Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/66)
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4888348
    Abstract: The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: December 19, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson
  • Patent number: 4874877
    Abstract: Intermediates and a stepwise process for the conversion of D-methionine or certain of its derivatives to optically active compounds of the formula ##STR1## wherein R is (C.sub.1 -C.sub.3) alkyl, phenyl or tolyl. The latter compounds are in turn useful as an intermediate in the preparation of penem antibiotic 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid and corresponding pharmaceutically acceptable salts and esters.
    Type: Grant
    Filed: April 19, 1988
    Date of Patent: October 17, 1989
    Assignee: Pfizer Inc.
    Inventor: Frank J. Urban
  • Patent number: 4864046
    Abstract: Intermediates and a stepwise process for the conversion of ethyl 4-chloro-3R-hydroxybutyrate to optically active compounds of the formula ##STR1## wherein R is (C.sub.1 -C.sub.3)alkyl, phenyl or tolyl. The later compounds are in turn useful as an intermediate in the preparation of penem antibiotic 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acic and corresponding pharmaceutically acceptable salts and esters.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: September 5, 1989
    Assignee: Pfizer Inc.
    Inventor: Robert A. Volkmann
  • Patent number: 4863503
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: September 5, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul de Fraine, Christopher R. A. Godfrey, Kevin Beautement
  • Patent number: 4857539
    Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Philip M. Carabateas
  • Patent number: 4833161
    Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different, are optionally substituted aryl radicals or optionally substituted heterocyclic radicals, A is a straight-chained or branched, saturated or unsaturated alkylene chain containing up to 10 carbon atoms which can contain an oxygen, sulphur or nitrogen atom and is optionally substituted by a hydroxyl group, Y is an S(O).sub.n group or an oxygen atom, n is 0, 1 or 2 and B is a valency bond or a saturated or unsaturated alkylene radical containing up to 5 carbon atoms; as well as the physiologically acceptable salts, esters and amides thereof, with the proviso that(a) R.sub.1 and R.sub.2 are not simultaneously aryl radicals and(b) when an unsaturated alkylene chain is present which contains a heteroatom, the heteroatom is not connected to an unsaturated aliphatic carbon atom.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: May 23, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Hans-Frieder Kuhnle
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4797456
    Abstract: Water-soluble sulfonium salts are converted, without the elimination of odorous volatile by-products, to water-insoluble products useful as binders in coating formulations by heating a water-soluble cyclic sulfonium salt in which the sulfonium sulfur is bonded only to aliphatic carbons.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: January 10, 1989
    Assignee: The Dow Chemical Company
    Inventors: Ritchie A. Wessling, Donald L. Schmidt, Kiyoshi I. Aikawa
  • Patent number: 4762848
    Abstract: 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: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4760067
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: July 26, 1988
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4746350
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Y is selected from phenyl, furyl, thienyl and pyrrolyl rings (each optionally substituted by group X), optionally branched alkylene or alkylenethio(oxy)alkylene;X which may be the same or different are independently selected from halogen, nitro, alkyl, substituted alkyl, hydroxy, alkoxy, carboxy, alkoxycarbonyl, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino and alkanoyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: May 24, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Keith G. Watson
  • Patent number: 4730005
    Abstract: The compounds represented by the following structural formula (I) ##STR1## wherein m is 1 or 2; n is 1, 2 or 3; R' is hydrogen or methyl; R is a radical selected from the group consisting of: ##STR2## wherein R.sub.1 is C.sub.8 to C.sub.13 alkyl, C.sub.7 to C.sub.12 alkoxy, C.sub.7 to C.sub.12 thioalkyl, C.sub.10 to C.sub.12 1-alkynyl, 11-dodecynyl, 1-trans-dodecenyl, 5-(4-acetyl-3-hydroxy-2-propylphenoxypentoxy, 2(Z), 5(Z)-undecadienyloxy, phenyl-C.sub.4 to C.sub.10 alkyl with the phenyl optionally mono substituted with bromo, chloro, trifluoromethyl, methoxy, methylthio or trifluoromethylthio, phenylthio-C.sub.3 to C.sub.9 alkyl with the phenyl optionally mono substituted with bromo, chloro, trifluoromethyl, methoxy, methylthio or trifluoromethylthio, phenyl-CH.dbd.CH--(CH.sub.2).sub.2-8, phenyl-C.sub.3 to C.sub.9 alkoxy, trifluoromethyl-C.sub.7 to C.sub.12 alkyl, cyclohexyl- C.sub.4 to C.sub.10 alkyl or ##STR3## wherein each q is 0, 1, 2 or 3 but the sum of both q's does not exceed 3, and R.sub.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: March 8, 1988
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Carl D. Perchonock
  • Patent number: 4721794
    Abstract: Thiophene-2-sulfonamides with a 5-alkyl-S(O).sub.n -substituent are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.
    Type: Grant
    Filed: July 30, 1986
    Date of Patent: January 26, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Kenneth L. Shepard, Samuel L. Graham
  • Patent number: 4704460
    Abstract: A novel compound useful in detecting leukocytes, esterase and protease in a test sample. The compound has the structure ##STR1## in which: A is an acid residue, R is lower alkyl, aryl, carboxyl, carboxyl ester, amido or cyano, R* is H or lower alkyl, and X is O, S, or NR', in which R' is H, lower alkyl or aryl.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: November 3, 1987
    Assignee: Miles Laboratories, Inc.
    Inventor: Paul F. Corey
  • Patent number: 4683330
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4681953
    Abstract: Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a .gamma.-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.
    Type: Grant
    Filed: August 22, 1975
    Date of Patent: July 21, 1987
    Assignee: Sagami Chemical Research Center
    Inventors: Kiyoshi Kondo, Kiyohide Matsui, Akira Negishi, Yuriko Takahatake
  • Patent number: 4670470
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4668814
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 26, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4665174
    Abstract: A process for preparing cyclopentenone derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted ar(lower)alkyl and A is the residue of a nucleophilic agent from which a hydrogen atom is excluded, which comprises reacting a 3-hydroxy-4-cyclopentenone compound of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above with a nucleophilic agent of the formulaA--H (III)wherein A is as defined above.The cyclopentenone derivatives of the formula (I) are useful as pharmaceuticals, agricultural chemicals, perfumes and as intermediates for the preparation of agricultural chemicals, pharmaceuticals and perfumes.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 12, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4645842
    Abstract: A novel compound useful in detecting leukocytes, esterase and protease in a test sample. The compound has the structure ##STR1## in which: A is an acid residue, R is lower alkyl, aryl, carboxyl, carboxyl ester, amido or cyano, R* is H or lower alkyl, and X is O, S, or NR', in which R' is H, lower alkyl or aryl.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: February 24, 1987
    Assignee: Miles Laboratories, Inc.
    Inventors: Paul F. Corey, Frederick E. Ward, Kin F. Yip, Meitak T. Yip
  • Patent number: 4596887
    Abstract: A cyclopropanecarboxylate of the formula ##STR1## is prepared by the reaction of a compound of the formula ##STR2## with an alkoxide in an ether type solvent. R.sup.1, R.sup.2, and R.sup.4 each independently is hydrogen or a hydrocarbon residue, R.sup.3 is an alcohol residue, X is halogen, and A is --CH.sub.2 --CX.sub.3 or --CH.dbd.CX.sub.2.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: June 24, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Kiyoshi Kondo, Kiyohide Matsui
  • Patent number: 4582855
    Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 15, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung T. Kam, William L. Matier
  • Patent number: 4558071
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: December 10, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4554363
    Abstract: Process for the preparation of bicyclic ketones containing blocked hydroxy groups, of general Formula I ##STR1## wherein R.sub.1 is the residues --CH.sub.2 OR.sub.2 wherein R.sub.2 means benzyl, dimethyl-tert-butylsilyl, diphenyl-tert-butylsilyl, dimethylphenylsilyl, tribenzylsilyl, or tetrahydropyranyl, ##STR2## with R.sub.2 having the meanings given above, R.sub.4 meaning hydrogen or methyl, and R.sub.5 meaning a straight-chain or branched-chain, saturated or unsaturated alkyl residue which can contain fluorine, chlorine, 1,2-methylene, 1,1-trimethylene, or methoxy substitutents, or a CH.sub.2 --X-Aryl residue with X meaning CH.sub.2 or O and Aryl meaning phenyl or a heterocyclic residue, which residues can be substituted by methyl, methoxy, fluorine, chlorine, bromine, or trifluoromethyl, or ##STR3## with the meanings for R.sub.2, R.sub.4, and R.sub.5 as indicated above, and R.sub.3 having the meanings set forth for R.sub.2, it being possible for R.sub.3 to be identical to R.sub.2 or different from R.sub.
    Type: Grant
    Filed: June 23, 1983
    Date of Patent: November 19, 1985
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbrueggen
  • Patent number: 4536595
    Abstract: Alpha-arylpropionic acids and alkaline salts thereof are prepared by catalytic reaction with carbon monoxide of the corresponding secondary halids in an anhydrous low alcohol solvent in the presence of a salt of cobalt hydrocarbonyl and in further presence of alkaline hydroxides under substantially ambient temperature and pressure conditions.The products obtained find useful applications in the field of pharmaceutics (analgesics, antipyretics, etc.) and as intermediates for chemical syntheses of fine chemicals, phytodrugs, etc.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: August 20, 1985
    Assignee: Montedison S.p.A.
    Inventors: Andrea Gardano, Franco Francalcanci, Marco Foa
  • Patent number: 4490552
    Abstract: A novel process for the preparation of aryl esters of organic carboxylic acids in high isomer purity by decomposing a compound of the formula ##STR1## wherein Ar is an aryl radical, X is an acyloxy of an organic carboxylic acid and Y is selected from the group consisting of an acyloxy of an organic carboxylic acid and an anion of a strong organic and mineral acid in an aqueous media in the presence of a palladium salt or in the form of a two-phase reaction, wherein the aryl thallium salt is dissolved in water and the catalytic palladium salt is dissolved in a water-immiscible organic solvent and the reaction takes place with mixing.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: December 25, 1984
    Assignee: Rutgerswerke AG
    Inventor: Ulrich Knips
  • Patent number: 4479966
    Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein the symbol between the carbon atoms in positions 5 and 6 represents a single or double bond, Y represents ethylene or trans-vinylene, R.sup.1 represents hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 12 carbon atoms, cycloalkyl of 4 to 7 carbon atoms optionally substituted by alkyl of 1 to 4 carbon atoms, phenyl optionally substituted by chlorine, trifluoromethyl, alkyl of 1 to 4 carbon atoms or phenyl, a --C.sub.m H.sub.2m COOR.sup.7 group (wherein m represents an integer of from 1 to 12 and R.sup.7 represents alkyl of 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.8 group (wherein n represents an integer of from 2 to 12 and R.sup.8 represents hydrogen or alkyl of 1 to 4 carbon atoms) or a ##STR2## group (wherein R.sup.9 and R.sup.10 each represent alkyl of 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents hydrogen or a hydroxy-protecting group, R.sup.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: October 30, 1984
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
  • Patent number: 4468521
    Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: August 28, 1984
    Assignee: Kuraray Co., Ltd.
    Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
  • Patent number: 4463014
    Abstract: Esters in their stereoisomeric form or mixtures thereof of the formula ##STR1## wherein R.sub.1 and R are different and individually selected from the group consisting of hydrogen, fluorine and bromine, R.sub.2 is selected from the group consisting of --CN and --C.tbd.CH and R.sub.3 is a hydrocarbyl group having pesticidal properties and their preparations.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: July 31, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4458090
    Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.
    Type: Grant
    Filed: October 15, 1981
    Date of Patent: July 3, 1984
    Assignee: Kuraray Co., Ltd.
    Inventors: Mori Fumio, Omura Yoshiaki, Nishida Takashi, Itoi Kazuo
  • Patent number: 4457940
    Abstract: Novel carboxylic acid ester derivatives, of the formula (I): ##STR1## process for manufacturing said derivatives, insecticides and acaricides containing said derivatives, and a method for killing insects and acarina by treating therewith.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: July 3, 1984
    Assignee: Dainippon Jochugiku Kabushiki Kaisha
    Inventors: Yoshio Katsuda, Hajime Hirobe, Yoshihiro Minamite
  • Patent number: 4431576
    Abstract: A compound in all its possible isomeric forms and mixtures thereof of the formula ##STR1## wherein R is selected from the group consisting of (a) alkyl of 1 to 12 carbon atoms optionally substituted with cycloalkyl or cycloalkenyl of 3 to 6 carbon atoms or a hydrocarbon chain of 2 to 8 carbon atoms optionally interrupted by an oxygen or ketone, (b) alkenyl and alkynyl of 3 to 8 carbon atoms, (c) cycloalkyl of 3 to 12 carbon atoms optionally containing at least one double bond and substituted with at least one alkyl and (d) aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and --CF.sub.3 and R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, --CHO, --COAlK.sub.1, --COOAlK.sub.2 and --CN, at least one being hydrogen, AlK.sub.1 and AlK.sub.2 are alkyl of 1 to 8 carbon atoms and R.sub.1 and R.sub.
    Type: Grant
    Filed: January 27, 1982
    Date of Patent: February 14, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Buendia, Francois Nezot
  • Patent number: 4424394
    Abstract: Arylacetic acids and their esters, of the formula Ar(CH.sub.2 -COOR).sub.n (where Ar=aryl, R is H or a hydrocarbon radical, and n is 1 or 2) are manufactured by carbonylation of halomethylaryl compounds Ar(CH.sub.2 C).sub.n (where X is Cl, Br or I) with carbon monoxide and a catalyst m.sup.+ ?Fe(O).sub.3 NO!.sup.- (where M is an alkali metal, ammonium or one equivalent of an alkaline earth metal) in the presence of stoichiometric amounts of an inorganic base or of an alcoholate of an alcohol ROH.
    Type: Grant
    Filed: November 8, 1979
    Date of Patent: January 3, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Kurt Schneider, Rudolf Kummer, Kurt Schwirten, Hans-Dieter Schindler, deceased, Maria E. Schindler, heir-at-law, Ute Lang, heir-at-law, Rainer Schindler, heir-at-law
  • Patent number: 4423064
    Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: December 27, 1983
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4421761
    Abstract: Thiophene derivatives of the formula ##STR1## wherein X, Y and Z are as herein defined, said compounds being useful as fungicides, are described.
    Type: Grant
    Filed: January 27, 1981
    Date of Patent: December 20, 1983
    Assignees: Hokko Chemical Industry Co. Ltd., Ube Industries, Ltd.
    Inventors: Shigeki Nagai, Takashi Yorie, Hisao Sugiura, Toru Hibi, Katsumi Sato, Takuo Wada, Masahiko Miyahara
  • Patent number: 4409227
    Abstract: 4-(((Heterocyclo)thio)methyl)benzoic acids, esters, amides and pharmaceutically-acceptable salts thereof having hypoglycemic activity in mammals, including a method of use and pharmaceutically-acceptable compositions.
    Type: Grant
    Filed: March 9, 1982
    Date of Patent: October 11, 1983
    Assignee: The Dow Chemical Co.
    Inventor: Donald P. Matthews
  • Patent number: 4398939
    Abstract: This invention covers thiophenesulfonylureas of Formula I, agriculturally suitable compositions containing them, and their method-of-use as general and/or selective preemergent and/or postemergent herbicides or plant growth regulants.
    Type: Grant
    Filed: May 4, 1981
    Date of Patent: August 16, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4388326
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: June 14, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4388475
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: June 14, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4380656
    Abstract: Novel 2-vinyl- and 2-ethylcyclopropane carboxylates useful as pesticides, herbicides and chemical intermediates are provided. The products of this invention contain two gem carboxylate ##STR1## groups, which can be the same or different. The carboxylate groups will contain an aliphatic, cycloaliphatic, aromatic, heteroalkyl or heterocyclic moiety.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: April 19, 1983
    Assignee: Emery Industries, Inc.
    Inventor: Richard G. Fayter, Jr.
  • Patent number: 4366102
    Abstract: In a process for the preparation of an aromatic chloroformic acid ester by contacting a phenol and phosgene, the improvement wherein the reaction is carried out in a homogeneous liquid phase at a temperature of 60.degree. to 180.degree. C. in the presence of organic phosphorus compound of the formulaR.sup.1 R.sup.2 R.sup.3 PR.sup.4.sub.n X.sub.nin whichR.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, alkyl, alkenyl, aralkyl, aryl or halogen and two of the said radicals together with the phosphorus atom can form a 5-membered or 6-membered phosphorus-containing saturated or unsaturated heterocyclic radical,X represents OH, homopolar-bonded halogen or an inorganic or organic acid anion,R.sup.4 denotes hydrogen or alkyl or, if X denotes halogen, can also denote halogen and n denotes 0 or 1,and in which, furthermore,R.sup.4 and X together can represent oxygen or sulfur.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: December 28, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Rauchschwalbe, Heinz U. Blank, Karl Mannes, Dietmar Mayer
  • Patent number: 4357159
    Abstract: A composition and a method for regulating the plant-metabolism, especially for promoting the abcission of citrus fruit and olives are disclosed, which use as active component a sulphonyl ester of the formula ##STR1## wherein R.sub.1 is an alkyl, alkenyl, phenyl naphthyl, diphenyl or thienyl radical,X is oxygen or sulphur andHal is a halogen atom.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: November 2, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Bernhard Gloor
  • Patent number: 4355168
    Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.
    Type: Grant
    Filed: December 2, 1980
    Date of Patent: October 19, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
  • Patent number: 4349689
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4334087
    Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: June 8, 1982
    Assignee: Zoecon Corporation
    Inventors: Ted A. Baer, Jeffrey N. Labovitz
  • Patent number: 4332815
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: June 1, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4328237
    Abstract: Pyrethroid type insecticides are described having the formula: ##STR1## Compounds of general formula I are endowed with a high insecticide and acaricide activity.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: May 4, 1982
    Assignee: Montedison S.p.A.
    Inventors: Paolo Piccardi, Francesco Corda, Franco Gozzo, Augusto Menconi, Angelo Longoni
  • Patent number: 4327109
    Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy of phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.
    Type: Grant
    Filed: April 22, 1980
    Date of Patent: April 27, 1982
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno