The Xanthene Ring System Is Three Cyclos Of A Polycyclo Ring System Having At Least Four Rings (e.g., Benz(c)fluorans, Etc.) Patents (Class 549/224)
  • Patent number: 6346536
    Abstract: Poly(ADP-ribose) polymerase (“PARP”) inhibitors and methods for treating neurodegenerative diseases, neural tissue damage related to cerebral ischemia and reperfusion injury, and cardiovascular in an animal.
    Type: Grant
    Filed: September 3, 1997
    Date of Patent: February 12, 2002
    Assignee: Guilford Pharmaceuticals Inc.
    Inventors: Jia-He Li, Paul F. Jackson, Keith M. Maclin, Jie Zhang
  • Patent number: 6303775
    Abstract: A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure wherein Y1 and Y2 are individually hydroxyl, amino, imminium, or oxygen, R1-R8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure where substituents R3-R7 correspond to like-referenced substituents in the structure of described above, and Y2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: October 16, 2001
    Assignee: The Perkin-Elmer Corporation
    Inventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
  • Publication number: 20010007905
    Abstract: Extended rhodamine compounds exhibiting favorable fluorescence characteristics having the structure 1
    Type: Application
    Filed: February 9, 2001
    Publication date: July 12, 2001
    Applicant: The Perkin-Elmer Corporation
    Inventors: Joe Y.L. Lam, Scott C. Benson, Steven M. Menchen
  • 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: 6140513
    Abstract: Provided is an electron donating dye precursor represented by the following formula (1), (2), (3) or (4) as defined in the specification which each singly develops two colors upon color forming reaction with one kind of an electron accepting color developer depending on change in the heat energy applied. Furthermore, a heat-sensitive recording material comprising a support and a recording layer containing said electron donating dye precursor and an electron accepting color developer is provided. Moreover, a method for heat sensitive recording of multi-color images using said heat-sensitive recording material is provided.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: October 31, 2000
    Assignee: Mitsubishi Paper Mills Limited
    Inventor: Kazuyuki Iida
  • Patent number: 6071853
    Abstract: Disclosed are a novel crystal form of the fluoran compound represented by formula (I) as characterised by specific X-ray powder diffraction pattern and melting range; process for the preparation of said novel crystal form and recording materials comprising the said crystal form.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: June 6, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Roy Alan Kirk, Jonathon Gawtrey, Michael Heneghan, John Whitworth, Ian Antony Dearden, James Philip Taylor, John Barry Henshall
  • Patent number: 6020481
    Abstract: A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein Y.sub.1 and Y.sub.2 are individually hydroxyl amino, imminium, or oxygen, R.sub.1 -R.sub.8 are hydrogen, fluorine, chlorine, alkyl, alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R.sub.9 is acetylene, alkane, alkene, cyano, substituted phenyl, and combinations thereof. The invention further includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure ##STR2## where substituents R.sub.3 -R.sub.7 correspond to like-referenced substituents in the structure of described above, and Y.sub.2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates.
    Type: Grant
    Filed: April 1, 1996
    Date of Patent: February 1, 2000
    Assignee: The Perkin-Elmer Corporation
    Inventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
  • Patent number: 6008379
    Abstract: A class of aromatic-substituted xanthene compounds useful as fluorescent dyes is disclosed, the compounds having the general structure where Y.sub.1 and Y.sub.2 taken separately are selected from the group consisting of hydroxyl, oxygen, imminium, linking group and amine, or Y.sub.1 taken together with R.sub.2 is cyclic imine, or Y.sub.2 taken together with R.sub.3 is cyclic amine; R.sub.2, R.sub.3, R.sub.5, and R.sub.7 taken separately are selected from the group consisting of hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, imminium, amido, nitrile, lower alkoxy, phenyl, and linking group; R.sub.1 taken separately is selected from the group consisting of phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, linking group and electron-rich heterocycle, or when taken together with R.sub.7 is selected from the group consisting of electron-rich heterocycle and indene; R.sub.
    Type: Grant
    Filed: October 1, 1997
    Date of Patent: December 28, 1999
    Assignee: The Perkin-Elmer Corporation
    Inventors: Scott Conrad Benson, Steven Michael Menchen, Peter David Theisen, Krishna Gajanan Upadhya, Joan Dale Hauser
  • Patent number: 5616729
    Abstract: Triggerable dioxetanes with a fluorescent substituent bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are carbon containing groups and wherein one of R.sub.1, R.sub.2 and R.sub.3 is a tethered fluorescent substitutent. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: April 1, 1997
    Assignee: Board of Governors of Wayne State University
    Inventors: Arthur P. Schaap, Hashem Akhavan-Tafti
  • Patent number: 5516864
    Abstract: This invention describes novel sensors for ions that are based on the combination of xanthylium-based dyes with metal-binding N,N'-diaryldiaza crown ethers. These sensors are primarily useful for detection and quantitation of alkali-metal ions in aqueous solution. Binding of the ion results in a change in the fluorescence properties of the indicating dye that can be correlated with the ion concentration. Methods are provided for attaching reactive groups on these sensors for conjugation to dyes, lipids and polymers and for enhancing entry of the indicators into living cells.
    Type: Grant
    Filed: January 19, 1995
    Date of Patent: May 14, 1996
    Assignee: Molecular Probes, Inc.
    Inventors: Michael A. Kuhn, Richard P. Haugland
  • 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: 5231069
    Abstract: Heat-sensitive recording paper which employs as a chromogenic compound a novel fluoran compound represented by the formula: ##STR1## and prepared reacting a benzoic acid derivative of the formula: ##STR2## with a diphenylamine derivative of the formula: ##STR3## wherein R is a lower alkyl group have excellent stability.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: July 27, 1993
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, 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: 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: 5188934
    Abstract: Long wavelength, narrow emission bandwidth fluorecein dyes are provided for detecting spacially overlapping target substances. The dyes comprise 4,7-dichlorofluoresceins, and particularly 1',2',7',8'-dibenzo-4,7-dichlorofluoresceins. Methods of using the dyes in automated DNA sequencing are described.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: February 23, 1993
    Assignee: Applied Biosystems, Inc.
    Inventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam Woo, Steven Fung
  • 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: 5055595
    Abstract: Etherified fluorescein compounds of the general formula ##STR1## in which X.sub.1 is alkyl having 4 to 12 carbon atoms or cycloalkyl and X.sub.2 is alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or cycloalkyl, the rings A and B, independently of one another, are unsubstituted or substituted by halogen, lower alkyl or lower alkoxy, and the ring D is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, amino, mono-lower alkylamino or di-lower alkylamino, with the exception that X.sub.1 and X.sub.2 are not at the same time n-butyl.These novel lactone compounds are particularly suitable for use a color formers in pressure-sensitive or heat-sensitive recording materials and they produce intense yellow, orange or rose-pink colorations.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: October 8, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Bernhard Wietfeld
  • Patent number: 5055594
    Abstract: A fluorogenic substrate for tryptophanase useful for identifying an unknown microorganism is a fluorescent dye linked to an amino acid by a carbamate or thiocarbamate group. In preferred substrates, the dye is fluorescein or 7-amino-4-methyl coumarin and the amino acid linked thereto is cysteine, threonine or serine.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Becton, Dickinson and Company
    Inventor: Patrick D. Mize
  • Patent number: 4954631
    Abstract: Fluoran compounds are disclosed of formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently represent hydrogen, halogen, lower alkoxy, C.sub.1 -C.sub.9 -alkyl, C.sub.5 or C.sub.6 -cycloalkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl or lower alkoxy, and further R.sub.1 and R.sub.2 as well as R.sub.3 and R.sub.4 taken together with Ring A, may form a naphthalene ring optionally substituted by halogen, lower alkyl or lower alkoxy, R.sub.5, R.sub.6 and R.sub.7 independently represent halogen, lower alkyl or lower alkoxy, B.sub.1 and B.sub.2 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl, lower alkoxy, or alkyl-substituted, X represents hydrogen atom or --NR.sub.8 R.sub.9 wherein R.sub.8 and R.sub.9 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.5 or C.sub.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: September 4, 1990
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Takeo Obitsu, Yutaka Ohnishi, Shinji Yoshinaka, Minoru Koguchi, Mitsuhiro Yanagita, Nobuyuki Hirai
  • Patent number: 4945171
    Abstract: Synthesis and applications of fluorescent dyes which are derivatives of benzo[c]xanthenes is described. The dyes exhibit pH dependent absorption and fluorescence spectra with pKas near the normal physiological range. Unlike fluorescein, the dyes exhibit emission of different characteristic wavelengths dependent on the pH of the medium. This permits several methods of measuring the pH of the medium in contact with the indicator including measuring two emissions with one excitation, selectively exiting the acid and base forms independently and measuring their emission at either single or dual wavelengths, or measuring the characteristic pH dependent absorption or fluorescence excitation spectral. Methods are presented for making the indicators permeant to cell membranes for the measurement of intracellular pH.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: July 31, 1990
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, James Whitaker
  • Patent number: 4933471
    Abstract: Novel xanthene dyes are disclosed which excite in the range of 450-650 nm and which will emit to the red of fluoroscein. These dyes may be coupled to tagging agents, such as monoclonal antibodies, and used to detect cells in a sample.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: June 12, 1990
    Assignee: Becton, Dickinson and Company
    Inventor: Linda Lee
  • Patent number: 4826976
    Abstract: This invention relates to a color-shifted dye compounds containing at least one thermally unstable carbamate moiety which are useful in thermal imaging. These compounds may be represented by the formula [M--(X).sub.q ].sub.p D wherein M is a carbamate moiety; X is --N.dbd., --SO.sub.2 -- or --CH.sub.2 --; D taken with X and M represents the radical of a color-shifted organic dye, said carbamate moiety M comprising a tert-alkoxycarbonyl group, ##STR1## wherein R' is halomethyl or alkyl.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: May 2, 1989
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Ernest W. Ellis, Donald A. McGowan
  • Patent number: 4775656
    Abstract: A recording material comprises a layer containing a leuco dye provided on a support, characterized in that the leuco dye has the formula (I): ##STR1## in which one of X and Y is a single bond and the other is sulfur atom; each of R.sub.1 and R.sup.2 independently is an alkyl group, a cycloalkyl group or an aralkyl group; each of R.sup.3 and R.sup.4 independently is hydrogen, a halogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, an aralkyl group or an aryloxy group; R.sup.5 is hydrogen, a halogen atom, an alkyl group, an alkoxy group, nitro or amino; and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may have one or more substituent groups.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 4, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toru Harada, Toshiyuki Watanabe
  • Patent number: 4687862
    Abstract: The fluoran compounds of the formula (I) are new red color forming chromogenic dyes. ##STR1## wherein R represents an isobutyl or isopentyl group, R.sub.1 represents a hydrogen or halogen atom or an alkyl group, R.sub.2 represents a hydrogen or halogen atom or an alkyl group, R.sub.3 represents a hydrogen atom, and R.sub.4 represents a hydrogen atom, or R.sub.4 and R.sub.1 as well as R.sub.2 and R.sub.3 taken together with the carbon atoms to which they are attached may form a benzene ring which may be substituted with a halogen atom. They are used, together with an acidic developer, in chromogenic recording materials for use in pressure sensitive copying paper, heat-sensitive recording paper and thermo-sensitive, reversible color changing composition.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: August 18, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Takeo Obitsu, Tetsuo Igaki, Kimiaki Kinoshita, Morio Nanbu, Shinichi Satoh
  • Patent number: 4668967
    Abstract: 3-N-isobutyl-ethylamino-7-phenylaminofluoran is a new green color former. It is used, together with an acidic substance, in color forming record materials for use in pressure sensitive copying paper, heat-sensitive recording paper and the like.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: May 26, 1987
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Takeo Obitsu, Tetsuo Igaki, Kazuyuki Horisawa, Morio Nanbu, Kimiaki Kinoshita, Sumio Manaka
  • Patent number: 4612558
    Abstract: A fluoran compound having the formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzyl group, Q is ##STR2## (wherein X is a hydrogen atom, a halogen atom, or a straight chain or branched alkyl group having from 1 to 8 carbon atoms), ##STR3## (wherein X is as defined above), or --(CH.sub.2).sub.n OR.sub.4 (wherein R.sub.4 is a straight chain or branched alkyl group having from 1 to 8 carbon atoms, a cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzyl group, and n is an integer of from 1 to 8), and R.sub.3 is a hydrogen atom, a halogen atom, a lower fluoroalkyl group, an acyl group, an alkoxy group, an alkoxyalkyl group, or a straight chain or branched alkyl group having from 1 to 8 carbon atoms.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: September 16, 1986
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Mitsutoshi Anzai, Masahiko Yamaguchi, Kazuyuki Wakasugi, Susumu Suzuka, Michihiro Gonda, Toshiyuki Abe, Katsumasa Kikkawa, Mikiko Kanasugi
  • Patent number: 4603202
    Abstract: Fluorans of the formula (I) ##STR1## where R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or unsubstituted or substituted alkyl, R.sup.3 is hydrogen, unsubstituted or substituted alkyl, cycloalkyl or unsubstituted or substituted phenyl, or ##STR2## is a 5-membered or 6-membered saturated heterocyclic radical, R.sup.4 and R.sup.5 independently of one another are each hydrogen, alkyl, alkoxy or halogen, R.sup.6 is hydrogen, halogen, alkyl, alkoxy, phenylalkoxy, phenoxy, phenyl or unsubstituted or substituted amino, or is pyrrolidinyl, piperidinyl or morpholinyl, R.sup.7 is hydrogen, alkyl or halogen, R.sup.8 is C.sub.1 -C.sub.5 -alkyl, and the radicals R.sup.4 and R.sup.5 and/or R.sup.6 and R.sup.7 together may furthermore each be a --CH.dbd.CH--CH.dbd.CH-- bridge, and the fused-on benzo ring may be further substituted, are used for the preparation of pressure-sensitive and heat-sensitive recording materials.
    Type: Grant
    Filed: October 12, 1984
    Date of Patent: July 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Mayer, Andreas Oberlinner
  • Patent number: 4410708
    Abstract: Certain 3-substituted amino-7-substituted fluoran derivatives useful as color recording materials.
    Type: Grant
    Filed: February 3, 1976
    Date of Patent: October 18, 1983
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Masakichi Yahagi, Shoichi Horiuchi, Takahumi Toyama, Akio Kashiwagi, Teruo Suzuki, Tetsuo Igaki, Kazuyuki Horisawa, Mituhiro Shoji
  • Patent number: 4362668
    Abstract: Ortho-quinones with alkyl, olefin polymer, or halogen substituents and a process for the preparation of these compounds comprising a base catalyzed halogen oxidation of alkylated phenol.
    Type: Grant
    Filed: July 31, 1979
    Date of Patent: December 7, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventor: Richard J. Lee