RU2399620C2 - Производные хинуклидина и их применение в качестве антагонистов мускариновых рецепторов м3 - Google Patents
Производные хинуклидина и их применение в качестве антагонистов мускариновых рецепторов м3 Download PDFInfo
- Publication number
- RU2399620C2 RU2399620C2 RU2007120454/04A RU2007120454A RU2399620C2 RU 2399620 C2 RU2399620 C2 RU 2399620C2 RU 2007120454/04 A RU2007120454/04 A RU 2007120454/04A RU 2007120454 A RU2007120454 A RU 2007120454A RU 2399620 C2 RU2399620 C2 RU 2399620C2
- Authority
- RU
- Russia
- Prior art keywords
- hydroxy
- isoxazol
- ylcarbamoylmethyl
- azoniumbicyclo
- octanbromide
- Prior art date
Links
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title 1
- 150000008584 quinuclidines Chemical class 0.000 title 1
- -1 9-hydroxy- 9H-fluoren-9-yl Chemical group 0.000 claims abstract 75
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000001404 mediated effect Effects 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- NGVBCVSVEUPNPV-UHFFFAOYSA-N bicyclo[2.2.2]octane;hydrobromide Chemical compound Br.C1CC2CCC1CC2 NGVBCVSVEUPNPV-UHFFFAOYSA-N 0.000 claims 7
- BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000002757 inflammatory effect Effects 0.000 claims 4
- IHUQZTZEAHEZQY-UHFFFAOYSA-N P(=O)(O)(O)O.C12CCC(CC1)CC2 Chemical compound P(=O)(O)(O)O.C12CCC(CC1)CC2 IHUQZTZEAHEZQY-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000000414 obstructive effect Effects 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
- 206010027654 Allergic conditions Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims 1
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000018569 Respiratory Tract disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 abstract 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 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
- 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
- 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
- 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
- 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)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0424284.8 | 2004-11-02 | ||
| GBGB0424284.8A GB0424284D0 (en) | 2004-11-02 | 2004-11-02 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007120454A RU2007120454A (ru) | 2008-12-10 |
| RU2399620C2 true RU2399620C2 (ru) | 2010-09-20 |
Family
ID=33515948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007120454/04A RU2399620C2 (ru) | 2004-11-02 | 2005-10-31 | Производные хинуклидина и их применение в качестве антагонистов мускариновых рецепторов м3 |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US7723356B2 (OSRAM) |
| EP (2) | EP1811999B1 (OSRAM) |
| JP (1) | JP4950896B2 (OSRAM) |
| KR (1) | KR101252307B1 (OSRAM) |
| CN (1) | CN101056634B (OSRAM) |
| AR (1) | AR054090A1 (OSRAM) |
| AT (1) | ATE481099T1 (OSRAM) |
| AU (1) | AU2005300710B2 (OSRAM) |
| BR (1) | BRPI0517945A (OSRAM) |
| CA (1) | CA2583237C (OSRAM) |
| CY (1) | CY1110952T1 (OSRAM) |
| DE (1) | DE602005023639D1 (OSRAM) |
| DK (1) | DK1811999T3 (OSRAM) |
| EC (1) | ECSP077424A (OSRAM) |
| ES (1) | ES2353142T3 (OSRAM) |
| GB (1) | GB0424284D0 (OSRAM) |
| HR (1) | HRP20100693T1 (OSRAM) |
| IL (1) | IL182695A0 (OSRAM) |
| JO (1) | JO2613B1 (OSRAM) |
| MA (1) | MA29080B1 (OSRAM) |
| MX (1) | MX2007005189A (OSRAM) |
| MY (1) | MY145207A (OSRAM) |
| NO (1) | NO20072371L (OSRAM) |
| NZ (1) | NZ554302A (OSRAM) |
| PE (1) | PE20060609A1 (OSRAM) |
| PL (1) | PL1811999T3 (OSRAM) |
| PT (1) | PT1811999E (OSRAM) |
| RU (1) | RU2399620C2 (OSRAM) |
| SI (1) | SI1811999T1 (OSRAM) |
| TN (1) | TNSN07164A1 (OSRAM) |
| TW (1) | TW200628154A (OSRAM) |
| WO (1) | WO2006048225A1 (OSRAM) |
| ZA (1) | ZA200702772B (OSRAM) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR044134A1 (es) * | 2003-05-02 | 2005-08-24 | Novartis Ag | Derivados de quinuclidina, metodo de preparacion y composiciones farmaceuticas. |
| EP1924553A1 (en) | 2005-08-08 | 2008-05-28 | Argenta Discovery Limited | Bicyclo[2.2.]hept-7-ylamine derivatives and their uses |
| EP1940775A2 (en) | 2005-08-11 | 2008-07-09 | University of Massachusetts | Methods and compositions for the efficient delivery of therapeutic agents to cells and animals |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| EP1894568A1 (en) * | 2006-08-31 | 2008-03-05 | Novartis AG | Pharmaceutical compositions for the treatment of inflammatory or obstructive airway diseases |
| TW200825084A (en) * | 2006-11-14 | 2008-06-16 | Astrazeneca Ab | New compounds 521 |
| EP2121137B1 (en) * | 2006-12-19 | 2012-04-25 | AstraZeneca AB | Quinuclidinol derivatives as muscarinic receptor antagonists |
| BRPI0816219B8 (pt) | 2007-09-07 | 2021-05-25 | Theravance Biopharma R&D Ip Llc | compostos contendo guanidina úteis como antagonistas de receptor muscarínico, composição farmacêutica e uso |
| EP2222637A1 (en) | 2007-12-14 | 2010-09-01 | Theravance, Inc. | Amidine-containing compounds useful as muscarinic receptor antagonists |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| GB0808707D0 (en) * | 2008-05-13 | 2008-06-18 | Argenta Discovery Ltd | New compounds 275 |
| RU2010147881A (ru) * | 2008-05-13 | 2012-06-20 | Астразенека Аб (Se) | ФАРМАЦЕВТИЧЕСКИЙ ПРОДУКТ, СОДЕРЖАЩИЙ АНТАГОНИСТ МУСКАРИНОВОГО РЕЦЕПТОРА И АГОНИСТ β2-АДРЕНОРЕЦЕПТОРА |
| US8329729B2 (en) * | 2008-05-13 | 2012-12-11 | Astrazeneca Ab | Quinuclidine derivatives as muscarinic M3 receptor antagonists |
| GB0808708D0 (en) * | 2008-05-13 | 2008-06-18 | Astrazeneca Ab | New compounds 274 |
| US20090326004A1 (en) * | 2008-06-03 | 2009-12-31 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| GB0811100D0 (en) * | 2008-06-17 | 2008-07-23 | Astrazeneca Ab | New combination |
| WO2009153536A1 (en) * | 2008-06-17 | 2009-12-23 | Argenta Discovery Limited | 1-aza-bicyclo [2.2.2] octane derivatives useful as muscarinic receptor antagonists |
| US8263623B2 (en) | 2008-07-11 | 2012-09-11 | Pfizer Inc. | Triazol derivatives useful for the treatment of diseases |
| EP2206712A1 (en) * | 2008-12-23 | 2010-07-14 | CHIESI FARMACEUTICI S.p.A. | "Alkaloid aminoester derivatives and medicinal composition thereof" |
| JP5902612B2 (ja) | 2009-04-09 | 2016-04-13 | ノバルティス アーゲー | ピロリジニウム塩の調製方法 |
| UA107499C2 (uk) * | 2010-06-22 | 2015-01-12 | Chiesi Farm Spa | Склад сухого порошку, який містить антимускариновий засіб |
| RU2569846C2 (ru) * | 2010-06-22 | 2015-11-27 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Алкалоидные производные сложных аминоэфиров и включающие их лекарственные композиции |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| CA2828219A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Pyrazolo [1,5-a] pyridines as trk inhibitors |
| JP2011195593A (ja) * | 2011-06-30 | 2011-10-06 | Astrazeneca Ab | ムスカリンｍ３受容体アンタゴニストとしてのキヌクリジン誘導体 |
| HK1212348A1 (en) | 2012-12-19 | 2016-06-10 | Novartis Ag | Autotaxin inhibitors |
| WO2015162558A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Autotaxin inhibitors |
| WO2015171753A1 (en) * | 2014-05-06 | 2015-11-12 | Visco Anthony G | Methods of treating or preventing preterm labor |
| CN109851615B (zh) * | 2019-04-22 | 2021-06-08 | 上海旭东海普药业有限公司 | 纯化戊乙奎醚的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2117669C1 (ru) * | 1991-09-14 | 1998-08-20 | Пфайзер Инк. | Эфиры хинуклидина, промежуточные соединения для их синтеза, фармацевтическая композиция и способ лечения |
| WO2001004118A2 (en) * | 1999-07-14 | 2001-01-18 | Almirall Prodesfarma S.A. | Quinuclidine derivatives and their use as muscarinic m3 receptor ligands |
| EP1300407A1 (en) * | 2000-06-27 | 2003-04-09 | Laboratorios S.A.L.V.A.T., S.A. | Carbamates derived from arylalkylamines |
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