CA2439763A1 - Pharmaceutical compositions based on anticholinergics and pde-iv inhibitors - Google Patents
Pharmaceutical compositions based on anticholinergics and pde-iv inhibitors Download PDFInfo
- Publication number
- CA2439763A1 CA2439763A1 CA002439763A CA2439763A CA2439763A1 CA 2439763 A1 CA2439763 A1 CA 2439763A1 CA 002439763 A CA002439763 A CA 002439763A CA 2439763 A CA2439763 A CA 2439763A CA 2439763 A1 CA2439763 A1 CA 2439763A1
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- Prior art keywords
- acid
- inhalable
- pharmaceutical composition
- composition according
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to novel medicament compositions on the basis of anticholinergics and PDE IV inhibitors, and to the use thereof in the therapy of respiratory tract diseases.
Claims (35)
1) Pharmaceutical composition characterised in that it contains one or more anticholinergics (1) combined with one or more PDE-IV inhibitors (2), optionally in the form of the enantiomers, mixtures of the enantiomers or in the form of the racemates thereof, optionally in the form of the solvates or hydrates and optionally together with a pharmaceutically acceptable excipient.
2) Pharmaceutical composition according to claim 1, characterised in that the active substances 1 and 2 are present either together in a single formulation or in two separate formulations.
3) Pharmaceutical composition according to one of claims 1 and 2, characterised in that 1 is selected from the group consisting of tiotropium salts, oxitropium salts or ipratropium salts, preferably tiotropium salts.
4) Pharmaceutical composition according to one of claims 1 to 3, characterised in that 1 is present in the form of the chloride, bromide, iodide, methanesulphonate, paratoluene sulphonate or methyl sulphate, preferably in the form of the bromide.
5) Pharmaceutical composition according to one of claims 1 to 4, characterised in that 2 is selected from among enprofylline, roflumilast, ariflo, Bay-198004, CP-325,366, BY343, D-4396 (Sch-351591), V-11294A, AWD-12-281 and the tricyclic nitrogen heterocycles of general formula 2a wherein R1 denotes C1-C5-alkyl, C5-C6-cycloalkyl, phenyl, benzyl or a 5- or 6-membered, saturated or unsaturated heterocyclic ring which may contain one or two heteroatoms selected from among oxygen and nitrogen;
R2 denotes C1-C5-alkyl or C2-C4-alkenyl;
R3 denotes C1-C5-alkyl which may optionally be substituted by C1-C4-alkoxy, C5-C6-cycloalkyl, phenoxy or a 5- or 6-membered, saturated or unsaturated heterocyclic ring which may contain one or two heteroatoms selected from among oxygen and nitrogen;
C5-C6-cycloalkyl or phenyl or benzyl optionally substituted by C1-C4-alkoxy, optionally in the form of their racemates, their enantiomers, in the form of the diastereomers and the mixtures thereof, optionally in the form of their tautomers and optionally the pharmacologically acceptable acid addition salts thereof.
R2 denotes C1-C5-alkyl or C2-C4-alkenyl;
R3 denotes C1-C5-alkyl which may optionally be substituted by C1-C4-alkoxy, C5-C6-cycloalkyl, phenoxy or a 5- or 6-membered, saturated or unsaturated heterocyclic ring which may contain one or two heteroatoms selected from among oxygen and nitrogen;
C5-C6-cycloalkyl or phenyl or benzyl optionally substituted by C1-C4-alkoxy, optionally in the form of their racemates, their enantiomers, in the form of the diastereomers and the mixtures thereof, optionally in the form of their tautomers and optionally the pharmacologically acceptable acid addition salts thereof.
6) Pharmaceutical composition according to one of claims 1 to 5, characterised in that 2 is selected from among enprofylline, roflumilast, ariflo, AWD-12-281 and the tricyclic nitrogen heterocycles of general formula 2a.
7) Pharmaceutical compositions according to one of claims 1 to 6, characterised in that the weight ratios of 1 to 2 are in the range from 1:300 to 50:1, preferably from 1:250 to 40:1.
8) Pharmaceutical composition according to one of claims 1 to 7, characterised in that a single administration corresponds to a dose of the active substance combination 1 and 2 of 0.01 to 10000µg, preferably from 0.1 to 2000µg.
9) Pharmaceutical composition according to one of claims 1 to 8, characterised in that it is in the form of a formulation suitable for inhalation.
10) Pharmaceutical composition according to claim 9, characterised in that it is a formulation selected from among inhalable powders, propellant-containing metering aerosols and propellant-free inhalable solutions or suspensions.
11) Pharmaceutical composition according to claim 10, characterised in that it is an inhalable powder which contains 1 and 2 in admixture with suitable physiologically acceptable excipients selected from among the monosaccharides, disaccharides, oligo- and polysaccharides, polyalcohols, salts, or mixtures of these excipients with one another.
12) Inhalable powder according to claim 11, characterised in that the excipient has a maximum average particle size of up to 250µm, preferably between 10 and 150µm.
13) Capsules, characterised in that they contain an inhalable powder according to claim 11 or 12.
14) Pharmaceutical composition according to claim 10, characterised in that it is an inhalable powder which contains only the active substances 1 and 2 as its ingredients.
15) Pharmaceutical composition according to claim 10, characterised in that it is a propellant-containing inhalable aerosol which contains 1 and 2 in dissolved or dispersed form.
16) Propellant-containing inhalable aerosol according to claim 15, characterised in that it contains, as propellant gas, hydrocarbons such as n-propane, n-butane or isobutane or halohydrocarbons such as chlorinated and/or fluorinated derivatives of methane, ethane, propane, butane, cyclopropane or cyclobutane.
17) Propellant-containing inhalable aerosol according to claim 16, characterised in that the propellant gas is TG134a, TG227 or a mixture thereof.
18) Propellant-containing inhalable aerosol according to claim 15, 16 or 17, characterised in that it optionally contains one or more other ingredients selected from among cosolvents, stabilisers, surfactants, antioxidants, lubricants and means for adjusting the pH.
19) Propellant-containing inhalable aerosol according to one of claims 15 to 18, characterised in that it may contain up to 5 wt.-% of active substance 1 and/or 2.
20) Pharmaceutical composition according to claim 10, characterised in that it is a propellant-free inhalable solution or suspension which contains water, ethanol or a mixture of water and ethanol as solvent.
21) Inhalable solution or suspension according to claim 20, characterised in that the pH is 2 - 7, preferably 2 -5.
22) Inhalable solution or suspension according to claim 21, characterised in that the pH is adjusted by means of an acid selected from among hydrochloric acid, hydrobromic acid, nitric acid, sulphuric acid, ascorbic acid, citric acid, malic acid, tartaric acid, maleic acid, succinic acid, fumaric acid, acetic acid, formic acid and propionic acid or mixtures thereof.
23) Inhalable solution or suspension according to one of claims 20 to 22, characterised in that it optionally contains other co-solvents and/or excipients.
24) Inhalable solution or suspension according to claim 23, characterised in that it contains as co-solvents ingredients which contain hydroxyl groups or other polar groups, e.g. alcohols - particularly isopropyl alcohol, glycols - particularly propyleneglycol, polyethyleneglycol, polypropyleneglycol, glycolether, glycerol, polyoxyethylene alcohols and polyoxyethylene fatty acid esters.
25) Inhalable solution or suspension according to one of claims 23 or 24, characterised in that it contains as excipients surfactants, stabilisers, complexing agents, antioxidants and/or preservatives, flavourings, pharmacologically acceptable salts and/or vitamins.
26) Inhalable solution or suspension according to claim 25, characterised in that it contains as complexing agent editic acid or a salt of editic acid, preferably sodium edetate.
27) Inhalable solution or suspension according to claim 25 or 26, characterised in that it contains, as antioxidants, compounds selected from among ascorbic acid, vitamin A, vitamin E and tocopherols.
28) Inhalable solution or suspension according to claim 25, 26 or 27, characterised in that it contains as preservatives compounds selected from cetyl pyridinium chloride, benzalkonium chloride, benzoic acid and benzoates.
29) Inhalable solution or suspension according to one of claims 23 to 28, characterised in that it contains, in addition to the active substances 1 and 2 and the solvent, only benzalkonium chloride and sodium edetate.
30) Inhalable solution or suspension according to one of claims 23 to 28, characterised in that it contains, in addition to the active substances 1 and 2 and the solvent, only benzalkonium chloride.
31) Inhalable solution or suspension according to one of claims 20 to 30, characterised in that it is a concentrate or a sterile ready-to-use inhalable solution or suspension.
32) Use of a capsule according to claim 13 in an inhaler, preferably in a Handyhaler.
33) Use of an inhalable solution according to one of claims 20 to 30 for nebulising in an inhaler according to WO 91/14468 or an inhaler as described in Figures 6a and 6b of WO 97/12687.
34) Use of an inhalable solution according to claim 31 for nebulising in an energy-operated free-standing or portable nebuliser which produces inhalable aerosols by means of ultrasound or compressed air according to the Venturi principle or other principles.
35) Use of a composition according to one of claims 1 to 31 for preparing a medicament for treating inflammatory or obstructive diseases of the respiratory tract.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10110772.2 | 2001-03-07 | ||
| DE10110772A DE10110772A1 (en) | 2001-03-07 | 2001-03-07 | New drug compositions based on anticholinergics and PDE-IV inhibitors |
| PCT/EP2002/001988 WO2002069945A2 (en) | 2001-03-07 | 2002-02-26 | Novel medicament compositions on the basis of anticholinergics and pde iv inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2439763A1 true CA2439763A1 (en) | 2002-09-12 |
| CA2439763C CA2439763C (en) | 2012-10-16 |
Family
ID=7676493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2439763A Expired - Fee Related CA2439763C (en) | 2001-03-07 | 2002-02-26 | Pharmaceutical compositions based on anticholinergics and pde-iv inhibitors |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1372649B1 (en) |
| JP (1) | JP2004521134A (en) |
| KR (1) | KR20030081501A (en) |
| CN (1) | CN1649588A (en) |
| AR (1) | AR034213A1 (en) |
| AU (1) | AU2002257587B2 (en) |
| BR (1) | BR0207883A (en) |
| CA (1) | CA2439763C (en) |
| CZ (1) | CZ20032635A3 (en) |
| DE (1) | DE10110772A1 (en) |
| EA (1) | EA009989B1 (en) |
| HU (1) | HUP0400782A3 (en) |
| IL (2) | IL157326A0 (en) |
| MX (1) | MXPA03008045A (en) |
| NZ (1) | NZ528621A (en) |
| PL (1) | PL363078A1 (en) |
| TW (1) | TWI332833B (en) |
| WO (1) | WO2002069945A2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10471063B2 (en) | 2013-03-15 | 2019-11-12 | Verona Pharma Plc | Drug combination of PDE3/PDE4 inhibitor and muscarinic receptor antagonist |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2165768B1 (en) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | NEW DERIVATIVES OF QUINUCLIDINE AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM. |
| ES2276942T3 (en) * | 2001-05-25 | 2007-07-01 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | COMBINATION OF A PDE4 AND TIOTROPE INHIBITOR OR A DERIVATIVE OF THE SAME TO TREAT OBSTRUCTIVE RESPIRATORY ROADS AND OTHER INFLAMMATORY DISEASES. |
| GB0118373D0 (en) * | 2001-07-27 | 2001-09-19 | Glaxo Group Ltd | Novel therapeutic method |
| US20030235538A1 (en) | 2002-04-09 | 2003-12-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Method for the administration of an anticholinergic by inhalation |
| DE10230769A1 (en) * | 2002-07-09 | 2004-01-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New drug compositions based on new anticholinergics and PDE-IV inhibitors |
| MXPA05010161A (en) * | 2003-03-28 | 2005-11-16 | Altana Pharma Ag | Synergistic combination comprising roflumilast and an anticholinergic agent selected from ipratropium, oxitropium and tiotropium salts for the treatment of respiratory diseases. |
| ATE384529T1 (en) * | 2003-03-28 | 2008-02-15 | Nycomed Gmbh | SYNERGISTIC COMBINATION CONTAINING ROFLUMILAST AND AN ANTICHOLINERGIC ACTIVE INGREDIENTS SELECTED FROM TIOTROPIUM SALTS FOR THE TREATMENT OF RESPIRATORY DISEASES |
| WO2004084894A1 (en) * | 2003-03-28 | 2004-10-07 | Altana Pharma Ag | Synergistic combination comprising roflumilast and revatropate for the treatment of respiratory diseases |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| WO2005013967A1 (en) * | 2003-07-28 | 2005-02-17 | Boehringer Ingelheim International Gmbh | Medicaments comprising pde iv inhibitors and a novel anticholinergic and their use for treating respiratory disorders |
| US7071333B2 (en) | 2003-07-30 | 2006-07-04 | Bristol-Myers Squibb Company | Triazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same |
| EP1504756A1 (en) * | 2003-08-06 | 2005-02-09 | Kyowa Hakko Kogyo Co., Ltd | Medicament compositions comprising a heterocyclic compound and an anticholinergic |
| JP2007517820A (en) * | 2004-01-09 | 2007-07-05 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Novel pharmaceutical compositions based on scopine esters and nicotinamide derivatives |
| AU2005210086A1 (en) * | 2004-02-06 | 2005-08-18 | Meda Pharma Gmbh & Co. Kg | Treatment of rhinitis with anticholinergics alone in combination with antihistamines phosphodiesterase 4 inhibitors, or corticosteroids |
| CN100569235C (en) | 2004-02-06 | 2009-12-16 | Meda制药有限及两合公司 | Be used for the anticholinergic of asthma and COPD long-term treatment and the combination of glucocorticoid |
| CN100512813C (en) * | 2004-02-06 | 2009-07-15 | Meda制药有限及两合公司 | Combination of anticholinergics and inhibitors of phosphodiesterase type 4 for the treatment of respiratory diseases |
| EP1720543A1 (en) * | 2004-02-27 | 2006-11-15 | Altana Pharma AG | Roflumilast and glycopryrronium combination |
| EP1616567A1 (en) * | 2004-07-16 | 2006-01-18 | Boehringer Ingelheim Pharma GmbH & Co.KG | Medicaments for inhalation comprising PDE IV inhibitors and glycopyrrolate salts |
| CN101128196B (en) | 2005-03-16 | 2013-01-02 | Meda制药有限及两合公司 | Combination of anticholinergics and leukotriene receptor antagonists for the treatment of respiratory diseases |
| GB0521563D0 (en) | 2005-10-21 | 2005-11-30 | Glaxo Group Ltd | Novel compounds |
| DK2098248T3 (en) | 2005-12-21 | 2012-09-17 | Meda Pharma Gmbh & Co Kg | Combination of anticholinergics, glucocorticoids and beta2 agonists for the treatment of inflammatory diseases |
| CA2659539A1 (en) | 2006-08-01 | 2008-02-07 | Glaxo Group Limited | Pyrazolo[3,4-b]pyridine compounds, and their use as pde4 inhibitors |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| US8470835B2 (en) | 2009-01-13 | 2013-06-25 | Glaxo Group Limited | Pyrimidinecarboxamide derivatives as inhibitors of Syk kinase |
| WO2012025474A1 (en) | 2010-08-24 | 2012-03-01 | Glaxo Group Limited | Indazole compounds |
| WO2012025473A1 (en) | 2010-08-24 | 2012-03-01 | Glaxo Group Limited | Cc.chemokine receptor 4 antagonists |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| CN102670607A (en) * | 2012-05-28 | 2012-09-19 | 海南卫康制药(潜山)有限公司 | Compound ambroxol hydrochloride composition and preparation method thereof |
| WO2014191826A1 (en) * | 2013-05-31 | 2014-12-04 | Nexpath Medical Sa | Acetabular reamer assembly |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000198734A (en) * | 1998-12-30 | 2000-07-18 | Pfizer Inc | Prokinetic agent for treating gastric hypomotility and related disease |
| MY134008A (en) * | 1999-12-22 | 2007-11-30 | Merck Frosst Canada Inc | Subtituted 8-arylquinoline phospohodiestrase-4 inhibitors |
| US6740655B2 (en) * | 2000-01-31 | 2004-05-25 | Pfizer Inc | Pyrimidine carboxamides useful as inhibitors of PDE4 isozymes |
| WO2001070746A1 (en) * | 2000-03-23 | 2001-09-27 | Takeda Chemical Industries, Ltd. | Furoisoquinoline derivatives, process for producing the same and use thereof |
| GB0009583D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Respiratory formulations |
| US20020052312A1 (en) * | 2000-05-30 | 2002-05-02 | Reiss Theodore F. | Combination therapy of chronic obstructive pulmonary disease using muscarinic receptor antagonists |
| AR029984A1 (en) * | 2000-07-27 | 2003-07-23 | Smithkline Beecham Corp | METHOD FOR REDUCING ASSOCIATED EXCERBATIONS COPD AMBITO |
-
2001
- 2001-03-07 DE DE10110772A patent/DE10110772A1/en not_active Withdrawn
-
2002
- 2002-02-26 EP EP02727329A patent/EP1372649B1/en not_active Expired - Lifetime
- 2002-02-26 IL IL15732602A patent/IL157326A0/en unknown
- 2002-02-26 NZ NZ528621A patent/NZ528621A/en not_active IP Right Cessation
- 2002-02-26 JP JP2002569122A patent/JP2004521134A/en active Pending
- 2002-02-26 CZ CZ20032635A patent/CZ20032635A3/en unknown
- 2002-02-26 KR KR10-2003-7011716A patent/KR20030081501A/en not_active Application Discontinuation
- 2002-02-26 CA CA2439763A patent/CA2439763C/en not_active Expired - Fee Related
- 2002-02-26 BR BR0207883-0A patent/BR0207883A/en active Pending
- 2002-02-26 MX MXPA03008045A patent/MXPA03008045A/en active IP Right Grant
- 2002-02-26 AU AU2002257587A patent/AU2002257587B2/en not_active Ceased
- 2002-02-26 WO PCT/EP2002/001988 patent/WO2002069945A2/en active IP Right Grant
- 2002-02-26 EA EA200300929A patent/EA009989B1/en not_active IP Right Cessation
- 2002-02-26 CN CNA02805346XA patent/CN1649588A/en active Pending
- 2002-02-26 PL PL02363078A patent/PL363078A1/en not_active Application Discontinuation
- 2002-02-26 HU HU0400782A patent/HUP0400782A3/en not_active Application Discontinuation
- 2002-03-06 TW TW091104144A patent/TWI332833B/en active
- 2002-03-06 AR ARP020100808A patent/AR034213A1/en active Pending
-
2003
- 2003-08-11 IL IL157326A patent/IL157326A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10471063B2 (en) | 2013-03-15 | 2019-11-12 | Verona Pharma Plc | Drug combination of PDE3/PDE4 inhibitor and muscarinic receptor antagonist |
Also Published As
| Publication number | Publication date |
|---|---|
| EA009989B1 (en) | 2008-04-28 |
| EP1372649B1 (en) | 2012-07-25 |
| WO2002069945A2 (en) | 2002-09-12 |
| MXPA03008045A (en) | 2003-12-04 |
| KR20030081501A (en) | 2003-10-17 |
| HUP0400782A2 (en) | 2004-07-28 |
| BR0207883A (en) | 2004-07-27 |
| AU2002257587B2 (en) | 2007-05-10 |
| IL157326A0 (en) | 2004-02-19 |
| CA2439763C (en) | 2012-10-16 |
| DE10110772A1 (en) | 2002-09-12 |
| WO2002069945A3 (en) | 2003-01-30 |
| HUP0400782A3 (en) | 2012-09-28 |
| PL363078A1 (en) | 2004-11-15 |
| EP1372649A2 (en) | 2004-01-02 |
| CZ20032635A3 (en) | 2004-09-15 |
| TWI332833B (en) | 2010-11-11 |
| IL157326A (en) | 2011-12-29 |
| CN1649588A (en) | 2005-08-03 |
| EA200300929A1 (en) | 2004-04-29 |
| JP2004521134A (en) | 2004-07-15 |
| NZ528621A (en) | 2005-04-29 |
| AR034213A1 (en) | 2004-02-04 |
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