NO314580B1 - 4-substituerte piperidinanaloger, farmasöytisk preparat og deres anvendelsefor fremstilling av et medikament for behandling av sykdommer somreagerer på selektiv blokade av N-metyl-D-aspartatreseptorsubtyper - Google Patents
4-substituerte piperidinanaloger, farmasöytisk preparat og deres anvendelsefor fremstilling av et medikament for behandling av sykdommer somreagerer på selektiv blokade av N-metyl-D-aspartatreseptorsubtyper Download PDFInfo
- Publication number
- NO314580B1 NO314580B1 NO19982870A NO982870A NO314580B1 NO 314580 B1 NO314580 B1 NO 314580B1 NO 19982870 A NO19982870 A NO 19982870A NO 982870 A NO982870 A NO 982870A NO 314580 B1 NO314580 B1 NO 314580B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- hydroxy
- piperidine
- alkyl
- pharmaceutically acceptable
- Prior art date
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- C—CHEMISTRY; METALLURGY
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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PCT/US1996/020872 WO1997023216A1 (en) | 1995-12-22 | 1996-12-20 | 4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
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TW498067B (en) * | 1996-07-19 | 2002-08-11 | Hoffmann La Roche | 4-hydroxy-piperidine derivatives |
US5972958A (en) * | 1997-02-18 | 1999-10-26 | American Home Products Corporation | 4-aminoalkoxy-1,3-dihydro-benzoimidazol-2-thiones |
AU746717B2 (en) * | 1997-02-18 | 2002-05-02 | Wyeth | 4-aminoalkoxy-1H-benzimidazole derivatives, their preparation and their use as dopamine autoreceptor (D2) agonists |
US6127380A (en) * | 1997-02-18 | 2000-10-03 | American Home Products Corporation | 4-aminoalkoxy-1H-benzoimidazoles |
IL131157A0 (en) * | 1997-02-18 | 2001-01-28 | American Home Prod | 4-Aminoalkoxy-1,3-dihydrobenzoimidazol-2-thione derivatives their preparation and their use as dopamine autoreceptor (d2) agonists |
US5922715A (en) * | 1997-02-18 | 1999-07-13 | American Home Products Corporation | 5-aminoalkoxy-1, 4-dihydroquinoxaline-2, 3-diones |
CN1248249A (zh) * | 1997-02-18 | 2000-03-22 | 美国家用产品公司 | 多巴胺激动剂5-氨基烷氧基-1,4-二氢喹喔啉-2,3-二酮类化合物 |
EP0905121B1 (de) * | 1997-09-24 | 2002-07-03 | Infineon Technologies AG | o-Nitro(thio)phenolderivate und deren Herstellung |
WO1999021539A1 (en) * | 1997-10-24 | 1999-05-06 | Warner-Lambert Company | Method for treating disease-related or drug-induced dyskinesias |
DE69830045T2 (de) * | 1997-10-31 | 2006-01-12 | Daiichi Suntory Pharma Co., Ltd. | Arylpiperidinopropanol und Arylpiperazinopropanol Derivate und dieselbe ent- haltende Pharmazeutika |
PT1049689E (pt) * | 1998-01-19 | 2002-09-30 | Pfizer | Compostos de 4-(2-ceto-1-benzimidazolinil)piperidina como agonistas do receptor orl1 |
AU1600599A (en) | 1998-02-27 | 1999-09-15 | Warner-Lambert Company | Heterocyclic substituted aniline calcium channel blockers |
US6166052A (en) | 1998-03-11 | 2000-12-26 | Warner-Lambert Company | Heteroaryl alkyl alpha substituted peptidylamine calcium channel blockers |
DE19812331A1 (de) | 1998-03-20 | 1999-09-23 | Merck Patent Gmbh | Piperidinderivate |
EP1077973A2 (en) * | 1998-05-14 | 2001-02-28 | Egis Gyogyszergyar Rt. | Benzofuran derivatives, pharmaceutical composition containing the same, and a process for the preparation of the active ingredient |
PE20000728A1 (es) | 1998-06-26 | 2000-08-21 | Cocensys Inc | Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda |
FR2787028B1 (fr) * | 1998-12-15 | 2002-10-18 | Aventis Pharma Sa | Utilisation du riluzole dans le traitement des traumatismes acoustiques |
AU5319700A (en) | 1999-06-02 | 2000-12-18 | S. Mbua Ngale Efange | Nicotine receptor ligands |
TWI254043B (en) | 1999-06-08 | 2006-05-01 | Hoffmann La Roche | Ethanesulfonyl-piperidine derivatives having good affinity to N-methyl-D-aspartate (NMDA) receptor |
AU5877500A (en) * | 1999-06-15 | 2001-01-02 | Neurogen Corporation | Piperidinyl and piperazinyl substituted benzofused lactams |
US6156758A (en) * | 1999-09-08 | 2000-12-05 | Isis Pharmaceuticals, Inc. | Antibacterial quinazoline compounds |
JP2003512422A (ja) * | 1999-10-29 | 2003-04-02 | メルク シャープ エンド ドーム リミテッド | ベンズイミダゾールnmda/nr2bアンタゴニストを使用する疼痛の治療方法 |
USRE46117E1 (en) | 1999-12-22 | 2016-08-23 | Teva Pharmaceuticals International Gmbh | Modulators of dopamine neurotransmission |
US6432985B2 (en) * | 2000-04-25 | 2002-08-13 | Hoffmann-La Roche Inc. | Neuroprotective substituted piperidine compounds with activity as NMDA NR2B subtype selective antagonists |
ES2291329T3 (es) | 2000-07-18 | 2008-03-01 | Dainippon Sumitomo Pharma Co., Ltd. | Inhibidores de la recaptacion de serotonina. |
AU9087301A (en) * | 2000-09-11 | 2002-03-26 | Sepracor Inc | Ligands for monoamine receptors and transporters, and methods of use thereof |
US7294637B2 (en) * | 2000-09-11 | 2007-11-13 | Sepracor, Inc. | Method of treating addiction or dependence using a ligand for a monamine receptor or transporter |
ZA200108038B (en) * | 2000-10-02 | 2003-04-01 | Pfizer Prod Inc | Prophylactic use of n-methyl-d-asparrate (NMDA) antagonists. |
IL145584A0 (en) | 2000-10-02 | 2002-06-30 | Pfizer Prod Inc | Nmda nr2b antagonists for treatment |
EP1674087A1 (en) | 2000-10-02 | 2006-06-28 | Pfizer Products Inc. | Prophylactic use of n-methyl-d-aspartate (NMDA) antagonists |
AUPR213700A0 (en) | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
CA2436699A1 (en) | 2000-12-21 | 2002-06-27 | Warner-Lambert Company Llc | Piperidine derivatives as subtype selective n-methyl-d-aspartate antagonists |
KR100849839B1 (ko) † | 2001-02-23 | 2008-08-01 | 머크 앤드 캄파니 인코포레이티드 | N-치환된 비-아릴-헤테로사이클릭 nmda/nr2b 길항제 및 이를 포함하는 약제학적 조성물 |
SI1598339T1 (sl) * | 2001-04-18 | 2009-12-31 | Euro Celtique Sa | Derivati 1-(4-amino.cikloheksil)-1,3-dihidro-2h-benzimidazol-2-ona in sorodne spojine kot nociceptinski analogi in ORL1 ligandi za zdravljenje bolečine |
EP1409477B1 (en) * | 2001-07-24 | 2008-09-17 | Richter Gedeon NYRT | Piperidine derivatives as nmda receptor antagonists |
DE10153346A1 (de) | 2001-10-29 | 2004-04-22 | Grünenthal GmbH | Substituierte Indole |
KR100579352B1 (ko) | 2001-11-30 | 2006-05-12 | 에프. 호프만-라 로슈 아게 | Ccr-3 수용체 길항제 ⅶ |
GB0130696D0 (en) * | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
EP1467986A1 (en) * | 2002-01-17 | 2004-10-20 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
GB0203778D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
PL212089B1 (pl) | 2002-03-13 | 2012-08-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory deacetylazy histonowej, kompozycja farmaceutyczna je zawierająca, ich zastosowanie, sposób wytwarzania, sposób wykrywania lub identyfikacji HDAC oraz kompozycja |
EA007270B1 (ru) | 2002-03-13 | 2006-08-25 | Янссен Фармацевтика Н.В. | Пиперазинил-, пиперидинил- и морфолинилпроизводные как новые ингибиторы гистондеацетилазы |
OA12789A (en) | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | Carbonylamino-derivatives as novel inhibitors of histone deacetylase. |
JP4725945B2 (ja) | 2002-03-13 | 2011-07-13 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ヒストンデアセチラーゼの新規な阻害剤としてのスルホニルアミノ誘導体 |
JP2005034165A (ja) * | 2002-06-26 | 2005-02-10 | Mu-Hyun Cho | マット一体型のストーンベッド |
US20040082543A1 (en) * | 2002-10-29 | 2004-04-29 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain |
US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
US20070021414A1 (en) * | 2003-10-08 | 2007-01-25 | Pfizer, Inc. | 1-'2-(4-Hydroxyphenyl)-2-hydroxyethyl!-piperidin-4-ol compounds as nmda receptor antagonists |
ES2347152T3 (es) * | 2003-11-26 | 2010-10-26 | Pfizer Products Inc. | Derivados de aminopirazol como inhibidores de gsk-3. |
SE0401465D0 (sv) | 2004-06-08 | 2004-06-08 | Carlsson A Research Ab | New substituted piperdines as modulators of dopamine neurotransmission |
US7763626B2 (en) * | 2004-06-18 | 2010-07-27 | Trustees Of Dartmouth College | Compositions and method for enhancing the therapeutic activity of opiods in treatment of pain |
AU2005263719A1 (en) * | 2004-07-16 | 2006-01-26 | Janssen Pharmaceutica N.V. | Dimeric piperidine derivatives |
DE102004036349A1 (de) * | 2004-07-27 | 2006-03-23 | Grünenthal GmbH | Substituierte 3-Phenylpiperidin-Derivate |
BRPI0512676B8 (pt) | 2004-07-28 | 2021-05-25 | Janssen Pharmaceutica Nv | derivados de indolil alquil amina substituídos como inibidores de histona desacetilase, composição farmacêutica que os compreende, seus processos de preparação e uso |
US20060106064A1 (en) * | 2004-11-03 | 2006-05-18 | University Of North Texas Health Science Center At Fort Worth | Butyrophenones and sigma-1 receptor antagonists protect against oxidative-stress |
DE102004061593A1 (de) * | 2004-12-21 | 2006-06-22 | Abbott Gmbh & Co. Kg | Substituierte N-heterocyclische Verbindungen und ihre therapeutische Verwendung |
WO2006137465A1 (ja) * | 2005-06-24 | 2006-12-28 | Shionogi & Co., Ltd. | 含窒素複素環誘導体 |
NZ567629A (en) | 2005-09-23 | 2011-08-26 | Ms Science Corp | Piperazine derivatives useful in the treatment of discorders of the central nervous system |
CA2630717C (en) | 2006-01-19 | 2015-02-24 | Janssen Pharmaceutica N.V. | Pyridine and pyrimidine derivatives as inhibitors of histone deacetylase |
EP2340835A1 (en) | 2006-01-27 | 2011-07-06 | M's Science Corporation | Piperidine and piperazine derivatives |
EP1878724A1 (en) * | 2006-07-15 | 2008-01-16 | sanofi-aventis | A regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles |
WO2008055945A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases |
WO2008065141A1 (en) | 2006-11-30 | 2008-06-05 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
EP2481408A3 (en) | 2007-03-01 | 2013-01-09 | Probiodrug AG | New use of glutaminyl cyclase inhibitors |
EP2865670B1 (en) | 2007-04-18 | 2017-01-11 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
TWI410420B (zh) * | 2008-02-05 | 2013-10-01 | Dainippon Sumitomo Pharma Co | 苄基哌啶化合物 |
NZ589764A (en) * | 2008-05-09 | 2012-10-26 | Univ Emory | NMDA receptor antagonists for the treatment of neuropsychiatric disorders |
DE102008053240A1 (de) | 2008-10-25 | 2010-04-29 | Saltigo Gmbh | Herstellung von (N-Heterozyklyl)-Arylethern |
WO2011016468A1 (ja) | 2009-08-04 | 2011-02-10 | 大日本住友製薬株式会社 | ベンジルピペリジン化合物 |
US8486940B2 (en) | 2009-09-11 | 2013-07-16 | Probiodrug Ag | Inhibitors |
JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤 |
EP2545047B9 (en) | 2010-03-10 | 2015-06-10 | Probiodrug AG | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
EP2560953B1 (en) | 2010-04-21 | 2016-01-06 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
JP6050264B2 (ja) | 2011-03-16 | 2016-12-21 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
MX2014004469A (es) | 2011-11-22 | 2014-08-01 | Univ California | Metodos y composiciones para tratar inflamacion y lesion isquemica. |
EA027748B1 (ru) | 2012-04-04 | 2017-08-31 | Тева Фармасьютикалз Интернэшнл Гмбх | Применение придопидина в комбинации с тетрабеназином для лечения двигательных нарушений и ожирения |
EP3145505A4 (en) | 2014-05-19 | 2018-02-28 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (naaa) inhibitors and their use thereof |
EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
EP3233077A4 (en) * | 2014-12-19 | 2018-08-08 | The Broad Institute Inc. | Dopamine d2 receptor ligands |
PL3461819T3 (pl) | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
US10689357B2 (en) | 2018-05-08 | 2020-06-23 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and use thereof |
CN113214140B (zh) * | 2020-02-03 | 2022-09-09 | 江苏谛奇医药科技有限公司 | 哌啶酰胺类衍生物、其药物组合物及其应用 |
AU2023235233A1 (en) | 2022-03-14 | 2024-09-12 | Slap Pharmaceuticals Llc | Multicyclic compounds |
Family Cites Families (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA696999A (en) * | 1964-11-03 | Ayerst, Mckenna And Harrison | Therapeutic compounds and their preparation | |
US3255196A (en) * | 1966-06-07 | Phenoxyalkyl piperidine derivatives | ||
US3091616A (en) * | 1963-05-28 | L-ortho-tolyloxyethyl-x-phenylpiperi- | ||
GB1052302A (bg) * | 1963-04-22 | |||
US3225052A (en) * | 1964-05-06 | 1965-12-21 | Janssen Pharmaceutica Nv | Benzimidazolinyl piperidine derivatives |
GB1055548A (en) * | 1965-08-23 | 1967-01-18 | Acraf | New substituted 1-aryl-3-aminopropynes and process for their preparation |
US3632767A (en) * | 1968-02-12 | 1972-01-04 | Mallinckrodt Chemical Works | Treatment of depression with 4-substituted piperidines |
US3686187A (en) * | 1970-05-25 | 1972-08-22 | Abbott Lab | 4-anilino-1-(4-p-fluorophenyl-1-butyl) piperidine compounds |
DE2651574A1 (de) * | 1976-11-12 | 1978-05-18 | Boehringer Mannheim Gmbh | Ein neues aminopropanol-derivat und verfahren zu dessen herstellung |
GB2056435A (en) * | 1979-06-26 | 1981-03-18 | Ciba Geigy Ag | Novel Tetrahydropyridine and Piperidine Substituted Benzofuranes and Related Compounds |
DE3034237A1 (de) * | 1979-09-18 | 1981-04-16 | Otsuka Pharmaceutical Co. Ltd., Tokyo | Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel |
DE2939292A1 (de) * | 1979-09-28 | 1981-04-09 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-phenoxyalkylpiperidin-derivate, verfahrenn zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
US4577020A (en) * | 1983-01-25 | 1986-03-18 | The Upjohn Company | Aminoalkyl and aminoalkenyl triazoles as anti-psychotic agents |
ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
DE3421641A1 (de) * | 1984-06-09 | 1985-12-12 | Merck Patent Gmbh, 6100 Darmstadt | Indolderivate |
JPS61115068A (ja) * | 1984-11-08 | 1986-06-02 | Hokuriku Seiyaku Co Ltd | 4−ベンジルピペリジニルプロポキシアニリン誘導体 |
US4567186A (en) * | 1985-01-14 | 1986-01-28 | Sterling Drug Inc. | 5-Heteryl-1,6-naphthyridin-2(1H)-ones, cardiotonic use thereof and intermediates therefor |
JPH0615529B2 (ja) * | 1985-04-01 | 1994-03-02 | エーザイ株式会社 | 新規ピペリジン誘導体 |
EP0235463A3 (en) * | 1985-12-20 | 1990-01-17 | A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation) | N-substituted-arylalkyl and arylalkylene piperidines as cardiovascular antihistaminic and antisecretory agents |
DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
DE3703435A1 (de) * | 1987-02-05 | 1988-08-18 | Thomae Gmbh Dr K | Neue thiazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
FR2620704B1 (fr) * | 1987-09-17 | 1991-04-26 | Sanofi Sa | Derives de (benzyl-4 piperidino)-1 propanol-2, leur preparation, leur utilisation comme antimicrobiens et les produits les contenant |
JP2779240B2 (ja) * | 1987-12-11 | 1998-07-23 | 三井化学株式会社 | 新規アミン類およびその用途 |
ZA891901B (en) * | 1988-03-17 | 1989-11-29 | Merrell Dow Pharma | Method for the treatment of the extrapyramidal side effects associated with neuroleptic therapy |
FR2640266B2 (fr) * | 1988-07-12 | 1992-07-10 | Synthelabo | Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2, quinoleinones-2, benzo(b)azepinones-2 et benzimidazolones-2, leur preparation et leur application en therapeutique |
US4902695A (en) * | 1989-02-13 | 1990-02-20 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
US5011834A (en) * | 1989-04-14 | 1991-04-30 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | PCP receptor ligands and the use thereof |
ES2098248T3 (es) * | 1989-05-17 | 1997-05-01 | Pfizer | Derivados de 2-piperidino-1-alcanoles como agentes antiisquemicos. |
ZA908641B (en) * | 1989-10-27 | 1992-06-24 | Du Pont | (n-phthalimidoalkyl)piperidines |
US5149817A (en) * | 1990-03-05 | 1992-09-22 | Shionogi & Co., Ltd. | Teirahydropyridine derivatives |
US5169855A (en) * | 1990-03-28 | 1992-12-08 | Du Pont Merck Pharmaceutical Company | Piperidine ether derivatives as psychotropic drugs or plant fungicides |
US5116846A (en) * | 1990-03-28 | 1992-05-26 | Du Pont Merck Pharmaceutical Company | N-aralkyl piperidine derivatives as psychotropic drugs |
DE69132141T2 (de) * | 1990-05-10 | 2000-09-21 | Pfizer Inc., New York | Neuroprotective indolone und verwandte derivate |
JPH04217945A (ja) * | 1990-07-18 | 1992-08-07 | Zeria Pharmaceut Co Ltd | 置換アルキルベンゼン誘導体およびそれを含有する抗潰瘍剤 |
MX9100513A (es) * | 1990-08-06 | 1992-04-01 | Smith Kline French Lab | Compuestos |
FR2668149B1 (fr) * | 1990-10-18 | 1994-09-23 | Synthelabo | Le 1-(3,4-dihydro-2-oxo-1h-quinolein-6-yl)-2-[4-(2-phenyl-ethyl)piperidin-1-yl]ethanol, sa preparation et son application en therapeutique. |
US5273977A (en) * | 1990-11-05 | 1993-12-28 | Warner-Lambert Company | Substituted tetrahydropyridines and hydroxypiperidines as central nervous system agents |
EP0488959A3 (en) * | 1990-11-28 | 1992-08-05 | Sandoz Ltd. | New uses of competitive nmda receptor antagonists |
DE4111861A1 (de) * | 1991-04-11 | 1992-10-15 | Schwabe Willmar Gmbh & Co | Benzopyranone, verfahren zu ihrer herstellung und verwendung |
JPH04312572A (ja) * | 1991-04-12 | 1992-11-04 | Takeda Chem Ind Ltd | 環状アミン化合物 |
US5231099A (en) * | 1991-04-15 | 1993-07-27 | Du Pont Merck Pharmaceutical Company | Use of sigma receptor antagonists to enhance the effects of antipsychotic drugs |
EP0524846A1 (fr) * | 1991-06-27 | 1993-01-27 | Synthelabo | Dérivés de 2-(pipéridin-1-y1) éthanol, leur préparation et leur application en thérapeutique |
WO1993000313A2 (en) * | 1991-06-27 | 1993-01-07 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
CA2113568A1 (en) * | 1991-07-17 | 1993-02-04 | Willard Mckowan Welch Jr. | 2-(4-hydroxypiperidino)-1-alkanol derivatives as antiischemic agents |
FR2681319B1 (fr) * | 1991-09-12 | 1995-02-17 | Synthelabo | Derives de 1-(phenoxyalkyl)piperidine, leur preparation et leur application en therapeutique. |
HU211019B (en) * | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
EP0629190A1 (en) * | 1992-01-28 | 1994-12-21 | Smithkline Beecham Plc | Compounds as calcium channel antagonists |
US5202346A (en) * | 1992-02-25 | 1993-04-13 | American Home Products Corporation | Piperidinyl and piperazinyl derivatives |
ES2060547B1 (es) * | 1992-06-04 | 1995-06-16 | Ferrer Int | Mejoras en el objeto de la patente de invencion n/ 9201158 que se refiere a "procedimiento de obtencion de nuevos derivados de la 4-bencilpiperidina". |
US5192751A (en) * | 1992-07-24 | 1993-03-09 | Eli Lilly And Company | Use of competitive NMDA receptor antagonists in the treatment of urinary incontinence |
EP0666854B1 (en) * | 1992-10-30 | 1997-03-26 | Pfizer Inc. | Neuroprotective 3,4-dihydro-2(1h)-quinolone compounds |
US5364867A (en) * | 1992-11-30 | 1994-11-15 | Sterling Winthrop Inc. | 4-phenylpiperdine agents for treating cns disorders |
US5922773A (en) * | 1992-12-04 | 1999-07-13 | The Children's Medical Center Corp. | Glaucoma treatment |
WO1994018172A1 (en) * | 1993-02-01 | 1994-08-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Imidazolylbenzene compound and use thereof as medicine |
US5352683A (en) * | 1993-03-05 | 1994-10-04 | Virginia Commonwealth University Medical College Of Virginia | Method for the treatment of chronic pain |
TW281670B (bg) * | 1993-09-02 | 1996-07-21 | Hoffmann La Roche | |
DE4335718A1 (de) * | 1993-10-20 | 1995-04-27 | Merck Patent Gmbh | Cyclische Aminderivate |
FR2717810B1 (fr) * | 1994-03-22 | 1996-04-26 | Adir | Nouvelles aminoalkyl benzoxazolinones et benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
DE4410822A1 (de) * | 1994-03-24 | 1995-09-28 | Schering Ag | Neue Piperidin-Derivate |
-
1996
- 1996-12-19 ZA ZA9610745A patent/ZA9610745B/xx unknown
- 1996-12-20 SK SK824-98A patent/SK82498A3/sk unknown
- 1996-12-20 DE DE69634447T patent/DE69634447D1/de not_active Expired - Lifetime
- 1996-12-20 EP EP96945682A patent/EP0869792B1/en not_active Expired - Lifetime
- 1996-12-20 NZ NZ330624A patent/NZ330624A/xx unknown
- 1996-12-20 WO PCT/US1996/020872 patent/WO1997023216A1/en not_active Application Discontinuation
- 1996-12-20 US US09/091,598 patent/US6124323A/en not_active Expired - Fee Related
- 1996-12-20 HU HU9901296A patent/HUP9901296A3/hu unknown
- 1996-12-20 CZ CZ981802A patent/CZ180298A3/cs unknown
- 1996-12-20 AT AT96945682T patent/ATE290380T1/de not_active IP Right Cessation
- 1996-12-20 PL PL96327493A patent/PL327493A1/xx unknown
- 1996-12-20 IL IL12506196A patent/IL125061A/en not_active IP Right Cessation
- 1996-12-20 BR BR9612686A patent/BR9612686A/pt not_active Application Discontinuation
- 1996-12-20 CA CA002240275A patent/CA2240275A1/en not_active Abandoned
- 1996-12-20 AU AU16899/97A patent/AU717185B2/en not_active Ceased
- 1996-12-20 EA EA199800592A patent/EA001323B1/ru not_active IP Right Cessation
-
1998
- 1998-06-19 MX MX9805031A patent/MX9805031A/es not_active IP Right Cessation
- 1998-06-19 NO NO19982870A patent/NO314580B1/no unknown
- 1998-06-19 BG BG102562A patent/BG63380B1/bg unknown
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HUP9901296A3 (en) | 2001-01-29 |
SK82498A3 (en) | 1999-02-11 |
DE69634447D1 (de) | 2005-04-14 |
IL125061A0 (en) | 1999-01-26 |
AU717185B2 (en) | 2000-03-16 |
BR9612686A (pt) | 1999-07-20 |
MX9805031A (es) | 1998-11-30 |
EP0869792A4 (en) | 1999-09-22 |
WO1997023216A1 (en) | 1997-07-03 |
EA001323B1 (ru) | 2001-02-26 |
EA199800592A1 (ru) | 1999-02-25 |
US6124323A (en) | 2000-09-26 |
NO982870L (no) | 1998-08-24 |
BG63380B1 (bg) | 2001-12-29 |
CZ180298A3 (cs) | 1999-01-13 |
PL327493A1 (en) | 1998-12-21 |
HUP9901296A2 (hu) | 1999-08-30 |
CA2240275A1 (en) | 1997-07-03 |
BG102562A (bg) | 1999-04-30 |
EP0869792B1 (en) | 2005-03-09 |
ATE290380T1 (de) | 2005-03-15 |
IL125061A (en) | 2004-05-12 |
EP0869792A2 (en) | 1998-10-14 |
NZ330624A (en) | 2000-03-27 |
AU1689997A (en) | 1997-07-17 |
NO982870D0 (no) | 1998-06-19 |
ZA9610745B (en) | 1997-06-24 |
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