RU2010139571A - Производные 4-(2-амино-1-гидроксиэтил)фенола в качестве агонистов b2-адренергического рецептора - Google Patents
Производные 4-(2-амино-1-гидроксиэтил)фенола в качестве агонистов b2-адренергического рецептора Download PDFInfo
- Publication number
- RU2010139571A RU2010139571A RU2010139571/04A RU2010139571A RU2010139571A RU 2010139571 A RU2010139571 A RU 2010139571A RU 2010139571/04 A RU2010139571/04 A RU 2010139571/04A RU 2010139571 A RU2010139571 A RU 2010139571A RU 2010139571 A RU2010139571 A RU 2010139571A
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- Prior art keywords
- hydroxy
- phenyl
- ethyl
- group
- amino
- Prior art date
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- 239000000048 adrenergic agonist Substances 0.000 title 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 title 1
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical class NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 60
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 15
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 239000012453 solvate Substances 0.000 claims abstract 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 31
- -1 phenyloxy group Chemical group 0.000 claims 25
- 239000004202 carbamide Substances 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 230000001575 pathological effect Effects 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 claims 3
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- PYWNXSDTPRPTMD-LOGQOBJBSA-N 1-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]propyl]phenyl]-3-(2-phenylphenyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NC(C)CC(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 PYWNXSDTPRPTMD-LOGQOBJBSA-N 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- XWOZZFOEVKMVJC-LJAQVGFWSA-N 1-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]-3-(2-phenylphenyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 XWOZZFOEVKMVJC-LJAQVGFWSA-N 0.000 claims 1
- PVLWTNWXLAPXJE-SANMLTNESA-N 1-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]-3-(3-phenylpropyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1NC(=O)NCCCC1=CC=CC=C1 PVLWTNWXLAPXJE-SANMLTNESA-N 0.000 claims 1
- TXCMHJXMEORYFQ-LJAQVGFWSA-N 1-[4-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]-3-(2-phenylphenyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 TXCMHJXMEORYFQ-LJAQVGFWSA-N 0.000 claims 1
- WIBVTGVCBBKVAE-SANMLTNESA-N 1-[4-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]-3-(3-phenylpropyl)urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1NC(=O)NCCCC1=CC=CC=C1 WIBVTGVCBBKVAE-SANMLTNESA-N 0.000 claims 1
- RHAYOMZUUNTCTB-LJAQVGFWSA-N 1-benzhydryl-3-[3-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1NC(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 RHAYOMZUUNTCTB-LJAQVGFWSA-N 0.000 claims 1
- BAKAALSDMKQZHQ-LJAQVGFWSA-N 1-benzhydryl-3-[4-[2-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]ethyl]phenyl]urea Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1NC(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 BAKAALSDMKQZHQ-LJAQVGFWSA-N 0.000 claims 1
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08382008A EP2096105A1 (en) | 2008-02-28 | 2008-02-28 | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| EP08382008.4 | 2008-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010139571A true RU2010139571A (ru) | 2012-04-10 |
Family
ID=39645317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010139571/04A RU2010139571A (ru) | 2008-02-28 | 2009-02-27 | Производные 4-(2-амино-1-гидроксиэтил)фенола в качестве агонистов b2-адренергического рецептора |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20110028442A1 (enExample) |
| EP (2) | EP2096105A1 (enExample) |
| JP (1) | JP2011517316A (enExample) |
| KR (1) | KR20100138886A (enExample) |
| CN (1) | CN101939291A (enExample) |
| AU (1) | AU2009218688A1 (enExample) |
| CA (1) | CA2716397A1 (enExample) |
| CO (1) | CO6251284A2 (enExample) |
| EC (1) | ECSP10010431A (enExample) |
| IL (1) | IL206236A0 (enExample) |
| MX (1) | MX2010008864A (enExample) |
| NZ (1) | NZ586049A (enExample) |
| RU (1) | RU2010139571A (enExample) |
| WO (1) | WO2009106351A1 (enExample) |
| ZA (1) | ZA201004009B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| ES2296516B1 (es) * | 2006-04-27 | 2009-04-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| ES2306595B1 (es) * | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| ES2320961B1 (es) * | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| EA201500651A1 (ru) | 2012-12-18 | 2015-11-30 | Альмираль, С.А. | НОВЫЕ ПРОИЗВОДНЫЕ ЦИКЛОГЕКСИЛ- И ХИНУКЛИДИНИЛКАРБАМАТА, ОБЛАДАЮЩИЕ АГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К β2 АДРЕНЕРГИЧЕСКОМУ РЕЦЕПТОРУ И АНТАГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К МУСКАРИНОВОМУ РЕЦЕПТОРУ М3 |
| CZ306252B6 (cs) * | 2013-03-15 | 2016-10-26 | Zentiva, K.S. | Způsob přípravy 5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1H)-chinolin-2-onu (indacaterolu) |
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| US3053865A (en) * | 1958-03-19 | 1962-09-11 | Merck & Co Inc | Novel 16-alkyl and 16-alkylene steroids and processes |
| US3007923A (en) * | 1959-01-22 | 1961-11-07 | Lab Francais Chimiotherapie | Process for the fluorination of 9beta, 11beta-epoxy and 5alpha, 6alpha-epoxy steroids |
| US3104246A (en) * | 1961-08-18 | 1963-09-17 | Roussel Uclaf | Process of preparation of beta-methasone |
| US3678137A (en) * | 1970-10-15 | 1972-07-18 | Smith Kline French Lab | Adamantyl-substituted-alkyl 2-aminoethyl phosphates and phosphonates |
| SE378109B (enExample) * | 1972-05-19 | 1975-08-18 | Bofors Ab | |
| US3975391A (en) * | 1973-12-26 | 1976-08-17 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]ethyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| US4068076A (en) * | 1972-12-29 | 1978-01-10 | Otsuka Pharmaceutical Co., Ltd. | 5-(1-Hydroxy-2-(heterocyclic amino))ethyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| US4026897A (en) * | 1974-01-31 | 1977-05-31 | Otsuka Pharmaceutical Company | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives |
| JPS5649907B2 (enExample) * | 1974-02-01 | 1981-11-25 | ||
| US4022784A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives |
| US3994901A (en) * | 1974-06-13 | 1976-11-30 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| US4145542A (en) * | 1974-06-13 | 1979-03-20 | Otsuka Pharmaceutical Co., Ltd. | 5- 1-Hydroxy-2-(heterocyclic-amino)!alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| EP0006735B1 (en) * | 1978-06-28 | 1983-06-15 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| IT7920688U1 (it) | 1979-02-05 | 1980-08-05 | Chiesi Paolo | Inalatore per sostanze medicamentose pulverulente, con combinata funzione di dosatore |
| DE3274065D1 (de) | 1981-07-08 | 1986-12-11 | Draco Ab | Powder inhalator |
| US4582855A (en) * | 1981-11-12 | 1986-04-15 | American Hospital Supply Corporation | Aromatic and esters of hydroxypropylamines |
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| FI69963C (fi) | 1984-10-04 | 1986-09-12 | Orion Yhtymae Oy | Doseringsanordning |
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| EP1078629A3 (en) | 1989-09-07 | 2001-05-23 | Glaxo Group Limited | Use of Salmeterol and salts for the treatment of inflammation and allergy |
| IT1237118B (it) | 1989-10-27 | 1993-05-18 | Miat Spa | Inalatore multidose per farmaci in polvere. |
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| GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| SG45171A1 (en) | 1990-03-21 | 1998-01-16 | Boehringer Ingelheim Int | Atomising devices and methods |
| GB9015522D0 (en) | 1990-07-13 | 1990-08-29 | Braithwaite Philip W | Inhaler |
| WO1992003175A1 (en) | 1990-08-11 | 1992-03-05 | Fisons Plc | Inhalation device |
| DE4027391A1 (de) * | 1990-08-30 | 1992-03-12 | Boehringer Ingelheim Kg | Treibgasfreies inhalationsgeraet |
| US5507281A (en) * | 1990-08-30 | 1996-04-16 | Boehringer Ingelheim Kg | Device for initiating a mechanical switching operation in synchronism with the breathing |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| ATE209938T1 (de) | 1990-09-26 | 2001-12-15 | Pharmachemie Bv | Wirbelkammer-pulverinhalator |
| GB9026025D0 (en) | 1990-11-29 | 1991-01-16 | Boehringer Ingelheim Kg | Inhalation device |
| AU650953B2 (en) * | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
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-
2008
- 2008-02-28 EP EP08382008A patent/EP2096105A1/en not_active Withdrawn
-
2009
- 2009-02-27 RU RU2010139571/04A patent/RU2010139571A/ru not_active Application Discontinuation
- 2009-02-27 JP JP2010548032A patent/JP2011517316A/ja active Pending
- 2009-02-27 EP EP09715428A patent/EP2254860A1/en not_active Withdrawn
- 2009-02-27 MX MX2010008864A patent/MX2010008864A/es not_active Application Discontinuation
- 2009-02-27 AU AU2009218688A patent/AU2009218688A1/en not_active Abandoned
- 2009-02-27 CN CN2009801051173A patent/CN101939291A/zh active Pending
- 2009-02-27 US US12/919,134 patent/US20110028442A1/en not_active Abandoned
- 2009-02-27 CA CA2716397A patent/CA2716397A1/en not_active Abandoned
- 2009-02-27 NZ NZ586049A patent/NZ586049A/en not_active IP Right Cessation
- 2009-02-27 KR KR1020107018606A patent/KR20100138886A/ko not_active Withdrawn
- 2009-02-27 WO PCT/EP2009/001431 patent/WO2009106351A1/en not_active Ceased
-
2010
- 2010-06-04 ZA ZA2010/04009A patent/ZA201004009B/en unknown
- 2010-06-07 IL IL206236A patent/IL206236A0/en unknown
- 2010-08-27 CO CO10105924A patent/CO6251284A2/es not_active Application Discontinuation
- 2010-08-27 EC EC2010010431A patent/ECSP10010431A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100138886A (ko) | 2010-12-31 |
| CO6251284A2 (es) | 2011-02-21 |
| EP2096105A1 (en) | 2009-09-02 |
| CA2716397A1 (en) | 2009-09-03 |
| US20110028442A1 (en) | 2011-02-03 |
| AU2009218688A1 (en) | 2009-09-03 |
| JP2011517316A (ja) | 2011-06-02 |
| WO2009106351A1 (en) | 2009-09-03 |
| CN101939291A (zh) | 2011-01-05 |
| NZ586049A (en) | 2011-07-29 |
| ECSP10010431A (es) | 2010-09-30 |
| EP2254860A1 (en) | 2010-12-01 |
| IL206236A0 (en) | 2010-12-30 |
| MX2010008864A (es) | 2010-09-07 |
| ZA201004009B (en) | 2011-02-23 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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