EP0719156A1 - Compositions contenant un sel d'acide amine d'un agent anti-inflammatoire non steroidien a base d'acide propionique et au moins un decongestionnant ou un expectorant ou un antihistaminique ou un antitussif - Google Patents

Compositions contenant un sel d'acide amine d'un agent anti-inflammatoire non steroidien a base d'acide propionique et au moins un decongestionnant ou un expectorant ou un antihistaminique ou un antitussif

Info

Publication number
EP0719156A1
EP0719156A1 EP94926020A EP94926020A EP0719156A1 EP 0719156 A1 EP0719156 A1 EP 0719156A1 EP 94926020 A EP94926020 A EP 94926020A EP 94926020 A EP94926020 A EP 94926020A EP 0719156 A1 EP0719156 A1 EP 0719156A1
Authority
EP
European Patent Office
Prior art keywords
cold
amino acid
expectorant
propionic acid
antitussive
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.)
Withdrawn
Application number
EP94926020A
Other languages
German (de)
English (en)
Inventor
Sekhar Mitra
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
Publication of EP0719156A1 publication Critical patent/EP0719156A1/fr
Withdrawn legal-status Critical Current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
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/10—Expectorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

Definitions

  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like and/or flu symptoms by administering a safe and effective amount of a composition comprising certain amino acid salts of propionic acid non-steriodal anti-inflammatory agents along with at least one of (a) a decongestant, (b) an expectorant, (c) an 0 antihistamine, and (d) an antitussive.
  • the common cold although not usually a serious illness, is a highly pre ⁇ valent, discomforting and annoying infliction.
  • the term "common cold” is applied to minor respiratory illnesses caused by a variety of different respiratory viruses. 5 While rhinoviruses are the major known cause of common colds, accounting for approximately 30 percent of colds in adults, viruses in several other groups are also important. While immune responses occur, and infection with some respiratory tract viruses therefore could be prevented by a vaccine, development of a polytypic vaccine to cover all possible agents is impractical. Thus, the problem of controlling 0 acute upper respiratory disease presents complex challenges, and the long-desired discovery of a single cure for the common cold is an unrealistic expectation.
  • Exemplary prior art formulations for treatment of cough, cold, cold-like and/or flu symptoms and the discomfort, pain, fever and general malaise associated therewith generally contain an analgesic (aspirin or acetaminophen) and one or more antihistaminics, decongestants, cough suppressants, antitussives and expectorants.
  • non-steroidal anti-inflammatory drugs to combat inflammation and attendant pain is accepted medical practice.
  • the non-steroidals are commonly employed to relieve pain and inflammation associated with, for example, bursitis, arthritis, headache and the like.
  • drugs of the non-narcotic analgesic class of drugs are aspirin, acetaminophen, ibuprofen and naproxen.
  • Aspirin, acetaminophen and ibuprofen have heretofore been included as the pain reliever and fever-reducing component in conventional cough/cold multi- -symptom alleviating compositions.
  • compositions comprising certain amino acid salts of the propionic acid NSAIDs with at least one of (a) a decongestant, (b) an expectorant (c) and antihistamine, and (d) an antitussive provides improved treatment, management or mitigation of cold, cold-like and/or flu symptoms.
  • symptoms refer to coryza, nasal congestion, sinus congestion, sinus pain, upper respiratory infections, allergic rhinitis, otitis, sinitis, etc.
  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like and/or flu symptoms by administering a safe and effective amount of a composition comprising an amino acid salt of a propionic acid NSAID along with at least one of (a) a de ⁇ congestant, (b) an expectorant, (c) an antihistamine and (d) an antitussive.
  • the present invention relates to compositions and methods for providing improved treatment, management or mitigation of cold, cold-like and/or flu symptoms by administering a safe and effective amount of a composition comprising an amino acid salt of a propionic acid NSAID along with at least one of (a) a de- congestant, (b) an expectorant (c) an antihistamine and (d) an antitussive.
  • amino acid salt refers to salts derived from pharmaceutically acceptable organic non-toxic bases of primary, secondary, tertiary and quaternary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as triethylamine, tripropylamine, 2-dimethylaminoethanol, 2-diethylaminoethanol, lysine, ornithine, arginine, histidine, caffeine, procaine, N-ethylpiperidine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglycamine, theobromine, purines, piperazine, piperidine, polyamine resins and the like.
  • the preferred non-steroidal anti-inflammatory agents useful in the com ⁇ position of the present invention include the amino acid salts of the propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen, flurbiprofen, ketoprofen, fenoprofen, fenbufen, indoprofen, pirprofen, carprofen, oxaprozin, pranoprofen, miroprofen, tioxaprofen, suprofen, alminoprofen, and tiaprofenic. Mixtures of these non-steroidal anti-inflammatory agents may also be employed. Of these propionic acid NSAIDs, ibuprofen, naproxen and ketoprofen are most preferred.
  • S(+) isomer of these NSAID salts.
  • S(+) as applied to the analgesic agents herein is intended to encompass the dextrorotatory or S(+) isomer of the amino acid salt derivatives thereof.
  • the expression "substantially free of the R(-) antipode” as used in conjunction with the term “S(+)” means that the S(+) enantiomer is sufficiently free it is R(-) antipode to exert the desired onset-hastened and enhanced analgesic effect. Practically speaking, this means that the active ingredient should contain at least 90% by weight of the S(+) enantiomer and 10% or less weight R(-) enantiomer.
  • the weight ratio of S(+) enantiomer to R(-) enantiomer is greater than 20:1, more preferably greater than 97:3. Most preferably the S(+) enantiomer is 99 or more % by weight free of R(-) enantiomer, i.e., the weight ratio of S to R is approximately equal to or greater than 99: 1.
  • the safe and effective amount of the amino acid salts of ibuprofen, naproxen, benoxaprofen, flurbiprofen, ketoprofen, fenoprofen, fenbufen, indo ⁇ profen, pirprofen, carprofen, oxaprozin, pranoprofen, miroprofen, tioxaprofen, suprofen, alminoprofen, and tiaprofenic generally ranges from about 7.5 mg to about lOOOmg, and are generally the same as their acid derivatives counterparts.
  • Useful dosage of these agents can be found in The Pbv. icians' Desk Reference, 47th Edition (1993) and in U.S. Patent 4,552,£99 to Sunshine et al., issued November 12, 1985, both of which are incorporated by reference herein.
  • the safe and effective amount of the amino acid salt of ibuprofen used in the compositions of the present invention generally ranges from about 50 to about 800 mg, preferably from about 50 to about 400 mg, more preferably from about 50 to about 200 mg and most preferably from about 50 to about 100 mg.
  • the safe and effective amount of the amino acid salt of flurbiprofen used in the compositions of the present invention generally ranges from about 12.5 to about 300 mg, preferably from about 12.5 to about 200 mg, more preferably from about 12.5 to about 100 mg and most preferably from about 12.5 to about 50 mg.
  • the safe and effective amount of the amino acid salt of ketoprofen used in the compositions of the present invention generally ranges from about 5 to about 100 mg, preferably from about 5 to about 75 mg, more preferably from about 5 to about 50 mg and most preferably from about 5 to about 25 mg.
  • the amount of the S(+) isomers of these agents will be about half of the amount of the racemic mixture.
  • compositions of the present invention also include at least one other pharmacological active selected from the following class: (a) a decongestant, (b) an expectorant (c) an antihistamine and (d) an antitussive.
  • a decongestant selected from the following class: (a) a decongestant, (b) an expectorant (c) an antihistamine and (d) an antitussive.
  • the decongestants useful in the compositions of the present invention include pseudoephedrine, phenyipro- panolamine, phenylephrine and ephedrine, their pharmaceutically acceptable salts, and mixtures thereof.
  • antitussives useful in the present invention include those such as dextromethorphan, chlophedianol, carbetapentane, caramiphen, noscapine, diphenhydramine, codeine, hydrocodone, hydromorphone, fominoben, their pharmaceutically-acceptable salts, and mixtures thereof.
  • the antihistamines useful in the present invention include those such as chlorpheniramine, brompheniramine, dexchlo heniramine, dexbromphreniramine, triprolidine, azatadine, doxylamine, tripelennamine, cyproheptadine, hydroxyzine, clemastine, carbinoxamine, phenindamine, bromodiphenhydramine, pyrilamine, their pharmaceutically acceptable salts, as well as the non-sedating antihistamines which include acrivastine, AHR-11325, astemizole, azelastine, cetirizine, ebastine, ketotifen, lodoxamide, loratidine, levocabastine, mequitazine, oxatomide, setastine, tazifylline, warmthlastine, and terfenadine, their pharmaceutically acceptable salts and mixtures thereof.
  • the expectorants also known as mucolytic agents
  • the expectorants include glyceryl guaiacolate, terpin hydrate, ammonium chloride, N- -acetylcysteine and bromhexine, ambroxol, their pharmaceutically acceptable salts, and mixtures thereof. All of these components, as well as their acceptable dosage ranges are described in the following: U.S. Patent 4,783,465 to Sunshine et al., is ⁇ sued November 8, 1988, U.S. Patent 4,619,934 to Sunshine et al., issued October 28, 1986, which are incorporated by reference herein.
  • the pharmaceutical compositions of the present invention comprise the analgesic agent and other pharmacological active in a ratio of anal- gesic agent: pharmacological active of from about 200: 1 to about 1 : 1, preferably from about 50: 1 to about 1 : 1 and most preferably from about 10: 1 to about 1: 1.
  • oral dosage forms can be used, including such solid forms as tablets, capsules, granules, lozenges and bulk powders and liquid forms such as syrups and suspensions. These oral forms comprise a safe and effective amount, usually at least about 5% of the active component.
  • Solid oral dosage forms preferably contain from about 5% to about 95%, more preferably from about 10% to about 95%, and most preferably from about 25% to about 95% of the active component.
  • Liquid oral dosage forms preferably contain from about 1% to about 50% and more preferably from about 1% to about 25% and most preferably from about 3% to about 10% of the active component.
  • Tablets can be compressed, 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 solutions, emul ⁇ sions, pseudo emulsions, suspensions, and solutions and/or suspensions recons ⁇ tituted from non-effervescent granules, containing suitable solvents, preservatives, emulsifying agents, suspending agents, diluents, sweeteners, taste-masking agents, coloring agents, and flavoring agents.
  • suitable solvents preservatives, emulsifying agents, suspending agents, diluents, sweeteners, taste-masking agents, coloring agents, and flavoring agents.
  • Typical carriers include simple aqueous solutions, syrups, dispersions and suspensions, and aqueous based emulsions such as the oil-in-water type.
  • the most preferred carrier is a suspension of the pharmaceutical composition in an aqueous vehicle containing a suitable suspending agent.
  • suitable suspending agents include Avicel RC-591 (a microcrystalline-cellulose/sodium carboxymethyl cellulose mixture available from FMC), guar gum and the like. Such suspending agents are well known to those skilled in the art.
  • the total water content based on the weight of the final composition, will generally range from about 20 to about 75%, and, preferably, from about 20 to about 40%, by weight/volume.
  • typical liquid formu- lations preferably contain a co-solvent, for example, propylene glycol, glycerin, sor- bitol solution and the like, to assist solubilization and incorporation of water-insoluble ingredients, such as flavoring oils and the like into the composition.
  • a co-solvent for example, propylene glycol, glycerin, sor- bitol solution and the like
  • the compositions of this invention preferably contain from about 5 to about 25 volume/volume percent and, most preferably, from about 10 to about 20 volume/ volume percent, of the co-solvent.
  • compositions of this invention may optionally contain one or more other known therapeutic agents, particularly those commonly utilized in cough/cold preparations, such as, for example, a s bronchodilator such as terbutaline, aminophylline, epinephrine, isoprenaline, metaproterenol, bitoteroL, theophylline and albuterol as well as other analgesic agents such as acetaminophen and aspirin.
  • a s bronchodilator such as terbutaline, aminophylline, epinephrine, isoprenaline, metaproterenol, bitoteroL, theophylline and albuterol
  • analgesic agents such as acetaminophen and aspirin.
  • a highly preferred optional component is caffeine.
  • 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 product, antioxidants, for example, butylated hydroxy anisole or butylated hydroxy toluene, and preservatives, for example, methyl or propyl paraben 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 or sodium benzoate
  • the amount of the pharmaceutical composition administered depends upon the percent of active ingredients within its formula, which is a function of the amount of the naphthalene derivative and any optional components such as a decongestant, cough suppressant, expectorant and/or antihistamine required per dose, stability, release characteristics and other pharmaceutical parameters.
  • each individual dosage of the pharma ⁇ ceutical compositions of the present invention range from about 1 mg/kg to about 25 mg kg, preferably from about 2 mg/kg to about 15 mg kg and most preferably from about 3 mg/kg to about 10 mg/kg.
  • a hard gelatin capsule composition for oral administration is prepared by combining the following ingredients:
  • Triturate active ingredients and q.s. with lactose to selected capsule size.
  • Administration of 1 or 2 of the above capsules to a human in need of treatment provides improved relief from cough, cold-like, flu and flu-like symptoms.
  • a hard gelatin capsule composition for oral administration is prepared by combining the following ingredients:
  • Triturate active ingredients and q.s. with lactose to selected capsule size are administered to selected capsule size.
  • Administration of 1 or 2 of the above capsules to a human in need of treatment provides improved relief from cough, cold-like, flu and flu-like symptoms.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% of the final batch volume) is poured into a batch container equipped with a lightnin' mixer.
  • the sodium citrate, citric acid, and actives other than ibuprofen are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then colorants added.
  • the colorants are added to purified water (approximately 0.5% of the final batch volume).
  • This colorant solution is then added to the first batch container.
  • the ketoprofen lysinate is added to the alcohol while stirring.
  • the propylene glycol, other actives and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.
  • Administration of 10 ml to 20 ml (2 to 4 teaspoonsful) to a human in need of treatment provides improved relief from cough, cold-like, flu and flu-like symptoms.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% of the final batch volume) is poured into a batch container equipped with a lightnin 1 mixer.
  • the sodium citrate, citric acid, pseudoephedrine HC1 and chlorpheniramine maleate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorants are added to purified water (approximately 0.5% of the final batch volume). This colorant solution is then added to the first batch con ⁇ tainer.
  • the ibuprofen argininate is added to the alcohol while stirring.
  • the propylene glycol and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.
  • a liquid composition for oral administration is prepared by combining the following ingredients:
  • the purified water (approximately 10% of the final batch volume) is poured into a batch container equipped with a lightnin' mixer.
  • the sodium citrate, citric acid, pseudoephedrine HC1 and chlorpheniramine maleate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorants are added to purified water (approximately 0.5% of the final batch volume). This colorant solution is then added to the first batch container.
  • the S (+) ibuprofen lysinate and dextro ⁇ methorphan HBr are added sequentially to the alcohol while stirring.
  • the propylene glycol and flavors are added to this alcohol premix and the resulting mixture is stirred until homogeneous and then added to the first container.
  • the remaining purified water is added to the resulting mixture and stirred.

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pain & Pain Management (AREA)
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Abstract

L'invention concerne des compositions et des procédés servant à améliorer le traitement ou l'allègement de symptomes de rhume, de refroidissement et/ou de grippe par administration d'une quantité efficace d'une composition composée de certains sels d'acide aminé d'agents anti-inflammatoires non stéroïdiens à base d'acide propionique et d'au moins (a) un décongestionnant ou (b) un expectorant ou (c) un antihistaminique ou (d) un antitussif.
EP94926020A 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'un agent anti-inflammatoire non steroidien a base d'acide propionique et au moins un decongestionnant ou un expectorant ou un antihistaminique ou un antitussif Withdrawn EP0719156A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US116927 1987-11-04
US11692793A 1993-09-07 1993-09-07
PCT/US1994/009581 WO1995007103A1 (fr) 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'un agent anti-inflammatoire non steroidien a base d'acide propionique et au moins un decongestionnant ou un expectorant ou un antihistaminique ou un antitussif

Publications (1)

Publication Number Publication Date
EP0719156A1 true EP0719156A1 (fr) 1996-07-03

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP94926020A Withdrawn EP0719156A1 (fr) 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'un agent anti-inflammatoire non steroidien a base d'acide propionique et au moins un decongestionnant ou un expectorant ou un antihistaminique ou un antitussif

Country Status (7)

Country Link
EP (1) EP0719156A1 (fr)
JP (1) JPH09502201A (fr)
CN (1) CN1130354A (fr)
AU (1) AU7604094A (fr)
BR (1) BR9407414A (fr)
CA (1) CA2170488A1 (fr)
WO (1) WO1995007103A1 (fr)

Families Citing this family (54)

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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
NZ332861A (en) * 1996-05-20 2000-08-25 G Potassium, sodium and tris oxaprozin salt pharmaceutical formulations
EP0811374A1 (fr) * 1996-05-29 1997-12-10 Pfizer Inc. Formulation d'une combinaison de cetirizine et pseudoephedrine
EP1007077B1 (fr) * 1997-01-13 2009-10-07 Emory University Glutathione destines au traitement de l'infection grippale
HUP9700654A2 (hu) * 1997-03-26 1999-09-28 Dezső Korbonits Teobromin tartalmú köhögéscsillapító készítmények
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JPH09502201A (ja) 1997-03-04
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AU7604094A (en) 1995-03-27
WO1995007103A1 (fr) 1995-03-16
BR9407414A (pt) 1996-11-12

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