EP0717624A1 - Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine - Google Patents

Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine

Info

Publication number
EP0717624A1
EP0717624A1 EP94926021A EP94926021A EP0717624A1 EP 0717624 A1 EP0717624 A1 EP 0717624A1 EP 94926021 A EP94926021 A EP 94926021A EP 94926021 A EP94926021 A EP 94926021A EP 0717624 A1 EP0717624 A1 EP 0717624A1
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
caffeine
amino acid
composition according
propionic acid
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Withdrawn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
EP94926021A
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 EP0717624A1 publication Critical patent/EP0717624A1/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Withdrawn legal-status Critical Current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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • 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 analgesic and/or anti-inflammatory effect by administering a safe and ef ⁇ fective amount of a composition comprising certain amino acid salts of propionic acid non-steroidal anti-inflammatory agents along with an amount of caffeine sufficient to hasten the onset.
  • Inflammation is the result of complex in ⁇ terconnected physiological events, including increased vascular permeability, fluid accumulations, and the migration of a changing population of inflammatory cells into the inflamed area.
  • the clinical manifestations of inflammation include swelling (edema), increased local temperature, erythema, and pain.
  • the inflammatory re ⁇ sponse can be triggered by any of a number 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 meperidine, 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 meperidine, and methadone
  • antipyretic analgesics such as aspirin, ibuprofen, phenacetin, acetaminophen, phenylbutazone, and indomethacin.
  • opioid 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.
  • 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.
  • compositions comprising certain amino acid salts of the propionic acid NSAIDs in combination with caffeine provides further 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, compris ⁇ ing administering to such human or lower animal a safe and effective amount of a composition comprising: a. an analgesically and anti-inflammatory effective amount of an amino acid salt of a propionic acid NSAID; and b. an amount of caffeine sufficient to hasten the onset of and enhance the analgesic response. All percentages and ratios used herein are by weight unless otherwise indi ⁇ cated.
  • the present invention relates to compositions and methods 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 ibuprofen lysinate, and an amount of caffeine sufficient to hasten the onset of and enhance the analgesic response.
  • 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.
  • S(+) M as applied to the analgesic agents herein is intended to encompass the dextrorotatory or S(+) isomer of the amino acid salt derivatives thereof.
  • substantially free of the R(-) antipode as used in conjunction with the term "S(+) M means that the S(+) enantiomer is sufficiently free it is R(-) antipode to exert the desired onset-hastened and enhanced analgesic effect.
  • 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.
  • 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 1000 mg., and are generally the same as their acid derivatives counterparts.
  • Useful dosage of these agents can be found in The Physicians' Desk Reference. 47th Edition (1993) and in U.S. Patent 4,552,899 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 ibup ⁇ rofen used in the compositions of the present invention generally ranges from about 50 to about 800 g, 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 tcuabout 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 useful in the compositions of the present invention generally ranges from about 5 to about 100 mg, preferably from about 5 to about 75 g, 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.
  • the pharmaceutical compositions of the present invention comprise the analgesic agent and caffeine in a ratio of from about 10: 1 to about 1 : 10, preferably from about 5: 1 to about 1 :5 and most preferably from about 2: 1 to about 1 :5.
  • 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 pref ⁇ erably 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 com ⁇ ponent.
  • 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, emul ⁇ sions, suspensions, and solutions and/or suspensions reconstituted 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.
  • Specific examples of pharmaceutically acceptable carriers and excipients that may be used to formulate oral dosage forms are de ⁇ scribed in U.S. Patent 3,903,297, Robert, issued September 2, 1975, incorporated by reference herein. Techniques and compositions for making solid oral dosage forms are described in Marshall, "Solid Oral Dosage Forms," Modern Pharmaceu- tics, Vol. 7.
  • 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 mix ⁇ ture available from FMC), guar gum and the like. Such suspending agents are well known to those skilled in the art. While the amount of water in the compositions of this invention can vary over quite a wide range depending upon the total weight and volume of the active component and other optional non-active ingredients, the total water content, based on the weight of the final composition, will generally range from 2 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 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 as well as other analgesic agents such as acetaminophen and aspirin.
  • a highly prefe ⁇ ed 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 ibuprofen and caffeine 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 50 mg to about 2000 mg, preferably from about 100 mg to about 600 mg and most preferably from about 100 mg to about 400 mg of the ibuprofen and from about 25 mg to about 200 mg, preferably from about 50 mg to about 200 mg and most preferably from about 50 mg to about 100 mg of caffeine. While dosages higher than the foregoing are effective to provide analgesic relief, care must be taken, as with any drug, in some individuals to prevent adverse side effects.
  • 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 analgesic and/or anti-inflammatory effect.
  • 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 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 and Caffeine 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 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 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: Ingredient % W/V
  • 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 HCl 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)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Compositions et procédés servant à produire un effet analgésique et/ou anti-inflammatoire 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 avec une quantité de caféine suffisante pour accélérer l'efficacité de l'action.
EP94926021A 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine Withdrawn EP0717624A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US117389 1980-02-01
US11738993A 1993-09-07 1993-09-07
PCT/US1994/009582 WO1995007079A1 (fr) 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine

Publications (1)

Publication Number Publication Date
EP0717624A1 true EP0717624A1 (fr) 1996-06-26

Family

ID=22372657

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94926021A Withdrawn EP0717624A1 (fr) 1993-09-07 1994-08-24 Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine

Country Status (6)

Country Link
EP (1) EP0717624A1 (fr)
JP (1) JPH09502202A (fr)
AU (1) AU7604194A (fr)
BR (1) BR9407415A (fr)
CA (1) CA2170485C (fr)
WO (1) WO1995007079A1 (fr)

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US5804560A (en) * 1995-01-06 1998-09-08 Sibia Neurosciences, Inc. Peptide and peptide analog protease inhibitors
US5863902A (en) * 1995-01-06 1999-01-26 Sibia Neurosciences, Inc. Methods of treating neurodegenerative disorders using protease inhibitors
AU718030B2 (en) * 1996-05-20 2000-04-06 G.D. Searle & Co. Potassium, sodium and tris oxaprozin salt pharmaceutical formulations
WO1999052528A1 (fr) * 1998-04-11 1999-10-21 Errekappa Euroterapici S.P.A. Preparations pharmaceutiques a base de sels de ketoprofene hydrosoluble et applications correspondantes
PL345340A1 (en) 1998-07-09 2001-12-17 Warner Lambert Co Compositions comprising gaba analogs and caffeine
US6211246B1 (en) * 1999-06-10 2001-04-03 Mcneil-Ppc, Inc. Rapidly absorbed liquid compositions
US20040115290A1 (en) 2001-06-20 2004-06-17 Tripp Matthew L. Modulation of inflammation by hops fractions and derivatives
US8158160B2 (en) 2001-11-13 2012-04-17 Eric Hauser Kuhrts Anti-inflammatory cyclooxygenase inhibitors
US7166641B2 (en) * 2002-10-02 2007-01-23 Yung Shin Pharmaceutical Industrial Co., Ltd. Pharmaceutically acceptable salts containing local anesthetic and anti-inflammatory activities and methods for preparing the same
TWI313598B (en) * 2002-12-18 2009-08-21 Wyeth Corp Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines
US9629847B2 (en) 2011-11-23 2017-04-25 Michael Leighton Compositions and methods for treating symptoms of inflammatory related conditions using a combination of an antihistamine and a stimulant
US9149474B2 (en) 2011-11-23 2015-10-06 Michael Leighton Compositions and methods for treating symptoms of inflammatory related conditions using a combination of an antihistamine and a stimulant
EP3406239B1 (fr) * 2017-05-22 2021-10-20 Epifarma Srl Solutions de sel de lysine de kétoprofène agréables au goût

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US4420483A (en) * 1982-07-22 1983-12-13 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising ibuprofen and methods of using same
DE3328401A1 (de) * 1983-08-05 1985-02-21 Merckle GmbH, 7902 Blaubeuren Injizierbare loesung zur behandlung von entzuendungen
WO1991006295A1 (fr) * 1989-11-06 1991-05-16 Sepracor, Inc. Composition analgesique contenant du s(+) flurbiprofene optiquement pur
US4994604A (en) * 1990-01-10 1991-02-19 Merck & Co., Inc. Formation and resolution of ibuprofen lysinate
EP0663819A4 (fr) * 1992-09-29 1998-05-27 Merck & Co Inc Association d'ibuprofene et de cafeine.
AU672279B2 (en) * 1992-12-21 1996-09-26 Procter & Gamble Company, The Compositions containing caffeine and S(+)-ibuprofen or S(+)-flurbiprofen or S(+)-ketoprofen
WO1994016703A1 (fr) * 1993-01-29 1994-08-04 Merck & Co., Inc. Combinaison de cyclobenzaprine et de cafeine utilisee comme myorelaxant

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Also Published As

Publication number Publication date
CA2170485C (fr) 2000-11-07
WO1995007079A1 (fr) 1995-03-16
AU7604194A (en) 1995-03-27
BR9407415A (pt) 1996-11-12
JPH09502202A (ja) 1997-03-04
CA2170485A1 (fr) 1995-03-16

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