Acyclic Patents (Class 564/143)
  • Patent number: 4946983
    Abstract: A process for the preparation of N-acyl-N-allylaniline. A solution of diallylaniline or a mixture of monoallyl and diallylaniline is placed in contact with a carboxylic acid halide.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: August 7, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Pierre Denis, Jean-Roger Desmurs, Jean-Pierre Lecouve
  • Patent number: 4871872
    Abstract: Compounds are provided of the following general structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or methyl and where R.sub.5 and R.sub.6 are independently selected from hydrogen or fluorine.These are useful for providing antiepileptic activity.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: October 3, 1989
    Assignee: Fisons Corporation
    Inventor: Ronald C. Griffith
  • Patent number: 4731480
    Abstract: A process for preparing 2-acyl-3,4-dialkoxyanilines is described. The 2-acyl-3,4-dialkoxyanilines are useful intermediates in the preparation of 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones. The substituted quinazolinones are active as cardiotonic agents.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: March 15, 1988
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Richard A. Conley, Donald L. Barton
  • Patent number: 4721797
    Abstract: N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines of the formula ##STR1## wherein R.sub.1 is methyl or ethyl, R.sub.2 is alkoxymethyl, chloromethyl or 2-tetrahydrofuryl, R.sub.3 is alkoxymethyl, carboxy or alkoxycarbonyl and R.sub.4 is hydrogen or methyl and, if R.sub.3 is carboxy or alkoxycarbonyl, R.sub.4 is also 2-alkoxyethyl and 2-alkoxypropyl, and R.sub.3 and R.sub.4, together with the carbon atom to which both radicals are attached, may also form a 2-oxotetrahydro-3-furyl radical or a 2-oxo-5-methyltetrahydro-3-furyl radical, are prepared by reacting a 2,6-dialkylaniline of the formula ##STR2## with a halide of the formula ##STR3## wherein X is chlorine or bromine, to give an N-alkyl-2,6-dialkylaniline of the formula ##STR4## then converting said compound by further reaction with an acylating agent of the formulaX.sub.1 --CO--R.sub.2wherein X.sub.1 is chlorine, bromine or -O-CO-R.sub.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: January 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Eckhardt, Hans Suess
  • Patent number: 4655972
    Abstract: Carbonamides are prepared from carboxylic acids and ammonia in the presence of a catalytic amount of a hydrated oxide.Preferably a hydrated titanium-, zirconium- or tin oxide in an amount between 0.05 to 10% by weight is used. The hydrated oxide contains at least 4% of water.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: April 7, 1987
    Assignee: Internationale Octrooi Maatschappij "Octropa" B.V.
    Inventors: Teunis Eikelboom, John A. Rand, Pieter M. van Dijk
  • 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: 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: 4511736
    Abstract: The invention relates to a novel process for preparing chloroacetanilides of the formula ##STR1## wherein: R.sub.1 and R.sub.2 represent independently from each other a hydrogen atom or a C.sub.1-8 alkyl or C.sub.1-8 alkoxy group; andR.sub.3 stands for a straight chained or branched C.sub.1-8 alkoxy group.Said process is characterized by chloroacetylating a 2,6-dialkylaniline of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, at a temperature of 10.degree. to 120.degree. C., optionally in a solvent medium in the presence of an acid binding agent, then reacting a thus-obtained intermediate with chloromethyl chloroformiate or, alternatively, reacting a compound of the formula (II) first with chloromethyl chloroformiate and subjecting then to chloroacetylation, thereafter reacting a thus-obtained intermediate with an alcohol of the formulaR.sub.3 --OH (III),wherein R.sub.
    Type: Grant
    Filed: January 7, 1983
    Date of Patent: April 16, 1985
    Assignee: Eszakmagyarorszagi Vegyimuvek
    Inventors: Ferenc Mogyorodi, Eniko Koppany, Tibor Bodi, Karoly Balogh, Istvan Toth, Rezso Bognar, Sandor Makleit, Gyorgy Litkei, Miklos Rakosi, Zoltan Dinya
  • Patent number: 4473508
    Abstract: A process for the production of .gamma.-chloroacetoacetic acid chloride by reaction of chlorine and diketene. The process has a throughput which is from 5 to 750 kg of product per liter reaction volume hour, which means the process achieves a large plant scale throughput of reactants. A solution of chlorine dissolved in an inert solvent and a solution of diketene dissolved in an inert solvent are introduced simultaneously in a continuous current into a tube reactor in such a way that the two solvents immediately mix homogeneously and a turbulent flow develops. The turbulent flow in the tube reactor has a Reynolds number of at least 2,500. None of the reactants or components are used in gaseous form in the reaction, and no gaseous phase forms during the reaction. The mole ratio of chlorine to diketene is between 0.9 to 1 and 1.2 to 1. The same inert solvent can be used in both the chlorine solution and the diketene solution. Preferably a chlorinated hydrocarbon is used as the inert solvent.
    Type: Grant
    Filed: May 11, 1983
    Date of Patent: September 25, 1984
    Assignee: Lonza Ltd.
    Inventor: Max Gross
  • 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: 4399306
    Abstract: The invention relates to an improved method for the preparation of a 2',6'-dialkyl-N-alkoxymethyl-2-chloro-acetanilide compound of the general formula (I), ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are identical or different and stand for straight-chained or branched C.sub.1-4 alkyl groups.According to the invention a dialkyl aniline of the general formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, is treated with aqueous formaldehyde solution in an apolar solvent at a temperature of 30.degree. to 80.degree. C., the solution of the resulting oxymethyl derivative formed with said apolar solvent is separated from the aqueous formaldehyde solution at an elevated temperature and then dehydrated, the resulting azomethine derivative is reacted with chloroacetyl chloride in the same apolar solvent medium, the resulting chloromethyl compound is reacted with an alcohol of the general formula (V),R.sub.3 -OH (V)wherein R.sub.
    Type: Grant
    Filed: December 18, 1979
    Date of Patent: August 16, 1983
    Assignees: Nitrokemia Ipartelepek, Nehezvegyipari Kutato Intezet, Mta Mezogazdasagi Kutato Intezet
    Inventors: Kornelia Domjan nee Pinter, Gyorgy Huszak, Zoltan Kolonics, Laszlo Lendvai, Jeno Pelyva, Endre Sumegi, Elemer Tomordi, Bela Gyorfi, Laszlo J. Szabo, Andras Haas, Miklos Kovacs, Taszlo Kulcsar, Miklos Nadasy, Balint Nagy, Andras Vass, Ervin Vertesi
  • Patent number: 4356291
    Abstract: Purified hexafluoropropylene oxide is produced by scrubbing to remove impurities that inhibit polymerization of hexafluoropropylene oxide, thus permitting the preparation of polymers having a degree of polymerization of more than 200, including end-capped and chain-extended derivatives thereof.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: October 26, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thomas R. Darling
  • Patent number: 4337357
    Abstract: A process for producing novel 1,4-benzothiazine derivatives (I), ##STR1## (in which X is a halogen atom) and their derivatives, ##STR2## wherein R is a (C.sub.1 -C.sub.5) alkyl, (C.sub.3 -C.sub.6) cycloalkyl, phenyl, substituted phenyl, phenyl (C.sub.1 -C.sub.5) alkyl or phenoxy (C.sub.1 -C.sub.5) alkyl group, and herbicides containing these compounds as an active ingredient.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: June 29, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamon Uematsu, Shunichi Hashimoto, Hiromichi Oshio
  • 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: 4317916
    Abstract: An improved process for producing N-substituted N-acetyl-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each methyl or ethyl, A is a 1,2-ethylene group which can be substituted by 1 or 2 methyl groups, or a 2-oxo-1,2-ethylene group which can be substituted by 1 or 2 methyl groups, R.sub.3 is an alkyl group having 1 to 3 carbon atoms, and X represents chlorine or an alkyl group having 1 to 3 carbon atoms, is disclosed, which process comprises reacting a N-substituted-2,6-dialkylaniline of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3 and A have the meaning given above with an acetyl chloride of the formulaX--CH.sub.2 --CO--Clin which X has the meaning given above, in an excess of said acetyl chloride as solvent.The N-substituted-N-acetyl-2,6-dialkylanilines of the above formula can be used for protecting plants from being infected by phytopathogenic microorganisms.
    Type: Grant
    Filed: September 4, 1980
    Date of Patent: March 2, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Degischer, Werner Angst
  • 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: 4293193
    Abstract: A group of novel, low temperature liquid crystalline compounds with terminal, primary or secondary amino polar electron donating groups are disclosed. These include, for example, p-alkyl-or alkoxy-phenylcyclohexanes, bicyclohexyls or biphenyl ring systems, substituted at the p' position with alkyl primary or secondary amines, of which one example is p-(4-trans-n-pentylcyclohexyl)benzylamine.
    Type: Grant
    Filed: August 15, 1979
    Date of Patent: October 6, 1981
    Assignee: Temple University
    Inventors: Mortimer M. Labes, John H. MacMillan
  • 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: 4278799
    Abstract: Dichloroacetylamides selected from the group consisting of:(a) N,N-diallyldichloroacetamide, and(b) N-dichloroacetyl oxazolidines having the formula ##STR1## in which R is hydrogen or C.sub.1 -C.sub.3 alkyl are produced in a continuous circulating process by reaction of dichloroacetyl chloride with respectively N,N-diallylamine or an oxazolidine having the formula ##STR2## in the presence of an aqueous solution of sodium hydroxide. The conduct of this process in a continuous circulating fashion produces the desired amide in greater yield than by the heretofore practiced batch processes.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: July 14, 1981
    Assignee: Stauffer Chemical Company
    Inventors: Alan H. Benke, Hue T. Morris, Louie A. Nady
  • 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