Nitrogen Containing (e.g., Zinc Ethionates, Etc.) Patents (Class 556/134)
  • Patent number: 6045776
    Abstract: The invention relates to a process for the production of metal-complex carboxylic acid amides, characterized in that a metal-complex carboxylic acid mixture that consists of the metal-complex carboxylic acid and at least one solubilizing substance in dimethyl sulfoxide (DMSO) is pretreated with a dehydrating reagent, optionally with the addition of a coupling adjuvant, and is then reacted with an amine of general formula IA(NH.sub.2).sub.n (I),in whichA stands for the radical of a natural or synthetic amine, andn stands for numbers 1 to 100.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: April 4, 2000
    Assignee: Schering Aktiengesellschaft
    Inventors: Johannes Platzek, Bernd Raduchel, Heribert Schmitt-Willich, Klaus-Dieter Graske
  • Patent number: 5962717
    Abstract: Plant micronutrient compounds comprising N-acyl ED3A or salts thereof. The N-acyl ED3A derivatives chelate various trace metals, including iron, copper, zinc, manganese, cobalt and nickel.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: October 5, 1999
    Assignee: Hampshire Chemical Corp.
    Inventors: Arthur M. Nonomura, Barry A. Cullen, Joseph J. Crudden, John J. Nishio
  • Patent number: 5958372
    Abstract: Disclosed are linear and cross-linked polymers suitable for use as a contrast agent for magnetic resonance imaging containing units comprising the residue of a poly(amine) moiety linked to a chelating agent and to one or more pendant (poly)alkylene oxides.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: September 28, 1999
    Assignee: Nycomed Imaging AS
    Inventor: David L. Ladd
  • Patent number: 5914097
    Abstract: The present invention relates to the preparation of amino-acyl-type and catecholamine-type compounds having multiple carboxylic acid functional groups. Paramagnetic metal (II) or (III) ion chelate complexes are formed using these compounds for use as intravenous contrast agents to produce enhanced contrast magnetic resonance images of the heart, liver, biliary tree or upper small intestine. The mono- and di-amino acids, their esters and amides, and catecholamine-like derivatives, of EDTA, DTPA, and the like are prepared. The paramagnetic metal (II) or (III) ion complexes are formed and produce T1-related contrast effects in MR images. The compounds and complexes also appear to have low toxicities and to be relatively rapidly and completely cleared from the tissue of a living mammal, e.g. a human being.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 22, 1999
    Assignee: Regents of the University of California
    Inventor: David L. White
  • Patent number: 5914095
    Abstract: There are provided polychelants and their metal chelates which are useful in diagnostic imaging and in radiotherapy and which comprise a plurality of macrocyclic chelant moieties, e.g. DOTA residues, conjugated to a dendritic polyamine backbone molecule, e.g. a starburst dendrimer. To produce a site-specific polychelate, one or more of the macrocyclic chelant carrying backbone molecules may be conjugated to a site-directed macromolecule, e.g. a protein.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: June 22, 1999
    Assignee: Salutar, Inc.
    Inventor: Alan D Watson
  • Patent number: 5885548
    Abstract: The invention relates to new, multiply substituted diethylenetriaminepentaacetic acid derivatives, their complexes and complex salts, that contain an element of atomic numbers 20-32, 39-51 or 57-83, pharmaceutical agents that contain these compounds, their use as contrast media and antidotes, and process for the production of pharmaceutical agents.
    Type: Grant
    Filed: November 30, 1995
    Date of Patent: March 23, 1999
    Assignee: Schering Aktiengesellschaft
    Inventors: Franz-Karl Maier, Michael Bauer, Werner Krause, Ulrich Speck, Gabriele Schuhmann-Giampiere, Andreas Muhler, Thomas Balzer, Wolf-Rudiger Press
  • Patent number: 5859214
    Abstract: Compounds of general formula I ##STR1## wherein Z.sup.1, Z.sup.2, X, R.sup.2 and R.sup.3 are as herein defined, are valuable pharmaceutical agents. In particular, the compounds are useful as contrast agents in NMR diagnosis.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: January 12, 1999
    Assignee: Schering Aktiengesellshaft
    Inventors: Heinz Gries, Erich Klieger, Bernd Raduchel, Heribert Schmitt-Willich, Hanns-Joachim Weinmann, Hubert Vogler, Gabriele Schuhmann-Giampieri, Jurgen Conrad
  • Patent number: 5808013
    Abstract: Process for the preparation of N-alkyl substituted metal carbamate solutions characterized in that a water solution of the salt of the metal of which the corresponding carbamate is to be obtained, is reacted with an organic solution, basically consisting of an aprotic solvent and a secondary amine, saturated with carbon dioxide.The above solutions can be used as catalysts in polymerization reactions of unsaturated monomers or for supporting metals on inorganic oxides.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: September 15, 1998
    Assignee: Enichem S.p.A.
    Inventors: Paolo Biagini, Gabriele Lugli, Fausto Calderazzo, Daniela Belli Dell'Amico, Alessandra Merigo
  • Patent number: 5804164
    Abstract: The present invention relates to water-soluble, lipophilic contrast-enhancing agents, pharmaceutical compositions thereof and methods for diagnostic analysis, particularly NMR or MRI analysis using these contrast-enhancing agents. The water-soluble, lipophilic contrast-enhancing agents are chelates of a paramagnetic, ferromagnetic or diamagnetic metal ion(s) complexed with completing acids which contain at least one short-chain fatty acyl moiety having from about 0 to about 6 carbon atoms in its structure.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: September 8, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Gabriel A. Elgavish
  • Patent number: 5804163
    Abstract: 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: Grant
    Filed: July 14, 1994
    Date of Patent: September 8, 1998
    Assignee: Magnetic Research, Inc.
    Inventors: Wendell A. Gibby, N. Rao Puttagunta
  • Patent number: 5798092
    Abstract: Compounds of general Formula I ##STR1## wherein Z.sup.1 and Z.sup.2 in each case independently mean the residue--(CH.sub.2).sub.m --(C.sub.6 H.sub.4).sub.q --(O).sub.k --(CH.sub.2).sub.n --(C.sub.6 H.sub.4).sub.l --(O).sub.r --R,whereinm and n means the numbers 0-20,k, l, q and r means the numbers 0 and 1, andR means a hydrogen atom, an optionally OR.sup.1 -substituted C.sub.1 -C.sub.6 -alkyl residue, or a CH.sub.2 COOR.sup.1 group with R.sup.1 meaning a hydrogen atom, a C.sub.1 -C.sub.6 -alkyl residue, or a benzyl group,with the proviso that at least two substituents X stand for a metal ion equivalent; that one of the substituents Z.sup.1 and Z.sup.2 stands for a hydrogen and the other is not H; that--if n and l each means the number 0--k and r do not simultaneously mean the number 1; that --(O).sub.r --R is not --OH; and that Z.sup.1 and Z.sup.2 are not --CH.sub.2 --C.sub.6 H.sub.4 --O--CH.sub.2 --COOCH.sub.2 C.sub.6 H.sub.5 or --CH.sub.2 --C.sub.6 H.sub.4 --O--(CH.sub.2).sub.5 --COOCH.sub.2 C.sub.6 H.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 25, 1998
    Assignee: Schering Aktiengesellschaft
    Inventors: Heribert Schmitt-Willich, Johannes Platzek, Heinz Gries, Gabrielle Schumann-Giampieri, Hanns-Joachim Weinmann, Hubert Vogler, Julius Deutsch, Juergen Conrad
  • Patent number: 5789610
    Abstract: Materials and methods for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding metallic ions, for adhesion of composite materials or resins, are disclosed. Preferably, the substrate is treated with an aqueous solution comprising at least one acid, acidic salt, or chelating or sequestering agent.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: August 4, 1998
    Assignee: American Dental Association Health Foundation
    Inventor: Rafael L. Bowen
  • Patent number: 5762910
    Abstract: 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: Grant
    Filed: December 9, 1996
    Date of Patent: June 9, 1998
    Assignee: ImaRx Pharmaceutical Corp.
    Inventors: Evan C. Unger, DeKang Shen
  • Patent number: 5759226
    Abstract: A substantially neutral metal alkanoate solution suitable for application of the constituent micronutrient metal to agricultural crops or acreage where such crops are to be grown, is disclosed. Alkanoates having from 2 to 6 carbon atoms are preferred, with acetates most preferred. Metals selected from the group consisting of boron, calcium, copper, iron, magnesium, manganese, molybdenum, potassium, sodium and zinc are preferred, with zinc particularly preferred. The compositions of the present invention remain soluble at and below freezing temperatures for extending periods, and exhibits a high degree of miscibility in fertilizers. A method of manufacturing the compositions of the present invention is disclosed, in which a metal oxide is dispersed in water, ammonia is added to the dispersion, and acid is added to the basic dispersion to solubilize and substantially neutralize the dispersion and create an aqueous micronutrient solution.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: June 2, 1998
    Assignee: Platte Chemical Company
    Inventors: Anthony E. Herold, James L. Hausmann
  • Patent number: 5756069
    Abstract: An amphipathic polychelating compound including a hydrophilic polymeric moiety having a main backbone and a plurality of reactive side groups, a lipid-soluble anchor linked to the N terminal of the polymeric moiety, and a plurality of chelating agents linked to the side groups of the polymeric moiety. The polychelating compounds are bound to liposomes or micelles for use as diagnostic and therapeutic agents.
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: May 26, 1998
    Inventors: Vladimir P. Torchilin, Vladimir S. Trubetskoy, Gerald L. Wolf
  • Patent number: 5756540
    Abstract: In accordance with the present invention, there are provided methods for the in vivo reduction of nitric oxide levels in a mammalian subject. In contrast to the inhibitory approach described in the prior art (i.e., wherein the function of the enzymes responsible for nitric oxide production is inhibited), the present invention employs a scavenging approach whereby overproduced nitric oxide is bound in vivo to a suitable nitric oxide scavenger. The resulting complex renders the nitric oxide harmless, and is eventually excreted in the urine of the host. Further in accordance with the present invention, there are provided compositions and formulations useful for carrying out the above-described methods. An exemplary nitric oxide scavenger contemplated for use in the practice of the present invention is a dithiocarbamate-ferrous iron complex. The present invention relates to methods for reducing in vivo levels of .multidot.NO as a means of treating subjects afflicted with inflammatory and/or infectious disease.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: May 26, 1998
    Assignee: MCW Research Foundation, Inc.
    Inventor: Ching-San Lai
  • Patent number: 5746995
    Abstract: The invention relates to new diethylenetriaminepentaacetic acid derivatives, their complexes and complex salts, that contain an element of atomic numbers 20-32, 39-51 or 57-83, pharmaceutical agents that contain these compounds and their use as contrast media and antidotes.
    Type: Grant
    Filed: November 30, 1995
    Date of Patent: May 5, 1998
    Assignee: Schering Aktiengesellschaft
    Inventors: Franz-Karl Maier, Michael Bauer, Werner Krause, Ulrich Speck, Gabriele Schuhmann-Giampieri, Andreas Muhler, Thomas Balzer, Wolf-Rudiger Press
  • Patent number: 5741815
    Abstract: The present invention employs a scavenging approach whereby overproduced nitric oxide is bound in vivo to a suitable nitric oxide scavenger. The resulting complex renders the nitric oxide harmless, and is eventually excreted in the urine of the host. Further in accordance with the present invention, there are provided compositions and formulations useful for carrying out the above-described methods. An exemplary nitric oxide scavenger contemplated for use in the practice of the present invention is a dithiocarbamate-ferrous iron complex. This complex binds to .NO, forming a stable, water-soluble dithiocarbamate-iron-NO complex having a characteristic three-line spectrum (indicative of a mononitrosyl-Fe complex) which can readily be detected at ambient temperatures by electron paramagnetic resonance (EPR) spectroscopy. The present invention relates to methods for reducing in vivo levels of .NO as a means of treating subjects afflicted with inflammatory and/or infectious disease.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: April 21, 1998
    Inventor: Ching-San Lai
  • Patent number: 5730956
    Abstract: The invention relates to diethylenetriaminepentaacetic acid monoamide derivatives, their complexes and complex salts, containing gadolinium, dysprosium, iron or manganese, pharmaceutical agents containing these compounds, their use as contrast media and process for their production.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 24, 1998
    Assignee: Schering Aktiengesellschaft
    Inventors: Johannes Platzek, Ulrich Niedballa, Peter Mareski, Bernd Raduchel, Hanns-Joachim Weinmann, Andreas Muhler, Bernd Misselwitz
  • Patent number: 5698724
    Abstract: The method and composition involves preparing a high yield of a metal amino acid complex visible as a source of highly bioavailable transition metal ions, highly bioavailable essential amino acid for a livestock animal is disclosed. The method involves preparing the metal amino acid complex from a protein starting material resulting product in high yield. The protein starting material is hydrolyzed to provide an amino acid hydrolyzate and thereafter a metal oxide corresponding to the desired metal for the metal amino complex is added to the amino acid hydrolyzate to react to form a high yield metal amino acid complex which is thereafter used to form a dose for supplementation of diet to assure adequate trace minerals and adequate essential amino acids in the diet of a livestock animal.
    Type: Grant
    Filed: April 30, 1996
    Date of Patent: December 16, 1997
    Assignee: Zinpro Corporation
    Inventors: Michael D. Anderson, Mahmoud M. Abdel-Monem
  • Patent number: 5693309
    Abstract: 1. Compounds of general Formula I ##STR1## wherein n and m in each case mean the numbers 0, 1, 2, 3 and 4,X stands for a hydrogen atom and/or a metal ion equivalent of an element of atomic numbers 21-29, 31, 32, 37-39, 42-44, 49 or 57-83,R.sup.1 and R.sup.2, being different, mean in each case a hydrogen atom or a straight-chain, branched, saturated or unsaturated C.sub.0 -C.sub.20 -alkylene group, this alkylene group exhibiting at the end either a second molecule of general Formula I.sub.A or I.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Julius Deutsch, Heinz Gries, Erich Klieger, Ulrich Niedballa, Franz-Josef Renneke, Jurgen Conrad, Wolfgang Muetzel, Heribert Schmitt-Willich
  • Patent number: 5681366
    Abstract: A substantially neutral metal alkanoate solution suitable for application of the constituent micronutrient metal to agricultural crops or acreage where such crops are to be grown, is disclosed. Alkanoates having from 2 to 6 carbon atoms are preferred, with acetates most preferred. Metals selected from the group consisting of boron, calcium, copper, iron, magnesium, manganese, molybdenum, potassium, sodium and zinc are preferred, with zinc particularly preferred. The compositions of the present invention remain soluble at and below freezing temperatures for extending periods, and exhibits a high degree of miscibility in fertilizers. A method of manufacturing the compositions of the present invention is disclosed, in which a metal oxide is dispersed in water, ammonia is added to the dispersion, and acid is added to the basic dispersion to solubilize and substantially neutralize the dispersion and create an aqueous micronutrient solution.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: October 28, 1997
    Assignee: Platte Chemical Company
    Inventors: Anthony E. Herold, James L. Hausmann
  • Patent number: 5681543
    Abstract: Polymers comprising a ligand containing a carboxylic acid group, optionally at least one ion of an element of the atomic numbers 21-29, 42, 44 or 57-83 as well as optionally cations of inorganic and/or organic bases, amino acids or amino acid amides are valuable complexing agents and complexes for diagnosis.
    Type: Grant
    Filed: August 10, 1994
    Date of Patent: October 28, 1997
    Assignee: Shering Aktiengesellschaft
    Inventors: Heribert Schmitt-Willich, Julius Deutsch, Heinz Gries, Jurgen Conrad, Reinhard Neumeier
  • Patent number: 5676923
    Abstract: Diethylenetriaminepentaacetic acid monoamide derivatives, their complexes and complex salts, containing an element of atomic numbers 21-29, 31, 32, 39, 42-44, 49 or 57-83, pharmaceutical agents containing these compounds, their use as contrast media and process for their production.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 14, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Johannes Platzek, Ulrich Niedballa, Peter Mareski, Bernd Raduchel, Hanns-Joachim Weinmann, Andreas Muhler, Bernd Misselwitz
  • Patent number: 5672335
    Abstract: Metal complexes containing a metal of atomic numbers 39-42, 44-51 or 56-83 and a complexing agent can be used for the production of contrast media for use in the contrast-enhanced computer tomography of the liver and the biliary tracts.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 30, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Krause, Thomas Balzer, Wolf-Rudiger Press, Gabriele Schuhmann-Giampieri, Ulrich Speck, Andreas Muhler
  • Patent number: 5661177
    Abstract: A process of treatment against seborrhea and/or for the cicatrization of wounds and/or for stimulation of skin cell growth involving a topical application and/or an oral administration of any composition that contains zinc cysteate, wherein zinc cysteate is based on the following formula--O--SO.sub.2 --CH.sub.2 --CH(NH.sub.2)--CO--O--ZN--and wherein the zinc cysteate is in an anhydrous or a hydrated form. Zinc cysteate is dehydrated and based on the formulaC.sub.3 H.sub.5 O.sub.5 NSZSa, 2H.sub.2 O.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: August 26, 1997
    Assignee: Chimie et Biologie
    Inventors: Jean Blum, Olivier Guillard
  • Patent number: 5637759
    Abstract: Novel organic compounds and metal ion-containing amino acid chelates are described which are useful in solid phase synthesis of polypeptides and as magnetic resonance imaging (MRI) enhancing agents. The present invention also relates to a convenient and straightforward method to synthesize a metal-ligating amino acid suitable as MRI enhancing agents or for introducing a strong metal binding site at any chosen position in a peptide. Some compounds are designed to be compatible with N-.alpha.-Fmoc peptide synthesis strategy, and can easily be prepared on large scale. Thus, flexible linkers of different lengths and containing various structures can be placed between the .alpha.-carbon backbone of peptides and metal binding moieties. These peptides will provide a variety of affinity cleaving reagents which can be directed against protein or nucleic acid targets. Therefore, these molecules can serve as an important tool to study protein folding, protein-protein and protein-nucleic acid interactions.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: June 10, 1997
    Assignee: The Regents of the University of California
    Inventors: John E. Hearst, Tariq M. Rana, Matt Ban
  • Patent number: 5637311
    Abstract: Zinc(II) complexes and methods relating thereto are disclosed. The zinc(II) complexes comprise a zinc(II) ion complexed by a multi-dentate ligand. Methods of this invention include the use of the zinc(II) complexes as anti-viral agents and/or as anti-inflammatory agents. Methods of this invention also include inhibition of viral infection, as well as inhibiting transmission of sexually transmitted diseases. Exemplary zinc(II) complexes include zinc(II):neocuproine (2:1) and zinc(II):bathocuproine disulfonic acid (2:1).
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: June 10, 1997
    Assignee: ProCyte Corporation
    Inventor: Alexander J. Pallenberg
  • Patent number: 5614653
    Abstract: The present invention is directed to methods for solubilizing boric acid to produce liquid, boron-containing solutions. In these methods, boric acid is added to a previously formed solution of a metal ion and ligand. The ligand must be capable of both complexing the metal ion and simultaneously coordinating or hydrogen bonding with the boric acid. Preferred metal ions are the transition metals. Preferred ligands are the alkanolamines, polyamines, dialkylaminoalkylamines and alkyldiaminecarboxylic acids and salts thereof. Using the methods of the present invention, stable, clear solutions, preferrably aqueous solutions, containing about 9-11 percent-by-weight or more boron are readily prepared.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: March 25, 1997
    Assignee: Stoller Enterprises, Inc.
    Inventor: Frank W. Dean
  • Patent number: 5582814
    Abstract: Paramagnetic metal complexes of 1-(p-n-butylbenzyl)diethylenetriamine pentaacetic acid and pharmaceutically acceptable salts thereof are effective as tissue-specific MRI contrast agents, and in particular as hepatobiliary MRI contrast agents.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: December 10, 1996
    Assignee: Metasyn, Inc.
    Inventors: Daniel M. Scott, Randall B. Lauffer
  • Patent number: 5571498
    Abstract: Emulsions of paramagnetic contrast agents, and processes of making and using them are disclosed. The emulsions contain water, a dispersed oil phase and a complex of a paramagnetic metal ion and an organic chelator having a C.sub.10 -C.sub.30 unsaturated aliphatic group. The emulsions are very stable and therapeutically acceptable for intravenous administration to enhance MRI.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: November 5, 1996
    Assignee: HemaGen/PFC
    Inventors: William P. Cacheris, Robert J. Kaufman, Thomas J. Richard, Raymond C. Grabiak
  • Patent number: 5562894
    Abstract: The present invention relates to the preparation of amino-acyl-type and catecholamine-type compounds having multiple carboxylic acid functional groups. Paramagnetic metal (II) or (III) ion chelate complexes are formed using these compounds for use as intravenous contrast agents to produce enhanced contrast magnetic resonance images of the heart, liver, biliary tree or upper small intestine. The mono- and di-amino acids, their esters and amides, and catecholamine-like derivatives, of EDTA, DTPA, and the like are prepared. The paramagnetic metal (II) or (III) ion complexes are formed and produce T1-related contrast effects in MR images. The compounds and complexes also appear to have low toxicities and to be relatively rapidly and completely cleared from the tissue of a living mammal, e.g. a human being.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: October 8, 1996
    Assignee: Regents of the University of California
    Inventor: David L. White
  • Patent number: 5554357
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: September 10, 1996
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: Raghavan Rajagopalan
  • Patent number: 5516925
    Abstract: A palatable metal amino acid chelate for administration to humans and other warm-blooded animals is disclosed wherein there are sufficient ligands to provide ionic and coordinate covalent bonds equal to the coordination number of the central metal ion while, at the same time, maintaining charge balance in the chelate molecule. There must be at least one ligand of the polydentate type which must be an .alpha.-amino acid with the further proviso that any unidentate or polydentate ligand(s) must be charge balanced organic ligands. Charge balancing may be accomplished by means of an organic acid and dicarboxylic, hydroxycarboxylic, hydroxydicarboxylic or hydroxytricarboxylic acids in particular, which maintains the chelate molecule as an optimum pH for purposes of stability and palatability.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: May 14, 1996
    Assignee: Albion International, Inc.
    Inventors: Mark Pedersen, H. DeWayne Ashmead
  • Patent number: 5506264
    Abstract: The present invention is concerned with the zinc tranexamate represented by the formula: ##STR1## or its pharmacologically acceptable organic acid salts. The zinc compounds of the present invention, when given in smaller doses than tranexamic acid and cetraxate hydrochloride, exhibit anti-inflammatory and anti-ulcer activities, and are tasteless and odorless, thus being easy to be administered; in particular, the organic acid salts are water-soluble and can be processed into the liquid dosage forms of injectable solution and liquid preparations for external uses.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: April 9, 1996
    Assignee: Zaidan Hojin Seisan Kaihatsu Kaguki Kenkyusho
    Inventors: Hajime Fujimura, Takahiro Yabuuchi, Teruo Tanaka
  • Patent number: 5494656
    Abstract: A second sphere contrast enhancing agent for magnetic resonance imaging comprises a paramagnetic metal ion having catecholate ligands coordinated thereto and having water molecules hydrogen bonded to the catecholate ligands.
    Type: Grant
    Filed: March 17, 1995
    Date of Patent: February 27, 1996
    Assignee: The University of Toledo
    Inventor: Julian A. Davies
  • Patent number: 5482700
    Abstract: 1. Compounds of general Formula I ##STR1## wherein n and m in each case mean the numbers 0, 1, 2, 3 and 4,X stands for a hydrogen atom and/or a metal ion equivalent of an element of atomic numbers 21-29, 31, 32, 37-39, 42-44, 49 or 57-83,R.sup.1 and R.sup.2, being different, mean in each case a hydrogen atom or a straight-chain, branched, saturated or unsaturated C.sub.0 -C.sub.20 -alkylene group which optionally contains imino, phenylenoxy, phenylenimino, amido, hydrazido, ester group(s), oxygen, sulfur and/or nitrogen atom(s) and is substituted, if desired, by hydroxy, mercapto, imino, epoxy, oxo, thioxo and/or amino group(s), this alkylene group exhibiting at the end either a second molecule of general Formula I.sub.A or I.sub.B ##STR2## a functional group, or, linked by way of this functional group, a bio- or macromolecule,are valuable diagnostic and therapeutic media.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: January 9, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Julius Deutsch, Heinz Gries, Erich Klieger, Ulrich Niedballa, Franz-Josef Renneke, Juergen Conrad, Wolfgang Muetzel
  • Patent number: 5476957
    Abstract: The heat-sensitive recording material disclosed comprises a colorless or pale colored dyestuff precursor, one or more salicylic acid derivative of the formula (1) or metal salt of the derivative and an aliphatic amide compound having 18.about.60 carbon atoms in molecular structure, and is excellent in thermal response and preservation stability of white portions and images. ##STR1## wherein X.sub.1 and X.sub.2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y.sub.1 and Y.sub.2 are an oxygen atom or a sulfur atom, R.sub.1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R.sub.2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: December 19, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshimitsu Tanabe, Yuki Kobayashi, Atsuo Otsuji, Masakatsu Nakatsuka, Akihiro Yamaguchi
  • Patent number: 5470876
    Abstract: SOD for treating hair loss is disclosed. The SOD has utility in a topical pharmaceutical formulation for the cosmetic treatment of hair loss and the cosmetic stimulation of hair growth. The SOD comprises copper salicylate, copper aspirinate, indomethacin-copper, or a complex of an amino acid or peptide and a transition metal.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: November 28, 1995
    Inventor: Peter H. Proctor
  • Patent number: 5466439
    Abstract: A polymeric contrast enhancing agent for magnetic resonance images having a chelating agent, which can be bound to metal ions having at least one unpaired electron, such as gadolinium. Examples of such chelating agents include DTPA-ethylenediamide-methacrylate copolymer and poly-(DTPA-ethylenediamide). These contrast enhancing agents, bound to the metal ions, are then administered to a patient, and following this the MR images are taken.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: November 14, 1995
    Assignee: Magnetic Research, Inc.
    Inventors: Wendell A. Gibby, N. Rao Puttagunta
  • Patent number: 5466438
    Abstract: 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: Grant
    Filed: December 27, 1993
    Date of Patent: November 14, 1995
    Assignee: ImaR.sub.x Pharmaceutical Corp.
    Inventors: Evan C. Unger, DeKang Shen
  • Patent number: 5463098
    Abstract: A residue free, antiperspirant gel stick composition is disclosed which comprises an antiperspirant compound which is soluble in a diol, a normally liquid, water soluble diol, a gelling agent and a zinc glycinate in amount sufficient to control the pH of the gel stick at about 4.1 to about 5.0, the glycine to zinc mole ratio of the zinc glycinate added being about 2.0/1 to about 3.0/1. The process for preparing a diol soluble antiperspirant active useful in preparing the residue free gel stick is also disclosed and comprises reacting an antiperspirant compound with a water soluble, normally liquid diol in a water solution by heating for about 1 to about 100 hours at a temperature of about 50.degree. C. to about 110.degree. C.; adding a zinc glycinate to the reaction mixture and removing the water to recover a powdered antiperspirant active.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: October 31, 1995
    Inventors: Rocco Giovanniello, Nelson P. Ayala
  • Patent number: 5460799
    Abstract: 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: Grant
    Filed: August 18, 1994
    Date of Patent: October 24, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Gabriel A. Elgavish, Sung K. Kim
  • Patent number: 5430164
    Abstract: Method of enhancing the water solubility of dry zinc methionine complex salts by reacting in water soluble zinc salt with mentionine in the presence of ferric ion with the amount being between about 15 mole percent and 30 mole percent of the amount of zinc present.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: July 4, 1995
    Assignee: Zinpro Corporation
    Inventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
  • Patent number: 5419894
    Abstract: Compounds of the general formula I: ##STR1## wherein 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## and X represents hydrogen atoms and/or metal ion equivalents, and their salts with physiologically harmless organic bases, are valuable complexing agents, complexes and complex salts for diagnostic imaging.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: May 30, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinz Gries, Franz-Josef Renneke, Hanns-Joachim Weinmann
  • Patent number: 5405601
    Abstract: 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: Grant
    Filed: July 2, 1993
    Date of Patent: April 11, 1995
    Assignee: Mallinckrodt Medical Inc.
    Inventors: T. Jeffrey Dunn, Dennis A. Moore, Muthanadar Periasamy, Milorad M. Rogic, Rebecca A. Wallace, David H. White, Steven R. Woulfe
  • Patent number: 5382421
    Abstract: 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: Grant
    Filed: September 17, 1993
    Date of Patent: January 17, 1995
    Assignee: The Regents of the University of California
    Inventors: David L. White, Barry L. Engelstad, Kurt Muetterties
  • Patent number: 5370860
    Abstract: 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: Grant
    Filed: July 29, 1993
    Date of Patent: December 6, 1994
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Gabriel A. Elgavish, Sung K. Kim
  • Patent number: 5344639
    Abstract: 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: Grant
    Filed: June 26, 1991
    Date of Patent: September 6, 1994
    Assignee: Medgenix Group S.A.
    Inventors: Kwok W. Chiu, Wassif Hussain, John R. Thornback
  • Patent number: 5330743
    Abstract: 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: Grant
    Filed: November 12, 1992
    Date of Patent: July 19, 1994
    Assignee: Magnetic Research, Inc.
    Inventors: Wendell A. Gibby, N. Rao Puttagunta