[go: up one dir, main page]

WO2005062722A2 - Composition pharmaceutique orale - Google Patents

Composition pharmaceutique orale Download PDF

Info

Publication number
WO2005062722A2
WO2005062722A2 PCT/IN2004/000362 IN2004000362W WO2005062722A2 WO 2005062722 A2 WO2005062722 A2 WO 2005062722A2 IN 2004000362 W IN2004000362 W IN 2004000362W WO 2005062722 A2 WO2005062722 A2 WO 2005062722A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
immediate release
release oral
fexofenadine
agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2004/000362
Other languages
English (en)
Other versions
WO2005062722A3 (fr
Inventor
Ashish Prabhakar Mungre
Manisha Saiprasad Nabar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sun Pharmaceutical Industries Ltd
Original Assignee
Sun Pharmaceutical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sun Pharmaceutical Industries Ltd filed Critical Sun Pharmaceutical Industries Ltd
Publication of WO2005062722A2 publication Critical patent/WO2005062722A2/fr
Publication of WO2005062722A3 publication Critical patent/WO2005062722A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • the present invention relates to an immediate release oral pharmaceutical composition of an antihistamine.
  • the present invention relates to an oral pharmaceutical composition of a piperidinoalkanol compound.
  • Fexofenadine hydrochloride is a piperidinoalkanol compound with the chemical name ( ⁇ )-4- [1 -hydroxy-4-[4-(hydroxydiphenylmethyl)- 1 -piperidinyl]butyl]-c ⁇ , ⁇ -dimethylbenzeneacetic acid hydrochloride.
  • Fexofenadine is a histamine H receptor antagonist useful as an antihistamine, anti-allergy agent and bronchodilator. It is indicated for the relief of symptoms associated with seasonal allergic rhinitis in adults and children 6 years of age and older. It is also indicated for treatment of uncomplicated skin manifestations of chronic idiopathic urticaria in adults and children 6 years of age and older.
  • the recommended dose of fexofenadine for treatment of allergic rhinitis in adults is 60 mg twice daily or 180 mg once daily.
  • the recommended dose of fexofenadine for treatment of chronic idiopathic urticaria in adults is 60 mg twice daily.
  • Fexofenadine hydrochloride is commercially available in the United States of America as Allegra ® capsules and Allegra tablets.
  • United States Patent Application Number 20030203020A1 (priority date Feb 28, 1995, assigned to Hoechst Marion Roussel, Inc) relates to a composition of piperidinoalkanol compounds obtained using specific excipients, and using piperidinoalkanol compound having a specific surface area greater than lm 2 /g.
  • the compositions described and exemplified in this application use the method of wet granulation.
  • the large surface area and the process of wet granulation may be expected to improve bioavailability of the piperidinoalkanol compounds.
  • use of solvents may cause change in the polymorphic form of the piperidinoalkanol and may adversely affect its bioavailability.
  • United States Patent Number 5,290,569 (priority date Apr 12, 1990, assigned to Shionogi and Co.) relates to orally administrable coated granules.
  • the granules are coated to a thickness such that the site and/or time for disintegration or dissolution can be properly regulated.
  • the compositions therefore provide modified release of the drug contained therein.
  • the patent does not suggest or teach immediate release oral compositions that can be obtained by the process of melt granulation.
  • United States Patent Application Number 20020160050A1 (priority date Sep 28, 1999, assigned to Lundbeck) claims melt granulated substantially homogenous composition comprising one or more hydrophilic cellulose ether polymers, a hydrophilic melt binder and a drug.
  • the compositions provide modified release of the drug contained therein, since the cellulose ether used acts as binder or matrix system that regulates release of the drug.
  • United States Patent Application Number 20030228368A1 (priority date Sep 28, 2001 , assigned to Johnson and Johnson) claims an edible solid composition comprising 25-40% w/w of at least one non-aqueous carrier which has a melting temperature less than about 45 degrees C, and about 15-60% w/w of at least one thermoplastic material which has a melting temperature greater than 50 degrees C.
  • the compositions are obtained by placing a mixture of the non-aqueous carrier material, the thermoplastic material and a drug in a mold, heating the mold to 50-100 degrees C, and cooling it to 0-25 degrees C.
  • United States Patent Number 6,723,348 (priority date Nov 16, 2001, assigned to Ethypharm) relates to orodispersible tablets of fexofenadine, which are able to disintegrate in the buccal cavity upon contact with saliva by formation of an easy-to-swallow suspension, in less than 60 seconds containing; fexofenadine, or one of its pharmaceutically acceptable salt, in the form of coated granules, and a mixture of excipients comprising at least one disintegrating agent, a soluble diluent agent and a lubricant.
  • the formulation of this invention is prepared by direct compression of the coated granules of fexofenadine and the mentioned excipients.
  • the patent does not relate to conventional tablet compositions that are meant to be swallowed and which disintegrate in the gastrointestinal tract.
  • Piperidinoalkanol compounds like fexofenadine are hydrophobic in nature and have low water solubility.
  • Direct compression is a method of choice for the manufacture of tablets because it involves minimum number of steps.
  • use of direct compression for preparation of compositions of fexofenadine cause problems such as capping and sticking.
  • tablets made using dry granulation process do not release fexofenadine at a desirable rate.
  • the use of wet granulation processes may cause a change in the polymorphic form of the piperidinoalkanol, and may adversely affect its bioavailability.
  • melt granulation process so that the hydrophobic piperidinoalkanol compounds are in intimate contact with the. thermomelting binding agent used.
  • the use of the process of melt granulation as per the present invention avoids micronisation of the piperidinoalkanol compounds to increase their surface area, avoids use of surfactants and other means such as large amounts of disintegrating agents, avoids use of solvents that may have a deleterious effect on the stability of the piperidinoalkanol compounds, and at the same time provides a process that is feasible and industrially applicable.
  • the present invention provides an immediate release oral pharmaceutical composition
  • an immediate release oral pharmaceutical composition comprising a therapeutically effective amount of fexofenadine or its pharmaceutically acceptable salts, a dissolution enhancing amount of a thermomelting binding agent and phamiaceutically acceptable excipients.
  • Melt granulation is a known process and involves mechanically working a paniculate substance mixed with a thermomelting binder which has a melting point of 40-100°C, so as to fo ⁇ n granules.
  • the thermomelting binding agent melts and adheres to the surface of the particulate drug. The process thus causes adhering of the particles to form granules, which are then processed by methods conventional in the art to obtain pharmaceutical compositions.
  • the the ⁇ nomelting binding agent is present in the oral composition of the present invention in a dissolution enhancing amount.
  • dissolution enhancing amount means that the rate of dissolution of fexofenadine or its pharmaceutically acceptable salt in the presence of the thermomelting binding agent is greater than the rate of dissolution in the absence of the thermomelting binding agent.
  • the amount of the thermomelting binding agent used depends on the agent used and the properties of the agent used.
  • the thermomelting binding agent may be any suitable substance with a melting point less than about 150°C.
  • the thermomelting binding agents used in the composition of this invention typically include hydrophobic agents, hydrophilic agents or mixtures thereof.
  • hydrophobic agent means a substance that has a hydrophilic-lipophilic balance of less than 10, and the term “hydrophilic agent” as used herein means a substance that has a hydrophilic- lipophilic balance of greater than 10. It excludes such hydrophobic agents that in any amounts will not function to enhance dissolution of fexofenadine or its phamiaceutically acceptable salt. However, the use of the term “hydrophobic agent” is not restricted to surfactants, i.e.
  • thermomelting binding agent amphiphilic compounds that have both hydrophobic and hydrophilic properties, but hydrophobic agents such as hydrogenated vegetable oils are also useful as the thermomelting binding agent of the present invention which is capable of enhancing dissolution of fexofenadine or its phamiaceutically acceptable salt.
  • Hydrophobic agents that are not capable by themselves of enhancing the dissolution of fexofenadine or its phamiaceutically acceptable salt, may be used in admixture with a suitable agent such that the mixture acts as a thermomelting binding agent capable of enhancing dissolution.
  • the thermomelting binding agent may be used in an amount ranging from about 5% to about 95% by weight of the composition.
  • thermomelting binding agent is used in an amount ranging from about 15% to about 75% by weight of the composition, more preferably in an amount ranging from about 30% to about 60% by weight of the composition, such that the composition provides an immediate release of fexofenadine or its pharmaceutically acceptable salt.
  • thermomelting binding agents that may be used in the oral pharmaceutical composition of the present invention include, but are not limited to, hydrophilic agents like polyethylene glycols having an average molecular weight of not less than about 400, preferably of not less than about 1,000, more preferably from about 2,000 to 20,000, polyethylene glycol derivatives, saccharides like D-glucose, maltose, fructose and the like, sugar alcohols like xylitol, D-mannitol, D-sorbitol and the like, surfactants like sorbitan, Pluronic F68 and the like and hydrophobic agents like straight-chain saturated hydrocarbons, fats and oils like cocoa butter, beef tallow, lard, hydrogenated soybean oil, and the like, animal and plant waxes like yellow beeswax, white beeswax and the like, higher fatty acids like stearic acid and the like, higher alcohols like stearyl alcohol and the like, hydrogenated plant oils like hydrogenated castor oil, hydrogenated
  • the phamiaceutically acceptable excipients that may be used in the present invention typically include one or more surfactants, disintegrants, binders, wicking agents, lubricants, fillers and the like.
  • surfactants or wetting agents include, but are not limited to, sodium lauryl sulfate, sorbitan fatty acid esters, polyoxyethylene stearates, polyoxyethylene fatty acid esters, poloxamers, polyoxyethylene ethers, sodium docusate, polyethoxylated castor oil and the like.
  • disintegrants examples include, but are not limited to, starch, cellulose derivatives, gums, crosslinked polymers and the like.
  • Binders examples include one or more of starch, gelatin, sugars, cellulose derivatives, polyvinylpyrrolidone and the like.
  • wicking agents include colloidal silicon dioxide, kaolin, titanium dioxide, fumed silicon dioxide, niacinamide, sodium lauryl sulfate, m-pyrol, vinylpy ⁇ olidone polymers such as povidone, or crosslinked polyvinylpyrrolidone such as crospovidone; cellulose and cellulose derivatives such as microcrystalline cellulose, methylcellulose, ethylcellulose, hydroxypropylcellulose, hydroxypropyl cellulose, carboxyalkyl celluloses or crosslinked carboxyalkylcelluloses and their alkali salts; sodium starch glycolate, starch and starch derivatives, ion-exchange resins and the like and mixtures thereof.
  • Fillers that may be used in the present invention include, but are not limited to, lactose, mannitol, calcium carbonate, dicalcium phosphate, starch, microcrystalline cellulose, and the like and mixtures thereof.
  • lubricants include talc, magnesium stearate, calcium stearate, aluminium stearate, stearic acid, hydrogenated vegetable oils, colloidal silicon dioxide, polyethylene glycol, cellulose derivatives such as carboxyalkyl cellulose and its alkali salts, and mixtures thereof.
  • the pharmaceutical excipients are used in amounts conventionally used in the pharmaceutical art and known to a person of skill in the art.
  • the oral pharmaceutical composition of the present invention is prepared by the process of melt granulation, wherein the piperidinoalkanol such as fexofenadine or its phamiaceutically acceptable salt is mixed with the thermomelting binding agent and other phamiaceutically acceptable excipients and heated in a jacketed vessel at a suitable temperature so as to obtain a molten mass.
  • the thermomelting binding agent may be heated so as to obtain a molten mass and the piperidinoalkanol may be added to it later.
  • This mass is then passed through a sieve to obtain granules, which are cooled and lubricated.
  • the lubricated mass is then either compressed to obtain tablets, or is filled in empty gelatin capsules.
  • the granules of the drug obtained from the molten mass may be mixed with placebo granules comprising conventional pharmaceutical excipients, and compressed to obtain tablets.
  • Compressed tablets may optionally be coated with a film coat for providing aesthetic appeal and/or for masking the taste of the piperidinoalkanol. Coating may be carried out using conventional methods and agents known to a person of skill in the pha ⁇ naceutical art.
  • the oral phaniiaceutical composition of the present invention has essentially the same bioavailability as that provided by commercially available compositions of fexofenadine whose New Drug Application (NDA) received approval of the United States Food and Drug Administration (USFDA).
  • NDA New Drug Application
  • USFDA United States Food and Drug Administration
  • the phrase "essentially the same bioavailability" as used herein means that if a pharmaceutical composition comprising fexofenadine or its phamiaceutically acceptable salt and a pharmaceutically acceptable carrier is tested in a crossover study (usually comprising a cohort of at least 10 or more human subjects), the average Area Under the Curve (AUC) and/or the Cmax for each crossover group is at least 80% of the (corresponding) average AUC and/or Cmax observed when the same cohort of subjects is dosed with the fexofenadine formulation whose NDA received approval of USFDA.
  • AUCs, Cmax and crossover studies is, of course well understood in the art.
  • the NDA product is approved for marketing on the basis of its therapeutic efficacy and safety demonstrated in human studies.
  • the therapeutic efficacy and safety parameter may change if there is a change in bioavailability and thus once the NDA is approved, then it continues to be manufactured in a reproducible manner to provide the same bioavailability as the originally approved product. If there is a change in the manufacturing process, then the NDA holder must submit to the USFDA data demonstrating that the bioavailability of the product obtained using the new process is the same as that of the originally approved product.
  • the NDA holder will no longer be able to market the product using the approval received on the original product, and will instead need to file a NDA for the new product to obtain USFDA approval for it.
  • the pha ⁇ naceutical compositions of the present invention are bioequivalent to commercially available preparations of fexofenadine.
  • Approval of a generic version (Abbreviated New Drug Application, AND A) of a proprietary drug (NDA) by the USFDA requires demonstration of "chemical equivalence” (similar quantities and availability of the active ingredient in proprietary and generic formulations), and "bioequivalence” (defined by absorption parameters generally falling between 80% and 125%o of those obtained with the proprietary agent under the same testing conditions).
  • a generic drug fonnulation to be approved by the USFDA has to be bioequivalent to the reference listed drug or the proprietary formulation.
  • the present invention provides a phaniiaceutical composition for the treatment of histamine-mediated conditions that releases fexofenadine in a manner to provide desirable blood level profile of fexofenadine that provides efficacy in the treatment of histamine-mediated conditions.
  • AUC plasma concentration-time curve
  • the term comparable means that 90 percent confidence intervals for die ratio of the population geometric means between the pha ⁇ naceutical composition of the present invention and the fexofenadine composition commercially available in the United States of America, namely Allegra*, based on log-transfonned data, is contained in the limits of 70-135 percent for AUC and C max . More preferred embodiments of the present invention are bioequivalent to fexofenadine composition commercially available in the United States of America. Bioequivalence may be determined according to USFDA guidelines and criteria.
  • Oral pharmaceutical composition in the fonn of tablets comprising fexofenadine hydrochloride was prepared as per Table 1 below. Table 1
  • Fexofenadine hydrochloride was mixed with direct compression grade lactose, Prosolv
  • Oral phaniiaceutical composition in the fonn of tablets comprising fexofenadine hydrochloride was prepared as per Table 2 below. Table 2
  • Fexofenadine hydrochloride was mixed with dibasic calcium phosphate, Prosolv SMCC 90, microcrystalline cellulose, sodium lauryl sulfate, colloidal silicon dioxide and magnesium stearate and blended to obtain a mixture.
  • the mixture obtained was compressed to obtained tablets.
  • the tablets thus obtained were subjected to dissolution testing using United States Pha ⁇ nacopoeia dissolution apparatus, type II, at a speed of 50 rpm.
  • the dissolution medium used was 1800ml of 0.001M HC1.
  • the dissolution was compared with that of Allegra ® tablets. The results are recorded in Table 3 below. Table 3
  • Example 1 The oral phaniiaceutical composition of the present invention was obtained as per the method given in Table 4 below. Table 4
  • Fexofenadine hydrochloride used had a particle size such that 90% of the particles are about 25 microns in diameter.
  • Xylitol, PVP K30 and sodium lauryl sulfate were sifted through a sieve #40 ASTM (ASTM stands for American Society for Testing and Materials) and mixed together in a polybag.
  • ASTM Standard stands for American Society for Testing and Materials
  • the above blend and Fexofenadine hydrochloride were taken in a stainless steel vessel and mixed well. The blend was heated in a stainless steel vessel using water bath maintained at 75-85°C and mixed continuously till a granular mass was obtained. The hot granulated mass was cooled to approximately 70°C with stimng and passed through ASTM 8# sieve. The granules were cooled for 7 hours.
  • the cooled granules were then sifted through ASTM 20# sieve.
  • the granules were blended with Avicel PH 200, sodium lauryl sulfate, colloidal silicon dioxide, sodium starch glycolate and talc.
  • the blend was lubricated with magnesium stearate and compressed into tablets at 600 mg tablet weight. Core tablets were coated using Opadry 035B6773 (Brown).
  • the dissolution profile of the composition of the example 1 was compared with the Allegra ® tablets.
  • the dissolution apparatus used was USP Type II at 50 rpm and the dissolution medium was 1800 ml of 0.001 M HC1. The results are given in table 5 below. Table 5
  • oral phaniiaceutical compositions of the present invention were obtained as per the method given in Table 6 and Table 7 below.
  • Placebo granules comprising lactose monohydrate, com starch and PVP K-30 were prepared by conventional wet granulation process and mixed with the melt-granulated product in amounts as specified in Table 6 above. The granules thus obtained were mixed with the extragranular excipients mentioned in Table 6 and compressed to obtain tablets.
  • Example 11 The oral phaniiaceutical composition of the present invention was obtained as per the method given below in Table 9. Table 9
  • Fexofenadine hydrochloride having a particle size such that d 90 is about 25 microns is used for this composition.
  • Xylitol, PVP K30 and sodium lauryl sulfate were sifted through ASTM #40 and mixed in a polybag.
  • Fexofenadine hydrochloride was then added to this mixture.
  • the blend thus obtained was heated in a stainless steel vessel using a water bath maintained at 80+10°C, and mixed continuously to obtain a granular mass. The mass was cooled to room temperature for about 2 hours, followed by sifting of the granules through ASTM #20.
  • the granules were then mixed with Avicel PH 200, starch 1500, sodium lauryl sulfate, colloidal silicon dioxide, sodium starch glycolate, talc and magnesium stearate. This mixture was then compressed to obtain tablet cores that were then coated with Opadry to a weight gain of about 3% by weight of the core.
  • the dissolution profile of the coated tablets thus obtained was compared with the Allegra ® tablets.
  • the dissolution apparatus used was USP Type II at 50 rpm and the dissolution medium was 1800 ml of 0.001 M HCl. The results are given in table 12 below. Table 12
  • the pham acokinetic assessment was based on the plasma levels of fexofenadine hydrochloride measured by blood sampling. Blood samples were obtained before dosing and at the following times after administration of both the reference and test medications: 0.5, 1.0, L5, 1.75, 2.0, 2.25, 2.5, 2.75, 3.0, 3.5, 4.0, 6.0, 8.0, 12.0, 16.0 and 24.0 hours.
  • the phaniiaceutical composition of example 12 was found to be bioequivalent to Allegra ® .

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une composition pharmaceutique orale à libération immédiate contenant une quantité efficace sur le plan thérapeutique de fexofénadine ou ses sels acceptables sur le plan pharmaceutique, une quantité augmentant la dissolution d'un agent de liaison thermofusible et des excipients acceptables sur le plan pharmaceutique.
PCT/IN2004/000362 2003-11-21 2004-11-22 Composition pharmaceutique orale Ceased WO2005062722A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1204MU2003 2003-11-21
IN1204/MUM/2003 2003-11-21

Publications (2)

Publication Number Publication Date
WO2005062722A2 true WO2005062722A2 (fr) 2005-07-14
WO2005062722A3 WO2005062722A3 (fr) 2005-09-22

Family

ID=34717597

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000362 Ceased WO2005062722A2 (fr) 2003-11-21 2004-11-22 Composition pharmaceutique orale

Country Status (1)

Country Link
WO (1) WO2005062722A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101884628A (zh) * 2010-07-13 2010-11-17 浙江万马药业有限公司 一种含盐酸非索非那定药物组合物的制备方法
WO2011151733A3 (fr) * 2010-04-21 2012-01-26 Sanofi-Aventis Composition à base de fexofénadine et sa méthode de préparation
WO2012159960A1 (fr) * 2011-05-20 2012-11-29 Aventis Pharmaceuticals Inc. Composition pharmaceutique contenant de la fexofénadine
US9289416B2 (en) 2010-08-04 2016-03-22 Gruenenthal Gmbh Pharmaceutical dosage forms comprising 6′-fluoro-(N-methyl- or N,N-dimethyl-)-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248363B1 (en) * 1999-11-23 2001-06-19 Lipocine, Inc. Solid carriers for improved delivery of active ingredients in pharmaceutical compositions
IN192750B (fr) * 2000-12-15 2004-05-15 Ranbaxy Lab Ltd
US6723348B2 (en) * 2001-11-16 2004-04-20 Ethypharm Orodispersible tablets containing fexofenadine

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011151733A3 (fr) * 2010-04-21 2012-01-26 Sanofi-Aventis Composition à base de fexofénadine et sa méthode de préparation
CN103002874A (zh) * 2010-04-21 2013-03-27 赛诺菲 基于非索非那定的组合物及其制备方法
TWI478713B (zh) * 2010-04-21 2015-04-01 Sanofi Sa 以菲索特芬那定（ｆｅｘｏｆｅｎａｄｉｎｅ）為主之組合物及其製備方法
CN103002874B (zh) * 2010-04-21 2015-04-08 赛诺菲 基于非索非那定的组合物及其制备方法
CN101884628A (zh) * 2010-07-13 2010-11-17 浙江万马药业有限公司 一种含盐酸非索非那定药物组合物的制备方法
US9289416B2 (en) 2010-08-04 2016-03-22 Gruenenthal Gmbh Pharmaceutical dosage forms comprising 6′-fluoro-(N-methyl- or N,N-dimethyl-)-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine
US10912763B2 (en) 2010-08-04 2021-02-09 Grünenthal GmbH Pharmaceutical dosage forms comprising 6′-fluoro-(N-methyl- or N,N-dimethyl-)-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine
WO2012159960A1 (fr) * 2011-05-20 2012-11-29 Aventis Pharmaceuticals Inc. Composition pharmaceutique contenant de la fexofénadine
CN103687592A (zh) * 2011-05-20 2014-03-26 安万特药物公司 包含非索非那定的药物组合物

Also Published As

Publication number Publication date
WO2005062722A3 (fr) 2005-09-22

Similar Documents

Publication Publication Date Title
AU2009200460B2 (en) Stable extended release oral dosage composition
US7741374B1 (en) Methods of use of fenofibric acid
US9278063B2 (en) Press-coated orally-disintegrating tablets
RU2467750C2 (ru) Ниацинсодержащие фармацевтическая композиция (варианты) и таблеточный препарат (варианты), способ снижения гиперемии и способ приготовления ниацинсодержащей таблетки
MX2008015359A (es) Forma de dosis farmaceutica de liberacion sostenida que contiene fenilefrina.
JP2017537168A (ja) 即放性乱用抑止性顆粒剤形
WO2008070072A2 (fr) Formes, compositions de carvédilol, et leurs procédés de préparation
JPWO2010147169A1 (ja) 溶出性の改善された医薬組成物
CA2451519C (fr) Comprime contenant de la cetirizine et de la pseudoephedrine
US20130143897A1 (en) Oral controlled release pharmaceutical compositions of blonanserin
US7226614B2 (en) Tablet comprising cetirizine and pseudoephedrine
JP2018104324A (ja) 徐放性製剤
US20140178484A1 (en) Multi-particulate pharmaceutical composition
WO2005062722A2 (fr) Composition pharmaceutique orale
US20050048118A1 (en) Modified release venlafaxine hydrochloride tablets
JP2023052494A (ja) 抗凝固薬の即時放出医薬製剤及びその調製方法
US20100143471A1 (en) Novel reduced dose pharmaceutical compositions of fexofenadine and pseudoephedrine
JP2005519053A (ja) 放出が改良された薬剤
PL194595B1 (pl) Preparat tiagabiny o przedłużonym uwalnianiu orazjego zastosowanie
JP2022031251A (ja) 医薬組成物
TW202224681A (zh) 用於治療或預防高血壓及高膽固醇血症之單一劑型的醫藥組成物
KR101199654B1 (ko) 안정한 서방출형의 경구 투여용 조성물
JP2022027636A (ja) 安定化方法
WO2005115092A2 (fr) Composition pharmaceutique orale
HK1064596B (en) Tablet comprising cetirizine and pseudoephedrine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DPEN Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

WWW Wipo information: withdrawn in national office

Country of ref document: DE

122 Ep: pct application non-entry in european phase