WO1993024109A1 - Palatable pharmaceutical compositions - Google Patents
Palatable pharmaceutical compositions Download PDFInfo
- Publication number
- WO1993024109A1 WO1993024109A1 PCT/US1993/005423 US9305423W WO9324109A1 WO 1993024109 A1 WO1993024109 A1 WO 1993024109A1 US 9305423 W US9305423 W US 9305423W WO 9324109 A1 WO9324109 A1 WO 9324109A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- drug
- coating
- composition
- coated
- poly
- Prior art date
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
- A61K9/0012—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
- A61K9/48—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
Definitions
- This invention relates to a composition and method for taste masking bitter, unpleasant tasting medicaments and provides for an immediate release of the medicament after injestion. More specifically, the invention relates to medicament cores coated with methacrylate ester copolymers which masks the bitter and unpleasant taste of the medicament. A method of preparing dosage units such as chewable tablets, employing the coated medicament is also described.
- the composition comprises a chewable tablet containing cimetidine coated with separate layers of methacrylate ester copolymers.
- the tablets do not exhibit the bitter taste of cimetidine and provides for an immediate release of the cimetidine.
- Cimetidine is a histamine - ⁇ -antagonist which has been shown to be useful in the treatment of duodenal, gastric, recurrent and stomal ulceration. It is also employed in the management of patients who are at high risk from hemorrhage of the upper gastrointestinal tract.
- Cimetidine is known to be one of many medicaments to have a pronounced bitter taste. This is not usually a problem when the dosage form employed is a capsule or a tablet designed to be swallowed, thereafter to disintegrate upon reaching the stomach. However, such dosage forms can be impractical when it is desired to administer a large amount of active ingredient, or to co-administer a relatively bulky second active ingredient such as an antacid or alginate. Moreover, many individuals have difficulty in swallowing a solid dosage form
- a conventional approach to administering relatively large amounts of active ingredient in a solid dosage form is by means of a chewable tablet, i.e., a tablet which disintegrates in the mouth upon being chewed. Such a tablet also circumvents the problem of a solid dosage being difficult to swallow.
- a further requirement of such a composition is that once the disintegrated tablet reaches the stomach, the individual particles should release the active ingredient rapidly and completely in order to ensure that substantially all of the active ingredient is absorbed; that is to say the formulation should be readily bioavailable.
- the formulation should be readily bioavailable.
- cimetidine because of its bitterness and solubility characteristics, the provision of such a dosage form represents a considerable problem.
- cimetidine granules have been coated with various compositions such as ethylcellulose and polyvinyl and acrylic polymers.
- a polymer mixture coating is employed.
- the mixture comprises a high temperature film forming copolymer of polymethyacrylic acid ester and acrylic acid ester and a low temperature film forming copolymers consisting of methacrylic acid ester and styrene acrylate.
- U.S. patent 4,892,740 discloses pharmaceutical preparations having improved flavouring characteristics obtained by the drug being coated by a polymeric substance which is soluble in gastic juice.
- a core results which is palatable and has good dissolution characteristics in the stomach.
- the coated core results in a taste masked medicament without reducing its bioavailability.
- the core particles which are to be coated can be composed of pure granular drug material or drug granules prepared in the conventional manner employing appropriate binding agents.
- the particle size of the core material is from about 180 to
- microns 420 microns. This range is preferable because larger particles tend to be ruptured during chewing and smaller particles present problems in the coating process.
- the particles should possess adequate hardness and friability characteristics to withstand attritive forces during the coating operation.
- Exemplary of bitter, unpleasant tasting drugs applicable to the taste-masking compositive of this invention are histamine ⁇ -antagonists, such as, for example, cimetidine, ranitidine, famotidine, nizatidine, etinidine, lupitidine, nifentidine, niperotidine, roxatidine, sulfotidine, tuvatidine and zaltidine; antibiotics, such as penicillin, ampicillin and erythromycin, acetaminophen; caffeine, dextromethorphan, diphenhydramine, theophylline, spironolactone and chloropheniramine.
- the above drugs are not limiting but merely exemplary of unpleasant tasting drugs that may be employed in this invention.
- the taste masking compositions of this invention will contain cimetidine or caffeine.
- the composition will contain from about 75 mg to 800 mg. Preferably it will containing from about 100 mg. to 400 mg. of cimetidine.
- the coating material is selected from the wide range of copolymers available under the tradename of Eudragits. These copolymers are manufactured and marketed by Rohm Pharma of Darmstadt, Germany.
- the coating composition is comprised of aqueous dispersions of ethyl acrylate (EA) and methyl methacrylate (MMA).
- EA ethyl acrylate
- MMA methyl methacrylate
- a particularly preferred coating composition of this invention is an aqueous dispersion of poly(EA-MMA) to which hydrophilic quaternary ammonium groups have been introduced to modify the permeability of the ester.
- Copolymerization of the above poly(EA-MMA)ester with different ratios of trimethylammonioethyl methacrylate chloride (TAMO) results in methacrylic ester copolymers of either high or low permeability.
- TAMO trimethylammonioethyl methacrylate chloride
- a coating film of high permeability results when poly (EA- MMA-TAMCl) are present in a 1:2:0.2 ratio.
- This copolymer is available under the tradename of Eudragit RL30D.
- a coating film of low permeability results when poly (EA-MMA-TAMC1) are present in a ratio of 1:2:0.1.
- This product is available under the tradename of Eudragit RS30D. Both Eudragit RL30D and RS30D are sold as 30% aqueous dispersions.
- the polymeric aqueous dispersions may also contain additives such as, plasticizers, pigments, talc and the like.
- Plasticizers are employed to assist in the film forming characteristics of the polymeric coating and also to provide greater integrity and elasticity to the films coat.
- Exemplary of plasticizers that may be employed in the coatings of this invention are triethyl citrate, triacetin, tributyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, dibutyl phthalate, dibutyl sebacate, vinyl pyrrolidone and propylene glycol.
- the amount of plasticizer present in the aqueous dispersion may be from 5% to about 30%.
- the plasticizer will be present in an amount of from about 15% to about 25% by weight of the dry polymers.
- pigments employed in the polymeric coating solutions of the invention may be color pigments such as FD&C or D&C approved lakes and dyes, iron oxide and titanium dioxide.
- the amount of pigment present in the coating solution may be from about 1% to about 20% by weight of the dry polymer.
- the method of coating the granular core particles comprises applying aqueous dispersions of Eudragit RL30D and RS30D to the core as distinct layers in subsequent coating steps.
- the polymers will be present in the dispersions in an amount of from about 10% to about 30% as the dry polymer.
- the core material is coated by subjecting them to air suspension coating technique.
- a Glatt Fluid Bed Wurster Coater is employed.
- An inner coating is applied by spraying (bottom spray) onto the fluidizing drug cores an aqueous dispersion of RL30D. The spraying is continued until a theoretical weight gain of from about 25% to about 50% of the batch is obtained.
- the coated material is retrieved and dedusted on a #60-80 U.S. mesh screen, equivalent to approximately 180-250 microns.
- a second coating layer comprising an aqueous dispersion of RS30D is applied to the above coated, dedusted particles to a theoretical weight gain of from about 5% to about 15% of the original batch.
- the particles are again dedusted using a #80 mesh screen resulting in a final product having a particle size of from about 200 to about 400 microns.
- the dedusting between coating steps is preferable particularly when friable drug particles are employed. More important, the dedusting steps result in a drug particle size which contributes to the immediate release and bioavailability characteristics of the coated drug granules.
- coated drug particles of this invention provide a method for formulating extremely palatable solid dosage units which contain unpleasant tasting drugs.
- orally administrable dosage units such as chewable tablets, troches, lozenges or sprinkle formulations may be prepared from the coated granules of this invention.
- the granules of the present invention are particularly suitable for use in preparing chewable tablets.
- conventional pharmaceutical excipients in addition to the coated core may be included.
- fillers, lubricants, binders, compression aids, and wetting agents may be employed.
- the fillers may be water soluble or insoluble such as lactose, sucrose or terra alba.
- Typical lubricants are stearic acid and its pharmaceutically acceptable alkali metal salts.
- binders are poly vinylpyrrolidones, polyethylene glycol, natural gums including veegum, tragacanth, acacia and gelatin.
- wetting agents include sodium lauryl sulfate, polysolbates and polyoxyethylene surfactants.
- Starch, alginates and their salts and maize would be representative of disintegrants.
- Typical compression aids would be microcrystalline cellulose, dicalcium phosphate and compressible sugar.
- the tablet can also contain sweeteners such as aspartame, sodium cyclamate and sodium saccharinate and flavorants such as orange, mint, cola, strawberry and the like.
- Example 2 Eudragit RL30D - Inner Coating Solution
- RS30D are applied as distinct coating layers as described hereinabove they not only produce extremely palatable granules which significantly minimizes the unpleasant taste associated with bitter drugs but also result in an immediate release of the drug in the stomach. This is surprising because both polymers are employed to produce either a sustained release or an enteric coated effect of the drug.
- a further advantage of this invention is that by employing an aqueous based coating medium the dangers associated with organic solvents, such as, for example, flammability, toxicity and pollution of the environment are eliminated.
- the coating system of this invention releases the drug by diffusion and not explosion.
- the release is influenced by drug solubility and media pH.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50088594A JP3839467B2 (en) | 1992-06-04 | 1993-06-04 | Tasteful pharmaceutical composition |
EP93914418A EP0650353B1 (en) | 1992-06-04 | 1993-06-04 | Palatable pharmaceutical compositions |
DE69331948T DE69331948T2 (en) | 1992-06-04 | 1993-06-04 | PLEASANT TASTING PHARMACEUTICAL COMPOSITIONS |
AT93914418T ATE217789T1 (en) | 1992-06-04 | 1993-06-04 | PLEASANT TASTING PHARMACEUTICAL COMPOSITIONS |
US08/347,325 US5578316A (en) | 1992-06-04 | 1993-06-04 | Palatable pharmaceutical compositions |
CA002137265A CA2137265C (en) | 1992-06-04 | 1993-06-04 | Palatable pharmaceutical compositions |
US08/713,878 US5837277A (en) | 1992-06-04 | 1996-09-13 | Palatable pharmaceutical compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89328892A | 1992-06-04 | 1992-06-04 | |
US07/893,288 | 1992-06-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993024109A1 true WO1993024109A1 (en) | 1993-12-09 |
Family
ID=25401342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1993/005423 WO1993024109A1 (en) | 1992-06-04 | 1993-06-04 | Palatable pharmaceutical compositions |
Country Status (8)
Country | Link |
---|---|
US (1) | US5578316A (en) |
EP (1) | EP0650353B1 (en) |
JP (1) | JP3839467B2 (en) |
AT (1) | ATE217789T1 (en) |
CA (1) | CA2137265C (en) |
DE (1) | DE69331948T2 (en) |
ES (1) | ES2174849T3 (en) |
WO (1) | WO1993024109A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0679391A2 (en) * | 1994-04-29 | 1995-11-02 | McNEIL-PPC, INC. | Solid pharmaceutical dosage form containing flavored film coating |
WO2000016742A1 (en) * | 1998-09-24 | 2000-03-30 | The Procter & Gamble Company | Chewable compositions containing dextromethorphan |
US6139865A (en) * | 1996-10-01 | 2000-10-31 | Eurand America, Inc. | Taste-masked microcapsule compositions and methods of manufacture |
WO2002036126A1 (en) * | 2000-10-30 | 2002-05-10 | Lupin Limited | Rapidly disintegrating sustained release cefuroxime axetil composition |
EP1235556A2 (en) * | 1999-03-19 | 2002-09-04 | Ranbaxy Laboratories, Ltd. | Taste masking coating compositions |
WO2012041788A1 (en) * | 2010-09-27 | 2012-04-05 | Basf Se | Protective coatings for acidic active ingredients |
US8617587B2 (en) | 2002-03-11 | 2013-12-31 | Novartis Ag | Tasted masked veterinary solid compositions |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5837277A (en) * | 1992-06-04 | 1998-11-17 | Smithkline Beecham Corporation | Palatable pharmaceutical compositions |
US5853756A (en) * | 1995-01-11 | 1998-12-29 | J. B. Chemicals & Pharmaceuticals Limited | Controlled release formulations of Ranitidine |
AUPN969796A0 (en) * | 1996-05-07 | 1996-05-30 | F.H. Faulding & Co. Limited | Taste masked liquid suspensions |
FR2752732B1 (en) * | 1996-08-28 | 1998-11-20 | Pf Medicament | EXTENDED RELEASE GALENIC FORM OF MILNACIPRAN |
DE19648576C2 (en) * | 1996-11-23 | 1999-08-12 | Lohmann Therapie Syst Lts | Lozenge for modified release of active substances in the gastrointestinal tract |
UA65607C2 (en) | 1998-03-04 | 2004-04-15 | Орто-Макнейл Фармацевтикал, Інк. | Pharmaceutical composition (variants) and process for its preparation |
US8231899B2 (en) * | 1998-09-10 | 2012-07-31 | Nycomed Danmark Aps | Quick release pharmaceutical compositions of drug substances |
US6270807B1 (en) | 1999-03-02 | 2001-08-07 | L. Perrigo Company | Taste-masked pharmaceutical composition |
WO2001035930A1 (en) * | 1999-11-16 | 2001-05-25 | Ranbaxy Laboratories Limited | Taste masked oral compositions |
CZ20023167A3 (en) * | 2000-02-29 | 2003-10-15 | Teva Pharmaceutical Industries Ltd. | Process for preparing clarithromycin and clarithromycin intermediate being substantially free of oxime and pharmaceutical preparation in which it is comprised |
JP2001253826A (en) * | 2000-03-09 | 2001-09-18 | Maruzen Pharmaceut Co Ltd | Internal medicine |
KR100510356B1 (en) * | 2001-02-27 | 2005-08-24 | 룀 게엠베하 운트 콤파니 카게 | Pharmaceutical formulations comprising a coating and binding agent with improved storage stability and process for the preparation thereof |
US7914811B2 (en) * | 2001-06-29 | 2011-03-29 | Mcneil-Ppc, Inc. | Brittle-coating, soft core dosage form |
WO2003020241A2 (en) * | 2001-09-05 | 2003-03-13 | Vectura Limited | Functional powders for oral delivery |
US7838026B2 (en) | 2001-09-28 | 2010-11-23 | Mcneil-Ppc, Inc. | Burst-release polymer composition and dosage forms comprising the same |
US7122143B2 (en) | 2001-09-28 | 2006-10-17 | Mcneil-Ppc, Inc. | Methods for manufacturing dosage forms |
US6723348B2 (en) * | 2001-11-16 | 2004-04-20 | Ethypharm | Orodispersible tablets containing fexofenadine |
US20030220351A1 (en) * | 2002-05-24 | 2003-11-27 | Gilbert Gonzales | Enteric coated caffeine tablet |
US7632521B2 (en) * | 2003-07-15 | 2009-12-15 | Eurand, Inc. | Controlled release potassium chloride tablets |
EP1673064A1 (en) * | 2003-08-28 | 2006-06-28 | Sandoz AG | Pharmaceutical composition comprising anticonvulsant with taste mask coating |
US20050181050A1 (en) * | 2004-01-28 | 2005-08-18 | Collegium Pharmaceutical, Inc. | Dosage forms using drug-loaded ion exchange resins |
US8609198B2 (en) * | 2004-07-21 | 2013-12-17 | Hewlett-Packard Development Company, L.P. | Pharmaceutical dose form with a patterned coating and method of making the same |
WO2006081518A2 (en) * | 2005-01-28 | 2006-08-03 | Collegium Pharmaceutical, Inc. | Non-ionic non-aqueous vehicles for topical and oral administration of carrier-complexed active agents |
JP2009541337A (en) * | 2006-06-19 | 2009-11-26 | マクニール−ピーピーシー・インコーポレーテツド | Enteric coated particles containing active ingredients |
US20130005874A1 (en) * | 2010-03-15 | 2013-01-03 | Taisho Pharmaceutical Co., Ltd | Pigment composition |
US9795576B2 (en) | 2010-09-27 | 2017-10-24 | Basf Se | Protective coatings for acidic active ingredients |
DK2637668T3 (en) | 2010-11-08 | 2016-08-29 | Albireo Ab | Ibat inhibitors for the treatment of liver diseases |
US10525010B2 (en) | 2012-05-02 | 2020-01-07 | Capsugel Belgium Nv | Aqueous dispersions of controlled release polymers and shells and capsules thereof |
WO2015065848A1 (en) | 2013-11-04 | 2015-05-07 | Capsugel Belgium Nv | Methods and systems for improved bioavailability of active pharmaceutical ingredients including esomeprazole |
WO2015130760A1 (en) | 2014-02-25 | 2015-09-03 | Orbis Biosciences, Inc. | Taste masking drug formulations |
JP6751020B2 (en) | 2014-06-25 | 2020-09-02 | Eaファーマ株式会社 | Solid preparation and method for preventing or reducing coloration thereof |
US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
US10786529B2 (en) * | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
WO2019032026A1 (en) | 2017-08-09 | 2019-02-14 | Albireo Ab | Cholestyramine granules, oral cholestyramine formulations and use thereof |
US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
WO2019245448A1 (en) | 2018-06-20 | 2019-12-26 | Albireo Ab | Crystal modifications of odevixibat |
US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5075114A (en) * | 1990-05-23 | 1991-12-24 | Mcneil-Ppc, Inc. | Taste masking and sustained release coatings for pharmaceuticals |
US5112621A (en) * | 1987-12-21 | 1992-05-12 | Synthelabo | Sustained release pharmaceutical composition of diltiazem |
Family Cites Families (12)
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US4800087A (en) * | 1986-11-24 | 1989-01-24 | Mehta Atul M | Taste-masked pharmaceutical compositions |
JPS63188621A (en) * | 1987-01-30 | 1988-08-04 | Taisho Pharmaceut Co Ltd | Flavor oral preparation |
JPH07551B2 (en) * | 1987-01-14 | 1995-01-11 | 久光製薬株式会社 | Manufacturing method of microcapsule formulation |
KR960011236B1 (en) * | 1987-05-08 | 1996-08-21 | 스미스 클라인 앤드 프렌취 라보라토리스 리미티드 | Pharmaceutical compositions of cimetidine |
JPH0774151B2 (en) * | 1987-10-12 | 1995-08-09 | 三井東圧化学株式会社 | Process for producing powder which masks unpleasant organoleptic properties of drug |
ES2052911T3 (en) * | 1988-05-04 | 1994-07-16 | Smith Kline French Lab | CHEWABLE TABLET. |
US4925675A (en) * | 1988-08-19 | 1990-05-15 | Himedics, Inc. | Erythromycin microencapsulated granules |
EP0425699B1 (en) * | 1989-05-11 | 1994-08-17 | Chugai Seiyaku Kabushiki Kaisha | Oral preparation which can be released at suitable region in intestine |
JPH0674206B2 (en) * | 1989-12-28 | 1994-09-21 | 田辺製薬株式会社 | Controlled release formulation and process for producing |
JP2856485B2 (en) * | 1990-03-07 | 1999-02-10 | 旭化成工業株式会社 | Granule-containing tablets |
US5084287A (en) * | 1990-03-15 | 1992-01-28 | Warner-Lambert Company | Pharmaceutically useful micropellets with a drug-coated core and controlled-release polymeric coat |
CA2068402C (en) * | 1991-06-14 | 1998-09-22 | Michael R. Hoy | Taste mask coatings for preparation of chewable pharmaceutical tablets |
-
1993
- 1993-06-04 AT AT93914418T patent/ATE217789T1/en not_active IP Right Cessation
- 1993-06-04 US US08/347,325 patent/US5578316A/en not_active Expired - Lifetime
- 1993-06-04 ES ES93914418T patent/ES2174849T3/en not_active Expired - Lifetime
- 1993-06-04 WO PCT/US1993/005423 patent/WO1993024109A1/en active IP Right Grant
- 1993-06-04 JP JP50088594A patent/JP3839467B2/en not_active Expired - Fee Related
- 1993-06-04 EP EP93914418A patent/EP0650353B1/en not_active Expired - Lifetime
- 1993-06-04 CA CA002137265A patent/CA2137265C/en not_active Expired - Fee Related
- 1993-06-04 DE DE69331948T patent/DE69331948T2/en not_active Expired - Lifetime
Patent Citations (2)
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US5112621A (en) * | 1987-12-21 | 1992-05-12 | Synthelabo | Sustained release pharmaceutical composition of diltiazem |
US5075114A (en) * | 1990-05-23 | 1991-12-24 | Mcneil-Ppc, Inc. | Taste masking and sustained release coatings for pharmaceuticals |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0679391A2 (en) * | 1994-04-29 | 1995-11-02 | McNEIL-PPC, INC. | Solid pharmaceutical dosage form containing flavored film coating |
EP0679391A3 (en) * | 1994-04-29 | 1996-05-15 | Mcneil Ppc Inc | Solid pharmaceutical dosage form containing flavored film coating. |
US6139865A (en) * | 1996-10-01 | 2000-10-31 | Eurand America, Inc. | Taste-masked microcapsule compositions and methods of manufacture |
WO2000016742A1 (en) * | 1998-09-24 | 2000-03-30 | The Procter & Gamble Company | Chewable compositions containing dextromethorphan |
EP1235556A2 (en) * | 1999-03-19 | 2002-09-04 | Ranbaxy Laboratories, Ltd. | Taste masking coating compositions |
EP1235556A4 (en) * | 1999-03-19 | 2003-07-16 | Ranbaxy Lab Ltd | Taste masking coating compositions |
WO2002036126A1 (en) * | 2000-10-30 | 2002-05-10 | Lupin Limited | Rapidly disintegrating sustained release cefuroxime axetil composition |
US6932981B2 (en) | 2000-10-30 | 2005-08-23 | Lupin Laboratories, Ltd. | Rapidly disintegrating sustained release cefuroxime axetil composition |
US8617587B2 (en) | 2002-03-11 | 2013-12-31 | Novartis Ag | Tasted masked veterinary solid compositions |
WO2012041788A1 (en) * | 2010-09-27 | 2012-04-05 | Basf Se | Protective coatings for acidic active ingredients |
CN103221038A (en) * | 2010-09-27 | 2013-07-24 | 巴斯夫欧洲公司 | Protective coatings for acidic active ingredients |
Also Published As
Publication number | Publication date |
---|---|
JPH07507549A (en) | 1995-08-24 |
CA2137265C (en) | 2003-10-28 |
ATE217789T1 (en) | 2002-06-15 |
EP0650353B1 (en) | 2002-05-22 |
DE69331948D1 (en) | 2002-06-27 |
JP3839467B2 (en) | 2006-11-01 |
DE69331948T2 (en) | 2002-11-28 |
EP0650353A1 (en) | 1995-05-03 |
CA2137265A1 (en) | 1993-12-09 |
ES2174849T3 (en) | 2002-11-16 |
EP0650353A4 (en) | 1996-02-28 |
US5578316A (en) | 1996-11-26 |
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