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WO2024128995A1 - Compositions pharmaceutiques de mirabégron - Google Patents

Compositions pharmaceutiques de mirabégron Download PDF

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Publication number
WO2024128995A1
WO2024128995A1 PCT/TR2022/051513 TR2022051513W WO2024128995A1 WO 2024128995 A1 WO2024128995 A1 WO 2024128995A1 TR 2022051513 W TR2022051513 W TR 2022051513W WO 2024128995 A1 WO2024128995 A1 WO 2024128995A1
Authority
WO
WIPO (PCT)
Prior art keywords
prolonged
composition according
release tablet
tablet composition
mirabegron
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/TR2022/051513
Other languages
English (en)
Inventor
Erol KIRESEPI
Ersin Yildirim
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.)
Santa Farma Ilac Sanayi AS
Original Assignee
Santa Farma Ilac Sanayi AS
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 Sanayi AS filed Critical Santa Farma Ilac Sanayi AS
Priority to PCT/TR2022/051513 priority Critical patent/WO2024128995A1/fr
Priority to EP22968683.7A priority patent/EP4633631A1/fr
Publication of WO2024128995A1 publication Critical patent/WO2024128995A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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
    • 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
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • 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

Definitions

  • the present invention relates to a homogenous pharmaceutical composition comprising mirabegron or a pharmaceutically acceptable salt thereof developed in the prolonged release of the solid dosage form with improved pharmaceutical properties.
  • BACKGROUND O F THE INVENTION Overactive bladder is a chronic distressing condition that has a tremendous impact on the health-related quality of life of the inflicted individuals (daily activities and social functions). According to the International Continence Society, the overactive bladder syndrome is characterized by urgency, with or without urinary incontinence, usually associated with increased daytime frequency and nocturia.
  • the aim of the pharmacotherapeutic treatment options indicated for the overactive bladder is to obtain the reduced or suppressed intensity of involuntary detrusor contraction.
  • overactive bladder There are many options for the treatment of overactive bladder such as; bladder training and drug therapy using antimuscarinic drugs.
  • antimuscarinic drugs are not always effective in controlling an overactive bladder due to the adverse effects, including dry mouth, nausea, constipation, and central nervous system adverse effects, that cause poor long-term adherence to treatment.
  • a novel active substance mirabegron developed by Astellas Pharmac Inc.
  • this compound has not only both an activity of promoting insulin secretion and an activity of enhancing insulin sensitivity, but also an antiobestic activity and an antihyperlipemic activity based on an activity of selectively stimulating a ⁇ 3 receptor, and is useful in treating diabetes. Further, it has been reported as an alternative option to antimuscarinic drugs for patients with overactive bladder accompanied by prostatic hyperplasia, or overactive bladder accompanied by urinary urgency, urinary incontinence, and urinary frequency.
  • Mirabegron is an active substance that chemical name is 2-(2-Amino-1,3-thiazol-4-yl)-N-[4- (2- ⁇ [(2R)-2-hydroxy-2-phenylethyl] amino ⁇ ethyl) phenyl] acetamide with the following structure Formula I.
  • the empirical formula is C21H24N4O2S.
  • the compound has a molecular weight of 396.506 g/mol.
  • Mirabegron appears as a white crystalline powder and is non-hygroscopic. It can be freely soluble in dimethyl sulfoxide, soluble in methanol, and soluble in water between neutral to acidic pH. Mirabegron has one chiral center and exhibits stereoisomerism.
  • the manufacture of the finished product consists of the R-enantiomer.
  • Mirabegron and its pharmaceutically acceptable salts thereof first have been described in EP1028111 numbered patent document by Yamanouchi Pharmaceutical Co. in which the preparation of mirabegron and its pharmaceutically acceptable salt thereof, with hydrochloride salt, in particular, Example 41 is also disclosed.
  • a patent document numbered EP1559427 was the first to disclose a pharmaceutical composition comprising mirabegron that could be used as a therapeutic agent for overactive bladders, such as overactive bladder accompanied by prostatic hyperplasia, or overactive bladder accompanied by urinary urgency, urinary incontinence, and urinary frequency.
  • EP2554168 relates to modified release pharmaceutical composition
  • modified release pharmaceutical composition comprising mirabegron or a pharmaceutically acceptable salt thereof, and a carrier for a sustained release pharmaceutical composition, wherein the dissolution rate of the drug from the composition is 75% or less after 1.5 hours from the beginning of the dissolution test, and also wherein the pharmaceutical composition is not a sustained release hydrogel formulation which contains an additive that allows water to penetrate into the formulation, and a hydrogel-forming polymer.
  • EP2345410 relates to modified release pharmaceutical composition
  • modified release pharmaceutical composition comprising mirabegron, at least one additive having a solubility such that the volume of water required for dissolving 1 g of the additive is 10 mL or less to ensure penetration of water into the pharmaceutical composition, and a hydrogel-forming polymer having an average molecular weight of approximately 100.000 or more, or viscosity of 12 cP or more at a 5% aqueous solution at 25°C.
  • WO2011122523 relates to a pharmaceutical composition comprising mirabegron or a pharmaceutically acceptable salt thereof, and a carrier for a sustained release pharmaceutical composition, and the drug dissolution rate after 30 minutes from the beginning of the dissolution test is less than 85%.
  • EP3345600 relates to a pharmaceutical composition
  • a pharmaceutical composition comprising mirabegron, hypromellose, and polyvinylpyrrolidone, wherein the spray-dried granulated product contains 100% or more by mass of the hypromellose, and the polyvinylpyrrolidone in total with respect to a content of the mirabegron.
  • WO2019072404 relates to a pharmaceutical composition for modified release comprising mirabegron presenting 5-25 w/w% to the total weight of the uncoated tablet, polyethylene oxide having an average molecular weight of approximately 7,000,000 or viscosity of 7500 to 10000 cps at a 1% aqueous solution at 25°C and polyethylene glycol having an average molecular weight of approximately 6000 to 10000, preferably 8000, wherein the weight ratio polyethylene oxide to polyethylene glycol ranges from 1:3 to 1:4.5.
  • EP3448366 relates to a pharmaceutical composition for modified release comprising; 5 to 25 w/w% mirabegron relative to the total weight of the formulation, 15 to 40 w%, relative to the total weightof the formulation, of a mixture of one or more polyethylene oxides having a viscosity of 100 to 800, preferably 400 to 800 cP at a 2% aqueous solution at 25°C, and a water- insoluble hydrophilic excipient.
  • EP3554480 relates to a solid prolonged release solid pharmaceutical oral dosage form comprising mirabegron or a pharmaceutically acceptable salt thereof wherein mirabegron is distributed in a sustained release matrix comprising a hydrogel generator selected from the group consisting of a mixture of at least two different hydroxypropyl methylcellulose, of alginate, alginic acid, poly (meth) acrylate-based polymer and carrageenan, and wherein dissolution rate of the drug from the composition is 20% to 40% in 3 hours, 44% to 64% in 5 hours and more than 80% in 8.5 hours.
  • WO2018169325 relates to a controlled-release pharmaceutical composition comprising mirabegron or a pharmaceutically acceptable salt thereof and a polyethylene oxide as a sustained-release agent.
  • WO2022125007 relates to a prolonged release formulation comprising mirabegron or a pharmaceutically acceptable salt thereof as an active ingredient in which the release profile of the active ingredient is controlled by using a specific hydrophobic polymer and a plasticizer at a specific range of ratio between 1:0.5 to 1:1 in the coating formulation.
  • the prolonged-release tablet dosage form comprising mirabegron leads to a slower absorption rate in the gastrointestinal tract than immediate-release formulations, even in fasted conditions, due to pharmacokinetic variation of mirabegron according to the presence or absence of food in the gastrointestinal tract.
  • the present object of this invention is to develop a pharmaceutical composition comprising a therapeutically effective amount of mirabegron or one of its pharmaceutically acceptable salts in prolonged-release dosage solid form with an improved qualitative formulation presents improved in vitro and in vivo characteristics.
  • Another object of the invention is to develop an improved pharmaceutical composition comprising mirabegron or one of its pharmaceutically acceptable salts used in the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency.
  • Another object of the present invention is related to a pharmaceutical composition comprising mirabegron or one of its pharmaceutically acceptable salts, wherein the mirabegron is free of salt, preferably it is in crystalline form, more preferably it is in alpha crystalline form.
  • Another object of the invention is related to the prolonged-release tablet composition comprising 25 mg to 50 mg mirabegron.
  • Another object of the invention is to design a qualitative prolonged-release tablet formulation that is in the form of tablet by using particular matrix agents.
  • Another object of the invention is to design a qualitative prolonged-release tablet formulation that is in the form of tablet by using particular matrix agents in a particular amount in the formulation with a particular ratio between them and wet granulation manufacturing method.
  • One of the object of the invention is to provide a successful tablet compression process with improved qualitative prolonged-release formulation that has compressibility properties.
  • Another object of the invention is to design a qualitative prolonged-release tablet formulation that in the dosage form of tablet compressed successfully along within a high range of hardness.
  • Another object of the invention is to design a qualitative prolonged-release tablet formulation obtained with a tablet compression process that is carried out between 150-300 kP.
  • Another object of the invention is to design a qualitative prolonged-release tablet formulation that presents proper in vitro and in vivo release profile.
  • the present invention provides a prolonged-release composition comprising a therapeutically effective amount of mirabegron or one of its pharmaceutically acceptable salts with an improved in vitro dissolution and in vivo release profiles.
  • the present invention provides a prolonged-release composition comprising a therapeutically effective amount of mirabegron or one of its pharmaceutically acceptable salts and one or more pharmaceutically acceptable excipient.
  • prolonged-release herein refers to any composition or dosage form which comprises active ingredient and which is designed to achieve or extend therapeutic effect by continuously releasing over an extended period of time after administration corresponding to immediate release dosage form administered by the same route.
  • the term “prolonged-release dosage form” involves a matrix form that provides prolonged-release behaviour by overcoming food effect resulting reduced maximum concentration (C max ) and the area under the concentration-time curve (AUC) following high or low fat meal compared to fasting.
  • the term “prolonged-release dosage form” involves a matrix form comprising homogenously dispersed the active ingredient throughout matrix agents ensure to control release rate of active ingredient by swelling to form a hydrogel layer allowing drug release through the outer surface of the gel.
  • one of the matrix agents is hydrogel forming polymer as polyethylene oxide (PEO) that has hydrophilic characteristics in the molecular weight range of 100,000 to 7,000,000 Da.
  • a prolonged-release solid tablet formulation comprises at least one pharmaceutically acceptable excipient that has another critical role in the matrix formulation.
  • a prolonged-release solid tablet formulation comprises another matrix agent being hydroxypropyl methylcellulose (HPMC) as at least one pharmaceutically acceptable excipient that has another critical role in the matrix formulation.
  • HPMC hydroxypropyl methylcellulose
  • the preferred embodiment of this invention provides a pharmaceutical composition comprising a therapeutically effective amount of mirabegron or one of its pharmaceutically acceptable salts in the prolonged-release dosage form manufactured by using a high-shear granulation optimized amounts of PEO and HPMC.
  • the manufacturing method of the prolonged-release tablet formulation comprising PEO and HPMC is wet granulation comprising improved granulation process to generate a hydrophilic matrix.
  • Granulation has been considered a pharmaceutical process of particle design that gathers small particles into a larger mass with the original particles still identifiable. Increasing the density of materials, minimizing the tablet weight variation, or improving the dissolution rate is one of the main objectives of the process. Thus, the selection of the manufacturing process and process parameters affect release properties.
  • a prolonged-release tablet pharmaceutical composition comprising a therapeutically effective amount of mirabegron or one of its pharmaceutically acceptable salts is manufactured by using a high-shear granulation.
  • the granulation solution can be a solvent or a solution comprising a binder or any excipient to be used to ensure particle adhesion once the granule is dried.
  • the granulation solution may include but is not limited to deionized water, methanol, ethanol, isopropyl alcohol, dichloromethane, acetone, and thereof.
  • the granulation solution is acetone an organic solvent.
  • the desired dissolution profile of mirabegron or its pharmaceutically acceptable salt thereof is provided with a developed pharmaceutical composition comprising a polymer, filler, diluent, binder, antioxidant, lubricant, glidant, and granulation solution selected as to be the most suitable ones with respect to the intended form of administration.
  • the filler may include but is not limited to dibasic calcium phosphate dehydrate, polysaccharides, microcrystalline cellulose, lactose, or mixtures thereof.
  • the filler is microcrystalline cellulose.
  • the binder may include but is not limited to hypromellose, sodium carboxymethyl cellulose, povidone, starch, sucrose or mixtures thereof.
  • the binder is hypromellose.
  • the antioxidant may include but is not limited to butylated hydroxytoluene, propyl gallate, butyl hydroxyanisole, ascorbic acid, sodium ascorbate, erythorbic acid, sodium nitrite, sodium bisulfite, sodium pyrosulfite, citric acid, and thereof.
  • the antioxidant is butylated hydroxytoluene.
  • the lubricant may include but is not limited to magnesium stearate, calcium stearate, talc, colloidal silica, and thereof.
  • the lubricant is magnesium stearate.
  • the glidant may include but is not limited to silicon dioxide, colloidal silicon dioxide, magnesium silicate, magnesium trisilicate, talc, and thereof.
  • the glidant is colloidal silicon dioxide.
  • the embodiment in accordance with the present invention was designed with an adjusted qualitative and quantitative composition composed of pharmaceutically acceptable ingredients mentioned above by using high-shear granulation.
  • the prolonged-release embodiment identified as Example 1 based on the invention provided a prolonged-release solid pharmaceutical formulation in critical quantitative ratio below: - the ratio of the amounts between Mirabegron and the matrix agents is between 0.5:1.0 - 1.0:1.0 - the hardness value during tablet compression is between 150-300 kP.
  • Example-1 the ratio between the matrix agents, polyethylene oxide and hydroxypropyl methylcellulose, is between 1.0:1.0 to 1.4:1.0 in Example 1.
  • the qualitative unit formula of Example-1 is as below: Ingredients Mirabegron Polyethylene oxide Hydroxypropyl methylcellulose Microcrystalline cellulose Hydroxypropyl cellulose Butylated hydroxytoluene Magnesium stearate Colloidal silicon dioxide Organic solvent Core tablet
  • Another object of the present invention relates to providing a high-shear granulation process for preparing the prolonged-release pharmaceutical composition, providing the steps: i. Mirabegron and at least one polymer screened through a proper sieve and transferred into the high-shear mixer and stirred, ii.
  • Step (i) Filler, the other polymer, and a binder were screened through a proper sieve and added to the granules prepared in Step (i) and stirred, iii.
  • the antioxidant was dissolved in a sufficient quantity of acetone and added to the preparation in Step (ii) to perform the granulation process, iv.
  • the granules prepared in Step (iii) were dried and shifted through a proper sieve, v.
  • Glidant and lubricant were screened through a proper sieve and added to the granules prepared in Step (iv) and stirred, vi.
  • Tablet compression was performed with the final blend in Step (v). According to the present invention, tablet compression was achieved by processing between 150 – 300 kP.
  • the hardness is important parameter to obtain desired in vitro and in vivo releases.
  • the final product was analysed the quality attributes based on the international guidelines. Compressed tablets were subjected to in vitro dissolution study set by US FDA.
  • the dissolution medium is phosphate buffer, pH 6.8. Other conditions are: - 900 ml dissolution medium - 37°C ⁇ 0.5°C temperature - 100 rpm rotation speed with basket apparatus, and - 12 hours duration of dissolution study.
  • the amount of dissolved active ingredient over time was determined by HPLC.
  • Table 2 Comparative dissolution profile for Example 1 in pH 6.8 phosphate buffer Time, hour Results, % Reference Drug Product Example 1 1 7 9 3 26 34 5 50 60 7 75 81 8.5 90 94 10 98 101 12 100 103 Based on the results presented in Table 2 above, the release pattern of Example 1 was similar to the reference drug product. According to The Guideline on the Investigation of Bioequivalence, the in vitro dissolution profile of two drug products is evaluated based on the value of similarity factor f2, if that value is higher than 50, the two drug products in comparison show similar dissolution profiles. The similarity factor f 2 of Example 1 and the reference drug product was calculated as 62 since this value was above 50 the products compared were similar.

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

Abstract

La présente invention concerne une composition pharmaceutique homogène contenant du mirabégron ou un sel pharmaceutiquement acceptable de celui-ci, mise au point sous une forme impliquant la libération prolongée de la forme posologique solide, présentant des propriétés pharmaceutiques améliorées.
PCT/TR2022/051513 2022-12-16 2022-12-16 Compositions pharmaceutiques de mirabégron Ceased WO2024128995A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/TR2022/051513 WO2024128995A1 (fr) 2022-12-16 2022-12-16 Compositions pharmaceutiques de mirabégron
EP22968683.7A EP4633631A1 (fr) 2022-12-16 2022-12-16 Compositions pharmaceutiques de mirabégron

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/TR2022/051513 WO2024128995A1 (fr) 2022-12-16 2022-12-16 Compositions pharmaceutiques de mirabégron

Publications (1)

Publication Number Publication Date
WO2024128995A1 true WO2024128995A1 (fr) 2024-06-20

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ID=91485397

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TR2022/051513 Ceased WO2024128995A1 (fr) 2022-12-16 2022-12-16 Compositions pharmaceutiques de mirabégron

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EP (1) EP4633631A1 (fr)
WO (1) WO2024128995A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104523635A (zh) * 2014-12-23 2015-04-22 深圳万乐药业有限公司 米拉贝隆缓释药物组合物
EP3345600A1 (fr) * 2015-09-01 2018-07-11 Sawai Pharmaceutical Co., Ltd. Comprimé contenant du mirabégron, procédé de production d'une préparation pharmaceutique contenant du mirabégron et procédé de production d'un produit sous forme granulée contenant du mirabégron
WO2019013583A2 (fr) * 2017-07-14 2019-01-17 주식회사 대웅제약 Préparation pharmaceutique et son procédé de préparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104523635A (zh) * 2014-12-23 2015-04-22 深圳万乐药业有限公司 米拉贝隆缓释药物组合物
EP3345600A1 (fr) * 2015-09-01 2018-07-11 Sawai Pharmaceutical Co., Ltd. Comprimé contenant du mirabégron, procédé de production d'une préparation pharmaceutique contenant du mirabégron et procédé de production d'un produit sous forme granulée contenant du mirabégron
WO2019013583A2 (fr) * 2017-07-14 2019-01-17 주식회사 대웅제약 Préparation pharmaceutique et son procédé de préparation

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