CA2517560A1 - Thyronamine derivatives and analogs and methods of use thereof - Google Patents

Thyronamine derivatives and analogs and methods of use thereof Download PDF

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Publication number
CA2517560A1
CA2517560A1 CA002517560A CA2517560A CA2517560A1 CA 2517560 A1 CA2517560 A1 CA 2517560A1 CA 002517560 A CA002517560 A CA 002517560A CA 2517560 A CA2517560 A CA 2517560A CA 2517560 A1 CA2517560 A1 CA 2517560A1
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CA
Canada
Prior art keywords
lower alkyl
compound
thyronamine
conh
nhco
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002517560A
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English (en)
French (fr)
Inventor
Thomas S. Scanlan
Matthew E. Hart
David K. Grandy
James R. Bunzow
Mononori Miyakawa
Edwin Saavedra Tan
Katherine L. Suchland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of California
Oregon Health Science University
Original Assignee
The Regents Of The University Of California
Thomas S. Scanlan
Matthew E. Hart
David K. Grandy
James R. Bunzow
Mononori Miyakawa
Edwin Saavedra Tan
Katherine L. Suchland
Oregon Health & Science University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US10/418,399 external-priority patent/US6979750B1/en
Application filed by The Regents Of The University Of California, Thomas S. Scanlan, Matthew E. Hart, David K. Grandy, James R. Bunzow, Mononori Miyakawa, Edwin Saavedra Tan, Katherine L. Suchland, Oregon Health & Science University filed Critical The Regents Of The University Of California
Publication of CA2517560A1 publication Critical patent/CA2517560A1/en
Abandoned legal-status Critical Current

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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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    • A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
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    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/52—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/16—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
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    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/50—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C255/00—Carboxylic acid nitriles
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    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • 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
    • C07C271/16—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 singly-bound oxygen atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • 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
CA002517560A 2003-04-18 2004-04-19 Thyronamine derivatives and analogs and methods of use thereof Abandoned CA2517560A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10/418,399 US6979750B1 (en) 2003-04-18 2003-04-18 Thyronamine derivatives and analogs and methods of use thereof
US10/418,399 2003-04-18
US10/825,881 2004-04-16
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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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
US20140288077A1 (en) * 2011-07-05 2014-09-25 St. Jude Children's Research Hospital Substituted 4-phenoxyphenol analogs as modulators of proliferating cell nuclear antigen activity
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
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
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
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
SG11202008251TA (en) 2018-03-02 2020-09-29 Univ Oregon Health & Science Amide prodrugs of small molecule nuclear receptor modulators
US11827596B2 (en) 2018-12-12 2023-11-28 Autobahn Therapeutics, Inc. Thyromimetics
WO2020180624A1 (en) 2019-03-01 2020-09-10 Autobahn Therapeutics, Inc. Novel thyromimetics

Family Cites Families (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3118942A (en) * 1961-02-10 1964-01-21 Wisconsin Alumni Res Found alpha-methyl-iodothyronamines
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
FR2266497B1 (US07321065-20080122-C00096.png) * 1974-04-03 1977-11-04 Roussel Uclaf
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)
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
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
CA1145767A (en) * 1978-07-03 1983-05-03 Jack Mills Phenethanolamines, compositions containing the same, and method for effecting weight control
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
US4376110A (en) * 1980-08-04 1983-03-08 Hybritech, Incorporated Immunometric assays using monoclonal antibodies
US4486530A (en) 1980-08-04 1984-12-04 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.
DE3234995A1 (de) * 1982-09-22 1984-03-22 Troponwerke GmbH & Co KG, 5000 Köln Wachstumsfoerdernde phenylethylamin-derivate
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
GB9015198D0 (en) 1990-07-10 1990-08-29 Brien Caroline J O Binding substance
US6172197B1 (en) * 1991-07-10 2001-01-09 Medical Research Council Methods for producing members of specific binding pairs
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
EP0590058B1 (en) 1991-06-14 2003-11-26 Genentech, Inc. HUMANIZED Heregulin ANTIBODy
JP2976038B2 (ja) * 1991-08-13 1999-11-10 大日本除蟲菊株式会社 新規アミジン誘導体、及びこれを含有する殺虫、殺ダニ剤
ES2136092T3 (es) * 1991-09-23 1999-11-16 Medical Res Council Procedimientos para la produccion de anticuerpos humanizados.
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
GB9207855D0 (en) * 1992-04-09 1992-05-27 Ici Plc Therapeutic amines
EP0672142B1 (en) * 1992-12-04 2001-02-28 Medical Research Council Multivalent and multispecific binding proteins, their manufacture and use
US5914241A (en) 1993-01-19 1999-06-22 Biosite Diagnostics, Inc. Assays and kits for detecting analytes in the presence of cross-reacting substances
JP3421702B2 (ja) * 1993-03-26 2003-06-30 大正製薬株式会社 シグマ受容体拮抗薬
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
WO1996040048A2 (en) * 1995-06-07 1996-12-19 Karo Bio Ab Novel uses for thyroid hormones or thyroid hormone-like compounds
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
GB9712818D0 (en) * 1996-07-08 1997-08-20 Cambridge Antibody Tech Labelling and selection of specific binding molecules
EP0827746B1 (en) * 1996-09-05 2002-04-03 Eli Lilly And Company Carbazole analogues as selective beta3 adrenergic agonists
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
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
US6410585B1 (en) * 1997-08-28 2002-06-25 Scott D. Larsen Inhibitors of protein tyrosine phosphatase
DE19807423A1 (de) * 1998-02-21 1999-08-26 Hoechst Marion Roussel De Gmbh Subustituierte Isoindolone, ihre Herstellung und ihre Verwendung in Arzneimitteln
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
CA2374262A1 (en) 1999-06-01 2000-12-07 The University Of Texas Southwestern Medical Center Method of treating hair loss
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
CN100393703C (zh) * 2000-03-14 2008-06-11 埃科特莱茵药品有限公司 1,2,3,4-四氢异喹啉的衍生物
US20020032238A1 (en) * 2000-07-08 2002-03-14 Henning Priepke Biphenylcarboxylic acid amides, the preparation thereof and the use thereof as medicaments
WO2002051232A2 (en) * 2000-12-27 2002-07-04 Actelion Pharmaceuticals Ltd. Novel benzazepines and related heterocyclic derivatives
AU2002230057A1 (en) 2001-01-29 2002-08-12 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
CN1655783A (zh) * 2002-04-02 2005-08-17 株式会社津村 含有吡啶丙烯酰胺衍生物的磷酸二酯酶iv抑制剂
US6951884B2 (en) 2002-06-12 2005-10-04 Hoffmann-La Roche Inc. Fluorobenzamides and uses thereof
UA77303C2 (en) * 2002-06-14 2006-11-15 Pfizer Derivatives of thienopyridines substituted by benzocondensed heteroarylamide useful as therapeutic agents, pharmaceutical compositions and methods for their use
SE0202539D0 (sv) 2002-08-27 2002-08-27 Astrazeneca Ab Compounds
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

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