ZA200600167B - Muscarinic acetylcholine receptor antagonists - Google Patents
Muscarinic acetylcholine receptor antagonists Download PDFInfo
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- ZA200600167B ZA200600167B ZA200600167A ZA200600167A ZA200600167B ZA 200600167 B ZA200600167 B ZA 200600167B ZA 200600167 A ZA200600167 A ZA 200600167A ZA 200600167 A ZA200600167 A ZA 200600167A ZA 200600167 B ZA200600167 B ZA 200600167B
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 229960001361 ipratropium bromide Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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Classifications
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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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- 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
- A61P11/02—Nasal agents, e.g. decongestants
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- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P11/16—Central respiratory analeptics
-
- 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
- A61P27/16—Otologicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48798203P | 2003-07-17 | 2003-07-17 |
Publications (1)
Publication Number | Publication Date |
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ZA200600167B true ZA200600167B (en) | 2007-01-31 |
Family
ID=34102736
Family Applications (1)
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ZA200600167A ZA200600167B (en) | 2003-07-17 | 2006-01-06 | Muscarinic acetylcholine receptor antagonists |
Country Status (19)
Country | Link |
---|---|
US (1) | US7495010B2 (no) |
EP (1) | EP1648461A4 (no) |
JP (1) | JP2007525478A (no) |
KR (1) | KR20060054316A (no) |
CN (1) | CN1822839A (no) |
AR (1) | AR045914A1 (no) |
AU (1) | AU2004259238A1 (no) |
BR (1) | BRPI0412537A (no) |
CA (1) | CA2532433A1 (no) |
IL (1) | IL172912A0 (no) |
IS (1) | IS8296A (no) |
MA (1) | MA27901A1 (no) |
MX (1) | MXPA06000663A (no) |
NO (1) | NO20060777L (no) |
PE (1) | PE20050250A1 (no) |
RU (1) | RU2006104851A (no) |
TW (1) | TW200519108A (no) |
WO (1) | WO2005009362A2 (no) |
ZA (1) | ZA200600167B (no) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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PL1677795T3 (pl) * | 2003-10-14 | 2011-05-31 | Glaxo Group Ltd | Antagoniści receptora muskarynowego acetylocholiny |
AP2006003575A0 (en) * | 2003-10-17 | 2006-04-30 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists. |
AR046225A1 (es) * | 2003-11-04 | 2005-11-30 | Glaxo Group Ltd | Compuesto de 8-azoniabiciclo(3.2.1)octano, composicion farmaceutica para el tratamiento de enfermedades mediadas por receptores de acetilcolina muscarinicos que lo comprende y uso del compuesto para preparar dicha composicion |
EP1725236A4 (en) * | 2004-03-11 | 2009-05-13 | Glaxo Group Ltd | NEW M3 MUSCARIN ACETYLCHOLINE RECEPTOR ANTAGONISTS |
US7384946B2 (en) * | 2004-03-17 | 2008-06-10 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
WO2005094251A2 (en) * | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | M3muscarinic acetylcholine receptor antagonists |
TWI363759B (en) * | 2004-04-27 | 2012-05-11 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
AU2012202307B2 (en) * | 2004-04-27 | 2015-05-07 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
EP1747219A4 (en) * | 2004-05-13 | 2010-05-26 | Glaxo Group Ltd | Antagonists of muscarinic acetylcholine receptor |
US7932247B2 (en) * | 2004-11-15 | 2011-04-26 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
WO2007016639A2 (en) * | 2005-08-02 | 2007-02-08 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
EP1937068A4 (en) * | 2005-08-18 | 2010-08-04 | Glaxo Group Ltd | ANTAGONISTS OF ACETYLCHOLINE MUSCARINIC RECEPTORS |
CL2009000249A1 (es) | 2008-02-06 | 2009-09-11 | Glaxo Group Ltd | Compuestos derivados de pirazolo[3,4-b] piridin-butanodiamida; composicion farmaceutica; y su uso en el tratamiento del asma, enfermedad pulmonar obstructiva cronica, rinitis, dermatitis atopica, psoriasis. |
PE20091552A1 (es) | 2008-02-06 | 2009-10-25 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
AR070564A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Derivados de 1h-pirazolo[3,4-b]piridin-5-ilo,inhibidores de fosfodiesterasas pde4 y antagonistas de receptores muscarinicos de acetilcolina(machr), utiles en el tratamiento y/o profilaxis de enfermedades respiratorias y alergicas,y composiciones farmaceuticas que los comprenden |
WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
EP3248970A1 (en) | 2016-05-27 | 2017-11-29 | Zentiva K.S. | Forms of umeclidinium bromide |
Family Cites Families (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2800482A (en) * | 1955-07-01 | 1957-07-23 | Smith Kline French Lab | Olefinic derivatives of 8-alkylnortropanes and the acid and quaternary ammonium salts thereof |
US2800478A (en) * | 1955-07-01 | 1957-07-23 | Smith Kline French Lab | 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof |
US2800481A (en) * | 1955-07-01 | 1957-07-23 | Smith Kline French Lab | Tertiary alcohol derivatives of 8-alkylnortropanes and the acid and quaternary ammonium salts thereof |
AT298118B (de) | 1967-06-08 | 1972-04-25 | Siemens Ag | Verfahren zur Umsetzung von Spannungen in digitale Werte und Vorrichtung zur Durchführung des Verfahrens |
CY1308A (en) | 1979-12-06 | 1985-12-06 | Glaxo Group Ltd | Device for dispensing medicaments |
CY1492A (en) | 1981-07-08 | 1990-02-16 | Draco Ab | Powder inhalator |
FI79651C (fi) | 1982-10-08 | 1990-02-12 | Glaxo Group Ltd | Doseringsanordning foer medicin. |
GB2169265B (en) | 1982-10-08 | 1987-08-12 | Glaxo Group Ltd | Pack for medicament |
GR861995B (en) | 1985-07-30 | 1986-11-04 | Glaxo Group Ltd | Devices for administering medicaments to patients |
IT1204826B (it) | 1986-03-04 | 1989-03-10 | Chiesi Farma Spa | Composizioni farmaceutiche per inalazione |
GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
US5780466A (en) | 1995-01-30 | 1998-07-14 | Sanofi | Substituted heterocyclic compounds method of preparing them and pharmaceutical compositions in which they are present |
EP0944626A4 (en) | 1996-12-02 | 2002-09-04 | Univ Georgetown | TROPANE DERIVATIVES AND SYNTHESIS METHOD |
US6248752B1 (en) | 1998-02-27 | 2001-06-19 | Charles Duane Smith | Azabicyclooctane compositions and methods for enhancing chemotherapy |
US6262066B1 (en) | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
EP1302458A4 (en) * | 2000-07-11 | 2005-10-19 | Banyu Pharma Co Ltd | ESTERDERIVATE |
RU2004110717A (ru) | 2001-10-17 | 2005-10-20 | Юсиби, С.А. (Be) | Производные хинуклидина, способы их получения и их применение в качестве и нгибиторов м2- и/или м3- мускариновых рецепторов |
AR040779A1 (es) | 2002-08-06 | 2005-04-20 | Glaxo Group Ltd | Compuesto de tiazol anilina su uso para preparar una formulacion farmaceutica dicha formulacion recipiente que la contiene y dispositivo adaptado para la administracion intranasal de la formulacion |
US7232841B2 (en) | 2003-04-07 | 2007-06-19 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
PE20050711A1 (es) | 2003-07-17 | 2005-09-10 | Glaxo Group Ltd | Compuestos 8-azoniabiciclo[3.2.1] octanos como antagonistas de los receptores muscarinicos de la acetilcolina |
UY28417A1 (es) | 2003-07-17 | 2005-02-28 | Glaxo Group Ltd | Antagonistas de los receptores muscarinicos de la acetilcolina |
PL1677795T3 (pl) | 2003-10-14 | 2011-05-31 | Glaxo Group Ltd | Antagoniści receptora muskarynowego acetylocholiny |
AP2006003575A0 (en) | 2003-10-17 | 2006-04-30 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists. |
AR046225A1 (es) | 2003-11-04 | 2005-11-30 | Glaxo Group Ltd | Compuesto de 8-azoniabiciclo(3.2.1)octano, composicion farmaceutica para el tratamiento de enfermedades mediadas por receptores de acetilcolina muscarinicos que lo comprende y uso del compuesto para preparar dicha composicion |
CA2543858C (en) | 2003-11-21 | 2014-04-15 | Theravance, Inc. | Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
PE20050897A1 (es) | 2003-12-03 | 2005-11-06 | Glaxo Group Ltd | Nuevos antagonistas del receptor muscarinico m3 de acetilcolina |
UY28646A1 (es) | 2003-12-03 | 2005-06-30 | Glaxo Group Ltd | Nuevos antagonistas del receptor muscarinico m3 de acetilcolina |
US7384946B2 (en) | 2004-03-17 | 2008-06-10 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
WO2005094835A1 (en) | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
WO2005094251A2 (en) | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | M3muscarinic acetylcholine receptor antagonists |
WO2005094834A1 (en) | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
TWI363759B (en) | 2004-04-27 | 2012-05-11 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
EP1747219A4 (en) | 2004-05-13 | 2010-05-26 | Glaxo Group Ltd | Antagonists of muscarinic acetylcholine receptor |
JP2008501020A (ja) | 2004-05-28 | 2008-01-17 | グラクソ グループ リミテッド | ムスカリン性アセチルコリン受容体アンタゴニスト |
JP2008518939A (ja) | 2004-10-29 | 2008-06-05 | グラクソ グループ リミテッド | ムスカリン性アセチルコリン受容体アンタゴニスト |
US7932247B2 (en) | 2004-11-15 | 2011-04-26 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
EP1827439A4 (en) | 2004-11-15 | 2009-11-18 | Glaxo Group Ltd | NEW M3 MUSCARIN ACETYLCHOLINE RECEPTOR ANTAGONISTS |
PE20061162A1 (es) | 2004-12-06 | 2006-10-14 | Smithkline Beecham Corp | Compuestos derivados olefinicos de 8-azoniabiciclo[3.2.1]octanos |
PE20060826A1 (es) | 2004-12-06 | 2006-10-08 | Smithkline Beecham Corp | Derivado oleofinico de 8-azoniabiciclo[3.2.1]octano y combinacion farmaceutica que lo comprende |
WO2006065788A2 (en) | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Novel muscarinic acetylcholine receptor antagonists |
WO2006065755A2 (en) | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Quaternary ammonium salts of fused hetearomatic amines as novel muscarinic acetylcholine receptor antagonists |
WO2007018508A1 (en) | 2005-07-28 | 2007-02-15 | Glaxo Group Limited | Novel m3 muscarinic acetycholine receptor antagonists |
WO2007018514A1 (en) | 2005-07-28 | 2007-02-15 | Glaxo Group Limited | Novel m3 muscarinic acetylcholine receptor antagonists |
US20080234315A1 (en) | 2005-08-02 | 2008-09-25 | Jakob Busch-Petersen | M3 Muscarinic Acetylcholine Receptor Antagonists |
WO2007016639A2 (en) | 2005-08-02 | 2007-02-08 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
EP1937068A4 (en) | 2005-08-18 | 2010-08-04 | Glaxo Group Ltd | ANTAGONISTS OF ACETYLCHOLINE MUSCARINIC RECEPTORS |
-
2004
- 2004-07-15 PE PE2004000674A patent/PE20050250A1/es not_active Application Discontinuation
- 2004-07-15 TW TW093121063A patent/TW200519108A/zh unknown
- 2004-07-15 AR ARP040102499A patent/AR045914A1/es unknown
- 2004-07-16 KR KR1020067001001A patent/KR20060054316A/ko not_active Application Discontinuation
- 2004-07-16 MX MXPA06000663A patent/MXPA06000663A/es unknown
- 2004-07-16 EP EP04778509A patent/EP1648461A4/en not_active Withdrawn
- 2004-07-16 AU AU2004259238A patent/AU2004259238A1/en not_active Abandoned
- 2004-07-16 RU RU2006104851/04A patent/RU2006104851A/ru not_active Application Discontinuation
- 2004-07-16 CN CNA2004800206526A patent/CN1822839A/zh active Pending
- 2004-07-16 JP JP2006520387A patent/JP2007525478A/ja active Pending
- 2004-07-16 BR BRPI0412537-1A patent/BRPI0412537A/pt not_active IP Right Cessation
- 2004-07-16 US US10/565,048 patent/US7495010B2/en not_active Expired - Fee Related
- 2004-07-16 WO PCT/US2004/023041 patent/WO2005009362A2/en active Application Filing
- 2004-07-16 CA CA002532433A patent/CA2532433A1/en not_active Abandoned
-
2005
- 2005-12-29 IL IL172912A patent/IL172912A0/en unknown
-
2006
- 2006-01-06 ZA ZA200600167A patent/ZA200600167B/en unknown
- 2006-01-06 MA MA28705A patent/MA27901A1/fr unknown
- 2006-02-13 IS IS8296A patent/IS8296A/is unknown
- 2006-02-17 NO NO20060777A patent/NO20060777L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2005009362A2 (en) | 2005-02-03 |
EP1648461A4 (en) | 2009-04-01 |
KR20060054316A (ko) | 2006-05-22 |
US20060178396A1 (en) | 2006-08-10 |
BRPI0412537A (pt) | 2006-09-19 |
CA2532433A1 (en) | 2005-02-03 |
EP1648461A2 (en) | 2006-04-26 |
MXPA06000663A (es) | 2006-03-30 |
TW200519108A (en) | 2005-06-16 |
RU2006104851A (ru) | 2006-06-27 |
JP2007525478A (ja) | 2007-09-06 |
MA27901A1 (fr) | 2006-05-02 |
CN1822839A (zh) | 2006-08-23 |
AR045914A1 (es) | 2005-11-16 |
IS8296A (is) | 2006-02-13 |
IL172912A0 (en) | 2006-06-11 |
WO2005009362A3 (en) | 2005-04-07 |
AU2004259238A1 (en) | 2005-02-03 |
NO20060777L (no) | 2006-04-11 |
US7495010B2 (en) | 2009-02-24 |
PE20050250A1 (es) | 2005-04-08 |
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