Of Carboxylic Acid Halide Patents (Class 564/142)
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Patent number: 5693859Abstract: 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: GrantFiled: December 26, 1995Date of Patent: December 2, 1997Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Moriyasu Masui
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Patent number: 5686609Abstract: 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: GrantFiled: March 11, 1994Date of Patent: November 11, 1997Assignee: SanofiInventors: Xavier Emonds-Alt, Pierre Goulaouic, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5679712Abstract: 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: GrantFiled: June 2, 1995Date of Patent: October 21, 1997Assignee: Hoechst AktiengesellschaftInventors: Jan-Robert Schwark, Heinz-Werner Kleemann, Hans-Jochen Lang, Andreas Weichert, Wolfgang Scholz, Udo Albus
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Patent number: 5675036Abstract: 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: GrantFiled: June 28, 1996Date of Patent: October 7, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Etsuko Fukuda, Atsushi Furutani, Hideki Ushio, Hirokazu Murata
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Patent number: 5670656Abstract: 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: GrantFiled: May 24, 1996Date of Patent: September 23, 1997Assignee: Zeneca LimitedInventors: John Michael Cox, Kevin James Gillen, Russell Martin Ellis, Shaheen Khatoon Vohra, Stephen Christopher Smith, Ian Richard Matthews
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Patent number: 5663434Abstract: 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: GrantFiled: January 29, 1996Date of Patent: September 2, 1997Assignee: Eastman Chemical CompanyInventor: Robert Joseph Maleski
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Patent number: 5663437Abstract: 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: GrantFiled: February 2, 1996Date of Patent: September 2, 1997Assignee: The United States of America as represented by the Secretary of the Air ForceInventor: Loon-Seng Tan
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Patent number: 5650540Abstract: 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: GrantFiled: October 30, 1995Date of Patent: July 22, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takashi Matsuda, Shinichi Sato, Noriyuki Koike
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Patent number: 5625082Abstract: There is provided a process for preparing intermediates having the structure ##STR1## from the corresponding aldehydes having the structure ##STR2##Type: GrantFiled: November 3, 1994Date of Patent: April 29, 1997Assignee: American Home Products CorporationInventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
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Patent number: 5621141Abstract: 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: GrantFiled: December 28, 1995Date of Patent: April 15, 1997Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Eric Rivadeneira, Werner Lindner
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Patent number: 5616799Abstract: 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: GrantFiled: April 17, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Siegfried Planker, Theodor Papenfuhs
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Patent number: 5587513Abstract: The present invention relates to novel polyether-substituted compounds of imides and their use as surface-active agents.Type: GrantFiled: January 20, 1995Date of Patent: December 24, 1996Inventors: Klaus Pohmer, Rainer Weber, Cornelia D orzbach-Lange, Reinhard Haida, Hans-Heinrich Moretto
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Patent number: 5523485Abstract: 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: GrantFiled: December 12, 1994Date of Patent: June 4, 1996Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Ernst Buschmann
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Patent number: 5502252Abstract: 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: GrantFiled: November 10, 1994Date of Patent: March 26, 1996Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Moriyasu Masui
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Patent number: 5442114Abstract: 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: GrantFiled: January 18, 1994Date of Patent: August 15, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
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Patent number: 5414122Abstract: 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: GrantFiled: August 17, 1993Date of Patent: May 9, 1995Assignee: Shionogi & Co., Ltd.Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
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Patent number: 5399760Abstract: 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: GrantFiled: August 11, 1993Date of Patent: March 21, 1995Assignee: Hoechst Celanese CorporationInventors: Edward G. Zey, Olan S. Fruchey, Thomas H. Shockley, Joe S. Trevino, B. Frank Wood, Daniel D. Lindley
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Patent number: 5367094Abstract: 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: GrantFiled: June 4, 1993Date of Patent: November 22, 1994Assignee: Yukong, Ltd.Inventor: Dae-won Chung
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Patent number: 5258551Abstract: 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: GrantFiled: December 3, 1992Date of Patent: November 2, 1993Assignee: Shionogi & Co., Ltd.Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
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Patent number: 5247125Abstract: 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: GrantFiled: February 28, 1991Date of Patent: September 21, 1993Assignee: Rohm and Haas CompanyInventors: Andrew W. Gross, William D. Emmons
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Patent number: 5081296Abstract: 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: GrantFiled: April 17, 1990Date of Patent: January 14, 1992Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Paul Herzig
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Patent number: 5004834Abstract: A method is described for preparation of polyamides using unstable diamines.Type: GrantFiled: April 5, 1990Date of Patent: April 2, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert S. Irwin
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Patent number: 4889656Abstract: 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: GrantFiled: October 30, 1987Date of Patent: December 26, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 4851127Abstract: 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: GrantFiled: November 23, 1984Date of Patent: July 25, 1989Assignee: Bend Research, Inc.Inventors: Eric K. L. Lee, Mark E. Tuttle
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Patent number: 4818771Abstract: 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: GrantFiled: December 12, 1986Date of Patent: April 4, 1989Assignee: Kurita Water Industries, Ltd.Inventors: Fumio Toda, Ayako Sekikawa, Hideo Sugi, Kenji Tahara
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Patent number: 4670546Abstract: 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: GrantFiled: June 28, 1984Date of Patent: June 2, 1987Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4670434Abstract: 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: GrantFiled: November 14, 1985Date of Patent: June 2, 1987Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4658054Abstract: 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: GrantFiled: July 29, 1985Date of Patent: April 14, 1987Assignee: Ortho Pharmaceutical CorporationInventor: Richard A. Conley
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Patent number: 4618713Abstract: 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: GrantFiled: September 7, 1983Date of Patent: October 21, 1986Assignee: Monsanto CompanyInventors: John P. Chupp, Michael J. Miller
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Patent number: 4608391Abstract: 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: GrantFiled: April 16, 1979Date of Patent: August 26, 1986Assignee: Cornell Research Foundation Inc.Inventors: James Z. Ginos, George C. Cotzias
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Patent number: 4596892Abstract: 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: GrantFiled: April 19, 1985Date of Patent: June 24, 1986Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4568765Abstract: 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: GrantFiled: May 12, 1982Date of Patent: February 4, 1986Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Yoshiyuki Tahara, Yasuhiro Komatsu, Hiroyasu Koyama, Reiko Kubota, Teruhito Yamaguchi, Toshihiro Takahashi
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Patent number: 4564705Abstract: 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: GrantFiled: May 21, 1981Date of Patent: January 14, 1986Assignee: E. I. Du Pont De Nemours and CompanyInventors: August H. Frazer, John F. Harris, Jr.
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Patent number: 4562201Abstract: 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: GrantFiled: July 26, 1982Date of Patent: December 31, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, William L. Matier
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Patent number: 4543213Abstract: 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: GrantFiled: August 7, 1979Date of Patent: September 24, 1985Assignee: The United States of America as represented by the United States Department of EnergyInventors: Frederick L. Weitl, Kenneth N. Raymond
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Patent number: 4534874Abstract: 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: GrantFiled: November 21, 1983Date of Patent: August 13, 1985Assignee: Ciba-Geigy CorporationInventors: David H. Steinberg, Raymond Seltzer, John J. Luzzi, Frank P. Cortolano
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Patent number: 4455309Abstract: 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: GrantFiled: August 20, 1981Date of Patent: June 19, 1984Assignee: Bayer AktiengesellschaftInventors: Helmut Ritter, Wilfried Paulus, Engelbert Kuhle, Hermann Genth
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Patent number: 4401832Abstract: 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: GrantFiled: August 10, 1981Date of Patent: August 30, 1983Assignee: American Home Products CorporationInventors: Dong H. Kim, Stanley C. Bell
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Patent number: 4385070Abstract: 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: GrantFiled: January 28, 1980Date of Patent: May 24, 1983Assignee: Imperial Chemical Industries LimitedInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4383949Abstract: 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: GrantFiled: June 26, 1981Date of Patent: May 17, 1983Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Hans-Jochem Riebel, Uwe Priesnitz, Erich Klauke
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Patent number: 4363766Abstract: 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: GrantFiled: April 17, 1979Date of Patent: December 14, 1982Assignee: Boehringer Ingelheim GmbHInventor: Bernard Bellegarde
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Patent number: 4341718Abstract: 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: GrantFiled: July 3, 1978Date of Patent: July 27, 1982Assignee: American Home Products CorporationInventors: Dong H. Kim, Stanley C. Bell
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Patent number: 4331815Abstract: 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: GrantFiled: September 26, 1980Date of Patent: May 25, 1982Assignee: Gulf Oil CorporationInventor: Roger P. Cahoy
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Patent number: 4299974Abstract: 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: GrantFiled: June 16, 1980Date of Patent: November 10, 1981Assignee: Merck & Co., Inc.Inventors: Thomas M. H. Liu, Ichiro Shinkai, Meyer Sletzinger
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Patent number: 4291060Abstract: 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: GrantFiled: February 5, 1979Date of Patent: September 22, 1981Assignee: Pfizer Inc.Inventor: Allen R. Kraska
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Patent number: 4288592Abstract: 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: GrantFiled: April 30, 1979Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Michael M. Rauhut, Shin-Shyong Tseng
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Patent number: 4288620Abstract: 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: GrantFiled: June 12, 1980Date of Patent: September 8, 1981Assignee: Ciba-Geigy AGInventor: Manfred Rosner
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Patent number: 4252804Abstract: 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: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin