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)
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Patent number: 6346536Abstract: 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: GrantFiled: September 3, 1997Date of Patent: February 12, 2002Assignee: Guilford Pharmaceuticals Inc.Inventors: Jia-He Li, Paul F. Jackson, Keith M. Maclin, Jie Zhang
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Patent number: 6303775Abstract: 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: GrantFiled: February 1, 2000Date of Patent: October 16, 2001Assignee: The Perkin-Elmer CorporationInventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
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Publication number: 20010007905Abstract: Extended rhodamine compounds exhibiting favorable fluorescence characteristics having the structure 1Type: ApplicationFiled: February 9, 2001Publication date: July 12, 2001Applicant: The Perkin-Elmer CorporationInventors: Joe Y.L. Lam, Scott C. Benson, Steven M. Menchen
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Patent number: 6162931Abstract: 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: GrantFiled: April 12, 1996Date of Patent: December 19, 2000Assignee: Molecular Probes, Inc.Inventors: Kyle R. Gee, Martin Poot, Dieter H. Klaubert, Wei-Chuan Sun, Richard P. Haugland, Fei Mao
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Patent number: 6140513Abstract: 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: GrantFiled: September 26, 1997Date of Patent: October 31, 2000Assignee: Mitsubishi Paper Mills LimitedInventor: Kazuyuki Iida
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Patent number: 6071853Abstract: 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: GrantFiled: November 24, 1998Date of Patent: June 6, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Roy Alan Kirk, Jonathon Gawtrey, Michael Heneghan, John Whitworth, Ian Antony Dearden, James Philip Taylor, John Barry Henshall
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Patent number: 6020481Abstract: 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: GrantFiled: April 1, 1996Date of Patent: February 1, 2000Assignee: The Perkin-Elmer CorporationInventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
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Patent number: 6008379Abstract: 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: GrantFiled: October 1, 1997Date of Patent: December 28, 1999Assignee: The Perkin-Elmer CorporationInventors: Scott Conrad Benson, Steven Michael Menchen, Peter David Theisen, Krishna Gajanan Upadhya, Joan Dale Hauser
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Patent number: 5616729Abstract: 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: GrantFiled: December 27, 1988Date of Patent: April 1, 1997Assignee: Board of Governors of Wayne State UniversityInventors: Arthur P. Schaap, Hashem Akhavan-Tafti
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Patent number: 5516864Abstract: 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: GrantFiled: January 19, 1995Date of Patent: May 14, 1996Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5324704Abstract: 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: GrantFiled: March 29, 1993Date of Patent: June 28, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5315015Abstract: 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: GrantFiled: November 10, 1992Date of Patent: May 24, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Raymond A. Hui, Kathryn S. Schwenzer
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Patent number: 5231069Abstract: 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: GrantFiled: December 4, 1992Date of Patent: July 27, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5220038Abstract: 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: GrantFiled: July 18, 1990Date of Patent: June 15, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5194632Abstract: 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: GrantFiled: July 31, 1990Date of Patent: March 16, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Masakatsu Nakatsuka, Atsuo Otsuji, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5188934Abstract: 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: GrantFiled: November 14, 1989Date of Patent: February 23, 1993Assignee: Applied Biosystems, Inc.Inventors: Steven M. Menchen, Linda G. Lee, Charles R. Connell, N. Davis Hershey, Vergine Chakerian, Sam Woo, Steven Fung
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Patent number: 5166350Abstract: 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: GrantFiled: September 30, 1991Date of Patent: November 24, 1992Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
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Patent number: 5055595Abstract: 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: GrantFiled: November 14, 1989Date of Patent: October 8, 1991Assignee: Ciba-Geigy CorporationInventor: Bernhard Wietfeld
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Patent number: 5055594Abstract: 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: GrantFiled: July 19, 1990Date of Patent: October 8, 1991Assignee: Becton, Dickinson and CompanyInventor: Patrick D. Mize
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Patent number: 4954631Abstract: 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: GrantFiled: February 2, 1989Date of Patent: September 4, 1990Assignee: Shin Nisso Kako Co., Ltd.Inventors: Takeo Obitsu, Yutaka Ohnishi, Shinji Yoshinaka, Minoru Koguchi, Mitsuhiro Yanagita, Nobuyuki Hirai
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Patent number: 4945171Abstract: 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: GrantFiled: August 10, 1987Date of Patent: July 31, 1990Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, James Whitaker
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Patent number: 4933471Abstract: 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: GrantFiled: August 31, 1988Date of Patent: June 12, 1990Assignee: Becton, Dickinson and CompanyInventor: Linda Lee
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Patent number: 4826976Abstract: 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: GrantFiled: December 18, 1987Date of Patent: May 2, 1989Assignee: Polaroid CorporationInventors: Alan L. Borror, Ernest W. Ellis, Donald A. McGowan
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Patent number: 4775656Abstract: 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: GrantFiled: October 30, 1987Date of Patent: October 4, 1988Assignee: Fuji Photo Film Co., Ltd.Inventors: Toru Harada, Toshiyuki Watanabe
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Patent number: 4687862Abstract: 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: GrantFiled: October 14, 1986Date of Patent: August 18, 1987Assignee: Shin Nisso Kako Co., Ltd.Inventors: Takeo Obitsu, Tetsuo Igaki, Kimiaki Kinoshita, Morio Nanbu, Shinichi Satoh
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Patent number: 4668967Abstract: 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: GrantFiled: May 28, 1986Date of Patent: May 26, 1987Assignee: Shin Nisso Kako Co., Ltd.Inventors: Masakichi Yahagi, Takeo Obitsu, Tetsuo Igaki, Kazuyuki Horisawa, Morio Nanbu, Kimiaki Kinoshita, Sumio Manaka
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Patent number: 4612558Abstract: 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: GrantFiled: March 12, 1985Date of Patent: September 16, 1986Assignee: Hodogaya Chemical Co., Ltd.Inventors: Mitsutoshi Anzai, Masahiko Yamaguchi, Kazuyuki Wakasugi, Susumu Suzuka, Michihiro Gonda, Toshiyuki Abe, Katsumasa Kikkawa, Mikiko Kanasugi
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Patent number: 4603202Abstract: 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: GrantFiled: October 12, 1984Date of Patent: July 29, 1986Assignee: BASF AktiengesellschaftInventors: Udo Mayer, Andreas Oberlinner
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Patent number: 4410708Abstract: Certain 3-substituted amino-7-substituted fluoran derivatives useful as color recording materials.Type: GrantFiled: February 3, 1976Date of Patent: October 18, 1983Assignee: Shin Nisso Kako Co., Ltd.Inventors: Masakichi Yahagi, Shoichi Horiuchi, Takahumi Toyama, Akio Kashiwagi, Teruo Suzuki, Tetsuo Igaki, Kazuyuki Horisawa, Mituhiro Shoji
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Patent number: 4362668Abstract: 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: GrantFiled: July 31, 1979Date of Patent: December 7, 1982Assignee: Standard Oil Company (Indiana)Inventor: Richard J. Lee