WO2006112596A1 - Preparation a liberation regulee contenant de l'hydrochlorure de tamsulosine - Google Patents

Preparation a liberation regulee contenant de l'hydrochlorure de tamsulosine Download PDF

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Publication number
WO2006112596A1
WO2006112596A1 PCT/KR2006/000489 KR2006000489W WO2006112596A1 WO 2006112596 A1 WO2006112596 A1 WO 2006112596A1 KR 2006000489 W KR2006000489 W KR 2006000489W WO 2006112596 A1 WO2006112596 A1 WO 2006112596A1
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Prior art keywords
tamsulosin hydrochloride
release
weight
preparation
low
Prior art date
Application number
PCT/KR2006/000489
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English (en)
Inventor
Hong-Ryeol Jeon
Do-Woo Kwon
Bong-Sang Lee
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Ctc Bio, Inc.
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Publication date
Application filed by Ctc Bio, Inc. filed Critical Ctc Bio, Inc.
Publication of WO2006112596A1 publication Critical patent/WO2006112596A1/fr

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    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
    • A61K9/2846—Poly(meth)acrylates
    • 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
    • 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
    • A61K31/18—Sulfonamides
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate

Definitions

  • the present invention relates to a controlled-release formulation containing tamsulosin hydrochloride, and more particularly, to a controlled release formulation that can release tamsulosin hydrochloride at zero-order rate regardless of ambient in vivo condition.
  • Tamsulosin hydrochloride is an alpha ( ⁇ ) 1 blocker that is selective to prostatic smooth muscle. Tamsulosin hydrochloride is a drug useful for the treatment of obstructive urinary tract disorders due to benign prostate enlargement. The usual daily dose of tamsulosin hydrochloride is 0.2-0.8 mg. Tamsulosin hydrochloride has greater selectivity for prostatic smooth muscle and acts weakly on blood vessels, unlike other alpha 1 blockers such as doxazosin and terazosin, thereby greatly decreasing occurrences of side effects such as orthostatic hypotension.
  • tamsulosin hydrochloride is highly potent, a very low dose is required. Also, excessive increase of blood concentration of tamsulosin hydrochloride due to fast absorption into the body may cause side effects such as orthostatic hypotension.
  • U.S. Patent No. 4,772,475 discloses a controlled release formulation containing tamsulosin hydrochloride.
  • tamsulosin hydrochloride is mixed with at least 50% by weight of a unit-forming substance selected from the group consisting of crystalline cellulose, chitin and chitosan.
  • a release-controlling agent selected from the group consisting of acrylic acid polymers, acrylic acid copolymers and mixtures thereof is added, followed by granulation, to produce sustained-release granules containing tamsulosin hydrochloride.
  • the controlled-release formulation according to the above patent does not show enough controlled-release property.
  • 16.2 to 60.4% of the drug is released from said formulation within one hour after start of release in a first acidic solution (pH: about 1.2), and more than 90% of the drug is released within one hour after start of release in the second neutral solution when release is carried out in a second neutral solution (pH: about 6.8) after the release in the first acid solution (See Korean patent application No. 10-2003-0015391).
  • Yamanouchi Co. Ltd.; FlomaxTM, Boehringer Ingelheim also exhibit distinct pH-dependent drug release property. It is reported that administration of these products into human before food intake results in 30% increase of bioavailability and 40-70% increase of maximum drug concentration in bloods (Cmax), as compared to after food intake (Physicians Desk Reference 2002). This report demonstrates that food intake influences the mobility of the gastric intestinal tract and the ambient pH of a drug- containing preparation.
  • the object of the present invention is to provide a tamsulosin hydrochloride -containing controlled-release preparation that releases constantly the drug irrespective of ambient in vivo pH, that is that releases the drug at regular rate (zero-order rate) from stomach to small intestine.
  • the object of the present invention is to provide a tamsulosin hydrochloride-containing preparation that maintains the effect of tamsulosin hydrochloride longer and reduces side effects such as orthostatic hypotension and abnormal ejaculation, which are caused by the large amount of absorption of tamsulosin hydrochloride during short time.
  • the present invention provides a tamsulosin hydrochloride- containing controlled-release preparation, wherein the preparation comprises:
  • a core tablet comprising tamsulosin hydrochloride; a binder selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low- viscosity hydroxypropylmethylcellulose, low- viscosity hydroxypropylcellulose and their mixtures; a diluent selected from the group consisting of lactose anhydrous, lactose hydrous, microcrystalline cellulose and their mixtures; low-viscosity hydroxypropylmethylcellulose for controlling drug release; and a disintegrator selected from the group consisting of sodium starch glycolate, croscarmellose sodium and their mixture, and
  • (B) a coated membrane comprising an enteric polymer; a pore-maker selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low- viscosity hydroxypropylmethylcellulose, low-viscosity hydroxypropylcellulose and their mixtures; and a surfactant for coating.
  • the present invention provides said tamsulosin hydrochloride- containing controlled-release preparation, wherein the preparation comprises:
  • binder 0.5-7% by weight of binder; 45-75% by weight of diluent; 10-27% by weight of low- viscosity hydroxypropylmethylcelmlose for controlling drug release; and 5-15% by weight of disintegrator, and
  • the present invention makes the core tablet itself control drug release by using appropriate ratio of mixture comprising low- viscosity hydroxypropylmethylcellulose (pH- independent polymer for controlling drug release), binder, diluent, etc., and in addition thereto, makes the preparation release tamsulosin hydrochloride at zero-order rate irrespective of ambient condition of stomach and small intestine by coating the core tablet with appropriate ratio of mixture comprising enteric polymer, pore-maker and surfactant.
  • the present invention provides a tamsulosin hydrochloride-containing controlled- release preparation, wherein the preparation comprises:
  • a core tablet comprising tamsulosin hydrochloride; a binder selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low- viscosity hydroxypropylmethylcellulose, low- viscosity hydroxypropylcellulose and their mixtures; a diluent selected from the group consisting of lactose anhydrous, lactose hydrous, microcrystalline cellulose and their mixtures; low-viscosity hydroxypropylmethylcellulose for controlling drug release; and a disintegrator selected from the group consisting of sodium starch glycolate, croscarmellose sodium and their mixture, and
  • (B) a coated membrane comprising an enteric polymer; a pore-maker selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low- viscosity hydroxypropylmethylcellulose, low-viscosity hydroxypropylcellulose and their mixtures; and a surfactant for coating.
  • the present invention provides said tamsulosin hydrochloride- containing controlled-release preparation, wherein the preparation comprises:
  • binder 0.5-7% by weight of binder; 45-75% by weight of diluent; 10-27% by weight of low- viscosity hydroxypropylmethylcellulose for controlling drug release; and 5-15% by weight of disintegrator, and
  • the core tablet (A) of the present invention comprises comprising 0.03-0.14% by weight of tamsulosin hydrochloride; 0.5-7% by weight of binder selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low- viscosity hydroxypropylmethylcellulose, low- viscosity hydroxypropylcellulose and their mixtures; 45-75% by weight of diluent selected from the group consisting of lactose anhydrous, lactose hydrous, microcrystalline cellulose and their mixtures; 10-27% by weight of low-viscosity hydroxypropylmethylcellulose for controlling drug release; and 5-15% by weight of disintegrator selected from the group consisting of sodium starch glycolate, croscarmellose sodium and their mixture based on the total weight of the preparation including the core tablet and the coated membrane.
  • binder selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vin
  • the controlled-release preparation of the present invention comprises a binder for binding powders to make granules for tabletting and controlling release of tamsulosin hydrochloride.
  • Preferable binder of the present invention includes polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low-viscosity hydroxypropylmethylcellulose, low-viscosity hydroxypropylcellulose and their mixtures.
  • Polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer and their mixture are more preferable in view of easy manufacturing of granules for tabletting and easy controlling property of drug release pattern.
  • Preferable content of the binder is 0.5-7% by weight and more preferable content of the binder is 1.5-4% by weight based on the total weight of the preparation.
  • the content of the binder is less than 0.5% by weight, it is difficult to make enough strong granules for tabletting.
  • the content of the binder is more than 7% by weight, drug release rate may be severely delayed because the binder itself blocks integration of the preparation and drug release from the preparation.
  • the controlled-release preparation of the present invention comprises a diluent for giving the preparation enough volume for administration and drawing proper amount of water into the core tablet during dissolution of the preparation.
  • the diluent has close relations with the other ingredients.
  • Preferable diluent of the present invention includes lactose anhydrous, lactose hydrous, microcrystalline cellulose and their mixtures.
  • Preferable content of the diluent is 45-75% by weight and more preferable content of the diluent is 50-70% by weight based on the total weight of the preparation.
  • Diluent consisting of 30-45% by weight of lactose and 15-30% by weight of microcrystalline cellulose is most preferable in view of easy manufacturing of the tablet. In case that the content of the diluent is less than 45% or more than 75% by weight, it is difficult to maintain good drug release rate.
  • the controlled-release preparation of the present invention comprises low- viscosity hydroxypropylmethylcellulose playing an important role in controlling the release of tamsulosin hydrochloride. More specifically, the low- viscosity hydroxypropylmethylcellulose of the present invention plays its role in controlling the drug release even after the preparation passes on into small intestine where the coated membrane of enteric polymer dissolves out.
  • the low- viscosity hydroxypropylmethylcellulose is not the only ingredient for controlling the release of tamsulosin hydrochloride, but the other ingredients contained in the preparation of the present invention, consisting of the core tablet and the coated membrane, play their roles in controlling the release of tamsulosin hydrochloride.
  • Preferable content of low-viscosity hydroxypropylmethylcellulose is 10-27% by weight based on the total weight of the preparation. In case that the content is less than 10% by weight, it is difficult to control the release of tamsulosin hydrochloride. In case that the content is more than 27% by weight, the release of tamsulosin hydrochloride is too slow to get a desirable release pattern.
  • low- viscosity in low-viscosity hydroxypropylmethylcellulose and low- viscosity hydroxypropylcellulose means that the viscosity of 2% water solution made with each polymer is from 20 to 150 cps at 2O 0 C, and more preferably, from 70 to 130 cps.
  • the controlled-release preparation of the present invention comprises a disintegrator.
  • Preferable disintegrator includes sodium starch glycolate, croscarmellose sodium (cross-linked polymer of carboxymethylcellulose sodium) and their mixture.
  • Preferable content of the disintegrator is 5-15% by weight based on the total weight of the preparation. In case that the content is less than 5% by weight, it is difficult to get a desirable release pattern. In case that the content is more than 15% by weight, the release of tamsulosin hydrochloride is too fast because of fast disintegration.
  • the controlled-release preparation of the present invention may further comprise a lubricant such as colloidal silica, talc, magnesium stearate and their mixtures to improve flowability of granules for tabletting and tabletting property within the scope not to obstruct the object of the present invention.
  • a lubricant such as colloidal silica, talc, magnesium stearate and their mixtures to improve flowability of granules for tabletting and tabletting property within the scope not to obstruct the object of the present invention.
  • the core tablet (A) of the present invention is enclosed by membrane comprising an enteric polymer; a pore-maker selected from the group consisting of polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low-viscosity hydroxypropylmethylcellulose, low-viscosity hydroxypropylcellulose and their mixtures; and a surfactant for coating.
  • the coated membrane of the present invention performs a role controlling the release in stomach.
  • the controlled-release preparation of the present invention comprises in the coated membrane an enteric polymer that does not dissolve in stomach so that the preparation of the present invention can control the release of tamsulosin hydrochloride in stomach.
  • enteric polymer includes hydroxypropylmethylcellulose phthalate, methacrylic acid copolymer, hydroxypropylmethylcellulose acetate succinate and their mixtures.
  • Preferable content of the enteric polymer is 3-8% by weight based on the total weight of the preparation. In case that the content is less than 3% by weight, the drag release in stomach is too fast.
  • the drug release in stomach is too slow and the difference of the drug release between stomach condition and small intestine condition is too big, that is, the large amount of tamsulosin hydrochloride is released and absorbed during short time, which may cause many side effects.
  • the controlled-release preparation of the present invention comprises a pore-maker in the coated membrane.
  • a material used as this pore-maker is dissolved in stomach and makes a pore in the membrane. Through this pore, tamsulosin hydrochloride is suitably released in stomach.
  • Preferable pore-maker includes polyvinylpyrrolidone, vinylpyrrolidone-vinylacetate copolymer, low-viscosity hydroxypropylmethyl- cellulose, low-viscosity hydroxypropylcellulose and their mixtures.
  • Preferable content of the pore-maker is 0.5-3% by weight based on the total weight of the preparation.
  • the content of the pore-maker is less than 0.5% by weight, it is difficult to release tamsulosin hydrochloride in stomach. In case that the content is more than 3% by weight, the release of tamsulosin hydrochloride in stomach is too fast to get a desirable release pattern.
  • the controlled-release preparation of the present invention comprises a surfactant for coating in the coated membrane to give plasticity to the enteric polymer.
  • a surfactant for coating includes dibutylsebacate, triethylcitrate, propylene glycol, poly ethylenegly col and their mixtures. More preferable surfactant is polyethyleneglycol and most preferable surfactant is polyethyleneglycol ⁇ OOO.
  • Preferable content of the surfactant is 05-2% by weight based on the total weight of the preparation.
  • the surfactant for coating according to the present invention performs an accessory role making a pore in the membrane comprising, for example, hydrox- ypropylmethylcellulose phthalate by being dissolved out in stomach, as well as a main role giving plasticity to the enteric polymer. That is, like the pore-maker, the surfactant controls the release of tamsulosin hydrochloride in stomach. In case that the content of the surfactant is less than 0.5% by weight, it is difficult to get a desirable plasticity for coating. In case that the content is more than 2% by weight, the release of the drag is too fast in stomach.
  • the coated membrane (B) according to the present invention may further comprise a lubricant (for example, talc), an agent for blocking light (for example, titanium oxide) and so on.
  • a lubricant for example, talc
  • an agent for blocking light for example, titanium oxide
  • Tamsulosin hydrochloride-containing controlled-release preparation according to the present invention can be made by a method known well to one of ordinary skill in the art.
  • a controlled-release preparation according to the present invention can be made by the following method, but the manufacturing method for the preparation of the present invention is not limited thereto.
  • tamsulosin hydrochloride and a binder are dissolved in adequate amount of solvent (for example, water, methanol, ethanol, isopropanol, acetone, methylene chloride and their mixtures) to make a binding solution, and then granules having appropriate size for tabletting are prepared with the binding solution and a diluent.
  • solvent for example, water, methanol, ethanol, isopropanol, acetone, methylene chloride and their mixtures
  • granules having appropriate size for tabletting are prepared with the binding solution and a diluent.
  • the granules, low- viscosity hydroxypropylmethylcellulose, a disintegrator, lubricant and so on are mixed and tabletted by using tabletting machine to make a core tablet.
  • coating process is performed as follows: an enteric polymer, a pore-maker, surfactant etc.
  • a conventional tablet-coating machine is used with the core tablet and the coating solution to make a tamsulosin hydrochloride-containing controlled release preparation of the present invention.
  • Figure 1 shows the results of dissolution tests for controlled-release preparations according to one example of the present invention and commercially-available products.
  • Figure 2 shows the results of dissolution tests for controlled-release preparations according to one example of the present invention and comparative examples. Mode for the Invention
  • Examples and comparative examples were manufactured with ingredients and contents shown in the below table 1. Almost 10,000 tablets were prepared at a time per each example. That is, 10,000 times amount of weight of each ingredient was measured and used to make each preparation.
  • example 1 was manufactured as follows: 2 g of tamsulosin hydrochloride and 50 g of polyvinylpyrrolidone were dissolved in 600 ml of ethanol to make a binding solution. The binding solution was combined with 936 g of lactose and 530 g of microcrystalline cellulose to make granules.
  • the granules were dried (6O 0 C, 4 hours) and sieved to make adequate size of granules, and then 440 g of low-viscosity hydroxypropylmethylcellulose, 220 g of sodium starch glycolate and 22 g of magnesium stearate were added to the granules.
  • the mixture was mixed well and tabletted with a tabletting machine (TMI 1400, Kisan, South Korea).
  • hydroxypropylmethylcellulose phthalate 24 g of polyvinylpyrrolidone, 26 g of polyethyleneglycol6000, 4 g of titanium oxide and 3 g of talc were dissolved or suspended in the mixture of 1,400 ml of ethanol and 1,000 ml of methylene chloride to make a coating solution.
  • the above manufactured tablets were coated with the coating solution with a conventional coating machine (KC400SF, Kisan, South Korea). More amount of the coating solution than needed was manufactured to supplement the loss in the coating process.
  • HPMC and HPMCP mean hydroxypropylmethylcellulose and hydroxypropylmethylcellulose phthalate, respectively.
  • [50] [51] ⁇ Dissolution tests of examples, comparative examples and commercially available products>
  • Dissolution tests were performed with the above manufactured examples 1-4, comparative examples 1-4 and commercially available products [TAMSNALTM(Yuhan Corp., South Korea), URONALTM(KyungDong Pharm. Co. Ltd., South Korea) and HARNALTM(Yamanouchi Korea Co. Ltd., South Korea)] according to the paddle method of the dissolution test method of Korea Pharmacopoeia.
  • the paddle was rotated at a rate of 100 rpm and the temperature of dissolution medium was 37 ⁇ 0.5°C.
  • example 2 showed a desirable release pattern even if a little less amount of the coated membrane and a little more amount of low- viscosity hydrox- ypropylmethylcellulose than example 1 were used.
  • Example 3 showed a desirable Table release pattern even if a little more amount of the coated membrane and a little less amount of low- viscosity hydroxypropylmethylcellulose were used.
  • Example 4 wherein the amounts of low- viscosity hydroxypropylmethylcellulose and hydroxypropylmethylcellulose phthalate are in boundary of the preferable scope of the present invention, showed a little slow release pattern.
  • comparative example 1 showed a fast release pattern because the content of the low- viscosity hydroxypropylmethylcellulose is less than the preferable scope of the present invention.
  • Comparative example 2 could not properly control the release of tamsulosin hydrochloride because the content of the disintegrator was too high.
  • Comparative example 3 showed very slow release pattern because of the large amount of coating.
  • Comparative example 4 could not properly control the release of tamsulosin hydrochloride because of the large amount of the pore-maker.
  • HPMC means hydroxypropylmethylcellulose
  • Acryl-EZETM is a methacrylic acid co-polymer
  • enteric polymer which can be purchased from Colorcon, Inc.
  • AQOATTM is hydroxypropylmethylcellulose acetate succinate
  • Water and mixture of ethanol and water were used for coating medium of Acryl-EZETM and AQOATTM, respectively.
  • the present invention provides a tamsulosin hydrochloride-containing controlled- release preparation that can maintain the effect of the drug longer and reduce side effects such as orthostatic hypotension and abnormal ejaculation by releasing constantly the drug irrespective of ambient in vivo pH, that is, releasing the drug at regular rate (zero-order rate) from stomach to small intestine.
  • the tamsulosin hydrochloride-containing controlled-release preparation of the present invention is simple to manufacture and cost-effective, and can be made with conventional tabletting machine and coating machine used usually so that it does not need a specific equipment for coating granules.

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Abstract

La présente invention concerne une préparation à libération régulée contenant de l'hydrochlorure de tamsulosine. La préparation de la présente invention peut libérer l'hydrochlorure de tamsulosine à une vitesse de libération d'ordre zéro indépendamment des conditions ambiantes de l'estomac et de l'intestin grêle, et, par conséquent, permet de réduire plusieurs effets secondaires tout en conservant l'effet du médicament de manière constante. En outre, la préparation à libération régulée contenant l'hydrochlorure de tamsulosine de la présente invention est facile à fabriquer et présente un bon rapport coût-efficacité. Elle peut être fabriquée au moyen d'une machine à fabriquer des comprimés et d'une machine à enrober classiques ne requérant pas d'équipement spécifique.
PCT/KR2006/000489 2005-02-11 2006-02-10 Preparation a liberation regulee contenant de l'hydrochlorure de tamsulosine WO2006112596A1 (fr)

Applications Claiming Priority (2)

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KR10-2005-0012239 2005-02-11
KR1020050012239A KR100678421B1 (ko) 2005-02-11 2005-02-11 염산 탐스로신 함유 방출조절 제제

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CN (1) CN101128190A (fr)
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Cited By (5)

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EP2047847A1 (fr) * 2007-10-12 2009-04-15 KRKA, tovarna zdravil, d.d., Novo mesto Composition pharmaceutique solide comprenant de la tamsulosine
WO2009047312A1 (fr) * 2007-10-12 2009-04-16 Krka, Tovarna Zdravil, D.D., Novo Mesto Composition pharmaceutique solide comprenant de la tamsulosine
CN105412020A (zh) * 2015-12-07 2016-03-23 黑龙江省智诚医药科技有限公司 一种盐酸坦洛新缓释微丸及其制备方法
US9457094B2 (en) 2012-06-28 2016-10-04 Boryung Pharmaceutical Co., Ltd. Pharmaceutical composition containing fimasartan and hydrochlorothiazide
EP3881832A4 (fr) * 2018-12-21 2022-08-31 Hanmi Pharm. Co., Ltd. Composition pharmaceutique contenant du chlorhydrate de tamsulosine présentant une excellente résistance aux acides et procédé de préparation associé

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CN101703488B (zh) * 2008-12-16 2013-02-20 北京科信必成医药科技发展有限公司 具有润滑层结构的双层渗透泵控释片及其制备方法
CN101987081B (zh) * 2010-07-16 2012-08-08 钟术光 一种控释制剂
CN103211790B (zh) * 2012-01-18 2018-07-10 北京天衡药物研究院有限公司 盐酸坦索罗辛膜控缓释微丸胶囊
MX2019000546A (es) * 2016-07-15 2019-10-04 Hanmi Pharm Ind Co Ltd Preparacion farmaceutica para la administración oral con uniformidad del contenido mejorada, que comprende perlas de liberación sostenida que continenen hidrocloruro de tamsulosina.
KR102389339B1 (ko) 2018-12-26 2022-04-22 (주)휴온스 방출 제어되는 고함량 탐스로신 정제 조성물 및 이의 제조방법
KR20210003323A (ko) * 2019-07-01 2021-01-12 한미약품 주식회사 탐수로신 또는 이의 염산염 함유 제약 조성물 및 이의 제조방법

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WO1996040080A1 (fr) * 1995-06-07 1996-12-19 Andrx Pharmaceuticals, Inc. Formulation a liberation controlee presentant un passage preforme
WO2003039531A1 (fr) * 2001-11-07 2003-05-15 Synthon B.V. Comprimes de tamsulosine a liberation modifiee
WO2004048711A1 (fr) * 2002-11-22 2004-06-10 Tec-Truss Holdings Pty Ltd Poutres composites
US20040253309A1 (en) * 2003-01-27 2004-12-16 Yamanouchi Pharmaceutical Co., Ltd. Enteric sustained-release fine particles of tamsulosin and its salt and manufacturing method thereof

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KR20050122397A (ko) * 2004-06-24 2005-12-29 주식회사 대우일렉트로닉스 Ｐｖｒ 내장형 디지털 방송 시스템의 채널 락 장치 및 방법

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WO1996040080A1 (fr) * 1995-06-07 1996-12-19 Andrx Pharmaceuticals, Inc. Formulation a liberation controlee presentant un passage preforme
WO2003039531A1 (fr) * 2001-11-07 2003-05-15 Synthon B.V. Comprimes de tamsulosine a liberation modifiee
WO2004048711A1 (fr) * 2002-11-22 2004-06-10 Tec-Truss Holdings Pty Ltd Poutres composites
US20040253309A1 (en) * 2003-01-27 2004-12-16 Yamanouchi Pharmaceutical Co., Ltd. Enteric sustained-release fine particles of tamsulosin and its salt and manufacturing method thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2047847A1 (fr) * 2007-10-12 2009-04-15 KRKA, tovarna zdravil, d.d., Novo mesto Composition pharmaceutique solide comprenant de la tamsulosine
WO2009047312A1 (fr) * 2007-10-12 2009-04-16 Krka, Tovarna Zdravil, D.D., Novo Mesto Composition pharmaceutique solide comprenant de la tamsulosine
US9457094B2 (en) 2012-06-28 2016-10-04 Boryung Pharmaceutical Co., Ltd. Pharmaceutical composition containing fimasartan and hydrochlorothiazide
RU2613900C2 (ru) * 2012-06-28 2017-03-21 Борюн Фармасьютикал Ко., Лтд. Фармацевтическая композиция, содержащая фимасартан и гидрохлортиазид
CN105412020A (zh) * 2015-12-07 2016-03-23 黑龙江省智诚医药科技有限公司 一种盐酸坦洛新缓释微丸及其制备方法
EP3881832A4 (fr) * 2018-12-21 2022-08-31 Hanmi Pharm. Co., Ltd. Composition pharmaceutique contenant du chlorhydrate de tamsulosine présentant une excellente résistance aux acides et procédé de préparation associé

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