KR20040099446A - 헤테로시클릭 화합물 - Google Patents
헤테로시클릭 화합물 Download PDFInfo
- Publication number
- KR20040099446A KR20040099446A KR10-2004-7016545A KR20047016545A KR20040099446A KR 20040099446 A KR20040099446 A KR 20040099446A KR 20047016545 A KR20047016545 A KR 20047016545A KR 20040099446 A KR20040099446 A KR 20040099446A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridine
- furo
- azabicyclo
- octane
- spiro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
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- 238000000034 method Methods 0.000 claims description 26
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- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 230000006735 deficit Effects 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 230000002265 prevention Effects 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229960002715 nicotine Drugs 0.000 claims description 11
- 208000028017 Psychotic disease Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 8
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- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 8
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- UTNQUMOIHZDNPR-FQEVSTJZSA-N (3r)-5'-(1,3-benzothiazol-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1=CC=C2SC(C=3C=C4C[C@]5(C6CCN(CC6)C5)OC4=NC=3)=NC2=C1 UTNQUMOIHZDNPR-FQEVSTJZSA-N 0.000 claims description 4
- YLVFFNFPLJAZEC-FQEVSTJZSA-N (3r)-5'-(1,3-benzoxazol-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1=CC=C2OC(C=3C=C4C[C@]5(C6CCN(CC6)C5)OC4=NC=3)=NC2=C1 YLVFFNFPLJAZEC-FQEVSTJZSA-N 0.000 claims description 4
- ZMMGHYIOVFHICY-INIZCTEOSA-N (3r)-5'-(1,3-oxazol-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=NC=CO1 ZMMGHYIOVFHICY-INIZCTEOSA-N 0.000 claims description 4
- PGMPAGCXAUEGDP-INIZCTEOSA-N (3r)-5'-(1,3-thiazol-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=NC=CS1 PGMPAGCXAUEGDP-INIZCTEOSA-N 0.000 claims description 4
- STWUDQAOEPYQAW-INIZCTEOSA-N (3r)-5'-(1,3-thiazol-4-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=CSC=N1 STWUDQAOEPYQAW-INIZCTEOSA-N 0.000 claims description 4
- JNEIQTNYQGYWIF-INIZCTEOSA-N (3r)-5'-(1,3-thiazol-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=CN=CS1 JNEIQTNYQGYWIF-INIZCTEOSA-N 0.000 claims description 4
- OPNPJEFFAANXTO-KRWDZBQOSA-N (3r)-5'-(2-methyl-1,3-thiazol-4-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C)=NC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 OPNPJEFFAANXTO-KRWDZBQOSA-N 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
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- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- RGLYDBOOHIFTEH-SFHVURJKSA-N (3r)-5'-(3,5-dimethyl-1,2-oxazol-4-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound CC1=NOC(C)=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 RGLYDBOOHIFTEH-SFHVURJKSA-N 0.000 claims description 3
- 206010057852 Nicotine dependence Diseases 0.000 claims description 3
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IAADVLIGDRQHCI-KRWDZBQOSA-N (3r)-5'-(2-methyl-1,3-thiazol-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C)=NC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 IAADVLIGDRQHCI-KRWDZBQOSA-N 0.000 claims description 2
- MFKLMAUXODZWDR-INIZCTEOSA-N (3r)-5'-[2-(trifluoromethyl)-1,3-thiazol-5-yl]spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C(F)(F)F)=NC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 MFKLMAUXODZWDR-INIZCTEOSA-N 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 239000003054 catalyst Substances 0.000 description 11
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201185A SE0201185D0 (sv) | 2002-04-18 | 2002-04-18 | Heterocyclic compounds |
| SE0201185-6 | 2002-04-18 | ||
| SE0203606A SE0203606D0 (sv) | 2002-12-04 | 2002-12-04 | Heterocyclic compounds |
| SE0203606-9 | 2002-12-04 | ||
| PCT/SE2003/000615 WO2003087104A1 (en) | 2002-04-18 | 2003-04-15 | Heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040099446A true KR20040099446A (ko) | 2004-11-26 |
Family
ID=29253787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7016545A Ceased KR20040099446A (ko) | 2002-04-18 | 2003-04-15 | 헤테로시클릭 화합물 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7417050B2 (https=) |
| EP (1) | EP1499616B1 (https=) |
| JP (1) | JP4523775B2 (https=) |
| KR (1) | KR20040099446A (https=) |
| CN (1) | CN1325501C (https=) |
| AT (1) | ATE433981T1 (https=) |
| AU (1) | AU2003224546B2 (https=) |
| BR (1) | BR0309345A (https=) |
| CA (1) | CA2482313A1 (https=) |
| DE (1) | DE60328010D1 (https=) |
| ES (1) | ES2326638T3 (https=) |
| HK (1) | HK1080470B (https=) |
| IL (1) | IL164511A0 (https=) |
| MX (1) | MXPA04010190A (https=) |
| NO (1) | NO20044995L (https=) |
| NZ (1) | NZ561993A (https=) |
| WO (1) | WO2003087104A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| HUP0402289A2 (hu) | 2001-10-02 | 2005-02-28 | Pharmacia & Upjohn Company | Gyógyhatású azabiciklusos csoporttal helyettesített kondenzált heteroaril-származékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk |
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| AR013184A1 (es) * | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
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| FR2788982B1 (fr) | 1999-02-02 | 2002-08-02 | Synthelabo | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| US6569865B2 (en) * | 2001-06-01 | 2003-05-27 | Astrazeneca Ab | Spiro 1-azabicyclo[2.2.2]octane-3,2′(3′h)-furo[2,3-b]pyridine |
| DE60218032T2 (de) | 2001-06-01 | 2007-08-16 | Astrazeneca Ab | Neuer, für die therapie geeigneter ligand für nikotinische acetylcholinrezeptoren |
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2003
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- 2003-04-15 KR KR10-2004-7016545A patent/KR20040099446A/ko not_active Ceased
- 2003-04-15 JP JP2003584060A patent/JP4523775B2/ja not_active Expired - Fee Related
- 2003-04-15 DE DE60328010T patent/DE60328010D1/de not_active Expired - Lifetime
- 2003-04-15 WO PCT/SE2003/000615 patent/WO2003087104A1/en not_active Ceased
- 2003-04-15 AU AU2003224546A patent/AU2003224546B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| HK1080470B (zh) | 2008-03-07 |
| WO2003087104A1 (en) | 2003-10-23 |
| HK1080470A1 (zh) | 2006-04-28 |
| DE60328010D1 (de) | 2009-07-30 |
| AU2003224546B2 (en) | 2008-11-06 |
| EP1499616A1 (en) | 2005-01-26 |
| NZ561993A (en) | 2008-09-26 |
| US7417050B2 (en) | 2008-08-26 |
| ATE433981T1 (de) | 2009-07-15 |
| IL164511A0 (en) | 2005-12-18 |
| JP2005534624A (ja) | 2005-11-17 |
| EP1499616B1 (en) | 2009-06-17 |
| CA2482313A1 (en) | 2003-10-23 |
| CN1662542A (zh) | 2005-08-31 |
| US20050131003A1 (en) | 2005-06-16 |
| ES2326638T3 (es) | 2009-10-16 |
| BR0309345A (pt) | 2005-02-15 |
| CN1325501C (zh) | 2007-07-11 |
| NO20044995L (no) | 2005-01-18 |
| AU2003224546A1 (en) | 2003-10-27 |
| MXPA04010190A (es) | 2005-02-03 |
| JP4523775B2 (ja) | 2010-08-11 |
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