WO1992004021A1 - Procede permettant d'ameliorer l'effet analgesique - Google Patents

Procede permettant d'ameliorer l'effet analgesique Download PDF

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Publication number
WO1992004021A1
WO1992004021A1 PCT/US1991/006398 US9106398W WO9204021A1 WO 1992004021 A1 WO1992004021 A1 WO 1992004021A1 US 9106398 W US9106398 W US 9106398W WO 9204021 A1 WO9204021 A1 WO 9204021A1
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WIPO (PCT)
Prior art keywords
carbon atoms
naving
medicament
mixtures
alkyl
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Application number
PCT/US1991/006398
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English (en)
Inventor
James Vincent Sorrentino
Original Assignee
Richardson Vicks Inc.
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 Richardson Vicks Inc. filed Critical Richardson Vicks Inc.
Priority to KR1019930700724A priority Critical patent/KR930701994A/ko
Priority to AU85384/91A priority patent/AU662297B2/en
Publication of WO1992004021A1 publication Critical patent/WO1992004021A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—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
    • 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

Definitions

  • the present invention relates to a method for providing improved analgesic and/or anti-inflammatory effect by administering a safe and effective amount of a composition comprising a naphthalene derivative aiong with a sympathomimetic amine.
  • Inflammation is the result of complex interconnected physiological events, including increased vascular permeability, fluid accumulations, and the migration of a cnanging population of inflammatory cells into the inflamed area.
  • the clinical manifestations of inflammation include swelling (edema), increased local temperature, erythema, and pain.
  • the inflammatory response can be triggered by any of a numcer of causative factors, including certain bacteria, radiation, hypersensitivity to chemical agents, arthritis-like conditions, and the like.
  • the inflammatory response is generally believed to be a primary defense mechanism in the body, but, unchecked, can become excessive and can result in functional impairment.
  • non-steroidal anti-inflammatory, anti-pyretic and analgesic drugs especially the salicylates, which include aspirin and aspirin derivatives, 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, and the like.
  • Analgesics can be further classified into two main categories: opioid analgesics, including morphine, codeine, levorphanol, and the morphine-like analgesics merperidine, and methadone; and antipyretic analgesics, such as aspirin, ibuprofen, phenacetin, acetaminophen, phenylbutazone, and indomethacin.
  • opioid analgesics including morphine, codeine, levorphanol, and the morphine-like analgesics merperidine, and methadone
  • antipyretic analgesics such as aspirin, ibuprofen, phenacetin, acetaminophen, phenylbutazone, and indomethacin.
  • opioid analgesics Although the precise pharmacological action of these analgesics is uncertain, there are certain effects which readily distinguish the opioid analgesics from the antipyretics.
  • the antipyretics are weak analgesics, with much of their effect in the peripheral nervous system, so that behavioral changes do not usually occur.
  • these analgesics relieve only pain originating from muscles, joints, tendons and fasciae, and are ineffective against deep visceral pain.
  • opioid analgesics are quite effective against all types of pain, with broad-based action in the central nervous system. Aside from potent analgesia, the opioids, also known as narcotics, often produce effects on mood and other behavioral changes.
  • opioid analgesics Perhaps the most notable side effect of opioid analgesics is the fact that their repeated use is associated with tolerance, as well as psychic and physical dependence.
  • Naproxen ((+)-2-(6 ⁇ -methoxy-naphthyl) propionic acid), a nonsteroidal anti-inflammatory drug (NSAID), became available in the U.S. for the treatment of rheumatoid arthritis in 1976. Naproxen has been further indicated for osteoarthritis, tendonitis and bursitis, ankylosing spondylitis and acute gout. Additional indications include mild to moderate pain and primary dysmenorrhea. Naproxen has also been demonstrated to have less severe gastrointestinal and central nervous system adverse effects than aspirin.
  • NSAID nonsteroidal anti-inflammatory drug
  • compositions comprising certain naphthalene derivatives in combination with sympathomimetic amines provide improved analgesic and/or anti- inflammatory effect.
  • the present invention relates to a method of eliciting a sustained, enhanced analgesic response in a human or lower animal in need of such treatment, comprising administering to such human or lower animal a safe and effective amount of a composition comprising:
  • R 1 is alkyl having up to 6 carbon atoms, cycloalkyl having from 3 to 7 carbon atoms, alkoxymethyl having up to 7 carbon atoms, trifluoromethyl, vinyl, ethynyl, halo (iodo, bromo, chloro or fluoro) alkoxy having up to 6 carbon atoms, difluoromethoxy, alkoxymethoxy having up to 7 carbon atoms, alkylthiomethyloxy having up to 7 carbon atoms, alkylthio having up to 6 carbon atoms, alkoxymethylthio having up to 7 carbon atoms, cyano difluoromethylthio, phenyl or alkyl substituted phenyl having up to 8 carbon atoms; one of R 2 and R 3 is hydrogen, the other being methyl, ethyl or difluoromethyl or R 2 or R 3 together are methylene; and R 4 is hydrogen, alkyl having up to 22 carbon atoms, unsaturated al
  • the present invention relates to a method of eliciting a sustained, enhanced analgesic response in a human or lower animal in need of such treatment, comprising administering to such human or lower animal a safe and effective amount of a composition comprising a naphthalene derivative, preferably a 2-(5'-substituted-2'-naphthyl)-acetic acid derivative, and salts and esters thereof along with a sympathomimetic amine.
  • a composition comprising a naphthalene derivative, preferably a 2-(5'-substituted-2'-naphthyl)-acetic acid derivative, and salts and esters thereof along with a sympathomimetic amine.
  • naphthalene derivatives of this invention are the carboxylic acids and carboxylic acid esters represented by the following formula, and the pharmaceutically acceptable salts of the carboxylic acids represented by the following formula:
  • R 1 is alkyl having up to 6 carbon atoms, cycloalkyl having from 3 to 7 carbon atoms, alkoxymethyl having up to 7 carbon atoms, trifluoromethyl, vinyl, ethynyl, halo (iodo, bromo, chloro or fluoro) alkoxy having up to 6 carbon atoms, difluoromethoxy, alkoxymethoxy having up to 7 carbon atoms, alkylthiomethyloxy having up to 7 carbon atoms, alkylthio having up to 6 carbon atoms, alkoxymethyl thio having up to 7 carbon atoms, cyano difluoromethylthio, phenyl or alkylsubstituted phenyl having up to 8 carbon atoms;
  • R 2 and R 3 is hydrogen, the other being methyl, ethyl or difluoromethyl or R 2 or R 3 together are methyl ene;
  • R 4 is hydrogen, alkyl having up to 22 carbon atoms, unsaturated alkyl having up to 22 carbon atoms, cycloalkyl having from 3 to 7 carbon atoms, cycloalkylmethyl having from 3 to 7 carbon atoms, cycloalkylmethyl having from 4 to 9 carbon atoms, 2-cycloalkyl ethyl having from 5 to 10 carbon atoms, 3-cyclopentyl ethyl having from 5 to 10 carbon atoms, 3-cyclopentylpropyl, 3-cyclohexylpropyl, benzyl, 2-phenylethyl or 3-phenylpropyl.
  • the 6'-substituent (represented by R 1 in the above formula) is methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, methoxy, ethoxy, methoxymethyloxy, difluoromethoxy, methylthio, ethylthio, methoxymethylthio, difluoro- methylthio or phenyl; one of R 2 and R 3 is hydrogen and the other is methyl; and R 4 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, hexyl, 2-hexyl, isohexyl, heptyl, isoheptyl, octyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl
  • alkyl refers to and includes branched and straight chain hydrocarbons. Typical alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, tertiary-butyl, neopentyl, isopentyl, hexyl, octyl, nonyl, isodecyl, 6-methyldecyl, tridecyl, isotetradecyl, pentadecyl, isohexadecyl, heptadecyl, eicosyl, docosyl, and the like.
  • unsaturated alkyl refers to unsaturated hydrocarbon groups such as vinyl, allyl, propenyl, crotyl, isopropenyl, 2-propynyl, 1-propenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-penten-4-ynyl and the like.
  • cycloalkyl refers to cyclo hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • alkoxy refers to straight or branched chain alkyl ether groups such as methoxy, ethoxy, 2-propoxy, butoxy, 3-pentoxy and the like.
  • alkoxymethyloxy refers to methyl ether groups substituted with one alkoxy group (defined above) such as methoxymethyloxy, ethoxymethloxy, isopropoxymethyloxy and the like.
  • alkylthio refers to straight or branched chain alkylthio ether groups such an methylthio, ethylthio, propylthio. 2-propylthio, 2-butylthio, pentylthio, 3-hexylthio and the like.
  • alkylthiomethyloxy refers to methyl ether groups substituted with an alkylthio group (defined above) such as methylthiomethyloxy, 2-propylthiomethyloxy, pentylthiomethloxy and the like.
  • alkylthiomethylthio as used herein denoted methylthio ether groups substituted with an alkylthio group such as methylthiomethylthio, ethylthiomethylthio and the like.
  • alkoxymethylthio refers to methylthio ether groups substituted with an alkoxy group such as methoxymethylthio, ethoxymethylthio, 2-propoxymethylthio and the like.
  • aryl refers to phenyl, or o-, m- and/or p- alkylsubstituted phenyl derivatives such as phenyl, o-tolyl, m-tolyl, p-tolyl, o-ethyl phenyl, m-ethylphenyl, p-ethylphenyl, xylyl and the like.
  • cycloalkylmethyl refers to cycloalkyl substituted methyl groups such as cyclopropylmethyl, cyclobutylmethy, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, and the like.
  • 2-cycloalkylethyl refers to an ethyl group substituted at the 2-position with a cycloalkyl group such as 2-cyclopropylethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, 2-cyclohexylethyl and 2-cycloheptylethyl.
  • the most preferred compound used herein is (+)-2-(6 ⁇ -methoxy- 2-napthyl) propionic acid, and salts and esters thereof.
  • salts refers to salts prepared from pharmaceutically acceptable non-toxic bases including inorganic bases and organic bases. Salts derived from nonorganic bases include sodium, potassium, lithium, ammonia, calcium, magnesium, ferrous, zinc, manganous, aluminum, ferric, manganic salts and the like.
  • Salts derived from pharmaceutically acceptable organic non- toxic bases include salts of primary, secondary, tertiary and quaternary ami nes , substituted ami nes i ncluding natural ly occurri ng substi tuted amines, cyclic amines and basic ion exchange resins, such as triethylamine, tripropyl amine, 2-dimethylaminoethanol, 2-diethylamino- ethanol, lysine, arginine, histidine, caffeine, procaine, N-ethylpip- eridine, hydrabamine, choline, betaine, ethyl enedi amine, glucosamine, methylglycamine, theobromine, purines, piperazine, piperidine, poly- amine resins and the like.
  • basic ion exchange resins such as triethylamine, tripropyl amine, 2-dimethylaminoethanol, 2-diethyla
  • the compounds of Formula 1 exist as pairs of enantiomorphs or optical isomers. Each enantiomorph and mixtures thereof are included within the present invention.
  • the compounds of Formula 1 which exist as pairs of enantiomorphs can be administered as racemic mixtures or they can be administered as resolved enantiomorphs. In some instances, one enantiomorph exhibits greater anti-inflammatory, analgesic and/or anti-pyretic activity than the other corresponding enantiomorph.
  • the most preferred derivatives for use herein are the S(+)enantiomorphs.
  • optical isomers can be resolved by conventional means, such as selective biological degradation or by the preparation of dias- tereo-isomeric salts of the naphthalene derivative with an optically active amine base such as cinchonidine and separating the diastereoisomers by fractional crystallization. The separated diastereoisomeric salts are then acid cleaved to yield the respective optical isomer.
  • Sympathomimetic amines are a well-known class of drugs which activate adrenergic receptors. These drugs are fully described in Respiratory Pharmacology and Therapeutics, Ziment, W.B., Saunders & Company (1978), pp. 316-339, which is incorporated by reference herein. Drugs that are particularly preferred for use herein are those which are known to stimulate the alpha adrenergic receptors.
  • the sympathomimetic amines useful herein include pseudoephedrine, phenylpropanolamine, phenylephrine and ephedrine, their pharmaceutically acceptable salts, and mixtures thereof.
  • the pharmaceutical compositions of the present invention comprise the naphthalene derivative and sympathomimetic amine in a ratio of naphthalene derivative:sympathomimetic amine 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, gelcaps 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, tablet triturates, 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.
  • Liquid oral dosage forms include aqueous and nonaqueous solutions, 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.
  • aqueous-based orally acceptable pharmaceutical carrier is one wherein the entire or predominant solvent content is water.
  • 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.
  • 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 cough suppressant such as dextromethorphan, chlophedianol, carbetapentane, caramiphen, noscapine, diphenhydramine, codeine, hydrocodone, hydromorphone, fominoben, their pharmaceutically-acceptable salts; an expectorant or mucolytic such as glyceryl guaiacolate, terpin, ammonium chloride, N-acetylcysteine and bromhexine, ambroxol, their pharmaceutically acceptable salts; and an antihistamine such as chlorpheniramine brompheniramine, dexchlorpheniramine, dexbrompheniramine, triprolidine, doxylamine, tripelennamine, cyproheptadine, carbinoxamine, bromodiphenhydramine, phenindamine, pyrilamine
  • bronchodilators such as theophylline and albuterol.
  • a highly preferred optional component is caffeine, which is preferably present at a level of from about 10% to about 50%.
  • 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, expectorant and/or antihistamine required per dose, stability, release characteristics and other pharmaceutical parameters.
  • each individual dosage of the pharmaceutical 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.
  • Typical unit dosage forms for oral administration generally comprise from about 100 mg to about 2000 mg, preferably from about 150 mg to about 600 mg and most preferably from about 150 mg to about 400 mg of the naphthalene derivative.
  • a soft 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 Triturate active ingredients and q.s. with lactose to selected capsule size.
  • a soft 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 Triturate active ingredients and q.s. with lactose to selected capsule size.
  • 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 Pseudoephedrine HCI are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorance are added to purified water (approximately 0.5% of the final batch volume). This colorance solution is then added to the first batch container.
  • the naproxen 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.
  • Administration of 30 ml to a human in need of treatment provides improved analgesic and/or anti-inflammatory effect.
  • 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 HCI and chlorpheniramine maleate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorance are added to purified water (approximately 0.5% of the final batch volume). This colorance solution is then added to the first batch container.
  • the naproxen 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 HCI and chlorpheniramine maleate are added sequentially and dissolved with agitation.
  • the glycerin and liquid sugar are then added.
  • the colorance are added to purified water (approximately 0.5% of the final batch volume). This colorance solution is then added to the first batch container.
  • the naproxen and dextromethorphan 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.
  • Administration of 30 ml to a human in need of treatment provides improved analgesic and/or anti-inflammatory effect.

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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)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pain & Pain Management (AREA)
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  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

Procédé permettant d'améliorer l'effet analgésique et/ou anti-inflammatoire en administrant une quantité sûre et efficace d'une composition comprenant un dérivé de naphtalène parallèlement à une amine sympathomimétique.
PCT/US1991/006398 1990-09-11 1991-09-09 Procede permettant d'ameliorer l'effet analgesique WO1992004021A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1019930700724A KR930701994A (ko) 1990-09-11 1991-09-09 개선된 진통 효과를 제공하는 방법
AU85384/91A AU662297B2 (en) 1990-09-11 1991-09-09 Method for providing improved analgesic effect

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58068590A 1990-09-11 1990-09-11
US580,685 1990-09-11

Publications (1)

Publication Number Publication Date
WO1992004021A1 true WO1992004021A1 (fr) 1992-03-19

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Application Number Title Priority Date Filing Date
PCT/US1991/006398 WO1992004021A1 (fr) 1990-09-11 1991-09-09 Procede permettant d'ameliorer l'effet analgesique

Country Status (9)

Country Link
JP (1) JPH06500784A (fr)
KR (1) KR930701994A (fr)
AU (1) AU662297B2 (fr)
CA (1) CA2090234C (fr)
IE (1) IE913185A1 (fr)
MA (1) MA22277A1 (fr)
MX (1) MX9101045A (fr)
PT (1) PT98919A (fr)
WO (1) WO1992004021A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994028872A1 (fr) * 1993-06-04 1994-12-22 Warner-Lambert Company Medication sans alcool contre les rhumes et pour les sinus
US5626831A (en) * 1995-12-20 1997-05-06 Van Moerkerken; Arthur Method for relief and prevention of common cold, and compositions
US7863287B2 (en) 2002-12-18 2011-01-04 Wyeth Llc Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4549618B2 (ja) * 2001-11-22 2010-09-22 第一三共ヘルスケア株式会社 鼻炎用組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985002540A1 (fr) * 1983-12-12 1985-06-20 Richardson-Vicks, Inc. Compositions analgesiques et anti-inflammatoires comprenant des xanthines et leurs procedes d'utilisation
WO1985003443A1 (fr) * 1984-02-08 1985-08-15 Richardson-Vicks, Inc. Compositions analgesiques et anti-inflammatoires comprenant de la diphenhydramine et leurs procedes d'utilisation
WO1985004589A1 (fr) * 1984-04-09 1985-10-24 Abraham Sunshine Melanges contre la toux et le rhume comprenant des medicaments anti-inflammatoires non steraniques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985002540A1 (fr) * 1983-12-12 1985-06-20 Richardson-Vicks, Inc. Compositions analgesiques et anti-inflammatoires comprenant des xanthines et leurs procedes d'utilisation
WO1985003443A1 (fr) * 1984-02-08 1985-08-15 Richardson-Vicks, Inc. Compositions analgesiques et anti-inflammatoires comprenant de la diphenhydramine et leurs procedes d'utilisation
WO1985004589A1 (fr) * 1984-04-09 1985-10-24 Abraham Sunshine Melanges contre la toux et le rhume comprenant des medicaments anti-inflammatoires non steraniques

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994028872A1 (fr) * 1993-06-04 1994-12-22 Warner-Lambert Company Medication sans alcool contre les rhumes et pour les sinus
US5626831A (en) * 1995-12-20 1997-05-06 Van Moerkerken; Arthur Method for relief and prevention of common cold, and compositions
US7863287B2 (en) 2002-12-18 2011-01-04 Wyeth Llc Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines

Also Published As

Publication number Publication date
IE913185A1 (en) 1992-03-11
CA2090234C (fr) 1998-08-11
MX9101045A (es) 1992-05-04
AU662297B2 (en) 1995-08-31
JPH06500784A (ja) 1994-01-27
PT98919A (pt) 1992-07-31
MA22277A1 (fr) 1992-04-01
CA2090234A1 (fr) 1992-03-12
AU8538491A (en) 1992-03-30
KR930701994A (ko) 1993-09-08

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