WO2003039517A1 - Process for preparing quick dissolving, high loading ribavirin compositions - Google Patents
Process for preparing quick dissolving, high loading ribavirin compositions Download PDFInfo
- Publication number
- WO2003039517A1 WO2003039517A1 PCT/US2002/034899 US0234899W WO03039517A1 WO 2003039517 A1 WO2003039517 A1 WO 2003039517A1 US 0234899 W US0234899 W US 0234899W WO 03039517 A1 WO03039517 A1 WO 03039517A1
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- WO
- WIPO (PCT)
- Prior art keywords
- ribavirin
- composition
- composition according
- weight percent
- disintegrant
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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
- A61K9/14—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
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- 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
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Definitions
- the present invention relates to a quick dissolving ribavirin composition which comprises at least 80% by weight ribavirin and is prepared by a wet granulation process.
- Ribavirin (C 8 H 12 N 4 O 5 ) is an antiviral agent which has been administered alone or in combination with interferon alpha-2b to treat patients with chronic hepatitis C infections.
- Ribavirin is commercially available in capsule form under the trademarks Virazole® and Rebetol®.
- U.S. Patent Nos. 6,051,252; 5,916,594; and 5,914,128 describe ribavirin compositions prepared by a dry compacting method at a compressing force from about 50 to about 75 kN. Such a high compressing force is necessary due to the poor compressibility of ribavirin. However, heat is produced during the dry compacting operation which may cause the formation of ribavirin polymorphic forms. Such polymorphic forms are undesirable.
- U.S. Patent No. 4,439,453 describes a wet granulation method for granulating acetaminophen which involves blending acetaminophen powder or crystals with excipients; wetting to a moist powder consistency with an aqueous binder solution; drying; milling; and then blending with more excipients and a lubricant.
- the wet granulation process requires a large amount of excipients, generally from about 25 to about 40 weight percent, based on the dried weight of the pharmaceutical composition.
- wet granulation as compared to roller compaction process are that wet granulation: (1) provides the material to be compressed with better wetting properties, particularly in the case of hydrophobic drug substances; (2) allows the use of a hydrophilic excipient in the process which makes the surface of a hydrophobic drug more hydrophilic which improves disintegration and dissolution; (3) improves content uniformity of the solid dosage forms because the granules obtained thereby usually contain approximately the same amount of ingredients, and thus, segregation of different ingredients of the material to be compressed due to different physical characteristics such as density is avoided; and (4) optimizes the particle size and shape of particles by creating approximately spherical granules.
- a granulated ribavirin composition which is quick dissolving, free flowing, and has adequate bulk density for processing into capsules.
- a further need is for such a granulation composition to provide a high load, for example, at least 80%, of ribavirin in the composition.
- the ribavirin composition should be substantially free of polymorphic forms of ribavirin.
- the invention provides a quick dissolving, high loading ribavirin composition which is essentially free of ribavirin polymorphic forms, said composition is prepared by a process comprising: (a) mixing ribavirin, at least one disintegrant and/or at least one filler to form an homogenous mixture; (b) granulating the mixture in the presence of water to form a granulation; (c) drying the granulation; and (d) mixing at least one disintegrant and/or at least one lubricant with the granulation to produce a ribavirin composition, wherein said ribavirin composition comprises at least 80 weight percent of ribavirin, based on the total weight of the composition.
- the invention provides a quick dissolving, high loading ribavirin composition which is essentially free of ribavirin polymorphic forms, said composition is prepared by a process comprising: (a) mixing ribavirin, at least one disintegrant and/or at least one filler to form an homogenous mixture; (b) granulating the mixture in the presence of a solvent to form a granulation; (c) drying the granulation; (c') milling the dried granulation; and (d) mixing at least one disintegrant and/or at least one lubricant with the milled granulation to produce a ribavirin composition, wherein said ribavirin composition comprises at least 80 weight percent of ribavirin, based on the total weight of the composition.
- the ribavirin compositions prepared by the wet granulation process of the invention are uniform, free flowing, and have adequate bulk density for processing into capsules.
- the ribavirin compositions contain at least 80 weight percent of ribavirin.
- the ribavirin compositions are substantially free of polymorphic forms of ribavirin, i.e., there are no signs of polymorphic change in ribavirin as determined by infrared spectrophotometry.
- the ribavirin compositions of the invention are quick dissolving.
- "quick dissolving” means that about 90% of the ribavirin from the compositions of the invention is consistently dissolved in water in 15 minutes and about 100% of the ribavirin from the compositions of the invention is dissolved in water in about 30 minutes.
- the ribavirin compositions preferably contain at least 80 weight percent of ribavirin, based on the total weight of the composition. More preferably, the compositions contain at least 90 weight percent of ribavirin.
- the ribavirin compositions are prepared by a wet granulation process. In the first step, step (a), ribavirin, at least one disintegrant and/or at least one filler are mixed to form an homogenous mixture.
- disintegrants include pharmaceutically acceptable disintegrants which are chemically and physically compatible with ribavirin.
- Preferred disintegrants are selected from croscarmellose sodium, hydroxypropyl cellulose, hydroxypropylmethyl cellulose, sodium starch glycolate, corn starch, pregelatinized starches, polacrillin potassium, polyacrylates such as Carbopol®, sodium carboxymethyl cellulose, potato starch, microcrystalline cellulose, cross-linked polyvinylpyrrolidone, magnesium aluminium silicate, bentonite, alginic acid and alginates.
- a combination of disintegrants may also be used.
- a preferred disintegrant is croscarmellose sodium.
- the amount of disintegrant in the compositions of the invention is preferably from about 0.1 to about 10 weight percent, based on the total weight of the ribavirin composition. More preferably, the amount of disintegrant in the ribavirin compositions is from about 2 to about 8 weight percent, most preferably about 3 to about 6 weight percent.
- fillers include any pharmaceutically acceptable filler which provides bulk to the ribavirin composition and which is physically and chemically compatible with ribavirin.
- Preferred fillers are selected from lactose anhydrous, microcrystalline cellulose, starch, pregelatinized starch, modified starch, dibasic calcium phosphate dihydrate, calcium sulfate trihydrate, calcium sulfate dihydrate, calcium carbonate, lactose, dextrose, sucrose, mannitol, and sorbitol.
- a combination of fillers may also be used.
- Preferred fillers are mannitol and lactose monohydrate.
- the amount of filler in the compositions of the invention is preferably from about 1 to about 20 weight percent, based on the total weight of the ribavirin composition. More preferably, the amount of filler in the ribavirin compositions is from about 5 to about 17 weight percent, most preferably about 10 to about 15 weight percent.
- a solvent is added to the homogenous mixture prepared in the first step to form a granulation:
- Suitable solvents include, but are not limited to, water, acetonitrile, ethyl acetate, acetone, benzene, toluene, dioxane, dimethylformamide, chloroform, methylene chloride, ethylene chloride, carbon tetrachloride, chlorobenzene, acetone, methanol, ethanol, isopropanol, and butanol.
- a combination of solvents may also be used.
- the solvent is water.
- step (c) the granulation prepared in the second step is dried. Drying is preferably performed using a VMA 1200 Vega drier.
- a milling step is employed in the process following drying.
- a preferred milling device is a BTS 200 high speed mill equipped with 1.1 mm.
- step (d) at least one disintegrant and/or at least one lubricant is mixed with either the dried granulation prepared in step (c) or with the milled granulation prepared in step (c').
- a preferred means of mixing the lubricant with the dried granulation is with a BIN blender.
- a pre-lubrication step may be employed wherein the dried granulation is mixed with a disintegrant prior to mixing with a lubricant.
- lubricants include any pharmaceutically acceptable solid or liquid lubricant which is used to enhance the flow and prevent sticking of the ribavirin composition after granulation and which is chemically and physically compatible with ribavirin.
- Preferred lubricants are selected from magnesium stearate, calcium stearate, zinc stearate, talc, propylene glycol, polyethylene glycol, stearic acid, vegetable oil, sodium benzoate, sodium lauryl sulfate, magnesium lauryl sulfate, mineral oil, and polyoxyethylene monostearate.
- a combination of lubricants may also be used.
- a preferred lubricant is magnesium stearate.
- the amount of lubricant in the compositions of the invention is preferably from about 0.1 to about 5 weight percent, based on the total weight of the ribavirin composition. More preferably, the amount of lubricant in the ribavirin compositions is from about 0.5 to about 2 weight percent, most preferably about 0.8 to about 1.8 weight percent.
- a specific compound used in the process of the invention may have more than one function.
- a disintegrant may also function as a lubricant, or vice versa, etc.
- the amount of such compound should be at least the minimum additive amount required for the respective functions.
- the ribavirin compositions of the invention are preferably in the form of a capsule.
- the ribavirin compositions are encapsulated.
- a preferred encapsulating device is a MG2 Suprema capsule filling machine equipped with a size 2 change part.
- the amount of ribavirin in the compositions of the invention is preferably from about 50 mg to 2500 mg. More preferably, the amount of ribavirin in the compositions is from 200 mg to 400 mg.
- compositions of the invention may contain additional ingredients.
- additional ingredients include natural and/or artificial ingredients which are commonly used to prepare pharmaceutical compositions.
- additional ingredients include enteric coating agents, diluents, binders, anti caking agents, amino acids, fibers, solubilizers, emulsifiers, flavorants, enzymes, buffers, stabilizers, colorants, dyes, antioxidants, anti-adherents, preservatives, electrolytes, glidants, and carrier materials.
- enteric coating agents include enteric coating agents, diluents, binders, anti caking agents, amino acids, fibers, solubilizers, emulsifiers, flavorants, enzymes, buffers, stabilizers, colorants, dyes, antioxidants, anti-adherents, preservatives, electrolytes, glidants, and carrier materials.
- a combination of additional ingredients may also be used.
- Such ingredients are known to those skilled in the art, and thus, only a limited number will be
- enteric coating agents include: hydroxypropylmethylcellulose phthalate, methacrylic acid-methacrylic acid ester copolymer, polyvinyl acetate-phthalate and cellulose acetate phthalate.
- binders include: starches, e.g., potato starch, wheat starch, corn starch; gums such as gum tragacanth, acacia gum, and gelatin; microcrystalline cellulose, e.g., products known under the registered trademarks Avicel, Filtrak, Heweten or Pharmacel, hydroxypropyl cellulose, hydroxyethyl cellulose, and hydroxypropylmethyl cellulose; and polyvinyl pyrrolidone, e.g., Povidone.
- starches e.g., potato starch, wheat starch, corn starch
- gums such as gum tragacanth, acacia gum, and gelatin
- microcrystalline cellulose e.g., products known under the registered trademarks Avicel, Filtrak, Heweten or Pharmacel, hydroxypropyl cellulose, hydroxyethyl cellulose, and hydroxypropylmethyl cellulose
- polyvinyl pyrrolidone e.g., Povidone.
- glidants include: silica, magnesium trisilicate, powdered cellulose, starch, talc and tribasic calcium phosphate.
- Colloidal silica e.g., Aerosil is particularly preferred.
- solubilizers and/or emulsifiers include: sorbitan fatty acid esters such as sorbitan trioleate, phosphatides such as lecithin, acacia, tragacanth, polyoxyethylated sorbitan monooleate and other ethoxylated fatty acid esters of sorbitan, polyoxyethylated fats, polyoxyethylated oleotriglycerides, linolizated oleotriglycerides, polyethylene oxide condensation products of fatty alcohols, alkylphenols or fatty acids or also 1 -methyl-3-(2- hydroxyethy!imidazolidone-(2).
- polyoxyethylated means that the substances in question contain polyoxyethylene chains, the degree of polymerization of which generally lies between 2 and 40 and in particular between 10 and 20.
- Example 1 Three different trials were conducted (Trials I, II, and III) using the ribavirin composition prepared.
- Example 1 In each trial a random sample of the ribavirin composition prepared in Example 1 was analyzed for bulk density and tap density.
- tap density means the measured mass of a powder attained at a limiting volume measured in a cylinder after being “tapped down", typically by a mechanical device. The tap density is measured in accordance with the procedure described in USP 23, NF 18, Supplement 6 (1997), procedure No. 616 at page 3768. The test results are summarized in Table I.
- the ribavirin composition prepared in Example 1 was analyzed using a infrared spectrophotometer which showed no signs of polymorphic change in the ribavirin.
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Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL16169702A IL161697A0 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
JP2003541808A JP2005511587A (en) | 2001-11-02 | 2002-10-31 | A method for the preparation of rapidly soluble highly filled ribavirin compositions |
HU0402364A HUP0402364A2 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
AU2002350082A AU2002350082B9 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
CA002465159A CA2465159A1 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
EP02786613A EP1443911A1 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
MXPA04004181A MXPA04004181A (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions. |
BR0213861-1A BR0213861A (en) | 2001-11-02 | 2002-10-31 | Process for the preparation of fast dissolving high load ribavirin compositions |
HR20040384A HRP20040384A2 (en) | 2001-11-02 | 2004-04-30 | Process for preparing quick dissolving high loading ribavirin compositions |
NO20042143A NO20042143L (en) | 2001-11-02 | 2004-05-25 | Process for the preparation of high-dissolving preparations with high content of ribavirin |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33685301P | 2001-11-02 | 2001-11-02 | |
US60/336,853 | 2001-11-02 |
Publications (1)
Publication Number | Publication Date |
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WO2003039517A1 true WO2003039517A1 (en) | 2003-05-15 |
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ID=23317956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2002/034899 WO2003039517A1 (en) | 2001-11-02 | 2002-10-31 | Process for preparing quick dissolving, high loading ribavirin compositions |
Country Status (16)
Country | Link |
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US (1) | US20030104050A1 (en) |
EP (1) | EP1443911A1 (en) |
JP (1) | JP2005511587A (en) |
KR (1) | KR20050042035A (en) |
CN (1) | CN1585631A (en) |
AU (1) | AU2002350082B9 (en) |
BR (1) | BR0213861A (en) |
CA (1) | CA2465159A1 (en) |
HR (1) | HRP20040384A2 (en) |
HU (1) | HUP0402364A2 (en) |
IL (1) | IL161697A0 (en) |
MX (1) | MXPA04004181A (en) |
NO (1) | NO20042143L (en) |
PL (1) | PL368550A1 (en) |
RU (1) | RU2004116821A (en) |
WO (1) | WO2003039517A1 (en) |
Cited By (6)
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US6720000B2 (en) | 2001-03-19 | 2004-04-13 | Three Rivers Pharmaceutical, Llc | Process for producing wet ribavirin pellets |
WO2004096187A1 (en) * | 2003-04-29 | 2004-11-11 | Pliva-Lachema A.S. | Pharmaceutical composition containing ribavirin as active substance and method of manufacturing thereof |
WO2006002365A2 (en) * | 2004-06-24 | 2006-01-05 | Angiotech International Ag | Microparticles with high loadings of a bioactive agent |
US7538094B2 (en) | 2002-09-19 | 2009-05-26 | Three Rivers Pharmacueticals, Llc | Composition containing ribavirin and use thereof |
WO2011029868A1 (en) | 2009-09-11 | 2011-03-17 | Ratiopharm Gmbh | Pharmaceutical formulation containing ribavirin |
EP2583681A1 (en) * | 2010-06-08 | 2013-04-24 | Laboratorio De Diagnostico Gam, S.a. | Oral veterinary composition for salmonids, comprising 1-beta-d-ribofuranosyl-1h-1,2,4-triazole-3-carboxamide and use thereof for the treatment of infectious salmon anaemia (isa) in salmonids |
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ES2523148T3 (en) * | 2004-05-24 | 2014-11-21 | Takeda Nycomed As | Particle-shaped material comprising a compound containing calcium and a sugar alcohol |
US7723310B2 (en) * | 2004-10-18 | 2010-05-25 | Three Rivers Pharmaceuticals, Llc | Large dose ribavirin formulations |
US20060110479A1 (en) * | 2004-11-24 | 2006-05-25 | Mitra Shankar K | Natural composition for curing hepatitis-B, methods for making the same and pharmaceutical formulations thereof |
US8263137B2 (en) | 2005-08-04 | 2012-09-11 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for women |
US7901710B2 (en) | 2005-08-04 | 2011-03-08 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for use under physiologically stressful conditions |
US8202546B2 (en) | 2005-08-04 | 2012-06-19 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for use under physiologically stressful conditions |
WO2008079343A2 (en) * | 2006-12-21 | 2008-07-03 | Mallinckrodt Inc. | Composition of and method for preparing orally disintegrating tablets containing a high dose of pharmaceutically active ingredients |
US8202996B2 (en) * | 2007-12-21 | 2012-06-19 | Bristol-Myers Squibb Company | Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-chloro-4-methoxy-1-isoquinolinyl)oxy)-N- ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide |
WO2010062996A2 (en) * | 2008-11-28 | 2010-06-03 | Adamas Pharmaceuticals, Inc. | Ribavirin composition |
US20190076467A1 (en) * | 2015-06-09 | 2019-03-14 | Commonwealth Scientific And Industrial Research Organisation | Antiviral conjugates of polyanionic polymer and antiviral drug |
CN106806345B (en) * | 2015-11-27 | 2020-10-13 | 北京科信必成医药科技发展有限公司 | Ribavirin taste masking granules and preparation method thereof |
CN108464972A (en) * | 2018-07-02 | 2018-08-31 | 福州大学 | A kind of anti-pulmonary hypertension oral tablet and preparation method thereof containing Snopori |
JP2023544420A (en) | 2020-10-05 | 2023-10-23 | エックスダブリューファーマ リミテッド | Modified release compositions of gamma-hydroxybutyric acid derivatives |
CN113304114B (en) * | 2021-06-08 | 2022-06-10 | 药大制药有限公司 | Ribavirin granules and preparation method thereof |
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US6541014B2 (en) * | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
US6720000B2 (en) * | 2001-03-19 | 2004-04-13 | Three Rivers Pharmaceutical, Llc | Process for producing wet ribavirin pellets |
-
2002
- 2002-10-31 CN CNA028222172A patent/CN1585631A/en active Pending
- 2002-10-31 JP JP2003541808A patent/JP2005511587A/en active Pending
- 2002-10-31 CA CA002465159A patent/CA2465159A1/en not_active Abandoned
- 2002-10-31 BR BR0213861-1A patent/BR0213861A/en not_active IP Right Cessation
- 2002-10-31 KR KR1020047006543A patent/KR20050042035A/en not_active Application Discontinuation
- 2002-10-31 WO PCT/US2002/034899 patent/WO2003039517A1/en not_active Application Discontinuation
- 2002-10-31 PL PL02368550A patent/PL368550A1/en not_active Application Discontinuation
- 2002-10-31 MX MXPA04004181A patent/MXPA04004181A/en unknown
- 2002-10-31 RU RU2004116821/15A patent/RU2004116821A/en not_active Application Discontinuation
- 2002-10-31 IL IL16169702A patent/IL161697A0/en unknown
- 2002-10-31 HU HU0402364A patent/HUP0402364A2/en unknown
- 2002-10-31 US US10/285,188 patent/US20030104050A1/en not_active Abandoned
- 2002-10-31 EP EP02786613A patent/EP1443911A1/en not_active Withdrawn
- 2002-10-31 AU AU2002350082A patent/AU2002350082B9/en not_active Ceased
-
2004
- 2004-04-30 HR HR20040384A patent/HRP20040384A2/en not_active Application Discontinuation
- 2004-05-25 NO NO20042143A patent/NO20042143L/en not_active Application Discontinuation
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US5914128A (en) * | 1997-12-22 | 1999-06-22 | Schering Corporation | Orally administrable solid dosage form |
US5916594A (en) * | 1997-12-22 | 1999-06-29 | Schering Corporation | Process of making solid ribavirin dosage forms |
US6051252A (en) * | 1997-12-22 | 2000-04-18 | Schering Corporation | Orally administrable solid dosage form |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6720000B2 (en) | 2001-03-19 | 2004-04-13 | Three Rivers Pharmaceutical, Llc | Process for producing wet ribavirin pellets |
US7538094B2 (en) | 2002-09-19 | 2009-05-26 | Three Rivers Pharmacueticals, Llc | Composition containing ribavirin and use thereof |
WO2004096187A1 (en) * | 2003-04-29 | 2004-11-11 | Pliva-Lachema A.S. | Pharmaceutical composition containing ribavirin as active substance and method of manufacturing thereof |
WO2006002365A2 (en) * | 2004-06-24 | 2006-01-05 | Angiotech International Ag | Microparticles with high loadings of a bioactive agent |
WO2006002365A3 (en) * | 2004-06-24 | 2006-03-02 | Angiotech Int Ag | Microparticles with high loadings of a bioactive agent |
WO2011029868A1 (en) | 2009-09-11 | 2011-03-17 | Ratiopharm Gmbh | Pharmaceutical formulation containing ribavirin |
EP2583681A1 (en) * | 2010-06-08 | 2013-04-24 | Laboratorio De Diagnostico Gam, S.a. | Oral veterinary composition for salmonids, comprising 1-beta-d-ribofuranosyl-1h-1,2,4-triazole-3-carboxamide and use thereof for the treatment of infectious salmon anaemia (isa) in salmonids |
Also Published As
Publication number | Publication date |
---|---|
AU2002350082B9 (en) | 2006-08-31 |
HUP0402364A2 (en) | 2005-02-28 |
NO20042143L (en) | 2004-05-25 |
RU2004116821A (en) | 2005-04-20 |
HRP20040384A2 (en) | 2005-08-31 |
AU2002350082B2 (en) | 2006-07-20 |
US20030104050A1 (en) | 2003-06-05 |
CA2465159A1 (en) | 2003-05-15 |
PL368550A1 (en) | 2005-04-04 |
IL161697A0 (en) | 2004-09-27 |
KR20050042035A (en) | 2005-05-04 |
EP1443911A1 (en) | 2004-08-11 |
MXPA04004181A (en) | 2005-01-25 |
JP2005511587A (en) | 2005-04-28 |
BR0213861A (en) | 2004-12-21 |
CN1585631A (en) | 2005-02-23 |
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