JP2002510689A - アザトリシクロ化合物 - Google Patents
アザトリシクロ化合物Info
- Publication number
- JP2002510689A JP2002510689A JP2000542322A JP2000542322A JP2002510689A JP 2002510689 A JP2002510689 A JP 2002510689A JP 2000542322 A JP2000542322 A JP 2000542322A JP 2000542322 A JP2000542322 A JP 2000542322A JP 2002510689 A JP2002510689 A JP 2002510689A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pyridyl
- aza
- compounds
- tricyclo
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 220
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 71
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 10
- NBQLPEVQGAAVEU-UHFFFAOYSA-N 8-pyridin-3-yl-1-azatricyclo[3.3.1.13,7]decan-4-one Chemical compound O=C1C(C2)CC3CC1CN2C3C1=CC=CN=C1 NBQLPEVQGAAVEU-UHFFFAOYSA-N 0.000 claims description 6
- KWBCVUZLCMSFAL-UHFFFAOYSA-N C1C(CO)(C2=O)CC3CC2CN1C3C1=CC=CN=C1 Chemical compound C1C(CO)(C2=O)CC3CC2CN1C3C1=CC=CN=C1 KWBCVUZLCMSFAL-UHFFFAOYSA-N 0.000 claims description 6
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VODCVOLSDCFBLD-UHFFFAOYSA-N OC1C(C2)CC3CC1CN2C3C1=CC=CN=C1 Chemical compound OC1C(C2)CC3CC1CN2C3C1=CC=CN=C1 VODCVOLSDCFBLD-UHFFFAOYSA-N 0.000 claims description 3
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 32
- -1 nicotine compound Chemical class 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
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- 238000003786 synthesis reaction Methods 0.000 description 24
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 23
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- 239000008194 pharmaceutical composition Substances 0.000 description 21
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- 239000005557 antagonist Substances 0.000 description 15
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 14
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- 150000003839 salts Chemical group 0.000 description 8
- INDYXBQOPZTSTJ-UHFFFAOYSA-N 2-pyridin-3-yl-1-azatricyclo[3.3.1.13,7]decane Chemical compound C1C(C2)CC3CC1CN2C3C1=CC=CN=C1 INDYXBQOPZTSTJ-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
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- 210000001218 blood-brain barrier Anatomy 0.000 description 5
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- OQUHYNMITHDQLD-UHFFFAOYSA-N (5-bromopyridin-3-yl)methanamine Chemical compound NCC1=CN=CC(Br)=C1 OQUHYNMITHDQLD-UHFFFAOYSA-N 0.000 description 4
- WDVDHJLKXYCOFS-UHFFFAOYSA-N (5-bromopyridin-3-yl)methanol Chemical compound OCC1=CN=CC(Br)=C1 WDVDHJLKXYCOFS-UHFFFAOYSA-N 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 4
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- 206010010904 Convulsion Diseases 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- HKQTYQDNCKMNHZ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)CCC21OCCO2 HKQTYQDNCKMNHZ-UHFFFAOYSA-N 0.000 description 3
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- 229960001860 salicylate Drugs 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 210000003594 spinal ganglia Anatomy 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000000101 transmission high energy electron diffraction Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- CHQOEHPMXSHGCL-UHFFFAOYSA-N trimethaphan Chemical compound C12C[S+]3CCCC3C2N(CC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 CHQOEHPMXSHGCL-UHFFFAOYSA-N 0.000 description 1
- 229940035742 trimethaphan Drugs 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/054,179 US5986100A (en) | 1998-04-02 | 1998-04-02 | Pharmaceutical compositions and methods for use |
| US09/054,179 | 1998-04-02 | ||
| PCT/US1999/004324 WO1999051601A1 (en) | 1998-04-02 | 1999-02-26 | Azatricyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002510689A true JP2002510689A (ja) | 2002-04-09 |
| JP2002510689A5 JP2002510689A5 (enExample) | 2006-01-19 |
Family
ID=21989278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000542322A Pending JP2002510689A (ja) | 1998-04-02 | 1999-02-26 | アザトリシクロ化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5986100A (enExample) |
| EP (1) | EP1066287B1 (enExample) |
| JP (1) | JP2002510689A (enExample) |
| KR (1) | KR100613050B1 (enExample) |
| AT (1) | ATE248839T1 (enExample) |
| AU (1) | AU2794899A (enExample) |
| BR (1) | BR9907191A (enExample) |
| CA (1) | CA2317570A1 (enExample) |
| DE (1) | DE69910993T2 (enExample) |
| DK (1) | DK1066287T3 (enExample) |
| ES (1) | ES2205778T3 (enExample) |
| MX (1) | MXPA00009624A (enExample) |
| PT (1) | PT1066287E (enExample) |
| WO (1) | WO1999051601A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010509239A (ja) * | 2006-11-06 | 2010-03-25 | アボット・ラボラトリーズ | アザアダマンタン誘導体およびこのニコチン性アセチルコリン受容体リガンドとしての使用 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EE200100096A (et) | 1998-08-18 | 2002-06-17 | Ucb, S.A. | Asatsüklilise tüvistruktuuriga tsükliline ühend, seda sisaldav farmatseutiline kompositsioon ning selle kasutamine ravimina |
| HUP0501017A3 (en) * | 2001-12-14 | 2010-06-28 | Targacept | Methods and compositions for treatment of central nervous system disorders |
| US20030162770A1 (en) | 2002-02-22 | 2003-08-28 | Davis Bonnie M. | Use of modulators of nicotinic receptors for treatment of cognitive dysfunction |
| US7897766B2 (en) * | 2005-09-23 | 2011-03-01 | Abbott Laboratories | Amino-aza-adamantane derivatives and methods of use |
| AU2012203831B2 (en) * | 2006-11-06 | 2013-12-19 | Abbvie Bahamas Ltd | Azaadamantane derivatives and their uses as nicotinic acetylcholine receptors ligands |
| MX2009010176A (es) * | 2007-03-23 | 2009-10-12 | Abbott Lab | Derivados de aza-adamantano 4-substituidos y metodos de uso de los mismos. |
| EP2069346B1 (en) * | 2007-03-23 | 2011-12-21 | Abbott Laboratories | Acetamide and carboxamide derivatives of azaadamantane and methods of use thereof |
| CN106074548A (zh) | 2010-09-23 | 2016-11-09 | 艾伯维巴哈马有限公司 | 氮杂金刚烷衍生物的一水合物 |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2022886A1 (en) * | 1989-08-08 | 1991-02-09 | Raymond Baker | Substituted pyridines, their preparation, formulations and use in dementia |
| US5110933A (en) * | 1989-11-13 | 1992-05-05 | Board Of Regents Of Oklahoma State University | Salts of 3-azabicyclo[3.3.1]nonanes as antiarrhythmic agents, and precursors thereof |
| EP0492903A1 (en) * | 1990-12-21 | 1992-07-01 | MERCK SHARP & DOHME LTD. | Substituted pyrazines, pyrimidines and pyridazines for use in the treatment of glaucoma |
| WO1995003306A1 (en) * | 1993-07-22 | 1995-02-02 | E.I. Du Pont De Nemours And Company | Arthropodicidal azacyclic heterocycles |
| US5510355A (en) * | 1994-09-06 | 1996-04-23 | Bencherif; Merouane | Depolarizing skeletal muscle relaxants |
| AU5383196A (en) * | 1995-05-17 | 1996-11-29 | R.J. Reynolds Tobacco Company | Pharmaceutical compositions for prevention and treatment of central nervous system disorders |
| US5583140A (en) * | 1995-05-17 | 1996-12-10 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of central nervous system disorders |
| US5684159A (en) * | 1995-05-30 | 1997-11-04 | Rhone-Poulenc Rorer S.A. | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
-
1998
- 1998-04-02 US US09/054,179 patent/US5986100A/en not_active Expired - Lifetime
-
1999
- 1999-02-26 MX MXPA00009624A patent/MXPA00009624A/es not_active IP Right Cessation
- 1999-02-26 PT PT99908541T patent/PT1066287E/pt unknown
- 1999-02-26 EP EP99908541A patent/EP1066287B1/en not_active Expired - Lifetime
- 1999-02-26 ES ES99908541T patent/ES2205778T3/es not_active Expired - Lifetime
- 1999-02-26 AT AT99908541T patent/ATE248839T1/de not_active IP Right Cessation
- 1999-02-26 DE DE69910993T patent/DE69910993T2/de not_active Expired - Fee Related
- 1999-02-26 DK DK99908541T patent/DK1066287T3/da active
- 1999-02-26 JP JP2000542322A patent/JP2002510689A/ja active Pending
- 1999-02-26 BR BR9907191-6A patent/BR9907191A/pt not_active Application Discontinuation
- 1999-02-26 CA CA002317570A patent/CA2317570A1/en not_active Abandoned
- 1999-02-26 WO PCT/US1999/004324 patent/WO1999051601A1/en not_active Ceased
- 1999-02-26 KR KR1020007008962A patent/KR100613050B1/ko not_active Expired - Fee Related
- 1999-02-26 AU AU27948/99A patent/AU2794899A/en not_active Abandoned
- 1999-07-21 US US09/358,590 patent/US6211372B1/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010509239A (ja) * | 2006-11-06 | 2010-03-25 | アボット・ラボラトリーズ | アザアダマンタン誘導体およびこのニコチン性アセチルコリン受容体リガンドとしての使用 |
| JP2013121969A (ja) * | 2006-11-06 | 2013-06-20 | Abbott Lab | アザアダマンタン誘導体およびこのニコチン性アセチルコリン受容体リガンドとしての使用 |
| JP2014193917A (ja) * | 2006-11-06 | 2014-10-09 | Abbott Laboratories | アザアダマンタン誘導体およびこのニコチン性アセチルコリン受容体リガンドとしての使用 |
| JP2015143260A (ja) * | 2006-11-06 | 2015-08-06 | アボット・ラボラトリーズＡｂｂｏｔｔ Ｌａｂｏｒａｔｏｒｉｅｓ | アザアダマンタン誘導体およびこのニコチン性アセチルコリン受容体リガンドとしての使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2205778T3 (es) | 2004-05-01 |
| EP1066287A1 (en) | 2001-01-10 |
| MXPA00009624A (es) | 2005-06-20 |
| DE69910993T2 (de) | 2004-07-22 |
| DK1066287T3 (da) | 2004-01-19 |
| CA2317570A1 (en) | 1999-10-14 |
| PT1066287E (pt) | 2004-01-30 |
| ATE248839T1 (de) | 2003-09-15 |
| US5986100A (en) | 1999-11-16 |
| BR9907191A (pt) | 2000-12-26 |
| DE69910993D1 (de) | 2003-10-09 |
| KR20010052172A (ko) | 2001-06-25 |
| KR100613050B1 (ko) | 2006-08-25 |
| EP1066287B1 (en) | 2003-09-03 |
| US6211372B1 (en) | 2001-04-03 |
| WO1999051601A1 (en) | 1999-10-14 |
| AU2794899A (en) | 1999-10-25 |
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