Acridines (including Hydrogenated) Patents (Class 546/102)
  • Patent number: 5777133
    Abstract: Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (eg., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: July 7, 1998
  • Patent number: 5750698
    Abstract: Acridans which are reactable with a peroxidase and peroxide. The acridans are characterized by having an aromatic leaving group ArO which is a di- or polyhalosubstituted phenoxy group. The compounds are useful in assays where one member of a binding pair is linked to the peroxidase and for detecting the peroxidase. The method can also be used to detect hydrogen peroxide.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: May 12, 1998
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka DeSilva, Zahra Arghavani, Barry A. Schoenfelner
  • Patent number: 5741662
    Abstract: The present invention provides specific binding solid phase assay methods and kits for the detection of the presence or absence of a microorganism by directly staining the microorganism and specifically capturing the stained microorganism on a solid support. The methods find particular utility in the detection of Candida. The methods may simultaneously detect the presence or absence of multiple microorganisms.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: April 21, 1998
    Assignee: Quidel Corporation
    Inventors: Randall D. Madsen, Lorraine S. Bautista, Jan W. Pawlak, Allan D. Pronovost
  • Patent number: 5721254
    Abstract: The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: February 24, 1998
    Assignee: Novo Nordisk A/S
    Inventors: Knud Erik Andersen, Uffe Bang Olsen, Hans Petersen, Frederik Christian Gr.o slashed.nvald, Ursula Sonnewald, Tine Krogh J.o slashed.rgensen, Henrik Sune Andersen
  • Patent number: 5710169
    Abstract: Compounds of formula I ##STR1## wherein Q.sup.1, Q.sup.2, Q.sup.3, Q.sup.4, and Q.sup.5 have any of the meanings given in the specification, their N-oxides, and their pharmaceutically acceptable salts are nonpeptide antagonists of SP and NKA are useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: January 20, 1998
    Assignee: Zeneca Limited
    Inventor: Keith Russell
  • Patent number: 5710273
    Abstract: A complex crystal is composed of anion of triiodine and cation of a fused compound consisting essentially of at least one nitrogen atom and at least 3 aromatic fused rings. Since the complex crystal has such a stable structure, it shows excellent heat resistance and excellent moisture resisting property. Furthermore, the complex crystal has light-polarizing performance because of an arrangement of the molecular chain of iodine. Moreover, the complex crystal exhibits excellent polarization because of an interaction between the fused compound and iodine. Therefore, the complex crystal is suitable for use as light-adjusting particles of a light valve or a light-adjusting glass.
    Type: Grant
    Filed: July 25, 1996
    Date of Patent: January 20, 1998
    Assignees: Toyota Jidosha Kabushiki Kaisha, Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Arimitsu Usuki, Hisato Takeuchi, Narihito Tatsuda, Akane Okada, Toshio Kurauchi, Hiromitsu Tanaka, Shinobu Okayama, Kazuo Tojima, Akio Fukui, Toshiro Okamoto
  • Patent number: 5693649
    Abstract: The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: December 2, 1997
    Assignee: Novo Nordisk A/S
    Inventors: Knud Erik Andersen, Uffe Bang Olsen, Hans Petersen, Frederik Christian Gr.o slashed.nvald, Ursula Sonnewald, Tine Krogh J.o slashed.rgensen, Henrik Sune Andersen
  • Patent number: 5688788
    Abstract: The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: November 18, 1997
    Assignee: Novo Nordisk A/S
    Inventors: Knud Erik Andersen, Uffe Bang Olsen, Hans Petersen, Frederik Christian Gr.o slashed.nvald, Ursula Sonnewald, Tine Krogh J.o slashed.rgensen, Henrik Sune Andersen
  • Patent number: 5641783
    Abstract: Disclosed are compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocycle. R.sub.3 may be either hydrogen or C.sub.1-3. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: June 24, 1997
    Assignee: Cell Therapeutics, Inc.
    Inventors: J. Peter Klein, Gail E. Underiner, Anil M. Kumar
  • Patent number: 5631279
    Abstract: This invention relates to perhydroisoindole derivatives of 08/448,402 formula (I), wherein radicals R are phenyl radicals optionally 2-or 3-substituted by a halogen atom or a methyl radical; R.sub.1 is optionally substituted phenyl, cyclohexadienyl, naphthyl, indenyl or optionally substituted heterocyclyl; R.sub.2 is H, halogen, OH, alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, acyloxy, acyloxy, carboxy, optionally substituted alkyloxycarbonyl, benzyloxycarbonyl, amino or acylamino; and R.sub.3 is optionally 2-substituted phenyl; optionally salts thereof where applicable; and preparation thereof. Said derivatives are particularly useful as neurokinin A antagonists.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 20, 1997
    Assignee: Rhone-Poulenc Rorer, S.A.
    Inventors: Andre Crespo, Veronique Fardin, Jean-Marc Guillaume, Jean-Luc Malleron, Jean-Francois Peyronel
  • Patent number: 5622964
    Abstract: Methods of treating asthma are provided which methods comprise administering to a mammal in need of such treatment an effective amount of a compound of Formula I ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 have any of the meanings given in the specification.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: April 22, 1997
    Assignee: Zeneca Limited
    Inventors: Cyrus J. Ohnmacht, Jr., Diane A. Trainor, Janet M. Forst, Mark M. Stein, Robert J. Harris
  • Patent number: 5616729
    Abstract: Triggerable dioxetanes with a fluorescent substituent bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are carbon containing groups and wherein one of R.sub.1, R.sub.2 and R.sub.3 is a tethered fluorescent substitutent. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: April 1, 1997
    Assignee: Board of Governors of Wayne State University
    Inventors: Arthur P. Schaap, Hashem Akhavan-Tafti
  • Patent number: 5595875
    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: October 19, 1994
    Date of Patent: January 21, 1997
    Assignee: Ciba Corning Diagnostics Corp.
    Inventors: Say-Jong Law, Uri Piran
  • Patent number: 5594112
    Abstract: Acridinium compounds represented by the general formula (I) where A is an intervening group which does not have activity for binding with a specific binding substance, Z is a labelling active group which has activity for binding with a specific binding substance, R.sup.1 is a halogen atom, an alkyl group or an aryl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a nitro group, a halogen atom or a carbonyl group, and Y is a counter ion. The acridinium compounds may form conjugates with specific binding substances. The acridinium compounds have high emission efficiency and stability and, hence, are useful as chemiluminescence labelling agents.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: January 14, 1997
    Assignee: Mochida Pharmaceutical Co., Ltd.
    Inventors: Naofumi Sato, Hiroshi Mochizuki, Toshinori Kanamori
  • Patent number: 5527921
    Abstract: Peroxycarboxylic ester photoinitiators derived from aromatic nitrogen containing heterocyclic carboxylic acids are described. The heterocyclic aromatic ring may contain additional nitrogen atoms, be fused with another aromatic ring system, be substituted with an additional peroxycarboxylic ester group and/or be substituted with an electron group having a Hammett sigma value greater than 0.1. The peroxycarboxylic ester photoinitiators have been found to be useful in photopolymerizable compositions and photosensitive elements.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: June 18, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Jeanne E. Haubrich
  • Patent number: 5523212
    Abstract: Aryl N-alkylacridanthiocarboxylate compounds which produce chemiluminescence. The compounds produce light with peroxide and peroxidase. The compounds are used as a substrate in assays for various analytes.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: June 4, 1996
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka DeSilva, Zahra Arghavani
  • Patent number: 5521103
    Abstract: New acridinium compounds are provided which comply with formula 1, whereinA is a divalent organic moiety, such as an alkylene chain,X is a group which can be transformed together with C-9 of the acridine into a dioxetane by reaction with hydrogen peroxide, such as an aryloxy group,Y is a counter ion, andZ is a functional group, such as a carboxyl derivative.These acridinium compounds are useful as chemiluminogenic labels for both heterogeneous and homogeneous immunoassays.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: May 28, 1996
    Assignee: Mochida Pharmaceutical Co., Ltd.
    Inventors: Gijsbert Zomer, Johannus F. C. Stavenuiter
  • Patent number: 5491072
    Abstract: N-alkylacridan carboxylic acid derivative compounds (I) are used to generate chemiluminescence by the action of a peroxidase enzyme and an oxidant. The compounds I are useful in assays of all types.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: February 13, 1996
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka Desilva, Katsuaki Sugioka
  • Patent number: 5489603
    Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5459264
    Abstract: A method for reducing an .alpha.,.beta.-unsaturated ketone of the present invention includes the step of treating the .alpha.,.beta.-unsaturated ketone with a silyl compound in the presence of a Lewis acid and alcohol to selectively reduce the carbonyl group of the .alpha.,.beta.-unsaturated ketone. According to this method, a deoxy-compound can be obtained from the .alpha.,.beta.-unsaturated ketone by selectively reducing the carbonyl group without reducing an .alpha.,.beta.-unsaturated bond.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: October 17, 1995
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Mitsuru Imuta, Makoto Kobayashi, Teruo Iizuka
  • Patent number: 5457122
    Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined herein, possess an antagonistic activity on leukotriene B.sub.4.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: October 10, 1995
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
  • Patent number: 5455253
    Abstract: Compounds of formula I ##STR1## wherein R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 have any of the meanings given in the specification, and their pharmaceutically acceptable salts are useful in the treatment of urinery incontinence. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: October 3, 1995
    Assignee: Zeneca Limited
    Inventors: Cyrus J. Ohnmacht, Jr., Diane Trainor, Janet M. Forst, Mark M. Stein, Robert J. Harris
  • 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: 5438139
    Abstract: Acridinium compounds represented by the general formula (I) where A is an intervening group which does not have activity for binding with a specific binding substance, Z is a labelling active group which has activity for binding with a specific binding substance, R.sup.1 is a halogen atom, an alkyl group or an aryl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a nitro group, a halogen atom or a carbonyl group, and Y is a counter ion. The acridinium compounds may form conjugates with specific binding substances. The acridinium compounds have high emission efficiency and stability and, hence, are useful as chemiluminescence labelling agents.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: August 1, 1995
    Assignee: Mochida Pharmaceutical Co., Ltd.
    Inventors: Naofumi Sato, Hiroshi Mochizuki, Toshinori Kanamori
  • Patent number: 5395752
    Abstract: An assay method incorporating at least two different chemiluminescent compounds for detection and/or quantitation of at least two substances in a test sample is described. The synthesis of chemiluminescent reagents or conjugates for use in such methods as well as kits incorporating such reagents are also disclosed. The assays have particular application in the field of clinical diagnostics.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: March 7, 1995
    Assignees: Ciba Corning Diagnostics Corp., Ciba-Geigy A.G.
    Inventors: Say-Jong Law, Qingping Jiang, Walter Fischer, John T. Unger, Elizabeth K. Krodel
  • Patent number: 5391553
    Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; X is alkyl of 3-18 carbon atoms, cycloalkyl of 3-7 carbon atoms or cycloalkylloweralkyl; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl or oxygen-bridged diarylloweralkyl; stereo isomers thereof and pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory, methods for synthesizing them, and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: February 21, 1995
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Gregory M. Shutske, Grover C. Helsley, Kevin J. Kapples
  • 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: 5312820
    Abstract: Carbamoyl and oxycarbonyl derivatives of biphenylmethylamines of structure I are angiotensin-II antagonists with balanced AT.sub.1 and AT.sub.2 activity useful in the treatment of hypertension and related disorders and ocular hypertension. ##STR1## where X is --O-- or --N(R.sup.7)--.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: May 17, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Wallace T. Ashton, Linda L. Chang, William J. Greenlee, Steven M. Hutchins, Ralph A. Rivero
  • 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: 5229442
    Abstract: Stabilizing compositions for organic polymers, composed of mixtures of at least one liquid phenolic antioxidant and at least one aminic antioxidant, subjected to thermal treatment, are characterized by their stabilizing capacity which is considerably higher than that of either single components or of corresponding untreated mixtures.These stabilizing compositions can be used in all field where the single components of the mixtures are generally used and, preferably, in the stabilization of organic polymers normally subject to deterioration due to oxidation processes.
    Type: Grant
    Filed: March 6, 1992
    Date of Patent: July 20, 1993
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Fabio Broussard, Carlo Busetto
  • 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: 5208332
    Abstract: An optical probe enables the study of enzyme activity by absorbance spectroscopy or by sensitive fluorescence methods. In particular, the probe provides the ability to monitor the activity of cytochrome P-450.sub.scc enzyme, the rate limiting enzyme for steroid biosynthesis. Located on the inner mitochondrial membrane, P-450.sub.scc catalyzes the conversion of cholesterol to pregnenolone and isocapraldehyde by sequential oxidations of the cholesterol side chain. The fluorogenic probe includes a cholesterol-like steroid linked to a chromophore through a linking group. The chromophore is selected to have little optical response when linked to the steroid substrate and an enhanced optical response when cleaved from the substrate and linking group. Thus, a fluorescent anion that can be optically detected is generated by the side-chain cleavage reaction during steroidogenesis.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: May 4, 1993
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Babetta L. Marrone, Daniel J. Simpson, Clifford J. Unkefer, Thomas W. Whaley
  • Patent number: 5166359
    Abstract: An optical recording medium contains novel azulenemethine dyes of the formula ##STR1## where R is unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, X.sup..crclbar. is an anion, A.sup..sym. is heterocyclic radical, of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, Y, Z and W are as defined, with the proviso that, when A.sup..sym. is a radical of the formula II f, II g, II i or II k, m is 2, A is 1, 2 or 3 and M is 1 or 2.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Acker, Peter Neumann, Wolfgang Schrott, Matthias Dust
  • 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: 5101059
    Abstract: This invention relates to compounds of the formula a compound of the formula ##STR1## wherein X is O, CR.sub.7 R.sub.8, S or NR.sub.9 wherein R.sub.7 and R.sub.8 are independently hydrogen, or lower alkyl, and R.sub.9 is lower alkyl;n is 0 or 1;R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, aryl, or nitro;R.sub.3 is hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, 9-fluorenylalkyl, cycloalkyl, aryl or aralkyl;R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, or aryl or one of R.sub.4 and R.sub.5 is 9-fluorenyl;R.sub.6 is H or COZ wherein Z is an amino acid, a peptide residue or a leaving group; andwith the provisos that when n is 0 and R.sub.3 is hydrogen, R.sub.1 and R.sub.2 are not hydrogen, halogen or nitro; that when n is 0 and R.sub.3 is lower alkyl, R.sub.1 and R.sub.2 are not hydrogen; and that when X is O or CR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are H, that R.sub.1, R.sub.2, R.sub.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: March 31, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, An-Chuu Wu
  • Patent number: 5081252
    Abstract: A process for the preparation of aromatic carboxylic acids or their salts comprises heating carboxyl-free aromatic compounds and aromatic carboxylic acid salts whose basic structures differ from those of the aromatic compounds, or heating polycyclic aromatic compounds with three or more rings and monocyclic or bicyclic aromatic carboxylic acid salts, under carbon dioxide pressure in the presence of one or more metal compounds selected from group (a) of compounds of zinc, cadmium, and thallium and one or more compounds selected from group (b) of compounds of cesium, Group II metals, And Group IIIa metals to effect the intermolecular transfer of the carboxyl groups.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: January 14, 1992
    Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.
    Inventors: Shuichi Mitamura, Yoshimi Kata, Koichi Fujishiro, Yasuhisa Tsutsumi
  • Patent number: 5068339
    Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the flurorescent molecule in the group as a signal.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: November 26, 1991
    Assignee: Board of Governors of Wayne State University
    Inventors: Arthur P. Schaap, Hashem Akhavan-Jaffi
  • Patent number: 5053513
    Abstract: A method of reducing a carbonyl containing acridine of the formula ##STR1## where n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, trifluoromethyl, or NR.sub.3 R.sub.4 where R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl and R.sub.1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl, is disclosed.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: October 1, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Thomas B. K. Lee, George E. Lee, George S. K. Wong, Donna M. Borek, Keith E. Goehring
  • Patent number: 5030631
    Abstract: Novel tricyclic arylsulfonamides useful for treating hypertension and bronchoconstiction, as well as to their pharmaceutical compositions and methods for using the same.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 9, 1991
    Assignee: Schering Corporation
    Inventor: Barr E. Bauer
  • Patent number: 4996320
    Abstract: A pyridine-compound is reacted with fluorine together with a Bronsted acid-compound or Lewis acid to form a N-fluoropyridinium salt which is very active to other compounds but is very selective for the preparation of a desired product and this product is very useful for a fluorine-introducing agent which makes it useful for the preparation of fluoro-compounds such as thyroid inhibitor.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: February 26, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa
  • Patent number: 4985430
    Abstract: There are disclosed a 9-acylamino-tetrahydroacridine derivative represented by the following formula (I): ##STR1## wherein R ##STR2## are as defined in the specification, its optical antipode or pharmaceutically acceptable acid addition salt thereof and a memory enhancing agent containing the same as an active ingredient.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: January 15, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Shuji Morita, Ken-Ichi Saito, Kunihiro Ninomiya, Akihiro Tobe, Issei Nitta, Mamoru Sugano
  • Patent number: RE35177
    Abstract: A pyridine-compound is reacted with fluorine together with a .[.Bronsted.]. .Iadd.Bronsted .Iaddend.acid-compound or Lewis acid to form a N-fluoropyridinium salt which is very active to other compounds but is very selective for the preparation of a desired product and this product is very useful for a fluorine-introducing agent which makes it useful for the preparation of fluoro-compounds such as thyroid inhibitor.
    Type: Grant
    Filed: February 17, 1994
    Date of Patent: March 12, 1996
    Assignees: Sagami Chemical Research Center, Chichibu Onoda Cement Corporation
    Inventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa