Monocyclic Patents (Class 562/493)
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Patent number: 5362909Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: October 29, 1992Date of Patent: November 8, 1994Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5359122Abstract: The preparation of 3-arylacrylic acids and their derivatives I ##STR1## where Ar is aryl which can additionally have substituents which do not react with ketene and are stable under the conditions of the reaction described below, andR.sup.1 is hydrogen, an alkali metal, an alkaline earth metal, ammonium or C.sub.1 -C.sub.20 -alkyl,comprises a first stage in which a dialkyl acetal of an aromatic aldehyde of the formula II ##STR2## where R.sup.2 is C.sub.1 -C.sub.4 -alkyl, is reacted with ketene of the formula CH.sub.2 .dbd.C.dbd.O in the presence of catalytic amounts of a protic or Lewis acid to give a 3-arylpropionic acid derivative of the formula III ##STR3## and a second stage in which this intermediate III is reacted in the presence of acid or base and, in the case where R.sup.1 is C.sub.1 -C.sub.20 -alkyl, additionally with a C.sub.1 -C.sub.20 -alkanol to give the final product I.Type: GrantFiled: February 8, 1994Date of Patent: October 25, 1994Assignee: BASF AktiengesellschaftInventors: Michael Huellmann, Josef Gnad, Rainer Becker
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Patent number: 5352823Abstract: A process for producing crystalline ibuprofen having a crystal habit characterized by a particle length larger than 75 microns average and a length to width aspect ratio of greater than about 4 to 1 to about 5 to 1. The process involves crystallizing ibuprofen from a saturated solution of ibuprofen in a liquid hydrocarbon solvent by seeding and cooling such solution to a temperature of about 0.degree. C. to about -20.degree. C. at a rate to retard primary nucleation and promote secondary nucleation. The crystalline ibuprofen is separated from the slurry produced from such cooling.Type: GrantFiled: October 20, 1992Date of Patent: October 4, 1994Assignee: Albemarle CorporationInventors: Lloyd E. Goddard, George A. Knesel
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Patent number: 5352701Abstract: 1. Leukotriene-B.sub.4 antagonists of formula I ##STR1## are described, in which X is a CH.sub.2 group or an oxygen atom,Y is C.sub.1 -C.sub.4 -alkoxy or --S(O).sub.p --C.sub.1 -C.sub.4 -alkyl,p is 0, 1 or 2Z is a hydrogen atom or the radical A-B-COOH with A being a hydroxymethylene group or a carbonyl group and B being an alkylene group with 1-6 atoms in the chain or a radical ##STR2## with the exception that B cannot mean the radical ##STR3## if X is a CH.sub.2 group, R.sub.1 is the radical OH, --O--(C.sub.1 --C.sub.4) -alkyl, --O--(C.sub.3-C.sub.6) -cycloalkyl, --O--(C.sub.7-C.sub.12) -aralkyl or the radical NHR.sub.4 with R.sub.4 being hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, C.sub.6 -C.sub.10 -aryl or (C.sub.7 -C.sub.12)-aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their use as pharmaceutical agents.Type: GrantFiled: May 5, 1993Date of Patent: October 4, 1994Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5347057Abstract: This invention teaches the oxidation of alkanes and cycloalkanes in the presence of air or oxygen and a ruthenium metal complex catalyst containing an end or bridged-oxo group with a liquid L and carboxylato groups. This oxidation process results in very high yields, utilizes very little energy and has a high catalyst turnover rate.Type: GrantFiled: January 25, 1993Date of Patent: September 13, 1994Inventor: Mirza M. T. Khan
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Patent number: 5336806Abstract: Disclosed is a process for isolating and purifying 2,4,5-trifluorobenzoic acid from a solution in a decarboxylating solvent such as NMP. The solution is neutralized with a hydroxide. This results in the formation of a salt of the 2,4,5-trifluorobenzoic acid, which precipitates. The slurry is filtered to collect the precipitated salt and the precipitated salt is dissolved in water. The aqueous solution of the salt is then acidified which results in the reformation and precipitation of the 2,4,5-trifluorobenzoic acid.Type: GrantFiled: September 20, 1993Date of Patent: August 9, 1994Assignee: Occidental Chemical CorporationInventor: Jian S. Qi
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Patent number: 5331011Abstract: Disclosed is an N-benzyl-N-phenoxyethylamine selected from the group consisting of the N-benzyl-N-phenoxyethylamine represented by the following formula (I): ##STR1## and an agriculturally acceptable acid addition salt represented by the following formula (II): ##STR2## wherein m represents a number of 1 or 2 with a proviso that when m is 1 and a chlorine atom in the ring A is present at para(4)-position of the ring A, two chlorine atoms in the ring B are present at 2,3-, 2,5-, 2,6-, 3,4- or 3,5-positions of the ring B, and HX represents an acid.Type: GrantFiled: April 7, 1993Date of Patent: July 19, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
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Patent number: 5321154Abstract: (.+-.)-2-(4-Isobutylphenyl)-propionic acid can be resolved into optically active isomers easily and with high yields. The method is characterized by the use of the optically active amine of the following general formula (I) or (II) as a resolving agent.Type: GrantFiled: July 31, 1992Date of Patent: June 14, 1994Assignee: Nagase & Company, Ltd.Inventor: Hiroyuki Nohira
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Patent number: 5318770Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize trifluorometyl derivatives of iodinated X-ray contrast media. Typical magnetic resonance contrast media within the scope of the present invention include bis(trifluoromethyl)benzene derivatives, tris(trifluoromethyl)benzene derivatives, tetrakis(trifluoromethyl)benzene derivatives, and other related trifluoromethylated benzene derivatives.Type: GrantFiled: October 25, 1991Date of Patent: June 7, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: David H. White, Steven R. Woulfe, Youlin Lin, Mills T. Kneller
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Patent number: 5302752Abstract: Compounds of formula ##STR1## where n is an integer from 1 to 12, R and R.sub.1 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl as well as their physiologically active salts and amides thereof and the enantiomers, mixtures and racemates are disclosed. Intermediates useful in preparing the above compounds are also disclosed as are processes for preparing these compounds.Type: GrantFiled: April 16, 1990Date of Patent: April 12, 1994Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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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: 5274186Abstract: Compounds of formula ##STR1## (wherein Ar, R, R.sub.1 and X have the meaning reported in the description) are useful intermediates for the preparation of a variety of organic compounds, also optically active, like alpha-haloketones, alpha-hydroxyketones or ketals, alpha-arylalkanoic acids.Type: GrantFiled: January 19, 1989Date of Patent: December 28, 1993Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi
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Patent number: 5264408Abstract: The present invention relates to ceramic materials containing a homogeneous dispersion of metal particles, particularly sol-gel ceramic materials, a method of preparing the same, and processes for hydrogenating and oxidizing organic compounds using the same.Type: GrantFiled: July 31, 1992Date of Patent: November 23, 1993Assignee: University of South CarolinaInventors: James M. Tour, Shekar L. Pendalwar, Joel P. Cooper
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Patent number: 5254714Abstract: 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: October 10, 1991Date of Patent: October 19, 1993Assignee: Ethyl CorporationInventor: Merrikh Ramezanian
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Patent number: 5241111Abstract: A process for producing a 5-fluorobenzoic acid of the formula (V), which comprises trichloromethylating a fluorobenzene of the formula (I) to obtain a 5-fluorobenzotrichloride of the formula (II), then reacting it with aqueous ammonia to obtain a 5-fluorobenzonitrile of the formula (III), reacting it with a fluorinating agent to obtain a 5-fluorobenzonitrile of the formula (IV) and hydrolyzing it: ##STR1## wherein each of X.sub.1, X.sub.3, Y.sub.1 and Y.sub.3 is a halogen atom, and each of X.sub.2 and Y.sub.2 is hydrogen or a halogen atom.Type: GrantFiled: November 15, 1990Date of Patent: August 31, 1993Assignees: Asahi Glass Company Ltd., Seimi Chemical Co., Ltd.Inventors: Seisaku Kumai, Masao Ohashi, Yutaka Yaginuma, Katsuhiko Takeda
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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: 5214193Abstract: A bisphenol monoester represented by the formula (I): ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 and R.sup.3 are each alkyl, and R.sup.4 is alkyl, alkenyl or phenyl, is produced by continuous two step reactions in which an aldehyde R.sup.1 -CHO and 2,4-dialkylphenol are subjected to a condensation reaction in a C.sub.6 -C.sub.10 aliphatic or C.sub.6 -C.sub.12 aromatic hydrocarbon solvent, and then a resulting bisphenol compound dissolved in the solvent is subjected to an esterification with a carboxylic acid R.sup.4 --COOH or its derivative. Prior to the esterification, the organic layer containing the bisphenol compound is subjected to a dehydration treatment, thereby enabling the two steps to proceed continuously without isolating the intermediate bisphenol compound. A purification process for the bisphenol monoester of the formula (I) is also disclosed in which the monoester is purified from a mixed solvent comprising a C.sub.6 -C.sub.12 aromatic hydrocarbon solvent and a C.sub.1 -C.sub.Type: GrantFiled: February 12, 1992Date of Patent: May 25, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Kikumitsu Inoue, Manji Sasaki, Kazuaki Yamamoto, Shinichi Yachigo
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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: 5202472Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: April 13, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
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Patent number: 5198576Abstract: Bicyclooctyl phosphines are disclosed having the formula: ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, halo, or C.sub.1 or C.sub.6 alkoxy; Ar is phenyl, substituted phenyl, naphthyl or substituted naphthyl; and x is 0 or 1.These phosphines are treated with ruthenium compounds to form a complex of the formula Ru.sub.x H.sub.y Cl.sub.z (anthraphos-m).sub.2 (S).sub.p, where S is a tertiary amine; and when y is 0, then x is 2, z is 4 and p is 1; and when y is 1, then x is 1, z is 1 and p is 0; where anthraphos-m is: ##STR2## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, C.sub.1 to C.sub.6 linear or branched alkoxy or halo; Ar is phenyl or substituted phenyl or naphthyl or substituted naphthyl; and m is 0 or 1.The complex is useful in a process for the asymmetric reduction of olefinic carboxylic acids of the formula: ##STR3## where R.sub.1 and R.sub.Type: GrantFiled: August 26, 1991Date of Patent: March 30, 1993Assignee: Ethyl CorporationInventor: Ralph T. Scannell
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Patent number: 5196590Abstract: Disclosed is a method of making 2,4,5-trihalobenzoic acid by heating to a temperature of about 130.degree. to about 190.degree. C. a composition that comprises water, a mineral acid, and a compound having the general formula ##STR1## where "X" is fluorine, chlorine, or bromine and "R" is alkyl from C.sub.1 to C.sub.10 or aryl. The fluorine product is useful in making quinolone antibacterial drugs.Type: GrantFiled: May 11, 1992Date of Patent: March 23, 1993Assignee: Occidental Chemical CorporationInventors: J. Steven Oi, Joseph J. Moritz
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Patent number: 5190905Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: March 2, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
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Patent number: 5191095Abstract: A process for the asymmetric reduction of olefinic amides of the formula ##STR1## where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: March 2, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
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Patent number: 5187281Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
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Patent number: 5187135Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
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Patent number: 5187136Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: W. Dirk Klobucar, Charles H. Kolich, Thanikavelu Manimaran
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Patent number: 5179230Abstract: A process for the preparation of 2,3,4,5,-tetrafluorobenzoic acid of the formula (1) ##STR1## by heating N'-substituted N-aminotetrafluorophthalimides of the formula (2) ##STR2## in which X is the radical ##STR3## where R.sub.1, R.sub.2 are a hydrogen atom, an alkyl-(C.sub.1 -C.sub.10)- group, aryl group, alkyl-(C.sub.1 -C.sub.6)-Co- group or aryl-CO- group, it being possible for the aryl or aryl-CO- group in the case of R.sub.1 and R.sub.2 to be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl-(C.sub.1 -C.sub.4)-groups, or R.sub.1 and R.sub.2 together are a phthaloyl radical which can be substituted on the aromatic ring by 4 chlorine atoms or 4 fluorine atoms, or where X is the radical ##STR4## which can be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl-(C.sub.1 -C.sub.4)- groups, in an aqueous medium at pH values of approximately -1 to approximately +1 at temperatures of approximately 160 to approximately 220.degree. C.Type: GrantFiled: April 23, 1992Date of Patent: January 12, 1993Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Ralf Pfirmann
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Patent number: 5177231Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: January 5, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
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Patent number: 5162577Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.Type: GrantFiled: February 1, 1991Date of Patent: November 10, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Raffaello Masciadri
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Patent number: 5113013Abstract: A method for the preparation of a fluorine-containing organic compound which comprises reacting a sulphonyl halide of the formula:RfSO.sub.2 Xwhere Rf represents a fluorinated organic radical and X represents a halogen atom, with a reactive organic halide in the presence of a metal known to complex with fluorinated organic radicals.Type: GrantFiled: April 26, 1990Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventors: Richard L. Powell, Charles A. Heaton
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Patent number: 5107053Abstract: A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula ##STR1## wherein R and R' are the same or different and are C.sub.1 to C.sub.6 linear or branched alkyl; R" is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.1 is C.sub.1 to C.sub.6 linear or branched alkyl; and n is an integer from 1 to 6.The phosphine complex is particularly useful in the asymmetric hydrogenation of unsaturated carboxylic acids or alkyl esters thereof.Type: GrantFiled: October 25, 1991Date of Patent: April 21, 1992Assignee: Ethyl CorporationInventor: Tse-Chong Wu
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Patent number: 5093529Abstract: In the process for the preparation of fluorinated benzoic acids of the formula I ##STR1## in which X and Y, for example, independently of one another denote chlorine or fluorine and X moreover denotes bromine, a fluorinated chloroacetophenone of the formula II ##STR2## in which Z denotes chlorine or hydrogen, is reacted with a hypohalite.Type: GrantFiled: July 16, 1990Date of Patent: March 3, 1992Assignee: Cassella AktiengesellschaftInventor: Horst Schmand
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Patent number: 5089661Abstract: A new process is described for the preparation of a 2-aryl-propionic acid, such as for instance 2-[4-(2-methyl-propyl)phenyl]propionic or 2-(6'-methoxy-2'-naphthyl)propionic acid, through hydrogenation of a complex salt which consists of the mono- and/or di-valent anion of the corresponding 2-hydroxy-2-aryl-propionic acid, a di- or tri-valent metal cation, such as for instance Al(+3), Fe(+3), Zn(+2), or Mg(+2), and optionally other anonic or neutral ligands.This new process is particularly advantageous in that the starting salt can be obtained directly via electrocarboxylation of the corresponding aryl methyl ketone, e.g. 4-(2-methyl-propyl)acetophenone or (6-methoxy-2-naphthyl) methyl ketone, with metal anodes which dissolve during the electrolysis.Type: GrantFiled: September 10, 1990Date of Patent: February 18, 1992Assignee: Enichem Synthesis S.p.A.Inventors: Federico Maspero, Oreste Piccolo, Ugo Romano, Salvatore Gambino
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Patent number: 5081252Abstract: A process for the preparation of aromatic carboxylic acids or their salts comprises heating carboxyl-free aromatic compounds and aromatic carboxylic acid salts whose basic structures differ from those of the aromatic compounds, or heating polycyclic aromatic compounds with three or more rings and monocyclic or bicyclic aromatic carboxylic acid salts, under carbon dioxide pressure in the presence of one or more metal compounds selected from group (a) of compounds of zinc, cadmium, and thallium and one or more compounds selected from group (b) of compounds of cesium, Group II metals, And Group IIIa metals to effect the intermolecular transfer of the carboxyl groups.Type: GrantFiled: June 5, 1989Date of Patent: January 14, 1992Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.Inventors: Shuichi Mitamura, Yoshimi Kata, Koichi Fujishiro, Yasuhisa Tsutsumi
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Patent number: 5072038Abstract: 2,3,4,5-trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: January 2, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5047538Abstract: Novel 8-alkenyl, alkynyl, allenyl and cycloalkyl-quinolinecarboxylic acids are described as antibacterial agents as well as methods of manufacture including novel intermediates used in said manufacture.Type: GrantFiled: April 12, 1990Date of Patent: September 10, 1991Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Mark J. Suto, William R. Turner
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Patent number: 5004832Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.Type: GrantFiled: February 6, 1989Date of Patent: April 2, 1991Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4999441Abstract: Tetrakis(dialkylamino)aromatics Ia to Ic ##STR1## where the radicals A may be identical or different and are n-C.sub.1 -C.sub.6 -alkyl and the radicals R may be identical or different and are hydrogen or C.sub.1 -C.sub.6 -alkyl, and their charge transfer complexes with electron acceptors, and the preparation of Ia to Ic from the corresponding N-unsubstituted amines by alkylation with A'--CHO (where A'.dbd.H or N-C.sub.1 -C.sub.5 -alkyl) and reduction with NaBH.sub.3 CN.The charge transfer complexes of Ia and Ic are used to prepare electrically conductive polymers.Type: GrantFiled: April 17, 1989Date of Patent: March 12, 1991Assignee: Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.Inventors: Heinz A. Staab, Karin Elbl
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Patent number: 4996355Abstract: The present invention comprises compounds of the formulas: ##STR1## wherein X is Cl or Br. These compounds are useful as intermediaries for the production of 2,4,5-trifluorobenzoic acid and 2,4,5-trifluorobenzoyl fluoride.Type: GrantFiled: April 14, 1989Date of Patent: February 26, 1991Assignee: Mallinckrodt, Inc.Inventor: Narayanasamy Gurusamy
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Patent number: 4994610Abstract: Fluorinated benzoyl compounds of the formula: ##STR1## wherein Q is a lower alkyl group, a halogen atom, --CH.sub.2 CO.sub.2 R.sup.1 wherein R.sup.1 is a lower alkyl group, or ##STR2## wherein each of R.sup.2 and R.sup.3 is a lower alkyl group, are disclosed.Type: GrantFiled: December 5, 1989Date of Patent: February 19, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki
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Patent number: 4990661Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: March 29, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
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Patent number: 4968830Abstract: Halogen substituted aromatic compounds of the formula ##STR1## wherein Y is selected from the group CO.sub.2 H, COF, COCl, COBr, CF.sub.3, CN, NCO, or F, and X and X' are independently hydrogen or a halogen selected from the group F-, Cl- and Br-, at least one of X and X' being halogen; may be prepared by the liquid phase reaction of a brominating agent, at temperatures below about 190.degree. Celsius, with a correspondingly substituted cyclohexene or cyclohexadiene.Type: GrantFiled: September 11, 1989Date of Patent: November 6, 1990Assignee: Occidental Chemical CorporationInventor: David Y. Tang
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Patent number: 4937379Abstract: A process is described for preparing alpha-arylalkanoic acids, which comprises preparing and subsequently rearranging ketals of formula ##STR1## (in which Ar, R, R.sub.1, R.sub.2 and R.sub.4 have the meanings given in the description).The ketals of formula II are prepared from the corresponding alpha-hydroxyketals.The rearrangement reaction is conducted under mild conditions.Type: GrantFiled: July 30, 1987Date of Patent: June 26, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Marco Villa
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Patent number: 4929755Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and H.sub.2 O or an organic hydroxyl compound to produce an N-acyl-.alpha.-amino acid or ester, respectively, the improvement comprising using as the .alpha.-enamide reactant, an .alpha.-enamide which has a chiral center that is essentially all L or D, thereby producing a reaction mixture containing diastereomeric N-acyl-.alpha.-amino acids or esters having two chiral centers, said mixture having essentially no enantiomeric pairs.Type: GrantFiled: December 19, 1986Date of Patent: May 29, 1990Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4927967Abstract: A process for the production of organic carboxylic acids by the catalytic reaction of organic formate esters in contact with carbon monoxide and a homogeneous catalyst system of rhodium metal atom, a phosphorus containing ligand in which there is present at least one oxo oxygen atom attached to a phosphorus atom or a carbon atom to form a Z group and the ##STR1## group in said Z group is located at least one carbon atom removed and preferably from 2-4 carbon atoms removed from the phosphorus atom of the molecules represented by the formulas ##STR2## and a halogen source, under mild reaction conditions, wherein R' is H, aryl, alkaryl, aralkyl or alkyl, and wherein 1 or more of said R' groups can be substituted with a Z group but not more than 3 of said R' groups in the molecule are so substituted; a is an integer from 0-4; b is an integer from 0-3; and Z is P(O)R'R'; --C(O)OR" or C(O)R", wherein R" is R'.Type: GrantFiled: November 6, 1985Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Richard W. Wegman
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Patent number: 4920120Abstract: Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: December 9, 1988Date of Patent: April 24, 1990Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Susan E. Hagen, John S. Kiely
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Patent number: 4918226Abstract: A process for converting formic acid esters or transesterification products thereof to carboxylic acids comprising contacting a formic acid ester of the formula (HCOO).sub.n --R where R is aliphatic, cycloaliphatic or aralkyl and n is 1 or 2 with a catalytically effective amount of a soluble iridium salt and an iodide promoter at a temperature of from about 100.degree. C. to about 300.degree. C. in the presence of an organic solvent containing at least one carboxylic acid.Type: GrantFiled: June 22, 1981Date of Patent: April 17, 1990Assignee: Exxon Research and Engineering CompanyInventor: Roy L. Pruett
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Patent number: 4910321Abstract: This invention provides a novel catalyst composed of a complex of an organic acid or its ester and a Lewis acid, preferably boron trichloride that can add olefin monomers to increase the molecular weight of the complex from as low as 200 to in excess of a million, with the complex being active viz., living, until the complex dies, viz., is decomposed or destroyed so that polymers in the liquid or easily liquefiable range of 300 to about 20,000 can be made or those more difficult to be liquefied or unliquefiable, viz., those of over 10,000 up to 100,000 or in some cases 500,000 and then those in the range of the elastomers, or moldable or extrudable plastics range having very high molecular weights, generally in excess of 100,000 up to in excess of 500,000 and having useful end groups such as the halogens and specifically chloride, allyl, acryl or methacryl, acetate or formate to name some of the more useful ones.Type: GrantFiled: February 16, 1988Date of Patent: March 20, 1990Assignee: University of AkronInventors: Joseph P. Kennedy, Rudolf Faust
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Patent number: 4904646Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have the structure ##STR1## including salts thereof, wherein R is OH, lower alkoxy or lower alkyl; R.sup.x is H or alkyl;X is --O-- or --NH--;n is 1 or 2Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds. New intermediates used in preparing the above compounds, pharmaceutical compositions containing such compounds and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.Type: GrantFiled: April 18, 1988Date of Patent: February 27, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Scott A. Biller, Eric M. Gordon
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek