NO331556B1 - Aza-bicykloalkylderivater, en farmasoytisk sammensetning inneholdende nevnte derivater, samt anvendelse derav i terapi - Google Patents
Aza-bicykloalkylderivater, en farmasoytisk sammensetning inneholdende nevnte derivater, samt anvendelse derav i terapi Download PDFInfo
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- NO331556B1 NO331556B1 NO20051626A NO20051626A NO331556B1 NO 331556 B1 NO331556 B1 NO 331556B1 NO 20051626 A NO20051626 A NO 20051626A NO 20051626 A NO20051626 A NO 20051626A NO 331556 B1 NO331556 B1 NO 331556B1
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- Norway
- Prior art keywords
- aza
- yloxy
- bicyclo
- octane
- phenyl
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GB0220581A GB0220581D0 (en) | 2002-09-04 | 2002-09-04 | Organic Compound |
PCT/EP2003/009772 WO2004022556A1 (en) | 2002-09-04 | 2003-09-03 | Aza-bicycloalkyl ethers and their use as alpha7-nachr agonist |
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EP (3) | EP1537104B1 (uk) |
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EC (1) | ECSP055621A (uk) |
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GB (1) | GB0220581D0 (uk) |
HK (2) | HK1077822A1 (uk) |
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SI (1) | SI1537104T1 (uk) |
WO (1) | WO2004022556A1 (uk) |
ZA (1) | ZA200500816B (uk) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS6262265A (ja) * | 1985-09-13 | 1987-03-18 | Hitachi Ltd | 復水器自動検査補修システム |
DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
DE602004031124D1 (de) | 2003-08-13 | 2011-03-03 | Neurosearch As | Neue chinuklidinderivative und deren pharmazeutische verwendung |
US7655657B2 (en) | 2003-12-22 | 2010-02-02 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
EP1824848A1 (en) * | 2004-12-10 | 2007-08-29 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US7160876B2 (en) * | 2003-12-22 | 2007-01-09 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US7309699B2 (en) | 2003-12-22 | 2007-12-18 | Abbott Laboratories | 3-Quinuclidinyl amino-substituted biaryl derivatives |
US20050245531A1 (en) * | 2003-12-22 | 2005-11-03 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US20050137203A1 (en) * | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-quinuclidinyl amino-substituted biaryl derivatives |
US7241773B2 (en) | 2003-12-22 | 2007-07-10 | Abbott Laboratories | 3-quinuclidinyl heteroatom bridged biaryl derivatives |
US20050137217A1 (en) * | 2003-12-22 | 2005-06-23 | Jianguo Ji | Spirocyclic quinuclidinic ether derivatives |
US20050137398A1 (en) * | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-Quinuclidinyl heteroatom bridged biaryl derivatives |
AR049401A1 (es) | 2004-06-18 | 2006-07-26 | Novartis Ag | Aza-biciclononanos |
GB0415746D0 (en) * | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
CA2580856A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
JP5149009B2 (ja) * | 2004-09-20 | 2013-02-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−CoAデサチュラーゼを阻害するためのピリダジン誘導体 |
GB0424564D0 (en) | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
CA2618646A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
GB0521508D0 (en) * | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
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GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
US7855208B2 (en) | 2006-02-14 | 2010-12-21 | Neurosearch A/S | 3, 9-diazabicyclo(3.3.1)non-3-yl-aryl methanone derivatives as nicotinic acetylcholine receptor agonists |
DE602007004307D1 (de) * | 2006-02-16 | 2010-03-04 | Neurosearch As | Enantiomerenreine chinuclidinyloxy-pyridazine und ihre verwendung als nikotin-acetylcholin-rezeptorliganden |
AU2007286807B2 (en) | 2006-08-21 | 2013-03-21 | Genentech, Inc. | Aza-benzothiophenyl compounds and methods of use |
RU2476220C2 (ru) * | 2007-08-02 | 2013-02-27 | Таргасепт, Инк. | (2s,3r)-n-(2-((3-пиридинил)метил)-1-азабицикло[2.2.2]окт-3-ил)бензофуран-2-карбоксамид, новые солевые формы и способы их применения |
US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
MX2010014559A (es) | 2008-07-01 | 2011-03-04 | Genentech Inc | Heterociclos bicíclicos sustituidos y metodos de uso. |
AU2009266953A1 (en) | 2008-07-01 | 2010-01-07 | Genentech, Inc. | Isoindolone derivatives as MEK kinase inhibitors and methods of use |
SG10201504102QA (en) | 2008-11-19 | 2015-06-29 | Forum Pharmaceuticals Inc | Treatment of cognitive disorders with (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
CN102802620A (zh) * | 2009-05-11 | 2012-11-28 | 英维沃医药有限公司 | 使用某种α-7烟酸受体与乙酰胆碱酯酶抑制剂结合治疗认知障碍 |
US20120157464A1 (en) * | 2009-07-23 | 2012-06-21 | Novartis Ag | Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives for the treatment or prevention of ataxia |
TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α7活化劑之用途 |
RU2012119488A (ru) | 2009-10-13 | 2013-11-20 | Мсд Осс Б.В. | Конденсированные азиновые производные для лечения заболеваний, связанных с ацетилхолиновым рецептором |
SG185594A1 (en) | 2010-05-17 | 2012-12-28 | Envivo Pharmaceuticals Inc | A crystalline form of (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
MX2013008704A (es) * | 2011-01-27 | 2013-08-21 | Novartis Ag | Uso de activadores del receptor de acetil-colina nicotinico alfa-7. |
KR20140018286A (ko) | 2011-03-18 | 2014-02-12 | 노파르티스 아게 | 파킨슨병에서의 도파민 유발 이상운동증에서 사용하기 위한 알파 7 니코틴성 아세틸콜린 수용체 활성화제 및 mGluR5 길항제의 조합물 |
TWI589576B (zh) * | 2011-07-15 | 2017-07-01 | 諾華公司 | 氮雜-雙環二芳基醚之鹽類及製造彼等或其前驅物之方法 |
JP6162705B2 (ja) * | 2011-10-20 | 2017-07-12 | ノバルティス アーゲー | アルファ7ニコチン性アセチルコリン受容体活性化剤による処置に対する応答性を予測するバイオマーカー |
EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
AU2013356914B2 (en) * | 2012-12-11 | 2017-01-05 | Novartis Ag | Biomarker predictive of responsiveness to alpha 7 nicotinic acetylcholine receptor activator treatment |
EP2742940B1 (en) * | 2012-12-13 | 2017-07-26 | IP Gesellschaft für Management mbH | Fumarate salt of (R)-3-(6-(4-methylphenyl)-pyridin-3-yloxy)-l-aza-bicyclo-[2.2.2]octane for adminstration once daily, twice daily or thrice daily |
KR101879920B1 (ko) * | 2013-01-15 | 2018-07-18 | 노파르티스 아게 | 알파 7 니코틴성 아세틸콜린 수용체 작용물질의 용도 |
US20150313884A1 (en) * | 2013-01-15 | 2015-11-05 | Novartis Ag | Use of alpha 7 nicotinic acetylcholine receptor agonists |
EP2945626B1 (en) * | 2013-01-15 | 2018-09-12 | Novartis AG | Use of alpha 7 nicotinic receptor agonists for the treatment of narcolepsy |
BR112015016992A8 (pt) * | 2013-01-15 | 2018-01-23 | Novartis Ag | uso de agonistas do receptor alfa 7 nicotínico de acetilcolina |
GB201301626D0 (en) | 2013-01-30 | 2013-03-13 | Dignity Sciences Ltd | Composition comprising 15-OHEPA and methods of using the same |
EP4251158A1 (en) | 2020-11-25 | 2023-10-04 | Vanda Pharmaceuticals Inc. | Treatment of public speaking anxiety with an alpha-7 nicotinic acetylcholine receptor agonist |
WO2023213740A1 (en) * | 2022-05-05 | 2023-11-09 | Philip Morris Products S.A. | Nicotinic acetylcholine receptor ligands |
Family Cites Families (96)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB809574A (en) | 1956-01-26 | 1959-02-25 | Gasaccumulator Svenska Ab | Improvements in or relating to electrical signal light systems |
US3539573A (en) | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
BE759371A (fr) | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
DE2139107A1 (de) | 1971-08-04 | 1973-02-15 | Merck Patent Gmbh | Heterocyclisch substituierte adenosinverbindungen |
ZA848275B (en) | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
US4605652A (en) | 1985-02-04 | 1986-08-12 | A. H. Robins Company, Inc. | Method of enhancing memory or correcting memory deficiency with arylamido (and arylthioamido)-azabicycloalkanes |
EP0247266B1 (en) | 1986-01-07 | 1993-03-10 | Beecham Group Plc | Indole derivatives having an azabicyclic side chain, process for their preparation, intermediates, and pharmaceutical compositions |
KR880007433A (ko) | 1986-12-22 | 1988-08-27 | 메리 앤 터커 | 3-아릴옥시-3-치환된 프로판아민 |
ATE133415T1 (de) | 1987-04-15 | 1996-02-15 | Beecham Group Plc | Am brückenkopf substituierte azabicyclenderivate |
GB8718445D0 (en) | 1987-08-04 | 1987-09-09 | Wyeth John & Brother Ltd | Pyridyl-ethers |
CA1307790C (en) | 1987-08-04 | 1992-09-22 | Ian Anthony Cliffe | Ethers |
US5006528A (en) | 1988-10-31 | 1991-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
DE8817121U1 (de) | 1988-11-22 | 1993-02-04 | Boehringer Ingelheim Kg, 55218 Ingelheim | Neue Quinuclidine |
GB8829079D0 (en) | 1988-12-13 | 1989-01-25 | Beecham Group Plc | Novel compounds |
CA2002182C (en) | 1989-11-03 | 2000-06-13 | Richard J. Wurtman | Compositions for treating the premenstrual or late luteal phase syndrome and methods for their use |
DE4116582A1 (de) | 1990-05-19 | 1991-11-21 | Boehringer Ingelheim Kg | Bicyclische 1-aza-cycloalkane |
YU84791A (sh) | 1990-05-19 | 1994-06-10 | Boehringer Ingelheim Kg. | Biciklicni 1-aza-cikloalkalni |
AU8405991A (en) | 1990-08-31 | 1992-03-30 | Nippon Shinyaku Co. Ltd. | Pyrimidine derivative and medicine |
JP3087763B2 (ja) | 1990-11-30 | 2000-09-11 | 三井化学株式会社 | 新規な複素環式化合物およびそれを含有する医薬組成物 |
US5260303A (en) | 1991-03-07 | 1993-11-09 | G. D. Searle & Co. | Imidazopyridines as serotonergic 5-HT3 antagonists |
AU1752792A (en) | 1991-03-08 | 1992-10-06 | Rhone-Poulenc Rorer International (Holdings) Inc. | Multicyclic tertiary amine polyaromatic squalene synthetase inhibitors |
US5385912A (en) * | 1991-03-08 | 1995-01-31 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Multicyclic tertiary amine polyaromatic squalene synthase inhibitors |
JPH05310732A (ja) | 1992-03-12 | 1993-11-22 | Mitsubishi Kasei Corp | シンノリン−3−カルボン酸誘導体 |
US5612352A (en) * | 1992-04-10 | 1997-03-18 | Zeneca Limited | Heterocyclic compounds |
IL107184A (en) | 1992-10-09 | 1997-08-14 | Abbott Lab | Heterocyclic ether compounds that enhance cognitive function |
AU7394394A (en) | 1992-10-13 | 1995-12-05 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | 3-hydroxyquinuclidin-3-ylphenylquinolines as squalene synthase inhibitors |
WO1994018201A1 (en) | 1993-02-12 | 1994-08-18 | Sankyo Company, Limited | Isoxazoleoxy derivative |
JPH06293768A (ja) | 1993-02-12 | 1994-10-21 | Sankyo Co Ltd | イソオキサゾールオキシ誘導体 |
JP3235913B2 (ja) | 1993-07-30 | 2001-12-04 | エーザイ株式会社 | アミノ安息香酸誘導体 |
JP4208267B2 (ja) | 1993-07-30 | 2009-01-14 | キヤノン株式会社 | 制御装置 |
US5998404A (en) | 1994-10-24 | 1999-12-07 | Eli Lilly And Company | Heterocyclic compounds and their use |
EP0853621A1 (en) | 1995-09-22 | 1998-07-22 | Novo Nordisk A/S | Novel substituted azacyclic or azabicyclic compounds |
SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
ZA984637B (en) | 1997-05-30 | 1998-12-21 | Neurosearch As | Spiro-quinuclidine derivatives their preparation and use |
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 |
US6432975B1 (en) | 1998-12-11 | 2002-08-13 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
SE9900100D0 (sv) | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
EP1202736B1 (en) | 1999-07-28 | 2008-09-17 | The Board Of Trustees Of The Leland Stanford Junior University | Nicotine in therapeutic angiogenesis and vasculogenesis |
SE9903760D0 (sv) | 1999-10-18 | 1999-10-18 | Astra Ab | New compounds |
SE9904176D0 (sv) | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
SE0000540D0 (sv) * | 2000-02-18 | 2000-02-18 | Astrazeneca Ab | New compounds |
WO2001066546A1 (fr) | 2000-03-09 | 2001-09-13 | Mitsubishi Pharma Corporation | Composes spiro, leur procede de preparation et leur utilisation comme medicaments |
GB0010955D0 (en) | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
JP4616971B2 (ja) | 2000-07-18 | 2011-01-19 | 田辺三菱製薬株式会社 | 1−アザビシクロアルカン化合物およびその医薬用途 |
EP1381603A2 (en) | 2000-08-18 | 2004-01-21 | PHARMACIA & UPJOHN COMPANY | Quinuclidine-substituedaryl moieties for treatment of disease ( nicotinic acetylcholine receptor ligands ) |
AU2001284646A1 (en) | 2000-08-21 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
GB0021885D0 (en) | 2000-09-06 | 2000-10-18 | Fujisawa Pharmaceutical Co | New use |
PE20021019A1 (es) | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
EP1438308A1 (en) | 2001-10-26 | 2004-07-21 | PHARMACIA & UPJOHN COMPANY | N-azabicyclo-substituted hetero-bicyclic carboxamides as nachr agonists |
DE10156719A1 (de) | 2001-11-19 | 2003-05-28 | Bayer Ag | Heteroarylcarbonsäureamide |
DE10162375A1 (de) | 2001-12-19 | 2003-07-10 | Bayer Ag | Bicyclische N-Aryl-amide |
AU2003214936A1 (en) | 2002-02-20 | 2003-09-09 | Pharmacia And Upjohn Company | Azabicyclic compounds with alfa7 nicotinic acetylcholine receptor activity |
DE10211415A1 (de) | 2002-03-15 | 2003-09-25 | Bayer Ag | Bicyclische N-Biarylamide |
DE10211416A1 (de) | 2002-03-15 | 2003-09-25 | Bayer Ag | Essig- und Propionsäureamide |
DE10234424A1 (de) | 2002-07-29 | 2004-02-12 | Bayer Ag | Benzothiophen-, Benzofuran- und Indolharnstoffe |
PL375533A1 (en) * | 2002-08-14 | 2005-11-28 | Neurosearch A/S | Novel quinuclidine derivatives and their use |
GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
JP4890762B2 (ja) | 2002-09-25 | 2012-03-07 | メモリー・ファーマシューティカルズ・コーポレイション | インダゾール、ベンゾチアゾール、及びベンゾイソチアゾール、並びにそれらの調製及び使用 |
AU2003284898A1 (en) | 2002-10-29 | 2004-05-25 | Micro, Inc. | Combinative nicotinic/d1 agonism therapy for the treatment of alzheimer's disease |
AU2003269413A1 (en) | 2002-11-01 | 2004-05-25 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
EP1562959A2 (en) | 2002-11-01 | 2005-08-17 | Pharmacia & Upjohn Company LLC | Compounds having both alpha7 nachr agonist and 5ht antagonist activity for treatment of cns diseases |
DE60309740T2 (de) | 2002-11-11 | 2007-03-29 | Neurosearch A/S | 1,4-dizabicyclo(3,2,2)nonane derivative, verfahren zu ihrer herstellung und therapeutical verwendung |
MXPA05005666A (es) | 2002-12-11 | 2005-07-26 | Pharmacia & Upjohn Co Llc | Tratamiento de enfermedades con combinaciones de agonistas del receptor nicotinico de acetilcolina alfa-7 y otros compuestos. |
CA2513433A1 (en) | 2003-01-22 | 2004-08-05 | Pharmacia & Upjohn Company Llc | Treatment of diseases with alpha-7 nach receptor full agonists |
WO2005013910A2 (en) | 2003-08-07 | 2005-02-17 | University Of South Florida | Cholinergic modulation of microglial activation via alpha-7 nicotinic receptors |
JP4226981B2 (ja) | 2003-09-24 | 2009-02-18 | 三井金属鉱業株式会社 | プリント配線板の製造方法及びその製造方法で得られたプリント配線板 |
EP1824848A1 (en) | 2004-12-10 | 2007-08-29 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US20050137203A1 (en) | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-quinuclidinyl amino-substituted biaryl derivatives |
US7160876B2 (en) | 2003-12-22 | 2007-01-09 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US20050245531A1 (en) | 2003-12-22 | 2005-11-03 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US20050137398A1 (en) | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-Quinuclidinyl heteroatom bridged biaryl derivatives |
US20070060588A1 (en) | 2003-12-22 | 2007-03-15 | Jianguo Ji | Fused bicycloheterocycle substituted quinuclidine derivatives |
US7241773B2 (en) | 2003-12-22 | 2007-07-10 | Abbott Laboratories | 3-quinuclidinyl heteroatom bridged biaryl derivatives |
US7655657B2 (en) | 2003-12-22 | 2010-02-02 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
US20050137204A1 (en) | 2003-12-22 | 2005-06-23 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
JP2007516275A (ja) | 2003-12-23 | 2007-06-21 | ファイザー・プロダクツ・インク | 認知増強および精神病性障害のための治療的組合せ |
US7875624B2 (en) | 2004-02-20 | 2011-01-25 | Novartis Vaccines And Diagnostics, Inc. | Modulating and measuring cellular adhesion |
AU2005233642A1 (en) | 2004-04-13 | 2005-10-27 | Astellas Pharma Inc. | Polycyclic pyridines as potassium ion channel modulators |
JP2007538046A (ja) | 2004-05-19 | 2007-12-27 | ノイロサーチ アクティーゼルスカブ | 新規なアザビシクロアリール誘導体 |
AR049401A1 (es) | 2004-06-18 | 2006-07-26 | Novartis Ag | Aza-biciclononanos |
GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
DE602005025902D1 (de) | 2004-10-15 | 2011-02-24 | Neurosearch As | Neue azabizyklische arylderivate und medizinische verwendung damit |
GB0424564D0 (en) | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
EP1866314B1 (en) | 2005-02-16 | 2010-09-15 | NeuroSearch A/S | Novel diazabicyclic aryl derivatives and their medical use |
EP1863485A2 (en) | 2005-03-18 | 2007-12-12 | Abbott Laboratories | Alpha7 neuronal nicotinic receptor ligand and antipsychotic compositions |
CA2606174A1 (en) | 2005-04-18 | 2006-10-26 | Saeed R. Khan | Design and synthesis of novel tubulin polymerization inhibitors: benzoylphenylurea (bpu) sulfur analogs |
FR2884822B1 (fr) | 2005-04-22 | 2007-06-29 | Aventis Pharma Sa | Derives de triazines, leur preparation et leur application en therapeutique |
GB0508314D0 (en) | 2005-04-25 | 2005-06-01 | Novartis Ag | Organic compounds |
CN101228163A (zh) | 2005-06-14 | 2008-07-23 | 先灵公司 | 天冬氨酰蛋白酶抑制剂 |
GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
GB0525672D0 (en) * | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
TW200813067A (en) | 2006-05-17 | 2008-03-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
JP5310732B2 (ja) | 2008-10-17 | 2013-10-09 | Nokクリューバー株式会社 | 潤滑グリース組成物およびその製造法 |
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