EP1667657A1 - Mousses aerosol topiques - Google Patents

Mousses aerosol topiques

Info

Publication number
EP1667657A1
EP1667657A1 EP04794159A EP04794159A EP1667657A1 EP 1667657 A1 EP1667657 A1 EP 1667657A1 EP 04794159 A EP04794159 A EP 04794159A EP 04794159 A EP04794159 A EP 04794159A EP 1667657 A1 EP1667657 A1 EP 1667657A1
Authority
EP
European Patent Office
Prior art keywords
formulation
emulsion
active agent
topical
agent
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.)
Withdrawn
Application number
EP04794159A
Other languages
German (de)
English (en)
Inventor
Jane Hirsh
John C. Ii Willis
Mark Hirsh
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.)
Precision Dermatology Inc
Original Assignee
Collegium Pharmaceutical Inc
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 Collegium Pharmaceutical Inc filed Critical Collegium Pharmaceutical Inc
Publication of EP1667657A1 publication Critical patent/EP1667657A1/fr
Withdrawn legal-status Critical Current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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
    • 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
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • 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
    • A61K9/10—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Definitions

  • Foams may be formulated in various ways to provide emollient or drying functions to the skin, depending on the formulation constituents. Therefore, this delivery technology should be a useful addition to the spectrum of formulations available for topical use; however, as yet, only a few are commercially available. The most convincing argument for the use of foams is ease of use by the patient, and consumer acceptance. Most foam dosage forms used in dermatology have incorporated corticosteroids to date, although some products have also been used to deliver antiseptics, antifungal agents, anti-inflammatory agents, local anesthetic agents, skin emollients, and protectants (American Journal of Drug Delivery, 2003, vol. 1(1), pp. 71-75).
  • the primary CFC substitute is the gas propellant known as hydrofluoroalkane, or HFA.
  • HFA hydrofluoroalkane
  • HFAs 1,1,1,2,3,3,3-heptafluoropropane (HFA-134a) and 1,1,1,2-tetrafluoroethane (HFA-227).
  • Hydrofluoroalkanes (HFAs) are also often referred to as hydrofluorocarbons (HFCs) and these terms are used interchangeably. Since replacing a component of any formulation means introducing new properties, and HFAs differ in their solvating power from CFCs and hydrocarbons, providing reproducible performance of reformulated aerosols for pharmaceutical uses represents a challenging task. Often a co-solvent (such as ethanol) needs to be incorporated into the formulation in order to produce a stable product (Pharmaceutical Aerosols, June 2003, p. 21).
  • a co-solvent such as ethanol
  • Alcohol co-solvents can dry and irritate the skin.
  • U.S. Patent No. 6,126,920 suggests that the use of alcohol co-solvents can lead to the burning, itching, and irritation observed in the use of topical foam for delivering betamethasone.
  • volatile alcohols are highly irritating to mucous membranes.
  • Formulations that contain volatile alcohols as well as alkanes are potential safety hazards due to the high flammability of the product.
  • the flammability characteristics of the product require expensive precautions during manufacturing, and may require controlled environments for storage and for disposal of containers after use.
  • WO 85/01876 describes the fire hazards associated with alcohol and alkane containing aerosol foam formulations. It is therefore an object of the invention to provide alcohol-free topical foam aerosol formulations that use hydrofluoroalkanes (HFAs) as the propellant.
  • HFAs hydrofluoroalkanes
  • the foam- forming formulation includes a HFA propellant and an active agent in an emulsion.
  • the emulsion has an oil phase and an aqueous, i.e. water- containing, phase.
  • the active agent may be present in either phase or dispersed in the emulsion.
  • the oil phase may consist at least in part of the HFA propellant.
  • Either or both of the oil phase and the aqueous phase may contain one or more surfactants, emulsifiers, emulsion stabilizers, buffers, and other excipients.
  • the aqueous phase contains a water-soluble active agent, for example, a local anesthetic, and the oil phase contains a water-insoluble second active agent.
  • the foam is stable on the skin, for example, for at least 10 minutes at body temperature, and disappears into the skin upon rubbing or after prolonged standing.
  • the formulation has the advantage of including an inert nonflammable hydrofluorocarbon propellant without requiring the use of additional co-solvents or co-propellants.
  • the composition is administered as a metered dose that can be applied to the skin or mucous membranes.
  • the gaseous propellant consists primarily of hydrofluoroalkanes (HFAs). Suitable propellants include HFAs such as 1,1,1,2-tetrafluoroethane (HFA 134a) and 1,1,1,2,3,3,3-heptafluoropropane (HFA 227), but mixtures and admixtures of these and other HFAs that are currently approved or may become approved for medical use are suitable.
  • HFAs hydrofluoroalkanes
  • HFA 134a 1,1,1,2-tetrafluoroethane
  • HFA 227 1,1,1,2,3,3,3-heptafluoropropane
  • the propellants preferably are not hydrocarbon propellant gases which can produce flammable or explosive vapors during spraying.
  • the compositions preferably contain no volatile alcohols, which can produce flammable or explosive vapors during use.
  • the active agent may be any material that has a desired effect when applied topically to a mammal, particularly a human. Suitable classes of active agents include anti-inflammatory agents, topical anesthetics, topical antibiotics including anti-fungal agents, and combinations thereof.
  • the anti-inflammatory agent can be a corticosteroid or a non- steroidal anti-inflammatory drug (NSAID).
  • Suitable corticosteroids include alclometasone dipropionate, amcinonide, beclametbasone dipropionate, betamethasone benzoate, betamethasone dipropionate, betamethasone valerate, budesonide, clobetasol propionate, clobetasone butyrate, desonide, desoxymethasone, diflorasone diacetate, diflucortolone valerate, flumethasone pivalate, fluclorolone acetonide, fluocinolone acetonide, fluocionoide, fluocortin butyl, flucortolones, fluprednidene acetate, flurandrenolone, halcinonide, hydrocortisone, hydrocortisone acetate, hydrocortisone butyrate, methylprednisolone acetate, nometasone furoate, triamcinolone acetonide, and de-ester
  • a preferred corticosteroid is hydrocortisone or a pharmaceutically acceptable lower alkyl ester thereof.
  • Suitable NSAIDs include diclofenac, ibuprofen, acetylsalicylic acid, piroxicam, ketoprofen, felbinac, and benzylamine. Such NSAIDs may be present with or without a hydrocortisone-type anti-inflammatory.
  • Suitable anesthetics include the aminoacylanilide compounds such as lidocaine, prilocaine, bupivacaine, levo-bupivacaine, ropivacaine, mepivacaine and related local anesthetic compounds having various substituents on the ring system or amine nitrogen; the aminoalkyl benzoate compounds, such as procaine, chloroprocaine, propoxycaine, hexylcaine, tetracaine, cyclomethycaine, benoxinate, butacaine, proparacaine, butamben, and related local anesthetic compounds; cocaine and related local anesthetic compounds; amino carbonate compounds such as diperodon and related local anesthetic compounds; N-phenylamidine compounds such as phenacaine and related anesthetic compounds; N-aminoalkyl amide compounds such as dibucaine and related local anesthetic compounds; aminoketone compounds such as falicaine, dyclonine and related local anes
  • the active agent is an antiobiotic, particularly an antifungal agent.
  • Suitable antifungal agents include clotrimazole, econazole, ketoconazole, itraconazole, miconazole, oxiconazole, sulconazole, butenaf ⁇ ne, naftiflne, terbinafine, undecylinic acid, tolnaftate, nystatin, and sertaconazole nitrate.
  • Emulsion is a preparation of one liquid distributed in small globules throughout the body of a second liquid.
  • the dispersed liquid is the discontinuous phase, and the dispersion medium is the continuous phase.
  • oil is the dispersed liquid and an aqueous solution is the continuous phase, it is known as an oil-in- water emulsion, whereas when water or aqueous solution is the dispersed phase and oil or oleaginous substance is the continuous phase, it is known as a water-in-oil emulsion.
  • the oil phase may consist at least in part of an HFA propellant.
  • Either or both of the oil phase and the aqueous phase may contain one or more surfactants, emulsif ⁇ ers, emulsion stabilizers, buffers, and other excipients.
  • Preferred excipients include surfactants, especially non-ionic surfactants; emulsifying agents, especially emulsifying waxes; and liquid non-volatile non-aqueous materials, particularly glycols such as propylene glycol.
  • the oil phase may contain other oily pharmaceutically approved excipients. For example, materials such as hydroxylated castor oil or sesame oil may be used in the oil phase as surfactants or emulsifiers. d.
  • Excipients Buffers preferably buffer the composition from a pH of about 4 to a pH of about 7.5, more preferably from a pH of about 4 to a pH of about 7, and most preferably from a pH of about 5 to a pH of about 7.
  • the buffer is triethanolamine.
  • Preservatives can be used to prevent the growth of fungi and microorganisms.
  • Suitable antifungal and antimicrobial agents include, but are not limited to, benzoic acid, butylparaben, ethyl paraben, methyl paraben, propylparaben, sodium benzoate, sodium propionate, benzalkonium chloride, benzethonium chloride, benzyl alcohol, cetypyridinium chloride, chlorobutanol, phenol, phenylethyl alcohol, and thimerosal.
  • Method of Making the Formulation a. Method of Preparing the Emulsion Concentrate
  • the oil phase is prepared by mixing together the surfactant(s) and emulsifier(s) and melting.
  • the aqueous phase is prepared separately by dissolving the preservatives in water with heating.
  • the aqueous phase is added to the oil phase with continuous high shear mixing to produce a milky emulsion.
  • the emulsion is cooled and the pH is adjusted by the addition of a buffer.
  • the active agent can be either pre-dissolved in aqueous or organic phase or suspended/dispersed in the final emulsion.
  • the concentration of the surfactant(s) in the concentrate is from about 0.5 to about 5% by weight of the final composition.
  • the concentration of the emulsifier(s) is from about 0.5% to about 5% by weight of the final composition.
  • the concentration of the buffer(s) is from about 0.1% to about 5% by weight of the final composition and the concentration of the stabilizer(s) is from about 5% to about 15% by weight of the final composition.
  • composition of the active agent is about 0.01% to about 30% by weight of the final composition.
  • concentration of anti- inflammatories is from about 0.01% to about 10% by weight for corticosteroids and from about 0.1% to about 3% by weight for NSAIDs.
  • concentration of topical anesthetics is from about 1% to about 10% by weight and the concentration anti-fungals and other antibiotics is from about 0.3% to about 5% by weight.
  • the topical anesthetic is preferably dissolved in the aqueous phase.
  • the emulsion concentrate is placed in pressure cans, preferably coated aluminum cans to prevent corrosion, such, as epoxy-coated cans.
  • the lid and dispensing apparatus are crimped in place.
  • the can is charged with propellant to the stated level, for example, by adding 30 grams of propellant per 70 grams of emulsion.
  • the mixture of the emulsion with the propellant may be insured by shaking, optionally with the aid of a mixing bead.
  • the dispenser may be metered or unmetered (continuous). Metered dispensing is preferred for highly active materials such as hydrocortisone and other steroids.
  • the can may be arranged for either "upside down" spraying with the valve at the bottom, or the can have a dip tube so that the foam can be sprayed while the can is upright with the valve at the top.
  • concentration of the HFA propellant(s) is from about 10% to about 60% by weight of the final composition, more preferably about 20% to about 50% by weight of the final composition.
  • the emulsion concentrate is mixed with an HFA propellant so that the final formulation in an aerosol can comprises about 50% to about 80% of concentrate and about 20% to about 50% of propellant.
  • the final formulation in an aerosol can contain 70% concentrate and 30% propellant.
  • the formulation is administered to the skin or mucous membranes of a patient to treat a disease of the skin or mucous membranes.
  • a selected amount of product is dispensed from the spray can, preferably onto the site to be treated.
  • the foam can be administered into the palm of the hand (the latter is also preferred when the application site in not visible).
  • the amount to be delivered can be determined by the prescribing physician or as directed in the instructions for non-prescription products. Alternatively, a fixed dose using the metering dispenser can be administered.
  • the foam is rubbed into the skin at the site to be treated. If contact with the hand is to be avoided, a glove may be worn; or, the foam may be left in place, wherein it will eventually collapse and deliver the active ingredient to the surface of the skin.
  • the oil phase is prepared by mixing the cetyl alcohol, Steareth-10, and emulsifying wax and heating to 70-80°C to melt.
  • the aqueous phase is prepared separately by dissolving the parabens in about 80% of the water listed above with heating to about 70 - 80°C. 3.
  • the aqueous phase is added to the oil phase with continuous high shear mixing to produce a milky emulsion. 4.
  • the emulsion is cooled to about 30 - 40°C; the emulsion thickens but remains a liquid. 5.
  • the pH is adjusted if necessary by the addition of triethanolamine. 6.
  • the hydrocortisone is suspended in propylene glycol and treated to eliminate any large aggregates.
  • the mixture is milled.
  • the final hydrocortisone particle size is small enough to allow aerosolization, for example, less than about 20 microns in diameter, preferably less than about 10 microns, more preferably, less than about 5 microns.
  • the hydrocortisone suspension is added to the emulsion with mixing.
  • the formulation is brought to the final weight with the addition of water.
  • the amount of triethanolamine is sensitive to the particular lots of ingredients, and the amount added determines the final pH of the product.
  • the preferred pH in this formulation is about pH 4 to about 7.
  • B. Propellant The concentrate is placed in an aerosol spray can, and the can is loaded with either isobutane-propane mixture or with HFA134a so that the composition is approximately 70% concentrate and 30% propellant (3 grams of propellant are added per 7 grams of concentrate).
  • Propellant The above formula is placed in an aerosol spray can, and the can is loaded with HFA134a so that the composition is approximately 70% concentrate and 30% HFA, i.e., 3 grams of propellant are added per 7 grams of concentrate.
  • the composition is mixed and dispensed essentially as described in Example 1.
  • a formulation incorporating both an anti-inflammatory and an anesthetic would be useful in treating skin inflammatory conditions.

Abstract

L'invention concerne une mousse aérosol topique stable. La formulation de formation de mousse comporte un propulseur HFA et un agent actif dans une émulsion. Cette dernière présente une phase huileuse et une phase aqueuse, c'est-à-dire qui contient de l'eau. L'agent actif peut être présent dans les deux phases ou dispersé dans l'émulsion. La phase huileuse peut être constituée au moins partiellement du propulseur HFA. L'une ou l'autre, ou les deux phases huileuse et aqueuse, peut contenir un ou plusieurs tensioactifs, émulsifiants, stabilisateurs d'émulsion, tampons, et d'autres excipients. Dans un autre mode de réalisation, la phase aqueuse contient un agent actif soluble dans l'eau, par exemple un anesthésique local, et la phase huileuse un second agent actif insoluble dans l'eau. La mousse est stable sur la peau, par exemple pendant au moins dix minutes à la température corporelle, et disparaîtra dans la peau par friction ou après une exposition prolongée. La formulation présente l'avantage d'un propulseur hydrofluorocarboné ininflammable inerte, sans nécessiter l'utilisation de co-solvants ou de co-propulseurs additionnels. La composition est administrée sur la peau ou sur des muqueuses.
EP04794159A 2003-10-03 2004-10-04 Mousses aerosol topiques Withdrawn EP1667657A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US50849503P 2003-10-03 2003-10-03
US56089004P 2004-04-09 2004-04-09
PCT/US2004/032714 WO2005032522A1 (fr) 2003-10-03 2004-10-04 Mousses aerosol topiques

Publications (1)

Publication Number Publication Date
EP1667657A1 true EP1667657A1 (fr) 2006-06-14

Family

ID=34426057

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04794159A Withdrawn EP1667657A1 (fr) 2003-10-03 2004-10-04 Mousses aerosol topiques

Country Status (4)

Country Link
EP (1) EP1667657A1 (fr)
CA (1) CA2528818C (fr)
MX (1) MXPA06003743A (fr)
WO (1) WO2005032522A1 (fr)

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Also Published As

Publication number Publication date
CA2528818A1 (fr) 2005-04-14
WO2005032522A1 (fr) 2005-04-14
CA2528818C (fr) 2010-08-10
MXPA06003743A (es) 2006-06-23

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