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EP1435922A1 - Utilisation d'un copolymere pour produire une forme galenique contenant un peptide ou une proteine comme agent actif - Google Patents

Utilisation d'un copolymere pour produire une forme galenique contenant un peptide ou une proteine comme agent actif

Info

Publication number
EP1435922A1
EP1435922A1 EP01274547A EP01274547A EP1435922A1 EP 1435922 A1 EP1435922 A1 EP 1435922A1 EP 01274547 A EP01274547 A EP 01274547A EP 01274547 A EP01274547 A EP 01274547A EP 1435922 A1 EP1435922 A1 EP 1435922A1
Authority
EP
European Patent Office
Prior art keywords
copolymer
methacrylic acid
weight
mixture
active ingredient
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Withdrawn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
EP01274547A
Other languages
German (de)
English (en)
Inventor
Hans-Ulrich Petereit
Thomas Beckert
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.)
Roehm GmbH Darmstadt
Original Assignee
Roehm GmbH Darmstadt
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 Roehm GmbH Darmstadt filed Critical Roehm GmbH Darmstadt
Publication of EP1435922A1 publication Critical patent/EP1435922A1/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Withdrawn legal-status Critical Current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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates

Definitions

  • the invention relates to the use of a copolymer for the production of a pharmaceutical form which contains a peptide or protein as an active ingredient, and to the pharmaceutical form obtained in accordance with the use.
  • US 5,591, 433, US 5,629,001, US 5, 783,193 and US 6,174,529 B1 describe the oral administration of therapeutically active proteins.
  • the therapeutically active proteins it can be e.g. B. to vaccines (vaccines), proteins for the treatment of autoimmune diseases or to proteins that are intended to prevent an abutment of foreign tissue in organ transplants.
  • the proteins are on cores (Nonpareils) together with stabilizing substances such as.
  • B. formulated lactose, mannitol or trehalose which should provide protection during the subsequent coating with a polymeric coating agent and during passage through the gastrointestinal tract.
  • Only aqueous emulsion polymers are suitable as polymeric coating agents. Suitable polymers are e.g. B.
  • hydroxypropyimethyl cellulose acetate succinate or EUDRAGIT® L 30 D a copolymer of 50 wt .-% methyl methacrylate and 50 wt .-% methacrylic acid.
  • the polymer can be used together with auxiliaries such as. B. 0 to 30 wt .-% plasticizer, 0 to 3 wt .-% talc and 0 to 0.0025 wt .-% antifoam, e.g. As silicone or sorbitan sesquioleate can be used.
  • the coating temperatures should be between 30 and 50 ° C.
  • EP 0 704 207 A2 describes thermoplastic materials for pharmaceutical casings soluble in intestinal juice. These are copolymers of 16 to 40% by weight of acrylic or methacrylic acid, 30 to 80% by weight of methyl acrylate and 0 to 40% by weight of other alkyl esters of acrylic acid and / or methacrylic acid.
  • EP 0 704 208 A2 describes coating agents and binders for intestinal juice-soluble pharmaceutical casings. These are copolymers of 10 to 25% by weight of methacrylic acid, 40 to 70% by weight of methyl acrylate and 20 to 40% by weight of methyl methacrylate. In addition to single-layer coatings, the description also mentions multi-layer coating systems. These can consist of a core, e.g. B. contains a basic or a water-sensitive active ingredient, have an insulating layer made of another coating material, such as cellulose ether, cellulose ester or a cationic polymethacrylate z. B. of type EUDRAGIT®, u. a. also EUDRAGIT® RS and RL, and are then additionally provided with the casing-soluble coating mentioned above.
  • a core e.g. B. contains a basic or a water-sensitive active ingredient
  • an insulating layer made of another coating material, such as cellulose ether, cellulose ester or a cationic polyme
  • Example 4 of EP 0 704 208 A2 describes the active ingredient release from pellets containing bisacodyl with a copolymer coating of 70% by weight methyl acrylate, 20% by weight methyl methacrylate and 10% by weight methacrylic acid. 99% of the active ingredient is released at pH 6.8 in just 45 minutes.
  • the dissolution behavior of glass beads coated with copolymer is shown in further examples. From pH 7.0, a steep curve is observed. The release of methylene blue from appropriately coated tablets is described in further examples.
  • Tablets with a copolymer coating of 65% by weight methyl acrylate, 25 % By weight of methyl methacrylate and 10% by weight of methacrylic acid did not dissolve in pH 6.8 buffer solution after 60 min, but disintegrated within 50 min at pH 7.5.
  • Coatings made from EUDRAGIT® L 30-D, a copolymer of 50% by weight of ethyl acrylate and 50% by weight of methacrylic acid also show an at least partially undesirable early release of active ingredient. This is particularly the case with active substances, the proteins or peptides being critical, since these are then exposed to the action of the proteolytic enzymes present in these sections of the intestine.
  • Another problem with active substances that are proteins or peptides is a possible denaturation of their structure. This can occur in whole or in part, particularly during storage of the pharmaceutical form due to acid groups present in the polymer coating or due to auxiliary substances such as plasticizers.
  • a pharmaceutical form should therefore be provided which is particularly suitable for active substances which are proteins or peptides.
  • the object is achieved by using a copolymer or a mixture of copolymers of C 1 -C 4 -alkyl esters of acrylic or methacrylic acid, containing 5 to 25% by weight of methacrylic acid, alone or based on the mixture, as a coating agent for a pharmaceutical form , consisting of a core containing a pharmaceutical active ingredient which is a peptide or a protein.
  • a pharmaceutical form consisting of a core with a pharmaceutical active ingredient which is a peptide or a protein, and a polymer coating which comprises a copolymer or a mixture of copolymers of d- to C -alkyl esters of acrylic or Methacrylic acid is, containing alone or based on the mixture 5 to 25 wt .-% methacrylic acid.
  • copolymers to be used according to the invention are known from EP 0 704 208 A2 and are obtained by radical polymerization, preferably emulsion polymerization, from 50 to 68, preferably 60 to 67% by weight methyl acrylate, 27 to 45, preferably 21 to 32% by weight ci- to C 4 alkyl esters of acrylic or methacrylic acid and 5 to 20% by weight, preferably 8 to 12 methacrylic acid.
  • methyl acrylate is apparently particularly critical. If this rises to above 68% by weight, this promotes rapid dissolution of the polymer coatings even at pH values around 6.8, which is undesirable for. In the range of 50 to 68. preferably 60 to 67% by weight of methyl acrylate, the desired release characteristic is obtained in combination with the likewise critical content of 5 to 20% by weight, preferably 8 to 12, methacrylic acid.
  • Ci to C alkyl esters contained in acrylic or methacrylic acid appear to be less critical for the release behavior.
  • Preferred C1 to C4 alkyl esters of acrylic or methacrylic acid are ethyl acrylate, butyl acrylate, butyl methacrylate and, particularly preferably, methyl methacrylate.
  • a mixture of a neutral copolymer of 20 to 40% by weight of ethyl acrylate and 60 to 80% by weight of methyl methacrylate and a copolymer of 25 to 60% by weight of methacrylic acid and 75 to 40% by weight can also be used for the polymer coating.
  • Methyl methacrylate or 75 to 40% by weight of ethyl acrylate, 5 to 25% by weight of methacrylic acid being present based on the mixture.
  • Such mixtures are e.g. B. known from EP-A 152 038 or EP-A 208 213.
  • copolymers to be used are preferably in the form of aqueous dispersions, e.g. B. with 20 to 50 wt .-% solids content, and are applied in a conventional manner as a spray application to active ingredient-containing cores or pellets.
  • aqueous dispersions e.g. B. with 20 to 50 wt .-% solids content
  • the weight of the coating can be 5 to 80, preferably 10 to 40% by weight, based on the weight of the core with the active pharmaceutical ingredient.
  • the pharmaceutical form obtained according to the use consists of a core with a pharmaceutical active ingredient which is a peptide or a protein, and a polymer coating which is a copolymer or a mixture of copolymers of C 1 -C 4 -alkyl esters of acrylic or methacrylic acid, containing alone or based on the mixture 5 to 25 wt .-% methacrylic acid.
  • the pharmaceutical form can have a polymer coating of a copolymer of 50 to 68% by weight of methyl acrylate, 27 to 45% by weight of d- to C -alkyl esters of acrylic or methacrylic acid and 5 to 20% by weight of methacrylic acid.
  • the pharmaceutical form can furthermore be a polymer coating composed of a mixture of a neutral copolymer of 20 to 40% by weight of ethyl acrylate and 60 to 80% by weight of methyl methacrylate and a copolymer of 25 to 60% by weight of methacrylic acid and 75 to 40% by weight. -% methyl methacrylate or 75 to 40% by weight ethyl acrylate.
  • auxiliaries can be contained, but these are not critical for the invention.
  • Carriers or cores for the coatings are tablets, granules, pellets, crystals of regular or irregular shape.
  • the size of granules, pellets or crystals is usually between 0.01 and 2.5 mm, that of tablets between 2.5 and 30.0 mm.
  • the carriers usually contain 1 to 95% of active ingredient and, if appropriate, further pharmaceutical auxiliaries.
  • Usual manufacturing processes are direct pressing, pressing of dry, moist or sinter granules, extrusion and subsequent rounding, moist or dry granulation or direct pelleting (e.g. on plates) or by binding powders (powder layering) to active substance-free balls (nonpareilles) or active substance-containing ones particles.
  • the cores can contain other pharmaceutical auxiliaries: binders, such as lactose, cellulose and their derivatives, polyvinylpyrrolidone (PVP), humectants, disintegrants, lubricants, disintegrants, starch and their derivatives, sugar solubilizers or others.
  • binders such as lactose, cellulose and their derivatives, polyvinylpyrrolidone (PVP), humectants, disintegrants, lubricants, disintegrants, starch and their derivatives, sugar solubilizers or others.
  • the cores can be provided in the usual way with a pharmaceutical active ingredient by adding the corresponding active ingredient, e.g. B. as an active ingredient powder on carrier particles (Nonpareilles) by means of an aqueous binder.
  • the active ingredient cores (pellets) can be obtained after drying and sieving in the desired size fraction (e.g. 0.7 to 1 mm). This process is referred to as "powder layering
  • Proteins or peptides are a group of organic macromolecules made up of amino acids linked together by peptide bonds.
  • the order in which the As are linked together results in the so-called primary structure of the proteins. If parts of such peptide chains spatially connect with each other (e.g. through the formation of hydrogen bridges), spiral-like structures ( ⁇ -helix) or leaflet-like forms (ß-folding plate structure) can arise, which are referred to as secondary structures.
  • Other interactions ionic and hydrophobic interactions as well as disulfide bridges
  • Several chains of the same or different quality can then merge into a quaternary structure (e.g. with hemoglobin).
  • the active pharmaceutical ingredient can e.g. B. an enzyme, a peptide hormone, an immunomodulatory protein, an antigen or antibody.
  • the active pharmaceutical ingredient can include a pancreatin, an insulin, a human growth hormone (hGH), corbaplatin, intron A, calcitonin, cromalyn, an interferon, a calcitonin, granulocyte colony stimulating factor (G-CSF) Interleukin, parathyroid hormones, glucagon, pro-somatostatin, a somatostatin, detirelix, cetrorelix, vasopressin, 1-deaminocysteine-8-D-arginine-vasopressin, leuprolide acetate or an antigen derived from grasses or other plants such as e.g. B. rye, wheat, barley, oats, Bermuda grass, horsetail, maple, elm, oak, plane tree, poplar, cedar, horsetail, thistles.
  • G-CSF granulocyte colony stimulating factor
  • Antibodies are protein compounds generated in the organism from the group of immunoglobulins; they stick together (agglutination) with penetrated foreign organic compounds (antigens) to form a harmless complex. Antibodies are produced in the lymph nodes of more developed animals and humans. When it comes to immunity, enough antibodies are available or are produced more quickly. If there are too many antibodies, allergy symptoms can occur with sudden agglutination.
  • the greatest therapeutic spread is IgG or monoclonal antibodies, which are produced by cells that are derived from a mother cell.
  • the (oral) pharmaceutical form described can be in the form of a coated tablet, in the form of a tablet made of compressed pellets or in the form of pellets which are placed in a capsule, e.g. B. from gelatin, starch or cellulose derivatives are filled.
  • auxiliaries can be used in a manner known per se. These auxiliaries can be contained in the core or in the coating agent. Drying agents (non-stick agents): Drying agents have the following properties: They have large specific surfaces, are chemically inert, are easy to pour and have fine particles. These properties reduce the stickiness of polymers which contain polar comonomers as functional groups.
  • drying agents are:
  • release agents are:
  • the usual proportions are in the range of 0 , 05% by weight to 5, preferably 0.1 to 3% by weight, based on the copolymer.
  • compositions B to name stabilizers, dyes, antioxidants, wetting agents, pigments, glossing agents etc. They primarily serve as processing aids and are intended to ensure a safe and reproducible manufacturing process and good long-term storage stability. Further pharmaceutically customary auxiliaries can be present in amounts of 0.001% by weight to 30% by weight, preferably 0.1 to 10% by weight, based on the copolymer.
  • Plasticizer The copolymer or the copolymer mixture is preferably without or with at most 10% by weight, e.g. B. formulated with 1 to 7 wt .-% of a plasticizer.
  • Suitable substances as plasticizers generally have a molecular weight between 100 and 20,000 and contain one or more hydrophilic groups in the molecule, e.g. B. hydroxyl, ester or amino groups. Citrates, phthalates, sebacates, castor oil are suitable. Examples of suitable plasticizers are citric acid alkyl ester, glycerol ester, alkyl phthalate, alkyl sebacate, sucrose ester, sorbitan ester, dibutyl sebacate and polyethylene glycols 4,000 to 20,000. Preferred plasticizers are tributyl citrate, triethyl citrate, acetyl triethyl citrate, dibutyl sebacate and diethyl sebacate.
  • EUDRAGIT® FS 30 D 30% dispersion containing a copolymer of 65% by weight methyl acrylate, 25% by weight, methyl methacrylate and 10% by weight methacrylic acid.
  • EUDRAGIT® NE 30 D 30% dispersion containing a copolymer of 30% by weight ethyl acrylate and 60 to 70% by weight methyl methacrylate.
  • EUDRAGIT® L 30 D-55 30% dispersion containing a copolymer of 50% by weight methacrylic acid and 50% by weight ethyl acrylate.
  • 500 g placebo pellets are coated in a fluidized bed device GPCG 1 (from GLATT, D-Binzen) with a solution of 9 g chicken egg albumin (ovalbumin), 45 g lactose D 80 and 45 g Kollidon 25 in 396 g water.
  • the spray rate was 0.7 g / min.
  • the product temperature was kept between 24 and 26 ° C and did not exceed 30 ° C during drying in the device.
  • the pellets were then mixed with 0.5% silica (AEROSIL 200) and dried overnight at room temperature.
  • AEROSIL 200 0.5% silica
  • 500 g of the ovalbumin pellets from Example 1 are coated in a fluidized bed device GPCG 1 (from GLATT, D-Binzen) film-forming spray suspension made from 500g EUDRAGIT ® FS 30 D, 75 g talc, 8 g triethyl citrate and 930 g water.
  • the spray rate was 4.8 g / min.
  • the product temperature was kept between 26 and 28 ° C and did not exceed 30 ° C during drying in the device.
  • the pellets were then mixed with 0.5% silica (AEROSIL 200) and in a drying cabinet at 40 ° C. for 2 hours.
  • AEROSIL 200 0.5% silica
  • 450 g of the ovalbumin pellets from Example 1 are coated in a fluidized bed device GPCG 1 (from GLATT, D-Binzen) with a film-forming spray suspension composed of 225 g EUDRAGIT ® NE 30 D, 225 g EUDRAGIT ® L 30 D-55, 23 g 0.1 N sodium hydroxide solution, 68 g talc and 273 g water.
  • the spray rate was 1.7 g / min.
  • the product temperature was kept between 29 and 30 ° C and did not exceed 30 ° C during drying in the device.
  • the pellets were then mixed with 0.5% silica (AEROSIL 200) and in the drying cabinet at 40 ° C. for 24 hours.
  • AEROSIL 200 0.5% silica

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

L'invention concerne l'utilisation d'un copolymère ou d'un mélange de copolymères, composé d'esters d'alkyle C1 à C4 d'acide acrylique ou d'acide méthacrylique, contenant seul ou sous forme de mélange 5 à 25 % en poids d'acide méthacrylique, en tant qu'agent d'enrobage d'une forme galénique composée d'un noyau comportant un agent pharmaceutique actif sous forme de peptide ou de protéine. La présente invention porte également sur la forme galénique même.
EP01274547A 2001-10-15 2001-10-15 Utilisation d'un copolymere pour produire une forme galenique contenant un peptide ou une proteine comme agent actif Withdrawn EP1435922A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2001/011899 WO2003032958A1 (fr) 2001-10-15 2001-10-15 Utilisation d'un copolymere pour produire une forme galenique contenant un peptide ou une proteine comme agent actif

Publications (1)

Publication Number Publication Date
EP1435922A1 true EP1435922A1 (fr) 2004-07-14

Family

ID=8164626

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01274547A Withdrawn EP1435922A1 (fr) 2001-10-15 2001-10-15 Utilisation d'un copolymere pour produire une forme galenique contenant un peptide ou une proteine comme agent actif

Country Status (12)

Country Link
US (1) US20030091637A1 (fr)
EP (1) EP1435922A1 (fr)
JP (1) JP2005506991A (fr)
KR (1) KR20040047915A (fr)
BR (1) BR0117149A (fr)
CA (1) CA2460132A1 (fr)
HU (1) HUP0401732A2 (fr)
IL (1) IL160190A0 (fr)
MX (1) MXPA04003540A (fr)
PL (1) PL367957A1 (fr)
SK (1) SK1732004A3 (fr)
WO (1) WO2003032958A1 (fr)

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MXPA04010956A (es) * 2003-01-30 2005-01-25 Roehm Gmbh Forma de dosis farmaceutica y metodo para la produccion de la misma.
US7094545B2 (en) 2003-04-30 2006-08-22 Ferring Bv Pharmaceutical composition as solid dosage form and method for manufacturing thereof
DE10332160A1 (de) * 2003-07-15 2005-02-03 Röhm GmbH & Co. KG Multipartikuläre Arzneiform, enthaltend mucoadhaesiv formulierte Peptid- oder Protein-Wirkstoffe, sowie ein Verfahren zur Herstellung der Arzneiform
ES2243840T3 (es) 2003-07-25 2005-12-01 Ferring B.V. Composicion farmaceutica de desmopresina como forma farmaceutica solida de dosificacion y metodo para la fabricacion de la misma.
CN1826099B (zh) * 2003-07-25 2010-06-09 凡林有限公司 固体剂型药物组合物及其制造方法
US7018653B2 (en) * 2003-12-29 2006-03-28 Ferring B.V. Method for preparing solid dosage form of desmopressin
CA2490601C (fr) * 2003-12-29 2006-05-02 Ferring B.V. Methode de preparation d'une forme pharmaceutique solide de desmopressine
SI1550439T1 (sl) * 2003-12-29 2006-08-31 Ferring Bv Postopek za pripravo trdne dozirne oblike dezmopresina
EP1883396B1 (fr) 2005-05-18 2013-07-03 DA Volterra Administration colonique d'adsorbants
DE102005024614A1 (de) * 2005-05-25 2006-11-30 Röhm Gmbh Verwendung von Polymermischungen zur Herstellung von überzogenen Arzneiformen sowie Arzneiform mit polymerem Mischüberzug
US8048413B2 (en) 2006-05-17 2011-11-01 Helene Huguet Site-specific intestinal delivery of adsorbents, alone or in combination with degrading molecules
JP5524624B2 (ja) * 2007-11-16 2014-06-18 旭化成ケミカルズ株式会社 水系フィルムコーティング液、および、フィルムコーティング顆粒、ならびに、これを用いた錠剤
EP3250191B1 (fr) * 2015-01-29 2024-01-17 Novo Nordisk A/S Comprimés contenant un agoniste de glp-1 et revêtement gastro-résistant

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Also Published As

Publication number Publication date
HUP0401732A2 (hu) 2004-12-28
KR20040047915A (ko) 2004-06-05
JP2005506991A (ja) 2005-03-10
BR0117149A (pt) 2004-11-23
SK1732004A3 (sk) 2005-06-02
MXPA04003540A (es) 2004-07-22
IL160190A0 (en) 2004-07-25
CA2460132A1 (fr) 2003-04-24
WO2003032958A1 (fr) 2003-04-24
PL367957A1 (en) 2005-03-07
US20030091637A1 (en) 2003-05-15

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