Nitro Bonded To Carbon In Acid Moiety Patents (Class 560/20)
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Patent number: 4727180Abstract: 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: GrantFiled: January 4, 1985Date of Patent: February 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul E. Aldrich, Gilbert H. Berezin
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Patent number: 4727199Abstract: 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: GrantFiled: July 10, 1985Date of Patent: February 23, 1988Assignee: Union Carbide CorporationInventor: Stephen W. King
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Patent number: 4723030Abstract: 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: GrantFiled: August 5, 1985Date of Patent: February 2, 1988Assignee: General Electric CompanyInventor: Gary C. Davis
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Patent number: 4717418Abstract: 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: GrantFiled: November 10, 1982Date of Patent: January 5, 1988Assignee: ICI Australia LimitedInventors: Richard B. Warner, Alexander Serban, Keith G. Watson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
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Patent number: 4710581Abstract: 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: GrantFiled: October 3, 1985Date of Patent: December 1, 1987Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4709107Abstract: 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: GrantFiled: October 11, 1985Date of Patent: November 24, 1987Assignee: General Electric CompanyInventors: Paul R. West, Gary C. Davis
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Patent number: 4703110Abstract: 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: GrantFiled: July 8, 1985Date of Patent: October 27, 1987Assignee: Koichi ShudoInventor: Koichi Shudo
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Patent number: 4693848Abstract: 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: GrantFiled: April 2, 1986Date of Patent: September 15, 1987Assignee: Basf AktiengesellschaftInventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
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Patent number: 4686309Abstract: 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: GrantFiled: February 15, 1985Date of Patent: August 11, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
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Patent number: 4684639Abstract: 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: GrantFiled: July 5, 1984Date of Patent: August 4, 1987Assignee: Beecham GroupInventors: George Burton, Desmond J. Best
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Patent number: 4680419Abstract: 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: GrantFiled: July 22, 1985Date of Patent: July 14, 1987Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4670581Abstract: 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: GrantFiled: January 10, 1984Date of Patent: June 2, 1987Assignee: Sugai Chemical Industry Co., Ltd.Inventor: Teiichi Tanigaki
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Patent number: 4664852Abstract: 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: GrantFiled: May 22, 1986Date of Patent: May 12, 1987Assignee: Sclavo S.p.A.Inventors: Paolo Casati, Claudio Fuganti
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Patent number: 4659372Abstract: 2-Aryl-1,3-cyclohexanedione enol ester compounds exhibit outstanding miticidal, mite ovicidal and herbicidal activity.Type: GrantFiled: November 28, 1983Date of Patent: April 21, 1987Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4659862Abstract: 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: GrantFiled: May 3, 1984Date of Patent: April 21, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thaliyil V. Rajanbabu
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Patent number: 4652672Abstract: 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: GrantFiled: October 17, 1983Date of Patent: March 24, 1987Inventor: Wolfgang F. Lindner
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Patent number: 4652303Abstract: 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: GrantFiled: July 2, 1984Date of Patent: March 24, 1987Assignee: ICI Australia LimitedInventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
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Patent number: 4647555Abstract: 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: GrantFiled: October 25, 1984Date of Patent: March 3, 1987Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Bernard F. Spielvogel, Andrew T. McPhail, Iris H. Hall
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Patent number: 4645305Abstract: 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: GrantFiled: November 23, 1984Date of Patent: February 24, 1987Assignee: Hitachi, Ltd.Inventors: Hisao Yokokura, Susumu Era, Hidetoshi Abe, Tadao Nakata, Teruo Kitamura, Akio Mukoh
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Patent number: 4643763Abstract: 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: GrantFiled: September 10, 1985Date of Patent: February 17, 1987Assignee: ICI Australia LimitedInventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
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Patent number: 4640706Abstract: 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: GrantFiled: March 20, 1985Date of Patent: February 3, 1987Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4640708Abstract: 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: GrantFiled: March 20, 1984Date of Patent: February 3, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
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Patent number: 4639541Abstract: 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: GrantFiled: April 25, 1985Date of Patent: January 27, 1987Assignee: Consortium fur elektrochemische Industrie GmbHInventors: Gerhard Staiger, Tassilo Selmayr, Peter Kinzel, Anneliese Reutter
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Patent number: 4639267Abstract: 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: GrantFiled: September 10, 1985Date of Patent: January 27, 1987Assignee: ICI Australia LimitedInventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
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Patent number: 4620027Abstract: 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: GrantFiled: December 21, 1984Date of Patent: October 28, 1986Assignee: Sun Refining and Marketing CompanyInventor: Chao-Yang Hsu
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Patent number: 4613681Abstract: 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: GrantFiled: June 30, 1980Date of Patent: September 23, 1986Assignee: Produits Chimiques Ugine KuhlmannInventors: Louis Foulletier, Andre Lantz
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Patent number: 4607053Abstract: 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: GrantFiled: April 4, 1985Date of Patent: August 19, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Martin F. Haslanger
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Patent number: 4605758Abstract: 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: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4604407Abstract: 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: GrantFiled: April 4, 1985Date of Patent: August 5, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Martin F. Haslanger, Donald S. Karanewsky
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Patent number: 4604243Abstract: 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: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4588531Abstract: 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: GrantFiled: October 18, 1984Date of Patent: May 13, 1986Assignee: BASF AktiengesellschaftInventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
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Patent number: 4584318Abstract: 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: GrantFiled: June 20, 1983Date of Patent: April 22, 1986Assignee: FMC CorporationInventors: Clinton J. Peake, Carmine P. DiSanzo, John F. Engel
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Patent number: 4582855Abstract: 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: GrantFiled: November 12, 1981Date of Patent: April 15, 1986Assignee: American Hospital Supply CorporationInventors: Sheung T. Kam, William L. Matier
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Patent number: 4581463Abstract: 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: GrantFiled: August 10, 1984Date of Patent: April 8, 1986Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4570006Abstract: 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: GrantFiled: October 24, 1984Date of Patent: February 11, 1986Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
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Patent number: 4567004Abstract: 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: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4562280Abstract: 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: GrantFiled: October 18, 1984Date of Patent: December 31, 1985Assignee: The Dow Chemical CompanyInventors: Jo Ann Gilpin, Lowell B. Lindy
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Patent number: 4551264Abstract: 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: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4532255Abstract: 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: GrantFiled: January 20, 1984Date of Patent: July 30, 1985Assignee: Torii & Co., Ltd.Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
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Patent number: 4524223Abstract: 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: GrantFiled: January 19, 1984Date of Patent: June 18, 1985Assignee: UOP Inc.Inventor: David W. House
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Patent number: 4514416Abstract: 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: GrantFiled: May 21, 1984Date of Patent: April 30, 1985Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
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Patent number: 4511729Abstract: 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: GrantFiled: March 10, 1983Date of Patent: April 16, 1985Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4511730Abstract: 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: GrantFiled: August 17, 1982Date of Patent: April 16, 1985Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4507491Abstract: 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: GrantFiled: November 29, 1982Date of Patent: March 26, 1985Assignee: Hoechst AktiengesellschaftInventors: Werner Wykypiel, Wolfgang Tronich
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Patent number: 4506089Abstract: 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: GrantFiled: March 6, 1984Date of Patent: March 19, 1985Assignee: BASF AktiengesellschaftInventors: Alfred Hackenberger, Manfred Patsch, Manfred Gaeng
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Patent number: 4503276Abstract: 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: GrantFiled: January 9, 1984Date of Patent: March 5, 1985Assignee: Monsanto CompanyInventor: Thomas E. Nickson
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Patent number: 4497745Abstract: 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: GrantFiled: September 30, 1982Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventor: Henry Martin
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Patent number: 4495362Abstract: 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: GrantFiled: November 4, 1982Date of Patent: January 22, 1985Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tadatoshi Honda, Yoichi Hosono
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Patent number: 4490388Abstract: 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: GrantFiled: February 22, 1982Date of Patent: December 25, 1984Assignee: Torii & Co., Ltd.Inventors: Setsuro Fujii, Takuo Aoyama, Yojiro Sakurai, Toyoo Nakayama, Shigeki Nunomura, Takashi Yaegashi, Toshiyuki Okutome
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Patent number: 4476315Abstract: 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: GrantFiled: December 23, 1982Date of Patent: October 9, 1984Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly