WO2000040223A1 - Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings - Google Patents
Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings Download PDFInfo
- Publication number
- WO2000040223A1 WO2000040223A1 PCT/US1999/028559 US9928559W WO0040223A1 WO 2000040223 A1 WO2000040223 A1 WO 2000040223A1 US 9928559 W US9928559 W US 9928559W WO 0040223 A1 WO0040223 A1 WO 0040223A1
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- WIPO (PCT)
- Prior art keywords
- composition
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- active ingredients
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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
- A61K9/20—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
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer
-
- 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
- the present invention relates to film forming compositions and more particularly it relates to compositions comprising hydroxypropylcellulose and sodium carboxymethylcellulose.
- sodium carboxymethylcellulose films dissolve much more rapidly than films e.g. hydroxypropymethyl cellulose and so are less likely to interfere with the dissolution of drug from a coated tablet.
- Hydroxypropylcellulose has been used very successfully in aqueous film coatings to enhance the utility of hydroxypropylmethylcellulose (The Use of Klucei hydroxy-propylcellulose (HPC), NF, to increase the Utility of hydroxypropylmethylcellulose (HPMC) in Aqueous Film Coating, Aqualon Technical Bulletin VC-556A). Hydroxypropylmethylcellulose has high tensile strength and a very low percent elongation. When Klucei HPC, with its high percent elongation, is added to the traditional hydroxypropylmethylcellulose film coating, the film flexibility and substrate adherence is greatly increased.
- HPC Klucei hydroxy-propylcellulose
- HPMC hydroxypropylmethylcellulose
- U.S. Patent No. 4,316,884 discloses that indoprofen can be used in increased safety at its effective anti-inflammatory dose in humans and that the activity of indoprofen is greatly prolonged by micro encapsulating micro particles of indoprofen in a solid protective coating of a cellulose ether such as ethylcellulose.
- composition comprising hydroxypropylcellulose and at least one anionic polymer e.g. carboxymethyl ether salts of cellulose, methacrylic acid polymers and copolymers, carboxyvinyl polymers and copolymers, alginic acid salts, pectinic acid salts, pectic acid salts, carrageenan, agar and carboxylic acid salts of polysaccharides.
- anionic polymer e.g. carboxymethyl ether salts of cellulose, methacrylic acid polymers and copolymers, carboxyvinyl polymers and copolymers, alginic acid salts, pectinic acid salts, pectic acid salts, carrageenan, agar and carboxylic acid salts of polysaccharides.
- composition comprising a substrate and a coating comprising hydroxypropylcellulose and at least one anionic polymer.
- Still further provided is a process for coating a substrate comprising (a) preparing an aqueous solution of hydroxypropylcellulose and anionic polymer and (b) applying said solution to the substrate.
- the term "consisting essentially of means that the named ingredients are essential, however, other ingredients which do not prevent the advantages of the present invention from being realized can also be included.
- compositions of hydroxypropylcellulose and anionic polymer such as sodium carboxymethylcellulose, have film-forming characteristics. Films of these compositions show good tensile strength and percent elongation as well as provide high gloss film coatings.
- Anionic polymers suitable for use in the present invention are carboxymethyl ether salts of cellulose, preferably SCMC, methacrylic acid polymers and copolymers, carboxyvinyl polymers and copolymers, alginic acid salts , pectinic acid salts, pectic acid salts, carrageenan, agar and carboxylic acid salts of polysaccharides.
- Sodium carboxymethyl cellulose suitable for use in the present invention has a degree of substitution (DS) of at least 0.2 and preferably at least about 0.5.
- the degree of substitution of the sodium carboxymethyl cellulose can be up to about 2.5, preferably up to about 0.9.
- the degree of polymerization (DP) of the sodium carboxymethylcellulose is at least about 100, preferably at least about 200.
- the sodium carboxymethylcellulose degree of polymerization can be up to about 4,000, preferably up to about 1 ,000.
- Hydroxypropylcellulose suitable for the present invention has a weight average molecular weight of at least about 80,000.
- the molecular weight of the hydroxypropylcellulose can be up to about 1 ,150,000, preferably up to about 95,000.
- the degree of substitution for the sodium carboxymethyl cellulose is given by carboxymethyl groups based on 3.0 as total substitution of available androhexoic sites.
- Sodium carboxymethylcellulose is a cellulose gum available as Aqualon® SCMC from Hercules Incorporated. As a 99.5% purity free flowing powder it meets all specifications of the US PHARMACOPEIA.
- Hydroxypropylcellulose is a cellulose gum available as Klucei® hydroxypropylcellulose from Hercules Incorporated. As a free flowing powder it meets all specifications of the US PHARMACOPEIA.
- the weight ratio of hydroxypropylcellulose to sodium carboxymethylcellulose is at least about 1 :20, preferably at least about 1 :4.
- the hydroxypropylcellulose:sodium carboxymethylcellulose weight ratio can be up to about 20:1 , preferably up to about 4:1.
- piasticizer can also be present in the composition of the present invention.
- Suitable plasticizers are ethanolamines, ethylene glycol, glycerol, 1 ,2,6- hexanetriol, mono-, di-, and triacetin, 1,5-pentanediol, sorbitol, polyethylene glycol (weight average molecular weight up to about 600), propylene glycol and trimethylolpropane.
- the preferred piasticizer is polyethylene glycol, preferably having a molecular weight of about 400.
- the piasticizer is at least one percent by weight based on the total composition, preferably at least about 5.5 percent by weight.
- the piasticizer when present, can be up to about 50% by weight, preferably up to about 20 percent by weight based on the total composition.
- composition of the present invention is particularly suitable for use as a coating on substrates e.g. for the coating of tablets, granules, beads etc.
- substrates e.g. for the coating of tablets, granules, beads etc.
- One specific area of use is for the coating of pharmaceutical substrates e.g. tablets containing pharmaceutically active ingredients, or may be applicable for novel pharmaceutic dosage forms.
- pharmaceutically approved piasticizer such as polyethylene glycol can be used.
- ingredients can also be incorporated in the coating composition, such as active pharmaceutical ingredients, active cosmetic ingredients, nutritional supplements, colorants, opacifying materials, surfactants, stabilizers, silicas, silicones, preservatives, surface treatment agents, flavorants, crosslinking agents, and other polymers deemed necessary and useful in promoting the utility, value and ease of preparation or coating of the tablets, granules, beads and other novel pharmaceutical dosage forms.
- active medicaments include antacids, anti- inflammatory substances, (including but not limited to non-steroidal anti-inflammatory drugs, NSAIDs, vasodilators, coronary vasodilators, cerebral vasodilators, and perpheral vasodilators), anti-infectives, phsychotropics, antimanics, stimulants, antihistamines, laxatives, decongestants, vitamines, gastrointestinal sedatives, antidiarrheal preparations, antianginal drugs, antiarrhythmics, antihypertensive drugs, vasoconstrictors and migraine treatments, anticoagulants and anti-thrombotic drugs, analgesics, anti-pyretics, hypnotics, sedatives, antiemetics, anti-nauseants, anticonvulsants, neuromuscular drugs, hyper-and hypoglycemic agents, thyroid and antithyroid preparations, diuretics, antispasmodics, uterine relaxants
- Examples of specific active medicaments include aluminum hydroxide, prednisolone, dexamethasone, aspirin, acetaminophen, ibuprofen, isosorbide dinitrate, nicotinic acid, tetracycline, ampicillin, dexbrompheniramine, chlorpheniramine, albuterol pseudophedrine, loratadine theophylline, ascorbic acid, tocopherol, pyridoxine, methoclopramide, magnesium hydroxide, verapamil, procainamide hydrochloride, propranolol, captopril, ergotamine, fiurazepam, diazepam, lithium carbonate, insulin, furosemide, hydrochlorothiazide, guaiphenesin, dextromethorphan and benzocaine, although any active medicament which is physically and chemically compatible with the hydroxypropyl cellulose and anionic polymer blend and other tablet ingredients.
- Formulations containing NSAIDs may also contain therapeutic amounts of other pharmaceutical actives conventionally employed with NSAID including but not limited to decongestants or bronchodilators (such as pseudoephedrine, phenylpropanolamine, phenylephrine and pharmaceutically acceptable salts thereof), antitussives (such as caraminophen, dextromethorphan and pharmaceutically acceptable salts thereof), antihistamines (such as chlorpheniramine, brompheniramine, dexchlorpheniramine, dexbrompheniramine, triprolidine, doxylamine, tripelennamine, cyproheptadine, pyrilamine, hydroxyzine, promethazine, azatadine and pharmaceutically accptable salts thereof), non-sedating antihistamines (such as acrivastine, astemizole, cetirizine, ketotifen, lorat
- muscle relaxants such as glycerylmonether SMRs, methocarbamol, mephenesin, mephenesin carbamate, cyclobenzaprine, chlorzoxazone, mephenesin acid succinate, chlorphenesin carbamate, or pharmaceutically acceptable salts thereof
- adjuvants such as diphenhydramine, caffeine, xanthine derivatives (including those disclosed in U.S. Pat. No. 4,558,051 , hereby incorporated by reference) and pharmaceutically acceptable salts thereof, nutritional supplements and combinations of any of the aforesaid pharmaceuticals.
- acetaminophen for the treatment of allergies, cough, colds, cold-like and/or flu symptoms in mammals including humans.
- these pharamaceuticals maybe combined with acetaminophen as sleep aids (such as diphenhydramine), or for other known purposes.
- Anionic polymers such as sodium carboxymethyl cellulose cross-link in the presence of certain polyvalent cations.
- Sodium carboxymethylcellulose (SCMC) is an anionic water-soluble polymer.
- SCMC Sodium carboxymethylcellulose
- the chemical and physical properties of SCMC make it useful in a wide range of applications, such as food, pharmaceuticals and personal care.
- Treatment of aqueous solutions of SCMC with certain polyvalent salts results in its precipitation.
- polyvalent cations such as Al +3
- SCMC solutions leads to uniform cross-linking of the polymer molecules through carboxymethyl groups. This produces a gel. The nature of the gel depends in turn, on the amount of cross-linking agent present, the concentration and the DP of the polymer molecules.
- the rate at which gelation occurs depends upon how quickly the Al +3 ions are allowed to dissociate into the aqueous system.
- the ultimate qualities of the gel and gelling times can be controlled by varying the viscosity grade and amount of SCMC used, the proportion of a polyvalent cation and the pH of the medium.
- the active ingredients that can be incorporated in the coating composition and in the substrate can be pharmaceutically active ingredients such as hypnotics, sedatives, antiepileptics, awakening agents, psychoneurotropic agents, neuromuscular blocking agents, antispasmodic agents, antihistaminics, antiailergics, cardiotonics, antiarrhythmics, diuretics, hypotensives, vasopressors, antitussive expectorants, thyroid hormones, sexual hormones, antidiabetics, antitumor agents, antibiotics, chemotherapeutics, and narcotics.
- pharmaceutically active ingredients such as hypnotics, sedatives, antiepileptics, awakening agents, psychoneurotropic agents, neuromuscular blocking agents, antispasmodic agents, antihistaminics, antiailergics, cardiotonics, antiarrhythmics, diuretics, hypotensives, vasopressors, antitussive expectorants, thyroid hormones, sexual hormones
- the coating composition and the substrate may contain cosmetically active agents such as breath freshening compounds like menthol, other flavors and fragrances commonly used for oral hygiene, and for dental and oral cleansing like quaternary ammonium bases.
- cosmetically active agents such as breath freshening compounds like menthol, other flavors and fragrances commonly used for oral hygiene, and for dental and oral cleansing like quaternary ammonium bases.
- the effect of flavors may be enhanced using flavor enhancers like tartaric acid, citric acid, vanillin, or the like.
- composition of the present invention is preferably applied from aqueous solution for the coating of substrates such as tablets.
- the preferred process for coating the substrate with the composition of the present invention comprises preparing an aqueous solution of hydroxypropylcellulose and anionic polymer, e.g. sodium carboxymethylcellulose and applying the aqueous solution to the substrate.
- piasticizer as indicated above can also be present in the coating composition.
- the solutions can be made up together or alternatively can be made up separately.
- Suitable coating weight will preferably be at least about 0.5%, more preferably at least about 0.75% by weight based on the total weight of the coated substrate.
- the coating weight can be up to about 10% by weight preferably up to about 2% by weight of the total coated composition.
- High gloss pharmaceutical tablets generally comprise at least one pharmaceutically active ingredient in a binder matrix core having a coating of anionic polymer, e.g., sodium carboxymethylcellulose, hydroxypropylcellulose and optionally a piasticizer.
- anionic polymer e.g., sodium carboxymethylcellulose, hydroxypropylcellulose and optionally a piasticizer.
- composition of the present invention has industrial applicability in the manufacturing of pharmaceutical formulations.
- Glatt GPCG5/9 available from Glatt Air Techniques was set up as follows:
- the tablets are pneumatically fluidized through a cylindrical coating partition past a spray nozzle which is mounted in the center of the bottom orifice plate of the product chamber. As the tablets pass through the spray they are coated with the aqueous solution. The region outside the partition is the down bed. The air flow in this region keeps the tablets in near weightless suspension so that they can move rapidly downward and can be drawn horizontally in to the gap at the base of the coating partition. This process continues until the tablets have achieved the desired coating.
- Example 2 With stirring 24.8 g of Aqualon® 7L2P sodium carboxymethyl cellulose was added to 595.2 g of deionized water, and 24.8 g of Klucei® EF hydroxypropylcellulose was mixed with 235.2 g of deionized water. Mixing was continued until the solution cleared. Then 3.9 g of polyethylene glycol, available from Union Carbide as PEG 400, was added to both solutions and mixed until uniform solutions were obtained. 3.1 g of aluminum chloride was dissolved in 50 g of deionized water. This solution was added to the hydroxypropylcellulose solution and mixed until a uniform solution was obtained.
- Solution viscosity was measured to obtain a value between 125 and 175 cps in order to provide good coating using the Glatt GPCG-5 were charged to the fluid bed and allowed to warm up for five minutes. The spraying was begun with a layer of sodium carboxymethyl cellulose followed by a layer of hydroxypropylcellulose. These layers were alternated and the final layer was sodium carboxymethyl cellulose. The weight gain was 1.7%.
- the disintegration time of the layered tablets was 8:10 minutes.
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- Pharmacology & Pharmacy (AREA)
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000591980A JP2002534373A (en) | 1998-12-31 | 1999-12-02 | Composition containing hydroxypropylcellulose and anionic polymer, and its use as a pharmaceutical film coating |
BR9908394-9A BR9908394A (en) | 1998-12-31 | 1999-12-02 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
CA002322293A CA2322293A1 (en) | 1998-12-31 | 1999-12-02 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
AU20371/00A AU2037100A (en) | 1998-12-31 | 1999-12-02 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
EP99964056A EP1058543A1 (en) | 1998-12-31 | 1999-12-02 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
BG104799A BG104799A (en) | 1998-12-31 | 2000-09-26 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22807598A | 1998-12-31 | 1998-12-31 | |
US09/228,075 | 1998-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000040223A1 true WO2000040223A1 (en) | 2000-07-13 |
Family
ID=22855672
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/028559 WO2000040223A1 (en) | 1998-12-31 | 1999-12-02 | Hydroxypropylcellulose and anionic polymer compositions and their use as pharmaceutical film coatings |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1058543A1 (en) |
JP (1) | JP2002534373A (en) |
CN (1) | CN1295469A (en) |
AR (1) | AR022118A1 (en) |
AU (1) | AU2037100A (en) |
BG (1) | BG104799A (en) |
BR (1) | BR9908394A (en) |
CA (1) | CA2322293A1 (en) |
ID (1) | ID26814A (en) |
WO (1) | WO2000040223A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150119473A1 (en) * | 2013-10-26 | 2015-04-30 | Zhongshan Capsule Starch Material Technology Co., Ltd. | Coating And Extruding Method For Producing Starch Softgel Capsules |
US20150267114A1 (en) * | 2014-03-24 | 2015-09-24 | Lamberti Spa | Moisturizing agents |
WO2018195205A1 (en) | 2017-04-18 | 2018-10-25 | Sensient Colors Llc | Dosage form coating composition and method of making and using the same |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006123765A1 (en) * | 2005-05-20 | 2006-11-23 | Daiichi Sankyo Company, Limited | Film coated preparation |
AU2010228257A1 (en) | 2009-03-25 | 2011-09-29 | Aska Pharmaceutical Co., Ltd. | Adhesion preventing composition, solid preparation and method for producing same |
CN105640819A (en) * | 2014-11-13 | 2016-06-08 | 广州十长生化妆品有限公司 | Skin tendering smoothening whitening exfoliating microsphere and application thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57145817A (en) * | 1981-03-05 | 1982-09-09 | Satoru Yamazaki | Remedy for peptic ulcer |
US4931286A (en) * | 1989-04-19 | 1990-06-05 | Aqualon Company | High gloss cellulose tablet coating |
US5080717A (en) * | 1991-01-24 | 1992-01-14 | Aqualon Company | Fluid suspensions of polysaccharide mixtures |
-
1999
- 1999-12-02 CA CA002322293A patent/CA2322293A1/en not_active Abandoned
- 1999-12-02 CN CN 99804552 patent/CN1295469A/en active Pending
- 1999-12-02 EP EP99964056A patent/EP1058543A1/en not_active Withdrawn
- 1999-12-02 AU AU20371/00A patent/AU2037100A/en not_active Abandoned
- 1999-12-02 ID IDW20001919A patent/ID26814A/en unknown
- 1999-12-02 WO PCT/US1999/028559 patent/WO2000040223A1/en not_active Application Discontinuation
- 1999-12-02 BR BR9908394-9A patent/BR9908394A/en not_active IP Right Cessation
- 1999-12-02 JP JP2000591980A patent/JP2002534373A/en active Pending
- 1999-12-20 AR ARP990106576 patent/AR022118A1/en not_active Application Discontinuation
-
2000
- 2000-09-26 BG BG104799A patent/BG104799A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57145817A (en) * | 1981-03-05 | 1982-09-09 | Satoru Yamazaki | Remedy for peptic ulcer |
US4931286A (en) * | 1989-04-19 | 1990-06-05 | Aqualon Company | High gloss cellulose tablet coating |
US5080717A (en) * | 1991-01-24 | 1992-01-14 | Aqualon Company | Fluid suspensions of polysaccharide mixtures |
Non-Patent Citations (4)
Title |
---|
"Handbook of Pharmaceutical Excipients", 1986, AMERICAN PHARMACEUTICAL ASSOCIATION, THE PHARMACEUTICAL SOCIETY OF GREAT BRITAIN, ISBN 0-917330-56-0, XP002136036 * |
DATABASE WPI Section Ch Week 198242, Derwent World Patents Index; Class A96, AN 1982-88806E, XP002136037 * |
FUKUMORI Y, ET AL.: "Computer simulation of agglomeration in the Wurster process", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 40, no. 8, 1992, ISSN 0009-2363, pages 2159 - 2163, XP002136034 * |
HARWOOD RL, ET AL.: "Hydroxypropyl cellulose" * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150119473A1 (en) * | 2013-10-26 | 2015-04-30 | Zhongshan Capsule Starch Material Technology Co., Ltd. | Coating And Extruding Method For Producing Starch Softgel Capsules |
US20150267114A1 (en) * | 2014-03-24 | 2015-09-24 | Lamberti Spa | Moisturizing agents |
US9464227B2 (en) * | 2014-03-24 | 2016-10-11 | Lamberti Spa | Moisturizing agents |
AU2015238528B2 (en) * | 2014-03-24 | 2019-02-21 | Lamberti Spa | Moisturizing agents |
WO2018195205A1 (en) | 2017-04-18 | 2018-10-25 | Sensient Colors Llc | Dosage form coating composition and method of making and using the same |
EP3612168A4 (en) * | 2017-04-18 | 2020-12-23 | Sensient Colors LLC | Dosage form coating composition and method of making and using the same |
Also Published As
Publication number | Publication date |
---|---|
ID26814A (en) | 2001-02-08 |
BG104799A (en) | 2001-05-31 |
CN1295469A (en) | 2001-05-16 |
JP2002534373A (en) | 2002-10-15 |
AR022118A1 (en) | 2002-09-04 |
EP1058543A1 (en) | 2000-12-13 |
BR9908394A (en) | 2000-10-31 |
AU2037100A (en) | 2000-07-24 |
CA2322293A1 (en) | 2000-07-13 |
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