WO2004105735A1 - Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation - Google Patents

Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation Download PDF

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Publication number
WO2004105735A1
WO2004105735A1 PCT/IB2004/001789 IB2004001789W WO2004105735A1 WO 2004105735 A1 WO2004105735 A1 WO 2004105735A1 IB 2004001789 W IB2004001789 W IB 2004001789W WO 2004105735 A1 WO2004105735 A1 WO 2004105735A1
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WO
WIPO (PCT)
Prior art keywords
layer
tolterodine
cellulose
core
composition according
Prior art date
Application number
PCT/IB2004/001789
Other languages
English (en)
Inventor
Pratik Kumar
Girish Kumar Jain
Ashok Rampal
Original Assignee
Ranbaxy Laboratories Limited
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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Priority to EP04743749A priority Critical patent/EP1635795A1/fr
Publication of WO2004105735A1 publication Critical patent/WO2004105735A1/fr

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Classifications

    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • 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
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose

Definitions

  • the technical field of the present invention pertains to controlled release pharmaceutical composition of tolterodine and processes for the preparation of multiple unit pharmaceutical composition of tolterodine.
  • overactive or unstable urinary bladder often also referred to as urinary incontinence.
  • the symptoms of an unstable or overactive bladder include urge incontinence, urgency and urinary frequency.
  • overactive bladder particularly urge incontinence, increases with age. It is assumed that unstable or overactive bladder is caused by uncontrolled contractions of the bundles of smooth muscle fibres forming the muscular coat of the urinary bladder (the detrusor muscle) during the filling phase of the bladder. These contractions are mainly controlled by cholinergic muscarinic receptors, and the pharmacological treatment of unstable or overactive bladder has been based on muscarinic receptor antagonists. The drug of choice for these conditions for a long time has been oxybutynin.
  • tolterodine (R) N, N-diisopropyl-3- (2-hydroxy-5-methylphenyl)-3-phenylpropanamine
  • tolterodine and its major, active metabolite the 5- hydroxymethyl derivative of tolterodine, which significantly contributes to the therapeutic effect, have considerably fewer side-effects than oxybutynin, especially regarding the tendency to cause dry mouth.
  • tolterodine is equipotent as oxybutynin in the bladder, its affinity for muscarinic receptors of the salivary gland is eight times lower than that of oxybutynin.
  • tolterodine is a film coated tablet containing 1 mg or 2 mg of tolterodine L-tartrate for immediate release in the gastrointestinal tract, the recommended dosage usually being 2 mg twice a day.
  • Tolterodine tartrate is also marketed by Pharmacia as DETROL LA extended release capsules. The capsules contain either 2 or 4 mg of the active ingredient.
  • PCT application WO 00/12069 discloses treatment of overactive bladder by the administration of a controlled release formulation that is purported to deliver tolterodine, a tolterodine-related compound, or a pharmacologically acceptable salt thereof such that a substantially constant serum level of the active moiety or moieties is maintained for at least 24 hours.
  • PCT application WO 00/27364 relates to a formulation containing controlled release beads, and to a method of preparing the beads.
  • These beads include: (i) a core unit of water-soluble or water-insoluble polymer; (ii) a first layer on the core unit of a substantially water-insoluble polymer; (iii) a second layer covering the first layer and containing the active ingredient and (iii) a third layer on the second layer of polymer effective for controlled release of active ingredient.
  • the first layer is adapted to control water penetration into the core.
  • a controlled release pharmaceutical composition of tolterodine that includes one or more coated units.
  • Each coated unit includes a core, a first layer, and a second layer.
  • the first layer surrounds at least a portion of the core and includes tolterodine and one or more hydrophilic polymers.
  • the second layer surrounds at least a portion of the first layer and includes one or more polymers that are effective for controlled release of the tolterodine from the first layer.
  • the controlled release pharmaceutical composition may include one or more of the following features.
  • the core may include one or more of an inert insoluble core, an inert soluble or swellable core, and a commercially available inert core material.
  • the insoluble inert core may include one or more of dicalcium phosphate and microcrystalline cellulose.
  • the soluble or swellable inert core may be one or more of glucose, mannitol, lactose, xylitol, dextrose, and sucrose.
  • the commercially available inert core material may be one or more of sugar sphere, non-pareil seed, and celphere.
  • the tolterodine may be one or more of tolterodine base, the (S)-enantiomer, the racemate, the active 5-hydroxymethyl metabolites, a prodrug form, a pharmaceutically acceptable salt thereof, and the tartarate salt thereof.
  • the hydrophilic polymer may be one or more of polyvinylpyrrolidone, a polyalkylene glycol, polyethylene glycol, gelatin, polyvinyl alcohol, starch and derivatives thereof, cellulose derivatives, hydroxypropyl methylcellulose, hydroxypropyl cellulose, carboxymethyl cellulose, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, carboxyethyl cellulose, carboxymethylhydroxyethyl cellulose, acrylic acid polymers, polymethacrylates, or any pharmaceutically acceptable polymer.
  • the ratio of tolterodine to hydrophilic polymer in the first layer may be between about 1 :20 to 20: 1.
  • the polymers in the second layer may be one or more of ethyl cellulose, hydroxypropyl methyl cellulose phthalate, cellulose acetate phthalate, cellulose acetate trimellitate, polymethacrylates, and mixtures thereof.
  • the second layer may further include one or more modifiers.
  • the modifiers may be one or more of hydroxypropyl methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, carboxymethylcellulose, polyethylene glycol, polyvinylpyrrolidone, polyvinyl alcohol, polymers with pH-dependent solubility, such as cellulose acetate phthalate or ammonio-methacrylate copolymer and methacrylic acid copolymer, and mixtures thereof.
  • the second layer may be from about 2 to 50% of the formulation.
  • Either or both of the first layer and the second layer may include one or more additional pharmaceutical excipients, which may be plasticizers and/or lubricants.
  • the additional pharmaceutical excipients may be one or more of plasticizers and lubricants.
  • the plasticizers may be one or more of propylene glycol, triethylene glycol, oleic acid, ethyleneglycol monoleate, triethyl citrate, triacetin, diethyl phthalate, glyceryl monostearate, dibutyl sebaccate, acetyl triethylcitrate, and castor oil.
  • the lubricants may be one or more of talc, anhydrous colloidal silica, magnesium stearate, glyceryl monostearate, and beeswax.
  • the coated units may be filled into hard gelatin capsules or compressed into tablets.
  • the coated units may further include a non-functional coating.
  • the controlled release pharmaceutical composition may show the following in vitro dissolution profile for tolterodine in 900 ml of Phosphate buffer pH 6.8 when tested using USP Apparatus I at 100 rpm: not more than about 50 percent released in 1 hour; between about 25 and about 85 percent released in 3 hours; and not less than about 50 percent released in 7 hours.
  • a process for preparing a controlled release pharmaceutical composition of tolterodine includes (a) providing a core; (b) applying a first layer to the core, the first layer comprising tolterodine and one or more hydrophilic polymers; and (c) applying a second layer onto the first layer to form a coated unit, the second layer comprising one or more polymers effective for controlled release of the tolterodine.
  • Embodiments of the process may include one or more of the following features or those described above.
  • the ratio of tolterodine to hydrophilic polymer in the first layer may be from about 1 :20 to 20: 1.
  • the core may be coated with tolterodine in a powder form or sprayed as a solution or dispersion.
  • the polymers in the second layer may be one or more of ethyl cellulose, hydroxypropyl methyl cellulose phthalate, cellulose acetate phthalate, cellulose acetate trimellitate, polymethacrylates, and mixtures thereof.
  • the second layer may further include one or more modifiers.
  • the modifiers may be one or more of hydroxypropyl methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, carboxymethylcellulose, polyethylene glycol, polyvinylpyrrolidone, polyvinyl alcohol, polymers with pH-dependent solubility, such as cellulose acetate phthalate or ammonio-methacrylate copolymer and methacrylic acid copolymer, and mixtures thereof.
  • the process may further include applying the polymers of the second layer as a solution or dispersion in a solvent.
  • the solvent may further include one or more of water, alcohols, ethyl alcohol, isopropyl alcohol; ketones, acetone, ethylmethylketone; halogenated hydrocarbons, dichloroethane, trichloroethane and mixtures thereof.
  • the process may further include drying the coated core and/or drying the coated unit.
  • the process may further include filling the coated units into hard gelatin capsules or compressing the coated units into tablets.
  • the process may further include applying a non-functional coating to the coated units.
  • the second layer may constitute about 2% to about 50% of the formulation. Either or both of the first coating layer and the second coating layer may further include one or more pharmaceutically inert excipients.
  • the controlled release pharmaceutical composition may show the following in vitro dissolution profile for tolterodine in 900 ml Phosphate buffer pH 6.8 when tested using USP Apparatus I at 100 rpm:
  • a method of treating an overactive bladder with symptoms of one or more of urinary frequency, urgency and urge incontinence includes administering a controlled-release pharmaceutical composition of tolterodine that includes one or more coated units.
  • Each coated unit includes a core, a first layer, and a second layer.
  • the first layer surrounds at least a portion of the core and includes tolterodine and one or more hydrophilic polymers.
  • the second layer surrounds at least a portion of the first layer and includes one or more polymers effective for controlled release of the tolterodine from the first layer.
  • Embodiments of the method may include any one or more of the features described above.
  • the pharmaceutical composition may further include at least one active ingredient selected from amongst oxybutynin, ⁇ -blockers and 5 ⁇ -reductase inhibitors.
  • controlled release pharmaceutical compositions of tolterodine may be formulated by layering the core directly with the active ingredient dispersed in hydrophilic polymer, without the need for a seal-coat or an extra polymer coat between the core and the active layer.
  • the term "multiple unit pharmaceutical composition” indicates a pharmaceutical composition that includes one or more individual coated units contained in the formulation in such a form that the individual units will be available from the formulation upon disintegration of the formulation in the stomach.
  • the multiple unit pharmaceutical composition or formulation may be a capsule or a tablet that disintegrates in the stomach to give individual units.
  • the multiple units may be formulated as granules, pellets or beads.
  • the inert core may be selected from one or more of pharmaceutically inert insoluble or soluble or swellable materials. Alternatively, the inert core may also be a commercially available product.
  • the insoluble inert cores are composed of dicalcium phosphate, microcrystalline cellulose and the like, either alone or in combination.
  • the soluble inert cores are composed of sugar selected from glucose, mannitol, lactose, xylitol, dextrose, sucrose and the like.
  • Commercially available inert cores are selected from sugar sphere, non-pareil seed, celphere and the like.
  • the cores may be of any geometric shape, though spheres are preferred for the ease of uniform coating.
  • the layer that includes the active ingredient may contain the active ingredient, e.g., tolterodine, with a polymer.
  • the polymer is usually hydrophilic but may be water-soluble or water-insoluble.
  • Exemplary polymers to be used in the first layer containing the active ingredient are hydrophilic polymers such as polyvinylpyrrolidone; polyalkylene glycol such as polyethylene glycol, gelatin, polyvinyl alcohol, starch and derivatives thereof; cellulose derivatives, such as hydroxypropyl methylcellulose, hydroxypropyl cellulose, carboxymethyl cellulose, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, carboxyethylcellulose, carboxy-methyl-hydroxy-ethyl cellulose, acrylic acid polymers, polymethacrylates, or any other pharmaceutically acceptable polymer.
  • Tolterodine for the purpose of the present invention may be selected from tolterodine base, i.e., (R)-N, N-diisopropyl-3-(2-hydroxy-5-methyTphenyl)-3 phenylpropanamine, as well as the corresponding (S)-enantiomer, the racemate and the active 5-hydroxymethyl metabolites, prodrug forms and pharmaceutically acceptable salts thereof such as tartarate.
  • the tolterodine used in the pharmaceutical compositions described herein can be prepared by any known method, such as, for example, using either of the procedures disclosed in U.S. Patent No. 5,382,600 or U.S. Patent No. 5,922,914. Both of these patents are incorporated herein in their entirety by reference.
  • the ratio of active ingredient to hydrophilic polymer in the first layer may be in the range of 1 :20 to 20: 1 (w/w).
  • the core particles may be coated with the first layer by coating with the active ingredient dispersed in the hydrophilic polymers by powder layering technique, i.e., the active ingredient is applied to the core in dry form as powder.
  • the polymer may be sprayed onto the cores as a solution or dispersion in such a way that solvent, preferably water, is evaporated, and the polymer is applied to the cores together with the active ingredient, i.e., forming a homogenous dispersion.
  • the pharmaceutically active ingredient is applied onto the core material preferably by spraying an aqueous/non aqueous solution/suspension in a fluidized bed with a Wurster or top spray technique.
  • the drug layered cores may be coated with a second layer that is a polymeric layer for modifying and controlling the drug release.
  • Suitable polymers may be selected from water-insoluble polymers or polymers with pH dependent or independent solubility, for example, ethyl cellulose, hydroxypropyl methyl cellulose phthalate, cellulose acetate phthalate, cellulose acetate trimellitate, polymethacrylates, or mixtures thereof.
  • the controlled release layer may include, in addition to the above polymers, one or more modifiers with different solubility characteristics. These modifiers are used to adjust the permeability, and thereby the release rate, of the controlled release layer.
  • Exemplary polymers that may be used as a modifier include: hydroxypropyl methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, carboxymethylcellulose, polyethylene glycol, polyvinylpyrrolidone, polyvinyl alcohol, polymers with pH-dependent solubility, such as cellulose acetate phthalate or ammonio methacrylate copolymer and methacrylic acid copolymer, or mixtures thereof.
  • Additives also may be included in the controlled release layer, if desired. Suitable additives include sucrose, lactose and pharmaceutical grade surfactants.
  • the polymers may be applied as a solution or dispersion in a solvent.
  • the solvent may be selected from water, alcohols such as ethyl alcohol or isopropyl alcohol; ketones such as acetone or ethylmethylketone; halogenated hydrocarbons such as dichloroethane and trichloroethane or mixtures thereof.
  • Any conventional coating equipment may be employed to facilitate coating, including equipment such as centrifugal fluidized bed coating apparatus and pan coating apparatus.
  • the coating may be applied using a conventional coating pan, a spray coater, a rotating perforated pan, or an automated system.
  • the coated multiple units may be dried in an oven or in a fluidized bed.
  • the coating may constitute about 2-50% w/w of the formulation.
  • the coating layers may additionally contain pharmaceutically inert excipients such as plasticizers and lubricants.
  • Suitable plasticizers include propylene glycol, triethylene glycol, oleic acid, ethyleneglycol monoleate, triethyl citrate, triacetin, diethyl phthalate, glyceryl monostearate, dibutyl sebacate, acetyl triethylcitrate , castor oil and the like.
  • Suitable lubricants include talc, anhydrous colloidal silica, magnesium stearate, glyceryl monostearate, beeswax and the like.
  • the multiple units may include a non-functional coating over the second layer.
  • coated multiple units are filled into hard gelatin capsules or compressed into tablets that disintegrate in the stomach to make available a multiplicity of individually coated units.
  • the controlled-release composition shows the following in vitro dissolution profile for tolterodine in 1000 ml Phosphate buffer pH 6.8, when tested using USP Apparatus I at 100 rpm:
  • Hydroxypropyl methylcellulose and tolterodine tartrate were dissolved in water and the solution obtained was sprayed onto non-pareil beads and the coating was dried to form drug coated beads.
  • the drug coated beads were further coated with a solution of ethyl cellulose and hydroxypropyl methylcellulose in a mixture of isopropyl alcohol and water (83: 17). The resulting coated beads were dried and filled into capsules.
  • Table 1 shows the dissolution data of tolterodine tartrate 4.0 mg capsules prepared as per composition of Example 1.
  • the dissolution was carried out in 1000 ml of phosphate buffer pH 6.8 using USP Apparatus Type I (basket) at a speed of 100 rpm.
  • Table 1 Comparative in vitro release of the tolterodine extended release capsules of Example 1 and Detrol LA capsules (4 mg; marketed by Pharmacia)
  • Hydroxypropyl methylcellulose and tolterodine tartrate were dissolved in water and the solution obtained was sprayed onto microcrystalline cellulose beads and the coating was dried for form drug coated beads.
  • the drug coated beads were further coated with a dispersion of ethyl cellulose and hydroxypropyl methylcellulose in a mixture of isopropyl alcohol and water. The coated beads were dried, lubricated and filled into capsules.
  • polyvinyl pyrrolidone, carboxymethyl cellulose, hydroxypropyl cellulose can be used as hydrophilic polymers for the first layer. Accordingly, it is not intended that the invention be limited, except as by the appended claims.

Abstract

La présente invention concerne des compositions pharmaceutiques de toltérodine à libération contrôlée, ainsi que des procédés pour la préparation d'une composition pharmaceutique de toltérodine à unités multiples. Ladite composition de toltérodine renferme une ou plusieurs unités enrobées. Chaque unité enrobée comporte un noyau, une première couche et une deuxième couche. La première couche entoure au moins une partie du noyau et renferme de la toltérodine et un ou plusieurs polymères hydrophiles. La deuxième couche entoure au moins une partie de la première couche et contient un ou plusieurs polymères actifs permettant la libération contrôlée de la toltérodine contenue dans la première couche.
PCT/IB2004/001789 2003-05-30 2004-06-01 Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation WO2004105735A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04743749A EP1635795A1 (fr) 2003-05-30 2004-06-01 Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation

Applications Claiming Priority (2)

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IN764DE2003 2003-05-30
IN764/DEL/2003 2003-05-30

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005105036A1 (fr) * 2004-04-28 2005-11-10 Natco Pharma Limited Matrice muco-adhesive a liberation controlee contenant de la tolterodine, et procede d'elaboration
WO2006106344A2 (fr) * 2005-04-06 2006-10-12 Mw Encap Limited Capsules a l'epreuve d'abus
WO2007011131A1 (fr) * 2005-07-22 2007-01-25 Chong Kun Dang Pharmaceutical Corp. Comprimes stables a liberation controlee contenant de la tolterodine
WO2007029087A2 (fr) * 2005-09-05 2007-03-15 Ranbaxy Laboratories Limited Preparations multi-unites a liberation controlee
EP1810668A1 (fr) * 2006-01-23 2007-07-25 LEK Pharmaceuticals D.D. Compositions pharmaceutiques enrobées à base de tartrate de toltérodine
WO2007109357A2 (fr) * 2006-03-21 2007-09-27 Teva Pharmaceutical Industries Ltd. Formule à libération contrôlée de toltérodine
CZ298448B6 (cs) * 2006-08-09 2007-10-03 Zentiva, A. S. Farmaceutická kompozice s obsahem tolterodinu
EP1839649A1 (fr) * 2006-03-31 2007-10-03 LEK Pharmaceuticals D.D. Formulations enrobées pour tolterodine
WO2007122015A1 (fr) * 2006-04-21 2007-11-01 Synthon B.V. Perles de tolterodine
WO2009003724A1 (fr) * 2007-07-03 2009-01-08 Synthon B.V. Bille de toltérodine
WO2009057138A2 (fr) * 2007-10-29 2009-05-07 Lupin Limited Compositions pharmaceutiques à libération régulée de toltérodine
WO2009121178A1 (fr) * 2008-04-01 2009-10-08 Pharmascience Inc. Nouvelles formulations pharmaceutiques orales à libération contrôlée
WO2011013082A1 (fr) 2009-07-31 2011-02-03 Ranbaxy Laboratories Limited Compositions pharmaceutiques à unités multiples multi-couches
WO2011095388A1 (fr) 2010-02-04 2011-08-11 Synthon Bv Microgranule de toltérodine
JP2013540100A (ja) * 2010-04-01 2013-10-31 セラヴィダ，インコーポレイテッド 過活動膀胱の治療のための医薬製剤
US8871275B2 (en) 2007-08-08 2014-10-28 Inventia Healthcare Private Limited Extended release compositions comprising tolterodine
EP2886110A1 (fr) 2013-12-23 2015-06-24 Ranbaxy Laboratories Limited Compositions pharmaceutiques d'unités multiples, multicouches
US9744157B2 (en) 2011-05-10 2017-08-29 Theravida, Inc. Combinations of solifenacin and salivary stimulants for the treatment of overactive bladder
US10328057B2 (en) 2016-01-20 2019-06-25 Theravida, Inc. Methods and compositions for treating hyperhidrosis

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Publication number Priority date Publication date Assignee Title
EP1629834A1 (fr) 2004-08-27 2006-03-01 KRKA, D.D., Novo Mesto Composition pharmaceutique de tolterodine avec liberation soutenue

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Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005105036A1 (fr) * 2004-04-28 2005-11-10 Natco Pharma Limited Matrice muco-adhesive a liberation controlee contenant de la tolterodine, et procede d'elaboration
WO2006106344A2 (fr) * 2005-04-06 2006-10-12 Mw Encap Limited Capsules a l'epreuve d'abus
WO2006106344A3 (fr) * 2005-04-06 2006-12-28 Mw Encap Ltd Capsules a l'epreuve d'abus
WO2007011131A1 (fr) * 2005-07-22 2007-01-25 Chong Kun Dang Pharmaceutical Corp. Comprimes stables a liberation controlee contenant de la tolterodine
WO2007029087A2 (fr) * 2005-09-05 2007-03-15 Ranbaxy Laboratories Limited Preparations multi-unites a liberation controlee
WO2007029087A3 (fr) * 2005-09-05 2007-07-12 Ranbaxy Lab Ltd Preparations multi-unites a liberation controlee
EP1810668A1 (fr) * 2006-01-23 2007-07-25 LEK Pharmaceuticals D.D. Compositions pharmaceutiques enrobées à base de tartrate de toltérodine
WO2007082770A1 (fr) * 2006-01-23 2007-07-26 Lek Pharmaceuticals D.D. Formules enrobées
WO2007109357A2 (fr) * 2006-03-21 2007-09-27 Teva Pharmaceutical Industries Ltd. Formule à libération contrôlée de toltérodine
JP2009530397A (ja) * 2006-03-21 2009-08-27 テバ ファーマシューティカル インダストリーズ リミティド トルテロジンの調節された開放性製剤
WO2007109357A3 (fr) * 2006-03-21 2008-02-28 Teva Pharma Formule à libération contrôlée de toltérodine
EP1839649A1 (fr) * 2006-03-31 2007-10-03 LEK Pharmaceuticals D.D. Formulations enrobées pour tolterodine
WO2007113207A2 (fr) * 2006-03-31 2007-10-11 Lek Pharmaceuticals D.D. Formulations enduites
WO2007113207A3 (fr) * 2006-03-31 2008-09-25 Lek Pharmaceuticals Formulations enduites
US8642078B2 (en) 2006-03-31 2014-02-04 Lek Pharmaceuticals, D.D. Coated formulations for tolterodine
WO2007122015A1 (fr) * 2006-04-21 2007-11-01 Synthon B.V. Perles de tolterodine
CZ298448B6 (cs) * 2006-08-09 2007-10-03 Zentiva, A. S. Farmaceutická kompozice s obsahem tolterodinu
WO2009003724A1 (fr) * 2007-07-03 2009-01-08 Synthon B.V. Bille de toltérodine
US8871275B2 (en) 2007-08-08 2014-10-28 Inventia Healthcare Private Limited Extended release compositions comprising tolterodine
WO2009057138A2 (fr) * 2007-10-29 2009-05-07 Lupin Limited Compositions pharmaceutiques à libération régulée de toltérodine
JP2011502140A (ja) * 2007-10-29 2011-01-20 ルピン・リミテッド トルテロジンの制御放出型医薬組成物
WO2009057138A3 (fr) * 2007-10-29 2009-07-23 Lupin Ltd Compositions pharmaceutiques à libération régulée de toltérodine
WO2009121178A1 (fr) * 2008-04-01 2009-10-08 Pharmascience Inc. Nouvelles formulations pharmaceutiques orales à libération contrôlée
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