Plural Nitrogens Bonded Directly To The Xanthene Ring System (e.g., 2,6 Diaminofluorans, Etc.) Patents (Class 549/226)
  • Publication number: 20150110715
    Abstract: The present invention relates to a compound or a pharmaceutically acceptable salt thereof having a chemical structure comprising: (A) at least one motif specifically binding to cell membranes of neoplastic cells; (B) at least one chelator moiety of radiometals; and (C) at least one dye moiety; wherein said compound has a molecular weight of not more than 5 kDa. Further, the invention refers to a method for producing such compound and to the in vivo and in vitro uses thereof.
    Type: Application
    Filed: July 18, 2014
    Publication date: April 23, 2015
    Applicants: RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG, DEUTSCHES KREBSFORSCHUNGSZENTRUM
    Inventors: Matthias Eder, Klaus Kopka, Martin Schaefer, Ulrike Bauder-Wuest, Uwe Haberkorn
  • Patent number: 9006437
    Abstract: The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.
    Type: Grant
    Filed: April 9, 2013
    Date of Patent: April 14, 2015
    Assignee: Biotium, Inc.
    Inventors: Fei Mao, Wai-Yee Leung, Ching-Ying Cheung
  • Patent number: 8940859
    Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.
    Type: Grant
    Filed: March 13, 2012
    Date of Patent: January 27, 2015
    Assignee: University of Georgia Research Foundation, Inc.
    Inventors: Geert-Jan Boons, Jun Guo, Xinghai Ning, Margaretha Wolfert
  • Publication number: 20140011208
    Abstract: The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.
    Type: Application
    Filed: April 9, 2013
    Publication date: January 9, 2014
    Inventors: Fei Mao, Wai-Yee Leung, Ching-Ying Cheung, Ching-Ying Cheung
  • Publication number: 20130321521
    Abstract: There is provided a coloring composition containing a compound represented by Formula (1): wherein D represents a residue structure in which four hydrogen atoms are removed from the compound represented by Formula (2), R1 and R2 represent R1?R2?H or R1?R and R2=-L-CO2M, R represents a hydrogen atom or a monovalent substituent, and when a plurality of R is present, R's may be the same or different, L represents a divalent linking group, and when a plurality of L is present, L's may be the same or different, M represents a hydrogen atom or a counteraction, and when a plurality of M is present, M's may be the same or different, and n represents the number of 1 to 4, and m represents the number of 0 to 3, provided that m+n is 4.
    Type: Application
    Filed: May 21, 2013
    Publication date: December 5, 2013
    Applicant: FUJIFILM Corporation
    Inventors: Yoshihiko FUJIE, Keiichi TATEISHI, Clive Edwin FOSTER
  • Patent number: 8586743
    Abstract: The present disclosure is directed to a reactive ester agent capable of conjugating a reporter molecule to a carrier molecule or solid support. The reactive ester agent has the general formula: wherein the variables are described throughout the application.
    Type: Grant
    Filed: January 30, 2008
    Date of Patent: November 19, 2013
    Assignee: Life Technologies Corporation
    Inventors: Kyle Gee, Aleksey Rukavishnikov, Diane M. Witczak
  • Publication number: 20120322974
    Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.
    Type: Application
    Filed: March 13, 2012
    Publication date: December 20, 2012
    Applicant: University of Georgia Research Foundation, Inc.
    Inventors: GEERT-JAN BOONS, Jun Guo, Xinghai Ning, Margaretha Wolfert
  • Publication number: 20120172575
    Abstract: 1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.
    Type: Application
    Filed: March 13, 2012
    Publication date: July 5, 2012
    Applicant: University of Georgia Research Foundation, Inc.
    Inventors: GEERT-JAN BOONS, Jun Guo, Xinghai Ning, Margaretha Wolfert
  • Publication number: 20120149918
    Abstract: A process for the preparation of 3-dibutylamino-6-methyl-7-anilinofluoran and a heating- and pressure sensitive recording material are claimed.
    Type: Application
    Filed: August 9, 2010
    Publication date: June 14, 2012
    Applicant: BASF SE
    Inventor: Robert Montgomery O'Neil
  • Patent number: 8114904
    Abstract: Provided herein are compounds or fluorogenic probes which can be used as reagents for measuring, detecting and/or screening ROS or RNS such as peroxynitrite or hypochlorite. Provided also herein are methods that can be used to measure, directly or indirectly, the amount of peroxynitrite or hypochlorite in chemical samples and biological samples such as cells and tissues in living organisms. Specifically, the methods include the steps of contacting the fluorogenic probes disclosed herein with the samples to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite or hypochlorite in chemical and biological samples.
    Type: Grant
    Filed: April 3, 2009
    Date of Patent: February 14, 2012
    Assignee: Versitech Limited & Morningside Ventures Limited
    Inventors: Dan Yang, Tao Peng
  • Patent number: 7985865
    Abstract: A compound having the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, wherein R1 comprises a chromophore that absorbs light from the visible wavelength range, and wherein n is an integer of at least 12. A solid phase change ink composition is also disclosed containing a colorant comprising a chromophore that absorbs light from the visible wavelength range and has the formula wherein R1, Z, and the carbonyl can be comprised by a common ring, and wherein n is an integer of at least 12. Also disclosed is a method of forming a colorant wherein a first compound having the formula is reacted with a second compound having the formula Z(CH2)nCH3 wherein n is an integer of at least 12 to form a third compound having the formula wherein the third compound comprises a chromophore that absorbs light from the visible wavelength range.
    Type: Grant
    Filed: December 14, 2007
    Date of Patent: July 26, 2011
    Assignee: Xerox Corporation
    Inventors: Jeffrey H Banning, Michael B. Meinhardt, Donald R Titterington, Clifford R King
  • Publication number: 20110166366
    Abstract: Provided are chalcogenoxanthylium compounds which can effectively be used as sensitizers in photodynamic therapy, virucides in photodynamic antimicrobial chemotherapy and reversal agents of Pgp function in cancer cells. Further provided is a general method for the preparation of chalcogenoxanthylium compounds.
    Type: Application
    Filed: March 11, 2011
    Publication date: July 7, 2011
    Inventors: Michael R. Detty, David J. Donnelly, Stephen J. Wagner
  • Publication number: 20110053895
    Abstract: The invention relates to pharmacology and medicine, in particular to a class of mitochondrially-addressed compounds which can be used in the pharmaceutical compositions of medicinal agents (preparations) for preventing and treating cardiovascular diseases and diseases and pathological conditions caused by disturbed blood circulation or oxygen supply to tissues and organs.
    Type: Application
    Filed: June 29, 2007
    Publication date: March 3, 2011
    Inventors: Maxim Vladimirovich Skulachev, Vladimir Petrovich Skulachev
  • Patent number: 7704756
    Abstract: Fluorogenic or chromogenic dyes are useful as reporter molecules for detecting cell entry by a specific molecule.
    Type: Grant
    Filed: January 30, 2006
    Date of Patent: April 27, 2010
    Assignee: Novartis Vaccines and Diagnostics, Inc.
    Inventors: Daniel J. Suich, Ronald N. Zuckermann
  • Patent number: 7615377
    Abstract: The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: November 10, 2009
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen J. Lippard, Elizabeth Marie Nolan
  • Patent number: 7399639
    Abstract: The present invention is directed, in part, to sensors for detecting metal ions, and methods of making and using the same.
    Type: Grant
    Filed: May 4, 2003
    Date of Patent: July 15, 2008
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen J. Lippard, Carolyn Crystal Woodroofe
  • Patent number: 6998493
    Abstract: Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +p wherein p is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, and R1, R2, R3, R4, R5, R6, R7, a, b, c, d, Y, Q?, A, and CA are as defined herein.
    Type: Grant
    Filed: June 26, 2003
    Date of Patent: February 14, 2006
    Assignee: Xerox Corporation
    Inventors: Jeffery H. Banning, Bo Wu, James M. Duff, Wolfgang G. Wedler, Jule W. Thomas, Jr., Randall R. Bridgeman
  • Patent number: 6916925
    Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds arc useful, inter alia, for determining the binding and/or receptor sites of the molecules.
    Type: Grant
    Filed: July 22, 2003
    Date of Patent: July 12, 2005
    Assignee: 3M Innovative Properties Co.
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Patent number: 6635602
    Abstract: A process for the manufacture of mixtures of fluoran compounds by the reaction of keto acids of formula (II) with a compound of formula (III) in the presence of a dehydrating condensation agent, wherein R1 and R2 independently represent hydrogen; an alkyl of 1-18 carbon, a secondary alkyl with respect to the carbon atom bonded to the nitrogen atom of 3-13 carbon atoms, a cycloalkyl of 4-8 carbon atoms or a phenyl, both of which may be substituted by at least one substituted selected from the group consisting of halogen atoms and alkyls having 1-4 carbon atoms, an aralkyl of 7-10 carbon atoms; or R1 and R2, together with the adjacent nitrogen atom from a heterocyclic ring; R3 is hydrogen, an alkyl of 1-4 carbon atoms, an alkoxy of 1-4 carbon atoms, a phenyl; a substituted phenyl or a halogen; R4 is an alkyl group of 1-18 carbon atoms, a carboxyalkyl of 1-18 carbon atoms, a carboxycycloalkyl of 4-8 carbon atoms, an alkylamino of 1-18 carbon atoms, a cycloalkylamino of 4-8 carbon atoms, a dialkylamino or dicyclo
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: October 21, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: James Philip Taylor, Michael Heneghan
  • Patent number: 6630588
    Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.
    Type: Grant
    Filed: February 19, 2002
    Date of Patent: October 7, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Patent number: 6605731
    Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodarnines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene, colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.
    Type: Grant
    Filed: October 4, 2002
    Date of Patent: August 12, 2003
    Assignee: Milliken & Company
    Inventors: Rajnish Batlaw, Patrick D. Moore
  • Publication number: 20030096192
    Abstract: Optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and, if desired, a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue or red light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one xanthene dye which contains at least two anionic groups and has at least one cation containing at least one conjugated &pgr; system having at least 6 &pgr; electrons as counterion, where the cation must not be benzyltrimethylammonium, benzyltriethylammonium, tetraphenylphosphonium, butyltriphenylphosphonium or ethyltriphenylphosphonium, is used as light-absorbent compound.
    Type: Application
    Filed: March 20, 2002
    Publication date: May 22, 2003
    Inventors: Horst Berneth, Friedrich-Karl Bruder, Wilfried Haese, Rainer Hagen, Karin Hassenruck, Serguei Kostromine, Peter Landenberger, Rafael Oser, Thomas Sommermann, Josef-Walter Stawitz, Thomas Bieringer
  • Publication number: 20030068668
    Abstract: Systems, including compositions and methods, for measuring pH, particularly in cells, organelles, and other samples. The compositions include pH-sensitive fluorescent and fluorogenic 2′,7′-dialkylfluorescein derivatives and associated nonfluorescent precursor compounds. The compositions may permit ratiometric measurement in the excitation spectrum and the emission spectrum. The methods include adding a precursor compound to a sample cell, incubating the sample cell to release the free indicator, illuminating the sample cell, and detecting the fluorescence response of the free indicator.
    Type: Application
    Filed: March 27, 2002
    Publication date: April 10, 2003
    Inventors: Zhenjun Diwu, Jesse J. Twu, Guoliang Yi, Luke D. Lavis, Yen-Wen Chen, Kelly J. Cassutt
  • Publication number: 20030050481
    Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodarnines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene, colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.
    Type: Application
    Filed: October 4, 2002
    Publication date: March 13, 2003
    Inventors: Rajnish Batlaw, Patrick D. Moore
  • Patent number: 6452020
    Abstract: Novel addition products of isocyanates with oxyalkylene-substituted aminophenol compounds as intermediates for the production of urethane-substituted xanthene colorants, particularly triphenylmethane derivatives such as rhodamines, are provided. The xanthene colorants exhibit improved wax and/or oil solubility and high purity. The urethane-substituted xanthene colorant features very good wax and/or oil solubility, and is believed to be relatively nontoxic. A method for producing this novel colorant is also provided.
    Type: Grant
    Filed: April 10, 2001
    Date of Patent: September 17, 2002
    Assignee: Milliken & Company
    Inventors: Rajnish Batlaw, Patrick D. Moore
  • Patent number: 6376669
    Abstract: Dye labeled imidazonaphthyridine, imidazopyridine and imidazoquinoline compounds having immune response modulating activity are disclosed. The compounds are useful, inter alia, for determining the binding and/or receptor sites of the molecules.
    Type: Grant
    Filed: November 2, 2000
    Date of Patent: April 23, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Michael J. Rice, Mark A. Tomai, Ai-Ping Wei
  • Patent number: 6162931
    Abstract: The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: December 19, 2000
    Assignee: Molecular Probes, Inc.
    Inventors: Kyle R. Gee, Martin Poot, Dieter H. Klaubert, Wei-Chuan Sun, Richard P. Haugland, Fei Mao
  • Patent number: 6143904
    Abstract: The invention describes a color former mixture comprising(a) a compound of formula (1) and/or of formula (2) and/or of formula (3) and(b) a compound of formula (4),or a color former mixture comprising at least two compounds of component (b).The color former mixture is suitable for pressure- and particularly for heat-sensitive recording materials and has excellent storage ability and superior paper whiteness.
    Type: Grant
    Filed: June 17, 1997
    Date of Patent: November 7, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Rudolf Zink, Klaus Huber
  • Patent number: 6130101
    Abstract: The present invention describes xanthene dyes, including rhodamines, rhodols and fluoresceins that are substituted one or more times by a sulfonic acid or a salt of a sulfonic acid. The dyes of the invention, including chemically reactive dyes and dye-conjugates are useful as fluorescent probes, particularly in biological samples.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: October 10, 2000
    Assignee: Molecular Probes, Inc.
    Inventors: Fei Mao, Wai-Yee Leung, Richard P. Haugland
  • Patent number: 5376617
    Abstract: The improved .beta.-type crystal modification of 2-(3-methylanilino)-3-methyl-6-diethylaminofluoran has high solubility in inner-phase solvents. The compound is very useful as a color former for pressure-sensitive recording materials and thermal recording materials. Recording materials that use this compound as color former exhibit good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and color fastness of image.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: December 27, 1994
    Assignee: Yamamoto Chemicals, Inc.
    Inventors: Yojiro Kumagae, Shigeo Fujita, Mansuke Matsumoto, Sayuri Wada, Shuuichi Hashimoto
  • Patent number: 5342967
    Abstract: The improved two types of crystal modification of 2-n-toluidino-3-methyl-6-di-n-butylaminofluoran, as well as the crystalline toluene adduct thereof have high solubility in inner-phase solvent(s). Recording materials that use those compounds as electron donating color formers exhibit particularly good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and image storage stability.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: August 30, 1994
    Assignee: Yamamoto Chemicals, Inc.
    Inventors: Shigeo Fujita, Mansuke Matsumoto, Yojiro Kumagae, Sayuri Wada, Shuichi Hashimoto
  • Patent number: 5338866
    Abstract: The improved .beta.-type crystal modification of 2-(3-methylanilino)-3-methyl-6-diethylaminofluoran has high solubility in inner-phase solvents. The compound is very useful as a color former for pressure-sensitive recording materials and thermal recording materials. Recording materials that use this compound as color former exhibit good performance in various characteristics such as whiteness of the background, its storage stability, color rendition, sensitivity for color formation and color fastness of image.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: August 16, 1994
    Assignee: Yamamoto Chemicals, Inc.
    Inventors: Yojiro Kumagae, Shigeo Fujita, Mansuke Matsumoto, Sayuri Wada, Shuuichi Hashimoto
  • Patent number: 5331097
    Abstract: A diamino-xanthene colorant is provided having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of at least 3 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.3, where R.sub.3 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.4, Cl and OH, where R.sub.4 is C1-C4 alkyl or aryl, and n is 0, 1, or 2; the colorant is synthesized by condensing two moles of an N,N-bis(poly(oxyalkylene))-p-methoxyaniline and o-formylbenzene sulfonic acid.
    Type: Grant
    Filed: August 13, 1991
    Date of Patent: July 19, 1994
    Assignee: Milliken Research Corporation
    Inventors: Timothy B. Gunnell, John B. Hines, Jr., Carey N. Barry, Jr.
  • Patent number: 5324704
    Abstract: Disclosed are novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are different groups selected from cyclohexyl, n-butyl and isobutyl, e.g., in the form of crystals characterized by a specific X-ray diffraction diagram; crystalline toluene adducts thereof; and recording materials containing these fluoran compounds.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: June 28, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5315015
    Abstract: Compounds of the formula ##STR1## wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: May 24, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Raymond A. Hui, Kathryn S. Schwenzer
  • Patent number: 5300661
    Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula (I) ##STR1## ,characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: April 5, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5283222
    Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula (I) ##STR1## , characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: February 1, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5274155
    Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: December 28, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: John K. Thottathil, David Kronenthal
  • Patent number: 5250708
    Abstract: A poly(oxyalkylene) substituted xanthene colorant is providing having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of from 3 to 400 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C8 alkyl, aryl and Y, provided that if either R.sub.1 or R.sub.2 are Y, the other is not H;R.sub.3 and R.sub.4 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.5, where R.sub.5 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.6, Cl, and OH, where R.sub.6 is C1-C4 alkyl or aryl, and n is 0, 1, 2 or 3.The colorant is synthesized using a novel poly(oxyalkylene) substituted aminophenol intermediate.
    Type: Grant
    Filed: August 13, 1991
    Date of Patent: October 5, 1993
    Assignee: Milliken Research Corporation
    Inventor: Carey N. Barry, Jr.
  • Patent number: 5248791
    Abstract: A fluorescence polarization immunoassay (FPIA) for detecting the presence of one or more amphetamine-class analytes in a test sample is provided. The immunoassay uses competition between the analyte and a fluorescently labeled tracer for the binding site on an antibody specific for phenethylamine derivatives. The concentration of amphetamine-class analyte in the sample determines the amount of tracer that binds to the antibody. The amount of tracer/antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of analyte in the test sample. The invention relates to tracers, to immunogens used to elicit antibodies for use as assay reagents, and to assay kits incorporating these tracers and assay reagents.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: September 28, 1993
    Assignee: Abbott Laboratories
    Inventors: Paul J. Brynes, Donald D. Johnson, Cynthia M. Molina, Charles A. Flentge, Patrick F. Jonas
  • Patent number: 5244769
    Abstract: A light-sensitive image-forming material is disclosed, comprising a support having thereon a recording layer containing a leuco dye which forms color upon oxidative development, a photo-oxidizing agent and a reducing agent, wherein the leuco dye is an xanthene compound having a cyclic amino group at the 2-position. The light-sensitive image-forming material of the present invention provides an image having satisfactory color density and stability to light after imagewise exposure and fixation.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: September 14, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Naoto Yanagihara, Akihiko Takeda, Akira Igarashi
  • Patent number: 5245049
    Abstract: Disclosed are a crystal and crystalline solvate of a fluoran compound represented by the formula ##STR1## wherein R.sub.1 is ##STR2## and which are useful as chromogenic compounds in recording materials such as pressure-sensitive and heat-sensitive recording materials, a process for preparation of said crystal and said crystalline solvate, and recording materials comprising said crystal or said crystalline solvate.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: September 14, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5220038
    Abstract: Disclosed are novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are different groups selected from cyclohexyl, n-butyl and isobutyl, e.g., in the form of crystals characterized by a specific X-ray diffraction diagram; crystalline toluene adducts thereof; and recording materials containing these fluoran compounds.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: June 15, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5210221
    Abstract: Disclosed are a crystal of a fluoran compound having the formula (I) comprising exhibiting high peaks at diffraction angles (2.theta.) of 7.5.degree. and 17.0.degree. and relatively high peaks at diffraction angles (2.theta.) of 15.1.degree., 19.1.degree., 21.5.degree. and 25.3.degree. in an X-ray diffraction diagram by the Cu-K.alpha. beam and a crystal of a fluoran compound having the formula (II) comprising exhibiting high peaks at diffraction angles (2.theta.) of 5.5.degree. and 19.2.degree. in an X-ray diffraction diagram by the Cu-K.alpha. beam, which is useful as a color forming compound in recording materials.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: May 11, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5208209
    Abstract: Novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 4 carbon atoms, preparation process of the fluoran compounds, and a heat-sensitive and a pressure-sensitive recording material comprising the fluoran compound, are disclosed.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 4, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5194632
    Abstract: Disclosed are a novel fluoran compound represented by the formula (I): ##STR1## and a heat-sensitive recording paper which is obtained by using the fluoran compound as a chromogenic compound and is excellent in preserving stability.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: March 16, 1993
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
  • Patent number: 5185453
    Abstract: Disclosed are novel crystal of the fluoran compound represented by the formula ##STR1## , characterized by a specific X-ray diffraction diagram; preparation process thereof; and recording materials comprising the crystal.
    Type: Grant
    Filed: June 19, 1991
    Date of Patent: February 9, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Kazuyoshi Kikkawa, Akihiro Yamaguchi
  • Patent number: 5166350
    Abstract: A process for the preparation of a fluoran compound of the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy,R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX.sub.3 X.sub.4, or (R.sub.1 and R.sub.2) or (R.sub.3 and R.sub.4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus,X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X.sub.1 and X.sub.2) or (X.sub.3 and X.sub.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
  • Patent number: 5149830
    Abstract: Substituted xanthene compounds are described which are capable of functioning as absorbers in high intensity light protective compositions and in materials used to prevent the transmission of high intensity light at selected wavelengths. Also described are high intensity light protective compositions containing an effective amount of a substituted xanthene compound and a polymeric compound and a material which prevents transmission of high intensity light at wavelengths between about 482 to about 556 nanometers. The material of this invention can be used to make protective eyewear, optical filters, shields for protecting a persons body from high intensity light, or shields for protecting components of an optical instrument from high intensity light.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: September 22, 1992
    Assignee: Steadfast, Inc.
    Inventors: Louis Locatell, Kenneth Norland, F. Donald Roberts, Charles Zepp
  • Patent number: 5110952
    Abstract: A method of producing a high melting point 3-dibutyl amino-6-methyl-7-anilinofluoran characterized by peaks at diffraction angle (2 .theta.) of 6.9.degree., 11.0.degree., 18.5.degree. and 18.9.degree. in X-ray diffractiometry using Cu-K .alpha. ray and having a melting point in the range of 179.degree.-186.degree. C., which comprises: condensing 2-(4-dibutylamino-2-hydroxy-benzoyl) benzoic acid with 4-methoxy-2-methyldiphenylamine in the presence of concentrated sulfuric acid to provide a phthalide at a temperature in the range of 0.degree.-50.degree. C., neutralizing the phthalide, and then subjecting the phthalide to ring closure reaction using an alkali in an amount of 0.5-15 mols per mol of the compound used in smaller amounts of 2-(4-dibutylamino-2-hydroxy-benzoyl) benzoic acid and 4-methoxy-2-methyldiphenylamine at a temperature of not less than 50.degree. C. in the presence or absence of an organic solvent.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: May 5, 1992
    Assignee: Yamamoto Chemicals, Inc.
    Inventors: Hiroaki Harada, Yasuhisa Iwasaki