Phenanthrolines (including Hydrogenated) Patents (Class 546/88)
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Patent number: 6031098Abstract: Duplex polynucleotides containing damage or errors are detected with hindered intercalating compounds which are capable of intercalating only in the presence of such damage or error. Conditions characterized by the presence of polynucleotide errors or damage are treated with such compounds that are capable of catalyzing polynucleotide cleavage with light. Suitable compound include compounds of the formula:Rh(R.sub.1)(R.sub.2)(R.sub.3).sup.3+where R.sub.1 and R.sub.2 are each independently aryl, heteroaryl, substituted aryl or substituted heteroaryl of 1 to 5 rings, and R.sub.3 is a group of the formula ##STR1## where x and z are each independently an integer from 1 to 4 and y is an integer from 1 to 2, and R.sub.4, R.sub.5, and R.sub.6 are each independently H--, halo, HO--, H.sub.2 N--, CN--, O.sub.2 N--, HS--, O.sub.3 S--, O.sub.3 SO--, --COOH, --CONH.sub.2, R, RO--, RNH--, R.sub.a R.sub.b N--, RO.sub.3 S--, RO.sub.3 SO--, --COOR, --CONHR, or --CONR.sub.a R.sub.b, where R, R.sub.a and R.sub.Type: GrantFiled: August 11, 1998Date of Patent: February 29, 2000Assignee: California Institute of TechnologyInventors: Jacqueline K. Barton, Brian A. Jackson, Brian P. Hudson
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Patent number: 5916898Abstract: The present invention provides a phenanthroline derivative of formula (I) ##STR1## wherein, for example, R.sup.1 is hydrogen, carboxy, cyano, nitro, (1-4C)alkyl, (1-6C)alkoxycarbonyl, (1-4C)alkylamino, (2-4C)alkanoyl, (1-4C)alkoxy-(2-4C)alkoxy-(2-4C)alkoxycarbonyl or N-?amino-(2-8C)alkyl!carbamoyl;R.sup.2 is, for example, hydrogen, carboxy, (1-6C)alkoxycarbonyl, carbamoyl, N-(1-8C)alkylcarbamoyl, N,N-di-(1-8C)alkylcarbamoyl, N-(1-4C)alkylcyclohexylcarbamoyl, 1,2,3,4-tetrahydro-isoquinolin-2-ylcarbonyl or N,N-?di-(1-4C)alkyl!thiocarbamoyl;R.sup.3 and R.sup.4, which may be the same or different, are, for example, hydrogen or halo; andR.sup.5 is, for example, hydrogen, di-(1-4C)alkylamino or halo; or a pharmaceutically-acceptable salt thereof.The invention further provides pharmaceutical compositions comprising phenanthroline derivatives, processes for making the same and their use in producing an anti-fibroproliferative effect.Type: GrantFiled: October 24, 1997Date of Patent: June 29, 1999Assignee: Zeneca LimitedInventors: Philip Neil Edwards, Michael Stewart Large, Neil James Hales
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Patent number: 5866587Abstract: Compound of formula (I): ##STR1## in which: m, n, which are identical or different, represent 0, 1 or 2,R.sub.1, R.sub.2, which are identical or different, represent hydrogen, optionally substituted alkyl, aryl, or form with the carbon atom carrying them carbonyl or (C.sub.3 -C.sub.7)cycloalkyl,R.sub.3 represents hydrogen, alkyl, hydroxyl or aryl,R.sub.4 represents any of the groups as defined in the description,X represents --SO.sub.2 --, --CO-- or --SO.sub.2 NH--,R.sub.5 represents optionally substituted alkyl, (C.sub.3 -C.sub.7)cycloalkyl, aryl or heterocyclic,A represents an aryl ring or a heterocycle,its isomers as well as its addition salts with a pharmaceutically acceptable acid or base and medicinal products containing the same are useful as metalloprotease inhibitors.Type: GrantFiled: April 25, 1997Date of Patent: February 2, 1999Assignee: Adir Et CompagnieInventors: Guillaume de Nanteuil, Joseph Paladino, Georges Remond, Ghanem Atassi, Alain Pierre, Gordon Tucker, Jacqueline Bonnet, Massimo Sabatini
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Patent number: 5858650Abstract: This invention relates to methods, reagents, and kits utilizing metal chelates to inactivate nucleotide sequences, especially to inactivate polymerase chain reaction (PCR) and ligase chain reaction (LCR) products and to inactivate nucleotide sequences in a bioprocess and bioproduct. A novel metal chelate class is also disclosed.Type: GrantFiled: April 3, 1992Date of Patent: January 12, 1999Assignee: Abbott LaboratoriesInventor: Joseph E. Celebuski
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Patent number: 5856334Abstract: Specified imidazoquinoline derivatives represented by the formula (I): ##STR1## where Q represents an optionally substituted phenyl, pyridyl or furyl group; Y represents either a hydrogen atom or, when taken together with Z, an oxygen atom and a methylene group; Z represents a hydrogen atom, a hydroxymethyl group, a carboxymethyl group, a 2-oxo-1-pyrrolidinyl group or the following formula (III):--A--R.sup.2 (III)(where A represents an oxygen atom, a sulfur atom or the group --NH--);or salts of such derivatives inhibit the increase of eosinophils and are useful as agents for preventing and/or treating diseases that manifest the increase of eosinophils.Type: GrantFiled: January 28, 1997Date of Patent: January 5, 1999Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Hidenori Mochizuki, Kazuo Kato, Ichiro Yamamoto, Kiyoshi Mizuguchi
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Patent number: 5648362Abstract: Fluoroalkylated amphiphilic ligands are derived from aromatic amines of the bipyridine (I) or phenanthroline (II) types, and form complexes with platinum, palladium and ruthenium. ##STR1## In formulae (I) and (II), R.sup.1 and R.sup.2 are independently a hydrogen atom, or a fluoroalkylated or hydrocarbon chain, provided at least one of R.sup.1 and R.sup.2 is a fluoroalkylated chain, and W represents a methylene, ester, ether, carbonyl or amide group.Fluoroalkylated ligands (I or II) and their complexes can be included in preparations comprising emulsions, dispersions, gels, or microemulsions, particularly in preparations for therapeutic use.Type: GrantFiled: January 25, 1995Date of Patent: July 15, 1997Assignee: Alliance Pharmaceutical Corp.Inventors: Jean G. Riess, Pierre Vierling, Nathalie Garelli
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Patent number: 5646284Abstract: A complex crystal is composed of anion of triiodine and cation of a fused compound consisting essentially of at least one nitrogen atom and at least 3 aromatic fused rings. Since the complex crystal has such a stable structure, it shows excellent heat resistance and excellent moisture resisting property. Furthermore, the complex crystal has light-polarizing performance because of an arrangement of the molecular chain of iodine. Moreover, the complex crystal exhibits excellent polarization because of an interaction between the fused compound and iodine. Therefore, the complex crystal is suitable for use as light-adjusting particles of a light valve or a light-adjusting glass.Type: GrantFiled: August 3, 1995Date of Patent: July 8, 1997Assignees: Toyota Jidosha Kabushiki Kaisha, Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Arimitsu Usuki, Hisato Takeuchi, Narihito Tatsuda, Akane Okada, Toshio Kurauchi, Hiromitsu Tanaka, Shinobu Okayama, Kazuo Tojima, Akio Fukui, Toshiro Okamoto
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Patent number: 5602142Abstract: Hypoxia selective cytotoxins having the structural formula ##STR1## wherein D, E, F and G, independently, are carbon or nitrogen, with the proviso that three or more of D, E, F and G are carbon; R.sub.1 and R.sub.2, independently, are selected from the group consisting of methyl, halo, hydro, trifluoromethyl, methoxy, cyano, and methylsulfo; R.sub.3 and R.sub.4, independently, are selected from the group consisting of methyl, ethyl, phenyl, naphthyl, tertiary butyl, halo, halomethylene, hydro, trifluoromethyl, cyano and methylsulfo, or R.sub.3 and R.sub.4 taken together are a substituted or unsubstituted five or six-membered nonaromatic ring system; n is an integer 1 through 5; X is carbon or nitrogen; and Z is a physiologically acceptable anion, are disclosed. The compounds are useful as radiosensitizers or chemosensitizers, especially in the treatment of cancer patients.Type: GrantFiled: December 21, 1994Date of Patent: February 11, 1997Assignee: Evanston Hospital CorporationInventors: Maria V. Papadopoulou-Rosenzweig, William D. Bloomer
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Patent number: 5576326Abstract: Copper amino acidate diimine nitrate compounds of the formula [Cu(N--N)(N--O)].sup.+NO.sub.3.sup.-, where (N--N) is a diimine selected from 1,10-phenanthroline or 4,7-dimethyl 1,10-phenanthroline and (N--O) is tyrosine-alaninate, threoninate, tryptophanate, valinate, isoleucinate, cysteinate, diglycinate, phenylalaninate, glycinate, histidinate, serinate, tryosinate, aspartate or alaninate and a process for preparing the compounds in which, while maintaining a pH between 5 and 7, a first aqueous solution of Cu(NO.sub.3).sub.2.5H.sub.2 O, having 30 to 35% by weight of elemental copper, is reacted with a second aqueous solution of the diimine having a ratio of 50 to 55% by weight diimine to solution to form a monodiimine nitrate as an intermediate reaction product having the formula [Cu(N--N)(H.sub.2 O).sub.2 ].sup.+ NO.sub.3.sup.Type: GrantFiled: September 8, 1994Date of Patent: November 19, 1996Assignee: Universidad Nacional Autonoma de Mexico (UNAM)Inventor: Lena R. Azuara
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Patent number: 5567710Abstract: In accordance with the present invention, there is provided a class of polycyclic fused ring compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors.Type: GrantFiled: October 13, 1994Date of Patent: October 22, 1996Assignee: SIBIA Neurosciences, Inc.Inventors: Jeffrey P. Whitten, Ian A. McDonald, Jean-Michel Vernier
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Patent number: 5556949Abstract: A class of site-specific DNA cleavage agents comprising a sequence-specific DNA binding protein and a nucleolytic moiety attached thereto at an amino acid that is close to DNA in the specific protein-DNA complex, but that is not close to DNA in the non-specific protein DNA complex. These site-specific DNA cleavage agents cleave DNA at specific DNA recognition sites and have little or no non-specific DNA cleavage activity.Type: GrantFiled: October 11, 1994Date of Patent: September 17, 1996Assignee: Rutgers UniversityInventors: Richard H. Ebright, Y. W. Ebright, P. Shannon Pendergrast
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Patent number: 5439794Abstract: This invention concerns a coordination complex or salt thereof which is spectroscopically or photoactively determinable when bound to DNA having the formula ##STR1## wherein M is a suitable transition metal and each of R.sub.1, R.sub.2 and R.sub.3 is ethylenediamine or a substituted derivative thereof, bipyridine or a substituted derivative thereof, phenanthroline or a substituted derivative thereof, diazfluorene-9-one or a substituted derivative thereof, phenanthrenequinonediimine or a substituted derivative thereof; wherein R.sub.1, R.sub.2 and R.sub.3 are bound to M by coordination bonds wherein R.sub.1 and R.sub.2 are the same and both are different from R.sub.3. The invention also concerns a method of labeling DNA with the coordination complex, a DNA molecule labeled with the coordination complex, a method of selectively labeling DNA conformation with the coordination complex and a method of detecting the presence of a conformation present in a double stranded DNA.Type: GrantFiled: February 28, 1992Date of Patent: August 8, 1995Assignee: The Trustees of Columbia University in the City of New YorkInventor: Jacqueline K. Barton
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Patent number: 5420136Abstract: A class of predominantly hydrophobic non-azo N-substituted 1,8-naphthalimide compounds, each bearing, at its 3-position, a nucleofuge and, at its 4-position, a heteroatomic electron-releasing group. The heteroatomic electron-releasing group is being characterized as having a heteroatom directly linked to the 4-position of the ring, and having at least one hydrogen directly attached to the heteroatom. Upon activation by an activating agent in an environment independent of the presence or absence of oxygen, these compounds generate activated species. The activated species initiate chemical changes in lipid bilayer membranes of viruses and other target cells. These changes can eradicate viruses and other target cells. The activated species can also cause structural changes in lipid and any associated proteins and polypeptides at a level beneath the surface of the membrane, leading to polymerization and crosslinking.Type: GrantFiled: August 9, 1993Date of Patent: May 30, 1995Assignee: MicroBioMed CorporationInventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
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Patent number: 5401856Abstract: A cyclocarbonylation process for making pyrrolidones under mild temperature and pressure conditions is disclosed. In the process, an allylic amine reacts with carbon monoxide in the presence of a rhodium carbonyl catalyst and an amount of a pyridine promoter effective to enhance the yield of pyrrolidone obtained in the process compared with the yield obtained in the absence of the promoter. The process can be used to make N-methyl-2-pyrrolidone from N-methylallylamine.Type: GrantFiled: February 28, 1994Date of Patent: March 28, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Roger A. Grey, Diandre Armstead
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Patent number: 5235045Abstract: A class of predominantly hydrophobic non-azo N-substituted 1,8-naphthalimide compounds, each bearing, at its 3-position, a nucleofuge and, at its 4-position, a heteroatomic electron-releasing group. The heteroatomic electron-releasing group is being characterized as having a heteroatom directly linked to the 4-position of the ring, and having at least one hydrogen directly attached to the heteroatom. Upon activation by an activating agent in an environment independent of the presence or absence of oxygen, these compounds generate activated species. The activated species initiate chemical changes in lipid bilayer membranes of viruses and other target cells. These changes can eradicate viruses and other target cells. The activated species can also cause structural changes in lipid and any associated proteins and polypeptides at a level beneath the surface of the membrane, leading to polymerization and crosslinking.Type: GrantFiled: March 19, 1992Date of Patent: August 10, 1993Assignee: MicroBioMed CorporationInventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
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Patent number: 5225556Abstract: This invention concerns a coordination complex and salts and optically resolved enantiomers thereof, of the formula (R).sub.3 --M, wherein R comprises 1,10-phenanthroline or a substituted derivative thereof, M comprises a suitable transition metal, e.g. ruthenium(II), RHODIUM(III) or cobalt(III), and R is bonded to M by a coordination bond.The complexes of this invention are useful in methods for labeling, nicking and cleaving DNA. The lambda enantiomer of complexes of this invention is useful in methods for specifically labeling, detecting, nicking and cleaving Z-DNA or A-DNA.The complexes may also be used in a method for killing tumor cells and may be combined with a pharmaceutically acceptable carrier to form a pharmaceutical composition for the treatment of tumor cells in a subject. The invention further concerns methods for treating a subject affilicted with tumor cells.Type: GrantFiled: August 10, 1992Date of Patent: July 6, 1993Assignee: The Trustees of Columbia University In The City of New YorkInventor: Jacqueline K. Barton
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Patent number: 5157032Abstract: This invention concerns a coordination complex or salt thereof which is spectroscopically or photoactively determinable when bound to DNA having the formula ##STR1## wherein M is a suitable transition metal and each of R.sub.1, R.sub.2 and R.sub.3 is ethylenediamine, bipyridine, phenanthroline, diazafluorene-9-one or a substituted derivative thereof, or phenanthrenequinonediimine or a substituted derivative thereof, dypyridophenazine or a substituted derivative thereof; wherein R.sub.1, R.sub.2 and R.sub.3 are bound to M by coordination bonds; provided that at least one of R1, R2 or R3 is dypyridophenazine or a substituted derivative thereof. The invention also concerns a labeled DNA probe which comprises the complex covalently bound to the DNA probe.Type: GrantFiled: June 18, 1990Date of Patent: October 20, 1992Assignee: The Trustees of Columbia University In The City of New YorkInventor: Jacqueline K. Barton
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Patent number: 5118688Abstract: The present invention comprises certain quinoline lactams of formula I; pharmaceutically acceptable salts of the compounds of formula I; pharmaceutical compositions containing a compound of formula I, or a pharmaceutically acceptable salt thereof, for use in the treatment of anxiety; and processes for the manufacture of the compounds of formula I, as well as intermediates for use in such manufacture.Type: GrantFiled: September 14, 1990Date of Patent: June 2, 1992Assignee: ICI Americas Inc.Inventor: James B. Campbell
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Patent number: 5112974Abstract: This invention concerns a coordination complex or salt thereof which is spectroscopically or photoactively determinable when bound to DNA having the formula ##STR1## wherein M is a suitable transition metal and each of R.sub.1, R.sub.2 and R.sub.3 is ethylenediamine, bipyridine, phenanthroline, diazafluorene-9-one or phenanthrenequinonediimine. In the complex, R.sub.1, R.sub.2 and R.sub.3 are bound to M by coordination bonds and R.sub.1 and R.sub.2 may be the same or different and both are different from R.sub.3. In the preferred embodiments, the invention concerns complexes of ruthenium(Ru) or rhodium(Rh) wherein R.sub.1 and R.sub.2 are the same. The invention also concerns the complex ##STR2## wherein M is Ru or Rh and R is 9-10-phenanthrenequinonediimine or 5-nitrophenanthroline.Type: GrantFiled: November 7, 1988Date of Patent: May 12, 1992Assignee: The Trustees of Columbia University in the City of New YorkInventor: Jacqueline K. Barton
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Patent number: 5107005Abstract: This invention refers to a process to obtain new mixed copper aminoacidates complexes from phenanthrolines of an aromatic type to be used as anticancerigenic agents preferably with a therapeutic use for the treatment of liquid and solid cancerigenic tumors such as leukemia. The complexes obtained are of the [Cu (N-N) (N-O)].+-. NO.sub.3 type in which the N-N ligand corresponds to 4, 7 - diphenyl-1, 10 phenanthroline and the N-O ligand preferably corresponds to one of the aminoacidates such as glycinate, alaninate, isoleucinate, leucinate, serinate and valinate. The process is characterized because it includes the following steps: making an aqueous solution based on an aliphatic alcohol and 4, 7 - diphenyl - 1, 10 phenanthroline react with a copper complex preferably Cu NO.sub.3 5H.sub.2 O at room temperature, and immediately after making the obtained product react in an aqueous aminoacidate solution adjusting a slightly alkaline pH.Type: GrantFiled: December 11, 1990Date of Patent: April 21, 1992Assignee: Universidad Nacional Autonoma de Mexico (UNAM)Inventor: Lena R. Azuara
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Regiospecific carbonylation process for making acyl compounds from aromatic heterocycles and olefins
Patent number: 5081250Abstract: A regiospecific, catalyzed process for preparing acyl derivatives of aromatic nitrogen-containing heterocyclic compounds in which the keto group is selectively added ortho to the nitrogen atom on the aromatic ring. In the presence of a ruthenium carbonyl compound, carbon monoxide and an olefin, the aromatic heterocyclic compound which has an unsubstituted carbon atom ortho to at least one of the heterocyclic atoms adds the acyl group essentially completely in ortho position.Type: GrantFiled: August 15, 1989Date of Patent: January 14, 1992Assignee: Amoco CorporationInventors: Eric J. Moore, Wayne R. Pretzer -
Patent number: 5051508Abstract: 1,4-Substituted 2,3-dihydropyrrolo[3,2-c]quinolines which are inhibitors of H.sup.+ K.sup.+ ATPase activity and useful as inhibitors of gastric acid secretion. A compound of the invention is 1-(2-methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline.Type: GrantFiled: June 19, 1990Date of Patent: September 24, 1991Assignee: SmithKline Beckman Intercredit B.V.Inventors: Thomas H. Brown, Robert J. Ife, Colin A. Leach
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Patent number: 5049672Abstract: The invention is a complex-forming polymer comprising at least one aryl group having a 2,2'-bipyridine complex-forming moiety or a 1,10-phenanthroline complex-forming moiety. The complex-forming polymers are prepared by contacting a substituted 2,2'-bipyridine or a substituted 1,10-phenanthroline compound with a metalating agent, and then reacting the metalated compound with an halomethylated polystyrene polymer, or alternatively, reacting the metalated compound with at least one vinylbenzyl halide and subsequently polymerizing the reaction product. The complex-forming polymers are hydrolytically stable and may be used as polymeric ligands as such or complexed with selected metal compounds.Type: GrantFiled: October 23, 1989Date of Patent: September 17, 1991Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4952707Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.Type: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
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Patent number: 4933455Abstract: The invention relates to nitrogen-containing bidentate compound immobilized on a solid carrier having the formula ##STR1## wherein the symbols have specified meanings intermediate thereto and to processes for the preparation.Type: GrantFiled: March 27, 1989Date of Patent: June 12, 1990Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4882346Abstract: Several analogues of hexamethylene bis[acetamide] were found to be effective differentiating agents. The most effective of these compounds was 3,3'-(1,6-hexandiyl)bis[5,5-dimethyl-2,4-imidazolinedione].Type: GrantFiled: June 16, 1987Date of Patent: November 21, 1989Assignee: The United States of America as reprsented by the Department of Health and Human ServicesInventors: John S. Driscoll, Alberto Haces, Theodore Breitman
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Patent number: 4873212Abstract: The invention relates to nitrogen-containing bidentate compound immobilized on a solid carrier having the formula ##STR1## wherein the symbols have specified meanings intermediate thereto and to processes for the preparation.Type: GrantFiled: March 7, 1988Date of Patent: October 10, 1989Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4873333Abstract: The invention relates to nitrogen-containing bidentate compound immobilized on a solid carrier having the formula ##STR1## wherein the symbols have specified meanings intermediate thereto and to processes for the preparation.Type: GrantFiled: March 27, 1989Date of Patent: October 10, 1989Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4853090Abstract: An analytical composition, electrode and method are useful for the detection of lithium ions in an aqueous liquid. The lithium ion-selective composition comprises a lipophilic group-substituted 1,10-phenanthroline, a compound capable of solvating the phenanthroline, and a supporting matrix. This composition can be used in a lithium ion-selective electrode as a lithium ion-selective membrane. The electrode can also comprise an internal reference electrode.Type: GrantFiled: April 28, 1988Date of Patent: August 1, 1989Assignee: Eastman Kodak CompanyInventors: Daniel S. Daniel, Mary H. Delton, Harold C. Warren, III
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Patent number: 4814457Abstract: The invention is a complex-forming polymer comprising at least one aryl group having a 2,2'-bipyridine complex-forming moiety or a 1,10-phenanthroline complex-forming moiety. The complex-forming polymers are prepared by contacting a substituted 2,2'-bipyridine or a substituted 1,10-phenanthroline compound with a metalating agent, and then reacting the metalated compound with an halomethylated polystyrene polymer, or alternatively, reacting the metalated compound with at least one vinylbenzyl halide and subsequently polymerizing the reaction product. The complex-forming polymers are hydrolytically stable and may be used as polymeric ligands as such or complexed with selected metal compounds.Type: GrantFiled: December 23, 1986Date of Patent: March 21, 1989Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4810708Abstract: Novel polycyclic quinoline, naphthyridine and pyrazinopyridine derivatives are disclosed which are useful for treating allergic reactions, inflammation, peptic ulcers, hypertension, and hyperproliferative skin diseases and for suppressing the immune response in mammals. Methods for preparing said compounds are also disclosed.Type: GrantFiled: February 17, 1987Date of Patent: March 7, 1989Assignee: Schering CorporationInventors: Ashit K. Ganguly, Richard J. Friary, John H. Schwerdt, Marvin I. Siegel, Sidney R. Smith, Vera A. Seidl, Edmund J. Sybertz
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Patent number: 4801722Abstract: There are described stable fluorescent labels comprising a complex of lanthanide metal and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of said lanthanide metal and at least two heteroatom-containing groups which form coordinate complexes with lanthanide metals and a third heteroatom-containing group or heteratom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, heptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.Type: GrantFiled: January 27, 1987Date of Patent: January 31, 1989Assignee: Eastman Kodak CompanyInventors: Jerald C. Hinshaw, John L. Toner, George A. Reynolds
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Patent number: 4772563Abstract: 1,10-phenanthroline-2,9-dicarboxylic acid and novel derivatives thereof such as 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid and 4,5,9,14-tetraaza-(1,2,3,4)-dibenzanthracene-3,5-dicarboxylic acid can be coupled to proteins through coupling groups to form conjugates which form higly fluorescent chelates in the presence of lanthanide salts. Derivatives of the above acids reactive toward proteins can be readily manufactured by relatively simple synthetic routes, and are useful in fluorescent immunoassay.Type: GrantFiled: August 8, 1985Date of Patent: September 20, 1988Assignee: HSC Research Development CorporationInventors: Ramon A. Evangelista, Alfred Pollak
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Patent number: 4721669Abstract: This invention concerns a coordination complex and salts and optically resolved enantiomers thereof, of the formula (R).sub.3 --M, wherein R comprises 1,10-phenanthroline or a substituted derivative thereof, M comprises a suitable transition metal, e.g. ruthenium(II) or cobalt(III), and R is bonded by M by a coordination bond.The complexes of this invention are useful in methods for labeling, nicking and cleaving DNA. The lambda enantiomer of complexes of this invention is useful in methods for specifically labeling, detecting, nicking and cleaving Z-DNA.The complexes may also be used in a method for killing tumor cells and may be combined with a pharmaceutically acceptable carrier to form a pharmaceutical composition for the treatment of tumor cells in a subject. The invention further concerns methods for treating a subject afflicted with tumor cells.Type: GrantFiled: January 18, 1985Date of Patent: January 26, 1988Assignee: The Trustees of Columbia University in the City of New YorkInventor: Jacqueline K. Barton
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Patent number: 4719302Abstract: There are disclosed compounds having the formula ##STR1## wherein R is hydrogen or lower alkyl;R.sup.1 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, phenyl or any of the foregoing substituted with halo;R.sup.2 is hydrogen, carboxy or lower alkoxy carbonyl; andR.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or any of the foregoing substituted with carboxy, methoxycarbonyl, hydroxy, amino, dilower alkyl amino, cyano, nitro or lower alkoxy;and their use as antifungal agents.Type: GrantFiled: March 13, 1987Date of Patent: January 12, 1988Assignee: American Home Products CorporationInventors: Jerauld S. Skotnicki, Donald P. Strike, Bruce A. Steinbaugh
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Patent number: 4699978Abstract: This invention concerns a coordination complex of the formula (R).sub.2 --M--(Y).sub.2 wherein M comprises a suitable transition metal, e.g. cobalt or ruthenium, R comprises 1,10-phenanthroline or a substituted derivative thereof, Y comprises a labile ligand, e.g. chloride, tartrate, malonate or ascorbate ion and R and Y are bonded to M by coordination bonds.A complex of this invention may be used for covalently labeling DNA with a complex of the formula (R).sub.2 --M, wherein R and M are as previously defined. A complex of this invention which contains cobalt may also be used in a method for nicking DNA by effecting single-stranded scission of at least one phosphodiester bond of the DNA with ultraviolet radiation.A complex of this invention is further useful in a method for killing tumor cells. A pharmaceutical composition for the treatment of tumor cells in a subject may be prepared containing an effective anti-tumor amount of a complex of this invention and a pharmaceutically acceptable carrier.Type: GrantFiled: January 18, 1985Date of Patent: October 13, 1987Assignee: The Trustees of Columbia University in the City of New YorkInventor: Jacqueline K. Barton
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Patent number: 4535162Abstract: A process is herein described for catalytically reducing nitroaromatic compounds by displacement of hydrogen from carbon monoxide and water or from synthesis gas to nitroaromatic compounds, the catalytic reduction being catalyzed by complexes of rhodium, iridium, ruthenium and osmium; said process is characterized in that the CO+H.sub.2 O system or the (CO+H.sub.2)+H.sub.2 O system is caused to react with a nitroaromatic compound of formula:Ar--(NO.sub.2).sub.x (I)wherein Ar is an aryl or hetero-aryl group, also substituted by inert groups; x is an integer from 1 to 3, in the presence of a complex catalyst of formula:[MChel(L).sub.2 ].sup.+ X.sup.- (II)or of a catalyst composed by carbonyl compounds and chelants of formula:Mz(CO).sub.y +nChel (III)wherein M=Rh, Ir, Ru, Os; "Chel" is a bidentate or tridentate aromatic nitrogen chelating compound; "L" is a molecule of carbon monoxide or of an olefin or half a molecule of a diolefin; X.sup.- is an anion selected from Cl.sup.-, Br.sup.-, I.sup.-, PF.sub.6.sup.Type: GrantFiled: June 16, 1983Date of Patent: August 13, 1985Assignee: Montedison S.p.A.Inventors: Giovanni Mestroni, Grazia Zassinovich, Enzo Alessio
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Patent number: 4511569Abstract: Disclosed are 5,6-dihydro benzo[f]quinolines and derivatives which are effective in increasing cardiac contractility. These compounds are useful in the treatment of congestive heart failure.Type: GrantFiled: August 26, 1982Date of Patent: April 16, 1985Assignee: Schering CorporationInventors: Elizabeth M. Smith, Ronald J. Doll, Bernard R. Neustadt
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Patent number: 4478834Abstract: New dihydropyridines are described. These compounds are useful in the treatment of asthma.Type: GrantFiled: February 11, 1983Date of Patent: October 23, 1984Assignee: USV Pharmaceutical CorporationInventors: James R. Shroff, Bernard Loev
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Patent number: 4474978Abstract: Process for the preparation of carbamates and/or derivatives thereof by reacting an organic compound containing at least one hydroxyl group with carbon monoxide and an organic nitrogeneous compound in the presence of a catalytic system based on palladium and a ligand according to the general formula: ##STR1## wherein L=N, P, As or Sb; R, R.sup.1, R.sup.2 and R.sup.3 are (un)substituted alkyl, aryl, alkaryl or aralkyl or R and R.sup.1 and/or R.sup.2 and R.sup.3 may form a ring together with the atom L to which they are attached; R.sup.4 and R.sup.5 are H or lower alkyl and n=2, 3 or 4, whereas carbon atoms between the groups L may be part of cyclic or non-cyclic unsaturated structures, and in the presence of an acid promoter.Type: GrantFiled: October 17, 1983Date of Patent: October 2, 1984Assignee: Shell Oil CompanyInventors: Eit Drent, Petrus W. N. M. Van Leeuwen
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Patent number: 4335130Abstract: A mixture of pyrido[3,4-g]isoquinoline (A) and 3,8-phenanthroline (B) in which the ratio of A:B is 37:63 is useful as an antifungal agent.Type: GrantFiled: May 12, 1981Date of Patent: June 15, 1982Assignee: Morton-Norwich Products, Inc.Inventors: Thomas J. Schwan, Joseph E. Gray
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Patent number: 4328230Abstract: There are described compounds of formula I, ##STR1## in which R.sub.5 to R.sub.8 may be a variety of substituents, or an adjacent pair of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a chain--COCH.dbd.C(COOH)NRh--,or one of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a group of formula II, ##STR2## in which Ra, Rb and Rc have the same significances as R.sub.5, R.sub.6, R.sub.7 and R.sub.8,X is an optionally interrupted or substituted hydrocarbon chain,Rg and Rh, which may be the same or different are each alkyl, alkenyl, phenyl-alkyl, alkanoyl, benzoyl or phenylalkanoyl,or Rg and R.sub.8 and/or Rh and Rc in formula II, together form a chain --(CH.sub.2).sub.n --, and n is 2, 3 or 4.There are also described processes for making the compounds and pharmaceutical, e.g. anti-allergic, compositions containing the compounds.Type: GrantFiled: March 5, 1979Date of Patent: May 4, 1982Assignee: Fisons LimitedInventors: Roger C. Brown, Hugh Cairns, Anthony R. Payne
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Patent number: 4297358Abstract: New 4,7-phenanthroline derivatives of the formula (I) ##STR1## in which Ch represents an optionally substituted 5,6-quinolinylene radical of which the 6-position is joined to the --N(R.sub.E)-- group, andR represents an optionally esterified or amidated carboxy group,and in which eitherR.sub.A and R.sub.B together represent oxo,R.sub.C and R.sub.D together represent an additional link, andR.sub.E represents a radical R.sub.1 which is hydrogen, or an aliphatic, cycloaliphatic, araliphatic or heterocyclic-aliphatic radical, orR.sub.A represents an optionally etherified hydroxy group andR.sub.B together with R.sub.C and R.sub.D together with R.sub.E in each case represents an additional link,and salts of salt-forming compounds of the formula (I), compounds of the formula (I) or the salts thereof have anti-allergic properties. They can be prepared in accordance with processes known per se and may be used as active substances in pharmaceutical preparations.Type: GrantFiled: January 4, 1980Date of Patent: October 27, 1981Assignee: Ciba-Geigy CorporationInventors: Georges Haas, Knut A. Jaeggi, Alberto Rossi, Alex Sele
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Patent number: 4220780Abstract: Cationic dyestuffs of the formula ##STR1## wherein A represents oxygen, sulphur or the groupings >N--R.sub.3, ##STR2## wherein R.sub.3 denotes an alkyl, aryl or aralkyl radical,R.sub.4 and R.sub.5 independently of one another denote an alkyl radical,R.sub.6 and R.sub.7 independently of one another denote hydrogen or an alkyl radical,R represents hydrogen or an alkyl group,R.sub.1 and R.sub.2 independently of one another represent hydrogen or an alkyl, aryl or aralkyl radical, orR.sub.1 can be bonded to R.sub.2 or to the ring b, andAn.sup.- represents an anion,and whereinthe rings a and b and the radicals R, R.sub.1, R.sub.2 and R.sub.3 can contain non-ionic substituents which are customary in dyestuff chemistry or carboxyl groups,are suitable for dyeing synthetic and natural materials, in particular paper.Type: GrantFiled: May 9, 1978Date of Patent: September 2, 1980Assignee: Bayer AktiengesellschaftInventor: Alfred Brack
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Patent number: 4125724Abstract: An improved and novel process is provided for the reduction of isocyanate groups in organic compounds to formamide groups by catalytic hydrogenation with a noble metal catalyst. The process allows preparation of formamides in consistently high yields from all types of isocyanates.Type: GrantFiled: October 6, 1977Date of Patent: November 14, 1978Assignee: Bristol-Myers CompanyInventor: Henry G. Howell
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Patent number: RE35458Abstract: This invention refers to a process to obtain new mixed copper aminoacidates complexes from phenanthrolines of an aromatic type to be used as anticancerigenic agents preferably with a therapeutic use for the treatment of liquid and solid cancerigenic tumors such as leukemia. The complexes obtained are of the [Cu (N-N) (N-O)].+-. NO.sub.3 type in which the N-N ligand corresponds to 4, 7-diphenyl-1, 10 phenanthroline and the N-O ligand preferably corresponds to one of the aminoacidates such as glycinate, alaninate, isoleucinate, leucinate, serinate and valinate. The process is characterized because it includes the following steps: making an aqueous solution based on an aliphatic alcohol and 4,7-diphenyl-1, 10 phehanthrolin react with a copper complex preferably Cu NO.sub.3 5H.sub.2 O at room temperature, and immediately after making the obtained product react in an aqueous aminoacidate solution adjusting a slightly alkaline pH.Type: GrantFiled: April 21, 1994Date of Patent: February 18, 1997Assignee: Universidad Nacional Autonoma De Mexica (UNAM)Inventor: Lena R. Azuara