EP0674527A1 - Verwendung von s(+) antipoden von analgetika zur herstellung einer zusammensetzung zur behandlung von atemwegserkrankungen - Google Patents
Verwendung von s(+) antipoden von analgetika zur herstellung einer zusammensetzung zur behandlung von atemwegserkrankungenInfo
- Publication number
- EP0674527A1 EP0674527A1 EP94902518A EP94902518A EP0674527A1 EP 0674527 A1 EP0674527 A1 EP 0674527A1 EP 94902518 A EP94902518 A EP 94902518A EP 94902518 A EP94902518 A EP 94902518A EP 0674527 A1 EP0674527 A1 EP 0674527A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- mixtures
- acceptable salts
- pharmaceutical composition
- cold
- 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- Withdrawn
Links
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
- 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 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
- a composition comprising an analgesic agent substantially free or of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof, and mixtures thereof along with at least one of (a) a decongestant, (b) an expectorant and (c) an antitussive.
- the common co ⁇ d although not usually a serious illness, is a highly prevalent, discomforting and annoying infliction.
- the term "common cold” is applied to minor respiratory illnesses caused by a variety of different respiratory viruses. 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 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 an general malaise associated therewith generally contain an analgesi (aspirin or acetaminophen) and one or more antihistaminics, decon gestants, cough suppressants, antitussives and expectorants.
- non-steroidal anti-inflammatory drugs to comba inflammation and attendant pain is accepted medical practice. Th non-steroidals are commonly employed to relieve pain and inflammatio associated with, for example, bursitis, arthritis, headache and th like.
- drugs of the non-narcotic anal- gesic class of drugs are aspirin, acetaminophen, ibuprofen and naprox- en.
- Aspirin, acetaminophen and ibuprofen have heretofore been includ ⁇ ed as the pain reliever and fever-reducing component in conventional cough/cold multi-symptom alleviating compositions.
- These commerciall marketed products generally contain in addition to aspirin, acetamino- phen or ibuprofen, one or more antihistaminics, decongestants, cough- suppressants, antitussives and expectorants.
- Ibuprofen or (+) 2-(p-isobutylphenyl)propionic acid
- Ibuprofen is well-known as a nonsteroidal anti-inflammatory drug having analgesic and antipyretic activity.
- Ibuprofen is currently marketed b prescription in the United States generically, as well as unde tradenames such as Motrin ® , which is available in 400, 600 and 800 mg tablets for oral administration.
- Ibuprofen has recently also become available in this country in non-prescription strength (200 mg) under a variety of tradenames, including Advil ® and Nuprin ® , as well as in generic form.
- For the treatment of mild to moderate pain 400 mg every 4 to 6 hours, not to exceed 3200 mg daily, is generally recommended for Motrin®.
- the lower dose over-the-counter products are generally recommended for minor aches and pains, to be used orally at the 200 to 400 mg level, every 4 to 6 hours, not to exceed 1200 m daily unless directed by a physician.
- Flurbiprofen or (+) [l,l'-biphenyl]-4-acetic acid 2-fluoro-alphamethyl, is also well-known as a nonsteroida anti-inflammatory drug having analgesic and antipyretic activity Flurbiprofen is currently marketed by prescription in the Unite States under the tradename Ansaid ® , which is available in 50 and 10 mg tablets for oral administration.
- Ketoprofen or (+) 2-(3-benzoylphenyl)propionic acid, anothe well-known nonsteroidal anti-inflammatory drug having analgesic an antipyretic activity is currently marketed by prescription in th United States under the tradename Orudis®, which is available in 25 50 and 75 mg capsules for oral administration.
- Orudis® for the treatment o mild to moderate pain, 25-50 mg every 6 to 8 hours, not to exceed 30 mg daily, is generally recommended for Orudis ® .
- Physician 's Des Reference, 46th edition, 1992, publisher Edward R. Barnhart, Medica Economics Company, Inc., Oradell, N.J. 07649, pp. 2351-54, 2319-20 an 2488-90 the disclosure of which is incorporated herein.
- these analgesi agents are racemic mixtures. It is only the racemic mixture of thes agents which have in fact ever been marketed. There have, however been some studies of the individual S(+) and R(-) enantiomer o ibuprofen. In the body, some of the R(-) enantiomer is converted t the S(+) enantiomer, which is the pharmaceutically active form o ibuprofen.
- compositions comprising an analgesic agent substantially free of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof and mixtures thereof, with at least one of (a) a decongestant, (b) an expectorant and (c) an antitussive provides improved treatment, management or mitigation of cold, cold-like and/or flu symptoms.
- an analgesic agent substantially free of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof and mixtures thereof, with at least one of (a) a decongestant, (b) an expectorant and (c) 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 analgesic agent substantially free or of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof, and mixtures thereof along with at least one of (a) a decongestant, (b) an expectorant and (c) an antitussive. All percentages and ratios used herein are by weight unless otherwise indicated.
- 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 analgesic agent substantially free or of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof, and mixtures thereof along with at least one of (a) a decongestant, (b) an expectorant and (c) an antitussive.
- an analgesic agent substantially free or of its R(-) antipode selected from the group consisting of (S+)-ibuprofen, (S+) flurbiprofen and (S+) ketoprofen, pharmaceutically-acceptable salts thereof, and mixtures thereof along with at least one of (a) a decongestant, (b) an expectorant and (c) an antitussive.
- S(+) as applied to the analgesic agents herein is intended to encompass not only the dextrorotatory or S(+) iso er of these agents but also any pharmaceutically acceptable, analgesically effective salt thereof.
- 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 S(+) 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 S(+) 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 S(+) 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.
- 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 quater ⁇ nary amines, substituted amines including naturally occurring substi ⁇ tuted amines, cyclic amines and basic ion exchange resins, such as triethylamine, tripropylamine, 2-dimethylaminoethanol, 2-diethylaminoethanol, lysine, arginine, histidine, caffeine, procaine, N-ethylpiperidine, hydraba ine, choline, betaine, ethylenediamine, glucosa ine, methylglycamine, theobromine, purines, piperazine, piperidine, polyamine resins and the like.
- basic ion exchange resins such as triethylamine, tripropylamine, 2-dimethylaminoethanol, 2-diethylaminoethanol, lysine, arginine, histidine, caffeine, procaine,
- compositions of the present invention also include at least one other pharmacological active selected from the following class: (a) a decongestant, (b) an expectorant and (c) an antitussive.
- a decongestant selected from the following class: (a) a decongestant, (b) an expectorant and (c) an antitussive.
- the decongestants useful in the compositions of the present invention include pseudoephedrine, phenylpropanolamine, phenylephrine and ephe- drine, their pharmaceutically acceptable salts, and mixtures thereof.
- the 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 expectorants (also known as mucolytic agents) useful in the present invention 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.
- compositions of the present invention comprise the S(+) enantiomer and other pharmacological active in a ratio of S(+) enantiomer: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 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, 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 accept ⁇ able carriers and excipients that may be used to formulate oral dosage forms are described in U.S. Patent 3,903,297, Robert, issued Sep ⁇ tember 2, 1975, incorporated by reference herein.
- 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 pharmaceuti ⁇ cal composition in an aqueous vehicle containing a suitable suspending agent.
- suitable suspending agents include Avicel RC-591 (a microcrys- talline cellulose/sodium carboxymethyl cellulose mixture available from FMC), guar gum and the like.
- 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 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, an antihistamine such as chlorpheniramine, brompheniramine, dexchlorphen- iramine, dexbromphreniramine, triprolidine, azatadine, doxylamine, tripelennamine, cyproheptadine, hydroxyzine, clemastine, carbinox- amine, phenindamine, bromodiphenhydramine, pyrila ine, their pharmaceutically acceptable salts, as well as the non-sedating anti- histamines which include acrivastine, AHR-11325, astemizole, azelas- tine, cetirizine, ebastine, ketotifen, lodoxamide, loratidine, levoca- bastine, mequitazine, oxato ide, setastine, tazifylline, warmthlastine
- bronchodilators such as terbutaline, aminophylline epinephrine, isoprenaline, metaproterenol, bitoterol, theophylline an albuterol as well as other analgesic agents such as acetaminophen an aspirin.
- a highly preferred optional component is caffeine.
- ingredients well known to the pharmacist's art ma also be included in amounts generally known for these ingredients, fo example, natural or artificial sweeteners, flavoring agents, colorant and the like to provide a palatable and pleasant looking final prod uct, antioxidants, for example, butylated hydroxy anisole or butylate hydroxy toluene, and preservatives, for example, methyl or propy paraben or sodium benzoate, to prolong and enhance shelf life.
- the amount of the pharmaceutical composition administered depend upon the percent of active ingredients within its formula, which is function of the amount of the naphthalene derivative and any optiona components such as a decongestant, cough suppressant, expectoran and/or antihista ine required per dose, stability, release character istics and other pharmaceutical parameters.
- each individual dosage of the pharmaceutical composition 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 preferabl 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: Ingredient Amount S(+) Ibuprofen 100 mg
- Triturate active ingredients and q.s. with lactose to selected capsule size 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: Ingredient Amount
- Glyceryl guaiacolate 100 mg Triturate active ingredients and q.s. with lactose to selected capsule size.
- a liquid composition for oral administration is prepared by ning the following iingredients:
- 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 ibuprofen is added to the alcohol while stirring.
- the propylene glycol, other actives and flavors are added to this alcohol pre ix 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' 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 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 10 ml to 20 ml (2 to 4 Teaspoonsful) 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 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 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)
- 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)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99970192A | 1992-12-21 | 1992-12-21 | |
US999701 | 1992-12-21 | ||
PCT/US1993/012022 WO1994014476A1 (en) | 1992-12-21 | 1993-12-09 | Use of s(+) antipodes of analgesic agents for the manufacture of a composition to treat respiratory disorders |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0674527A1 true EP0674527A1 (de) | 1995-10-04 |
Family
ID=25546608
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94902518A Withdrawn EP0674527A1 (de) | 1992-12-21 | 1993-12-09 | Verwendung von s(+) antipoden von analgetika zur herstellung einer zusammensetzung zur behandlung von atemwegserkrankungen |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0674527A1 (de) |
JP (1) | JPH08506808A (de) |
CA (1) | CA2151912A1 (de) |
MX (1) | MX9400040A (de) |
WO (1) | WO1994014476A1 (de) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2293099A (en) * | 1994-09-15 | 1996-03-20 | Mailway Packaging Group Ltd | Drug formulation |
GB9523833D0 (en) * | 1995-11-22 | 1996-01-24 | Boots Co Plc | Medical treatment |
AU7916798A (en) * | 1997-05-22 | 1998-12-11 | Boots Company Plc, The | Pharmaceutical compositions of flurbiprofen and burn-masking agent for treating sore throat |
US6211246B1 (en) * | 1999-06-10 | 2001-04-03 | Mcneil-Ppc, Inc. | Rapidly absorbed liquid compositions |
NZ532019A (en) * | 2001-09-04 | 2007-04-27 | Boehringer Ingelheim Int | Anti-influenza drugs |
DE10203104A1 (de) * | 2002-01-25 | 2003-08-07 | Boehringer Ingelheim Pharma | Ambroxol für die Behandlung chronischer Schmerzen |
TWI313598B (en) | 2002-12-18 | 2009-08-21 | Wyeth Corp | Compositions of non-steroidal anti-inflammatory drugs, decongestants and anti-histamines |
US20050192355A1 (en) * | 2004-02-17 | 2005-09-01 | Wyeth | Compositions of non-steroidal anti-inflammatory drugs and decongestants or anti-histamines |
ES2486296T3 (es) | 2007-07-12 | 2014-08-18 | Ge Healthcare As | Agentes de contraste |
JP5364330B2 (ja) * | 2007-10-10 | 2013-12-11 | 第一三共ヘルスケア株式会社 | アゼラスチンとアンブロキソールとを含有する医薬組成物 |
WO2015163832A1 (en) | 2014-04-25 | 2015-10-29 | Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A.Ş. | An ibuprofen and famotidine combined composition having improved stability |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4552899A (en) * | 1984-04-09 | 1985-11-12 | Analgesic Associates | Cough/cold mixtures comprising non-steroidal anti-inflammatory drugs |
US4999226A (en) * | 1988-06-01 | 1991-03-12 | Merrell Dow Pharmaceuticals Inc. | Pharmaceutical compositions for piperidinoalkanol-ibuprofen combination |
US4990535A (en) * | 1989-05-03 | 1991-02-05 | Schering Corporation | Pharmaceutical composition comprising loratadine, ibuprofen and pseudoephedrine |
US5164398A (en) * | 1991-04-01 | 1992-11-17 | Merck & Co., Inc. | Ibuprofen-antitussive combinations |
JPH06506684A (ja) * | 1991-04-01 | 1994-07-28 | メルク エンド カンパニー インコーポレーテッド | イブプロフェン−充血除去剤配合物 |
-
1993
- 1993-12-09 JP JP6515219A patent/JPH08506808A/ja active Pending
- 1993-12-09 WO PCT/US1993/012022 patent/WO1994014476A1/en not_active Application Discontinuation
- 1993-12-09 EP EP94902518A patent/EP0674527A1/de not_active Withdrawn
- 1993-12-09 CA CA002151912A patent/CA2151912A1/en not_active Abandoned
-
1994
- 1994-01-03 MX MX9400040A patent/MX9400040A/es unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9414476A1 * |
Also Published As
Publication number | Publication date |
---|---|
JPH08506808A (ja) | 1996-07-23 |
WO1994014476A1 (en) | 1994-07-07 |
CA2151912A1 (en) | 1994-07-07 |
MX9400040A (es) | 1994-07-29 |
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