WO2011057686A1 - Oral formulations with high oral bioavailability consisting of mixtures of lipophilic and hydrophilic fractions obtained from propolis - Google Patents
Oral formulations with high oral bioavailability consisting of mixtures of lipophilic and hydrophilic fractions obtained from propolis Download PDFInfo
- Publication number
- WO2011057686A1 WO2011057686A1 PCT/EP2010/003843 EP2010003843W WO2011057686A1 WO 2011057686 A1 WO2011057686 A1 WO 2011057686A1 EP 2010003843 W EP2010003843 W EP 2010003843W WO 2011057686 A1 WO2011057686 A1 WO 2011057686A1
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- WIPO (PCT)
- Prior art keywords
- propolis
- lipophilic
- compositions according
- hydrophilic
- carrier
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Classifications
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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
- A61K9/14—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
- A61K9/145—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 compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
- A61K35/63—Arthropods
- A61K35/64—Insects, e.g. bees, wasps or fleas
- A61K35/644—Beeswax; Propolis; Royal jelly; Honey
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/282—Organic compounds, e.g. fats
Definitions
- the present invention relates to oral formulations containing propolis. More particularly, the present invention relates to sachets, orodispersible forms, capsules, simple/film-coated normal- or controlled-release tablets, consisting of a reconstituted 1 : 1 mixture of two fractions of propolis extracts caused to interact by suitable techniques with hydrophilic carriers and lipophilic carriers, in order to maximise the oral bioavailability of ingredients with an insufficiently hydrophilic and/or insufficiently lipophilic chemico-physical profile, so that it is sufficient to ensure their complete absorption.
- Propolis is a resin that covers the buds of some plants. It is collected and modified by bees with their salivary secretions and with the addition of wax.
- Propolis possesses bacteriostatic and bactericidal, anti-inflammatory, antifungal, antiviral, immunostimulating, vasoprotective, antioxidant, wound-healing and cell-regenerating activities. Its use in traditional medicine has extremely ancient origins.
- Propolis is used orally in the form of extracts, tinctures and water-alcohol solutions to prepare drops, mouthwashes and syrups; as dried extract to prepare tablets, effervescent tablets, granulates and the like, and in the form of mouthwashes, sprays, creams, lotions, emulsions, cleansers, fatty ointments, ointments, mixtures, lotions and pastes for local/topical use.
- Propolis is used above all for the treatment of upper respiratory tract disorders (throat inflammations, coughing, rhinitis and colds); in the prevention and treatment of gastrointestinal disorders (gastritis, colitis and gastro-duodenal ulcers) and viral diseases; to facilitate and regularise the digestion; to combat inflammations and infections; in urogenital infections and prostate disorders; it is used in general to strengthen the body's defences, to treat infections of the oral cavity (gingivitis, stomatitis), in dermatology (as a wound healer, against dermatitis, wounds, burns, eczema, rosacea, chilblains, chapping and varicose ulcers), for hair and scalp care and for dental and skin hygiene.
- gastrointestinal disorders gastritis, colitis and gastro-duodenal ulcers
- viral diseases to facilitate and regularise the digestion
- to combat inflammations and infections in urogenital infections and prostate disorders
- it is used in general to strengthen the body's defences,
- propolis consists of a mixture of aromatic and phenolic compounds (aromatic acids, aromatic aldehydes, caffeic, ferulic and fumaric acids), waxes (also containing group B vitamins, vitamins C and E, together with essential oils), polyphenols (in particular flavonoids, such as quercetin, galangin, isalpinin, kaempferide and rhamnocitrin), and also contains fatty acids, terpenes, amino acids, mineral salts (in particular calcium, copper, iron and manganese), resins and balsams.
- aromatic and phenolic compounds aromatic acids, aromatic aldehydes, caffeic, ferulic and fumaric acids
- waxes also containing group B vitamins, vitamins C and E, together with essential oils
- polyphenols in particular flavonoids, such as quercetin, galangin, isalpinin, kaempferide and rhamnocitrin
- fatty acids terpenes, amino acids, mineral salts
- said extracts a) and b) preferably being present in a weight ratio of 1 : 1.
- Increased hydrophilia can be obtained according to the invention by means of micronisation, mixing, chelating procedures, etc. co-grinding and/or ter-clathration with compounds such as amino acids (preferably L-glycine), cyclodextrins, maltodextrins, and hydrophilic vitamins (preferably ascorbic acid).
- the ratios between carrier and active fraction range between 10: 1 and 1 : 10, preferably between 2: 1 and 1 :2.
- Increased lipophilia can be obtained by phytosome or liposome processes mixing, chelation, co-grinding and/or ter-clathration with compounds such as phospholipids, fatty acids, oils, lipophilic amino acids, branched-chain amino acids and lipophilic vitamins (preferably alpha/beta/gamma- tocopherols).
- “Phytosome process” means placing the propolis extract in contact with a phospholipid such as lecithin, phosphatidylcholine, phosphatidylserine or other phospholipids, possibly mixed with one another. Under suitable conditions, a complex is formed wherein the polar and apolar functions present in the propolis substances and the phospholipid interact with mainly ionic bonds, to form a stable chemical entity (Phytosome®) which can be isolated and characterised. Examples of phytosome processes are disclosed in EP 275005, EP 209038, US 504323 and EP 1837030.
- the ter-clathration process consists of high-energy grinding of the propolis fraction, the carrier and an adjuvant, until an inclusion compound is obtained.
- a ter-clathration process is described in EP 1572155.
- the ratios between carrier and active fraction will range between 10:1 and 1 : 10, preferably between 2: 1 and 1 :2.
- the end product is reconstituted by mixing in ratios which can vary within a wide range, e.g. from 5 : 1 to 1 :5. However the ratio 1 : 1 is preferred.
- the reconstituted treated fractions are then formulated in pharmaceutical compositions according to conventional techniques.
- the forms according to the invention are gastroprotected, for example with shellac, hydroxypropyl methylcellulose or derivatives thereof.
- Preparation A 10 kg of dried propolis extract titrated in fiavonoids expressed as 12% galangin is mixed and homogenised for 10 minutes in a rotary mixer with 75 kg of beta-cyclodextrins. When said period has elapsed, the mixture is loaded into a vibrating mill and subjected to co-grinding with a vibration amplitude of between 5 and 12 mm for 1 hour. When said period has elapsed, the product obtained is a fine flowable powder with a minimum yield of 98.6%.
- Preparation B in the same way, a further 10 kg of the same propolis is reacted in aprotic solvent with 20 kg of distearoylphosphatidylcholine for 15 minutes. When that time has elapsed, the complex obtained is dehydrated and restored to a fine, flowable powder.
- the two preparations A and B are then placed in a rotary mixer for 30 minutes.
- the mixture is further mixed with excipients, acting quickly to prevent demixing, and then subjected to compressive forces in punches, or distributed through a capsule-filling machine to give final doses of approx. 100 mg/dose of propolis (related to the initial weight, before any complexing procedure).
- the tablets undergo a film-coating process with 0.5-1% shellac in a rotary coating pan for 1-4 hours, whereas in the second case, the process has ended.
- Preparation A 10 kg of dried propolis extract titrated in flavonoids expressed as 12% galangin is mixed and homogenised for 10 minutes in a rotary mixer with 5 kg of L-glycine. When said period has elapsed, the mixture is loaded into a vibrating mill and subjected to co-grinding with a vibration amplitude of between 5 and 12 mm for 1 hour. When said period has elapsed, the product obtained is a fine flowable powder with a minimum yield of 98.6%.
- Preparation B in the same way, a further 10 kg of the same propolis is mixed with 30 kg of dehydrogenated palm oil for 25 minutes. When that time has elapsed, the complex obtained is dehydrated and restored to a fine, flowable powder.
- the two preparations A and B are then placed in a rotary mixer for 30 minutes.
- the mixture is further mixed with excipients, acting quickly to prevent demixing, and then subjected to compressive forces in punches, or distributed through a capsule- filling machine to give final doses of approx. 100 mg/dose of propolis (related to the initial weight, before any complexing procedure).
- the tablets undergo a film-coating process with 0.5- 1% shellac in a rotary coating pan for 1-4 hours, whereas in the second case, the process has ended.
- Preparation A 10 kg of dried propolis extract titrated in flavonoids expressed as 12% galangin is processed in a microniser able to determine powders with a particle size of 1- 10 micrometers.
- the micronised powder When the micronised powder has been obtained, it is mixed and homogenised for 10 minutes in a rotary mixer with 10 kg of glutamic acid.
- the mixture When said period has elapsed, the mixture is loaded into a vibrating mill and subjected to co-grinding with a vibration amplitude of between 5 and 12 mm for 1 hour.
- the product obtained is a fine flowable powder with a minimum yield of 98.6%.
- Preparation B in the same way, a further 10 kg of the same propolis is mixed with 30 kg of distearoylphosphatidylserine for 15 minutes. When that time has elapsed, the complex obtained is dehydrated and restored to a fine, flowable powder.
- the two preparations A and B are then placed in a rotary mixer for 30 minutes. When said time has elapsed, the mixture is further mixed with excipients, acting quickly to prevent demixing, and then distributed, through a rotary screw, between disposable sachets, to give final doses of approx. 500 mg/dose of propolis (related to the initial weight, before any complexing procedure).
- the products obtained in the preceding examples may be mixed with excipients that modify their release on a time- or pH-dependent basis.
- Compounds such as the following may be used for this purpose: polyvinylpolypyrrolidone XL and derivatives thereof to promote immediate release, within 5-10 seconds; Explocel® and derivatives thereof to promote rapid release, 3-5 minutes; Avicel®, Microcel®, mannitol and dicalcium phosphate and derivatives thereof to obtain non-controlled release, dictated only by the compression forces used in the manufacture of the finished product; Methocel® or Metholose® with different degrees of curing and derivatives thereof to promote delayed release, between the next 2 and 12 hours; mixtures of ammonium carbonate, triethyl citrate and shellac to promote pH-dependent release.
- immediate release forms may contain conventional excipients as binder agents, such as polyvinylpyrrolidone, carboxymethylcellulose, microcrystalline cellulose, lactose, saccharose, mannitol, gum arabic, pectin, gelatin and the like; disintegrating agents such as croscarmellose sodium, starch, sorbitol, sodium starch glycolate, alginates, polyvinylpyrrolidone and the like; lubricants, such as talc, magnesium stearate, stearic acid, silica gel and the like; diluents and glide agents, such as calcium phosphate, silicon dioxide, starch, talc and the like; coating agents, such as sodium carboxymethylcellulose, wax, gelatin, shellac, titanium dioxide and the like; flavourings and sweeteners, such as acesulfame potassium and the like.
- binder agents such as polyvinylpyrrolidone, carboxymethylcellulose, microcrystalline cellulose, lactose, sac
- normal-release forms may contain conventional excipients as disintegrating agents, such as croscarmellose sodium, magnesium stearate, alginates, silicon dioxide, sodium carboxymethylcellulose and the like, and calcium phosphate.
- disintegrating agents such as croscarmellose sodium, magnesium stearate, alginates, silicon dioxide, sodium carboxymethylcellulose and the like, and calcium phosphate.
- slow-release forms may contain conventional excipients as retardants, such as ethylcellulose, methylcellulose, polyvinyl acetate, methacrylic acid esters, cellulose acetate, fatty alcohols, glycerol esters of fatty acids, paraffin wax, natural gums and hydrogenated vegetable oils, together with the above-mentioned conventional excipients.
- retardants such as ethylcellulose, methylcellulose, polyvinyl acetate, methacrylic acid esters, cellulose acetate, fatty alcohols, glycerol esters of fatty acids, paraffin wax, natural gums and hydrogenated vegetable oils, together with the above-mentioned conventional excipients.
- the product can be prepared by wet granulation and subsequent drying, dry granulation or compression; the third of said procedures is the most commonly used.
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- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
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- Public Health (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Insects & Arthropods (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Inorganic Chemistry (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2009A001219 | 2009-07-09 | ||
ITMI2009A001219A IT1395351B1 (it) | 2009-07-09 | 2009-07-09 | Formulazioni orali ad elevata biodisponibilita' orale costituite da miscele di frazioni lipofile e idrofile ottenute a partire dalla propoli |
Publications (1)
Publication Number | Publication Date |
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WO2011057686A1 true WO2011057686A1 (en) | 2011-05-19 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP2010/003843 WO2011057686A1 (en) | 2009-07-09 | 2010-06-28 | Oral formulations with high oral bioavailability consisting of mixtures of lipophilic and hydrophilic fractions obtained from propolis |
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Country | Link |
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IT (1) | IT1395351B1 (it) |
WO (1) | WO2011057686A1 (it) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016010440A1 (en) * | 2014-07-18 | 2016-01-21 | Manuka Health New Zealand Limited | Propolis and extracts thereof for the treatment of skin cancers and improvement of skin health |
CN113559060A (zh) * | 2021-08-12 | 2021-10-29 | 广东药科大学 | 蜂胶磷脂复合物的亚微乳剂及其制备方法 |
EP4159198A1 (fr) * | 2021-10-04 | 2023-04-05 | Larena | Procédé de fabrication d'une poudre comprenant un support biologique sur lequel est déposé un extrait biologique |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US504323A (en) | 1893-09-05 | btje kle | ||
EP0209038A1 (en) | 1985-07-17 | 1987-01-21 | I D B Holding S.P.A. | Complexes of flavanolignanes with phospholipids, preparation thereof and associated pharmaceutical compositions |
EP0275005A2 (en) | 1987-01-14 | 1988-07-20 | INDENA S.p.A. | Complex compounds of bioflavonoids with phospholipids, their preparation and use, and pharmaceutical and cosmetic compositions containing them |
US6241975B1 (en) * | 1999-07-24 | 2001-06-05 | Pacific Corporation | Method for preparation of plant extract powder |
WO2004050063A1 (en) * | 2002-12-02 | 2004-06-17 | Actimex S.R.L. | Quaternary compounds comprising propolis as the active substance |
WO2007053874A1 (de) * | 2005-11-09 | 2007-05-18 | Martin Imhof | Verwendung von propolis zur herstellung eines medikaments |
EP1837030A1 (en) | 2006-03-09 | 2007-09-26 | INDENA S.p.A. | Phospholipid complexes of curcumin having improved bioavailability |
-
2009
- 2009-07-09 IT ITMI2009A001219A patent/IT1395351B1/it active
-
2010
- 2010-06-28 WO PCT/EP2010/003843 patent/WO2011057686A1/en active Application Filing
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US504323A (en) | 1893-09-05 | btje kle | ||
EP0209038A1 (en) | 1985-07-17 | 1987-01-21 | I D B Holding S.P.A. | Complexes of flavanolignanes with phospholipids, preparation thereof and associated pharmaceutical compositions |
EP0275005A2 (en) | 1987-01-14 | 1988-07-20 | INDENA S.p.A. | Complex compounds of bioflavonoids with phospholipids, their preparation and use, and pharmaceutical and cosmetic compositions containing them |
US6241975B1 (en) * | 1999-07-24 | 2001-06-05 | Pacific Corporation | Method for preparation of plant extract powder |
WO2004050063A1 (en) * | 2002-12-02 | 2004-06-17 | Actimex S.R.L. | Quaternary compounds comprising propolis as the active substance |
EP1572155A1 (en) | 2002-12-02 | 2005-09-14 | Actimex S.R.L. | Quaternary compounds comprising propolis as the active substance |
WO2007053874A1 (de) * | 2005-11-09 | 2007-05-18 | Martin Imhof | Verwendung von propolis zur herstellung eines medikaments |
EP1837030A1 (en) | 2006-03-09 | 2007-09-26 | INDENA S.p.A. | Phospholipid complexes of curcumin having improved bioavailability |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016010440A1 (en) * | 2014-07-18 | 2016-01-21 | Manuka Health New Zealand Limited | Propolis and extracts thereof for the treatment of skin cancers and improvement of skin health |
CN113559060A (zh) * | 2021-08-12 | 2021-10-29 | 广东药科大学 | 蜂胶磷脂复合物的亚微乳剂及其制备方法 |
EP4159198A1 (fr) * | 2021-10-04 | 2023-04-05 | Larena | Procédé de fabrication d'une poudre comprenant un support biologique sur lequel est déposé un extrait biologique |
FR3127696A1 (fr) * | 2021-10-04 | 2023-04-07 | Larena | Procédé de fabrication d’une poudre comprenant un support biologique sur lequel est déposé un extrait biologique |
Also Published As
Publication number | Publication date |
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IT1395351B1 (it) | 2012-09-14 |
ITMI20091219A1 (it) | 2011-01-10 |
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