Naphthyl In Acid Moiety Patents (Class 560/100)
  • Patent number: 5705167
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5696162
    Abstract: Compounds of Formula 1 ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH.sub.2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; Y is an aromatic group such as phenyl or naphthyl, or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: December 9, 1997
    Assignee: Allergan
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5686586
    Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.In the formula, X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: November 11, 1997
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5675033
    Abstract: Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R.sub.4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.4 groups, the divalent Y radical being substituted by the Z and --CR.sub.1 .dbd.CR.sub.1 --CR.sub.1 .dbd.CR.sub.1 groups on adjacent carbons; X is S, O, or NR.sub.5 ; n is 1 or 2; R.sub.1 and R.sub.2 independently are H, lower alkyl or fluoroalkyl; R.sub.3 is hydrogen, lower alkyl, Cl or Br; R.sub.4 is lower alkyl, fluoroalkyl or halogen; R.sub.5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
  • Patent number: 5648514
    Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification, have retinoid-like biological activity.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: July 15, 1997
    Assignee: Allergan
    Inventors: Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Roshantha A. Chandraratna
  • Patent number: 5643495
    Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 1, 1997
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Ekkehard Bartmann, Ulrich Finkenzeller
  • Patent number: 5616803
    Abstract: A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of the substituents are herein defined.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: April 1, 1997
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Takashi Nomoto, Masahiro Hayashi, Jun Shibata, Yoshikazu Iwasawa, Morihiro Mitsuya, Yoshiaki Iida, Katsumasa Nonoshita, Yasufumi Nagata
  • Patent number: 5599966
    Abstract: Compounds of the formula (I): Ar.sub.1 --CH(OH)--CH.sub.2 --NH--CH.sub.2 --X--CH.sub.2 --E--(CH.sub.2).sub.n --Y--Ar.sub.2, in which the substituents and symbols have the meanings given in the description, are novel active compounds having, in particular, a broncholytic action.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: February 4, 1997
    Assignee: BYK Nederland BV
    Inventors: Jan Bron, Geert J. Sterk, Hendrik Timmerman, Meta E. J. Veerman, Jan F. Van Der Werf
  • Patent number: 5597839
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: January 28, 1997
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5574017
    Abstract: The present invention provides methods and pharmaceutical preparations for inhibiting the growth of bacterial microorganisms.
    Type: Grant
    Filed: July 5, 1994
    Date of Patent: November 12, 1996
    Inventor: William G. Gutheil
  • Patent number: 5563292
    Abstract: Novel compounds of Formula 1 ##STR1## or a pharmaceutically acceptable salt or solvate thereof are disclosed. Also disclosed are pharmaceutical compositions containing compounds of Formula 1. Methods of treating allergy, inflammation and hyperproliferative skin diseases with compounds of Formula 1 are also disclosed.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: October 8, 1996
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina
  • Patent number: 5536874
    Abstract: There is provided a process for preparing an arylacetic acid or arylpropionic acid divative from an arylcarbinol which comprises the step of subjecting said arylcarbinol to suitable carbonylation conditions for a sufficient period of time and under suitable pressure and temperature to form said acid derivative, with the proviso that said carbonylation conditions include conducting the reaction in a two-phase system wherein one phase is an aqueous medium which contains (1) a catalyst which is a water-soluble metal complex consisting essentially of a Group VIII metal and a hydrophilic ligand such as palladium complexed with trisulfonated triphenylphosphine, and (2) optionally an acid, and wherein the second phase comprises said arylcarbinol.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 16, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Roger A. Sheldon, Leendert Maat, Georgios Papadogianakis
  • Patent number: 5534188
    Abstract: An acetylene derivative represented by general formula (I): ##STR1## wherein R.sup.1 is saturated or unsaturated alkyl group having 3-20 carbon atoms, R.sup.2 is saturated or unsaturated alkyl group having 1-20 carbon atoms which may optionally be substituted by halogen atom or alkoxyalkyl group having 2-20 carbon atoms, A and B represent phenylene group or the like or taken as --A--B-- represent naphthalene group or the like, m and s are each 0 or 1, n is integer of 1-6, and * means asymmetric carbon atom; a process for producing said acetylene derivative, a liquid crystal composition using the same as active ingredient, and a liquid crystal element using said composition.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: July 9, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Takayuki Higashii, Shoji Toda, Naoyuki Takano, Kayoko Ueda, Koichi Fujisawa
  • Patent number: 5523457
    Abstract: This invention relates to a retinoid mpound of formula I ##STR1## in which Y is --CO--NH--, --CR.sup.2 .dbd.CR.sup.3 --, --CO--O--, --O--CO--, --C(.dbd.S)--NH--, --C.tbd.C--, --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --CH.sub.2 --;A is --(CH.sub.2).sub.t -- or a bond;Q is phenyl optionally substituted with one to three same or different C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halogen, or --CO.sub.2 R.sup.4 ;R.sup.1 is --CO.sub.2 Z, --CONHR.sup.5, C.sub.1-6 alkyl, --CH.sub.2 OH, or --CHO;R.sup.2, R.sup.3, R.sup.4, R.sup.5, and Z are independently hydrogen or C.sub.1-6 alkyl;t is one to six.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 4, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: John E. Starrett, Jr., Muzammil M. Mansuri, David R. Tortolani
  • Patent number: 5484935
    Abstract: Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.3 are each C.sub.1-4 alkyl or C.sub.1-4 alkyl-carbonyl, and R.sup.2 is carboxy, tetrazolyl, C.sub.1-4 alkyl-sulphonamido or --CR.sup.4 R.sup.5 CO.sub.2 H where R.sup.4 and R.sup.5 are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.1 and R.sup.3 are both methyl and when R.sup.1 and R.sup.3 are both methylcarbonyl, R.sup.2 is not carboxy; and salts and esters thereof.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: January 16, 1996
    Assignee: Lilly Industries Limited
    Inventors: Peter T. Gallagher, Terence A. Hicks, William M. Owton
  • Patent number: 5470999
    Abstract: Compounds of Formula 1 ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: November 28, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5466861
    Abstract: Bridged bicyclic aromatic compounds are provided having the structure ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n are as defined herein. The novel compounds are useful for modulating gene expression of retinoic acid receptors, vitamin D receptors and thyroid receptors. Pharmaceutical compositions and methods for modulating gene expression are provided as well.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: November 14, 1995
    Assignees: SRI International, La Jolla Cancer Research Foundation
    Inventors: Marcia L. Dawson, James F. Cameron, Peter D. Hobbs, Ling Jong, Magnus Pfahl, Xiao-kun Zhang, Jurgen M. Lehmann
  • Patent number: 5458806
    Abstract: Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: October 17, 1995
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Herbert Plach
  • Patent number: 5455265
    Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 3, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5439925
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use is in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: August 8, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, Willliam R. Pilgrim
  • Patent number: 5422038
    Abstract: Optically active naphthalene derivatives including optically active naphthylcarboxylic acid derivative, hydroxynaphthalene derivative, alkoxynaphthylalkanol derivative and alkylnaphthylalkanol derivative have the following structural formula: ##STR1## wherein R.sup.1 denotes an alkyl group of 3-20 carbon atoms, R.sup.2 denotes an alkyl group of 1-20 carbon atoms optionally substituted with halogen atom(s) or an alkoxyalkyl group of 2-20 carbon atoms optionally substituted with halogen atom(s), X denotes --COO-- or --OCO--, k, l and m denotes 0 or 1 respectively, n denotes an integer of 0-6, p denotes 0 or 1, and the asterisk indicates an asymmetric carbon atom, with the proviso that when k is 0, l and m are not 1 at the same time, and when k is 1, m is 1, and when n is 0 and m is 1, X is --COO--.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: June 6, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shoji Toda, Takayuki Higashii, Isao Kurimoto, Masayoshi Minai, Chizu Sekine, Takeshi Tani, Koichi Fujisawa
  • Patent number: 5403952
    Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: April 4, 1995
    Assignee: Merck & Co., Inc.
    Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
  • Patent number: 5399747
    Abstract: A new process for preparing aryl-substituted aliphatic carboxylic acids is provided. Aryl-substituted aliphatic ether or thioether compound is reacted with carbon monoxide in aqueous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An acid such as hydrochloric acid may be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: March 21, 1995
    Assignee: Albemarle Corporation
    Inventors: Kannappan Chockalingam, Tse-Chong Wu
  • Patent number: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5359122
    Abstract: The preparation of 3-arylacrylic acids and their derivatives I ##STR1## where Ar is aryl which can additionally have substituents which do not react with ketene and are stable under the conditions of the reaction described below, andR.sup.1 is hydrogen, an alkali metal, an alkaline earth metal, ammonium or C.sub.1 -C.sub.20 -alkyl,comprises a first stage in which a dialkyl acetal of an aromatic aldehyde of the formula II ##STR2## where R.sup.2 is C.sub.1 -C.sub.4 -alkyl, is reacted with ketene of the formula CH.sub.2 .dbd.C.dbd.O in the presence of catalytic amounts of a protic or Lewis acid to give a 3-arylpropionic acid derivative of the formula III ##STR3## and a second stage in which this intermediate III is reacted in the presence of acid or base and, in the case where R.sup.1 is C.sub.1 -C.sub.20 -alkyl, additionally with a C.sub.1 -C.sub.20 -alkanol to give the final product I.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: October 25, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Josef Gnad, Rainer Becker
  • Patent number: 5356561
    Abstract: In accordance with the present invention, there are provided carboxylate compounds represented by the following formula [A] and liquid crystal material comprising said compounds ##STR1## wherein R is a group selected from the group consisting of alkyl, alkoxy and halogenated alkyl group of 3-20 carbon atoms, X and Y represent each a group selected from the group consisting of --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --S--S--, ##STR2## or a single bond, A and B represent each a group selected from the group consisting of specific divalent aromatic and alicyclic group such as phenylene, cyclohexylene and tetrahydronaphthalene and R* is an optically active group of 4-20 carbon atoms containing at least one asymmetric carbon atom (hydrogen atoms attached to the carbon atoms of said optically active group may be substituted with halogen atoms), and m and n are each an integer of 0-2, with the proviso that both m and n do not become 0 at the same time.
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: October 18, 1994
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toyoji Shimizu, Shinichi Nishiyama, Nobuyuki Doi, Shoichi Miyakoshi, Tooru Yamanaka, Katsuo Taniguchi, Hideo Hama
  • Patent number: 5352820
    Abstract: The invention is an expedient route to synthesizing substituted or unsubstituted aryl-2-propenoic esters. The substituted or unsubstituted aryl-2-propenoic esters are useful in preparing optically active substituted or unsubstituted 2-arylpropanoic acids known to be active anti-inflammatory agents.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: October 4, 1994
    Inventor: Jeremy I. Levin
  • Patent number: 5352822
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5344960
    Abstract: A cobalt based catalyst, and the method for preparing it, are disclosed. The catalyst is obtained from the reaction between NaCo(CO).sub.4 and s-trichloro triazine and is advantageously used in the processes of carbonylation of naphthalene mono- and disulfonates in order to yield naphthalene esters and acids.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 6, 1994
    Assignee: Enichem S.p.A.
    Inventors: Giuseppe Cometti, Annick Du Vosel, Franco Francalanci, Roberto Santi
  • Patent number: 5344959
    Abstract: Compounds of the formula ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.
    Type: Grant
    Filed: May 18, 1993
    Date of Patent: September 6, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5344970
    Abstract: 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: Grant
    Filed: December 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Albemarle Corporation
    Inventor: Charles H. Kolich
  • Patent number: 5330678
    Abstract: Disclosed are novel liquid crystal compounds containing a naphthalene ring, having an excellent light leaking ratio at tristable states, and represented by the following formula: ##STR1## wherein R.sub.1 is a C.sub.6 -C.sub.16 linear alkyl group or C.sub.6 -C.sub.16 linear alkoxy group, R.sub.2 is a C.sub.4 -C.sub.12 linear alkyl group, R.sub.3 is a C.sub.1 -C.sub.3 alkyl group or C.sub.1 -C.sub.3 haloalkyl group, and C having an asterisk indicates an asymmetric atom.The liquid crystal compounds are expected to find their applications in electrooptical devices and liquid crystal displays utilizing a S*.sub.(3) liquid crystal phase which shows tristable states.
    Type: Grant
    Filed: May 25, 1993
    Date of Patent: July 19, 1994
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Nobuhiro Okabe, Hiroyuki Mogamiya, Noriko Yamakawa
  • Patent number: 5328641
    Abstract: Liquid crystal compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each is a C.sub.1-18 alkyl group or an aralkyl group, R' is haloalkyl group, X is --O--, --CO--, --COO-- or direct bond, Y is --COO--, --OCO-- or --CH.sub.2 O--, (A) and (B) each is ##STR2## and p and l each is zero or one.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: July 12, 1994
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshihiko Aihara, Tadaaki Isozaki, Hioyuki Mogamiya, Yuvraj Negi, Toru Ooide
  • Patent number: 5322959
    Abstract: A new process for preparing aryl substituted aliphatic carboxylic acid esters is provided. A 1-aryl substituted aliphatic halo compound is reacted with carbon monoxide in the presence of an alcohol in anhydrous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of anhydrous alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: June 21, 1994
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5321044
    Abstract: 15,16-Seco-19-nor progestins are provided which display elevated progestational activity with a minimum of ancillary hormonal activity. Processes for the preparation of the novel progestins are provided as are methods of use. A preferred method of use is in the suppression of ovulation in the human female.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: June 14, 1994
    Assignee: SRI International
    Inventors: Richard H. Peters, Masato Tanabe
  • Patent number: 5315029
    Abstract: A new process for preparing alkyl esters of ibuprofen is provided. A 1-halo-1-(4-isobutylphenyl)ethane is reacted with carbon monoxide in the presence of an anhydrous alcohol at a temperature between about 10.degree. C. and about 200.degree. C. An excess of several moles of alcohol is preferred. An acid such as trifluoroacetic acid is also added. As catalyst, a palladium compound and at least one acid-stable ligand over palladium are present; however, an excess of ligand over palladium is advantageous.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: May 24, 1994
    Assignee: Ethyl Corporation
    Inventor: Kannappan Chockalingam
  • Patent number: 5315026
    Abstract: A catalytic process for preparing aryl substituted aliphatic carboxylic acid esters is disclosed. A 1-aryl substituted olefinic compound is reacted with carbon monoxide in the presence of an alcohol in anhydrous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of anhydrous 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 is used with at least one acid-stable cyclic phosphine having the formula: ##STR1## where R' is the same or different than R" and is alkyl or aryl, said aryl, either substituted or unsubstituted, and Ar' is phenyl, naphthyl, substituted phenyl or substituted naphthyl and n is an integer from 3 to 6.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: May 24, 1994
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5315030
    Abstract: A new process for preparing aliphatic carboxylic acid esters is provided. A substituted aliphatic ether or thioether compound is reacted with carbon monoxide in the presence of an alcohol in anhydrous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of anhydrous alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: May 24, 1994
    Assignee: Ethyl Corporation
    Inventors: Kannappan Chockalingam, Tse-Chong Wu
  • Patent number: 5315028
    Abstract: A new process for preparing aryl substituted aliphatic carboxylic acid esters is provided. A 1-aryl substituted olefinic compound is reacted with carbon monoxide in the presence of an alcohol in anhydrous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of anhydrous 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: May 12, 1993
    Date of Patent: May 24, 1994
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5306833
    Abstract: 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: Grant
    Filed: February 3, 1993
    Date of Patent: April 26, 1994
    Assignee: Societe Francaise Hoechst
    Inventors: Jean-Claude Vallejos, Yani Christidis
  • Patent number: 5302751
    Abstract: A process is disclosed that is useful for separating the enantiomers of a racemic mixture of an aliphatic carboxylic acid having the formula ##STR1## where R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3 and R.sub.4 are independently different and are hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl, substituted heteroaryl, haloalkyl, alkoxyalkyl, alkylthioalkyl, phenylalkyl, substituted phenylalkyl, heteroalkylalkyl, substituted heteroalkylalkyl or cycloalkylalkyl.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: April 12, 1994
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, Alicia A. Potter
  • Patent number: 5294511
    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## wherein 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: December 29, 1992
    Date of Patent: March 15, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Mitsunori Ono
  • Patent number: 5292928
    Abstract: In a process for reacting a low molecular weight hydroxy compound with a carboxylic acid halide, a small amount of the acid halide is introduced into the reaction vessel and the remainder of the acid halide and the hydroxy compound are added gradually in an approximately stoichiometric ratio. The hydrogen halide formed is thus prevented from dissolving in the reaction medium. The heat of reaction to be dissipated is negligible.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karlheinz Miltenberger
  • Patent number: 5290478
    Abstract: Optically active compounds having the following formulae (1), (2) or (3) ##STR1## wherein R and R' are C.sub.1-20 alkyl groups; X and Y.sub.1 are --, O, S, or divalent groups such as COO, OOC and OCOO; m is 0 or 1; n is 0 to 5; A.sub.2 is a cyclic group, such as p,p'-biphenylene, 2,6-naphthylene, 2,5-pyrimidinylene-1,4-phenylene, A.sub.1 --Y.sub.2 -pyridylene or A.sub.4 --Y.sub.2 --A.sub.5 ; Y.sub.2 is CH.sub.2 CH.sub.2 or C.tbd.C; A.sub.3 is 2,6-naphthylene, A.sub.1 --Y.sub.2 -pyridylene or A.sub.6 --CH.sub.2 CH.sub.2 --A.sub.7 ; and A.sub.1, A.sub.4, A.sub.5, A.sub.6 and A.sub.7 are cyclic groups, such as 1,4-phenylene and/or 4,4'-biphenylene.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: March 1, 1994
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Masahiro Satoh, Tetsuya Watanabe, Kunikiyo Yoshio, Hiroshi Kishiki
  • Patent number: 5278337
    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; and3) 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: January 11, 1994
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
  • Patent number: 5278333
    Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: January 11, 1994
    Assignee: Tessenderlo Chemie N.V.
    Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; 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.3 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 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5264152
    Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5262560
    Abstract: A process for preparing purified dimethyl-2,6-naphthalenedicarboxylate by the esterification of 2,6-naphthalenedicarboxylic acid is disclosed and which process provides for the efficient removal of the mono methyl ester of 2,6-naphthalenedicarboxylic acid produced during the esterification reaction.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: November 16, 1993
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, David A. Young, Martin A. Zeitlin, Paul K. Behrens
  • Patent number: RE34805
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##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 --O--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 conjunctive tissues.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: December 6, 1994
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon