Nitrogen, Other Than As Nitro Or Nitroso, Attached Directly Or Indirectly To The Acridine Ring System By Nonionic Bonding Patents (Class 546/104)
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Patent number: 6296787Abstract: Novel heterocyclic compounds which generate chemiluminescence on reaction with a phosphatase enzyme are provided as well as a process for their preparation and intermediates useful therein. The compounds comprise a nitrogen, oxygen or sulfur-containing heterocyclic ring system bearing an exocyclic carbon—carbon double bond. The double bond is further substituted at the distal carbon with a phosphate group and an oxygen or sulfur atom-containing group. Novel compositions further comprising a cationic aromatic compound (CAC) in addition to the heterocyclic phosphate compound are provided. The addition of the CAC in the composition greatly increases the production of chemiluminescence and provides improved detection sensitivity. Compositions further comprising an anionic surfactant and a non-ionic surfactant provide additional improvements in detection sensitivity.Type: GrantFiled: April 26, 2000Date of Patent: October 2, 2001Assignee: Lumigen, Inc.Inventors: Hashem Akhavan-Tafti, Zahra Arghavani, Renuka DeSilva
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Patent number: 6274768Abstract: This invention relates to intermediates in the preparation of acridin derivatives of general formula or pharmaceutically acceptable salts thereof, and to a method of producing them.Type: GrantFiled: March 30, 2000Date of Patent: August 14, 2001Assignee: Gruenenthal GmbHInventors: Claudia Katharina Puetz, Wolfgang Werner Alfred Strassburger, Oswald Zimmer, Werner Guenter Englberger
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Patent number: 6248884Abstract: Extended rhodamine compounds exhibiting favorable fluorescence characteristics having the structure are disclosed. In addition, novel intermediates for synthesis of these dyes are disclosed, such intermediates having the structure In addition, methods of making and using the dyes as fluorescent labels are disclosed.Type: GrantFiled: June 3, 1999Date of Patent: June 19, 2001Assignee: The Perkin-Elmer CorporationInventors: Joe Y. L. Lam, Scott C. Benson, Steven M. Menchen
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Patent number: 6214816Abstract: The compounds are N-substituted azaheterocyclic compounds of formula I wherein R1 and R2 independently are hydrogen, halogen, trifluoromethyl, hydroxy, C1-6-alkyl or C1-6-alkoxy; and Y is >N—CH2— wherein only the underscored atom participates in the ring system; and X is —C(R6R7)—, —CH2CH2—, —CH═CH—CH2—, —CH2—CH═CH—, —CH2—(C═O)—, —(C═O)—CH2—, —CH2CH2CH2—, —CH═CH—, CH(R10)CH2—, —CH2CH(R10) or —(C═O)— wherein R6 and R7 independently are hydrogen or C1-6-alkyl and wherein R10 is C1-6-alkyl or phenyl; and r is 0, 1 or 2; and Z is selected from wherein A is —CH2—, —O—, —S— or —N(R5)— wherein R5 is H or C1-6-alkyl; and R3 is —(CH2)pCOR4 wherein p is 1, 2, 3 or 4 and R4 is OH, NH2, NHOH or C1-6-alkoxy; or a pharmaceutically acceptable salt thType: GrantFiled: March 10, 1999Date of Patent: April 10, 2001Assignee: Novo Nordisk A/SInventors: Rolf Hohlweg, Tine Krogh Jørgensen, Knud Erik Andersen, Uffe Bang Olsen, Zdenék Polivka, Karel Sindelar
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Patent number: 6197825Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: May 28, 1998Date of Patent: March 6, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 6172058Abstract: A pharmaceutical compound of the formula in which R1 is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-10 alkyl, C3-10 cycloalkyl-C2-10 alkenyl, C3-10 cycloalky-C2-10 alkynyl, optionally substituted phenyl-C1-10 alkyl, optionally substituted phenyl-C2-10 alkenyl, optionally substituted phenyl-C2-10 alkynyl, optionally substituted naphthyl, optionally substituted naphthyl-C1-10 alkyl, C1-10 alkoxy-C1-10 alkyl, C3-10 cycloalkoxy-C1-10 alkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl-C1-10 alkyl, optionally substituted phenyl fused to C5-10 cycloalkyl, optionally substituted tricyclic, optionally substituted tricyclic-C1-10 alkyl, or [optionally substituted phenyl(CH2)n]2-C1-10 alkyl, where n is 0 or 1 to 4, and R2 is hydrogen or one of the values for R1; or a salt or ester thereof.Type: GrantFiled: April 3, 1998Date of Patent: January 9, 2001Assignee: Lilly, SAInventors: Concepci{acute over (o)}n Pedregal Tercero, Ivan Collado Cano, Angel Maz{acute over (o)}n Ruiz
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Patent number: 6171520Abstract: Disclosed are SH-labeling reagents containing acridine compounds represented by the following formula (I): wherein A represents the following group: —(CH2)m1— or —(CH2)m2—Q—(CH2)n— in which Q represents a group —S+RX−—, a group —N+RR1X−— wherein R1 represents an alkyl group having 1 to 6 carbon atoms or an aryl group, a group wherein R2 and R3 may be the same or different and are each independently a group —(CH2)k— (k: a number of 1 to 3) or —O(CH2CH2O)l— (l: a number of 1 to 3), m1 stands for a number of 1 to 6, m2 denotes a number of 0 to 2, n means a number of 1 to 2; R represents an alkyl group having 1 to 6 carbon atoms or an aryl group; and X− represents an anion, or intermediates thereof; preparation processes of the acridine compounds; and methods for labeling analytes by using the compounds.Type: GrantFiled: November 14, 1997Date of Patent: January 9, 2001Assignee: SS Pharmaceutical Co., Ltd.Inventors: Kazuhiro Imai, Hiromichi Eto, Takeshi Kotsugai, Tadashi Narita
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Patent number: 6162610Abstract: Xanthan esters and acridans are substrates for horseradish peroxidase. These stable, enzymatically cleavable chemiluminescent esters are substrates for horseradish peroxidase which, together with peroxide is among the extensively used enzyme in enzyme-linked detection methods, including immunoassays, oligonucleotide detection and nucleic acid hybridization. The novel compounds are used, together with peroxide, alkali and the peroxidase, to indicate the presence and/or concentration of target compounds. The assays may be enhanced by the use of polymeric quaternary onium enhancement compounds or similar compounds selected to enhance the chemiluminescence emitted.Type: GrantFiled: September 11, 1998Date of Patent: December 19, 2000
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Patent number: 6162918Abstract: The invention relates to new and known tricyclic dione derivatives of the general formula ##STR1## and to their salts which are inhibitors of herpes simplex virus thymidine kinase in the treatment and prophylaxis of infections caused by herpes simplex virus.Type: GrantFiled: June 28, 1999Date of Patent: December 19, 2000Assignee: Hoffmann-La Roche Inc.Inventors: Joseph Armstrong Martin, Bradley Stuart Sherborne, Gareth Mark Taylor
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Patent number: 6130228Abstract: Compounds of Formula (I), methods for their preparation, pharmaceutical formulations and use thereof.Type: GrantFiled: August 25, 1998Date of Patent: October 10, 2000Assignee: University of StrathclydeInventors: George Rennet Proctor, Alan Lang Harvey, Maureen Theresa McKenna, Steven John Mullins
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Patent number: 6126870Abstract: Chemiluminescent labeling compounds and chemiluminescent labeled conjugates are provided. The compounds comprise an acridan ring bearing an exocyclic double bond and further contain a labeling substituent which permits attachement to compounds of interest. The novel chemiluminescent compounds and labeled conjugates generated chemiluminescence rapidly after undergoing a reaction with an acid, an oxidant and a base. The compounds and conjugates are useful in assays of an analyte in a sample and in assays employing labeled specific binding pairs.Type: GrantFiled: June 17, 1998Date of Patent: October 3, 2000Assignee: Lumigen, Inc.Inventor: Hashem Akhavan-Tafti
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Patent number: 6114332Abstract: A compound which is a bis(acridinecarboxamide) or bis(phenazinecarboxamide) derivative of formula (I): ##STR1## wherein each X, which may be the same or different in a given molecule, is --CH.dbd. or --N.dbd. each of R.sub.1 to R.sub.4 which may be the same or different, H, C.sub.1 -C.sub.4 alkyl, OH, SH, NH.sub.2, C.sub.1 -C.sub.4 alkoxy, aryloxy, NHR, N(R).sub.2, SR, SO.sub.2 R wherein R is C.sub.1 -C.sub.4 alkyl, CF.sub.3, NO.sub.2 or halogen, or R.sub.1 and R.sub.2 together form a methylenedioxy group; each of R.sub.5 and R.sub.6, which may be the same or different, is H or C.sub.1 -C.sub.4 alkyl; Z is (CH.sub.2).sub.n, (CH.sub.2).sub.n O(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.m N(R.sub.7)(CH.sub.2).sub.n or (CH.sub.2).sub.n N(CH.sub.2 CH.sub.2).sub.2 N(CH.sub.2).sub.n wherein R.sub.7 is H or C.sub.1 -C.sub.Type: GrantFiled: June 18, 1999Date of Patent: September 5, 2000Assignee: Xenova LimitedInventors: William Alexander Denny, Swarnalatha Akuritaya Gamage, Julie Ann Spicer, Bruce Charles Baguley, Graeme John Finlay
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Patent number: 6111109Abstract: A process for producing an acridine carboxamide of formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.5 and R.sup.6, which may be the same or different, is H or an organic subsituent, x is from 1 to 6 and Y is N(R)2 wherein R is C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 18, 1999Date of Patent: August 29, 2000Assignee: Xenova LimitedInventors: William Alexander Denny, Swarnalatha Akuratiya Gamage, Julie Ann Spicer, Michael Wright, David Frank Hayman
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Patent number: 6087502Abstract: Acridinium compounds and their conjugates exhibiting high chemiluminescence yield are provided. Such compounds may be used to enable a highly sensitive specific binding assay. The acridinium compounds are represented by formula (I): ##STR1## wherein A is a linker; Z is a binding group; Y is a counter ion; R.sup.1 and R.sup.2 are independently a substituent; p and m are independently an integer of from 0 to 4; n is an integer of from 2 to 5; and X is an organic intervening moiety with a functionality of at least n, having an aryloxy group or an arylsulfonamide group through which X binds to carbonyl carbon bonded to 9-position of the acridinium ring.Type: GrantFiled: July 31, 1996Date of Patent: July 11, 2000Assignee: Mochida Pharmaceuticals Co., Ltd.Inventor: Naofumi Sato
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Patent number: 6083988Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: September 4, 1997Date of Patent: July 4, 2000Inventor: David Alan Becker
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Patent number: 6077845Abstract: This invention relates to acridin derivatives of general formula ##STR1## or pharmaceutically acceptable salts thereof, to a method of producing them and to their use as analgesics.Type: GrantFiled: June 29, 1999Date of Patent: June 20, 2000Assignee: Gruenenthal GmbHInventors: Claudia Katharina Puetz, Wolfgang Werner Alfred Strassburger, Oswald Zimmer, Werner Guenter Englberger
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Patent number: 6071908Abstract: A method of treating neoplastic disease wherein a patient in need of such treatment is administered an effective amount of a radiation-activated cytotoxin prodrug (RACP) which has low toxicity, which is reducible by reducing agents generated by the radiolysis of water and which, upon reduction, releases a sufficient amount of a cytotoxic effector of sufficient cytotoxic potency to kill tumor cells. The tumor cells are irradiated with ionizing radiation to reduce the prodrug which is present at the locus of the tumor cells to release the cytotoxic effector.Type: GrantFiled: May 7, 1998Date of Patent: June 6, 2000Assignee: Auckland Uniservices LimitedInventors: William A. Denny, Moena Tercel, William R. Wilson
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Patent number: 6045727Abstract: Novel heterocyclic compounds which generate chemiluminescence on reaction with a phosphatase enzyme are provided as well as a process for their preparation and intermediates useful therein. The compounds comprise a nitrogen, oxygen or sulfur-containing heterocyclicring system bearing an exocyclic carbon-carbon double bond. The double bond is further substituted at the distal carbon with a phosphate group and an oxygen or sulfur atom-containing group. Novel compositions further comprising a cationic aromatic compound (CAC) in addition to the heterocyclic phosphate compound are provided. The addition of the CAC in the composition greatly increases the production of chemiluminescence and provides improved detection sensitivity. Compositions further comprising an anionic surfactant and a non-ionic surfactant provide additional improvements in detection sensitivity.Type: GrantFiled: August 13, 1997Date of Patent: April 4, 2000Assignee: Lumigen, Inc.Inventors: Hashem Akhavan-Tafti, Zahra Arghavani, Renuka DeSilva
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Patent number: 6037347Abstract: The invention relates to a composition which is a pharmaceutical combination preparation comprising a compound which has an acetylcholinesterase-inhibitory action or exhibits muscarinergic action and a compound which increases the endogenous extracellular adenosine level, wherein the combination preparation is suitable for the treatment of dementia. The invention further relates to a process for the production of the combination preparation. The invention additionally relates to a process for treating patients in need of suitable therapy with the combination preparation.Type: GrantFiled: February 25, 1998Date of Patent: March 14, 2000Assignee: Hoechst AktiengesellschaftInventors: Hans-Peter Schubert, Hildegard Nimmesgern, Karl Rudolphi
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Patent number: 6020131Abstract: The present invention has an object to provide an easy method for detecting a nucleic acid polymer in aqueous phase.The present invention provides a method for detecting the amount of nucleic acid polymer, which comprises the steps of modifying an intercalator to be amphiphilic by using a hydrophobic group, spreading the amphiphilic intercalator on an aqueous solution containing a nucleic acid polymer to form a monolayer of said nucleic acid polymer and said amphiphilic intercalator at the gas-water interface, and measuring surface pressures per unit area of said monolayer.Type: GrantFiled: November 7, 1997Date of Patent: February 1, 2000Assignee: Research Development Corporation of JapanInventors: Kunihara Ijiro, Masatsugu Shimomura
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Patent number: 6018047Abstract: 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: GrantFiled: June 7, 1995Date of Patent: January 25, 2000Inventors: Gijsbert Zomer, Johannus Franciscus Cornelius Stavenuiter
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Patent number: 6002007Abstract: 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: GrantFiled: July 20, 1993Date of Patent: December 14, 1999Assignee: Dade Behring Marburg GmbHInventors: Tonio Kinkel, Peter Molz, Erwin Schmidt, Gerd Schnorr, Heinz Jurgen Skrzipczyk
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Patent number: 5969139Abstract: The invention relates to new and known tricyclic dione derivatives of the general formula ##STR1## wherein W represents hydrogen or lower alkyl;X represents lower alkyl;Y represents NR1;R.sup.1 represents hydrogen, lower alkyl, lower alkoxycarbonyl or lower alkoxycarbonyl-lower alkyl;Z represents aryl or heteroaryl optionally substituted by one or more halo, cyano, nitro, lower alkyl, halo-lower alkyl, lower alkoxy, halo-lower alkoxy, COR.sup.2, OCOR.sup.2, CO.sub.2 R.sup.2, OR.sup.2, S(O).sub.n R.sup.2, NR.sup.2 R.sup.3, N(R.sup.4)COR.sup.5, Ar, Ar-lower alkyl, Het or Het-lower alkyl substituents and/or on adjacent carbon atoms by lower alkylenedioxy;R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each individually represent hydrogen, lower alkyl, Ar, Ar-lower alkyl, Het or Het-lower alkyl substituents; or R.sup.2 and R.sup.3 together represent the group --CH.dbd.CH--CH.dbd.CH-- or --CH.dbd.N--CH.dbd.Type: GrantFiled: August 6, 1997Date of Patent: October 19, 1999Assignee: Hoffmann-La Roche Inc.Inventors: Joseph Armstrong Martin, Bradley Stuart Sherborne, Gareth Mark Taylor
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Patent number: 5891886Abstract: A new treatment schedule for administration of N-?2-(dimethylamino)ethyl!acridine-4-carboxamide and other related carboxamide anticancer drugs in which the drug is administered in a divided-dose schedule comprising two or more administrations at frequent intervals, for example every hour. Schedules to produce cyclic peaks/troughs in plasma levels are mentioned. The compounds can be used for circumventing multidrug resistance in cancers and may, for example, be used in combination with other cytotoxic drugs, especially non-topo II inhibitors. Treatment of melanoma and advanced colon cancer is included.Type: GrantFiled: August 29, 1997Date of Patent: April 6, 1999Assignee: Xenova LimitedInventors: Bruce Charles Baguley, Graham John Atwell, William Alexander Denny, Graeme John Finlay, Gordon William Rewcastle
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Patent number: 5892042Abstract: An acridine derivative metal complex of formula 2 having a large absorption in the near-infrared range and a reduced absorption in the visible range, which acridine derivative metal complex is used in a transparent recording medium: ##STR1## where M is a metal atom, and X is a negative ion.Type: GrantFiled: September 18, 1997Date of Patent: April 6, 1999Assignee: Nippon Paper Industries Co., Ltd.Inventors: Reiji Ohashi, Yukiko Ryu, Tomoaki Nagai, Hidetoshi Yoshioka
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Patent number: 5883256Abstract: A process for removing aromatic heterocyclic compounds from a product-containing solution, in particular a protein solution, by bringing the solution into contact with a support material. The process is preferably carried out following a virus inactivation with acridine or acridine derivatives and makes it possible to remove these virus-inactivating agents from the solution without there being any significant product losses or changes in the biological activity of the solution.Type: GrantFiled: November 26, 1996Date of Patent: March 16, 1999Assignee: Behringwerke AktiengesellschaftInventors: Eckhard Schuler, Karl-Heinz Wenz
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Patent number: 5879888Abstract: 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: GrantFiled: October 30, 1996Date of Patent: March 9, 1999Assignee: Iatron Laboratories, Inc.Inventors: Masuo Aizawa, Yoshihito Ikariyama, Eiry Kobatake, Minoru Ogasawara, Mitsunao Tanaka
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Patent number: 5834157Abstract: Compounds of the formula ##STR1## are suitable as photoinitiators in free-radical-polymerizable mixtures and are notable for a reduced tendency to diffusion and sublimation than comparable known compounds.Type: GrantFiled: December 23, 1996Date of Patent: November 10, 1998Assignee: Agfa-Gevaert AGInventors: Siegfried Scheler, deceased, Klaus-Peter Bergmann, Gerhard Buhr
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Patent number: 5834462Abstract: Novel tricyclic heterocyclic sulfonamide derivatives and sulfonic ester derivatives which have each an antitumor action and are represented by the following general formula (I) and processes for producing the same are provided. These compounds have each an excellent antitumor activity.A sulfonamide derivative or a sulfonic ester derivative represented by the following general formula (I): ##STR1## {G represents an aromatic 5- or 6-membered ring; L represents 0 or --N(R.sup.1)-- (R.sup.1 represents hydrogen or lower alky); and M represents a tricyclic structure selected from among the following ones; ##STR2## ?rings A and B represent each an unsaturated 5- or 6-membered ring; X represents N(R.sup.2), (wherein R.sup.2 represents hydrogen or lower alkyl), or NHCO;Y represents O, S(O).sub.n, C(R.sup.3)(R.sup.4), C(O), N(R.sup.5), CH(R.sup.6)CH(R.sup.7), C(R.sup.8).dbd.C(R.sup.9), N(R.sup.10)C(O), N.dbd.C(R.sup.11), OCH(R.sup.12), S(O).sub.n CH(R.sup.13) or N(R.sup.14)CH(R.sup.15);Z represents nitrogen or C(R.sup.Type: GrantFiled: March 23, 1995Date of Patent: November 10, 1998Assignee: Eisai Co., Ltd.Inventors: Hiroshi Yoshino, Norihiro Ueda, Jun Niijima, Toru Haneda, Yoshihiko Kotake, Kentaro Yoshimatsu, Tatsuo Watanabe, Takeshi Nagasu, Naoko Tsukahara, Nozomu Koyanagi, Kyosuke Kitoh
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Patent number: 5792863Abstract: An acridine derivative metal complex of formula 1 or formula 2 having a large absorption in the near-infrared range and a reduced absorption in the visible range, which acridine derivative metal complex is used in a transparent recording medium: ##STR1## where M is a metal atom, and X is a negative ion.Type: GrantFiled: April 15, 1996Date of Patent: August 11, 1998Assignee: Nippon Paper Industries Co., Ltd.Inventors: Reiji Ohashi, Yukiko Ryu, Tomoaki Nagai, Hidetoshi Yoshioka
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Patent number: 5783699Abstract: Acridinium sulfonylamides and isomers, such as phenanthridinium sulfonylamides, may be employed in applications including chemiluminmescent immunoassays. Methods for synthesis of these compounds include contacting an amine with a sulfonylhalide to form a sulfonamide and acylating with an activated carboxylic acid of an acridine or isomer thereof. The N-sulfonyl-9-acridinium carboxamide and isomers may be conjugated to antigens, haptens, antibodies, and nucleic acids for use in chemiluminescent assays.Type: GrantFiled: May 16, 1995Date of Patent: July 21, 1998Assignee: Abbott LaboratoriesInventors: Phillip Gregory Mattingly, Larry Gene Bennett
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Patent number: 5783696Abstract: 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: GrantFiled: June 7, 1995Date of Patent: July 21, 1998Assignee: Hoechst AktiengesellschaftInventors: Tonio Kinkel, Peter Molz, Erwin Schmidt, Gerd Schnorr, Heinz Jurgen Skrzipczyk
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Patent number: 5669819Abstract: Acridinium sulfonylamides and isomers, such as phenanthridinium sulfonylamides, may be employed in applications including chemiluminmescent immunoassays. Methods for synthesis of these compounds include contacting an amine with a sulfonylhalide to form a sulfonamide and acylating with an activated carboxylic acid of an acridine or isomer thereof. The N-sulfonyl-9-acridinium carboxamide and isomers may be conjugated to antigens, haptens, antibodies, and nucleic acids for use in chemiluminescent assays.Type: GrantFiled: May 16, 1995Date of Patent: September 23, 1997Assignee: Abbott LaboratoriesInventors: Phillip Gregory Mattingly, Larry Gene Bennett
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Patent number: 5668129Abstract: 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: GrantFiled: March 27, 1996Date of Patent: September 16, 1997Assignee: Novo Nordisk A/SInventors: 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
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Patent number: 5663074Abstract: This invention is directed to novel nucleophilic polysubstituted aryl acridinium conjugates and the methods for preparation thereof. The novel nucleophilic polysubstituted aryl acridinium conjugates 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: GrantFiled: March 17, 1993Date of Patent: September 2, 1997Assignee: Chiron Diagnostics CorporationInventor: Say-Jong Law
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Patent number: 5622964Abstract: 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: GrantFiled: August 18, 1995Date of Patent: April 22, 1997Assignee: Zeneca LimitedInventors: Cyrus J. Ohnmacht, Jr., Diane A. Trainor, Janet M. Forst, Mark M. Stein, Robert J. Harris
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Patent number: 5594112Abstract: 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: GrantFiled: April 28, 1995Date of Patent: January 14, 1997Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Naofumi Sato, Hiroshi Mochizuki, Toshinori Kanamori
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Patent number: 5583148Abstract: This invention relates to new pyridyl, quinoline and acridine bis-acyloxymethyl compounds; to compositions comprising these compounds; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer in warm-blooded animals.Type: GrantFiled: July 15, 1991Date of Patent: December 10, 1996Assignee: Research Foundation Of State University Of New YorkInventors: Wayne K. Anderson, Dennis C. Dean
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Patent number: 5550110Abstract: Novel antagonists of endothelin are described, as well as methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, metabolic, endocrinological, neurological disorders especially cerebral vasospasm, stroke, and head injury, congestive heart failure, endotoxic shock, subarachnoid hemorrhage, arrhythmias, asthma, preeclampsia, atherosclerotic disorders including Raynaud's disease, restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, hemorrhagic shock, ischemic bowel disease, and diabetes.Type: GrantFiled: June 30, 1994Date of Patent: August 27, 1996Assignee: Warner-Lambert CompanyInventors: Wayne L. Cody, Annette M. Doherty, John G. Topliss
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Patent number: 5543524Abstract: Acridinium sulfonylamides and isomers, such as phenanthridinium sulfonylamides, may be employed in applications including chemiluminmescent immunoassays. Methods for synthesis of these compounds include contacting an amine with a sulfonylhalide to form a sulfonamide and acylating with an activated carboxylic acid of an acridine or isomer thereof. The N-sulfonyl-9-acridinium carboxamide and isomers may be conjugated to antigens, haptens, antibodies, and nucleic acids for use in chemiluminescent assays.Type: GrantFiled: May 16, 1995Date of Patent: August 6, 1996Assignee: Abbott LaboratoriesInventors: Phillip G. Mattingly, Larry G. Bennett
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Patent number: 5521103Abstract: 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: GrantFiled: June 24, 1991Date of Patent: May 28, 1996Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Gijsbert Zomer, Johannus F. C. Stavenuiter
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Patent number: 5476644Abstract: The present invention provides compounds of the formula ##STR1## chelated with a paramagnetic metal ion wherein Z1 and Z2 each represent the atoms necessary to complete a monocyclic or polycyclic carbocyclic or heterocyclic ring system, said Z1 and Z2 independently optionally substituted with R.sup.6 and R.sup.7, respectively;R.sup.l, R.sup.2, R.sup.3 and R.sup.4 are independently carboxyalkyl (C.sub.1 -C.sub.2), --(CH.sub.2).sub.n --C(.dbd.O)--NH--R.sup.8, or --(CH.sub.2).sub.n --C(.dbd.O)--O--R.sup.8R.sup.5 is carboxyalkyl (C.sub.1 -C.sub.2);R.sup.6 and R.sup.7 are independently hydrogen, benzyl, or benzyloxy, said benzyl or benzyloxy optionally substituted with one, two or three substituents selected from the group consisting of amino, isocyanato (--N.dbd.C.dbd.O), isothiocyanato (--N.dbd.C.dbd.S), --NH--C(.dbd.O)--X or --NH--C(.dbd.S)--X;R.sup.8 is alkyl (C.sub.1 -C.sub.20), --(CH.sub.2).sub.m --Ar, or polyhydroxyalkyl (C.sub.1 -C.sub.Type: GrantFiled: April 13, 1994Date of Patent: December 19, 1995Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Thomas J. Caulfield, John L. Toner, Peng Guo, David L. Ladd
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Patent number: 5468646Abstract: Acridinium sulfonylamides and isomers, such as phenanthridinium sulfonylamides, may be employed in applications including chemiluminmescent immunoassays. Methods for synthesis of these compounds include contacting an amine with a sulfonylhalide to form a sulfonamide and acylating with an activated carboxylic acid of an acridine or isomer thereof. The N-sulfonyl-9-acridinium carboxamide and isomers may be conjugated to antigens, haptens, antibodies, and nucleic acids for use in chemiluminescent assays.Type: GrantFiled: January 3, 1995Date of Patent: November 21, 1995Assignee: Abbott LaboratoriesInventors: Phillip G. Mattingly, Larry G. Bennett
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Patent number: 5468870Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.Type: GrantFiled: October 20, 1994Date of Patent: November 21, 1995Assignee: AGFA-GAVAERT, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5457122Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined herein, possess an antagonistic activity on leukotriene B.sub.4.Type: GrantFiled: July 13, 1993Date of Patent: October 10, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
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Patent number: 5455253Abstract: 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: GrantFiled: April 14, 1994Date of Patent: October 3, 1995Assignee: Zeneca LimitedInventors: Cyrus J. Ohnmacht, Jr., Diane Trainor, Janet M. Forst, Mark M. Stein, Robert J. Harris
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Patent number: 5449556Abstract: 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: GrantFiled: March 17, 1993Date of Patent: September 12, 1995Assignee: Ciba Corning Diagnostics Corp.Inventors: Say-Jong Law, Uri Piran
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Patent number: 5449778Abstract: Novel cyclic amino acids which are useful in preparing biologically active peptides as well as a process for the preparation of D and L enantiomers of the cyclic amino acids are described where an N-protected derivative of the racemic cyclic amino acid is treated with (-)cinchonidine and the resulting salt resolved into the desired enantiomers, as well as derivatives thereof and valuable intermediates used in the process.Type: GrantFiled: September 8, 1994Date of Patent: September 12, 1995Assignee: Warner-Lambert CompanyInventors: Vladimir Beylin, Huai G. Chen, Om P. Goel, Mark E. Marlatt, John G. Topliss
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Patent number: 5438139Abstract: 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: GrantFiled: January 31, 1994Date of Patent: August 1, 1995Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Naofumi Sato, Hiroshi Mochizuki, Toshinori Kanamori
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Patent number: 5395938Abstract: A unique class of chemiluminescent labels containing biotin substitution that are suitable for chemiluminescent assays using inter alia a streptavidin and/or avidin conjugate. The chemiluminescent labels of the invention have the ability to bind to streptavidin and/or avidin per se or to streptavidin and/or avidin conjugated with an analyte. Label structures are disclosed that have hydrolytic stability to meet the most demanding commercial assay conditions. The invention encompasses conjugates containing associated versions of the labeling compounds, assays and kits for performing such assay utilizing the conjugates.Type: GrantFiled: August 21, 1992Date of Patent: March 7, 1995Assignee: Nichols Institute DiagnosticsInventor: Kastooriranganathan Ramakrishnan