WO2016130094A1 - Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c - Google Patents

Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c Download PDF

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Publication number
WO2016130094A1
WO2016130094A1 PCT/TR2015/000046 TR2015000046W WO2016130094A1 WO 2016130094 A1 WO2016130094 A1 WO 2016130094A1 TR 2015000046 W TR2015000046 W TR 2015000046W WO 2016130094 A1 WO2016130094 A1 WO 2016130094A1
Authority
WO
WIPO (PCT)
Prior art keywords
pseudoephedrine
ibuprofen
vitamin
tablet composition
pharmaceutical composition
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/TR2015/000046
Other languages
English (en)
Inventor
Ersin Yildirim
Hakan Gürpinar
Soner ALBOY
Tolga Ramazan KARASU
Mustafa Serkan SOLMAZ
Mesut ERDOĞAN
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.)
Pharmactive Ilac Sanayi Ve Ticaret AS
Original Assignee
Pharmactive Ilac Sanayi Ve Ticaret AS
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 Pharmactive Ilac Sanayi Ve Ticaret AS filed Critical Pharmactive Ilac Sanayi Ve Ticaret AS
Priority to PCT/TR2015/000046 priority Critical patent/WO2016130094A1/fr
Priority to TR2017/10637T priority patent/TR201710637T1/tr
Publication of WO2016130094A1 publication Critical patent/WO2016130094A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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

Definitions

  • This invention relates to stable pharmaceutical composition
  • ibuprofen pseudoephedrine and vitamin C.
  • Non-steroidal anti-inflammatory drugs are ideaiiy suited for use in cold formulations for their analgesic, anti-infiammatory, and antipyretic activity and low incidence of untoward side effects.
  • Decongestants are effective for controlling symptoms of nasal and sinus congestion. Swollen, inflamed mucous membranes cause congestion. Decongestants constrict the blood vessels in swollen mucous membranes. This constriction makes tissues shrunk and decongested because constricted blood vessels allow for less fluid to leak into the inflamed tissues.
  • Vitamins are substances that human body needs to grow and develop normally. There are many vitamins human body needs. Some of them; vitamin A, B vitamins (thiamine, riboflavin, niacin, pantothenic acid, biotin, vitamin B-6, vitamin B-12 and folate), vitamin C, vitamin D, vitamin E, vitamin K.Each vitamin has specific jobs.
  • ibuprofen chemical name is 2-(4-isobutylphenyl) propionic acid, is a well-known antiinflammatory drug having a molecular weight of 206.28. Ibuprofen is now marketed generically and is patented in the 60's.
  • Ibuprofen has been used in humans for many years. It is a member of nonsteroidal antiinflammatory drugs (NSAID). Ibuprofen is used for relieving pain and reducing inflammation. And also it has antipyretic properties to reduce fever. Ibuprofen is regarded one of the safest NSAIDs available. However ibuprofen can not be very effective to relief flu, if used alone. researchers have improved combinations of ibuprofen with decongestants to get quick and effective solutions to treat flu syndromes. Ibuprofen is combined pseudoephedrine, phenylefrine, diphenhydramine in market.
  • NSAID nonsteroidal antiinflammatory drugs
  • ibuprofen is a racemic mixture. It is only the racemic mixture which has in fact ever been marketed.
  • the S(+) enantiomer is the active form of ibuprofen.
  • Pseudoephedrine chemical name is (1 S,2S)-2-methylamino-1-phenylpropan-1-ol
  • Pseudoephedrine is commonly used as decongestant.
  • Pseudoephedrine has been used either as a single ingredient or (more commonly) in combination with dextromethorphan or paracetamol or NSAIDs.
  • EP2139455 relates to a tablet comprising at least a first (pseudoephedrine) and second active (ibuprofen).
  • the first and second active are blended together optionally with other excipients and formed into a tablet.
  • the present invention relates to administration of solid oral dosage form comprising ibuprofen, pseudoephedrine, vitamin C and one or more pharmaceutically acceptable excipients, to a patient in need of Vitamin C combined with ibuprofen- pseudoephedrine treatment having a flu and/or prone to that.
  • the invention provides a pharmaceutical composition in the form of bilayer tablet consisting essentially of:
  • first active ingredient such as ibuprofen
  • second active ingredient pseudoephedrine is mixed with the first active with additional excipients.
  • second portion containing a third active ingredient vitamin C with additional excipients same or different from excipients used at first portion.
  • first portion mixture and the second portion mixture is compressed as bilayer tablet wherein the compressed two portions are going to be coated.
  • pharmaceutical composition may include many active ingredients. These active ingredients can be a vitamin, an analgesic, a NSAID or a decongestant drug.
  • taking vitamins during cold&flu symptoms is extremely important to get the body stronger.
  • Present invention has the advantage to shorten the period of illness compared to vitamin unused treatment conditions. Therefore, it becomes important to support cold relief combinations with vitamins for an effective treatment period.
  • composition is a bilayer tablet composition for use in the treatment of cold and flu, characterized in that it comprises a) a therapeutically effective amount of ibuprofen or pharmaceutical a
  • ibuprofen compound and pseudoephedrine compound are in the same layer and vitamin C is in the separate layer.
  • pharmaceutical composition may be formulated, for example, in the form of pharmaceutical compositions for oral administration such as granules, fine granules, powders, tablets, caplets, hard capsules, soft capsules, syrups, emulsions, suspensions, solutions and the like, or in the, form for sublingual a buccal administration.
  • tablet may include multiple layer-compressed tablets, bilayer tablets, mouth dissolving tablets or orally disintegrating tablets, water dispersible tablets, and chewable tablets wherein tablet is scored or unscored.
  • pharmaceutical composition can be prepared by various formulation techniques known to the person skilled in the art, such as, but not limited to direct compression, wet or dry granulation, slugging, hot melt granulation, extrusion-spheronization, hot melt extrusion, fluidized bed granulation, spray drying spray coating, and solvent evaporation and the like.
  • present invention is a pharmaceutical composition containing a therapeutically effective amount of ibuprofen, pseudoephedrine and Vitamin C both active ingredients being present in the free state or in the form of a pharmaceutically acceptable salt, solvate, enantiomer.
  • Another object of the present invention is a pharmaceutical composition in a form being able to be administered by the oral route.
  • present invention relates to bilayer coated tablet formulations of three active ingredients.
  • the second active ingredient that is granulated with first active ingredient selected from pseudoephedrine or pharmaceutical acceptable salts thereof is in the form of hydrochloride or hydrobromide salt thereof.
  • L- ascorbic acid is mixed with one or more excipients as the second portion of the invention.
  • the process of preparing the stable pharmaceutical composition comprises steps of preparing a first layer comprising ibuprofen or pharmaceutical acceptable salts or enantiomer thereof, and pseudoephedrine or pharmaceutical acceptable salts thereof, the second layer comprising Vitamin C followed by compressing of bilayer tablet and coating by a protective layer.
  • composition and its formulation process involve avoiding chemical interaction of ibuprofen and pseudoephedrine with ascorbic acid, using pharmaceutically acceptable formulation technique and excipients in the dosage form.
  • An object of the invention is a pharmaceutical composition having a first layer containing ibuprofen and pseudoephedrine, being present in the free state or in the i
  • composition being intimately mixed in the composition; and a second layer containing ascorbic acid not being intimately mixed with the first layer.
  • step (e) optionally, coating a protective layer over the bilayer tablet prepared in step (d).
  • pharmaceutical composition may comprise single or plurality of multiple- compression tablets which are formed by two or more compression cycles.
  • Each compression cycle uses, alternatively, separate or combined portions of each of ibuprofen, pseudoephedrine and ascorbic acid.
  • a multiple-compression tablet can exist as, for example, a layered tablet, as a compression-coated tablet, or as an inlay tablet.
  • a layered tablet is a tablet which is made up of two or more distinct cores of granulation compressed together with the individual layers lying one on top of another.ln one embodiment this formulation discloses a bilayer pharmaceutical compressed tablet capable of liberating two or more drugs at different or same release rates.
  • the tablet consists of two layers wherein one layer is made from Formulation (A) and the other layer is made from Formulation (B), resulting in a bilayer tablet.
  • the components of the pharmaceutical composition according to the present invention are brought together into a bilayer tablet for oral administration according to standard practice and procedures well known to one of ordinary skill in the art using conventional formulation and manufacturing techniques such as that described in the following examples.
  • the barrier layer may be formed by any method, including compression, molding, dipping, or spray coating.
  • An object of the present invention is to provide a pharmaceutical composition in oral dosage form as a bilayer tablet which provides immediate release of a ibuprofen/pseudoephedrine combination and again immediate release of a Vitamin C drug that exhibits acceptable bioavailability of each compound.
  • An additional object of the invention is to provide a pharmaceutical composition in bilayer tablet form of high integrity consisting of an immediate release form of two layers. By this way, chemical interaction of Vitamin C with other active ingredients can be eliminated. Because vitamin C is incompatible with ibuprofen and pseudoephedrine. Oral daily dose of ibuprofen is varying from 600 mg to 3200 mg. Approve
  • ibuprofen administration includes 200 to 400 mg orally every 4 to 6 hours for dysmenorrhea, 400 to 800 mg orally every 6 to 8 hours for osteoarthritis, for rheumatoid arthritis, 200 to 400 mg orally every 4 to 6 hours for pain, 200 to 400 mg orally every 4 to 6 hours for fever.
  • the recommended dosage for pseudoephedrine hydrochloride in a sustained release formulation can be 120 mg twice daily (b.i.d.).
  • compositions of the present invention are generally formulated in dosage units containing from 200 to 600 mg of ibuprofen and 30 to 120 mg of pseudoephedrine and 100 to 400 mg of Vitamin C per unit dosage.
  • Another object of the present invention is a pharmaceutical composition containing 200 mg of ibuprofen and 30 mg of pseudoephedrine and 300 mg of Vitamin C or 400 mg of ibuprofen and 60 mg of pseudoephedrine and 300 mg of Vitamin C.
  • the pharmaceutical composition of the invention is suitable for BID.TID or QID administrations.
  • BID,TID,QID refer to two times a day, three times a day, four times a day respectively.
  • composition of the present invention may further comprise diluents, binders, suspending agents, disintegrants, stabilizing agents, adsorbents, surfactants, lubricants, disinfectants, glidants, flavoring agents, sweeteners and other pharmaceutical additives or excipient to facilitate the physical formulation of various dosage forms like tablets, capsules, orally disintegrating tablets, chewable tablets and suspensions (including dry powders or granules for suspension).
  • Binders can be selected from the group, but are not limited to, methyicellulose, sodium carboxymethycellulose, calcium carboxymethycellulose, ethyl cellulose, hydroxypropyl methyicellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, silicified microcrystalline cellulose(SMCC), polyvinyl pyrrolidone (Povidon), gelatine, polyvinyl alcohol, acacia, tragacanth, guar, pectin, starch paste, pre-gelatinized starch, alginic acid, compressible sugar, liquid glucose, dextrates, dextrin, dextrose, maltodextrin, magnesium aluminium silicate, polymethacrylates, sorbitol and other materials known to one of ordinary skill in the art.
  • a preferred binder is polyvinylpyrrolidone.
  • a mixture of binders may also be used. The binder is preferably used in an amount of from about 0.5 to about
  • Diluents can be selected from the group, but are not limited to, calcium carbonate, calcium phosphate, calcium sulphate, carboxymethylcellulose calcium, carboxymethylcel!ulose sodium, compressible sugar, confectioner's sugar, dextrates, dextrin, dextrose, dibasic calcium phosphate dihydrate, dibasic calcium phosphate, fructose, glyceryl palmitostearate, glycine, hydrogenated vegetable oil-type 1 , kaolin, lactose, maize starch, magnesium carbonate, magnesium oxide, maltodextrin, mannitol, microcrystalline cellulose, polymethacrylates, potassium chloride, powdered cellulose, pregelatinised starch, sodium chloride, sorbitol, starch, sucrose, sugar spheres, talc, tribasic calcium phosphate, and xylitol or mixture thereof.
  • a preferred diluent is calcium hydrogen phosphate and/or microcrystalline cellulose. Diluent
  • the combination of above-mentioned disintegrants can also be used.
  • the preferred disintegrants are croscarmellose sodium and microcrystalline cellulose.
  • the disintegrant is preferably used in an amount of from about 0.5% to about 20% by weight.
  • Lubricants can be selected from the group, but are not limited to, vegetable oils, such as hydrogenated vegetable oil or hydrogenated castor oil, polyethylene glycols, such as polyethylene glycol (PEG)-4000 and PEG-6000; stearic acid; derivatives of stearic acid, such as magnesium stearate, sodium stearate, calcium stearate, zinc stearate, glyceryl monostearate, glyceryl palmitostearate and sodium stearyl fumarate; mineral salts, such as talc; inorganic salts; organic salts, such as sodium benzoate, sodium acetate, sodium chloride and sodium oleate; and polyvinyl alcohols, microcrystalline cellulose, sodium lauryl sulfate, silica, colloidal silica, cornstarch, calcium silicate, magnesium silicate, silicon hydrogel and other materials known to one of ordinary skill in the art.
  • the preferred lubricant is talc and hydrogenated castor oil.
  • G!idants can be selected from the group, but are not limited to, colloidal silicon dioxide, colloidal silica, cornstarch, talc, calcium silicate, magnesium silicate, magnesium trisilicate, amorphous silica, colloidal silicon, silicon hydrogel, powdered cellulose, silicon dioxide, talc, tribasic calcium phosphate and other materials known to one of ordinary skill in the art. Glidants are used in an amount from about 0.1 to about 30% percent by weight.
  • Dispersing agents or dispersants can be selected from the group, but are not limited to, colloidal silicon dioxide, talc, magnesium stearate and titanium dioxide and other materials known to one of ordinary skill in the art.
  • Stabilizing agent can be selected from the group, but are not limited to, consisting of polysorbates, cellulose derivatives such as hydroxylpropylce!lulose, hydroxylpropylmethylcellulose, poloxamers, carbomers, silicon dioxide, carbonates, sulfates phosphates, hydroxides of alkaline or alkaline earth metals, sodium carboxymethyl cellulose, polyvinylpyrrolidone, Labrasol®, Gelucire®, gelatin, lecithin (phosphatides), gum acacia, cholesterol, tragacanth, carotenoids, polyoxyethylene alkyl ethers, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters, sorbitan fatty acid esters, polyethylene glycols, polyoxyethylene stearates, mono and diglycerides, colloidal silicon dioxide, sodium dodecylsulfate, magnesium aluminum silicate, triethanolamine, stearic acid, calcium stearate, glycerol
  • Polymers can be selected from the group, but are not limited to, hydroxypropylmethyl cellulose, microcrystalline cellulose, hydroxypropyl cellulose, ethyl cellulose, hydroxypropylmethyl cellulose phthalate, hydroxypropylmethyl cellulose ⁇ ⁇
  • cellulose acetate phthalate cellulose acetate phthalate
  • methacrylic polymers aminoalkyl methacrylate copolymer
  • Surfactants can be selected from the group, but are not limited to, also polyoxyethylene hardened castor oil, glyceryl monostearate, sorbitan monostearate, sorbitan monopalmitate, sorbitan monolaurate, polyoxyethylene-polyoxypropylene block copolymers, polysorbates 80, sodium laurylsulfate, macrogols, sucrose esters of fatty acids and other materials known to one of ordinary skill in the art.
  • Example 1 and 2 show us the development of ibuprofen/pseudoephedrine studies. Final formula of ibuprofen/pseudoephedrine combination is fixed as shown in example 2.
  • tablet consists of two layers wherein one layer is consisting ibuprofen/pseudoephedrine combination and the other layer is consisting ascorbic acid, resulting in a bilayer tablet.
  • the components of the pharmaceutical composition according to the present invention are brought together into a bilayer tablet for oral administration as shown in examples 3, 4, and 5.
  • the following examples are understood to be illustrative only.
  • the final mixture is then compressed to form a tablet.
  • the tablets are finally coated with opadry yellow.
  • isopropyl alcohol, povidone and talc is mixed in a stainless container for 10 minutes.
  • the ibuprofen and povidone parts are then combined together to form a next mixture. Then the mixture is dried.
  • Mixture of ibuprofen, calcium hydrogen phosphate and croscarmellose sodium mixture is granulated by addition of separately prepared isopropyl alcohol, povidone and talc mixture and let it to dry.
  • Half amounts of colloidal silicon dioxide and microcrystalline cellulose are added to dried mixture and mixed for extra 10 minutes.
  • the remained parts of colloidal silicon dioxide, microcystalline cellulose and pseudoephedrine hydrochloride is mixed separately and added to final mixture.
  • First layer mixture is prepared after addition of croscarmellose sodium and oil to the final mixture.
  • Second layer mixture is prepared separately by mixing ascorbic acid, microcrystailine cellulose, colloidal silicon dioxide and oil.
  • Tablets are prepared according to procedure followed at example 3. Separately prepared two parts are then compressed according to spesifications to form a bilayer tablet. The tablets are finally coated with opadry blue.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une composition de type comprimé bicouche comprenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine C, le composé d'ibuprofène et le composé de pseudo-éphédrine étant dans la même couche et la vitamine C dans l'autre.
PCT/TR2015/000046 2015-02-10 2015-02-10 Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c Ceased WO2016130094A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/TR2015/000046 WO2016130094A1 (fr) 2015-02-10 2015-02-10 Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c
TR2017/10637T TR201710637T1 (tr) 2015-02-10 2015-02-10 Ibuprofen, psödoefedri̇n ve vi̇tami̇n c i̇çeren bi̇r farmasöti̇k kompozi̇syon

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/TR2015/000046 WO2016130094A1 (fr) 2015-02-10 2015-02-10 Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c

Publications (1)

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WO2016130094A1 true WO2016130094A1 (fr) 2016-08-18

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PCT/TR2015/000046 Ceased WO2016130094A1 (fr) 2015-02-10 2015-02-10 Composition pharmaceutique contenant de l'ibuprofène, une pseudo-éphédrine et de la vitamine c

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TR (1) TR201710637T1 (fr)
WO (1) WO2016130094A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190388363A1 (en) * 2018-06-21 2019-12-26 Sawai Pharmaceutical Co., Ltd. Sustained-release preparation containing pseudoephedrine or a pharmaceutically acceptable salt thereof
WO2021150178A1 (fr) * 2020-01-23 2021-07-29 Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A.Ş. Compositions pharmaceutiques comprenant de l'ibuprofène, de la pseudoéphédrine et de l'acide ascorbique

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6120802A (en) * 1995-10-23 2000-09-19 Basf Aktiengesellschaft Method of producing multi-layer medicaments in solid form for oral or rectal administration
US6251945B1 (en) * 1999-01-14 2001-06-26 Knoll Aktiengesellschaft Pharmaceutical mixture comprising a combination of a profen and other active compounds
US20010043959A1 (en) * 2000-02-23 2001-11-22 Daniel Gelber Composition and method for treating the effects of diseases and maladies
JP2007302578A (ja) * 2006-05-09 2007-11-22 Sorm Co Ltd 総合感冒薬組み合わせ製剤
EP2139455A2 (fr) 2007-03-24 2010-01-06 Reckitt Benckiser Healthcare (UK) Limited Comprimé présentant une stabilité améliorée avec au moins deux ingrédients actifs

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6120802A (en) * 1995-10-23 2000-09-19 Basf Aktiengesellschaft Method of producing multi-layer medicaments in solid form for oral or rectal administration
US6251945B1 (en) * 1999-01-14 2001-06-26 Knoll Aktiengesellschaft Pharmaceutical mixture comprising a combination of a profen and other active compounds
US20010043959A1 (en) * 2000-02-23 2001-11-22 Daniel Gelber Composition and method for treating the effects of diseases and maladies
JP2007302578A (ja) * 2006-05-09 2007-11-22 Sorm Co Ltd 総合感冒薬組み合わせ製剤
EP2139455A2 (fr) 2007-03-24 2010-01-06 Reckitt Benckiser Healthcare (UK) Limited Comprimé présentant une stabilité améliorée avec au moins deux ingrédients actifs

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190388363A1 (en) * 2018-06-21 2019-12-26 Sawai Pharmaceutical Co., Ltd. Sustained-release preparation containing pseudoephedrine or a pharmaceutically acceptable salt thereof
US10842760B2 (en) * 2018-06-21 2020-11-24 Sawai Pharmaceutical Co., Ltd. Sustained-release preparation containing pseudoephedrine or a pharmaceutically acceptable salt thereof
WO2021150178A1 (fr) * 2020-01-23 2021-07-29 Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A.Ş. Compositions pharmaceutiques comprenant de l'ibuprofène, de la pseudoéphédrine et de l'acide ascorbique

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