UA75626C2 - Quinuclidine derivatives and medicinal compositions containing the same - Google Patents
Quinuclidine derivatives and medicinal compositions containing the same Download PDFInfo
- Publication number
- UA75626C2 UA75626C2 UA2003066042A UA2003066042A UA75626C2 UA 75626 C2 UA75626 C2 UA 75626C2 UA 2003066042 A UA2003066042 A UA 2003066042A UA 2003066042 A UA2003066042 A UA 2003066042A UA 75626 C2 UA75626 C2 UA 75626C2
- Authority
- UA
- Ukraine
- Prior art keywords
- hydroxy
- thien
- azoniabicyclo
- group
- cyclopentyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 60
- 150000008584 quinuclidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 211
- -1 5, 6, 7, 8- tetrahydronaphthalenyl Chemical group 0.000 claims abstract description 141
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000005605 benzo group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000006267 biphenyl group Chemical group 0.000 claims abstract description 3
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 126
- 238000000034 method Methods 0.000 claims description 106
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 60
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 41
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 208000023504 respiratory system disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 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 description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 208000014001 urinary system disease Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 208000012931 Urologic disease Diseases 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- DJLYFOLCFWQWQG-UHFFFAOYSA-N octane;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCCCCCC DJLYFOLCFWQWQG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
- 125000005615 azonium group Chemical group 0.000 claims description 7
- 208000010643 digestive system disease Diseases 0.000 claims description 7
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 230000000241 respiratory effect Effects 0.000 claims description 7
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 6
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 6
- 239000000043 antiallergic agent Substances 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 150000002617 leukotrienes Chemical class 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000004305 biphenyl Chemical group 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 229920002554 vinyl polymer Chemical group 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
- 238000005956 quaternization reaction Methods 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 113
- 239000013067 intermediate product Substances 0.000 description 70
- 239000000543 intermediate Substances 0.000 description 62
- 238000002360 preparation method Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- 229910002027 silica gel Inorganic materials 0.000 description 11
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000012458 free base Substances 0.000 description 10
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- 238000004440 column chromatography Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 9
- 229950001870 spizofurone Drugs 0.000 description 9
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 8
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 238000010561 standard procedure Methods 0.000 description 7
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- MEFKEPWMEQBLKI-UHFFFAOYSA-N 2-amino-4-[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate Chemical compound OC1C(O)C(C[S+](CCC(N)C([O-])=O)C)OC1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-UHFFFAOYSA-N 0.000 description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
-
- 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
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200003130 | 2000-12-28 | ||
| PCT/EP2001/015168 WO2002053564A2 (en) | 2000-12-28 | 2001-12-20 | Quinuclidine derivatives and their use as m3 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75626C2 true UA75626C2 (en) | 2006-05-15 |
Family
ID=8496180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003066042A UA75626C2 (en) | 2000-12-28 | 2001-12-20 | Quinuclidine derivatives and medicinal compositions containing the same |
Country Status (33)
| Country | Link |
|---|---|
| US (4) | US7122558B2 (et) |
| EP (1) | EP1353919B1 (et) |
| JP (1) | JP4295985B2 (et) |
| KR (1) | KR100869721B1 (et) |
| CN (1) | CN1250545C (et) |
| AR (1) | AR032072A1 (et) |
| AT (1) | ATE334128T1 (et) |
| AU (1) | AU2002238471B2 (et) |
| BG (1) | BG66162B1 (et) |
| BR (1) | BR0116624A (et) |
| CA (1) | CA2433128C (et) |
| CY (1) | CY1105719T1 (et) |
| CZ (1) | CZ301209B6 (et) |
| DE (1) | DE60121813T2 (et) |
| DK (1) | DK1353919T3 (et) |
| EC (1) | ECSP034672A (et) |
| EE (1) | EE05404B1 (et) |
| ES (1) | ES2266291T3 (et) |
| HU (1) | HUP0303524A3 (et) |
| IL (2) | IL156558A0 (et) |
| MX (1) | MXPA03005862A (et) |
| MY (1) | MY136067A (et) |
| NO (1) | NO328772B1 (et) |
| NZ (1) | NZ526674A (et) |
| PE (1) | PE20020721A1 (et) |
| PL (1) | PL363807A1 (et) |
| PT (1) | PT1353919E (et) |
| RU (1) | RU2282629C2 (et) |
| SI (1) | SI1353919T1 (et) |
| SK (1) | SK287414B6 (et) |
| UA (1) | UA75626C2 (et) |
| WO (1) | WO2002053564A2 (et) |
| ZA (1) | ZA200305008B (et) |
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| SI1353919T1 (sl) * | 2000-12-28 | 2006-12-31 | Almirall Prodesfarma Ag | Novi derivati kinuklidina in medicinske zmesi, kijih vsebujejo. |
| GB0118373D0 (en) * | 2001-07-27 | 2001-09-19 | Glaxo Group Ltd | Novel therapeutic method |
| ES2203327B1 (es) | 2002-06-21 | 2005-06-16 | Almirall Prodesfarma, S.A. | Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen. |
| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| MXPA05000434A (es) | 2002-07-08 | 2005-04-19 | Ranbaxy Lab Ltd | Derivados de hexano [3.1.0] azabiciclo 3,6-disustituido utiles como antagonistas de receptor muscarinico. |
| WO2004014363A1 (en) * | 2002-08-09 | 2004-02-19 | Ranbaxy Laboratories Limited | 3,6-disubstituted azabicyclo [3.1.0] hexane derivatives useful as muscarinic receptor antagonist |
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| EP1626957A1 (en) * | 2003-04-11 | 2006-02-22 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| CN100445281C (zh) * | 2003-05-02 | 2008-12-24 | 诺瓦提斯公司 | 与毒蕈碱性m3受体结合的奎宁环衍生物 |
| AR044134A1 (es) | 2003-05-02 | 2005-08-24 | Novartis Ag | Derivados de quinuclidina, metodo de preparacion y composiciones farmaceuticas. |
| JP4616264B2 (ja) | 2003-05-28 | 2011-01-19 | セラヴァンス， インコーポレーテッド | ムスカリン性レセプターアンタゴニストとしてのアザビシクロアルカン化合物 |
| US7368463B2 (en) | 2003-07-11 | 2008-05-06 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
| US20050026887A1 (en) * | 2003-07-29 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a steroid |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
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2001
- 2001-12-20 SI SI200130596T patent/SI1353919T1/sl unknown
- 2001-12-20 US US10/250,447 patent/US7122558B2/en not_active Expired - Fee Related
- 2001-12-20 AT AT01986924T patent/ATE334128T1/de active
- 2001-12-20 EE EEP200300312A patent/EE05404B1/et not_active IP Right Cessation
- 2001-12-20 CA CA2433128A patent/CA2433128C/en not_active Expired - Fee Related
- 2001-12-20 RU RU2003123120/04A patent/RU2282629C2/ru not_active IP Right Cessation
- 2001-12-20 SK SK799-2003A patent/SK287414B6/sk not_active IP Right Cessation
- 2001-12-20 AU AU2002238471A patent/AU2002238471B2/en not_active Ceased
- 2001-12-20 UA UA2003066042A patent/UA75626C2/uk unknown
- 2001-12-20 KR KR1020037008651A patent/KR100869721B1/ko not_active Expired - Fee Related
- 2001-12-20 JP JP2002555087A patent/JP4295985B2/ja not_active Expired - Fee Related
- 2001-12-20 NZ NZ526674A patent/NZ526674A/en unknown
- 2001-12-20 WO PCT/EP2001/015168 patent/WO2002053564A2/en not_active Ceased
- 2001-12-20 ES ES01986924T patent/ES2266291T3/es not_active Expired - Lifetime
- 2001-12-20 HU HU0303524A patent/HUP0303524A3/hu unknown
- 2001-12-20 IL IL15655801A patent/IL156558A0/xx unknown
- 2001-12-20 DE DE60121813T patent/DE60121813T2/de not_active Expired - Lifetime
- 2001-12-20 PT PT01986924T patent/PT1353919E/pt unknown
- 2001-12-20 EP EP01986924A patent/EP1353919B1/en not_active Expired - Lifetime
- 2001-12-20 CZ CZ20031812A patent/CZ301209B6/cs not_active IP Right Cessation
- 2001-12-20 MX MXPA03005862A patent/MXPA03005862A/es active IP Right Grant
- 2001-12-20 PL PL01363807A patent/PL363807A1/xx unknown
- 2001-12-20 CN CNB018222420A patent/CN1250545C/zh not_active Expired - Fee Related
- 2001-12-20 DK DK01986924T patent/DK1353919T3/da active
- 2001-12-20 BR BR0116624-7A patent/BR0116624A/pt not_active Application Discontinuation
- 2001-12-26 PE PE2001001302A patent/PE20020721A1/es not_active Application Discontinuation
- 2001-12-27 MY MYPI20015907A patent/MY136067A/en unknown
- 2001-12-27 AR ARP010106065A patent/AR032072A1/es unknown
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2003
- 2003-06-19 IL IL156558A patent/IL156558A/en not_active IP Right Cessation
- 2003-06-25 EC EC2003004672A patent/ECSP034672A/es unknown
- 2003-06-26 ZA ZA2003/05008A patent/ZA200305008B/en unknown
- 2003-06-27 BG BG107950A patent/BG66162B1/bg unknown
- 2003-06-30 NO NO20033002A patent/NO328772B1/no not_active IP Right Cessation
-
2006
- 2006-08-31 US US11/515,335 patent/US7893087B2/en not_active Expired - Fee Related
- 2006-08-31 US US11/514,590 patent/US7879874B2/en not_active Expired - Fee Related
- 2006-10-20 CY CY20061101508T patent/CY1105719T1/el unknown
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2010
- 2010-05-21 US US12/785,345 patent/US20100234332A1/en not_active Abandoned
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