ZA200605931B - New quaternized quinuclidine esters - Google Patents
New quaternized quinuclidine esters Download PDFInfo
- Publication number
- ZA200605931B ZA200605931B ZA200605931A ZA200605931A ZA200605931B ZA 200605931 B ZA200605931 B ZA 200605931B ZA 200605931 A ZA200605931 A ZA 200605931A ZA 200605931 A ZA200605931 A ZA 200605931A ZA 200605931 B ZA200605931 B ZA 200605931B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- azoniabicyclo
- ylacetoxy
- dithien
- octane
- Prior art date
Links
- 150000008584 quinuclidines Chemical class 0.000 title 1
- -1 - O(CO)R’ Chemical group 0.000 claims description 134
- 150000001875 compounds Chemical class 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 43
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 208000023504 respiratory system disease Diseases 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 208000014001 urinary system disease Diseases 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000000241 respiratory effect Effects 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 208000012931 Urologic disease Diseases 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 208000010643 digestive system disease Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- DYEHDACATJUKSZ-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;bromide Chemical compound [Br-].C1CC2CC[NH+]1CC2 DYEHDACATJUKSZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000286 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 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000013066 combination product Substances 0.000 claims 2
- 229940127555 combination product Drugs 0.000 claims 2
- ODVSUCSYVTXUQA-HJOILIIGSA-L OC(C(=O)O[C@H]1C[N+]2(CCC1CC2)C(C)C)(C=2SC=CC2)C=2SC=CC2.[Br-].CC(=CCC[N+]21C[C@@H](C(CC2)CC1)OC(C(C)(C=1SC=CC1)C=1SC=CC1)=O)C.[Br-] Chemical compound OC(C(=O)O[C@H]1C[N+]2(CCC1CC2)C(C)C)(C=2SC=CC2)C=2SC=CC2.[Br-].CC(=CCC[N+]21C[C@@H](C(CC2)CC1)OC(C(C)(C=1SC=CC1)C=1SC=CC1)=O)C.[Br-] ODVSUCSYVTXUQA-HJOILIIGSA-L 0.000 claims 1
- OFIWZJORXIJIHD-AEDYTTQKSA-M [(3r)-1-(4-methylpent-3-enyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C12=CC=CC=C2CCC2=CC=CC=C2C1C(=O)O[C@@H](C1)C2CC[N+]1(CCC=C(C)C)CC2 OFIWZJORXIJIHD-AEDYTTQKSA-M 0.000 claims 1
- HXHWSQWXNXXJHG-YWHDHPDTSA-L [Br-].S1C(=CC=C1)C(C(=O)O[C@H]1C[N+]2(CCC1CC2)CCC=C(C)C)C=2SC=CC2.[Br-].S2C(=CC=C2)C(C(=O)O[C@H]2C[N+]1(CCC2CC1)CCC=C(C)C)C=1SC=CC1 Chemical compound [Br-].S1C(=CC=C1)C(C(=O)O[C@H]1C[N+]2(CCC1CC2)CCC=C(C)C)C=2SC=CC2.[Br-].S2C(=CC=C2)C(C(=O)O[C@H]2C[N+]1(CCC2CC1)CCC=C(C)C)C=1SC=CC1 HXHWSQWXNXXJHG-YWHDHPDTSA-L 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 150000001649 bromium compounds Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010561 standard procedure Methods 0.000 description 6
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
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- IVLICPVPXWEGCA-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC2[C@@H](O)CN1CC2 IVLICPVPXWEGCA-ZETCQYMHSA-N 0.000 description 4
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- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- 239000012528 membrane Substances 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical class C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 3
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- JOZJQRGYHZCPIS-WZSPKAJJSA-M ethyl 5-[(3r)-3-(2-hydroxy-2,2-dithiophen-2-ylacetyl)oxy-1-azoniabicyclo[2.2.2]octan-1-yl]pentanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O([C@@H]1C2CC[N+](CC2)(C1)CCCCC(=O)OCC)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 JOZJQRGYHZCPIS-WZSPKAJJSA-M 0.000 description 1
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- HZUKZELWMDCYOZ-UHFFFAOYSA-N methyl 2,2-dithiophen-2-ylacetate Chemical compound C=1C=CSC=1C(C(=O)OC)C1=CC=CS1 HZUKZELWMDCYOZ-UHFFFAOYSA-N 0.000 description 1
- SYHWYWHVEQQDMO-UHFFFAOYSA-N methyl 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound C=1C=CSC=1C(O)(C(=O)OC)C1=CC=CS1 SYHWYWHVEQQDMO-UHFFFAOYSA-N 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Cardiology (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 |
|---|---|---|---|
| ES200400638A ES2239546B1 (es) | 2004-03-15 | 2004-03-15 | Nuevos esteres de quinuclidina cuaternizados. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605931B true ZA200605931B (en) | 2007-11-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605931A ZA200605931B (en) | 2004-03-15 | 2006-07-18 | New quaternized quinuclidine esters |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US20080214600A1 (es) |
| EP (1) | EP1725552B1 (es) |
| JP (1) | JP2007529444A (es) |
| KR (1) | KR20070003940A (es) |
| CN (1) | CN1930158A (es) |
| AR (1) | AR048004A1 (es) |
| AT (1) | ATE399166T1 (es) |
| AU (1) | AU2005223310A1 (es) |
| BR (1) | BRPI0508177A (es) |
| CA (1) | CA2560157A1 (es) |
| CY (1) | CY1108324T1 (es) |
| DE (1) | DE602005007714D1 (es) |
| DK (1) | DK1725552T3 (es) |
| EC (1) | ECSP066770A (es) |
| ES (2) | ES2239546B1 (es) |
| HK (1) | HK1101855A1 (es) |
| HR (1) | HRP20080338T3 (es) |
| IL (1) | IL177341A0 (es) |
| MY (1) | MY142036A (es) |
| NO (1) | NO20064659L (es) |
| NZ (1) | NZ548583A (es) |
| PE (1) | PE20060005A1 (es) |
| PL (1) | PL1725552T3 (es) |
| PT (1) | PT1725552E (es) |
| RS (1) | RS50566B (es) |
| RU (1) | RU2382041C2 (es) |
| SI (1) | SI1725552T1 (es) |
| TW (1) | TW200604196A (es) |
| UA (1) | UA88634C2 (es) |
| WO (1) | WO2005090342A1 (es) |
| ZA (1) | ZA200605931B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| ES2298049B1 (es) * | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| US20100056565A1 (en) * | 2007-02-15 | 2010-03-04 | Argenta Discovery Limited | Heterocyclic Derivatives as M3 Muscarinic Receptors |
| CN101796026B (zh) | 2007-09-07 | 2013-10-23 | 施万制药 | 可用作毒蕈碱受体拮抗剂的含胍化合物 |
| CA2608561A1 (en) * | 2007-10-29 | 2009-04-29 | Carl Paluszkiewicz | Motorcycle wind deflector accessory support |
| JP2011506477A (ja) | 2007-12-14 | 2011-03-03 | セラヴァンス， インコーポレーテッド | ムスカリン受容体拮抗薬として有用なアミジン含有化合物 |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| US20090326004A1 (en) | 2008-06-03 | 2009-12-31 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| ES2617680T3 (es) * | 2009-04-09 | 2017-06-19 | Novartis Ag | Proceso para la preparación de sales de pirrolidinio |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| WO2014086852A1 (en) * | 2012-12-05 | 2014-06-12 | Chiesi Farmaceutici S.P.A. | Phenylethylpyridine derivatives as pde4-inhibitors |
| CN103755699A (zh) * | 2014-01-06 | 2014-04-30 | 万特制药(海南)有限公司 | 一种2-羟基-2,2-二噻吩-2-基乙酸-1-氮杂二环[2,2,2]辛-3(r)-基酯制备方法 |
| CN103755698A (zh) * | 2014-01-06 | 2014-04-30 | 万特制药(海南)有限公司 | 一锅法制备阿地溴铵的工艺 |
| KR101511090B1 (ko) | 2014-04-24 | 2015-04-10 | 고려대학교 산학협력단 | 염증성 질환의 예방 또는 치료용 약학 조성물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1219606A (en) * | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| US4843074A (en) * | 1988-05-17 | 1989-06-27 | Marion Laboratories, Inc. | 1-azabicyclo[2.2.2]octan-3-yl 2-aryl-3-azacyclo-2-hydroxypropionates and their quaternary salts |
| ES2165768B1 (es) * | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| CN1250545C (zh) * | 2000-12-28 | 2006-04-12 | 阿尔米雷尔普罗迪斯制药有限公司 | 新的奎宁环衍生物类及含有这类衍生物的药物组合物 |
| PL370087A1 (en) * | 2001-10-17 | 2005-05-16 | Ucb, S.A. | Quinuclidine derivatives, processes for preparing them and their uses as m2 and/or m3 muscarinic receptor inhibitors |
| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| AR044134A1 (es) * | 2003-05-02 | 2005-08-24 | Novartis Ag | Derivados de quinuclidina, metodo de preparacion y composiciones farmaceuticas. |
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2004
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2005
- 2005-03-10 KR KR1020067018902A patent/KR20070003940A/ko not_active Application Discontinuation
- 2005-03-10 WO PCT/EP2005/002523 patent/WO2005090342A1/en active Application Filing
- 2005-03-10 CA CA002560157A patent/CA2560157A1/en not_active Abandoned
- 2005-03-10 CN CNA2005800082369A patent/CN1930158A/zh active Pending
- 2005-03-10 DE DE602005007714T patent/DE602005007714D1/de active Active
- 2005-03-10 RU RU2006136085/04A patent/RU2382041C2/ru not_active IP Right Cessation
- 2005-03-10 US US10/592,787 patent/US20080214600A1/en not_active Abandoned
- 2005-03-10 SI SI200530293T patent/SI1725552T1/sl unknown
- 2005-03-10 PL PL05729711T patent/PL1725552T3/pl unknown
- 2005-03-10 BR BRPI0508177-7A patent/BRPI0508177A/pt not_active IP Right Cessation
- 2005-03-10 RS RSP-2008/0334A patent/RS50566B/sr unknown
- 2005-03-10 DK DK05729711T patent/DK1725552T3/da active
- 2005-03-10 ES ES05729711T patent/ES2307168T3/es active Active
- 2005-03-10 PT PT05729711T patent/PT1725552E/pt unknown
- 2005-03-10 AU AU2005223310A patent/AU2005223310A1/en not_active Abandoned
- 2005-03-10 PE PE2005000281A patent/PE20060005A1/es not_active Application Discontinuation
- 2005-03-10 AT AT05729711T patent/ATE399166T1/de not_active IP Right Cessation
- 2005-03-10 EP EP05729711A patent/EP1725552B1/en active Active
- 2005-03-10 NZ NZ548583A patent/NZ548583A/en unknown
- 2005-03-10 JP JP2007503242A patent/JP2007529444A/ja not_active Withdrawn
- 2005-03-11 AR ARP050100934A patent/AR048004A1/es unknown
- 2005-03-15 TW TW094107865A patent/TW200604196A/zh unknown
- 2005-03-15 MY MYPI20051090A patent/MY142036A/en unknown
- 2005-10-03 UA UAA200610595A patent/UA88634C2/ru unknown
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2006
- 2006-07-18 ZA ZA200605931A patent/ZA200605931B/en unknown
- 2006-08-07 IL IL177341A patent/IL177341A0/en unknown
- 2006-08-14 EC EC2006006770A patent/ECSP066770A/es unknown
- 2006-10-13 NO NO20064659A patent/NO20064659L/no not_active Application Discontinuation
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2007
- 2007-05-29 HK HK07105721.8A patent/HK1101855A1/xx not_active IP Right Cessation
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2008
- 2008-07-09 HR HR20080338T patent/HRP20080338T3/xx unknown
- 2008-09-09 CY CY20081100965T patent/CY1108324T1/el unknown
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