Aromatic Patents (Class 562/405)
  • Patent number: 4898883
    Abstract: The present invention relates to 1-substituted derivatives of 4-methoxy-2,3,6-trimethylbenzene which are useful in cosmetic or pharmaceutical preparations for use in the treamtnet of dermatological complaints connected with a keratinisation disorder, dermatological complaints having an inflammatory and/or immuno-alleric component or ophthalmological complaints.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: February 6, 1990
    Assignee: L'Oreal
    Inventors: Gerard Lang, Serge Forestier, Alain Lagrange, Braham Shroot
  • 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: 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: 4879368
    Abstract: Condensation products of benzyl chlorides and aromatic hydroxycarboxylic acids are suitable for use as color developers in pressure- or heat-sensitive recording materials.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: November 7, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Gert Jabs
  • Patent number: 4868347
    Abstract: Substituted fluorobenzenes which are produced in aprotic, polar solvents or in mixtures which contain such solvents can be obtained by extracting the substituted fluorobenzenes from the solvents or solvent mixtures with aliphatic extracting agents and then seaprating the extracting agents from the substituted fluorobenzenes.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: September 19, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Edwin Ritzer
  • Patent number: 4864057
    Abstract: A process is provided for the oxydehydrogenation of saturated carboxylic acids or a lower alkyl ester thereof with oxygen in the presence of iron phosphorus oxide catalysts containing promoters selected from the group Ag, Al, B, Be, Cd, Co, Cu, Ga, Ge, In, Mn, Ni, Te, Th, Ti, Tl, U, V, Zn, Zr, rare earths and mixtures thereof.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: September 5, 1989
    Inventors: S. Erik Pedersen, James L. Callahan, Harley F. Hardman
  • 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: 4804670
    Abstract: Substituted hexatriene derivatives of the formula I ##STR1## where R.sup.1 has the meaning given in the description, and their preparation, are described. The compounds may be used to treat acne and psoriasis.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: February 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Joachim Paust, Klaus Schmieder, Axel Nuerrenbach
  • 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: 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: 4739098
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where n is 0-5 and A is H, lower alkyl, or --COOH or ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: April 19, 1988
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4723028
    Abstract: The application discloses certain stilbene compounds, pharmaceutical compositions thereof, method of treating thereof, method of diagnosis therewith, and method for the preparation thereof. The compounds and compositions are useful for diagnosis of leukemia types, the treatment of dermatological disorders, and as differentiation-inducing agents for neoplastic cells.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: February 2, 1988
    Inventor: Koichi Shudo
  • Patent number: 4605758
    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: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4582856
    Abstract: Pesticidally active 2,2-dimethyl-3-(2-halogeno-vinyl)-cyclopropanecarboxylic acid esters of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent alkyl or halogenoalkyl,R.sup.3 represents alkyl or the grouping --(CH.sub.2)--.sub.n R.sup.4,in whichn represent 0 or 1 andR.sup.4 represents halogenoalkyl, optionally substituted aryl or the grouping --XR.sup.5,in whichX represents oxygen or sulphur andR.sup.5 represents alkyl, halogenoalkyl, optionally substituted aryl or optionally substituted aralkyl,Hal represents fluorine, chlorine or bromine andR represents an alcohol radical which can be used in the case of pyrethroids.Intermediates carrying an acid, acid chloride or alkyl ester group in place of --COOR are also new.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: April 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Benedikt Becker, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4578498
    Abstract: Phenylethylene derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and A have the meanings given in the description, and their preparation.The novel compounds are useful for combating disorders.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: March 25, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4570011
    Abstract: The invention is a process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: February 11, 1986
    Assignee: The Dow Chemical Company
    Inventor: Ying-Hung So
  • Patent number: 4564700
    Abstract: An improved process for the preparation of fluorene-9-carboxylic acid comprising reacting fluorene and a dialkyl carbonate with alkyls of 1 to 5 carbon atoms in the presence of a member of the group consisting of alkali metal hydrides or potassium alcoholate of an aliphatic alcohol of 1 to 5 carbon atoms, neutralizing the mixture and saponifying the resulting fluorene-9-carboxylic acid ester to obtain fluorene-9-carboxylic acid in good yields.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: January 14, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Winfried Orth, Emmerich Pastorek, Werner Fickert
  • Patent number: 4560763
    Abstract: A base precursor for heat-developable photosensitive material is disclosed. The precursor is comprised of a compound represented by general formula (I) or (II):(R--C.tbd.C--CO.sub.2 H).sub.x.B (I)R--C.tbd.C--CO.sub.2 H).sub.2.B.sub.y (II)The substituents within the general formulae are defined within the specification. The use of this novel base precursor makes it possible to obtain a material which is very stable at normal temperatures and which smoothly decomposes under heating at 80.degree. C. or higher in order to release a basic constituent.
    Type: Grant
    Filed: March 30, 1984
    Date of Patent: December 24, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Hiroyuki Hirai
  • Patent number: 4544766
    Abstract: This invention relates to a process for preparing an aryl acetic acid derivative represented by the formulaAr--CH.sub.2 COY).sub.ncomprising hydrolyzing in an alkaline substance a dichloroethenyl compound represented by the formulaAr--CH.dbd.CCl.sub.2).sub.n.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: October 1, 1985
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventor: Tatsuya Shono
  • Patent number: 4532343
    Abstract: Aromatic retinoic acid analogues of the formula ##STR1## where X is hydrogen or fluorine, Y is hydrogen, halogen of atomic number 9 or 17, hydroxy, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms and R is hydroxy, alkoxy, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl, or aryl and R.sup.2 is alkyl or aryl, with the proviso that when Y is hydrogen, X is fluorine. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
    Type: Grant
    Filed: November 19, 1982
    Date of Patent: July 30, 1985
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Peter D. Hobbs
  • Patent number: 4499304
    Abstract: Color-forming para-sulfonamidodiphenylamines and their corresponding sulfonimide dyes are useful in imaging materials. The color-forming sulfonamidodiphenylamines are prepared by condensation reactions. The corresponding sulfonimide dyes are formed by oxidation of the color-forming sulfonamidodiphenylamines by means of a suitable oxidizing agent, such as the oxidized form of a cross-oxidizing silver halide developing agent.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: February 12, 1985
    Assignee: Eastman Kodak Company
    Inventors: Rolf S. Gabrielsen, Patricia A. Graham, James E. Klijanowicz, Max H. Stern
  • Patent number: 4492800
    Abstract: A process for the preparation of a 1,1-dichloro-alkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or together are alkanediyl,in the presence of at least an equimolar amount of magnesium. Advantageously,R.sup.1 is hydrogen,R.sup.2 is a C.sub.2 to C.sub.5 alkenyl radical or a radical of the formula ##STR4## Z is a cyano, acetal, carboxyl or C.sub.1 to C.sub.4 alkoxycarbonyl radical, or a radical of the formula COOM, andM is sodium or potassium,R.sup.3 each individually is a C.sub.1 to C.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: January 8, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4485252
    Abstract: 2-Phenyl-alk-1-enyl-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R each independently is hydrogen, halogen, cyano, nitro and, in each case optionally halogen-substituted, alkyl, alkoxy, alkylenedioxy or alkylthio,R.sup.1 is optionally halogen-substituted alkyk, andR.sup.2 is a radical customary in the alcohol part of pyrethroidswhich exhibit insecticidal and acaricidal activity. They are made from the corresponding alkyl esters which are new and made by novel processes.
    Type: Grant
    Filed: May 5, 1982
    Date of Patent: November 27, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4482731
    Abstract: The invention relates to a process for preparing trans-3-(Z-2-chloro-2-(4-aryl)-vinyl)-2,2-dimethyl-cyclopropane-1-carboxyl ic acid derivatives of Formula (I) from corresponding dehalogenated compounds of Formula (II) by dehalogenation. The invention also includes to the novel compounds of Formula (III) and a halogenation process for their production. The compounds of the invention are useful as intermediates and/or insecticides or acaricides.
    Type: Grant
    Filed: August 28, 1981
    Date of Patent: November 13, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Wilhelm Stendel
  • Patent number: 4480118
    Abstract: This invention relates to a novel carboxylic acid ester represented by the following general formula (I) and an insecticidal and/or acaricidal composition containing the same as an active ingredient: ##STR1## wherein X is represented by the formula, ##STR2## and further also relates to a carboxylic acid or a reactive derivative thereof represented by the general formula, ##STR3## wherein R.sub.16 is hydroxy group, chlorine or bromine atom, or a C.sub.1-2 alkoxy group, W is oxygen atom or --CH.sub.2 -- group, k is an integer of 0 or 1, E is hydrogen, chlorine, fluorine or bromine atom, and n is an integer of 1 to 4.
    Type: Grant
    Filed: December 30, 1981
    Date of Patent: October 30, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Makoto Hatakoshi, Toshihiko Yano, Nobushige Itaya
  • Patent number: 4478760
    Abstract: The process for making a fluorinated product comprising reacting a perfluoroalkyl iodide and an olefin in the presence of a finely divided zinc and an acidic solvent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 23, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
  • Patent number: 4465833
    Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: August 14, 1984
    Assignees: Hughes Aircraft Company, Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Robert H. Boschan
  • Patent number: 4461910
    Abstract: A process for the co-production of an alkylidene dicarboxylate and a carboxylic acid, which comprises hydrogenating a carboxylic acid anhydride in the presence of carbon monoxide and a homogeneous iridium- and/or rhodium-containing catalyst, together with an organo phosphorus (III), arsenic (III), or antimony (III) compound and either molecular oxygen or a phosphorus (V), arsenic (V) or antimony (V) compound containing a X=O moiety, where X is a phosphorus, arsenic or antimony atom.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 24, 1984
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4461899
    Abstract: A series of ester and salt derivatives of fluorene-9-carboxylic acid and fluorene-1-carboxylic acid exhibit significant plant growth regulating properties, useful in controlling the size, shape, dormancy time, flowering time and/or fruit setting of plants, depending upon the concentrations used. They may also be used to control the growth rate, texture and color of turf grass. Presently preferred compounds include the cis-2,5-dimethylpyrrolidine salt of 1-fluorenecarboxylic acid, 9-cis-2,5-dimethyl-1-pyrrolidinyl-2-chlorofluorene-9-carboxylic acid, methyl ester, the 2,6-dimethylpiperidine salt of 1-fluorenecarboxylic acid, and the cis-2,5-dimethylpyrrolidine salt of 9-hydroxyfluorene-9-carboxylic acid.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: July 24, 1984
    Assignee: Diamond Shamrock Chemicals Company
    Inventors: William J. Pyne, Han S. Ku, Robert E. Holm
  • Patent number: 4439614
    Abstract: 5,6-Methano-5,6-dihydroretinoids such as ethyl (E)-5,6-methano-5,6-dihydroretinoate and (E)-1-(4-carbethoxyphenyl)-2-methyl-4-(2,2,6-trimethylbicyclo[4.1.0]hept-1 -yl)-1,3-butadiene are disclosed. These componds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: March 27, 1984
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
  • Patent number: 4424166
    Abstract: In the preparation of a 1,1-dihalogenoalkene of the formula ##STR1## in which R.sup.1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, andX.sup.1 and X.sup.2 each independently is a halogen atom,wherein a carbonyl compound of the formula ##STR2## is reacted with a trihalogenoacetate of the formula ##STR3## in which X.sup.3 is a halogen atom, andM.sup..sym. is an alkali metal ion or one equivalent of an alkaline earth metal ion,in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: January 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4423066
    Abstract: A pentafluorobenzyl 2,2-dimethyl-3-vinylcyclopropane carboxylate of the formula ##STR1## in which R is hydrogen or halogen, andR.sup.1 is optionally substituted phenyl, orR and R.sup.1 together constitute an alkylene chain with at least two carbon atoms,which possess arthropodicidal properties.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: December 27, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4407823
    Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein n is an integer of 2 to 5; ##STR2## R.sub.1 is hydrogen, halogen, trifluoromethyl, nitro or amino; R.sub.2 and R.sub.3 each independently is hydrogen or lower alkyl; or together form an ethylene group;X.sub.1 represents two hydrogen atoms or an oxo group; andY.sub.1 is cyano, hydroxyamidocarbonyl, carbamoyl, 5-tetrazolyl or carboxyl;and for derivatives wherein Y is carboxyl, salts thereof with physiologically compatible bases, esters thereof from physiologically acceptable alcohols and amides thereof from physiologically acceptable amines have valuable pharmacological activity, e.g., as antiinflammatory agents.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: October 4, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerald Kirsch, Joachim-Friedrich Kapp, Clemens Rufer
  • Patent number: 4358409
    Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: November 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4358607
    Abstract: The invention is a novel chloro-substituted cyclopropane carboxylic acid useful for the preparation of novel insecticidal-acaricidal pyrethroids.
    Type: Grant
    Filed: July 21, 1978
    Date of Patent: November 9, 1982
    Assignee: American Cyanamid Co.
    Inventor: Dale G. Brown
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4311600
    Abstract: The disclosure is of the use of a particular humate to reduce the viscosity of water-based drilling fluids. The humate is usually found in association with titanium minerals and bears a unique compositional make-up. The composition is particularly advantageous as a drilling mud thinner, imparting high temperature stability to water-based drilling muds.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: January 19, 1982
    Assignee: Union Camp Corporation
    Inventor: William C. Firth, Jr.
  • Patent number: 4307232
    Abstract: Process for preparing the substituted phosphonoalkanoic acid of the formula ##STR1## wherein: R.sup.1 is alkyl of 1-8 carbon atoms, aralkyl of 7-10 carbon atoms, phenyl, or substituted phenyl of 6-10 carbon atoms;R.sup.2 is H, hydrocarbyl of 1-18 carbon atoms, or substituted hydrocarbyl of 1-18 carbon atoms, wherein in said hydrocarbyl groups the carbon atom attached to the ##STR2## moiety is substituted with two or three hydrogen atoms or is a carbon atom of an aromatic ring; andY is oxygen or sulfur,which process comprises contacting and reacting, at a temperature of about -70.degree. C. to about 125.degree. C., a pressure of about 1-100 atmospheres (0.1-10 MPa), and for a time sufficient to effect reaction, the phosphite ester of the formula ##STR3## wherein R.sup.1 and Y are as defined above, with the .alpha.-halocarboxylic acid of the formula R.sup.2 CHXCO.sub.2 H, wherein X is Cl, Br, or I and R.sup.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: December 22, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David R. Brittelli
  • Patent number: 4307034
    Abstract: An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: December 22, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
  • Patent number: 4297371
    Abstract: Combating ectoparasites with the substantially pure isomer mixture (.+-.)-trans-3-(E/Z-2-Chloro-2-(4-chlorophenyl)-vinyl)-2,2-dimethyl-cyclop ropanecarboxylic acid (.+-.)-(.alpha.-cyano-3-phenoxy-4-fluoro-benzyl) ester or the individual E- and Z-isomers of the formula ##STR1## The intermediate free acids, acid chlorides and esters thereof are also shown.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: October 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Bernd Gallenkamp, Wilhelm Stendel
  • Patent number: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4246281
    Abstract: Acenaphthenes of formula (I) ##STR1## where Ph represents an optionally substituted phenyl group and wherein R.sup.1 represents hydrogen or C.sub.1-4 alkyl are useful anti-inflammatory agents.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: January 20, 1981
    Assignee: Lilly Industries Limited
    Inventor: William R. N. Williamson
  • Patent number: 4243677
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: January 6, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4235727
    Abstract: The disclosure is of the use of a particular humate to reduce the viscosity of water-based drilling fluids. The humate is usually found in association with rutile sand and bears a unique compositional make-up. The composition is particularly advantageous as a drilling mud thinner, imparting high temperature stability to water-based drilling muds.
    Type: Grant
    Filed: April 6, 1978
    Date of Patent: November 25, 1980
    Assignee: Union Camp Corporation
    Inventor: William C. Firth, Jr.
  • Patent number: 4234515
    Abstract: N,N-difluoroamines are prepared by fluorination of compounds containing a >C.dbd.N-- bond using molecular fluorine or a hypofluorite in which the fluoroxy group is bonded to an inert electron attracting group, such hypofluorites including fluoroalkyl hypofluorites such as trifluoromethyl hypofluorite. The fluorination is advantageously conducted in the presence of an alkanol or other nucleophilic compound. Suitable starting materials include imino ethers and esters and aliphatic and aromatic Schiff's bases, use of the latter being particularly convenient.
    Type: Grant
    Filed: May 9, 1978
    Date of Patent: November 18, 1980
    Assignee: Research Institute for Medicine & Chemistry Inc.
    Inventors: Derek H. R. Barton, Robert H. Hesse
  • Patent number: 4189598
    Abstract: Esters of .alpha.-indenyl substituted aliphatic acids, intermediates therefor, synthesis thereof, and the use of said esters and compositions thereof for the control of pests.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: February 19, 1980
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4178300
    Abstract: A novel process is described for the preparation of novel organic solutions of organooxy magnesium compounds of low viscosity, which solutions are formed in the presence of at least 5 mol % based on the magnesium compound of an organooxy compound of a transition metal of Groups IV through VI of the Periodic Table.
    Type: Grant
    Filed: October 31, 1978
    Date of Patent: December 11, 1979
    Assignee: Stamicarbon, B.V.
    Inventor: Cornelis E. P. V. van den Berg
  • Patent number: 4167640
    Abstract: Invention relates to improved processes for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indenyl-3-acetic acid, to intermediates thereof, and to the preparation of said intermediates.
    Type: Grant
    Filed: July 17, 1978
    Date of Patent: September 11, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Roger J. Tull, David G. Melillo
  • Patent number: 4166131
    Abstract: This invention provides new compounds of formula I, ##STR1## wherein R.sub.1 is lower alkyl,R.sub.2 is hydrogen or lower alkyl,R.sub.3 is hydrogen or lower alkyl,R.sub.4 is hydrogen or lower alkyl,R.sub.5 is hydrogen, chlorine or lower alkyl, and each ofR.sub.6 and R.sub.7 is hydrogen, or, when R.sub.5 is hydrogen, R.sub.6 may also be chlorine or lower alkyl, and R.sub.7 chlorine or lower alkyl,Useful as anti-phlogistic and anti-arthritic agents.
    Type: Grant
    Filed: October 24, 1974
    Date of Patent: August 28, 1979
    Assignee: Hexachimie Societe Anonyme
    Inventor: Trevor G. Payne