Naphthyl In Acid Moiety Patents (Class 560/100)
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Patent number: 5260482Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process combines an aryl substituted aliphatic carboxylic acid, a base and water in an inert solvent to make a hydrated salt of the said acid. The process leads to enhanced yield of an enantiomerically enriched hydrated salt of the carboxylic acid.Type: GrantFiled: October 14, 1992Date of Patent: November 9, 1993Assignee: Ethyl CorporationInventors: Patricia Pringle, William T. Murray, Douglas K. Thompson, Azfar A. Choudhury, Deepak R. Patil
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Patent number: 5258532Abstract: A fused ring compound having hydroxy, carboxylic acid and hydroxyalkyl substituent groups and the metal salts or complexes thereof. The hydroxyalkyl group is especially a hydroxymethyl group. The compound is prepared by reaction of the hydroxy carboxylic acid derivative with formaldehyde in an alkaline medium at a temperature of not more than 50.degree. C. The compounds, especially the metal salts or complexes thereof, can be used to provide corrosion inhibition of metals, for example iron.Type: GrantFiled: December 10, 1991Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries PlCInventor: John R. Lawson
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Patent number: 5258547Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.Type: GrantFiled: January 9, 1992Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries plcInventor: Gary N. Sheldrake
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Patent number: 5256694Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.Type: GrantFiled: May 22, 1992Date of Patent: October 26, 1993Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
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Patent number: 5256816Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. In this process, the aryl-substituted aliphatic carboxylic acid is reacted with an inorganic base in the presence of an organic base to substantially enrich the precipitate in one of the enantiomers and an improved yield. 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: October 26, 1993Assignee: Ethyl CorporationInventors: William T. Murray, Robert E. Young, Azfar A. Choudhury, Deepak R. Patil
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Patent number: 5256811Abstract: compounds of formula I ##STR1## wherein R.sup.1 represents a C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.3-8 cycloalkyl(C.sub.1-8)alkyl, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkylthio, phenyl or substituted phenyl;R.sup.3 represents a C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, CO2(C.sub.1-8)alkyl, CO.sub.2 (C.sub.2-8) alkenyl, C.sub.1-8 alkylthio, (C.sub.1-2)alkyl CO.sub.2 (C.sub.1-8) alkyl or C.sub.1-8 aldehydroalkyl where the aldehyde function is protected by a suitable protecting group (for example, an acetal such as a dimethyl acetal);R.sup.4 represents a hydrogen atom, C.sub.1-8 alkyl or C.sub.2-8 alkenyl;Z represents a group (CH.sub.2).sub.n or a branched alkyl chain;n is 1 to 8;and each of a, b and c is independently a single or a double bond;can be prepared relatively easily and in good xxx at room temperature by reacting a compound of general formula II ##STR2## wherein R.sup.2, R.sup.3, R.sup.Type: GrantFiled: December 6, 1991Date of Patent: October 26, 1993Assignee: British Bio-Technology LimitedInventors: Richard S. Todd, Maxwell Reeve
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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: 5254720Abstract: A new process for preparing aryl substituted aliphatic carboxylic acids or then alkyl esters is provided. A 1-aryl substituted olefin is reacted with carbon monoxide in the presence of water or an alcohol at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of water or alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a mixture of a palladium compound and a copper compound with at least one acid-stable ligand are present.Type: GrantFiled: December 28, 1992Date of Patent: October 19, 1993Assignee: Ethyl CorporationInventor: Tse-Chong Wu
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Patent number: 5248807Abstract: The present invention provides triterpene derivatives of the following formula: ##STR1## wherein, R.sup.1 is hydrogen or metabolic ester-residue; R.sup.3 is optionally substituted aryl or optionally substituted aromatic heterocycle; X is hydrogen and Y is hydroxy or X and Y may form together oxo; Z is an oxygen or two hydrogen atoms, or the salts thereof, which have anti-endothelin activities and are useful for preventing or treating cardiovascular failure, and pharmaceutical compositions thereof.Type: GrantFiled: July 8, 1992Date of Patent: September 28, 1993Assignee: Shionogi & Co., Ltd.Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
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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: 5241100Abstract: Disclosed are 2,4,6-trialkyl-3-hydroxybenzyl esters of monocarboxylic resin acids and olefin polymer compositions stabilized therewith.Type: GrantFiled: July 15, 1991Date of Patent: August 31, 1993Assignee: Himont IncorporatedInventor: Charles M. Wright
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Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (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; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
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Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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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: 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: 5230828Abstract: Optically active dopants of the formula ##STR1## wherein C* denotes a chiral carbon atom and R.sup.1 signifies C.sub.2 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkoxycarbonyl or C.sub.3 -C.sub.12 -alkenyloxycarbonyl, their manufacture, liquid crystalline mixtures which contain such dopants and their use for optical or electro-optical purposes.Type: GrantFiled: March 22, 1991Date of Patent: July 27, 1993Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5220053Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a 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 solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.Type: GrantFiled: January 24, 1992Date of Patent: June 15, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5214191Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.Type: GrantFiled: May 22, 1990Date of Patent: May 25, 1993Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
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Patent number: 5212303Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents (i) ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --0--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues.Type: GrantFiled: September 28, 1992Date of Patent: May 18, 1993Assignee: Centre International de Recherches Dermatologiques (CIRD)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5204217Abstract: A photosensitive composition containing a compound having a group represented by formula (I) or (II), said group, when irradiated with actinic radiation, forming a carboxylic acid or a sulfonic acid: ##STR1## where R.sub.1 represents hydrogen, an alkyl group, or an aryl group; andR.sub.2 to R.sub.6 may be the same or different and each represents hydrogen, a halogen, an alkoxyl group, an aryloxyl group, cyano group, or an alkyl group, provided that at least one of R.sub.2 to R.sub.6 represents an alkoxyl or aryloxyl group and two of R.sub.2 to R.sub.6 may link to form a ring.Type: GrantFiled: January 16, 1991Date of Patent: April 20, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Mitsunori Ono
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Patent number: 5198567Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 -acyloxy or hydroxyl;R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;R" is either a polyene chain or a benzene ringare useful in cosmetics and in the treatment of various dermatological and other complaints.Type: GrantFiled: July 23, 1991Date of Patent: March 30, 1993Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
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Patent number: 5198568Abstract: This invention relates to novel compositions of matter which are esters with enhanced water solubility, for use in aqueous enzymatic resolution reactions of racemic mixtures of these esters for producing the separate chiral isomers of the racemic mixture. The invention also relates to novel methods for preparing these esters. The importance of the production of the separate chiral isomers of the racemic mixtures resides in the isolation of the isomers which frequently have different biological activities. Of particular significance regarding the water soluble esters of this invention is that they are derivatized with groups which enhance their aqueous solubility and their reactivity with enzymatic resolving methods which are mediated in an aqueous environment.Type: GrantFiled: September 9, 1991Date of Patent: March 30, 1993Assignee: Sepracor, Inc.Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
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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: 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
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Patent number: 5175348Abstract: The invention relates to a novel process for the preparation of halogenated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl, R.sub.2 hydrogen is alkyl or cycloalkyl, and R.sub.3 is halogen having an atomic number of from 9 up to and including 53, which process comprises reacting an acylal of formula II ##STR2## with a hydrogen halide of the formula H--R.sub.3 (III).Type: GrantFiled: March 10, 1992Date of Patent: December 29, 1992Assignee: Saurefabrik SchweizerhallInventors: Pasquale Gallegra, Gerhard Degischer
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Patent number: 5171879Abstract: The invention relates to a novel process for the preparation of chlorinated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl and R.sub.2 hydrogen is alkyl or cycloalkyl, which process comprises reacting an acylal of formula II ##STR2## with thionyl chloride.Type: GrantFiled: March 10, 1992Date of Patent: December 15, 1992Assignee: Saurefabrik SchweizerhallInventors: Pasquale Gallegra, Gerhard Degischer
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Patent number: 5169958Abstract: A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy,R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen andR.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula IIIR.sup.3 --Mg--Y (III)where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.Type: GrantFiled: October 1, 1991Date of Patent: December 8, 1992Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
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Patent number: 5164518Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.Type: GrantFiled: July 12, 1991Date of Patent: November 17, 1992Assignee: Iowa State University Research Fondation Inc.Inventor: Richard C. Larock
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Patent number: 5143644Abstract: This invention relates to carboxylic acid ester compounds or liquid crystal compounds represented by the following formula [A], liquid crystal compositions and liquid crystal elements using these compounds, the method of producing said liquid crystal elements, and other uses. ##STR1## wherein R represents one radical selected from the group consisting of an alkyl group having 6-18 carbon atoms, an alkoxy group having 6-18 carbon atoms, and a halogenated alkyl group having 6-18 carbon atoms, X represents --CF.sub.3 or --CH.sub.2 --CH.sub.3, m is an integral number of 1-10 when X is --CF.sub.3, and an integral number of 2-10 when X is --CH.sub.2 --CH.sub.3, and C* represents an asymmetric carbon atom.Type: GrantFiled: April 6, 1990Date of Patent: September 1, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hideo Yamaoka, Toyoji Shimizu, Fujihisa Matsunaga, Shinichi Nishiyama, Toru Yamanaka, Shoichi Miyakoshi
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Patent number: 5138025Abstract: A method for stabilizing molten diesters of naphthalenedicarboxylic acids and stabilized naphthalenedicarboxylic acid diester compositions are disclosed.Type: GrantFiled: August 30, 1990Date of Patent: August 11, 1992Assignee: Amoco CorporationInventor: Allen B. Mossman
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Patent number: 5130335Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.Type: GrantFiled: July 27, 1990Date of Patent: July 14, 1992Assignee: Allergan, Inc.Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
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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: 5095135Abstract: A process for the preparation of naphthalenecarboxylic acid esters in which a substituted naphthalene is oxidized with molecular oxygen in the presence of a heavy metal-based catalyst in a solvent comprising a lower aliphatic monocarboxylic acid to form a naphthalenecarboxylic acid and the resulting acid is then esterified. The esterified product is purified by washing, recrystallization, and distillation in that order. Heavy metals are recovered as carbonates from filtrates and washings obtained by seeparation of crude acid and ester products and by washing thereof.Type: GrantFiled: April 4, 1991Date of Patent: March 10, 1992Assignee: Sumikin Chemical Co., Ltd.Inventors: Teruaki Yamada, Kazuhiko Maeda, Ryohei Minami, Yukio Nagao, Kazuki Sugiura
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Patent number: 5093517Abstract: There is disclosed a method for making compounds such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) which comprises reacting an alkyl thiopropionate with a glycol at temperatures between 50.degree. C. and 180.degree. C. in the presence of a catalytic amount of a dialkyl tin oxide.Type: GrantFiled: March 9, 1987Date of Patent: March 3, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5087731Abstract: A process of alkoxycarbonylation making use of a new catalyst consisting of a palladium-phosphine complex, the phosphine having a pKa greater than or equal to 7, a chlorinated aromatic compound, carbon monoxide and an alcohol.Type: GrantFiled: October 2, 1990Date of Patent: February 11, 1992Assignee: Rhone-Poulenc ChimieInventors: Marc Huser, John Osborn
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Patent number: 5082587Abstract: Achiral fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion and a hydrocarbon or another fluorocarbon terminal portion, the terminal portions being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases. The compounds are useful in liquid crystal display devices both along and in mixtures with other materials. Also provided is a process for preparing these compounds.Type: GrantFiled: September 23, 1988Date of Patent: January 21, 1992Inventor: Eugene P. Janulis
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Patent number: 5072019Abstract: A method for the manufacture of the four geometric isomers of 4-(2-butenyl)idene)-3,5,5-trimethy-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.Type: GrantFiled: February 1, 1991Date of Patent: December 10, 1991Assignee: Givaudan CorporationInventors: Daniel Helmlinger, Frank Kienzle, Erich Widmer
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Patent number: 5061399Abstract: Optically active naphthalene compounds having the formula: ##STR1## in which X and Y are selected from combinations (a), (b) and (c): (a) X is C.sub.1-10 alkyl or alkoxy and Y is C.sub.4-16 optically active alkyl, (b) X is C.sub.1-10 alkyl or alkoxy and Y is ##STR2## where R.sup.2 is C.sub.4-16 optically active alkyl, (c) X is ##STR3## where R.sup.1 is C.sub.1-10 alkyl or alkoxy and Y is C.sub.4-16 optically active alkyl. Ferroelectric smectic liquid crystal materials being compositions containing these compounds are also described.Type: GrantFiled: April 27, 1987Date of Patent: October 29, 1991Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: John A. Jenner, Ian C. Sage, Stephen J. Lewis
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Patent number: 5055594Abstract: A fluorogenic substrate for tryptophanase useful for identifying an unknown microorganism is a fluorescent dye linked to an amino acid by a carbamate or thiocarbamate group. In preferred substrates, the dye is fluorescein or 7-amino-4-methyl coumarin and the amino acid linked thereto is cysteine, threonine or serine.Type: GrantFiled: July 19, 1990Date of Patent: October 8, 1991Assignee: Becton, Dickinson and CompanyInventor: Patrick D. Mize
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Patent number: 5055451Abstract: Thiol protease inhibitors are disclosed having the formula: ##STR1## or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein:n is 0 or 1;m is 0, 1 or 2;X is H or an N-protecting group;each Y is independently an optionally protected .alpha.-amino acid residue;R is an optionally protected .alpha.-amino acid side chain that is H or CH.sub.3 or that is bonded to the .alpha.-carbon atom to which it is attached by a methylene, methine or phenyl radical; andR' is optionally substituted aryl.Type: GrantFiled: December 7, 1987Date of Patent: October 8, 1991Assignee: Syntex Inc.Inventors: Alexander Krantz, Heinz W. Pauls, Roger A. Smith, Robin W. Spencer
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Patent number: 5055223Abstract: Aryl-sulfur pentafluorides of the formula I ##STR1## wherein R, A, Z, n, m and X.degree. have the meaning indicated in claim 1 are suitable for use as components of liquid-crystal phases for field-effect and/or bi-stability effect displays.Type: GrantFiled: December 27, 1989Date of Patent: October 8, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Rudolf Eidenschink, Georg Weber
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Patent number: 5051447Abstract: Oxime ethers of the general formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or alkyl,R.sup.3 is hydrogen, halogen, cyano, aryl or aryloxy, the aromatic ring being unsubstituted or substituted, or R.sup.3 is heteroaryl, adamantyl, fluorenyl or cycloalkyl or cycloalkenyl, these radicals being unsubstituted or substituted,X is saturated or unsaturated C.sub.1 -C.sub.12 -alkylene which is unsubstituted or substituted, andn is 0 or 1,and fungicides containing these compounds.Type: GrantFiled: July 20, 1989Date of Patent: September 24, 1991Assignee: BASF AktiengesellschaftInventors: Bernd Wenderoth, Franz Schuetz, Siegbert Brand, Hubert Sauter, Eberhard Ammermann, Gisela Lorezn
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Patent number: 5045229Abstract: Difluoromethylene compounds of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Q--CF.sub.2 --(A.sup.3 --Z.sup.2).sub.n --A.sup.4 --R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, A.sup.4, Z.sup.1, Z.sup.2, m and n are as defined herein and Q is --CO--, --O-- or --S--, can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.Type: GrantFiled: March 16, 1990Date of Patent: September 3, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Reinhard Hittich, Hans-Adolf Kurmeier, Eike Poetsch, Herbert Plach
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Patent number: 5028733Abstract: Bicyclooctane and bicycloheptane prostaglandin intermediates have been synthesized.Type: GrantFiled: December 12, 1989Date of Patent: July 2, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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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: 5011579Abstract: A process for treating naphthenic fractions with a caustic blend of sodium and potassium hydroxide, preflashing the naphthenic fraction to remove water and then flashing the dewatered fraction to remove the neutral oils and the materials that were not formed into the acid salts. The naphthenic salt mixture is then quenched and acidified so as to recover the naphthenic acids. Naphthenic acids recovered from the process of the present invention have acid numbers which are generally higher than the naphthenic acids heretofore produced from the corresponding feed streams. The process provides for the flashing of the water which otherwise would cause foaming and not permit the recovery of the acid salt for the enhanced separation of the naphthenic acids.Type: GrantFiled: January 16, 1990Date of Patent: April 30, 1991Assignee: Merichem CompanyInventor: Gerald E. Davis
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Patent number: 4990650Abstract: 1. An aromatic derivative having the formula (I) or the salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, hydroxyl, a halogen atom, or OR.sup.3 wherein R.sup.3 is C.sub.1 -C.sub.10 alkyl; A-B represents a hydrocarbon moiety having 1 to 10 carbon atoms and containing at least one double bond or a sulfur- or oxygen-containing hydrocarbon moiety having 1 to 10 carbon atoms; n is an integer of 2 to 4; X represents a group ##STR2## and Y represents a hydrogen atom; alkyl having 1 to 5 carbon atoms which may be substituted with aryl; alkenyl having 2 to 5 carbon atoms which may be substituted with aryl or aryl substituted with at least one C.sub.1 -C.sub.5 alkoxy; aryl which may be substituted with at least one carboxy or C.sub.1 -C.sub.5 alkoxycarbonyl or C.sub.1 -C.sub.5 alkoxy; provided that, when R.sup.1 and R.sup.2 are both hydrogen, the moiety --A--B--(CH.sub.2).sub.n --X--Y does not represent ##STR3## wherein n=2 to 4 and R.sup.4 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: May 29, 1990Date of Patent: February 5, 1991Assignee: Teijin LimitedInventors: Atsuo Hazato, Seizi Kurozumi
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Patent number: 4967016Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of the compound barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: January 29, 1990Date of Patent: October 30, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4959187Abstract: The invention provides novel bleaching compositions comprising peracid precursors with the general structure ##STR1## with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.Type: GrantFiled: October 14, 1988Date of Patent: September 25, 1990Assignee: The Clorox CompanyInventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske