Carboxyl, Or Salt Thereof, Not Bonded Directly To Ring Patents (Class 562/496)
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Patent number: 5352791Abstract: Shaped organosiloxane amine copolycondensates are described which contain Pd, Pt, Ru and/or Rh, as well as optional promotors and/or moderators. The shaped copolycondensate function as a carrier for metals and are made up of units of: ##STR1## and/or units of Y--R.sup.6. R.sup.2 to R.sup.6 are a group represented by the formula: ##STR2## wherein R.sup.7 is a group bound to N, X, or Y (for example, an alkylene group) and R.sup.1 is R.sup.7 --SiO.sub.3/2, H, CH.sub.3, C.sub.2 H.sub.5, or C.sub.3 H.sub.7. X stands for a double-bonded group such as --S--, --S.sub.2 --, --S.sub.3 --, --S.sub.4 --, --HN--CS--NH-- and Y stands for a monovalent groups such as --CN, --SCN, --SH, --S--CH.sub.3, --NH.sub.2, --NH--(CH.sub.2).sub.2 --NH.sub.2. The carrier substance may be cross-linked with cross-linking agents containing Si, Ti, Zr or Al. The metal-containing product is spherical in form and is defined by the parameters of sphere diameter, specific surface and pore volume as well as bulk density.Type: GrantFiled: September 16, 1993Date of Patent: October 4, 1994Assignee: Degussa AktiengesellschaftInventors: Peter Panster, Stefan Wieland
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Patent number: 5344970Abstract: A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl.This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.Type: GrantFiled: December 22, 1993Date of Patent: September 6, 1994Assignee: Albemarle CorporationInventor: Charles H. Kolich
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Patent number: 5344843Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.2 ' X, Y, Z, A, B, Q and n are as described herein. Their pharmaceutically acceptable salts, and when appropriate, enantiomers, racemates, diastereomers or mixtures thereof or geometric isomer or mixtures thereof, and pharmaceutically acceptable salts thereof. The compounds of formula I inhibit enzyme carnitine acyltransferase 1 (CAT-1) and are therefore useful in the prevention of injury to ischemic tissue, and can limit infarct size, improve cardiac function and prevent arrhythmias during and following a myocardial infarction.Type: GrantFiled: March 13, 1992Date of Patent: September 6, 1994Assignee: Hoffman-La Roche Inc.Inventors: Robert W. Guthrie, John G. Mullin, Jr., David F. Kachensky, Richard W. Kierstead, Jefferson W. Tilley, Guy P. Heathers, Alan J. Higgins, Ronald A. LeMahieu
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Patent number: 5332834Abstract: There is disclosed and claimed a process whereby S(+)-ibuprofen L-lysinate salt is produced by selective precipitation from a mixture containing enantiomers of ibuprofen and L-lysine. The quantity of L-lysine is not more than about a molar equivalent of the quantity of S(+)-ibuprofen in the ibuprofen enantiomeric mixture. The mother liquors after separating the above salt are enriched in R-ibuprofen which is racemized by a novel thermal racemization process and may then be recycled.Type: GrantFiled: December 2, 1992Date of Patent: July 26, 1994Assignee: Hoechst Celanese CorporationInventors: Apurba Bhattacharya, John R. Fritch, Carl D. Murphy, Larry D. Zeagler, Carina Araullo-McAdams
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Patent number: 5310961Abstract: A novel neomorphic form of ibuprofen and processes for preparing the ibuprofen are provided. The neomorphic form is characterized by having a distinctively less bitter taste and causes less burning sensation upon swallowing. The neomorphic form of ibuprofen is an amorphous ibuprofen and is prepared by imparting kinetic energy to supercooled ibuprofen.Type: GrantFiled: July 2, 1993Date of Patent: May 10, 1994Assignee: Affinity Biotech, Inc.Inventors: Robert P. Geyer, Vinod V. Tuliani
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Patent number: 5310960Abstract: A novel neomorphic form of ibuprofen and processes for its preparation are provided. The neomorphic ibuprofen is characterized by having a distinctively less bitter and acidic taste commonly associated with conventional ibuprofen and which causes less burning sensation upon swallowing. The neomorphic form of ibuprofen is an amorphous ibuprofen and is prepared by resolidifying supercooled ibuprofen at a process temperature below 0.degree. C.Type: GrantFiled: July 2, 1993Date of Patent: May 10, 1994Assignee: Affinity Biotech, Inc.Inventors: Robert P. Geyer, Vinod V. Tuliani
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Patent number: 5306833Abstract: Process for obtaining an arylacetic acid of general formula (I):Ar--CHR--COOH (I)in which R=H, C.sub.1 -C.sub.4 alk, Ar=2-thienyl, 3-thienyl, 1-naphthyl, 2-naphthyl, 1-(2-methoxy naphthyl), 3,4-methylenedioxy phenyl or phenyl of general formula (II): ##STR1## in which R.sub.1 =H, OH or C.sub.1 -C.sub.4 alkoxy, R.sub.2 =H, C.sub.1 -C.sub.4 alk, C.sub.1 -C.sub.4 alkoxy or OH, as well as their alkali metal salts, by reaction in a solvent of the corresponding arylglycolic acid of general formula (III):Ar-CR(OH)--COOH (III)or one of its alkali metal salts with a hydrogen donor agent chosen from the group constituted by: formic acid, or one of its alkali metal salts, phosphonic acid, phosphinic acid, or one of their alkali metal salts, in the presence of a hydrogen transfer catalyst, which if desired is isolated or salified, and use for the preparation of certain acids of formula (I).Type: GrantFiled: February 3, 1993Date of Patent: April 26, 1994Assignee: Societe Francaise HoechstInventors: Jean-Claude Vallejos, Yani Christidis
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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: 5300681Abstract: 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: June 10, 1993Date of Patent: April 5, 1994Assignee: Ethyl CorporationInventor: Merrikh Ramezanian
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Patent number: 5254728Abstract: Complexes containing S(+)-ibuprofen, method for the production of these complexes and pharmaceutical preparations containing these complexes are described.Type: GrantFiled: November 15, 1991Date of Patent: October 19, 1993Assignee: Medice Chem.-pharm. Fabrik Putter GmbH & Co. KGInventor: Henrich H. Paradies
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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: 5250325Abstract: Coating composition comprising:A) an organic film-forming binder; andB) a corrosion-inhibiting amount of a water-insoluble salt of i) a carboxylic acid having the formula (I): ##STR1## and ii) a base selected from a) a cation of Group Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, VIa, VIIa or VIIIa of the Periodic Table of Elements, b) an amine of formula II: ##STR2## c) a guanidine of formula III:R.sub.7 --N.dbd.C(NH.sub.2).sub.2 IIId) an amidine of formula IV:R.sub.7 --C(.dbd.NH)NH.sub.2 IVor e) melamine.Type: GrantFiled: January 21, 1993Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Emyr Phillips, William P. Armstrong
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Patent number: 5248815Abstract: The present invention relates to a stereospecific chemical synthesis of optically pure enantiomers of 2-aryl-alkanoic acids, especially those of the biologically active (S)-aryl-propionic acids, in good chemical yields, useful for preparing large quantities thereof, and having a high optical purity.Type: GrantFiled: December 27, 1991Date of Patent: September 28, 1993Inventor: Henrich H. Paradies
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Patent number: 5235101Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5233084Abstract: Process for preparing .alpha.-arylpropionic acids by catalytically asymmetrically hydrogenating .alpha.-arylpropenoic acids prepared from .alpha.-aryl ketones.Type: GrantFiled: December 3, 1990Date of Patent: August 3, 1993Assignee: Monsanto CompanyInventor: Albert S. C. Chan
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Patent number: 5223640Abstract: This invention provides a process to prepare optically active .alpha.-aryl propionic acids without the need for resolving a racemic mixture. In one embodiment of the process, an acetophenone is sequentially converted to a 1-alkyne, then to an .alpha.-aryl .beta.-silylated acrolein, and then to an acrylic acid, which is then asymmetrically hydrogenated to an optically active .alpha.-aryl propionic acid.Type: GrantFiled: December 23, 1992Date of Patent: June 29, 1993Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Sambasivarao Kotha, Kenneth G. Davenport
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Patent number: 5206262Abstract: The salts, in the crystalline form, of ibuprofen and naproxen with N-(2-hydroxyethyl) pyrrolidine are prepared by dissolving ibuprofen and naproxen respectively in a suitable organic solvent, by adding N-(2-hydroxyethyl) pyrrolidine, by letting the compounds react, by removing the solvent and by crystallizing the obtained salt from a solution in an apolar and aprotic solvent.Said salts have a high solubility in water and are used for preparing pharmaceutic compositions for oral and other administrations.Type: GrantFiled: June 23, 1992Date of Patent: April 27, 1993Assignee: Altergon S.A.Inventors: Elisabetta Donati, Irina Rapaport, Paolo Lualdi
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Patent number: 5202474Abstract: Process for preparing .alpha.-arylpropionic acids by catalytically asymmetrically hydrogenating .alpha.-arylpropenoic acids utilizing an asymmetric hydrogenation catalyst at low temperatures and, optionally, at high pressures.Type: GrantFiled: March 2, 1990Date of Patent: April 13, 1993Assignee: Monsanto CompanyInventor: Albert S. C. Chan
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Patent number: 5202473Abstract: A ruthenium-phosphine complex represented by the formula:[RuXY(BINAP].sub.nwherein n is an integer of from 1 to about 10; and X and Y independently represent nonchelating anionic ligands.Type: GrantFiled: July 23, 1992Date of Patent: April 13, 1993Assignee: Monsanto CompanyInventors: Albert S. C. Chan, Scott A. Laneman
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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: 5200558Abstract: S(+)-ibuprofen-L-amino acids and S(+)-ibuprofen-D-amino acids, substantially free of other ibuprofen-amino acid stereoisomers, give an onset-hastened, enhanced analgesic response in humans.Type: GrantFiled: August 9, 1991Date of Patent: April 6, 1993Assignee: Merck & Co., Inc.Inventor: King C. Kwan
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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: 5191114Abstract: Direct compressible ibuprofen particles are formed by treating commercially available, dry ibuprofen with a hydrophilic solvent in one embodiment, a mixture of a hydrophilic solvent and one or more hydrophobic organic solvents in a second embodiment and one or more hydrophobic organic solvents in a third embodiment, to change at least the external crystalline shape of the ibuprofen from a flow-retarding shape to a free-flowing, easily compressible configuration. A typical hydrophilic solvent is water and among the hydrophobic solvents which may be used are acetone, methyl alcohol, ethyl alcohol, isopropyl and N-propyl alcohol. Direct compressible ibuprofen particles having superior flow characteristics may also be prepared by mixing commercially available, dry ibuprofen with micron size, amorphous silica gel in various formulations.Type: GrantFiled: October 9, 1991Date of Patent: March 2, 1993Assignee: Sage Pharmaceuticals, Inc.Inventor: Jivn-Ren Chen
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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: 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: 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: 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: 5176850Abstract: The present invention provides a composition in contact with a corrodable metal surface, comprising a functional fluid and, as corrosion inhibitor, a compound having the formula 1A ##STR1## as well as salts or esters thereof, wherein R.sup.3 is C.sub.9 -C.sub.20 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl;R.sup.4 is C.sub.1 -C.sub.3 alkyl;X is CH.sub.2, O or S;Y is O or S; andZ is--(CH.sub.2).sub.n -in which n is 1,2,3,4 or 5, or Z is--CH.sub.2 --CH(CH.sub.3)-.Type: GrantFiled: February 15, 1991Date of Patent: January 5, 1993Assignee: Ciba-Geigy CorporationInventor: Robert M. O'Neil
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Patent number: 5144067Abstract: Disclosed is a process for the coproduction of (1) an alkyl iodide and (2) an .alpha.-iodocarboxylic acid, a mono-.alpha.-iodocarboxylic anhydride or a mixture thereof which comprises contacting a mixture of an iodine compound and a carboxylic anhydride with a peroxide at an elevated temperature.Type: GrantFiled: September 29, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier, Brent A. Tennant
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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: 5097061Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.Type: GrantFiled: June 19, 1989Date of Patent: March 17, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
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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: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Patent number: 5049455Abstract: Amphiphilic anthracene derivatives having a hydrophobic substituent and a hydrophilic substituent at 9 position and 10 position of the anthracene nucleus, respectively are disclosed. The amphiphilic anthracene derivatives have an excellent film forming property, heat resistance and electroluminescene effect.Type: GrantFiled: September 5, 1990Date of Patent: September 17, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Yasunori Yoshioka
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Patent number: 5041641Abstract: Pentafluorophenyl derivatives are expressed by the formula (I): ##STR1## where X represents an alkyl group having from 1 to 4 carbon atoms or a halogen atom; Y represents any group of --CH.sub.2 OH, --COOH, --COCl, --CON.sup.1 R.sup.2, or --OSO.sub.2 R.sup.3 ; R.sup.1, R.sup.2 and R.sup.3 represent an alkyl group which may have a substituted group, an aryl group which may have a substituted group, or a hydrogen atom except for R.sup.3. However, when X to a halogen atom, Y is the aforementioned groups other than --OSO.sub.2 R.sup.3. A racemate and/or an optical active form of the pentafluorophenyl derivatives can be used suitably as derivatizing agents for electron capture detection and optical resolution for analysis and as intermediates for medicines, agricultural chemicals, functional polymers, etc. The pentafluorophenyl derivatives are produced from pentafluorostyrene oxide.Type: GrantFiled: April 11, 1989Date of Patent: August 20, 1991Assignee: Nippon Mining Company LimitedInventors: Osamu Takahashi, Keizo Furuhashi, Junko Umezawa
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Patent number: 5036156Abstract: Compounds of formula ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or halogen, are prepared by reacting an aldehyde of formula: ##STR2## with CHBr.sub.3 and KOH in a mixture of an inert solvent and water. Further an ester of compound (I) wherein R.sub.1 is H and R.sub.2 is 2-Cl is reacted with 4,5,6,7-tetrahydrothieno[3,2-c]pyridine to produce a compound of formula III: ##STR3## which is useful as a medicament.Type: GrantFiled: June 19, 1990Date of Patent: July 30, 1991Assignee: SanofiInventors: Michel Bouisset, Joel Radisson
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Patent number: 5015764Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt and (iv) separating said precipitated diastereomeric salt.Type: GrantFiled: June 18, 1990Date of Patent: May 14, 1991Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Fred J. Impastato
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Patent number: 5013482Abstract: The present invention provides a composition in contact with a corrodable metal surface, comprising a functional fluid and, as corrosion inhibitor, a compound having the formula I: ##STR1## as well as salts or esters thereof, wherein R.sup.1 is C.sub.4 -C.sub.20 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl;R.sup.2 is C.sub.1 -C.sub.12 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl, or arylalkyl containing 7-20 carbon atoms;X is CH.sub.2, O or S;Y is O or S; andZ is --(CH.sub.2).sub.n -- in which n is 1, 2, 3, 4 or 5, or Z is --CH.sub.2 --CH(CH.sub.3)--.Some of the compounds of formula I are new.Type: GrantFiled: July 17, 1989Date of Patent: May 7, 1991Assignee: Ciba-Geigy CorporationInventor: Robert M. O'Neil
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Patent number: 5001288Abstract: A monoalkylaromatic hydrocarbon is haloethylated to a 1-halo-1-arylethane with minimal co-formation of diarylalkane by-product by reacting it with hydrogen chloride or bromide and acetaldehyde at a temperature in the range of abaout +10.degree. C. to about -35.degree. C. in the presence of at least about 1.4 mols of hydrogen sulfate per mol of the aromatic hydrocarbon and in the absence of more than about 15% by weight of water, based on the weight of the hydrogen sulfate; the temperature being not higher than about -10.degree. C. when hydrogen chloride is employed.Type: GrantFiled: August 17, 1989Date of Patent: March 19, 1991Assignee: Ethyl CorporationInventor: George A. Knesel
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Patent number: 4994607Abstract: Process for preparing .alpha.-arylpropionic acids by catalytically asymmetrically hydrogenating .alpha.-arylpropenoic acids utilizing an asymmetric hydrogenation catalyst at low temperatures and, optionally, at high pressures.Type: GrantFiled: June 22, 1989Date of Patent: February 19, 1991Assignee: Monsanto CompanyInventor: Albert S. C. Chan
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Patent number: 4994604Abstract: A process is disclosed for the formation and resolution of (S)-ibuprofen-(S)-lysine. The process employs preferential crystallization to separate a pair of diasteromeric salts, (S)-ibuprofen-(S)-lysine and (R)-ibuprofen-(S)-lysine.Type: GrantFiled: January 10, 1990Date of Patent: February 19, 1991Assignee: Merck & Co., Inc.Inventors: Hsien-Hsin Tung, Stanley Waterson, Scott D. Reynolds
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Patent number: 4983765Abstract: A process is described in which a mixture of enantiomeric arylpropionic acid is split and one of enantiomeric forms of the acid is recovered. The mixture is transformed into a diastereoisomeric salt by a reaction with a chiralic base and an inert solvent, and the desired acid enantiomer is removed from the reaction product. The transformation to a diastereoisomeric salt takes place in a polar solvent. The salt produced is recrystallized several times and the thus purified salt is split in a dilute mineral acid.Type: GrantFiled: June 27, 1989Date of Patent: January 8, 1991Assignee: PAZ Arzneimittel-Entwicklungsgesellschaft mbHInventors: Helmut Lukas, Otto Schuster, Gunther Rau
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Patent number: 4965361Abstract: Process is disclosed for the preparation of 4-substituted aryl olefins from 4-substituted aryl iodides. 4-Substituted aryl iodides are contacted with an olefin in an ester solvent in the presence of a catalyst system comprising a palladium compound and a Bronsted base.Type: GrantFiled: February 27, 1989Date of Patent: October 23, 1990Assignee: Eastman Kodak CompanyInventor: Kevin J. Edgar
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Patent number: 4962230Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.Type: GrantFiled: November 16, 1987Date of Patent: October 9, 1990Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4946997Abstract: A process is described for the racemization of an optically active carboxylic acid of structure (I): ##STR1## which comprises the treatment of (I) with an acid anhydride and its conjugate base.Type: GrantFiled: June 7, 1989Date of Patent: August 7, 1990Assignee: Merck & Co., Inc.Inventors: Robert D. Larsen, Paul Reider
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Patent number: 4946864Abstract: Novel HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.Type: GrantFiled: February 1, 1988Date of Patent: August 7, 1990Assignee: Merck & Co., Inc.Inventors: John Prugh, Albert A. Deana, Clarence S. Rooney
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Patent number: 4940813Abstract: A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.Type: GrantFiled: March 31, 1989Date of Patent: July 10, 1990Assignee: Merck & Co., Inc.Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
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Patent number: 4937263Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.Type: GrantFiled: July 17, 1989Date of Patent: June 26, 1990Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Ta J. Lee, Robert L. Smith, Clarence S. Rooney
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Patent number: 4937264Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.Type: GrantFiled: June 30, 1989Date of Patent: June 26, 1990Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Ta J. Lee, Clarence S. Rooney