WO2022115056A1 - Compositions de formulation à libération prolongée comprenant de la propivérine - Google Patents

Compositions de formulation à libération prolongée comprenant de la propivérine Download PDF

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Publication number
WO2022115056A1
WO2022115056A1 PCT/TR2020/051189 TR2020051189W WO2022115056A1 WO 2022115056 A1 WO2022115056 A1 WO 2022115056A1 TR 2020051189 W TR2020051189 W TR 2020051189W WO 2022115056 A1 WO2022115056 A1 WO 2022115056A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
sustained release
release pharmaceutical
composition according
propiverine
Prior art date
Application number
PCT/TR2020/051189
Other languages
English (en)
Inventor
Erol KIRESEPI
Ersin Yildirim
Original Assignee
Santa Farma Ilac Sanayii A.S.
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 Santa Farma Ilac Sanayii A.S. filed Critical Santa Farma Ilac Sanayii A.S.
Priority to EP20963798.2A priority Critical patent/EP4251154A1/fr
Priority to PCT/TR2020/051189 priority patent/WO2022115056A1/fr
Publication of WO2022115056A1 publication Critical patent/WO2022115056A1/fr

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Classifications

    • 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
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, 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

Definitions

  • the present invention relates to a novel sustained release solid pharmaceutical composition for oral administration comprising propiverine or a pharmaceutically acceptable salt thereof with at least one pH independent release controlling polymer for use in the treatment of urinary urgency, frequency and urge incontinence, all symptoms of overactive bladder syndrome.
  • Propiverine is a typical anticholinergic agent, and also acts as a calcium channel antagonist, thus it is widely used in many countries to treat urinary incontinence, as well as frequency associated with detrusor over activity, such as neurogenic bladder and bladder irritation.
  • Overactive bladder is characterized by symptoms of urgency, with or without urgency incontinence, usually with frequency and notarial. Overactive bladder symptoms are suggestive of urodynamic demonstrable detrusor over activity. There are two main options for primary treatment of overactive bladder such as; bladder training and drug therapy using anticholinergic agents. Anticholinergic agents are often used to reduce detrusor over activity and improve overactive bladder symptoms.
  • propiverine is l-methyl-4-piperidyl diphenylpropoxyacetate and the empirical formula is C23H30CINO3. The compound has a molecular weight of 403.95 g/mol.
  • the structural formula of propiverine is shown in the Formula I.
  • Propiverine as hydrochloride salt is an orally an anti-muscarinic agent, and which is currently on the market under the name of the MICTONORM ® as immediate release and modified release for the treatment of urinary incontinence and/or increased urinary frequency and urgency in patients with overactive bladder syndrome with the authorization holder of Apogepha Arzneistoff GmbH.
  • the immediate release tablet dosage form is marketed in the strength of 15 mg propiverine hydrochloride that is equivalent to 13.64 mg propiverine per tablet, whereas the modified release capsule dosage form is marketed in the strengths of 30 mg and 45 mg propiverine hydrochloride which are respectively equivalent to 27.28 mg and 40.92 mg propiverine per capsule.
  • DD 106643 numbered patent is the basic patent that is first mentioned about propiverine and its salts.
  • EP 1435915 (Apogepha Arzneiffen GmbH) provides a prolonged-release pharmaceutical composition comprising 4 mg to 60mg of propiverine or acceptable salts thereof, where the composition is adapted for once-a-day oral administration and has specific in vitro release characteristics measured in 750 ml of 0. IN hydrochloric acid during the first hour and following measured in 750 ml USP buffer at pH 5.8 using a Ph. Eur. basket method at 100 rpm and 37°C.
  • W02006046560 (Taiho Pharmaceutical) provides oral preparation that ensures good sensation upon administration thereof obtaining a suspension resulting from mixing of propiverine hydrochloride, a surfactant, a pH adjusting agent and water and having its pH value adjusted between 6.5 and 8.0, and subsequently granulating the suspension together with common additives for preparation.
  • EP2276472 provides a pharmaceutical composition by comprising a plurality of controlled-release particles, wherein a core comprising a weekly basic drug, an alkaline buffer layer disposed over the core and a water insoluble polymer of the controlled release coating disposed over the alkaline buffer layer. Enteric effect is provided by multiple coatings.
  • CN102579404A discloses a sustained-release capsule containing propiverine hydrochloride.
  • the sustained capsule comprises micro-pills which have uniform particle size and micro-pills comprise pill cores containing drug accounting for 75 to 97 percent and the sustained release layers accounting for 3 to 25 percent by weight percentage.
  • WO2012154892 discloses a pharmaceutical composition comprising a therapeutically effective amount of extended release propiverine, or a pharmaceutically acceptable salt thereof, and a therapeutically effective amount of pilocarpine, or a pharmaceutically acceptable salt thereof.
  • WO 2007/105229 provides a novel controlled release pharmaceutical composition comprising at least one active agent(s), at least one pH dependent polymer(s), at least one pH independent polymer(s) and at least one channel forming agent(s), optionally with other pharmaceutically acceptable excipients, wherein the ratio of the pH dependent polymer and the pH independent polymer is 1 : 10 to 10:1.
  • EP0173928 (AB Leo) provides a controlled-release pharmaceutical preparation having biphasic release profile, comprising a drug tablet and a coating applied on it, wherein the coating consists of a film-forming polymer which is insoluble in water and gastro-intestinal fluids and a water- soluble pore-creating material being randomly distributed in said polymer characterized in that the pore-creating material includes a drug active substance in a therapeutically effective amount.
  • US5695781 and US6083532 disclose a three-component release rate controlling matrix composition that is composed of a pH dependent polymer and an independent gelling polymer and an enteric polymer.
  • EP2851073 (Taiho Pharmaceutical CO LTD) provides a superior prophylactic agent and/or therapeutic agent comprising an effective amount of 4-piperidyl diphenylpropoxy acetate (propiverine) or a salt thereof, and a pharmaceutical carrier for treating stress urinary incontinence.
  • EP3331502A (Santa Farma Ilac San. A. ⁇ ) provides a controlled release pharmaceutical compositions for oral administration comprising propiverine or a pharmaceutically acceptable salt thereof having biphasic in vitro release characteristics wherein said composition also comprises at least one hydrophilic polymer, at least one water soluble pore forming agent and at least two pH dependent polymers in a matrix formation.
  • This composition provides a dissolution profile of propiverine less than 50.0% after nine hours and more than 85.0% after 24 hours as measured by USP Type I apparatus (basket) at 100 rpm, in 750 mL of 0.1 N hydrochloric acid for the first hour, subsequently in 750 mL USP buffer at pH 5.8 until nine hours, and subsequently in 750 mL of pH 6.8 USP buffer until 24 hours.
  • W02020101586A (Santa Farma Ilac San. A. ⁇ ) provides a controlled release pharmaceutical compositions for oral administration comprising propiverine or a pharmaceutically acceptable salt thereof.
  • This composition comprises at least two pH dependent polymers in the core matrix and an enteric coating in an amount of the range between 0.5% to 2.5% by weight of core tablet wherein pH dependent polymers in the core matrix are Methacrylic Acid - Methyl Methacrylate Copolymer (1:1) soluble starting from pH 6 and Methacrylic Acid - Ethyl Acrylate Copolymer (1: 1) Type A soluble starting from pH 5.5.
  • the resorption rate is related with the half-life period of the substance in the organism deciding whether at the end of the dosage intervals.
  • the resorption rate is related with the half-life period of the substance in the organism deciding whether at the end of the dosage intervals.
  • Propiverine is nearly completely absorbed from the gastrointestinal tract and it undergoes extensive first pass metabolism due to its weak acid.
  • the controlled release dosage form of propiverine is developed with absorbing from the gastrointestinal tract with maximal plasma concentrations reached after 9 to 10 hours and the mean absolute bioavailability is 60.8 ⁇ 17.3%.
  • composition comprising propiverine and one or more pharmaceutically acceptable excipients is developed in sustained release oral solid dosage form which extends the release of propiverine into 24 hours with a design of comprising at least one pH independent release controlling polymer(s).
  • the object of this invention is to develop a sustained release oral pharmaceutical composition
  • a sustained release oral pharmaceutical composition comprising a therapeutically effective amount of propiverine or one of its pharmaceutically acceptable salts, at least two pH independent polymers and pharmaceutically acceptable excipients.
  • a sustained release oral pharmaceutical composition comprising propiverine or one of its pharmaceutically acceptable salts, is used in the treatment of urinary incontinence and/or increased urinary frequency and urgency in patients with overactive bladder syndrome.
  • Another object of the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising propiverine and one or more pharmaceutically acceptable excipients, wherein the propiverine is in hydrochloride form.
  • Another object of the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising propiverine hydrochloride in the matrix with at least one pH independent polymer in a specified range of the total tablet weight to form a gel layer to present sustained release in the intestine region.
  • Another object of the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising propiverine hydrochloride and one or more pharmaceutically acceptable excipients manufactured by using wet granulation method.
  • Another object of the present invention is related to a pharmaceutical composition comprising at least two pH independent polymers in the matrix located in the core.
  • Another object of the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising a pH independent polymer having a viscosity of 70.000 to 140.000 cP in a 2% aqueous solution with an amount range of 8% to 10% by weight of the total tablet in the matrix located in the core.
  • Another object of the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising a pH independent polymer having a viscosity of 80 to 120 cP in a 2% aqueous solution with an amount range of 2% to 4% by weight of the total tablet in the matrix located in the core.
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising propiverine hydrochloride and pharmaceutically acceptable excipients wherein at least two pH independent polymers is used to exhibit a sustained release profile of the drug.
  • Propiverine and its pharmaceutically acceptable salt thereof is a weakly basic drug an has particularly pH dependent solubility.
  • sustained release 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.
  • Sustained release compositions include, inter alia, those compositions described elsewhere as “extended release”, “delayed release”, “controlled release”, “prolonged release”, “programmed release”, “modified release”, “time release” and/or “rate controlled” compositions or dosage forms.
  • sustained release compositions include a core comprising at least two pH independent polymers with different viscosities to overcome the pH dependent solubility of propiverine and its pharmaceutically acceptable salts thereof.
  • the solubility of pH independent release controlling polymer is independent of pH and hence its performance does not depend on the pH of the environment it encounters.
  • the pH independent polymers are selected from the group comprising ethyl cellulose, cellulose acetate, vinyl acetate/vinyl chloride copolymers, acrylate/methacrylate copolymers, polyethylene oxide, hydroxypropyl methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, karaya gum, acacia gum, tragacanth gum, locust bean gum, guar gum, methyl cellulose, beeswax, carnauba wax, cetyl alcohol, hydrogenated vegetable oils, and stearyl alcohol.
  • at least two pH independent polymers are different kinds of hydroxypropyl methylcellulose.
  • At least one of the pH independent polymer is high viscosity hydroxypropyl methyl cellulose, and at least one of two pH independent polymers is low viscosity hydroxypropyl methyl cellulose to get desired dissolution profile in the sustained release dosage form.
  • Hydroxypropyl methylcellulose HPMC
  • HPMC Hydroxypropyl methylcellulose
  • Viscosity grades of HPMC is important to get desired dissolution profile. The pores of high- viscosity HPMC block up quickly and inhibit further liquid uptake.
  • the first part is a letter (E, F or K) relates to the degree of substitution.
  • the K grades have a methoxy substitution of 19-24% and a hydroxypropyl substitution of 7-12%.
  • F have a methoxy substitution of 27-30% and a hydroxypropyl substitution of 4.0- 7.5%.
  • E grades have a methoxy substitution of 28-30% and a hydroxypropyl substitution of 7-12%.
  • This first letter is followed by an indication of the viscosity of their aqueous 2% w/w gels at 20°C.
  • the low viscosity matrix forming polymer is selected from the group comprising a hydroxypropyl methylcellulose selected from HPMC K100LV, HPMC E50LV, HPMC E5, HPMC E15LV or a combination of two or more thereof; and the high viscosity matrix forming polymer includes a hydroxypropyl methylcellulose selected from HPMC K4M, HPMC K15M, HPMC K100M, HPMC E4M and combinations of two or more thereof.
  • low viscosity polymer has a viscosity within the range of 80 to 120 cP in 2% aqueous solution.
  • high viscosity matrix forming polymer has a viscosity within the range of 70.000 to 140.000 cP in 2% aqueous solution.
  • low viscosity polymer is present within the range of 8% to 10% by weight of the composition. In a preferred embodiment of the present invention, low viscosity polymer is present within the range of 2% to 4% by weight of the composition
  • the said invention is achieved by combining propiverine or one of its pharmaceutically acceptable salts with at least two pH independent polymers may further include one or more of other pharmaceutically acceptable excipients selected from, but not limited to, binder, diluent, lubricant, buffering agent and solvent selected as to be the most suitable ones with respect to the intended form of administration.
  • the pharmaceutical composition comprises at least a binder can be selected from hypromellose, sodium carboxymethyl cellulose, cellulose or cellulose derivatives, povidone, starch, sucrose, polyethylene glycol, or mixtures thereof.
  • the binder is sodium carboxymethyl cellulose, povidone or a mixture thereof, more preferably is a mixture thereof.
  • the pharmaceutical composition comprises at least one diluent can be selected from the group consisting of dibasic calcium phosphate dihydrate, polysaccharides, microcrystalline cellulose, lactose and the like and mixtures thereof.
  • the diluent is microcrystalline cellulose.
  • the pharmaceutical composition comprises at least one lubricant, selected from sodium stearyl fumarate, magnesium stearate, calcium stearate talc, stearic acid and mixtures thereof.
  • the lubricant is magnesium stearate.
  • the pharmaceutical composition comprises at least one buffering agent, selected from citric acid, tartaric acid, succinic acid, maleic acid, and fumaric acid.
  • the buffering agent is citric acid.
  • citric acid is known to be widely used in pharmaceutical formulations to adjust the pH of tablet matrices for colon- specific drug delivery.
  • citric acid also affects positively to increase the release profile of propiverine with at least two pH independent polymer throughout the intestinal tract, regardless of the nature of the present propiverine salt, for example, salts of strong acids such as the hydrochloride.
  • the pharmaceutical composition comprises at least one solvent, selected from deionized water, methanol, ethanol, isopropyl alcohol, dichloromethane, acetone, ethyl acetate, dimethylsulfoxide and their mixtures thereof.
  • the solvent is deionized water.
  • a sustained release compositions are compressed into solid dosage form such as tablet, film-coated tablet, enteric-coated tablet, mini-tablet, granule, powder and capsule.
  • Example 1 Three embodiments called Example 1, Example 2 and Example 3 in accordance with the present invention were designed with determined quantitative composition composed of pharmaceutically acceptable ingredients mentioned above.
  • the prepared pharmaceutical compositions comprising propiverine hydrochloride, at least two pH independent polymers and at least one pharmaceutically acceptable excipient.
  • Example 1 Example 2 and Example 3, pH independent polymers with different viscosity grades, were used within a specified range to adjust the viscosity range to get desired drug release profile. Moreover, propiverine hydrochloride and the excipients were also used in the specified range in all the examples. Examples were manufactured by using wet granulation method.
  • the proposed embodiments based on the invention provides a sustained release pharmaceutical composition wherein the amounts in w/w% by weight of the composition are as stated below:
  • the dissolution conditions were designated considering the gastrointestinal pathway of orally applied dosage forms.
  • the first step of the dissolution test is performed in 0.1N HCI solution for 2 hours and then continues in 900 ml pH 6.8 phosphate buffer at 37°C ⁇ 0.5°C with maintaining USP apparatus I (basket) at 100 rpm rotation speed.
  • the amount of dissolved active ingredient over time was determined by HPLC.
  • a similarity factor ⁇ 2 is the most common comparison index that is used to indicate the similarity of dissolution profiles between examples and reference drug product.
  • the present invention provides a pharmaceutical composition comprising propiverine hydrochloride and at least two pH independent release controlling polymer wherein one of the polymer is selected as low viscosity polymer within the range of from about to 80 to 120 cP in a 2% aqueous solution present in the range of 8% to 10% by weight of the total composition, and other pH independent polymer is selected as high viscosity polymer having viscosity within the range of 95.000 to 140.000 cP in a 2% aqueous solution present in the range of 2% to 4% by weight of the total composition to form matrix structure to get desired dissolution profile in the sustained release dosage form.

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

Abstract

La présente invention concerne une nouvelle composition pharmaceutique solide à libération prolongée pour administration orale comprenant de la propivérine ou un sel pharmaceutiquement acceptable de celle-ci avec au moins un polymère de régulation de libération indépendant du pH destiné à être utilisé dans le traitement de l'urgence urinaire, de la fréquence et de l'incontinence impérieuse, tous les symptômes du syndrome de la vessie hyperactive.
PCT/TR2020/051189 2020-11-27 2020-11-27 Compositions de formulation à libération prolongée comprenant de la propivérine WO2022115056A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP20963798.2A EP4251154A1 (fr) 2020-11-27 2020-11-27 Compositions de formulation à libération prolongée comprenant de la propivérine
PCT/TR2020/051189 WO2022115056A1 (fr) 2020-11-27 2020-11-27 Compositions de formulation à libération prolongée comprenant de la propivérine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/TR2020/051189 WO2022115056A1 (fr) 2020-11-27 2020-11-27 Compositions de formulation à libération prolongée comprenant de la propivérine

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Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD106643A1 (fr) 1973-07-12 1974-06-20
EP0173928A1 (fr) 1984-09-06 1986-03-12 Ab Leo Préparation pharmaceutique à libération contrôlée
US5695781A (en) 1995-03-01 1997-12-09 Hallmark Pharmaceuticals, Inc. Sustained release formulation containing three different types of polymers
US6083532A (en) 1995-03-01 2000-07-04 Duramed Pharmaceuticals, Inc. Sustained release formulation containing three different types of polymers and tablet formed therefrom
EP1435915A1 (fr) 2001-10-09 2004-07-14 APOGEPHA ARZNEIMITTEL GmbH Formes d'administration orale de propiverine ou de ses sels pharmaceutiquement acceptables, a liberation prolongee des agents actifs
WO2006046560A1 (fr) 2004-10-29 2006-05-04 Taiho Pharmaceutical Co., Ltd. Préparation orale particulaire contenant de la propivérine et procédé de fabrication de ladite préparation
WO2007105229A1 (fr) 2006-03-14 2007-09-20 Panacea Biotec Ltd. Composition pharmaceutique a liberation controlee et procede associe
EP2276472A1 (fr) 2008-04-15 2011-01-26 Eurand, Inc. Compositions comprenant des médicaments faiblement basiques et formes posologiques à libération contrôlée
CN102579404A (zh) 2012-01-17 2012-07-18 广州科的信医药技术有限公司 一种盐酸丙哌维林缓释胶囊及其制备方法
US20120244221A1 (en) * 2010-07-08 2012-09-27 Wellesley Pharmaceuticals, Llc Extended-release formulation for reducing the frequency of urination and method of use thereof
WO2012154892A1 (fr) 2011-05-10 2012-11-15 Theravida, Inc. Combinaisons de propivérine et de stimulants salivaires destinées au traitement de l'hyperactivité vésicale
EP2851073A1 (fr) 2012-05-15 2015-03-25 Taiho Pharmaceutical Co., Ltd. Agent prophylactique et/ou agent thérapeutique pour l'incontinence urinaire d'effort
EP3331502A1 (fr) 2015-08-07 2018-06-13 Santa Farma Ilaç Sanayi A.S. Formulations de propivérine à libération contrôlée
WO2020101586A1 (fr) 2018-11-16 2020-05-22 Santa Farma İlaç Sanayi̇ A.Ş. Formulations de propivérine à libération contrôlée

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD106643A1 (fr) 1973-07-12 1974-06-20
EP0173928A1 (fr) 1984-09-06 1986-03-12 Ab Leo Préparation pharmaceutique à libération contrôlée
US5695781A (en) 1995-03-01 1997-12-09 Hallmark Pharmaceuticals, Inc. Sustained release formulation containing three different types of polymers
US6083532A (en) 1995-03-01 2000-07-04 Duramed Pharmaceuticals, Inc. Sustained release formulation containing three different types of polymers and tablet formed therefrom
EP1435915A1 (fr) 2001-10-09 2004-07-14 APOGEPHA ARZNEIMITTEL GmbH Formes d'administration orale de propiverine ou de ses sels pharmaceutiquement acceptables, a liberation prolongee des agents actifs
WO2006046560A1 (fr) 2004-10-29 2006-05-04 Taiho Pharmaceutical Co., Ltd. Préparation orale particulaire contenant de la propivérine et procédé de fabrication de ladite préparation
WO2007105229A1 (fr) 2006-03-14 2007-09-20 Panacea Biotec Ltd. Composition pharmaceutique a liberation controlee et procede associe
EP2276472A1 (fr) 2008-04-15 2011-01-26 Eurand, Inc. Compositions comprenant des médicaments faiblement basiques et formes posologiques à libération contrôlée
US20120244221A1 (en) * 2010-07-08 2012-09-27 Wellesley Pharmaceuticals, Llc Extended-release formulation for reducing the frequency of urination and method of use thereof
WO2012154892A1 (fr) 2011-05-10 2012-11-15 Theravida, Inc. Combinaisons de propivérine et de stimulants salivaires destinées au traitement de l'hyperactivité vésicale
CN102579404A (zh) 2012-01-17 2012-07-18 广州科的信医药技术有限公司 一种盐酸丙哌维林缓释胶囊及其制备方法
EP2851073A1 (fr) 2012-05-15 2015-03-25 Taiho Pharmaceutical Co., Ltd. Agent prophylactique et/ou agent thérapeutique pour l'incontinence urinaire d'effort
EP3331502A1 (fr) 2015-08-07 2018-06-13 Santa Farma Ilaç Sanayi A.S. Formulations de propivérine à libération contrôlée
WO2020101586A1 (fr) 2018-11-16 2020-05-22 Santa Farma İlaç Sanayi̇ A.Ş. Formulations de propivérine à libération contrôlée

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