CA2472149A1 - New fluorenecarboxylic acid esters, process for the manufacture thereof and use thereof as medicaments - Google Patents
New fluorenecarboxylic acid esters, process for the manufacture thereof and use thereof as medicaments Download PDFInfo
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- CA2472149A1 CA2472149A1 CA002472149A CA2472149A CA2472149A1 CA 2472149 A1 CA2472149 A1 CA 2472149A1 CA 002472149 A CA002472149 A CA 002472149A CA 2472149 A CA2472149 A CA 2472149A CA 2472149 A1 CA2472149 A1 CA 2472149A1
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
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- 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
- A61P9/06—Antiarrhythmics
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- 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
-
- 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
-
- 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
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The invention relates to novel fluorene carboxylic acid esters of general formula (I) wherein X-- and the groups A, R, R1, R2, R3, R3', R4 and R4' have the designations cited in the claims and in the description. The invention also relates to methods for producing said novel fluorene carboxylic acid esters and to the use of the same as pharmaceuticals.
Claims (12)
1) Compounds of general formula 1 wherein A denotes a double-bonded group selected from among X - denotes an anion with a single negative charge, R denotes hydroxy, methyl, ethyl, -CF3, CHF2 or fluorine;
R1 and R2 which may be identical or different denote C1-C5-alkyl which may optionally be substituted by C3-C6-cycloalkyl, hydroxy or halogen, or R1 and R2 together denote a -3-C5-alkylene bridge;
R3, R4, R3' and R4' which may be identical or different denote hydrogen, -C1-alkyl, -C1-C4-alkyloxy, hydroxy, -CF3, -CHF2, CN, NO2 or halogen.
R1 and R2 which may be identical or different denote C1-C5-alkyl which may optionally be substituted by C3-C6-cycloalkyl, hydroxy or halogen, or R1 and R2 together denote a -3-C5-alkylene bridge;
R3, R4, R3' and R4' which may be identical or different denote hydrogen, -C1-alkyl, -C1-C4-alkyloxy, hydroxy, -CF3, -CHF2, CN, NO2 or halogen.
2) Compounds of general formula 1 according to claim 1, wherein A denotes a double-bonded group selected from among X - denotes an anion with a single negative charge selected from among chloride, bromide, 4-toluenesulphonate and methanesulphonate, preferably bromide;
R denotes hydroxy, methyl or fluorine;
R1 and R2 which may be identical or different denote methyl, ethyl or fluoroethyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen, methyl, methyloxy, hydroxy, -CF3, -CHF2 or fluorine.
R denotes hydroxy, methyl or fluorine;
R1 and R2 which may be identical or different denote methyl, ethyl or fluoroethyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen, methyl, methyloxy, hydroxy, -CF3, -CHF2 or fluorine.
3) Compounds of general formula 1 according to one of claims 1 or 2, wherein A denotes a double-bonded group selected from among X - denotes an anion with a single negative charge selected from among chloride, bromide and methanesulphonate, preferably bromide;
R denotes hydroxy, methyl or fluorine, preferably methyl or hydroxy;
R1 and R2 which may be identical or different denote methyl or ethyl, preferably methyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen, -CF3, -CHF2 or fluorine, preferably hydrogen or fluorine.
R denotes hydroxy, methyl or fluorine, preferably methyl or hydroxy;
R1 and R2 which may be identical or different denote methyl or ethyl, preferably methyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen, -CF3, -CHF2 or fluorine, preferably hydrogen or fluorine.
4) Compounds of general formula 1 according to one of claims 1, 2 or 3, wherein A denotes a double-bonded group selected from among X - denotes bromide;
R denotes hydroxy or methyl, preferably methyl;
R1 and R2 which may be identical or different denote methyl or ethyl, preferably methyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen or fluorine.
R denotes hydroxy or methyl, preferably methyl;
R1 and R2 which may be identical or different denote methyl or ethyl, preferably methyl;
R3, R4, R3' and R4' which may be identical or different represent hydrogen or fluorine.
5) Compounds of general formula 1 according to one of claims 1 to 4, optionally in the form of the individual optical isomers, mixtures of the individual enantiomers or racemates thereof.
6) Use of a compound of general formula 1 according to one of claims 1 to 5 as a medicament.
7) Use of a compound of general formula 1 according to one of claims 1 to 5 for preparing a pharmaceutical composition for the treatment of diseases in which anticholinergics can develop a therapeutic benefit.
8) Use of a compound of general formula 1 according to one of claims 1 to 5 for preparing a pharmaceutical composition for the treatment of asthma, COPD, vagally induced sinus bradycardia, heart rhythm disorders, spasms in the gastrointestinal tract, spasms in the urinary tract and menstrual pain.
9) Pharmaceutical preparations, containing as active substance one or more compounds of general formula 1 according to one of claims 1 to 5 or the physiologically acceptable salts thereof optionally in combination with conventional excipients and/or carriers.
10) Pharmaceutical preparations according to claim 9, characterised in that they contain, in addition to one or more of the compounds of formula 1 , at least one other active substance which is selected from among the betamimetics, antiallergics, PAF
antagonists, PDE IV inhibitors, leukotriene antagonists, p38 kinase inhibitors, EGFR kinase inhibitors and corticosteroids.
antagonists, PDE IV inhibitors, leukotriene antagonists, p38 kinase inhibitors, EGFR kinase inhibitors and corticosteroids.
11) Intermediate products of general formula 4 wherein the groups A, R, R1, R3, R3', R4 and R4' may have the meanings given in claims 1 to 4, optionally in the form of the acid addition salts thereof.
12) Use of compounds of general formula 2 wherein the groups A and R1 may have the meanings given in claims 1 to 4, optionally in the form of the acid addition salts thereof, for preparing compounds of formula 1 according to one of claims 1 to 5.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10203741A DE10203741A1 (en) | 2002-01-31 | 2002-01-31 | New fluorene carboxylic acid esters, process for their preparation and their use as medicaments |
| DE10203741.8 | 2002-01-31 | ||
| PCT/EP2003/000534 WO2003064419A1 (en) | 2002-01-31 | 2003-01-21 | Novel fluorene carboxylic acid esters, methods for the production thereof, and use of the same as pharmaceuticals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2472149A1 true CA2472149A1 (en) | 2003-08-07 |
| CA2472149C CA2472149C (en) | 2011-01-11 |
Family
ID=27588159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2472149A Expired - Fee Related CA2472149C (en) | 2002-01-31 | 2003-01-21 | New fluorenecarboxylic acid esters, process for the manufacture thereof and use thereof as medicaments |
Country Status (29)
| Country | Link |
|---|---|
| EP (2) | EP1472251B1 (en) |
| JP (1) | JP4484522B2 (en) |
| KR (1) | KR100950869B1 (en) |
| CN (1) | CN100348598C (en) |
| AR (1) | AR038379A1 (en) |
| AT (1) | ATE299880T1 (en) |
| AU (1) | AU2003210172C1 (en) |
| BR (1) | BR0307294A (en) |
| CA (1) | CA2472149C (en) |
| DE (2) | DE10203741A1 (en) |
| EA (1) | EA006966B1 (en) |
| EC (1) | ECSP045209A (en) |
| ES (1) | ES2245443T3 (en) |
| HK (1) | HK1082376A1 (en) |
| HR (1) | HRP20040690B1 (en) |
| IL (1) | IL162527A0 (en) |
| ME (1) | MEP43408A (en) |
| MX (1) | MXPA04007245A (en) |
| MY (1) | MY134582A (en) |
| NO (1) | NO328929B1 (en) |
| NZ (1) | NZ534784A (en) |
| PE (1) | PE20031029A1 (en) |
| PL (1) | PL209037B1 (en) |
| PT (1) | PT1472251E (en) |
| RS (1) | RS50918B (en) |
| TW (1) | TWI352077B (en) |
| UA (1) | UA78544C2 (en) |
| UY (1) | UY27633A1 (en) |
| WO (1) | WO2003064419A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| US7709474B2 (en) | 2006-08-22 | 2010-05-04 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, manufacturing and use thereof |
| US8394791B2 (en) | 2008-02-22 | 2013-03-12 | Boehringer Ingelheim International Gmbh | Crystalline, enantiomerically pure salt form of a beta-agonist, and the use thereof as a drug |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2533791C (en) * | 2003-07-28 | 2012-05-22 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising betamimetics and an anticholinergic agent |
| CA2533786A1 (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 |
| ES2326320T3 (en) * | 2003-07-28 | 2009-10-07 | Boehringer Ingelheim International Gmbh | INHALATION DRUGS THAT INCLUDE STEROIDS AND NEW ESTER OF FLUORENCARBOXILIC ACID. |
| JP2007500676A (en) * | 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 | Inhalable drugs including anticholinergics and beta receptor stimulants |
| DE102004001607A1 (en) * | 2004-01-09 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New drug combinations based on scopin or tropic acid esters with EGFR kinase inhibitors |
| 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 |
| WO2005079794A1 (en) * | 2004-02-20 | 2005-09-01 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on anticholinergics and pegsunercept |
| DE102004016179A1 (en) * | 2004-03-30 | 2005-10-20 | Boehringer Ingelheim Pharma | Compounds for the treatment of proliferative processes |
| US20060034776A1 (en) * | 2004-08-10 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Inhalable medicaments containing a new anticholinergic, corticosteroids, and betamimetics |
| DE102004038885A1 (en) * | 2004-08-10 | 2006-02-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosol formulation for inhalation containing an anticholinergic |
| ATE427108T1 (en) * | 2004-08-11 | 2009-04-15 | Boehringer Ingelheim Pharma | MEDICINAL PRODUCTS CONTAINING ANTICHOLINERGICS FOR THE TREATMENT OF DISEASES OF THE URINARY TRACT |
| DE102005001297A1 (en) * | 2005-01-12 | 2006-07-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosol formulation for inhalation containing an anticholinergic |
| CA2597942A1 (en) * | 2005-02-16 | 2006-08-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions comprising anticholinergics and etiprednol |
| CA2600636A1 (en) * | 2005-03-09 | 2006-09-14 | Boehringer Ingelheim International Gmbh | New pharmaceutical compositions based on anticholinergics and pde 5-inhibitors |
| CA2609429A1 (en) * | 2005-05-31 | 2006-12-07 | Boehringer Ingelheim International Gmbh | Medicament containing a betamimetic in conjunction with an anticholinergic and a pde iv inhibitor |
| DE102005030733A1 (en) | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New drug combinations for the treatment of respiratory diseases containing long-acting beta-2 agonists and at least one other active ingredient |
| DE502007006951D1 (en) | 2006-08-07 | 2011-05-26 | Boehringer Ingelheim Pharma | MEDICINAL COMBINATIONS FOR THE TREATMENT OF RESPIRATORY DISEASES |
| EP1925296A1 (en) * | 2006-11-22 | 2008-05-28 | Boehringer Ingelheim Pharma GmbH & Co. KG | Stable powder formulation containing a new antichinolinergic agent |
| EP1997819A1 (en) * | 2007-05-25 | 2008-12-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | Method for manufacturing scopinium esters |
| ES2569359T3 (en) | 2007-07-06 | 2016-05-10 | Vectura Delivery Devices Limited | Inhaler |
| CA2688669A1 (en) * | 2007-07-18 | 2009-01-22 | Boehringer Ingelheim International Gmbh | New combinations for the treatment of respiratory diseases |
| 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 |
| 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 |
| EP2082766A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Blister Strip Coil Forming |
| GB0918450D0 (en) | 2009-10-21 | 2009-12-09 | Innovata Ltd | Composition |
| CN102876318B (en) * | 2012-09-28 | 2014-07-16 | 宁波大学 | Fluorene acid ester fluorescent material and preparation method thereof |
| WO2019071147A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
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| US2221828A (en) * | 1936-04-25 | 1940-11-19 | Merck & Co Inc | Esters of amino alcohols with 9-hydroxyfluorene-9-carboxylic acid and processes for their production |
| DE4108393A1 (en) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | NEW ESTERS BI-AND TRICYCLIC AMINO ALCOHOLS, THEIR PREPARATION AND THEIR USE IN MEDICINAL PRODUCTS |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| US7709474B2 (en) | 2006-08-22 | 2010-05-04 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, manufacturing and use thereof |
| US8394791B2 (en) | 2008-02-22 | 2013-03-12 | Boehringer Ingelheim International Gmbh | Crystalline, enantiomerically pure salt form of a beta-agonist, and the use thereof as a drug |
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