Of Carboxylic Acid Halide Patents (Class 564/142)
  • Patent number: 5693859
    Abstract: There is disclosed a process of producing an .alpha.-ketamide as an intermediate for use in the production of various alkoxyiminoacetamide compounds which are useful as fungicides. Also disclosed is an intermediate to be used in this process.
    Type: Grant
    Filed: December 26, 1995
    Date of Patent: December 2, 1997
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Moriyasu Masui
  • Patent number: 5686609
    Abstract: The invention relates to compounds of the formula ##STR1## in which: m is 2 or 3;Ar and Ar' independently are a thienyl group; a substituted or unsubstituted phenyl group; or an imidazolyl group; it also being possible for Ar' to be a benzothienyl group which is unsubstituted or substituted by a halogen; a naphthyl group which is unsubstituted or substituted by a halogen; a biphenyl group; or a substituted or unsubstituted indolyl;X is hydrogen;X' is hydrogen or a hydroxyl group or is joined to X" below to form a carbon-carbon bond, or X and X' together form an oxo group or a dialkylaminoalkoxyimino group of the formula .dbd.N--O--(CH.sub.2).sub.p --Am, in which p is 2 or 3 and Am is a dialkylamino group;Y is a nitrogen atom or a group C(X"), in which X" is hydrogen or forms a carbon-carbon bond with X';Q is hydrogen, a C.sub.1 -C.sub.4 alkyl group or an aminoalkyl group of the formula --(CH.sub.2).sub.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: November 11, 1997
    Assignee: Sanofi
    Inventors: Xavier Emonds-Alt, Pierre Goulaouic, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5679712
    Abstract: Benzoylguanidines of the formula I ##STR1## are described in which: R(1), R(2), R(3), R(4), R(5) are as defined in the specification, and pharmaceutically tolerated salts thereof.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: October 21, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jan-Robert Schwark, Heinz-Werner Kleemann, Hans-Jochen Lang, Andreas Weichert, Wolfgang Scholz, Udo Albus
  • Patent number: 5675036
    Abstract: 3-?4-(4-Phenyl-1-butoxy)benzoyl!amino-2-hydroxyacetophenone is prepared by reacting a benzoate ester with a halobutylbenzene in the presence of a basic compound and an aprotic polar compound in an aromatic hydrocarbon solvent to obtain a corresponding ether, alkali hydrolyzing the ether in an aromatic hydrocarbon solvent and precipitating a hydrolysate with an acid to obtain 4-(4-phenyl-1-butoxy)benzoic acid, reacting a halogenating agent with this benzoic acid derivative in an aromatic hydrocarbon solvent to obtain an acid halide, and reacting the acid halide in an aromatic hydrocarbon solvent with a corresponding aromatic amine.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: October 7, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Etsuko Fukuda, Atsushi Furutani, Hideki Ushio, Hirokazu Murata
  • Patent number: 5670656
    Abstract: A process for the preparation of a compound of general formula II: ##STR1## wherein R.sup.1 is hydrogen, or C.sub.1 -C.sub.10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms, either of which may optionally be substituted; each R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen or C.sub.1 -C.sub.4 alkyl; A is an optionally substituted aromatic or heteroaromatic ring system; and R.sup.21 is hydrogen, halogen, OH or OCONHR.sup.1, wherein R.sup.1 is as defined above; the process comprising cyclizing a compound of general formula III: ##STR2## wherein A, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.21 are as defined in general formula II and R.sup.25 is a leaving group such as a halogen atom; under basic conditions.
    Type: Grant
    Filed: May 24, 1996
    Date of Patent: September 23, 1997
    Assignee: Zeneca Limited
    Inventors: John Michael Cox, Kevin James Gillen, Russell Martin Ellis, Shaheen Khatoon Vohra, Stephen Christopher Smith, Ian Richard Matthews
  • Patent number: 5663434
    Abstract: The present invention provides a process for preparing N-(3-amino-4-chlorophenyl) acylamides of Formula I: ##STR1## comprising reacting, in a solvent comprising at least one polar solvent, in the presence of at least one acid acceptor, 1-chloro-2,4-diaminobenzene with at least one acyl chloride of formula I:Cl--X--Rwherein X is --CO-- or --SO.sub.2 --; R is selected from the group C.sub.1 -C.sub.25 alkyl; C.sub.1 -C.sub.25 alkyl substituted with one or more groups selected from C.sub.1 -C.sub.12 alkoxy, aryl, aryloxy and C.sub.5 -C.sub.7 cycloalkyl; aryl; C.sub.5 -C.sub.7 cycloalkyl. The present invention further comprises the step of purifying said N-(3-amino-4-chlorophenyl) acylamides by crystallizing from a non-polar solvent or conducting the reaction in a mixture of at least one polar and at least one non-polar solvent.
    Type: Grant
    Filed: January 29, 1996
    Date of Patent: September 2, 1997
    Assignee: Eastman Chemical Company
    Inventor: Robert Joseph Maleski
  • Patent number: 5663437
    Abstract: A new benzidine monomer composition containing an asymmetrically situated benzamide (iminobenzoyl) group: ##STR1## was prepared from the benzolyation reaction of 4,4'-dinitro-2-biphenylamine and benzoyl chloride, followed by catalytic hydrogenation. The compound can be used as a comonomer in the preparation of soluble thermoplastic polyamides, polyimides and other high performance polymers whose preparations require a diamine monomer.
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: September 2, 1997
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventor: Loon-Seng Tan
  • Patent number: 5650540
    Abstract: Provided is a method of producing a highly pure amide compound in a high yield, wherein a silazane compound and/or a silane compound having at least one silicone-nitrogen bond are added to a reaction mixture obtained by reacting an acylfluoride group-containing compound with an amino compound, wherein the amide compound is present together with hydrogen fluroide and/or the amine hydrofluoride, thereby removing the hydrogen fluoride and/or the amine hydrofluoride from the reaction mixture.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: July 22, 1997
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takashi Matsuda, Shinichi Sato, Noriyuki Koike
  • Patent number: 5625082
    Abstract: There is provided a process for preparing intermediates having the structure ##STR1## from the corresponding aldehydes having the structure ##STR2##
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: April 29, 1997
    Assignee: American Home Products Corporation
    Inventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
  • Patent number: 5621141
    Abstract: The Application describes a new process for the preparation of alkylcarboxylic acid 4-hydroxyanilides by reaction of aminophenols with carboxylic acid derivatives in organic solvents without the addition of a base reacts.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Eric Rivadeneira, Werner Lindner
  • Patent number: 5616799
    Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Planker, Theodor Papenfuhs
  • Patent number: 5587513
    Abstract: The present invention relates to novel polyether-substituted compounds of imides and their use as surface-active agents.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: December 24, 1996
    Inventors: Klaus Pohmer, Rainer Weber, Cornelia D orzbach-Lange, Reinhard Haida, Hans-Heinrich Moretto
  • Patent number: 5523485
    Abstract: A process for preparing high-purity isobutyramide which comprises reacting isobutyryl chloride in toluene or xylene at -15.degree. to 30.degree. C. with ammonia is described.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: June 4, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Ernst Buschmann
  • Patent number: 5502252
    Abstract: There is disclosed a process of producing an .alpha.-ketamide as an intermediate for use in the production of various alkoxyiminoacetamide compounds which are useful as fungicides. Also disclosed is an intermediate to be used in this process.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: March 26, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Moriyasu Masui
  • Patent number: 5442114
    Abstract: There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: August 15, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
  • Patent number: 5414122
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produce the .alpha.-ketoacetamide.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: May 9, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • Patent number: 5399760
    Abstract: A method is provided for purifying crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a solution of the crude APAP; and b) subsequently contacting the solution with substoichiometric quantifies of an acetylating agent for a sufficient period of time to convert said color bodies or their precursors to substantially non-color bodies/stable, colorless substances; said quantities of acetylating agent provided is such that substantially none of the APAP is converted to other compounds.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: March 21, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward G. Zey, Olan S. Fruchey, Thomas H. Shockley, Joe S. Trevino, B. Frank Wood, Daniel D. Lindley
  • Patent number: 5367094
    Abstract: This invention pertains to an improved process for preparing chiral or racemic phenylalaninol (PAO) by hydrogenation of L(+)- or racemic 2-amino-1-phenyl-1,3-propanediol (APPD) in the presence of a strong volatile acid. Furthermore, a more valuable form of PAO such like N-blocked PAO was found to be directly produceable from the hydrogenation mixture without isolation of PAO, when a volatile acid was used as the medium of the hydrogenation reaction.
    Type: Grant
    Filed: June 4, 1993
    Date of Patent: November 22, 1994
    Assignee: Yukong, Ltd.
    Inventor: Dae-won Chung
  • Patent number: 5258551
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produced the .alpha.-ketoacetamide.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: November 2, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • Patent number: 5247125
    Abstract: Novel thiol-terminated hydroxyamides, and processes for their preparation and use are provided. These hydroxyamide compounds may be prepared by the reaction of a mercapto-functional alkyl ester, such as methylmercaptopropionate, with a molar excess of an alcohol-substituted amine, such as a b-hydroxyalkyl amine. The thiol-terminated hydroxyamides are useful as polymerization chain transfer agents, particularly when it is desirable to form polymers or oligomers containing functional hydroxyamide end groups. By chain terminating such polymers or oligomers with reactive hydroxyamide end groups the polymers or oligomers can be further reacted with acid-containing monomers or polymers to form block or graft copolymers.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: September 21, 1993
    Assignee: Rohm and Haas Company
    Inventors: Andrew W. Gross, William D. Emmons
  • Patent number: 5081296
    Abstract: This application relates to intermediates useful for the preparation of fiber-reactive dyes, said intermediates having the formulae ##STR1## in which B is a --(CH.sub.2).sub.n -- or --O--(CH.sub.2).sub.n -- radical, where n is 1 to 6; Q is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo; and A is an amino substituent of the formula ##STR2## and Z and Z', independently of one another, are .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-haloethyl or vinyl.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: January 14, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig
  • Patent number: 5004834
    Abstract: A method is described for preparation of polyamides using unstable diamines.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: April 2, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert S. Irwin
  • Patent number: 4889656
    Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: December 26, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard M. Flynn, Patricia M. Savu
  • Patent number: 4851127
    Abstract: Novel amine-based precursor compounds comprising the condensation products of dialkylenetriamine and alpha, beta-unsaturated acid halides are disclosed, as well as composite membranes containing such compounds, the membranes being useful in RO-type processes for desalination and the removal of low molecular weight organic compounds such as phenols and carboxylic acids.
    Type: Grant
    Filed: November 23, 1984
    Date of Patent: July 25, 1989
    Assignee: Bend Research, Inc.
    Inventors: Eric K. L. Lee, Mark E. Tuttle
  • Patent number: 4818771
    Abstract: Diphenic acid bis(dicyclohexylamide) represented by the following formula: ##STR1## A process for producing diphenic acid bis(dicyclohexylamide) represented by the above formula, which comprises dimerizing a diazonium salt of o-aminobenzoic acid in the presence of a reducing agent, followed by acidification to give 2,6'-dicarboxylbiphenyl; converting this dicarboxylic acid to 2,6'-dichloroformylbiphenyl by chlorination; and reacting this acid chloride with dicyclohexylamine.Sustained release antimicrobial compositions comprising a clathrate compound consisting of a microbial agent and diphenic acid bis(dicyclohexylamide) represented by the above formula.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: April 4, 1989
    Assignee: Kurita Water Industries, Ltd.
    Inventors: Fumio Toda, Ayako Sekikawa, Hideo Sugi, Kenji Tahara
  • Patent number: 4670546
    Abstract: Compounds of the formula ##STR1## in metal-free, 1:1 or 1:2 metal complex form, or in acid addition salt form, where the symbols are defined in the specification, useful as dyes for, for example, regenerated cellulose, cotton, synthetic polyamides and polyesters modified to contain acid groups and polymers and copolymers of acrylonitrile and 1,1-dicyanoethylene.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: June 2, 1987
    Assignee: Sandoz Ltd.
    Inventors: Jacky Dore, Reinhard Pedrazzi
  • Patent number: 4670434
    Abstract: This invention relates to compounds of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein the various substituents are defined herein. These compounds are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents in mammals.
    Type: Grant
    Filed: November 14, 1985
    Date of Patent: June 2, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Michael C. Venuti
  • Patent number: 4658054
    Abstract: A process for the preparation of 5,6-dialkoxyanthranilic acids is described. The 5,6-dialkoxyanthranilic acids are useful in the preparation of substituted quinazolinediones which are active cardiotonic agents.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: April 14, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventor: Richard A. Conley
  • Patent number: 4618713
    Abstract: This invention relates to a process for preparing 2'-methyl-2-haloacetanilides by selective catalytic hydrogenation of 2'-(halomethyl)-2-haloacetanilides. The 2'-(halomethyl)-2-haloacetanilides are initially prepared by reacting an ortho-(halomethyl) aniline or its anilinium salt with a haloacetyl halide.
    Type: Grant
    Filed: September 7, 1983
    Date of Patent: October 21, 1986
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Michael J. Miller
  • Patent number: 4608391
    Abstract: New dopamine derivatives are disclosed, which are tertiary amines and which exhibit especially dopaminergic properties, and which have the formula ##STR1## wherein R.sub.1 signifies an alkyl group containing at least 4 carbon atoms, a cycloalkyl alkyl group, a cycloalkyl group or a phenylalkyl group and R.sub.2 signifies an alkyl group, a cycloalkyl alkyl group, a cycloalkyl group, or a phenylalkyl group.
    Type: Grant
    Filed: April 16, 1979
    Date of Patent: August 26, 1986
    Assignee: Cornell Research Foundation Inc.
    Inventors: James Z. Ginos, George C. Cotzias
  • Patent number: 4596892
    Abstract: 2,2'-Bridged[1,1'-biphenyl]-3-ylmethyl carboxamides and insecticidal compositions containing these carboxamides are useful for the control of a broad range of insects and acarids.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: June 24, 1986
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4568765
    Abstract: This invention relates to new isoprenylamine derivatives and acid addition salts thereof, which are useful as medicines for controlling virus infection of vertebrate animals, or the intermediates therefor.
    Type: Grant
    Filed: May 12, 1982
    Date of Patent: February 4, 1986
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Yasuhiro Komatsu, Hiroyasu Koyama, Reiko Kubota, Teruhito Yamaguchi, Toshihiro Takahashi
  • Patent number: 4564705
    Abstract: Aromatic-aliphatic diamines of the formula ##STR1## in which Ar is an arylene or substituted arylene are useful in preparing thermally stable, rigid, polyamides, polyureas and polyurethanes having a repeating unit of the formula ##STR2## in which Ar is arylene or substituted arylene, X is --NH-- or --O--, n is 0 or 1, and R is a divalent organic radical.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: January 14, 1986
    Assignee: E. I. Du Pont De Nemours and Company
    Inventors: August H. Frazer, John F. Harris, Jr.
  • Patent number: 4562201
    Abstract: The present invention relates to new compounds of the formula ##STR1## where X is ##STR2## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted aryl. These compounds are useful in the treatment of various cardiac arrhythmias.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: December 31, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, William L. Matier
  • Patent number: 4543213
    Abstract: A compound of the formula: ##STR1## wherein X is hydrogen or a conventional electron-withdrawing group, particularly --SO.sub.3 H or a salt thereof; n is 2, 3, or 4; m is 2, 3, or 4; and p is 2 or 3. The present compounds are useful as specific sequestering agents for actinide (IV) ions. Also described is a method for the 2,3-dihydroxybenzamidation of azaalkanes.
    Type: Grant
    Filed: August 7, 1979
    Date of Patent: September 24, 1985
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Frederick L. Weitl, Kenneth N. Raymond
  • Patent number: 4534874
    Abstract: The title compounds correspond to the formula ##STR1## wherein A is a monovalent, bivalent, trivalent or tetravalent radical of a mono-, di-, tri- or tetraamine. These compounds are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 13, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: David H. Steinberg, Raymond Seltzer, John J. Luzzi, Frank P. Cortolano
  • Patent number: 4455309
    Abstract: New halo-methyl-thioamino-benzamides of the formula ##STR1## wherein X.sup.1 represents optionally substituted alkylene, arylene or alkarylene, it being possible for the alkylene and/or arylene and/or alkarylene groups to be linked via oxo, thio, carboxo, carboxamido or sulphoxo groups,A.sup.1 denotes the radical ##STR2## wherein Hal represents halogen,the various substituents R can be identical or different and represent hydrogen, optionally substituted alkyl or aryl or a substituted R, in the case where X.sup.1 denotes optionally substituted ethylene and m.sup.1 and n.sup.1 represent the number 1, forms an ethylene bridge by being linked to a second R,m.sup.1 denotes an integer from 1 to 5 and indicates the number of linkages of ##STR3## with X.sup.1, and n.sup.1 denotes a number from 1 to 100;a process for preparing the same by reaction of a halo-methyl-thioamino-benzoic acid fluoride with an amine in the presence of a base and the use of such halo-methyl-thioamino-benzamides as microbicidal agents.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: June 19, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Ritter, Wilfried Paulus, Engelbert Kuhle, Hermann Genth
  • Patent number: 4401832
    Abstract: Disclosed herein are .alpha.-[(alkylamino)methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: August 30, 1983
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4385070
    Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: May 24, 1983
    Assignee: Imperial Chemical Industries Limited
    Inventors: Philip D. Bentley, Nazim Punja
  • Patent number: 4383949
    Abstract: A process for the preparation of a 3-bromo-4-fluorobenzaldehyde acetal of the formula ##STR1## in which R.sup.1 is methyl or ethyl,which comprises reacting a 3-bromo-4-fluoro-benzoic acid halide with ammonia to form 3-bromo-4-fluoro-benzoic acid amide, dehydrating said amide to form 3-bromo-4-fluoro-benzonitrile, reacting the nitrile with formic acid in the presence of a catalyst at a temperature between about 0.degree. and 150.degree. C. to form 3-bromo-4-fluorobenzaldehyde, and reacting said aldehyde with R.sup.1 OH or a derivative thereof capable of forming an acetal. The amide and nitrile are new compounds. The acetals are known intermediates in the synthesis of pyrethroid-like insecticides.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: May 17, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Hans-Jochem Riebel, Uwe Priesnitz, Erich Klauke
  • Patent number: 4363766
    Abstract: A process for the preparation of sulfur-containing N-benzyl-amino acids of the formula ##STR1## wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen;R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.2 is hydrogen, alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl;R.sub.3 is hydrogen or acyl; andn is 1 or 2;which comprises the steps of converting anthranilic acid or a halogenated anthranilic acid into the corresponding aldehyde, reacting the aldehyde with a compound of the formula ##STR2## wherein R.sub.1, R.sub.2 and n have the meanings previously defined, to form the corresponding Schiff's base, reducing the said Schiff's base, and recovering the reaction product.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: December 14, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventor: Bernard Bellegarde
  • Patent number: 4341718
    Abstract: Disclosed herein are .alpha.-[(alkylamino)-methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: July 3, 1978
    Date of Patent: July 27, 1982
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4331815
    Abstract: In the manufacture of an N-benzyl-N-isopropyl amide by reaction of N-benzyl-N-isopropylamine with an acid chloride, the amide product is obtained in better purity and yield by employing excess benzylisopropylamine as the acid accepting agent and recovering the amine for re-use by reacting the amine hydrochloride by-product with aqueous sodium hydroxide.
    Type: Grant
    Filed: September 26, 1980
    Date of Patent: May 25, 1982
    Assignee: Gulf Oil Corporation
    Inventor: Roger P. Cahoy
  • Patent number: 4299974
    Abstract: Disclosed is a process for preparing N-protected 2-aminoethanethiol which proceeds via the silyl covered sulfur intermediate: ##STR1## wherein R.sup.1 is triorganosilyl and R.sup.2 is a readily removable N-protecting group.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: November 10, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, Ichiro Shinkai, Meyer Sletzinger
  • Patent number: 4291060
    Abstract: Novel compounds derived from formylphenoxyacetic acid such as N,N-dihexadecyl-4-(aminomethyl)phenoxy acetamide and N,N-dihexacecyl-2-(4-(aminomethyl)phenoxy) ethylamine and their non-toxic acid addition salts are useful for combating viral infections in vertebrate animals.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: September 22, 1981
    Assignee: Pfizer Inc.
    Inventor: Allen R. Kraska
  • Patent number: 4288592
    Abstract: There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Michael M. Rauhut, Shin-Shyong Tseng
  • Patent number: 4288620
    Abstract: A process for the production of 4-acylamido-2-nitro-1-alkoxybenzenes by acylating p-alkoxyaniline with an acylating agent to 4-acylamido-alkoxybenzenes and subsequently nitrating these latter to 4-acylamido-2-nitro-1-alkoxybenzenes, which process comprises carrying out the reaction in an inert solvent, without isolation of the intermediates, using 88 to 95% sulfuric acid in the weight ratio of 6:1 to 10:1, based on the p-alkoxyaniline employed, during the nitration step.
    Type: Grant
    Filed: June 12, 1980
    Date of Patent: September 8, 1981
    Assignee: Ciba-Geigy AG
    Inventor: Manfred Rosner
  • Patent number: 4252804
    Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: February 24, 1981
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin