Acyclic Patents (Class 564/143)
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Patent number: 4946983Abstract: 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: GrantFiled: December 23, 1988Date of Patent: August 7, 1990Assignee: Rhone-Poulenc ChimieInventors: Jean-Pierre Denis, Jean-Roger Desmurs, Jean-Pierre Lecouve
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Patent number: 4871872Abstract: 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: GrantFiled: January 20, 1988Date of Patent: October 3, 1989Assignee: Fisons CorporationInventor: Ronald C. Griffith
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Patent number: 4731480Abstract: 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: GrantFiled: July 29, 1985Date of Patent: March 15, 1988Assignee: Ortho Pharmaceutical CorporationInventors: Richard A. Conley, Donald L. Barton
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Patent number: 4721797Abstract: 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: GrantFiled: September 2, 1986Date of Patent: January 26, 1988Assignee: Ciba-Geigy CorporationInventors: Wolfgang Eckhardt, Hans Suess
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Patent number: 4655972Abstract: 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: GrantFiled: July 3, 1984Date of Patent: April 7, 1987Assignee: Internationale Octrooi Maatschappij "Octropa" B.V.Inventors: Teunis Eikelboom, John A. Rand, Pieter M. van Dijk
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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: 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: 4511736Abstract: 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: GrantFiled: January 7, 1983Date of Patent: April 16, 1985Assignee: Eszakmagyarorszagi VegyimuvekInventors: Ferenc Mogyorodi, Eniko Koppany, Tibor Bodi, Karoly Balogh, Istvan Toth, Rezso Bognar, Sandor Makleit, Gyorgy Litkei, Miklos Rakosi, Zoltan Dinya
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Patent number: 4473508Abstract: 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: GrantFiled: May 11, 1983Date of Patent: September 25, 1984Assignee: Lonza Ltd.Inventor: Max Gross
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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: 4399306Abstract: 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: GrantFiled: December 18, 1979Date of Patent: August 16, 1983Assignees: Nitrokemia Ipartelepek, Nehezvegyipari Kutato Intezet, Mta Mezogazdasagi Kutato IntezetInventors: 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
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Patent number: 4356291Abstract: 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: GrantFiled: April 3, 1981Date of Patent: October 26, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thomas R. Darling
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Patent number: 4337357Abstract: 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: GrantFiled: October 24, 1980Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Tamon Uematsu, Shunichi Hashimoto, Hiromichi Oshio
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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: 4317916Abstract: 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: GrantFiled: September 4, 1980Date of Patent: March 2, 1982Assignee: Ciba-Geigy CorporationInventors: Gerhard Degischer, Werner Angst
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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: 4293193Abstract: 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: GrantFiled: August 15, 1979Date of Patent: October 6, 1981Assignee: Temple UniversityInventors: Mortimer M. Labes, John H. MacMillan
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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: 4278799Abstract: 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: GrantFiled: April 28, 1980Date of Patent: July 14, 1981Assignee: Stauffer Chemical CompanyInventors: Alan H. Benke, Hue T. Morris, Louie A. Nady
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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