ATE553086T1 - Substituierte heterocyclische verbindungen und deren verwendung zur behandlung der multipler medikamentenresistenz - Google Patents

Substituierte heterocyclische verbindungen und deren verwendung zur behandlung der multipler medikamentenresistenz

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Publication number
ATE553086T1
ATE553086T1 AT01981711T AT01981711T ATE553086T1 AT E553086 T1 ATE553086 T1 AT E553086T1 AT 01981711 T AT01981711 T AT 01981711T AT 01981711 T AT01981711 T AT 01981711T AT E553086 T1 ATE553086 T1 AT E553086T1
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Austria
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substituted heterocyclic
heterocyclic compounds
drug resistance
multiple drug
treating multiple
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AT01981711T
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English (en)
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Charles Degenhardt
David Eickhoff
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H Lee Moffitt Cancer Ct & Res
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    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28Radicals substituted by singly-bound oxygen or sulphur atoms
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AT01981711T 2000-10-17 2001-10-16 Substituierte heterocyclische verbindungen und deren verwendung zur behandlung der multipler medikamentenresistenz ATE553086T1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24112700P 2000-10-17 2000-10-17
US09/740,391 US6693099B2 (en) 2000-10-17 2000-12-19 Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
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Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6376514B1 (en) * 2000-10-17 2002-04-23 The Procter & Gamble Co. Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof
US6693099B2 (en) * 2000-10-17 2004-02-17 The Procter & Gamble Company Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
JP3945985B2 (ja) * 2000-12-28 2007-07-18 株式会社リコー デジタルカメラ装置
US20030211040A1 (en) 2001-08-31 2003-11-13 Paul Greengard Phosphodiesterase activity and regulation of phosphodiesterase 1B-mediated signaling in brain
JP2006510670A (ja) * 2002-12-05 2006-03-30 シーブイ・セラピューティクス・インコーポレイテッド 置換ヘテロ環化合物
JP2006514066A (ja) * 2003-01-03 2006-04-27 シーブイ・セラピューティクス・インコーポレイテッド 置換ヘテロ環化合物
KR100580743B1 (ko) * 2003-10-08 2006-05-15 한미약품 주식회사 다약제 내성 저해 활성을 갖는 신규한 크로몬 유도체 또는이의 약제학적으로 허용가능한 염 및 이들의 제조 방법
JP5084725B2 (ja) 2005-06-06 2012-11-28 武田薬品工業株式会社 有機化合物
US20080194592A1 (en) * 2005-08-23 2008-08-14 Intra-Cellular Therapies, Inc. Organic Compounds
DK2041088T3 (da) 2006-06-28 2014-04-07 Amgen Inc Glycintransporter-1 inhibitorer
EP2081431B1 (de) 2006-11-13 2013-01-16 Intra-Cellular Therapies, Inc. Organische verbindungen
JP5837278B2 (ja) 2006-12-05 2015-12-24 イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. 新規使用
WO2009029206A1 (en) * 2007-08-24 2009-03-05 Wake Forest University Health Sciences Chemotherapeutic for inducing an msh2-dependent apoptotic pathway
GB0813142D0 (en) 2008-07-17 2008-08-27 Glaxo Group Ltd Novel compounds
US11464781B2 (en) 2009-02-25 2022-10-11 Intra-Cellular Therapies, Inc. PDE1 inhibitors for ophthalmic disorders
US8673920B2 (en) 2009-05-06 2014-03-18 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
JP2012526810A (ja) 2009-05-13 2012-11-01 イントラ−セルラー・セラピーズ・インコーポレイテッド 有機化合物
SG10201507362TA (en) 2009-08-05 2015-10-29 Intra Cellular Therapies Inc Novel Regulatory Proteins And Inhibitors
EP2632465B1 (de) 2010-10-27 2015-12-30 Merck Sharp & Dohme Corp. Inhibitoren des renalen kaliumkanals der äusseren medulla
US9056859B2 (en) 2010-10-29 2015-06-16 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
ES2605164T3 (es) 2011-08-19 2017-03-13 Merck Sharp & Dohme Corp. Inhibidores del canal de potasio de la médula renal externa
US9527830B2 (en) 2011-09-16 2016-12-27 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
US8999991B2 (en) 2011-10-25 2015-04-07 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
EP2771005B1 (de) 2011-10-25 2016-05-18 Merck Sharp & Dohme Corp. Inhibitoren des renalen kaliumkanals der äusseren medulla
US9139585B2 (en) 2011-10-31 2015-09-22 Merck Sharp & Dohme Corp. Inhibitors of the Renal Outer Medullary Potassium channel
EP2773206B1 (de) 2011-10-31 2018-02-21 Merck Sharp & Dohme Corp. Inhibitoren des renalen kaliumkanals der äusseren medulla
WO2013066718A2 (en) 2011-10-31 2013-05-10 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
US9206199B2 (en) 2011-12-16 2015-12-08 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
AR092031A1 (es) 2012-07-26 2015-03-18 Merck Sharp & Dohme Inhibidores del canal de potasio medular externo renal
EP2925322B1 (de) 2012-11-29 2018-10-24 Merck Sharp & Dohme Corp. Inhibitoren des renalen kaliumkanals der äusseren medulla
US9573961B2 (en) 2012-12-19 2017-02-21 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
EP2956141A4 (de) 2013-02-17 2016-10-26 Intra Cellular Therapies Inc Neuartige verwendungen
WO2014126944A2 (en) 2013-02-18 2014-08-21 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
EP2968338B1 (de) 2013-03-15 2019-01-09 Intra-Cellular Therapies, Inc. Pde1-inhibitoren zur verwendung bei der behandlung und/oder prävention von zns-verletzungen und pns-krankheiten, störungen oder verletzungen
US9765074B2 (en) 2013-03-15 2017-09-19 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
PL2970279T3 (pl) 2013-03-15 2021-05-31 Intra-Cellular Therapies, Inc. Związki organiczne
WO2015017305A1 (en) 2013-07-31 2015-02-05 Merck Sharp & Dohme Corp Inhibitors of the renal outer medullary potassium channel
DK3157926T3 (da) 2014-06-20 2019-08-19 Intra Cellular Therapies Inc Organiske forbindelser
US10131671B2 (en) 2014-08-07 2018-11-20 Intra-Cellular Therapies, Inc. Organic compounds
US10285992B2 (en) 2014-08-07 2019-05-14 Intra-Cellular Therapies, Inc. Combinations of PDE1 inhibitors and NEP inhibitors and associated methods
RU2711442C2 (ru) 2014-09-17 2020-01-17 Интра-Селлулар Терапиз, Инк. Соединения и способы
US10682354B2 (en) 2016-03-28 2020-06-16 Intra-Cellular Therapies, Inc. Compositions and methods
EP3509589B1 (de) 2016-09-12 2021-11-17 Intra-Cellular Therapies, Inc. Neuartige verwendungen
CN111093662B (zh) 2017-06-20 2023-10-03 安布里亚制药公司 用于提高心脏代谢效率的组合物和方法
US11839614B2 (en) 2018-01-31 2023-12-12 Intra-Cellular Therapies, Inc. Methods for treating or mitigating cardiotoxicity characterized by inhibition of adenosine A2 signaling and/or adenosine A2 receptor expression
WO2020081361A1 (en) 2018-10-17 2020-04-23 Imbria Pharmaceuticals, Inc. Methods of treating rheumatic diseases using trimetazidine-based compounds
EP3976101A4 (de) 2019-05-31 2023-06-21 Imbria Pharmaceuticals, Inc. Verfahren zur behandlung von fibrose unter verwendung von verbindungen zur förderung der glucoseoxidation
JP7612672B2 (ja) 2019-09-03 2025-01-14 イントラ-セルラー・セラピーズ・インコーポレイテッド 新規化合物
US12364695B2 (en) 2020-06-02 2025-07-22 Intra-Cellular Therapies, Inc. Methods of treating inflammatory disease
US11780811B2 (en) 2020-06-30 2023-10-10 Imbria Pharmaceuticals, Inc. Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate
US11530184B2 (en) 2020-06-30 2022-12-20 Imbria Pharmaceuticals, Inc. Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate
US11883396B2 (en) 2021-05-03 2024-01-30 Imbria Pharmaceuticals, Inc. Methods of treating kidney conditions using modified forms of trimetazidine
CN115872859A (zh) * 2021-09-28 2023-03-31 佳化化学(上海)有限公司 一种醇醚羧酸的制备方法

Family Cites Families (191)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE563610R (fr) 1957-12-30 1960-06-17 Morren H Derives du 2-propanol.
US4029801A (en) * 1970-09-03 1977-06-14 John Wyeth & Brother Limited Pharmaceutical compositions and methods of treating hypertension
FR2267104A1 (en) * 1974-04-12 1975-11-07 Ferlux Labo Sa Hypotensive and antiarrhythmic piperazines - 1-(3-phenoxy-2-hydroxy propyl)-4-substd. piperazines
PT66682B (pt) * 1976-06-18 1978-11-15 Ind Biolog Francaise /(quinolyl-4)-propyl-1/-4 piperidines leur preparation et leur utilisation comme medicaments /(quinolyl-4)-propyl/-4 piperidines leur preparation et leur utilisation comme medicaments
GB1583811A (en) * 1977-05-09 1981-02-04 Laroche Navarron Sa Chromene derivatives
NL7908031A (nl) * 1979-11-01 1981-06-01 Acf Chemiefarma Nv Nieuwe chinolinederivaten en farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werk- wijze voor het bereiden van deze verbindingen.
FR2471981A1 (fr) * 1979-12-21 1981-06-26 Pharmindustrie Nouveaux derives de la (piperidyl-4)-2 (quinolyl-4)-1 ethanone, produits intermediaires et procedes pour leur preparation, et leur utilisation comme medicaments
US4806552A (en) * 1980-03-01 1989-02-21 John Wyeth & Brother, Limited Pyridyl- and/or pyridoyl-(piperid-4-yl) ureas and analogues thereof
US4442107A (en) * 1980-03-06 1984-04-10 Acf Chemiefarma N.V. Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods for treating cardiovascular conditions with them
US4443453A (en) * 1980-03-06 1984-04-17 Acf Chemiefarma N.V. Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods for treating cardiovascular conditions with them
IL62240A0 (en) * 1980-03-06 1981-05-20 Acf Chemiefarma Nv Novel quinoline derivatives,pharmaceutical compositions containing such compounds,and methods for the preparation of these compounds
FR2485014A1 (fr) * 1980-06-20 1981-12-24 Pharmindustrie Nouveaux derives de (quinolyl-2, -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments
FR2495470A1 (fr) * 1980-12-05 1982-06-11 Pharmindustrie Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol
US4962115A (en) * 1981-10-01 1990-10-09 Janssen Pharmaceutica N.V. Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives
US4567264A (en) * 1983-05-18 1986-01-28 Syntex (U.S.A.) Inc. Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
FR2552083B1 (fr) * 1983-09-15 1986-05-09 Cerm Cent Europ Rech Mauvernay Derives de (alkynyloxy-3 hydroxy-2-propyl)-4 piperazinyl-1 n-phenyl acetamide, leur preparation et leur application en therapeutique
US4584303A (en) * 1984-04-09 1986-04-22 The Boc Group, Inc. N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds
GB2163150B (en) 1984-07-19 1988-05-25 Sandoz Ltd 3-aminopropoxyaryl derivatives
DE3524955A1 (de) 1984-07-19 1986-01-30 Sandoz-Patent-GmbH, 7850 Lörrach 3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel
US4911923A (en) * 1985-06-27 1990-03-27 Conoco Inc. Biocide for petroleum operations
DE3614363A1 (de) * 1986-04-28 1987-10-29 Hoechst Ag Benzothiazinon-derivate, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und deren verwendung
US4963553A (en) * 1986-10-16 1990-10-16 American Cyanamid Co. 4-[(substituted) alkylcarbonyl]-4,5-dihydro- and -4,5,6,7-tetrahydro-7-[(substituted)phenyl]pyrazolo[1,5-a]pyrimidines
JPS63135381A (ja) 1986-11-26 1988-06-07 Kyorin Pharmaceut Co Ltd 多剤耐性癌細胞に対する感受性増強剤及びその製造方法
US4916142A (en) * 1987-02-02 1990-04-10 Boc, Inc. N-heterocyclic-N-(4-piperidinyl)amides and pharmaceutical compositions and their use as analgesics
US5928637A (en) * 1987-06-16 1999-07-27 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Methods of inducing multidrug resistance using human MDR1 cDNA
FR2618780B1 (fr) * 1987-07-29 1989-12-08 Irceba Derives du thiazole appartenant a la famille des 2-piperazinoacetamido-4-methylthiazoles, procede de preparation et utilisation en therapeutique
US5013742A (en) * 1987-11-02 1991-05-07 Boc, Inc. 4-phenyl-4-N-(phenyl) amido piperidine derivatives and pharmaceutical compositions and method employing such compounds
US4980351A (en) * 1987-11-04 1990-12-25 Warner-Lambert Company 3-aminopropoxyaryl derivatives having cardiotonic and antihypertensive use and compositions thereof
US4791120A (en) * 1987-12-31 1988-12-13 The Boc Group, Inc. 4-heteropentacyclic-4-[N-(phenyl)amino] piperidine derivatives and pharmaceutical compositions and method employing such compounds
DK733788A (da) * 1988-01-14 1989-07-15 Fujisawa Pharmaceutical Co Indolylpiperidinderivater og fremgangsmaade til fremstilling deraf
US5216172A (en) 1988-02-24 1993-06-01 Ajinomoto Co., Inc. 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells
CA1331613C (en) 1988-07-28 1994-08-23 Nikken Chemicals Co., Ltd. 1,4-dihydropyridine derivative
CA1334752C (en) 1988-08-02 1995-03-14 Ryozo Sakoda Drug effect-enhancing agent for antitumor drug
JP2850376B2 (ja) 1988-08-02 1999-01-27 日産化学工業株式会社 抗癌剤薬効増強剤
DE3832362A1 (de) 1988-09-23 1990-03-29 Sandoz Ag Neue cyclopeptolide, verfahren zu ihrer herstellung und ihre verwendung
CA1340821C (en) * 1988-10-06 1999-11-16 Nobuyuki Fukazawa Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components
US5204348A (en) 1988-10-06 1993-04-20 Mitsui Toatsu Chemicals Inc. Heterocyclic compounds and anticancer-drug potentiaters conaining them as effective components
GB8914062D0 (en) 1989-06-19 1989-08-09 Wellcome Found Agents for potentiating the effects of antitumour agents and combating multiple drug resistance
US5098915A (en) * 1989-09-05 1992-03-24 G. D. Searle & Co. Substituted N-benzylpiperidine amides
JPH03141258A (ja) * 1989-10-25 1991-06-17 Kowa Co 新規なピペラジン誘導体
ZA908852B (en) 1989-11-13 1991-09-25 Merrell Dow Pharma Treatment of multi-drug resistant tumors with pyridyloxazole-2-ones
ZA908936B (en) 1989-11-13 1991-09-25 Merrell Dow Pharma Treatment of multi-drug resistant tumors with quinolyloxazole-2-ones
US5182293A (en) 1989-11-13 1993-01-26 Merrell Dow Pharmaceuticals Inc. Treatment of multi-drug resistant tumors with pyridyloxazole-2-ones
US5190957A (en) 1989-11-13 1993-03-02 Merrell Dow Pharmaceuticals Inc. Treatment of multi-drug resistant tumors with quinolyl-and isoquinolyloxazole-2-ones
WO1991009846A1 (de) 1989-12-22 1991-07-11 Byk Gulden Lomberg Chemische Fabrik Gmbh Neue dihydropyridine
US5160727A (en) 1990-02-13 1992-11-03 Warner-Lambert Company Tumor cell sensitization method using quinazolinedione derivatives
US5190946A (en) 1990-02-23 1993-03-02 Hoffmann-La Roche Inc. Methods and compounds
US5272159A (en) 1990-02-26 1993-12-21 Merck & Co., Inc. Adjuncts in cancer chemotherapy
US5114919A (en) 1990-02-26 1992-05-19 Merck & Co., Inc. Adjuncts in cancer chemotherapy
US4996321A (en) 1990-02-26 1991-02-26 Merck & Co., Inc. Dibenzo[a,d]cycloheptenylidene compounds
US5091187A (en) * 1990-04-26 1992-02-25 Haynes Duncan H Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
US5514664A (en) 1990-05-26 1996-05-07 Byk Gulden Lomberg Chemische Fabrik Gmbh 1,4-dihydropyridines for application in combatting resistance to drugs
US5196799A (en) 1990-07-12 1993-03-23 Drexel University Method and apparatus for testing a protective barrier material for pinholes and tear strength
DK178490D0 (da) * 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
FR2667243B1 (fr) 1990-09-27 1994-11-04 Adir Utilisation de s derives de la triazine et de la pyrimidine pour l'obtention de medicaments reversant la resistance aux agents anticancereux et antimalariques.
US5416091A (en) 1990-12-18 1995-05-16 Burroughs Wellcome Co. Agents for potentiating the effects of antitumor agents and combating multiple drug resistance
US5693767A (en) * 1991-01-22 1997-12-02 Harrier Inc. Glycoside derivatives of acetaminophen
JPH04356466A (ja) 1991-01-28 1992-12-10 Mitsui Toatsu Chem Inc 新規キノリン誘導体及びそれを有効成分として含有する制癌剤効果増強剤
FR2673627B1 (fr) 1991-03-07 1993-05-07 Adir Triazines et pyrimidines trisubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant.
US5939420A (en) * 1991-04-08 1999-08-17 Duquesne University Of The Holy Ghost Pyrrolo 2,3d!derivatives
IT1245712B (it) 1991-04-09 1994-10-14 Boehringer Mannheim Italia Ammine eterocicliche utili terapia dell'asma e dell'infiammazione delle vie aeree
US5292757A (en) 1991-04-26 1994-03-08 Ajinomoto Company, Inc. 1,4-dihydropyridine compounds useful as reverse resistance agents
US5723459A (en) 1991-05-09 1998-03-03 Vertex Pharmaceuticals Incorporated Biologically active acylated amino acid derivatives
US5620971A (en) 1991-05-09 1997-04-15 Vertex Pharmaceuticals Incorporated Biologically active acylated amino acid derivatives
WO1992020661A1 (en) 1991-05-22 1992-11-26 Merck & Co., Inc. N, n-diacylpiperazines
ZA925185B (en) 1991-07-18 1993-04-29 Hoffmann La Roche Dithianes.
WO1993003729A1 (en) 1991-08-12 1993-03-04 Research Corporation Technologies, Inc. N-substituted phenoxazines for treating multidrug resistant cancer cells
AU653060B2 (en) * 1991-08-23 1994-09-15 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivative and platelet agglutination inhibitor
US5173486A (en) 1991-08-26 1992-12-22 Bristol-Myers Squibb Company Dibenz[b,f][1,4]oxazepin-11(10H)-ones for multidrug resistance reversing agents
CA2074061A1 (en) 1991-08-26 1993-02-27 Ivo Monkovic Benzamide multidrug resistance reversing agents
GB9119983D0 (en) 1991-09-19 1991-11-06 Erba Carlo Spa Dihydropyridine derivatives useful in antitumor therapy
US5536722A (en) 1991-11-12 1996-07-16 Pfizer Inc. Triazine derivatives for enhancing antitumor activity
FR2686879B1 (fr) 1992-02-05 1994-03-18 Adir Cie Nouveaux composes de 1,4-dihydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant.
JPH07503728A (ja) 1992-02-06 1995-04-20 メレルダウファーマスーティカルズ インコーポレイテッド テトラアリールエチレン類による多剤耐性の逆転
CA2129337A1 (en) 1992-02-19 1993-09-02 Jotham W. Coe Heterocyclic compounds for enhancing antitumor activity
US5605896A (en) * 1992-02-25 1997-02-25 Recordati S.A., Chemical And Pharmaceutical Company Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities
US5521184A (en) 1992-04-03 1996-05-28 Ciba-Geigy Corporation Pyrimidine derivatives and processes for the preparation thereof
DE69310367T2 (de) 1992-07-10 1997-08-14 Glaxo Lab Sa Anilide-derivate
GB9217331D0 (en) 1992-08-14 1992-09-30 Xenova Ltd Pharmaceutical compounds
US5516775A (en) 1992-08-31 1996-05-14 Ciba-Geigy Corporation Further use of pyrimidine derivatives
AU5127893A (en) 1992-09-11 1994-04-12 Research Corporation Technologies, Inc. 1,2 dihydro-3-h-dibenz(de,h) isoquinoline 1,3 dione and their use as anticancer agents
NZ314207A (en) 1992-09-28 2000-12-22 Vertex Pharma 1-(2-Oxoacetyl)-piperidine-2-carboxylic acid derivatives as multi drug resistant cancer cell sensitizers
IT1255704B (it) 1992-09-30 1995-11-10 Boehringer Mannheim Italia Ammine eterocicliche utili nella terapia dell'asma e dell'infiammazione delle vie aeree
US5840319A (en) * 1992-10-08 1998-11-24 Alakhov; Valery Yu Biological agent compositions
CA2146548A1 (en) 1992-11-09 1994-05-26 Giorgio Attardo Antineoplastic heteronaphthoquinones
WO1994014809A1 (de) 1992-12-23 1994-07-07 Byk Gulden Lomberg Chemische Fabrik Gmbh Anellierte uracilderivate
ATE150748T1 (de) 1993-01-21 1997-04-15 Merrell Pharma Inc Als mittel gegen mehrfach resistente tumorenverwendbare diarylalkylpiperidine
CA2155759A1 (en) 1993-03-29 1994-10-13 Bernd Janssen 1-amino-3-phenoxy propane derivatives as modulators of multi-drug resistance
WO1994022846A1 (en) 1993-03-30 1994-10-13 Pfizer Inc. Compounds enhancing antitumor activity of other cytotoxic agents
US5336685A (en) 1993-04-12 1994-08-09 Sloan-Kettering Institute For Cancer Research Use of flavonoids to treat multidrug resistant cancer cells
WO1994024105A1 (en) * 1993-04-15 1994-10-27 Merck Sharp & Dohme Limited Indole derivatives as dopamine d4 antagonists
US5643909A (en) 1993-04-19 1997-07-01 Syntex (U.S.A.) Inc. 10,11-Methanodibenzosuberane derivatives
DE4315153A1 (de) * 1993-05-07 1994-11-10 Hoechst Schering Agrevo Gmbh Substituierte Chinolinverbindungen, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener
CA2165176A1 (en) * 1993-06-18 1995-01-05 Samuel L. Graham Inhibitors of farnesyl-protein transferase
US5409690A (en) 1993-06-23 1995-04-25 Chemex Pharmaceuticals, Inc. Treatment of multidrug resistant diseases in cancer cell by potentiating with masoprocol
US5387685A (en) 1993-07-16 1995-02-07 American Cyanamid Co MDR reversal agents
AU691829B2 (en) * 1993-07-16 1998-05-28 Merck & Co., Inc. Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists
WO1995005824A1 (en) 1993-08-24 1995-03-02 Smithkline Beecham Corporation Aaptamines and method of use thereof
JPH07126165A (ja) 1993-10-29 1995-05-16 Masao Oguro 腫瘍治療剤
US5436243A (en) 1993-11-17 1995-07-25 Research Triangle Institute Duke University Aminoanthraquinone derivatives to combat multidrug resistance
WO1995021381A1 (en) * 1994-02-01 1995-08-10 The Rockefeller University Methods and agents for measuring and controlling multidrug resistance
GB9402809D0 (en) 1994-02-14 1994-04-06 Xenova Ltd Pharmaceutical compounds
US5610165A (en) 1994-02-17 1997-03-11 Merck & Co., Inc. N-acylpiperidine tachykinin antagonists
US5744485A (en) 1994-03-25 1998-04-28 Vertex Pharmaceuticals Incorporated Carbamates and ureas as modifiers of multi-drug resistance
US5763443A (en) 1994-04-05 1998-06-09 Universiteit Van Pretoria MDR resistance treatment and novel pharmaceutically active riminophenazines
JPH10500394A (ja) 1994-06-01 1998-01-13 チバ−ガイギー アクチェンゲゼルシャフト 多重薬剤耐性細胞を抗腫瘍剤に対して感受性にするための多環式ラクタム誘導体
WO1995032975A1 (en) 1994-06-01 1995-12-07 Ciba-Geigy Ag Indolocarbazole derivatives for sensitizing multidrug-resistant cells to antitumor agents
JPH10501526A (ja) 1994-06-01 1998-02-10 チバ−ガイギー アクチェンゲゼルシャフト 多薬物耐性に対する作用物質としてのカルバゾール誘導体
US5571687A (en) 1994-06-07 1996-11-05 Duke University Modulators of multidrug resistance transporters
US5525606A (en) 1994-08-01 1996-06-11 The United States Of America As Represented By The Department Of Health And Human Services Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines
US5670521A (en) 1994-08-05 1997-09-23 Merrell Pharmaceuticals Inc. Reversal of multi-drug resistance by triphenyl-azacycloalkane derivatives
US5543428A (en) 1994-08-31 1996-08-06 Eli Lilly And Company Method for treating resistant tumors
IL115582A0 (en) 1994-10-14 1996-01-19 Lilly Co Eli Methods for treating resistant tumors
EP0709384B1 (de) * 1994-10-31 1998-12-23 MERCK PATENT GmbH Benzylpiperidinderivate mit hoher Affinität zu Bindungsstellen von Aminosäure-Rezeptoren
US5543423A (en) 1994-11-16 1996-08-06 Vertex Pharmaceuticals, Incorporated Amino acid derivatives with improved multi-drug resistance activity
IL115685A (en) 1994-11-16 2000-08-31 Vertex Pharma Amino acid derivatives pharmaceutical compositions containing the same and processes for the preparation thereof
GB9426090D0 (en) 1994-12-23 1995-02-22 Xenova Ltd Pharmaceutical compounds
GB9426224D0 (en) 1994-12-23 1995-02-22 Xenova Ltd Pharmaceutical compounds
GB9426071D0 (en) 1994-12-23 1995-02-22 Xenova Ltd Pharmaceutical compounds
US5789402A (en) * 1995-01-17 1998-08-04 Eli Lilly Company Compounds having effects on serotonin-related systems
JPH0912577A (ja) 1995-04-28 1997-01-14 Takeda Chem Ind Ltd カルバペネム化合物、その製造法および剤
US5726184A (en) 1995-05-19 1998-03-10 Vertex Pharmaceuticals Incorporated Tetralin compounds with improved MDR activity
US5700826A (en) 1995-06-07 1997-12-23 Ontogen Corporation 1,2,4,5-tetra substituted imidazoles as modulators of multi-drug resistance
US5756527A (en) 1995-06-07 1998-05-26 Ontogen Corporation Imidazole derivatives useful as modulators of multi drug resistances
CA2179574A1 (en) * 1995-06-26 1996-12-27 Tomomi Okada Substituted piperidine derivative and medicine comprising the same
US5834014A (en) * 1995-10-06 1998-11-10 The Regents Of The University Of Michigan Stimulation of hair follicles
US5670508A (en) 1995-10-25 1997-09-23 National Science Council 2-amino-6-alkyl-5-(4-substituted-1-piperazinyl) pyrimidin-4-ones, the preparation and use thereof
WO1997017069A1 (en) 1995-11-07 1997-05-15 Eli Lilly And Company Methods for treating resistant tumors
US6011069A (en) 1995-12-26 2000-01-04 Nisshin Flour Milling Co., Ltd. Multidrug resistance inhibitors
DE19548797A1 (de) 1995-12-27 1997-07-03 Thomae Gmbh Dr K Substituierte 2-Amino-imidazole, ihre Herstellung und ihre Verwendung als Arzneimittel
ES2218660T3 (es) 1996-01-16 2004-11-16 Bristol-Myers Squibb Company Inhibidores aromaticos conformacionalmente restringidos de la proteina de transferencia de trigliceridos microsomales y procedimiento.
US5733911A (en) 1996-01-26 1998-03-31 Hitachi Chemical Co., Ltd. Method for inducing death of neoplastic cells using piperazne derivatives
DE69700887T2 (de) 1996-01-31 2000-06-29 Nisshin Flour Milling Co., Ltd. Isoprenderivate
AU1597197A (en) 1996-02-01 1997-08-22 Byk Gulden Lomberg Chemische Fabrik Gmbh Thienoquinolines
TW527186B (en) 1996-03-19 2003-04-11 Janssen Pharmaceutica Nv Fused imidazole derivatives as multidrug resistance modulators
US5717092A (en) 1996-03-29 1998-02-10 Vertex Pharmaceuticals Inc. Compounds with improved multi-drug resistance activity
US5885786A (en) 1996-04-19 1999-03-23 John Wayne Cancer Institute Methods for screening of substances for inhibition of multidrug resistance
AU2908997A (en) 1996-05-24 1998-01-05 University Of Pretoria, The Use of riminophenazines as antimicrobial and antimalarial agents
EP0812830A1 (de) 1996-06-14 1997-12-17 Ontogen Corporation Modulatoren von Mehrfachresistenz gegen Medikamente
WO1997048689A1 (en) 1996-06-17 1997-12-24 Eli Lilly And Company Drug resistance and multidrug resistance modulators
US5869650A (en) 1996-06-21 1999-02-09 Fox Chase Cancer Center Dendroamide compounds and their use in chemosensitizing multidrug resistant cells
DK0927168T3 (da) 1996-08-28 2003-03-10 Procter & Gamble 1,3-diheterocykliske metalloproteaseinhibitorer
PL331854A1 (en) * 1996-08-28 1999-08-16 Procter & Gamble Phosphinamides as inhibitors of metaloprotease matrix
GB2317030A (en) 1996-08-30 1998-03-11 Xenova Ltd Defining a pharmacophore for the design of MDR modulators
US5811434A (en) 1996-11-13 1998-09-22 Vertex Pharmacueticals Incorporated Methods and compositions for stimulating neurite growth
KR20000057157A (ko) * 1996-11-22 2000-09-15 피터 지. 스트링거 약물 내성 및 복합 약물 내성 조절제
US5811452A (en) 1997-01-08 1998-09-22 The Research Foundation Of State University Of New York Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof
CA2198645A1 (en) 1997-02-27 1998-08-27 Peter Juranka Use of dillapiol and its analogues and derivatives to affect multidrug resistant cells
TWI242011B (en) * 1997-03-31 2005-10-21 Eisai Co Ltd 1,4-substituted cyclic amine derivatives
JPH111476A (ja) * 1997-04-25 1999-01-06 Ontogen Corp 多剤耐性のモジュレータ
GB9710612D0 (en) 1997-05-23 1997-07-16 Glaxo Group Ltd Synthesis of acridine derivatives
US5776939A (en) 1997-06-12 1998-07-07 Eli Lilly And Company Drug resistance and multidrug resistance modulators
US5840721A (en) 1997-07-09 1998-11-24 Ontogen Corporation Imidazole derivatives as MDR modulators
WO1999010340A1 (en) 1997-08-29 1999-03-04 Vertex Pharmaceuticals Incorporated Compounds possessing neuronal activity
AU1146099A (en) 1997-09-18 1999-04-05 Janssen Pharmaceutica N.V. Fused imidazole derivatives for improving oral bioavailability of pharmaceuticalagents
ZA9810210B (en) 1997-11-10 1999-07-14 Searle & Co Use of alkylated iminosugars to treat multidrug resistance.
EP1034164B1 (de) 1997-11-24 2004-05-19 Merck & Co., Inc. Beta-alanin-derivate als zell-adhäsions-inhibitoren
US6248752B1 (en) 1998-02-27 2001-06-19 Charles Duane Smith Azabicyclooctane compositions and methods for enhancing chemotherapy
US6066673A (en) * 1998-03-12 2000-05-23 The Procter & Gamble Company Enzyme inhibitors
US6399629B1 (en) 1998-06-01 2002-06-04 Microcide Pharmaceuticals, Inc. Efflux pump inhibitors
US6331537B1 (en) 1998-06-03 2001-12-18 Gpi Nil Holdings, Inc. Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
GB9812189D0 (en) 1998-06-05 1998-08-05 Glaxo Group Ltd Methods and compositions for increasing penetration of HIV protease inhibitors
CA2333554A1 (en) 1998-06-17 1999-12-23 Chu-Baio Xue Cyclic hydroxamic acids as metalloproteinase inhibitors
TWI250152B (en) 1998-07-21 2006-03-01 Eisai Co Ltd N,N-substituted cyclic amine compounds used as calcium antagonizer
US6329872B1 (en) * 1998-08-14 2001-12-11 Nortel Networks Limited Charge pump circuit for a phase locked loop
US6307049B1 (en) 1998-09-30 2001-10-23 The Procter & Gamble Co. Heterocyclic 2-substituted ketoamides
ES2221440T3 (es) * 1998-10-16 2004-12-16 Daiichi Suntory Pharma Co Ltd Derivados de acido aminofenoxiacetico como neuroprotectores.
KR20010081115A (ko) 1998-12-18 2001-08-27 둘락 노먼 씨. 파르네실 단백질 트랜스퍼라제 억제제
US6200990B1 (en) * 1998-12-21 2001-03-13 Alcon Laboratories, Inc. Neuroprotective agents having antioxidant and NMDA antagonist activity
FR2789076B1 (fr) * 1999-02-02 2001-03-02 Synthelabo Derives de alpha-azacyclomethyl quinoleine, leur preparation et leur application en therapeutique
FR2790260B1 (fr) 1999-02-26 2001-05-04 Fournier Ind & Sante Nouveaux composes de n-(benzenesulfonamide), procede de preparation et utilisation en therapeutique
HUP9902628A3 (en) * 1999-08-02 2001-07-30 Ivax Gyogyszerki Kft Angiogenesis inhibiting borrelidin derivatives, their use and pharmaceutical compositions containing them
US6403610B1 (en) * 1999-09-17 2002-06-11 Aventis Pharma S.A. Quinolylpropylpiperidine derivatives, their preparation and the compositions which comprise them
US6476041B1 (en) * 1999-10-29 2002-11-05 Merck & Co., Inc. 1,4 substituted piperidinyl NMDA/NR2B antagonists
US6258526B1 (en) * 2000-01-19 2001-07-10 M.D.R. Test Ltd Ex-vivo test kit for testing the effectiveness of reversers of multidrug resistance
EA200200847A1 (ru) 2000-02-11 2003-02-27 Вертекс Фармасьютикалз Инкорпорейтед Производные пиперазина и пиперидина для лечения и профилактики поврежденных нейронов
CN101230034A (zh) * 2000-03-06 2008-07-30 阿卡蒂亚药品公司 用于治疗5-羟色胺相关性疾病的氮杂环化合物
US7018988B2 (en) 2000-03-27 2006-03-28 Applied Research Systems Ars Holding N.V. Pharmaceutically active pyrrolidine derivatives as Bax inhibitors
US6498170B2 (en) * 2000-07-17 2002-12-24 Wyeth Cyclamine sulfonamides as β-3 adrenergic receptor agonists
US20020119979A1 (en) * 2000-10-17 2002-08-29 Degenhardt Charles Raymond Acyclic compounds and methods for treating multidrug resistance
US20020115659A1 (en) * 2000-10-17 2002-08-22 Degenhardt Charles Raymond Compounds having heterocyclic groups containing two nitrogen atoms for treating multidrug resistance
US20020091120A1 (en) 2000-10-17 2002-07-11 Degenhardt Charles Raymond 2-substituted heterocyclic compounds for treating multidrug resistance
US6809093B2 (en) * 2000-10-17 2004-10-26 H. Lee Moffitt Cancer & Research Institute, Inc. 2-substituted heterocyclic compounds
US20020128269A1 (en) * 2000-10-17 2002-09-12 Degenhardt Charles Raymond Substituted heterocyclic compounds for treating multidrug resistance
US6693099B2 (en) 2000-10-17 2004-02-17 The Procter & Gamble Company Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
US6376514B1 (en) * 2000-10-17 2002-04-23 The Procter & Gamble Co. Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof
US20020082262A1 (en) * 2000-10-17 2002-06-27 Degenhardt Charles Raymond Substituted bicyclic compounds for treating multidrug resistance
AU2002233598B2 (en) * 2001-02-28 2007-06-14 Ge Healthcare Niagara Inc. An imaging fluorometer for time resolved fluorescence
US6803362B2 (en) * 2001-03-09 2004-10-12 Ortho-Mcneil Pharmaceutical Inc. Heterocyclic compounds
US6602884B2 (en) * 2001-03-13 2003-08-05 Aventis Pharma S.A. Quinolylpropylpiperidine derivatives, their preparation, and compositions containing them
US8249317B2 (en) 2007-07-20 2012-08-21 Eleckta Ltd. Methods and systems for compensating for changes in anatomy of radiotherapy patients

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CA2420996C (en) 2010-06-22
US20020123498A1 (en) 2002-09-05
WO2002032874A8 (en) 2003-11-13
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US7304053B2 (en) 2007-12-04
US6693099B2 (en) 2004-02-17

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