EP1335707A2 - Nouvelles formulations de carvedilol - Google Patents

Nouvelles formulations de carvedilol

Info

Publication number
EP1335707A2
EP1335707A2 EP01273804A EP01273804A EP1335707A2 EP 1335707 A2 EP1335707 A2 EP 1335707A2 EP 01273804 A EP01273804 A EP 01273804A EP 01273804 A EP01273804 A EP 01273804A EP 1335707 A2 EP1335707 A2 EP 1335707A2
Authority
EP
European Patent Office
Prior art keywords
carvedilol
acid
pharmaceutically acceptable
organic acid
formulation
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.)
Withdrawn
Application number
EP01273804A
Other languages
German (de)
English (en)
Other versions
EP1335707A4 (fr
Inventor
Vlassios Andronis
Kimberly A. Lamey
Choon K. Oh
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.)
SmithKline Beecham Corp
Original Assignee
SmithKline Beecham Corp
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 SmithKline Beecham Corp filed Critical SmithKline Beecham Corp
Publication of EP1335707A2 publication Critical patent/EP1335707A2/fr
Publication of EP1335707A4 publication Critical patent/EP1335707A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, 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
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, 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
    • A61K9/14—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

  • This invention relates to novel formulations of carvedilol and to the use of such formulations in the treatment of hypertension, congestive heart failure and angina.
  • Carvedilol is useful in the treatment of hypertension, congestive heart failure and angina.
  • the current commercial formulation for carvedilol is immediate release, and it is administered twice daily.
  • the immediate release formulation of carvedilol is rapidly and extensively absorbed following oral administration, with the terminal elimination half-life ranging between 7-10 hours.
  • a once-daily dosing formulation for carvedilol is commercially desirable, would simplify a patient's dosing regimen and may improve compliance rates.
  • carvedilol can be formulated in novel formulations for once-daily dosing.
  • the present invention provides for the use of a pharmaceutically acceptable organic acid in formulations comprising carvedilol.
  • This invention also provides for the use of such formulations for the treatment of hypertension, congestive heart failure and angina. Description of the Invention
  • compositions of carvedilol are provided in spray-dried powder form or standard drug substance form.
  • the spray-dried powder compositions are prepared using a process that involves wet milling.
  • the suspension, thus produced, is spray dried using a spray dryer or granulated using a fluid bed granulator.
  • the composition may then be formulated, for example, in the form of tablets or capsules. Orally administrated formulations are preferred.
  • the present invention provides for a formulation comprising carvedilol, which further comprises of a pharmaceutically acceptable organic acid.
  • pharmaceutically acceptable organic acid refers to organic acids which are without pharmacological effect per se, have acceptable organoleptic properties, have acceptable density, do not have an extreme pH and are preferably solid.
  • Examples include mono-carboxylic acids and poly-carboxylic acids having from 2 to 25, preferably from 2 to 10, carbon atoms; monocyclic and polycyclic aryl acids, such as benzoic acid; as well as monohydrogen, dihydrogen and metal salts of multi-valent acids.
  • a single pharmaceutically acceptable organic acid may be used, or two or more of such may be used in combination.
  • the organic acid is a C(2-l ⁇ ) a lkyl- or alkenyl- carboxylic acid having from one, two or three carboxylic acid groups, and optionally with one or more hydroxy substituents or an additional CO group in the carbon chain, for instance malonic acid, succinic acid, fumaric acid, maleic acid, adipic acid, lactic acid, levulimc acid, sorbic acid, glutamic acid, aspartic acid, oleic acid, glutaric acid, glycine, arginine or a fruit acid, such as tartaric acid, malic acid, ascorbic acid or citric acid, most preferably citric acid.
  • malonic acid succinic acid, fumaric acid, maleic acid, adipic acid, lactic acid, levulimc acid, sorbic acid, glutamic acid, aspartic acid, oleic acid, glutaric acid, glycine, arginine or a fruit acid, such as tartaric acid, malic acid
  • Spray drying of milled compositions is carried out most suitably using a spray dryer, such as Yamato GA-32 Spray Dryer [Yarnato Scientific America Inc., Orangeburg, NY].
  • granulation of milled compositions is carried out most suitably using a fluid bed granulator, such as Glatt fluid bed granulator, or a high shear granulator.
  • the spray-dried powder, thus produced, is then used in tablets for oral administration in a unit dose.
  • These oral tablets comprise conventional controlled release formulations, such as tablets, having a sustained release or an enteric coating, or otherwise modified to control the release of the active compound, for example by the inclusion of gel forming polymers or matrix forming waxes.
  • carvedilol drug substance is mixed with an organic acid in either solution or suspension to form a drug medium to subsequently layer onto pellets or granules.
  • the drug layered pellets or granules are then coated to consist of a standard seal coat, enteric coat or a sustained release coat permeable to gastrointestinal juices.
  • the controlled release formulations are prepared, for example, as described in U. S. Patent No. 4,524,060, issued June 18, 1985, and U. S. Patent No. 4,983,401, issued January 8, 1991.
  • Other controlled release formulations are described in U. S. Patent No. 4,880,830, issued November 14, 1989, and U. S. Patent No. 5,068,112, issued November 26, 1991.
  • the controlled release formulations containing carvedilol and organic acid may also be in the form of a non-compressed drug layered pellet loaded into a standard capsule. This capsule is then enteric coated for delayed release and then subsequently coated with an immediate release portion of Carvedilol for a two burst system.
  • Tablets or capsules for oral administration are usually presented in a unit dose, and contain conventional excipients such as binding agents, fillers and diluents (tableting or compression aids), lubricants, disintegrants, colorants, flavourings, and wetting agents.
  • the tablets may be coated according to techniques well known in the art.
  • oral formulations may be prepared by conventional methods of blending, filling, tableting, or the like. Repeated blending operations may be used to distribute the active agent throughout those compositions employing large quantities of fillers. Such operations are, of course, well known in the art.
  • the present invention provides for the use of a pharmaceutically acceptable organic acid in the formulations comprising carvedilol.
  • the formulation is adapted for oral administration.
  • the formulation is presented as a unit dose. Such a formulation is taken once daily.
  • the preferred unit dosage forms include tablets or capsules comprising 25 mg or 50 mg of carvedilol; however, the present invention also includes doses from 6.25 mg to 100 mg.
  • Examples 1 & 2 - Carvedilol 50 mg Controlled Release Aqueous Film Coated Tablets The carvedilol 50 mg controlled release (CR) aqueous film coated (AFC) tablets were prepared from a carvedilol spray-dried powder which was blended with external excipients and a lubricant, compressed, and finally coated with a clear aqueous film coat followed by a Eudragit®-based coat.
  • Product CE tablets were made with fumaric acid, whereas Product CF tablets are made with citric acid.
  • Carvedilol Spray-Dried Powder consisting of: (78.06 1 )
  • Examples 3 & 4 - Carvedilol 50 mg Controlled Release Matrix Tablets The carvedilol controlled release (CR) matrix tablets (Products CG and CH) are prepared from a carvedilol granulation containing either a carvedilol spray-dried powder or standard carvedilol drug substance, respectively. A citric acid granulation is prepared separately. The desired carvedilol granulation and the citric acid granulation are blended together along with external excipients and finally a lubricant to produce the mix from which tablets are then compressed.
  • CR carvedilol controlled release
  • Carvedilol Spray-Dried Powder (78.21 4 ) consisting of:
  • Poloxamer 407 10.40 4
  • the carvedilol controlled release (CR) capsule is prepared from carvedilol drug layered pellets containing standard carvedilol drug substance, aspartic acid and Opadry Clear. The drug layered pellets are then coated with a sustained release coat, Aquacoat ECD-30, and filled into standard capsule shells for administration.
  • Carvedilol Drug Layered Pellets consisting of: (480.7)
  • the carvedilol controlled release (CR) capsule is prepared from carvedilol drug layered pellets containing standard carvedilol drug substance, aspartic acid and Opadry Clear.
  • 22.5 mg strength drug layered pellets are filled into standard capsule shells.
  • the capsules are enteric coated for the delayed release portion and a 2.5 mg strength immediate release top-coat is then applied for the initial burst effect.
  • Carvedilol Drug Layered Pellets consisting of: (432.7)
  • the bioavailability of the formulations according to the present invention are evaluated in healthy human volunteers.
  • the study is an open-label, single dose, randomized, four-period, incomplete block, crossover study. Each subject receives a single dose of the immediate release formulation in addition to single oral doses of 3 of the 4 controlled-release formulations according to a randomization schedule.
  • the regimens for the study are tabulated below:
  • Pharmacokinetic sampling for measurement of plasma carvedilol concentrations is conducted over a 48-hour period following administration of study medication in each study session. There is a washout period of at least 7 days between dosing in sessions. Female subjects return 7-10 days following dosing in the last study session for a follow-up pregnancy test. The total duration (from screening to end of the study) of each subject's participation will be five to eight weeks.
  • the primary endpoint is the AUC of carvedilol. Secondary endpoints include Cmax, Tmax, and Tl/2, as data permit.

Abstract

L'invention concerne de nouvelles formulations à base de carvedilol ainsi que des méthodes d'utilisation de ces formulations pour traiter l'hypertension, l'insuffisance cardiaque globale et l'angine de poitrine.
EP01273804A 2000-10-24 2001-10-23 Nouvelles formulations de carvedilol Withdrawn EP1335707A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24291100P 2000-10-24 2000-10-24
US242911P 2000-10-24
PCT/US2001/050872 WO2002065834A2 (fr) 2000-10-24 2001-10-23 Nouvelles formulations de carvedilol

Publications (2)

Publication Number Publication Date
EP1335707A2 true EP1335707A2 (fr) 2003-08-20
EP1335707A4 EP1335707A4 (fr) 2005-07-06

Family

ID=22916614

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01273804A Withdrawn EP1335707A4 (fr) 2000-10-24 2001-10-23 Nouvelles formulations de carvedilol

Country Status (5)

Country Link
EP (1) EP1335707A4 (fr)
JP (1) JP2004518734A (fr)
AU (1) AU2001297631A1 (fr)
CA (1) CA2426811A1 (fr)
WO (1) WO2002065834A2 (fr)

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JP4533531B2 (ja) 1998-04-03 2010-09-01 ビーエム リサーチ エイ／エス 制御放出組成物
IN191028B (fr) * 2001-05-17 2003-09-13 Sun Pharmaceutical Ind Ltd
EP1429739A1 (fr) * 2001-09-21 2004-06-23 Egalet A/S Systeme de liberation a base de polymere
DK1429734T3 (da) * 2001-09-21 2008-05-13 Egalet As Faste dispersioner af carvedilol til kontrolleret afgivelse
US20040253310A1 (en) 2001-09-21 2004-12-16 Gina Fischer Morphine polymer release system
EP1562552A1 (fr) 2002-11-08 2005-08-17 Egalet A/S Compositions de carvedilol a liberation commandee
EP2301526B1 (fr) 2003-03-26 2016-03-23 Egalet Ltd. Système de libération contrôlée de morphine
JP4989217B2 (ja) 2003-03-26 2012-08-01 エガレット エイ／エス 薬剤物質の送達制御用マトリックス組成物
JP5072364B2 (ja) * 2003-11-25 2012-11-14 スミスクライン ビーチャム （コーク） リミテッド カルベジロール遊離塩基、カルベジロール塩、無水形態またはその溶媒和物、対応する医薬組成物、制御放出処方および治療またはデリバリー方法
EP1686967A4 (fr) * 2003-11-25 2012-08-08 Smithkline Beecham Cork Ltd Base libre de carvedilol, ses sels, formes anhydres ou solvats, compositions pharmaceutiques correspondantes, formulations a liberation controlee, et methodes de traitement ou d'administration
JP5042041B2 (ja) * 2005-02-25 2012-10-03 ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン 心筋症及び心臓病を処置及び予防するための組成物及び方法
HU227490B1 (en) * 2005-08-26 2011-07-28 Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag Sustained release pharmaceutical preparation containing carvedilol
CN103271935A (zh) 2006-08-01 2013-09-04 普里克萨斯医药股份有限公司 泊洛沙姆用于预防和/或治疗心力衰竭的用途
HU227881B1 (en) * 2007-02-23 2012-05-29 Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag Sustained release pharmaceutical preparation containing carvedilol
WO2008114276A1 (fr) * 2007-03-16 2008-09-25 Lupin Limited Nouvelle composition orale de carvédilol à libération contrôlée
CA2682234A1 (fr) 2007-04-05 2008-10-16 Phrixus Pharmaceuticals, Inc. Compositions et procedes pour le traitement de l'insuffisance cardiaque
US8821928B2 (en) 2007-06-04 2014-09-02 Egalet Ltd. Controlled release pharmaceutical compositions for prolonged effect
FR2936709B1 (fr) * 2008-10-02 2012-05-11 Ethypharm Sa Comprimes alcoolo-resistants.
EP2393484A1 (fr) 2009-02-06 2011-12-14 Egalet Ltd. Composition à libération immédiate résistant à une maltraitance par prise d'alcool
NZ603579A (en) 2009-06-24 2014-02-28 Egalet Ltd Controlled release formulations
TWI415604B (zh) * 2009-09-29 2013-11-21 Tsh Biopharm Corp Ltd 調控釋放卡菲蒂羅劑型
EA201590165A1 (ru) 2012-07-06 2015-08-31 Эгалет Лтд. Сдерживающие злоупотребление фармацевтические композиции для контролируемого высвобождения

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DE19816036A1 (de) * 1998-04-09 1999-10-14 Roche Diagnostics Gmbh Verfahren zur Herstellung schnellauflösender pharmazeutischer Zubereitungen von schwerlöslichen Wirkstoffen
WO2000000179A1 (fr) * 1998-06-27 2000-01-06 Won Jin Biopharma Co., Ltd. Preparation a dispersion solide d'un medicament faiblement hydrosoluble contenant de l'huile, un acide gras ou leurs melanges
WO2000004902A1 (fr) * 1998-07-23 2000-02-03 Roche Diagnostics Gmbh Solution pour injection de carvedilol stabilise
WO2000032174A2 (fr) * 1998-11-27 2000-06-08 F. Hoffmann-La Roche Ag Specialite pharmaceutique combinee
WO2001035958A1 (fr) * 1999-11-15 2001-05-25 Smithkline Beecham Corporation Methane-sulfonate de carvedilol
WO2001074356A1 (fr) * 2000-04-03 2001-10-11 F. Hoffmann-La Roche Ag Solutions concentrees de carvedilol

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Publication number Priority date Publication date Assignee Title
DE19816036A1 (de) * 1998-04-09 1999-10-14 Roche Diagnostics Gmbh Verfahren zur Herstellung schnellauflösender pharmazeutischer Zubereitungen von schwerlöslichen Wirkstoffen
WO2000000179A1 (fr) * 1998-06-27 2000-01-06 Won Jin Biopharma Co., Ltd. Preparation a dispersion solide d'un medicament faiblement hydrosoluble contenant de l'huile, un acide gras ou leurs melanges
WO2000004902A1 (fr) * 1998-07-23 2000-02-03 Roche Diagnostics Gmbh Solution pour injection de carvedilol stabilise
WO2000032174A2 (fr) * 1998-11-27 2000-06-08 F. Hoffmann-La Roche Ag Specialite pharmaceutique combinee
WO2001035958A1 (fr) * 1999-11-15 2001-05-25 Smithkline Beecham Corporation Methane-sulfonate de carvedilol
WO2001074356A1 (fr) * 2000-04-03 2001-10-11 F. Hoffmann-La Roche Ag Solutions concentrees de carvedilol

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Title
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Also Published As

Publication number Publication date
WO2002065834A8 (fr) 2003-06-26
AU2001297631A1 (en) 2002-09-04
EP1335707A4 (fr) 2005-07-06
JP2004518734A (ja) 2004-06-24
AU2001297631A8 (en) 2005-09-15
CA2426811A1 (fr) 2002-08-29
WO2002065834A2 (fr) 2002-08-29
WO2002065834A3 (fr) 2002-10-03

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