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WO1994008551A2 - Procedes et compositions pharmaceutiques destines au traitement des symptomes du rhume - Google Patents

Procedes et compositions pharmaceutiques destines au traitement des symptomes du rhume Download PDF

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Publication number
WO1994008551A2
WO1994008551A2 PCT/US1993/008887 US9308887W WO9408551A2 WO 1994008551 A2 WO1994008551 A2 WO 1994008551A2 US 9308887 W US9308887 W US 9308887W WO 9408551 A2 WO9408551 A2 WO 9408551A2
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical
pharmaceutical composition
ine
cold
diol
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/US1993/008887
Other languages
English (en)
Other versions
WO1994008551A3 (fr
Inventor
James Grigg Upson
Carmelita Macklin Russell
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to CA002146637A priority Critical patent/CA2146637C/fr
Priority to JP6510004A priority patent/JPH08502288A/ja
Priority to EP93921692A priority patent/EP0662840A1/fr
Priority to AU49307/93A priority patent/AU678561B2/en
Publication of WO1994008551A2 publication Critical patent/WO1994008551A2/fr
Publication of WO1994008551A3 publication Critical patent/WO1994008551A3/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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to orally or nasally administrate pharmaceutical compositions comprising at least one pharmaceutical active, 3-1-menthoxy propane 1,2-diol (herein referred to as "MPD") and pharmaceutically-acceptable carrier material(s).
  • MPD 3-1-menthoxy propane 1,2-diol
  • the present invention also relates to methods for treating cough, cold, cold-like, allergy and/or flu symptoms in a human or lower animal by adminis ⁇ tering, orally or nasally, a composition comprising MPD.
  • compositions safe and effective for treating colds, flu, and allergies are well known. Over-the-counter edica- tions provide symptomatic relief of such illnesses. Typical symptoms of the common cold are mild malaise, sore throat and nasal complaints. Nasal discharge, nasal congestion and/or sneezing frequently are present. Also common are sore, dry or scratchy throat and hoarseness and cough. Other symptoms may include mild burning of the eyes, loss of smell and taste, a feeling of pressure or fullness in the sinuses or ears, headache, and vocal impairment. Flu symptoms are similar but usually of greater severity, including fever, generalized aches and pains, fatigue and weakness, and chest discomfort. Allergy symptoms are more akin to the common cold, with more frequent/severe sinus pressure, drainage and headaches.
  • Prior art formulations for treating cough, cold, cold-like, allergy and/or flu symptoms and the discomfort, pain, fever and general malaise associated therewith typically contain one or more of the pharmaceutical actives which are analgesics, anesthetics, antihis- tamines, decongestants, cough suppressants, antitussives and expector ⁇ ants.
  • compositions and methods useful for treating cough, cold, cold-like, allergy and flu symptoms in humans and lower animals in need of such treatment Another object is to provide such compositions and methods having increased perceived efficacy, e.g., speed of relief and/or duration of relief, and/or improved aesthetics.
  • the present invention is directed to pharmaceutical compositions comprising: (a) a safe and effective amount of at least one pharma ⁇ ceutical cold active; (b) 3-1-menthoxy propane 1,2-diol; and (c) a pharmaceutically-acceptable carrier material suitable for oral or nasal administration.
  • the present invention is also directed to methods for treating cough, cold, cold-like, allergy, and flu symptoms in a human or lower animal, said method comprising administering to a human or lower animal in need of such treatment, by oral or nasal administration, a composition comprising 3-1-menthoxy propane 1,2-diol.
  • the present invention relates to pharmaceutical compositions comprising: (a) at least one pharmaceutical cold active; (b) 3-1- menthoxy propane 1,2-diol ("MPD"); and (c) pharmaceutically-acceptable carrier material suitable for oral or nasal administration.
  • MPD 3-1- menthoxy propane 1,2-diol
  • pharmaceutically-acceptable carrier material suitable for oral or nasal administration.
  • compositions according to the present inven- tion comprise pharmaceutical cold actives useful for treating cough, cold, cold-like, allergy and/or flu symptoms.
  • pharmaceutical actives are well known, and are generally recognized as being an active having analgesic, anti-inflammatory, anesthetic, antihistamine, decongestant, cough suppressant, demulcents, antitussive, and/or expectorant properties.
  • compositions of this invention therefore contain one or more known pharmaceutical cold actives, particularly those commonly utilized in cough/cold preparations, such as, for example, a decon ⁇ gestant such as pseudoephedrine, phenylpropanolamine, phenylephrine " and ephedrine, their pharmaceutically acceptable salts; an antitussive such as dextromethorphan, chlophedianol, carbetapentane, caramiphen, noscapine, diphenhydramine, codeine, menthol, hydrocodone, hydromor- phone, fo inoben, their pharmaceutically-acceptable salts; an expec- torant or ucolytic such as glyceryl guaiacolate, terpin hydrate, ammonium chloride, N-acetylcysteine and bromhexine, ambroxol, their pharmaceutically acceptable salts; and an antihistamine such as chlorpheniramine, brompheniramine, dexchlorpheni
  • Patent 4,783,465 to Sunshine et al. issued November 8, 1988
  • U.S. Patent 4,619,934 to Sunshine et al. issued October 28, 1986, which are incorporated by reference herein.
  • broncho- dilators such as terbutaline, atropine, aminophylline, epinephrine, isoprenaline, metaproterenol, bitoterol, theophylline and albuterol.
  • analgesic compounds such as aspirin, acetaminophen, ibuprofen, and naproxen; and topical anesthetics/analgesics such as phenol, benzocaine, hexyl resorcinol, and dyclonine.
  • compositions of the present invention comprise a safe and effective amount of at least one pharmaceutical cold active.
  • safe and effective amount means an amount of a compound or composition high enough when administered orall or nasaTly to significantly positively modify the condition to be treated, but low enough to avoid serious side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgment.
  • the safe and effective amount of the pharmaceutical cold active will vary with the particular condition being treated, the age and physical condition of the patient being treated, the severity of the condition, the duration of the treatment, the nature of concurrent therapy, the specific pharmaceutical cold active employed, the particular pharma ⁇ ceutically-acceptable carrier utilized, and like factors within the knowledge and expertise of the attending physician.
  • the pharmaceutical cold active(s) comprise from about 0.001% to about 99.9%, by weight, of the pharmaceutical compositions of the present invention, preferably from about 0.001% to about 75%, and most prefer- ably from about 0.01% to about 30%.
  • 3-1-Menthoxy Propane 1.2-Diol
  • compositions of the present invention also comprise 3-1-menthoxy propane 1,2-diol ("MPD").
  • MPD 3-1-menthoxy propane 1,2-diol
  • This material is described in detail in U.S. Patent 4,459,425, issued July 10, 1984 to Amano et. al, incorporated herein by reference in its entirety. While not to be limited by theory, it is believed that the benefits obtained by the use of MPD in the compositions of the present invention are the result of the unique cooling profile for this compound.
  • MPD is commercially available, being sold by Takasago Perfumery Co., Ltd., Tokyo, Japan.
  • MPD typically comprises from about 0.001% to about 10% by weight of the pharmaceutical compositions of the present invention, prefer ⁇ ably from about 0.01% to about 5%, and most preferably from about 0.01% to about 0.5%.
  • pharmaceutically-acceptable carrier materials means one or more compatible solid or liquid filler diluents or encapsulating substances which are suitable for oral and/or nasal administration to a human or lower animal.
  • compatible means that the components of the com ⁇ positions of the present invention are capable of being commingled with the pharmaceutical cold active, and with each other, in a manner such that there is no interaction which would substantially reduce the pharmaceutical efficacy of the compositions under ordinary use situa ⁇ tions.
  • Pharmaceutically-acceptable carrier materials must, of course, be of sufficiently high purity and sufficiently low toxicity to render them suitable for administration to the human being treated.
  • compositions comprise from about 0.1% to about 99.99% of one or more pharmaceutically-acceptable carrier materials.
  • Solid oral dosage forms preferably contain from about 0.1% to about 99%, more preferably from about 25% to about 99%, and most preferably from about 50% to about 99% of the pharmaceutical cold active compo ⁇ nent.
  • Liquid oral dosage forms preferably contain from about 0.001% to about 25% and more preferably from about 0.001% to about 10% and most preferably from about 0.01% to about 5% of the pharmaceutical cold active component.
  • Tablets can be compressed, molded, triturated, enteric-coated, sugar-coated, film-coated or multiple compressed, containing suitable binders, lubricants, diluents, disintegrating agents, coloring agents, flavoring agents, preservatives and flow-inducing agents. Also useful are soft gelatin capsules.
  • Liquid oral dosage forms include aqueous and nonaqueous solu ⁇ tions, emulsions, pseudo emulsions, suspensions, and solutions and/or suspensions reconstituted from non-effervescent granules, containing suitable solvents, preservatives, emulsifying agents, suspending agents, diluents, sweeteners, coloring agents, and flavoring agents.
  • suitable solvents preservatives, emulsifying agents, suspending agents, diluents, sweeteners, coloring agents, and flavoring agents.
  • typical liquid formulations preferably contain a co-solvent, for example, propylene glycol, polyethylene glycol, alcohol, glycerin, sorbitol solution and the like, to assist solubili- zation and incorporation of water-insoluble ingredients, such as flavoring oils and the like into the composition.
  • a co-solvent for example, propylene glycol, polyethylene glycol, alcohol, glycerin, sorbitol solution and the like, to assist solubili- zation and incorporation of water-insoluble ingredients, such as flavoring oils and the like into the composition.
  • ingredients well known to the pharmacist's art may also be included in amounts generally known for these ingredients, for example, natural or artificial sweeteners, flavoring agents, colorants and the like to provide a palatable and pleasant looking final prod ⁇ uct, antioxidants, for example, butylated hydroxy anisole or butylated hydroxy toluene, and preservatives, for example, methyl or propyl paraben, potassium sorbate, or sodium benzoate, to prolong and enhance shelf life.
  • natural or artificial sweeteners for example, butylated hydroxy anisole or butylated hydroxy toluene
  • preservatives for example, methyl or propyl paraben, potassium sorbate, or sodium benzoate
  • a preferred optional component is also materials other than MPD having cooling properties, such as menthol and menthol-like compounds such as N-ethyl-p-menthane-3-carboxamide (preferably at from about 0.001% to about 5%, more preferably from about 0.001% to about 0.5%), and mixtures thereof.
  • a preferred optional component is also caffeine.
  • the present invention also relates to a method for treating cough, cold, cold-like, allergy and flu symptoms in a human or lower animal.
  • Said method comprises administering to a human or lower animal in need of such treatment, by oral or nasal administration, a composition comprising MPD.
  • Preferred pharmaceutical compositions for administration according to the present invention method comprise from about 0.001% to about 10% (preferably from about 0.01% to about 0.5%) of MPD, and from about 0.1% to about 99.999% (preferably from about 70%-to about 99.99%) of-pharmaceutically-acceptable carrier material(s).
  • Preferred is administering, either orally or nasally, a safe and effective amount of a composition according to the present invention. Most preferred is oral administration.
  • This composition is prepared by first dissolving the dextromethor- phan and glyceryl guaiacolate in alcohol and then adding with constant mixing the menthol, MPD and WS-3. In separate containers dissolve the sucrose in a small portion of the water, dissolve the coloring agent in a separate small portion of the water, and in still another con ⁇ tainer dissolve the sodium citrate and citric acid in a small portion of the water. Finally, all the premixes and the remaining water are mixed with constant mixing to prepare a composition of the present invention having 20 mg of dextromethorphan and 200 mg of glyceryl guaiacolate per 15 ml of composition.
  • Administration by sucking of drops to a human patient having a cough- associated with the common cold provides rapid, long lasting relief of the cough in said human patient.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Compositions pharmaceutiques comprenant une dose sûre et efficace d'au moins un produit pharmaceutique agissant contre le rhume; 3-1-menthoxy propane 1,2-diol; et un excipient pharmaceutiquement acceptable convenant à une administration orale ou nasale. La présente invention se rapporte également à des procédés de traitement de la toux, du rhume, des allergies, de symptômes analogues au rhume et/ou de symptômes grippaux chez l'homme ou l'animal. Ce procédé consiste à administrer à un homme ou un animal nécessitant un tel traitement, par voie orale ou nasale, une composition comprenant 3-1-menthoxy propane 1,2-diol.
PCT/US1993/008887 1992-10-09 1993-09-22 Procedes et compositions pharmaceutiques destines au traitement des symptomes du rhume Ceased WO1994008551A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002146637A CA2146637C (fr) 1992-10-09 1993-09-22 Compositions pharmaceutiques et methodes pour traiter les symptomes du rhume
JP6510004A JPH08502288A (ja) 1992-10-09 1993-09-22 感昌症状を治療するための医薬組成物及び用法
EP93921692A EP0662840A1 (fr) 1992-10-09 1993-09-22 Procedes et compositions pharmaceutiques destines au traitement des symptomes du rhume
AU49307/93A AU678561B2 (en) 1992-10-09 1993-09-22 Pharmaceutical compositions and methods for treating cold symptoms

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95501392A 1992-10-09 1992-10-09
US07/955,013 1992-10-09

Publications (2)

Publication Number Publication Date
WO1994008551A2 true WO1994008551A2 (fr) 1994-04-28
WO1994008551A3 WO1994008551A3 (fr) 1994-06-23

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ID=25496254

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Application Number Title Priority Date Filing Date
PCT/US1993/008887 Ceased WO1994008551A2 (fr) 1992-10-09 1993-09-22 Procedes et compositions pharmaceutiques destines au traitement des symptomes du rhume

Country Status (7)

Country Link
EP (1) EP0662840A1 (fr)
JP (1) JPH08502288A (fr)
AU (1) AU678561B2 (fr)
CA (1) CA2146637C (fr)
MX (1) MX9306295A (fr)
NZ (1) NZ256346A (fr)
WO (1) WO1994008551A2 (fr)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025003A1 (fr) * 1993-04-30 1994-11-10 The Procter & Gamble Company Compositions aromatiques s'administrant par voie nasale
WO1995025518A1 (fr) * 1994-03-18 1995-09-28 Ciba-Geigy Ag Solution aqueuse de levocabastine a usage ophtalmique
US5626831A (en) * 1995-12-20 1997-05-06 Van Moerkerken; Arthur Method for relief and prevention of common cold, and compositions
US5698181A (en) * 1994-12-09 1997-12-16 Warner-Lambert Company Breath-freshening edible compositions comprising menthol and an N-substituted-P-menthane carboxamide and methods for preparing same
WO1998015275A3 (fr) * 1996-10-09 1998-08-06 Algos Pharm Corp Therapie et composition pharmaceutique potentialisee efficaces contre la migraine
WO1998047484A1 (fr) * 1997-04-21 1998-10-29 The Procter & Gamble Company Dragee fourree
WO1998047482A1 (fr) * 1997-04-21 1998-10-29 The Procter & Gamble Company Compositions adoucissantes pour la gorge
US6013632A (en) * 1997-01-13 2000-01-11 Emory University Compounds and their combinations for the treatment of influenza infection
US6469009B1 (en) 1996-04-08 2002-10-22 Ucb, S.A. Pharmaceutical compositions for the treatment of rhinitis
WO2003020258A1 (fr) * 2001-09-04 2003-03-13 Boehringer Ingelheim International Gmbh Medicament contre la grippe de type a
US6939550B2 (en) 1998-06-01 2005-09-06 Schering Corporation Stabilized antihistamine syrup
BG64741B1 (bg) * 1998-03-31 2006-02-28 Asta Medica Aktiengesellschaft Твърди, бързоразтварящи се лекарствени форми на цетиризин
WO2006034495A3 (fr) * 2004-09-23 2006-09-14 Jonathan R Matias Procedes d'utilisation de propyleneglycol-carbonate menthole et ses analogues destines a produire des effets anti-inflammatoires et anti-angiogeniques
US20070249566A1 (en) * 2006-04-21 2007-10-25 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US20070249727A1 (en) * 2006-04-21 2007-10-25 The Proctor & Gamble Company Compositions and kits useful for treatment of respiratory illness
US7364761B2 (en) 1997-09-18 2008-04-29 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents and method of preparing
US7482022B2 (en) 2002-04-04 2009-01-27 Pfizer Inc. Palatable chewable tablet
WO2012104571A1 (fr) * 2011-02-02 2012-08-09 GILHOLM, Stephen, Philip Compositions de monoterpénoïdes pour le traitement de la grippe
US9492444B2 (en) 2013-12-17 2016-11-15 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
AU2016219620B2 (en) * 2006-04-21 2017-05-11 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US9707184B2 (en) 2014-07-17 2017-07-18 Pharmaceutical Manufacturing Research Services, Inc. Immediate release abuse deterrent liquid fill dosage form
US9901585B2 (en) 2002-06-14 2018-02-27 Cipla Limited Combination of azelastine and fluticasone for nasal administration
US10172797B2 (en) 2013-12-17 2019-01-08 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
US10195153B2 (en) 2013-08-12 2019-02-05 Pharmaceutical Manufacturing Research Services, Inc. Extruded immediate release abuse deterrent pill
US10959958B2 (en) 2014-10-20 2021-03-30 Pharmaceutical Manufacturing Research Services, Inc. Extended release abuse deterrent liquid fill dosage form
CN112972439A (zh) * 2019-12-16 2021-06-18 南京亿华药业有限公司 一种愈美泡腾片及其制备方法
WO2021156698A1 (fr) 2020-02-03 2021-08-12 Johnson & Johnson Consumer Inc. Comprimé à mâcher monocouche comprenant de la cétirizine
US11911517B2 (en) 2018-05-16 2024-02-27 Bayer Healthcare Llc High concentration suspension formulation for cold and flu soft gel capsule medications

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1353381A (en) * 1971-02-04 1974-05-15 Wilkinson Sword Ltd Substituted p-menthanes and compositions containing them
JPS5888334A (ja) * 1981-11-20 1983-05-26 Takasago Corp ３−ｌ−メントキシプロパン−１、２−ジオ−ル
SK121293A3 (en) * 1991-04-04 1994-07-06 Procter & Gamble Ingestible pharmaceutical compositions for treating upper gastrointestinal tract disorder

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025003A1 (fr) * 1993-04-30 1994-11-10 The Procter & Gamble Company Compositions aromatiques s'administrant par voie nasale
WO1995025518A1 (fr) * 1994-03-18 1995-09-28 Ciba-Geigy Ag Solution aqueuse de levocabastine a usage ophtalmique
US5698181A (en) * 1994-12-09 1997-12-16 Warner-Lambert Company Breath-freshening edible compositions comprising menthol and an N-substituted-P-menthane carboxamide and methods for preparing same
US5626831A (en) * 1995-12-20 1997-05-06 Van Moerkerken; Arthur Method for relief and prevention of common cold, and compositions
US6469009B1 (en) 1996-04-08 2002-10-22 Ucb, S.A. Pharmaceutical compositions for the treatment of rhinitis
US6489329B2 (en) 1996-04-08 2002-12-03 Ucb S.A. Pharmaceutical compositions for the treatment of rhinitis
WO1998015275A3 (fr) * 1996-10-09 1998-08-06 Algos Pharm Corp Therapie et composition pharmaceutique potentialisee efficaces contre la migraine
US5891885A (en) * 1996-10-09 1999-04-06 Algos Pharmaceutical Corporation Method for treating migraine
US5939425A (en) * 1996-10-09 1999-08-17 Algos Pharmaceutical Corporation Method for treating a migraine
US6013632A (en) * 1997-01-13 2000-01-11 Emory University Compounds and their combinations for the treatment of influenza infection
US6107281A (en) * 1997-01-13 2000-08-22 Nutri-Quest, Inc. Compounds and their combinations for the treatment of influenza infection
WO1998047482A1 (fr) * 1997-04-21 1998-10-29 The Procter & Gamble Company Compositions adoucissantes pour la gorge
WO1998047484A1 (fr) * 1997-04-21 1998-10-29 The Procter & Gamble Company Dragee fourree
US7364761B2 (en) 1997-09-18 2008-04-29 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents and method of preparing
BG64741B1 (bg) * 1998-03-31 2006-02-28 Asta Medica Aktiengesellschaft Твърди, бързоразтварящи се лекарствени форми на цетиризин
US6939550B2 (en) 1998-06-01 2005-09-06 Schering Corporation Stabilized antihistamine syrup
WO2003020258A1 (fr) * 2001-09-04 2003-03-13 Boehringer Ingelheim International Gmbh Medicament contre la grippe de type a
US7482022B2 (en) 2002-04-04 2009-01-27 Pfizer Inc. Palatable chewable tablet
US9901585B2 (en) 2002-06-14 2018-02-27 Cipla Limited Combination of azelastine and fluticasone for nasal administration
WO2006034495A3 (fr) * 2004-09-23 2006-09-14 Jonathan R Matias Procedes d'utilisation de propyleneglycol-carbonate menthole et ses analogues destines a produire des effets anti-inflammatoires et anti-angiogeniques
US20070249727A1 (en) * 2006-04-21 2007-10-25 The Proctor & Gamble Company Compositions and kits useful for treatment of respiratory illness
US12403103B2 (en) 2006-04-21 2025-09-02 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US20070249566A1 (en) * 2006-04-21 2007-10-25 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US12083117B2 (en) 2006-04-21 2024-09-10 The Procter & Gamble Company Compositions and kits useful for treatment of respiratory illness
US11491151B2 (en) 2006-04-21 2022-11-08 The Procter & Gamble Company Compositions and kits useful for treatment of respiratory illness
US11141415B2 (en) 2006-04-21 2021-10-12 The Procter & Gamble Company Compositions and kits useful for treatment of respiratory illness
AU2016219620B2 (en) * 2006-04-21 2017-05-11 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US11083697B2 (en) 2006-04-21 2021-08-10 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US10688089B2 (en) 2006-04-21 2020-06-23 The Procter & Gamble Company Compositions and kits useful for treatment of respiratory illness
US10022339B2 (en) * 2006-04-21 2018-07-17 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US10098873B2 (en) 2006-04-21 2018-10-16 The Procter & Gamble Company Compositions and kits useful for treatment of respiratory illness
US11077074B2 (en) 2006-04-21 2021-08-03 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
US10772848B2 (en) 2006-04-21 2020-09-15 The Procter & Gamble Company Compositions and methods useful for treatment of respiratory illness
WO2012104570A1 (fr) * 2011-02-02 2012-08-09 GUILHOLM, Stephen Philip Composition de monoterpénoïdes à propriétés bactéricides
WO2012104571A1 (fr) * 2011-02-02 2012-08-09 GILHOLM, Stephen, Philip Compositions de monoterpénoïdes pour le traitement de la grippe
WO2012104568A1 (fr) * 2011-02-02 2012-08-09 GILHOLM, Stephen Philip Composition de monoterpénoïdes pour stimuler le système immunitaire
US9023888B2 (en) 2011-02-02 2015-05-05 Max Reynolds Composition of monoterpenoids having bactericidal properties
US10195153B2 (en) 2013-08-12 2019-02-05 Pharmaceutical Manufacturing Research Services, Inc. Extruded immediate release abuse deterrent pill
US10639281B2 (en) 2013-08-12 2020-05-05 Pharmaceutical Manufacturing Research Services, Inc. Extruded immediate release abuse deterrent pill
US9492444B2 (en) 2013-12-17 2016-11-15 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
US10792254B2 (en) 2013-12-17 2020-10-06 Pharmaceutical Manufacturing Research Services, Inc. Extruded extended release abuse deterrent pill
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CA2146637C (fr) 2001-02-13
EP0662840A1 (fr) 1995-07-19
NZ256346A (en) 1997-04-24
MX9306295A (es) 1994-04-29
AU4930793A (en) 1994-05-09
JPH08502288A (ja) 1996-03-12
WO1994008551A3 (fr) 1994-06-23
AU678561B2 (en) 1997-06-05

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