EP1231899A2 - Mehrschichtige zubereitung zur gesteuerten, pulsartigen abgabe von wirkstoffen - Google Patents
Mehrschichtige zubereitung zur gesteuerten, pulsartigen abgabe von wirkstoffenInfo
- Publication number
- EP1231899A2 EP1231899A2 EP00990596A EP00990596A EP1231899A2 EP 1231899 A2 EP1231899 A2 EP 1231899A2 EP 00990596 A EP00990596 A EP 00990596A EP 00990596 A EP00990596 A EP 00990596A EP 1231899 A2 EP1231899 A2 EP 1231899A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- layers
- active ingredient
- preparation according
- layer
- active
- 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- Withdrawn
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
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
Definitions
- the invention relates to a multilayer preparation for the controlled, pulsed delivery of active ingredients.
- dosage forms with pulse-like release characteristics is of great advantage, for example, in nicotine substitution for smoking cessation, possibly also in substitution therapies for other addiction disorders.
- Nicotine consumption is increasingly in the foreground of public interest, not only because of its harmful effects on smokers themselves, but also because of the problem of passive smoking and the associated nuisance or health damage to other people. Therefore, there are active ingredients and dosage forms on the market that aim to gradually wean the smoker from the "daily nicotine requirement. For other products, the weaning effect is not the focus, but they are only intended to provide the required amount of nicotine in a form that does not include disturbing and harmful side effects of smoking are consumed can.
- Well-known representatives of these groups are, for example, nicotine patches and nicotine chewing gums.
- No. 5,783,207 describes a nicotine-containing lollipop which is composed of two or more layers containing nicotine.
- the layers can have different dissolution rates, and in particular the outermost layer can be designed as a rapidly releasing layer. However, because of the presence of nicotine in all layers, the desirable pulse-like release does not occur.
- Another dosage form containing nicotine is known from US Pat. No. 5,525,351. This consists of two nicotine-containing layers, the first causing a fast and the second slowly releasing nicotine. In this case too, repeated, pulsed release cannot be achieved.
- EP 0 348 683 describes a tablet consisting of three layers. This contains two active ingredients in two layers that are not compatible with each other. Between these two layers is a third layer, which is pharmacologically ineffective and only serves as a separating layer. Here, the layer structure only serves to keep two incompatible active substances in spatial separation.
- a three-layer tablet is also known from US Pat. No. 5,650,169, in which a barrier layer is located between two layers containing an active substance.
- the tablet as a whole - with the exception of a small area - is possible polymer layer.
- the layer structure is not concentric.
- the barrier layer and the second active substance-containing layer are coated with an impermeable, water-insoluble, but soluble in an alkaline environment. This means that these layers only become physiologically accessible after the covering has been destroyed or dissolved. More than two layers can also be present within the casing. As with the multilayer system described in US Pat. No. 5,650,169, the structure is also not concentric here.
- a multilayer dosage form with special properties is known from US Pat. No. 5,575,819. These are pollen grains, which are filled with the active ingredient and then provided with a multi-layer coating, the surrounding layers also being able to contain active ingredients. These pollen grains are placed in capsules, tablets, etc. for administration. They are primarily intended for the veterinary field.
- US 5,011,692 describes a multilayer dosage form in which only every second layer contains an active ingredient.
- the layered layers are covered on their face by a water-insoluble layer; the latter also covers one side of the layers.
- a periodic, pulse-like release characteristic such as is required, for example, for the purpose of weaning nicotine or other comparable application situations, cannot be achieved or only approximately. It was therefore an object of the present invention to provide a dosage form for active ingredients which enables controlled, pulsed release of active ingredients.
- the task was to create a preparation containing nicotine which, due to its pulse-like release characteristics, is particularly suitable for nicotine withdrawal.
- a multilayer preparation according to the main claim which has at least four layers, of which at least two non-adjacent layers contain any active ingredient A.
- a pulsed release of the active ingredient A can take place over a desired period of time.
- Those layers, or at least some of these layers, which do not contain the active ingredient A can preferably be designed such that they are dissolved or eroded more slowly than those layers which contain the active ingredient A. This can be achieved through different layer thicknesses, as well as through a different composition of the individual layers, or both.
- the dissolution or erosion of the layers not containing the active ingredient A can take up 1.01 to 100,000 times the time, preferably 1.2 to 10000 times the time, particularly preferably twice to 100 times the time, based on the time is required for the dissolution or erosion of the layer containing active ingredient A.
- the rate of dissolution or erosion of individual layers can be between one second and one month, depending on the embodiment of the invention. Solution speeds in the range of 1 second are preferred. isme and 1 day, particularly preferably in the range of 1 second and 10 minutes.
- the layers containing active ingredient A can be designed as rapidly disintegrating, eroding or soluble layers, which leads to a correspondingly accelerated release of active ingredient ("quick release").
- the release characteristics in particular the interval length between the active ingredient peaks and the pulse shape, can be controlled by a suitable choice of the solubility or erosion or decay properties of the layers.
- the preparations according to the invention have a concentric, either centrally symmetrical structure, for example spherical or approximately spherical (FIG. 1), or an axially symmetrical structure (FIGS. 2 and 3), preferably oblong-ellipsoidal or cylindrical.
- the layers are concentric, like an onion skin, arranged around a central core that represents the innermost layer. Depending on the requirements, this may also contain the active ingredient A or other active ingredients, or be free thereof.
- the individual layers are arranged as a flat laminate, so that there is no concentric structure.
- Fig. 4 shows such an embodiment in a sectional view (Fig. 4a) or top view or plan view (Fig. 4b), the shape of the laminate being round or angular May have structural feature ⁇ .
- At least one of the layers can be a pressure sensitive adhesive that joins the individual layers together.
- these faces can be provided with at least one water-impermeable layer (4).
- the multilayer preparation is in the form of a lollipop.
- the preparations according to the invention can be produced in the form of tablets, film-coated tablets, lozenges or dragees.
- the multi-layer tablet is designed as a lozenge, with a nicotine-containing layer with rapid release characteristics being followed by a nicotine-free layer, which dissolves only slowly.
- a tip of the active ingredient is released during the sucking, then the subsequent nicotine-free layer must be loosened by sucking before the next nicotine-containing layer becomes accessible and a further tip of the active ingredient can be released.
- the nicotine dosing scheme of a cigarette can be simulated by several such layers. Such a structure meets the demand for an interval-like, pulse-like nicotine release in order to achieve an optimal weaning effect.
- the invention also includes embodiments of the type just described in which nicotine is replaced by another active ingredient.
- the individual layers can additionally contain flavors, colorants, decay accelerating additives, absorption accelerators or sweeteners. All layers, including, if appropriate, the core, can have the same additives. However, the invention also encompasses embodiments in which the individual layers, and possibly the core, differ in terms of the content of additives.
- a variant of the invention is particularly preferred in which every second layer contains the active ingredient A and the layer in between is free of active ingredient A, so that there is an alternating sequence of active ingredient-containing and active ingredient-free layers.
- the invention also includes those embodiments in which two or more layers which do not contain this active ingredient are arranged between the layers containing active ingredient A. An alternating sequence can be observed (FIG. 5), but other types of arrangement (FIG. 6) can also be advantageous.
- the outermost layer of the preparation can also contain active ingredient A and / or at least one other active ingredient, but it can also, if it is advantageous, be free of active ingredients.
- the multilayer preparation can preferably have up to 60 layers containing the active ingredient A, a structure of 5 to 30 such layers being more preferred, and a structure of 6 to 15 such layers being particularly preferred.
- the total number of layers is at least four, but preferably at least five, and embodiments with at least 10 layers are particularly preferred.
- the layer thickness of the individual layers is between 1 and 5000 ⁇ m, preferably between 10 and 2000 ⁇ m, particularly preferably between 20 and 500 ⁇ m. The selection of the layer thickness depends, among other things, on the desired erosion or dissolution rate, as described above. Embodiments are provided in which all layers have approximately the same layer thickness, as well as those in which at least one layer has a thickness which differs from the other layers.
- the preparation can also contain two or more active ingredients, which are released after oral intake after a certain period of time.
- the z. B. contains three active ingredients in a separate layer containing an active ingredient, release the first active ingredient shortly after ingestion (e.g. in the morning), the second active ingredient after a certain period of time (e.g. at noon) and the third active ingredient after one further period (e.g. in the evening).
- the concentration of active substance can be the same in the individual layers, but in some cases it may be necessary for the layers, or at least some of the layers Layers that have different concentrations of active ingredient.
- the problem arises that the active substance content per layer becomes smaller and smaller due to the radii decreasing towards the center.
- it may be appropriate, for example, to increase the active substance concentrations in the layers accordingly, or to vary the thickness of the layers or their solubility, or suitable additives such as, for. B. Add enhancer.
- Differences in the concentration of the active substance (s) in the individual layers can not only serve to compensate for the regions of different active substance contents due to the geometrical design, but also to modulate the active substance release in a desired manner.
- aspirin is used as another particularly preferred active ingredient A.
- active ingredients which can be added to the layers of the preparation either as active ingredient A or as additional active ingredients:
- Active substances from the active substance groups of the parasympatholytics e.g. scopolamine, atropine, berlactyzine
- the cholinergics e.g. physostigmine, nicotine
- the neuroleptics e.g.
- Chlorpromazine, haloperidol the monoamine oxidase inhibitor (e.g. tranylcypromine, selegiline), the sympathomimetic and antisy pathotonic (e.g. propanolol, timolol, bupranolol, clonidine, dihydroergotamine, naphazoline), the anxiolytics (e.g. , Triazolam), local anesthetics (e.g.
- Lidocaine Lidocaine
- the central analgesics e.g. fentanyl, sufenanil
- the anti-rheumatic drugs e.g. indomethacin, piroxicam, lornoxicam
- the coronary therapeutic agents e.g. glycerol trinitrate, isosorbide dinitrate
- the estrogens, progestogens and androgens e.g. diphenhydramine, clema- stin, terfenadine
- the prostaglandin derivatives e.g. diphenhydramine, clema- stin, terfenadine
- the vitamins e.g. vitamin E, cholecalciferol
- the cytostatics e.g. calcium glycosides
- cardioactive glycosides such as digitoxin and digoxin.
- Active ingredients which are centrally active and tend to have a habituation effect on the receptors when continuously released are particularly preferred. With regard to pharmacokinetics, they have a high level of flooding. H. they reach the receptor in question very quickly. In addition, they are quickly degradable, i. H. they are metabolized quickly, e.g. B. in the seconds or minutes range.
- the multilayer preparations according to the invention are preferably used as tablets or lozenges for oral administration. Depending on the active ingredients used and the particular field of application, however, other embodiments may be more advantageous, for example for rectal or vaginal administration, or in the form of implants. In addition, the preparations according to the invention are also suitable for the administration of active ingredients in veterinary medicine.
- the multilayer preparations according to the invention can be used advantageously wherever the pulsed, intermittent release of an active ingredient or other substance to the surrounding environment is important. This includes applications in the fields of agriculture, horticulture, industry and the household (eg tablets for detergents or detergents).
- the following constituents can be contained in the base material of the active ingredient-containing, but also active ingredient-free layers: polymers such as polyisobutylene, esters of polyvinyl alcohol, polyacrylic, polymethacrylic and polymethyl methacrylic acid and their derivatives, natural rubber, styrene, isoprene and styrene and butadiene Polymers or silicone polymers, resin components such as saturated or unsaturated hydrocarbon resins, derivatives of abietyl alcohol and ß-pinene; also plasticizers such as phthalic acid esters, triglycerides and fatty acids, and a number of other substances known to the person skilled in the art.
- All or individual layers e.g.
- only the outermost layer or layers can be designed to be enteric-resistant. This can be done by using e.g. As wax, sealing wax, ethyl cellulose or other materials known to those skilled in the art can be achieved.
- Embodiments are preferred in which at least one layer is made resistant to gastric juice. This can be the outermost layer or at least one of the inner layers, depending on the intended use.
- the layers of the dosage form according to the invention can also contain further auxiliaries as additives.
- auxiliaries are classified according to their function into plasticizers, tackifiers, absorption mediators, stabilizers or flow regulators. Such substances, which must be physiologically harmless, are generally known to the person skilled in the art.
- Substances with solubility, erosion or swelling properties that meet the requirements are used as carrier or fillers.
- Typical substances for this are, for example, lactose, Cellulose types, sugar alcohols such as B. mannitol and sorbitol, various types of starch and alginates.
- acrylic acid derivatives for example as Eudragit L or Eudragit S, Po lyvinylalkohole, hydroxpropyl or cellulose acetate phthalate, as polyacrylates such as Eudragit ® E30D, polyacrylic acid derivatives, shellac or cellulose such as methyl or ethyl cellulose used in the small intestine-soluble substances.
- the following methods can advantageously be used in the production of the dosage form according to the invention: spray coating, the compression or sintering method known to the person skilled in the art, and the lamination of individual layers to form a laminate, or multiple coating by means of the hot-melt method or other methods known to the person skilled in the art for multiple coating.
- the process according to the invention shows how concentric or sheet-like preparations according to the invention can be produced in a relatively simple manner by a combination of suitable process steps.
- Figure 1 shows a section through a centrally symmetrical embodiment of the invention.
- the active substance-free layers (2) are marked light, the active substance-containing layers (1) are marked dark.
- Figure 2 shows a section through an axially symmetrical embodiment of the invention.
- the active substance-free layers (2) are marked light, the active substance-containing layers (1) are marked dark.
- Figure 3 shows a section through an axially symmetrical embodiment of the invention, in which all layers their end face come into contact with the surrounding medium.
- the active substance-free layers (2) are marked light, the active substance-containing layers (1) are marked dark.
- FIG. 4 shows a sheet-like laminate, comprising an alternating number of layers (2) which do not contain the active ingredient A (1) and the active ingredient A.
- FIG. 4 a shows the laminate in a side view (sectional view), with the optional water-impermeable layer (4) on the end faces, and
- FIG. 4 b shows embodiments of different geometries in the top view.
- FIG. 5 shows a section through a centrally symmetrical embodiment of the invention, which contains active substance-free and active substance-containing layers in an alternating sequence.
- the active ingredient-free layers (2) are light, the active ingredient-containing layers (1) are dark, and another layer (3) is marked black.
- FIG. 6 shows a section through a centrally symmetrical embodiment of the invention, which has active substance-free layers and active substance-containing layers in a non-alternating sequence.
- the active substance-free layers (2) are light, the active substance-containing layers (1) are dark, and another layer (3) is marked in black.
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Addiction (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Laminated Bodies (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19956486A DE19956486A1 (de) | 1999-11-24 | 1999-11-24 | Mehrschichtige Zubereitung zur gesteuerten, pulsartigen Abgabe von Wirkstoffen |
DE19956486 | 1999-11-24 | ||
PCT/EP2000/010934 WO2001037813A2 (de) | 1999-11-24 | 2000-11-06 | Mehrschichtige zubereitung zur gesteuerten, pulsartigen abgabe von wirkstoffen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1231899A2 true EP1231899A2 (de) | 2002-08-21 |
Family
ID=7930143
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00990596A Withdrawn EP1231899A2 (de) | 1999-11-24 | 2000-11-06 | Mehrschichtige zubereitung zur gesteuerten, pulsartigen abgabe von wirkstoffen |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1231899A2 (de) |
JP (1) | JP2003514846A (de) |
KR (1) | KR100690518B1 (de) |
CN (1) | CN1399544A (de) |
AR (1) | AR026590A1 (de) |
AU (1) | AU782141B2 (de) |
CA (1) | CA2391962A1 (de) |
DE (1) | DE19956486A1 (de) |
IL (2) | IL149836A0 (de) |
WO (1) | WO2001037813A2 (de) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AUPR839001A0 (en) * | 2001-10-19 | 2001-11-15 | Eli Lilly And Company | Dosage form, device and methods of treatment |
WO2003037244A2 (en) * | 2001-10-29 | 2003-05-08 | Therics, Inc. | System for manufacturing controlled release dosage forms, such as a zero-order release profile dosage form manufactured by three-dimensional printing |
US20050232995A1 (en) | 2002-07-29 | 2005-10-20 | Yam Nyomi V | Methods and dosage forms for controlled delivery of paliperidone and risperidone |
DE10353186A1 (de) * | 2003-11-13 | 2005-06-16 | Röhm GmbH & Co. KG | Mehrschichtige Arzneiform, enthaltend eine in Bezug auf die Wirkstoffabgabe modulatorisch wirkende Substanz |
US7670624B2 (en) * | 2004-01-29 | 2010-03-02 | Astella Pharma Inc. | Gastrointestinal-specific multiple drug release system |
CN101111231A (zh) * | 2005-03-29 | 2008-01-23 | 罗姆有限公司 | 包含具有影响调节物质递送的基质的小丸的多颗粒药用形式 |
BRPI0609598A2 (pt) * | 2005-03-29 | 2010-04-20 | Roehm Gmbh | forma farmacêutica multiparticulada compreendendo péletes com uma substáncia possuindo um efeito modular em relação à liberação de ingrediente ativo |
GB0707489D0 (en) * | 2007-04-18 | 2007-05-23 | Renaissance Pharma | Compounds |
CN102764243B (zh) * | 2011-05-06 | 2014-10-29 | 上海医药工业研究院 | 一种阿司匹林脉冲释放微丸和其制剂及其制备方法 |
KR20180014778A (ko) * | 2015-06-03 | 2018-02-09 | 트리아스텍 인코포레이티드 | 제형 및 이의 용도 |
WO2017074262A1 (en) * | 2015-10-26 | 2017-05-04 | Agency For Science, Technology And Research | Core-shell composite material |
JP7040418B2 (ja) * | 2018-11-21 | 2022-03-23 | 株式会社村田製作所 | 錠剤 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB793808A (en) * | 1954-07-22 | 1958-04-23 | Frank Mario Bardani | Sustained action pill |
NL109170C (de) * | 1958-02-03 | |||
JPS62133189A (ja) * | 1985-12-02 | 1987-06-16 | Bando Chem Ind Ltd | ゴム製床カバ−材 |
JPH0778017B2 (ja) * | 1985-12-28 | 1995-08-23 | 住友製薬株式会社 | パルス的かつ持続放出性製剤 |
US5236713A (en) * | 1987-10-21 | 1993-08-17 | Teikoku Seiyaku Kabushiki Kaisha | Preparation for intermittently releasing active agent applicable to oral cavity |
AU632602B2 (en) * | 1989-08-02 | 1993-01-07 | John David Arnold | Method and preparation for reducing risk of myocardial infarction |
AU7568394A (en) * | 1993-08-19 | 1995-03-14 | Cygnus Therapeutic Systems | Water-soluble pressure-sensitive mucoadhesive and devices provided therewith for emplacement in a mucosa-lined body cavity |
US6156343A (en) * | 1994-12-27 | 2000-12-05 | Akzo Nobel N.V. | Controlled release preparation |
-
1999
- 1999-11-24 DE DE19956486A patent/DE19956486A1/de not_active Withdrawn
-
2000
- 2000-11-06 CA CA002391962A patent/CA2391962A1/en not_active Abandoned
- 2000-11-06 AU AU30034/01A patent/AU782141B2/en not_active Ceased
- 2000-11-06 IL IL14983600A patent/IL149836A0/xx active IP Right Grant
- 2000-11-06 CN CN00816260A patent/CN1399544A/zh active Pending
- 2000-11-06 EP EP00990596A patent/EP1231899A2/de not_active Withdrawn
- 2000-11-06 WO PCT/EP2000/010934 patent/WO2001037813A2/de active IP Right Grant
- 2000-11-06 JP JP2001539428A patent/JP2003514846A/ja not_active Withdrawn
- 2000-11-06 KR KR1020027006438A patent/KR100690518B1/ko not_active IP Right Cessation
- 2000-11-23 AR ARP000106187A patent/AR026590A1/es unknown
-
2002
- 2002-05-23 IL IL149836A patent/IL149836A/en not_active IP Right Cessation
Non-Patent Citations (1)
Title |
---|
See references of WO0137813A2 * |
Also Published As
Publication number | Publication date |
---|---|
AU782141B2 (en) | 2005-07-07 |
AR026590A1 (es) | 2003-02-19 |
JP2003514846A (ja) | 2003-04-22 |
AU3003401A (en) | 2001-06-04 |
IL149836A (en) | 2008-08-07 |
CA2391962A1 (en) | 2001-05-31 |
IL149836A0 (en) | 2002-11-10 |
DE19956486A1 (de) | 2001-06-21 |
WO2001037813A3 (de) | 2001-12-27 |
CN1399544A (zh) | 2003-02-26 |
KR20020058027A (ko) | 2002-07-12 |
KR100690518B1 (ko) | 2007-03-09 |
WO2001037813A2 (de) | 2001-05-31 |
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