WO2016133471A1 - Composition topique contenant de la mupirocine et du dexpanthénol - Google Patents

Composition topique contenant de la mupirocine et du dexpanthénol Download PDF

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Publication number
WO2016133471A1
WO2016133471A1 PCT/TR2015/000057 TR2015000057W WO2016133471A1 WO 2016133471 A1 WO2016133471 A1 WO 2016133471A1 TR 2015000057 W TR2015000057 W TR 2015000057W WO 2016133471 A1 WO2016133471 A1 WO 2016133471A1
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WO
WIPO (PCT)
Prior art keywords
mupirocin
composition
dexpanthenol
topical pharmaceutical
pharmaceutical composition
Prior art date
Application number
PCT/TR2015/000057
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English (en)
Inventor
Ersin Yildirim
Tolga Ramazan KARASU
Koray YILMAZ
Murat Muhibbi IŞIK
Derya AKSU
Mustafa Serkan SOLMAZ
Prabaharan RAMACHANDRAN
Original Assignee
Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A. Ş.
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 Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A. Ş. filed Critical Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A. Ş.
Priority to PCT/TR2015/000057 priority Critical patent/WO2016133471A1/fr
Publication of WO2016133471A1 publication Critical patent/WO2016133471A1/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
    • A61K9/0012—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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • A61K9/08—Solutions

Definitions

  • the present invention relates to the topical pharmaceutical composition containing mupirocin antibiotic, dexpanthenol as cicatrizant.
  • Topical preparations have been used for treating many diseases in many years. Combinations can also be used for topical preparations. Topical semi-solid dosage forms are normally presented in the form of creams, gels, ointments or pastes.
  • Transdermal drug delivery offers many potential advantages over conventional methods of drug administration.
  • Topical formulations are applied directly to the skin. Advantages of this include a) increased dose of medication where it is needed, b) reduced side effects and toxicity to other organs.
  • the amount of the active ingredient that is absorbed through the skin depends on the following factors:
  • Antibiotics are well known active agents used to treat infections and related diseases. Depending upon the antibiotic class, any one of a variety of mechanism of action is used to target and treat the infection.
  • Mupirocin is an antibiotic of the monoxycarbolic acid class. It was antibiotic from a strain of Pseudomonas fluorescens, developed by Beecham. It is a broad-spectrum antibiotic, which can be obtained by fermentation from Pseudomonas fluorescens.
  • Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.lt is used topically and is effective against Gram-positive bacteria, including methicillin-reststant Staphylococcus aureus (MRSA), which is a significant cause of death in hospitalized patients having received systemic antibiotic therapy.lt is used as a topical treatment for bacterial skin infections, e.g. furuncle, impetigo, open wounds. It is indicated for the topical treatment of impetigo due to Staphylococcus aureus and Streptococcus pyogenes.
  • MRSA methicillin-reststant Staphylococcus aureus
  • Mupirocin helps by stopping the production of essential proteins needed by the bacteria to survive. It has shown excellent activity against gram-positive staphylococci and streptococci. l
  • the antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.
  • Topical antibacterial compositions comprising mupirocin mupirocin are marketed under the trade names Bactroban ® Ointment, Bactroban ® Nasal and Bactroban ® Cream, by SmithKline Beecham.
  • the first contains mupirocin, while the other two contain crystalline mupirocin calcium dihydrate.
  • the formulation of Bactroban ® Ointment is described in U.S Patent No. 4,524,075.
  • the formulation of Bactroban ® Nasal is described in U.S Patent No. 4,790,989.
  • the cream base of Bactroban ® Cream is described in world WO 95/10999 and U.S Patent No. 6,025,389.
  • U.S. Patent No. 6,025,389 discloses a pharmaceutical or veterinary composition containing about 2.4% by weight of mupirocin or a pharmaceutically acceptable salt thereof; about 50.9% by weight mineral oil USP; about 6% by weight polyethylene glycol monocetyl ether; about 3.5% by weight stearyl alcohol; about 3.5% by weight cetyl alcohol; about 0.5% by weight phenoxyethanol; about 1% by weight benzyl alcohol; about 0.2% by weight xanthan gum; and about 32% by weight purified water.
  • WO2009/047788 relates to a topical pharmaceutical composition, comprising mupirocin and beciomethasone, useful for the treatment of infected dermatoses caused by bacteria or for preventing secondary bacterial infections in patients of steroid responsive dermatoses.
  • WO/2012/052472 discloses a pharmaceutical or veterinary anhydrous topical gel composition of mupirocin.
  • EP1 174133A1 discloses topical compositions based in the use of a hydrophobic phase, in particular a composition comprising amorphous mupirocin calcium, a hydrophobic phase, and hexylene glycol as solvent.
  • WO200410988A1 discloses aqueous compositions of mupirocin with ethylcellulose as a rate modulating hydrophobic polymer.
  • Cicatrizant refers to agents including natural substances such as herbs, oils, or essences, or conventional pharmaceutical drugs, that promote healing of the skin by the formation of scar tissue.
  • Panthenol is a member of cicatrizant group. Panthenol (pantothenol) is the alcohol analog of pantothenic acid (vitamin B 5 ). For topical applications is usually given panthenol in ointment form, even in ophthalmology. Only D-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties.
  • Dexpanthenol can be used for mouth and throat disorders, pantothenic acid deficiency, eye disorders, wounds, burns, sensation of burning in feet, upper respiratory-tract disorders, skin disorders.
  • a cream with dexpanthenol regularly can apply to the skin to improve the moisture content of dry skin significantly.
  • Dexpanthenol cream can use for an emollient.
  • An ointment with dexpanthenol can prevent erythema due to UV light.
  • Dexpanthenol ointment also can protect the lips against solar herpes, sun burns, mild burns, skin irritations, dry or cracked skin, cosmetic or shaving rashes, post chemical peeling treatment, post laser resurfacing treatment.
  • Dexpanthenol is effective for preventing / treating nappy dermatitis in infants.
  • Panthenol chemical name is 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyibutanamide, is a cicatrizant.
  • the compound having the figure 2 is known as panthenol.
  • EP0610655 describes to a sterile medicament for topical administration of dexpanthenol, containing a polyacrylate carrier to improve stability of active agent.
  • WO2005/063224 relates to a topical pharmaceutical preparation containing dimethyl sulfoxide and dexpanthenol, useful e.g. for treating inflammation, pain, rheumatic disease or neuralgia.
  • a topical pharmaceutical composition characterized in that it comprises:
  • the present invention relates to a topical pharmaceutical composition
  • a topical pharmaceutical composition comprising mupirocin and dexpanthenol.
  • the composition comprises mupirocin in the range of about 1-5% w/w and dexpanthenol in the range of about 0.05— 10% w/w based on the total weight of the composition.
  • the composition may comprise about 2% w/w of mupirocin and about 5% w/w of dexpanthenol based on the total weight of the composition.
  • the composition may further contain one or more pharmaceutically acceptable excipients.
  • the composition further comprises poly (substituted or unsubstituted alkylene) glycol or a derivative thereof and a pharmaceutically acceptable carrier.
  • composition can be in the form of an ointment, cream, lotion, solution or gel.
  • suitable pharmaceutically acceptable excipients for the topical composition include, but are not limited to, solvents, vehicles, ointment/cream bases, emulsifiers, preservatives, buffers, emollients, humectants, surfactants, and transport enhancers or mixtures there of.
  • a topical pharmaceutical composition characterized in that it comprises:
  • mupirocin as used herein includes mupirocin free base and/or its pharmaceutically acceptable salts or esters thereof.
  • Suitable pharmaceutically acceptable salts are well known in the art and include alkali metal salts such as sodium and lithium and alkaline earth metal salts such as calcium, of which the calcium salt is preferred, in particular the crystalline dihydrate form thereof described in EP 0 167 856-A (Beecham Group), as well as other metal salts, for instance silver, aluminium, ammonium and substituted ammonium salts.
  • the salts may be anhydrous or may be in the form of pharmaceutically acceptable solvates, for instance alcoholates and, especially, hydrates.
  • Preferred salts include the calcium, silver and lithium salts, in particular the calcium salt.
  • the crystalline salt preferably the crystalline hydrated calcium salt, more preferably the crystalline dihydrate salt
  • Mupirocin Calcium is the dihydrate crystalline calcium hemi-salt of the mupirocin.
  • Suitable pharmaceutically acceptable esters are well known in the art and include lower alkyl esters, especially the methyl and ethyl esters. Mupirocin is used in preference to a salt or ester thereof.
  • diexpanthenol as used herein includes dexpanthenol free base and/or its pharmaceutically acceptable salts or esters thereof.
  • the present invention may be used for the treatment of infected dermatoses caused by bacteria. This includes the treatment of lesions like eczema, atopic dermatitis, allergic dermatitis, contact dermatitis, and psoriasis, (which are primarily inflammatory in nature and responsive to treatment with corticosteroids) that have been further infected by bacterial infection which signifies secondary bacterial infection. It may also be used for the prevention of steroid responsive dermatoses in patients who are at high risk of developing infection.
  • the topical composition can be used to prevent the exacerbation of steroid-responsive dermatoses.
  • composition of present invention may further comprise corticosteroid.
  • corticosteroid means a compound including, but not limited to:hydrocortisone,cortisone, tixocortol, desonide, prednisolone, methylprednisolone, prednisone, triamcinolone, halometasone, fluocortolone, clobetasol, clobetasone, mometasone, amcinonide, budesonide, fluocinonide, fluocinolone, dexamethasone, betamethasone, halcinonide.prednicarbate, alclometasone, flupredntdene or a combination thereof and their pharmaceutically acceptable salts.
  • Formulations of the present invention may be produced by conventional pharmaceutical techniques.
  • ointments and creams are conveniently prepared by melting and mixing together the solid or semi-solid vehicles, and stirring in the therapeutic agent and any other ingredients. The product is then slowly cooled and filled into containers such as collapsible metal or plastic tubes.
  • composition includes suitable dosage forms, such as ointments, creams, lotions, gels or solutions, and may contain appropriate conventional additives, such as preservatives, solvents and emollients, cream or ointment bases, viscosity modifiers, stiffening agents, emulsifiers, preservatives, buffers, vehicles and mixtures there of.
  • suitable dosage forms such as ointments, creams, lotions, gels or solutions
  • suitable dosage forms such as ointments, creams, lotions, gels or solutions
  • suitable conventional additives such as preservatives, solvents and emollients, cream or ointment bases, viscosity modifiers, stiffening agents, emulsifiers, preservatives, buffers, vehicles and mixtures there of.
  • Such carriers may comprise from about 1% to about 98% of the formulation.
  • the major subject of the present inventions are to provide a formulation which has resistant against physical and enviromental conditions and also have a high bioavailability.
  • the present invention provides topical drug delivery systems which release a therapeutically effective amount of one or more active pharmaceutical ingredients to the site of absorption or action.
  • Another object of the present invention is to increase the rate of percutaneous penetration, thereby shortening the time period in which the active agents can show their effect.
  • the present invention showswell physical properties in the formulation depends on its solubility characteristics in appropriate excipients for topical formulations.lt shows good properties on rheology, particle or droplet size, pH, and visual appearance to provide basic physical stability.
  • the present invention maybe used for relieving dry skin, preventing and treating sore nipples during breast-feeding, and promoting healing of burns and poorly-healing wounds.
  • the present invention can be used for in the treatment of chronic wounds such as leg ulcers, decubitus ulcers.
  • the formulation of the present invention comprises mupirocin in combination with dexpanthenol.
  • the formulations of the present invention are topical and may be in the form of an ointment, cream, liquid, lotion, or gel which can apply on affected skin surface.
  • the present invention relates to an easily applicable mupirocin and dexpanthenol combination, eliminating all problems and bringing additional advantages to the relevant prior art.
  • Another object of the present invention is to increase the rate of percutaneous penetration, thereby shortening the time period in which the active agents can show their effect.
  • a safe and effective amount of a skin smoothing or skin healing active may be added to the present composition, preferably, more preferably from about 0.5% to about 10 %, by weight of the composition formed.
  • Skin soothing or skin healing actives suitable for use herein include panthenoic acid derivatives (including panthenol, dexpanthenol, ethyl panthenol), aloe vera, allantoin, bisabolol, and dipotassium glycyrrhizinate.
  • said novelty is realized with mupirocin or a pharmaceutically acceptable salt thereof together with dexpanthenol, wherein the amount of dexpanthenol makes up 1 to 10%, preferably 4 to 6%, and more preferably 5% of the total weight of composition, the formulation further comprising mupirocin and relevant excipients.
  • corticosteroids can be incorporated into composition of present invention in an amount of 0.01 % to 1%.
  • topical as used herein is meant to encompass any condition, disease or disorder manifested on body surfaces such as the skin or mucousal membranes such as the vagina, anus, throat, eyes and ears, including any tissue covering a body of a mammalian subject consisting of the outer, thinner epidermis (epithelial tissue) and the inner, thicker dermis (connective tissue), that is anchored to the subcutaneous layer.
  • composition or kit of the invention is intended for dermatological use on any type of skin area, being an exterior exposed area (such as for example areas of the skin, scalp, hair, and nails), an interior skin area such as a mucosal membrane (such as for example mucosal membrane around on the nostrils, the lips, the ears, the genital area, and the anus) or any vicinal areas in close proximity with the treated skin or mucosal membrane areas wherein said composition and agents comprised in said composition may reach via any kind of diffusion mechanisms to a skin area or mucosal membrane.
  • an exterior exposed area such as for example areas of the skin, scalp, hair, and nails
  • an interior skin area such as a mucosal membrane (such as for example mucosal membrane around on the nostrils, the lips, the ears, the genital area, and the anus) or any vicinal areas in close proximity with the treated skin or mucosal membrane areas wherein said composition and agents comprised in said composition may reach via any kind of diffusion mechanisms to a skin area or
  • composition of the present invention may comprise one or more pharmaceutically acceptable excipient(s).
  • Pharmaceutically acceptable excipients comprise, but are not limited to, gelling agents, emulsifiers, preservatives, thickeners, plastizers, moisturizers, stabilizers, solubilizers, emollients, surfactants, aromatic agents, penetration enhancers, pH adjusters and the mixtures thereof.
  • Penetration enhancers can be selected from the group, but are not limited to, propylene glycol, calcium chelators such as EDTA, methylated P-cyclodextrin, and polycarboxylic acids; surfactants such as sodium lauryl sulfate, sodium dodecyl sulfate, carnitine, carnitine esters, and tween; bile salts such as sodium taurocholate; fatty acids such as oleic and linoleic acid; and non-surfactants such as dialkyl sulfoxides; E-flux inhibitors such as D-a-tocopheryl polyethylene glycol 1000 succinate (TPGS), and peppermint oil; chitosan and chitosan derivatives such as N-methyl chitosan, N-trimethyl chitosan, mono-N-carboxymethyl chitosan, quaternized chitosan derivatives; SNAC (N- (8-(2-hydroxybenzo
  • Gelling agents can be selected from the group, but are not limited to, acacia, alginic acid, bentonite, carbopols, carbomer 940, carbomer 941 , gelatin, carbomer copolymer, aluminum monostearat, dextrin, magnesium aluminum silicate, silicon dioxide, sodium alginate, triethanolamine, polyvinyl alcohol, pectin, methylcellulose, hydroxypropyl cellulose, aqueous thickening agents such as neutral, anionic-cationic polymers and other materials known to one of ordinary skill in the art and mixtures thereof.
  • pH adjusting agents can be selected from the group, but are not limited to, triethanolamine, triethylamine, diethylmethylamine, ethyldimethylamine, isopropyldimethylamine.one or more adipic acids, glycines, citric acids, calcium hydroxides, magnesium aluminometasilicates, buffers, typically Bronsted-Lowry and/or Lewis acids and/or bases, or any combinations thereofand other materials known to one of ordinary skill in the art.
  • Moisturizers can be selected from the group, but are not limited to, polyethylene glycol, propylene glycol, dipropylene glycol, 1 ,3-butylene glycol, glycerin, diglycerin, xylitol, maltitol, maltose, D-mannitol, glucose, fructose, sodium chondroitin sulfate, sodium hyaluronate, sodium lactate, glucosamine, cyclodextrin, cococaprylate/caprateand other materials known to one of ordinary skill in the art and mixtures thereof.
  • Emulsifiers can be selected from the group, but are not limited to, ceteth-20, laureth-3, glyceryl stearate, polyethylene glycol, macrogol cetostearyl ether, stearic acid, stearyl alcohol, polysorbate 60, Irish moss, Tween 80, sorbitol monostearate.glycol esters, fatty acids, fatty alcohols, fatty acid glycol esters, fatty esters, fatty ethers, esters of glycerin, esters of propylene glycol, fatty acid esters of polyethylene glycol, fatty acid esters of polypropylene glycol, esters of sorbitol, esters of sorbitan anhydrides, carboxylic acid copolymers, esters and ethers of glucose, ethoxylated ethers, ethoxylated alcohols, alkyl phosphates, polyoxyethylene fatty ether phosphates, fatty acid amides, acyl lac
  • Emollients can be selected from the group, but are not limited to, liquid vaseline.paraffinum liquidum, petrolatum, proplylene glycol, fatty acid esters, mineral oil including dimethicone, waxes including white wax, spermacetic wax, squalene, cetearyl alcohol, cetostearyl alcohol, stearyl alcohol, 2-Octyldodecanol, mineral oil USP, light mineral oil NF, liquid paraffin BP, light liquid paraffin BP.candellilla wax, sweet almond oil, apricot oil, emu oil, argan oil, glycerin, coconut oil, grape seed oil, honey, lanolinand other materials known to one of ordinary skill in the art and mixtures thereof.
  • Surfactants can be selected from the group, but are not limited to, a polysorbate, polyoxyethylene (20) sorbitan monostearate, polyoxyethylene (20) sorbitan monooleate, a polyoxyethylene fatty acid ester, Myrj 45, Myrj 49, Myrj 52 and Myrj 59; a polyoxyethylene alkylyl ether, polyoxyethylene cetyl ether, polyoxyethylene palmityl ether, polyethylene oxide hexadecyl ether, polyethylene glycol cetyl ether, a sucrose ester, a partial ester of sorbitol, sorbitan monolaurate, sorbitan monolaurate a monoglyceride, a diglyceride, isoceteth-20, a sucrose ester, or selected from the group consisting of steareth 2, glyceryl monostearate/PEG 100 stearate, Glyceryl Stearate, Steareth-21 , peg 40 stearate,
  • Preservatives can be selected from the group, but not limited to, methylparaben and propylparaben and the salts thereof (e.g. sodium or potassium salts), sodium benzoate, diazolidinyi urea, phenoxyethanol, DMDM hydantoin, sorbic acid, benzyl alcohol, formaldehyde, triclosan.methylisothiazolinone, methylchloroisothiazolinone, caffeine, citric acid, benzoic acid, butylated hydroxytoluene, propylene glycol, organic acids, esters of parahydroxybenzoic acid(methyl, ethyl, propyl and butyl esters of parahydroxy benzoic acid, and their sodiumsalts etc), chloform,chlorocresol,phenoxyethanol,quaternary ammonium compoundsand butylated hydroxyanisole, and the mixtures thereof.
  • salts thereof e.g. sodium or potassium salts
  • sodium benzoate
  • Aromatic agents can be selected from the group, but are not limited to, menthol, lavender, mint, cinnamon, chocolate, vanillin, and fruit extracts such as cherry, orange, strawberry, grape.fenouil oil, eucalyptus oil, carnation oil, ginger oil, sweet orange oil, and the mixtures thereof.
  • Solvents can be selected from the group, but not limited to, ethyl alcohol, polyethylene glycol, propylene glycol, isopropyl alcohol, purified waterand other materials known to one of ordinary skill in the art and mixtures thereof.
  • Thickeners can be selected from the group, but not limited to, beeswax, cocoa butter, shea butter, woo! wax, cetyl alcohol, gum acacia, gum tragacanth, locust bean gum, guar gum, hydroxypropyl guar, xanthan gum, cellulose gum, sclerotium gum, carrageenan gum, karaya gum, cellulose gum, rosin, anionic polymers such as polyacrylic acid, carboxymethylcellulose, methylcellulose.hydroxyethylcellulose, hydroxypropylcellulose, hydroxymethylcellulose, polyethylene glycol, acrylic acid polymers, PEG- 150 distearate, decyl alcohol, SMDI copolymer, faponite XLG, ethyl cellulose, natrosol and other materials known to one of ordinary skill in the art and mixtures thereof.
  • anionic polymers such as polyacrylic acid, carboxymethylcellulose, methylcellulose.hydroxyethylcellulose, hydroxypropy
  • Plasticizers can be selected from the group, but not limited to, glycerol, propylene glycol or another glycol, peppermint oil, eucalyptol oil, geranyl acetate or geraniol, phthalate, sebacate and citrate esters, triacetin, sorbitol, sucrose, triethyl citrate, dibutyl phthalate and other materials known to one of ordinary skill in the art and mixtures thereof.

Abstract

La présente invention concerne des compositions pharmaceutiques topiques contenant de la mupirocine, du dexpanthénol et des excipients pharmaceutiquement acceptables.
PCT/TR2015/000057 2015-02-20 2015-02-20 Composition topique contenant de la mupirocine et du dexpanthénol WO2016133471A1 (fr)

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EP0167856A2 (fr) 1984-06-19 1986-01-15 Beecham Group Plc Pseudomonate de calcium cristallin et son usage
US4790989A (en) 1986-06-26 1988-12-13 Beecham Group P.L.C. Treatment of fungal infections
EP0610655A1 (fr) 1993-02-10 1994-08-17 Dr. GERHARD MANN chem.-pharm. Fabrik GmbH Medicament contenant du dexpanthénole pour l'application topique
WO1995010999A1 (fr) 1993-10-22 1995-04-27 Smithkline Beecham Corporation Nouvelle composition
EP1174133A1 (fr) 2000-07-18 2002-01-23 Agis Industries (1983) Ltd Composition pharmaceutiques contenant de mupirocine amorphe
WO2004010988A1 (fr) 2002-07-31 2004-02-05 Connetics Australlia Pty Ltd Systeme d'administration par voie percutanee et ungueale
WO2005063224A1 (fr) 2003-12-23 2005-07-14 Merckle Gmbh Preparations topiques contenant du dimethylsulfoxyde et du dexpanthenol
US20060275218A1 (en) * 2003-08-04 2006-12-07 Foamix Ltd. Foamable vehicle and pharmaceutical compositions thereof
US20080299220A1 (en) * 2003-08-04 2008-12-04 Dov Tamarkin Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses
WO2009047788A2 (fr) 2007-08-06 2009-04-16 Glenmark Pharmaceuticals Limited Combinaison topique contenant une combinaison de mupirocine et de béclométhasone
WO2010124280A2 (fr) * 2009-04-24 2010-10-28 New Century Pharmaceuticals, Inc. Onguent topique à base de sérum-albumine humaine pour le traitement de l'acné, du psoriasis, de la toxicité induite par egfr, le vieillissement prématuré de la peau et autres affections cutanées
WO2012052472A1 (fr) 2010-10-20 2012-04-26 Laboratorios Ojer Pharma S.L. Composition topique pharmaceutique de mupirocine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4524075A (en) 1982-05-28 1985-06-18 Beecham Group P.L.C. Pharmaceutical formulations containing pseudomonic acid
EP0167856A2 (fr) 1984-06-19 1986-01-15 Beecham Group Plc Pseudomonate de calcium cristallin et son usage
US4916155A (en) 1984-06-19 1990-04-10 Beecham Group P.L.C. Crystalline calcium pseudomonate
US4790989A (en) 1986-06-26 1988-12-13 Beecham Group P.L.C. Treatment of fungal infections
EP0610655A1 (fr) 1993-02-10 1994-08-17 Dr. GERHARD MANN chem.-pharm. Fabrik GmbH Medicament contenant du dexpanthénole pour l'application topique
US6025389A (en) 1993-10-22 2000-02-15 Smithkline Beecham Corporation Pharmaceutical and veterinary compositions of mupirocin and methods for their preparation
WO1995010999A1 (fr) 1993-10-22 1995-04-27 Smithkline Beecham Corporation Nouvelle composition
EP1174133A1 (fr) 2000-07-18 2002-01-23 Agis Industries (1983) Ltd Composition pharmaceutiques contenant de mupirocine amorphe
WO2004010988A1 (fr) 2002-07-31 2004-02-05 Connetics Australlia Pty Ltd Systeme d'administration par voie percutanee et ungueale
US20060275218A1 (en) * 2003-08-04 2006-12-07 Foamix Ltd. Foamable vehicle and pharmaceutical compositions thereof
US20080299220A1 (en) * 2003-08-04 2008-12-04 Dov Tamarkin Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses
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