Plural Benzothiazoles (including Hydrogenated) Patents (Class 548/156)
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Patent number: 6956032Abstract: The present invention pertains to luminescent dyes and methods for covalently attaching the dyes to a component or mixture of components so that the components may be detected and/or quantified by luminescence detection methods. The dyes are cyanine and cyanine-type dyes that contain or are derivatized to contain a reactive group. The reactive group is covalently reactive with amine, hydroxy and/or sulfhydryl groups on the component so that the dye can be covalently bound to the component. In addition, the dyes are preferably soluble in aqueous or other medium in which the component is contained. The components to be labeled can be either biological materials, such as antibodies, antigens, peptides, nucleotides, hormones, drugs, or non-biological materials, such as polymers, glass, or other surfaces. Any luminescent or light absorbing detecting step can be employed in the method of the invention.Type: GrantFiled: December 19, 2000Date of Patent: October 18, 2005Assignee: Carnegie Mellon UniversityInventor: Alan S. Waggoner
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Patent number: 6884891Abstract: Methine dye compounds represented by formula (1) and highly sensitive silver halide photographic materials containing these compounds: Dye1-(L1-(Dye2)m1)m2 (CI1)y1??(1) wherein L1 represents a linkage group represented by formula (2), m1 represents an integer of 1 to 5, m2 represents an integer of 1 to 5, Dye1 represents a first chromophore, Dye 2 represents a second chromophore, CI1 represents an ion for neutralization of electric charge, and y1 represents a number of the ions required for neutralization of electric charges; -G1-A1-Y1-G2-Y2-A2-G3-??(2) wherein A1 and A2 each individually represent a carbonyl group or a sulfonyl group, Y1 and Y2 each individually represent —O—, —S— or —NR1—, R1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group, and G1, G2 and G3 each individually represent a divalent linkage group.Type: GrantFiled: July 11, 2002Date of Patent: April 26, 2005Assignee: Fuji Photo Film Co., Ltd.Inventor: Katsumi Kobayashi
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Patent number: 6867304Abstract: Provided are new TPA chromophores of the formula: wherein R is an alkyl group having 1 to 20 carbon atoms and Q is —C6H13, —CH2—C6H5, or —C6H11.Type: GrantFiled: February 23, 2004Date of Patent: March 15, 2005Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Loon-Seng Tan, Ramamurthi Kannan
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Patent number: 6849742Abstract: The present invention provides a binaphthol compound represented by formula [1]: and a salt thereof. The binaphthol compound of the present invention is useful for manufacturing antiseptic compounds or chiral catalysts. According to the method of the present invention, binaphthol compounds can be prepared in high yield with low cost.Type: GrantFiled: April 18, 2002Date of Patent: February 1, 2005Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
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Publication number: 20040260072Abstract: This invention relates to new fluorescence dyes from the class of cyanine dyes, especially indotricarbocyanines with an absorption and fluorescence maximum in the spectral range of 700 to 900 nm, a thiol-specific reactive group, and three, preferably four, sulfonate groups, to an increase of water solubility as well as the production of dyes. This invention also relates to the conjugates of these dyes with biomolecules and uses thereof.Type: ApplicationFiled: January 23, 2004Publication date: December 23, 2004Inventors: Kai Licha, Christin Perlitz
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Publication number: 20040186278Abstract: Disclosed are cyanine dyes having meso-substituents in the polymethine chain linking the heterocyclic ring systems.Type: ApplicationFiled: March 21, 2003Publication date: September 23, 2004Inventors: Chung-Yuan Chen, Shiv Kumar
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Patent number: 6737532Abstract: An organic electroluminescent compound of the formula (I) wherein: X1 is selected from the group consisting of oxygen, sulfur, C(CH3)2 and N—R, wherein R is hydrogen, alkyl of from 1 to 20 carbon atoms or aryl; and Ar1 and Ar2 are individually aryl or heterocyclic systems. Applying the compound to an electroluminescent (EL) device provides a highly efficient blue and green emitting organic EL device.Type: GrantFiled: April 5, 2002Date of Patent: May 18, 2004Assignees: Chi Mei Optoelectronics Corporation, Kyocera CorporationInventors: Ruey-Min Chen, Jun-Wen Chung
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Patent number: 6730793Abstract: Provided are chromophores of the formula Q—(—L—Z)x, wherein x is 2 or 3, wherein Q is selected from the group consisting of wherein L is wherein R is an alkyl group having 1 to 20 carbon atoms, and wherein Z is selected from the group consisting ofType: GrantFiled: June 13, 2002Date of Patent: May 4, 2004Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Ramamurthi Kannan, Loon-Seng Tan, Bruce A. Reinhardt, Richard A. Vaia
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Patent number: 6716413Abstract: Highly hydrophilic indole and benzoindole derivatives that absorb and fluoresce in the visible region of light are disclosed. These compounds are useful for physiological and organ function monitoring. Particularly, the molecules of the invention are useful for optical diagnosis of renal and cardiac diseases and for estimation of blood volume in vivo.Type: GrantFiled: October 16, 2000Date of Patent: April 6, 2004Assignee: Mallinckrodt, Inc.Inventors: Samuel Achilefu, Raghavan Rajagopalan, Richard B. Dorshow, Joseph E. Bugaj
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Publication number: 20040029925Abstract: The present invention provides a genus of bis-benzimidazole compounds, methods and pharmaceutical compositions that are useful as modulators of potassium ion channels. The compounds of the invention are of use in both therapeutic and diagnostic methods.Type: ApplicationFiled: May 13, 2003Publication date: February 12, 2004Applicant: ICAgen, Inc.Inventors: Xiaodong Wang, Alan B. Fulp, Albert M. van Rhee, Kerry L. Spear
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Publication number: 20040014981Abstract: A compound of the formula (I) is provided: (I), wherein Z is O, S, or NR35 wherein R35 is H or alkyl; R1-R5 are each independently H, alkyl, halo, carboxyl, amino, or SO331 Cat+, wherein Cat+ is a cation and at least one of R1-R5 is SO3−Cat+; R6 and R7 are each H, alkyl, or optionally, together with the (a) group to which they are bonded, form a ring; m and n are each independently integers from 0 to 5; X and Y are each independently O, S, Se or CR19R20, wherein R19 and R20 are each independently alkyl, or optionally form a ring together with the carbon atom to which they are bonded; R8 and R13 are each independently alkyl, (CH2)rR25 or (CH2)rR18; wherein at least one of R8 and R13 (CH2)rR18 and wherein r is an integer from 1 to 50, and R25 is a functional group that does not directly react with a carboxyl, hydroxyl, amino or a thiol group, and R18 is a functional group that can react with 1Type: ApplicationFiled: January 28, 2003Publication date: January 22, 2004Inventors: Ananda G. Lugade, Narasimhachari Narayanan, Daniel R. Draney
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Patent number: 6669926Abstract: Highly hydrophilic indole and benzoindole derivatives that absorb and fluoresce in the visible region of light are disclosed. These compounds are useful for physiological and organ function monitoring. Particularly, the molecules of the invention are useful for optical diagnosis of renal and cardiac diseases and for estimation of blood volume in vivo.Type: GrantFiled: October 16, 2000Date of Patent: December 30, 2003Assignee: Mallinckrodt, Inc.Inventors: Samuel Achilefu, Raghavan Rajagopalan, Richard B. Dorshow, Joseph E. Bugaj
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Patent number: 6667330Abstract: Furanone derivatives and the pharmaceutically acceptable salts thereof have cytoprotective activity and protective activity for neuroinflammation, and neurodegenerative disorders; they are useful in the treatment of stroke, cerebral ischemia, myocardial infarction, myocardial ischemia, chronic heart failure, inflammation and other oxidative stress-related conditions, as well as Alzheimer's disease and senile dementia; they are also useful in the manufacture of pharmaceutical formulations for the treatment of such conditions.Type: GrantFiled: January 28, 2003Date of Patent: December 23, 2003Assignee: Galileo Pharmaceuticals, Inc.Inventors: Bing Wang, Wei Zhang, Jiangao Song, Ughetta del Balzo, Lesley Brown, Gail Walkinshaw
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Patent number: 6660529Abstract: Chemiluminescent heteroaryl substituted benzothiazole 1,2-dioxetane compounds capable of producing light energy when decomposed are provided. These chemiluminescent compounds are represented by the general formula: The heteroaryl substituent Y can be, for example, a pyridyl group or a benzothiazolyl group. The heteroaryl substituted benzothiazole compounds are substantially stable at room temperature. Kits including the heteroaryl substituted dioxetane compounds as well as methods for using these compounds for detecting the presence of one or more analytes in a sample are also provided.Type: GrantFiled: September 5, 2001Date of Patent: December 9, 2003
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Publication number: 20030191320Abstract: The present invention provides a process for the preparation of a compound of formula (I) wherein Y represents —O—, —S— or —N(R2)—, R2 being hydrogen, C1-C10alkyl or aralkyl; Z represents a 2,5-furanyl, 2,5-thiophenyl, 4,4′-stilbenyl or a 1,2-ethyleny residue and R1 represents hydrogen, halogen, C1-C10alkoxyl, cyano, COOM or SO3M, M being hydrogen or an alkaline or alkaline earth metal, characterized by reacting a compound of formula (II) with a dicarboxylic acid of formula (III): HOOC-Z-COOH, or an ester thererof, Y, Z and R1 being as previously defined, in N-methylpyrrolidone or N,N-dimethylacetamide, in the presence of an acidic catalyst and, optionally, in the presence of a secondary solvent capable of removing water from the reaction mixture, which are useful as optical whitening agents for natural and synthetic materials.Type: ApplicationFiled: April 16, 2003Publication date: October 9, 2003Inventors: Victor Paul Eliu, Julia Hauser
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Patent number: 6630470Abstract: Invented are G-CSF mimetics. Also invented are selected octacyclic compounds, pharmaceutical compositions containing these compounds, and methods of using these compounds as G-CSF mimetics. Also invented are novel processes used in preparing these compounds.Type: GrantFiled: November 20, 2000Date of Patent: October 7, 2003Assignee: SmithKline Beecham CorporationInventors: Juan I Luengo, Kevin J Duffy
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Publication number: 20030138663Abstract: This invention relates to a low-molecular-weight compound which is soluble in solvents and useful for a luminescent material and to an organic electroluminescent element (EL element) which comprises said luminescent material in its electroluminescent layer.Type: ApplicationFiled: October 25, 2002Publication date: July 24, 2003Inventors: Tatsuo Mori, Teruyoshi Mizutani, Toru Takeda, Hiroshi Miyazaki, Koichi Yamashita
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Patent number: 6576780Abstract: The current invention discloses hydroxyamidino derivatives useful as nitric oxide synthase inhibitors.Type: GrantFiled: October 13, 2000Date of Patent: June 10, 2003Assignee: GD Searle & CompanyInventors: Rolando E. Gapud, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Barnett S. Pitzele, Suzanne S. Metz, R. Keith Webber, Foe S. Tjoeng, Robert E. Manning, Mihaly V. Toth
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Patent number: 6552199Abstract: The subject matter of the invention are new xanthene derivatives of the formula I, wherein R1,R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and X, Y, are as defined herein. The compounds according to the invention provide molecules that are—due to their spectral properties (absorption maxima in the range of approx. 650 nm and above as well as emission maxima above 670 nm)—very suitable for the use as dyes and in particular as fluorescence dyes. The compounds of the formula I according to the invention are used for the production of fluorescence conjugates, for their application in immunoassays, for DNA analytics, for in-vivo diagnostics or as a laser dye.Type: GrantFiled: May 11, 2000Date of Patent: April 22, 2003Assignee: Roche Diagnostics GmbHInventors: Ewald Daltrozzo, Alexander Reiss
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Publication number: 20030022094Abstract: The invention provides a negative image-recording material for heat-mode exposure systems, which comprises (A) an IR absorbent including cyanine dye having a substituent that contains an atom having an atomic weight of at least 28 such as halogen atom, or a substituent that contains a non-covalent electron pair such as carbonyl group, (B) a radical generator and (C) a radically-polymerable compound, and which is imagewise exposed to IR rays for image formation thereon.Type: ApplicationFiled: January 15, 2002Publication date: January 30, 2003Inventors: Ippei Nakamura, Tadahiro Sorori
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Patent number: 6498004Abstract: This invention provides a photographic element comprising at least one silver halide emulsion layer in which the silver halide is sensitized with a compound of the formula (a): &Dgr;−(t)m−XY′ (a) XY′−(t)m−&Dgr; (b) &Dgr;−(t)m−XY′−(t)m−&Dgr; (c) wherein &Dgr; is protective group that is eliminated during development of the photographic element, t is a timing group, m is an integer from 0 to 3, and XY′ is a fragmentable electron donor moiety in which X is an electron donor group and Y′ is a leaving proton H or a leaving group Y, with the proviso that if Y′ is a proton, a base, &bgr;−, is present in the emulsion or is covalently linked directly or indirectly to X, and wherein: 1) X—Y′ has an oxidation potential between 0 and about 1.Type: GrantFiled: December 28, 2000Date of Patent: December 24, 2002Assignee: Eastman Kodak CompanyInventors: Jerome R. Lenhard, Annabel A. Muenter, Stephen A. Godleski, Paul A. Zielinski, Deepak Shukla, Donald R. Diehl
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Publication number: 20020156288Abstract: A symmetric cyanine of the formula: 1Type: ApplicationFiled: January 2, 2002Publication date: October 24, 2002Inventors: Giuseppe Caputo, Leopoldo Della Ciana
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Publication number: 20020133019Abstract: This invention relates to novel thioflavin derivatives, methods of using the derivatives in, for example, in vivo imaging of patients having neuritic plaques, pharmaceutical compositions comprising the thioflavin derivatives and method of synthesizing the compounds. The compounds find particular use in the diagnosis and treatment of patients having diseases where accumulation of neuritic plaques are prevalent. The disease states or maladies include but are not limited to Alzheimer's Disease, familial Alzheimer's Disease, Down's Syndrome and homozygotes for the apolipoprotein E4 allele.Type: ApplicationFiled: August 24, 2001Publication date: September 19, 2002Inventors: William E. Klunk, Chester A. Mathis, Yanming Wang
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Patent number: 6451988Abstract: Novel naphthol derivatives, and various azo compounds and metal complexes prepared by using the derivatives are provided. The instant invention provides naphthol derivatives represented by general formula (1); wherein at least one of Y1 and Y2 is a group represented by formula (2); wherein X1 is —O—, —S— or —NH—; and Z is an optionally substituted aromatic group or heterocyclic group having conjugated double bonds, and salts thereof; mono-, bis-, and trisazo compounds prepared from the derivatives; and metal complexes containing the derivatives as the ligand.Type: GrantFiled: January 16, 2002Date of Patent: September 17, 2002Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
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Patent number: 6437141Abstract: A cyanine dye having the formula 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.Type: GrantFiled: April 2, 2001Date of Patent: August 20, 2002Assignee: NEN Life Science Products, Inc.Inventors: Malcolm Harry Randall, Philip Richard Buzby, Thomas Joseph Erickson, Joseph David Trometer, Joseph John Miller, Jr., David George Ahern, Mark Norman Bobrow
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Publication number: 20020094453Abstract: A metal coordination compound suitable as an organic material for a luminescent device is represented by the following formula (1): 1Type: ApplicationFiled: November 29, 2001Publication date: July 18, 2002Inventors: Takao Takiguchi, Shinjiro Okada, Akira Tsuboyama, Koji Noguchi, Takashi Moriyama, Jun Kamatani, Manabu Furugori
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Patent number: 6420130Abstract: The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods.Type: GrantFiled: April 28, 1999Date of Patent: July 16, 2002Assignee: Aurora Biosciences CorporationInventors: Lewis R. Makings, Gregor Zlokarnik
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Patent number: 6403807Abstract: Bridged fluorescent dyes of the cyanine and squaraine families are disclosed. The dyes are useful as markers in assay techniques and offer advantages of undergoing excitation at a common wavelength but emitting at structure dependent different wavelengths.Type: GrantFiled: July 6, 2000Date of Patent: June 11, 2002Assignee: SurroMed, Inc.Inventors: Rajendra Singh, Gregory Gorski, Gary Frenzel
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Patent number: 6399392Abstract: The quenching compounds of the invention are nitrogen-substituted xanthenes that are substituted by one or more aromatic or heteroaromatic quenching moieties. The quenching compounds of the invention exhibit little or no observable fluorescence and efficiently quench a broad spectrum of luminescent compounds. The chemically reactive quenching compounds possess utility for labeling a wide variety of substances, including biomolecules. These labeled substances are highly useful for a variety of energy-transfer assays and applications.Type: GrantFiled: April 21, 2000Date of Patent: June 4, 2002Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Victoria L. Singer, Stephen T. Yue
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Publication number: 20020055133Abstract: The invention provides peptide synthons having protected functional groups for attachment of desired moieties (e.g. functional molecules or probes). Also provided are peptide conjugates prepared from such synthons, and synthon and conjugate preparation methods including procedures for identifying the optimum probe attachment site. Biosensors are provided having environmentally sensitive dyes that can locate specific biomolecules within living cells and detect chemical and physiological changes in those biomolecules as the living cell is moving, metabolizing and reacting to its environment. Methods are included for detecting GTP activation of a Rho GTPase protein using polypeptide biosensors. When the biosensor binds GTP-activated Rho GTPase protein, the environmentally sensitive dye emits a signal of a different lifetime, intensity or wavelength than when not bound.Type: ApplicationFiled: April 20, 2001Publication date: May 9, 2002Inventors: Klaus M. Hahn, Alexei Toutchkine, Rajeev Muthyala, Vadim Kraynov, Steven J. Bark, Dennis R. Burton, Chester Chamberlain
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Patent number: 6335450Abstract: This invention provides cyclic-bridged dyes, particularly cyclic-bridged cyanine dyes, of the general formula: In this formula, each dotted line represents carbon atoms necessary to form a fused substituted or unsubstituted aromatic ring; n=1-18; m=1-18, selected independently from n. X and Y are selected independently from the group consisting of S, O, N, CH2 and C(CH3)2; at least one of said R1 and R2 comprises a sulfonic acid or sulfonate group attached to the aromatic ring; and R3 and R4 are independently selected from the group consisting of carboxyl, activated carboxyl and methyl, wherein at least one of said R3 and R4 groups is carboxylate or activated carboxylate. Methods of making and using the cyclic-bridged dyes are also provided.Type: GrantFiled: November 9, 2000Date of Patent: January 1, 2002Assignee: Beckman Coulter, Inc.Inventors: Firdous Farooqui, Maged A. Michael, M. Parameswara Reddy
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Patent number: 6331632Abstract: This invention provides dye phosphoramidites, particularly phosphoramidites of cyanine and related dyes, of the general formula: In this formula, each dotted line represents carbon atoms necessary to form a fused substituted or unsubstituted aromatic ring; m is an integer from 1 to 18; Y and Z are independently selected from the group consisting of S, O, N, CH2 and C(CH3)2; R1 is an alkyl; (PAM) is a phosphoramidite group; X⊖ is a negative ion; and Q is or wherein n is 1, 2 or 3. Methods of making and using the dye phosphoramidites are also provided.Type: GrantFiled: November 9, 2000Date of Patent: December 18, 2001Assignee: Beckman Coulter, Inc.Inventors: M. Parameswara Reedy, Firdous Farooqui, Maged A. Michael
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Patent number: 6300502Abstract: Provided are chromophores with very large two-photon absorption cross-sections. One group of these chromophores has the formula: (T—Q)n—N—Phm wherein Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-3 and m has a value of 3−n, and wherein T is wherein R1 and R2 are alkyl groups having 1 to 20 carbon atoms, provided that when Q is a single bond, the value of n is 2 or 3. Another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as defined above, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-4 and m has a value of 4−n, and wherein G is a 4-arm core unit. Yet another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as described previously, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-6 and m has a value of 6−n, and wherein G is a 6-arm core unit.Type: GrantFiled: December 8, 2000Date of Patent: October 9, 2001Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Ramamurthi Kannan, Bruce A. Reinhardt, Loon-Seng Tan
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Patent number: 6284924Abstract: A novel compound represented by the general formula (1) or salts thereof. The compound is useful as a structural component of polymers such as polyesters and polyamides. The compound wherein Y1, Y2, Y3, and/or Y4 are carboxy groups is especially useful as a structural component of a liquid crystal polymer with improved weld strength and anisotropy.Type: GrantFiled: January 4, 2001Date of Patent: September 4, 2001Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Naoko Mori
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Patent number: 6224644Abstract: A cyanine dye having the formula 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.Type: GrantFiled: November 24, 1999Date of Patent: May 1, 2001Assignee: NEN Life Science Products, Inc.Inventors: Malcolm Harry Randall, Philip Richard Buzby, Thomas Joseph Erickson, Joseph David Trometer, Joseph John Miller, Jr., David George Ahern, Mark Norman Bobrow
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Patent number: 6225050Abstract: Cyanine and related dyes, such as merocyanine, styryl and oxonol dyes, are strongly light-absorbing and highly luminescent. Cyanine and related dyes having functional groups make them reactive with amine, hydroxy and sulfhydryl groups are covalently attached to proteins, nucleic acids, carbohydrates, sugars, cells and combinations thereof, and other biological and nonbiological materials, to make these materials fluorescent so that they can be detected. The labeled materials can then be used in assays employing excitation light sources and luminescence detectors. For example, fluorescent cyanine and related dyes can be attached to amine, hydroxy or sulfhydryl groups of avidin and to antibodies and to lectins. Thereupon, avidin labeled with cyanine type dyes can be used to quantify biotinvlated materials and antibodies conjugated with cyanine-type dyes can be used to detect and measure antigens and haptens. In addition, cyanine-conjugated lectins can be used to detect specific carbohydrate groups.Type: GrantFiled: November 12, 1996Date of Patent: May 1, 2001Assignee: Carnegie Mellon UniversityInventor: Alan S. Waggoner
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Patent number: 6204389Abstract: A cyanine dye having the formula 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.Type: GrantFiled: November 24, 1999Date of Patent: March 20, 2001Assignee: NEN Life Science Products, Inc.Inventors: Malcolm Harry Randall, Philip Richard Buzby, Thomas Joseph Erickson, Joseph David Trometer, Joseph John Miller, Jr., David George Ahern, Mark Norman Bobrow
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Patent number: 6197956Abstract: A cyanine dye having the formula 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.Type: GrantFiled: November 24, 1999Date of Patent: March 6, 2001Assignee: NEN Life Science Products, Inc.Inventors: Malcolm Harry Randall, Philip Richard Buzby, Thomas Joseph Erickson, Joseph David Trometer, Joseph John Miller, Jr., David George Ahern, Mark Norman Bobrow
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Patent number: 6156772Abstract: There are disclosed compounds of formula (I) ##STR1## and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.Type: GrantFiled: May 14, 1999Date of Patent: December 5, 2000Assignee: Merck & Co., Inc.Inventors: Mark Goulet, Thomas F. Walsh, Feroze Ujjainwalla, Matthew J. Wyvratt, Jr.
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Patent number: 6048982Abstract: Cyanine and related dyes, such as merocyanine, styryl and oxonol dyes, are strongly light-absorbing and highly luminescent. Cyanine and related dyes having functional groups make them reactive with amine, hydroxy and sulfhydryl groups are covalently attached to proteins, nucleic acids, carbohydrates, sugars, cells and combinations thereof, and other biological and nonbiological materials, to make these materials fluorescent so that they can be detected. The labeled materials can then be used in assays employing excitation light sources and luminescence detectors. For example, fluorescent cyanine and related dyes can be attached to amine, hydroxy or sulfhydryl groups of avidin and to antibodies and to lectins. Thereupon, avidin labeled with cyanine type dyes can be used to quantify biotinylated materials and antibodies conjugated with cyanine-type dyes can be used to detect and measure antigens and haptens. In addition, cyanine-conjugated lectins can be used to detect specific carbohydrate groups.Type: GrantFiled: June 12, 1997Date of Patent: April 11, 2000Assignee: Carnegie Mellon UniversityInventor: Alan S. Waggoner
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Patent number: 6011033Abstract: This invention relates to a phenylene derivative represented by the following formula (1) or a salt thereof and also to a medicine containing it as an effective ingredient. ##STR1## wherein R.sup.1 represents H or halogen; A represents --CH.dbd.CH--, --CH.dbd.N--, --N(R.sup.2)--, --O-- or --S--; W represents --CH.dbd.CH-- or --CH.sub.2 O--; X represents --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 N(R.sup.3)--, --CH.dbd.N--, --COO-- or --CONH--; Y represents ##STR2## B.sup.1 represents --C(R.sup.7)(R.sup.8)(CH.sub.2).sub.l --, --S(O).sub.m (CH.sub.2).sub.n -- or --CH.dbd.C(R.sup.9)--; B.sup.2 represents --CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.sub.2 --; Z.sup.1 and Z.sup.2 each represents O or S; etc. The phenylene derivative or salt thereof has antileukotrienic action and antihistaminic action and is useful as a medicine such as an asthma preventive or curative.Type: GrantFiled: November 13, 1998Date of Patent: January 4, 2000Assignee: Kowa Co., Ltd.Inventors: Henk Timmerman, Mingqiang Zhang, Kazuhiro Onogi, Masahiro Tamura, Tsutomu Toma, Yasushi Wada
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Patent number: 6008243Abstract: The present invention is directed to compound of the formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, X, Y, and ##STR2## are as defined herein. These compounds are useful for inhibiting the activity of a metalloproteinase by contacting the metalloproteinase with an effective amount of the inventive compounds.Type: GrantFiled: March 25, 1997Date of Patent: December 28, 1999Assignees: Agouron Pharmaceuticals, Inc., Syntex (U.S.A.), Inc.Inventors: Steven L. Bender, Arlindo L. Castelhano, Wesley K. M. Chong, Melwyn A. Abreo, Jian Jeffrey Chen, Judith G. Deal
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Patent number: 6004536Abstract: The present invention relates to a family of cyanine dyes possessing lipophilic alkyl chains and either one or more reactive functional groups, bromo or chloro, or phenyl, sulfophenyl or polysulfophenyl substituents or combinations thereof. The dyes of the invention are useful for staining membranes in cells or isolated from cells, and are well-retained therein. Additionally, the reactive dyes of the invention are useful for preparing dye-conjugates, thereby conferring the membrane staining ability of the subject dye onto the resulting dye-conjugate.Type: GrantFiled: August 14, 1996Date of Patent: December 21, 1999Assignee: Molecular Probes, Inc.Inventors: Wai-Yee Leung, Richard P. Haugland, Fei Mao
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Patent number: 5998626Abstract: Disclosed are bisbenzazole compounds capable of emitting strong fluorescence, with the compounds having at particular positions specific substituent groups, such as alkoxy, aryloxy, dialkylamino, diarylamino or N-arylamino groups, to ensure high stability in organic photoluminescence elements. For example, bisbenzazole compounds show below are disclosed.Type: GrantFiled: January 27, 1999Date of Patent: December 7, 1999Assignee: Fuji Photo Film Co., Ltd.Inventor: Tadahisa Sato
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Patent number: 5968479Abstract: A diagnostic marker containing (a) a detection system such as an antibody and (b) a fluorescent functional group that is bound to the detection system and represented by the following formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent hydrogen atom, an alkyl group or the like; R.sup.3 represents an alkyl group, a sulfonic acid-alkyl group or the like; X.sup.- represents an anion species, if required; Y represents a C.sub.1 -C.sub.10 alkylene group or a C.sub.1 -C.sub.10 alkylene group containing one or more atoms selected from the group consisting of oxygen atom, nitrogen atom and sulfur atom. The diagnostic marker emits fluorescence having a wavelength of 780 nm or more when irradiated with near or far infrared rays, and thus useful for infrared endoscopic diagnosis or identification of a focus in surgical operation.Type: GrantFiled: September 17, 1997Date of Patent: October 19, 1999Assignee: Daiichi Pure Chemicals Co., Ltd.Inventors: Susumu Ito, Masayuki Nozawa, Masanobu Shiga, Kazumi Sasamoto, Kazuhiro Takesako, Hiroshi Takeuchi
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Patent number: 5942547Abstract: This invention provides a compound having the formula: ##STR1## wherein R.sup.1 and R.sup.3 independently are hydrogen, --CHO, --COCH.sub.3, --COR.sup.7, --A--Ar--(Q).sub.z, etc.; wherein D is a C.sub.1-6 linear, C.sub.3-8 branched or cyclic group having from 4 to about 15 atoms, consisting of C, etc.; wherein D is unsubstituted or substituted with one or more groups independently selected from the group consisting of --OH, NH.sub.2, --NHR.sub.7, etc.; wherein each Q is independently --CNH(NHY), --NHCNH(NHY), --SO.sub.2 W, --SOW, etc.; wherein Y is hydrogen, alkyl, alkenyl, --B--NH.sub.2, --B--NHR.sup.8, etc.; wherein W is alkyl, alkenyl, --B--NH.sub.2, etc.; wherein A nd B independently are a bond, or a C.sub.1-6 linear, C.sub.3-8 branched or cyclic linking group having from 1 to about 15 atoms, consisting of C, optionally interrupted by N, S, P and O; wherein A and B independently are unsubstituted or substituted with --OH, NH.sub.2, etc.; wherein R.sup.7 is an alkyl, a branched alkyl, etc.; wherein R.sup.Type: GrantFiled: September 6, 1996Date of Patent: August 24, 1999Assignee: Scriptgen Pharmaceuticals, Inc.Inventors: Gary R. Gustafson, David G. Powers, Mark A. Wuonola
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Patent number: 5880287Abstract: Fluorescent dyes which are free of aggregation and serum binding are provided. These dyes are suitable for applications such as fluorescence immunoassays, in vivo imaging and in vivo tumor therapy. Fluorescence immunoassays methods are provided which use fluorescent dyes which are free of aggregation and serum binding. Such immunoassay methods are thus, particularly useful for the assay of biological fluids, such as serum, plasma, whole blood and urine. The present invention is directed to compositions comprising an oligonucleotide linked to a detectably labeled marker component comprising a fluorophore moiety which comprises a substantially planar, multidentate macrocyclic ligand coordinated to a central atom capable of coordinating with two axial ligands and two polyoxyhydrocarbyl moieties which are attached as axial ligands to the central atom. The present invention is also directed to nucleic acid hybridization and amplification methods employing such compositions.Type: GrantFiled: June 7, 1995Date of Patent: March 9, 1999Assignee: Hyperion, Inc.Inventors: Walter B. Dandliker, Robert Francis Devlin, Peter Olaf Gustaf Arrhenius, Mao-Lin Hsu
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Patent number: 5859251Abstract: A two-photon absorbing chromophore of the formulaE--Ar--Ewherein the Ar core is selected from the group consisting of ##STR1## wherein R.sub.1 and R.sub.2 are alkyl groups having 8 to 12 carbon atoms, and wherein R.sub.1 and R.sub.Type: GrantFiled: September 18, 1997Date of Patent: January 12, 1999Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Ramamurthi Kannan, Lawrence L. Brott, Stephen J. Clarson
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Patent number: 5846666Abstract: An electroluminescent device comprised of a metal thioxinoid of the formula ##STR1## wherein M represents a metal; each n is a number of from 1 to 3; N is nitrogen, S is sulfur, and Z represents an aromatic moiety.Type: GrantFiled: February 27, 1997Date of Patent: December 8, 1998Assignee: Xerox CorporationInventors: Nan-Xing Hu, Shuang Xie, Beng S. Ong, Zoran D. Popovic, Ah-Mee Hor
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Patent number: 5783586Abstract: Compounds having the formula: ##STR1## wherein W.sup.1 and W.sup.2 are independently selected from optionally substituted quinolyl, optionally substituted benzothiazolyl, optionally substituted benzoxazolyl, optionally substituted benzimidazolyl, optionally substituted quinoxalyl, optionally substituted naphthyl; R.sup.1 and R.sup.2 are independently selected from hydrogen, alkyl, halolalkyl, alkoxy, halogen; R.sup.3 is selected from thienyl, furyl, phenyl, naphthyl, benzo?b!thienyl, alkyl, hydroxyl, and hydrogen; Y an alkylene of one to six carbon atoms; and M is selected from (a) a pharmaceutically acceptable metabolically cleavable group, (b) --OR.sup.4, (c) --NR.sup.5 R.sup.6, (d)--NR.sup.4 SO.sub.2 R.sup.7 (e)--NH--Tetrazolyl, and (f) glycinyl; inhibit leukotriene biosynthesis and are useful in the treatment of allergic and inflammatory disease states. Also disclosed are leukotriene biosynthesis inhibiting compositions and a method of inhibiting leukotriene biosynthesis.Type: GrantFiled: October 1, 1996Date of Patent: July 21, 1998Assignee: Abbott LaboratoriesInventors: Teodozyj Kolasa, Clint D. W. Brooks, David E. Gunn