TWI311137B - Diazabicyclic central nervous system active agents - Google Patents
Diazabicyclic central nervous system active agents Download PDFInfo
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- TWI311137B TWI311137B TW090110172A TW90110172A TWI311137B TW I311137 B TWI311137 B TW I311137B TW 090110172 A TW090110172 A TW 090110172A TW 90110172 A TW90110172 A TW 90110172A TW I311137 B TWI311137 B TW I311137B
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- Prior art keywords
- pyridyl
- cis
- ratio
- formula
- etoac
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- 210000003169 central nervous system Anatomy 0.000 title description 6
- 239000013543 active substance Substances 0.000 title description 2
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- 150000003839 salts Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
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- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US55994300A | 2000-04-27 | 2000-04-27 | |
| US09/833,914 US6809105B2 (en) | 2000-04-27 | 2001-04-12 | Diazabicyclic central nervous system active agents |
Publications (1)
| Publication Number | Publication Date |
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| TWI311137B true TWI311137B (en) | 2009-06-21 |
Family
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Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
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| TW090110172A TWI311137B (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
| TW100130949A TW201141871A (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
| TW095100404A TWI323733B (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
| TW097145362A TWI357903B (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
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| TW100130949A TW201141871A (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
| TW095100404A TWI323733B (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
| TW097145362A TWI357903B (en) | 2000-04-27 | 2001-05-22 | Diazabicyclic central nervous system active agents |
Country Status (22)
| Country | Link |
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| JP (2) | JP4981232B2 (enExample) |
| KR (4) | KR100947188B1 (enExample) |
| CN (3) | CN102863441A (enExample) |
| AR (1) | AR030421A1 (enExample) |
| AU (2) | AU2001266559C1 (enExample) |
| BG (2) | BG66151B1 (enExample) |
| BR (1) | BR0107246A (enExample) |
| CA (2) | CA2407094C (enExample) |
| CZ (4) | CZ302038B6 (enExample) |
| HK (1) | HK1054375A1 (enExample) |
| HU (1) | HUP0300602A3 (enExample) |
| IL (3) | IL152231A0 (enExample) |
| MX (1) | MXPA02010594A (enExample) |
| MY (3) | MY137020A (enExample) |
| NO (1) | NO324250B1 (enExample) |
| NZ (1) | NZ521734A (enExample) |
| PE (1) | PE20011305A1 (enExample) |
| PL (2) | PL398491A1 (enExample) |
| SK (2) | SK287658B6 (enExample) |
| TW (4) | TWI311137B (enExample) |
| WO (1) | WO2001081347A2 (enExample) |
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| AU777911B2 (en) | 1999-12-10 | 2004-11-04 | Pfizer Products Inc. | Pyrrolo(2,3-d)pyrimidine compounds |
| SE0100326D0 (sv) * | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| BR0316470A (pt) * | 2002-11-21 | 2005-10-11 | Pfizer Prod Inc | Derivados de 3-amino-piperadina e métodos de preparação |
| US7354937B2 (en) | 2004-05-21 | 2008-04-08 | Abbott Laboratories | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane |
| US20040242641A1 (en) * | 2003-05-27 | 2004-12-02 | Buckley Michael J. | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent |
| US20050261348A1 (en) * | 2004-05-21 | 2005-11-24 | Buckley Michael J | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent |
| US20050043407A1 (en) * | 2003-08-22 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| GB0322140D0 (en) * | 2003-09-22 | 2003-10-22 | Pfizer Ltd | Combinations |
| US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| US20050171079A1 (en) | 2004-02-04 | 2005-08-04 | Schrimpf Michael R. | Amino-substituted tricyclic derivatives and methods of use |
| JP2007535553A (ja) | 2004-04-29 | 2007-12-06 | アボット・ラボラトリーズ | アミノ−テトラゾール類縁体および使用方法 |
| US7351833B2 (en) | 2004-07-23 | 2008-04-01 | Abbott Laboratories | (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate |
| CA2634305A1 (en) * | 2005-12-20 | 2007-06-28 | Marc Chapdelaine | Substituted cinnoline derivatives as gabaa-receptor modulators and method for their synthesis |
| US20070184490A1 (en) * | 2006-01-17 | 2007-08-09 | Marleen Verlinden | Neuronal nicotinic receptor ligands and their use |
| US7728031B2 (en) | 2006-02-24 | 2010-06-01 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole derivatives |
| EP2083921A2 (en) | 2006-09-04 | 2009-08-05 | Neurosearch A/S | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
| UY30846A1 (es) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
| WO2008118742A1 (en) | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Azaadamantane ester and carbamate derivatives and methods of use thereof |
| CA2691782A1 (en) | 2007-09-11 | 2009-03-19 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole n-oxides |
| UY31443A1 (es) | 2007-10-31 | 2009-04-30 | Diaminas en puente o fusionadas sustituidas con arilo como moduladores de leucotrieno a4 hidrolasa | |
| JP5628043B2 (ja) * | 2007-11-21 | 2014-11-19 | アッヴィ・インコーポレイテッド | ビアリール置換ジアザビシクロアルカン誘導体 |
| EP2623504A1 (de) | 2007-12-07 | 2013-08-07 | Abbott GmbH & Co. KG | 5,6-Disubstituierte Oxindol-Derivate und ihre Verwendung zur Herstellung eines Medikaments zur Behandlung von Vasopressin-abhängigen Erkrankungen |
| WO2009071687A1 (de) | 2007-12-07 | 2009-06-11 | Abbott Gmbh & Co. Kg | Amidomethyl-substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen |
| CA2707669C (en) | 2007-12-07 | 2016-07-05 | Wilfried Braje | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressine-dependent diseases |
| US8703774B2 (en) | 2007-12-07 | 2014-04-22 | AbbVie Deutschland GmbH & Co. KG | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
| MX2010006111A (es) | 2007-12-18 | 2010-06-25 | Actelion Pharmaceuticals Ltd | Derivados de 5-aminociclilmetil-oxazolidin-2-ona y su uso como antibacteriales. |
| PT2336125E (pt) | 2008-04-11 | 2013-03-18 | Janssen Pharmaceutica Nv | Tiazolopiridina-2-iloxi-fenil e tiazolopirazin-2-iloxifenil aminas como moduladores de leucotrieno a4 hidrolase |
| US8148408B2 (en) * | 2008-05-09 | 2012-04-03 | Abbott Laboratories | Selective substituted pyridine ligands for neuronal nicotinic receptors |
| US8263632B2 (en) * | 2009-03-24 | 2012-09-11 | Vertex Pharmaceuticals Incoporated | Aminopyridine derivatives having Aurora A selective inhibitory action |
| WO2010132599A1 (en) | 2009-05-14 | 2010-11-18 | Janssen Pharmaceutica Nv | Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene a4 hydrolase |
| WO2010138600A2 (en) | 2009-05-29 | 2010-12-02 | Abbott Laboratories | Pharmaceutical compositions for the treatment of pain |
| US8268853B2 (en) | 2009-06-25 | 2012-09-18 | Abbott Laboratories | 3,9-diazaspiro[5,5]undecane amides and ureas and methods of use thereof |
| HUE043522T2 (hu) | 2009-09-04 | 2019-08-28 | Biogen Ma Inc | Bruton tirozinkináz inhibitorok |
| DK3093291T3 (da) | 2009-10-23 | 2019-07-29 | Janssen Pharmaceutica Nv | Disubstituerede octahy-dropyrrolo [3,4-c]pyrroler som orexinreceptormodulatorer |
| JP5848251B2 (ja) * | 2009-10-23 | 2016-01-27 | ヤンセン ファーマシューティカ エヌ．ベー． | オレキシン受容体調節因子としての縮合複素環式化合物 |
| WO2011050200A1 (en) | 2009-10-23 | 2011-04-28 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as orexin receptor modulators |
| US9586962B2 (en) | 2011-04-20 | 2017-03-07 | Janssen Pharmaceutica Nv | Disubstituted octahydropyrrolo [3,4-C] pyrroles as orexin receptor modulators |
| AR091273A1 (es) | 2012-06-08 | 2015-01-21 | Biogen Idec Inc | Inhibidores de pirimidinil tirosina quinasa |
| KR101655787B1 (ko) | 2014-05-08 | 2016-09-22 | 대우조선해양 주식회사 | 선박의 하이브리드 공기조화시스템 및 그 방법, 그리고 이를 포함하는 선박 또는 해양구조물 |
| KR20160021679A (ko) | 2014-08-18 | 2016-02-26 | 대우조선해양 주식회사 | 극저온 환경의 장비용 히팅장치 및 방법 그리고 이를 구비하는 선박 |
| CN107108597B (zh) | 2014-10-31 | 2020-04-17 | 英立维尔英国有限公司 | 多巴胺d3受体拮抗剂化合物 |
| IL288321B2 (en) | 2016-03-10 | 2025-08-01 | Janssen Pharmaceutica Nv | Methods of treating depression using orexin-2 receptor antagonists |
| EP3487852A1 (en) | 2016-07-21 | 2019-05-29 | Biogen MA Inc. | Succinate forms and compositions of bruton's tyrosine kinase inhibitors |
| WO2019057123A1 (zh) * | 2017-09-20 | 2019-03-28 | 杭州英创医药科技有限公司 | 作为ido抑制剂和/或ido-hdac双重抑制剂的多环化合物 |
| GB201809295D0 (en) | 2018-06-06 | 2018-07-25 | Institute Of Cancer Res Royal Cancer Hospital | Lox inhibitors |
| CR20210240A (es) | 2018-11-14 | 2021-06-08 | Janssen Pharmaceutica Nv | Métodos sintéticos mejorados para elaborar compuestos heterocíclicos fusionados como moduladores del receptor de orexina |
| WO2020239073A1 (zh) * | 2019-05-30 | 2020-12-03 | 中国科学院上海药物研究所 | 一种并环化合物、其制备方法和用途 |
| CN112047878B (zh) * | 2020-10-15 | 2022-04-19 | 郑州猫眼农业科技有限公司 | 4-溴-6-氯吡啶-2-羧酸的制备方法 |
| WO2024189472A1 (en) | 2023-03-14 | 2024-09-19 | Janssen Pharmaceutica Nv | Improved synthetic methods of making substituted pyrimidine intermediates for synthesis of orexin receptor modulators |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59009705D1 (de) * | 1989-04-17 | 1995-11-02 | Bayer Ag | Verfahren zur Herstellung von 2,7-Diazabicyclo(3.3.0)octanen. |
| NL9201810A (nl) | 1992-10-19 | 1994-05-16 | Dsm Nv | Werkwijze voor de omzetting van een olefine of een olefinemengsel. |
| NO301165B1 (no) | 1992-12-25 | 1997-09-22 | Daiichi Seiyaku Co | Bicykliske aminderivater og antibakterielle midler inneholdende disse |
| US5817679A (en) * | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| US5478939A (en) * | 1994-07-20 | 1995-12-26 | American Cyanamid Company | (R,R) and (S,S) 2,5-diazabicyclo [2,2,1]heptane derivatives |
| US5472958A (en) | 1994-08-29 | 1995-12-05 | Abbott Laboratories | 2-((nitro)phenoxymethyl) heterocyclic compounds that enhance cognitive function |
| US5585388A (en) | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
| WO1997005139A1 (en) * | 1995-07-28 | 1997-02-13 | Abbott Laboratories | Furopyridine, thienopyridine, pyrrolopyridine and related pyrimidine, pyridazine and triazine compounds useful in controlling chemical synaptic transmission |
| GB9519558D0 (en) * | 1995-09-26 | 1995-11-29 | Merck Sharp & Dohme | Therapeutic agents |
| JPH09172344A (ja) | 1995-12-19 | 1997-06-30 | Murata Mfg Co Ltd | 圧電共振子 |
| US5733912A (en) | 1997-02-19 | 1998-03-31 | Abbott Laboratories | 7A-heterocycle substituted hexahydro-1H-pyrrolizine compounds useful in controlling chemical synaptic transmission |
| KR100589872B1 (ko) * | 1997-05-30 | 2006-06-15 | 뉴로서치 에이/에스 | 8-아자비사이클로(3,2,1)옥트-2-엔 유도체 및 이의 제조방법 |
| JP2002502383A (ja) * | 1997-05-30 | 2002-01-22 | ニューロサーアチ・アクティーゼルスカブ | ニコチンＡＣｈレセプターに於けるコリン作動性リガンドとしての９−アザビシクロ（３．３．１）ノン−２−エン及びノナン誘導体 |
| GB9722343D0 (en) * | 1997-10-22 | 1997-12-17 | British Telecomm | Distributed virtual environment |
| PL203140B1 (pl) * | 1997-10-27 | 2009-08-31 | Neurosearch As | Pochodna homopiperazyny, kompozycja farmaceutyczna zawierająca te pochodne i zastosowanie tej pochodnej |
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| DK1068208T3 (da) * | 1998-04-02 | 2003-09-01 | Targacept Inc | Azatricyclo[3.3.1.1]dekanderivater og farmaceutiske sammensætninger, der indeholder dem |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| JP2000026408A (ja) | 1998-07-02 | 2000-01-25 | Dai Ichi Seiyaku Co Ltd | 対掌体的に純粋なピロリジン誘導体、その塩、それらの製造方法 |
| US6804251B1 (en) | 1998-11-12 | 2004-10-12 | Broadcom Corporation | System and method for multiplexing data from multiple sources |
| FR2786769B1 (fr) * | 1998-12-04 | 2002-10-25 | Synthelabo | Derives de 2,5-diazabicyclo[2.2.1]heptane, leur preparation et leur application en therapeutique |
| ES2209825T3 (es) * | 1999-01-29 | 2004-07-01 | Abbott Laboratories | Derivados diazabiciclicos utiles como ligandos del receptor nicotinico de la acetilcolina. |
| EP1177196B1 (en) * | 1999-05-04 | 2004-03-10 | Neurosearch A/S | Heteroaryl diazabicycloalkanes, their preparation and use |
| DK1178982T3 (da) * | 1999-05-21 | 2004-11-08 | Abbott Lab | Heterocykliske, substituerede aminoazacykliske forbindelser, der er nyttige som midler til centralnervesystemet |
| ATE289607T1 (de) * | 1999-12-14 | 2005-03-15 | Neurosearch As | Neue heteroaryl-diazabizykloalkane |
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