Nitrogen In Acid Moiety Patents (Class 560/12)
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Patent number: 4251258Abstract: This disclosure relates to N-(substituted carbonyl) triester derivatives of N-phosphinylmethylglycine wherein a substituted thiocarbonyl, RS(CO)--, a substituted sulfinylcarbonyl, ##STR1## or a substituted sulfonyl carbonyl, ##STR2## group is bonded to the nitrogen atom, to herbicidal compositions containing the same and to the herbicidal use thereof.Type: GrantFiled: September 29, 1978Date of Patent: February 17, 1981Assignee: Monsanto CompanyInventor: Robert J. Kaufman
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Patent number: 4244871Abstract: The invention relates to novel sulfonamidobenzoic acid derivatives having the general formula ##STR1## wherein R.sup.1 denotes a C.sub.1-4 alkoxy group or a hydrazino group or an NR.sup.4 R.sup.5 group, wherein R.sup.4 and R.sup.5 denote each a hydrogen atom or an identical or different C.sub.1-4 alkyl group; furthermore R.sup.4 may denote an aralkyl or substituted aralkyl group provided that R.sup.5 denotes a hydrogen atom; furthermore NR.sup.4 R.sup.5 may denote a morpholine or piperazine ring;R.sup.2 and R.sup.3 may denote each a hydrogen atom or an identical or different C.sub.1-4 aliphatic group; furthermore R.sup.2 may denote a cycloaliphatic, aralkyl, substituted aralkyl or amino group provided that R.sup.3 denotes a hydrogen atom; furthermore R.sup.2 and R.sup.3 may denote together with the adjacent nitrogen atom a morpholino ring, an unsubstituted piperazine ring or a substituted piperazine ring,and to their pharmaceutically acceptable acid addition salts.Type: GrantFiled: July 12, 1979Date of Patent: January 13, 1981Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Judit Kosary, Endre Kasztreiner, Zsuzsa Huszti, Agnes Kenessey, Gyorgy Cseh, Veronika Szilagyi nee Pap, Judit Stverteczky nee Sztrokay
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Patent number: 4238621Abstract: This invention relates to novel o-carbonylbenzenesulfonyl isocyanates and their use as intermediates for the preparation of sulfonylureas which are known to be active herbicides.Type: GrantFiled: June 18, 1979Date of Patent: December 9, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4232173Abstract: Synthetic prostaglandin E compounds having carboxylic acid, ester, tetrazol, sulfonamide or imide substitutions at C-1, a methanesulfonamido group replacing the C-15 hydroxy and an aryloxy group at C-16 are disclosed. They exhibit antisecretory biological activity.Type: GrantFiled: September 17, 1979Date of Patent: November 4, 1980Assignee: Pfizer Inc.Inventors: Thomas K. Schaaf, James F. Eggler
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Patent number: 4230875Abstract: Fungi, mites and mite eggs are killed by applying thereto sulfonamides of the formula ##STR1## wherein R and R.sup.1 individually are alkyl, cycloalkyl, aryl, carbamylalkyl, or alkoxycarbonylalkyl and R.sup.2 is haloalkyl, with the proviso that one R or R.sup.1 group is carbamylalkyl or alkoxycarbonylalkyl.Type: GrantFiled: July 3, 1978Date of Patent: October 28, 1980Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4230628Abstract: This disclosure describes novel 4-[(carboxyl- and sulfamyl-substituted alkyl)amino]benzoic acids and analogs which are useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: April 12, 1978Date of Patent: October 28, 1980Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4230874Abstract: N-(substituted benzenesulfonyl) carbamates as new compositions of matter useful as active herbicidal antidotes to protect against and decrease crop injury when used with a thiocarbamate herbicide when applied in various methods; improved herbicidal compositions and utility of said compositions to protect against and decrease phytotoxic crop injury when employing thiocarbamate herbicides and a two-part herbicide system comprising a first-part of one or more thiocarbamate herbicide and a second part of an effective antidote therefor compound said antidote compounds of the class N-benzene sulfonyl carbamates having the formula ##STR1## wherein X is hydrogen, bromo, chloro, methoxy, trifluoromethyl, and methyl; n is an integer from 1 to 3 inclusive, provided that when X is bromo, trifluoromethyl, or methoxy, n is 1; and R is selected from alkyl, haloalkyl wherein halo is chloro or fluoro, alkenyl, haloalkenyl and wherein halo is chloro, alkynyl, trifluoroacetamidomethyl, dialkylamino cyanoalkylthioalkyl, phosphonType: GrantFiled: September 13, 1976Date of Patent: October 28, 1980Assignee: Stauffer Chemical CompanyInventors: Ferenc M. Pallos, Edmund J. Gaughan
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Patent number: 4227015Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.Type: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: 4225725Abstract: Esters of certain 2,4,6-triiodobenzoic acid derivatives are useful as X-Ray contrast media. Representative compounds are the ethoxymethyl esters of acetrizoic, iothalamic and iodobenzamic acids.Type: GrantFiled: October 20, 1975Date of Patent: September 30, 1980Assignee: Mallinckrodt, Inc.Inventor: George B. Hoey
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Patent number: 4224418Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: June 15, 1979Date of Patent: September 23, 1980Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4224454Abstract: Acyloin urethans can be employed to effect photopolymerization of free radical-polymerizable compositions in inert and oxygen-containing atmospheres.Type: GrantFiled: October 13, 1978Date of Patent: September 23, 1980Assignee: Lord CorporationInventors: John R. McDowell, Dennis D. Howard, Vincent J. Pascarella
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Patent number: 4219661Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.Type: GrantFiled: April 23, 1979Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
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Patent number: 4215139Abstract: Carbamic acid derivatives, processes for their preparation, as well as pesticidal compositions containing the carbamic acid derivatives, and methods for their use, are disclosed.Type: GrantFiled: March 6, 1979Date of Patent: July 29, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Ulf Fischer, Fernand Schneider, Rene Zurflueh
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Patent number: 4205085Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: March 9, 1978Date of Patent: May 27, 1980Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4199597Abstract: Omega-[4-(polyfluoro-2-hydroxy-2-propyl)-2,3,6-substituted-phenoxy and phenylthio]alkanoic acids and compounds related thereto having antihypertensive activity are preparable by reaction of the appropriate 2,3,6-substituted-4-(polyfluoro-2-hydroxy-2-propyl)phenol or thiophenol with an alkyl ester of a bromoalkanoic acid, followed by hydrolysis to the free acid.Type: GrantFiled: May 4, 1979Date of Patent: April 22, 1980Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4199595Abstract: The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.Type: GrantFiled: March 20, 1978Date of Patent: April 22, 1980Assignee: American Cyanamid CompanyInventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4186269Abstract: An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration.Type: GrantFiled: December 31, 1975Date of Patent: January 29, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyate, Makoto Aiga
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Patent number: 4178460Abstract: The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and .alpha.-cyano-m-phenoxybenzyl esters.Type: GrantFiled: March 20, 1978Date of Patent: December 11, 1979Assignee: American Cyanamid Co.Inventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4174434Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: July 31, 1978Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4170596Abstract: A novel monoester of cis-cyclopentenediol of the following formula ##STR1## wherein ##STR2## is an optically active acyl moiety. The monoester can be prepared by reacting cis-2-cyclopentene-1,4-diol with an optically active carboxylic acid of the following formula ##STR3## wherein ##STR4## is the same as defined above, or its reactive derivative, and separating the resulting reaction product into the two individual diastereomers. Lactones can be prepared from the monoesters selectively and with commercial advantage.Type: GrantFiled: October 4, 1977Date of Patent: October 9, 1979Assignee: Kowa Company, Ltd.Inventors: Shun-Ichi Yamada, Shiro Terashima, Masahiko Nagakura, Munehiko Nara
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Patent number: 4164408Abstract: 2-Nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: September 26, 1977Date of Patent: August 14, 1979Assignee: Mobil Oil Corp.Inventor: Robert J. Theissen
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Patent number: 4164409Abstract: 2-Nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: May 5, 1978Date of Patent: August 14, 1979Assignee: Mobil Oil Corp.Inventor: Robert J. Theissen
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Patent number: 4164410Abstract: 2-Nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: May 5, 1978Date of Patent: August 14, 1979Assignee: Mobil Oil Corp.Inventor: Robert J. Theissen
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Patent number: 4154756Abstract: This disclosure describes 2-substituted 4'-(monoalkylamino)-acetophenones useful as hypolipidemic and anti-atherosclerotic agents.Type: GrantFiled: December 15, 1977Date of Patent: May 15, 1979Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4152457Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.Type: GrantFiled: October 11, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4146557Abstract: N,N-dichloro-N-acyl compounds, such as N,N-dichlorocarbamates, sulfonamides and amidosulfonamides selectively react with conjugated dienes to yield the corresponding 1,4-adducts, i.e. N-chloro-N-chlorocrotyl compounds. The N-chloro group of these adducts can be selectively reduced by aqueous sodium sulfite. Both the original and the reduced adducts are novel compositions useful as biologically active compounds and vulcanizing agents. The N-chlorocrotyl sulfonamides and their N-chloro derivatives are particularly claimed compositions.Type: GrantFiled: May 21, 1975Date of Patent: March 27, 1979Assignee: Exxon Research & Engineering Co.Inventors: Francis A. Daniher, Alexis A. Oswald
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Patent number: 4119658Abstract: The present invention relates to isocyanato-polysulphonic acids comprising from 1 to 3 aromatically bound isocyanate groups which may be present at least partly in the dimerized form as uretdione groups and from 2 to 6 sulphonic acid groups for each non-dimerized isocyanato-polysulphonic acid or for each monomeric isocyanato-polysulphonic acid on which the dimer is based. These acids are produced by reacting mono- or poly-isocyanates having exclusively aromatically bound isocyanate groups with sulphur trioxide at -10.degree. C to 140.degree. C, wherein the isocyanate used as starting material which is to be sulphonated is reacted with at least 50% by weight of sulphur trioxide, based on the quantity of isocyanate used as starting material. Alternatively they may be produced using isocyanate-monosulphonic acids which have exclusively aromatically bound isocyanate-groups.Type: GrantFiled: March 30, 1977Date of Patent: October 10, 1978Assignee: Bayer AktiengesellschaftInventor: Dieter Dieterich
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Patent number: 4115105Abstract: L-2-amino-4-(2-aminoethoxy)-butanoic acid, methods for its preparation and novel intermediates employed in these processes are disclosed. L-2-amino-4-(2-aminoethoxy)-butanoic acid enhances ethylene production in fruit and therefore has utility as a ripening agent and as an abscission agent.Type: GrantFiled: August 29, 1977Date of Patent: September 19, 1978Assignee: Hoffmann-La Roche Inc.Inventors: James Parnell Scannell, Arthur Stempel
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Patent number: 4113463Abstract: A method for regulating the elongation of plants so as to increase their resistance to lodging by applying a plant regulating effective amount of a plant growth regulator containing as active ingredient a benzenesulfonamide compound of the formula ##STR1## wherein X, R.sub.1, R.sub.2 and n are as defined hereinbelow.Type: GrantFiled: March 11, 1977Date of Patent: September 12, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Hiromichi Oshio, Hiroyuki Konishi, Shiunzi Matsumura, Kikuichi Ishikawa, Eiichi Yoneyama
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Patent number: 4112237Abstract: Fungi, mites and mite eggs are killed by applying thereto sulfonamides of the formula ##STR1## wherein R and R.sup.1 individually are alkyl, cycloalkyl, aryl, carbamylalkyl, or alkoxycarbonylalkyl and R.sup.2 is haloalkyl, with the proviso that one R or R.sup.1 group is carbamylalkyl or alkoxycarbonylalkyl.Type: GrantFiled: October 22, 1976Date of Patent: September 5, 1978Assignee: Chevron Research CompanyInventor: David Cheong King Chan
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Patent number: 4112236Abstract: Interphenylene 8-aza-9-dioxothia-11,12-secoprostaglandins are prepared by the two-stage alkylation of the anion of a lower alkyl sulfonamide, R.sup.1 SO.sub.2 NH.sub.2, using first a compound of the formula: ##STR1## and second, a compound of the formula: ##STR2## The compounds produced have renal vasodilatory activity when administered orally and are therefore useful for treating patients with renal impairment.Type: GrantFiled: April 4, 1977Date of Patent: September 5, 1978Assignee: Merck & Co., Inc.Inventors: John B. Bicking, Edward J. Cragoe, Jr.
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Patent number: 4108887Abstract: Disclosed are compounds of formula I ##STR1## in which R.sub.1 and R.sub.4, independently, are hydrogen, a non-chromophoric second order substituent, or alkyl or alkenyl unsubstituted or substituted by a non-chromophoric group,R.sub.2 and R.sub.5, independently, are hydrogen or alkyl or alkenyl, unsubstituted or substituted by a non-chromophoric group,R.sub.3 and R.sub.6, independently, are hydrogen, alkyl, carboxyl or a non-chromophoric esterified carboxyl group, orR.sub.2, together with R.sub.3, and/or R.sub.5 together with R.sub.6, signify an alkylene bridge,R.sub.7 and R.sub.8, independently, signify hydrogen or a non-chromophoric substituent, or, whenR.sub.7 is in the 3-position and/or R.sub.8 in the 3' position, R.sub.7 together with R.sub.2, and/or R.sub.8 together with R.sub.5 signify an alkylene bridge,With the proviso that no more than one of R.sub.1 and R.sub.2 and no more than one of R.sub.4 and R.sub.5 signify hydrogen, their production and use as optical brightening agents.Type: GrantFiled: January 29, 1976Date of Patent: August 22, 1978Assignee: Sandoz Ltd.Inventors: Fritz Fleck, Juerg Heller
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Patent number: 4105790Abstract: The invention concerns .alpha.-aminoacyl derivatives of phenyl-, phenoxy-, thiophenoxy- and phenylsulphinylalkanoic acids together with their amides, esters and pharmaceutically acceptable salts; processes for their preparation; and pharmaceutical compositions for therapeutic use in inhibiting the formation of thrombi and also in reducing the persistence of thrombi formed in the blood of warm blooded animals. Representative compounds of the invention are methyl 4-(aminoacetyl)phenoxyacetate, 4-(aminoacetyl)phenoxyacetic acid and methyl 4-(aminoacetyl)-thiophenoxyacetate, preferably as their hydrochlorides.Type: GrantFiled: November 9, 1976Date of Patent: August 8, 1978Assignee: Imperial Chemical Industries LimitedInventors: Clifford R. Hughes, Stephen J. Jackson, John Preston, Peter L. Walton
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Patent number: 4098900Abstract: N,N'-Diphenyl-guanidine derivative of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each represent hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 -halogenalkyl, C.sub.1 -C.sub.5 -alkoxy, (C.sub.1 -C.sub.5 -alkyl)-carbonyl, (C.sub.1 -C.sub.5 -alkoxy)-carbonyl, cyano and/or nitro and R.sub.6 represents C.sub.1 -C.sub.5 -alkylsulfonyl or optionally substituted phenylsulphonyl, processes for their production, and their use in pest control.Type: GrantFiled: March 3, 1976Date of Patent: July 4, 1978Assignee: Ciba-Geigy CorporationInventors: Volker Dittrich, Werner Topfl, Odd Kristiansen
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Patent number: 4097526Abstract: An in-situ process for preparing organic sulfone compounds by oxidizing the corresponding sulfide compound with a mixture of hydrogen peroxide, a carboxylic acid in the presence of a catalytic amount of a mineral acid or an organic sulfonic acid.Type: GrantFiled: February 10, 1977Date of Patent: June 27, 1978Assignee: Union Carbide CorporationInventor: John Kai-Fai Chan
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Patent number: 4094863Abstract: A process for the cross-linking or chain-extension of hydrocarbon polymers which contain ethylenically unsaturated groups which comprises forming an intimate mixture of the polymer with a mono-sulphonyloxycarbamate of the formula:A -- O -- CO -- NH -- O -- SO.sub.2 R (1)wherein A is an alkyl group, a cycloalkyl group, an alkenyl group, a substituted alkyl group, a substituted aryl group or a heterocyclic group, and R is an optionally substituted alkyl or aryl group.The process is useful for natural and synthetic rubbers. The rate and extent of cross linking may be modified by the additives such as tertiary amines or conventional rubber additives e.g. tetramethyl and zinc diethyl dithiocarbamates, which contain tertiary amino groups.Type: GrantFiled: February 22, 1977Date of Patent: June 13, 1978Assignee: Imperial Chemical Industries LimitedInventors: John Langshaw Brooks, Richard Budziarek
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Patent number: 4093445Abstract: Herbicidal compositions consisting of an active herbicidal compound and an antidote therefor and the methods of use of the herbicide compositions are described herein. The antidote compound corresponds to the formula ##STR1## wherein R.sub.1 can be selected from the group consisting of alkyl, haloalkyl, halogen, isocyanate, alkenylamino, halophenylamino, phenyl, substituted phenyl wherein said substituents can be selected from alkyl, alkoxy, halogen, nitro, amino and haloalkylaminosulfonyl; R.sub.2 and R.sub.3 can be the same or different and can be selected from hydrogen, alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, alkynoxy, haloalkoxycarbonyl, alkynoxycarbonyl, carbamoyl, haloalkylthio, diacetonitrilocarbamyl, phenyl, substituted phenyl wherein said substituents can be selected from alkoxy, halogen, hydroxy, nitro and carbamoyl, and R.sub.2 and R.sub.3 taken together form the ring structure alkyloxazolidyl.Type: GrantFiled: January 24, 1977Date of Patent: June 6, 1978Assignee: Stauffer ChemicalInventors: Duane R. Arneklev, Don R. Baker
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Patent number: 4086255Abstract: Phenyl-substituted perfluoroalkanesulfonanilides in which the phenyl rings are linked by sulfur, sulfinyl or sulfonyl and salts thereof in which the rings and the perfluoroalkylsulfonamido nitrogen are optionally substituted. The compounds are active herbicides and some are anti-inflammatory agents and analgesic agents.Type: GrantFiled: January 10, 1977Date of Patent: April 25, 1978Assignee: Minnesota Mining and Manufacturing CompanyInventors: George G. I. Moore, Joseph Kenneth Harrington
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Patent number: 4080365Abstract: Aromatic urethanes can be produced in exceedingly improved yield when an aromatic nitro compound, an organic compound containing hydroxyl groups, and carbon monoxide are reacted in the presence of a catalyst composed of metallic (elemental) selenium or a selenium compound and a base serving as promoter, to which reaction system an aromatic amino compound and/or an aromatic urea compound which will be secondarily produced by the reaction has been previously added in order to suppress side reactions. For instance, when nitrobenzene, methanol and carbon monoxide are interacted in the presence of metallic selenium and triethylenediamine, the conversion of nitrobenzene is 68% and the percentage of formed methyl N-phenylcarbamate to the interacted nitrobenzene is 80%, whereas when the reaction is effected under the same reaction conditions indicated above with addition to the reaction system of aniline in an amount of about 15 wt.Type: GrantFiled: May 19, 1976Date of Patent: March 21, 1978Assignee: Mitsui Toatsu ChemicalsInventors: Yutaka Hirai, Katsuharu Miyata, Seiji Hasegawa
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Patent number: 4071686Abstract: Certain nuclear substituted benzylidene amino oxyalkyl carboxylic acids esters, amides and salts thereof have been found to have a strong anti-inflammatory activity and a potent analgetic activity. In addition, some of the compounds have an activity against Rhino virus. An example is [(4-chlorobenzylideneamino)oxy] acetic acid.Type: GrantFiled: December 17, 1976Date of Patent: January 31, 1978Assignee: U.S. Philips CorporationInventors: Jan van Dijk, Volkert Claassen, Johannes Maria Antonius Zwagemakers
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Patent number: 4071351Abstract: Herbicidal compositions consisting of an active herbicidal compound and an antidote therefor and the methods of use of the herbicide compositions are described herein. The antidote compound corresponds to the formula ##STR1## wherein R.sub.1 can be selected from the group consisting of alkyl, haloalkyl, halogen, isocyanate, alkenylamino, halophenylamino, phenyl, substituted phenyl wherein said substituents can be selected from alkyl, alkoxy, halogen, nitro, amino and haloalkylaminosulfonyl; R.sub.2 and R.sub.3 can be the same or different and can be selected from hydrogen, alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, alkynoxy, haloalkoxycarbonyl, alkynoxycarbonyl, carbamoyl, haloalkylthio, diacetonitrilocarbamyl, phenyl, substituted phenyl wherein said substituents can be selected from alkoxy, halogen, hydroxy, nitro and carbamoyl, and R.sub.2 an R.sub.3 taken together form the ring structure alkyloxazolidyl.Type: GrantFiled: January 24, 1977Date of Patent: January 31, 1978Assignee: Stauffer Chemical CompanyInventors: Duane R. Arneklev, Don R. Baker
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Patent number: 4070178Abstract: Diphenyl ethers of the formula ##STR1## whereinR.sup.1 is hydrogen or halogen,R.sup.2 is hydrogen, halogen, or cyano,R is ##STR2## wherein R.sup.3 is hydrogen, halogen, nitro, alkyl, or alkoxy,R.sup.4 is a divalent alkylene radical, andR.sup.5 is cyano or -COR.sup.6, wherein R.sup.6 is alkoxy, hydroxy or salt thereof, allyloxy, alkoxyalkoxy, amino, alkyl or dialkyl amino, aminoalkoxy, or alkyl or dialkylaminoalkoxy,And diphenyl sulfides, sulfoxides, and sulfones of the formula ##STR3## wherein R.sup.8 is hydrogen, halogen, cyano, nitro, alkyl, alkoxy, or trifluoromethyl,R.sup.2 is hydrogen, halogen or cyano,X is sulfur, sulfinyl, or sulfonyl, andR is as defined above,And compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: July 30, 1976Date of Patent: January 24, 1978Assignee: Rohm and Haas CompanyInventors: Wayne O. Johnson, Roy Y. Yih
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Patent number: 4069343Abstract: Anti-allergic agents of aromatic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of .alpha.-naphthyl, .beta.-naphthyl, phenyl, 2,6-dichlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals;And pharmaceutically acceptable salts thereof.Type: GrantFiled: March 23, 1976Date of Patent: January 17, 1978Assignee: American Home Products CorporationInventors: John H. Sellstedt, Charles J. Guinosso, Albert J. Begany
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Patent number: 4057418Abstract: Novel benzoic acid compounds of the formula ##STR1## in which R is alkyl or substituted alkyl of up to 6 carbon atoms, where the substituents are selected from halogen, orR is aryl which is optionally substituted by halogen and/or by alkyl of up to 4 carbon atoms,R.sup.1 is alkyl, alkoxy or alkylmercapto, of in each case up to 4 carbon atoms, or halogen,R.sup.2 is hydrogen,R.sup.3 is hydrogen or halogen,R.sup.4 is hydroxyl, alkoxy of 1 to 6 carbon atoms or an amino group which is optionally substituted by one or two alkyl radicals each of up to 6 carbon atoms, andR.sup.5 is halogen or alkyl of up to 4 carbon atoms; are outstandingly effective and selective as herbicides.Type: GrantFiled: January 19, 1976Date of Patent: November 8, 1977Assignee: Bayer AktiengesellschaftInventors: Wolfgang Hofer, Fritz Maurer, Hans-Jochem Riebel, Rolf Schroder, Ludwig Eue
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Patent number: 4057556Abstract: Tropone derivatives characterized by having a derivative of oxamic acid at positions 2 and/or 5 are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of said compounds are disclosed.Type: GrantFiled: June 17, 1976Date of Patent: November 8, 1977Assignee: Ayerst, McKenna & Harrison Ltd.Inventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4057555Abstract: 1,2-Benzoisothiazole-3-on-1, 1-dioxide having the formula ##STR1## wherein X represents hydrogen, halogen, nitro, lower alkyl or lower alkoxy and Y represents hydrogen, halogen, lower alkyl, or lower alkoxy is prepared by reacting phosgene with an o-sulfobenzoic acid compound having the formula: ##STR2## or an alkali metal salt or alkaline earth metal salt thereof in the presence of dimethylformamide, thereby producing a mixture of a dichlorotolylsultone and a chlorosulfonylbenzoylchloride; (b) reacting the reaction products of step (a) with an alcohol of the formula ROH wherein R represents a lower alkyl group; and then (c) reacting the product of step (b) with ammonia.Type: GrantFiled: April 15, 1976Date of Patent: November 8, 1977Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Takahiro Kimoto, Sadayoshi Matsui
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Patent number: 4054740Abstract: This invention relates to a synthesis of biotin by the reduction of dehydrobiotin. The dehydrobiotin is prepared from 6-hydroxy-7-nitro-heptanoic acid methyl ester. Novel intermediates are also obtained by this synthesis.Type: GrantFiled: September 5, 1975Date of Patent: October 18, 1977Assignee: Hoffmann-La Roche Inc.Inventor: George Francis Field
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Patent number: 4054593Abstract: Poly-sulphonyloxyurethanes of the formulaA[O--CO--NH--O--SO.sub.2 --R].sub.n (1)wherein A is a linking group to which the oxygen atoms are attached at alkyl, cycloalkyl or aryl carbon atoms, n is an integer of value at least 2, and each R which may be the same or different, is an optionally substituted alkyl or aryl group, and their salts, especially salts with cations based on tertiary amines, are useful cross-linking or chain-extending agents for natural or synthetic polymers, or may be used as adhesives for binding these materials to each other or to metal substrates.Type: GrantFiled: February 9, 1976Date of Patent: October 18, 1977Assignee: Imperial Chemical Industries LimitedInventors: John Langshaw Brooks, Richard Budziarek
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Patent number: RE29608Abstract: The invention provides novel 5- and 6-benzoxazolyl alkanoic acids, optionally substituted in the 2-position, and derivatives thereof which possess anti-inflammatory, anti-pyretic and analgesic activity. Also provided is a process for preparing such compounds by cyclizing an appropriately substituted o-aminophenol and, if necessary, converting the resultant benzoxazole to the desired compound.Type: GrantFiled: February 1, 1977Date of Patent: April 11, 1978Assignee: Lilly Industries LimitedInventors: Delme Evans, David William Dunwell, Terence Alan Hicks