Naphthyl In Acid Moiety Patents (Class 560/100)
  • Patent number: 5260482
    Abstract: 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: Grant
    Filed: October 14, 1992
    Date of Patent: November 9, 1993
    Assignee: Ethyl Corporation
    Inventors: Patricia Pringle, William T. Murray, Douglas K. Thompson, Azfar A. Choudhury, Deepak R. Patil
  • Patent number: 5258532
    Abstract: 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: Grant
    Filed: December 10, 1991
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries PlC
    Inventor: John R. Lawson
  • Patent number: 5258547
    Abstract: 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: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5256694
    Abstract: 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: Grant
    Filed: May 22, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 5256816
    Abstract: 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: Grant
    Filed: October 14, 1992
    Date of Patent: October 26, 1993
    Assignee: Ethyl Corporation
    Inventors: William T. Murray, Robert E. Young, Azfar A. Choudhury, Deepak R. Patil
  • Patent number: 5256811
    Abstract: 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: Grant
    Filed: December 6, 1991
    Date of Patent: October 26, 1993
    Assignee: British Bio-Technology Limited
    Inventors: Richard S. Todd, Maxwell Reeve
  • Patent number: 5254714
    Abstract: 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: Grant
    Filed: October 10, 1991
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventor: Merrikh Ramezanian
  • Patent number: 5254720
    Abstract: 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: Grant
    Filed: December 28, 1992
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5248807
    Abstract: 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: Grant
    Filed: July 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
  • Patent number: 5248813
    Abstract: 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: Grant
    Filed: October 14, 1992
    Date of Patent: September 28, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
  • Patent number: 5241100
    Abstract: Disclosed are 2,4,6-trialkyl-3-hydroxybenzyl esters of monocarboxylic resin acids and olefin polymer compositions stabilized therewith.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: August 31, 1993
    Assignee: Himont Incorporated
    Inventor: Charles M. Wright
  • Patent number: 5235095
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
  • Patent number: 5235100
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5235101
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5233075
    Abstract: 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: Grant
    Filed: October 15, 1991
    Date of Patent: August 3, 1993
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Andrew J. Matosky
  • Patent number: 5230828
    Abstract: 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: Grant
    Filed: March 22, 1991
    Date of Patent: July 27, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • Patent number: 5221765
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: June 22, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5220053
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: June 15, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5214191
    Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: May 25, 1993
    Assignee: Cortech, Inc.
    Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
  • Patent number: 5212303
    Abstract: 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: Grant
    Filed: September 28, 1992
    Date of Patent: May 18, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5204217
    Abstract: 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: Grant
    Filed: January 16, 1991
    Date of Patent: April 20, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Mitsunori Ono
  • Patent number: 5198567
    Abstract: 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: Grant
    Filed: July 23, 1991
    Date of Patent: March 30, 1993
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 5198568
    Abstract: 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: Grant
    Filed: September 9, 1991
    Date of Patent: March 30, 1993
    Assignee: Sepracor, Inc.
    Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
  • Patent number: 5196541
    Abstract: 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: Grant
    Filed: August 2, 1991
    Date of Patent: March 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Alexander Klausener, Peter C. Knuppel, Fritz Maurer
  • Patent number: 5177250
    Abstract: 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: Grant
    Filed: May 13, 1991
    Date of Patent: January 5, 1993
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo
  • Patent number: 5175348
    Abstract: 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: Grant
    Filed: March 10, 1992
    Date of Patent: December 29, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171879
    Abstract: 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: Grant
    Filed: March 10, 1992
    Date of Patent: December 15, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5169958
    Abstract: 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: Grant
    Filed: October 1, 1991
    Date of Patent: December 8, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
  • Patent number: 5164518
    Abstract: 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: Grant
    Filed: July 12, 1991
    Date of Patent: November 17, 1992
    Assignee: Iowa State University Research Fondation Inc.
    Inventor: Richard C. Larock
  • Patent number: 5143644
    Abstract: 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: Grant
    Filed: April 6, 1990
    Date of Patent: September 1, 1992
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hideo Yamaoka, Toyoji Shimizu, Fujihisa Matsunaga, Shinichi Nishiyama, Toru Yamanaka, Shoichi Miyakoshi
  • Patent number: 5138025
    Abstract: A method for stabilizing molten diesters of naphthalenedicarboxylic acids and stabilized naphthalenedicarboxylic acid diester compositions are disclosed.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: August 11, 1992
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 5130335
    Abstract: 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: Grant
    Filed: July 27, 1990
    Date of Patent: July 14, 1992
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
  • Patent number: 5107053
    Abstract: 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: Grant
    Filed: October 25, 1991
    Date of Patent: April 21, 1992
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5095135
    Abstract: 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: Grant
    Filed: April 4, 1991
    Date of Patent: March 10, 1992
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Teruaki Yamada, Kazuhiko Maeda, Ryohei Minami, Yukio Nagao, Kazuki Sugiura
  • Patent number: 5093517
    Abstract: 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: Grant
    Filed: March 9, 1987
    Date of Patent: March 3, 1992
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
  • Patent number: 5087731
    Abstract: 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: Grant
    Filed: October 2, 1990
    Date of Patent: February 11, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, John Osborn
  • Patent number: 5082587
    Abstract: 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: Grant
    Filed: September 23, 1988
    Date of Patent: January 21, 1992
    Inventor: Eugene P. Janulis
  • Patent number: 5072019
    Abstract: 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: Grant
    Filed: February 1, 1991
    Date of Patent: December 10, 1991
    Assignee: Givaudan Corporation
    Inventors: Daniel Helmlinger, Frank Kienzle, Erich Widmer
  • Patent number: 5061399
    Abstract: 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: Grant
    Filed: April 27, 1987
    Date of Patent: October 29, 1991
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: John A. Jenner, Ian C. Sage, Stephen J. Lewis
  • Patent number: 5055594
    Abstract: 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: Grant
    Filed: July 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Becton, Dickinson and Company
    Inventor: Patrick D. Mize
  • Patent number: 5055451
    Abstract: 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: Grant
    Filed: December 7, 1987
    Date of Patent: October 8, 1991
    Assignee: Syntex Inc.
    Inventors: Alexander Krantz, Heinz W. Pauls, Roger A. Smith, Robin W. Spencer
  • Patent number: 5055223
    Abstract: 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: Grant
    Filed: December 27, 1989
    Date of Patent: October 8, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Rudolf Eidenschink, Georg Weber
  • Patent number: 5051447
    Abstract: 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: Grant
    Filed: July 20, 1989
    Date of Patent: September 24, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wenderoth, Franz Schuetz, Siegbert Brand, Hubert Sauter, Eberhard Ammermann, Gisela Lorezn
  • Patent number: 5045229
    Abstract: 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: Grant
    Filed: March 16, 1990
    Date of Patent: September 3, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Reinhard Hittich, Hans-Adolf Kurmeier, Eike Poetsch, Herbert Plach
  • Patent number: 5028733
    Abstract: Bicyclooctane and bicycloheptane prostaglandin intermediates have been synthesized.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: July 2, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5015764
    Abstract: 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: Grant
    Filed: June 18, 1990
    Date of Patent: May 14, 1991
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, Fred J. Impastato
  • Patent number: 5011579
    Abstract: 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: Grant
    Filed: January 16, 1990
    Date of Patent: April 30, 1991
    Assignee: Merichem Company
    Inventor: Gerald E. Davis
  • Patent number: 4990650
    Abstract: 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: Grant
    Filed: May 29, 1990
    Date of Patent: February 5, 1991
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4967016
    Abstract: 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: Grant
    Filed: January 29, 1990
    Date of Patent: October 30, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4959187
    Abstract: 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: Grant
    Filed: October 14, 1988
    Date of Patent: September 25, 1990
    Assignee: The Clorox Company
    Inventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske