The Hetero Ring Contains At Least Three Nitrogens Patents (Class 540/474)
-
Patent number: 5376357Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with aminoalkylamide derivatives of diethylenetriaminepentaacetic acid ("DTPA") or ethylenediaminetetraacetic acid ("EDTA") or other polyaminocarboxylic or cyclic polyaminocarboxylic chelating agents, These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: December 21, 1990Date of Patent: December 27, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Muthunadar P. Periasamy
-
Patent number: 5374416Abstract: The invention relates to ligands of formula ##STR1## in which B represents an ##STR2## W representing the ##STR3## group, in which groups X and Z represent a heterocycle. The invention also relates to the monometallic or polymetallic complexes formed by these ligands with metal ions chosen from lanthanide ions, transition metal ions. barium, bismuth, lead and the radioisotopes .sup.99m Tc, .sup.111 In, .sup.90 Y, .sup.64 Cu and .sup.169 Yb, as well as the physiologically acceptable salts of these complexes.The salts of these complexes may be used as diagnostic or therapeutic agents in nuclear magnetic resonance imaging and X-ray radiology, as in-vivo chemical shift agents and in nuclear medicine.Type: GrantFiled: November 17, 1992Date of Patent: December 20, 1994Assignee: Guerbet S.A.Inventors: Olivier Rousseaux, Michel Schaefer, Anne Bouillot, Dominique Meyer
-
Patent number: 5373093Abstract: Functionalized water soluble macrocyclic complexes of lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of: (1) a functionalized 1,2-diaminoethane and a dicarbonyl compound selected from the group consisting of 2,6-dicarbonylpyridine, 2,6-diformylpyridine, 2,5-dicarbonylfuran, 2,5-diformylfuran, 2,5-dicarbonylthiophene and 2,5-diformylthiophene; or (2) 1,2-diaminoethane and a ring-substituted heterocyclic dicarbonyl compound selected from a group consisting of substituted 2,6-dicarbonylpyridine, substituted 2,6-diformylpyridine, substituted 2,5-dicarbonylfuran, substituted 2,5-diformylfuran; substituted 2,5-dicarbonyl thiophene, and substituted 2,5-diformylthiophene. Coordination complexes thus formed are kinetically stable in dilute aqueous solution.Type: GrantFiled: March 15, 1991Date of Patent: December 13, 1994Inventors: Lidia M. Vallarino, Robert C. Leif
-
Patent number: 5364614Abstract: Cascade polymers, containing complex-forming ligands, optionally at least five ions of an element of atomic numbers 21-29, 39, 42, 44 or 57-83, as well as, if desired, cations of inorganic and/or organic bases, amino acids or amino acid amides, are valuable complexing compounds and complexes for diagnostics and therapy.Type: GrantFiled: November 21, 1990Date of Patent: November 15, 1994Assignee: Schering AktiengesellschaftInventors: Johannes Platzek, Heribert Schmitt-Willich, Heinz Gries, Gabriele Schuhmann-Giampieri, Hubert Vogler, Hanns-Joachim Weinmann, Hans Bauer
-
Patent number: 5362476Abstract: The present invention relates to a new polyazamacrocyclic compound or a salt thereof and its uses as a tissue specific chelator. The compound has the formula ##STR1## where x is 2, 3 or a combination of p 2(s) and q 3(s) where p+q=y;y is 4;R is ( CH.sub.2).sub.z P(=0)OR.sup.1 OR.sup.2 ;R.sup.1 is H or CH.sub.3 ;R.sup.2 is C.sub.n H.sub.1+2n ;n is 4 to 6;z is 1 to 3.M is a heavy metal ion.These compounds may be used for magnetic resonance imaging.Type: GrantFiled: July 31, 1992Date of Patent: November 8, 1994Assignees: Board of Regents, The University of Texas System, Dow Chemical CompanyInventors: A. Dean Sherry, Garry E. Kiefer
-
Patent number: 5342606Abstract: The present invention relates to a new polyazamacrocyclic compound or a salt thereof and its uses. The compound has the formula ##STR1## where x is 2, 3 or a combination of p 2(s) and q 3(s) where p+q=y;y is 3 or 4;R is (CH.sub.2).sub.z P(=0)R.sup.1 R.sup.2 ;R.sup.1 is R.sup.3 or OR.sup.3 where R.sup.3 is alkyl, cycloalkyl or aryl;R.sup.2 is H, alkyl or ##STR2## where R.sup.4 is alkyl, cycloalkyl or aryl; and z is 1 to 3.In one important embodiment, this compound may be complexed with a metal to be a polyazamacrocyclic compound-metal complex having the formula ##STR3## where r is 2 or 3; andMe is a metal ion.Type: GrantFiled: November 19, 1990Date of Patent: August 30, 1994Assignee: Board of Regents, The University of Texas SystemInventors: A. Dean Sherry, Istvan Lazar, Erno Brucher, Ravichandran Ramasamy
-
Patent number: 5342936Type: GrantFiled: October 2, 1992Date of Patent: August 30, 1994Inventors: David Parker, Michael A. W. Eaton
-
Patent number: 5326861Abstract: An improved process for preparing triazacyclo compounds and, in particular, 1,4,7-tritosyl-1,4,7-triazyacyclononane. The process involves reacting a diethylenetriamine triarylsulphonate with a cyclising agent selected from the group consisting of diaryl sulphonates, dialkyl sulphonates, ethylene dibromide, ethylene dichloride and diacetylglycol in the presence of ultrasound.Type: GrantFiled: October 21, 1992Date of Patent: July 5, 1994Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Stephen A. Madison, Jean H. Koek, Johan J. W. Eshuis, Ronald P. Potman
-
Patent number: 5324857Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.Type: GrantFiled: April 28, 1992Date of Patent: June 28, 1994Assignee: Solvay InteroxInventor: Noel S. Shehad
-
Patent number: 5324334Abstract: There are disclosed macrocyclic and polycyclic polyamine lubricating oil additives formed by cyclodehydration of reaction products of hydrocarbon substituted succinic anhydrides or carboxylic acids with poly 3-amino propyl compounds or by acylation of macrocyclic polyamines and polycyclic polyamines with hydrocarbon substituted succinic anhydride or carboxylic acids. These compounds are useful as dispersants and dispersants-V.I. improvers in both gasoline and diesel engine lubricating oil compositions and are also useful fuel additives.Type: GrantFiled: October 28, 1992Date of Patent: June 28, 1994Assignee: Exxon Research & EngineeringInventors: Stanley J. Brois, Antonio Gutierrez
-
Patent number: 5314680Abstract: Novel magnetic resonance imaging agents comprise complexes of paramagnetic ions with hydrazide derivatives of polyaminocarboxylic acid chelating agents. These novel imaging agents are characterized by excellent NMR image-contrasting properties and by high solubilities in physiological solutions.A novel method of performing an NMR diagnostic procedure involves administering to a warm-blooded animal an effective amount of a complex as described above and then exposing the warm-blooded animal to an NMR imaging procedure, thereby imaging at least a portion of the body of the warm-blooded animal.Type: GrantFiled: May 4, 1993Date of Patent: May 24, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Raghavan Rajagopalan, Rebecca A. Wallace, Muthunadar P. Periasamy
-
Patent number: 5284944Abstract: An improved process is described for obtaining triazacyclononanes, esepcially 1,4,7-trimethyl-1,4,7-triazacyclononame. The first step involves reacting diethylenetriamine (DET) with a sulfonylation agent to form a sulfonamidated DET, in an aqueous medium with an inorganic base. In a second step, but preferably within the same reactor vessel without isolating intermediates, the sulfonamidated DET aqueous mixture is contacted with an aprotic organic solvent in the presence of a cyclizing unit such as ethylene glycol ditosylate or ethylene dibromide, thereby resulting in a cyclized sulfonamidated triamine compound. Thereafter the protecting groups are removed and the amine is alkylated, preferably within a single reaction vessel without isolation of intermediates.Type: GrantFiled: June 30, 1992Date of Patent: February 8, 1994Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Steven A. Madison, David J. Batal
-
Patent number: 5281704Abstract: There are disclosed polychelant compounds, that is multi-site metal chelating agents, and chelates formed therewith. The polychelants and especially their paramagnetic metal, heavy metal or radioactive metal polychelates are particularly suitable for use in diagnostic imaging, heavy metal detoxification or radiotherapy. The polychelants have a linear or branched oligomeric structure comprising alternating chelant and linker moieties bound together by amide or ester moieties the carbonyl groups whereof being adjacent the chelant moieties, each polychelant comprising at least two said chelant moieties capable of complexing a metal ion.Type: GrantFiled: January 19, 1990Date of Patent: January 25, 1994Assignee: Salutar, Inc.Inventors: David B. Love, William C. Dow, Richard J. Himmelsbach, Alan D. Watson, Scott M. Rocklage
-
Patent number: 5271927Abstract: The conjugation of antibodies to a macrocyclic conjugate compound wherein the conjugate compound has the structure (I), wherein R.sup.1 is --(CH.sub.2).sub.p --R.sup.6 --CH.sub.2).sub.q -- where p and q are the same or different and are 0, 1 or 2, and --R.sup.6 -- is --((CH.sub.2).sub.n --, where n is 0 or 1, --NH--, --O--, --S-- or (II), R.sup.1 optionally being alkyl substituted, provided that neither p nor q is 0 unless R.sup.6 is --CH.sub.2 --; R.sup.2 are --CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.sub.2 --, optionally alkyl, alkoxyalkyl or hydroxyalkyl substituted; R.sup.3 are the same or different and are --H, alkyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl, carboxyalkyl ester, phosphate, sulphonate or phosphonate; R.sup.4 is one of the compounds of formula (III) optionally alkyl substituted, wherein R.sup.7 is --H, alkyl, hydroxyalkyl, or alkoxyalkyl provided that when R.sup.4 is (III d), R.sup.3 is not carboxyalkyl, R.sup.5 is a linker, and Ab is an antibody.Type: GrantFiled: March 18, 1993Date of Patent: December 21, 1993Assignee: Celltech LimitedInventors: David Parker, Thomas A. Millican
-
Patent number: 5247075Abstract: Tri-aza macrocycles of formula (I), wherein m and n, which may be the same or different, is each zero or an integer 1, 2, or 3; p is zero or an integer 1 or 2; q is zero or an integer from 1 to 6 inclusive; R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, is each a hydrogen atom or an alkyl, alkoxyalkyl, --CO.sub.2 H, ---SO.sub.3 H, PO.sub.3 H.sub.2 or aryl group; L is a covalent bond or linker group; Z is a hydrogen atom or a reactive functional group, with the proviso that when L is a covalent bond Z is a reactive functional group; and metal complexes and/or salts thereof are described together with processes for their preparation and compositions containing them. The compounds are useful for imaging and in the treatment of abnormal cell disorders, such as in the treatment of tumours, and are particularly suitable for coupling to other molecules such as proteins for use in diagnosis and therapy.Type: GrantFiled: October 22, 1991Date of Patent: September 21, 1993Assignee: Celltech LimitedInventors: David Parker, Thomas A. Millican
-
Patent number: 5247077Type: GrantFiled: March 31, 1992Date of Patent: September 21, 1993Assignee: Celltech LimitedInventors: David Parker, Michael A. W. Eaton
-
Patent number: 5245026Abstract: The present invention provides linear, cyclic and trifurcate tri- and tetramine backbone multidentate chelating agents based on the 8-hydroxyquinoline chelating unit. The chelating agents may optionally be substituted with a substrate reactive moiety and antibody-metal ion conjugates may be produced for in vivo diagnostic and therapeutic methods.Type: GrantFiled: May 21, 1991Date of Patent: September 14, 1993Assignees: Abbott Laboratories, Tobishi Yakuhin Kogyo Kabushiki KaishaInventors: David K. Johnson, Steven J. Kline
-
Patent number: 5240573Abstract: Phosphate ion-sensitive composition and ion-selective electrode are disclosed incorporating an ionophore having the formula:R.sub.1 -X (a)orX-Z-X (b)wherein R.sub.1 is H or a hydrophobic substituent, Z is a spacing unit and X is represented by the formula: ##STR1## wherein n=0 or 1 and R.sub.2 and R'.sub.2 are independently selected from the group consisting of CH.sub.2, C(O) or C(S).Type: GrantFiled: January 14, 1993Date of Patent: August 31, 1993Assignee: C & R Approaches, Inc.Inventor: Clifton Carey
-
Patent number: 5236695Abstract: Polyphosphonate ligands containing three or more phosphonate groups, combined with paramagnetic metal cations and administered in the form of pharmacologically acceptable salts, are useful as MRI contrast enhancement agents, which tend to localize in bone tissue without being conjugated to bone-specific biomolecules. Triazacyclononanes and tetraazacyclododecanes, with dihydroxyphosphorylmethyl or dihydroxyphosphorylethyl groups, optionally substituted at the methyl or ethyl bridges with alkyl, aryl, hydroxyl or amino groups, are particularly preferred.Type: GrantFiled: September 11, 1991Date of Patent: August 17, 1993Assignee: Concat, Ltd.Inventors: Harry S. Winchell, Joseph Y. Klein, Elliot D. Simhon, Rosa L. Cyjon, Ofer Klein, Haim Zaklad
-
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
-
Patent number: 5188816Abstract: The present invention relates to a method of using a polyazamacrocyclic compound or a salt thereof to measure intracellular metal ions formula ##STR1## where x is 2, 3 or a combination of p 2(s) and q 3(s) where p +q=y;y is 3 or 4;R is (CH.sub.2).sub.z P(=O)R.sup.1 R.sup.2;R.sup.1 is R.sup.3 or OR.sup.3 where R.sup.3 is alkyl, cycloalkyl or aryl;R.sup.2 is H, alkyl or ##STR2## where R.sup.4 is alkyl, cycloalkyl or aryl; and z is 1 to 3.Type: GrantFiled: November 26, 1991Date of Patent: February 23, 1993Assignee: Board of Regents, The University of Texas SystemInventors: A. Dean Sherry, Istvan Lazar, Erno Brucher, Ravichandran Ramasamy
-
Patent number: 5162526Abstract: There are disclosed macrocyclic and polycyclic polyamide lubricating oil additives formed by cyclodehydration of reaction products of hydrocarbon substituted succinic anhydrides or carboxylic acids with poly 3-amino propyl compounds or by acylation of macrocyclic polyamines and polycyclic polyamines with hydrocarbon substituted succinic anhydride or carboxylic acids. These compounds are useful as dispersants and dispersants-V.I. improvers in both gasoline and diesel engine lubricating oil compositions and are also useful fuel additives.Type: GrantFiled: July 29, 1991Date of Patent: November 10, 1992Assignee: Exxon Chemical Patents Inc.Inventors: Stanley J. Brois, Antonio Gutierrez
-
Patent number: 5087696Abstract: A conjugate compound has the structure (I), wherein R.sup.1 is --(CH.sub.2).sub.p --R.sup.6 --(CH.sub.2).sub.q -- where p and q are the same or different and are 0, 1 or 2, and --R.sup.6 -- is --(CH.sub.2).sub.n --, where n is 0 or 1, --NH--, --O--, --S-- or (II), R.sup.1 optionally being alkyl substituted, provided that neither p nor q is 0 unless R.sup.6 is --CH.sub.2 --; R.sup.2 are --CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.sub.2 --, optionally alkyl, alkoxyalkyl or hydroxyalkyl substituted; R.sup.3 are the same or different and are --H, alkyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl, carboxyalkyl ester, phosphate, sulphonate or phosphonate; R.sup.4 is one of the compounds of formula (III) optionally alkyl substituted, wherein R.sup.7 is --H, alkyl, hydroxyalkyl, or alkoxyalkyl provided that when R.sup.4 is (III d), R.sup.3 is not carboxyalkyl, R.sup.5 is a linker, and Ab is an antibody.Type: GrantFiled: December 14, 1987Date of Patent: February 11, 1992Assignee: Celltech LimitedInventors: David Parker, Thomas A. Millican
-
Patent number: 5068324Abstract: The present invention deals with novel amphoteric polymers and their application as softening, anti-tangle, and conditioning agents. The properties of these novel compositions which make them well suited for these applications is their substantivity to fibers, hair and skin and that they are very mild to the skin and eyes. The subject compositions are prepared by the polymerization of amphoteric monomers compounds with epichlorohydrin. The amphoteric monomer compounds are prepared by the reaction of commercially available multifunctional amines with an alpha beta unsaturated acid.Type: GrantFiled: September 5, 1989Date of Patent: November 26, 1991Assignee: LCE PartnershipInventor: Anthony J. O'Lenick, Jr.
-
Patent number: 5064956Abstract: The invention relates to a novel process to prepare selectively mono-N-alkylated polyazamacrocycles which requires an electrophile with between about one and five equivalents of a suitable macrocycle in a solvent which will not promote a proton transfer.Type: GrantFiled: July 9, 1990Date of Patent: November 12, 1991Assignee: The Dow Chemical CompanyInventor: William J. Kruper, Jr.
-
Patent number: 5053503Abstract: A bifunctional chelating agent for joining an antibody or antibody fragment and a metallic radionuclide is disclosed. The agent consists of a derivative of 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid or a 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, an organic linking radical which optionally contains a cleavable group, and a function capable of reacting with a site on a protein. Radiodiagnostic or radiotherapeutic precursors comprising an antibody or antibody fragment and the above-described bifunctional chelating agent and radiodiagnostic or radiotherapeutic agent comprising a metallic radionuclide and the above mentioned precursor are also disclosed.Type: GrantFiled: February 17, 1989Date of Patent: October 1, 1991Assignee: CentocorInventors: Richard T. Dean, Robert W. Weber
-
Patent number: 5049667Abstract: The subject of the invention is nitrogen-containing cyclic ligands and metal complexes formed by these ligands, the uses of these complexes as magnetic resonance imaging (MRI) agents, as X-ray contrast agents and as chemical shift reagents in vivo.Type: GrantFiled: October 16, 1989Date of Patent: September 17, 1991Assignee: Guerbet S.A.Inventors: Michel Schaefer, Didier Doucet, Bruno Bonnemain, Dominique Meyer, Dominique Paris
-
Patent number: 5047527Abstract: Process for the preparation of monofunctionalized cyclic tertramines of formula I ##STR1## in which R denotes a saturated or unsaturated, especially polymerizable, organic radical, characterized in that the corresponding tetraazacycloalkane compound (according to formula II) is prepared, in which three of the four nitrogen atoms are bonded via covalent bonds with a single atom or group of intracyclic atoms A, in that this triprotected compound is reacted with an organic compound RX (of formula III), X denoting a nucleophobic group, and in that the tetraazacycloalkane compound which is tri-protected and monofunctionalized on the unprotected nitrogen (according to formula IV) thus obtained is deprotected.Type: GrantFiled: March 19, 1990Date of Patent: September 10, 1991Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Henri Handel, Jean-Jacques Yaouanc, Ayoub F. Zegzouti, Denis Malouala, Herve des Abbayes, Jean-Claude Clement, Helene Bernard, Guenaelle Le Gall
-
Patent number: 5041545Abstract: Hydrazide functionalized 2-hydroxybenzophenone ultraviolet light and heat stabilizers and derivatives are disclosed having the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X, Y, Z, all substituents thereof, and n are set forth in the Summary of the Invention. Y--N(R.sup.6)--Z is the hydrazide or derivative group and --X--R.sup.5 -- links the hydrazide group to an aromatic nucleus of the optionally substituted benzophenone group. Derivatives are, for example, acyl hydrazides, diacyl hydrazides (including imides), hydrazones and alkyl hydrazides. The compounds are useful as ultraviolet light absorbers and heat stabilizers for plastics.Type: GrantFiled: April 6, 1989Date of Patent: August 20, 1991Assignee: Atochem North America, Inc.Inventor: Terry N. Myers
-
Patent number: 5023376Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from the problems of in situ generation of nitrosamines, which are allegedly carcinogens, as impurities and impaired product formation, especially in the presence of transition metals.The problems can be ameliorated by employing a selected range of alkyleneaminopoly(methylenephosphonic acid) compounds such as cyclohexane-1,2-diaminotetra(methylenephosphonic acid).Type: GrantFiled: July 17, 1989Date of Patent: June 11, 1991Assignee: Interox AmericaInventors: Noel S. Shehad, Laurie L. Dussack, Dirk van Hemelrijk
-
Patent number: 5021567Abstract: The present invention provides linear, cyclic and trifurcate tri- and tetramine backbone multidentate chelating agents based on the 8-hydroxyquinoline chelating unit. The chelating agents may optionally be substituted with a substate reactive moiety and antibody-metal ion conjugates may be produced for in vivo diagnostic and therapeutic methods.Type: GrantFiled: September 24, 1987Date of Patent: June 4, 1991Assignee: Abbott LaboratoriesInventors: David K. Johnson, Steven J. Kline
-
Patent number: 5021409Abstract: Pharmaceutical compositions containing as active ingredients a linked cyclic compound of the general formula IZ--(A).sub.n --Y (I)in which Z and Y are independently cyclic polyamine moieties having from 9 to 32 ring members and from 3 to 8 amine nitrogen atoms in the ring, A is a linking atom or groups and n is O or an integer from 1 to 6, are indicated for the treatment of viral infections, and preventative administration, especially for retroviral infections.Type: GrantFiled: December 21, 1989Date of Patent: June 4, 1991Assignee: Johnson Matthey PLCInventors: Barry A. Murrer, David A. Schwartz
-
Patent number: 4990614Abstract: A compound of the formula: ##STR1## wherein ##STR2## represents a cyclic amino group, A represents a methylene group or a carbonyl group, m represents an integer of 1 to 3, n represents an integer of 0 to 4 and p represents an integer of 1 to 2, or a salt thereof, which has glutamate receptor inhibiting activity is provided.Type: GrantFiled: October 5, 1988Date of Patent: February 5, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Terumi Nakajima, Koichi Shudo, Giichi Goto
-
Patent number: 4937333Abstract: High purity ethylenediaminetetra(methylenephosphonic acid) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetra(methylenephosphonic acid) are prepared by dissolving the aminomethylenephosphonic acid in an aqueous base, acidifying with a mineral acid at an elevated temperature to precipitate the crystals, maintaining the solution at an elevated temperature for a period of time sufficient to assure crystallization, cooling to a lower temperature and maintaining at that temperature for a time sufficient to precipitate the crystals and filtering the resulting crystals at that temperature, washing the crystals with water and recovering the desired high purity aminophosphonic acid. The ethylenediaminetetra(methylenephosphonic acid) is obtained in a purer state during its synthesis if the crystals are filtered hot without prior cooling.Type: GrantFiled: August 4, 1989Date of Patent: June 26, 1990Assignee: The Dow Chemical CompanyInventors: Joseph R. Garlich, Jaime Simon, Tipton T. Masterson
-
Patent number: 4923985Abstract: A process for synthesizing a 12 membered ring tetraaza macromolecule comprising. The process involves condensing an amide of ethylene diamine having a general formula A: ##STR1## wherein n is an integer from 1 to 5 and w is a member selected from the group consisting of --NO.sub.2, --NH.sub.2, --NCS, --COOH, --OCH.sub.2 OOCH.sub.3, --NCOCH.sub.2 --Z with Z being a member selected from the group consisting of Br and I with a nitrogen blocked active ester of a general formula B: ##STR2## wherein PG is an amino protecting group and E is a leaving group.Type: GrantFiled: May 25, 1988Date of Patent: May 8, 1990Assignee: The United States of America as represented by the Department of Health & Human ServicesInventors: Otto A. Gansow, Krishan Kumar
-
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
-
Patent number: 4882323Abstract: Disclosed herein are novel 1,4-substituted-2,3,5,6-tetrahydro[1,3,6]triazocino[1,2-a]benzimidazole of Formulas I and II: ##STR1## wherein R.sup.1 may be phenyl, m- or p-nitrophenyl, m- or p-methylsulfonylaminophenyl, naphthyl, naphthyl mono-substituted by nitro or methylsulfonylamino, benzofurazanyl, 2-pyrimidinyl, 2- or 4-pyridinyl, 2- or 4-naphthyridinyl, pyrazinyl, isoquinolinyl, or quinolinyl;R.sup.2 may be hydrogen; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.4 alkylphenyl or C.sub.1 -C.sub.4 alkyl-substituted-phenyl, in which phenyl may have one to three substituents selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine or bromine; phenyl or substituted-phenyl in which the phenyl substituents are the same as for c.sub.1 -C.sub.4 alkyl-substituted-phenyl; 2- or 4-pyrimidinyl; pyrazinyl; imidazolyl; C.sub.1 -C.sub.4 alkanoyl; halo or dihalo-(C.sub.1 -C.sub.4)alkanoyl, in which halo is fluoro or chloro; benzoyl or benzoyl substituted on the phenyl ring by one or two C.sub.1 -C.sub.Type: GrantFiled: February 23, 1988Date of Patent: November 21, 1989Assignee: American Home ProductsInventors: Michael W. Winkley, James L. Diebold
-
Patent number: 4880923Abstract: There are disclosed macrocyclic and polycyclic polyamine lubricating oil additives formed by cyclodehydration of reaction products of hydrocarbon substituted succinic anhydrides or carboxylic acids with poly 3-amino propyl compounds or by acylation of macrocyclic polyamines and polycyclic polyamines with hydrocarbon substituted succinic anhydride or carboxylic acids. These compounds are useful as dispersants and dispersants-V.I. improvers in both gasoline and diesel engine lubricating oil compositions and are also useful fuel additives.Type: GrantFiled: September 2, 1986Date of Patent: November 14, 1989Assignee: Exxon Research & Engineering CompanyInventors: Stanley J. Brois, Antonio Gutierrez
-
Patent number: 4851524Abstract: Thio-bis-(hydrocarbyl substituted diacid materials), such as thio-bis-(polyalkyl lactone acid) and/or their precursors, the adducts of sulfur chloride and unsaturated diacid materials, e.g., 4,8-bis-polyalkyl-4, 8-dichloro-6-thiaundecane-1,2,10,11-tetracarboxylic acid bis-anhydride and especially their dehydrochlorinated analogs, when treated with an amine preferably polyalkylene polyamines such as tetraethylene pentamine, directly or in the presence of a metal template reagent, yield aminated thio-bis-(alkyl lactone acid) and thio-bis-(hydrocarbyl diacid) materials or their metal complexes which can be characterized in part, as macrocyclic and/or macrocyclic-like amide and/or imide structures, are useful as stable additives in lubricating compositions, e.g., as varnish inhibiting dispersants and/or inhibitors for lubricating oils and fuels.Type: GrantFiled: November 27, 1985Date of Patent: July 25, 1989Assignee: Exxon Research and Engineering CompanyInventors: Stanley J. Brois, Antonio Gutierrez
-
Patent number: 4843159Abstract: A compound of formula (I) ##STR1## in which R.sub.1 and R.sub.2 are e.g. hydrogen or methyl, R.sub.3 is e.g. a group ##STR2## or a group R.sub.5 X-- with R.sub.5 being e.g. hydrogen, C.sub.1 -C.sub.18 -alkyl or C.sub.3 -C.sub.18 -alkenyl and X being e.g. --O--, --S-- or ##STR3## and R.sub.6 is as defined for R.sub.5, or R.sub.3 represents a 5-membered to 7-membered nitrogen containing heterocyclic group with the free valency on the nitrogen, n is an integer from 2 to 6, and R.sub.4 is a nitrogen containing organic radical of a valency equal to n.The compounds of formula (I) are particularly effective in stabilizing organic material against oxidative, thermal and/or light induced degradation.Type: GrantFiled: June 8, 1987Date of Patent: June 27, 1989Assignee: Ciba-Geigy CorporationInventors: Giuseppe Cantatore, Valerio Borzatta
-
Patent number: 4775406Abstract: The salts of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring, of the general formula (I) ##STR1## exhibit a good plant growth-regulating activity. In the general formula the symbols have the following meaning:Y is an ammonium ion substituted up to fourfold by (substituted) alkyl, (substituted) alkenyl, alkynyl, (substituted) cycloalkyl, cycloalkenyl, and (substituted) phenyl, wherein the charged N may be part of a heterocyclic radial (NH.sub.4.sup.+ is excepted); phosphonium ion substituted fourfold by alkyl, (substituted) phenyl or (substituted) benzyl; sulfonium- or sulfoxonium ion substituted threefold by alkyl, (substituted) phenyl or (substituted) benzyl; the guanidinium ion or an O-alkylisourea cation;R.sup.1, R.sup.2 independently of each other are alkyl;R.sup.3 is alkyl, alkoxy or halogen; andn is 0, 1, 2 or 3.Type: GrantFiled: November 21, 1985Date of Patent: October 4, 1988Assignee: Hoechst AktiengesellschaftInventors: Roland Schmierer, Ernst-Friedrich Schulze, Helmut Bustell, Erwin Hacker
-
Patent number: 4760179Abstract: Substituted aminoxy propionamide derivatives corrsponding to the formula ##STR1## said derivatives being useful as color improvers and stabilizers in various polymeric substrates.Type: GrantFiled: April 4, 1986Date of Patent: July 26, 1988Assignee: Ciba-Geigy CorporationInventor: Ramanathan Ravichandran
-
Patent number: 4702998Abstract: There are disclosed a processing solution having bleaching ability for use in light-sensitive silver halide photographic material, which comprises at least one selected from metal complexes of large cyclic polyamine derivatives and a method for processing of light-sensitive silver halide photographic material, which comprises carrying out development processing of an exposed light-sensitive silver halide photographic material and then processing the developed material with the processing solution.The processing solution of the present invention has potent bleaching power, and can afford excellent photographic image characteristics by processing therewith.Type: GrantFiled: March 24, 1986Date of Patent: October 27, 1987Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: M. Tanaka, Kazuhiro Kobayashi, Shigeharu Koboshi