1,2,3-thiadiazoles (including Hydrogenated) Patents (Class 548/127)
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Patent number: 4788292Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of one another, represent hydrogen, hydroxy or halogen or are alkyl, alkoxy, alkanoyloxy, or alkanoylamino groups which are unsubstituted or substituted by alkoxy, hydroxyl, halogen, aryl, cycloalkyl, azacycloalkyl, cyano or by polyalkyleneoxy, or two or more of adjacent R.sub.1 -R.sub.4 together form one or more fused rings of 5-8 members each; R is alkylene of up to 16 carbon atoms which is unsubstituted or substituted by hydroxy, lower alkoxy, or halo and which may be interrupted by oxygen, sulfur, carboxamido, sulfonamido, aminosulfonyl, aminocarbonyl, carbonyloxy, sulfinyl, or sulfonyl; and R.sub.f is perfluoroalkyl or perfluoroalkoxyalkyl of 4 to 16 carbon atoms; or mixtures thereof. Such compounds are useful as oil soluble corrosion inhibitors.Type: GrantFiled: July 31, 1986Date of Patent: November 29, 1988Assignee: Ciba-Geigy CorporationInventors: Kirtland P. Clark, Athanasios Karydas
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Patent number: 4782083Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 -polymethylene;either R.sub.3 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together are a bond;R.sub.5 is hydrogen C.sub.1-6 alkyl optionally substituted by halogen hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C.sub.1-6 alkyl groups, or C.sub.2-6 alkenyl, amino optionally substituted by a C.sub.1-6 alkyl or C.sub.1-6 alkenyl group or by a C.sub.1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or aryl or hetroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C.sub.1-6 alkyl, C.sub.Type: GrantFiled: August 29, 1986Date of Patent: November 1, 1988Assignee: Beecham Group P.L.C.Inventors: Frederick Cassidy, Geoffrey Stemp, John M. Evans
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Patent number: 4775406Abstract: The salts of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring, of the general formula (I) ##STR1## exhibit a good plant growth-regulating activity. In the general formula the symbols have the following meaning:Y is an ammonium ion substituted up to fourfold by (substituted) alkyl, (substituted) alkenyl, alkynyl, (substituted) cycloalkyl, cycloalkenyl, and (substituted) phenyl, wherein the charged N may be part of a heterocyclic radial (NH.sub.4.sup.+ is excepted); phosphonium ion substituted fourfold by alkyl, (substituted) phenyl or (substituted) benzyl; sulfonium- or sulfoxonium ion substituted threefold by alkyl, (substituted) phenyl or (substituted) benzyl; the guanidinium ion or an O-alkylisourea cation;R.sup.1, R.sup.2 independently of each other are alkyl;R.sup.3 is alkyl, alkoxy or halogen; andn is 0, 1, 2 or 3.Type: GrantFiled: November 21, 1985Date of Patent: October 4, 1988Assignee: Hoechst AktiengesellschaftInventors: Roland Schmierer, Ernst-Friedrich Schulze, Helmut Bustell, Erwin Hacker
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Patent number: 4772622Abstract: Novel diamino oxadiazoles, wherein one of the amine functions is connected to a basicly-substituted heterocyclic group through a linear or cyclic connecting group, which are useful for the suppression of gastric acid secretions in mammals. Compositions employing these compounds and processes for the preparation of such compounds from known N-cyano-S-methylisothiourea precursors by treatment with hydroxylamine and for alkylation of amine groups are also disclosed.Type: GrantFiled: June 16, 1986Date of Patent: September 20, 1988Assignee: Merck & Co., Inc.Inventors: Susan F. Britcher, William C. Lumma, Jr.
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Patent number: 4772309Abstract: A 5-Acylamino-pyrazole derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, halogen or nitro,R.sup.2 represents hydrogen, alkyl, alkenyl, alkinyl or optionally substituted cycloalkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,X represents oxygen or sulphur,n represents the integer 0, 1 or 2,Ar represents in each case optionally substituted phenyl or pyridyl andHet represents an optionally substituted 5- or 6- membered heterocyclic radical linked via a carbon atom,which exhibit herbicidal and plant growth regulating activity.Type: GrantFiled: March 19, 1987Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Reinhold Gehring, Otto Schallner, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
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Patent number: 4762848Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.Type: GrantFiled: March 10, 1986Date of Patent: August 9, 1988Assignee: Hoechst AktiengesellschaftInventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
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Patent number: 4748165Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.Type: GrantFiled: May 11, 1982Date of Patent: May 31, 1988Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4743690Abstract: 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: January 16, 1987Date of Patent: May 10, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thaliyil V. Rajanbabu
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Patent number: 4742060Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.Type: GrantFiled: January 21, 1986Date of Patent: May 3, 1988Assignee: Nihon Tokushu Noyaku Seizo K. K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4740231Abstract: 1-Aryl-5-alkoximinoalkylamino-pyrazoles of the formula ##STR1## in which R represents cyano or nitro, or represents an optionally substituted heterocyclic radical,R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen or alkyl, or represents optionally substituted aryl,R.sup.3 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl or aryl andAr represents optionally substituted phenyl or pyridyl,are active as herbicides and plant growth regulants. Compounds of the formula ##STR2## in which R" has the same definition as R other than cyano, are also active and useful as intermediates as well.Type: GrantFiled: May 22, 1986Date of Patent: April 26, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhold Gehring, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
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Patent number: 4731364Abstract: 2-Alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-2-(1H-azolyl(C.sub.1 -C.sub.2)alkyl)benzo[b]thiophenes especially 2-alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-3-hydroxy-2-(1H-1-imidazolylmethyl)-4-,5-,6- and 7-halobenzo[b]thiophenes and related derivatives having antifungal activity are disclosed. Pharmaceutical compositions comprising compounds of the invention and their use in treating fungal infections in susceptible hosts such as humans are also disclosed.Type: GrantFiled: August 12, 1985Date of Patent: March 15, 1988Assignee: Schering CorporationInventors: Dinanath F. Rane, Russell E. Pike
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Patent number: 4721712Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.Type: GrantFiled: November 13, 1984Date of Patent: January 26, 1988Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4695567Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.Type: GrantFiled: January 17, 1986Date of Patent: September 22, 1987Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
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Patent number: 4695311Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.Type: GrantFiled: May 9, 1986Date of Patent: September 22, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer
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Patent number: 4692513Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.Type: GrantFiled: December 20, 1985Date of Patent: September 8, 1987Assignee: The Procter & Gamble CompanyInventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
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Patent number: 4690943Abstract: Certain novel 2-oxindole compounds, having an acyl substituent at both the 1-position and the 3-position, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and antiinflammatory agents in mammalian subjects. These 1,3-diacyl-2-oxindole compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases such as rheumatoid arthritis and osteoarthritis.Type: GrantFiled: June 20, 1985Date of Patent: September 1, 1987Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4675412Abstract: There is disclosed a process for preparing 5-mercapto-1,2,3-thiadiazole salts comprising reacting a hydrazone compound represented by the formula:X.sub.3 C--CH.dbd.N--NH--SO.sub.2 Arwherein X represents a halogen atom and Ar represents an aryl group, with a polysulfide compound represented by the formula:M.sub.2 S.sub.xwherein M represents an alkali metal atom or an NH.sub.4 group and x is an integer of 2 to 6.The present invention provides the 5-mercapto-1,2,3-thiadiazole salt with remarkably increased yield as compared with the conventional method.Type: GrantFiled: September 19, 1985Date of Patent: June 23, 1987Assignee: Ube Industries, Ltd.Inventors: Hiroshi Yoshida, Teruhiko Inoue
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Patent number: 4670041Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.Type: GrantFiled: September 13, 1982Date of Patent: June 2, 1987Assignee: E. I. du Pont de Nemours and CompanyInventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
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Patent number: 4666502Abstract: The invention provides 5-membered heteroaromatic compounds of formula IArN(Y)COCH.sub.2 Cl Iwherein Ar is a 5-membered heteroaromatic group comprising 1 or 2 heteroatoms selected from O, S and N and linked by a ring C-atom to the N-atom of the N(Y)COCH.sub.2 Cl group to which it is bound, whereby where Ar is pyrazolyl, said N(Y)COCH.sub.2 Cl group is in the 4-position,and Y is as specified in the description,the use of these compounds as herbicides, compositions for facilitating such use and the preparation of the chloroacetamides.Type: GrantFiled: February 3, 1983Date of Patent: May 19, 1987Assignee: Sandoz Ltd.Inventors: Karl Seckinger, Fred Kuhnen, Karlheinz Milzner
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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: 4658037Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. Certain 2-oxindole compounds unsubstituted at the 1-position but having an acyl substituent at C-3 of the formula ##STR1## and the base salts thereof, wherein X is hydrogen, 5-fluoro, 5-chloro or 5-trifluoromethyl; Y is hydrogen, 6-fluoro, 6-chloro or 6-trifluoromethyl; and R.sup.1 is benzyl, furyl, thienyl or thienylmethyl; provided that when X and Y are both hydrogen, R.sup.1 is not benzyl are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.Type: GrantFiled: December 30, 1985Date of Patent: April 14, 1987Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4644006Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.Type: GrantFiled: June 22, 1984Date of Patent: February 17, 1987Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4629495Abstract: Herbicidal compounds of the formula: ##STR1## wherein A represents R.sup.1 R.sup.2 N-- (wherein R.sup.1 represents C.sub.1-8 alkyl or C.sub.2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C.sub.1-6 alkoxy, carboxy, C.sub.2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by C.sub.1-8 alkyl or C.sub.2-8 alkenyl, C.sub.1-8 alkoxyaminocarbonyl, C.sub.1-8 alkanesulphonamidocarbonyl, --C(.dbd.O)Het, where Het represents a nitrogen-containing heterocyclic group, or one or more halogen atoms or R.sup.1 represents C.sub.3-6 cycloalkyl optionally substituted by C.sub.1-4 alkyl and R.sup.2 represents H or R.sup.1, or R.sup.1 represents C.sub.1-4 alkylthio and R.sup.2 represents H, or A represents R.sup.p (R.sup.q)--C.dbd.N-- (wherein R.sup.p represents C.sub.1-4 alkoxy or amino substituted by one or two C.sub.1-4 alkyl groups and R.sup.q represents H or C.sub.1-4 alkyl) or A represents 2-oxo-azetidin-1-yl, 2-oxo-pyrrolidin-1-yl or 2-oxo-piperidin-1-yl optionally substituted by C.sub.Type: GrantFiled: July 13, 1983Date of Patent: December 16, 1986Assignee: May & Baker LimitedInventors: Leslie R. Hatton, Edgar W. Parnell, David A. Roberts
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Patent number: 4624696Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings stated in the description, herbicides which contain these compounds and a method for controlling undesirable plant growth.Type: GrantFiled: October 9, 1985Date of Patent: November 25, 1986Assignee: BASF AktiengesellschaftInventors: Michael Keil, Rainer Becker, Dieter Jahn, Dieter Kolassa, Ulrich Schirmer, Wolfgang Will, Bruno Wuerzer, Norbert Meyer
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Patent number: 4617389Abstract: Antineoplastic compounds of the formula, IIa, ##STR1## wherein: Y is hydrogen or lower alkyl; and Z is a lower alkoxy substituted quinolinylamino radical, a cyano substituted pyrazolylamino radical or a mono- or di-lower alkyl substituted thiazolamino radical, ora nitrogen-containing heterocyclic radical, ora cyano, phenyl, carboxamido or lower alkoxycarbonyl substituted 1-aziridinyl radical ora lower alkyl, formyl or acetylphenyl substituted 1-piperazinyl radical, oran hydroxy or piperidyl substituted 1-piperidyl radical, ora lower alkoxy, amino or halo substituted pyridylamino radical, ora carboxamido, mercapto or methylenedioxy substituted anilino radical, ora radical of the formula, ##STR2## wherein R is hydrogen or lower alkyl and R" is a nitrogen-containing heterocyclic radical, ora butyrolactonyl radical, oran adamantyl radical, ora mono- lower alkoxy substituted phenyl radical, ora substituted lower alkyl radical selected from the group consisting of mercapto lower alkyl, carboxy lower alkyl, mono-, dType: GrantFiled: December 15, 1983Date of Patent: October 14, 1986Assignee: University Patents, Inc.Inventor: William A. Remers
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Patent number: 4609394Abstract: Compounds of the formula ##STR1## wherein the symbols have assigned meanings, and their use as herbicides.Type: GrantFiled: October 18, 1985Date of Patent: September 2, 1986Assignee: Shell Oil CompanyInventors: Michael T. Clark, David Munro, Ian J. Gilmore
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Patent number: 4607026Abstract: This invention relates to stereoisomeric forms and mixtures thereof of compounds of the formula ##STR1## having insecticidal, nematocidal, and acaricidal properties.Type: GrantFiled: September 29, 1982Date of Patent: August 19, 1986Assignee: Roussel UclafInventors: Jean Tessier, Andre Teche
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Patent number: 4606755Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.Type: GrantFiled: December 21, 1984Date of Patent: August 19, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer
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Patent number: 4604131Abstract: This invention relates to novel herbicidally active sulfonylurea compounds substituted in the positions ortho to the sulfonylurea bridge, agriculturally suitable compositions thereof and methods of their use as preemergent or postemergent herbicides or plant growth regulants.Type: GrantFiled: July 12, 1984Date of Patent: August 5, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mary A. Hanagan
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Patent number: 4604132Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A, B and D are selected from CH and N;E is selected from oxygen and sulfur;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, phenyl, substituted phenyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;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.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;R.sup.Type: GrantFiled: April 27, 1984Date of Patent: August 5, 1986Assignee: ICI Australia LimitedInventors: Richard J. Conway, Keith G. Watson, Graeme J. Farquharson
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Patent number: 4598147Abstract: Thiazole intermediates for cephalosporins have been prepared.Type: GrantFiled: December 3, 1984Date of Patent: July 1, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Toshiyuki Chiba, Kiyoshi Tsuji
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Patent number: 4594424Abstract: There is disclosed a 5-mercapto-1,2,3-thiadiazoles composition comprising a 5-mercapto-1,2,3-thiadiazole combined with (A) one or more compounds selected from the group consisting of water, an alcohol, an aromatic hydrocarbon and a halogenated hydrocarbon and (B) a halide of an alkali metal and process for preparing the same.Said composition can remarkably reduce the explosiveness of a 5-mercapto-1,2,3-thiadiazole to make its handling easy and to make it usable for various applications with a sense of security, for example, for manufacturing pharmaceuticals and agricultural chemicals.Type: GrantFiled: July 10, 1984Date of Patent: June 10, 1986Assignee: UBE Industries, Ltd.Inventors: Fumio Iwata, Takato Nakamura, Tadakazu Sakata
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Patent number: 4594094Abstract: Oxacycloalkane-alpha-(thio)carboxylic acid derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or optionally-substituted alkyl; n is 0 or 1; X is O or S and Y is NR.sup.4 R.sup.5 or when X is O then Y is also OH or OR.sup.3 in which R.sup.3, R.sup.4 and R.sup.5 is H or an optionally-substituted hydrocarbyl group; and W is an optionally-substituted unsaturated, cycloalkyl, secondary alkyl, aromatic or heterocyclic group, are useful as plant growth regulators, herbicides, intermediates and the like.Type: GrantFiled: April 4, 1983Date of Patent: June 10, 1986Assignee: Shell Oil CompanyInventor: Willy D. Kollmeyer
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Patent number: 4591376Abstract: New 1,2,3-thiadiazol-3-in-5-yliden-urea derivatives are disclosed of the general formula ##STR1## in which R.sub.1 is hydrogen or an, if necessary, interrupted one or more times oxygen or sulfur atom, C.sub.1 -C.sub.4 -alkyl group,R.sub.2 is an, if necessary interrupted one or more times by oxygen or sulfur atoms C.sub.1 -C.sub.4 -alkyl group, an, if necessary, substituted one or more times by alkyl C.sub.3 -C.sub.8 cycloalkyl group, an, if necessary, substituted one or more times by alkyl and/or halogen and/or alkylthio and/or alkoxy and/or trifluoromethyl and/or nitro aromatic hydrocarbon group or an, if necessary, substituted heterocyclic, at least one N-atom-containing, hydrocarbon group or R.sub.1 and R.sub.2 together with the N-atom are morpholino-, piperidino- or pyrolidino,R.sub.3 is an, if necessary, substituted C.sub.1 -C.sub.10 -alkyl group, a C.sub.2 -C.sub.6 -alkenyl, or C.sub.3 -C.sub.6 -alkenyl group, or an, if necessary, substituted aryl-C.sub.1 -C.sub.Type: GrantFiled: May 21, 1984Date of Patent: May 27, 1986Assignee: Schering AktiengesellschaftInventors: Hansjorg Krahmer, Reinhart Rusch, Hans-Rudolf Kruger, Volkert Sjut
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Patent number: 4588821Abstract: Compound of the formula ##STR1## wherein X is --C(O)Hal, --CN, or --C(O)Y in which Y is OR.sup.1 or NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 are H or hydrocarbyl or the like and R are certain optionally substituted hydrocarbyl and heterocyclic groups, are useful as herbicides and plant growth regulators or intermediates thereto. The intermediate 6-hydroxy and 6-oxo-2-oxabicyclo[2.2.1]heptane-4-carbonitriles are also new.Type: GrantFiled: June 15, 1984Date of Patent: May 13, 1986Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4588817Abstract: Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.Type: GrantFiled: June 4, 1984Date of Patent: May 13, 1986Assignee: The Upjohn CompanyInventors: Barney J. Magerlein, Howard A. Whaley
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Patent number: 4582906Abstract: Herbicidally active thiolcarbamates are employed in combination with certain 4-phenyl-1,2,3-thiadiazoles having the formula ##STR1## in which R.sup.4 is selected from the group consisting of trifluoromethyl and ##STR2## in which R.sup.5 is selected from the group consisting of C.sub.1 -C.sub.3 alkyl, phenyl, and phenyl substituted with one or more members selected from the group consisting of halogen and trifluoromethyl. In a typical application, the 4-phenyl-1,2,3-thiadiazole is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.Type: GrantFiled: December 4, 1984Date of Patent: April 15, 1986Assignee: Stauffer Chemical CompanyInventors: Joanna K. Hsu, Arnold D. Gutman
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Patent number: 4578388Abstract: The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino). N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido) groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.Type: GrantFiled: June 30, 1983Date of Patent: March 25, 1986Assignee: SmithKline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin
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Patent number: 4577046Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.Type: GrantFiled: June 11, 1984Date of Patent: March 18, 1986Assignee: University of New MexicoInventors: Mark D. Hylarides, Fred A. Mettler, Jr.
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Patent number: 4571406Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.Type: GrantFiled: May 16, 1984Date of Patent: February 18, 1986Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Frederick Cassidy
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Patent number: 4569942Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.Type: GrantFiled: March 22, 1985Date of Patent: February 11, 1986Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4568684Abstract: N-substituted 2-methylnaphthylamides of the general formula I ##STR1## where R is an unsubstituted or substituted furyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazol-2-yl or C.sub.1 -C.sub.5 -alkyl radical, or the group --CH.sub.2 --Y--R.sup.1, where Y is oxygen or sulfur and R.sup.1 is C.sub.1 -C.sub.6 -alkoxyethyl or C.sub.1 -C.sub.6 -alkoxyethoxyethyl, or R is C.sub.2 -C.sub.5 -alkenyl, C.sub.2 -C.sub.5 -alkynyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyl or C.sub.3 -C.sub.7 -cycloalkyl, and fungicides containing these compounds.Type: GrantFiled: December 17, 1984Date of Patent: February 4, 1986Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Karl Eicken, Hans Theobald, Bernd Zeeh, Ernst-Heinrich Pommer, Eberhard Ammermann
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Patent number: 4556672Abstract: Certain new 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and in alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.Type: GrantFiled: December 21, 1984Date of Patent: December 3, 1985Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4544751Abstract: 3,7-disubstituted-3-cephem-4-carboxylic acid compounds having bacteriostatic properties and the following formula: ##STR1## in which R.sup.1 is thiadiazolyl or isothiazolyl, each of which may have suitable substituent(s), or thiazolyl; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is carboxy or protected carboxy; R.sup.4 is hydrogen, acyloxy or a heterocyclicthio group which may have suitable substituent(s); and R.sup.5 is hydrogen or lower alkoxy, process for making same and treating infectious diseases therewith.Type: GrantFiled: July 9, 1982Date of Patent: October 1, 1985Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Toshiyuki Chiba, Zenzaburo Tozuka
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Patent number: 4540794Abstract: A method for preparing a 5-mercapto-1,2,3-thiadiazole salt represented by the general formula (I) is disclosed: ##STR1## the method comprises the steps of: providing a sulfonylhydrazone derivative represented by the general formula (II): ##STR2## providing a sulfide represented by the general formula (III):M--S--M' (III)(wherein R is an aryl group, X is a chlorine or bromine atom, M is an alkali metal atom and M' is a hydrogen atom or an alkali metal atom);combining the sulfonylhydrazone derivative represented by the general formula (II) and the sulfide represented by the general formula (III) and allowing a reaction to occur; andobtaining the 5-mercapto-1,2,3-thiadiazole salt represented by the general formula (I).Type: GrantFiled: September 16, 1983Date of Patent: September 10, 1985Assignee: Lederle (Japan), Ltd.Inventors: Kunikazu Sakai, Daiei Tunemoto, Takeo Kobori, Kiyosi Kondo
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Patent number: 4540429Abstract: Herbicidally active thiolcarbamates are employed in combination with certain 4-phenyl-1,2,3-thiadiazoles having the formula ##STR1## in which R.sup.4 is selected from the group consisting of trifluoromethyl and ##STR2## in which R.sup.5 is selected from the group consisting of C.sub.1 -C.sub.3 alkyl, phenyl, and phenyl substituted with one or more members selected from the group consisting of halogen and trifluoromethyl. In a typical application, the 4-phenyl-1,2,3-thiadiazole is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.Type: GrantFiled: June 1, 1982Date of Patent: September 10, 1985Assignee: Stauffer Chemical CompanyInventors: Joanna K. Hsu, Arnold D. Gutman
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Patent number: 4537903Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: October 12, 1983Date of Patent: August 27, 1985Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
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Patent number: 4535092Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are substituents defined in claim 1; wherein R.sup.4 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R.sup.5 as stated below;wherein R.sup.5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R.sup.4 to form an oxycarbonyl group such that together with the --N--CO--C-- part of the molecule it forms an oxazolidinedione group;wherein R.sup.6 is alkyl or halogenoalkyl of up to 4 carbon atoms;and wherein R.sup.7 is 5- or 6- membered saturated or unsaturated heterocyclic which contains one, two or three hetero atoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two substituents defined in claim 1;processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity.Type: GrantFiled: November 1, 1982Date of Patent: August 13, 1985Assignee: Imperial Chemical Industries PLCInventor: Leslie R. Hughes
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Patent number: 4532250Abstract: Described are compounds of the formula ##STR1## wherein R is heteroaryl and R.sub.1 is hydrogen or loweralkyl, or a pharmaceutically acceptable salt thereof.The compounds exhibit cardiotonic activity.Type: GrantFiled: November 23, 1983Date of Patent: July 30, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, Diane M. Yamamoto
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Patent number: 4517010Abstract: There is provided a new class of derivatives of 2-nitro-5-(substituted-phenoxy) benzoyl compounds that have pre- and post-emergence herbicidal activity. The derivatives include certain substituted phenyl esters, phenyl thioesters; heterocyclic esters; substituted alkyl and alkylthio esters; carbonates and thiocarbonates; benzoyl phosphonates; substituted alkanones and substituted amides.Type: GrantFiled: April 15, 1983Date of Patent: May 14, 1985Assignee: Rhone-Poulenc Inc.Inventor: Robert J. Theissen