutic activity from Petasites hybridus, with a content of from 60 to 75% petasin
EP0281656A1 (fr) 1987-03-12 1988-09-14 Plantamed Arzneimittel GmbH Utilisation d'extraits de pétasites pour la préparation d'un médicament pour le traitement de maladies gastro-intestinales
DE3910831C1 (fr) 1989-04-04 1990-12-06 Vogel & Weber Gmbh, 8084 Inning, De
DE4111141A1 (de) 1991-04-06 1992-10-08 Sueddeutsche Kalkstickstoff Verfahren zur herstellung von extrakten aus rhizoma petasitidis
DE4141749A1 (de) 1991-12-14 1993-06-17 Weber & Weber Gmbh Verfahren zur herstellung von extrakten aus rhizoma petasitidis
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