JP2006523718A - チロナミン誘導体およびチロナミンアナログならびにこれらを使用する方法 - Google Patents
チロナミン誘導体およびチロナミンアナログならびにこれらを使用する方法 Download PDFInfo
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- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
Applications Claiming Priority (3)
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US10/418,399 US6979750B1 (en) | 2003-04-18 | 2003-04-18 | Thyronamine derivatives and analogs and methods of use thereof |
US10/825,881 US7321065B2 (en) | 2003-04-18 | 2004-04-16 | Thyronamine derivatives and analogs and methods of use thereof |
PCT/US2004/011893 WO2004093800A2 (en) | 2003-04-18 | 2004-04-19 | Thyronamine derivatives and analogs and methods of use thereof |
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JP2010239126A Division JP2011026345A (ja) | 2003-04-18 | 2010-10-25 | チロナミン誘導体およびチロナミンアナログならびにこれらを使用する方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7321065B2 (en) * | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
CA2557794A1 (en) * | 2004-03-15 | 2005-10-06 | Eli Lilly And Company | Opioid receptor antagonists |
WO2007059039A1 (en) * | 2005-11-11 | 2007-05-24 | Oregon Health & Science University | Thyroxine derivatives for preconditioning against stroke |
WO2008005407A2 (en) * | 2006-07-03 | 2008-01-10 | Fred Hutchinson Cancer Research Center | Trace amine-associated receptors in the olfactory epithelium |
GB0725214D0 (en) * | 2007-12-24 | 2008-02-06 | Karobio Ab | Pharmaceutical compounds |
EP2098226A1 (de) * | 2008-03-06 | 2009-09-09 | Forschungsverbund Berlin e.V. | AKAP-PKA-Interaktionshemmer zur Anwendung in der Behandlung von Herzkrankheiten |
TWI449533B (zh) * | 2008-04-18 | 2014-08-21 | Intervet Int Bv | 防備胞內勞森菌(Lawsonia intracellularis)、豬肺炎黴漿菌(Mycoplasma hyopneumoniae)及豬環狀病毒(Porcine circo virus)用疫苗 |
KR101112731B1 (ko) * | 2009-11-02 | 2012-03-13 | 연세대학교 산학협력단 | 3-아이오도타이로나민의 제조방법 |
US8956859B1 (en) | 2010-08-13 | 2015-02-17 | Aviex Technologies Llc | Compositions and methods for determining successful immunization by one or more vaccines |
CN102464618B (zh) | 2010-11-03 | 2014-07-23 | 中国中化股份有限公司 | 吡唑酰胺类化合物及其应用 |
WO2013006734A1 (en) * | 2011-07-05 | 2013-01-10 | St. Jude Children's Research Hospital | Substituted 4-phenoxyphenol analogs as modulators of proliferating cell nuclear antigen activity |
CN103772369B (zh) | 2012-10-25 | 2016-12-21 | 沈阳中化农药化工研发有限公司 | 胡椒乙胺类化合物及其用途 |
CN104684900B (zh) | 2012-10-25 | 2017-04-12 | 沈阳中化农药化工研发有限公司 | 取代嘧啶类化合物及其用途 |
WO2015151068A1 (en) * | 2014-04-03 | 2015-10-08 | Universita' Di Pisa | Synthetic analogues of 3-iodothyronamine (t1am) and uses thereof |
KR20160083806A (ko) * | 2014-12-30 | 2016-07-12 | 연세대학교 산학협력단 | 콜레스테롤 관련 질환의 예방 및 치료용 조성물 |
KR101755255B1 (ko) | 2015-04-30 | 2017-07-07 | 연세대학교 원주산학협력단 | 저대사 유도용 조성물, 저대사 유도방법 및 그 기술을 이용한 어류 운송방법 |
US11974970B2 (en) | 2015-06-29 | 2024-05-07 | University Industry Foundation, Yonsei University Wonju Campus | Muscular atrophy-inducing agent using hypometabolism-inducing substance T1AM, and use thereof in treating muscular hypertrophy |
WO2017003177A1 (ko) * | 2015-06-29 | 2017-01-05 | 연세대학교 원주산학협력단 | 저대사 유도물질 t1am을 이용한 근위축 유도제 및 이의 근비대증 치료 용도 |
KR102004930B1 (ko) | 2015-06-29 | 2019-07-29 | 연세대학교 원주산학협력단 | 저대사 유도물질 t1am을 이용한 근위축 유도제 및 이의 근비대 치료 용도 |
CN114195672A (zh) | 2018-03-02 | 2022-03-18 | 俄勒冈健康科学大学 | 小分子核受体调节剂的酰胺前药 |
JP2022513449A (ja) | 2018-12-12 | 2022-02-08 | オートバーン セラピューティクス,インク. | 新規な甲状腺模倣物 |
EP3931180A1 (en) | 2019-03-01 | 2022-01-05 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
Citations (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3118942A (en) * | 1961-02-10 | 1964-01-21 | Wisconsin Alumni Res Found | alpha-methyl-iodothyronamines |
DE2514630A1 (de) * | 1974-04-03 | 1975-10-09 | Roussel Uclaf | Thyronamin-derivate, herstellungsverfahren dafuer und pharmazeutische zusammensetzungen |
FR2291743A1 (fr) * | 1974-11-21 | 1976-06-18 | Roussel Uclaf | Nouveau derive de la thyronamine et ses sels, leur procede de preparation et leur application comme medicaments |
JPS559096A (en) * | 1978-07-03 | 1980-01-22 | Lilly Co Eli | Phenethanol amines |
JPS5984849A (ja) * | 1982-09-22 | 1984-05-16 | バイエル・アクチエンゲゼルシヤフト | 成長促進性フエニルエチルアミン誘導体類 |
JPH0543536A (ja) * | 1991-08-13 | 1993-02-23 | Dainippon Jochugiku Co Ltd | 新規アミジン誘導体、及びこれを含有する殺虫、殺ダニ剤 |
JPH06329535A (ja) * | 1993-03-26 | 1994-11-29 | Taisho Pharmaceut Co Ltd | シグマ受容体拮抗薬 |
JPH06511259A (ja) * | 1992-04-09 | 1994-12-15 | ゼネカ リミテッド | 治療用アミン |
JPH0959230A (ja) * | 1995-06-14 | 1997-03-04 | Taisho Pharmaceut Co Ltd | 光学活性置換フェニルアルキルアミン誘導体 |
JPH11508241A (ja) * | 1995-06-07 | 1999-07-21 | カロ バイオ エービー | 甲状腺ホルモンまたは甲状腺ホルモン様化合物に関する新規な使用 |
JPH11302235A (ja) * | 1998-04-15 | 1999-11-02 | Taisho Pharmaceut Co Ltd | フェノキシアルキルアミン誘導体 |
JP2001500152A (ja) * | 1996-09-16 | 2001-01-09 | ナイコメッド・アマーシャム・ピーエルシー | 標識化エラスターゼ・インヒビター |
WO2001068609A1 (en) * | 2000-03-14 | 2001-09-20 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisoquinoline derivatives |
JP2002503721A (ja) * | 1998-02-21 | 2002-02-05 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換イソインドロンおよび医薬におけるサイクリックgmp調節剤としてのそれらの使用 |
US20020032238A1 (en) * | 2000-07-08 | 2002-03-14 | Henning Priepke | Biphenylcarboxylic acid amides, the preparation thereof and the use thereof as medicaments |
JP2002513387A (ja) * | 1996-09-05 | 2002-05-08 | イーライ・リリー・アンド・カンパニー | 選択的β▲下3▼アドレナリン作動性アゴニスト |
WO2002051838A1 (en) * | 2000-12-27 | 2002-07-04 | Actelion Pharmaceuticals Ltd. | Novel benzazepines and related heterocyclic derivatives which are useful as orexin receptor antagonists |
JP2002539115A (ja) * | 1999-03-10 | 2002-11-19 | ビオヴィトルム・アクチボラゲット | タンパク質チロシンホスファターゼ阻害剤 |
WO2003086396A1 (fr) * | 2002-04-02 | 2003-10-23 | Tsumura & Co. | Inhibiteur de phosphodiesterase iv contenant un derive de pyridylacrylamide |
WO2003106462A1 (en) * | 2002-06-14 | 2003-12-24 | Pfizer Inc. | Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use |
WO2004020415A1 (en) * | 2002-08-27 | 2004-03-11 | Astrazeneca Ab | 2,5-dioxoimidazolidin-4-yl acetamides and analogues as inhibitors of metalloproteinase mmp12. |
Family Cites Families (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL154600B (nl) | 1971-02-10 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van specifiek bindende eiwitten en hun corresponderende bindbare stoffen. |
NL154598B (nl) | 1970-11-10 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van laagmoleculire verbindingen en van eiwitten die deze verbindingen specifiek kunnen binden, alsmede testverpakking. |
NL154599B (nl) | 1970-12-28 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van specifiek bindende eiwitten en hun corresponderende bindbare stoffen, alsmede testverpakking. |
US3817837A (en) | 1971-05-14 | 1974-06-18 | Syva Corp | Enzyme amplification assay |
US3901654A (en) | 1971-06-21 | 1975-08-26 | Biological Developments | Receptor assays of biologically active compounds employing biologically specific receptors |
US3853987A (en) | 1971-09-01 | 1974-12-10 | W Dreyer | Immunological reagent and radioimmuno assay |
US3867517A (en) | 1971-12-21 | 1975-02-18 | Abbott Lab | Direct radioimmunoassay for antigens and their antibodies |
NL171930C (nl) | 1972-05-11 | 1983-06-01 | Akzo Nv | Werkwijze voor het aantonen en bepalen van haptenen, alsmede testverpakkingen. |
US3850578A (en) | 1973-03-12 | 1974-11-26 | H Mcconnell | Process for assaying for biologically active molecules |
US3935074A (en) | 1973-12-17 | 1976-01-27 | Syva Company | Antibody steric hindrance immunoassay with two antibodies |
US3996345A (en) | 1974-08-12 | 1976-12-07 | Syva Company | Fluorescence quenching with immunological pairs in immunoassays |
US4034074A (en) | 1974-09-19 | 1977-07-05 | The Board Of Trustees Of Leland Stanford Junior University | Universal reagent 2-site immunoradiometric assay using labelled anti (IgG) |
US3984533A (en) | 1975-11-13 | 1976-10-05 | General Electric Company | Electrophoretic method of detecting antigen-antibody reaction |
US4098876A (en) | 1976-10-26 | 1978-07-04 | Corning Glass Works | Reverse sandwich immunoassay |
US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
US4391904A (en) * | 1979-12-26 | 1983-07-05 | Syva Company | Test strip kits in immunoassays and compositions therein |
US4486530A (en) | 1980-08-04 | 1984-12-04 | Hybritech Incorporated | Immunometric assays using monoclonal antibodies |
US4376110A (en) * | 1980-08-04 | 1983-03-08 | Hybritech, Incorporated | Immunometric assays using monoclonal antibodies |
US4366241A (en) * | 1980-08-07 | 1982-12-28 | Syva Company | Concentrating zone method in heterogeneous immunoassays |
US4517288A (en) * | 1981-01-23 | 1985-05-14 | American Hospital Supply Corp. | Solid phase system for ligand assay |
CH652145A5 (de) * | 1982-01-22 | 1985-10-31 | Sandoz Ag | Verfahren zur in vitro-herstellung von hybridomen welche humane monoklonale antikoerper erzeugen. |
US4634666A (en) * | 1984-01-06 | 1987-01-06 | The Board Of Trustees Of The Leland Stanford Junior University | Human-murine hybridoma fusion partner |
CA1291031C (en) * | 1985-12-23 | 1991-10-22 | Nikolaas C.J. De Jaeger | Method for the detection of specific binding agents and their correspondingbindable substances |
US5225539A (en) * | 1986-03-27 | 1993-07-06 | Medical Research Council | Recombinant altered antibodies and methods of making altered antibodies |
US5530101A (en) * | 1988-12-28 | 1996-06-25 | Protein Design Labs, Inc. | Humanized immunoglobulins |
IL162181A (en) | 1988-12-28 | 2006-04-10 | Pdl Biopharma Inc | A method of producing humanized immunoglubulin, and polynucleotides encoding the same |
IL94466A (en) | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
US5427908A (en) | 1990-05-01 | 1995-06-27 | Affymax Technologies N.V. | Recombinant library screening methods |
US6172197B1 (en) * | 1991-07-10 | 2001-01-09 | Medical Research Council | Methods for producing members of specific binding pairs |
GB9015198D0 (en) * | 1990-07-10 | 1990-08-29 | Brien Caroline J O | Binding substance |
DE69230142T2 (de) * | 1991-05-15 | 2000-03-09 | Cambridge Antibody Tech | Verfahren zur herstellung von spezifischen bindungspaargliedern |
US5858657A (en) * | 1992-05-15 | 1999-01-12 | Medical Research Council | Methods for producing members of specific binding pairs |
ATE255131T1 (de) | 1991-06-14 | 2003-12-15 | Genentech Inc | Humanisierter heregulin antikörper |
US5565332A (en) * | 1991-09-23 | 1996-10-15 | Medical Research Council | Production of chimeric antibodies - a combinatorial approach |
US5733743A (en) * | 1992-03-24 | 1998-03-31 | Cambridge Antibody Technology Limited | Methods for producing members of specific binding pairs |
DE4210569A1 (de) * | 1992-03-31 | 1993-10-07 | Hoechst Ag | Verwendung von substituierten µ-Hydroxyethylaminen als fungizide Wirkstoffe |
DK0672142T3 (da) * | 1992-12-04 | 2001-06-18 | Medical Res Council | Multivalente og multispecifikke bindingsproteiner samt fremstilling og anvendelse af disse |
US5914241A (en) | 1993-01-19 | 1999-06-22 | Biosite Diagnostics, Inc. | Assays and kits for detecting analytes in the presence of cross-reacting substances |
US5877218A (en) * | 1994-01-10 | 1999-03-02 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
GB9712818D0 (en) * | 1996-07-08 | 1997-08-20 | Cambridge Antibody Tech | Labelling and selection of specific binding molecules |
WO1998027972A2 (en) | 1996-12-23 | 1998-07-02 | Texas A & M University | Anti-amyloidogenic agents |
US5965375A (en) | 1997-04-04 | 1999-10-12 | Biosite Diagnostics | Diagnostic tests and kits for Clostridium difficile |
AR018470A1 (es) | 1999-06-01 | 2001-11-14 | Procter & Gamble | Metodo para el tratamiento de la perdida del cabello con un compuesto que no afecta el corazon |
AU6936500A (en) * | 1999-08-24 | 2001-03-19 | Regents Of The University Of California, The | Non-quinoline inhibitors of malaria parasites |
AU2001234689A1 (en) | 2000-02-01 | 2001-08-14 | Cor Therapeutics, Inc. | Bivalent phenylene inhibitors of factor xa |
WO2002060375A2 (en) | 2001-01-29 | 2002-08-08 | Insight Strategy And Marketing Ltd | Diphenyl ether derivatives and their uses as heparanase inhibitors |
FR2826571B1 (fr) | 2001-06-29 | 2005-10-07 | Oreal | Compositions contenant un derive d'hydroxydiphenyl ether inhibant le developpement des odeurs corporelles |
US6951884B2 (en) | 2002-06-12 | 2005-10-04 | Hoffmann-La Roche Inc. | Fluorobenzamides and uses thereof |
US7321065B2 (en) | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
-
2004
- 2004-04-16 US US10/825,881 patent/US7321065B2/en not_active Expired - Fee Related
- 2004-04-19 EP EP04759961A patent/EP1625111A4/en not_active Withdrawn
- 2004-04-19 JP JP2006513092A patent/JP2006523718A/ja active Pending
- 2004-04-19 CA CA002517560A patent/CA2517560A1/en not_active Abandoned
- 2004-04-19 AU AU2004231999A patent/AU2004231999B2/en not_active Ceased
- 2004-04-19 WO PCT/US2004/011893 patent/WO2004093800A2/en active Application Filing
-
2005
- 2005-04-05 US US11/099,959 patent/US7355079B2/en not_active Expired - Fee Related
-
2007
- 2007-11-30 US US11/948,902 patent/US20090105347A1/en not_active Abandoned
-
2010
- 2010-10-25 JP JP2010239126A patent/JP2011026345A/ja active Pending
- 2010-11-26 AU AU2010246462A patent/AU2010246462A1/en not_active Abandoned
Patent Citations (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3118942A (en) * | 1961-02-10 | 1964-01-21 | Wisconsin Alumni Res Found | alpha-methyl-iodothyronamines |
DE2514630A1 (de) * | 1974-04-03 | 1975-10-09 | Roussel Uclaf | Thyronamin-derivate, herstellungsverfahren dafuer und pharmazeutische zusammensetzungen |
FR2291743A1 (fr) * | 1974-11-21 | 1976-06-18 | Roussel Uclaf | Nouveau derive de la thyronamine et ses sels, leur procede de preparation et leur application comme medicaments |
JPS559096A (en) * | 1978-07-03 | 1980-01-22 | Lilly Co Eli | Phenethanol amines |
JPS5984849A (ja) * | 1982-09-22 | 1984-05-16 | バイエル・アクチエンゲゼルシヤフト | 成長促進性フエニルエチルアミン誘導体類 |
JPH0543536A (ja) * | 1991-08-13 | 1993-02-23 | Dainippon Jochugiku Co Ltd | 新規アミジン誘導体、及びこれを含有する殺虫、殺ダニ剤 |
JPH06511259A (ja) * | 1992-04-09 | 1994-12-15 | ゼネカ リミテッド | 治療用アミン |
JPH06329535A (ja) * | 1993-03-26 | 1994-11-29 | Taisho Pharmaceut Co Ltd | シグマ受容体拮抗薬 |
JPH11508241A (ja) * | 1995-06-07 | 1999-07-21 | カロ バイオ エービー | 甲状腺ホルモンまたは甲状腺ホルモン様化合物に関する新規な使用 |
JPH0959230A (ja) * | 1995-06-14 | 1997-03-04 | Taisho Pharmaceut Co Ltd | 光学活性置換フェニルアルキルアミン誘導体 |
JP2002513387A (ja) * | 1996-09-05 | 2002-05-08 | イーライ・リリー・アンド・カンパニー | 選択的β▲下3▼アドレナリン作動性アゴニスト |
JP2001500152A (ja) * | 1996-09-16 | 2001-01-09 | ナイコメッド・アマーシャム・ピーエルシー | 標識化エラスターゼ・インヒビター |
JP2002503721A (ja) * | 1998-02-21 | 2002-02-05 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換イソインドロンおよび医薬におけるサイクリックgmp調節剤としてのそれらの使用 |
JPH11302235A (ja) * | 1998-04-15 | 1999-11-02 | Taisho Pharmaceut Co Ltd | フェノキシアルキルアミン誘導体 |
JP2002539115A (ja) * | 1999-03-10 | 2002-11-19 | ビオヴィトルム・アクチボラゲット | タンパク質チロシンホスファターゼ阻害剤 |
WO2001068609A1 (en) * | 2000-03-14 | 2001-09-20 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisoquinoline derivatives |
US20020032238A1 (en) * | 2000-07-08 | 2002-03-14 | Henning Priepke | Biphenylcarboxylic acid amides, the preparation thereof and the use thereof as medicaments |
WO2002051838A1 (en) * | 2000-12-27 | 2002-07-04 | Actelion Pharmaceuticals Ltd. | Novel benzazepines and related heterocyclic derivatives which are useful as orexin receptor antagonists |
WO2003086396A1 (fr) * | 2002-04-02 | 2003-10-23 | Tsumura & Co. | Inhibiteur de phosphodiesterase iv contenant un derive de pyridylacrylamide |
WO2003106462A1 (en) * | 2002-06-14 | 2003-12-24 | Pfizer Inc. | Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use |
WO2004020415A1 (en) * | 2002-08-27 | 2004-03-11 | Astrazeneca Ab | 2,5-dioxoimidazolidin-4-yl acetamides and analogues as inhibitors of metalloproteinase mmp12. |
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EP1625111A4 (en) | 2007-04-25 |
AU2004231999B2 (en) | 2010-08-26 |
WO2004093800A2 (en) | 2004-11-04 |
US20050096485A1 (en) | 2005-05-05 |
US7355079B2 (en) | 2008-04-08 |
US20060035980A1 (en) | 2006-02-16 |
WO2004093800A3 (en) | 2005-01-06 |
AU2010246462A1 (en) | 2010-12-16 |
EP1625111A2 (en) | 2006-02-15 |
US7321065B2 (en) | 2008-01-22 |
US20090105347A1 (en) | 2009-04-23 |
AU2004231999A1 (en) | 2004-11-04 |
CA2517560A1 (en) | 2004-11-04 |
JP2011026345A (ja) | 2011-02-10 |
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