Boron Containing Patents (Class 546/13)
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Patent number: 5502065Abstract: The present invention provides compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: September 21, 1994Date of Patent: March 26, 1996Assignee: Pfizer Inc.Inventors: Alan D. Brown, Roger P. Dickinson, Martin J. Wythes
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Patent number: 5496951Abstract: 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: GrantFiled: January 27, 1995Date of Patent: March 5, 1996Assignees: Sankyo Company, Limited, Ube Industries LimitedInventors: Masayuki Iwata, Tomio Kimura, Teruhiko Inoue, Yoshimi Fujihara, Tetsushi Katsube
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Patent number: 5495020Abstract: 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: GrantFiled: August 2, 1990Date of Patent: February 27, 1996Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
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Patent number: 5493046Abstract: The novel process of the invention for the preparation of a compound of the formula ##STR1##Type: GrantFiled: October 27, 1994Date of Patent: February 20, 1996Assignee: Roussel-UclafInventors: Neerja Bhatnagar, Jean Buendia, Christine Griffoul
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Patent number: 5466798Abstract: 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: GrantFiled: October 15, 1993Date of Patent: November 14, 1995Assignee: The Regents of the University of CaliforniaInventors: Bakthan Singaram, Gary B. Fisher, Joseph C. Fuller, John Harrison, Christian T. Goralski
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Patent number: 5451663Abstract: 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: GrantFiled: April 8, 1993Date of Patent: September 19, 1995Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland
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Patent number: 5446157Abstract: 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: GrantFiled: February 19, 1993Date of Patent: August 29, 1995Inventors: Lee R. Morgan, Joseph H. Boyer
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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: 5329046Abstract: 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: GrantFiled: June 25, 1992Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Hans-Tobias Macholdt, Siegfried Schiessler, Jorg Gitzel, Erwin Dietz
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Patent number: 5290934Abstract: 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: GrantFiled: June 4, 1991Date of Patent: March 1, 1994Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
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Patent number: 5286864Abstract: The invention relates to new quinuclidines, processes for their preparation and their use as medicaments having cholinomimetic properties.Type: GrantFiled: October 16, 1992Date of Patent: February 15, 1994Assignee: Boehringer Ingelheim KGInventors: Gerhard Walther, Karl H. Weber, Werner Stransky, Franz J. Kuhn, Enzio Muller, Helmut Ensinger
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Patent number: 5280119Abstract: 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: GrantFiled: November 1, 1991Date of Patent: January 18, 1994Assignee: Boron Biologicals, Inc.Inventors: Bernard F. Spielvogel, Anup Sood, Iris H. Hall
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Patent number: 5274113Abstract: 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: GrantFiled: November 1, 1991Date of Patent: December 28, 1993Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland
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Patent number: 5264574Abstract: 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: GrantFiled: April 3, 1992Date of Patent: November 23, 1993Assignee: Merck & Co., Inc.Inventors: James D. Carroll, David J. Mathre, Edward G. Corley, Andrew S. Thompson
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Patent number: 5264585Abstract: 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: GrantFiled: October 26, 1992Date of Patent: November 23, 1993Assignee: Merck & Co., Inc.Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
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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: 5221761Abstract: 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: GrantFiled: April 29, 1992Date of Patent: June 22, 1993Assignees: Instituto Guido Donegani, Enichem America, Inc.Inventors: Kwan-Yue A. Jen, Terence Moran
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Patent number: 5212035Abstract: 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: GrantFiled: July 18, 1991Date of Patent: May 18, 1993Assignee: Eastman Kodak CompanyInventors: John C. Wilson, Alexandra D. Bermel
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Patent number: 5189177Abstract: 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: GrantFiled: July 15, 1991Date of Patent: February 23, 1993Assignee: Merck & Co., Inc.Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
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Patent number: 5185337Abstract: 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: GrantFiled: April 25, 1991Date of Patent: February 9, 1993Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Setsuro Fujii, deceased, Kaoruko Takada, legal heir, Hiroshi Ishikawa, Hidetsugu Tsubouchi, Koichiro Jitsukawa
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Patent number: 5169841Abstract: 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: GrantFiled: November 3, 1988Date of Patent: December 8, 1992Assignee: Hoechst AktiengesellschaftInventors: Heinz-Werner Kleeman, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
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Patent number: 5164502Abstract: 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: GrantFiled: November 8, 1991Date of Patent: November 17, 1992Assignee: DowElancoInventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
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Patent number: 5157117Abstract: The invention relates to novel compounds of the formula: ##STR1## useful as an intermediate in the preparation of quinoline carboxylic acid medicaments.Type: GrantFiled: July 1, 1991Date of Patent: October 20, 1992Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Naomi Takagi, Hironobu Fubasami, Hiroshi Matsukubo
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Patent number: 5151520Abstract: 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: GrantFiled: January 30, 1990Date of Patent: September 29, 1992Assignee: The Mead CorporationInventors: Peter Gottschalk, Douglas C. Neckers, Gary B. Schuster
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Patent number: 5144036Abstract: 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: GrantFiled: July 31, 1990Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Peter S. Alexandrovich, John C. Wilson
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Patent number: 5144032Abstract: 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: GrantFiled: April 19, 1991Date of Patent: September 1, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Anthony J. Arduengo
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Patent number: 5126063Abstract: 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: GrantFiled: September 27, 1990Date of Patent: June 30, 1992Assignee: Mobil Oil CorporationInventors: Angeline B. Cardis, Liehpao O. Farng, Abraham O. M. Okorodudu, Andrew G. Horodysky
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Patent number: 5116982Abstract: 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: GrantFiled: August 6, 1990Date of Patent: May 26, 1992Assignee: DowElancoInventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
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Patent number: 5091530Abstract: 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: GrantFiled: November 23, 1988Date of Patent: February 25, 1992Assignee: 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
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Patent number: 5073556Abstract: 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: GrantFiled: February 22, 1991Date of Patent: December 17, 1991Assignees: Sankyo Company Limited, Ube Industries LimitedInventors: Masayuki Iwata, Tomio Kimura, Teruhiko Inoue, Yoshimi Fujihara, Tetsushi Katsube
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Patent number: 5070203Abstract: 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: GrantFiled: July 31, 1990Date of Patent: December 3, 1991Assignee: Eastman Kodak CompanyInventors: John C. Wilson, Peter S. Alexandrovich
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Patent number: 5053537Abstract: 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: GrantFiled: November 2, 1989Date of Patent: October 1, 1991Assignee: Hoechst AktiengesellschaftInventors: Jorg Gitzel, Hans-Tobias Macholdt, Frank Wehowsky, Gunther Prossel
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Patent number: 5041625Abstract: 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: GrantFiled: July 31, 1990Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventors: John C. Wilson, Peter S. Alexandrovich
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Patent number: 5039802Abstract: 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: GrantFiled: April 18, 1990Date of Patent: August 13, 1991Assignee: Merck & Co., Inc.Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
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Patent number: 5023513Abstract: 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: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: Boron Biologicals, Inc.Inventors: Bernard F. Spielvogel, Anup Sood
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Patent number: 4997943Abstract: 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: GrantFiled: March 31, 1987Date of Patent: March 5, 1991Assignees: Sankyo Company Limited, Ube Industries LimitedInventors: Masayuki Iwata, Tomio Kimura, Yoshimi Fujihara, Tetsushi Katsube
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Patent number: 4981966Abstract: 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: GrantFiled: January 10, 1989Date of Patent: January 1, 1991Assignee: 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
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Patent number: 4963568Abstract: 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: GrantFiled: May 31, 1989Date of Patent: October 16, 1990Assignee: Abbott LaboratoriesInventors: 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
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Patent number: 4954414Abstract: 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: GrantFiled: November 8, 1988Date of Patent: September 4, 1990Assignee: The Mead CorporationInventors: Paul C. Adair, Peter Gottschalk
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Patent number: 4943635Abstract: 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: GrantFiled: July 29, 1988Date of Patent: July 24, 1990Assignee: President & Fellows of Harvard CollegeInventor: Elias J. Corey
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Patent number: 4940794Abstract: 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: GrantFiled: December 2, 1988Date of Patent: July 10, 1990Assignee: 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
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Patent number: 4935519Abstract: 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: GrantFiled: September 13, 1989Date of Patent: June 19, 1990Assignee: Allied-Signal Inc.Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
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Patent number: 4921862Abstract: 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: GrantFiled: September 21, 1988Date of Patent: May 1, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. M. Walker, John J. Bruno, Gregory R. Martinez
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Patent number: 4870177Abstract: 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: GrantFiled: December 17, 1987Date of Patent: September 26, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4839260Abstract: 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: GrantFiled: June 30, 1987Date of Patent: June 13, 1989Assignee: Eastman Kodak CompanyInventor: Margaret E. Logan
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Patent number: 4839274Abstract: 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: GrantFiled: June 30, 1987Date of Patent: June 13, 1989Assignee: Eastman Kodak CompanyInventor: Margaret E. Logan
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Patent number: 4822800Abstract: 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: GrantFiled: June 9, 1986Date of Patent: April 18, 1989Assignee: Ortho Pharmaceutical CorporationInventors: Robert Falotico, Ramesh M. Kanojia, Jeffery B. Press, Alfonso J. Tobia
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Patent number: 4814452Abstract: 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: GrantFiled: July 3, 1986Date of Patent: March 21, 1989Assignee: Merck & Co., Inc.Inventors: Ralph P. Volante, Edward Corley, Ichiro Shinkai
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Patent number: 4806645Abstract: 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: GrantFiled: August 7, 1987Date of Patent: February 21, 1989Assignee: 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
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Patent number: 4803274Abstract: 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: GrantFiled: August 7, 1987Date of Patent: February 7, 1989Assignee: 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