Manganese Or Rhenium Containing (mn Or Re) Patents (Class 556/45)
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Patent number: 5827880Abstract: The invention provides antioxidant salen-metal complexes, compositions of such antioxidant salen-metal complexes having superoxide activity, catalase activity, and/or peroxidase activity, compositions of salen-metal complexes in a form suitable for pharmaceutical administration to treat or prevent a disease associated with cell or tissue damage produced by free radicals such as superoxide, and cosmetic and free radical quenching formulations of salen metal compounds.Type: GrantFiled: January 26, 1995Date of Patent: October 27, 1998Assignee: Eukarion, Inc.Inventors: Bernard Malfroy-Camine, Susan Robin Doctrow
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Patent number: 5804161Abstract: Compounds of formula (I)?M.sub.6 Q.sub.8 B.sub.n L.sub.6-n !.sup.xwhere M is Re or Rh;each Q is a bridging atom selected from O, S, Se and Te;B is a monovalent non-bridging atom or moiety;L is a PR.sub.3 group in which R is C.sub.1-6 alkyl or aryl, optionally substituted on the alkyl or aryl group by one or more water-solubilizing groups such as an amine or hydroxidy group, or the three R groups together form a C.sub.6-10 trivalent group which may also contain up to three nitrogen or oxygen atoms;n is an integer from 0 to 6;and x is an integer from -2 to +4, representing the overall charge of the cluster, which when non-zero is accompanied by one or more counter ions of equal and balancing charge, and contrast media, particularly X-ray contrast media, containing them.Type: GrantFiled: August 26, 1996Date of Patent: September 8, 1998Assignee: Nycomed Salutar Inc.Inventors: Jeffrey R. Long, Xhiping Xheng, Richard H. Holm, Shi-Bao Yu, Michael Droege, William A. Sanderson
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Patent number: 5801228Abstract: The invention provides polymeric polychelants containing polymer repeat units of formula ?L--Ch--L--B! (where Ch is a polydentate chelant moiety; L is an amide or ester linkage; B is a hydrophobic group providing a carbon chain of at least 4 carbon atoms between the L linkages it interconnects) or a salt or chelate thereof, with the proviso that where Ch is 2,5-biscarboxymethyl-2,5-diazahex-1,6-diyl, the polychelant is metallated with lanthanide or manganese ions or B provides a carbon chain of at least 10 carbon atoms between the L linkages it interconnects and their salts and chelates. The paramagnetic polychelates of the polychelants of the invention have remarkably high R.sub.1 relaxivities.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: Nycomed Imaging ASInventors: Kenneth Robert Hollister, Kenneth Edmund Keller, Dong Wei, Xin Peng, David Lee Ladd, Paul Mark Henrichs, Robert Allen Snow
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Patent number: 5756790Abstract: The invention provides a method for preparing an optically active alcohol comprising the step of reacting a ketone compound with a hydride reagent in the presence of an optically active metal compound. The resulting optically active alcohols are useful as intermediates for the synthesis of physiologically active compounds such as drugs and pesticides, functional materials such as liquid crystals, and raw materials for synthesis in fine chemistry. A novel optically active cobalt (II) complex useful as a catalyst is also provided.Type: GrantFiled: September 27, 1996Date of Patent: May 26, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Teruaki Mukaiyama, Kiyotaka Yorozu, Takushi Nagata, Toru Yamada, Kiyoaki Sugi
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Patent number: 5741920Abstract: A process for inhibiting the re-absorption of migrating dyes in the wash liquor comprises introducing into a wash liquor containing a peroxide-containing detergent, from 0.5 to 150 mg, per liter of wash liquor, of one or more manganese compounds having the formula (1), (2), (3), (4), (5), (6) or (7) as defined in the specification. The manganese compounds do not exhaust at all on to cotton, polyamide or polyester fibres so that the compounds cannot lead to fibre discolouration problems.Type: GrantFiled: June 6, 1995Date of Patent: April 21, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Claude Eckhardt, Dieter Reinehr
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Patent number: 5733341Abstract: A process is described for inhibiting the re-absorption of migrating dyes in the wash liquor, comprising introducing into a wash liquor containing a peroxide-containing detergent, from 0.5 to 150, preferably from 1.5 to 75, especially from 7.5 to 40 mg, per liter of wash liquor, of one or more compounds having the formula (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13) or (14) as defined in the specification. The compounds of formula (1), (2), (3), (4), (5), (6), (8), (9) (10), (11), (12), (13) or (14) are new compounds. The compounds used do not exhaust at all on to cotton, polyamide or polyester fibers, so that the compounds cannot lead to fiber discoloration problems.Type: GrantFiled: December 14, 1995Date of Patent: March 31, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Claude Eckhardt, Dieter Reinehr, Georges Metzger
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Patent number: 5663393Abstract: Chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed, together with methods of using such catalysts. In accordance with one aspect of the invention, the catalyst is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of, producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5654455Abstract: Catalyst systems which comprise a transition metal and a tris(organophosphite) ligand are particularly effective as catalysts for hydrosilation reactions.Type: GrantFiled: December 21, 1995Date of Patent: August 5, 1997Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5637739Abstract: Methods of using chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed. In accordance with one aspect of the invention, the catalyst used is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: October 15, 1992Date of Patent: June 10, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5618958Abstract: A novel catalyst comprising the formula:LRE(O)nwhereinL is selected from the group consisting of(a) (R.sub.1)(AL)wherein R.sub.1 is an alkyl side chain containing at least one carbon-rhenium covalent bond, andAL is a molecule having C.sub.2 to C.sub.50, and has at least one hetero atom selected from the group consisting of N, O, S, and P wherein there is at least one hetero-rhenium dative bond, and has at least one chiral center. and(b) R.sub.AL is a straight or branched chain alkyl or arylalkyl group containing C.sub.2 to C.sub.50 and containing at least one heteroatom selected from the group consisting of N, O, S, and P, with the proviso that said alkyl group contains at least one carbon-rhenium covalent bond and at least one hetero-rhenium dative bond, and has at least one chiral center:and n is an integer which is 2, 3, 4, or 5 and which has utility in areas such as epoxidation of olefins.Type: GrantFiled: August 8, 1996Date of Patent: April 8, 1997Assignee: Hoechst Celanese CorporationInventors: Charles E. Tucker, Kenneth G. Davenport
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Patent number: 5616750Abstract: A compound of formula (I): ##STR1## n which M is a transition metal ion; A is a counter-ion if required;r, s and t are independently 0 to 3 such that r+s+t is in the range of 1 to 3;R.sup.a, R.sup.b, R.sup.c are each independently hydrogen or CH.sub.2 OR' where R' is hydrogen or an organic group;B and E are independently oxygen, CH.sub.2, NR.sup.d in which R.sup.d is alkyl, hydrogen, alkylcarbonyl, or arylcarbonyl or SO.sub.n where n is 0 or an integer 1 or 2, with the proviso that B and E are not simultaneously CH.sub.2 and that when B is oxygen, NR.sup.d or SO.sub.n, then r cannot be 0, and when E is oxygen, NR.sup.d or SO.sub.n, then t cannot be 0;R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are independently hydrogen, alkyl or alkoxy.Type: GrantFiled: October 6, 1993Date of Patent: April 1, 1997Assignee: SmithKline Beecham plcInventors: David Bell, David Miller, Robin P. Attrill
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Patent number: 5602267Abstract: Asymmetric synthesis using a novel catalyst comprising the formula: ##STR1## and which has utility in areas such as epoxidation of olefins.Type: GrantFiled: May 26, 1995Date of Patent: February 11, 1997Assignee: Hoechst CelaneseInventor: Shu-Hai Zhao
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Patent number: 5599957Abstract: An optically active manganese complex of the formula I.sub.a, I.sub.b, I.sub.c and I.sub.d ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen atom, C.sub.1 -.sub.4 alkyl group, phenyl group which may be substituted by a halogen atom, C.sub.1 -.sub.4 alkyl group, C.sub.1 -.sub.4 alkoxyl group, cyano group or nitro group; and any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 together form a C.sub.4 -.sub.8 ring, X.sup.- represents a counter anion which may form a salt, Y represents hydrogen atom, halogen atom, C.sub.1 -.sub.4 alkyl group, C.sub.1 -.sub.4 alkoxyl group, nitro group or cyano group, R represents hydrogen atom, C.sub.1 -.sub.4 alkyl group, phenyl group which may be substituted by halogen atom, C.sub.1 -.sub.4 alkyl group or C.sub.1 -.sub.4 alkoxyl group, or substituted silyl group and a process for producing epoxy compounds using the complex as a catalyst.Type: GrantFiled: May 30, 1995Date of Patent: February 4, 1997Assignee: Nissan Chemical Industries, Ltd.Inventors: Tsutomu Katsuki, Ryo Irie, Hidehiko Sasaki
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Patent number: 5596016Abstract: Mineral absorption is promoted in warm-blooded animals by means of a class of 1,2-disubstituted aromatic mineral chelates wherein the 1 and 2 substituents each donates a pair of electrons to a metal ion for formation of a five-member chelate ring. 2-Alkoxyphenols are particularly preferred. The chelates contain from one to three alkoxyphenol ligands, with two ligands being preferred. A preferred alkoxyphenol is vanillin, and the minerals are selected from the group consisting of Mg, Ca, Cr, Mn, Fe, Co, Cu, Zn, Mo, and Se. Vanillin metal chelates have a slight to neutral taste, and are absorbed more readily than inorganic mineral salts.Type: GrantFiled: August 19, 1994Date of Patent: January 21, 1997Assignee: Albion International, Inc.Inventors: Stephen Ashmead, Harvey H. Ashmead
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Patent number: 5596115Abstract: The present invention concerns new compounds of rhenium and aluminum corresponding to the general formula: O.sub.3 Re--O--[Al(OR)(L).sub.x --O].sub.n --ReO.sub.3 in which R is a hydrocarbyl residue, for example alkyl, cycloalkyl, alkenyl, aryl and aryl or cycloalkyl which are substituted, containing from 1 to 40 carbon atoms, which residue can be substituted by alkoxy groups or by halogens, L is the synthesis solvent, x is equal to 0 or 1 and n is an integer of from 1 to 10. The invention also concerns derived compounds of the formula O.sub.3 Re(L')--O--[Al(OR)(L).sub.x --O].sub.n --ReO.sub.3 (L') in which L' is a stabilising ligand. The invention also concerns the preparation of such compounds and the use thereof in the preparation of catalysts.Type: GrantFiled: November 6, 1995Date of Patent: January 21, 1997Assignee: Institut Francais Du PetroleInventor: Dominique Commereuc
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Patent number: 5591581Abstract: Electrochemiluminescent moieties having the formula(Re(P).sub.m (L.sup.1).sub.n (L.sup.2).sub.o (L.sup.3).sub.p (L.sup.4).sub.t (B).sub.uwhereinP is a polydentate ligand of Re;L.sup.1, L.sup.2, L.sup.3 and L.sup.4 are ligands of Re, each of which may be the same as or not the same as each other ligand;B is a substance which is a ligand of Re or is conjugated to one or more of P, L.sup.1, L.sup.2, L.sup.3 and L.sup.4 ;m is an integer equal to or greater than 1;each of n, o, p, q, r and s is zero or an integer;t is an integer equal to or greater than 1; andu is an integer equal to or greater than 1;P, L.sup.1, L.sup.2, L.sup.3, L.sup.4 and B being of such composition and number that the chemical moiety can be induced to electrochemiluminesce and the total number of bonds to Re provided by the ligands of Re being equal to the coordination number of Re are disclosed.Type: GrantFiled: April 15, 1994Date of Patent: January 7, 1997Assignee: IGEN, Inc.Inventors: Richard J. Massey, Michael J. Powell, Walter J. Dressick, Jonathan K. Leland, Janel K. Hino, Mohindar S. Poonian, Leopoldo D. Ciana
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Patent number: 5585468Abstract: This invention relates to chelating agents useful for coupling metal ions to biologically active molecules. In particular, substantial thioureas for chelating metals such as technetium are provided that can be conjugated to a targeting molecule such as an antibody, a peptide or a protein.Type: GrantFiled: June 27, 1994Date of Patent: December 17, 1996Assignee: Cytogen CorporationInventors: Daniel J. Coughlin, Benjamin A. Belinka, Jr.
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Patent number: 5531978Abstract: There are provided chelating agents particularly useful for the preparation of diagnostic and therapeutic agents for magnetic resonance imaging, scintigraphy, ultrasound imaging, radiotherapy and heavy metal detoxification, said agents being compounds of formula IX--CHR.sub.1 --NZ--(CHR.sub.1).sub.n --A--(CHR.sub.1).sub.m --NZ--CHR.sub.1 --X (I)wherein n and m are 2, 3 or 4; and A, X, R.sub.1 and Z are as defined in the specification.Type: GrantFiled: February 8, 1993Date of Patent: July 2, 1996Assignee: Nycomed Imaging ASInventors: Arne Berg, Torsten Almen, Jo Klaveness, Pal Rongved, Terje Thomassen, Harald Dugstad
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Patent number: 5527522Abstract: An NMR contrast agent composition contains a complex of a selected metal ion and a selected ligand.Type: GrantFiled: March 3, 1995Date of Patent: June 18, 1996Assignee: The General Hospital CorporationInventors: Randall B. Lauffer, Scott K. Larsen
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Patent number: 5516940Abstract: A compound and method of making a compound for use as a diagnostic or therapeutic pharmaceutical comprises either a phosphorous or germanium core and at least two hydrazine groups forming a ligand for bonding to a metal extending from the phosphorous or germanium core.Type: GrantFiled: April 29, 1994Date of Patent: May 14, 1996Assignee: Curators of the University of MissouriInventors: Kattesh V. Katti, Wynn A. Volkert, Alan R. Ketring, Prahlad R. Singh
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Patent number: 5508458Abstract: A novel catalyst comprising the formula: ##STR1## and which has utility in areas such as epoxidation of olefins.Type: GrantFiled: May 26, 1995Date of Patent: April 16, 1996Assignee: Hoechst Celanese CorporationInventor: Shu-Hai Zhao
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Patent number: 5426201Abstract: A method of preparing manganous enolates by the treatment of alkali metal or alkaline earth metal enolates with manganous compounds in a solvent for the Mn enolate to be prepared.Type: GrantFiled: April 25, 1994Date of Patent: June 20, 1995Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Patrick Clery, Jean-Alex Laffitte
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Patent number: 5424057Abstract: 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 carbonyl 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: April 8, 1994Date of Patent: June 13, 1995Assignee: Ciba-Geigy Corp.Inventors: Heinrich Peter, Theophile Moerker
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Patent number: 5420314Abstract: An optically active manganese complex of the formula I or I': ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 independently represent hydrogen atom, C.sub.1 -C.sub.4 alkyl group, phenyl group which may be substituted by a halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxyl group, cyano group or nitro group; and any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 together form the C.sub.4 -C.sub.8 ring, X.sup.- represents a counter anion which may form a salt, Y represents hydrogen atom, halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxyl group, nitro group or cyano group, R represents hydrogen atom, C.sub.1 -C.sub.4 alkyl group, phenyl group which may be substituted by halogen atom, C.sub.1 -C.sub.4 alkyl group or C.sub.1 -C.sub.4 alkoxyl group, or substituted silyl group and a process for producing epoxy compounds using the complex as a catalyst.Type: GrantFiled: March 14, 1994Date of Patent: May 30, 1995Assignee: Nissan Chemical Industries, Ltd.Inventors: Tsutomu Katsuki, Ryo Irie, Hidehiko Sasaki
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Patent number: 5412129Abstract: A precursor used in an MOCVD reactor for production of thin films of certain metal oxides is stabilized by introducing a ligand into the precursor during the precursor synthesis and thereby protecting the precursor from premature oxidation, nucleation, and decomposition.Type: GrantFiled: June 17, 1994Date of Patent: May 2, 1995Inventor: Stephen A. DiCarolis
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Patent number: 5405601Abstract: The present invention provides new and structurally diverse compositions for diagnostic imaging comprising compounds of the general formula: ##STR1## wherein A is N or CR.sub.1, R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, or C.sub.6 -C.sub.10 aryl, where the alkyl or aryl group may be optionally substituted with one or more hydroxy, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 hydroxyaryl, C.sub.6 -C.sub.10 aryloxy, --CO.sub.2 R.sub.2, --CONR.sub.3 R.sub.4, or NR.sub.3 R.sub.4 ; D is O, --O(CH.sub.2).sub.2 O--, --O(CH.sub.2).sub.3 O--, or NR.sub.5 ; E is O, --O(CH.sub.2).sub.2 O--, --O(CH.sub.2).sub.3 O-- or NR.sub.6 ; F is O, --O(CH.sub.2).sub.2 O--, --O(CH.sub.2).sub.3 O-- or NR.sub.7 ; R.sub.2 -R.sub.7 are as defined within; g, h, i, j, k and m may be the same or different and are an integer from one to about six; X is --CO.sub.2 H, --PO.sub.3 H.sub.2, --SO.sub.3 H or --CONHOH.Type: GrantFiled: July 2, 1993Date of Patent: April 11, 1995Assignee: Mallinckrodt Medical Inc.Inventors: T. Jeffrey Dunn, Dennis A. Moore, Muthanadar Periasamy, Milorad M. Rogic, Rebecca A. Wallace, David H. White, Steven R. Woulfe
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Patent number: 5399339Abstract: Process for the preparation of nitride complexes of transition metals for use as radiopharmaceutical products or for the synthesis of novel pharmaceutical products. The process consists in reacting an oxygenic transition metal compound such as 99m.sub.Tc, 186.sub.Re or 188.sub.Re, with a first nitrogenous ligand such as sodium nitride or a nitrogenous compound such as S-methyl, N-methyl dithiocarbazate, and a reducing agent consisting of either tin (II) or a dithionite. The product so obtained can be used for the preparation of radiopharmaceutical products by a reaction with a second ligand such as sodium dithiocarbamate.Type: GrantFiled: January 21, 1993Date of Patent: March 21, 1995Assignee: CIS BIO InternationalInventors: Roberto Pasqualini, Veronique Comazzi, Emmanuel Bellande
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Patent number: 5389675Abstract: Mixed ligand metal complexes of nitric oxide-nucleophile adducts, useful as cardiovascular agents of the formula KA, wherein A is[(M).sub.x.sup.x' (L).sub.y (R.sup.1 R.sup.2 N-N.sub.2 O.sub.2).sub.x ], andK is a pharmaceutically acceptable counterion present in the composition when the overall charge of A is not zero, counterion K being present only in an amount to neutralize A. Methods of treating mammals with such compounds are provided. Pharmaceutical compositions containing such compounds are also provided.Type: GrantFiled: March 27, 1992Date of Patent: February 14, 1995Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Danae D. Christodoulou, David A. Wink, Jr., Larry K. Keefer
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Patent number: 5385724Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize trifluoromethyl derivatives of iodinated X-ray contrast media. Typical magnetic resonance contrast media within the scope of the present invention include bis(trifluoromethyl)benzene derivatives, tris(trifluoromethyl)benzene derivatives, tetrakis(trifluoromethyl)benzene derivatives, and other related trifluoromethylated benzene derivatives.Type: GrantFiled: March 4, 1994Date of Patent: January 31, 1995Assignee: Mallinckrodt Medical, Inc.Inventors: David H. White, Steven R. Woulfe, Youlin Lin, Mills T. Kneller
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Patent number: 5344948Abstract: Neutral single-source molecular organic precursors containing tetradentate tripodal chelating ligands are provided that are useful for the preparation of films using chemical vapor deposition. These complexes can be generally represented by the formula ##STR1## wherein "M" is selected from the group consisting of a lanthanide, an actinide, a Group IIIA metal, a Group IIIA metalloid, a Group IVA metal, a Group IVA metalloid, a Group VA metal, a Group VA metalloid, a Group IIIB metal, a Group IVB metal, a Group VB metal, a Group VIB metal, a Group VIIB metal, and a Group VIIIB metal. The ligand "Z" can be present or absent, i.e., k=0-1, and is selected from the group consisting of hydrogen, halide, and a group bonded to "M" through N, O, P, S, As, Si, or C. In the tetradentate tripodal chelating ligand "E.sub.c " is N, P, or As, and m=0-1. When "E.sub.t " is N, P, or As, m=1, and when "E.sub.t " is O, S, or Se, m=0. Each "R.sup.1 " is independently selected from the group consisting of hydrogen, (C.sub.1 -C.Type: GrantFiled: July 10, 1992Date of Patent: September 6, 1994Assignee: Iowa State University Research Foundation, Inc.Inventor: John G. Verkade
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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: 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: 5326856Abstract: This invention relates to chelating agents useful for coupling metal ions to biologically active molecules. In particular, isothiocyanate derived thiocarbonyls for chelating metals such as technetium are provided that can be conjugated to a targeting molecule such as an antibody, a peptide or a protein.Type: GrantFiled: April 9, 1992Date of Patent: July 5, 1994Assignee: Cytogen CorporationInventors: Daniel J. Coughlin, Benjamin A. Belinka, Jr.
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Patent number: 5318771Abstract: An NMR contrast agent composition contains a complex of a selected metal ion and a selected ligand.Type: GrantFiled: August 4, 1993Date of Patent: June 7, 1994Assignee: The General Hospital CorporationInventors: Randall B. Lauffer, Scott K. Larsen
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Patent number: 5280117Abstract: A process is described for the preparation of a manganese complex catalyst having the formula: ##STR1## wherein Mn is manganese in the +4 oxidation state; R is a C.sub.1 -C.sub.20 radical selected from the group consisting of alkyl, cycloalkyl, aryl, benzyl and radical combinations thereof;at least two R radicals may also be connected to one another so as to form a bridging unit between two oxygens that coordinate with the manganese;L is a ligand selected from a C.sub.3 -C.sub.60 radical having at least 3 nitrogen atoms coordinating with the manganese; andY is an oxidatively-stable counterion;the process includes the steps of:(i) reacting in an nonaqueous alcoholic medium a manganese (II) salt with the ligand L to form a manganese coordinated substance, a counterion salt M.sub.z Y.sub.Type: GrantFiled: September 9, 1992Date of Patent: January 18, 1994Assignee: Lever Brothers Company, a Division of Conopco, Inc.Inventors: Judith L. Kerschner, Vikki Chin Quee-Smith
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Patent number: 5274147Abstract: A process for preparing a dinuclear manganese complex of formula (A) ##STR1## wherein: Mn represents manganese in the III or IV oxidation state, each X is independently a co-ordinating or bridging species selected from H.sub.2 O, O.sub.2.sup.-, O.sup.2-, OH.sup.-, SH.sup.-, S.sup.2-,>S=O, Cl.sup.-, N.sub.3.sup.-, SCN.sup.-, N.sup.3-, RCOO.sup.-, NH.sub.2.sup.- and NR.sub.Type: GrantFiled: July 6, 1992Date of Patent: December 28, 1993Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Judith Kerschner, Jean H. Koek, Ronald P. Potman, Lodewijk Van der Wolf
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Patent number: 5250285Abstract: An NMR contrast agent composition contains a complex of a selected metal ion and a selected ligand.Type: GrantFiled: February 20, 1992Date of Patent: October 5, 1993Assignee: The General Hospital CorporationInventors: Randall B. Lauffer, Scott K. Larsen
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Patent number: 5248430Abstract: Ammonium salts of aromatic sulpho group-containing condensation products of at least one sulpho group-containing aromatic compound and at least one dihydroxydiphenylsulphone with formaldehyde or a formaldehyde-yielding compound or of defined starting mono- or oligosulphones which are partially metallized and compositions containing them, optionally together with UV-absorbers, are suitable as assistants in the treatment of various substrates and act in particular as improvers of the light-fastness of synthetic polyamide fibres and their dyeings, as assistants in the dyeing or tanning of leather and in the production of paper and as wood-preserving agents.Type: GrantFiled: June 14, 1990Date of Patent: September 28, 1993Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
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Patent number: 5223631Abstract: Disclosed is an olefin epoxidation process that contacting an olefinically unsaturated substrate with oxygen in the presence of catalytic amount of a bimetallic complex under the reaction conditions such that the olefin is at least partially oxidized. The metals introduced in the bimetallic complex are independently selected from vanadium, chromium, manganese, iron, cobalt, nickel, copper, molybdenum, ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridum or platinum.Type: GrantFiled: June 30, 1992Date of Patent: June 29, 1993Assignee: National Science CouncilInventors: Cheu P. Cheng, Yaw H. Hwang, Ching C. Liu
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Patent number: 5221797Abstract: A process for the purification of pseudo-ionone, which comprises preparing pseudo-ionone by a reaction of citral with acetone, followed by bringing the reaction medium into contact with a metal derivative and thereafter distilling the pseudo-ionone.Type: GrantFiled: April 17, 1992Date of Patent: June 22, 1993Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Noel Crenne
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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: 5187136Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: W. Dirk Klobucar, Charles H. Kolich, Thanikavelu Manimaran
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Patent number: 5185368Abstract: 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 carbonyl 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: July 20, 1988Date of Patent: February 9, 1993Assignee: Ciba-Geigy CorporationInventors: Heinrich Peter, Theophile Moerker
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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: 5175311Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.Type: GrantFiled: March 29, 1990Date of Patent: December 29, 1992Assignee: Research Corporation Technologies, Inc.Inventor: Michael F. Doyle
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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: 5166381Abstract: Charge blocking materials include a complex or salt of a film forming material containing at least one nitrogen-containing compound, such as an amino, an imino or a tertiary amine group, chelated to a metal ion or atom. The charge blocking materials may be used in a charge blocking layer of an electrophotographic imaging member. The charge blocking materials may be used with transparent conductive layers, for example, comprising cuprous iodide.Type: GrantFiled: October 17, 1991Date of Patent: November 24, 1992Assignee: Xerox CorporationInventors: Leon A. Teuscher, Ronald F. Ziolo
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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: 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
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Patent number: 5135737Abstract: Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines.Type: GrantFiled: September 5, 1989Date of Patent: August 4, 1992Assignee: The State of Oregon Acting by and through the State Board of Higher Education on behalf of the University of OregonInventor: John F. W. Keana