WO2000064415A1 - Verfahren zur herstellung einer wasserunlöslichen amorphen oder teilamorphen retardmatrix - Google Patents

Verfahren zur herstellung einer wasserunlöslichen amorphen oder teilamorphen retardmatrix Download PDF

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Publication number
WO2000064415A1
WO2000064415A1 PCT/EP2000/003612 EP0003612W WO0064415A1 WO 2000064415 A1 WO2000064415 A1 WO 2000064415A1 EP 0003612 W EP0003612 W EP 0003612W WO 0064415 A1 WO0064415 A1 WO 0064415A1
Authority
WO
WIPO (PCT)
Prior art keywords
matrix
extrusion
release
active substance
dosage form
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.)
Ceased
Application number
PCT/EP2000/003612
Other languages
German (de)
English (en)
French (fr)
Inventor
Hubert Rein
Klaus-Jürgen Steffens
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.)
Euro Celtique SA
Original Assignee
Euro Celtique SA
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
Priority to BRPI0009927-9A priority Critical patent/BR0009927B1/pt
Priority to DE20022720U priority patent/DE20022720U1/de
Priority to AU45542/00A priority patent/AU763609B2/en
Priority to IL14575500A priority patent/IL145755A0/xx
Priority to US09/980,727 priority patent/US8557286B1/en
Priority to CA002372025A priority patent/CA2372025C/en
Priority to HU0200843A priority patent/HU227001B1/hu
Priority to DE50014164T priority patent/DE50014164D1/de
Priority to DK00927010T priority patent/DK1171101T3/da
Priority to JP2000613406A priority patent/JP4575599B2/ja
Application filed by Euro Celtique SA filed Critical Euro Celtique SA
Priority to KR10-2001-7013353A priority patent/KR100511113B1/ko
Priority to EP00927010A priority patent/EP1171101B1/de
Publication of WO2000064415A1 publication Critical patent/WO2000064415A1/de
Anticipated expiration legal-status Critical
Priority to CY20071100766T priority patent/CY1106478T1/el
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • 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
    • A61K9/2095—Tabletting processes
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Definitions

  • the invention relates to a method for producing pharmaceutical forms or precursors thereof by means of extrusion.
  • the invention further relates to a pharmaceutical form that can be produced by means of extrusion processes.
  • Extrusion is a particularly widespread process for the modification of polysaccharides, especially starches, in the adhesive industry or plastics processing.
  • Extrusion for the production of starchy preparations, such as pasta, the so-called peanut flips or various sweets, is known from food technology.
  • starchy preparations such as pasta, the so-called peanut flips or various sweets
  • Products selected the manufacturing conditions so that foamed, so-called popped products are formed.
  • extrusion is used to process waxes, fatty alcohols, fats and various
  • thermosets Thermoplastics and thermosets.
  • extruded matrices made of various plastic compounds are described in EP-A2-0 240 904, EP-A2-0 240 906 and in EP-A2-0 358 105.
  • the processing of starchy mixtures into pharmaceutical products (capsule shells) by means of an injection molding process is described EP-B2-0 118 240. Little is known in this connection how the polysaccharides used are changed during extrusion.
  • the method described there is not suitable for preparations containing starch as the main component.
  • the pharmaceutical forms that are taken orally for example tablets, coated tablets or capsules, are by far the most important.
  • These also include the so-called sustained-release dosage forms, which contain a relatively high dose of active ingredient and release it in a controlled and controlled manner over a longer period of time. For the patient, this means that the frequency of ingestion can be significantly reduced.
  • the advantage of the slow-release forms is that the active substance concentration in the blood is very even, which leads to a long-lasting effect and few side effects.
  • the so-called matrix form plays an important role in the formulation of sustained-release pharmaceutical forms.
  • Matrix is understood to mean a shaped body, for example a tablet or a dragee, made of indifferent auxiliary substances, from which the active substances in the gastrointestinal tract are released in a controlled manner.
  • the active substances are generally released partly by diffusion, partly by the slow degradation of the matrix.
  • such matrices are made from synthetic polymers, such as polyacrylate or polyethylene.
  • extrusion processes for the production of slow-release molds from synthetic raw materials are also known.
  • a fundamental disadvantage of the pharmaceutical forms previously produced by means of extrusion processes is the use of active substance carriers such as plastics, waxes or even fatty alcohols.
  • active substance carriers such as plastics, waxes or even fatty alcohols.
  • These non-biodegradable and partially environmentally harmful auxiliaries, such as residual monomers in the polymers used, have so far been indispensable for pharmaceutical forms which are produced by extrusion processes and which allow controlled and slow release of active ingredients.
  • there is no known extrusion process for the production of pharmaceutical forms which allow rapid release of active ingredients There is therefore a strong need to provide an extrusion process for the production of pharmaceutical forms with regulated, that is to say optionally delayed or also rapid, active ingredient release, which overcomes the disadvantages of the prior art, in particular the use of non-biodegradable and in some cases even environmentally toxic carriers . Further objects result from the following description of the invention.
  • the pharmaceutical form has a matrix which essentially contains the active substance content, the essential properties of which are formed by the extrusion, and a biodegradable polysaccharide and / or derivative thereof and / or a complex thereof and / or any mixture of the aforementioned substances with other substances and / or saccharides and / or derivatives thereof as a constituent of the matrix and at least one pharmaceutically active substance.
  • the active ingredient release of the pharmaceutical form is regulated by adding auxiliaries and / or varying the extrusion process parameters, such as temperature, nozzle geometry and / or extrusion speed.
  • the matrix of the pharmaceutical form produced according to the invention is amorphous or partially amorphous.
  • the invention further relates to a method in which the pharmaceutical form according to the invention comprises, as a polysaccharide, starch or a derivative thereof, in particular amorphous or partially amorphous starch or a derivative thereof, in the matrix.
  • the invention relates to a production process in which the pharmaceutical form comprises a water-insoluble and preferably swellable matrix.
  • the pharmaceutical form produced according to the invention is a sustained-release matrix.
  • compositions in a pharmaceutical form produced according to the invention which has an active substance release which essentially obeys the lapidus function and particularly preferably an active substance release which can be set over 24 hours or longer.
  • Another important object of the invention is to provide a pharmaceutical form which essentially does not require non-biodegradable ingredients.
  • a pharmaceutical form which comprises a matrix which essentially contains the active substance content and is essentially formed by extrusion, and a polysaccharide and / or a derivative thereof and / or a complex thereof and / or any mixture of the aforementioned substances with other substances and / or saccharides and / or derivatives thereof as an essential component of the matrix and at least one pharmaceutically active substance.
  • the invention further relates to the use of the pharmaceutical form according to the invention as an adjuvant in direct tableting, for the production of granules for Tableting and capsule filling, for further processing by means of injection molding and / or for the production of monoblock drug forms.
  • an amorphous or partially amorphous matrix is generated from the crystalline or partially crystalline polysaccharides, in particular from starch or derivatives thereof, or from mixtures of these components.
  • the extrusion conditions such as temperature, nozzle geometry and extrusion speed are of great importance in the reproducible production of pharmaceutical forms which are based on the extrusion of polysaccharides and derivatives thereof.
  • native starch can be completely plasticized or vitrified under suitable extrusion conditions, so that homogeneous plastic-like moldings are produced.
  • the formulations used in the process according to the invention consist of a mixture of polysaccharides and / or derivatives thereof, preferably of a mixture of starch and / or starch derivatives, a wide variety of starch types being suitable. Furthermore, the mixture contains at least one pharmaceutically active substance in amounts of up to 50% and preferably of up to 30% based on the total weight of the formulation, and can also comprise further other substances.
  • the thoroughly blended dry formulation should be used in the process according to the invention.
  • Water in concentrations of up to 15% can be added. When using a positive extruder, less than 15% water is sufficient.
  • the premix obtained should preferably be sieved free of lumps in order to obtain a to ensure perfect conveying by the stuffing screw.
  • the extruder can be started up and cleaned, for example, with corn grits.
  • the temperature at the outlet of the extruder under normal pressure should not exceed 100 ° C., since the formation of a pore-free matrix should be very difficult at temperatures above 100 ° C.
  • the total energy to be supplied to the process in the form of shear forces, temperature, heat or pressure should be as constant as possible and sufficient to achieve the glass transition.
  • the optimum screw speed and nozzle geometry can be matched to the mixture of the carrier according to the invention and water. at
  • Extrusion temperatures below 100 ° C and a suitable screw speed usually result in transparent and completely amorphous products.
  • the degree of plasticization of the active ingredient / polysaccharide, preferably active ingredient / starch, mixtures is closely linked to the screw speed. While extrusion is no longer possible below the lowest speed, an excessively high screw speed leads to the partial "popping up" of the dosage form.
  • Varying the extrusion process parameters enables the production of pharmaceutical forms according to the method according to the invention, which have a regulated release of active ingredient.
  • “regulated” means that both rapid-release dosage forms and delayed-release dosage forms, so-called sustained release dosage forms with release times of up to 24 hours or longer, can be produced by the extrusion process according to the invention.
  • processing temperature in relation to the regulation of the
  • Drug release is important. Rapidly releasing dosage forms are obtained e.g. by extrusion below the gelatinization temperature of the polysaccharides used in each case. Because among other things the density of the matrix influences the release of the incorporated active substances, corresponding prolonged-release drug forms can be achieved through partial to complete glazing, i.e. by transition to the amorphous
  • such an amorphous or partially amorphous matrix produced by the process according to the invention preferably from amorphous or partially amorphous starch or derivatives thereof or from mixtures of these components, is essentially not water-soluble, but is preferably swellable and water-insoluble.
  • the pharmaceutically active substance or the pharmaceutically active substances can be present in the matrix in dissolved, solid or liquid form.
  • starches examples include tapioca starch, wheat starch, potato starch, Starch 1500® (partially pre-gelatinized / pregelatinized corn starch sold by Colorcon), Waxylis® (waxy corn starch from Roquette), Eurylon 7 ® (amylomais starch from Roquette), maize starch, acetyl starch.
  • compositions are also available according to the extrusion process according to the invention which have an active ingredient release regulated by the addition of auxiliary substances.
  • auxiliary substances for example, the following can be added:
  • hydrophilic or amphiphilic solids water-soluble substances such as e.g. Sodium chloride, lactose, surfactants such as Sodium lauryl sulfate, silicon dioxide (colloidally dispersed and / or as a xerogel), - hydrophilic or amphiphilic liquids,
  • Polyglycols such as Glycerol, polyethylene glycol, surfactants such as Polysorbates, gases such as Nitrogen, carbon dioxide.
  • a reduction in the active ingredient release by obstructing the diffusion can be brought about, for example, by adding the following auxiliary substances: lipophilic or amphiphilic auxiliaries of natural, synthetic and / or partially synthetic origin such as fats, fatty acids, waxes in solid or liquid state, - saturated or unsaturated hydrocarbons,
  • Metal soaps such as Magnesium stearate.
  • a reduction in the drug release can be caused by the formation of stoichiometric or unstoichiometric complexes such as e.g. Iodine starch complex, miltefosine amylose complex can be achieved.
  • stoichiometric or unstoichiometric complexes such as e.g. Iodine starch complex, miltefosine amylose complex can be achieved.
  • the release of the incorporated active ingredients can be influenced by using suitable mixtures of the constituents of the matrix, preferably by using mixtures of different starches and / or derivatives thereof. Further factors which can additionally influence the release of the active ingredient are the surface of the shaped body of the dosage form and its particle size or the distribution of the active ingredient or the active ingredients within the particle.
  • the pharmaceutical form can be dried solely by the heat of friction generated, so that no final drying step is necessary.
  • a production extruder preferably in a twin-screw extruder, particularly preferably in a positive-feeding twin-screw extruder, all process steps, such as metering, moistening, mixing, extruding and molding, can take place continuously.
  • the method according to the invention can thus combine the mixing, granulating and drying process, for which no additional energy has to be expended, in one device.
  • the number of possible incompatibilities is also reduced, since the pharmaceutical form comprises, for example, only a carrier, preferably starch or a derivative thereof, and a pharmaceutically active substance.
  • the matrix produced by the method according to the invention also prevents possible, unwanted segregation.
  • Brabender single-screw extrader type 81 1201. The device has three segments that can be independently temperature controlled, the inlet area, the screw area and the nozzle.
  • a screw conveyor was used, without compaction, with a screw length of 22 cm, a screw diameter of 19 mm, a core diameter of 16 mm and a pitch of 15 mm.
  • Nozzles with different nozzle diameters between 2.5 and 7 mm were used.
  • the batch size in the tests was between 350 and 600 grams.
  • the active ingredient and starch were mixed thoroughly in a Stephan mixer, moistened with 15% water and this premix was sieved without lumps.
  • Temperatures of approximately 65 ° C. in the inlet region of the extruder, of approximately 80 ° C. in the screw region and of approximately 98 ° C. at the die have proven to be a suitable temperature choice for carrying out the process according to the invention.
  • Differential thermal analysis can be used to detect the transition from crystalline or semi-crystalline starch to the amorphous state.
  • the starch With suitable extrusion conditions, the starch is completely vitrified, ie it changes to the amorphous state.
  • an investigation was carried out with tapioca starch as the polysaccharide and caffeine as the active ingredient.
  • the thermogram of the premix shown in Figure la, consisting of 90% tapioca starch and 10 % Caffeine, with added water still shows the typical endothermic peaks in the range of about 65 ° C.
  • the transition from the crystalline or partially crystalline to the amorphous or partially amorphous state can also be detected using X-ray diffractometry.
  • X-ray diffractometry For the following exemplary investigation, a sample consisting of 80% potato starch and
  • the X-ray diffractogram of the corresponding extradate does not show any method
  • the rate of drug release can also be regulated via the type of polysaccharide or the polysaccharide mixture.
  • a premix consisting of potato starch and 10% caffeine was used for the quantitative investigation of the active ingredient release.
  • the change in the type of starch, together with the lower dosage of active ingredient, leads to a significant slowdown in the release of the active ingredient.
  • the diagram shown in Figure 5 shows that the extrudate produced by the process according to the invention brings about an active ingredient release over a period of 24 hours.
  • the duration and the course of the total active substance release can be regulated.
  • Very long drug release times such as about 24 hours in the previous example, are to be regarded as advantageous with regard to the development of a new retardation principle, since this gives "reserves" for extremely well water-soluble drugs.
  • the active ingredient release can be influenced in a targeted manner by the polysaccharides used or corresponding derivatives and mixtures thereof, by adding appropriate auxiliaries and / or by the extrusion process parameters.
  • Faster drug release times can also be achieved by the process according to the invention.
  • the table below shows an example that the process parameter changes, such as incomplete glazing, can regulate the drug release times over a wide range.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Psychiatry (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2000/003612 1999-04-22 2000-04-20 Verfahren zur herstellung einer wasserunlöslichen amorphen oder teilamorphen retardmatrix Ceased WO2000064415A1 (de)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DK00927010T DK1171101T3 (da) 1999-04-22 2000-04-20 Fremgangsmåde til fremstilling af en vanduoplöselig amorf depotmatrix
AU45542/00A AU763609B2 (en) 1999-04-22 2000-04-20 Method for producing a water-insoluble amorphous or partially amorphous controlled release matrix
IL14575500A IL145755A0 (en) 1999-04-22 2000-04-20 Method for producing a water-insoluble amorphous or partially amorphous controlled release matrix
US09/980,727 US8557286B1 (en) 1999-04-22 2000-04-20 Method for producing a water-insoluble amorphous or partially amorphous controlled release matrix
CA002372025A CA2372025C (en) 1999-04-22 2000-04-20 Method for producing a water-insoluble amorphous or partially amorphous controlled release matrix
HU0200843A HU227001B1 (en) 1999-04-22 2000-04-20 Method for producing a water-insoluble amorphous or partially amorphous controlled release matrix
DE50014164T DE50014164D1 (de) 1999-04-22 2000-04-20 Verfahren zur herstellung einer wasserunlöslichen amorphen retardmatrix
BRPI0009927-9A BR0009927B1 (pt) 1999-04-22 2000-04-20 mÉtodo para produzir uma matriz de liberaÇço controlada, amàrfica ou parcialmente amàrfica insolével em Água.
DE20022720U DE20022720U1 (de) 1999-04-22 2000-04-20 Arzneiform
JP2000613406A JP4575599B2 (ja) 1999-04-22 2000-04-20 非水溶性の非晶質または部分的に非晶質の放出制御基材を製造する方法
KR10-2001-7013353A KR100511113B1 (ko) 1999-04-22 2000-04-20 비수용성 비정질 또는 부분비정질 서방성 매트릭스의 제조방법
EP00927010A EP1171101B1 (de) 1999-04-22 2000-04-20 Verfahren zur herstellung einer wasserunlöslichen amorphen retardmatrix
CY20071100766T CY1106478T1 (el) 1999-04-22 2007-06-11 Μεθοδος για την παραγωγη αμορφης επιβραδυντικης μητρας μη διαλυτης στο υδωρ

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19918325.2 1999-04-22
DE19918325A DE19918325A1 (de) 1999-04-22 1999-04-22 Verfahren zur Herstellung von Arzneiformen mit regulierter Wirkstofffreisetzung mittels Extrusion

Publications (1)

Publication Number Publication Date
WO2000064415A1 true WO2000064415A1 (de) 2000-11-02

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PCT/EP2000/003612 Ceased WO2000064415A1 (de) 1999-04-22 2000-04-20 Verfahren zur herstellung einer wasserunlöslichen amorphen oder teilamorphen retardmatrix

Country Status (18)

Country Link
US (1) US8557286B1 (https=)
EP (2) EP1839651A1 (https=)
JP (2) JP4575599B2 (https=)
KR (1) KR100511113B1 (https=)
CN (1) CN1214783C (https=)
AT (1) ATE356617T1 (https=)
AU (1) AU763609B2 (https=)
BR (1) BR0009927B1 (https=)
CA (1) CA2372025C (https=)
CY (1) CY1106478T1 (https=)
DE (3) DE19918325A1 (https=)
DK (1) DK1171101T3 (https=)
ES (1) ES2284495T3 (https=)
HU (1) HU227001B1 (https=)
IL (1) IL145755A0 (https=)
PT (1) PT1171101E (https=)
RU (1) RU2208436C2 (https=)
WO (1) WO2000064415A1 (https=)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP1429735A2 (de) * 2001-09-26 2004-06-23 Klaus-Jürgen Steffens Verfahren und vorrichtung zur herstellung von granulaten umfassend mindestens einen pharmazeutischen wirkstoff

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US6375957B1 (en) 1997-12-22 2002-04-23 Euro-Celtique, S.A. Opioid agonist/opioid antagonist/acetaminophen combinations
EP1041987B1 (en) 1997-12-22 2006-04-19 Euro-Celtique S.A. Pharmaceutical oral dosage form comprising a combination of an opioid agonist and naltrexone
DE19918325A1 (de) * 1999-04-22 2000-10-26 Euro Celtique Sa Verfahren zur Herstellung von Arzneiformen mit regulierter Wirkstofffreisetzung mittels Extrusion
EP1387673B1 (en) 2001-05-11 2010-12-29 Endo Pharmaceuticals Inc. Abuse-resistant controlled-release opioid dosage form
HUE032656T2 (en) 2002-04-05 2017-10-30 Euro Celtique Sa Pharmaceutical composition containing oxicodone and naloxone
EP1479381A1 (en) * 2003-05-19 2004-11-24 Euro-Celtique S.A. Pharmaceutical dosage form comprising a solid solution
EP1604667A1 (en) 2004-06-08 2005-12-14 Euro-Celtique S.A. Opioids for the treatment of the restless leg syndrome
EP1604666A1 (en) 2004-06-08 2005-12-14 Euro-Celtique S.A. Opioids for the treatment of the Chronic Obstructive Pulmonary Disease (COPD)
US8367105B2 (en) 2004-11-10 2013-02-05 Teva Pharmaceutical Industries, Ltd. Compressed solid dosage form manufacturing process well-suited for use with drugs of low aqueous solubility and compressed solid dosage forms made thereby
EP1702558A1 (en) 2005-02-28 2006-09-20 Euro-Celtique S.A. Method and device for the assessment of bowel function
DE102007028869A1 (de) 2007-06-22 2008-12-24 Ratiopharm Gmbh Verfahren zur Herstellung eines Arzneimittels enthaltend Tadalafil
SG174286A1 (en) 2009-03-10 2011-10-28 Euro Celtique Sa Immediate release pharmaceutical compositions comprising oxycodone and naloxone
DE102011011889B4 (de) 2011-02-21 2015-11-05 Leistritz Extrusionstechnik Gmbh Vorrichtung und Verfahren zur kontinuierlichen Herstellung von biplan geschnittenen Formkörpern enthaltend wenigstens einen Füllstoff
DE102011015370A1 (de) * 2011-03-29 2012-10-04 Emodys Gmbh Matrix für eine orale Darreichungsform, Verfahren zu deren Herstellung sowie Verwendung derselben
AU2012357848C1 (en) * 2011-12-21 2018-07-19 Bayer Pharma Aktiengesellschaft Preparations containing amorphous emodepside
JP2016525138A (ja) 2013-07-23 2016-08-22 ユーロ−セルティーク エス．エイ． 疼痛および腸内ディスバイオシスをもたらす疾患および／または腸内細菌移行に対するリスクを高める疾患に罹患している患者における痛みの治療への使用のためのオキシコドンおよびナロキソンの組み合わせ
ES2938608T3 (es) 2017-09-20 2023-04-13 Tillotts Pharma Ag Método para preparar una forma farmacéutica sólida que comprende anticuerpos mediante granulación en húmedo, extrusión y esferonización

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DK1171101T3 (da) 2007-07-16
HUP0200843A2 (hu) 2002-07-29
EP1171101B1 (de) 2007-03-14
JP4575599B2 (ja) 2010-11-04
DE20022720U1 (de) 2002-02-28
AU4554200A (en) 2000-11-10
CY1106478T1 (el) 2012-01-25
EP1171101A1 (de) 2002-01-16
BR0009927A (pt) 2002-01-08
ES2284495T3 (es) 2007-11-16
AU763609B2 (en) 2003-07-31
US8557286B1 (en) 2013-10-15
DE50014164D1 (de) 2007-04-26
CN1347315A (zh) 2002-05-01
CA2372025C (en) 2007-09-25
RU2001128233A (ru) 2004-02-27
PT1171101E (pt) 2007-06-08
KR20010112440A (ko) 2001-12-20
JP5022086B2 (ja) 2012-09-12
IL145755A0 (en) 2002-07-25
CA2372025A1 (en) 2000-11-02
HUP0200843A3 (en) 2003-04-28
KR100511113B1 (ko) 2005-08-31
CN1214783C (zh) 2005-08-17
HU227001B1 (en) 2010-04-28
ATE356617T1 (de) 2007-04-15
JP2007211019A (ja) 2007-08-23
DE19918325A1 (de) 2000-10-26
BR0009927B1 (pt) 2011-12-27
RU2208436C2 (ru) 2003-07-20
EP1839651A1 (de) 2007-10-03
JP2002542276A (ja) 2002-12-10

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