Nitro Bonded To Carbon In Acid Moiety Patents (Class 560/20)
  • Patent number: 4727180
    Abstract: Polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides, and esters, such as methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepro panoate, are useful as antihypertensive agents.
    Type: Grant
    Filed: January 4, 1985
    Date of Patent: February 23, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul E. Aldrich, Gilbert H. Berezin
  • Patent number: 4727199
    Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventor: Stephen W. King
  • Patent number: 4723030
    Abstract: A method is provided for enhancing the production rate of arylhydroxylamines by moderated catalytic hydrogenation reactions. Small quantities of acid introduced to the reaction medium doubles the hydrogenation rate of nitroaromatic compounds without a significant loss in selectivity to arylhydroxylamines.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: February 2, 1988
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 4717418
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl; andn is an integer chosen from 2 to 5.The compounds are cereal selective herbicides and in further embodiments of the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of compounds of formula I, herbicidal compositions containing as active ingredient a compound of formula I, and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: January 5, 1988
    Assignee: ICI Australia Limited
    Inventors: Richard B. Warner, Alexander Serban, Keith G. Watson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
  • Patent number: 4710581
    Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: December 1, 1987
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4709107
    Abstract: A method for preparing nitrones from mixtures of arylhydroxylamines and alkylhydroxylamines containing zinc oxide solids is provided which does not require filtration of the mixture prior to reaction. This is accomplished by introducing a dilute acid solution to the mixture so as to solubilize the zinc oxide powder. The hydroxylamines within solution may be reacted with an aldehyde to produce a nitrone where the dilute acid dissolves the zinc oxide.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: November 24, 1987
    Assignee: General Electric Company
    Inventors: Paul R. West, Gary C. Davis
  • Patent number: 4703110
    Abstract: The application discloses certain benzoic acid compounds, the same being more adequately described as benzoic acid derivatives having a para substituent which is a substituted phenyl radical attached to the benzoic acid in the para position by any one of a variety of linking groups, representative compounds being p-(3,4-diisopropylphenylcarbamoyl) benzoic acid and p-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarbamoyl)benzoic acid, pharmaceutical compositions thereof, method of treating therewith, 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: October 27, 1987
    Assignee: Koichi Shudo
    Inventor: Koichi Shudo
  • Patent number: 4693848
    Abstract: Alkali metal and alkaline earth metal salts of acyloxybenzenesulfonic acids of the formula I ##STR1## where R is a saturated or unsaturated alkyl radical of 1 to 17 carbon atoms or is phenyl which is unsubstituted or monosubstituted or disubstituted by alkyl of 1 to 3 carbon atoms, halogen, methoxy or nitro, are prepared by neutralization, by a method in which a liquid acyloxybenzenesulfonic acid of the formula I and an aqueous solution of an alkali metal or alkaline earth metal hydroxide, carbonate or bicarbonate are combined in water, at from 0.degree. to 60.degree. C. and while mixing thoroughly, so that the pH is kept at from 2.5 to 7.0, and, if desired, the resulting salt is isolated from the aqueous solution in a conventional manner.
    Type: Grant
    Filed: April 2, 1986
    Date of Patent: September 15, 1987
    Assignee: Basf Aktiengesellschaft
    Inventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
  • Patent number: 4686309
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: August 11, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4684639
    Abstract: A compound having the partial structure (I) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a group --COR.sup.5 or --CO--OR.sup.5 wherein R.sup.5 represents an optionally substituted hydrocarbon group; R.sup.3 is halogen and R.sup.4 is hydrogen, methoxy, hydroxymethyl or formamido.These compounds are suitably bicyclic .beta.-lactam antibiotics.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: August 4, 1987
    Assignee: Beecham Group
    Inventors: George Burton, Desmond J. Best
  • Patent number: 4680419
    Abstract: This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.
    Type: Grant
    Filed: July 22, 1985
    Date of Patent: July 14, 1987
    Assignee: The Upjohn Company
    Inventor: Stephen J. Nelson
  • Patent number: 4670581
    Abstract: New biphenyl compounds and a process for producing them are provided. These new compounds have an acyloxy group in the 2- or 4-position of the biphenyl and an acyl hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl or, alternatively a hydroxyl group in the 2- or 4-position of the biphenyl and an acyl, hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl. These compounds can be produced easily from 2- or 4-acyloxybiphenyl compounds.
    Type: Grant
    Filed: January 10, 1984
    Date of Patent: June 2, 1987
    Assignee: Sugai Chemical Industry Co., Ltd.
    Inventor: Teiichi Tanigaki
  • Patent number: 4664852
    Abstract: A process for preparing L-carnitine (I) wherein(a) diketene (II) is reacted with chlorine, and the chlorination product thus obtained is submitted to amidation by the methylester of an optically-active aminoacid, having formula: ##STR1## wherein R=CH.sub.2 A.sub.r or A.sub.
    Type: Grant
    Filed: May 22, 1986
    Date of Patent: May 12, 1987
    Assignee: Sclavo S.p.A.
    Inventors: Paolo Casati, Claudio Fuganti
  • Patent number: 4659372
    Abstract: 2-Aryl-1,3-cyclohexanedione enol ester compounds exhibit outstanding miticidal, mite ovicidal and herbicidal activity.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: April 21, 1987
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4659862
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: April 21, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • Patent number: 4652672
    Abstract: For the analytical and preparative separation of the optical isomers of optically active alkanolamines into their optically pure antipodes a new resolution method is presented which involves an ester formation of the alkanolamines with optically pure and symmetrically O,O disubstituted (R,R)- or (S,S)-tartaric acids. The derivitization reactions are carried out in aprotic solvents and the primary and secondary functions are blocked via ion-pair formations with strong acids, e.g. dichloroacetic acid. The tartaric acid anhydrides are predominantly used as reagents but other ester formation methods are also practicable. The mixture of the diastereomeric alkanolamine tartaric acid monoesters are separable into their optically active and pure isomers by various chromotographic separation techniques, e.g. straight or reverse phase LC, but also by extraction methods e.g. Soxhlet extraction.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: March 24, 1987
    Inventor: Wolfgang F. Lindner
  • Patent number: 4652303
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: March 24, 1987
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4647555
    Abstract: Ester analogues of boron analogues of amino acid are disclosed. Also disced is a method of forming the ester analogues in high yield by condensation of the corresponding acids and alcohols with dicylohexylcarbodiimide at room temperature in dichloromethane. The disclosed compounds have shown interesting biological activities, in particular, hypolipidemic activity as well as significant antitumor and antiarthritic activities.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: March 3, 1987
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Bernard F. Spielvogel, Andrew T. McPhail, Iris H. Hall
  • Patent number: 4645305
    Abstract: The present liquid crystal compounds are novel ester-type compounds showing a smectic liquid crystal phase and being capable of increasing a dielectric constant anisotropy, represented by the following general formula: R--X.sub.1 --Y.sub.1 --X.sub.2 --Y.sub.2 --NO.sub.2, wherein R is an alkyl group; X.sub.1 and X.sub.2 are the same or different from each other and are group --COO-- and --OOC--, and when X.sub.1 is group --COO--, ##STR1## The present liquid composition contains the novel compound, and the present liquid crystal display device uses the liquid crystal composition for utilizing the characteristics of the novel compound. Particularly, the present liquid crystal display device is a thermally addressed display device.
    Type: Grant
    Filed: November 23, 1984
    Date of Patent: February 24, 1987
    Assignee: Hitachi, Ltd.
    Inventors: Hisao Yokokura, Susumu Era, Hidetoshi Abe, Tadao Nakata, Teruo Kitamura, Akio Mukoh
  • Patent number: 4643763
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: February 17, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4640706
    Abstract: Novel cyclohexenonecarboxylic acid derivatives exhibit herbicidal and plant growth regulating activity.The cyclohexenonecarboxylic derivatives are of the formula I ##STR1## wherein A is an aliphatic or aromatic alcohol, or is an amino group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano, or is a heterocyclic amino group which is unsubstituted or substituted,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,B is an aliphatic or aromatic radical or is an aliphatic or aromatic carbonyl or sulfonyl group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano.The compounds are suitable for selectively controlling grasses in crops of useful plants.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: February 3, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4640708
    Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: February 3, 1987
    Assignee: ICI Australia Limited
    Inventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
  • Patent number: 4639541
    Abstract: Substituted phenylactic acid iodopropargyl ester compounds of the general formula: ##STR1## in which R may represent hydrogen, fluorine, chlorine, bromine, iodine, methoxy, 1-imidazolyl or 1,2,4-triazolyl, X represents one or more of the same or different substituents selected from fluorine, chlorine, bromine, iodine, cyano, nitro, carboxyl, an alkyl having from 1 to 12 carbon atoms, an alkoxy having from 1 to 12 carbon atoms, a cycloalkyl having from 3 to 6 carbon atoms, formyl, acetyl, propionyl, benzoyl, phenylsulfonyl, phenyl, phenoxy, and substituted phenyl and phenoxy groups having from 1 to 3 substituents selected from fluorine, chlorine, bromine, nitro, methyl or methoxy, and n is an integer from 1 to 5 and may be zero provided that R does not represent hydrogen. The invention also relates to a process of making the compounds, which are effective ingredients of biocidal agents.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: January 27, 1987
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Gerhard Staiger, Tassilo Selmayr, Peter Kinzel, Anneliese Reutter
  • Patent number: 4639267
    Abstract: The invention concerns novel compounds of the formula I and isomers thereof ##STR1## wherein: n is an integer selected from 2 to 4;m is zero or an integer selected from 1 to 3;X, which may be the same or different, are independently selected from halogen, alkyl, alkoxy and alkylthio;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: January 27, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4620027
    Abstract: A method of preparing esters of cinnamic acid comprising catalytically reacting a styrene compound with carbon monoxide, oxygen, and an aliphatic alcohol. The catalyst is a combination of a palladium (II) compound, an alkali metal carboxylate and a copper salt.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: October 28, 1986
    Assignee: Sun Refining and Marketing Company
    Inventor: Chao-Yang Hsu
  • Patent number: 4613681
    Abstract: This invention relates to a process for the preparation of a fluorinated compound of the general formulaR.sub.F C.sub.2 H.sub.4 ORcomprising reacting an iodide of the general formula R.sub.F C.sub.2 H.sub.4 I with a percarboxylic acid of the general formula R.sup.1 CO.sub.3 H at a temperature and for a time sufficient to form said fluorinated compound; in said formulae R.sub.F is a straight or branched chain perfluorinated radical containing 1 to 20 C atoms, R is a hydrogen atom or --COR.sup.1, and R.sup.1 is a hydrogen atom or an aliphatic or aromatic hydrocarbon radical.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: September 23, 1986
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Louis Foulletier, Andre Lantz
  • Patent number: 4607053
    Abstract: Arylhydroxamates are provided having the structure ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, aryl, lower alkenyl, cycloalkenyl, aralkyl, or ##STR2## wherein n is 1 to 4 and X is hydroxy, alkoxy, amino, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -dialkylamino.R.sup.2 is hydrogen or lower alkyl; andR.sup.3 is C.sub.1 -C.sub.20 alkyl or C.sub.3 -C.sub.20 alkenyl, aryl, aryl-alkyl, cycloalkyl, aryl-alkenyl, lower alkoxy, lower alkenyloxy, aryl-alkoxy or cycloalkyloxy.These compound are useful as inhibitors of .DELTA..sup.5 -lipoxygenase and as such are useful as antiallergy agents.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: August 19, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Donald S. Karanewsky, Martin F. Haslanger
  • 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: 4604407
    Abstract: Hydroxamates are provided having the structure ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, aryl, lower alkenyl, cycloalkenyl, aralkyl, or ##STR2## wherein n is 1 to 4 and X is hydroxy, alkoxy, amino, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -dialkylamino.R.sup.2 is hydrogen or lower alkyl; andR.sup.3 is C.sub.1 -C.sub.20 alkyl or C.sub.3 -C.sub.20 alkenyl, aryl, aryl-alkyl, cycloalkyl, aryl-alkenyl, lower alkoxy, lower alkenyloxy, aryl-alkoxy or cycloalkyloxy, and m is 0 to 5. These compounds are useful as inhibitors of .DELTA..sup.5 -lipoxygenase and as such are useful as antiallergy agents.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: August 5, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Martin F. Haslanger, Donald S. Karanewsky
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4588531
    Abstract: Alkali metal and alkaline earth metal salts of acyloxybenzenesulfonic acids of the formula I ##STR1## where R is a saturated or unsaturated alkyl radical of 1 to 17 carbon atoms or is phenyl which is unsubstituted or monosubstituted or disubstituted by alkyl of 1 to 3 carbon atoms, halogen, methoxy or nitro, are prepared by neutralization, by a method in which a liquid acyloxybenzenesulfonic acid of the formula I and an aqueous solution of an alkali metal or alkaline earth metal hydroxide, carbonate or bicarbonate are combined in water, at from 0.degree. to 60.degree. C. and while mixing throughly, so that the pH is kept at from 2.5 to 7.0, and, if desired, the resulting salt is isolated from the aqueous solution in a conventional manner.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: May 13, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
  • Patent number: 4584318
    Abstract: A method is described for the control of nematodes in agricultural crops which comprises applying to the situs of infestation of a nematicidal composition containing as active ingredient a compound of the formula ##STR1## wherein Q is hydroxy, carbamoyloxy, or acyloxy, R is alkyl, alkenyl, alkynyl, X is halogen or methyl, n is 1 or 2. Preparation of active ingredient compounds is described, and nematicidal utility of compositions is exemplified.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: April 22, 1986
    Assignee: FMC Corporation
    Inventors: Clinton J. Peake, Carmine P. DiSanzo, John F. Engel
  • Patent number: 4582855
    Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 15, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung T. Kam, William L. Matier
  • Patent number: 4581463
    Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4570006
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsine, anti-plasmin, anti-kallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
  • Patent number: 4567004
    Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters
  • Patent number: 4562280
    Abstract: The invention is a process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: December 31, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jo Ann Gilpin, Lowell B. Lindy
  • Patent number: 4551264
    Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: November 5, 1985
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber
  • Patent number: 4532255
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and antithrombin agents. Having strong anti-C1 (C1r, C1s) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula ##STR2## with 6-amidino-2-naphthol and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: July 30, 1985
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
  • Patent number: 4524223
    Abstract: A general method of resolution of chiral alcohols is based on the relatively facile chromatographic resolution of their diastereomeric esters with optically active amino acids. The naturally occurring L-amino acids and D-(-)-phenylglycine are especially useful, and the method is applicable to a range of alcohols of diverse structure.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: June 18, 1985
    Assignee: UOP Inc.
    Inventor: David W. House
  • Patent number: 4514416
    Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: April 30, 1985
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
  • Patent number: 4511729
    Abstract: Nitrophenoxy- or nitrophenylthiobenzeneacetic acid esters are prepared by reacting a nitrophenoxy- or nitrophenylthiobenzene with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The products are useful as intermediates for the synthesis of pharmaceuticals, such as fenoprofen.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: April 16, 1985
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4511730
    Abstract: This invention relates to carbamates of beta-hydroxyethylsulfoxides which are useful as cosurfactants in enhanced oil recovery, surfactants and biocides, and as hydraulic fluids when of sufficiently low molecular weight.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: April 16, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4507491
    Abstract: To prepare a 1-nitrobenzene-2-alkyloxycarbonyl-5-carboxylic acid, a dialkyl benzene-1,4-dicarboxylate is first nitrated in a customary manner and the dialkyl 1-nitrobenzene-2,5-dicarboxylate compound obtained is subjected to a partial acidic ester hydrolysis without isolating the nitro compound prepared as an intermediate. The acidic ester hydrolysis is carried out in the presence of a catalytic amount of an organic solvent which is completely or partially miscible with water and has a boiling point of above 90.degree. C. and/or of an emulsifier; it is preferably carried out at a temperature between 65.degree. and 110.degree. C.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: March 26, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Wykypiel, Wolfgang Tronich
  • Patent number: 4506089
    Abstract: Methyl m-nitrobenzoate is prepared by a process in which an isomer mixture is treated with from 10 to 1000% by weight of water in the presence of from 0.05 to 20% by weight of an emulsifier, the percentages being based on the weight of the isomer mixture,(a) in a first stage at from 55.degree. to 100.degree. C. and a pH from 2 to 8 and then(b) in a second stage at from 10.degree. to 40.degree. C. and a pH of not less than 9.The methyl m-nitrobenzoate obtainable by the process of the invention is a useful starting material for the preparation of dyes and crop protection agents.
    Type: Grant
    Filed: March 6, 1984
    Date of Patent: March 19, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hackenberger, Manfred Patsch, Manfred Gaeng
  • Patent number: 4503276
    Abstract: This invention pertains to a process for separating nitration isomers of 1,3-disubstituted and 1,2,4-trisubstituted benzene compounds. The separated isomers have a variety of uses including precursors for 2-haloacetanilide herbicides.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: March 5, 1985
    Assignee: Monsanto Company
    Inventor: Thomas E. Nickson
  • Patent number: 4497745
    Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 5, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 4495362
    Abstract: A process for preparing alkyl nitroacetates by reacting an alkyl phenyl carbonate with a nitroparaffin in a polar aprotic solvent in the presence of a cyanide ion. The process permits a higher reaction rate, and thus the reaction can be completed even at room temperature.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: January 22, 1985
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tadatoshi Honda, Yoichi Hosono
  • Patent number: 4490388
    Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with 4-(.beta.-amidinoethenyl)phenol represented by the formula (III) ##STR2## and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 25, 1984
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Takuo Aoyama, Yojiro Sakurai, Toyoo Nakayama, Shigeki Nunomura, Takashi Yaegashi, Toshiyuki Okutome
  • Patent number: 4476315
    Abstract: Nitroarylacetic acid esters are prepared by reacting a nitroaromatic compound which is devoid of halogen on the aromatic ring carrying a nitro group with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base so that the ester undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-substituent functions as a leaving group. Nitrobenzene acetic acids and their esters are useful intermediates for the synthesis of pharmaceuticals.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: October 9, 1984
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly