WO1999024017A1 - Novel oral dosage form for carvedilol - Google Patents
Novel oral dosage form for carvedilol Download PDFInfo
- Publication number
- WO1999024017A1 WO1999024017A1 PCT/US1998/024102 US9824102W WO9924017A1 WO 1999024017 A1 WO1999024017 A1 WO 1999024017A1 US 9824102 W US9824102 W US 9824102W WO 9924017 A1 WO9924017 A1 WO 9924017A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carvedilol
- formulation
- release
- coating
- matrix
- Prior art date
Links
- OGHNVEJMJSYVRP-UHFFFAOYSA-N COc(cccc1)c1OCCNCC(COc1c(c2ccccc2[nH]2)c2ccc1)O Chemical compound COc(cccc1)c1OCCNCC(COc1c(c2ccccc2[nH]2)c2ccc1)O OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A61K9/10—Dispersions; Emulsions
-
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/28—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
- 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
- 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
- A61K9/5005—Wall or coating material
- A61K9/5015—Organic compounds, e.g. fats, sugars
Definitions
- the present invention relates to a novel formulation containing carvedilol, or a pharmaceutically acceptable salt thereof, and to its use in the treatment and/or prophylaxis of certain disorders.
- U.S. Patent No 4,503,067 describes a compound which is known as carvedilol.
- This compound is a novel multiple action drug useful in the treatment of mild to moderate hypertension.
- Carvedilol is known to be both a competitive non-selective ⁇ -adrenoceptor antagonist and a vasodilator.
- the vasodilatory actions of carvedilol result primarily from ⁇ i -adrenoceptor blockade, whereas the ⁇ -adrenoceptor blocking activity of the drug prevents reflex tachycardia when used in the treatment of hypertension.
- These multiple actions of carvedilol are responsible for the antihypertensive efficacy of the drug.
- carvedilol as a consequence of its antioxidant action in attenuating oxygen free radical- initiated lipid peroxidation, is useful in organ protection, in particular, cardioprotection. Additionally, carvedilol is useful in the treatment of congestive heart failure.
- the current formulation of carvedilol is a conventional swallow tablet, taken twice daily.
- This formulation is in immediate release form; that is to say the nature of the formulation is such that by the time carvedilol leaves the stomach, it is either in solution or it is in the form of a suspension of fine particles, i.e., a form from which carvedilol can be readily absorbed.
- the present invention provides a controlled release or delayed release formulation containing carvedilol or a pharmaceutically acceptable salt thereof.
- the present invention provides a controlled release or delayed release formulation comprising carvedilol, which is (l-(carbazol-4-yloxy-3-[[2-(o-methoxyphenoxy)- ethyl]amino]-2-propanol), of the formula (I): or a pharmaceutically acceptable salt thereof, in an oral dosage unit form.
- carvedilol which is (l-(carbazol-4-yloxy-3-[[2-(o-methoxyphenoxy)- ethyl]amino]-2-propanol), of the formula (I): or a pharmaceutically acceptable salt thereof, in an oral dosage unit form.
- the present invention also provides for a matrix formulation comprising carvedilol in an oral dosage unit form and for an enteric coated formulation comprising carvedilol in an oral dosage unit form.
- Carvedilol may be conveniently prepared as described in U.S. Pat. No. 4,503.067. Reference should be made to said patent for its full disclosure, the entire disclosure of which is incorporated herein by reference.
- carvedilol is suitably in the form of the free base or a pharmaceutically acceptable salt thereof.
- carvedilol is in the form of the free base.
- controlled release is meant any formulation that achieves slow release of drug over an extended period of time.
- a portion of the carvedilol in the formualtion is made available as a priming dose and the remainder is released in a sustained fashion.
- An example of a controlled release system is a matrix formulation.
- delayed release any formulation that utilizes repetitive, intermittent dosings of carvedilol from one or more immediate release units incorporated into a single dosage form.
- delayed release systems include repeat action tablets and capsules, and enteric-coated tablets where timed release is achieved by a barrier coating.
- controlled release formulations which are suitable for incorporating carvedilol are described in:
- delayed release formulations which are suitable for incorporating carvedilol are described in:
- controlled release formulations containing carvedilol may be in the form of a non-compressed pellet, having an enteric coat or a sustained release coat permeable to gastrointestinal juices.
- These 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.
- Such controlled release formulations are preferably formulated in a manner such that release of carvedilol is affected predominantly during the passage through the stomach and the small intestine, and delayed release formulations are preferably formulated such that release of the carvedilol is avoided in the stomach and is affected predominantly during passage through the small intestine
- Said formulations are preferably formulated such that the release of the carvedilol is predominantly l ⁇ z to 3 hours post ingestion.
- the small intestine is suitably the duodenum, the ileum or the jejunem.
- formulations of the present invention allow for once-a-day dosing.
- the controlled release formulation may be a matrix formulation.
- This formulation may comprise a plurality of matrix cores containing carvedilol, said matrix cores having different release rates of the drug.
- the preferred formulation comprises an immediate release phase of carvedilol, as well as a sustained release phase.
- the sustained release phase matrix core may be uncoated or coated. with a release-delaying substance.
- the release-delaying substance when the matrix core is coated with a release- delaying substance, is present in an amount of from 2 to 30% (w/w) relative to the matrix core. More preferably, the release-delaying substance is present in an amount of from 5 to 25% (w/w).
- the release-delaying substance of the present invention is a coating agent or a blend of agents thereof, which protects carvedilol from immediate degradation in the stomach.
- the overcoating depending on the release rate desired, may allow for continual release, or slow release, or delayed release.
- a preferred release-delaying substance is enteric coating, i.e., a medicinal preparation treated to pass through the stomach unaltered, which disintegrates in the intestines.
- the matrix formulations of the present invention may be prepared using three types of materials: insoluble plastics, hydrophilic polymers or fatty compounds.
- Plastic matrices include methyl acrylate-methacrylate, polyvinyl chloride and polyethylene.
- Hydrophilic polymers include methylcellulose, hydroxypropylmethylcellulose (HMPC) and sodium carboxymethylcellulose.
- Fatty compounds include various waxes such as carnauba wax and glyceryl tristearate. The most common method of preparation is to mix carvedilol with the matrix material and then compress the mixture into tablets. In the case of wax matrices, carvedilol is generally dispersed in molten wax, which is then congealed, granulated and compressed into cores.
- the priming dose (the portion of the carvedilol that is immediately available in the formulation) is placed in a coat of the tablet.
- the coat can be applied by press coating or by conventional pan or air suspension coating.
- the carvedilol matrix tablet formulation comprises a mixture of HMPC and Carbopol.
- the carvedilol matrix tablet formulation comprises a mixture of HMPC, Carbopol and mannitol.
- carvedilol, mannitol, and HPMC is granulated with purified water, wet screened, and then dried. The dry granules are screened. The resultant internal granulation is blended with pre-screened Carbomer 941 until homogeneous. Pre-screened magnesium stearate is mixed with the blend to create the compression mix. Tablets are compressed as round cores and are coated to an approximate 3 % weight gain with an Opadry® white solution, followed by an approximate 0.5 % weight gain with an Opadry® clear solution.
- the present invention also provides for various combinations of immediate release and controlled release forms.
- the uncoated sustained release matrix core may be in combination with an immediate release form of carvedilol and/or a coated matrix form.
- the matrix core may be comprised of a multitude of pellets coated independently with different release-delaying substances, all of which may be combined with uncoated or immediate release forms of carvedilol.
- Delayed release formulations containing carvedilol may be prepared either by coating particles or granules of carvedilol with varying thicknesses of slowly soluble polymers, or by microencapsulation.
- a hydrophilic substance acts as the coating material around a microcapsule.
- the hydrophilic substance can be selected from a variety of natural and synthetic polymers including shellacs, waxes, starches, cellulose acetate phthlate or butyrate, polyvinylpyrrolidone and polyvinyl chloride. Once the coating material dissolves, all the carvedilol in the microcapsule is immediatley available for dissolution and absorption.
- the release of carvedilol can be controlled by adjusting the thickness and the dissolution rate of the coat.
- the thickness can be varied from less than 1 micromolar to 200 micromolar by changing the amount of coating material from 3 to 30% of the total weight. If only a few different thicknesses are used, usually three or four, carvedilol will be released at different predetermined times to give a delayed release effect, i.e., repeat action. If a spectrum of different thicknesses is employed, a more uniform blood level of carvedilol can be obtained.
- the coated particles can be directly compressed into tablet, or placed in capsules. Carvedilol in the form of a controlled release or delayed release formulation can be used to treat hypertension, angina and congestive heart failure.
- the formulations of the instant invention may also be used in organ protection, for example, in cardioprotection.
- the present invention provides a method of treating hypertension, angina and congestive heart failure by administering an effective amount of a controlled release or delayed release formulation containing carvedilol or a pharmaceutically acceptable salt thereof, to a sufferer in need thereof.
- the present invention further provides the use of a controlled release or delayed release formulation containing carvedilol or a pharmaceutically acceptable salt thereof in the manufacture of a medicament, for treating hypertension, angina and congestive heart failure.
- the present invention also provides a pharmaceutical composition for use in the treatment of hypertension, angina and congestive heart failure which comprises a controlled release or delayed release formulation, preferably a matrix formulation, containing carvedilol or a pharmaceutically acceptable salt thereof. No unacceptable toxicological effects are expected when carvedilol is used according to the present invention.
- Step 1 Weigh out the exact amounts of carvedilol, mannitol, hydroxypropyl methylcellulose, and purified water.
- Step 2 Transfer the carvedilol, mannitol, and hydroxypropyl methylcellulose into a high shear mixer product bowl.
- Step 3 Pre-blend ingredients for 2 minutes with the impeller and chopper at low speed setting.
- Step 4 Granulate with purified water at low speed until desired granule appearance is achieved.
- Step 5 Discharge granulation into stainless steel container for the wet- milling process.
- Step 6 Slowly add the wet granules through the Quadro Comil (with screen) into a stainless steel container.
- Step 7 Transfer the milled granulation to the pre-heated fluid bed product bowl.
- Step 8 Dry the granules by maintaining the target inlet temperature of approximately 70°C (65°C - 75°C) until the product temperature reaches the target temperature (40 - 47°C) and the loss on drying is within the target range (0.5 - 1.8%).
- Step 9 Set-up the Quadro Comil (variable speed) and attach the screen for milling.
- Step 10 Add the dry granules through the Quadro Comil (with screen) into pre- tared polyethylene bags.
- Step 11 Screen an excess amount of Carbomer 941 (Carbopol 97 IP) to de- aggregate by passing though a #20 mesh stainless steel screen by hand.
- Step 12. Weigh out the exact amount of pre-screened Carbomer 941 (Carbopol 97 IP) onto the weigh paper.
- Step 13 Weigh out the exact amount of carvedilol internal granulation into properly labelled polyethylene bags.
- Step 14 Set-up a suitable size V-Blender.
- Step 15 Transfer l/3rd of the carvedilol internal granulation into the V blender.
- Step 16 Add l/3rd of the Carbomer 941 (Carbopol 971P) to the V blender.
- Step 17 Repeat Steps 15 and 16 until all internal granulation and Carbomer 941 (Carbopol 97 IP) is in the V blender.
- Step 18 Mix for 30 minutes or until homogeneous.
- Step 19 Remove samples for in-process testing.
- Step 20 Screen an excess amount of magnesium stearate (to de-aggregate) by passing though a #40 mesh stainless steel screen by hand.
- Step 21 Weigh out the exact amount of pre-screened magnesium stearate onto the weigh paper.
- Step 22 Load the magnesium stearate into the blender (containing the unlubricated granulation) and mix for 3 minutes.
- Step 23 Transfer the compression mix to the hopper of a rotary tablet press using 7/16" x 5/8" round standard tooling.
- Step 24 Compress tablets to meet the physical properties targets.
- Step 25 Remove samples for in-process testing throughout the run.
- Step 26 Separately weigh out the exact amount of carvedilol round active cores, Opadry® White and Opadry® Clear into polyethylene bags. If necessary, the round active cores may be bulked using oval placebo cores to achieve the batch size necessary to fill the coating pan.
- Step 27 Transfer into a suitable, clean tared container, the required quantity of purified water to produce a 12% solids concentration of Opadry® White.
- Step 28 With a vortex mixing action, slowly add the Opadry® White to the purified water. Continue mixing until no solid constituents are visible. Use this solution within 24 hours of manufacture.
- Step 29 Transfer into a suitable, clean tared container, the required quantity of purified water to produce a 5 % solids concentration of Opadry® Clear.
- Step 30 With a vortex mixing action, slowly add the Opadry® Clear to the
- Step 31 Set-up the Accela Coater coating pan. Set pump to deliver white and clear coating solution to spray at a rate of approximately 35 g/minute.
- Step 32 Transfer the cores to the coating pan. Pre heat the cores: Set the inlet temperature to 55°C (40°C - 70°C) while jogging the pan periodically. When product temperature reaches approximately 42°C (37°C - 45°C) start spray. Spray the entire quantity of white coating solution to obtain approximately a 3% weight gain coat. Under with clear coating solution to obtain approximately a 0.5% weight gain coat.
- Step 33 Remove coated tablets from coating pan into double polyethylene-lined drum. If placebo cores were used to bulk up the coating batch size, a sorting/inspection process is performed after completion of the coating run, to separate the oval placebo cores from the round active cores.
- Opadry White (OY-S-9603) NC 7.5 15.0 15.0
- Tablet Coating (apply approximately 6-10% of tablet core weight) %w/w
- Tablet Coating (apply approximately 6-10% of tablet core weight) %w/w
- Tablet Coating (apply approximately 5-12% of tablet core weight) %w/w
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL98340456A PL340456A1 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form of carvedilol |
NZ504418A NZ504418A (en) | 1997-11-12 | 1998-11-12 | Delayed release oral dosage form of carvedilol |
KR1020007005059A KR20010031952A (en) | 1997-11-12 | 1998-11-12 | Novel Oral Dosage Form for Carvedilol |
HU0004345A HUP0004345A3 (en) | 1997-11-12 | 1998-11-12 | Novel oral pharmaceutical compositions containing from carvedilol |
BR9814127-9A BR9814127A (en) | 1997-11-12 | 1998-11-12 | New oral dosage form for carvedilol |
EP98958546A EP1030651A4 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form for carvedilol |
CA002309542A CA2309542A1 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form for carvedilol |
AU14569/99A AU751117B2 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form for carvedilol |
JP2000520110A JP2001522794A (en) | 1997-11-12 | 1998-11-12 | New oral dosage form of carvedilol |
IL13602898A IL136028A0 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form for carvedilol |
NO20002439A NO20002439L (en) | 1997-11-12 | 2000-05-11 | New oral dosage forms for carvediol |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6545697P | 1997-11-12 | 1997-11-12 | |
US60/065,456 | 1997-11-12 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09554307 A-371-Of-International | 2000-05-11 | ||
US09/974,460 Continuation US20020054911A1 (en) | 1997-11-12 | 2001-10-09 | Novel oral dosage form for carvedilol |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999024017A1 true WO1999024017A1 (en) | 1999-05-20 |
Family
ID=22062830
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/024102 WO1999024017A1 (en) | 1997-11-12 | 1998-11-12 | Novel oral dosage form for carvedilol |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1030651A4 (en) |
JP (1) | JP2001522794A (en) |
KR (1) | KR20010031952A (en) |
CN (1) | CN1285738A (en) |
AU (1) | AU751117B2 (en) |
BR (1) | BR9814127A (en) |
CA (1) | CA2309542A1 (en) |
HU (1) | HUP0004345A3 (en) |
IL (1) | IL136028A0 (en) |
NO (1) | NO20002439L (en) |
NZ (1) | NZ504418A (en) |
PL (1) | PL340456A1 (en) |
TR (1) | TR200001362T2 (en) |
WO (1) | WO1999024017A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004056336A2 (en) * | 2002-12-20 | 2004-07-08 | Ranbaxy Laboratories Limited | Controlled release, multiple unit drug delivery systems |
EP1691789A4 (en) * | 2003-11-25 | 2012-08-08 | Smithkline Beecham Cork Ltd | Carvedilol free base, salts, anhydrous forms or solvate thereof, corresponding pharmaceutical compositions, controlled release formulations, and treatment or delivery methods |
US8449914B2 (en) | 2002-11-08 | 2013-05-28 | Egalet Ltd. | Controlled release carvedilol compositions |
US9629808B2 (en) | 2010-02-22 | 2017-04-25 | Daiichi Sankyo Company, Limited | Sustained-release solid preparation for oral use |
KR20170093589A (en) * | 2016-02-05 | 2017-08-16 | 삼진제약주식회사 | Carvedilol immediate release formulation having improved madescent |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050169994A1 (en) * | 2003-11-25 | 2005-08-04 | Burke Matthew D. | Carvedilol free base, salts, anhydrous forms or solvates thereof, corresponding pharmaceutical compositions, controlled release formulations, and treatment or delivery methods |
WO2007112579A1 (en) * | 2006-04-03 | 2007-10-11 | Isa Odidi | Drug delivery composition |
TWI415604B (en) | 2009-09-29 | 2013-11-21 | Tsh Biopharm Corp Ltd | Controlled release carvediolol formulation |
EP2540317A4 (en) * | 2010-02-22 | 2014-04-16 | Daiichi Sankyo Co Ltd | Sustained-release solid preparation for oral use |
WO2011102506A1 (en) * | 2010-02-22 | 2011-08-25 | 第一三共株式会社 | Sustained-release solid preparation for oral use |
EP2893928B1 (en) | 2012-09-03 | 2018-10-24 | Daiichi Sankyo Company, Limited | Hydromorphone hydrochloride-containing oral sustained-release pharmaceutical composition |
KR102492147B1 (en) | 2020-12-30 | 2023-01-26 | 단국대학교 천안캠퍼스 산학협력단 | Carvedilol loaded solid oral compositions using self-nanoemulsifying drug delivery system and methods for their preparation |
KR102525298B1 (en) | 2020-12-30 | 2023-04-25 | 단국대학교 천안캠퍼스 산학협력단 | Carvedilol loaded solid dispersion with increased oral bioavailability and methods for their preparation |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4287221A (en) * | 1979-01-16 | 1981-09-01 | Shin-Etsu Chemical Co., Ltd. | Method for providing enteric coating on solid dosage forms |
US4343789A (en) * | 1979-07-05 | 1982-08-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sustained release pharmaceutical composition of solid medical material |
US4503067A (en) * | 1978-04-13 | 1985-03-05 | Boehringer Mannheim Gmbh | Carbazolyl-(4)-oxypropanolamine compounds and therapeutic compositions |
US4680323A (en) * | 1983-12-01 | 1987-07-14 | Hans Lowey | Method and composition for the preparation of controlled long-acting pharmaceuticals for oral administration |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2082994T3 (en) * | 1990-10-23 | 1996-04-01 | Davband Pty Ltd | BACK SUPPORT FOR A CHAIR OR SEAT. |
US5760069A (en) * | 1995-02-08 | 1998-06-02 | Boehringer Mannheim Pharmaceuticals Corporation-Smithkline Beecham Corporation Limited Partnership #1 | Method of treatment for decreasing mortality resulting from congestive heart failure |
DE19637082A1 (en) * | 1996-09-12 | 1998-03-19 | Boehringer Mannheim Gmbh | Rapidly disintegrating pellets |
-
1998
- 1998-11-12 BR BR9814127-9A patent/BR9814127A/en not_active IP Right Cessation
- 1998-11-12 IL IL13602898A patent/IL136028A0/en not_active IP Right Cessation
- 1998-11-12 JP JP2000520110A patent/JP2001522794A/en active Pending
- 1998-11-12 KR KR1020007005059A patent/KR20010031952A/en not_active Application Discontinuation
- 1998-11-12 PL PL98340456A patent/PL340456A1/en unknown
- 1998-11-12 EP EP98958546A patent/EP1030651A4/en not_active Withdrawn
- 1998-11-12 WO PCT/US1998/024102 patent/WO1999024017A1/en not_active Application Discontinuation
- 1998-11-12 CN CN98813082A patent/CN1285738A/en active Pending
- 1998-11-12 TR TR2000/01362T patent/TR200001362T2/en unknown
- 1998-11-12 CA CA002309542A patent/CA2309542A1/en not_active Abandoned
- 1998-11-12 NZ NZ504418A patent/NZ504418A/en unknown
- 1998-11-12 AU AU14569/99A patent/AU751117B2/en not_active Ceased
- 1998-11-12 HU HU0004345A patent/HUP0004345A3/en unknown
-
2000
- 2000-05-11 NO NO20002439A patent/NO20002439L/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US4503067A (en) * | 1978-04-13 | 1985-03-05 | Boehringer Mannheim Gmbh | Carbazolyl-(4)-oxypropanolamine compounds and therapeutic compositions |
US4287221A (en) * | 1979-01-16 | 1981-09-01 | Shin-Etsu Chemical Co., Ltd. | Method for providing enteric coating on solid dosage forms |
US4343789A (en) * | 1979-07-05 | 1982-08-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sustained release pharmaceutical composition of solid medical material |
US4680323A (en) * | 1983-12-01 | 1987-07-14 | Hans Lowey | Method and composition for the preparation of controlled long-acting pharmaceuticals for oral administration |
Non-Patent Citations (1)
Title |
---|
See also references of EP1030651A4 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8449914B2 (en) | 2002-11-08 | 2013-05-28 | Egalet Ltd. | Controlled release carvedilol compositions |
WO2004056336A2 (en) * | 2002-12-20 | 2004-07-08 | Ranbaxy Laboratories Limited | Controlled release, multiple unit drug delivery systems |
WO2004056336A3 (en) * | 2002-12-20 | 2004-09-10 | Ranbaxy Lab Ltd | Controlled release, multiple unit drug delivery systems |
EP1691789A4 (en) * | 2003-11-25 | 2012-08-08 | Smithkline Beecham Cork Ltd | Carvedilol free base, salts, anhydrous forms or solvate thereof, corresponding pharmaceutical compositions, controlled release formulations, and treatment or delivery methods |
USRE47084E1 (en) | 2003-11-25 | 2018-10-16 | Flamel Ireland Limited | Oral medicinal product with modified release of at least one active principle in multimicrocapsular form |
US9629808B2 (en) | 2010-02-22 | 2017-04-25 | Daiichi Sankyo Company, Limited | Sustained-release solid preparation for oral use |
KR20170093589A (en) * | 2016-02-05 | 2017-08-16 | 삼진제약주식회사 | Carvedilol immediate release formulation having improved madescent |
Also Published As
Publication number | Publication date |
---|---|
AU751117B2 (en) | 2002-08-08 |
IL136028A0 (en) | 2001-05-20 |
NO20002439D0 (en) | 2000-05-11 |
BR9814127A (en) | 2000-10-03 |
AU1456999A (en) | 1999-05-31 |
JP2001522794A (en) | 2001-11-20 |
NO20002439L (en) | 2000-05-11 |
PL340456A1 (en) | 2001-02-12 |
KR20010031952A (en) | 2001-04-16 |
HUP0004345A2 (en) | 2001-06-28 |
TR200001362T2 (en) | 2000-09-21 |
NZ504418A (en) | 2003-02-28 |
CN1285738A (en) | 2001-02-28 |
EP1030651A1 (en) | 2000-08-30 |
EP1030651A4 (en) | 2006-05-31 |
HUP0004345A3 (en) | 2001-10-29 |
CA2309542A1 (en) | 1999-05-20 |
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