Plural Halogens Attached Indirectly To The Sulfonate Group By Acyclic Bonding Patents (Class 558/54)
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Patent number: 5716990Abstract: Nitrogen mustard pro-drugs of the formula ##STR1## are disclosed where R is the residue of an .alpha.-amino acid RNH.sub.2 and M is a disubstituted amino "mustard" group, useful in antibody directed enzyme pro-drug therapy in the treatment of cancer.Type: GrantFiled: September 9, 1996Date of Patent: February 10, 1998Assignee: Cancer Research Campaign Technology LimitedInventors: Kenneth D. Bagshawe, Michael Jarman, Caroline Joy Springer
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Patent number: 5674949Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5623084Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-l-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: May 18, 1995Date of Patent: April 22, 1997Assignee: Monsanto CompanyInventor: Peter G. Ruminski
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Patent number: 5596017Abstract: Novel pesticidal sulfamide derivatives of the formula ##STR1## in which X is halogen or C.sub.1 -C.sub.4 -halogenoalkyl,R.sup.1 is C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -halogenoalkyl,R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl, andR.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonylmethyl.Type: GrantFiled: May 19, 1995Date of Patent: January 21, 1997Assignee: Nihon Bayer Agrochem K.K.Inventors: Yuichi Otsu, Yoshinori Kitagawa, Yumi Hattori, Katsuaki Wada, Toru Obinata
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Patent number: 5563174Abstract: A hydrazone compound of the general formula (I): ##STR1## wherein X is halogen; R.sup.1 is hydrogen, optionally substituted C.sub.1 -C.sub.4 alkyl or optionally substituted C.sub.1 -C.sub.4 alkoxy; R.sup.2 's are independently hydrogen or fluorine; R.sup.3 is a group of the general formula: CH.sub.2 R.sup.4 wherein R.sup.4 is cyano or C.sub.1 -C.sub.4 alkoxy; or R.sup.3 is a group of the general formula: SR.sup.5 wherein R.sup.5 is optionally substituted C.sub.1 -C.sub.16 alkyl; optionally substituted phenyl, or the like, has excellent insecticidal activity and rather low toxicity to mammals. The hydrazone compound is useful as an active ingredient of insecticides for controlling harmful insects.Type: GrantFiled: January 10, 1995Date of Patent: October 8, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroki Tomioka, Taro Hirose, Toshiaki Taki, Hirosi Kisida, Shigeru Saito
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Patent number: 5550273Abstract: A process for preparing fluorocarbon fluoroalkanesulfonates comprises (a) forming a mixture comprising at least one fluoroalkanesulfonyl halide, e.g., perfluoromethanesulfonyl fluoride, at least one fluorocarbon-substituted carbinol, e.g., 1,1-dihydroperfluorobutoxyethoxyethanol, and at least one base, e.g., triethyl amine; and (b) allowing the mixture to react in the absence of solvent at a temperature below ambient. The process is volume-efficient and provides high yields of fluorocarbon fluoroalkanesulfonates useful as intermediates in, e.g., drug synthesis.Type: GrantFiled: November 16, 1994Date of Patent: August 27, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventor: Patricia M. Savu
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Patent number: 5541224Abstract: The present invention is directed to anticoccidial methods, animal feed premixes, and animal feeds, employing a specified carbanilide compound. The present invention is also directed to anticoccidial methods, animal feed premixes, and animal feeds employing the specified carbanilide compound and a polyether antibiotic.Type: GrantFiled: February 21, 1995Date of Patent: July 30, 1996Assignee: Eli Lilly and CompanyInventor: George O. P. O'Doherty
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Patent number: 5539059Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: July 23, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5536748Abstract: The present invention provides a hydrazone compound of the formula I: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are independently hydrogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, methoxymethyl or cyanomethyl, with the proviso that the R.sup.1 and R.sup.2 are not simultaneously hydrogen; R.sup.3 is trifluoromethyl or methyl; and X is halogen, and an insecticide containing the hydrazone compound as an active ingredient. The hydrazone compound has good insecticidal activity and lower acute toxicity to mammals.Type: GrantFiled: October 6, 1994Date of Patent: July 16, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Taro Hirose, Toshiaki Taki, Hiroki Tomioka, Hirosi Kisida, Shigeru Saito
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Patent number: 5523475Abstract: The present invention relates to novel derivatives of 3-hydroxyanthranilic acid, 3-HANA, of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and selected from H, alkyl, aryl and arylalkyl; X and Y are the same or different and selected from alkoxy, aryloxy, alkyl, alkylthio, arylthio, fluoroalkyl, halogen, cyano, OSO.sub.2 CH.sub.3, OSO.sub.2 CF.sub.3, OCF.sub.3 and SCF.sub.3 with the proviso that the compound of formula I wherein R.sup.1 and R.sup.2 =H, X=Br and Y=Me is excluded;or a pharmaceutically acceptable salt thereof, methods and intermediates for their preparation, novel pharmaceutical compositions and the use thereof for inhibiting the enzyme 3-hydroxyanthranilate oxygenase, 3-HAO, responsible for the production of the endogenous neurotoxin quinolinic acid, QUIN.Type: GrantFiled: February 24, 1994Date of Patent: June 4, 1996Assignees: Aktiebolaget Astra, Cornell Research Foundation, Inc., The University of Maryland at BaltimoreInventors: Susanna K. M. Bjork, Barry K. Carpenter, Birgitta K. Gotthammar, Mats T. Linderberg, Johan P. Luthman, Kerstin M. I. Persson, Robert Schwarcz
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Patent number: 5468466Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract wherein ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy;n=1-5;y=0-4; andw=1-4in an aqueous pharmaceutically acceptable carrier.Type: GrantFiled: February 1, 1994Date of Patent: November 21, 1995Assignee: Sterling Winthrop, Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5372800Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.Type: GrantFiled: February 4, 1994Date of Patent: December 13, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
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Patent number: 5340837Abstract: Compounds of the formula ##STR1## wherein each of o and p, independently of the other, is 0, 1, 2, 3, 4 or 5, the radicals R.sub.1 being the same or different when o is greater than 1 and the radicals R.sub.2 being the same or different when p is greater than 1;each of R.sub.1 and R.sub.2, independently of the other, is C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halogen, --NO.sub.2, --OH, C.sub.1 -C.sub.4 alkoxy, halo-C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, halo-C.sub.1 -C.sub.4 alkylthio, --O--S(.dbd.O)--R.sub.6, --O--S(.dbd.O).sub.2 --R.sub.6, phenoxy or --N(R.sub.11)SO.sub.2 R.sub.12 and/or two substituents R.sub.1 and/or two substituents R.sub.2 are, independently of one another, together --Y--Z--Y--;R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or halo-C.sub.1 -C.sub.4 alkyl;R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, unsubstituted phenyl or naphthyl or mono- or di-substituted phenyl or naphthyl;R.sub.5 is --S--R.sub.7, --S(.dbd.O)--R.sub.7, --S(.dbd.O).Type: GrantFiled: June 25, 1993Date of Patent: August 23, 1994Assignee: Ciba-Geigy CorporationInventors: Roger G. Hall, Alfons Pascual, Odd Kristiansen
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5302725Abstract: Aryl triflate compounds can generate a strong acid when exposed to irradiation of radiation and can be used as an acid generator in a radiologically-acid-producing agent system and a radiosensitive composition.Type: GrantFiled: October 20, 1992Date of Patent: April 12, 1994Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, S. Peter Pappas
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Patent number: 5245073Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of --SO.sub.2 Alk.sub.1, --SO.sub.2 Ar, ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted with at least one halogen, Ar is aryl of 6 to 14 carbon atoms optionally substituted with at least one halogen Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.Type: GrantFiled: August 20, 1991Date of Patent: September 14, 1993Assignee: Roussel UclafInventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
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Patent number: 5241044Abstract: A process for preparing poly(p-phenylene)s comprises reacting dihydroxy aromatic compounds such as orthoquinone and bisphenols with halogen-substituted aliphatic sulfonic acids, halogen sulfonic acid, or their anhydrides. The monomers thus formed are subsequently polymerized with Ni(0) catalysts to yield the desired polymers. The monomers or polymers may be functionalized with reactive groups.Type: GrantFiled: March 20, 1992Date of Patent: August 31, 1993Assignee: Edison Polymer Innovation CorporationInventor: Virgil Percec
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Patent number: 5200544Abstract: A class of resist compositions sensitive to deep ultraviolet radiation includes a resin sensitive to acid and a composition that generates acid upon exposure to such radiation. A group of nitrobenzyl materials is particularly suitable for use as the acid generator.Type: GrantFiled: January 24, 1992Date of Patent: April 6, 1993Assignee: AT&T Bell LaboratoriesInventors: Francis M. Houlihan, Thomas X. Neenan, Elsa Reichmanis
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Patent number: 5129946Abstract: A composition for treating timber comprising a boron-containing preservative, a thickening agent and, optionally, a fluorosurfactant. The thickening agent can be at least one polysaccharide, such as xanthan gum, or two or more polyacrylamides. The boron-containing preservative can be in the form of a colloidal micro-crystalline suspension of a boron-containing salt. The composition allows the boron-containing preservative to be more readily absorbed by, and diffused into, the timber.Type: GrantFiled: February 7, 1991Date of Patent: July 14, 1992Assignee: Hickson International PLcInventor: David L. Evans
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Patent number: 5110989Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from alkyl, alkenyl and alkynyl;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof, and an alkylene group which bridges two adjacent carbon atoms of the benzene ring;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.Type: GrantFiled: July 17, 1990Date of Patent: May 5, 1992Assignee: ICI Australia LimitedInventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Linsay E. Cross
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Patent number: 5101058Abstract: Novel fluorinated (poly)sulfates, halosulfonates, halohydrins and expoxides, as well as novel processes for producing them are disclosed.Type: GrantFiled: December 11, 1989Date of Patent: March 31, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 5093432Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: September 28, 1989Date of Patent: March 3, 1992Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5089046Abstract: Cyclic 1-one-2-ene-3-ol compounds substituted in 2-position by an aroyl or heteroaroyl group bearing a hydrocarbylsulfonyloxy or hydrocarbylsulfonylamino substituent exhibiting herbicidal activity.Type: GrantFiled: October 2, 1989Date of Patent: February 18, 1992Assignee: Sandoz Ltd.Inventors: Shy-Fuh Lee, Richard J. Anderson, Gary W. Luehr, G. Wayne Craig, Joel L. Kirkpatrick, Takashi Nishizaka, Kenichi Komatsubara
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Patent number: 4980373Abstract: A compound of the formula: ##STR1## which is useful as an insecticide.Type: GrantFiled: August 18, 1989Date of Patent: December 25, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Hirosi Kisida, Kenichi Mikitani, Yoko Torisu, Tomotoshi Imahase, Sumio Nishida
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Patent number: 4925874Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of --SO.sub.2 Alk.sub.1, --SO.sub.2 Ar, ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms no substituted or substituted with at least one functional group, Ar is aryl of 6 to 14 carbon atoms no substituted or substituted with at least one functional group, Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.Type: GrantFiled: November 20, 1987Date of Patent: May 15, 1990Assignee: Roussel UclafInventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4855292Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.Type: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4837307Abstract: A 2,2'-bridged[1,1'-biphenyl]-3-ylmethyl compound of the following formula is an intermediate to insecticidal esters. ##STR1## wherein n is 1-4 and Y is a leaving group readily displaced by carboxylate anions.Type: GrantFiled: January 16, 1984Date of Patent: June 6, 1989Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4734516Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.Type: GrantFiled: March 19, 1986Date of Patent: March 29, 1988Assignee: Ciba-Geigy CorporationInventor: Robert W. Lang
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Patent number: 4668792Abstract: Substituted [1,1'-biphenyl]-3-ylmethyl compounds carrying leaving groups are intermediates to insecticidal esters.Type: GrantFiled: December 20, 1983Date of Patent: May 26, 1987Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4649209Abstract: A process for preparing methyl chlorosulfates by reacting methylene chloride with sulfur trioxide, stabilizing and distilling the reaction mixture, and recovering at least one methyl chlorosulfate as a distillate is disclosed. Preferably, the reaction produces two methyl chlorosulfates, i.e. chloromethyl chlorosulfate and methylene bis-(chlorosulfate), which are separated and recovered by fractional distillation.Type: GrantFiled: August 5, 1985Date of Patent: March 10, 1987Assignee: Occidental Chemical CorporationInventor: Emil J. Geering