WO1998052545A1 - Compositions pharmaceutiques a base de flurbiprofene et d'un agent de masquage de brulure pour le traitement de l'angine - Google Patents

Compositions pharmaceutiques a base de flurbiprofene et d'un agent de masquage de brulure pour le traitement de l'angine Download PDF

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Publication number
WO1998052545A1
WO1998052545A1 PCT/EP1998/003180 EP9803180W WO9852545A1 WO 1998052545 A1 WO1998052545 A1 WO 1998052545A1 EP 9803180 W EP9803180 W EP 9803180W WO 9852545 A1 WO9852545 A1 WO 9852545A1
Authority
WO
WIPO (PCT)
Prior art keywords
flurbiprofen
compound
throat
therapeutically effective
burn
Prior art date
Application number
PCT/EP1998/003180
Other languages
English (en)
Inventor
David Michael Barrett
Huw Lyn Jones
Idwal Jones
Carl Simon Smith
Original Assignee
The Boots Company Plc
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
Priority claimed from GBGB9710632.2A external-priority patent/GB9710632D0/en
Priority claimed from GBGB9710525.8A external-priority patent/GB9710525D0/en
Application filed by The Boots Company Plc filed Critical The Boots Company Plc
Priority to AU79167/98A priority Critical patent/AU7916798A/en
Publication of WO1998052545A1 publication Critical patent/WO1998052545A1/fr

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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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays

Definitions

  • the present invention relates to new pharmaceutical compositions containing the non-steroidal anti-inflammatory drug flurbiprofen which also has analgesic and antipyretic activity.
  • the invention also relates to the use of these new pharmaceutical compositions in the treatment of the symptoms of colds and flu, particularly sore throat.
  • the flurbiprofen molecule exists in two enantiomeric forms and the term flurbiprofen as used herein is intended to embrace the individual enantiomers and mixtures thereof in any proportion including a 1 :1 mixture which is herein referred to as the racemic form.
  • Flurbiprofen can exist in the form of pharmaceutically acceptable salts or in the form of derivatives such as esters and such salts or esters are embraced by the term flurbiprofen as used herein.
  • Flurbiprofen would be expected to cause an unpleasant burning sensation at the back of the mouth when retained in the mouth. This would clearly be unacceptable to the patient being treated.
  • the present applicants have surprisingly found that an unacceptable burning sensation is not experienced when the pharmaceutical compositions of the present invention are used to treat the symptoms of colds and flu, particularly sore throat, but that the patient does receive relief of the symptoms of the cold or flu eg sore throat.
  • a first aspect of the present invention provides pharmaceutical compositions comprising a combination of a therapeutically effective amount of flurbiprofen with a therapeutically effective amount of one or more active ingredients selected from an antihistamine, a cough suppressant, a decongestant, an expectorant, a muscle relaxant, a centrally acting analgesic, a local anaesthetic, an antibacterial compound, an antiviral compound, an antibiotic compound, an antifungal compound, minerals and vitamins in the form of a masticable or suckable solid dosage form or a liquid or a spray.
  • active ingredients selected from an antihistamine, a cough suppressant, a decongestant, an expectorant, a muscle relaxant, a centrally acting analgesic, a local anaesthetic, an antibacterial compound, an antiviral compound, an antibiotic compound, an antifungal compound, minerals and vitamins in the form of a masticable or suckable solid dosage form or a liquid or a spray.
  • Suitable antihistamines include acrivastine, azatadine, buclizine, cetirizine, cinnarizine, clemastine, loratidine and pharmaceutically acceptable salts thereof.
  • Suitable cough suppressants include codeine, dextromethorphan or pholcodine and pharmaceutically acceptable salts thereof.
  • Suitable decongestants include pseudoephedrine, phenylpropanolamine and phenylephrine and pharmaceutically acceptable salts thereof.
  • Suitable expectorant include acetylcysteine, ammonium chloride, carbocysteine, guaifensin and potassium citrate.
  • a suitable muscle relaxant is methocarbamol.
  • Suitable centrally acting analgesics include codeine and its salts and hydrocodone.
  • Suitable local anaesthetics include benzocaine, lignocaine, mepivacaine, prilocaine, and pharmaceutically acceptable salts thereof.
  • Suitable antibacterial compounds include amylmetacresol, dichlorobenzyl alcohol, quaternary ammonium compounds such as cetrimide, or benzalkonium chloride.
  • Suitable antiviral compounds include zinc salts (for example the acetate, gluconate and ascorbate salts), acyclovir and its sodium salt.
  • a suitable antibiotic is metronidazole.
  • Suitable antifungal compounds include nystatin, amphotericin, imidazoles such as miconazole and triazoles such as fluconazole.
  • Suitable minerals include zinc and selenium salts.
  • Suitable vitamins include vitamins A, C, D, E and K, sodium ascorbate, riboflavine and thiamine hydrochloride.
  • a further aspect of the present invention provides pharmaceutical compositions comprising a combination of a therapeutically effective amount of flurbiprofen with a bum-masking amount of an agent which has a warming effect on the mucosa of the throat in the form of a masticable or suckable solid dosage form or a liquid or a spray.
  • Suitable warming agents include ginger, chilli and agents containing or consisting of anethole.
  • Anethole (1-methoxy-4-(1-propenyl)benzene or p-propenylanisole) is found naturally as the chief constituent of anise oil, star anise oil and fennel oil. It can be incorporated into the compositions in the present invention in substantially pure form, produced either by extraction from the above oils or synthetically, or it may be incorporated as one of the above oils. The amount of anethole should be such that the required amount of taste masking is obtained.
  • compositions of the present invention are intended for use in the treatment of the symptoms of colds and flu including particularly sore throat by the administration to a patient in need thereof of a pharmaceutical composition according to the present invention in the form of a masticable or suckable solid dosage form or a liquid or a spray containing a therapeutically effective amount of flurbiprofen which releases the flurbiprofen in the oral cavity so as to deliver the flurbiprofen to the surface of the sore throat.
  • the solid dosage form may be a lozenge which is intended to be sucked by the patient or a masticable or suckable tablet, capsule, pastille or gum, for example chewing gum.
  • the term "lozenge” as used herein is intended to embrace all dosage forms where the product is formed by cooling a sugar-based or sugar alcohol based (eg isomalt) molten mass containing the active material.
  • the term "tablet” as used herein is intended to embrace unit dosage forms made from compressed powders or granules or compressed pastes.
  • a preferred pharmaceutical composition is a lozenge prepared by cooling a heated lozenge base containing the flurbiprofen and active ingredient(s) and/or burn-masking agent and other excipients to form solid lozenges.
  • the therapeutically effective amount of the flurbiprofen has been found to be from 5% to 40% of the normal adult dose of the flurbiprofen when given by ingestion to achieve a systemic antiinflammatory and/or analgesic effect.
  • the flurbiprofen may therefore be present in the pharmaceutical composition in an amount from 2.5 to 20mg preferably 5 to 12.5mg, more preferably about 8.75mg.
  • the amount of the salt used should be such as to provide the desired amount of flurbiprofen.
  • Suitable salts include the alkali metal salts eg the sodium salt or amino acid salts eg the lysine, arginine or meglumine salts.
  • Solid dosage forms may be prepared by methods which are well known in the art for the production of lozenges, tablets, capsules or chewing gums and may contain other ingredients known in such dosage forms such as acidity regulators, opacifiers, stabilising agents, buffering agents, flavourings, sweeteners, colouring agents, buffering agents, flavourings, sweeteners, colouring agents and preservatives. Any additional ingredient which is added should not react with any other component of the pharmaceutical compositions of the present invention. If such interactions are possible the components concerned should be kept separate for example by encapsulating one or both of the possibly reacting components, by including one of the components in a coating applied to the lozenge after manufacture or by having the components in different layers of a multilayer product.
  • flavour or component of the flavour or an excipient or carrier for the flavour contains an alcohol moiety
  • esterification of the carboxylic acid moiety in the flurbiprofen can be prevented or minimised by the methods outline above.
  • the preferred solid formulations of the present invention may be prepared as lozenges by heating the lozenge base under vacuum to remove excess water.
  • the lozenge base may be a sugar-based or sugar alcohol-based composition. If the lozenge base is sugar-based, it may comprise a single sugar (eg sucrose) or a mixture of sugars (eg a mixture of sucrose and glucose). If the lozenge base is sugar-alcohol based it may comprise sorbitol, xylitol, maltitol, maltitol syrup, lactitol, mannitol or mixtures thereof which may be in the form of the free sugar alcohols, derivatives thereof or mixtures thereof.
  • One preferred lozenge base comprises an approximately equimolar mixture of alpha-D-glucopyranosyl-1 ,6-D-sorbitol and alpha-D-glucosopyranosyl-1 J-D-mannitol (isomalt) optionally in conjunction with a hydrogenated glucose syrup such as lycasin.
  • the lozenge base is preferably heated to a temperature in the range 110 to 170°C under vacuum to remove water to give a moisture content which is preferably less than 2%, more preferably less than 1% before the remaining components of the pharmaceutical lozenge formulation are added.
  • the remaining ingredients may be blended into the lozenge base mixture as powders or liquids. Powders may be granulated prior to the mixing step.
  • the molten mixture may then be passed to individual moulds in which each lozenge is formed or may be drawn into a continuous cylindrical mass from which the individual lozenges are formed.
  • the lozenges are then cooled, subjected to a visual check and packed into suitable packaging.
  • suitable packaging is a blister pack of a water-impermeable plastics material (eg polyvinylchloride) closed by a metallic eg aluminium foil. The patient removes the lozenge by applying pressure to the blister to force the lozenge to rupture and pass through the metal foil seal. Lozenges will normally be sucked by the patient to release the flurbiprofen.
  • Masticable solid dose formulations may be made by the methods used to prepare chewable candy products or chewing gums.
  • a chewable solid dosage form may be prepared from an extruded mixture of sugar and glucose syrup to which the flurbiprofen has been added with optional addition of whipping agents, humectants, lubricants, flavours and colourings.
  • whipping agents humectants
  • lubricants lubricants
  • flavours and colourings See Pharmaceutical Dosage Forms: Tablets, Volume 1 , Second Edition edited by H A Lieberman, L Lachman and J B Schwartz published in 1989).
  • Liquid and spray formulations may be prepared by dissolving or suspending the flurbiprofen in a liquid medium which may also contain other ingredients such as stabilising agents, buffering agents, flavourings, sweeteners, colouring agents, buffering agents, flavourings, sweeteners, colouring agents and preservatives.
  • the formulation may then be packaged into an appropriate container.
  • a spray may be prepared by dissolving water soluble components in water and non-water soluble ingredients in a co-solvent (eg alcohol). The two phases are then mixed and the resulting mixture filtered and placed into dispensing containers.
  • the dispensing containers may be fitted with a metered, manually-operated spray mechanism or the dispenser may contain a pressurised propellant and be fitted with a suitable dispensing valve.
  • compositions which can be sucked or chewed by the patient and which slowly release the flurbiprofen and any active ingredient and/or bum-masking agent.
  • the flurbiprofen and active ingredient then pass over the mucous membrane of the throat where some is absorbed providing topical relief.
  • the unabsorbed flurbiprofen and active ingredient is then ingested by the patient and absorbed into the blood stream.
  • the flurbiprofen so absorbed can act systematically to provide analgesia, anti-inflammatory and anti-pyretic activity in addition to the relief that comes from the topical application of flurbiprofen to the mucous membrane of the throat.
  • Any active ingredient present may also exert its pharmacological effect systemically.
  • a second form of preferred formulations for use in the present invention are sprays which are administered so that the liquid composition is brought into contact with the mucous membrane of the throat so that some of the active components of the composition (the flurbiprofen and other active ingredients) and/or bum-masking agent is absorbed providing topical relief.
  • Ingestion of the liquid composition then means that the unabsorbed flurbiprofen can be absorbed in to the blood stream to provide systemic analgesic, anti-inflammatory or antipyretic activity in addition to the relief that comes from the topical application of the flurbiprofen to the mucous membrane of the throat.
  • Any active ingredient present may also exerts its pharmacological effect systemically.
  • the component identified in Examples 1 to 3 as "Active ingredient” can be any one or more of the active ingredients selected from an antihistamine, a cough suppressant, a decongestant, an expectorant, a muscle relaxant, a centrally acting analgesic, a local anaesthetic, an antibacterial compound, an antibiotic compound, an antifungal compound, an antiviral compound, minerals and vitamins.
  • Particularly preferred active ingredients are any one or more of the compounds specifically identified hereinbefore.
  • Lozenges are prepared containing the following ingredients expressed as the weight in milligrammes per lozenge.
  • the mixture of the sugar and liquid glucose is heated to 140° and a vacuum applied to reduce the water content of the mixture.
  • the flavouring is added in a sealed vessel.
  • the flurbiprofen, the active ingredient and the calcium carbonate are blended and the blend added to the remainder of the ingredients.
  • the resulting mixture is cooled and formed into a continuous cylindrical mass from which the individual lozenges are formed.
  • the individual solid lozenges are visually inspected and then packed.
  • the resulting lozenges provide palatable, stable and effective treatment for the symptoms of colds and flu particularly including sore throats.
  • a mixture of flurbiprofen, the active ingredient, sorbitol and glycerin is dissolved in aqueous alcohol to provide a pharmaceutical formulation which can be packed into a dispensing container fitted with a metered manually-operated spray mechanism which enables the formulation to be sprayed on to the mucous membrane of the throat as a fine spray.
  • a pharmaceutical lozenge formulation is prepared containing the following components expressed in milligrams per lozenge.
  • the flurbiprofen, the active ingredient and calcium carbonate are blended for two minutes and the blend granulated with a solution of the polyvinylpyrrolidine in isopropanol.
  • the granules are dried and the colloidal silicon dioxide and magnesium stearate are added and the resulting mixture blended for five minutes.
  • a molten lozenge base is prepared by dissolving the isomalt in the minimum amount of water.
  • the lycasin is added and the mixture heated at 110-120°C.
  • the mixture is then heated to 145°C under vacuum to remove water to give the molten lozenge base.
  • the blended granule and the anethole are then added to the molten lozenge base.
  • the resulting mixture is cooled and formed into a continuous cylindrical mass from which individual lozenges are prepared.
  • Lozenges are prepared containing the following ingredients expressed as the weight in milligrammes per lozenge.
  • the mixture of sugar and liquid glucose is heated to 140°C and a vacuum applied to reduce the water content of the mixture.
  • the flavouring is added in a sealed vessel.
  • the flurbiprofen and calcium carbonate are blended and the blend and flavourings are added to the remainder of the ingredients.
  • the resulting mixture is cooled and formed into a continuous cylindrical mass from which the individual lozenges are formed.
  • the individual solid lozenges were visually inspected and then packed.
  • the resulting lozenges provide palatable, stable and effective treatment for symptoms of colds and flu, particularly including sore throat.
  • a mixture of racemic flurbiprofen, anethole, sorbitol and glycerin is dissolved in aqueous alcohol to provide a pharmaceutical formulation which can be packed into a dispensing container fitted with a metered manually-operated spray mechanism which enables the formulation to be sprayed on to the mucous membrane of the throat as a fine spray.
  • a pharmaceutical lozenge formulation is prepared containing the following components expressed in milligrams per lozenge.
  • the flurbiprofen and calcium carbonate are blended for two minutes and the blend granulated with a solution of the polyvinylpyrrolidine in isopropanol.
  • the granules are dried and the colloidal silicon dioxide and magnesium stearate are added and the resulting mixture blended for five minutes.
  • a molten lozenge base is prepared by dissolving the isomalt in the minimum amount of water.
  • the lycasin is added and the mixture heated at 110-120°C.
  • the mixture is then heated to 145°C under vacuum to remove water to give the molten lozenge base.
  • the blended granule and the anethole are then added to the molten lozenge base.
  • the resulting mixture is cooled and formed into a continuous cylindrical mass from which individual lozenges are prepared.
  • the effectiveness of the treatment can be demonstrated by means of clinical trials in which patients suffering from sore throats are administered the formulations described in any one of the Examples or a placebo.
  • the patient is asked to assess the effectiveness of the treatment on parameters such as the relief of the pain associated with the sore throat, the reduction in the swelling of the throat and/or the improvement in swallowing following treatment.
  • the patients are also examined by a clinician to determine the amount of tonsillopharyngitis.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Zoology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne des compositions pharmaceutiques comprenant une combinaison de flurbiprofène avec (a) une quantité efficace sur le plan thérapeutique d'un ou de plusieurs ingrédients actifs sélectionnés dans le groupe formé par un antihistaminique, un antitussif, un décongestionnant, un expectorant, un myorelaxant, un analgésique à action centrale, un anesthésique local, un composé antibactérien, un composé antiviral, un composé antibiotique, un composé antifongique, des minéraux et des vitamines; et/ou (b) un agent en quantité permettant de masquer la brûlure, agent exerçant un effet de réchauffement sur les muqueuses de la gorge; les compositions sont destinées à s'utiliser dans le traitement de symptômes du rhume et de la grippe, y compris et notamment l'angine. Le traitement consiste en l'administration à un patient d'une composition pharmaceutique sous la forme d'une dose solide à mâcher ou à sucer ou de liquide ou de substance à pulvériser libérant le flurbiprofène et les ingrédients actifs; et/ou en l'administration d'un agent de soulagement de brûlures dans la cavité buccale de manière à déposer les composants actifs à la surface de la gorge présentant une angine.
PCT/EP1998/003180 1997-05-22 1998-05-22 Compositions pharmaceutiques a base de flurbiprofene et d'un agent de masquage de brulure pour le traitement de l'angine WO1998052545A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU79167/98A AU7916798A (en) 1997-05-22 1998-05-22 Pharmaceutical compositions of flurbiprofen and burn-masking agent for treating sore throat

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9710632.2A GB9710632D0 (en) 1997-05-22 1997-05-22 Pharmaceutical composition
GBGB9710525.8A GB9710525D0 (en) 1997-05-22 1997-05-22 Pharmaceutical composition
GB9710525.8 1997-05-22
GB9710632.2 1997-05-22

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WO1998052545A1 true WO1998052545A1 (fr) 1998-11-26

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Cited By (25)

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Publication number Priority date Publication date Assignee Title
WO2000041694A2 (fr) * 1999-01-11 2000-07-20 The Procter & Gamble Company Compositions possedant une stabilite amelioree
WO2001007050A1 (fr) * 1999-07-26 2001-02-01 Schering Corporation Agonistes du recepteur orl-1 de la nociceptine utilises pour le traitement de la toux
US6391886B1 (en) 2000-12-04 2002-05-21 The Procter & Gamble Company Oral compositions having improved consumer aesthetics
WO2003089007A1 (fr) * 2002-04-22 2003-10-30 Adcock Ingram Intellectual Property (Proprietary) Limited Compositions pharmaceutiques comprenant un decongestionnant et d'autres ingredients actifs pour traiter la toux et la grippe
EP1391201A1 (fr) * 2001-05-25 2004-02-25 SSP Co., Ltd. Compositions medicinales
WO2004019905A1 (fr) * 2002-08-29 2004-03-11 Novadel Pharma Inc. Capsule ou vaporisateur buccal, polaire et non polaire contenant des medicaments pour le traitement de troubles musculaires et squelettiques
US6846495B2 (en) 1999-01-11 2005-01-25 The Procter & Gamble Company Compositions having improved delivery of actives
EP1992333A1 (fr) 2007-05-08 2008-11-19 Sanovel Ilaç Sanayi Ve Ticaret Anonim Sirketi Flurbiprofène et combinaisons pour le relâchement musculaire
EP2074990A1 (fr) * 2007-12-26 2009-07-01 Sanovel Ilac Sanayi ve Ticaret A.S. Flurbiprofène à libération prolongée et combinaisons pour le relâchement musculaire
US7588793B1 (en) 1998-06-05 2009-09-15 Cadbury Adams Usa, Llc Enhanced flavoring compositions containing N-ethyl-p-menthane-3-carboxamide and method of making and using same
EP2298280A2 (fr) 2009-09-18 2011-03-23 Sanovel Ilac Sanayi ve Ticaret A.S. Gel comprenant une combinaison de flurbiprofène et de relaxant musculaire
US8101208B2 (en) 2004-08-11 2012-01-24 Kraft Foods Global Brands Llc Sensate compositions and delivery systems therefor
WO2012144964A1 (fr) * 2011-04-18 2012-10-26 Ak Kimya Ithalat-Lhracat Ve Sanayii A.S. Combinaisons de thiocolchicoside, de diclofénac et de lansoprazole
WO2013095319A2 (fr) 2011-12-23 2013-06-27 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Formulations de flurbiprofène et de diacéréine
WO2013095318A2 (fr) 2011-12-23 2013-06-27 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Formulations de flurbiprofène à désintégration orale
WO2013095320A1 (fr) 2011-12-23 2013-06-27 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Formulations de flurbiprofène
WO2013095317A3 (fr) * 2011-12-23 2013-10-10 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Formulations pharmaceutiques de flurbiprofène et glucosamine
WO2013115736A3 (fr) * 2012-01-31 2013-10-24 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Formulations pour comprimés bicouches de flurbiprofène et glucosamine
WO2013115737A3 (fr) * 2012-01-31 2013-12-05 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Nouvelles compositions pharmaceutiques de flurbiprofène et glucosamine
US8846007B2 (en) 2005-12-23 2014-09-30 Intercontinental Great Brands Llc Compositions providing a heating sensation for oral or dermal delivery
EP2848261A1 (fr) 2013-09-12 2015-03-18 Sanovel Ilac Sanayi ve Ticaret A.S. Formulations pharmaceutiques comprenant un relaxant des muscles et une combinaison d'un analgésique
US9078816B2 (en) 1997-10-01 2015-07-14 Suda Ltd. Buccal, polar and non-polar spray containing ondansetron
US9456985B2 (en) 2009-09-17 2016-10-04 Upsher-Smith Laboratories, Inc. Sustained-released product comprising a combination of a non-opioid amine and a non-steroidal, anti-inflammatory drug
WO2018138652A1 (fr) * 2017-01-26 2018-08-02 Laboratorios Liomont, S.A. De C.V. Composition pharmaceutique de loratadine, phényléphrine, paracétamol et amantadine pour administration orale, dans le traitement allopathique d'un rhume
US11433037B2 (en) 2016-07-05 2022-09-06 Glaxosmithkline Consumer Healthcare Holdings (Us) Llc Oral dosage form containing a fast release exterior coating

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MIRA E. ET AL: "Treatment of pharyngitis and pharyngolaryngitis. Comparison of phenylprenazone and flurbiprofen administered orally and rectally", CLIN. TRIALS J., vol. 21, no. 2, 1984, pages 100 - 108, XP002078979 *
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