Naphthyl Group Patents (Class 562/490)
  • 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: 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: 5196577
    Abstract: 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzoic acid marked with tritium is used as a radioactive marker in the titration of nuclear receptors and CRABP, in the measurement of the affinity of retinoids for nuclear receptors and CRABP, in the titration of known retinoids, the characterization of antibodies directed against 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzoic acid, and in the study of the distribution and metabolism of said benzoic acid derivative.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: March 23, 1993
    Assignee: Centre International de Recherches Dermatologiques
    Inventors: Braham Shroot, Yves M. Darmon, Philippe Nedoncelle, Claude Martin
  • Patent number: 5183590
    Abstract: A composition and method for inhibiting corrosion of ferrous metals in contact with an aqueous solution comprising adding to the system from 0.1 to 500 ppm of an aminohydroxysuccinic acid compound selected from group consisting of compounds of the generalized formulas: ##STR1## wherein R is H or C.sub.1 to C.sub.6 alkyl, optionally substituted with --OH, --CO.sub.2 H, --SO.sub.3 H or phenyl, C.sub.4 C.sub.7 cycloalkyl, or phenyl which is optionally substituted with --OH, or --CO.sub.2 H, and R' is H, C.sub.1 to C.sub.6 alkyl, optionally substituted with --OH or CO.sub.2 H; and ##STR2## wherein R' is as above, and Z is selected from the group consisting of i) --(CH.sub.2).sub.n -- wherein n is an integer from 2 to 10, ii) --(CH.sub.2).sub.2 --X--(CH.sub.2).sub.2 -- wherein X is --O--, --S--, --NR"--; wherein R" is selected from the group consisting of H, C.sub.1 to C.sub.6 alkyl, hydroxyalkyl, carboxyallkyl, acyl, --C(O)OR"' wherein R"' is C.sub.1 C.sub.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: February 2, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Charles G. Carter, Vladimir Jovancicevic, Judith A. Hartman, Robert P. Kreh
  • Patent number: 5139702
    Abstract: A composition useful for treating aqueous systems comprising a naphthylamine polycarboxylic acid having the formula: ##STR1## wherein X is CO.sub.2 H or SO.sub.3 H, Y is H, C.sub.1 to C.sub.6 alkyl, CO.sub.2 H or SO.sub.3 H, R is H, C.sub.1 to C.sub.6 alkyl, CO.sub.2 R' or COR', R' is C.sub.1 to C.sub.6 alkyl, n is an integer from 1 to 20, and water soluble salts thereof.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: August 18, 1992
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Charles G. Carter, Robert P. Kreh, Lai-Duien G. Fan
  • 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: 5104492
    Abstract: Carboxylic acids are recovered from wet organic solutions by reducing the solutions' water content thus causing the acids to precipitate as recoverable crystals.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: April 14, 1992
    Assignee: The Regents of the University of California
    Inventors: C. Judson King, John Starr
  • Patent number: 5081252
    Abstract: A process for the preparation of aromatic carboxylic acids or their salts comprises heating carboxyl-free aromatic compounds and aromatic carboxylic acid salts whose basic structures differ from those of the aromatic compounds, or heating polycyclic aromatic compounds with three or more rings and monocyclic or bicyclic aromatic carboxylic acid salts, under carbon dioxide pressure in the presence of one or more metal compounds selected from group (a) of compounds of zinc, cadmium, and thallium and one or more compounds selected from group (b) of compounds of cesium, Group II metals, And Group IIIa metals to effect the intermolecular transfer of the carboxyl groups.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: January 14, 1992
    Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.
    Inventors: Shuichi Mitamura, Yoshimi Kata, Koichi Fujishiro, Yasuhisa Tsutsumi
  • 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: 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: 5004832
    Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: April 2, 1991
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano
  • 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: 4970336
    Abstract: This invention relates to methods of preparing and purifying .alpha.-substituted acetic acids, which comprise treating an .alpha.aromatic-substituted acetic acid represented by a specific general formula with a weak alkali while shielding light, or subjecting an .alpha.-aromatic-substituted acetonitrile represented by a specific general formula to acid hydrolysis, followed by treatment with a weak alkali while shielding light; and treating the alkali salt of .alpha.-substituted acetic acid thus formed with a decolorizing agent.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: November 13, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Yoshikazu Yoshioka, Isao Hashiba, Suketoshi Tsukamoto
  • Patent number: 4962230
    Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: October 9, 1990
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
  • Patent number: 4940696
    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: November 16, 1987
    Date of Patent: July 10, 1990
    Assignee: Centre International de Recherches Dermatologioues (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4937379
    Abstract: A process is described for preparing alpha-arylalkanoic acids, which comprises preparing and subsequently rearranging ketals of formula ##STR1## (in which Ar, R, R.sub.1, R.sub.2 and R.sub.4 have the meanings given in the description).The ketals of formula II are prepared from the corresponding alpha-hydroxyketals.The rearrangement reaction is conducted under mild conditions.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: June 26, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Marco Villa
  • Patent number: 4931589
    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 ring are useful in cosmetics and in the treatment of various dermatological and other complaints.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: June 5, 1990
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 4927967
    Abstract: A process for the production of organic carboxylic acids by the catalytic reaction of organic formate esters in contact with carbon monoxide and a homogeneous catalyst system of rhodium metal atom, a phosphorus containing ligand in which there is present at least one oxo oxygen atom attached to a phosphorus atom or a carbon atom to form a Z group and the ##STR1## group in said Z group is located at least one carbon atom removed and preferably from 2-4 carbon atoms removed from the phosphorus atom of the molecules represented by the formulas ##STR2## and a halogen source, under mild reaction conditions, wherein R' is H, aryl, alkaryl, aralkyl or alkyl, and wherein 1 or more of said R' groups can be substituted with a Z group but not more than 3 of said R' groups in the molecule are so substituted; a is an integer from 0-4; b is an integer from 0-3; and Z is P(O)R'R'; --C(O)OR" or C(O)R", wherein R" is R'.
    Type: Grant
    Filed: November 6, 1985
    Date of Patent: May 22, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Richard W. Wegman
  • Patent number: 4910337
    Abstract: .alpha.-Arylalkanoic acids are prepared by a method comprising the step of reacting an alkylaromatic compound corresponding to the desired .alpha.-arylalkanoic acid with a new metallation reagent solution. The reagent comprises the reaction product of alkyllithium or aryllithium and about two to five molar equivalents of potassium tert-alkoxide in a trialkylamine solvent.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: March 20, 1990
    Assignee: Mine Safety Appliances Company
    Inventors: Kuen-Wai Chiu, Mary H. Staruch, David H. Ellenberger
  • Patent number: 4897473
    Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: January 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Bernard D. Dombek
  • Patent number: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4894482
    Abstract: A process is provided for removing water from a mixture of hydrogen fluoride (HF), a carboxylic acid, e.g., acetic acid, and water by extractive distillation in the presence of a Lewis base as solvent, which does not azeotrope with water, forms bonds with the HF and carboxylic acid which can be broken by heat and has a boiling point at atmospheric pressure at least about 20.degree. C. above that of the carboxylic acid, e.g., N-methyl-2-pyrrolidone, and taking off an overhead vapor comprising a major proportion of the water in said mixture. The extractive distillation may be advantageously integrated in an overall process with the production of an aromatic ketone, e.g., 4-hydroxyacetophone, by the Friedel-Crafts acylation of an aromatic compound, e.g., phenol, with the carboxylic acid, using HF as catalyst, to produce a product mixture comprising the aromatic ketone, HF, carboxylic acid and water, and the removal of aromatic ketone from the product mixture by means of a solvent assisted distillation.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: January 16, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Daniel D. Lindley, Carl D. Murphy
  • Patent number: 4894471
    Abstract: A continuous process for the alkylation of CH-acid compounds with dialkyl carbonates in gas-liquid phase transfer catalysis conditions is described, consisting of contacting a mixture of a CH-acid compound (arylacetonitrile or malonic diester) and of a dialkylcarbonate, optionally added with an inert carrier (constituted by a polar or aprotic polar liquid or by a gas), with a catalytic bed comprising alumina spheres carrying a base and a phase transfer catalyst.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: January 16, 1990
    Assignee: Consiglio Nazionale Delle Richerche
    Inventors: Enrico Angeletti, Franco Trotta, Pietro Tundo, Paolo Venturello
  • Patent number: 4892940
    Abstract: An aromatic naphthyl compound of the formula ##STR1## wherein n is 0 or 1,R' is hydrogen, OH, acyloxy, alkoxy or NH.sub.2,R" is hydrogen or lower alkoxy, or R' and R" taken together form an oxo, methano or hydroxy-imino radical,R is --CH.sub.2 OH or --COR.sub.8,R.sub.8 is hydrogen, --OR.sub.9 or ##STR2## R.sub.9 is hydrogen, alkyl having 1-20 carbon atoms, mono or polyhydroxyalkyl, aryl, aralkyl, the residue of a sugar or ##STR3##is 1, 2 or 3,r' and r" each independently represent hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, benzyl, the residue of amino acid or the residue of aminated sugar, or r' and r" together form a heterocycle,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen, lower alkyl, alkoxy having 1-4 carbon atoms, fluoroalkoxy, CF.sub.3, cycloalkyl, lower acyl, halogen, OH, amino, acylamino or alkoxy carbonyl,R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl or when n=1, R.sub.5 and R.sub.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: January 9, 1990
    Assignee: L'Oreal
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
  • Patent number: 4886907
    Abstract: New polysubstituted derivatives of naphtalene.These derivatives correspond to the following formula: ##STR1## in which: R.sub.1 to R.sub.4 is H or CH.sub.3R.sub.5 is(i) ##STR2## (ii) --C.tbd.N (iii) ##STR3## or (iv) the radical: 2-oxazolinylm is 0 or 1R.sub.8 is H, alkyl, OR.sub.11, R.sub.11 being H, alkyl or ##STR4## R.sub.13 being alkyl or aryl or R.sub.8 is ##STR5## when m=1, r' and r" representing H, alkyl mono or polyhydroxyalkyl, aryl or a heterocycle when they are taken together, R.sub.9 is H or alkyl, R.sub.10 is H, alkyl and the acetals of the said compounds, ##STR6## --OR.sub.14, R.sub.14 being H, alkyl, mono or polyhydroxyalkyl, aryl or aralkyl a rest of a sugar or represents ##STR7## being 0, 1, 2, or 3 R.sub.6 represents a hydrogen atom or a lower alkyl radical,R.sub.7 represents H, alkyl, halogen, hydroxyl, sulfydryl, alkoxy, alkylthio, acyloxy, acylthio, acylamino or primary, secondary or tertiary amino and the salts of the said compounds.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: December 12, 1989
    Assignee: Centre International De Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
  • Patent number: 4876381
    Abstract: The invention relates to a compound of the formula (II) ##STR1## and the corresponding isomers and salts, in which formula: a and b are integers which independently of one another can assume the values 0 or 1,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 -alkyl radical or a C.sub.1 -C.sub.4 -alkoxy radical,R.sub.6 represents a C.sub.1 -C.sub.6 -alkyl radical,R.sub.5 and R.sub.12 represent a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, with the proviso that R.sub.5 cannot represent hydrogen if a=b=0 andR.sub.11 has various meanings.These compounds have useful dermatological properties.
    Type: Grant
    Filed: August 18, 1987
    Date of Patent: October 24, 1989
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
  • Patent number: 4871740
    Abstract: A glycyrrhetic acid derivative of the formula ##STR1## wherein X and Y are hydrogen atom, respectively or X is oxygen atom together with Y, A.sub.1 is methylene or carbonyl radical, A.sub.2 is hydrogen atom, cyano, carbamoyl, carboxyl radical or alkoxycarbonyl group, m and n are an integer, respectively, R.sub.1 is a radical of ##STR2## in which R.sub.2 is an alkyl, alkenyl group, phenyl radical or a substituted phenyl radical, A.sub.3 is S, O or NH, and l is an integer, a process for the preparation of the derivatives, and use of the derivative as a pharmaceutical agent.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: October 3, 1989
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Masayasu Kurono, Ryoichi Unno, Hiromoto Kimura, Mitsuru Oka, Keiko Hasegawa, Shinichi Ikeda, Noboru Kuboyama, Takashi Ito, Kiichi Sawai, Shunshuke Ito
  • Patent number: 4866197
    Abstract: Process for the production of N-[[2-alkoxy-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-meth ylglycine esters and intermediates for their production. Said esters are themselves intermediates for the manufacture of compounds which inhibit aldose reductase and are useful for the treatment of diabetic complications.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: September 12, 1989
    Assignee: American Home Products Corporation
    Inventor: John G. Bauman
  • Patent number: 4849530
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 18, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Gerhard Zol, Gerhard Pfarrhofer
  • Patent number: 4814494
    Abstract: An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of:(I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and(II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: March 21, 1989
    Assignee: Nippon Petrochemicals Company, Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4810694
    Abstract: The invention relates to a compound of formula (I) ##STR1## in which formula: R.sub.1, R.sub.3 and R.sub.4 denote, independently of each other a hydrogen atom, a C.sub.1 -C.sub.8 alkyl radical, a C.sub.1 -C.sub.8 alkoxy radical, a C.sub.1 -C.sub.8 acryloxy radical or a hydroxy ra dical;R, R' and R" denote, independently of each other, either one of the meanings given above for R.sub.1, R.sub.3 and R.sub.4, or a halogen atom, or a primary, secondary or tertiary amino radical,A having various meanings.The invention also relates to a process for the preparation of compounds of formula (I) and to medicinal and cosmetic compositions in which they are present.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: March 7, 1989
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Jean R. Maignan, Braham Shroot, Serge A. Restle
  • Patent number: 4806558
    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 dermatological disorders.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: February 21, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 4783549
    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 indepenently 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 ring are useful in cosmetics and in the treatment of various dermatological and other complaints.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: November 8, 1988
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 4783548
    Abstract: A process for preparing a 3,4-dihydro 2-naphthanoic acid or an ester thereof comprises heating an alpha-vinyl cinnamic acid or a (C.sub.1 -C.sub.12)alkyl, (C.sub.6 -C.sub.12)aryl, (C.sub.6 -C.sub.12)aralkyl or (C.sub.6 -C.sub.12)alkylaryl ester thereof at a temperature effective to cyclize said acid or ester thereof and obtain the corresponding 3,4-dihydro 2-naphthanoic acid or ester thereof. The alpha-vinyl cinnamic acid or ester thereof may be obtained by contacting crotonic anhydride and a benzaldehyde substituted with halo or (C.sub.1 -C.sub.12)alkyl, acyl, acyloxy, carboxy, carbalkoxy, alkylthiol or alkoxy.A process for preparing 2-naphthanoic acid or an ester thereof comprises the above steps to prepare a 3,4-dihydro-2-naphthanoic acid, and dehydrogenating said 3,4-dihydro 2-naphthanoic acid or ester thereof to obtain the 2-naphthanoic acid.
    Type: Grant
    Filed: September 16, 1987
    Date of Patent: November 8, 1988
    Assignee: Eastman Kodak Company
    Inventor: Joseph R. Zoeller
  • Patent number: 4782057
    Abstract: A benzo[h]cinnoline compound of the formula: ##STR1## wherein each of X and Y is hydrogen, halogen, trifluoromethyl, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, alkanoylamido having 2 to 4 carbon atoms, nitro, cyano, alkanoyl having 2 to 4 carbon atoms; Ar is phenyl or pyridyl which may be optionally substituted by at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, alkanoylamido having 2 to 4 carbon atoms, nitro and cyano; and the bond position indicated by dotted line is single bond or double bond, a method of preparing said compound and a pharmaceutical composition containing said compound.Since these compounds possess high affinity for benzodiazepine receptor and antianxiety activity, they are useful as neutralizers to an excess dose of antianxiety agents or as antianxiety agents.
    Type: Grant
    Filed: March 25, 1986
    Date of Patent: November 1, 1988
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tetsuya Tahara, Minoru Kawakami, Shuzo Takehara, Masamitsu Sakamori
  • Patent number: 4767882
    Abstract: Tetrahydronaphthalene derivatives of the formula: ##STR1## wherein either one of R.sup.1 and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and the other is acetyl and R.sup.3 is hydrogen or methyl in a racemic or optically active form, which are useful as perfumes or intermediates for production of perfumes, are prepared from an R.sup.4 -benzene and pyrocine through the intermediary compounds of the formula: ##STR2## wherein R.sup.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy present at either one of 6- and 7-positions and A is hydrogen, carboxyl, C.sub.2 -C.sub.5 alkoxycarbonyl, halogen, methyl, hydroxymethyl or halomethyl.
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: August 30, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Gohfu Suzukamo, Yoji Sakito
  • Patent number: 4767784
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 30, 1988
    Inventors: Gerhard Zolss, Gerhard Pfarrhofer
  • Patent number: 4762948
    Abstract: An optically active arylacetic acid derivative of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are each an hydrogen atom, a lower alkyl group or a phenyl group; and Ar is a group of the formula: ##STR2## a group of the formula: ##STR3## wherein R.sub.3 and R.sub.4 are the same or different and are each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a difluoromethoxy group, a trifluoromethyl group or a phenyl group is prepared in good conversion and optical yield by asymmetrically reducing an ethylenically unsaturated compound of the formula: ##STR4## wherein R.sub.1, and R.sub.2 and Ar are the same as defined above with hydrogen in the presence of a metal catalyst modified with a ligand selected from the group consisting of a specific optically active metallocenyl phosphine derivative and a specific optically active binaphthyl derivative.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: August 9, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshihiko Ito, Tamio Hayashi, Norio Kawamura, Ichiki Takemoto
  • Patent number: 4761497
    Abstract: 2-Naphtanoic acid or ester thereof is prepared by heating a compound selected from the group consisting of ketals and enol ethers or esters of an alpha-acetyl cinnamic acid or ester thereof at a temperature effective to cyclize the compound and form said 2-naphthanoic acid or ester thereof.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: August 2, 1988
    Assignee: Eastman Kodak Company
    Inventors: Joseph R. Zoeller, Charles E. Sumner, Jr.
  • Patent number: 4749804
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 7, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: George C. Schloemer
  • Patent number: 4748272
    Abstract: This invention relates to new lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties. The present new compounds are of the formula: ##STR1## and salts thereof; whereinAr is phenyl, naphthyl or sulfur, oxygen or nitrogen heterocyclic;X is O, S, NR.sub.5, or a chemical bond;R is H, lower alkoxy, aryloxy, hydroxy, lower alkyl, aryl or lower aralkyl;R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkoxy, lower alkyl, aryl, aryloxy, lower aralkyl, lower aralkoxy, formyl, lower alkanoyl, benzoyl, and lower aralkanoyl;R.sub.3 and R.sub.4 are independently hydrogen, halogen, hydroxy, lower alkoxy, aryloxy, lower aralkoxy, trifluoromethyl, lower carbalkoxy, carboxy, cyano, nitro, lower alkyl, lower alkenyl, lower alkynyl, aryl or lower aralkyl;R.sub.5 is H, lower alkyl, lower aralkyl or aryl;R.sub.6 is hydroxy or hydroxy-substituted lower alkyl;n and m are independently 0, 1, 2 or 3.
    Type: Grant
    Filed: August 1, 1986
    Date of Patent: May 31, 1988
    Assignee: Rorer Pharmaceutical Corp.
    Inventor: Raymond D. Youssefyeh
  • Patent number: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4727181
    Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: February 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4717720
    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 --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 conjuctive tissues.
    Type: Grant
    Filed: April 10, 1986
    Date of Patent: January 5, 1988
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4675418
    Abstract: Process for preparing alkanoic acid or their esters by rearrangement of alpha-halo-ketones in protic medium and in the presence of a non-noble metal salt.The protic medium is preferably an aliphatic alcohol having low molecular weight or water and the reaction is carried out at a temperature from 0.degree. C. to the boiling-point of the diluent or of the diluents mixture.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: June 23, 1987
    Assignee: Blaschim S.p.a.
    Inventors: Claudio Giordano, Giovanni Villa, Fulvio Uggeri, Graziano Castaldi
  • Patent number: 4663465
    Abstract: 2,2-Dimethyl-3-arylcyclopropanecarboxylic acids and esters, suitable as insecticide intermediates, of the formula ##STR1## in which Ar is naphthyl or substituted furyl, thienyl or phenyl, andR.sup.1 is hydrogen or alkyl, are produced by subjecting ##STR2## to radical polymerization to produce ##STR3## reacting that with chlorine or bromine to produce ##STR4## and reacting that with an alkali metal or alkaline earth metal hydroxide or carbonate. Various intermediates II and III are new.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: May 5, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4654438
    Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: March 31, 1987
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer