WO2000040254A1 - Composition pharmaceutique destinee a une administration par voie orale presentant une activite therapeutique sur des troubles gastro-intestinaux - Google Patents

Composition pharmaceutique destinee a une administration par voie orale presentant une activite therapeutique sur des troubles gastro-intestinaux Download PDF

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Publication number
WO2000040254A1
WO2000040254A1 PCT/KR1999/000209 KR9900209W WO0040254A1 WO 2000040254 A1 WO2000040254 A1 WO 2000040254A1 KR 9900209 W KR9900209 W KR 9900209W WO 0040254 A1 WO0040254 A1 WO 0040254A1
Authority
WO
WIPO (PCT)
Prior art keywords
aluminum
weight
hydroxide
magnesium hydroxide
aceglutamide
Prior art date
Application number
PCT/KR1999/000209
Other languages
English (en)
Inventor
Hak Hyung Kim
Jong Wan Lee
Jang Hoon Kweon
Jong Keun Chung
Original Assignee
Daewoong Pharmaceutical Co., Ltd.
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 Daewoong Pharmaceutical Co., Ltd. filed Critical Daewoong Pharmaceutical Co., Ltd.
Priority to KR10-2001-7000075A priority Critical patent/KR100370391B1/ko
Priority to AU34442/99A priority patent/AU3444299A/en
Publication of WO2000040254A1 publication Critical patent/WO2000040254A1/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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K31/28—Compounds containing heavy metals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • A61K33/08—Oxides; Hydroxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the present invention relates to a pharmaceutical composition for oral administration of aceglutamide aluminum (pentakis(N -acetyl-L-glutam -inato)tetrahydroxytrialuminum, C35Hs Al 3 N ⁇ o0 2 ) useful as an anti-ulcerative agent and/or a mixture of aluminum hydroxide and magnesium hydroxide usefiil as an antacid agent. More specifically, the present invention relates to the pharmaceutical composition for oral administration having therapeutic activity on gastrointestinal disorders which comprises aceglutamide aluminum, the mixture of aluminum hydroxide and magnesium hydroxide, or aceglutamide aluminum and the mixture of aluminum hydroxide and magnesium hydroxide as active ingredient, and carrageenan as taste masking agent.
  • aceglutamide aluminum penentakis(N -acetyl-L-glutam -inato)tetrahydroxytrialuminum, C35Hs Al 3 N ⁇ o0 2
  • the present invention relates to the pharmaceutical composition for oral administration having therapeutic activity
  • Aceglutamide aluminum promotes rapid regeneration of damaged gastric mucosa by displaying stimulating activity on production of mucin and constituents of mucosa (Tanaka, H., Gastric cytoprotection of aceglutamide aluminum in rats, Drug Res., 36, 1485-1489(1986)) and recovery of damaged granulation tissue by displaying stimulating activity on formation of granulation (Tanaka, H., Kojima, T. and Marumo, H., Effect of N-acetyl-L-glutamine aluminum complex(KW-HO) on hexosamine content in gastric mucosa, Pharmacometrics 9, 519-522(1975)).
  • aceglutamide aluminum is an anti-ulcerative agent which has various mechanisms.
  • Korean patent publication No. 96-11773 disclosed that aceglutamide aluminum is administered in combination with antacid agent comprising aluminum hydroxide and magnesium hydroxide in a weight ratio of 1 to 1, wherein a weight ratio of aceglutamide aluminum to the antacid agent is 1 to 1.1 —2.3, thereby to obtain excellent therapeutic effects on digestive ulcers such as gastric or duodenal ulcer.
  • the method (i) is inexpensive and simple but has problems in that when active ingredient is very bitter, due to a sweet taste of sweetener, it feels much bitterer than sweetener-free agent on the contrary. Also, in the case of aceglutamide aluminum, although attempts were made to mask its astringent taste by combining it with saccharides such as sucrose, sorbitol, aspartame, etc., its astringent taste became reversely stronger and hence, it became more difficult to take. The method (ii) can effectively mask tastes which cause rejection by patients but the unit cost of manufacturing is elevated since it requires additional manufacturing steps and equipments, and yield is inevitably lowered by involving a coating step.
  • Carrageenan is a high molecular weight polymer extracted from plant, seaweed or animal collagen and is a hydrocolloid belonging to polysaccharide family. Structure of carrageenan consists of alternating copolymers of -(l ⁇ 3)-D-galactose and (l ⁇ 4)-3,6-anhydro-D- or L-galactose. Several members of the family are known; they differ in the amount of sulfate ester and/or other substituent groups they carry, for example, t ' ⁇ ta-carrageenan, kappa-carrageenan, etc.
  • carrageenan has been used as gelling agents, emulsifying agents, stabilizing agents and viscosity builders in foods and non-foods, but especially milk or water systems.
  • carrageenan has never been used in combination with aceglutamide aluminum, aluminum hydroxide or magnesium hydroxide for any use and furthermore, has never been used for masking various tastes including a bitter taste or an astringent taste in any case.
  • the present inventors repeated the extensive studies to develop a novel method by which without involving any additional manufacturing step, a bitter and an astringent taste of aceglutamide aluminum and/or a mixture of aluminum hydroxide and magnesium hydroxide can be effectively masked without any adverse effects on pharmacological activity thereof and particularly, in the case of being manufactured into suspension or solution, precipitates are not formed during a period of preservation after being manufactured to obtain a physically stable dosage form.
  • the purpose of the present invention is to provide a pharmaceutical composition for oral administration of aceglutamide aluminum and/or a mixture of aluminum hydroxide and magnesium hydroxide, which can effectively mask a bitter and an astringent taste thereof without involving any additional manufacturing step and cost, thereby to improve compliance of patients, to facilitate long-term administration, and furthermore, to obtain a physically stable suspension or solution thereof.
  • the present invention provides a pharmaceutical composition for oral administration having therapeutic activity on gastrointestinal disorders characterized by comprising at least one selected from the group consisting of aceglutamide aluminum and a mixture of aluminum hydroxide and magnesium hydroxide as active ingredient and carrageenan as taste masking agent.
  • the composition may comprise aceglutamide aluminum alone as active ingredient.
  • the composition may comprise aceglutamide aluminum and the mixture of aluminum hydroxide and magnesium hydroxide as active ingredient.
  • a weight ratio of aluminum hydroxide to magnesium hydroxide is preferably 1 to 1 and a weight ratio of aceglutamide aluminum to the mixture of aluminum hydroxide and magnesium hydroxide is preferably 1 to 1J — 2.3.
  • the above-described compositions comprise 1 —30 parts by weight of aceglutamide aluminum and 0.01 — 10 parts by weight of carrageenan per 100 parts by weight of the composition.
  • the composition according to the present invention may comprise the mixture of aluminum hydroxide and magnesium hydroxide as active ingredient.
  • the present composition preferably comprises aluminum hydroxide and magnesium hydroxide in a weight ratio of 1 to 1. And it preferably comprises 20 — 50 parts by weight of the mixture of aluminum hydroxide and magnesium hydroxide and 0.01 — 10 parts by weight of carrageenan per 100 parts by weight of the composition.
  • the pharmaceutical composition according to the present invention may be pharmaceutically manufactured into a dosage form selected from the group consisting of powder, granule, dry syrup, suspension, solution and chewable tablet in combination with pharmaceutically acceptable excipients. It is preferable that the composition is pharmaceutically manufactured into suspension or solution.
  • the composition preferably comprises 0.01 — 0J parts by weight of carrageenan per 100 parts by weight of the composition. More preferably, the composition further comprises sweeteners or aromatics.
  • the bitter and the astringent taste can be effectively masked without involving any additional manufacturing step or cost.
  • the present inventors performed many experiments to find out which polysaccharides can effectively mask the bitter and the astringent taste among many kinds of polysaccharides and as a result, found out that carrageenan only can effectively mask the tastes. Also, they discovered that carrageenan can most effectively mask the bitter and the astringent taste of aceglutamide aluminum, aluminum hydroxide and magnesium hydroxide, among various agents.
  • aceglutamide aluminum in a pharmaceutical composition for oral administration comprising aceglutamide aluminum, although an amount of aceglutamide aluminum is variable according to its dosage form, it is preferably 1 — 30 parts by weight, more preferably, 2 — 20 parts by weight, per 100 parts by weight of the composition, since within the above range of amount, aceglutamide aluminum is expected to sufficiently display its pharmacological effects.
  • a pharmaceutical composition for oral administration of a mixture of aluminum hydroxide and magnesium hydroxide preferably comprises 20 — 50 parts by weight of the mixture of aluminum hydroxide and magnesium hydroxide per 100 parts by weight of the composition.
  • the above-described compositions comprise 0.01 — 10 parts by weight of carrageenan, since in the case of more than 10 parts by weight, their viscosity becomes too high and thus, they involve some problems in being pharmaceutically manufactured into dosage forms by conventional methods, and in the case of less than 0.01 parts by weight, due to too small amount of carrageenan, tastes cannot be effectively masked.
  • the present composition comprises aceglutamide aluminum in combination with a mixture of aluminum hydroxide and magnesium hydroxide, according to Korean patent publication No. 96-11773, the content of which is incorporated hereinto by reference, it is preferable that a weight ratio of aluminum hydroxide to magnesium hydroxide is 1 to 1 and a weight ratio of aceglutamide aluminum to the mixture of aluminum hydroxide and magnesium hydroxide is 1 to 1J — 2.3, since excellent therapeutic effects on digestive ulcers can be obtained in the above-described ratios.
  • the pharmaceutical composition according to the present invention may be pharmaceutically manufactured into various dosage forms, for example, powder, granule, dry syrup, suspension, solution or chewable tablet, in combination with pharmaceutically acceptable excipients, by conventional methods.
  • Carrageenan has characteristic flow, so called “pseudoplastic flow", characterized by without any external stimulus, high viscosity being maintained but with any external stimulus, viscosity being steeply decreased. Therefore, carrageenan is the optimal excipient for suspension wherein suspension stability is important during a period of preservation, or solution. Therefore, provided that the composition according to the present invention is manufactured into suspension or solution, it can be comfortably taken by patients and is stable without precipitates during a period of preservation after being manufactured.
  • the present composition preferably comprises 0.01 — 0J parts by weight of carrageenan per 100 parts by weight of the composition. That is, if more than 0J parts by weight of carrageenan is present, the composition will have too high viscosity and thus, lose fluidity, a principal characteristic of liquid dosage forms. If less than 0.01 parts by weight of carrageenan is present, an amount of carrageenan is too small and thus, tastes cannot be effectively masked.
  • liquid dosage forms such as suspension or solution are characterized in that patients feel bitterer or more astringent than solid dosage forms
  • a bitter and an astringent taste are preliminary masked and subsequently, to be rendered to have tastes suitable for taking
  • it preferably further comprises conventional sweeteners.
  • sweeteners sucrose, sorbitol, stevioside or mixtures thereof may be added thereto.
  • a weight ratio of aceglutamide aluminum to sweeteners is 1 to 1 — 10.
  • it may also further comprise conventional aromatics.
  • Powder of aceglutamide aluminum was manufactured according to a conventional method for manufacturing powder, using the composition as shown in the following table 1.
  • Granules of aceglutamide aluminum were manufactured according to a conventional method for manufacturing granules, using the composition as shown in the following table 2.
  • Solution of aceglutamide aluminum was manufactured according to a conventional method for manufacturing solution, using the composition as shown in the following table 3.
  • Chewable tablets of aceglutamide aluminum, a weight of which was 2.5g/tablet, were manufactured according to a conventional method for manufacturing chewable tablets, using the composition as shown in the following table 5. Table. 5
  • Solution of aceglutamide aluminum was manufactured in the substantially same method as in example 3 except that carrageenan was not used.
  • organoleptic tests were carried out on solutions of aceglutamide aluminum obtained from example 3 and comparative example 1, respectively. Organoleptic tests were proceeded with by two-point contrast method which can be used in judgement of simple differences, indication of differences and selection of quality. Panel participating in the tests consisted of 27 members regardless of sex who had no prejudice on dosage forms according to the present invention. In the case of the above described method, a percentage of a correct answer was 50% and results were tested according to ⁇ test and significance test table of two-point contrast method. In addition, after the members tasted, grade No. 1 was given to a preferable sample and grade No. 2 given to an unpreferable sample. The results were shown in the following table 6.
  • the pharmaceutical composition according to the present invention can effectively mask a bitter and an astringent taste of aceglutamide aluminum and/or a mixture of aluminum hydroxide and magnesium hydroxide without involving any additional manufacturing step or cost thereby to improve compliance of patients, to facilitate long-term administration and furthermore, to obtain a physically stable suspension or solution.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Biophysics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une composition pharmaceutique destinée à être administrée par voie orale, présentant une activité thérapeutique sur des troubles gastro-intestinaux caractérisée en ce qu'elle comprend au moins un élément choisi dans le groupe contenant de l'acéglutamide aluminium et un mélange d'hydroxyde d'aluminium et d'hydroxyde de magnésium en tant que principe actif, ainsi que de la carragénine en tant qu'agent de masquage du goût, lequel peut masquer efficacement le goût amère et astringent d'un principe actif sans impliquer une éventuelle étape ou un éventuel coût de fabrication supplémentaire afin d'améliorer la collaboration des patients, de manière à faciliter l'administration à long terme et en outre d'obtenir une suspension ou une solution stable physiquement.
PCT/KR1999/000209 1998-12-31 1999-04-29 Composition pharmaceutique destinee a une administration par voie orale presentant une activite therapeutique sur des troubles gastro-intestinaux WO2000040254A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR10-2001-7000075A KR100370391B1 (ko) 1998-12-31 1999-04-29 위장질환 치료용 경구투여 제제 조성물
AU34442/99A AU3444299A (en) 1998-12-31 1999-04-29 Pharmaceutical composition for oral administration having therapeutic activity on gastrointestinal disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1019980063716A KR20000046974A (ko) 1998-12-31 1998-12-31 아세글루타미드 알루미늄의 경구 투여용 제제 조성물ㅇ
KR1998/63716 1998-12-31

Publications (1)

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WO2000040254A1 true WO2000040254A1 (fr) 2000-07-13

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KR (2) KR20000046974A (fr)
CN (1) CN1175820C (fr)
AU (1) AU3444299A (fr)
WO (1) WO2000040254A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010130393A2 (fr) * 2009-05-12 2010-11-18 Ratiopharm Gmbh Comprimé à fondre contenant un sel de vardenafil
JP2020516660A (ja) * 2017-04-13 2020-06-11 デーウン ファーマシューティカル カンパニー リミテッド 水酸化アルミニウムと水酸化マグネシウムを含む懸濁液及びその製造方法
RU2795006C2 (ru) * 2017-04-13 2023-04-27 Тэвун Фармасьютикал Ко., Лтд. Суспензия, содержащая гидроксид алюминия и гидроксид магния, и способ ее получения

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2446807C2 (ru) * 2007-12-20 2012-04-10 Н.В. Нютрисиа Жидкий продукт, содержащий нуклеотиды/нуклеозиды

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0248740A2 (fr) * 1986-06-06 1987-12-09 Terumo Kabushiki Kaisha Composition contenant un gel d'hydroxyde d'aluminium
US5013557A (en) * 1989-10-03 1991-05-07 Warner-Lambert Company Taste masking compositions comprising spray dried microcapsules containing sucralfate and methods for preparing same
JPH10101580A (ja) * 1996-09-27 1998-04-21 Eisai Co Ltd 薬物の不快な味を隠蔽する組成物
WO1998043675A1 (fr) * 1997-03-28 1998-10-08 Eisai Co., Ltd. Preparations pharmaceutiques orales dont on a reduit l'amertume au moyen d'un masquant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0248740A2 (fr) * 1986-06-06 1987-12-09 Terumo Kabushiki Kaisha Composition contenant un gel d'hydroxyde d'aluminium
US5013557A (en) * 1989-10-03 1991-05-07 Warner-Lambert Company Taste masking compositions comprising spray dried microcapsules containing sucralfate and methods for preparing same
JPH10101580A (ja) * 1996-09-27 1998-04-21 Eisai Co Ltd 薬物の不快な味を隠蔽する組成物
WO1998043675A1 (fr) * 1997-03-28 1998-10-08 Eisai Co., Ltd. Preparations pharmaceutiques orales dont on a reduit l'amertume au moyen d'un masquant

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 122, no. 15-22, May 1995, Columbus, Ohio, US; abstract no. 256024C, JANG ET. AL.: "Effect of Antacids, Aceglutamide Alumnium or their Combination on Acute and Chronid Ulcer Models in Rats." page 102; column 1; *
PATENT ABSTRACTS OF JAPAN *
YAKHAK HOECHI, vol. 38, no. 5, 1994, KOREAN *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010130393A2 (fr) * 2009-05-12 2010-11-18 Ratiopharm Gmbh Comprimé à fondre contenant un sel de vardenafil
WO2010130393A3 (fr) * 2009-05-12 2011-10-20 Ratiopharm Gmbh Comprimé à fondre contenant un sel de vardenafil
JP2020516660A (ja) * 2017-04-13 2020-06-11 デーウン ファーマシューティカル カンパニー リミテッド 水酸化アルミニウムと水酸化マグネシウムを含む懸濁液及びその製造方法
EP3610857A4 (fr) * 2017-04-13 2020-09-16 Daewoong Pharmaceutical Co., Ltd. Suspension comprenant de l'hydroxyde d'aluminium et de l'hydroxyde de magnésium et son procédé de préparation
US11135165B2 (en) 2017-04-13 2021-10-05 Daewoong Pharmaceutical Co., Ltd. Suspension comprising aluminum hydroxide and magnesium hydroxide and preparation method therefor
JP7090641B2 (ja) 2017-04-13 2022-06-24 デーウン ファーマシューティカル カンパニー リミテッド 水酸化アルミニウムと水酸化マグネシウムを含む懸濁液及びその製造方法
RU2795006C2 (ru) * 2017-04-13 2023-04-27 Тэвун Фармасьютикал Ко., Лтд. Суспензия, содержащая гидроксид алюминия и гидроксид магния, и способ ее получения
AU2018251519B2 (en) * 2017-04-13 2023-06-15 Daewoong Pharmaceutical Co., Ltd. Suspension comprising aluminum hydroxide and magnesium hydroxide and preparation method therefor

Also Published As

Publication number Publication date
CN1175820C (zh) 2004-11-17
AU3444299A (en) 2000-07-24
KR20000046974A (ko) 2000-07-25
CN1332630A (zh) 2002-01-23
KR20010086297A (ko) 2001-09-10
KR100370391B1 (ko) 2003-01-30

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