WO2000063296A3 - Cyanine dyes and synthesis methods thereof - Google Patents

Cyanine dyes and synthesis methods thereof Download PDF

Info

Publication number
WO2000063296A3
WO2000063296A3 PCT/US2000/010533 US0010533W WO0063296A3 WO 2000063296 A3 WO2000063296 A3 WO 2000063296A3 US 0010533 W US0010533 W US 0010533W WO 0063296 A3 WO0063296 A3 WO 0063296A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyanine dyes
synthesis methods
alkyl group
dye
group
Prior art date
Application number
PCT/US2000/010533
Other languages
French (fr)
Other versions
WO2000063296A2 (en
Inventor
Malcolm Harry Randall
Philip Richard Buzby
Thomas Joseph Erickson
Joseph David Trometer
Joseph John Miller Jr
David George Ahern
Mark N Bobrow
Original Assignee
Nen Life Science Prod Inc
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
Application filed by Nen Life Science Prod Inc filed Critical Nen Life Science Prod Inc
Priority to EP00923522A priority Critical patent/EP1112254B1/en
Priority to CA2335240A priority patent/CA2335240C/en
Priority to JP2000612377A priority patent/JP2002542365A/en
Priority to AU43631/00A priority patent/AU767368B2/en
Publication of WO2000063296A2 publication Critical patent/WO2000063296A2/en
Publication of WO2000063296A3 publication Critical patent/WO2000063296A3/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A61K49/0032—Methine dyes, e.g. cyanine dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0052—Small organic molecules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0056—Peptides, proteins, polyamino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Abstract

A cyanine dye having formula (II), wherein R1-R8 are each independently selected from a group consisting of hydrogen, C1-C6 alkyl group, and C0-C4 alkyl group having a hydrophilic substituent thereon. R11 and R12 are chosen to include a free or protected thiol, amine or hydroxyl substituent capable of reacting with a target molecule through a nucleophilic displacement mechanism. The dye is useful in labeling a variety of target molecules. Processes are described for synthesizing suitable heterocyclic and indole derivatives as precursors for the aforementioned cyanine dyes.
PCT/US2000/010533 1999-04-19 2000-04-19 Cyanine dyes and synthesis methods thereof WO2000063296A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP00923522A EP1112254B1 (en) 1999-04-19 2000-04-19 Cyanine dyes and synthesis methods thereof
CA2335240A CA2335240C (en) 1999-04-19 2000-04-19 Cyanine dyes and synthesis methods thereof
JP2000612377A JP2002542365A (en) 1999-04-19 2000-04-19 Cyanine dyes and their synthesis
AU43631/00A AU767368B2 (en) 1999-04-19 2000-04-19 Cyanine dyes and synthesis methods thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/294,678 US6114350A (en) 1999-04-19 1999-04-19 Cyanine dyes and synthesis methods thereof
US09/294,678 1999-04-19

Publications (2)

Publication Number Publication Date
WO2000063296A2 WO2000063296A2 (en) 2000-10-26
WO2000063296A3 true WO2000063296A3 (en) 2001-02-15

Family

ID=23134462

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/010533 WO2000063296A2 (en) 1999-04-19 2000-04-19 Cyanine dyes and synthesis methods thereof

Country Status (6)

Country Link
US (5) US6114350A (en)
EP (1) EP1112254B1 (en)
JP (1) JP2002542365A (en)
AU (1) AU767368B2 (en)
CA (1) CA2335240C (en)
WO (1) WO2000063296A2 (en)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6593148B1 (en) 1994-03-01 2003-07-15 Li-Cor, Inc. Cyanine dye compounds and labeling methods
US20080050836A1 (en) * 1998-05-01 2008-02-28 Isabelle Guyon Biomarkers for screening, predicting, and monitoring benign prostate hyperplasia
JP2000095758A (en) 1998-09-18 2000-04-04 Schering Ag Near-infrared, fluorescent contrast medium, and its production
US7547721B1 (en) 1998-09-18 2009-06-16 Bayer Schering Pharma Ag Near infrared fluorescent contrast agent and fluorescence imaging
US6114350A (en) * 1999-04-19 2000-09-05 Nen Life Science Products, Inc. Cyanine dyes and synthesis methods thereof
US20040044219A1 (en) * 2000-06-07 2004-03-04 Jennie Sandstrom Probe for analysis of nucleic acids
DE10046215B4 (en) * 2000-09-19 2004-04-15 Institut für Chemo- und Biosensorik Münster e.V. i.Ins. Fluorochromes and their use
ATE352586T2 (en) * 2000-09-29 2007-02-15 Molecular Probes Inc MODIFIED CARBOCYANINE DYES AND CONJUGATES THEREOF
US6663847B1 (en) * 2000-10-13 2003-12-16 Mallinckrodt Inc. Dynamic organ function monitoring agents
US6379622B1 (en) 2001-04-11 2002-04-30 Motorola, Inc. Sensor incorporating a quantum dot as a reference
US6694158B2 (en) 2001-04-11 2004-02-17 Motorola, Inc. System using a portable detection device for detection of an analyte through body tissue
US7521019B2 (en) * 2001-04-11 2009-04-21 Lifescan, Inc. Sensor device and methods for manufacture
US6454710B1 (en) 2001-04-11 2002-09-24 Motorola, Inc. Devices and methods for monitoring an analyte
US6887690B2 (en) * 2001-06-22 2005-05-03 Pe Corporation Dye-labeled ribonucleotide triphosphates
US9261460B2 (en) 2002-03-12 2016-02-16 Enzo Life Sciences, Inc. Real-time nucleic acid detection processes and compositions
US20050123913A1 (en) * 2001-08-30 2005-06-09 Emory University Human mitochondrial dna polymorphisms, haplogroups, associations with physiological conditions, and genotyping arrays
US7166478B2 (en) * 2002-03-12 2007-01-23 Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. Labeling reagents and labeled targets, target labeling processes and other processes for using same in nucleic acid determinations and analyses
US9353405B2 (en) 2002-03-12 2016-05-31 Enzo Life Sciences, Inc. Optimized real time nucleic acid detection processes
AU2003232089A1 (en) * 2002-05-06 2003-11-17 Perkinelmer Life Sciences, Inc. Separation process and dyes for use therewith
AU2003280470A1 (en) * 2002-07-01 2004-01-19 Guava Technologies, Inc. Fluorescent dyes, energy transfer couples and methods
CN1307263C (en) * 2002-07-08 2007-03-28 通用电气医疗集团英国有限公司 Reagent and method for saturation labelling of proteins
CA2501144C (en) * 2002-10-23 2015-10-06 University Of Utah Research Foundation Amplicon melting analysis with saturation dyes
US20040132092A1 (en) * 2003-01-03 2004-07-08 Stetson Christopher M. Determining the density of functional moieties on polymer reagents
AU2003234038B2 (en) * 2003-05-28 2008-02-21 Ge Healthcare Uk Limited Differential analysis of cell surface proteins on closed membrane structures by labelling with dyes in the presence of an internal standard
US7619059B2 (en) * 2003-07-29 2009-11-17 Life Technologies Corporation Bimolecular optical probes
US7727752B2 (en) 2003-07-29 2010-06-01 Life Technologies Corporation Kinase and phosphatase assays
CA2445420A1 (en) * 2003-07-29 2005-01-29 Invitrogen Corporation Kinase and phosphatase assays
US7271265B2 (en) * 2003-08-11 2007-09-18 Invitrogen Corporation Cyanine compounds and their application as quenching compounds
CA2538797A1 (en) * 2003-09-12 2005-03-24 Invitrogen Corporation Multiplex binding and activity assays
US7776529B2 (en) 2003-12-05 2010-08-17 Life Technologies Corporation Methine-substituted cyanine dye compounds
EP1720944B1 (en) * 2003-12-05 2013-07-17 Life Technologies Corporation Cyanine dye compounds
JP4127204B2 (en) * 2003-12-17 2008-07-30 セイコーエプソン株式会社 Manufacturing method of liquid crystal display device
US7705150B2 (en) * 2004-02-04 2010-04-27 Biosearch Technologies, Inc. Cyanine dyes
US9657347B2 (en) 2004-04-20 2017-05-23 University of Utah Research Foundation and BioFire Defense, LLC Nucleic acid melting analysis with saturation dyes
US7387887B2 (en) * 2004-04-20 2008-06-17 University Of Utah Research Foundation Nucleic acid melting analysis with saturation dyes
US7456281B2 (en) * 2005-04-20 2008-11-25 Idaho Technology, Inc. Nucleic acid melting analysis with saturation dyes
US7598390B2 (en) * 2005-05-11 2009-10-06 Life Technologies Corporation Fluorescent chemical compounds having high selectivity for double stranded DNA, and methods for their use
US7737281B2 (en) * 2005-05-24 2010-06-15 Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. Purine based fluorescent dyes
US7569695B2 (en) * 2005-05-24 2009-08-04 Enzo Life Sciences, Inc. Dyes for the detection or quantification of desirable target molecules
US8357801B2 (en) 2005-05-24 2013-01-22 Enzo Life Sciences, Inc. Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits
FR2889700B1 (en) 2005-08-11 2012-11-23 Synthinnove Lab MARKERS, METHOD FOR PRODUCING THE SAME, AND APPLICATIONS THEREOF
JP2008133458A (en) * 2006-10-27 2008-06-12 Fujifilm Corp Radioisotope-labeled pigment compound
FR2921258A1 (en) * 2007-09-24 2009-03-27 Oreal TINCTORIAL COMPOSITION COMPRISING AT LEAST ONE COLOR DISULFIDE / THIOL PRECURSOR, COLORING PROCESS FROM THE COMPOSITION
US20100291706A1 (en) * 2009-05-15 2010-11-18 Millipore Corporation Dye conjugates and methods of use
US8536323B2 (en) 2010-04-21 2013-09-17 Pierce Biotechnology, Inc. Modified nucleotides
US9206216B2 (en) 2010-04-21 2015-12-08 Pierce Biotechnology, Inc. Modified nucleotides methods and kits
WO2012027623A2 (en) 2010-08-25 2012-03-01 Pacific Biosciences Of California, Inc. Cyanine dyes
US20120088262A1 (en) * 2010-10-06 2012-04-12 Millipore Corporation Cyanine compounds, conjugates and method of use
WO2012103678A1 (en) * 2011-01-31 2012-08-09 大连理工大学 Pentamethine cyanine fluorescent dyes, preparation methods and uses thereof
US9416153B2 (en) 2011-10-11 2016-08-16 Enzo Life Sciences, Inc. Fluorescent dyes
US9315864B2 (en) 2012-05-18 2016-04-19 Pacific Biosciences Of California, Inc. Heteroarylcyanine dyes with sulfonic acid substituents
WO2013173844A1 (en) 2012-05-18 2013-11-21 Pacific Biosciences Of California, Inc. Heteroarylcyanine dyes
US10300153B2 (en) 2015-11-30 2019-05-28 Asthra, Llc Immunological detection of altered cells
CN109206351B (en) * 2018-09-18 2021-06-29 许昌学院 Cyanine structure based near-infrared fluorescent probe for detecting palladium ions, and preparation method and application thereof
CN109467523A (en) * 2018-12-17 2019-03-15 苏州华道生物药业股份有限公司 A kind of green synthesis method of the third sulfonic acid chloride of 3- chlorine
WO2020186483A1 (en) * 2019-03-20 2020-09-24 深圳大学 Pentamethine cyanine dye and preparation method therefor
US10947253B2 (en) 2019-08-05 2021-03-16 Ankh Life Sciences Limited Fused polycyclic dimers
KR102550713B1 (en) * 2021-01-18 2023-07-03 (주)바이오액츠 Fluorescent compound with cyanuric-hydroxide and the preparation method thereof

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4263397A (en) * 1977-05-24 1981-04-21 Konishiroku Photo Industry Co., Ltd. Photographic products
US4859572A (en) * 1988-05-02 1989-08-22 Eastman Kodak Company Dye sensitized photographic imaging system
US5149610A (en) * 1987-01-19 1992-09-22 Canon Kabushiki Kaisha Color toner and two-component developer containing same
US5401100A (en) * 1992-12-18 1995-03-28 Pymah Corporation Axillary thermometer packaging
US5744511A (en) * 1995-04-19 1998-04-28 Tokuyama Corporation Visible ray polymerization initiator and visible ray polymerizable composition
US5786123A (en) * 1996-03-19 1998-07-28 Eastman Kodak Company Optical recording elements comprising a polymeric dye
WO1998047538A2 (en) * 1997-04-23 1998-10-29 Institut für Diagnostikforschung GmbH an der Freien Universität Berlin Acid-labile and enzymatically divisible dye compounds for diagnosis with near infrared light and for therapy
US5863727A (en) * 1996-05-03 1999-01-26 The Perkin-Elmer Corporation Energy transfer dyes with enhanced fluorescence
US5990317A (en) * 1995-05-30 1999-11-23 Gliatech, Inc. 2-(1H-4(5)-imidazoyl) cyclopropyl compounds
US6010842A (en) * 1996-08-30 2000-01-04 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US6015989A (en) * 1996-06-28 2000-01-18 Mitsubishi Denki Kabushiki Kaisha Semiconductor device having a capacitor electrode formed of iridum or ruthenium and a quantity of oxygen
US6057311A (en) * 1996-03-08 2000-05-02 James Black Foundation Limited Benzodiazonine derivatives binding to cholecystokinin or gastrin receptors

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138551A (en) * 1975-03-18 1979-02-06 Ciba-Geigy Ag Spectral sensitization of photographic material and new spectral sensitizers
JPS62123454A (en) * 1985-08-08 1987-06-04 Fuji Photo Film Co Ltd Silver halide photographic sensitive material
US5268486A (en) * 1986-04-18 1993-12-07 Carnegie-Mellon Unversity Method for labeling and detecting materials employing arylsulfonate cyanine dyes
US5627027A (en) * 1986-04-18 1997-05-06 Carnegie Mellon University Cyanine dyes as labeling reagents for detection of biological and other materials by luminescence methods
US4981977A (en) * 1989-06-09 1991-01-01 Carnegie-Mellon University Intermediate for and fluorescent cyanine dyes containing carboxylic acid groups
US5378634A (en) * 1992-08-20 1995-01-03 Matsushita Electric Industrial Co., Ltd. Labelling color for detecting methamphetamine
US5658751A (en) * 1993-04-13 1997-08-19 Molecular Probes, Inc. Substituted unsymmetrical cyanine dyes with selected permeability
US5688966A (en) * 1996-07-26 1997-11-18 E. I. Du Pont De Nemours And Company Compounds and method for synthesizing sulfoindocyanine dyes
US6027709A (en) * 1997-01-10 2000-02-22 Li-Cor Inc. Fluorescent cyanine dyes
US5986086A (en) * 1997-06-20 1999-11-16 Amersham Pharmacia Biotech Inc. Non-sulfonated cyanine dyes for labeling nucleosides and nucleotides
US6114350A (en) * 1999-04-19 2000-09-05 Nen Life Science Products, Inc. Cyanine dyes and synthesis methods thereof

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4263397A (en) * 1977-05-24 1981-04-21 Konishiroku Photo Industry Co., Ltd. Photographic products
US5149610A (en) * 1987-01-19 1992-09-22 Canon Kabushiki Kaisha Color toner and two-component developer containing same
US4859572A (en) * 1988-05-02 1989-08-22 Eastman Kodak Company Dye sensitized photographic imaging system
US5401100A (en) * 1992-12-18 1995-03-28 Pymah Corporation Axillary thermometer packaging
US5744511A (en) * 1995-04-19 1998-04-28 Tokuyama Corporation Visible ray polymerization initiator and visible ray polymerizable composition
US5990317A (en) * 1995-05-30 1999-11-23 Gliatech, Inc. 2-(1H-4(5)-imidazoyl) cyclopropyl compounds
US6057311A (en) * 1996-03-08 2000-05-02 James Black Foundation Limited Benzodiazonine derivatives binding to cholecystokinin or gastrin receptors
US5824768A (en) * 1996-03-19 1998-10-20 Eastman Kodak Company Polymeric dyes for optical recording layers and elements
US5786123A (en) * 1996-03-19 1998-07-28 Eastman Kodak Company Optical recording elements comprising a polymeric dye
US5863727A (en) * 1996-05-03 1999-01-26 The Perkin-Elmer Corporation Energy transfer dyes with enhanced fluorescence
US6015989A (en) * 1996-06-28 2000-01-18 Mitsubishi Denki Kabushiki Kaisha Semiconductor device having a capacitor electrode formed of iridum or ruthenium and a quantity of oxygen
US6010842A (en) * 1996-08-30 2000-01-04 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
WO1998047538A2 (en) * 1997-04-23 1998-10-29 Institut für Diagnostikforschung GmbH an der Freien Universität Berlin Acid-labile and enzymatically divisible dye compounds for diagnosis with near infrared light and for therapy

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEM. ABSTRACT, (COLUMBUS, OHIO, USA); LEE ET AL.: "Energy transfer dyes with enhanced fluorescence, reagents containing them and their use in nucleic acid sequencing", XP002935809, accession no. STN Database accession no. 131:166214 *
DATABASE CA [online] CHEM. ABSTRACTS, (COLUMBUS, OHIO, USA); LICHA ET AL.: "Acid-labile and enzymically cleavable dye conjugates for diagnosis with near-IR radiation and for therapy", XP002935810, accession no. STN Database accession no. 129:335785 *
DATABASE USPATFULL [online] (COLUBMUS, OHIO, USA); SUGA ET AL.: "Silver halide photographic light-sensitive material", XP002935801, accession no. STN Database accession no. 2000:1685 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); BURNS ET AL.: "Optical recording elements comprising a polymeric dye", XP002935803, accession no. STN Database accession no. 1998:88618 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); BURNS ET AL.: "Polymeric dyes for optical recording layers and elements", XP002935802, accession no. STN Database accession no. 1998:128354 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); FARID ET AL.: "Dye sensitized photographic imaging system", XP002935807, accession no. STN Database accession no. 89:69670 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); GLUCHOWSKI ET AL.: "Use of alpha-1C specific compounds to treat benign prostatic hyperplasia", XP002935812, accession no. STN Database accession no. 2000:7320 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); HORIKOSHI ET AL.: "Photographic products", XP002935808, accession no. STN Database accession no. 81:22065 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); KALINDJIAN ET AL.: "Benzodiazonine derivatives binding to cholecystokinin or gastrin receptors", XP002935811, accession no. STN Database accession no. 2000:54094 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); KAZAMA ET AL.: "Visible ray polymerization initiator & visible ray polymerizable composition", XP002935804, accession no. STN Database accession no. 1998:45245 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); KOBAYASHI ET AL.: "Color toner and two-component developer containing same", XP002935806, accession no. STN Database accession no. 92:78799 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); PHILLIPS ET AL.: "Cyclopropyl compounds", XP002935813, accession no. STN Database accession no. 1999:151417 *
DATABASE USPATFULL [online] (COLUMBUS, OHIO, USA); THACKSON ET AL.: "Axillary thermometer packaging", XP002935805, accession no. STN Database accession no. 95:26672 *
See also references of EP1112254A4 *

Also Published As

Publication number Publication date
EP1112254A2 (en) 2001-07-04
WO2000063296A2 (en) 2000-10-26
US6204389B1 (en) 2001-03-20
EP1112254B1 (en) 2013-02-27
CA2335240A1 (en) 2000-10-26
US6114350A (en) 2000-09-05
AU767368B2 (en) 2003-11-06
EP1112254A4 (en) 2005-03-16
JP2002542365A (en) 2002-12-10
US6197956B1 (en) 2001-03-06
US20010020098A1 (en) 2001-09-06
US6224644B1 (en) 2001-05-01
US6437141B2 (en) 2002-08-20
CA2335240C (en) 2013-11-26
AU4363100A (en) 2000-11-02

Similar Documents

Publication Publication Date Title
WO2000063296A3 (en) Cyanine dyes and synthesis methods thereof
Beija et al. Synthesis and applications of Rhodamine derivatives as fluorescent probes
WO2004085539A3 (en) Cyanine dye labelling reagents with meso-substitution
WO2008111473A1 (en) Glucokinase activator
PL351878A1 (en) Amino compound derivatives
AU2003227918A1 (en) Trisazo dyes for ink jet printing
US10753942B2 (en) Methods to detect remnant cancer cells
EP1731519A4 (en) Novel indole derivative for alkylating specific base sequence of dna and alkylating agent and drug each comprising the same
BG104505A (en) Process for the preparation of thiazolidinedione derivatives
DE60101903D1 (en) FIBER REACTIVE DISCOVER CONNECTIONS
US10239891B2 (en) Compositions to detect remnant cancer cells
MY117159A (en) Indolyl-pyrrolydenemethylpyrrole derivatives and process for their preparation.
ATE248833T1 (en) SQUARYLIUM COMPOUND AND OPTICAL RECORDING MEDIUM CONTAINING SAME
EP2006289A4 (en) Pyrazole-type cyanine dye
KR950008623A (en) Tetrakisazo Compounds and Inks Containing the Compounds
WO2006024405A3 (en) Derivatives of avermectin, avermectin monosaccharide and avermectin aglycone
Tietze et al. Synthesis of New Water‐Soluble DNA‐Binding Subunits for Analogues of the Cytotoxic Antibiotic CC‐1065 and Their Prodrugs
Esteves et al. Unnatural benz-X-azolyl asparagine derivatives as novel fluorescent amino acids: synthesis and photophysical characterization
Dabbagh et al. New azoic dyes containing (1H)-tetrazole and azido group
WO2001023352A3 (en) Preparation of sulfonyl imine compounds
Banfi et al. Intramolecular transamidation of β-lactams as a means for the enzymatic control of ring opening: Effect of substituents on the rate of reaction
WO2001015737A3 (en) Method for coupling molecules
Sawa et al. Tryptamine-based human β3-adrenergic receptor agonists. Part 2: SAR of the methylene derivatives
US7034163B2 (en) Synthesis of pyrroles
Phoon et al. Traceless synthesis of urea, semicarbazide and carbamate derivatives using bromo-Wang resin and bromo-Wang SynPhaseTM lantern

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

ENP Entry into the national phase

Ref document number: 2335240

Country of ref document: CA

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2000923522

Country of ref document: EP

AK Designated states

Kind code of ref document: A3

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

WWP Wipo information: published in national office

Ref document number: 2000923522

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642