WO2001054673A1 - Procede de preparation et d'administration de materiau a base de plante medicinale - Google Patents

Procede de preparation et d'administration de materiau a base de plante medicinale Download PDF

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Publication number
WO2001054673A1
WO2001054673A1 PCT/CA2001/000106 CA0100106W WO0154673A1 WO 2001054673 A1 WO2001054673 A1 WO 2001054673A1 CA 0100106 W CA0100106 W CA 0100106W WO 0154673 A1 WO0154673 A1 WO 0154673A1
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WO
WIPO (PCT)
Prior art keywords
plant material
echinacea
polymer
extract
solid dispersion
Prior art date
Application number
PCT/CA2001/000106
Other languages
English (en)
Inventor
Robert A. Miller
Original Assignee
The University Of British Columbia
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 The University Of British Columbia filed Critical The University Of British Columbia
Priority to AU29929/01A priority Critical patent/AU2992901A/en
Publication of WO2001054673A1 publication Critical patent/WO2001054673A1/fr

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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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin

Definitions

  • This application relates to a method of preparing and administering a solid dispersion comprising medicinal plant material.
  • the solid dispersion comprises a co-precipitate of plant material in a continuous phase of an enteric polymer.
  • the invention may be employed for delivering compositions comprising plant extracts to the alkaline regions of the gastrointestinal tract where they are available for absorption into the systemic circulation.
  • echinacea A large number of common herbs are known to have medicinal activity. For example, the expressed juice of E. purpurea, as well as hydroalcoholic extracts of the root of E. angustifolia and E. purpurea, have been shown to have immune stimulant properties.
  • the identity of the specific chemical constituent(s) of echinacea responsible for its medicinal activity is the subject of on-going study, but likely candidates include hydrophilic polysaccharides, caffeic acid derivatives and lipophilic isobutylamides.
  • echinacea is a hriinistered principally in tablet, capsule, lozenge, syrup or tincture form. Some of the active ingredients of the herb may be absorbed to some degree in the oral cavity.
  • echinacea extracts and other plant-based materials may be diminished by inactivation of active plant constituents in the acidic environment of the stomach before reaching more alkaline regions of the gastrointestinal tract where absorption into the systemic circulation commonly occurs
  • other commercially important botanicals such as garlic, ginseng, eleuthero ('Siberian ginseng'), devil's claw and maitake mushrooms include active ingredients that are degraded by stomach acid.
  • crushing, cutting or chewing garlic cloves activates the enzyme allinase which converts the odorless alliin of garlic to allicin that is believed to be the most active ingredient and has the typical odour and taste of fresh garlic.
  • Allicin undergoes further chemical transformations when ingested to produce other sulfur-containing derivatives with differing pharmacological activities.
  • garlic is dehydrated and consumed orally in capsule or tablet form, without enteric coating, dissolution in the presence of stomach acid leads to inactivation of the enzyme allinase and prevents conversion of alliin to allicin, the primary active principle.
  • Ginseng oligosaccharides prominent in traditional hot-water extracts of the root, are likely inactivated to some degree by gastric fluid.
  • Devil's claw extract claimed effective in treating certain forms of arthritis, has also been found to be inactive when administered orally, but active when administered intraperitoneally or inrraduodenally. Again, it is believed that the difference in activity depending upon the route of administration may be due to gastric acid degradation of the active principle(s).
  • gastric and intestinal enzymes may also have a negative impact on bioactivity of some plant preparations.
  • Drug delivery systems for delayed release of acid-sensitive drugs or other biologically active materials are well known in the prior art.
  • international application No. WO 98/19668 published 14 May, 1998 relates to a delayed delivery system comprising an enteric barrier layer.
  • the enteric layer is relatively insoluble in gastric fluid but rapidly or immediately soluble in intestinal fluid, whereby the drug is released in a pulsatile manner in the proximal segment of the gastrointestinal tract.
  • enteric polymers i.e. polymers which are relatively insoluble in acidic gastric fluid
  • the drug to be delivered is formulated into a discrete structure and the polymer is then applied as a coating around this structure.
  • Such structures comprising enteric barriers cannot be administered in dosage forms where small particle sizes are necessary, such as oral suspensions.
  • enterically coated tablets and the like Another drawback of such enterically coated tablets and the like is that the active ingredients are not available for absorption in the oral cavity to confer, for example, a local analgesic effect in addition to a systemic effect.
  • a method of preparing a solid dispersion of a pharmacologically active plant material includes the steps of (a) providing an extract comprising the plant material and a non-toxic liquid solvent; (b) dissolving an enteric polymer in the extract; and (c) removing the solvent from the extract to yield the solid dispersion, the dispersion comprising a co-precipitate of the extract and the polymer.
  • the plant material may comprise herbs selected from the group consisting of echinacea, garlic, eleuthero, maitake mushrooms, astragalus, bilberry, black cohosh, cayenne, chamomile, devil's claw, dong quai, evening primrose oil, feverfew, ginger, ginkgo, ginseng, goldenseal, gotu kola, grape seed extract, hawthorn, kava kava, licorice, milk thistle, St. John's wort, saw palmetto, tea tree and valerian.
  • herbs selected from the group consisting of echinacea, garlic, eleuthero, maitake mushrooms, astragalus, bilberry, black cohosh, cayenne, chamomile, devil's claw, dong quai, evening primrose oil, feverfew, ginger, ginkgo, ginseng, goldenseal, gotu kola, grape seed extract, hawthorn, kava
  • the solvent may comprise ethanol and water.
  • the percentage of ethanol in the solvent is preferably within the range of 75 - 95%.
  • the plant material is echinacea
  • the enteric polymer is hydroxypropylmethylcellulose phthalate
  • the alcohol content of the solvent is approximately 80%.
  • This application also relates to a homogenous solid dispersion prepared in accordance with the above-described method and a method for administering a therapeutically effective amount of the solid dispersion.
  • the solid dispersion may be formulated together with a pharmaceutically effective carrier suitable for oral administration.
  • Figure 1 is a plot showing dissolution of a solid dispersion of echinacea prepared in accordance with the invention in 0.1 N HC1 and pH 7.2 phosphate buffer as measured by ultraviolet absorbance at 260 nm.
  • This application relates to a method for preparing a solid dispersion of plant material in a continuous phase of an enteric polymer and the use of such a solid dispersion for therapeutic purposes.
  • the following terms shall have the corresponding meanings:
  • Solid dispersion means a dispersion of one material in a continuous solid phase of another material.
  • the term solid dispersion includes a solid solution where the dispersed material is present at a molecular or microparticular level and is not visible; and solid suspensions where the dispersed material is present in a visible particulate form.
  • Plant material means material extracted or otherwise derived from plants and having some demonstrated or potential medicinal activity.
  • Plant material includes herbal remedies such as echinacea, garlic, eleuthero, maitake mushrooms, astragalus, bilberry, black cohosh, cayenne, chamomile, devil's claw, dong quai, evening primrose oil, feverfew, ginger, ginkgo, ginseng, goldenseal, gotu kola, grape seed extract, hawthorn, kava kava, licorice, milk thistle, St. John's wort, saw palmetto, tea tree and valerian.
  • herbal remedies such as echinacea, garlic, eleuthero, maitake mushrooms, astragalus, bilberry, black cohosh, cayenne, chamomile, devil's claw, dong quai, evening primrose oil, feverfew, ginger, ginkgo, ginseng, goldenseal, gotu kola,
  • Enteric polymer means a polymer which is capable of forming a powder precipitate and is relatively insoluble in gastric fluid, such as hydroxypropylmethylcellulose phthalate.
  • Other possible enteric polymers include methacrylic acid copolymers, polyvinylacetate phthalate, shellac, alginic acid and appropriate salts of enteric polymers such as cellulose acetate phthalate, cellulose acetate trimellitate, cellulose acetate butyrate and cellulose acetate propionate.
  • Non-toxic liquid solvent means a solvent that does not leave a residue when dried that is potentially toxic when ingested by human beings.
  • Examples of non-toxic solvents include water, ethanol and combinations thereof.
  • the term does not include potentially hazardous volatile solvents such as acetone, ethyl acetate or chlorinated solvents.
  • echinacea has been shown to have analgesic and immune stimulant properties.
  • the specific chemical constituents of echinacea which confer its medicinal activity is the subject of on-going study, but likely includes polysaccharides and isobutylamides. It is commonplace for consumers to take echinacea in tincture or capsule form when the first sign of cold or flu symptoms occurs. Recent surveys suggest that approximately 15 - 20% of North Americans consume echinacea from time to time.
  • Oral ingestion of plant materials exposes such materials to the body's digestive processes. Such processes have evolved to extract nutrition from ingested materials.
  • medicinal effectiveness of echinacea and other herbs may be limited by the fact that medicinal ingredients are inactivated in the acidic environment of the stomach before reaching more alkaline regions of the gastrointestinal tract where absorption into the systemic circulation commonly occurs.
  • the applicant's invention involves a method for preparing a solid dispersion of plant material and an enteric polymer.
  • the solid dispersion may be formulated as a composition suitable for oral ingestion and which is not inactivated in the acidic regions of the gastrointestinal tract.
  • the method involves providing a plant extract comprising plant material suspended in a non-toxic liquid solvent. Tinctures comprising macerated plant material in a hydroalcoholic solvent may be used, for example, as the starting material.
  • a suitable enteric polymer is then dissolved in the solvent. Enteric polymers have little or no solubility in acidic media, such as gastric fluid, but are soluble in alkaline media, such as intestinal fluids.
  • the solvent is then removed by processes such as spray-drying to yield a solid dispersion comprising a co-precipitate of the plant material and the enteric polymer.
  • the plant material is uniformly dispersed in a continuous phase of the enteric polymer.
  • the co-precipitate of plant material and polymer may be produced in a range of particle sizes.
  • This enables the invention to be administered by means of a wide variety of drug delivery systems, including oral systems such as tablets, capsules, lozenges or suspensions.
  • Other delivery systems could include topical semi-solids, topical suspensions, rectal suspensions or suppositories, pulmonary aerosols or other delivery systems where fine particles are required.
  • the solid dispersion consists of plant material uniformly dispersed throughout the continuous phase of the enteric polymer. Accordingly some of the plant material is exposed at the surface of the particles and is therefore capable of having a therapeutic effect at the site of ingestion. The amount of plant material so exposed may be reduced or increased by varying the plant material to polymer ratio.
  • the solid dispersion is ordinarily prepared so that the amount of plant material at the surface of the particles potentially exposed to gastrointestinal fluids is minimal.
  • dissolution of the solid dispersion depends upon the dissolution properties of the continuous phase. Since the continuous phase is an enteric polymer in the present invention, very little dissolution would occur until the dispersion reaches the small intestine, which is normally the site of the most efficient absorption.
  • the polymeric medium in which the plant material is dispersed enhances the stability of the plant materials by reducing the opportunity for oxidative and hydrolytic degradation due to reduced permeability to oxygen and water imparted by the enteric polymer when the dispersion is orally ingested.
  • the enteric polymer may also confer a degree of protection against destructive pancreatic enzymes in the intestinal tract.
  • a solid dispersion comprising a co-precipitate of echinacea and hydroxypropylmethylcellulose phthalate NF(HPMCP) polymer is administered orally in the form of a syrup or lozenge.
  • the echinacea including its active ingredients, is uniformly dispersed throughout the polymer, some of the active ingredients are available for local absorption in the oral cavity or upper respiratory tract of the patient as discussed above, unlike conventional enterically coated drugs.
  • the active ingredients may have a local analgesic effect in the mouth and throat (i.e. upper respiratory tract) of the patient in addition to a systemic effect when the active ingredients are absorbed in the alkaline regions of the gastrointestinal tract downstream from the stomach.
  • the fact that the majority of the active ingredients are protected from inactivation by gastric fluids does not preclude the advantages of local absorption of some active ingredients in the upper gastrointestinal tract upstream from the stomach. Further, formulating the echinacea plant material as a solid dispersion helps to mask the taste and odour of echinacea which some consumers consider unpleasant.
  • An important feature of the invention is the versatility of its application in different formulation media and formats. Since the solid dispersion comprising plant material can be prepared in an extremely fine powder form, this enables the plant material to be formulated for effective delivery in a wide variety of commercially important delivery formats having a pleasant taste and smell, such as ice cream, teas, jellied drinks, soft drinks and fruit juices, cough syrups and a wide variety of food products including candies, lollipops and cough drops. The invention thus enables the ingestion of a high dosage of potentially therapeutic plant materials while masking potentially unpleasant taste and odour.
  • Echinacea purpurea root and tops was obtained in the form of a commercially available hydroalcoholic tincture comprising 55% ethanol and 45% water. The amount of ethanol in the extract was then increased to approximately 80%. A quantity of a cellulosic enteric polymer , namely hydroxypropylmethylcellulose phthalate NF (HPMPCP), equivalent to the weight of plant solids contained in the extract, was dissolved in the extract. The hydroalcoholic solvent was then removed from the extract by spray-drying to yield a solid dispersion comprising co-precipitate of echinacea and HPMPCP. The solid dispersion consists of a fine off-white to beige powder with particles ranging in size from five microns to less than one micron.
  • HPMPCP hydroxypropylmethylcellulose phthalate NF
  • the co-precipitate was not noticeably odoriferous suggesting that the applicant's process can effectively mask the scent of plant material.
  • a similar effect may be achieved by forming solid dispersions of enteric polymers and other markedly odoriferous prominent plant preparations such as those from garlic cloves and valerian root.
  • Acid resistance of the solid dispersion was tested using USP Dissolution Apparatus II using 0.1 N HCl as the test fluid as illustrated in Figure 1. Release in alkaline fluids was also determined using pH 7.2 phosphate buffer as the test fluid. The first samples were withdrawn from the dissolution flasks approximately two minutes after the materials were introduced into each flask. The resulting absorbance of approximately 0.3 indicates that there is a rapid release of some component(s) of each sample, presumably from the surface of the particles of powder. The horizontal plot of samples in 0.1 N HCl indicates that no further material is released during the test period. The positive slope for samples in pH 7.2 phosphate buffer indicates a further release of material into solution as a function of time.
  • a plant extract of St. John's Wort was obtained in the form of a commercially available hydroalcoholic tincture comprising 55% ethanol and 45% water. The amount of ethanol in the extract was then increased to approximately 80%.
  • the hydroalcoholic solvent was then gradually removed from the extract by spray-drying to yield a solid dispersion comprising a co-precipitate of St. John's Wort and HPMCP.
  • the solid dispersion consists of a fine light brown powder with particles ranging in size from five microns to less than one micron. This co-precipitate was not noticeably odoriferous suggesting that the applicant's process can effectively mask the scent of plant material.
  • John's Wort co-precipitate from acid exposure until the liquid reached a pH that allowed dissolution of the HPMCP and release of the hypericins.
  • a sample of a commercially available of St. John's Wort Tincture was treated in a similar manner.
  • the total hypericins content was found to be 15 micrograms per gram after 30 minutes exposure to gastric juice.
  • St. John's Wort tincture had been destroyed by the gastric juice during the 30 minute exposure period. Since the acidic pH had already destroyed the hypericins in the unprotected St. John's Wort, increasing the pH of the solution to 6.8 did not change the total hypericins content. This indicates that the invention protects the hypericins in St. John's Wort from destruction in the stomach environment yet can release the hypericins in the small intestine for local therapeutic effect or for absorption into the blood stream for a systemic therapeutic effect.
  • a plant extract of Valerian was obtained in the form of a commercially available hydroalcoholic tincture comprising 45% ethanol and 55% water. The amount of ethanol in the extract was then increased to approximately 80%.
  • the hydroalcoholic solvent was then removed from the extract by spray-drying to yield a solid dispersion comprising a co-precipitate of valerian and HPMCP.
  • the solid dispersion consists of an off-white powder with particles ranging in size from five microns to less than one micron. This co-precipitate was not noticeably odoriferous suggesting that the applicant's process can effectively mask the scent of plant material.
  • enteric polymers could be substituted for HPMPCP.
  • such polymers should be soluble in water or hydroalcoholic solvents. This avoids the need to use potentially hazardous volatile solvents such as acetone, ethyl acetate or chlorinated solvents.
  • enteric polymers which are not soluble in a mixture of ethanol and water, such as cellulose acetate phthalate and cellulose acetate rrimellitate, are not preferred unless used in a form, such as a salt, which does not require the use of said hazardous solvents.
  • the process claimed in this application reduces both the complexity and the material requirements for delivering medicinal plant components in a way that they are protected against gastric inactivation. If conventional formulations were used, a larger mass of plant material would be required to formulate an effective dose. In a typical situation a quantity of the plant material, for example 300 mg, would be required for a normal dose. If this material were to be aclministered in the form of an enteric coated tablet, the core tablet could require up to an additional 300 mg of excipients and require a labour-intensive process such as wet granulation to overcome the variable properties of the plant materials and produce a granulation which could be easily compressed into a robust core tablet. This core tablet, weighing as much as 600 mg, then would require 60 mg or more of the enteric polymer to achieve protection against gastric acid.
  • a hydroalcoholic extract of the plant material may be used in which the amount of material extracted may only be 5% or less of the starting material. If this is applied to the above-mentioned material, the amount of material extracted from 300 mg of the crude plant material would be as little as 15 mg. In a 1: 1 co-precipitate, this would mean that the amount of the enteric polymer required would be reduced by 75%. Furthermore, the greater uniformity and reduced level of material (30 mg vs. 300 mg), could be easily incorporated into a direct compression tablet formulation thereby eliminating more complex granulation procedures and eliminating the need for a final coating operation.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

L'invention concerne un procédé de préparation et d'administration de compositions, comprenant un matériau à base de plante, destinées à être administrées dans les régions alcalines du tractus gastro-intestinal où elles peuvent être absorbées dans la grande circulation. Le procédé permet d'obtenir une dispersion solide contenant un coprécipité du matériau à base de plante dans une phase continue d'un polymère entéro-soluble.
PCT/CA2001/000106 2000-01-31 2001-01-31 Procede de preparation et d'administration de materiau a base de plante medicinale WO2001054673A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29929/01A AU2992901A (en) 2000-01-31 2001-01-31 Method for preparing and administering medicinal plant material

Applications Claiming Priority (2)

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US49450400A 2000-01-31 2000-01-31
US09/494,504 2000-01-31

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Publication Number Publication Date
WO2001054673A1 true WO2001054673A1 (fr) 2001-08-02

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1602364A1 (fr) * 2004-05-25 2005-12-07 Cognis IP Management GmbH Microcapsules (XXX), comprenant des extraits végétaux et procédé pour leur préparation
FR2884828A1 (fr) * 2005-04-26 2006-10-27 Patrice Chauvin Base de produits composes de plantes ayant des proprietes st imulantes pour le systeme nerveux et psychotrope,antioxydant e energetique aphrodisiaque et depurative
GB2432788B (en) * 2004-07-07 2009-09-30 Mediherb Holdings Ltd An echinacea formulation
WO2010023066A3 (fr) * 2008-09-01 2010-08-05 Unilever Plc Améliorations de compositions pharmaceutiques
WO2014008353A2 (fr) 2012-07-05 2014-01-09 Nutramax Laboratories, Inc. Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et un extrait ou une poudre de champignon
WO2022001976A1 (fr) * 2020-06-30 2022-01-06 北京诺康达医药科技股份有限公司 Procédé de détection rapide de la résistance à l'acide d'un comprimé à enrobage gastro-résistant
WO2022251524A1 (fr) 2021-05-26 2022-12-01 Nutramax Laboratories, Inc. Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et des constituants de plant de moringa

Citations (5)

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Publication number Priority date Publication date Assignee Title
US4313930A (en) * 1978-11-11 1982-02-02 Kali-Chemie Pharma Gmbh Stable valepotriate compounds and process for their preparation
EP0722719A1 (fr) * 1995-01-18 1996-07-24 MADAUS Aktiengesellschaft Procédé de fabrication de préparations à base de flavano-lignanes
US5578307A (en) * 1992-01-17 1996-11-26 Alfatec-Pharma Gmbh Shaped articles containing plant extract(s), in particular pellets, and their pharmaceutical or cosmetic use
JP2000026317A (ja) * 1998-07-07 2000-01-25 Sanki Shoji Kk マスキング組成物
WO2000006188A1 (fr) * 1998-07-28 2000-02-10 Mediko Pty. Ltd. Compositions de pousse/conservation des cheveux et methodes faisant appel auxdites compositions

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US4313930A (en) * 1978-11-11 1982-02-02 Kali-Chemie Pharma Gmbh Stable valepotriate compounds and process for their preparation
US5578307A (en) * 1992-01-17 1996-11-26 Alfatec-Pharma Gmbh Shaped articles containing plant extract(s), in particular pellets, and their pharmaceutical or cosmetic use
EP0722719A1 (fr) * 1995-01-18 1996-07-24 MADAUS Aktiengesellschaft Procédé de fabrication de préparations à base de flavano-lignanes
JP2000026317A (ja) * 1998-07-07 2000-01-25 Sanki Shoji Kk マスキング組成物
WO2000006188A1 (fr) * 1998-07-28 2000-02-10 Mediko Pty. Ltd. Compositions de pousse/conservation des cheveux et methodes faisant appel auxdites compositions

Non-Patent Citations (1)

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Title
CHEMICAL ABSTRACTS, vol. 132, no. 9, 28 February 2000, Columbus, Ohio, US; abstract no. 113087, HAYASHI, NORIAKI ET AL: "Masking compositions containing shellac" XP002167264 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1602364A1 (fr) * 2004-05-25 2005-12-07 Cognis IP Management GmbH Microcapsules (XXX), comprenant des extraits végétaux et procédé pour leur préparation
GB2432788B (en) * 2004-07-07 2009-09-30 Mediherb Holdings Ltd An echinacea formulation
US9205121B2 (en) 2004-07-07 2015-12-08 Integria Healthcare (Australia) PTY LTD Echinacea formulation
FR2884828A1 (fr) * 2005-04-26 2006-10-27 Patrice Chauvin Base de produits composes de plantes ayant des proprietes st imulantes pour le systeme nerveux et psychotrope,antioxydant e energetique aphrodisiaque et depurative
WO2010023066A3 (fr) * 2008-09-01 2010-08-05 Unilever Plc Améliorations de compositions pharmaceutiques
WO2014008353A2 (fr) 2012-07-05 2014-01-09 Nutramax Laboratories, Inc. Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et un extrait ou une poudre de champignon
EP3666277A1 (fr) 2012-07-05 2020-06-17 Nutramax Laboratories, Inc. Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et un extrait ou une poudre de champignon
WO2022001976A1 (fr) * 2020-06-30 2022-01-06 北京诺康达医药科技股份有限公司 Procédé de détection rapide de la résistance à l'acide d'un comprimé à enrobage gastro-résistant
WO2022251524A1 (fr) 2021-05-26 2022-12-01 Nutramax Laboratories, Inc. Compositions comprenant du sulforaphane ou un précurseur de sulforaphane et des constituants de plant de moringa

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