Containing -c(=x)x-, Wherein The X's Are The Same Or Diverse Chalcogens Patents (Class 534/16)
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Patent number: 5132409Abstract: Macrocyclic derivatives of 1,4,7,10-tetraazacyclododecane of general formula (I) hereinbelow, wherein A is a group of formula (II) hereinbelow, in which R is H or alkyl or optionally substituted benzyl or a H(OCH.sub.2 CH.sub.2).sub.1-4-, Me(OCH.sub.2 CH.sub.2).sub.1-4-, or Et(OCH.sub.2 CH.sub.2).sub.1-4- group, X or O--R.sub.1, in which R.sub.1 is H or alkyl, hydroxyalkyl, alkoxyalkyl, alkoxyhydroxyalkyl or a polyoxaalkyl group or X is --NR.sub.2 R.sub.3, in which R.sub.2 and R.sub.3 are H or alkyl, hydroxyalkyl, alkoxyalkyl or alkoxyhydroxyalkyl, and B.sub.1, B.sub.2 and B.sub.3 have the same meanings as A or are H or a group of formula (III) hereinbelow, in which R.sub.4 is H or alkyl, Y is a O--R.sub.5 group, wherein R.sub.5 is H or alkyl, hydroxyalkyl, alkoxyalkyl, alkoxyhydroxyalkyl or a polyoxaalkyl group, or Y is a --NR.sub.6 R.sub.7 group, wherein R.sub.6 and R.sub.Type: GrantFiled: November 27, 1989Date of Patent: July 21, 1992Assignee: Bracco Industria Chimica S.p.A.Inventors: Ernst Felder, Carlo Musu, Luciano Fumagalli, Fulvio Uggeri
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Patent number: 5130120Abstract: Novel magnetic resonance imaging agents and methods which utilize complexes of paramagnetic ions with alkoxyalkylamide derivatives of diethylenetriaminepentaacetic acid ("DTPA") or ethylenediaminetetraacetic 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, Z, of 2 or 3; the R groups may be the same or different and are selected from the group consisting of -O.sup..crclbar. and lower alkoxyalkylamino groups having from 2 to about 6 carbon atoms, wherein the number of R groups -O.sup..crclbar. equals Z and the remaining R groups are lower alkoxyalkylamino, equal to 4-Z when A is --CH.sub.2 CH.sub.Type: GrantFiled: July 19, 1988Date of Patent: July 14, 1992Assignee: Mallinckrodt Medical, Inc.Inventor: Robert W. Weber
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Patent number: 5109129Abstract: 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 formula of FIG. 4 of the attached drawings; their metal complexes have the formula of FIG. 2. 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, prophyrin derivative or metal complex are encapsulated within the molecules of the cyclodextrin. The solvent for the solutions can be a product of the reaction of ethylene oxide with castor oil.Type: GrantFiled: August 3, 1990Date of Patent: April 28, 1992Assignee: The University of Toledo, Medical College of OhioInventors: Alan R. Morgan, Steven H. Selman
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Patent number: 5106957Abstract: 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: April 21, 1992Assignee: Baxter Diagnostics Inc.Inventors: Ron L. Hale, Dennis W. Solas
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Patent number: 5077037Abstract: Methods and compositions for enhancing magnetic resonance imaging in at least a portion of a warm-blooded animal.Type: GrantFiled: August 3, 1990Date of Patent: December 31, 1991Assignee: Mallinckrodt Medical, Inc.Inventor: Rebecca A. Wallace
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Patent number: 5051415Abstract: 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: August 2, 1989Date of Patent: September 24, 1991Assignees: The 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: 5043101Abstract: This invention provides particle compositions possessing ferromagnetic, paramagnetic or diamagnetic properties. The particles are especially useful when used in the disease diagnostic and treatment regimens as described in U.S. Pat. Nos. 4,106,448, 4,136,683 and 4,303,636.Type: GrantFiled: March 29, 1988Date of Patent: August 27, 1991Inventor: Robert T. Gordon
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Patent number: 5034550Abstract: Mixed heavy bimetallic alkoxide-carboxylate compositions are formed by reaction of a heavy metal tetraalkoxide (e.g., a zirconium alkoxide) and a heavy metal tricarboxylate (e.g., yttrium acetate) with elimination of distillable ester by-product therefrom. Hydrolysis of said compositions produced novel bimetallic hydroxy-carboxylates. Calcination of the hydrolysis products give bimetallic oxides.Type: GrantFiled: June 7, 1990Date of Patent: July 23, 1991Assignee: Akzo N.V.Inventor: Fawzy G. Sherif
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Patent number: 5032677Abstract: 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: November 6, 1987Date of Patent: July 16, 1991Assignee: Baxter International Inc.Inventors: Ron L. Hale, Dennis W. Solas
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Patent number: 4987227Abstract: A 13 or 14 member macrocyclic compound having the following ring nucleus: ##STR1##This work was supported by grants from the National Institutes of Health (GM-34841) and the National Science Foundation (CHE-8706616).Type: GrantFiled: February 23, 1990Date of Patent: January 22, 1991Assignee: The Research Foundation of State University of New YorkInventors: Cynthia Burrows, Heungsik Yoon, Thomas R. Wagler
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Patent number: 4968322Abstract: Disclosed herein are a fuel composition comprising a fuel oil added with at least two kinds of soaps selected from cerium, neodymium and lanthanum soaps and a fuel additive comprising an organic solution that contains at least two kinds of soaps selected from cerium, neodymium and lanthanum soaps.Type: GrantFiled: April 7, 1989Date of Patent: November 6, 1990Assignee: Nippon Mining Company, LimitedInventors: Shintaro Miyawaki, Kiyomi Ishii, Mamoru Yamane
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Patent number: 4965211Abstract: Species-linked diamine triacetic acids of the formula ##STR1## wherein T is an organic species containing at least one amine, hydroxyl, or thiol functional group, L is the residue of at least one of those functional groups and R is a two or more atom long covalent bridge, are disclosed. Methods for their preparation, for the preparation of metal chelates from them and for the use of the chelates are also disclosed. In a preferred embodiment, the metal ions employed in the formation of the chelates are rare earth metal ions capable of forming fluorescent chelates which can in turn be employed in fluoroassay techniques.Type: GrantFiled: November 9, 1983Date of Patent: October 23, 1990Assignee: Irwin WiederInventors: Irwin Wieder, Robert H. Wollenberg
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Patent number: 4957939Abstract: Pharmaceutical compositions comprising gadolinium chelates are useful for enhancing NMR images.Type: GrantFiled: June 20, 1986Date of Patent: September 18, 1990Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Douwe Rosenberg, Hanns-Joachim Weinmann
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Patent number: 4920195Abstract: A fluorescing lanthanide chelate of a lanthanide cation and a compound having the structure ##STR1## where X.sup.3, X.sup.4 and X.sup.5 that may be the same or different, each denotes a substituted ethynyl group, hydrogen, an alkyl group, an aryl group, a hydroxyl group, an alkoxyl group or an amino group, wherein at least one of X.sup.3, X.sup.4 and X.sup.5 denotes a substituted ethynyl group, and Z.sup.2 and Z.sup.6 that may be the same or different, each denotes a chelating group, hydrogen, an alkyl group or an amino group, wherein at least one of Z.sup.2 and Z.sup.6 denotes a chelating group.Type: GrantFiled: January 25, 1988Date of Patent: April 24, 1990Inventors: Jouko Kankare, Harri Takalo, Paavo Pasanen
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Patent number: 4916246Abstract: Compounds suitable for NMR imaging having the formula: ##STR1## wherein a is 2 or 3;b is an integer from 0 to 4;Me.sup.(a+) is Fe.sup.(2+), Fe.sup.(3+), Gd.sup.(3+), or Mn.sup.(2+) ;E.sup.(b+) is an ion of an alkali metal, alkaline earth metal, alkyl ammonium, alkanol ammonium, polyhydroxyalkyl ammonium, or basic protonated amino acid, said ions representing a total charge of b;m is an integer from 1 to 5;R is H, alkyl with from 1 to 8 carbon atoms, alkyl with from 1 to 8 carbon atoms wherein from 1 to 5 carbons are substituted with OH; aralkyl with 1 to 4 aliphatic carbon atoms; phenyl or phenyl substituted by halogen, hydroxyl, carboxyl, carboxamide, ester, SO.sub.3 H, sulfonamide, lower alkyl, lower hydroxy alkyl, amino, acylamino; (poly)oxa-alkyl with 1 to 50 oxygen atoms and from 3 to 150 carbon atoms, wherein 1 to 5 hydrogen atoms may be substituted by OH;R.sub.1 is the same as R.sub.2 oris --CH.sub.2 COOZ, --CH(CH.sub.3)COOZ, CH.sub.2 CH.sub.2 --N(CH.sub.2 COOZ).sub.Type: GrantFiled: January 12, 1987Date of Patent: April 10, 1990Assignee: Bracco Chimica S.p.A.Inventors: Ernst Felder, Fulvio Uggeri, Luciano Fumagalli, Giorgio Vittadini
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Patent number: 4886624Abstract: A process is provided for preparing colloidal dispersions of alcohol-dispersible association complexes of ceric dioxide and a hydroxyphenyl carboxylic acid having from about seven to about twenty carbon atoms in a molar ratio CeO.sub.2 /acid of at least about 6:1 which comprises:(1) mixing(a) ceric dioxide comprising ammonium nitrate or ammonium and nitrate ions in an amount within the range from about 3 to about 14% by weight of the ceric dioxide and a member selected from the group consisting of water, methanol, acetic acid and mixtures thereof in an amount usually from about 10 to about 60 g per mole of CeO.sub.2, sufficient to effect reaction with(b) a hydroxyphenyl carboxylic acid having from about seven to about twenty carbon atoms(c) an aliphatic alcohol, such as methanol, isopropanol, 2-ethoxy ethanol, etc.at a temperature within the range from room temperature to about 100.degree. C., thereby effecting dispersion of the ceric dioxide in the aliphatic alcohol.Type: GrantFiled: August 18, 1987Date of Patent: December 12, 1989Assignee: Rhone-Poulenc, Inc.Inventors: Peter S. Gradeff, Carlos Ramirez
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Patent number: 4885363Abstract: Metal-chelating liquids having the formula ##STR1## wherein Y is oxygen or ##STR2## R.sub.Type: GrantFiled: December 23, 1987Date of Patent: December 5, 1989Assignee: E. R. Squibb & Sons, Inc.Inventors: Michael F. Tweedle, Glen T. Gaughan, James T. Hagan
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Patent number: 4877872Abstract: Dimers which are either esters or amides of (1) a purpurin, a chlorin or a metal complex and (2) hematoporphyrin or a purpurin, a chlorin or a metal complex are disclosed. The purpines 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, 19-28, 39-43 or 49-53 of the attached drawings. Solutions of the purpurins, chlorins and 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 dimers to the patient.Type: GrantFiled: June 24, 1986Date of Patent: October 31, 1989Assignee: The University of ToledoInventors: Alan R. Morgan, Steven H. Selman, Greta M. Garbo, Rick W. Keck
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Patent number: 4867951Abstract: An organic extracting solution and an extraction method useful for separating elements of the actinide series of the periodic table from elements of the lanthanide series, where both are in trivalent form. The extracting solution consists of a primary ligand and a secondary ligand, preferably in an organic solvent. The primary ligand is a substituted monothio-1,3-dicarbonyl, which includes a substituted 4-acyl-2-pyrazolin-5-thione, such as 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT). The secondary ligand is a substituted phosphine oxide, such as trioctylphosphine oxide (TOPO).Type: GrantFiled: March 31, 1988Date of Patent: September 19, 1989Assignee: The United States of America as represented by the United States Department of EnergyInventors: Barbara F. Smith, Gordon D. Jarvinen, Robert R. Ryan
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Patent number: 4857475Abstract: Labellable reagents for fluormetric assays comprise a cyclic condensation product of a .beta.-diketone, an aldehyde and an NH.sub.2 -bearing macromolecule, for example an antigen or antibody or a substance having an active group to which an antibody or antigen is linked. The reagents can chelate lanthanide metal ions such as Eu(II) and Tb(III) to form fluorescing complexes which can be used as labelled reagents for fluorometric assay of organic substances, for example antigens, antibodies and other substances occurring in body fluids.Type: GrantFiled: April 17, 1986Date of Patent: August 15, 1989Assignee: Roger Philip EkinsInventor: Salifu Dakubu
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Patent number: 4849207Abstract: A porphyrin compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.3, --CH(O-lower alkanoyl)CH.sub.3, --CH(OR)CH.sub.3 or --CH(O-lower alkylene-OR)CH.sub.3 ; R.sub.3 is --H, --COOH, --COO-lower alkyl, --COO-lower alkylene-OR or --COO-lower alkylene-OOC-Z; R.sub.4 is --H, -lower alkyl or -lower alkylene-OR; R is --H, -lower alkyl or a residue of a polyfunctional carboxyl compound excluding a hydrogen atom therefrom; Z is a residue of the compound of the formula (I) excluding R.sub.3 therefrom; A is --CH.sub.2 -- or --CO--; and the dotted line from the gamma-position indicates no bonding or a single direct bond; and the dotted line between the 7- and 8-positions indicates the presence of a single bond or a double bond; and its complexes with a metal(s) in the porphine skeleton and/or at the residue of the polyfuntional carboxyl compound, at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: October 23, 1986Date of Patent: July 18, 1989Assignees: Nihon Medi-Physics Co., Ltd., Toyo Hakka Kogyo Co., Ltd.Inventors: Isao Sakata, Susumu Nakajima, Koichi Koshimizu, Natsuki Samejima, Kazumi Inohara, Hiroyuki Takata, Hirohiko Yamauchi, Nobuo Ueda, Masaaki Hazue
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Patent number: 4826673Abstract: The disclosure is directed to compounds of the formula: ##STR1## wherein n=0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 may be the sam e or different and are selected from the group consisting of hydrogen and lower alkyl and hydroxy lower alkyl groups containing between 1 and 6 carbon atoms. Complexes of iron(II), iron(III), manganese(II), manganese(III), gadolinium(III), chromium(III), cobalt(II), and nickel(II) and such compounds are useful for enhancing magnetic resonance images of body organs and tissues. Illustrative complexes include (N,N"-bis[N-(2,3-dihydroxypropyl) carbamoylmethyl]diethylenetriamine-N,N',N"-triaceto)-iron(III), (N,N"-bis[N-(2,3-dihydroxypropyl)carbamoylmethyl]diethylenetriamine-N,N',N "-triaceto)manganese(II), (N,N"-bis[N-(2,3-dihydroxypropyl) )carbamoylmethyl]diethylenetriamine-N,N',N"-triaceto)gadolinium(III) and (N,N'-bis[N-(2,3-dihydroxypropyl)-carbamoylmethyl]ethylenediamine-N,N'-dia ceto)manganese(II).Type: GrantFiled: January 9, 1985Date of Patent: May 2, 1989Assignee: Mallinckrodt, Inc.Inventors: Richard T. Dean, Youlin Lin, Robert W. Weber, David H. White
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Patent number: 4803291Abstract: The disclosed particulate composition of simple or mixed oxalate of ferromagnetic metals is characterized in that it is provided in the form of needle-shaped particles having a length comprised between 0.05 and 0.5 micrometer, with a proportion higher than 60% of particles having a length equal to the average length .+-.0.1 .mu.m. and an acicular ratio higher than 3, said average length being comprised between 0.15 and 0.35 .mu.m; its preparation and its application are also disclosed.Type: GrantFiled: July 2, 1987Date of Patent: February 7, 1989Assignees: Centre National de la Recherche Scientifique, Universite Paul SabatierInventors: Abel Rousset, Christiane B. Salvaing, Paul Mollard, Alain Manoux, Philippe Tailhades
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Patent number: 4801722Abstract: There are described stable fluorescent labels comprising a complex of lanthanide metal and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of said lanthanide metal and at least two heteroatom-containing groups which form coordinate complexes with lanthanide metals and a third heteroatom-containing group or heteratom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, heptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.Type: GrantFiled: January 27, 1987Date of Patent: January 31, 1989Assignee: Eastman Kodak CompanyInventors: Jerald C. Hinshaw, John L. Toner, George A. Reynolds
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Patent number: 4749560Abstract: The present invention relates to a class of compositions and a method for NMR imaging using an NMR signal affecting amount of a paramagnetic, diamagnetic or ferromagnetic metal ion chelated with an organo phosphorous compound.Gadolinium bis(bis-dihydroxyphosphonylmethylphosphinate) is an example of such a composition.Type: GrantFiled: August 13, 1984Date of Patent: June 7, 1988Assignee: Research CorporationInventor: Gabriel A. Elgavish
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Patent number: 4746507Abstract: Ethylene Diamine Hydroxy Phenylacetic Acid (EDHPA) type chelators strongly bind paramagnetic metal ions to provide excellent contrast agents for magnetic resonance (MR) imaging. The magnetic dipole generated by unpaired electrons within the paramagnetic (PM) atom, causes a local reduction in the bulk magnetic field of the MR system. The resulting shortening of the T1 (spin lattice) relaxation time in the hydrogen protons within the area of interest, causes an intense "free induction signal" and a corresponding modulation in the collected scanning data. The tissue of organ of interest appears on the MR display as a high intensity of white area. Background tissue is displayed as darker or lower intensity greys. Each member chelator EDHPA' of the EDHPA family of chelators, is a phenolic analog of EDTA, with variations in the para position radical (PR) of the phenol ring.Type: GrantFiled: April 2, 1985Date of Patent: May 24, 1988Assignee: Salutar, Inc.Inventor: Steven C. Quag
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Patent number: 4735796Abstract: This invention provides particle compositions possessing ferromagnetic, paramagnetic or diamagnetic properties. The particles are especially useful when used in the disease diagnostic and treatment regimens as described in U.S. Pat. Nos. 4,106,448, 4,136,683 and 4,303,636.Type: GrantFiled: May 7, 1985Date of Patent: April 5, 1988Inventor: Robert T. Gordon
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Patent number: 4730066Abstract: Complexes of iron(II), iron(III), manganese(II), manganese(III), gadolinium(III) or chromium(III) and a compound of the formula: ##STR1## wherein m=2, 3, 4, or 5, are useful for enhancing magnetic resonance images of body organs and tissues, such as magnetic resonance images of the hepatobiliary system. An illustrative complex of this type is monosodium [ethylenediamine-di(o-hydroxyphenylaceto)]iron(III) hydrate.Type: GrantFiled: May 6, 1986Date of Patent: March 8, 1988Assignee: Mallinckrodt, Inc.Inventor: David H. White
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Patent number: 4714607Abstract: There are provided NMR contrast agents comprising water-soluble paramagnetic metal chelates, preferably of Cr(III), Fe(III) or Gd(III), wherein the chelating entity is an anilide group containing organic moiety, preferably a compound of formula I ##STR1## wherein R.sup.1 to R.sup.5 may represent hydrogen or halogen atoms, optionally halogenated alkyl or alkoxy groups or carboxyl groups. The agents are especially suitable for use in NMR imaging of the hepatobiliary system.Type: GrantFiled: May 30, 1985Date of Patent: December 22, 1987Assignee: Nycomed ASInventor: Jo Klaveness
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Patent number: 4687659Abstract: Homologs of Diamide-DTPA-Paramagnetic compounds (such as diamido acetyl diethylene triamine triacetic acid) provide excellent contrast agents for magnetic resonance (MR) imaging. The magnetic dipole generated by the unpaired electron within the paramagnetic (PM) atom, causes a local reduction in the bulk magnetic field of the MR system. The resulting shorting of the T1 (spin lattice) relaxation time in the local hydrogen protons within the area of interest, causes an intense "free induction signal" and a corresponding modulation in the collected scanning data. The tissue or organ of interest appears on the MR display highlighted in white. Background tissue is displayed as darker or lower intensity greys. A surface highlighted image of the small and large intestine may be obtained by venous injection of the diamide contrast agent. The contrast agent is formed by replacing two carboxylic acids on the DTPA chelator with functional amide groups.Type: GrantFiled: November 13, 1984Date of Patent: August 18, 1987Assignee: Salutar, Inc.Inventor: Steven C. Quay
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Patent number: 4572803Abstract: Rare-earth metal salts of organic carboxylic acids of this invention constitute themselves phosphors which exhibit unusually high luminescence efficiency, excel in chemical and physical stability and weatherability, show high affinity for other chemical substances and promise extensive usefulness in the field of high-performance luminescent products.Type: GrantFiled: June 30, 1982Date of Patent: February 25, 1986Assignee: Asahi Dow LimitedInventors: Katsuhiko Yamazoe, Akira Yoshino, Yoshiharu Kitahama, Isamu Iwami
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Patent number: 4568360Abstract: A mixed organometallic composition suitable for use as fuel additives contains an organic acid salt of at least one metal from the lanthanide group and of at least one metal selected from the group formed by manganese and the metals of the iron group wherein the ratio of total number of metal atoms to number of organic acid equivalents is greater then the stoichiometric proportion, and preferably greater than 2.Type: GrantFiled: December 8, 1983Date of Patent: February 4, 1986Assignees: Compagnie Francaise de Raffinage, Gamlen Europe S.A.Inventors: Guy Brisset, Michel Mas, Alain Muller, Jean Peyrot