Monocyclic Acid Moiety Patents (Class 560/103)
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Patent number: 5659068Abstract: Polyoxyalkylene glycol monoesters of carboxylic acids are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a carboxylic acid and of an anhydrous heteropolyacid catalyst.Type: GrantFiled: May 31, 1994Date of Patent: August 19, 1997Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5659069Abstract: This invention discloses an improved method for the [2+2+2] cyclotrimerization reaction in aqueous solutions using a water soluble transition metal catalyst.Type: GrantFiled: March 20, 1996Date of Patent: August 19, 1997Assignee: NeXstar Pharmaceuticals, Inc.Inventors: Bruce Eaton, Matthew S. Sigman
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Patent number: 5654452Abstract: Aromatic acid-derived lipophilic polyhalogenated compounds are provided for use as contrast agents in diagnostic imaging or as therapeutic agents. These compounds are particularly useful when incorporated into an oil-in-water emulsion for tissue-specific delivery to the liver. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm and having a composition simulating naturally-occuring chylomicron remnants.Type: GrantFiled: June 7, 1995Date of Patent: August 5, 1997Assignee: Molecular Biosystems, Inc.Inventors: Rolf Lohrmann, Dung K. Hong
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Patent number: 5648512Abstract: Compounds having the active site of natural lipoxins, but a longer tissue hlf-life are disclosed. These small molecules are useful for treating vasoconstrictive, inflammatory, myeloid suppressive, cardiovascular, and gastrointestinal diseases.Type: GrantFiled: May 31, 1995Date of Patent: July 15, 1997Assignee: Brigham & Womens HospitalInventor: Charles N. Serhan
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Patent number: 5637757Abstract: A method of preparing tetrabromobenzoate compounds from tetrabromophthalic anhydride by reacting tetrabromophthalic anhydride with alcohol in the presence of a decarboxylation catalyst. The reaction may be carried out in an excess of alcohol, or with a near stoichiometric amount of alcohol by performing the reaction in an inert solvent.Type: GrantFiled: April 11, 1995Date of Patent: June 10, 1997Assignee: Great Lakes Chemical CorporationInventors: John E. Hill, Nicolai A. Favstritsky, Rastko I. Mamuzic, Bhabatosh Bhattacharya
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Patent number: 5635571Abstract: Polyoxazolines having the structural formula: ##STR1## wherein R is phenylene or alkylene containing 2 to 18 carbon atoms, R.sup.2 is C.sub.1-4 alkyl and R.sub.1 is selected from the group consisting of C.sub.1-12 alkyl, vinyl, isopropylidene, pentafluoroethyl, phenyl, hydroxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups, C.sub.1-2 -alkoxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups and .paren open-st.CH.sub.2 CH.sub.2 --O.paren close-st..sub.r CH.sub.3 in which r ranges from 1-20, X is NH.sub.2 or OH, n ranges from 2 to 50 and m ranges from 0 to 50, wherein R.sub.1 is hydroxyphenyl optionally interrupted by up to 20 ethylene oxide groups only when X is NH.sub.2, are polymerizable to form hyperbranched polymers which have a number average molecular weight ranging from 5,000 to 150,000, a weight average molecular weight ranging from 5,500 to 5,000,000 and a polydispersity ranging from 1.Type: GrantFiled: June 5, 1996Date of Patent: June 3, 1997Assignee: Cornell Research Foundation, Inc.Inventors: Jean M. J. Frechet, Koji Yui
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Patent number: 5618320Abstract: Aromatic esters of polyalkylphenoxyalkanols having the formula: ##STR1## or a fuel soluble salt thereof, wherein R is hydroxy, nitro or --(CH.sub.2).sub.x --NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and x is 0 or 1;R.sub.1 is hydrogen, hydroxy, nitro or --NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: May 14, 1996Date of Patent: April 8, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5603916Abstract: This invention relates to methods of x-ray diagnostic imaging the blood pool, liver, spleen and/or lymph system of a mammal comprising administering a contrast effective amount of a contrast agent having the structure: ##STR1## wherein: n is 2;R.sup.1 is H or alkyl containing from 1 to 4 carbon atoms'R.sup.2 is H, alkyl containing from 1 to 4 carbon atoms, aryl or heteroaryl;and R.sup.3 is alkyl containing from 1 to 18 carbon atoms.This invention further relates to novel contrast agents having the above structure wherein R.sup.1 is H and R.sup.2 and R.sup.3 are CH.sub.3 to x-ray contrast compositions comprising such agents, and to method of x-ray diagnostic imaging utilizing such agents.Type: GrantFiled: May 22, 1995Date of Patent: February 18, 1997Assignee: Nano Systems L.L.C.Inventor: Baldev Singh
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Patent number: 5554641Abstract: The small nonpeptides of the instant invention are tachykinin antagonists. The compounds are highly selective and functional NK.sub.3 antagonists expected to be useful in the treatment of pain, depression, anxiety, panic, schizophrenia, neuralgia, addiction disorders, inflammatory diseases, gastrointestinal disorders, vascular disorders, and neuropathological disorders.Type: GrantFiled: March 20, 1995Date of Patent: September 10, 1996Inventors: David C. Horwell, Martyn C. Pritchard, Jennifer Raphy
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: 5543550Abstract: The present invention relates to a process for the preparation of 5-fluoroanthranilic alkyl esters and/or 5-fluoroanthranilic acid, which comprises dissolving a 3-fluorobenzoic alkyl ester in sulfuric acid and reacting the solution with a nitrating acid at from -10.degree. to 30.degree. C., then adding water, separating off the nitrated reaction product and reacting it with hydrogen at from 50.degree. to 120.degree. C. under elevated pressure in the presence of a catalyst comprising a metal of the platinum group and sulfur, and, if desired, removing 5-fluoroanthranilic alkyl esters by distillation and hydrolyzing them to give 5-fluoroanthranilic acid.Type: GrantFiled: October 6, 1994Date of Patent: August 6, 1996Assignee: Hoechst AktiengesellschaftInventors: Jochen Rapp, Siegfried Planker, Theodor Papenfuhs, G unter Bartels
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Patent number: 5536870Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 17, 1995Date of Patent: July 16, 1996Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 5532405Abstract: A process for the esterification of acids or anhydrides with alcohols or a polyhydroxy compound wherein the lower boiling point reactant is added to the reaction vessel in stages such that it is present in an amount of at least about 5% of the stoichiometric requirements of the total lower boiling point reactant required to react with the limiting reagent, and wherein the concentration of the lower boiling point reactant is monitored so that additional reactant having the lower boiling point can be subsequently added in stages to the reaction mixture in order to maintain a certain predetermined concentration of the lower boiling point reactant.Type: GrantFiled: April 29, 1994Date of Patent: July 2, 1996Assignee: Exxon Chemical Patents Inc.Inventor: John Lyford, IV
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Patent number: 5493048Abstract: The new fluoro-trifluoromethylbenzoic acid derivatives of the general formula (I) ##STR1## wherein the substituents R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning given in the description, are suitable as starting substances for the preparation of antibacterial agents and feed additives.Type: GrantFiled: January 12, 1994Date of Patent: February 20, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Peter Andres
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Patent number: 5488133Abstract: Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; n is an integer from 0 to 20;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy, acylamino, acetamidoalkyl, acetamidoaryl, --COO-alkyl, --COO-aryl, --COO-aralkyl, --CO-alkyl, --CO-aryl, --CO-heterocyclyl, cyano or heterocyclyl;R.sup.5 is H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl, heterocyclyl, or a Z-CO.sub.2 -CR.sup.1 R.sup.2 (CR.sup.3 R.sup.4).sub.n group, wherein Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined above, m is an integer from 0 to 10, p is an integer from 0 to 10, and m+p.gtoreq.1 are useful as contrast agents in x-ray imaging compositions and methods.Type: GrantFiled: March 10, 1994Date of Patent: January 30, 1996Assignee: Eastman Kodak CompanyInventors: Baldev Singh, Edward R. Bacon, Shaughnessy Robinson
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Patent number: 5478964Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.Type: GrantFiled: December 10, 1992Date of Patent: December 26, 1995Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5468897Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha., .alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.Type: GrantFiled: May 4, 1994Date of Patent: November 21, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5446190Abstract: Process for the preparation of alcohol fluorobenzoates of the formula (I) ##STR1## in which R is an alkyl radical and F.sub.n is 1 to 4 fluorine atoms which, independently of one another, are bonded to the aromatic ring, by reacting a fluorobenzyl chloride of the formula (II) ##STR2## in which F.sub.n is as defined above, with an at least stoichiometric amount of an alkali metal alcoholate ROM in which R is as defined above and M is an alkali metal from the group consisting of Li, Na and K, in the corresponding alcohol ROH at temperatures from -10.degree. C. to 150.degree. C., the solvent is distilled off, if appropriate, and the alkali metal chloride formed is separated off by treating the mixture with water or by filtration.Type: GrantFiled: November 15, 1994Date of Patent: August 29, 1995Assignee: Hoechst AktiengesellschaftInventors: Gilbert Billeb, Wolfgang Tronich
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Patent number: 5416240Abstract: Polyoxyalkylene glycols are prepared by a process in which tetrahydrofuran is polymerized with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals in the absence of water and in the presence of a monohydric alcohol or of a monocarboxylic acid with the aid of an anhydrous heteropoly acid catalyst, and the polyoxyalkylene glycol is liberated from the resulting polyoxyalkylene glycol monoethers or polyoxyalkylene glycol monoesters by cleavage of the monoether or monoester bond.Type: GrantFiled: March 2, 1993Date of Patent: May 16, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Franz Merger, Herbert Mueller
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5380719Abstract: Angiotensin II inhibition is exhibited by ##STR1## wherein: X is --CH.sub.2 -- or O;R is hydrogen, alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl;R.sup.1 and R.sup.2 are each independently O or absent;R.sup.3 is hydrogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, aralkyl, cycloalkylalkyl, halo, haloalkyl, or haloalkoxy;R.sup.4 is hydrogen, alkyl, alkenyl, alkoxy, aryl, cycloalkyl, aralkyl, cycloalkylalkyl, --R.sup.8 --OH, or --R.sup.8 CO.sub.2 R.sup.9 ;and the remaining symbols are as defined in the specification.Type: GrantFiled: April 28, 1992Date of Patent: January 10, 1995Assignee: E. R. Squibb & Sons, Inc.Inventor: Kyoung S. Kim
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Patent number: 5374376Abstract: Disclosed are herein optically active aromatic compounds represented by the formula (I): ##STR1## wherein X represents --COO-- or --OCO--; Y represents --COO--, --OCO-- or --O--; R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms unsubstituted or substituted by a halogen atom; R.sub.1 represents an alkyl group having 3 to 20 carbon atoms;Z represents ##STR2## wherein p represents a number of 1 to 5 and * indicates an asymmetric carbon atom; l and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1, which are useful as a liquid crystal.Type: GrantFiled: September 21, 1993Date of Patent: December 20, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Shigeaki Chika, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5371209Abstract: The process entails adding salt in an amount of 1% to 5% by weight slurry to an aqueous slurry of cyclodextrin-guest complex at a temperature of 100.degree. C. to 150.degree. C. for a period of 5 minutes to 2 hours and a pressure of 15 psia to 70 psia to prevent the slurry from boiling and to cause the complex to break apart. The individual cyclodextrin and guest are then recovered.Type: GrantFiled: June 15, 1993Date of Patent: December 6, 1994Assignee: American Maize-Products CompanyInventors: Wen Shieh, Allan Hedges
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Patent number: 5366517Abstract: A fuel additive composition comprising:(a) a poly(oxyalkylene) hydroxyaromatic ether having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.5 is hydrogen, alkyl having 1 to 30 carbon atoms, phenyl, aralkyl or alkaryl having 7 to 36 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, or aralkyl or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10; and(b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range.Type: GrantFiled: December 18, 1992Date of Patent: November 22, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
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Patent number: 5350872Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.Type: GrantFiled: October 29, 1993Date of Patent: September 27, 1994Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5344961Abstract: An improved process for the carbonylation of aryl halides comprises contacting the aryl halide with carbon monoxide under carbonylation conditions in the presence of a co-reactant, a base, and a catalyst system formed from a source of palladium and a bidentate phosphine ligand wherein at least one monovalent phosphorus substituent is aromatic and is substituted on at least one aromatic ring carbon atom with an electron-withdrawing group.Type: GrantFiled: May 27, 1993Date of Patent: September 6, 1994Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5342986Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphonocarboxylic acids or phosphinocarboxylic acids, and the use thereof as surface-active agents.Type: GrantFiled: November 24, 1993Date of Patent: August 30, 1994Assignee: Bayer AGInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Cornelia Dorzhach-Lange, Hans-Heinrich Moretto
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Patent number: 5342835Abstract: Compounds of formula ##STR1## in which: CYCLE surrounded by a semicircle represents, with the two carbon atoms to which the semicircle is linked, a carbon-containing, optionally heterocyclic, ring containing at least one ethylenic or aromatic bond between the two carbon atoms which carry the --C(Z).dbd.Y group and the phenyl group, Y is oxygen or sulphur, Z is NR.sub.1 R.sub.2, R.sub.1 and R.sub.2, each represents optionally substituted alkyl, alkoxy or cycloalkyl; alkenyl or alkynyl; or --NR.sub.1 R.sub.2 represents saturated or unsaturated heterocyclyl;R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.Type: GrantFiled: January 3, 1992Date of Patent: August 30, 1994Assignee: Rhone-Poulenc AgrochimieInventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
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Patent number: 5340810Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl and C.sub.1-6 alkoxy;R.sup.2 represents a phenyl group substituted by a group selected from ##STR2## and optionally further substituted by one or two substituents selected from halogen atoms, C.sub.1-6 alkoxy, hydroxy, and C.sub.1-6 alkyl;R.sup.3 represents the group ##STR3## R.sup.4 and R.sup.5, which may be the same or different each independently represent a hydrogen atom or a halogen atom or a group selected from hydroxy, C.sub.1-6 alkoxy and C.sub.1-6 alkyl;R.sup.6 represents a hydrogen atom or a group selected from --NR.sup.9 R.sup.10 and a C.sub.1-6 alkyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkoxy, hydroxy, C.sub.1-6 acyloxy and --SO.sub.2 R.sup.11 ;R.sup.7, R.sup.8 and R.sup.Type: GrantFiled: September 17, 1992Date of Patent: August 23, 1994Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Malcolm Carter
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Patent number: 5334370Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.Type: GrantFiled: February 4, 1993Date of Patent: August 2, 1994Assignee: Sterling Winthrop Inc.Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
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Patent number: 5332856Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r'' represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r'' taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.Type: GrantFiled: December 16, 1992Date of Patent: July 26, 1994Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5312966Abstract: There is disclosed a process for efficiently producing a carboxylic acid ester and formamide by reacting a carboxylic acid amide with a formic acid ester or with an alcohol and carbon monoxide in the presence of a strongly basic anion-exchange resin. By the use of the strongly basic anion-exchange resin as the catalyst, the process of the present invention enables the efficient production of the carboxylic acid ester as well as formamide from the Carboxylic acid amide and Formic acid ester, etc. with a high selectivity under mild reaction conditions and facilitates the separation of the catalyst from the reaction product, thereby greatly enhancing the industrial significance of itself.Type: GrantFiled: September 14, 1992Date of Patent: May 17, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Yoshiyuki Nishide, Nobuyuki Muro, Hirofumi Higuchi
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Patent number: 5308607Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.Type: GrantFiled: February 4, 1993Date of Patent: May 3, 1994Assignee: Sterling Winthrop Inc.Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
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Patent number: 5302746Abstract: A process for producing a carboxylic acid ester which comprises reacting a carboxylic acid with an alcohol in the presence of an acid catalyst to produce a reaction solution and neutralizing the reaction solution, characterized by using a countercurrently contacting column for neutralization, into which the esterified reaction solution is introduced at the lower portion of the column, an aqueous strong alkaline solution at a middle portion and an aqueous weak alkaline solution at an upper portion, removing a neutralized oil phase containing the carboxylic acid ester from the top of the column and removing an aqueous phase from the bottom, thereby continuously neutralizing the reaction solution.Type: GrantFiled: April 12, 1993Date of Patent: April 12, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Seiji Koono, Osamu Moriya, Toshio Noguchi, Haruki Okamura
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Patent number: 5292928Abstract: In a process for reacting a low molecular weight hydroxy compound with a carboxylic acid halide, a small amount of the acid halide is introduced into the reaction vessel and the remainder of the acid halide and the hydroxy compound are added gradually in an approximately stoichiometric ratio. The hydrogen halide formed is thus prevented from dissolving in the reaction medium. The heat of reaction to be dissipated is negligible.Type: GrantFiled: July 31, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventor: Karlheinz Miltenberger
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Patent number: 5278333Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.Type: GrantFiled: July 30, 1992Date of Patent: January 11, 1994Assignee: Tessenderlo Chemie N.V.Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
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Patent number: 5258172Abstract: Contrast agents comprising stable aqueous emulsions of iophendylate and their use in radiological examination of the small and large intestine after oral administration are described.Type: GrantFiled: August 15, 1990Date of Patent: November 2, 1993Inventor: Daniel L. Rubin
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Patent number: 5254732Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.Type: GrantFiled: February 28, 1992Date of Patent: October 19, 1993Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5248813Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:(1) has at least one eutectic point;(2) a composition that is not at the eutectic point; and(3) a eutectic composition that is closer to the racemic composition than is the eutectic composition of said aryl-substituted carboxylic acid.Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.Type: GrantFiled: October 14, 1992Date of Patent: September 28, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
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Patent number: 5237092Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.Type: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
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Patent number: 5233075Abstract: A process comprising preparing an aromatic carboxylic ester and an alkyl iodide by carboxylating an aromatic iodide in the presence of an alkylating agent and a catalytic amount of a transition metal under aromatic carboxylic ester and alkyl iodide forming conditions of temperature, pressure and ultrasound.Type: GrantFiled: October 15, 1991Date of Patent: August 3, 1993Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Andrew J. Matosky
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Patent number: 5214195Abstract: The present invention provides new allyl esters of the general formula:X--CH.sub.2 --CR.sup.1 .dbd.CR.sup.2 --CO--Y--R.sup.3 --A (I)wherein R.sup.1 and R.sup.2, which can be the same or different, are hydrn or halogen atoms or alkyl or aryl radicals, R.sup.3 is a linking grouping (spacer), X is an acyloxy radical in which acyl in the acyloxy radical is the residue of an aliphatic carboxylic acid or is the radical RCO-- in which R is an organic radical, Y is an oxygen or sulphur atom or especially an --NH-- group and A is a grouping which can react with a solid carrier material F, which contains appropriate functional groups B, either after selective deblocking or directly, whereby A and B are atom groupings which react with one another with condensation and/or addition and formation of a linkage between the solid carrier material and the radical X--CH.sub.2 --CR.sup.1 .dbd.CR.sup.2 --CO--Y--R.sup.3 --.The present invention also provides processes for the preparation of these new allyl esters.Type: GrantFiled: August 31, 1990Date of Patent: May 25, 1993Assignee: Orpegen Medizinisch-Molekular Biologische Forschungsgesellschaft mbHInventors: Horst Kung, Winfried Kosch, Joachim Marz
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Patent number: 5208366Abstract: An improved process is provided for the preparation of esters of polyhalophthalic acids, polyhalobenzoic acids, and polyhalophthalic anhydride useful as flame retardants for thermoplastic and thermosetting resins, which comprises the reaction of the above acids or anhydride with alcohols in the presence of certain metal and metallorganic compounds as catalysts. Also provided are certain esters per se.Type: GrantFiled: August 19, 1991Date of Patent: May 4, 1993Assignee: Elf Atochem North America, Inc.Inventors: Joseph M. Bohen, Anthony J. Mancuso
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Patent number: 5206423Abstract: This invention provides process embodiments for acyloxylation of C.sub.1 -C.sub.4 alkylaromatic compounds to produce alpha-acyloxy C.sub.1 -C.sub.4 alkyl-substituted aromatic compounds, utilizing a palladium-tin catalyst which exhibits efficient oxidation selectivity and oxidation rate stability.Toluene is acetoxylated to benzyl acetate and benzylidene diacetate.Type: GrantFiled: November 6, 1991Date of Patent: April 27, 1993Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventors: Robert L. Augustine, Setrak K. Tanielyan
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Patent number: 5200550Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or monoor polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.Type: GrantFiled: July 17, 1990Date of Patent: April 6, 1993Assignee: Centre International de Recherces Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon
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Patent number: 5196541Abstract: There is described a new process for the preparation of substituted 3-aminoacrylic esters of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n have the meaning given in the description.The 3-aminoacrylic esters of the formula (I) are obtained by reacting acetic esters of the formula (II)R.sup.1 --(X).sub.n --CH.sub.2 --COOR.sup.Type: GrantFiled: August 2, 1991Date of Patent: March 23, 1993Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Alexander Klausener, Peter C. Knuppel, Fritz Maurer
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Patent number: 5194668Abstract: Carboxylic acid esters and formamide are efficiently obtained by reacting carboxylic acid amides and formic acid esters, or by reacting carboxylic acid amides, alcohols and carbon monoxide in the presence of a dehydrated condensate of carboxylic acid amide with an alkali metal hydroxide or an alkaline earth metal hydroxide catalyst.Type: GrantFiled: June 8, 1990Date of Patent: March 16, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
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Patent number: 5177250Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.Type: GrantFiled: May 13, 1991Date of Patent: January 5, 1993Assignee: Ethyl CorporationInventor: Kathleen S. Laurenzo