WO2008061677A1 - Transdermales therapeutisches system mit ionenpaar-mikroreservoiren - Google Patents
Transdermales therapeutisches system mit ionenpaar-mikroreservoiren Download PDFInfo
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- WO2008061677A1 WO2008061677A1 PCT/EP2007/009926 EP2007009926W WO2008061677A1 WO 2008061677 A1 WO2008061677 A1 WO 2008061677A1 EP 2007009926 W EP2007009926 W EP 2007009926W WO 2008061677 A1 WO2008061677 A1 WO 2008061677A1
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- Prior art keywords
- transdermal therapeutic
- therapeutic system
- additive
- matrix
- ion pair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- 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
- A61K31/60—Salicylic acid; Derivatives thereof
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- 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
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- 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
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- Transdermal Therapeutic Systems have been known for a number of years. Such systems are for. B. for agents such as estradiol, norethisterone acetate, nicotine, fentanyl, toluubuterol, acetylsalicylic acid, buprenorphine and a number of other agents introduced into the therapy.
- agents such as estradiol, norethisterone acetate, nicotine, fentanyl, toluubuterol, acetylsalicylic acid, buprenorphine and a number of other agents introduced into the therapy.
- the pharmaceutically suitable active ingredients in the group of neutral substances (norethisterone acetate, estradiol, nitroglycerin, etc.), the acidic agents (acetylsalicylic acid, ketoprofen, ibuprofen, etc.) and in particular the basic active ingredients (nicotine, fentanyl, toluubuterol, buprenorphine, moxonidine, Selegiline, salbutamol and many others).
- acidic agents or compounds should be understood here as those that are electrophilic and thus can act as Elektronenparakzeptoren (anion), as "basic” agents or compounds such as nucleophilic and thus can react as Elektronenpackdonatoren (cation former).
- the former are neutral acids (eg HCL), cationic acids (eg NH 4 + ) or anionic acids (eg HCO 3 ' ).
- the basic substances are neutral bases (eg NH 3 and organic amines), cation bases (eg NH 2 -NH 3 + ) and anion bases (eg CLO 4 ' ).
- transdermal therapeutic systems is usually thin and layered, so that with the help of the directly skin-facing side (adhesive layer) results in an at least temporarily sticky compound to the skin over which the drug is delivered.
- liquid components of the system are used in addition to polymers, resins and other pharmaceutical excipients, which are known in the narrower sense as permeation enhancers. Their goal is to improve the delivery of active ingredients through the skin.
- permeation enhancers can exert their effect purely physically by improving the diffusion of the active substance within the pharmaceutical system, or else by simultaneously improving the solution and, after diffusion into the skin there trigger thermodynamic activation (EP 1 191 927 B) or (enhancer in the narrower sense) by direct influence on the diffusibility in the skin allow an increase in the supply of substances to the body.
- ion pairing agents can be distinguished chemically, which in the case of the abovementioned acidic active compounds is physiologically acceptable nucleophilic basic additives, such as, for example, ammonia, propylamine, tromethamol, triethanolamine and many others known from the literature
- nucleophilic basic additives such as, for example, ammonia, propylamine, tromethamol, triethanolamine and many others known from the literature
- acidic, ie electrophilic additives such as oleic acid, lauric acid, levulinic acid and other fatty acids, but also aromatic acids such as benzoic acid or sulfonic acids such as hexanesulfonic acid used to form an ion pair
- ion pairs are physicochemical molecular associates consist of two charged molecules which, by an effective neutralization of the ionic conditions, form an outwardly almost neutral and thus more lipophilic associate, so that the active substance, which is always a part of this associate, turns into
- a task deriving from this prior art is therefore to provide a matrix for transdermal systems which comprises ion pairs of active substances which can be charged and physiologically contains acceptable opposing ion-pair-forming additives, this matrix does not have the disadvantages of insufficient drug saturation or disadvantageous plasticization of the polymer base.
- silicones and silicone adhesives have been known for some time as basic constituents of transdermal matrices and are used in particular because of their good compatibility. However, these usually have low solubilities for active ingredients with high diffusibility. Because of their unfavorable dissolution behavior they have been used as a dispersing medium for so-called microreservoirs which contain "ambiphilic" solvents for the active substance (EP 1 191 927 B) According to this publication, these ambiphilic solvents dissolve the active ingredient during storage so that it does not dissolve crystallized out, leaving the matrix after migration of the transdermal therapeutic system by migrating into the skin and then leave a supersaturation with subsequent increased thermodynamic activity of the drug, ion pairs and ion pair forming agents are not the subject of this publication.
- a comparable publication (DE 101 41 651 A1) relates to systems for the transdermal delivery of fentanyl and fentanyl derivatives comprising silicone matrices with micro-reservoirs therein, wherein solvents are present as easily diffusible neutral substances such as dipropylene glycol or 1, 3-butanediol.
- solvents are present as easily diffusible neutral substances such as dipropylene glycol or 1, 3-butanediol.
- permeation enhancers can be used as additional ingredients.
- this list also contains fatty acids without any indication of where they are to be housed within the transdermal therapeutic systems and in which form of state.
- the object of the invention is to provide a transdermal therapeutic system comprising as at least one system component a matrix consisting of a polysiloxane polymer base material containing microreservoirs, characterized in that said active agent is in the form of an ion pair in said microreservoirs is contained in a charge-capable active ingredient and a counter charge physiologically acceptable additive without the presence of solvents, said additive capable of ion pair formation being present in at least an equimolar amount.
- suitable active ingredient ion pairs may consist of a combination of an initially active substance part which initially reacts nucleophilically, that is to say react nucleophilically, with an acidic, that is to say electrophilic, additive part which is added at least equimolarly.
- suitable active ingredients are, for example, nicotine, moxonidine, clonidine, scopolamine, atropine, buprenorphine, fentanyl, salbutamol, memantine, uva highly effective, in particular aminic active ingredients.
- active substances whose daily dose does not exceed 30 mg, since there are special advantages due to the limited skin permeation here.
- Suitable electrophilic additives for forming an ion pair are saturated and unsaturated fatty acids which are branched or unbranched, unmodified or hydroxylated (ricinoleic acid, levulinic acid) or else derivatized in another way.
- Aromatic compounds are also very suitable, provided that they also have the ability to form cationic ion-pair complexes with active ingredients.
- Benzoic acid, heptanesulfonic acid, but also citric acid, tartaric acid and even inorganic acids, such as phosphoric acid or hydrochloric acid, may be mentioned as examples here. Since the efficiency of ion pairing for favoring transdermal absorption is particularly achieved by lyophilic acids, acid additives are preferred, which have a Octano l / buffer (pH 5.5 distribution coefficient of more than 1).
- the subject of this invention is a transdermal therapeutic system characterized in that ion pairs in the microreservoirs are acidic, i. electrophilic agents capable of anionic charge and basic, i. nucleophile-reactive additives with the ability to cationic charge, which are present in at least equimolar amount, are present.
- acid i. electrophilic reactants are diclofenac, ketoprofen, ibuprofen, acetylsalicylic acid, salicylic acid, and many other agents with preference for those having a systemic daily dose of less than 30 mg.
- Suitable additives for such ion pairs are all amines, preferably diethanolamine, triethanolamine, dimethylaminoethanol, tromethamol and any other physiologically compatible substance which is capable of forming ion pairs with anionic active substances as a base.
- the ion pairs according to the invention are embedded in a discrete physical phase as a semi-solid / solid or liquid inner phase within the matrix consisting essentially of polysiloxanes.
- the matrix and also the inner phase with the ion pair may contain further substances, e.g. Enhancers, plasticizers, hydrophilic or lipophilic polymers, etc. included.
- particularly preferred according to the invention are matrices whose inner phase consists exclusively of the ion pair ("physical / chemical mixture" of the active ingredient and at least one ion pair formation added in an equimolar amount).
- the effect of the invention namely the reduction of the effect on the cohesion of the surrounding silicone matrix and on the other hand, the maximum increase in the saturation (thermodynamic activity) of the active ingredient (drug-ion pair) can be achieved.
- the matrix according to the invention can be provided with a backing layer, which as a rule is impermeable to the substance and which avoids bonding with textiles, for which polyester materials are particularly suitable. If the silicone polymers used are silicone adhesives, the matrix can be provided as a direct adhesive to the skin. Other solutions exist in a combination with controlling membranes, other adhesive layers or reservoir layers, as are known in the art.
- the polysiloxane or polysiloxane derivative provided for the matrix outer phase is admixed with a solvent that is volatile at room temperature, usually immiscible with water, in order to achieve flowability, thus obtaining a spreadable composition.
- a solvent that is volatile at room temperature usually immiscible with water
- “Anionssentner” and “cation formers” are added and it is achieved under intensive shearing and stirring a combination of finely dispersed single particles to single droplets, which is due to a reaction of the two additives.
- the mass is then coated in a transdermal therapeutic system appropriate layer thickness on a suitable denosiv equipped sheet and dried with heat application so that the most lipophilic solvent is completely removed except for traces.
- a modification of this technique is based on the already in solution polysiloxane or polysiloxane derivative with a pre-solution of another solvent, the active ingredient and an at least equimolar added amount of the counterion former to complete prior resolution. Subsequently, intensive stirring, so that the later added inner phase is homogeneously distributed.
- Example 1 The mass prepared according to Example 1 is admixed with 50 g of micronized and cross-linked polyvinylpyrrolidone and stirring is continued for about five minutes. Under these circumstances, an inner-phase microreservoir size, which is determined by the grain size through the added swellable polyvinylpyrrolidone particles, is formed which remains even after the coating and drying which takes place analogously to Example 1.
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Abstract
Description
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Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2007323357A AU2007323357A1 (en) | 2006-11-21 | 2007-11-16 | Transdermal therapeutic system comprising ion pair micro-reservoirs |
DE502007003630T DE502007003630D1 (de) | 2006-11-21 | 2007-11-16 | Transdermales therapeutisches system mit ionenpaar-mikroreservoiren |
MX2009005342A MX2009005342A (es) | 2006-11-21 | 2007-11-16 | Sistema terapeutico transdermico que comprende microdepositos de pares de iones. |
EP07846633A EP2094250B1 (de) | 2006-11-21 | 2007-11-16 | Transdermales therapeutisches system mit ionenpaar-mikroreservoiren |
CA002669308A CA2669308A1 (en) | 2006-11-21 | 2007-11-16 | Transdermal therapeutic system comprising ion pair micro-reservoirs |
JP2009537518A JP5578851B2 (ja) | 2006-11-21 | 2007-11-16 | イオン対マイクロリザーバを含む経皮治療システム |
AT07846633T ATE465724T1 (de) | 2006-11-21 | 2007-11-16 | Transdermales therapeutisches system mit ionenpaar-mikroreservoiren |
US12/515,769 US9089527B2 (en) | 2006-11-21 | 2007-11-16 | Transdermal therapeutic system comprising ion pair microreservoirs |
BRPI0719093A BRPI0719093B8 (pt) | 2006-11-21 | 2007-11-16 | sistema transdérmico terapêutico com micro reservatórios de pares de ions |
CN2007800377256A CN101522178B (zh) | 2006-11-21 | 2007-11-16 | 含有离子对-微贮库的透皮治疗系统 |
KR1020147010404A KR101525369B1 (ko) | 2006-11-21 | 2007-11-16 | 이온 쌍 마이크로저장기를 포함하는 경피 치료 시스템 |
IL198745A IL198745A0 (en) | 2006-11-21 | 2009-05-14 | Transdermal therapeutic system comprising ion fair micro-reservoirs |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102006054732.2 | 2006-11-21 | ||
DE102006054732A DE102006054732B4 (de) | 2006-11-21 | 2006-11-21 | Transdermales therapeutisches System mit Ionenpaar-Mikroreservoiren |
Publications (1)
Publication Number | Publication Date |
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WO2008061677A1 true WO2008061677A1 (de) | 2008-05-29 |
Family
ID=39106260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/009926 WO2008061677A1 (de) | 2006-11-21 | 2007-11-16 | Transdermales therapeutisches system mit ionenpaar-mikroreservoiren |
Country Status (15)
Country | Link |
---|---|
US (1) | US9089527B2 (de) |
EP (1) | EP2094250B1 (de) |
JP (2) | JP5578851B2 (de) |
KR (2) | KR101629516B1 (de) |
CN (1) | CN101522178B (de) |
AT (1) | ATE465724T1 (de) |
AU (1) | AU2007323357A1 (de) |
BR (1) | BRPI0719093B8 (de) |
CA (1) | CA2669308A1 (de) |
DE (2) | DE102006054732B4 (de) |
ES (1) | ES2340971T3 (de) |
IL (1) | IL198745A0 (de) |
MX (1) | MX2009005342A (de) |
RU (1) | RU2009123366A (de) |
WO (1) | WO2008061677A1 (de) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6289378B2 (ja) | 2011-12-12 | 2018-03-07 | エルテーエス ローマン テラピー−ジステーメ アーゲー | ブプレノルフィンを含む経皮送達システム |
DE102011090178A1 (de) * | 2011-12-30 | 2013-07-04 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System mit geringer Neigung zur Spontankristallisation |
DE102012213321A1 (de) | 2012-07-30 | 2014-01-30 | Robert Bosch Gmbh | Verfahren und Vorrichtung zum Betreiben eines Fahrzeugs |
MA38698B1 (fr) | 2013-06-04 | 2017-10-31 | Lts Lohmann Therapie Systeme Ag | Système d'administration transdermique |
US9650338B1 (en) | 2016-07-29 | 2017-05-16 | VDM Biochemicals, Inc. | Opioid antagonist compounds and methods of making and using |
US10238600B2 (en) | 2017-04-13 | 2019-03-26 | Richard C. Fuisz | Package, system and methods for custody and control of drugs, and method and composition for making an oral soluble film, containing at least one active agent |
US9901545B1 (en) | 2017-04-13 | 2018-02-27 | Richard C. Fuisz | Method and composition for making an oral soluble film, containing at least one active agent |
CN111093638B (zh) * | 2017-09-04 | 2024-03-26 | 罗曼治疗系统股份公司 | 包含乳化剂的透皮递送系统 |
CN109432061B (zh) * | 2018-11-09 | 2020-10-30 | 北京德默高科医药技术有限公司 | 含有布洛芬或其结构类似物的多层经皮给药系统 |
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WO2002041878A2 (en) * | 2000-11-16 | 2002-05-30 | Euro-Celtique, S.A. | Titratable dosage transdermal delivery system |
DE102005010255A1 (de) * | 2005-03-07 | 2006-09-14 | Lts Lohmann Therapie-Systeme Ag | Faserfreies transdermales therapeutisches System und Verfahren zu seiner Herstellung |
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- 2007-11-16 BR BRPI0719093A patent/BRPI0719093B8/pt active IP Right Grant
- 2007-11-16 EP EP07846633A patent/EP2094250B1/de active Active
- 2007-11-16 CA CA002669308A patent/CA2669308A1/en not_active Abandoned
- 2007-11-16 KR KR1020097010300A patent/KR101629516B1/ko active IP Right Grant
- 2007-11-16 MX MX2009005342A patent/MX2009005342A/es active IP Right Grant
- 2007-11-16 DE DE502007003630T patent/DE502007003630D1/de active Active
- 2007-11-16 AU AU2007323357A patent/AU2007323357A1/en not_active Abandoned
- 2007-11-16 JP JP2009537518A patent/JP5578851B2/ja active Active
- 2007-11-16 ES ES07846633T patent/ES2340971T3/es active Active
- 2007-11-16 AT AT07846633T patent/ATE465724T1/de active
- 2007-11-16 KR KR1020147010404A patent/KR101525369B1/ko active IP Right Grant
- 2007-11-16 US US12/515,769 patent/US9089527B2/en active Active
- 2007-11-16 CN CN2007800377256A patent/CN101522178B/zh active Active
- 2007-11-16 WO PCT/EP2007/009926 patent/WO2008061677A1/de active Application Filing
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2009
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2014
- 2014-03-05 JP JP2014042346A patent/JP2014132020A/ja active Pending
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Also Published As
Publication number | Publication date |
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KR20090082412A (ko) | 2009-07-30 |
JP2014132020A (ja) | 2014-07-17 |
BRPI0719093A2 (pt) | 2013-12-03 |
BRPI0719093B1 (pt) | 2020-03-24 |
US20100112064A1 (en) | 2010-05-06 |
DE102006054732A1 (de) | 2008-05-29 |
IL198745A0 (en) | 2010-02-17 |
CN101522178B (zh) | 2012-10-03 |
ATE465724T1 (de) | 2010-05-15 |
EP2094250A1 (de) | 2009-09-02 |
JP2010510264A (ja) | 2010-04-02 |
RU2009123366A (ru) | 2010-12-27 |
KR20140057398A (ko) | 2014-05-12 |
KR101629516B1 (ko) | 2016-06-10 |
AU2007323357A1 (en) | 2008-05-29 |
DE102006054732B4 (de) | 2010-12-30 |
BRPI0719093B8 (pt) | 2021-05-25 |
US9089527B2 (en) | 2015-07-28 |
JP5578851B2 (ja) | 2014-08-27 |
KR101525369B1 (ko) | 2015-06-09 |
MX2009005342A (es) | 2009-06-01 |
DE502007003630D1 (de) | 2010-06-10 |
EP2094250B1 (de) | 2010-04-28 |
CN101522178A (zh) | 2009-09-02 |
CA2669308A1 (en) | 2008-05-29 |
ES2340971T3 (es) | 2010-06-11 |
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