WO2006005844A1 - Composition moussante pressurisee pour le traitement topique du psoriasis - Google Patents
Composition moussante pressurisee pour le traitement topique du psoriasis Download PDFInfo
- Publication number
- WO2006005844A1 WO2006005844A1 PCT/FR2005/001496 FR2005001496W WO2006005844A1 WO 2006005844 A1 WO2006005844 A1 WO 2006005844A1 FR 2005001496 W FR2005001496 W FR 2005001496W WO 2006005844 A1 WO2006005844 A1 WO 2006005844A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- composition
- surfactant
- vitamin
- corticosteroid
- 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
Links
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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A61K9/122—Foams; Dry foams
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
Definitions
- the present invention relates to topical compositions for the treatment of psoriasis.
- Psoriasis is a chronic inflammatory skin disease affecting about 5% of the French population. This disease is manifested by red patches covered with whitish films that are detached from the skin: these are the dander. Psoriasis plaques are often located at the elbows, scalp and knees, but can also reach other parts of the body such as the face, hands, feet, mucous membranes. Psoriasis is neither contagious nor allergic in nature, but it is likely to be transmitted by heredity, in the form of a sensitivity to develop the disease. Psoriasis can occur at any age, but the first flares appear mostly between 10 and 30 years of age.
- corticosteroids in the treatment of psoriasis.
- the mechanism of action of corticosteroids is attributed to their inhibition of inflammatory processes (Lange K et al,
- US 4,610,978 discloses the use of vitamin D or a vitamin D analogue, optionally combined with a corticosteroid for the treatment of psoriasis. It is known to date to use a combination of active agents in the treatment of psoriasis, and in particular a combination of a corticosteroid and vitamin D or a vitamin D analogue. In fact, combined therapy is advantageous because it reduces the doses of the assets administered, and thus reduce the side effects of these assets.
- WO 00/64450 discloses, for the treatment of psoriasis, a pharmaceutical composition for dermal use comprising at least one vitamin D analogue and at least one corticosteroid. These compositions are presented in the form of lotions or creams.
- WO 02/34235 describes, for the treatment of psoriasis, a pharmaceutical composition in the form of a gel for application to the skin, comprising at least one vitamin D analogue, at least one corticosteroid and a viscosity-increasing excipient.
- composition for the treatment of psoriasis which is in the form of a pressurized aqueous foam and which contains the combination of a vitamin D analog and corticosteroid.
- the present invention relates to a stable pressurized aqueous foaming pharmaceutical composition for topical use, intended for the treatment of psoriasis, comprising a hydrophilic phase, at least one hydrophobic phase, a surfactant, and as active principle a combination of vitamin D analog such as calcitriol and corticosteroid such as clobetasol propionate and at least one propellant.
- pressurized means a composition which comprises at least one propellant.
- the foaming pharmaceutical composition can optionally comprising a co-surfactant, a solvent and an organic cosolvent, a gelling agent.
- foaming pharmaceutical compositions of the invention are numerous. Indeed, since the foams are easy to apply, especially in the scalp, they improve patient compliance.
- composition for topical use a composition intended to be applied to all parts of the body such as the scalp, mucous membranes, elbows, knees, hands, feet, face etc. .
- hydrophilic phase is meant a phase composed mainly of water.
- the hydrophobic phase also hereinafter referred to as the hydrophobic solvent, can be, without being limited to, a vegetable oil, an animal oil, a mineral oil which is liquid or solid at ambient temperature, a silicone oil or a synthetic oil. mixtures.
- the hydrophobic phase can act as the solvent of (s) active (s).
- the active agent may be solubilized in an organic solvent that is different from the hydrophobic phase.
- This solvent may be derived from glycol, for example propylene glycol, a fatty acid ester such as a C12-C15 alkyl chain alkyl benzoate, a medium or long chain alcohol, a fatty alcohol, an aromatic pyrolidinone or alkyl, a cyclic ketone, an ether cyclic, linear, branched or cyclic chain alkane.
- Gelling agents that may be mentioned include polysaccharides and derivatives such as alginates, chitosans, starches and derivatives, natural and derived gums such as xanthan gum, clays, synthetic polymers such as cellulose derivatives, polyvinylpyrrolidones and derivatives, carboxyvinyl polymers, acrylic coproplymers such as copolymers of acrylates / alkylacrylates, polyacrylamides Pemulen.
- Examples of vegetable oils include soybean oil, cottonseed oil, sweet almond oil, palm oil, sesame oil, sunflower oil.
- animal oil include lanolin oil, squalene, fish oil, mink oil.
- mineral oil include paraffin oils of different viscosities such as Primol 352, Marcol 82, Marcol 152 sold by the company Esso.
- synthetic oils mention may be made of an ester such as cetearyl isononanoate sold under the name Cetiol SN by Cognis France, isopropyl palmitate, octyl palmitate, isostearic acid derivatives and neopentylglycol.
- dicaprylate / dicaprate hydrogenated glycerides
- diisopropyl adipate sold under the name Ceraphyl 230 by the company ISF
- isopropyl palmitate sold under the name of Crodamol IPP by the company Croda
- the isononyl isononanoate sold under the name of Dub Inin by Stéarinerie Dubois
- the caprylic / capric triglyceride such as Miglyol 812 sold by the company HuIs / Lambert River.
- silicone oil are non-silicone silicones the
- the hydrophobic solvent may be present in a concentration ranging from 20% to 75% by weight relative to the total weight of the composition (w / w), preferably from 20% to 50% (w / w).
- the gelling agent may be present in a concentration ranging from 0.1% to 5.0% (w / w).
- vitamin D analogue is calcitriol, tacalcitol, calcipotriol, and any other vitamin D analog mentioned in the patent.
- the vitamin D analog is calcitriol.
- corticosteroid As an example of a corticosteroid, mention may be made of clobetasol and its esters, such as clobetasol 17-propionate (also referred to as clobetasol propionate), bethametasone and its esters, fluocinonide, hydrocortisone and any other corticosteroid mentioned in the patent. WO 00/64450.
- the corticosteroid is clobetasol propionate.
- the surfactant may be a nonionic, zwitterionic, anionic or cationic surfactant, or a mixture of these surfactants.
- the nonionic surfactant may be selected from the group consisting of ethoxylated sorbitan stearate, ethoxylated sorbitan palmitate, the
- Ethoxylated sorbitan oleate nonyl phenol ethoxyls, fatty alcohol ethoxyls, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, sucrose esters, pegylated esters or mixtures thereof.
- the zwitterionic surfactant may be a cocamidoalkylamine, and especially a cocamidopropylamine and / or cocamidopropylamine oxide.
- the cationic surfactant may be a betaine.
- the anionic surfactant may be sodium lauryl sulfate.
- the surfactant is nonionic.
- the co-surfactant is selected from co-surfactants having an HLB between 6 and 10, preferably between 6 and 8.
- the present invention also relates to a composition comprising at least one propellant gas.
- This propellant may be a gas known to those skilled in the art, such as hydrocarbons, CFCs, HFCs, nitrogen, carbon dioxide, air, or mixtures thereof.
- An example of these gases is propane, butane, isobutane, dichloro-difluoromethane, dichloro-tetrafluoroethane, octafluorocyclobutane, dimethyl ether or mixtures thereof.
- the propellant gas is in liquefied form and its concentration is between 5-30% of the total composition.
- composition which is the subject of the present invention may furthermore comprise an emulsifying agent, one or more absorption promoters, a suitable buffer substance, preservatives and / or an antioxidant.
- emollient agent By way of example of an emollient agent, mention may be made of glycerine, panthenol or sorbitol.
- buffer substances examples include acetic acid / sodium acetate, citric acid / sodium citrate, phosphoric acid / sodium phosphate or anhydrous citric acid / potassium citrate.
- the antioxidant may be 4-aminosalicylic acid, 5-aminosalicylic acid, butyl hydroxytoluene, butyl hydroxyanisole, propyl gallate, superoxide dismutase, ubiquinol, ⁇ -tocopherol and derivatives or certain metal chelants.
- the antioxidants preferentially used in the composition according to the invention are D, L ⁇ -tocopherol, butyl hydroxyanisole and butyl hydroxytoluene.
- the asset can be encapsulated in a drug transport system to increase its stability.
- a drug carrier is a lipid carrier, a cyclodextrin, a direct or reverse micellar system.
- the surfactant is present in an amount ranging from 0.1% to 15% by weight relative to total weight of the composition, preferably from 0.1% to 10%, preferably from 0.2% to 5%.
- the vitamin D analogue is present in an amount of from 0.0001% to 1%, preferably from
- the corticosteroid is present in an amount ranging from 0.001% to 1%, preferably from 0.001% to 0.2% and most preferably from 0.005% to 0.1% by weight relative to the total weight of the composition.
- the propellant is present in an amount ranging from 3% to 30%, preferably from 3% to 10% by weight relative to the total weight of the composition.
- the hydrophobic phase is present in an amount ranging from 20% to 75%, preferably from 20% to 50% by weight relative to the total weight of the composition.
- the present invention also relates to an aerosol can comprising a composition as defined above.
- the present invention also relates to a process for preparing a foaming pharmaceutical composition, as defined above, in an aerosol container.
- the process for preparing the foaming composition that is the subject of the present invention is characterized in that it comprises the following steps: (a) the active ingredients are solubilized separately in a suitable solvent;
- the present invention further relates to the use of a mixture of vitamin D analogue and a corticosteroid for the manufacture of a foaming pharmaceutical composition for topical use for the treatment of psoriasis.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002567687A CA2567687A1 (fr) | 2004-06-17 | 2005-06-15 | Composition moussante pressurisee pour le traitement topique du psoriasis |
| EP05777132A EP1778185A1 (fr) | 2004-06-17 | 2005-06-15 | Composition moussante pressurisée pour le traitement topique du psoriasis |
| JP2007515998A JP2008502663A (ja) | 2004-06-17 | 2005-06-15 | 乾癬の局所治療用加圧型発泡性組成物 |
| BRPI0510840-3A BRPI0510840A (pt) | 2004-06-17 | 2005-06-15 | composição farmacêutica, composição pressurizada, bomba aerossol e uso de uma mistura de análogo de vitamina d e de um corticosteróide |
| MXPA06014409A MXPA06014409A (es) | 2004-06-17 | 2005-06-15 | Composicion de espuma presurizada para tratamiento topico de psoriasis. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0406613A FR2871696B1 (fr) | 2004-06-17 | 2004-06-17 | Composition topique pour le traitement du psoriasis |
| FR0406613 | 2004-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006005844A1 true WO2006005844A1 (fr) | 2006-01-19 |
Family
ID=34949090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR2005/001496 Ceased WO2006005844A1 (fr) | 2004-06-17 | 2005-06-15 | Composition moussante pressurisee pour le traitement topique du psoriasis |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20050281755A1 (fr) |
| EP (1) | EP1778185A1 (fr) |
| JP (1) | JP2008502663A (fr) |
| KR (1) | KR20070024598A (fr) |
| CN (1) | CN1968681A (fr) |
| AU (1) | AU2005261571A1 (fr) |
| BR (1) | BRPI0510840A (fr) |
| CA (1) | CA2567687A1 (fr) |
| FR (1) | FR2871696B1 (fr) |
| MX (1) | MXPA06014409A (fr) |
| RU (1) | RU2007101540A (fr) |
| WO (1) | WO2006005844A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008027532A3 (fr) * | 2006-08-29 | 2008-04-17 | Teva Pharma | Compositions actives pharmacologiquement stables à base de vitamine d et de corticostéroïdes, compatibles avec un faible ph |
| JP2010524888A (ja) * | 2007-04-18 | 2010-07-22 | ピエール、ファブレ、デルモ‐コスメティーク | シクロピロクスオラミンおよび亜鉛ピリチオンを含む抗真菌泡ならびにその医療用途および化粧用途 |
| EP1917072A4 (fr) * | 2005-06-01 | 2010-10-13 | Stiefel Res Australia Pty Ltd | Preparation vitaminee |
| US8263580B2 (en) | 1998-09-11 | 2012-09-11 | Stiefel Research Australia Pty Ltd | Vitamin formulation |
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| AUPP583198A0 (en) * | 1998-09-11 | 1998-10-01 | Soltec Research Pty Ltd | Mousse composition |
| US8512718B2 (en) | 2000-07-03 | 2013-08-20 | Foamix Ltd. | Pharmaceutical composition for topical application |
| IL152486A0 (en) | 2002-10-25 | 2003-05-29 | Meir Eini | Alcohol-free cosmetic and pharmaceutical foam carrier |
| US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
| US7820145B2 (en) | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| US9265725B2 (en) | 2002-10-25 | 2016-02-23 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
| US8119109B2 (en) | 2002-10-25 | 2012-02-21 | Foamix Ltd. | Foamable compositions, kits and methods for hyperhidrosis |
| US20060018937A1 (en) * | 2002-10-25 | 2006-01-26 | Foamix Ltd. | Steroid kit and foamable composition and uses thereof |
| US7700076B2 (en) | 2002-10-25 | 2010-04-20 | Foamix, Ltd. | Penetrating pharmaceutical foam |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
| US8486376B2 (en) | 2002-10-25 | 2013-07-16 | Foamix Ltd. | Moisturizing foam containing lanolin |
| CA2502986C (fr) | 2002-10-25 | 2011-08-23 | Foamix Ltd. | Mousse cosmetique et pharmaceutique |
| US8119150B2 (en) | 2002-10-25 | 2012-02-21 | Foamix Ltd. | Non-flammable insecticide composition and uses thereof |
| US20080138296A1 (en) | 2002-10-25 | 2008-06-12 | Foamix Ltd. | Foam prepared from nanoemulsions and uses |
| US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| US10117812B2 (en) | 2002-10-25 | 2018-11-06 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
| US7575739B2 (en) | 2003-04-28 | 2009-08-18 | Foamix Ltd. | Foamable iodine composition |
| US8486374B2 (en) | 2003-08-04 | 2013-07-16 | Foamix Ltd. | Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses |
| US8795693B2 (en) | 2003-08-04 | 2014-08-05 | Foamix Ltd. | Compositions with modulating agents |
| US8211449B2 (en) * | 2004-06-24 | 2012-07-03 | Dpt Laboratories, Ltd. | Pharmaceutically elegant, topical anhydrous aerosol foam |
| CA2610662A1 (fr) | 2005-05-09 | 2007-05-18 | Foamix Ltd. | Excipient expansible et compositions pharmaceutiques contenant celui-ci |
| GB2443161B (en) * | 2006-10-28 | 2011-03-23 | Nupharm Lab Ltd | Clobetasol spray |
| GB2443162B (en) * | 2006-10-28 | 2011-02-09 | Nupharm Lab Ltd | Betamethasone spray |
| US20080260655A1 (en) | 2006-11-14 | 2008-10-23 | Dov Tamarkin | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
| US9532936B2 (en) | 2007-03-08 | 2017-01-03 | Strength Of Nature, Llc | Compositions and methods for removing hair styling aids |
| EP1970048A1 (fr) * | 2007-03-15 | 2008-09-17 | Drug Delivery Solutions Limited | Composition topique de type polyaphron avec de la vitamine D |
| EP1970049A1 (fr) * | 2007-03-15 | 2008-09-17 | Drug Delivery Solutions Limited | Composition topique du type polyaphron avec de la vitamine D et un corticosteroide |
| US10265265B2 (en) | 2007-03-15 | 2019-04-23 | Drug Delivery Solutions Limited | Topical composition |
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| WO2009072007A2 (fr) | 2007-12-07 | 2009-06-11 | Foamix Ltd. | Porteurs, formulations, procédés pour formuler des agents actifs instables pour application externe et utilisations associées |
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| FR3041538B1 (fr) * | 2015-09-29 | 2018-11-30 | Galderma Research & Development | Mousse chimique non rincee contenant du propionate de clobetasol, et son utilisation dans le traitement du psoriasis. |
| GB201604316D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
| GB201604318D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
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| CA3037582A1 (fr) | 2016-09-21 | 2018-03-29 | Avexxin As | Composition pharmaceutique |
| EP3542788A1 (fr) | 2018-03-19 | 2019-09-25 | MC2 Therapeutics Limited | Composition topique comprenant calcipotriol et dipropionate de bétaméthasone |
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| US5223244A (en) * | 1988-06-20 | 1993-06-29 | Shiseido Company, Ltd. | Aerosol composition |
| US5185166A (en) * | 1988-12-07 | 1993-02-09 | San-Ei Chemical Industries, Ltd. | Process for the production of milk mineral concentrate and drink containing minerals |
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2004
- 2004-06-17 FR FR0406613A patent/FR2871696B1/fr not_active Expired - Fee Related
- 2004-10-15 US US10/965,195 patent/US20050281755A1/en not_active Abandoned
-
2005
- 2005-06-15 RU RU2007101540/15A patent/RU2007101540A/ru unknown
- 2005-06-15 MX MXPA06014409A patent/MXPA06014409A/es not_active Application Discontinuation
- 2005-06-15 JP JP2007515998A patent/JP2008502663A/ja not_active Withdrawn
- 2005-06-15 WO PCT/FR2005/001496 patent/WO2006005844A1/fr not_active Ceased
- 2005-06-15 BR BRPI0510840-3A patent/BRPI0510840A/pt not_active Application Discontinuation
- 2005-06-15 AU AU2005261571A patent/AU2005261571A1/en not_active Abandoned
- 2005-06-15 CA CA002567687A patent/CA2567687A1/fr not_active Abandoned
- 2005-06-15 EP EP05777132A patent/EP1778185A1/fr not_active Withdrawn
- 2005-06-15 KR KR1020067026292A patent/KR20070024598A/ko not_active Withdrawn
- 2005-06-15 CN CNA2005800199993A patent/CN1968681A/zh active Pending
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263580B2 (en) | 1998-09-11 | 2012-09-11 | Stiefel Research Australia Pty Ltd | Vitamin formulation |
| EP1917072A4 (fr) * | 2005-06-01 | 2010-10-13 | Stiefel Res Australia Pty Ltd | Preparation vitaminee |
| US8298515B2 (en) | 2005-06-01 | 2012-10-30 | Stiefel Research Australia Pty Ltd. | Vitamin formulation |
| US8629128B2 (en) | 2005-06-01 | 2014-01-14 | Stiefel West Coast, Llc | Vitamin formulation |
| WO2008027532A3 (fr) * | 2006-08-29 | 2008-04-17 | Teva Pharma | Compositions actives pharmacologiquement stables à base de vitamine d et de corticostéroïdes, compatibles avec un faible ph |
| JP2010502624A (ja) * | 2006-08-29 | 2010-01-28 | テバ ファーマシューティカル インダストリーズ リミティド | 低pH親和性を有するコルチコステロイド化合物及びビタミンD含有化合物を含む安定な薬理活性組成物 |
| JP2010524888A (ja) * | 2007-04-18 | 2010-07-22 | ピエール、ファブレ、デルモ‐コスメティーク | シクロピロクスオラミンおよび亜鉛ピリチオンを含む抗真菌泡ならびにその医療用途および化粧用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2567687A1 (fr) | 2006-01-19 |
| JP2008502663A (ja) | 2008-01-31 |
| BRPI0510840A (pt) | 2007-11-27 |
| MXPA06014409A (es) | 2007-02-19 |
| US20050281755A1 (en) | 2005-12-22 |
| FR2871696A1 (fr) | 2005-12-23 |
| CN1968681A (zh) | 2007-05-23 |
| KR20070024598A (ko) | 2007-03-02 |
| FR2871696B1 (fr) | 2006-11-10 |
| EP1778185A1 (fr) | 2007-05-02 |
| AU2005261571A1 (en) | 2006-01-19 |
| RU2007101540A (ru) | 2008-07-27 |
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