EP1347749A2 - Systeme therapeutique transdermique contenant l'agent actif oxybutynine - Google Patents

Systeme therapeutique transdermique contenant l'agent actif oxybutynine

Info

Publication number
EP1347749A2
EP1347749A2 EP01985337A EP01985337A EP1347749A2 EP 1347749 A2 EP1347749 A2 EP 1347749A2 EP 01985337 A EP01985337 A EP 01985337A EP 01985337 A EP01985337 A EP 01985337A EP 1347749 A2 EP1347749 A2 EP 1347749A2
Authority
EP
European Patent Office
Prior art keywords
tts according
oxybutynin
phase
active ingredient
weight
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Withdrawn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
EP01985337A
Other languages
German (de)
English (en)
Inventor
Stefan Bracht
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.)
LTS Lohmann Therapie Systeme AG
Original Assignee
LTS Lohmann Therapie Systeme 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 LTS Lohmann Therapie Systeme AG filed Critical LTS Lohmann Therapie Systeme AG
Publication of EP1347749A2 publication Critical patent/EP1347749A2/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Withdrawn legal-status Critical Current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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • 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
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7092—Transdermal patches having multiple drug layers or reservoirs, e.g. for obtaining a specific release pattern, or for combining different drugs
    • 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

Definitions

  • the present invention relates to transdermal therapeutic systems (TTS) for the administration of the active ingredient oxybutynin. It also relates to a production process for active ingredient layers of transdermal therapeutic systems containing oxybutynin.
  • TTS transdermal therapeutic systems
  • Oxybutynin is an anticholinergic and spasmolytic, which is mainly used to treat bladder dysfunction, especially urge to urinate, incontinence or nocturia.
  • This active ingredient is usually administered orally as oaybutynin hydrochloride, for example in the form of tablets. Capsules or syrup.
  • transdermal therapeutic systems have been described in the literature which are intended to enable the administration of this active substance via the skin.
  • ALZA US 5,500,222, US 5,411,740, US 5,900,250 and EP 721 349
  • Theratech US 5,834,010
  • Schwarz Pharma AG DE 198 12 413 Cl
  • enhancers are associated with an increased risk of skin irritation.
  • the addition of enhancers should be avoided if possible if the required transdermal absorption rates can also be achieved without such an addition. It was indeed possible to show in DE 198 12 413 Cl that the required flow rates can also be achieved with a transdermal system without the addition of an enhancer.
  • the system structures described there are geared towards hot melt technology. These enhancer-free formulations are produced on the basis of (meth) acrylate polymers containing ammonio groups.
  • the hot melt process used here requires the addition of plasticizers, in this case from the group of citric acid esters. This is a severe limitation because the clear majority of TTS market products and the existing production facilities are geared towards solvent-based production and not towards hot melt technology.
  • the object of the present invention was therefore to provide transdermal therapeutic systems for the administration of oxybutynin, with which therapeutically effective absorption rates can be achieved without the addition of permeation-promoting substances (enhancers) being necessary, and which are economical and economical on the basis of solvent-containing processes can be produced on a large scale and do not require the use of hot melting processes.
  • the TTS according to the invention with the features mentioned in the preamble of claim 1 are characterized in that they have at least one active substance-containing matrix layer which is essentially composed of two immiscible phases (2, 3). These are an inner and an outer phase, the inner phase (2) containing the active ingredient oxybutynin base or oxybutynin hydrochloride and being dispersed in droplets in the outer phase (3).
  • the outer phase is one based on coal Pressure sensitive adhesives produced from oxygen polymers and / or silicone polymers.
  • a further embodiment provides that in addition to oxybutynin, the pharmacodynamically active main metabolite desethyloxybutynin is also contained in the inner phase.
  • Oxybutynin and desethyloxybutynin are preferably present in a weight ratio of 1:10 to 10: 1.
  • oxybutynin and, if contained in the TTS, desethyloxybutynin are at least 90% present as (S) -enantiomers.
  • the active substance (s) is preferably in dissolved form, with at least 50% by weight of the active substance being dissolved, particularly preferably 90-100%.
  • the matrix according to the invention By constructing the matrix according to the invention from two phases, the active substance solution or active substance-containing preparation being dispersed or emulsified in droplet form in a surrounding polymer phase, an optimal outward scavenging of the thermodynamic activity of the active substance can be achieved. As a result, it is not necessary to add enhancer substances in order to achieve adequate skin permeation rates.
  • the structure of a transdermal therapeutic system is shown by way of example in FIG. 1 (sectional view).
  • the active substance (s) or the active substance solution forms the inner phase (2) and is distributed in droplet form in a surrounding, pressure-sensitive adhesive outer phase (3).
  • the system is equipped on the side facing away from the skin with a backing layer (1) which is preferably permeable to water and pounds, and on the skin contact side with a removable protective layer (4).
  • This exemplary basic type can be modified in various ways, as described below.
  • the TTS can be in different geometric surface shapes are produced, e.g. B. round, oval or oblong.
  • the inner phase (2) consists exclusively of the liquid active ingredient solution or dispersion. This corresponds to a droplet-like distribution of the active ingredient within an outer phase oversaturated with the active ingredient and ensures its maximum thermodynamic activity.
  • the active phase-containing inner phase (2) contains an addition of one or more binders (also called thickeners). In this way it can be prevented that the active substance from the droplet-like inner phase accumulates at the interfaces or surfaces of the matrix layer, as a result of which the adhesive force of the pressure-sensitive adhesive matrix layer could be impaired.
  • the drug solution emerging at the interfaces would undesirably act as a release agent, so that these layers are no longer covered with foils, e.g. B. PET films as the backing layer (1) could be laminated.
  • the proportion of binder polymer in the inner phase should correspond at most to the proportion by weight of the oxybutynin contained. Too high a proportion of binder polymer in the inner phase could unnecessarily reduce the thermodynamic activity of the active ingredient due to its solubility in the binder.
  • the binder or thickener is preferably present in one proportion of at least 10% by weight, preferably of 10-50% by weight, based on the inner phase.
  • the inner phase of the matrix layer according to the invention which is composed of two phases, contains at least 25% by weight, preferably at least 50% by weight and particularly preferably more than 70% by weight oxybutynin, optionally in combination with desethyloxybutynin.
  • binders or thickeners which have the advantages described above are polymers from the group of acrylate copolymers and methacrylate copolymers, preferably basic polymers, eg. B. (meth) acrylate copolymers containing amino groups.
  • a poly (meth) acrylate copolymer of neutral methacrylic acid esters and dimethylaminoethyl methacrylate is particularly preferably used; one of these is sold under the name Eudragit E by the company Röhm Pharma.
  • binders or thickeners are in particular neutral (meth) acrylate copolymers, for example a copolymer based on methacrylic acid methyl ester and methacrylic acid butyl ester (eg plastoid B; manufacturer: Röhm Pharma), or carboxyl group-free polyacrylate - pressure sensitive adhesive (e.g. Durotak 387-2516; National Starch).
  • neutral (meth) acrylate copolymers for example a copolymer based on methacrylic acid methyl ester and methacrylic acid butyl ester (eg plastoid B; manufacturer: Röhm Pharma), or carboxyl group-free polyacrylate - pressure sensitive adhesive (e.g. Durotak 387-2516; National Starch).
  • two or more of the polymers mentioned can also be present as a combination or mixture in the inner phase.
  • binder polymer (s) it is important to ensure that a stable dispersion or emulsion with small droplet sizes of the inner phase containing the active ingredient is obtained in the formulation batch.
  • the outer, pressure-sensitive adhesive phase (3) is preferably composed of pure hydrocarbon polymers and / or of silicone polymers.
  • hydrocarbon polymers which can be used are polyisobutylene, polyisoprene, polybutene and Block copolymers of the types styrene-isoprene-styrene and styrene-butadiene-styrene can be used.
  • tackifiers from the group of pressure sensitive or soft resins can be added.
  • the outer phase can be based on pressure sensitive adhesive
  • Silicone polymers are manufactured; amine-resistant polydimethylsiloxanes are particularly preferred.
  • the invention also includes those embodiments in which the outer phase contains a combination of at least two different types of polymer.
  • the outer phase has adhesive properties and serves to anchor the system on the skin; it also has the lowest possible solubility for the active ingredient so as not to hinder its release.
  • Polymers from the group of pure hydrocarbons or silicones are distinguished by a particularly low solubility for the active ingredient oxybutynin base.
  • the outer phase consists essentially of a mixture of at least two different polyisobutylenes which have at least two different molecular weights. Furthermore, in the case of the use of silicone pressure-sensitive adhesives, a preferred embodiment is provided in which the outer phase essentially consists of a mixture of at least two different silicone pressure-sensitive adhesives which have at least two different levels of initial tack.
  • Those embodiments of the TTS according to the invention in which the active substance-containing matrix layer (s) contain no enhancer substances are particularly preferred, so that the risk of skin irritation is reduced or eliminated.
  • Such oxybutynin-containing TTS are essentially free of enhancer substances, ie the content of such substances is less than 0.1% by weight, based on the matrix layer.
  • the TTS according to the invention are usually fastened by means of the adhesive properties of the outer phase.
  • the system can also be provided with an active ingredient-free adhesive patch for better fixation on the skin; Suitable possibilities for this are known to the person skilled in the field of TTS.
  • a further layer, which controls the release of the active ingredient or / and improves the anchoring on the skin for example a membrane which controls the release of active ingredient, is arranged between the skin-side delivery side of the matrix layer and the detachable protective layer. Appropriate means and methods for this are known to the person skilled in the art.
  • polyester foils are particularly suitable, which are characterized by particular strength, but also almost any other skin-compatible plastic foils, such as, for. B. polyvinyl chloride, ethylene vinyl acetate, vinyl acetate, polyethylene, polypropylene, polyethylene terephthalate, cellulose derivatives and many others.
  • the foils used are preferably impermeable to water vapor.
  • the backing layer can be provided with an additional layer, e.g. B. by vapor deposition with metals or other diffusion-blocking additives such as silicon dioxide, aluminum oxide or similar substances which are known to the person skilled in the art.
  • additional layer e.g. B. by vapor deposition with metals or other diffusion-blocking additives such as silicon dioxide, aluminum oxide or similar substances which are known to the person skilled in the art.
  • removable protective film (4) as for the backing layer, provided that they can be treated by suitable surface treatment, such as. B. Siliconization is removable.
  • suitable surface treatment such as. B. Siliconization is removable.
  • other removable protective layers such as polytetrafluoroethylene treated paper, cellophane, polyvinyl chloride, or the like can be used.
  • the polymers of the inner or the outer phase are dissolved in a solvent, oxybutynin, optionally in combination with desethyloxybutynin, being additionally added to the inner phase.
  • the polymer solutions of the inner or outer phase are then mixed with one another with stirring, so that a stable emulsion is produced.
  • the emulsion thus obtained is coated on a carrier film and dried.
  • Low molecular weight hydrocarbons e.g. n-hexane, cyclohexane, n-heptane, n-octane
  • solvents for the polymers of the outer phase and short-chain alcohols, particularly preferably ethanol or isopropanol, are preferred as solvents for the polymers of the inner phase used.
  • Particularly stable emulsions are obtained under these conditions.
  • Mixtures of the solvents mentioned can also be used, for example mixtures of the alcohols mentioned with ethyl acetate or other alkyl acetate.
  • Oxybutynin base was isolated from oxybutynin hydrochloride (from Denk Feinchemie). For this purpose, the aqueous solution of the hydrochloride was adjusted to a pH of 10-11 and the free base was extracted with diethyl ether. The ether phase was dried over sodium sulfate and then concentrated to constant weight in a nitrogen stream.
  • the example formulations mentioned in Table 1 were processed as solutions in organic solvents.
  • the raw materials Oppanol BIO and B100 were dissolved in suitable amounts of petrol, Bio PSA 4301 was used in the form supplied by Dow Corning as a solution in n-heptane.
  • Eudragit E 100 was used as a solution in ethanol
  • plastoid B was prepared in ethanol / ethyl acetate 1: 1 (m / m) and
  • Durotak 387-2516 was used in the form of a solution supplied by the manufacturer National Starch.
  • Oppanol BIO and B100 are polyisobutylenes (from BASF), Bio PSA 4301 is a silicone-based pressure sensitive adhesive. Oppanol or Bio PSA form the outer phase of the matrix layer.
  • the details in Table 1 denote the respective proportions in% by weight, based on the weight of the dried matrix layer. Table 1
  • the adhesive emulsions obtained after thorough stirring with a blade stirrer were coated on siliconized polyester film (PET 100 .mu.m) and dried in an air-drying cabinet for 10 minutes in the ambient air and 10 minutes at 80.degree.
  • the films obtained had the almost identical basis weights mentioned in Table 1.
  • FIGS. 2 and 3 each come from skin samples from the same skin donor.
  • the formulations according to the invention consistently achieve absorption rates which make transdermal therapy with oxybutynin possible with plaster sizes of not more than 30 cm 2 .
  • Examples 2 and 4 in particular show short lag times until a constant release of active ingredient through the skin is achieved in vitro.
  • Flux values of up to 4 ⁇ g / cm 2 x h-1 were achieved at steady state.
  • TTS according to the invention containing oxybutynin can be used to achieve sufficient rates of active substance release without the need for addition of Substanzennhancer substances.

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  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un système thérapeutique transdermique destiné à l'administration de l'agent actif oxybutynine, présentant une couche de doublure (1) essentiellement imperméable à la vapeur d'eau, au moins une couche matricielle adhésive (2, 3) reliée à ladite couche de doublure, et une pellicule de protection détachable (4). Le système selon l'invention est caractérisé en ce que ladite couche matricielle comporte deux phases non miscibles, c.-à-d. une phase intérieure et une phase extérieure. La phase intérieure (2) contient l'agent actif oxybutynine basique ou hydrochlorure d'oxybutynine et est dispersée sous forme de gouttelettes dans la phase extérieure (3), et la phase extérieure est un adhésif fabriqué à base de polymères d'hydrocarbures et/ou de polymères de silicone.
EP01985337A 2000-12-06 2001-11-24 Systeme therapeutique transdermique contenant l'agent actif oxybutynine Withdrawn EP1347749A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10060550A DE10060550C1 (de) 2000-12-06 2000-12-06 Transdermales therapeutisches System mit dem Wirkstoff Oxybutynin und Verfahren zur Herstellung Oxybutynin enthaltender Wirkstoffschichten
DE10060550 2000-12-06
PCT/EP2001/013678 WO2002045699A2 (fr) 2000-12-06 2001-11-24 Systeme therapeutique transdermique contenant l'agent actif oxybutynine

Publications (1)

Publication Number Publication Date
EP1347749A2 true EP1347749A2 (fr) 2003-10-01

Family

ID=7665959

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01985337A Withdrawn EP1347749A2 (fr) 2000-12-06 2001-11-24 Systeme therapeutique transdermique contenant l'agent actif oxybutynine

Country Status (7)

Country Link
US (1) US20040057985A1 (fr)
EP (1) EP1347749A2 (fr)
JP (1) JP2004514738A (fr)
KR (1) KR100677840B1 (fr)
AU (1) AU2002234525A1 (fr)
DE (1) DE10060550C1 (fr)
WO (1) WO2002045699A2 (fr)

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WO2002045699A3 (fr) 2002-08-08
US20040057985A1 (en) 2004-03-25
JP2004514738A (ja) 2004-05-20
KR100677840B1 (ko) 2007-02-05
WO2002045699A2 (fr) 2002-06-13
DE10060550C1 (de) 2002-04-18
AU2002234525A1 (en) 2002-06-18
KR20030064805A (ko) 2003-08-02

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