Plural Nitrogens, Other Than As Nitro Or Nitroso, Attached Directly To The Carbocyclic Rings Of The Acridine Ring System (e.g., 3,6-diaminoacridines, Etc.) Patents (Class 546/107)
  • Patent number: 8937121
    Abstract: A condensed heterocyclic compound which is shown by the following formula (I) and a composition containing an (a) organic material and (b) at least one type of the condensed heterocyclic compound are provided. (Y indicates a chemical single bond, —S(?O)—, or —SO2—. Ra and Rb indicate substitutable C1 to C30 organic groups. Za and Zb indicate chemical single bonds or —SO2—. X1 and X2 indicate hydrogen atoms etc. n and m respectively independently indicate integers of 0 to 2, where one of n and m is not 0).
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: January 20, 2015
    Assignee: Zeon Corporation
    Inventors: Kei Sakamoto, Satoshi Kiriki, Tomonori Ogawa, Masanobu Shinohara
  • Publication number: 20140073058
    Abstract: Methods of using dyes and associated technology are provided. A dye, such as a monomeric dye or a dimeric dye, may be used in a nucleic acid gel staining application and/or a nucleic acid detection application. Such a dye and a salt that comprises an anion that is associated with a strong acid and a cation that is associated with a strong base may be used in such an application. A dimeric dye, such as a dimeric dye capable of forming a hairpin-like structure, may be used to stain and/or detect nucleic acids via a release-on-demand mechanism. A dimeric dye having low background fluorescence in the absence of nucleic acids and high fluorescence in the presence of nucleic acids, upon binding therewith, may be used to stain and/or detect nucleic acids.
    Type: Application
    Filed: August 8, 2013
    Publication date: March 13, 2014
    Applicant: Biotium, Inc.
    Inventors: Fei Mao, Wai-Yee Leung
  • Patent number: 8632893
    Abstract: Organic compounds and organic electroluminescence devices employing the same are provided. The organic compound has a chemical structure represented as follows: wherein R are each independently an hydrogen, or a C1-8 alkyl group, and wherein R1 and R2 are each independently an hydrogen, or a C1-8 alkyl group, R3 is a hydrogen, and R1 and R2 are not hydrogen group simultaneously; or wherein R1 and R2 link together with the carbon atoms bonded thereto to form a phenyl group; wherein R2 and R3 link together with the carbon atoms bonded thereto to form a phenyl group.
    Type: Grant
    Filed: September 15, 2011
    Date of Patent: January 21, 2014
    Assignee: Industrial Technology Research Institute
    Inventors: Chi-Jen Lin, Heh-Lung Huang, Jin-Sheng Lin, Chien-Hong Cheng, Mei-Rurng Tseng
  • Publication number: 20140004051
    Abstract: The invention provides co-crystals and salts of contrast agents as well as methods to use and prepare the co-crystals and salts.
    Type: Application
    Filed: June 28, 2013
    Publication date: January 2, 2014
    Inventor: Leonard R. MacGillivray
  • Publication number: 20130150254
    Abstract: The present invention provides systems and methods for production of activatable diazo-derivatives for use in labeling nucleotides. Labeling nucleotides is accomplished by contacting a stable hydrazide derivative of a detectable moiety with an activating polymer reagent which is used to directly label the nucleotide sample. Labeling occurs on the phosphate backbone of the nucleotide which does not perturb hybridization of the labeled nucleotide with its anti-sense strand. Since the method involves direct labeling, all types of nucleotides can be labeled without prior amplification or alteration.
    Type: Application
    Filed: December 6, 2011
    Publication date: June 13, 2013
    Inventors: John J. Naleway, Ying Jiang, Ryan Link-Cole
  • Publication number: 20120259098
    Abstract: The present invention relates to novel dendrimer compounds and methods of synthesizing the same. In particular, the present invention is directed to novel polyamidoamine (PAMAM) dendrimers, novel dendrimer branching units, methods for synthesizing such novel PAMAM dendrimers and functionalized dendrimers, as well as systems and methods utilizing the dendrimers (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease diagnosis and/or therapy, etc.))).
    Type: Application
    Filed: October 7, 2010
    Publication date: October 11, 2012
    Applicant: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
    Inventors: James R. Baker, JR., Baohua Huang
  • Patent number: 8173274
    Abstract: Organic compounds and organic electroluminescence devices employing the same are provided. The organic compound has a chemical structure represented as follows: wherein, R1 and R2 are independent and can be aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, or R1 and R2 link together with the carbon atoms to which they are attached to form a fused aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, and R3, R4, and R5 are independent and can be H, C1-8 alkyl, C1-8 alkoxy, C1-8 halo-alkyl, aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: May 8, 2012
    Assignee: Industrial Technology Research Institute
    Inventors: Chi-Jen Lin, Heh-Lung Huang, Jin-Sheng Lin, Chien-Hong Cheng, Mei-Rurng Tseng
  • Patent number: 8110562
    Abstract: This invention provides nuclear hormone receptor binding compounds, compositions comprising the same and methods of uses thereof in treating a variety of diseases or conditions in a subject, including, inter-alia, prostate cancer and/or diseases or disorders of bone and muscle.
    Type: Grant
    Filed: July 19, 2007
    Date of Patent: February 7, 2012
    Assignees: University of Tennessee Research Foundation, The Ohio State University Research Foundation
    Inventors: James T. Dalton, Duane D. Miller, Igor Rakov, Casey Bohl, Michael L. Mohler
  • Publication number: 20110263457
    Abstract: We describe herein a cell-based multiplexing technique called detectable cell barcoding (DCB). In DCB, each individual sample is labeled with a different DCB signature that distinguishes each sample by one or both of detected intensity or type of detection characteristic. The samples are then combined and analyzed for a detectable characteristic of interest (e.g., presence of an analyte). By employing multiple distinct DCB labels at varying concentrations, one can perform multiplex analyses on up to hundreds or thousands (or more) of cell samples in a single reaction tube. DCB reduces reagent consumption by factors of 100-fold or more, significantly reduces data acquisition times and allows for stringent control sample analysis.
    Type: Application
    Filed: July 1, 2011
    Publication date: October 27, 2011
    Inventors: Peter O. Krutzik, Garry Nolan
  • Publication number: 20110077221
    Abstract: This invention provides nuclear hormone receptor binding compounds, compositions comprising the same and methods of uses thereof in treating a variety of diseases or conditions in a subject, including, inter-alia, prostate cancer and/or diseases or disorders of bone and muscle.
    Type: Application
    Filed: July 19, 2007
    Publication date: March 31, 2011
    Inventors: James T. Dalton, Duane D. Miller, Igor Rakov, Casey Bohl, Michael L. Mohler
  • Publication number: 20100019658
    Abstract: Organic compounds and organic electroluminescence devices employing the same are provided. The organic compound has a chemical structure represented as follows: wherein, R1 and R2 are independent and can be aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, or R1 and R2 link together with the carbon atoms to which they are attached to form a fused aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, and R3, R4, and R5 are independent and can be H, C1-8 alkyl, C1-8 alkoxy, C1-8 halo-alkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, or a cycloaliphatic group.
    Type: Application
    Filed: December 19, 2008
    Publication date: January 28, 2010
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Chi-Jen LIN, Heh-Lung HUANG, Jin-Sheng LIN, Chien-Hong CHENG, Mei-Rurng TSENG
  • Patent number: 7153968
    Abstract: 8-(biaryl) quinolines wherein the bi-aryl group at the 8-position is in a meta relationship to the quinoline group, are PDE4 inhibitors useful in the treatment of asthma, chronic bronchitis, chronic obstructive pulmonary disease, eosinophilic granuloma, psoriasis and other benign or malignant proliferative skin diseases, endotoxic shock, laminitis in horses, colic in horses, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and brain, inflammatory arthritis, chronic glomerulonephritis, atopic dermatitis, urticaria, adult respiratory distress syndrome, chronic obstructive pulmonary disease in animals, diabetes insipidus, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, arterial restenosis, ortherosclerosis, atherosclerosis, neurogenic inflammation, pain, cough, rheumatoid arthritis, ankylosing spondylitis, transplant rejection, graft versus host disease, hypersecretion of gastric acid, bacterial, fungal induced sepsis, viral induced sepsis, fungal induced
    Type: Grant
    Filed: June 23, 2003
    Date of Patent: December 26, 2006
    Assignee: Merck Frosst Canada, Ltd.
    Inventors: Daniel Dube, Michel Gallant, Patrick Lacombe, Denis Deschenes, Laurence Dube, Yves Girard, Dwight Macdonald
  • Patent number: 7122671
    Abstract: A compound for use as a chemiluminescent label in immunoassay comprises an aryl acridinium ester linked to an N-succinimidyl moiety. The compound is conveniently linked to a monoclonal antibody or other protein and is used in a two-site immunoassay for the quantitation of an antigen of interest, by initiation of the luminescent reaction and subsequent measurement of the photonic emission of the immune complex formed during the immunological reaction.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: October 17, 2006
    Assignee: University College Cardiff Consultants Limited
    Inventors: Anthony Keith Campbell, James Stuart Woodhead, Ian Weeks
  • Patent number: 6872828
    Abstract: Novel compounds comprising a C—C double bond substituted at one carbon with two sulfur atom-containing groups are disclosed. The compounds are useful in methods and compositions for generating chemiluminescence rapidly by reaction with a peroxidase enzyme and a peroxide. The chemiluminescence thus produced can be used as a detectable signal in assays for peroxidase enzymes or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.
    Type: Grant
    Filed: December 20, 2001
    Date of Patent: March 29, 2005
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka de Silva, Wenhua Xie
  • Patent number: 6858733
    Abstract: Novel compounds comprising a C—C double bond substituted at one carbon with two sulfur atom-containing groups are disclosed. The compounds are useful in methods and compositions for generating chemiluminescence rapidly by reaction with a peroxidase enzyme and a peroxide. The chemiluminescence thus produced can be used as a detectable signal in assays for peroxidase enzymes or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: February 22, 2005
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka de Silva, Wenhua Xie
  • Patent number: 6743817
    Abstract: Disclosed are compounds of the formula and the pharmaceutically acceptable salts thereof wherein R, Ar, A, n, R1 and R2 are defined herein. These compounds are highly selective agonists, antagonists or inverse agonists for GABAA brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAA brain receptors and are therefore useful in the diagnosis and treatment of anxiety, depression, Down Syndrome, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory. Pharmaceutical compositions, including packaged pharmaceutical compositions, are also disclosed.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: June 1, 2004
    Assignee: Neurogen Corporation
    Inventors: George Maynard, LingHong Xie, Stanislaw Rachwal
  • Patent number: 6414152
    Abstract: A compound for use as a chemiluminescent label in immunoassay comprises an aryl acridinium ester linked to an N-succinimidyl moiety. The compound is conveniently linked to a monoclonal antibody or other protein and is used in a two-site immunoassay for the quantitation of an antigen of interest, by initiation of the luminescent reaction and subsequent measurement of the photonic emission of the immune complex formed during the immunological reaction.
    Type: Grant
    Filed: October 24, 1994
    Date of Patent: July 2, 2002
    Assignee: University of Wales College of Medicine of Heath Park
    Inventors: Anthony Keith Campbell, James Stuart Woodhead, Ian Weeks
  • Patent number: 6015902
    Abstract: Intercalator compounds of formula I-T.sub.m as defined herein are provided which are comprised of intercalator moieties, or substituted intercalator moieties, having one or more functionalized chains, or moieties, and which compounds provide a high affinity for binding to the DNA molecule and show reduced self-quenching, while providing superior transport kinetics. The compounds have been found to provide enhanced fluorescence when bound to a DNA molecule within a fluorescent flow cytometry environment which is about eight to ten times brighter in fluorescence than "bis" structure conventional intercalating agents and other known intercalating agents utilized in flow cytometry environment.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: January 18, 2000
    Assignee: Abbott Laboratories
    Inventors: Christopher Bieniarz, Jeffrey Bruce Huff, Denis R. Henrard
  • Patent number: 6002007
    Abstract: Chemiluminescent acridinium derivatives of the formula I ##STR1## in which R.sup.4 represents a radical of the formula II or III ##STR2## and A.sup..theta., X--, R.sup.1 -R.sup.3, R.sup.5 and R.sup.6 have the stated meanings, as well as processes for the preparation of the compounds of the formula (I) and the use thereof in chemiluminescence immunoassays.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: December 14, 1999
    Assignee: Dade Behring Marburg GmbH
    Inventors: Tonio Kinkel, Peter Molz, Erwin Schmidt, Gerd Schnorr, Heinz Jurgen Skrzipczyk
  • Patent number: 5879888
    Abstract: A light emitting method of an acridinium ester, comprising reacting said acridinium ester and a superoxide anion, and a method of detecting a substance to be examined, comprising detecting a light emitted by reacting a superoxide anion with an acridinium ester used as a label are described. It is possible to carry out the reaction not under strongly alkaline conditions but around the neutral point and to generate strong luminescence which is stable over a long period of time.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: March 9, 1999
    Assignee: Iatron Laboratories, Inc.
    Inventors: Masuo Aizawa, Yoshihito Ikariyama, Eiry Kobatake, Minoru Ogasawara, Mitsunao Tanaka
  • Patent number: 5565554
    Abstract: Novel fluorescent DNA-staining dyes are provided combining asymmetric cyanine azole-indolenine dyes, which provide for strong DNA affinity, large Stokes shifts and emission in the red region of the spectrum. The dyes find particular application in gel electrophoresis and for labels which may be bound to a variety of compositions in a variety of contexts.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: October 15, 1996
    Assignee: The Regents of the University of California
    Inventors: Alexander N. Glazer, Scott C. Benson
  • Patent number: 5538901
    Abstract: This invention is directed to the novel assay methods utilizing nucleophilic polysubstituted aryl acridinium ester conjugates as the tracers. Conjugates prepared by covalent coupling of novel nucleophilic polysubstituted aryl acridinium esters with biological compounds including small organic molecules such as Vitamin B12, folate, cortisol, estradiol, and thromboxane B2, were found useful in the development of highly sensitive assays for the analytes of diagnostic interest.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: July 23, 1996
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Steve C. S. Chang, Carol K. Klukas, Christine A. Vitkauskas
  • Patent number: 5455252
    Abstract: A compound of the formula ##STR1## wherein: R.sup.1 is independently selected from hydrogen, lower-alkyl, cycloalkyl, cycloalkyl lower-alkyl, lower-alkoxy, formyl, (lower-alkyl)-hydroxylmethyl, aryl, benzyl, arylmethyl, pyridylmethyl,where aryl, benzyl, arylmethyl and pyridylmethyl are unsubstituted or independently mono, di or tri substituted with hydrogen, hydroxy, thiol, amino, halo, nitro, lower-alkylthio, lower-alkoxy, mono-lower-alkylamino, di-lower-alkylamino, hydroxycarbonyl, lower-alkoxycarbonyl, hydroxysulfonyl, lower-alkoxysulfonyl, lower-alkylsulfonyl, lower-alkylsulfinyl, trifluoromethyl, cyano, tetrazoyl, carbamoyl, lower-alkylcarbamoyl, and di-lower-alkylcarbamoyl; andR.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as set forth in the specification.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: October 3, 1995
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Robert S. Wilhelm, Paul R. Fatheree, Ronnie L. Chin
  • Patent number: 5449556
    Abstract: A method for the detection of an analyte in a fluid sample using liposomes encapsulating acridinium esters (lumisomes). Hydrophilic polysubstituted aryl acridinium esters are useful as chemiluminescent markers and can be encapsulated within liposome vesicles without significant leakage of the esters from the vesicles. The lumisomes can be coupled to molecules with biological activity, such as antigens, antibodies, and nucleic acids, and used in luminescent assays.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: September 12, 1995
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Uri Piran
  • Patent number: 5401847
    Abstract: Heteromultimeric fluorophores are provided for binding to DNA, which allow for the detection of DNA in electrical separations and preparation of probes having high-fluorescent efficiencies and large Stokes shifts. In addition, by appropriate choice of fluorescent molecules, one can use a single narrow wavelength band excitation light source, while obtaining fluorescent emissions having sufficient separation to be readily discriminated.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: March 28, 1995
    Assignee: Regents of the University of California
    Inventors: Alexander N. Glazer, Scott C. Benson
  • Patent number: 5338847
    Abstract: Described are a class of chemiluminescent compound characterized by the presence an aryl ester, thioester or amide of a carboxylic acid substituted heterocyclic ring that is susceptible to chemical attack (such as by oxidic attack) to dissociate the heterocyclic ring to a transient compound. The heterocyclic ring is ring carbon-bonded to the carbonyl of the ester, thioester and amide moiety and possesses a heteroatom in an oxidation state that allows chemiluminescence by dissociating a compound ("intermediate") that decays to produce chemiluminescence, at the carbon bonded to the carbonyl. The aryl ring or ring system is ring carbon-bonded to the oxygen, sulfur or nitrogen of the ester, thioester or amide, as the case may be, and contains at least three substituents on a six-member ring. The substitution on the six-member ring comprises three or more groups acting in concert to sterically and electronically hinder hydrolysis of the ester, thioester or amide linkage.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: August 16, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5321136
    Abstract: A chemiluminescent label compound and conjugate containing the same, in which the compound involves a fused ring system comprising a(i) hetercyclic ring as a fused member thereof in which the heterocyclic ring contains(a) one or more nitrogen heteroatoms in the ring;(b) at least one saturated or unsaturated ring in fused state with the heterocyclic ring;(c) an available carbon atom in the heterocyclic ring that is adjacent to a carbon forming a fused ring with the heterocyclic ring; and(d) at least one substituent that is peri relative said available carbon of the heterocyclic ring, which substituent serves to enhance the hydrolytic stability of the chemiluminescent label compound; and(ii) a leaving group coupled to the heterocyclic ring through a carbon adjacent to a fused ring carbon such that the leaving group and heterocyclic ring join to form a difunctional carboxy-containing linkage in which the carboxy carbon is directly bonded to the carbon of the heterocyclic ring adjacent to a fused ring carbon,(a)
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 14, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5290936
    Abstract: A novel chemiluminescent labeling compositions comprising an ester, thiolester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinguished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with --NO.sub.2 meta or para substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: March 1, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Iraj Beheshti, Harlen Koelling
  • Patent number: 5284951
    Abstract: A novel chemiluminescent labeling compositions comprising an ester, thioester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinguished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with meta and/or para substituents thereon that possess an electron withdrawing capacity characterized as a .sigma..sub.p value greater than 0 and less than 1.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 8, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Frank McCapra, Iraj Beheshti
  • Patent number: 5284952
    Abstract: A chemiluminescent labeling composition comprising an ester, thioester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinquished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with meta and/or para --SO.sub.2 -- substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 8, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Kastooriranganathan Ramakrishnan
  • Patent number: 5283334
    Abstract: A chemiluminescent compound possessing an aryl ester, thioester or amide of a carboxylic acid substituted heterocyclic ring or ring system that is susceptible to chemical attack to dissociate the heterocyclic ring to a transient compound. The heterocyclic ring is ring carbon-bonded to the carbonyl of the ester, thioester or amide moiety and possesses a heteroatom in an oxidation state that allows chemiluminescence by dissociating a compound at the carbon bonded to the carbonyl that decays to produce chemiluminescence. The heterocyclic ring or ring sustem contains bonded to it through an organic moiety, a functional group that is functionally reactive with an active hydrogen containing compound. The aryl ring is a ring or ring system that is ring carbon-bonded to the oxygen, sulfur or nitrogen of the ester, thioester or amide, as the case may be, and contains substituents on a six-member ring that act to sterically and electronically hinder hydrolysis of the ester, thioester or amide linkage.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 1, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5281712
    Abstract: A novel chemiluminescent labeling compositions comprising an ester or thiolester covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinquished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with quaternary ammonium meta or para substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: January 25, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Frank McCapra, Beheshti Iraj, Kastooriranganathan Ramakrishnan
  • Patent number: 5241070
    Abstract: This invention is directed to novel nucleophilic polysubstituted aryl acridinium esters and to novel conjugates thereof. The novel nucleophilic polysubstituted aryl acridinium esters and novel conjugates thereof are useful in biological assays, including novel assays for the determination of Vitamin B.sub.12, folate, cortisol, estradiol, and thromboxane B.sub.2.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: August 31, 1993
    Assignee: Ciba Corning Diagnostics Corp.
    Inventor: Say-Jong Law
  • Patent number: 5227489
    Abstract: A method for the detection of an analyte in a fluid sample using liposomes encapsulating acridinium esters (lumisomes). Hydrophilic polysubstituted aryl acridinium esters are useful as chemiluminescent markers and can be encapsulated within liposome vesicles without significant leakage of the esters from the vesicles. The lumisomes can be coupled to molecules with biological activity, such as antigens, antibodies, and nucleic acids, and used in luminescent assays.
    Type: Grant
    Filed: January 22, 1992
    Date of Patent: July 13, 1993
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Uri Piran
  • Patent number: 5151518
    Abstract: A process for the N-arylation of isatins with organo bismuth reagents is disclosed.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: September 29, 1992
    Assignee: Abbott Laboratories
    Inventors: James E. Dombrowski, Phillip G. Mattingly
  • Patent number: 5120745
    Abstract: This invention relates to 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles of the formula ##STR1## wherein the substituents are as defined herein, compositions containing those compounds and methods of use.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: June 9, 1992
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Richard M. Jacobson, Luong T. Nguyen, Muthuvelu Thirugnanam
  • Patent number: 5110932
    Abstract: The present invention relates to novel acridinium esters which are useful as luminescent labels in specific binding assays such as immunoassays or nucleic acid hybridization assays. More particularly, polysubstituted aryl acridinium esters are highly stable labels for use in a chemiluminescent immunoassay.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: May 5, 1992
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Steve C. S. Chang, Stephen A. Palmacci, Roger S. Cubicciotti
  • Patent number: 5086179
    Abstract: This invention is directed to certain dibenzofurancarboxamides and dibenzofurancarboxamide acids and their use as 5HT.sub.3 antagonists having unique CNS, anti-emetic and gastric prokinetic activity void of any significant D.sub.2 receptor binding properties. Further, this invention relates to a process for the synthesis of stereoisomeric compounds having such CNS, anti-emetic and gastric prokinetic activity.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: February 4, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Matthew R. Powers, Raymond D. Youssefyeh, William L. Studt, Frederick A. Golec
  • Patent number: 5075556
    Abstract: Quaternized derivatives of acridine orange and reagents incorporating such derivatives and their use in quantitatively determining reticulocyte levels in whole blood specimen by fluorescence flow cytometry techniques are disclosed. The quaternized derivatives of acridine orange are of the general formula: ##STR1## wherein Y is bromide (Br.sup.-) or iodide (I.sup.-), andX may be R.sub.1 and/or R.sub.2 substituted benzyl group ##STR2## R.sub.1 is hydrogen or fluorine, and R.sub.2 is fluorine, trifluoromethyl or hydrogen, or X may be hydroxyl ethylene.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: December 24, 1991
    Assignee: Technicon Instruments Corporation
    Inventors: Sophie Fan, Gena Fischer
  • Patent number: 5049673
    Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • Patent number: 5013741
    Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R.sub.1 is hydrogen, alkyl, aryl, arylloweralkyl, naphthyl, furyl, thienyl, pyridinyl or pyrrolyl; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.2 or --NR.sub.3 R.sub.4 where R.sub.2 is hydrogen or loweralkyl, and R.sub.3 and R.sub.4 are independently hydrogen, loweralkyl or cycloalkyl; stereo, optical and geometrical isomers thereof, and pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: May 7, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventor: Gregory M. Shutske
  • Patent number: 4946958
    Abstract: A compound for use as a chemiluminescent label in immunoassay comprises an aryl acridinium ester linked to an N-succinimidyl moiety. The compound is conveniently linked to a monoclonal antibody or other protein and is used in a two-site immunoassay for the quantitation of an antigen of interest, by initiation of the luminescent reaction and subsequent measurement of the photonic emission of the immune complex formed during the immunological reaction.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: August 7, 1990
    Assignee: The Welsh National School of Medicine
    Inventors: Anthony K. Campbell, James S. Woodhead, Ian Weeks
  • Patent number: 4918192
    Abstract: The present invention relates to novel acridinium esters which are useful as luminescent labels in specific binding assays such as immunoassays or nucleic acid hybridization assays. More particularly, polysubstituted aryl acridinium esters are highly stable labels for use in a chemiluminescent immunoassay.
    Type: Grant
    Filed: December 14, 1987
    Date of Patent: April 17, 1990
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Steve C. S. Chang, Stephen A. Palmacci, Roger S. Cubicciotti
  • Patent number: 4861564
    Abstract: The compounds of the invention comprise the condensation product, as well as derivatives thereof, of two equivalents of a trimethyl cyclohexane-anhydride acid chloride derivative with one equivalent of an aromatic diamine. The scope of the invention includes the method of using the compounds of the invention as chelating agents for metals, metal ions or ions of metal complexes. In a preferred embodiment of the invention the binding moieties of the cyclohexane derivatives are rigidly held opposite each other, by restricting their rotation about the N-C aryl bonds, in order to more effectively bind the metals or the ions.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: August 29, 1989
    Assignee: Year Laboratories, Inc.
    Inventor: Julius Rebek
  • Patent number: 4851536
    Abstract: There are disclosed compounds of the formula ##STR1## wherein X is O, S, SO, SO.sub.2 or CR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently hydrogen, lower alkyl, carboxyl, lower alkoxy carbonyl, lower cycloalkyl, phenyl, naphthyl, pyridyl, quinolinyl, pyrazinyl, pyridinyl, pyridazinyl, pyrimidinyl, quinoxalinyl, quinazolinyl or any of the foregoing aryl or hetaryl substituents substituted with halo, lower alkyl, lower alkyl carbonyl, benzoyl, COOR.sup.3, OR.sup.3, N(R.sup.3).sub.2, CON(R.sup.3).sub.2, SO.sub.3 R.sup.3, SO.sub.2 N(R.sup.3).sub.2, phenylsulfonyl, lower alkyl sulfonyl, cyano, nitro or trifluoromethyl;R.sup.3 is hydrogen, lower alkyl or phenyl;R.sup.4 is halo, morpholino, 4-methylpiperazino, R.sup.5 NNHR.sup.6,R.sup.5 NCH.sub.2 CH.sub.2 OCH.sub.3, or ##STR2## R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen, lower alkyl, lower alkanoyl, lower cycloalkyl or phenyl; andR.sup.7 and R.sup.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 25, 1989
    Assignee: American Home Products Corporation
    Inventors: Jerauld S. Skotnicki, Steven C. Gilman
  • Patent number: 4822878
    Abstract: Novel chromophor derivatives of cyclic anhydrides are provided which have the ability to react with a variety of organic substrates forming adducts which are useful in analytical techniques for the detection and measurement of biological compounds.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: April 18, 1989
    Assignee: Viomedics, Inc.
    Inventor: Spyros Theodoropulos
  • Patent number: 4788292
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of one another, represent hydrogen, hydroxy or halogen or are alkyl, alkoxy, alkanoyloxy, or alkanoylamino groups which are unsubstituted or substituted by alkoxy, hydroxyl, halogen, aryl, cycloalkyl, azacycloalkyl, cyano or by polyalkyleneoxy, or two or more of adjacent R.sub.1 -R.sub.4 together form one or more fused rings of 5-8 members each; R is alkylene of up to 16 carbon atoms which is unsubstituted or substituted by hydroxy, lower alkoxy, or halo and which may be interrupted by oxygen, sulfur, carboxamido, sulfonamido, aminosulfonyl, aminocarbonyl, carbonyloxy, sulfinyl, or sulfonyl; and R.sub.f is perfluoroalkyl or perfluoroalkoxyalkyl of 4 to 16 carbon atoms; or mixtures thereof. Such compounds are useful as oil soluble corrosion inhibitors.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: November 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Kirtland P. Clark, Athanasios Karydas
  • Patent number: 4767718
    Abstract: Fluorescent reagents useful as opioid receptor probes. Opioids labeled at the 3 position with fluorescers are useful in various in vivo and in vitro methods for the detection and quantification of receptor sites in tissue cells and subcellular particles.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: August 30, 1988
    Assignee: Southern Illinois University Foundation
    Inventor: Vera K. Meyers
  • Patent number: 4745181
    Abstract: The present invention relates to novel acridinium esters which are useful as luminescent labels in specific binding assays such as immunoassays or nucleic acid hybridization assays. More particularly, polysubstituted aryl acridinium esters are highly stable labels for use in a chemiluminescent immunoassay.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: May 17, 1988
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Steve C. S. Chang, Stephen A. Palmacci, Roger S. Cubicciotti
  • Patent number: RE39047
    Abstract: A light emitting method of an acridinium ester, comprising reacting said acridinium ester and a superoxide anion, and a method of detecting a substance to be examined, comprising detecting a light emitted by reacting a superoxide anion with an acridinium ester used as a label am described. It is possible to carry out the reaction not under strongly alkaline conditions but around the neutral point and to generate strong luminescence which is stable over a long period of time.
    Type: Grant
    Filed: March 8, 2001
    Date of Patent: March 28, 2006
    Assignee: Mitsubishi Kagaku Iatron, Inc.
    Inventors: Masuo Aizawa, Michiko Ikariyama, Eiry Kobatake, Minoru Ogasawara, Mitsunao Tanaka, Yoshihito Ikariyama