Containing -c(=x)x-, Wherein The X's Are The Same Or Diverse Chalcogens Patents (Class 534/16)
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Patent number: 5384108Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with hydrazide derivatives of polyaminocarboxylic acid chelating agents. The complexes are represented by the formula of: ##STR1## wherein A is --CHR.sup.2 --CHR.sup.3 -- or ##STR2## M.sup.+Z is a paramagnetic ion of an element with an atomic number of 21-29, 42-44 58-70, and a valence, Z, of +2 or +3; R.sup.1 groups may be the same or different and are selected from the group consisting of --O.sup.- and ##STR3## The R.sup.4, R.sup.5 and R.sup.6 groups are as defined in the disclosure. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions. A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: April 24, 1989Date of Patent: January 24, 1995Assignee: Mallinckrodt Medical, Inc.Inventor: Raghavan Rajagopalan
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Patent number: 5382421Abstract: A method is provided utilizing contrast agents which provide increased diagnostic information in the magnetic resonance image of the hepatobiliary system and alimentary tract, especially the small intestine. Novel contrast agents which are N-carboxylated desferrioxamine B complexes with metal ions are provided.Type: GrantFiled: September 17, 1993Date of Patent: January 17, 1995Assignee: The Regents of the University of CaliforniaInventors: David L. White, Barry L. Engelstad, Kurt Muetterties
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Patent number: 5376358Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with aminoalkylamide derivatives of diethylenetriaminepentaacetic acid ("DTPA") or ethylenediaminetetraacetic acid ("EDTA") or other polyaminocarboxylic or cyclic polyaminocarboxylic chelating agents. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: December 21, 1990Date of Patent: December 27, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Muthunadar P. Periasamy
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Patent number: 5374416Abstract: The invention relates to ligands of formula ##STR1## in which B represents an ##STR2## W representing the ##STR3## group, in which groups X and Z represent a heterocycle. The invention also relates to the monometallic or polymetallic complexes formed by these ligands with metal ions chosen from lanthanide ions, transition metal ions. barium, bismuth, lead and the radioisotopes .sup.99m Tc, .sup.111 In, .sup.90 Y, .sup.64 Cu and .sup.169 Yb, as well as the physiologically acceptable salts of these complexes.The salts of these complexes may be used as diagnostic or therapeutic agents in nuclear magnetic resonance imaging and X-ray radiology, as in-vivo chemical shift agents and in nuclear medicine.Type: GrantFiled: November 17, 1992Date of Patent: December 20, 1994Assignee: Guerbet S.A.Inventors: Olivier Rousseaux, Michel Schaefer, Anne Bouillot, Dominique Meyer
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Patent number: 5369101Abstract: The present invention involves a novel tripyrrole dimethine-derived "expanded porphyrin" (texaphyrin), the synthesis of such compounds, their analogs or derivatives and their uses. These expanded porphyrin-like macrocycles are efficient chelators of divalent and trivalent metal ions. Metal complexes of these compounds are active as photosensitizers for the generation of singlet oxygen and thus potentially for inactivation or destruction of human immunodeficiency virus (HIV-1), mononuclear or other cells infected with such virus and tumor cells as well. A variety of texaphyrin derivatives have been produced and many more are readily obtainable. Various metal (e.g., transition, main group, and lanthanide) complexes with the texaphyrin and texaphyrin derivatives of the present invention have unusual water solubility and stability which render them particularly useful. These metallotexaphyrin complexes have optical properties making them unique as compared to existing porphyrin-like or other macrocycles.Type: GrantFiled: December 16, 1993Date of Patent: November 29, 1994Assignee: Board of Regents, The University of Texas SystemInventors: Jonathan L. Sessler, Gregory W. Hemmi, Toshiaki Murai
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Patent number: 5362475Abstract: A diagnostic medium contains at least one physiologically well tolerated complex salt comprising an anion of a complexing acid and one or more Gadolinium ions and, optionally, one or more physiologically biocompatible cation or cations of an inorganic and/or organic base or amino acid, optionally, with additives customary in galenic formulations, dissolved or suspended in an aqueous medium.Type: GrantFiled: July 10, 1992Date of Patent: November 8, 1994Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Douwe Rosenberg, Hanns-Joachim Weinmann, Ulrich Speck, Wolfgang Mutzel, Georg-Alexander Hoyer, Heinrich Pfeiffer, deceased, Franz-Josef Renneke
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Patent number: 5360898Abstract: A method for making a rare earth metal salt of an organic acid, for example neodymium naphthenate, is provided. The method includes the steps of producing a three-phase system which comprises an aqueous phase in which is dissolved a salt of a rare earth metal or an alkali metal or alkaline earth metal salt, a solid water-insoluble rare earth compound suspended in the aqueous phase, and an organic phase containing the organic acid. The organic acid is allowed to distribute between the organic and aqueous phases, react with the dissolved inorganic salt and release an inorganic acid. This leads to some of the water-insoluble rare earth compound becoming dissolved in the aqueous phase and reacting with the organic acid to form a rare earth metal salt of the organic acid. The rare earth metal salt of the organic acid is allowed to transfer to the organic phase from whence it is recovered.Type: GrantFiled: February 19, 1993Date of Patent: November 1, 1994Assignee: Sentrachem LimitedInventors: Amor Jordaan, Petrus J. Stander
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Patent number: 5358704Abstract: Novel compounds of the formula ##STR1## and metal chelates of the compounds are useful particularly for MRI of the hepatobiliary system.Type: GrantFiled: September 30, 1993Date of Patent: October 25, 1994Assignee: Bristol-Myers SquibbInventors: Jean F. Desreux, Michael F. Tweedle, Peter C. Ratsep, Thomas R. Wagler, Edmund R. Marinelli
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Patent number: 5352431Abstract: There is disclosed an imaging agent for diagnosis comprising a compound composed of a polynuclear type compound of the formula I or II: ##STR1## wherein each X is a hydrogen atom or a bifunctional ligand, at least one of them are bifunctional ligand and m or n is an integer or 1 to 6, and at least one metal ion being coordinated with at least one bifunctional ligand moiety, said metal ion being selected from the group consisting of metal ions having the atomic number of 21-29, 31, 32, 37-39, 42-44, 49 and 56-83.Type: GrantFiled: September 13, 1993Date of Patent: October 4, 1994Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Yuji Hashiguchi, Kumiko Iwai, Shigemi Seri, Susumu Kondo, Makoto Azuma
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Patent number: 5344639Abstract: The present invention relates to a contrast agent for NMR imaging constituted by a complex between a chelating agent and paramagnetic metal cations, wherein said complex corresponds to the formula I: ##STR1## or a physiologically acceptable salt of this complex, in which formula: n and n' are whole numbers from 1 to 4R.sub.1 -R.sub.7 are selected from among H, a halogen, alkyl, alkoxy, aryl, alkenyl, and cycloalkyl groups; with the alkyl groups being optionally substituted by halogen, alkoxy, alkyl, nitrile, nitro or amino; >C(R.sub.6, R.sub.7) can in addition represent >C=O;the three substituents Y are identical or different and represent H or an ionic equivalent of a divalent or trivalent paramagnetic metal cation or of a physiologically acceptable cation derived from an inorganic or organic base,with the condition that at least two of the substituents Y represent ionic equivalents of paramagnetic metal cations.Type: GrantFiled: June 26, 1991Date of Patent: September 6, 1994Assignee: Medgenix Group S.A.Inventors: Kwok W. Chiu, Wassif Hussain, John R. Thornback
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Patent number: 5336762Abstract: The present invention includes an image-enhancing agent comprising a biodegradable, water-soluble polymer, synthetic or naturally derived and having repeating hydrophilic monomeric units with amino or hydroxyl groups. This agent also includes chelating agents comprising functional groups bound to an amino or hydroxyl group of the monomeric units. These chelating agents have a formation constant for divalent or trivalent metal cations of at least about 10.sup.8 at physiological temperature and pH. This image-enhancing agent is biodegradable to intermediary metabolites, excretable chelates, oligomers, monomers or combinations thereof of low toxicity. These image-enhancing agents may further comprise a paramagnetic metal ion for enhancement of the image arising from induced magnetic resonance signals. Images resulting from scanning of gamma particle emissions may be enhanced when the image-enhancing agent of the present invention comprises radioisotopic metal ions emitting gamma particles.Type: GrantFiled: January 16, 1991Date of Patent: August 9, 1994Assignee: Access Pharmaceuticals, Inc.Inventor: David F. Ranney
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Patent number: 5334371Abstract: The macrocyclic compounds of the following formula I and IV, defined herein and their salts with inorganic and/or organic bases, amino acids or amino acid amides are valuable diagnostic and therapeutic agents.Type: GrantFiled: July 6, 1992Date of Patent: August 2, 1994Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Bernd Raduchel, Johannes Platzek, Hanns-Joachim Weinmann, Wolf-Rudiger Press, Ulrich Speck
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Patent number: 5332558Abstract: An improved method is proposed for the preparation of a powder of rare earth oxide of which the particles have a predominantly polyhedral configuration with a relatively large particle size to be suitable, for example, as a host of phosphors. The method comprises the steps of (a) precipitating a rare earth ammonium oxalate by the admixture of an aqueous solution of a rare earth salt and ammonium oxalate, (b) separating the precipitates from the aqueous medium, (c) washing the same with deionized water to be freed from electrolytes, (d) dispersing and keeping the precipitates in a hot water bath at 50.degree. C. or higher for at least 15 minutes, (e) collecting the precipitates and (f) calcining the precipitates of the rare earth ammonium oxalate into oxide. It is essential that the steps (a) to (c) are conducted at a temperature of 40.degree. C. or below or, preferably, 30.degree. C. or below.Type: GrantFiled: May 10, 1993Date of Patent: July 26, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masami Kaneyoshi, Tomoyuki Yamada, Norifumi Yoshida
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Patent number: 5330743Abstract: A contrast enhancing agent for magnetic resonance images having a chelating agent, which can be bound to metals having at least one unpaired electron. Examples of such chelating agents include 3,6,9-tris(carboxymethyl)-1, 11-bis(dimethylamine)-3,6,9-triazaundecane; 3,6,9-tris(carboxymethyl)-1, 11-bis(diethanolamino) 3,6,9-triazaundecane; 3,6,9-tris(carboxymethyl)-1, 11-bis(tris(hydroymethyl) aminomethane)-3,6,9-triazaundecane; 3,6-bis(carboxymethyl-1,8-bis(N-carboxymethylglucosamino)-3,6-diazoctane; DTPA-bis(galactosamide), DTPA-Bis(glucosamide), DTPA-Bis(pyridoxamide), and poly-(DTPA-ethylenediamide).Type: GrantFiled: November 12, 1992Date of Patent: July 19, 1994Assignee: Magnetic Research, Inc.Inventors: Wendell A. Gibby, N. Rao Puttagunta
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Patent number: 5328992Abstract: Compounds of the formula ##STR1## in which R is alkyl having up to 4 carbon atoms, n has an average value of at least 9, X is a radical of the formula --C(.dbd.O)--(NH--SO.sub.2).sub.m -- in which m is 0 or 1 and, if m is 1, the carhonyl group may be bonded to the oxygen atom or to the nitrogen atom, and each of the radicals A.sub.1, A.sub.2 and A.sub.3, independently of the others, is hydrogen or an acyl radical, and salts of salt-forming compounds of formula I, as well as metal complexes of compounds of formula I, in which A.sub.1, A.sub.2 and A.sub.3 are hydrogen can be used as metal chelators and as auxiliaries in diagnosis.Type: GrantFiled: October 27, 1992Date of Patent: July 12, 1994Assignee: Ciba-Geigy Corp.Inventors: Heinrich Peter, Theophile Moerker
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Patent number: 5326891Abstract: Novel hydrophobicized double-layer hydroxide compounds, processes for their production by reaction of double-layer hydroxides with aliphatic mono- and/or dicarboxylic acids, and their uses as alkoxylation catalysts for compounds containing active H atoms or for fatty acid esters.The hydrophobicized double-layer hydroxide compounds correspond to formula (I)(M(II).sub.1-x M(III).sub.x (OH).sub.2)A.sub.a B.sub.b * z H.sub.2 O (I)in whichM(II) is a divalent metal cation selected from the group consisting of magnesium, zinc, calcium, iron, cobalt, copper, cadmium, nickel and manganese;M(III) is a trivalent metal cation selected from the group consisting of aluminum, iron, chromium, manganese, bismuth and cerium;A is an equivalent of a monoanion of an aliphatic C.sub.2-34 monocarboxylic acid or an equivalent of a dianion of an aliphatic C.sub.Type: GrantFiled: April 29, 1993Date of Patent: July 5, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolfgang Breuer, Hans-Christian Raths
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Patent number: 5324503Abstract: Hybrid agents for enhancing in vivo diagnostic imaging of body organs and tissues, and methods of preparing and using the same.Type: GrantFiled: February 6, 1992Date of Patent: June 28, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Youlin Lin, Muthanadar P. Periasamy, Donald R. VanDeripe
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Patent number: 5324825Abstract: The invention pertains to terpyridine compounds having structure (I). These compounds form fluorescent lanthanide chelates with the appropriate metal ions. The fluorescent metal chelates are useful as probes in time-resolved fluorescence spectroscopy.Type: GrantFiled: October 28, 1992Date of Patent: June 28, 1994Assignee: Wallac OYInventors: Jouko Kankare, Harri Takalo, Elina Hanninen, Matti Helenius, Veli-Matti Mukkala
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Patent number: 5322681Abstract: The invention provides novel condensed macrocyclic chelants of formula [X(CR.sup.2 R.sup.3).sub.n ].sub.m, (wherein each X independently represents an oxygen or sulphur atom or a group of formula NH, N(CR.sup.2 R.sup.3).sub.p R.sup.4, N(CR.sup.2 R.sup.3).sub.p Y, or N(CR.sup.2 R.sup.3).sub.n- N((CR.sup.2 R.sup.3).sub.p Y).sub.2 ; each Y independently represents a group COZ, SO.sub.2 Z, POZ.sub.2, CON(OH)R.sup.2, CH.sub.2 SR.sup.2, CS.sub.2 R.sup.2 or CSZ; each Z independently represents a group OR.sup.2 or NR.sup.2 R.sup.2 ; n is an integer of 1 to 4; m is an integer of 3 to 8; p is an integer of 1 to 3; each R.sup.2 independently represents a hydrogen atom or a C.sub.1-8 alkyl group optionally mono- or poly-substituted by hydroxyl or C.sub.1-8 alkoxy groups and at least one pair of R.sup.2 groups, in each pair one being from a (CR.sup.2 R.sup.3).sub. n moiety and the other being from a (CR.sup.2 R.sup.3).sub.n or (CR.sup.2 R.sup.3).sub.Type: GrantFiled: July 17, 1992Date of Patent: June 21, 1994Assignee: Nycomed Imaging ASInventor: Jo Klaveness
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Patent number: 5322934Abstract: The use of continuous deionization as an alternative or substitute method for the purification of a crude magnetic resonate.Type: GrantFiled: September 2, 1992Date of Patent: June 21, 1994Assignee: Mallinckrodt Medical, Inc.Inventor: Mills T. Kneller
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Patent number: 5316756Abstract: Compounds of the general formula I: ##STR1## R.sup.1 signifies a COOX group or the group ##STR2## R.sup.2 and R.sup.3 are the same or different and signify a hydrogen atom, a lower straight- or branched-chain, hydrocarbon radical, a phenyl or benzyl group or either R.sup.2 or R.sup.3 signifies the group ##STR3## or R.sup.2 or R.sup.3 together signify a trimethylene or tetramethylene radical, R.sup.4 represents a straight- or branched-chain mono- or poly-hydroxyalkyl radical, R.sup.5 represents a hydrocarbon atom, a lower straight- or branched-chain, optionally mono- or poly-hydroxylated, hydrocarbon radical, Q signifies an oxygen or sulfur atom or the group ##STR4## wherein j signifies the numbers 1 to 4 and R.sup.Type: GrantFiled: April 13, 1990Date of Patent: May 31, 1994Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Franz-Josef Renneke, Hanns-Joachim Weinmann
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Patent number: 5314680Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with hydrazide derivatives of polyaminocarboxylic acid chelating agents. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: May 4, 1993Date of Patent: May 24, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Rebecca A. Wallace, Muthunadar P. Periasamy
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Patent number: 5312617Abstract: Novel complexes of paramagnetic ions and compounds bearing long acyl chains have been synthesized as magnetic resonance imaging contrast agents. These novel liposoluble contrast agents may be administered alone, or with lipids, suspending agents or other additives. The lipids may be in the form of liposomes, micelles or lipid emulsions. The contrast agents of the invention have particular use in magnetic resonance imaging of the liver, blood pool and reticuloendothelial system.Type: GrantFiled: May 22, 1992Date of Patent: May 17, 1994Inventors: Evan C. Unger, DeKang Shen
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Patent number: 5308548Abstract: Preparing a novel cerium (IV) compound, well adopted for the production of aqueous colloidal sols therefrom, has the general formula (I): ##STR1## wherein M is an alkali metal or a quaternary ammonium radical; t ranges from 0.1 to 0.3; n is 0 or 1; x ranges from 0.1 to 0.7; y is a number such that y=4+t-x-z; and z ranges from 0.3 to 0.6.Type: GrantFiled: July 8, 1992Date of Patent: May 3, 1994Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Jean-Yves Chane-Ching
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Boron-gadolinium compounds and method of conducting imaging and/or neutron capture therapy with same
Patent number: 5286853Abstract: A gadolinium (3.sup.+) complex of polyamine polyacetate, comprising a polyamine nucleus having a pendant boron-containing substituent on one of the nitrogen or carbon atoms of the polyamine nucleus. The boron-gadolinium compound may suitably be of the formula: ##STR1## wherein: is a polyamine coordination structure capable of covalently bonding the substitutents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 and of complexing with Gd;R.sub.1, R.sub.2, and R.sub.3 are independently selected from carboxyl, carboxylic salt groups, carboxylic ester groups, and carboxylate anion;R.sub.4 is a boron-containing group; andx is a number from zero to 4.Type: GrantFiled: September 11, 1992Date of Patent: February 15, 1994Assignee: Boron Biologicals, Inc.Inventors: Bernard F. Spielvogel, Anup Sood -
Patent number: 5284647Abstract: Porphyrin complex compounds, consisting of a mesotetraphenylporphyrin ligand, optionally at least one ion of an element with atomic numbers 13, 21, 32, 37-39, 42-44, 49, 50 or 57-83 as well as optionally cations of inorganic and/or organic bases, amino acids or amino acid amides, are valuable diagnostic and therapeutic agents.Type: GrantFiled: January 9, 1992Date of Patent: February 8, 1994Assignee: Schering AktiengesellschaftInventors: Ulrich Niedballa, Hanns-Joachim Weinmann, Heinz Gries, Jurgen Conrad, Sabina Hofmann, Ulrich Speck
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Patent number: 5277895Abstract: Tetraazacyclododecane compounds of general formula I ##STR1## in which E and Q are defined herein and their salts with inorganic and/or organic bases, amino acids or amino acid amides are valuable pharmaceutical agents.Type: GrantFiled: November 8, 1991Date of Patent: January 11, 1994Assignee: Schering AktiengesellschaftInventors: Johannes Platzek, Heinz Gries, Hanns-Joachim Weinmann, Wolf-Rudiger Press, Hubert Vogler
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Patent number: 5274082Abstract: A chelating compound of the formula:(R--NHOC--CH.sub.2).sub.n --A--(CH.sub.2 COOH).sub.m (I)wherein R is an aromatic ring-containing organic group, A is a residue of an aminopolyacetic acid excluding acetic acid groups (--CH.sub.2 COOH) therefrom, m is an integer of at least two and n is an integer of 1 or 2, or its salt, which has a specificity to a hepatobiliary system so that a complex formed between said chelating compound and a metallic element through a coordinate bond is useful as a diagnostic or therapeutic agent for hepatobiliary organs and tissues.Type: GrantFiled: February 25, 1992Date of Patent: December 28, 1993Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Shigemi Seri, Hirohiko Yamauchi, Makoto Azuma, Yoji Arata
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Patent number: 5271924Abstract: There is disclosed an imaging agent for diagnosis comprising a compound composed of a polynuclear type compound of the formula I or II: ##STR1## wherein each X is a hydrogen atom or a bifunctional ligand, at least one of them are bifunctional ligand and m or n is an integer of 1 to 6, and at least one metal ion being coordinated with at least one bifunctional ligand moiety, said metal ion being selected from the group consisting of metal ions having the atomic number of 21-29, 31, 32, 37-39, 42-44, 49 and 56-83.Type: GrantFiled: September 29, 1992Date of Patent: December 21, 1993Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Yuji Hashiguchi, Kumiko Iwai, Shigemi Seri, Susumu Kondo, Makoto Azuma
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Patent number: 5271929Abstract: There is disclosed a nuclear magnetic resonance imaging agent comprising a complex compound composed of (a) a dialdehyde-saccharide having a molecular weight of from 500 to 10,000, at least one of the constituent monosaccharides of which is oxidation-cleaved, (b) at least one complexing agent which is chemically coupled to an aldehyde group of the dialdehyde-saccharide and (c) a paramagnetic metal ion which is chemically coupled to the complexing agent.Type: GrantFiled: July 8, 1992Date of Patent: December 21, 1993Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Yuji Hashiguchi, Kumiko Iwai, Shigemi Seri, Susumu Kondo, Makoto Azuma
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Patent number: 5252720Type: GrantFiled: January 21, 1992Date of Patent: October 12, 1993Assignee: Board of Regents, The University of Texas SystemInventors: Jonathan L. Sessler, Gregory W. Hemmi, Tarak D. Mody
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Patent number: 5250668Abstract: A family of benzochlorins, a family of verdins, a family of porphyrin derivatives and metal complexes thereof are disclosed. The benzochlorins have the formula of FIG. 3 of the attached drawings; their metal complexes have the formula of FIG. 1 . The verdins have the formulas of FIGS. 4 and 6 of the attached drawings; their metal complexes have the formulas of FIGS. 2 and 5. The porphyrin derivatives have the formula of FIG. 9 of the attached drawings; their metal complexes have the formula of FIG. 10 . Solutions of the benzochlorins, verdins, porphyrin derivatives and metal complexes which are physiologically acceptable for intravenous administration are also disclosed, as are emulsions or suspensions of the solutions, and compositions which additionally include cyclodextrin, and wherein the molecules of the benzochlorin, verdin, porphyrin derivative or metal complex are encapsulated within the molecules of the cyclodextrin.Type: GrantFiled: January 8, 1992Date of Patent: October 5, 1993Inventors: Alan R. Morgan, Steven H. Selman
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Patent number: 5246696Abstract: Substantially nontoxic manganese or gadolinium complexes of compounds of the formula: ##STR1## wherein n and m=1, 2, 3 or 4, y=1, 2 or 3, and x is selected from the group consisting of S, CHOH and CHSH, are useful for enhancing magnetic resonance images of body organs and tissues. Illustrative manganese and gadolinium complexes of such compounds include disodium [[(2-hydroxytrimethylene)dinitrilo]tetraaceto]manganese(II) and sodium [[(2-hydroxytrimethylene)dinitrilo]tetraaceto)gadolinium(III).Type: GrantFiled: July 10, 1992Date of Patent: September 21, 1993Assignee: Mallinckrodt Medical, Inc.Inventor: Richard T. Dean
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Patent number: 5245038Abstract: A class of fluorescent rare earth chelates and the ligands upon which they are based whose molecular structure incorporates a plurality of substituted arylpyridine diacid units attached to a central template structure is disclosed. These ligands function as efficient energy transfer groups in fluorescent tagging reagents and tracers.Type: GrantFiled: March 27, 1991Date of Patent: September 14, 1993Assignee: Baxter Diagnostics Inc.Inventors: Ron L. Hale, Dennis W. Solas
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Patent number: 5242681Abstract: The present invention relates to contrast enhancing agents, conjugates thereof, pharmaceutical compositions thereof, and methods for diagnostic analysis, particularly NMR image analysis using these agents. The contrast enhancing agents are chelates of paramagnetic, ferromagnetic or diamagnetic metal ion(s) complexed with new lipophilic complexing acids related to polyaminopolycarboxylic acids.Type: GrantFiled: August 4, 1992Date of Patent: September 7, 1993Assignee: Research Corporation Technologies, Inc.Inventors: Gabriel A. Elgavish, Sung K. Kim
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Patent number: 5242683Abstract: There is provided a contrast medium comprising a physiologically tolerable paramagnetic metal species containing substance together with a water soluble iodinated X-ray contrast agent. The contrast medium can be used for both X-ray and magnetic resonance imaging of the gastro-intestinal tract but overcomes or greatly reduces the side effects experienced by mannitol-containing prior art contrast media.Type: GrantFiled: December 10, 1991Date of Patent: September 7, 1993Assignee: Nycomed Imaging ASInventor: Jo Klaveness
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Patent number: 5217706Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with hydrazide derivatives of polyaminocarboxylic acid chelating agents. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: June 3, 1992Date of Patent: June 8, 1993Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Rebecca A. Wallace, Muthunadar P. Periasamy
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Patent number: 5216134Abstract: A chelate formed between Eu.sup.3+, Tb.sup.3+, Dy.sup.3+ and Sm.sup.3+ and a compound having the formula ##STR1## where A.sub.1-6 are single carbon or nitrogen atoms; n=1 or 2; R.sub.1-6 is nothing when A is a nitrogen, and hydrogen or an organic group when A is a carbon; Z and Z' are selected among --N(CH.sub.2 CH.sub.2 COO.sup.-).sub.2, --N(CH.sub.2 COO.sup.-).sub.2, --N(CH.sub.2 OPO.sub.3.sup.2-).sub.2 and --N(CH.sub.2 PO.sub.3.sup.2-).sub.2 ;--species that --X--Y is a substituent replacing a hydrogen anywhere in the parent compound; and --X--Y represents an organic group containing no chelating heteroatom closer than four atoms from a chelating heteroatom in the parent compound and X is a stable bridge containing certain groups and Y is selected from (a) specified relative groups allowing coupling to other compounds and (b) residues of compounds participating in biospecific affinity reactions.Type: GrantFiled: March 6, 1991Date of Patent: June 1, 1993Assignee: Wallac OyInventors: Veli-Matti Mukkala, Christian Sund, Marek Kwiatkowski
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Patent number: 5216012Abstract: Families of chlorins, families of purpurins and metal complexes thereof are disclosed. The purpurins and their metal complexes have the structures of FIGS. 1, 7, 14-18, 29-38, 44-48 and 54-58 of the attached drawings. The chlorins and their metal complexes have the formulas of FIGS. 2, 8, 19, 20, 22, 23, 24, 25, 27, 28, 39, 40, 42, 43 and 49-53 of the attached drawings. Solutions of the purpurins, of the foregoing and other chlorins and of the metal complexes which are physiologically acceptable for intravenous administration are also disclosed, as are emulsions or suspensions of the solutions. The solvent for the solutions can be a product of the reaction of ethylene oxide with castor oil. A method for detecting and treating tumors in human and animal patients is also disclosed. The method comprises administering one of the purpurins, chlorins or metal complexes to the patient.Type: GrantFiled: September 23, 1991Date of Patent: June 1, 1993Assignees: University of Toledo, Medical College of Ohio, St. Vincent Medical CenterInventors: Alan R. Morgan, Steven H. Selman, Martha Kreimer-Birnbaum
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Patent number: 5208324Abstract: There are provided paramagnetic compounds comprising a paramagnetic metal species chelated by a chelating moiety bound by an amide group to a linker group itself bound by an ester group to a macromolecule, wherein said linker group provides a carbon chain of at least 2 atoms between said amide group and said ester group. The novel compounds are particularly suitable as contrast agents, e.g. in magnetic resonance imaging.Type: GrantFiled: July 26, 1990Date of Patent: May 4, 1993Assignee: Nycomed Imaging ASInventors: Jo Klaveness, Pal Rongved, Per Strande
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Patent number: 5198208Abstract: There are provided chelating agents particularly useful for the preparations of diagnostic and therapeutic agents for magnetic resonance imaging, scintigraphy, ultrasound imaging, radiotherapy and heavy metal detoxification, said agents being compounds of formula X--CHR.sub.1 --NZ--(CHR.sub.1).sub.n --A--(CHR.sub.1).sub.m --NZ--CHR.sub.1 --X wherein (each of the groups Z is a group --CHR.sub.1 X or the groups Z together are a group --(CHR.sub.1).sub.q --A'--(CHR.sub.1).sub.r --, where A' is an oxygen or sulphur atom or a group --N--Y; A is a group --N--Y or A--(CHR.sub.1).sub.m -- represents a carbon-nitrogen bond or, when the groups Z together are a group --(CHR.sub.1).sub.q --A'--(CHR.sub.1).sub.r --, A may also represent an oxygen or sulphur atom; each Y, which may be the same or different, is a group --(CHR.sub.1).sub.p --N(CHR.sub.1 X).sub.2 or a group --CHR.sub.1 X; each X, which may be the same or different, is a carboxyl group or a derivative thereof or a group R.sub.1 ; each R.sub.Type: GrantFiled: March 16, 1990Date of Patent: March 30, 1993Assignee: Nycomed Imaging ASInventors: Arne Berg, Torsten Almen, Jo Klaveness, Pal Rongved, Terje Thomassen
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Patent number: 5182370Abstract: Comounds having the formula ##STR1## wherein: a is 2 or 3; b is an integer from 0 to 4;Me.sup.(a+) is an ion of an element of atomic number from 57 to 70 or an ion of a transition metal of atomic number 21-29, 42 or 44;E.sup.(b+) is one or more physiologically biocompatible cation of an inorganic or an organic base or amino acid, said cation representing a total positive charge of b units;S is the group --A--O--R wherein:A is --(CH.sub.2).sub.m --; --CH.sub.2 --C(CH.sub.3).sub.2 --; m is an integer from 1 to 5; R is H; linear or branched alkyl of 1 to 8 carbon atoms, said carbon atoms being unsubstituted or substituted by one or more hyroxy group; aralkyl of 1 to 4 aliphatic carbon atoms; phenyl or phenyl substituted by halogen, amino, hydroxy or trifluoromethyl; (poly)-oxa-alkyl of 1 to 10 oxygen atoms and from 3 to 30 carbon atoms;R.sub.1 is R.sub.2 or --CH.sub.2 COOZ; --CH(CH.sub.3)COOZ; --(CH.sub.2).sub.n --N(CH.sub.2 COOZ).sub.Type: GrantFiled: December 13, 1989Date of Patent: January 26, 1993Assignee: Bracco Industria Chimica S.p.A.Inventors: Ernst Felder, Luciano Fumagalli, Fulvio Uggeri, Giorgio Vittadini
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Patent number: 5171847Abstract: Novel metallo-organic complexes of the formula (M.sub.x X.sub.z. nL)y where M is an alkaline earth metal, a transition metal(at. Nos. 21-30, 39-48 and 72-80 inclusive) or a rare earth metal (at. Nos. 57-71 inclusive), X is an anion e.g. Cl.sup.-, Br.sup.-, NO.sub.3 -, NCS.sup.- etc. and L is a Lewis base, are prepared by reacting a source of the metal M under anhydrous conditions with an anhydrous ammonium salt of the anion X in the presence of the Lewis base, and cooling the reaction mixture to precipitate the complex.Type: GrantFiled: July 5, 1990Date of Patent: December 15, 1992Assignee: The Associated Octel Company LimitedInventors: Ronald Snaith, Dominic S. Wright, Alan T. Brooker, Simon R. Drake
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Patent number: 5162109Abstract: A diagnostic composition suitable for administration to a warm-blooded animal, which comprises a MRI-effective amount of a zwitterionic complex of a paramagnetic ion having a cyclic or open chain structure and a pharmaceutically acceptable carrier and a method for performing a MRI diagnostic procedure using the same.Type: GrantFiled: September 13, 1990Date of Patent: November 10, 1992Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Donald R. VanDeripe
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Patent number: 5162509Abstract: The present invention involves a novel tripyrrole dimethine-derived "expanded porphyrin" (texaphyrin), the synthesis of such compounds, their analogs or derivatives and their uses. These expanded porphyrin-like macrocycles are efficient chelators of divalent and trivalent metal ions. Metal complexes of these compounds are active as photosensitizers for the generation of singlet oxygen and thus potentially for inactivation or destruction of human immunodeficiency virus (HIV-1), mononuclear or other cells infected with such virus and tumor cells as well. A variety of texaphyrin derivatives have been produced and many more are readily obtainable. Various metal (e.g., transition, main group, and lanthanide) complexes with the texaphyrin and texaphyrin derivatives of the present invention have unusual water solubility and stability which render them particularly useful. These metallotexaphyrin complexes have optical properties making them unique as compared to existing porphyrin-like or other macrocycles.Type: GrantFiled: June 18, 1990Date of Patent: November 10, 1992Assignee: Board of Regents, The University of Texas SystemInventors: Jonathan L. Sessler, Gregory W. Hemmi, Toshiaki Murai
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Patent number: 5155215Abstract: The present invention includes an image-enhancing agent comprising a biodegradable, water-soluble polymer, synthetic or naturally derived and having repeating hydrophilic monomeric units with amino or hydroxyl groups. This agent also includes chelating agents comprising functional groups bound to an amino or bydroxyl group of the monomeric units. These chelating agents have a formation constant for divalent or trivalent metal cations of at least about 10.sup.8 at physiological temperature and pH. This image-enhancing agent is biodegradable to intermediary metabolites, excretable chelates, oligomers, monomers or combinations thereof of low toxicity.These image-enhancing agents may further comprise a paramagnetic metal ion for enhancement of the image arising from induced magnetic resonance signals.Images resulting from scanning of gamma particle emissions may be enhanced when the image-enhancing agent of the present invention comprise radioisotopic metal ions emitting gamma particles.Type: GrantFiled: November 7, 1990Date of Patent: October 13, 1992Assignee: Access Pharmaceuticals Inc.Inventor: David F. Ranney
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Patent number: 5145605Abstract: A novel cerium (IV) material, well adopted for the production of aqueous colloidal sols therefrom, has the general formula (I):Ce(M).sub.t (CH.sub.3 --CH.sub.2 ].sub.n COO.sup.-).sub.x (OH.sup.-).sub.y (NO.sub.3.sup.-).sub.z (I)whereein M is an alkali metal or a quaternary ammonium radical; t ranges from 0.1 to 0.3; n is 0 or 1; x ranges from 0.1 to 0.7; y is a number such that y=4+t-x-z; and z ranges from 0.3 to 0.6.Type: GrantFiled: September 16, 1991Date of Patent: September 8, 1992Assignee: Rhone-Poulenc Specialties ChimiquesInventor: Jean-Yves Chane-Ching
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Patent number: 5141740Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with hydrazide derivatives of polyaminocarboxylic acid chelating agents. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions. A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: November 21, 1990Date of Patent: August 25, 1992Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Rebecca A. Wallace, Muthunadar P. Periasamy
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Patent number: 5138040Abstract: Methods and compositions for enhancing magnetic resonance imaging in at least a portion of a warm-blooded animal.Type: GrantFiled: July 2, 1991Date of Patent: August 11, 1992Assignee: Mallinckrodt Medical, Inc.Inventors: Dennis A. Moore, Rebecca A. Wallace
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Patent number: 5137711Abstract: Novel magnetic resonance imaging agents methods utilize complexes of paramagnetic ions with alkoxyalkylamide deriviatives of diethylenetriaminepentaacetic acid ("DTPA") or ethylenediaminetetyraacetic acid ("EDTA"). These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.The complexes are represented by the following formula: ##STR1## wherein A is --CH.sub.2 CH.sub.2 -- or ##STR2## and M.sup.+Z is a paramagnetic ion of an element with an atomic number of 21-29, 42-44 or 58-70, and a valence number, Z, of 2 or 3; R.sup.1 is --O.sup.- or R.sup.3 --N--R.sup.2, R.sup.2 is --(CH.sub.2 CH.sub.2 O).sub.n --R.sup.4, n is 1-10, R.sup.4 is alkyl or aryl, R.sup.3 is H, R.sup.2, alkyl, hydroxy, alkoxy, cycloalkyl or aryl, wherein Z of the R.sup.1 groups are --O.sup.- and the remainder of the R.sup.1 groups are R.sup.2 -N--R.sup.3 groups.Type: GrantFiled: July 13, 1989Date of Patent: August 11, 1992Assignee: Mallickrodt Medical, Inc.Inventors: Robert W. Weber, Muthunadar P. Periasamy