EP0577757A1 - Ibuprofen-decongestant combinations - Google Patents
Ibuprofen-decongestant combinationsInfo
- Publication number
- EP0577757A1 EP0577757A1 EP92910669A EP92910669A EP0577757A1 EP 0577757 A1 EP0577757 A1 EP 0577757A1 EP 92910669 A EP92910669 A EP 92910669A EP 92910669 A EP92910669 A EP 92910669A EP 0577757 A1 EP0577757 A1 EP 0577757A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ibuprofen
- substantially free
- salt
- phenylpropanolamine
- phenylephrine
- 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- Withdrawn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
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Definitions
- NSAID NSAID
- Ibuprofen (2-(4-isobutylphenyl)propionic acid) is a well known and commonly employed NSAID.
- S-ibuprofen single enantiomer
- racemic ibuprofen see for example U.S. Patent 4,877,620.
- the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine are sympathomimetic agents (Decongestants) which are useful for the treatment of nasal congestion arising from cold, allergy, flu or sinus conditions. These agents function by constricting the smaller arterioles of the nasal passages producing a decongestant effect.
- compositions for use in the treatment of pain and inflammation and the relief of nasal congestion and sinus pressure symptoms in a mammalian organism, said composition comprising:
- This invention is also directed to a method of treating pain and inflammation and the relief of nasal congestion and sinus pressure in a mammalian organism in need of such treatment comprising administering to such organism: (i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen; and
- This invention is also directed to a method of treating pain and inflammation and the relief of nasal congestion and sinus pressure in a mammalian organism in need of such treatment comprising administering to such organism:
- compositions and methods of the present invention may be used to treat pain and inflammation, or pain alone or inflammation alone where only one is present, along with the treatment of nasal congestion and sinus pressure symptoms.
- Substantially free of (R)-ibuprofen should be taken to mean that the ratio of (S)-ibuprofen to (R)-ibuprofen is at least 90:10.
- Substantially free with respect to a sympathomimetic amine stereoisomer should be taken to mean that the ratio of that stereoisomer to all other stereoisomers of the sympathomimetic amine is at least 90:10.
- Salts of (S)-ibuprofen include salts with alkali metals, such as sodium or potassium, salts with alkaline earth metals, such as calcium, or salts with other metals such as magnesium, aluminum, iron, zinc, copper, nickel or cobalt.
- Salts of (S)-ibuprofen further include the amino acid salts, particularly the basic a ino acids such as lysine or arginine. Specifically included within the above composition is (S)-ibuprofen- (S)-lysine and (S)-ibuprofen-(R)-lysine.
- Salts of the sympathomimetic amine include, but are not limited to, the hydrochloride, sulfate or bitartrate.
- (S)-ibuprofen may be prepared following the procedures disclosed in U.S. Patent 4,877,620.
- Metal salts of ibuprofen may be obtained by contacting a hydroxide, or carbonate with ibuprofen.
- Amino acid salts of ibuprofen may be obtained by contacting an amino acid in solution with ibuprofen.
- (S)-ibuprofen in an analgesic/decongestant combination offers significant advantages over the combination of racemic ibuprofen with a decongestant.
- (S)-ibuprofen provides a faster onset of pain relief and an enhanced degree of relief compared to racemic ibuprofen. These benefits are increased in an (S)-ibuprofen/decongestant combination as the decongestant may potentiate the action of (S)-ibuprofen. This has not heretofore been observed because the art has not proposed the combination of the (S)-ibuprofen enantiomer, absent (R)-ibuprofen, with a decongestant.
- the decongestant also may potentiate the duration of the analgesic and anti-inflammatory response.
- the presence of the (R)-ibuprofen may blur the potentiated effect.
- the absence of (R)-ibuprofen provides significant benefits particularly to the subject in the weakened state of a cold, flu, or allergy condition.
- the allergic contraindications sometimes associated with ibuprofen administration, and which may be particularly detrimental to the cold/allergy/flu sufferer, may be absent or reduced in a composition wherein the (R)-ibuprofen is absent.
- (R)-enantiomer or the removal of this enantiomer.
- the absence of inversion reduces or eliminates the formation and incorporation into fatty tissue of hybrid-ibuprofen containing trigylcerides.
- the renal burden and renal toxicities sometimes associated with ibuprofen therapy are reduced or absent in a substantially (R)-ibuprofen free composition.
- the absence of inactive enantiomers, particularly (R)-ibuprofen provides for significant size and weight advantages in a combination dosage form, particularly a sustained release dosage form.
- a sustained release dosage of ibuprofen may have required 800 to 1000 mg
- the employment of (S)-ibuprofen reduces the weight to 650 to 800 mg and provides for a more practical size tablet for an ibuprofen/decongestant combination.
- the absence of the inactive substances in the present composition may avoid undesirable toxic interactions and clearly avoids the metabolism necessary to remove the nonactive entity.
- An effective amount of (S)-ibuprofen, or a salt thereof, for use in an unit dose composition of this invention may range from 50 to 800 mg (S)-ibu- profen.
- the preferred amount of (S)-ibuprofen is about 100 to 400 mg.
- the amount of a salt such as (S)-ibuprofen-(S)-lysine is determined based on the amount of (S)-ibuprofen contained therein.
- the sympathomimetic amine (Decongestant) employed herein is selected from phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a pharmaceutically acceptable salt. Included within this invention are any diastereomers and/or enantio ers of each decongestant. Where a particular therapeutically active stereoisomer is not commercially available it may be prepared following standard resolution chemistry from the available racemic mixture.
- the amount of the decongestant useful in the practice of the present invention may vary from about 1 mg to 100 mg depending on the specific decongestant.
- the amount of a salt, such as pseudoephedrine hydrochloride, is determined based on the amount of active decongestant, such as pseudoephedrine, contained therein.
- compositions may be administered in the form of tablets, capsules, elixirs, syrups drops, granules, liquids, nasal spray inhaler, or a suspension.
- active components may be admixed with a pharmaceutically acceptable diluent such as lactose, starch, sucrose, cellulose, magnesium stearate, dicalcium phosphate, calcium sulfate, mannitol and in a liquid composition, ethyl alcohol.
- Acceptable binders such as PVP, starch, gelatin, natural sugars, corn sweeteners, natural and synthetic gums such as acacia, sodium alginate, carboxymethylcellulose, polyethylene glycol and waxes, may also be admixed with the active components.
- lubricants such as magnesium stearic acid talc, and disintegrators such as starch, methylcellulose, agar, bentonite and guar gum and super disintegrators such as docusate sodium, sodium starch glycollate or cross linked PVP may also be included.
- the active components may also be formulated in sustained release formulations. These formulations may be employed in oral, dermal, rectal or vaginal administrations. Such sustained release forms also include layered formulations which provide for distinct release ratio and thus may be more beneficial in allowing for short and long term relief.
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Compositions pharmaceutiques destinées au traitement des douleurs et des inflammations et au soulagement de la congestion nasale et de la compression sinusale chez les organismes mammifères. La composition comporte (i) une quantité à efficacité analgésique et anti-inflammatoire d'ibuprofène-(S), ou d'un sel de celui-ci, sensiblement dépourvu d'ibuprofène-(R); et (ii) une quantité à efficacité sympathomimétique d'au moins une amine sympathomimétique sélectionnée parmi la phényléphrine, la phénylpropanolamine, la pseudo-éphédrine, l'oxymétazoline, l'éphinéphrine, la naphazoline, la xylométazoline, la propylhexédrine, la lévo-désoxyéphédrine ou un stéréoisomère thérapeutiquement actif de celle-ci, sensiblement dépourvue de ses autres stéréoisomères, ou son sel pharmaceutiquement acceptable.Pharmaceutical compositions for the treatment of pain and inflammation and for the relief of nasal congestion and sinus compression in mammalian organisms. The composition includes (i) an analgesic and anti-inflammatory amount of ibuprofen- (S), or a salt thereof, substantially free of ibuprofen- (R); and (ii) a sympathomimetic amount of at least one sympathomimetic amine selected from phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-deoxyephedrine or a therapeutically active stereoisomer thereof, substantially free of its other stereoisomers, or its pharmaceutically acceptable salt.
Description
TITLE OF THE INVENTION IBUPROFEN-DECONGESTANT COMBINATIONS
BACKGROUND OF THE INVENTION The non-steroidal anti-inflammatory drugs
(NSAID) have been utilized in the treatment of pain/ inflammation and have been disclosed as useful in the treatment, management and mitigation of cold symptoms and the pain associated therewith. Ibuprofen (2-(4-isobutylphenyl)propionic acid) is a well known and commonly employed NSAID. Recently, it has been found that a faster onset of pain relief and an enhanced analgesic response can be obtained by the utilization of the single enantiomer (S)-ibuprofen in comparison to racemic ibuprofen, (see for example U.S. Patent 4,877,620).
The sympathomimetic amines, phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine are sympathomimetic agents (Decongestants) which are useful for the treatment of nasal congestion arising from cold, allergy, flu or sinus conditions. These agents function by constricting the smaller arterioles of the nasal passages producing a decongestant effect.
Combinations of ibuprofen with decongestants have been disclosed, however despite the fact that the cold/pain sufferer is in need of quick and enhanced relief there has been no consideration given to the employment of (S)-ibuprofen, or a salt thereof, in combination with a decongestant for the treatment of pain and the relief of allergy, cold symptoms.
DETAILED DESCRIPTION OF THE INVENTION
This invention relates to pharmaceutical compositions for use in the treatment of pain and inflammation and the relief of nasal congestion and sinus pressure symptoms in a mammalian organism, said composition comprising:
(i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen; and
(ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline,
xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other εtereoisomers or a pharmaceutically acceptable salt thereof. This invention is also directed to a method of treating pain and inflammation and the relief of nasal congestion and sinus pressure in a mammalian organism in need of such treatment comprising administering to such organism: (i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen; and
(ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers or a pharmaceutically acceptable salt thereof.
This invention is also directed to a method of treating pain and inflammation and the relief of nasal congestion and sinus pressure in a mammalian organism in need of such treatment comprising administering to such organism:
(i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen; and
(ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline,
xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers or a pharmaceutically acceptable salt thereof. The compositions and methods of the present invention may be used to treat pain and inflammation, or pain alone or inflammation alone where only one is present, along with the treatment of nasal congestion and sinus pressure symptoms. Substantially free of (R)-ibuprofen should be taken to mean that the ratio of (S)-ibuprofen to (R)-ibuprofen is at least 90:10. Substantially free with respect to a sympathomimetic amine stereoisomer should be taken to mean that the ratio of that stereoisomer to all other stereoisomers of the sympathomimetic amine is at least 90:10.
Salts of (S)-ibuprofen include salts with alkali metals, such as sodium or potassium, salts with alkaline earth metals, such as calcium, or salts with other metals such as magnesium, aluminum, iron, zinc, copper, nickel or cobalt.
Salts of (S)-ibuprofen further include the amino acid salts, particularly the basic a ino acids such as lysine or arginine. Specifically included within the above composition is (S)-ibuprofen- (S)-lysine and (S)-ibuprofen-(R)-lysine.
Salts of the sympathomimetic amine include, but are not limited to, the hydrochloride, sulfate or bitartrate. (S)-ibuprofen may be prepared following the procedures disclosed in U.S. Patent 4,877,620. Metal salts of ibuprofen may be obtained by contacting a
hydroxide, or carbonate with ibuprofen. Amino acid salts of ibuprofen may be obtained by contacting an amino acid in solution with ibuprofen.
The utilization of (S)-ibuprofen in an analgesic/decongestant combination offers significant advantages over the combination of racemic ibuprofen with a decongestant. (S)-ibuprofen provides a faster onset of pain relief and an enhanced degree of relief compared to racemic ibuprofen. These benefits are increased in an (S)-ibuprofen/decongestant combination as the decongestant may potentiate the action of (S)-ibuprofen. This has not heretofore been observed because the art has not proposed the combination of the (S)-ibuprofen enantiomer, absent (R)-ibuprofen, with a decongestant. Furthermore the decongestant also may potentiate the duration of the analgesic and anti-inflammatory response. The presence of the (R)-ibuprofen may blur the potentiated effect. Furthermore, the absence of (R)-ibuprofen provides significant benefits particularly to the subject in the weakened state of a cold, flu, or allergy condition. The allergic contraindications sometimes associated with ibuprofen administration, and which may be particularly detrimental to the cold/allergy/flu sufferer, may be absent or reduced in a composition wherein the (R)-ibuprofen is absent.
The subject using the (S)-ibuprofen/decon¬ gestant combination will no longer need to divert metabolic energy to the inversion of the
(R)-enantiomer or the removal of this enantiomer. The absence of inversion reduces or eliminates the
formation and incorporation into fatty tissue of hybrid-ibuprofen containing trigylcerides. The renal burden and renal toxicities sometimes associated with ibuprofen therapy are reduced or absent in a substantially (R)-ibuprofen free composition. The absence of inactive enantiomers, particularly (R)-ibuprofen, provides for significant size and weight advantages in a combination dosage form, particularly a sustained release dosage form. Where a sustained release dosage of ibuprofen may have required 800 to 1000 mg, the employment of (S)-ibuprofen reduces the weight to 650 to 800 mg and provides for a more practical size tablet for an ibuprofen/decongestant combination. Where only a single stereoisomer of the decongestant is active (therapeutically active stereoisomer), the absence of the inactive substances in the present composition may avoid undesirable toxic interactions and clearly avoids the metabolism necessary to remove the nonactive entity.
An effective amount of (S)-ibuprofen, or a salt thereof, for use in an unit dose composition of this invention may range from 50 to 800 mg (S)-ibu- profen. The preferred amount of (S)-ibuprofen is about 100 to 400 mg. The amount of a salt such as (S)-ibuprofen-(S)-lysine is determined based on the amount of (S)-ibuprofen contained therein.
The sympathomimetic amine (Decongestant) employed herein is selected from phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a pharmaceutically acceptable salt. Included within
this invention are any diastereomers and/or enantio ers of each decongestant. Where a particular therapeutically active stereoisomer is not commercially available it may be prepared following standard resolution chemistry from the available racemic mixture.
The amount of the decongestant useful in the practice of the present invention may vary from about 1 mg to 100 mg depending on the specific decongestant. The amount of a salt, such as pseudoephedrine hydrochloride, is determined based on the amount of active decongestant, such as pseudoephedrine, contained therein.
The present compositions may be administered in the form of tablets, capsules, elixirs, syrups drops, granules, liquids, nasal spray inhaler, or a suspension. For oral administration the active components may be admixed with a pharmaceutically acceptable diluent such as lactose, starch, sucrose, cellulose, magnesium stearate, dicalcium phosphate, calcium sulfate, mannitol and in a liquid composition, ethyl alcohol. Acceptable binders such as PVP, starch, gelatin, natural sugars, corn sweeteners, natural and synthetic gums such as acacia, sodium alginate, carboxymethylcellulose, polyethylene glycol and waxes, may also be admixed with the active components. Where necessary lubricants such as magnesium stearic acid talc, and disintegrators such as starch, methylcellulose, agar, bentonite and guar gum and super disintegrators such as docusate sodium, sodium starch glycollate or cross linked PVP may also be included.
The active components may also be formulated in sustained release formulations. These
formulations may be employed in oral, dermal, rectal or vaginal administrations. Such sustained release forms also include layered formulations which provide for distinct release ratio and thus may be more beneficial in allowing for short and long term relief.
The following examples illustrate the compositions of the present invention and as such are not to be considered as limiting the invention set forth in the claims appended hereto.
EXAMPLE 1
(S)-ibuprofen-(S)-lvsine. Decongestant Tablet
(S)-ibuprofen-(S)-lysine 342 mg
Pseudoephedrine HC1
PVP
Avicel PH101
Magnesium Stearate
(S)-ibuprofen-(S)-lvsine. Decongestant Sustained Release
(S)-ibuprofen-(S)-lysine 685 mg
Pseudoephedrine HC1 60 mg
PVP 30 mg
Avicel PH101 80 mg
Magnesium Stearate 8 mg Methocel E10MCR 66 mg
Methocel K100MLV 200 mg
EXAMPLE 3
(S)-ibuprofen. Decongestant Sustained Release
(S)-ibuprofen Pseudoephedrine HC1 PVP
Avicel PH101 Magnesium Stearate Methocel E10MCR Methocel K100MLV
(S)-ibuprofen-(S)-lvsine/decongestant Solution
(S)-ibuprofen-(S)-lysine 342 mg Pseudoephedrine HC1 15 mg q.s. syrup 5 ml
Claims
1. A pharmaceutical composition for use in the treatment of pain and inflammation and the relief of nasal congestion and sinus pressure in a mammalian organism and adapted for unit dosage oral administration said composition comprising:
(i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen; and
(ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers or a pharmaceutically acceptable salt thereof.
2. A composition of Claim 1 where the ibuprofen is present as the salt (S)-ibuprofen- (S)-lysine, or (S)-ibuprofen-(R)-lysine.
3. A composition of Claim 1 comprising at least 50 mg of (S)-ibuprofen.
4. A composition of Claim 3 wherein the sympathomimetic amine is selected from: phenylephrine, phenylpropanolamine, pseudoephedrine, or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers, or a pharmaceutically acceptable salt.
5. A method of treating pain and inflammation and the relief of allergy and cold symptoms in a mammalian organism in need of such treatment comprising administering to such organism: (i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen;
(ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers or a pharmaceutically acceptable salt thereof.
6. A method of eliciting an onset hastened and enhanced response for the treatment of pain and inflammation and the relief of allergy and cold symptoms in a mammaliam organism in need of such treatment comprising administering to such organism, (i) an analgesically and anti-inflammatory effective amount of (S)-ibuprofen, or a salt thereof, substantially free (R)-ibuprofen; and (ii) a sympathomimetically effective amount of at least one of the sympathomimetic amines phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers or a pharmaceutically acceptable salt thereof.
7. A method of reducing the side effects associated with the administration of an ibuprofen/ decongestant combination which comprises the administration of (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen, and at least one of the sympathomimetic amines, phenylephrine, phenylpropanolamine, pseudophedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active stereoisomer thereof substantially free of its other stereoisomers, or a pharmaceutically acceptable salt thereof.
8. A method of reducing the size and weight of an ibuprofen/decongestant combination dosage form which comprises combining (S)-ibuprofen, or a salt thereof, substantially free of (R)-ibuprofen and at least one of the sympathomimetic amines, phenylephrine, phenylpropanolamine, pseudoephedrine, oxymetazoline, ephinephrine, naphazoline, xylometazoline, propylhexedrine, levo-desoxyephedrine or a therapeutically active steroisomer thereof substantially free of its other stereoisomers, or a pharmaceutically acceptable salt thereof.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67877391A | 1991-04-01 | 1991-04-01 | |
| US678773 | 1991-04-01 | ||
| US81252391A | 1991-12-20 | 1991-12-20 | |
| US812523 | 1991-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0577757A1 true EP0577757A1 (en) | 1994-01-12 |
| EP0577757A4 EP0577757A4 (en) | 1994-02-23 |
Family
ID=27102083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92910669A Withdrawn EP0577757A1 (en) | 1991-04-01 | 1992-03-24 | Ibuprofen-decongestant combinations |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0577757A1 (en) |
| JP (1) | JPH06506684A (en) |
| AU (1) | AU1766292A (en) |
| CA (1) | CA2107331A1 (en) |
| WO (1) | WO1992017171A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2151912A1 (en) * | 1992-12-21 | 1994-07-07 | Richard Wilfred D'souza | Use of s(+) antipodes of analgesic agents for the manufacture of a composition to treat respiratory disorders |
| BR9407414A (en) * | 1993-09-07 | 1996-11-12 | Procter & Gamble | Compositions containing a non-steroidal propionic acid anti-inflammatory agent amino acid salt and at least one decongestant an expectorant an antihistamine and an antitussive |
| DE69928806T2 (en) * | 1998-07-01 | 2006-07-20 | Warner-Lambert Co. Llc | (-) - PSEUDOEPHEDRINE AS A SYMPATHOMIMETIC MEDICINAL PRODUCT |
| US7973068B2 (en) * | 1998-10-20 | 2011-07-05 | Omeros Corporation | Arthroscopic irrigation solution and method for peripheral vasoconstriction and inhibition of pain and inflammation |
| US20030087962A1 (en) | 1998-10-20 | 2003-05-08 | Omeros Corporation | Arthroscopic irrigation solution and method for peripheral vasoconstriction and inhibition of pain and inflammation |
| US6211246B1 (en) | 1999-06-10 | 2001-04-03 | Mcneil-Ppc, Inc. | Rapidly absorbed liquid compositions |
| AU2011244930B2 (en) * | 1999-06-10 | 2012-08-30 | Mcneil-Ppc, Inc. | Rapidly absorbed liquid compositions |
| JP2004508324A (en) * | 2000-09-08 | 2004-03-18 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | Prevent acute sinusitis and sinus attacks |
| US7863287B2 (en) | 2002-12-18 | 2011-01-04 | Wyeth Llc | 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 |
| AU2022201576A1 (en) * | 2022-03-08 | 2023-09-28 | Aft Pharmaceuticals Limited | Medication |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008302A1 (en) * | 1987-04-24 | 1988-11-03 | Abraham Sunshine | Cough/cold mixtures comprising non-sedating antihistamine drugs |
| WO1989000421A1 (en) * | 1987-07-10 | 1989-01-26 | Abraham Sunshine | A pharmaceutical composition containing s(+) ibuprofen substantially free of its r(-) antipode |
| US4877620A (en) * | 1986-11-14 | 1989-10-31 | MEDICE Chem.- Pharm. Fabrik Putter GmbH & Co. KG | Ibuprofen-containing medicament |
| WO1990014081A1 (en) * | 1989-05-25 | 1990-11-29 | Sterling Drug Inc. | Onset-hastened/enhanced antipyretic response |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4840962A (en) * | 1984-04-09 | 1989-06-20 | Analgesic Associates | Cough/cold mixtures comprising non-steroidal anti-inflammatory drugs |
-
1992
- 1992-03-24 JP JP4509691A patent/JPH06506684A/en active Pending
- 1992-03-24 WO PCT/US1992/002388 patent/WO1992017171A1/en not_active Application Discontinuation
- 1992-03-24 EP EP92910669A patent/EP0577757A1/en not_active Withdrawn
- 1992-03-24 AU AU17662/92A patent/AU1766292A/en not_active Abandoned
- 1992-03-24 CA CA002107331A patent/CA2107331A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4877620A (en) * | 1986-11-14 | 1989-10-31 | MEDICE Chem.- Pharm. Fabrik Putter GmbH & Co. KG | Ibuprofen-containing medicament |
| WO1988008302A1 (en) * | 1987-04-24 | 1988-11-03 | Abraham Sunshine | Cough/cold mixtures comprising non-sedating antihistamine drugs |
| WO1989000421A1 (en) * | 1987-07-10 | 1989-01-26 | Abraham Sunshine | A pharmaceutical composition containing s(+) ibuprofen substantially free of its r(-) antipode |
| WO1990014081A1 (en) * | 1989-05-25 | 1990-11-29 | Sterling Drug Inc. | Onset-hastened/enhanced antipyretic response |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO9217171A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06506684A (en) | 1994-07-28 |
| WO1992017171A1 (en) | 1992-10-15 |
| AU1766292A (en) | 1992-11-02 |
| EP0577757A4 (en) | 1994-02-23 |
| CA2107331A1 (en) | 1992-10-02 |
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