WO2009057138A2 - Compositions pharmaceutiques à libération régulée de toltérodine - Google Patents

Compositions pharmaceutiques à libération régulée de toltérodine Download PDF

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Publication number
WO2009057138A2
WO2009057138A2 PCT/IN2008/000695 IN2008000695W WO2009057138A2 WO 2009057138 A2 WO2009057138 A2 WO 2009057138A2 IN 2008000695 W IN2008000695 W IN 2008000695W WO 2009057138 A2 WO2009057138 A2 WO 2009057138A2
Authority
WO
WIPO (PCT)
Prior art keywords
cellulose
controlled release
poly
pharmaceutical composition
release pharmaceutical
Prior art date
Application number
PCT/IN2008/000695
Other languages
English (en)
Other versions
WO2009057138A3 (fr
Inventor
Anirudha Bhagirath Kute
Rahul Manorajan Sammohi
Nikhil Prabhakar Malewar
Makarand Krishnakumar Avachat
Original Assignee
Lupin 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 Lupin Limited filed Critical Lupin Limited
Priority to JP2010531645A priority Critical patent/JP2011502140A/ja
Publication of WO2009057138A2 publication Critical patent/WO2009057138A2/fr
Publication of WO2009057138A3 publication Critical patent/WO2009057138A3/fr

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
    • A61K9/48—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
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50

Definitions

  • the present invention relates to controlled release pharmaceutical compositions comprising tolterodine or pharmaceutically acceptable salts thereof.
  • the symptoms of an unstable or overactive bladder comprise urge incontinence, urgency and urinary frequency. 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.
  • Tolterodine is. well-known . antimuscarinic agent specifically developed for treatment of patients with overactive bladder.. It was disclosed in US Patent 5,382,600. Tolterodine is marketed under the brand name Detrol ®film-coated tablets containing 1 mg or 2 mg of tolterodine L-tartrate for immediate release in the gastrointestinal tract. Additionally it is marketed under the brand name Detrol LA ® long acting capsules These capsules contain either 2 or 4 mg of the active ingredient.
  • US patent 6,911,217 relates to a controlled release bead comprising: (i) a core unit of a substantially water-soluble or water-swellable inert material; (ii) a first layer on the core unit of a substantially water-insoluble polymer; (iii) a second layer covering the first layer and containing an active ingredient; and (iv) a third layer of polymer on the second layer effective for controlled release of the active ingredient, wherein the first layer is adapted to control water penetration into the core.
  • WO 2004/105735 discloses 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.
  • WO 2005/079748 discloses a pharmaceutical preparation for sustained release of a pharmaceutically active ingredient(s), which preparation comprises particles having an imier core (1) and a first coating (2) provided thereon, wherein said coating (2) contains a mixture of (a) copolymer of ethyl acrylate, methylmethacrylate and trimethylamminoethyl methacrylate chloride (b) copolymer of ethylacrylate and methacrylic acid, (c) between 1 % and 40% by weight of the pharmaceutically active ingredient.
  • WO 2005/016321 discloses a mucoadhesive delivery system for the local or systemic administration of a pharmaceutical agent.
  • the delivery system of the invention effectively and facilely enables transport of the pharmaceutical agent through mucosal membranes and into the vasculature of the mucosa.
  • the delivery system includes an at least partially water- soluble bioadhesive layer and an at least partially water-soluble backing layer. Incorporated within either or both of these layers are the pharmaceutical agent and a mucosal penetration enhancing agent.
  • WO 2005/048979 discloses a modified release pharmaceutical composition consists of casing comprising at least two micro tablets, which are coated with rate controlling agent(s) optionally in combination with auxiliary pharmaceutical excepient(s), wherein each micro tablet comprises core particles comprising pharmaceutical active ingredient and rate controlling agent(s), the said core particles optionally coated with rate controlling agent(s).
  • compositions of tolterodine or pharmaceutically acceptable salts thereof comprising immediate release core and a single coating layer comprising rate controlling agent(s).
  • composition comprising tolterodine or pharmaceutically acceptable salts thereof, wherein composition provides a dissolution profile having a reduced dependency from the pH- value and/or the ionic strength of the dissolving medium of the controlled release composition
  • Tolterodine for the purpose of the present invention may be selected from tolterodine base, i. e., (R)-N, N-diisopropyl-3- (2-hydroxy-5-methylphenyl)-3 phenylpropanamine, as well as the corresponding (S)-enantiomer, the racemate and the active 5-hydroxymethyl metabolites, prodrug forms and pharmaceutically acceptable salts thereof.
  • the preferred salt of tolterodine is tartrate.
  • the first object of the present invention provides controlled release pharmaceutical compositions comprising tolterodine or pharmaceutically acceptable salts thereof wherein the core comprises tolterodine and auxiliary excipients and a single coating layer comprising rate controlling agent(s).
  • Yet another object of the invention provides controlled release pharmaceutical compositions comprising tolterodine or pharmaceutically acceptable salts thereof comprising an immediate release core wherein said core comprises tolterodine and pharmaceutically acceptable salts thereof, water insoluble inert material with one or more auxiliary pharmaceutical excipients and a single coating layer comprising rate controlling hydrophobic and/or hydropbilic agents(s).
  • Yet another object of the present invention provides controlled release pharmaceutical compositions of tolterodine or pharmaceutically acceptable salts thereof wherein additionally a composition contains dissolution enhancing agents comprising organic acids.
  • the dosage forms of the invention typically contain 1 to 20 mg tolterodine as base.
  • the dosage forms of the invention optionally may comprise salts of tolterodine, preferably tolterodine tartrate.
  • immediate release core refers to core comprising tolterodine or pharmaceutically acceptable salts thereof devoid of any release-controlling agent(s).
  • controlled release compositions refers to any composition or dosage form which comprises an active drug and which is formulated to provide a longer duration of pharmacological response after administration of the dosage form than is ordinarily experienced after administration of a corresponding immediate release composition comprising the same drug in the same amount.
  • Controlled release compositions include, inter alia, those compositions described elsewhere as “extended release”, “delayed release”, “sustained release”, “prolonged release”, “programmed release”, “time release” and/or "rate controlled” compositions or dosage forms.
  • the hydrophilic release controlling agents are selected from but are not limited to 5 hydroxypropyl methyl cellulose (HPMC), hydroxypropyl cellulose (HPC), hydroxyethyl cellulose (HEC) polyethylene oxide, polyvinyl alcohol, polyvinylpyrrolidone, xanthan gum, guar gum, chitosan and its derivatives, carbomer, carrageenan, carboxymethyl cellulose, sodium alginate, polyglycolized glycerides, polyethylenglycol, or mixture thereof.
  • HPMC hydroxypropyl methyl cellulose
  • HPC hydroxypropyl cellulose
  • HEC hydroxyethyl cellulose
  • the hydrophobic release controlling agents are selected from but are not limited to polyvinyl acetate dispersion, ethyl cellulose, cellulose acetate, cellulose propionate (lower, medium or higher molecular weight), cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate phthalate, cellulose triacetate, poly (methyl methacrylate), poly (ethyl methacrylate), poly (butyl methacrylate), poly (isobutyl methacrylate), and poly (hexyl methacrylate), poly
  • controlled release pharmaceutical compositions includes a pharmaceutical composition that encompasses one or more individual coated units.
  • the coated units may be 25 a capsule or tablet of may be in form of granules, pellets, minitablets or beads.
  • compositions of the present invention can also include other materials such as dissolution enhancing agents, binders, diluents, anti-adherents, glidants and lubricants.
  • Dissolution enhancing agents include pharmaceutically acceptable organic acids. Examples include but not limited to ascorbic acid, succinic acid, malonic acid, oxalic acid, tartaric acid, fumaric acid, adipic acid, glucono delta-lactone and malic acid.
  • Diluents may be, for example, any pharmaceutically acceptable, non-toxic diluent. Particular examples include lactose, dextrose, sucrose, maltose, microcrystalline cellulose, starch, calcium hydrogen phosphate, mannitol and the like.
  • Binders may be, for example, starch, sugars, gums, low molecular weight hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose or the like.
  • Lubricants may be, for example, talc, magnesium stearate, calcium stearate, stearic acid, sodium stearyl fumarate, sodium benzoate or the like.
  • Antiadherents and Glidants may be, for example, colloidal silicon dioxide, talc or the like.
  • Solid oral dosage forms of the present invention may be prepared by any conventional techniques for example dry granulation, direct compression, wet granulation, and extrusion- spheronization. Wet granulation and extrusion-spheronization are the preferred techniques.
  • wet granulation and extrusion-spheronization are the preferred techniques.
  • tolterodine or pharmaceutically acceptable salt thereof and other auxiliary pharmaceutical ingredients are granulated with a granulating fluid (e.g., isopropyl alcohol, ethyl alcohol, and water) in a planetary mixer, high shear mixer, or fluidized bed granulator.
  • the binder and organic acid solution is prepared in suitable vehicles, both can be mixed. Only binder or mixed solution of binder and organic acid can be used to granulate the powder mass.
  • the wet granules are dried in an oven or fluidized bed dryer, and then sieved through a suitable screen to obtain free flowing granules.
  • the resulting granules are blended with a suitable lubricant and glidant.
  • These granules are compressed into solid dosage from of suitable, size.
  • These are further coated with the one or more hydrophobic and/or hydrophilic controlling agent(s) effective for the controlled release of tolterotidine or pharmaceutical acceptable salts thereof.
  • tolterodine and pharmaceutically acceptable salts is geometrically mixed with water insoluble inert material.
  • the binder and organic acid solution is prepared in suitable vehicles, both can be mixed.
  • binder or mixed solution of binder and organic acid is used to granulate the blend of active material with water insoluble inert material. Then wet mass is extrudated using suitable extruder and spheronized using spheronizer. Pellets or spheroids thus obtained are dried and coated with release controlling hydrophilic and/or hydrophobic controlling agent(s). The so-formed multiple units may be filled into hard shell capsules or compressed into a tablet.
  • step 5 Granulate the. powder mass of step 1 with solution of step 4 6 Extrudate the wet mass through 1 mm sieve using extruder and spheronized using spheronizer.
  • step 2 Granulate the powder mass of step 1 with purified water.
  • step 3 Dry the granules of step 2 in a suitable dryer

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention porte sur une composition pharmaceutique à libération régulée qui contient un noyau comportant de la toltérodine ou des sels acceptables du point de vue pharmaceutique de celle-ci, des excipients auxiliaires et une seule couche d'enrobage comportant un ou des agents de régulation de vitesse. L'invention porte également sur une composition pharmaceutique à libération régulée qui comporte de la toltérodine ou des sels acceptables du point de vue pharmaceutique de celle-ci, le noyau comportant de la toltérodine ou des sels acceptables du point de vue pharmaceutique de celle-ci, des excipients auxiliaires et une seule couche d'enrobage comportant un ou des agents de régulation de la vitesse, ladite composition comportant en outre un ou des agents améliorant la dissolution.
PCT/IN2008/000695 2007-10-29 2008-10-22 Compositions pharmaceutiques à libération régulée de toltérodine WO2009057138A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2010531645A JP2011502140A (ja) 2007-10-29 2008-10-22 トルテロジンの制御放出型医薬組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1475KO2007 2007-10-29
IN1475/KOL/2007 2007-10-29

Publications (2)

Publication Number Publication Date
WO2009057138A2 true WO2009057138A2 (fr) 2009-05-07
WO2009057138A3 WO2009057138A3 (fr) 2009-07-23

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PCT/IN2008/000695 WO2009057138A2 (fr) 2007-10-29 2008-10-22 Compositions pharmaceutiques à libération régulée de toltérodine

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JP (1) JP2011502140A (fr)
WO (1) WO2009057138A2 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010131265A1 (fr) * 2009-05-11 2010-11-18 Lupin Limited Nouvelles compositions pharmaceutiques de fénofibrate de choline
WO2011102506A1 (fr) * 2010-02-22 2011-08-25 第一三共株式会社 Préparation solide à libération prolongée pour usage oral
US20120128773A1 (en) * 2009-05-11 2012-05-24 Ratiopharm Gmbh Desfesoterodine in the form of a tartaric acid salt
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
US9629808B2 (en) 2010-02-22 2017-04-25 Daiichi Sankyo Company, Limited Sustained-release solid preparation for oral use
US9744157B2 (en) 2011-05-10 2017-08-29 Theravida, Inc. Combinations of solifenacin and salivary stimulants for the treatment of overactive bladder
US9827199B2 (en) 2012-09-03 2017-11-28 Daiichi Sankyo Company, Limited Hydromorphone hydrochloride-containing oral sustained-release pharmaceutical composition
US10328057B2 (en) 2016-01-20 2019-06-25 Theravida, Inc. Methods and compositions for treating hyperhidrosis
US11229599B2 (en) 2015-07-28 2022-01-25 Board Of Regents, The University Of Texas System Implant compositions for the unidirectional delivery of therapeutic compounds to the brain

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105735A1 (fr) * 2003-05-30 2004-12-09 Ranbaxy Laboratories Limited Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation
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
WO2007029087A2 (fr) * 2005-09-05 2007-03-15 Ranbaxy Laboratories Limited Preparations multi-unites a liberation controlee
WO2007113207A2 (fr) * 2006-03-31 2007-10-11 Lek Pharmaceuticals D.D. Formulations enduites
WO2008012346A1 (fr) * 2006-07-28 2008-01-31 Farmaprojects, S. A. Préparation pharmaceutique de métoprolol à libération prolongée et son procédé de préparation
WO2009019599A2 (fr) * 2007-08-08 2009-02-12 Themis Laboratories Private Limited Compositions à libération prolongée comprenant de la toltérodine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59175414A (ja) * 1983-03-23 1984-10-04 Toyo Jozo Co Ltd マクロライド抗生物質の安定な経口用製剤および安定化法
JP2001316292A (ja) * 1999-09-03 2001-11-13 Takeda Chem Ind Ltd 医 薬

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105735A1 (fr) * 2003-05-30 2004-12-09 Ranbaxy Laboratories Limited Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation
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
WO2007029087A2 (fr) * 2005-09-05 2007-03-15 Ranbaxy Laboratories Limited Preparations multi-unites a liberation controlee
WO2007113207A2 (fr) * 2006-03-31 2007-10-11 Lek Pharmaceuticals D.D. Formulations enduites
WO2008012346A1 (fr) * 2006-07-28 2008-01-31 Farmaprojects, S. A. Préparation pharmaceutique de métoprolol à libération prolongée et son procédé de préparation
WO2009019599A2 (fr) * 2007-08-08 2009-02-12 Themis Laboratories Private Limited Compositions à libération prolongée comprenant de la toltérodine

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8871275B2 (en) 2007-08-08 2014-10-28 Inventia Healthcare Private Limited Extended release compositions comprising tolterodine
US20120128773A1 (en) * 2009-05-11 2012-05-24 Ratiopharm Gmbh Desfesoterodine in the form of a tartaric acid salt
US9085507B2 (en) * 2009-05-11 2015-07-21 Ratiopharm Gmbh Desfesoterodine in the form of a tartaric acid salt
WO2010131265A1 (fr) * 2009-05-11 2010-11-18 Lupin Limited Nouvelles compositions pharmaceutiques de fénofibrate de choline
WO2011102506A1 (fr) * 2010-02-22 2011-08-25 第一三共株式会社 Préparation solide à libération prolongée pour usage oral
US9629808B2 (en) 2010-02-22 2017-04-25 Daiichi Sankyo Company, Limited Sustained-release solid preparation for oral use
US9968556B2 (en) 2010-04-01 2018-05-15 Theravida, Inc. Pharmaceutical formulations
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
JP2016147884A (ja) * 2010-04-01 2016-08-18 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
US10786457B2 (en) 2010-04-01 2020-09-29 Theravida, Inc. Pharmaceutical formulations
JP2018058885A (ja) * 2010-04-01 2018-04-12 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
US9744157B2 (en) 2011-05-10 2017-08-29 Theravida, Inc. Combinations of solifenacin and salivary stimulants for the treatment of overactive bladder
US9827199B2 (en) 2012-09-03 2017-11-28 Daiichi Sankyo Company, Limited Hydromorphone hydrochloride-containing oral sustained-release pharmaceutical composition
US11229599B2 (en) 2015-07-28 2022-01-25 Board Of Regents, The University Of Texas System Implant compositions for the unidirectional delivery of therapeutic compounds to the brain
US10328057B2 (en) 2016-01-20 2019-06-25 Theravida, Inc. Methods and compositions for treating hyperhidrosis
US10610519B2 (en) 2016-01-20 2020-04-07 Theravida, Inc. Methods and compositions for treating hyperhidrosis
US11185533B2 (en) 2016-01-20 2021-11-30 Theravida, Inc. Methods and compositions for treating hyperhidrosis
US11779569B2 (en) 2016-01-20 2023-10-10 Theravida, Inc. Methods and compositions for treating hyperhidrosis

Also Published As

Publication number Publication date
WO2009057138A3 (fr) 2009-07-23
JP2011502140A (ja) 2011-01-20

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