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EP0866689A1 - Pulverisateur d'hydrocortisone pour administration topique - Google Patents

Pulverisateur d'hydrocortisone pour administration topique

Info

Publication number
EP0866689A1
EP0866689A1 EP96939798A EP96939798A EP0866689A1 EP 0866689 A1 EP0866689 A1 EP 0866689A1 EP 96939798 A EP96939798 A EP 96939798A EP 96939798 A EP96939798 A EP 96939798A EP 0866689 A1 EP0866689 A1 EP 0866689A1
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
dermal
combination
component
active ingredient
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
EP96939798A
Other languages
German (de)
English (en)
Inventor
Hans Georg Weder
Marc Antoine Weder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vesifact AG
Original Assignee
Vesifact AG
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 Vesifact AG filed Critical Vesifact AG
Publication of EP0866689A1 publication Critical patent/EP0866689A1/fr
Ceased legal-status Critical Current

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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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

Definitions

  • the present invention relates to a pharmaceutical composition for the dermal application of hydrocortisone or a derivative thereof, a process for the preparation of this pharmaceutical composition and its use in therapy
  • the body's own glucocorticoid hormone hydrocortisone (cortisol), Merck Index Elevenlh Edition (1989), No. 47J0, page 4711, chemical name: 11, 17, 21-trihydroxypregn-4- en-3,20-dione, is used dermally as an anti-inflammatory agent for treatment of inflammatory skin diseases, e.g. Eczema, psoriasis, dermatitis, contact allergies, etc. administered The Index Nominum 1992/93, Swiss Pharmaceutical Society, Medpharm, Be ent ß c Publ. D-Stuttgari, lists 81 dermal preparations with registered trademarks for the active ingredient hydrocortisone. There are also numerous of the derivatives, especially the 21 acetate
  • the present invention is therefore based on the object of producing a dermal preparation for the active ingredient hydrocortisone with improved effectiveness at low dosage.
  • the present invention is therefore based on the object in the narrower sense, to produce an improved dermal preparation for the active ingredient hydrocortisone, which is suitable for over-the-counter dispensing as a so-called OTC preparation (over-the-counter preparation) as part of the so-called self-medication
  • the solution to the problem is based on the consideration that by increasing the solubility of the active ingredient hydrocortisone in the formulation base, an improvement in activity should be achieved with a consistently low concentration.
  • Hydrocortisone itself is poorly soluble in water, which is an essential component in dermal formulations.
  • Merck Index, loc. eit. indicates a water solubility of 0.28 mg / ml (25 ° C)
  • the active ingredient is more soluble in ethanol 15 mg / ml (25 ° C)
  • the addition of large amounts of ethanol to improve the solubility of the active ingredient is for dermal preparations unfavorable, since ethanol also acts as a solvent for other components of the formulation and requires the skin to dry out.
  • a lipophilic formulation base consisting of a partial fatty acid ester of polyoxyethylene sorbitan, a phospholipid and a neutralol is suitable for producing a particularly homogeneous, finely dispersed, nanodispersion of the active ingredient hydrocortisone
  • the subject of the present invention is a pharmaceutical composition for the dermal application of a corticoid, which contains the following components: a) the active ingredient 1 l, 17,21-trihydroxypregn-4-en-3,20-dione (hydrocortisone) or a derivative thereof, optionally in combination with a wound treatment agent, b) at least one partial fatty acid ester of polyoxyethylene sorbitan or a combination thereof; c) at least one essentially pure phospholipid of the formula:
  • R C ⁇ o- 2 o-acyl, R 2 hydrogen or C ⁇ o- 2 o-acyl, R 3 hydrogen, 2-trimethylamino-1-ethyl, 2-amino-1-ethyl, C M - alkyl, C ⁇ - 5 alkyl substituted by Carboxy, C 2 .5-alkyl substituted by hydroxy, C 2 . 5- alkyl substituted by carboxy and hydroxy or C ⁇ -s-alkyl substituted by carboxy and amino, which mean inositol or the glyceryl group, or salts of these compounds; d) a triglyceride of the formula:
  • Ri, R 2 and R 3 Cg. 24 is acyl; e) water as carrier liquid in the purity required for dermal application; and optionally f) excipients suitable for dermal dosage forms.
  • This pharmaceutical composition is characterized by favorable phase properties of the solubilized active ingredient. With opalescence and transparency in the backlight, it can only be seen from an extremely low milky haze that the suspension still shows physical differences from the ideal state of a real molecular solution. Electron microscopic images show that a population of more than 98% of the active ingredient is in a Gaussian distribution as a dispersion of particles (nanoparticles) with a particle size smaller than approx. 50 nm (nanodispersion).
  • a preferred embodiment relates to a pharmaceutical composition
  • a pharmaceutical composition comprising a) the active ingredient hydrocortisone or the 21 acetate, optionally in combination with dexpanthenol, b) the combination consisting of polysorbate 20, 80 and 60, c) purified lecithin from soybeans, d) a triglyceride the group of neutral oils, and e) water as carrier liquid in the purity required for dermal application, and optionally f) auxiliaries suitable for dermal dosage forms
  • the active ingredient hydrocortisone - component a) - is contained in the pharmaceutical composition defined above in the dosage permissible for dermal application.
  • the active ingredient hydrocortisone - component a) - is contained in the pharmaceutical composition defined above in the dosage permissible for dermal application.
  • the commercial formulations according to the Red List or Medicinal Compendium of Switzerland, Documed Basel, Switzerland there is one dose in non-prescription dermal preparations from about 0.1 to 0.5% (converted to free hydrocortisone)
  • a derivative of hydrocortisone is in particular 21-acetate, 21-acetate-17-propionate (aceponate), 21-bendazac, 17 ⁇ -butyrate, 17 ⁇ -butyrate-21-propionate, 21-cipionate (cyclopentane propionate), 21-dinatium phosphate , 21-hydrogen succinate, 21 -sodium succ ⁇ nate, 21 - tebutate (tert-butyl acetate), 17-valerate or the xanthate
  • the active ingredient hydrocortisone or one of the derivatives mentioned can be contained in the pharmaceutical composition in combination with a known wound treatment agent or epithelizing agent, for example dexpanthenol
  • Component b) - partial fatty acid ester of polyoxyethylene sorbitan preferably consists of an essentially pure or a mixture of different esters of sorbitan, in which the structure of the fatty acid groups and the length of the polyoxyethylene chains vary.
  • the sorbitan is preferably etherified by three hydrophilic polyoxyethylene chains and esterified by a hydrophobic fatty acid group But the sorbitan can only be done by one or two hydrophilic polyoxyethylene chains must be etherified and correspondingly esterified by three or two hydrophobic fatty acid groups.
  • the sorbitan basic body is substituted by at least one to a maximum of three hydrophilic polyoxyethylene groups and accordingly by a maximum of three and at least one hydrophobic fatty acid group
  • the polyoxyethylene chain is straight-chain and preferably has 4-10, in particular 4-8, ethylene oxide units.
  • the ester groups on the sorbitan base are derived from a saturated or unsaturated, straight-chain carboxylic acid and an even number of 8-20 carbon atoms.
  • the ester group derived from this carboxylic acid is preferably straight-chain with 12, 14, 16 and 18 carbon atoms, for example n-dodecanoyl, n-tetradecanoyl, n-hexadecanoyl or n-octadecanoyl
  • the ester group derived from an unsaturated carboxylic acid with an even number of 8-20 C atoms is preferably straight-chain with 12, 14, 16 and 18 C atoms, for example Oleoyl.
  • the esters of sorbitan mentioned fulfill the information given in the British Pharmacopoeia (special monograph) or Ph. Helv. VII.
  • the product descriptions published by the named manufacturers with the information on data sheets for the relevant product apply, in particular specifications such as shape, color, HLB value, viscosity, rising melting point and solubility
  • Suitable partial fatty acid esters of polyoxyethylene sorbitan are commercially available under the word symbol Tween * 81 from ICI and have the chemical names polyoxyethylene (20 or 4) sorbitan monolaurate (TWEEN 20 and 21), polyoxyethylene (20) sorbitan monopalmitate or monostearate ( TWEEN 40 and 60), polyoxyethylene (4 or 20) sorbitan monostearate or tristearate (TWEEN 61 and 65), polyoxyethylene (20 or 5) sorbitan mono oleate (TWEEN 80 or 81) or polyoxyethylene (20) -sorbitan trioleate (TWEEN 85) known
  • a combination consisting of TWEEN 20, TWEEN 80 and TWEEN 60 or polysorbate 20, 80 and 60 is used as component b)
  • Component b) is contained in the pharmaceutical composition in a proportion (based on the total weight of the formulation) of approximately 1.0% to 5.0%, preferably 1.0% to 3.0% Component c) - Phospholipid of the formula I
  • the nomenclature of the phosphohpides (I) and the numbering of the C atoms is carried out using the "Nomenclature of Lipids" from the IUPAC-IUB Commission on in Eur J ofBiochem 79, 1 1-21 (1977) Biochemical Nomenclature (CBN) given recommendations (sn-nomenclature, stereospecific numbe ⁇ ng)
  • R 1 and R 2 with the meanings C ] 0-2 o-acyl are preferably straight-chain C 10 .
  • Straight-chain C 10-20 alkanoyl R 1 and R 2 with an even number of C atoms are, for example, n-dodecanoyl, n-tetradecanoyl, n-hexadecanoyl or n-octadecanoyl
  • Straight-chain C ⁇ o- 2 o-alkenoyl R 1 and R 2 with a double bond and an even number of carbon atoms are, for example, 6-cis or 6-trans, 9-cis or 9-trans-dodecenoyl, tetradecenoyl, hexadecenoyl , Octadecenoyl or icosenoyl, in particular 9-cis-octa-decenoyl (oleoyl), further 9,12-cis-octadecadienoyl or 9, 12,15-cis-octadecatrienoyl
  • a phospholipid (I) in which R 3 denotes 2-trimethylamino-1-ethyl is designated with the trivial name lecithin and a phospholipid (I) in which R 3 denotes 2-amino-1-ethyl with the trivial name cephalin are suitable, for example naturally occurring cephalin or lecithin, for example cephalin or lecithin from soybeans or chicken eggs with different or identical acyl groups R 1 and R 2 , or mixtures thereof
  • the phospholipid (I) can also be of synthetic origin.
  • synthetic phospholipid is used to define phosphohpides which have a uniform composition with respect to R 1 and R 2 .
  • Such synthetic phosphohpides are preferably the lecithins and cephalins defined above, whose acyl groups R 1 and R 2 have a defined structure and are derived from a defined fatty acid with a purity higher than about 95%.
  • R 1 and R 2 can be the same or different and unsaturated or saturated
  • Rj is preferably saturated, for example n-hexadecanoyl, and R 2 is unsaturated, for example 9-c ⁇ s- octadecenoyl (oleoyl)
  • phospholipid (I) defines phosphohpides which have no uniform composition with respect to Rj and R 2 .
  • Pholipids are also lecithins and kephalins, the acyl groups R 1 and R 2 of which are structurally indefinable and derived from naturally occurring fatty acid mixtures
  • the requirement "essentially pure" phospholipid (I) defines a degree of purity of more than 90% (by weight), preferably more than 95%, of the phospholipid (I), which can be determined using suitable determination methods, for example paper chromatography, with thin-layer chromatography HPLC or enzymatic. Color test, is detectable
  • R 3 is C M alkyl, for example methyl or ethyl. The meaning methyl is preferred
  • R 3 with the meanings C ⁇ _ 5 alkyl substituted by carboxy, C 2 . 5 - Alkyl substituted by hydroxy or C 2 .5-alkyl substituted by carboxy or hydroxy are for example 2-hydroxyethyl, 2,3-dihydroxy-n-propyl, carboxymethyl, 1- or 2-carboxyethyl, dicarboxymethyl, 2-carboxy -2-hydroxyethyl or 3-carboxy-2,3-dihydroxy-n-propyl
  • R 3 with the meaning C 2 - 5 alkyl substituted by carboxy and amino is for example 3-Am ⁇ no-3-carboxy-n-propyl or 2-amino-2-carboxy-n-propyl, preferably 2-Am ⁇ no-2- carboxyethy!
  • Phosphohpides (I) with these groups can be in salt form, for example as the sodium or potassium salt
  • Phosphohpides (1) in which Ri denotes the inositol or glyceryl group, are known under the names phosphatidylinositol and phosphatidylglycerol
  • 9-cis-dodecenoyl (lauroleoyl), 9-cis-tetradecenoyl (myristoleoyl), 9-cis-hexadecenoyl (palmitoleoyl), 6-cis-octadecenoyl (petroseloyl), 6-trans-octadecenoyl (petroselecoyoyl), 9 (Oleoyl), 9-trans-octadecenoyl (Elaidoyl), 9,12-cis-octadecadienoyl (Linoleoyl), 9,12, 15-cis-octadecatrienoyl (Linolenoyl), l l-cis-octadecenoyl (Vaccenoyl), 9-cis Icosenoyl (gadoleoyl), 5,8, 11,14-cis-eicosatetra
  • Component c) is added in a preferred concentration of about 0.05 to 1.0% by weight, preferably 0.05 to 0.1% by weight, based on the total weight of the formulation.
  • purified is used Lecithin from soybeans of the quality LIPOID S 100
  • R 1, R 2 and R 3 are straight-chain Cs- 24- acyl with an even number of C atoms, in particular n-octanoyl, n-dodecanoyl, n-tetradecanoyl, n -Hexadecanoyl, n-octadecanoyl, 9-cis-dodecenoyl, 9-cis-tetradecenoyl, 9-cis-hexadecenoyl, 9-cis-octadecenoyl or 9-cis- icosenoyl.
  • Ri, R 2 and R 3 can be identical or different
  • the individual groups R 1 , R 2 and R 3 are themselves structurally uniformly defined. This is characteristic of synthetic or semisynthetic triglycerides, R 1, R 2 and R-, but can also consist of different acyl groups of different structure. This is for triglycerides of natural origin characteristic
  • a triglyceride of the formula II is a semisynthetic or synthetic, essentially pure triglyceride or a pharmaceutically usable triglyceride of natural origin.
  • a triglyceride of natural origin is preferred, eg peanut, sesame, sunflower, olive, corn germ, soybean, castor -, Cottonseed, rapeseed, safflower, grape seed, fish or coconut oil
  • a triglyceride defined by the term neutralol with different acyl groups of different structure is used, for example a triglyceride of the fractionated coconut fatty acids C 8 -Cio of the Migiyol ® type, for example MIGLYOL 812
  • the triglyceride (II) is contained in the pharmaceutical composition defined above in a preferred concentration range of approximately 0.1 to 2.0% by weight, preferably 0.1 to 1.0% by weight, based on the total weight of the formulation Component e) - water as carrier liquid in the purity required for dermal application - is germ and pyrogen free according to the regulations of the national pharmacopoeia
  • auxiliaries suitable for dermal formulations - is contained as an optional component.
  • auxiliaries are contained in creams, ointments, gels, lotions, pastes, foams, tinctures or lotions
  • ethanol in particular in small amounts of approx. 0.1 to 5%, isopropanol, furthermore preservatives, for example benzalkonium chloride, phenoxyethanol, furthermore benzoic acid or its salts, 4-hydroxy-benzoic acid ester (PHB ester), phenols, eg tert -Butyl-4-methoxy- or di-tert-butyl-4-methylphenol, benzyl alcohol, 4-chloro- or 2,4-dichlorobenzyl alcohol, 2-phenylethanol, chlorhexidine diacetate or digluconate, thiabendazole, cetyltriammonium bromide, cetylpyridinium bromidium bromide, phenododecarboxylic acid, phenodinodinodromide , Antioxidants, e.g.
  • the present invention also relates to the known process for the preparation of the pharmaceutical composition, which is characterized in that a lipophilic phase consisting of components a) to d) with the aqueous carrier liquid, which optionally contains water-soluble excipients suitable for dermal dosage forms , mixed and, if desired, the available clear, opalescent dispersion based on nanoparticles - nanodispersion - undergoes the following post-operations, adding a further amount of water as carrier liquid and, if appropriate, further water-soluble auxiliaries which are suitable for dermal dosage forms, and, if appropriate, filtration (e.g. Sterile filtration) of the nanodispersion, and / or further processing of the nanodispersion into a dermal preparation
  • a lipophilic phase consisting of components a) to d) with the aqueous carrier liquid, which optionally contains water-soluble excipients suitable for dermal dosage forms , mixed and, if desired, the available clear, opalescent dispersion based
  • a lipophilic phase "oil phase” consisting of component c) - phospholipid (I) -, ethanol, component b), - partial fatty acid ester of polyoxyethylene sorbitan -, component a) - active ingredient, and component d) - triglyceride (II) - forth.
  • the components are mixed at low speed at room temperature using a conventional stirrer with a propeller or a blade, a magnetic stirrer or a static mixer.
  • a combination of different partial fatty acid esters of polyoxyethylene sorbitan is used, in particular the combination consisting of polysorbate 20, 80 and 60. Attention is paid to the sequence by first mixing the phospholipid and the ethanol with one another and then polysorbate 20, 80 in succession and 60 adds. Neutralol is then added by mixing the lipophilic phase ("oil phase") with the aqueous phase which contains water-soluble optional additives, e.g.
  • Preservatives which can contain a low-speed agitator (200 to 1,000 rpm) or a static mixer, form the pharmaceutical composition defined above, which can be defined as a dispersion of colloidal nanoparticles of the lipophilic active ingredient hydrocortisone or simply as nanodispersion due to lasers -Light scatter measurements and electron microscope images distinguish the colloidal particles present in the nanodispersion from other structures such as liquid crystals, micelles, reverse micelles or liposomes.
  • an average particle size is smaller than 50 nm characteristic
  • the nanodispersion can be applied directly after adding the desired amount of water and, if necessary, other auxiliary substances that can be used for dermal dosage forms, e.g. as a dosing spray.
  • auxiliary substances that can be used for dermal dosage forms, e.g. as a dosing spray.
  • a particular advantage over conventional dermal preparations is the possibility of sterile filtration.If desired, sterile filtration can be used to remove all those in the dispersion larger particles with a diameter larger than approx. 200 nm, as well as suspended and solid matter, and so produce a nanodispersion with a fraction of particles of relatively uniform size.
  • Suitable containers are e.g. containers for pump sprays or dosing sprays or plastic containers with a discharge device
  • composition described above with the anti-inflammatory hydrocortisone is suitable as a dermal preparation for the treatment of all diseases of the skin and on the eye.
  • the preparation is used in the prescribed dosage
  • the aqueous phase is prepared by adding (9) in (8) at room temperature.
  • the oil phase is obtained by introducing (1) in (2) until the solution becomes clear.
  • the active ingredient (6) is added in three portions and heated to 60 ° C. until no more crystals are visible. (7) add, mix until the solution becomes clear and cool to room temperature
  • the aqueous phase is combined with the oil phase by introducing the aqueous phase at room temperature and stirring at 300-400 rpm with a magnetic stirrer.
  • the oil phase is then slowly injected into the aqueous phase over a period of about two minutes at a level another 5-10 min avoiding foaming and filters the nanodispersion through a germ filter (0.2 ⁇ m)

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une préparation pharmaceutique d'application dermique d'hydrocortisone. Ce principe actif est dispersé par adjonction d'un ester d'acide gras partiel de sorbitanne de polyéthylène et d'autres auxiliaires tels que la lécithine et l'huile neutre. Ce système permet d'obtenir une suspension de particules de l'ordre du nanomètre du principe actif hydrocortisone liphophile.
EP96939798A 1995-12-12 1996-12-09 Pulverisateur d'hydrocortisone pour administration topique Ceased EP0866689A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH3499/95 1995-12-12
CH349995 1995-12-12
PCT/CH1996/000434 WO1997021428A1 (fr) 1995-12-12 1996-12-09 Pulverisateur d'hydrocortisone pour administration topique

Publications (1)

Publication Number Publication Date
EP0866689A1 true EP0866689A1 (fr) 1998-09-30

Family

ID=4257316

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96939798A Ceased EP0866689A1 (fr) 1995-12-12 1996-12-09 Pulverisateur d'hydrocortisone pour administration topique

Country Status (4)

Country Link
EP (1) EP0866689A1 (fr)
AU (1) AU7689996A (fr)
CA (1) CA2238263A1 (fr)
WO (1) WO1997021428A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59710082D1 (de) * 1996-12-13 2003-06-18 Vesifact Ag Baar Kosmetische Präparate in Form einer Nanodispersion
TWI241915B (en) * 1998-05-11 2005-10-21 Ciba Sc Holding Ag A method of preparing a pharmaceutical end formulation using a nanodispersion
TW592713B (en) * 1998-05-11 2004-06-21 Ciba Sc Holding Ag Use of nanodispersions in cosmetic end formulations
US7381423B2 (en) 1998-05-11 2008-06-03 Ciba Specialty Chemicals Corp. Use of nanodispersions in cosmetic end formulations
WO2000015763A1 (fr) * 1998-09-14 2000-03-23 Vesifact Ag Utilisation de nanocellules dans des produits finis sous forme de milieux de culture
AU770803B2 (en) 1998-12-23 2004-03-04 Idea Ag Improved formulation for topical non-invasive application in vivo
FR2820320B1 (fr) * 2001-02-02 2003-04-04 Oreal Suspension de nanospheres de principe actif lipophile stabilisee par des polymeres hydrodispersibles
EP1256337A1 (fr) 2001-05-08 2002-11-13 Vesifact Ag Méthode et compositions pour appliquer un agent sur un substrat
KR100772327B1 (ko) 2004-04-22 2007-10-31 주식회사유한양행 하이드로코티손 또는 그 염을 함유하는 나노에멀젼 조성물
GB0623838D0 (en) * 2006-11-29 2007-01-10 Malvern Cosmeceutics Ltd Novel compositions
CL2008000037A1 (es) * 2007-01-16 2008-10-10 Bayer Consumer Care Ag Solucion coloidal que comprende al menos un ingrediente activo, al menos una molecula formadora de membrana y al menos un componente espumante; procedimiento para fabricar la solucion coloidal; y su uso para tratar trastornos dermatologicos.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2648462B1 (fr) * 1989-06-15 1994-01-28 Oreal Procede pour ameliorer l'efficacite therapeutique de corticosteroides liposolubles et composition pour la mise en oeuvre de ce procede
US5260065A (en) * 1991-09-17 1993-11-09 Micro Vesicular Systems, Inc. Blended lipid vesicles
IL101387A (en) * 1992-03-26 1999-11-30 Pharmos Ltd Emulsion with enhanced topical and/or transdermal systemic effect utilizing submicron oil droplets
EP0711557A1 (fr) * 1994-11-09 1996-05-15 Ciba-Geigy Ag Base pour formulations pharmaceutiques
WO1996037192A1 (fr) * 1995-05-26 1996-11-28 Vesifact Ag Compositions pharmaceutiques et cosmetiques contenant des sphingolipides et des glycolipides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9721428A1 *

Also Published As

Publication number Publication date
AU7689996A (en) 1997-07-03
CA2238263A1 (fr) 1997-06-19
WO1997021428A1 (fr) 1997-06-19

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