UA73804C2 - Anticholinergic agents being used as medicaments, a method for the preparation thereof and a pharmaceutical composition - Google Patents
Anticholinergic agents being used as medicaments, a method for the preparation thereof and a pharmaceutical composition Download PDFInfo
- Publication number
- UA73804C2 UA73804C2 UA2003054186A UA2003054186A UA73804C2 UA 73804 C2 UA73804 C2 UA 73804C2 UA 2003054186 A UA2003054186 A UA 2003054186A UA 2003054186 A UA2003054186 A UA 2003054186A UA 73804 C2 UA73804 C2 UA 73804C2
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- Ukraine
- Prior art keywords
- group
- methyl
- compounds
- general formula
- residue
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title abstract description 9
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title abstract description 7
- 239000000812 cholinergic antagonist Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- -1 methyloxy, ethyloxy Chemical group 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 239000013543 active substance Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 229940126601 medicinal product Drugs 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
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- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
-
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- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10050994A DE10050994A1 (de) | 2000-10-14 | 2000-10-14 | Neue als Arneimittel einsetzbare Anticholinergika sowie Verfahren zu deren Herstellung |
| PCT/EP2001/011226 WO2002032899A1 (de) | 2000-10-14 | 2001-09-28 | Neue als arzneimittel einsetzbare anticholinergika sowie verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73804C2 true UA73804C2 (en) | 2005-09-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003054186A UA73804C2 (en) | 2000-10-14 | 2001-09-28 | Anticholinergic agents being used as medicaments, a method for the preparation thereof and a pharmaceutical composition |
Country Status (38)
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| EP (2) | EP1325001B1 (zh) |
| JP (2) | JP4109106B2 (zh) |
| KR (1) | KR100830359B1 (zh) |
| CN (1) | CN1275962C (zh) |
| AR (1) | AR035589A1 (zh) |
| AT (1) | ATE259805T1 (zh) |
| AU (2) | AU2002213975B2 (zh) |
| BG (1) | BG66225B1 (zh) |
| BR (1) | BR0114635A (zh) |
| CA (1) | CA2425557C (zh) |
| DE (2) | DE10050994A1 (zh) |
| DK (1) | DK1325001T3 (zh) |
| EA (1) | EA005816B1 (zh) |
| EC (1) | ECSP034542A (zh) |
| EE (1) | EE05179B1 (zh) |
| ES (1) | ES2215147T3 (zh) |
| HK (1) | HK1060566A1 (zh) |
| HR (1) | HRP20030278B1 (zh) |
| HU (1) | HUP0301203A3 (zh) |
| IL (2) | IL155334A0 (zh) |
| ME (1) | MEP39908A (zh) |
| MX (1) | MXPA03003160A (zh) |
| MY (1) | MY127144A (zh) |
| NO (1) | NO328207B1 (zh) |
| NZ (1) | NZ525836A (zh) |
| PE (1) | PE20020433A1 (zh) |
| PL (1) | PL207311B1 (zh) |
| PT (1) | PT1325001E (zh) |
| RS (1) | RS50464B (zh) |
| SA (1) | SA01220414B1 (zh) |
| SI (1) | SI1325001T1 (zh) |
| SK (1) | SK287138B6 (zh) |
| TR (1) | TR200400376T4 (zh) |
| TW (1) | TWI306098B (zh) |
| UA (1) | UA73804C2 (zh) |
| UY (1) | UY26958A1 (zh) |
| WO (1) | WO2002032899A1 (zh) |
| ZA (1) | ZA200302914B (zh) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10200943A1 (de) * | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US7405224B2 (en) | 2002-01-31 | 2008-07-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthenecarboxylates, processes for preparing them, and their use as pharmaceutical compositions |
| DE10203753A1 (de) * | 2002-01-31 | 2003-08-14 | Boehringer Ingelheim Pharma | Neue Xanthencarbonsäureester, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
| US7417051B2 (en) | 2002-04-12 | 2008-08-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments comprising betamimetics and a novel anticholinergic |
| US7084153B2 (en) | 2002-04-12 | 2006-08-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments comprising steroids and a novel anticholinergic |
| DE10256317A1 (de) * | 2002-04-12 | 2003-10-23 | Boehringer Ingelheim Pharma | Arzneimittel enthaltend Betamimetika und ein neues Anticholinergikum |
| DE10216429A1 (de) * | 2002-04-12 | 2003-10-23 | Boehringer Ingelheim Pharma | Arzneimittel enthaltend Steroide und ein neues Anticholinergikum |
| BR0309185A (pt) * | 2002-04-12 | 2005-02-15 | Boehringer Ingelheim Pharma | Medicamento contendo beta-miméticos e um novo anticolinérgico |
| DE10224091A1 (de) * | 2002-05-31 | 2003-12-11 | Boehringer Ingelheim Pharma | Technisches Verfahren zur Herstellung von Tropenol |
| DE10230751A1 (de) * | 2002-07-09 | 2004-01-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkompositionen auf der Basis neuer Anticholinergika und EGFR-Kinase-Hemmern |
| DE10230769A1 (de) * | 2002-07-09 | 2004-01-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkompositionen auf der Basis neuer Anticholinergika und PDE-IV-Inhibitoren |
| EP1707205A2 (en) | 2002-07-09 | 2006-10-04 | Boehringer Ingelheim Pharma GmbH & Co. KG | Pharmaceutical compositions of anticholinergics and p38 kinase inhibitors in the treatment of respiratory diseases |
| DE10230750A1 (de) * | 2002-07-09 | 2004-01-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkompositionen auf der Basis neuer Anticholonergika und NK1-Rezeptor-Antagonisten |
| RS51396B (en) * | 2002-08-14 | 2011-02-28 | Boehringer Ingelheim Pharma Gmbh & Co.Kg. | AEROSOLIC INHALATION FORMULATION CONTAINING ANTICHOLINERGIC |
| US7244742B2 (en) | 2002-08-17 | 2007-07-17 | Boehringer Ingelheim Pharma Gmbh & Co Kg | Pharmaceutical compositions for inhalation containing an anticholinergic, corticosteroid and betamimetic |
| DE10237739A1 (de) * | 2002-08-17 | 2004-02-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Inhalative Arzneimittel enthaltend ein neues Anticholinergikum in Kombination mit Corticosteroiden und Betamimetika |
| US7056916B2 (en) | 2002-11-15 | 2006-06-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments for the treatment of chronic obstructive pulmonary disease |
| DE10317461A1 (de) | 2003-04-16 | 2004-10-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Radioaktiv markierte Mikropartikel, Verfahren zu deren Herstellung und deren Verwendung |
| DE10323966A1 (de) * | 2003-05-27 | 2004-12-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen |
| US7332175B2 (en) | 2003-05-27 | 2008-02-19 | Boehringer Ingelheim International Gmbh | Long-acting drug combinations for the treatment of respiratory complaints |
| DE10331350A1 (de) * | 2003-07-11 | 2005-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pulverformulierungen für die Inhalation enthaltend ein neues Anticholinergikum |
| US7462367B2 (en) | 2003-07-11 | 2008-12-09 | Boehringer Ingelheim International Gmbh | Anticholinergic powder formulations for inhalation |
| US7273603B2 (en) * | 2003-07-11 | 2007-09-25 | Boehringer Ingelheim International Gmbh | HFC solution formulations containing an anticholinergic |
| EP1651221B1 (en) * | 2003-07-28 | 2009-01-14 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising betamimetics and an anticholinergic agent |
| JP2007500147A (ja) * | 2003-07-28 | 2007-01-11 | 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 | ステロイド及びフルオレンカルボン酸エステルを含有する吸入用医薬品 |
| JP2007500148A (ja) * | 2003-07-28 | 2007-01-11 | 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 | Ｐｄｅｉｖ阻害薬と新規な抗コリン作用薬とを含有する医薬品ならびに呼吸器疾患治療のための該医薬品の使用 |
| JP2007500676A (ja) * | 2003-07-31 | 2007-01-18 | 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 | 抗コリン作用薬とベータ受容体刺激薬を含む吸入用薬剤 |
| EP1504756A1 (en) * | 2003-08-06 | 2005-02-09 | Kyowa Hakko Kogyo Co., Ltd | Medicament compositions comprising a heterocyclic compound and an anticholinergic |
| DE10345065A1 (de) | 2003-09-26 | 2005-04-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| WO2005067929A1 (en) * | 2004-01-09 | 2005-07-28 | Boehringer Ingelheim International Gmbh | New pharmaceutical compositions based on a scopineester and nicotinamide derivatives |
| JP2007523116A (ja) * | 2004-02-20 | 2007-08-16 | 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 | 抗コリン作用薬及びｐｅｇｓｕｎｅｒｃｅｐｔを基にした新規な医薬組成物 |
| US7507745B2 (en) | 2004-02-20 | 2009-03-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on fluorenecarboxylic acid esters and soluble TNF receptor fusion proteins |
| US20050186175A1 (en) * | 2004-02-20 | 2005-08-25 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on benzilic acid esters and soluble TNF receptor fusion proteins |
| DE102004016179A1 (de) * | 2004-03-30 | 2005-10-20 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von proliferativen Prozessen |
| US7220742B2 (en) | 2004-05-14 | 2007-05-22 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments |
| DE602004020337D1 (de) * | 2004-08-11 | 2009-05-14 | Boehringer Ingelheim Pharma | Anticholinergika enthaltende Arzneimittel zur Behandlung von Krankheiten der ableitenden Harnwege |
| DE102004056578A1 (de) * | 2004-11-23 | 2006-05-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Inhalative Arzneimittel enthaltend ein neues Anticholinergikum, Formoterol und ein Steroid |
| JP2008530177A (ja) * | 2005-02-16 | 2008-08-07 | 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 | 抗コリン作用薬及びエチプレドノールを含有する医薬組成物 |
| WO2006094924A2 (en) * | 2005-03-09 | 2006-09-14 | Boehringer Ingelheim International Gmbh | New pharmaceutical compositions based on anticholinergics and pde 5-inhibitors |
| JP2008542332A (ja) * | 2005-05-31 | 2008-11-27 | 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 | 呼吸器疾患治療用新規医薬組成物 |
| EP1898894A1 (en) * | 2005-06-17 | 2008-03-19 | Boehringer Ingelheim International GmbH | Mrp iv inhibitors for the treatment of respiratory diseases |
| DE102005030733A1 (de) | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff |
| MX2008001976A (es) | 2005-08-15 | 2008-03-25 | Boehringer Ingelheim Int | Procedimiento para la preparacion de betamimeticos. |
| WO2007045979A1 (en) | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of muscarinic receptor antagonists |
| DE102005055961A1 (de) * | 2005-11-24 | 2007-05-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| DE102005055957A1 (de) * | 2005-11-24 | 2007-07-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| DE102005055963A1 (de) * | 2005-11-24 | 2007-07-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| CA2660186A1 (en) | 2006-08-07 | 2008-02-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of respiratory diseases |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| NZ579645A (en) | 2007-03-14 | 2012-01-12 | Ranbaxy Lab Ltd | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| ES2569359T3 (es) | 2007-07-06 | 2016-05-10 | Vectura Delivery Devices Limited | Inhalador |
| CA2688669A1 (en) * | 2007-07-18 | 2009-01-22 | Boehringer Ingelheim International Gmbh | New combinations for the treatment of respiratory diseases |
| EP2077132A1 (en) | 2008-01-02 | 2009-07-08 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dispensing device, storage device and method for dispensing a formulation |
| EP2082766A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Blister Strip Coil Forming |
| EP2082772A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082771A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082768A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082767A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| EP2414560B1 (de) | 2009-03-31 | 2013-10-23 | Boehringer Ingelheim International GmbH | Verfahren zur beschichtung einer oberfläche eines bauteils |
| JP5763053B2 (ja) | 2009-05-18 | 2015-08-12 | 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 | アダプタ、吸入器具及びアトマイザ |
| GB0918450D0 (en) | 2009-10-21 | 2009-12-09 | Innovata Ltd | Composition |
| JP5658268B2 (ja) | 2009-11-25 | 2015-01-21 | 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 | ネブライザ |
| WO2011064164A1 (en) | 2009-11-25 | 2011-06-03 | Boehringer Ingelheim International Gmbh | Nebulizer |
| US10016568B2 (en) | 2009-11-25 | 2018-07-10 | Boehringer Ingelheim International Gmbh | Nebulizer |
| WO2011160932A1 (en) | 2010-06-24 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Nebulizer |
| WO2012130757A1 (de) | 2011-04-01 | 2012-10-04 | Boehringer Ingelheim International Gmbh | Medizinisches gerät mit behälter |
| US9827384B2 (en) | 2011-05-23 | 2017-11-28 | Boehringer Ingelheim International Gmbh | Nebulizer |
| WO2013152894A1 (de) | 2012-04-13 | 2013-10-17 | Boehringer Ingelheim International Gmbh | Zerstäuber mit kodiermitteln |
| LT3473255T (lt) | 2012-12-21 | 2022-03-10 | Boehringer Ingelheim Vetmedica Gmbh | Farmacinė vaisto forma, apimanti ciklezonidą |
| NZ706573A (en) | 2012-12-21 | 2019-11-29 | Boehringer Ingelheim Vetmedica Gmbh | Ciclesonide for the treatment of airway disease in horses |
| JP6643231B2 (ja) | 2013-08-09 | 2020-02-12 | 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 | ネブライザ |
| EP2835146B1 (en) | 2013-08-09 | 2020-09-30 | Boehringer Ingelheim International GmbH | Nebulizer |
| JP6580070B2 (ja) | 2014-05-07 | 2019-09-25 | 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 | 容器、ネブライザ、及び使用 |
| LT3928818T (lt) | 2014-05-07 | 2023-03-27 | Boehringer Ingelheim International Gmbh | Purkštuvas ir talpa |
| PL3139984T3 (pl) | 2014-05-07 | 2021-11-08 | Boehringer Ingelheim International Gmbh | Nebulizator |
| EP3157522B1 (en) * | 2014-06-18 | 2019-09-04 | Boehringer Ingelheim Vetmedica GmbH | Muscarinic antagonists and combinations thereof for the treatment of airway disease in horses |
| JP6736661B2 (ja) * | 2015-09-04 | 2020-08-05 | ヤンセン ファーマシューティカ エヌ．ベー． | 治療化合物及び合成 |
| CN113292574B (zh) * | 2020-02-21 | 2022-05-03 | 四川大学 | 一类手性多环的托品烷化合物及其制备方法和用途 |
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| DE4003270A1 (de) * | 1990-02-03 | 1991-08-08 | Boehringer Ingelheim Kg | Neue treibgase und ihre verwendung in arzneimittelzubereitungen |
| DE4108393A1 (de) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln |
-
2000
- 2000-10-14 DE DE10050994A patent/DE10050994A1/de not_active Withdrawn
-
2001
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- 2001-09-28 EP EP01982374A patent/EP1325001B1/de not_active Expired - Lifetime
- 2001-09-28 IL IL15533401A patent/IL155334A0/xx active IP Right Grant
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- 2001-09-28 AU AU2002213975A patent/AU2002213975B2/en not_active Expired
- 2001-09-28 EA EA200300459A patent/EA005816B1/ru not_active IP Right Cessation
- 2001-09-28 UA UA2003054186A patent/UA73804C2/uk unknown
- 2001-09-28 EP EP03023933A patent/EP1382606A3/de not_active Withdrawn
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- 2001-09-28 ES ES01982374T patent/ES2215147T3/es not_active Expired - Lifetime
- 2001-09-28 KR KR1020037005256A patent/KR100830359B1/ko not_active IP Right Cessation
- 2001-09-28 EE EEP200300151A patent/EE05179B1/xx not_active IP Right Cessation
- 2001-09-28 AU AU1397502A patent/AU1397502A/xx active Pending
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- 2001-09-28 DK DK01982374T patent/DK1325001T3/da active
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- 2001-09-28 MX MXPA03003160A patent/MXPA03003160A/es active IP Right Grant
- 2001-09-28 WO PCT/EP2001/011226 patent/WO2002032899A1/de active IP Right Grant
- 2001-09-28 BR BR0114635-1A patent/BR0114635A/pt not_active Expired - Fee Related
- 2001-09-28 SI SI200130085T patent/SI1325001T1/xx unknown
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2003
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2008
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