Boron Containing Patents (Class 546/13)
  • Patent number: 5502065
    Abstract: The present invention provides compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: March 26, 1996
    Assignee: Pfizer Inc.
    Inventors: Alan D. Brown, Roger P. Dickinson, Martin J. Wythes
  • Patent number: 5496951
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 represents fluorinated methoxy: R.sup.2 represents a nitrogen-containing heterocyclic group and R.sup.3 represents hydrogen or amino) and pharmaceutically acceptable salts, esters and amides thereof are valuable antibacterial agents, which may be prepared by reacting a compound similar to that of formula (I) but in which R.sup.2 is replaced by a halogen atom with a compound providing the required group R.sup.2.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: March 5, 1996
    Assignees: Sankyo Company, Limited, Ube Industries Limited
    Inventors: Masayuki Iwata, Tomio Kimura, Teruhiko Inoue, Yoshimi Fujihara, Tetsushi Katsube
  • Patent number: 5495020
    Abstract: Useful as intermediates for antimicrobacterial agents are compounds of the formulas ##STR1## wherein R.sup.1A is a cyclopropyl which may be substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkyl and a halogen atom; a phenyl which may be substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkoxy, a halogen atom and hydroxy on the phenyl group; a C.sub.1 -C.sub.6 alkyl which may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkanoyloxy or hydroxy; a C.sub.2 -C.sub.6 alkenyl; or thienyl,R.sup.3A is a C.sub.1 -C.sub.6 alkyl group, or a halogen atom,R.sup.4 is a C.sub.1 -C.sub.6 alkyl group,R.sup.14 is a hydrogen atom, a lower alkyl group, or a group of the formula ##STR2## R.sup.31 is hydrogen or a C.sub.1 -C.sub.6 alkyl group, and X and X.sup.4 are halogen atoms, and salts thereof.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: February 27, 1996
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
  • Patent number: 5493046
    Abstract: The novel process of the invention for the preparation of a compound of the formula ##STR1##
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: February 20, 1996
    Assignee: Roussel-Uclaf
    Inventors: Neerja Bhatnagar, Jean Buendia, Christine Griffoul
  • Patent number: 5466798
    Abstract: The present invention relates to novel, powerful reducing agents, lithium aminoborohydrides which are prepared by addition of BH.sub.3 .cndot.THF to the corresponding dialkylamine at 25.degree. C. to give the intermediate amineborane complex. Subsequent deprotonation by strong base, e.g. n-BuLi, yields the aminoborohydride quantitatively. Lithium aminoborohydrides are powerful reducing agents, comparable in strength to lithium aluminum hydride. The activity is determined by the dialkylamine. Lithium pyrrolidinoborohydride has unique activity and selectivity in its reducing properties. Esters, lactones and anhydrides are reduced cleanly at 25.degree. C. to give the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that lithium pyrrolidinoborohydride is also capable of reducing a wide range of functional groups including amides, epoxides, oximes, nitriles and halides.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: November 14, 1995
    Assignee: The Regents of the University of California
    Inventors: Bakthan Singaram, Gary B. Fisher, Joseph C. Fuller, John Harrison, Christian T. Goralski
  • Patent number: 5451663
    Abstract: This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials to form dye-conjugates. The dye-conjugates generally have the structure: ##STR1## wherein at least one of the substituents R.sub.1 -R.sub.7, covalently bonds to a specific binding pair member, and further where at least one of the substituents R.sub.1 -R.sub.7 contains a bathochromic moiety that is heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: September 19, 1995
    Assignee: Molecular Probes, Inc.
    Inventors: Hee C. Kang, Richard P. Haugland
  • Patent number: 5446157
    Abstract: A new group of fluorescent organic compounds having a variety of uses are described. They are especially useful as dye compounds in dye laser systems, and as photochemical agents in the treatment of diseased tissues using photodynamic therapy techniques. The compounds include a tri-cyclic compound having the following structure: ##STR1## Preferably R.sub.1 -R.sub.5 .dbd.R.sub.9 -R.sub.12 .dbd.C; R.sub.7 .dbd.B; R.sub.6 and R.sub.8 .dbd.N; R.sub.14 .dbd.lower n-alkyl or an electron withdrawing group such as CN.sup.- ; R.sub.16 and R.sub.19 are independently selected from the group consisting of lower n-alkyl, a sulfate or an acid or salt thereof, or hydrogen; and R.sub.20 .dbd.R.sub.21 .dbd.F.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: August 29, 1995
    Inventors: Lee R. Morgan, Joseph H. Boyer
  • Patent number: 5420136
    Abstract: 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: Grant
    Filed: August 9, 1993
    Date of Patent: May 30, 1995
    Assignee: MicroBioMed Corporation
    Inventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
  • Patent number: 5329046
    Abstract: The invention relates to biscationic acid amide and acid imide derivatives with an anion of formula (BR.sub.9 R.sub.10 R.sub.11 R.sub.12)--, where R.sub.9 to R.sub.12 are aliphatic, iso- or heterocyclic aromatic residues or aralkyl residues, which may be substituted by C.sub.1 -C.sub.4 -alkyl residues, C.sub.1 -C.sub.4 -alkoxy residues, aryl residues or halogen atoms (e.g. fluorine atoms), and mixtures of these compounds and mixed crystals with mixed anions and/or cations. The invention also relates to a process for preparing them. The new compounds are excellent colorless charge controllers in toners and developers for electrophotographic recording and as charge-enhancers in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: July 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Tobias Macholdt, Siegfried Schiessler, Jorg Gitzel, Erwin Dietz
  • Patent number: 5290934
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: March 1, 1994
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
  • Patent number: 5286864
    Abstract: The invention relates to new quinuclidines, processes for their preparation and their use as medicaments having cholinomimetic properties.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: February 15, 1994
    Assignee: Boehringer Ingelheim KG
    Inventors: Gerhard Walther, Karl H. Weber, Werner Stransky, Franz J. Kuhn, Enzio Muller, Helmut Ensinger
  • Patent number: 5280119
    Abstract: Heterocyclic amine-borane compounds of the formula: ##STR1## wherein: A is a heterocyclic amine moiety selected from the group consisting of piperidine, substituted piperidine, piperazine, substituted piperazine, imidazole, substituted imidazole, pyrazole, substituted pyrazole, pyrazine, substituted pyrazine, pyrrole, substituted pyrrole, pyrrolidine, substituted pyrrolidine, indole, substituted indole, indoline, substituted indoline, quinoline, substituted quinoline, isoquinoline, substituted isoquinoline, thiazole, substituted thiazole, oxazole, substituted oxazole, thiazolidine, and substituted thiazolidine, wherein substitution is at any or all substituent positions, and comprises substituents selected from the group consisting of alkyl (preferably C.sub.1 -C.sub.10 linear or branched alkyl), alkylaryl, aryl, aralkyl, nitro, alkoxy, hydroxy, cyano, thiol, and halo;R.sub.1 is selected from H, alkyl (preferably C.sub.1 -C.sub.10 linear or branched alkyl), alkylaryl, aryl, and arylalkyl; andR.sub.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: January 18, 1994
    Assignee: Boron Biologicals, Inc.
    Inventors: Bernard F. Spielvogel, Anup Sood, Iris H. Hall
  • Patent number: 5274113
    Abstract: This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials. The dyes generally have the structure: ##STR1## wherein at least one of the substituents R.sub.1 -R.sub.7, is a reactive functional group, and at least one of the substituents R.sub.1 -R.sub.7 contains a bathochromic moiety. The bathochromic moiety is an unsaturated organic group, preferably heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo. The dyes are used to make novel conjugates with members of specific binding pairs that are ligands or receptors.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: December 28, 1993
    Assignee: Molecular Probes, Inc.
    Inventors: Hee C. Kang, Richard P. Haugland
  • Patent number: 5264574
    Abstract: Oxazaborolidine-borane complexes are prepared by adding a C.sub.5-8 alkane, typically hexane, to an aged solution of oxazaborolidine and a source of borane such as borane-dimethyl sulfide or gaseous diborane to crystallize the oxazaborolidine complex.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: November 23, 1993
    Assignee: Merck & Co., Inc.
    Inventors: James D. Carroll, David J. Mathre, Edward G. Corley, Andrew S. Thompson
  • Patent number: 5264585
    Abstract: The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of diborane, borane-dimethyl sulfide or borane-tetrahydrofuran reductions of ketones to secondary alcohols.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: November 23, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
  • Patent number: 5235045
    Abstract: 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: Grant
    Filed: March 19, 1992
    Date of Patent: August 10, 1993
    Assignee: MicroBioMed Corporation
    Inventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
  • Patent number: 5221761
    Abstract: A melt transesterification process for the production of polycarbonates, wherein at least one bis(aryl)carbonate is reacted with at least one dihydric phenol in the melted state, in the presence of a transesterification catalyst comprising at least one heterocyclic borate salt of the formula:M.sup.+ B(R).sub.n (A).sup.-.sub.4-n (I)where M.sup.+ is an alkali metal, tetra-alkylammonium, tetra-arylammonium, tetra-alkylphosphonium and tetra-arylphosphonium ion; R is H, alkyl, aryl or aralkyl; n is an integer from 0-3; and A is an aromatic or aliphatic heterocyclic ring.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: June 22, 1993
    Assignees: Instituto Guido Donegani, Enichem America, Inc.
    Inventors: Kwan-Yue A. Jen, Terence Moran
  • Patent number: 5212035
    Abstract: New electrostatographic toners and developers are provided containing novel charge control agents comprising ester-containing quaternary pyridinium salts having the structure: ##STR1## wherein R.sub.1 is alkyl or aryl, X is CH.sub.2n, Y is hydrogen, alkyl, alkoxy or halogen, Z.crclbar. is an anion and n is an integer from 2 to 6.Such ester-containing quaternary pyridinium salts also cause toner particles containing them to display lower fusing temperatures and improved adhesion indexes.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: May 18, 1993
    Assignee: Eastman Kodak Company
    Inventors: John C. Wilson, Alexandra D. Bermel
  • Patent number: 5189177
    Abstract: The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of diborane, borane-dimethyl sulfide or borane-tetrahydrofuran reductions of ketones to secondary alcohols.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: February 23, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
  • Patent number: 5185337
    Abstract: There is described pyrroloquinoline derivatives of general formula: ##STR1## wherein R' is a C.sub.1 -C.sub.6 alkyl group, R.sup.2 is a group: ##STR2## or group: ##STR3## wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined, or salt thereof. These compounds have an antimicrobial activity.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: February 9, 1993
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Setsuro Fujii, deceased, Kaoruko Takada, legal heir, Hiroshi Ishikawa, Hidetsugu Tsubouchi, Koichiro Jitsukawa
  • Patent number: 5169841
    Abstract: The invention relates to compounds of the formula 1 ##STR1## in which A.sup.1 denotes a radical of the formulae ##STR2## A.sup.2 is absent or represents a radical of the formula ##STR3## R.sup.2, R.sup.3 and R.sup.4 are as defined in the specification, and X and Y, independently of one another, represent --O-- or --NR.sup.13 --, and to the salts thereof. Also described is a process for the preparation of the compounds of the formula 1, corresponding pharmaceutical products, and the use thereof as medicines, and intermediates for the preparation of these compounds.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: December 8, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz-Werner Kleeman, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
  • Patent number: 5164502
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: November 17, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5157117
    Abstract: The invention relates to novel compounds of the formula: ##STR1## useful as an intermediate in the preparation of quinoline carboxylic acid medicaments.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: October 20, 1992
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Naomi Takagi, Hironobu Fubasami, Hiroshi Matsukubo
  • Patent number: 5151520
    Abstract: A cationic dye-borate anion compound represented by the formula: ##STR1## where D+ is a cationic dye moiety selected from the group consisting of cationic cyanine, carbocyanine, hemicyanine, rhodamine, and azamethine dyes; R.sup.1 is alkyl; and R.sup.2, R.sup.3, and R.sup.4 are aryl. Such cationic dye-borate anion compounds are useful photoinitiators of free radical addition reactions.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: September 29, 1992
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Douglas C. Neckers, Gary B. Schuster
  • Patent number: 5144036
    Abstract: New N-substituted quinolinium salts are provided having advantageous utility as charge agents in electrostatographic toners and developers. The salts have the structure: ##STR1## wherein R is a straight or branched chain alkyl group having from 1 to 5 carbon atoms, aralkyl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, R' and R", which are the same or different, represent hydrogen or a straight or branched chain alkyl or alkoxy group having from 1 to 24 carbon atoms, aralkyl or alkaryl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, unsubstituted aryl having from 6 to 14 carbon atoms or aryl having from 6 to 14 carbon atoms substituted with one or more nitro, alkoxy or halo groups and X is hydrogen, chlorine, bromine, fluorine or iodine.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: September 1, 1992
    Assignee: Eastman Kodak Company
    Inventors: Peter S. Alexandrovich, John C. Wilson
  • Patent number: 5144032
    Abstract: An improved curing agent for use in coatings, laminates, moldings, castings and adhesives comprising the use of an amine-boron adduct component along with anhydride and epoxy component mixtures. Also provided is an improved process for the preparation of tertiary amine borane curing agents.
    Type: Grant
    Filed: April 19, 1991
    Date of Patent: September 1, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Anthony J. Arduengo
  • Patent number: 5126063
    Abstract: Lubricating oil and grease compositions contain borated hydroxyalkyl esters of amine or metal salts of diorganodithiocarbamic acid, such as N,N'-di-(2-ethylhexyl) dithiocarbamic acid, and hydrocarbylene oxie, such as propylene oxide, as antioxidant, load-carrying and friction modifying additives.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: June 30, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Angeline B. Cardis, Liehpao O. Farng, Abraham O. M. Okorodudu, Andrew G. Horodysky
  • Patent number: 5116982
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: May 26, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5091530
    Abstract: The invention relates to a new process for the preparation of compounds of the general Formula I ##STR1## /wherein R stands for piperazinyl, 4-methyl-piperazinyl or 4-ethyl-piperazinyl group/ and pharmaceutically acceptable salts thereof which comprises reacting a compound of the general Formula II ##STR2## /wherein R.sup.1 and R.sup.2 stand for halogen, for an aliphatic acyloxy group containing 2 to 6 carbon atoms and optionally substituted by halogen, or for an aromatic acyloxy group containing 7 to 11 carbon atoms/ with a piperazine derivative of the general Formula ##STR3## /wherein R.sup.3 stands for hydrogen, methyl or ethyl/ or a salt thereof and subjecting the compound of the general Formula IV ##STR4## thus obtained /wherein R, R.sup.1 and R.sup.2 are as stated above/ to hydrolysis after or without isolation and if desired converting the compound of the general Formula I thus obtained into a salt thereof or setting free the same from its salt.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: February 25, 1992
    Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Hermecz, Geza Kereszturi, Lelle Vasvari, Agnes Horvath, Marie Balogh, Peter Ritli, Judit Sipos, Aniko Pajor, Katalin Marmarosi
  • Patent number: 5073556
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 represents fluorinated methoxy; R.sup.2 represents a nitrogen-containing heterocyclic group and R.sup.3 represents hydrogen or amino) and pharmaceutically acceptable salts, esters and amides thereof are valuable antibacterial agents, which may be prepared by reacting a compound similar to that of formula (I) but in which R.sup.2 is replaced by a halogen atom with a compound providing the required group R.sup.2.
    Type: Grant
    Filed: February 22, 1991
    Date of Patent: December 17, 1991
    Assignees: Sankyo Company Limited, Ube Industries Limited
    Inventors: Masayuki Iwata, Tomio Kimura, Teruhiko Inoue, Yoshimi Fujihara, Tetsushi Katsube
  • Patent number: 5070203
    Abstract: New N,N'-substitutedbis(pyridinium) salts are provided having advantageous utility as charge agents in electrostatographic toners and developers. The salts have the structure: ##STR1## wherein R is alkylene having from 1 to 20 carbon atoms or arylenedialkylene wherein each alkylene moiety has 1 to 6 carbon atoms and the arylene moiety has from 6 to 14 carbon atoms, R' and R", which are the same or different, represent hydrogen, a straight or branched chain alkyl or alkoxy group having from 1 to 24 carbon atoms, aralkyl or alkaryl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, aryl having 6 to 14 carbon atoms which is unsubstituted or aryl having 6 to 14 carbon atoms which is substituted with one or more nitro, alkoxy or halo groups and X and X', which are the same or different, are chlorine, bromine, fluorine or iodine.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: December 3, 1991
    Assignee: Eastman Kodak Company
    Inventors: John C. Wilson, Peter S. Alexandrovich
  • Patent number: 5053537
    Abstract: Ammonium compounds of the formula (I) ##STR1## in which at least one of the radicals R.sub.1 to R.sub.4 denotes a fluorine-containing alkyl radical having 4 to 30 carbon atoms and not more than three of the radicals R.sub.1 to R.sub.4 independently of one another denote hydrogen atoms or alkyl or hydroxyalkyl radicals having 1 to 30 carbon atoms, and R.sub.5 to R.sub.8 denote aryl, alkylaryl or halogenoaryl radicals or fluorine atoms, and iminium compounds of the formula (II) ##STR2## in which Q, together with the constituent ##STR3## forms a ring system having 4 to 17 carbon atoms, which can be interrupted by 1 to 4 hetero atoms and contain 2 to 9 double bonds, and which can be substituted by fluorine, chlorine, bromine or iodine atoms or alkyl (C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), nitro or amino groups, R.sub.9 denotes a fluorine-containing alkyl (C.sub.1 -C.sub.30) radical, R.sub.10 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom or an alkyl(C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.
    Type: Grant
    Filed: November 2, 1989
    Date of Patent: October 1, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jorg Gitzel, Hans-Tobias Macholdt, Frank Wehowsky, Gunther Prossel
  • Patent number: 5041625
    Abstract: New electrostatographic toners and developers are provided containing new charge-control agents comprising N,N'-substitutedbis(pyridinium) salts having the structure: ##STR1## wherein R is alkylene having from 1 to 20 carbon atoms or arylenedialkylene wherein each alkylene moiety has 1 to 6 carbon atoms and the arylene moiety has from 6 to 14 carbon atoms, R' and R", which are the same or different, represent hydrogen, a straight or branched chain alkyl or alkoxy group having from 1 to 24 carbon atoms, aralkyl or alkaryl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, aryl having 6 to 14 carbon atoms which is unsubstituted or aryl having 6 to 14 carbon atoms which is substituted with one or more nitro, alkoxy or halo groups and X and X', which are the same or different, are chlorine, bromine, fluorine or iodine.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventors: John C. Wilson, Peter S. Alexandrovich
  • Patent number: 5039802
    Abstract: The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl-methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of borane-dimethyl sulfide reductions of ketones to secondary alcohols.
    Type: Grant
    Filed: April 18, 1990
    Date of Patent: August 13, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
  • Patent number: 5023513
    Abstract: Novel amine-alkylborane derivatives are disclosed which exhibit significant antineoplastic and antihyperlipidemic activities. Methods for preparing the compounds are disclosed as well as methods for utilizing the compounds to induce antineoplastic and antihyperlipidemic activity.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: June 11, 1991
    Assignee: Boron Biologicals, Inc.
    Inventors: Bernard F. Spielvogel, Anup Sood
  • Patent number: 4997943
    Abstract: Compounds of formula (I): ##STR1## (in which R.sup.1 is alkoxy, R is alkyl, haloalkyl, alkylamino, cycloalkyl or optionally substituted phenyl, X is chlorine or fluorine and Y is selected from certain specific heterocycles) have excellent antibacterial activity. They may be prepared by introducing the group represented by Y into the corresponding compound in which Y is replaced by a halogen atom.
    Type: Grant
    Filed: March 31, 1987
    Date of Patent: March 5, 1991
    Assignees: Sankyo Company Limited, Ube Industries Limited
    Inventors: Masayuki Iwata, Tomio Kimura, Yoshimi Fujihara, Tetsushi Katsube
  • Patent number: 4981966
    Abstract: The invention relates to a new process for the preparation of compounds of the Formula I ##STR1## (wherein R stands for hydrogen or methyl) and pharmaceutically acceptable salts thereof which comprises reacting a compound of the Formula V ##STR2## (wherein R.sup.1 and R.sup.2 stand for an aliphatic acyloxy group comprising 2-6 carbon atoms and optionally substituted by halogen; or for an aromatic acyloxy group comprising 7-11 carbon atoms) with an amine of the Formula VI ##STR3## (wherein R has the same meaning as stated above) or a salt thereof and subjecting the compound of the Formula VII ##STR4## thus obtained (wherein R, R.sup.1 and R.sup.2 are as stated above) to hydrolysis after or without isolation and if desired converting the compound of the Formula I thus obtained into a salt thereof or setting free the same from its salt.The compounds of the Formula I are known antibacterial agents.
    Type: Grant
    Filed: January 10, 1989
    Date of Patent: January 1, 1991
    Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Hermecz, Geza Kereszturi, Lelle Vasvari nee Debreczy, Agnes Horvath, Maria Balogh, Gabor Kovacs, Tamas Szuts, Peter Ritli, Judit Sipos, Aniko Pajor
  • Patent number: 4963568
    Abstract: Novel compounds which are selective dopamine agonists are useful for treating disorders characterized by abnormal dopamine levels, such as Parkinson's Disease, as well as cardiovascular disorders.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: October 16, 1990
    Assignee: Abbott Laboratories
    Inventors: Robert W. Schoenleber, John W. Kebabian, Yvonne C. Martin, Michael P. DeNinno, Richard J. Perner, David M. Stout, Chi-Nung W. Hsiao, Stanley DiDomenico, Jr., John F. DeBernardis, Fatima Z. Basha, Michael D. Meyer, Biswanath De
  • Patent number: 4954414
    Abstract: A composition including a cationic transition metal coordination complex and a borate anion, wherein said composition is capable of absorbing actinic radiation and producing free radicals which can initiate free radical addition polymerization of a free radical addition polymerizable or crosslinkable monomer is disclosed. The compositions are particularly useful as visible light photoinitiators.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: September 4, 1990
    Assignee: The Mead Corporation
    Inventors: Paul C. Adair, Peter Gottschalk
  • Patent number: 4943635
    Abstract: Chiral 1,3,2-oxazaborolidines and tetrahydro-1,3,2-oxazaborines are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: July 24, 1990
    Assignee: President & Fellows of Harvard College
    Inventor: Elias J. Corey
  • Patent number: 4940794
    Abstract: The invention relates to new quinoline-3-carboxylic acid anhydride intermediates of the Formula I ##STR1## wherein R stands for cyclopropyl, a group of the Formula --CH.sub.2 CR.sup.5 R.sup.6 R.sup.7 wherein R.sup.5, R.sup.6 and R.sup.7 stand for hydrogen or halogen, or phenyl optionally substituted by 1 or 2 halogen,R.sup.1 and R.sup.2 stand for halogen, or an aliphatic acyloxy group containing 2 to 6 carbon atoms optionally substituted by halogen, or an aromatic acyloxy group containing 7 to 11 carbon atoms,R.sup.3 stands for chlorine or fluorine andR.sup.4 stands for hydrogen or fluorine. The compounds of the Formula I are new intermediates for the preparation of known quinoline-3-carbocxylic acids showing antibacterial activity.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: July 10, 1990
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara/Rt.
    Inventors: Istvan Hermecz, Geza Kereszturi, Lelle Vasvari, Agnes Horvath, Maria Halogh, Peter Ritli, Judit Sipos, Aniko Pajor, Katalin Marmarosi
  • Patent number: 4935519
    Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: June 19, 1990
    Assignee: Allied-Signal Inc.
    Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
  • Patent number: 4921862
    Abstract: The invention concerns a method of inhibiting both thromboxane synthetase and cyclic-AMP phosphodiesterase in a mammal having a disease characterized by elevated thromboxane levels or an imbalance of prostacyclin/thromboxane levels with a compound of the formula: ##STR1## or a pharmaceutically acceptable acid addition salt or ester thereof, wherein:X is chosen from the group consisting of: ##STR2## and a covalent bond in which R.sup.1 is H, alkyl having 1-6 carbon atoms, optionally substituted phenyl or optionally substituted phenyl lower alkyl, when R.sup.2 is H or OH, or R.sup.1 and R.sup.2 taken together represent oxo, alkylidene having 1-6 carbon atoms or optionally substituted benzylidene;R.sup.3 is H or alkyl having 1-6 carbon atoms, R.sup.4 is H and R.sup.3 and R.sup.4 are either cis or trans to each other, or R.sup.3 and R.sup.4 taken together represent a covalent bond;n is an integer from 0-3;Het is 1-imidazolyl or 3-pyridyl; and the dotted line represents an optional covalent bond.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: May 1, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, John J. Bruno, Gregory R. Martinez
  • Patent number: 4870177
    Abstract: Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 26, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4839260
    Abstract: Polymethine dyes and ultraviolet absorbers are disclosed containing a basic electron donating terminal nucleus and an acidic electron accepting terminal nucleus satisfying the formula: ##STR1## where Ar is independently in each occurrence an aromatic group andD is an oxy or amino group.These polymethines are useful in imaging materials.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: June 13, 1989
    Assignee: Eastman Kodak Company
    Inventor: Margaret E. Logan
  • Patent number: 4839274
    Abstract: Polymethine dyes and ultraviolet absorbers are disclosed containing a basic electron donating terminal nucleus and an acidic electron accepting terminal nucleus comprised of a triarylborylisocyano group. The dyes are useful in imaging materials.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: June 13, 1989
    Assignee: Eastman Kodak Company
    Inventor: Margaret E. Logan
  • Patent number: 4822800
    Abstract: Substituted 3-isoquinolinol compounds of the general formula ##STR1## that exhibit cardiotonic, renal vasodilating and phosphodiesterase fraction III properties are pharmacologically active in the treatment of cardiac conditions. Methods for synthesizing and using those compounds are described.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: April 18, 1989
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Robert Falotico, Ramesh M. Kanojia, Jeffery B. Press, Alfonso J. Tobia
  • Patent number: 4814452
    Abstract: An enantioselective synthesis of 1,3,4,6,7,12b(S)-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin-2-one provides a key intermediate for the preparation of the .alpha..sub.2 -adrenergic antagonist (2R,12bS)-N-(1,3,4,6,7,12-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin-2-yl) -N-methyl-2-hydroxyethanesulfonamide hydrochloride, useful as an anti-depressant.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: March 21, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Ralph P. Volante, Edward Corley, Ichiro Shinkai
  • Patent number: 4806645
    Abstract: The invention relates to new 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid/boric acid anhydrides of the general Formula I ##STR1## (wherein R and R.sup.1 stand for halogen; an aliphatic acyloxy group comprising 2-6 carbon atoms and optionally substituted by halogen; or an aromatic acyloxy group comprising 7-11 carbon atoms).The new compounds of the general Formula I are valuable intermediates useful in the preparation of the antibacterial agent 6-fluoro-1-methylamino-7-(4-methyl-piperazino)-4-oxo-1,4-dihydro-quinoline -3- carboxylic acid.The new compounds of the general Formula I may be prepared by reacting a compound of the Formula II ##STR2## or a compound of the general Formula III ##STR3## (wherein R.sup.2 stands for alkyl comprising 1-4 carbon atoms) with hydrogen fluoro borate of the Formula IVHBF.sub.4 /IV/or a borone trihalide of the general Formula VBX.sub.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: February 21, 1989
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Hermecz, Geza Kereszturi, Lelle Vasvari, Agnes Horvath, Maria Balogh, Gabor Kovacs, Zoltan Meszaros, deceased, Peter Ritli, Judit Sipos, Aniko Pajor
  • Patent number: 4803274
    Abstract: The invention relates to a process for the preparation of compounds of the Formula I ##STR1## (wherein R and R.sup.1 stand for an aliphatic acyloxy group comprising 2-5 carbon atoms and optionally substituted by halogen or for an aromatic acyloxy group comprising 7-11 carbon atoms), which comprises reacting a compound of the general Formula II ##STR2## (wherein R.sup.2 stands for hydrogen or alkyl comprising 1-4 carbon atoms) with a boron derivative of the Formula III ##STR3## (wherein R.sup.3, R.sup.4 and R.sup.5 stand for an alkyl group comprising 1-4 carbon atoms and optionally substituted by halogen or for an aryl group comprising 6-10 carbon atoms).The new compounds of the general Formula I are useful pharmaceutical intermediates.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: February 7, 1989
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Hermecz, Geza Kereszturi, Lelle Vasvari, Agnes Horvath, Maria Balogh, Gabor Kovacs, Zoltan Meszaros, deceased, Peter Ritli, Judit Sipos, Aniko Pajor