Halogen In Acid Moiety Patents (Class 560/161)
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Patent number: 4549994Abstract: A process for the preparation of a compound according to claim 1, comprising reacting a compound of the formula ##STR1## in which R.sup.3, R.sup.4 and R.sup.5 each independently is CH.sub.3 or CH.sub.2 Cl, at least one of the radicals R.sup.3, R.sup.4 and R.sup.5 being CH.sub.2 Cl,with a metal fluoride at elevated temperature. The products are new and useful as intermediates for making other compounds, especially carbamate insecticide synergists.Type: GrantFiled: July 13, 1984Date of Patent: October 29, 1985Assignee: Bayer AktiengesellschaftInventors: Hermann Hagemann, Erich Klauke, Ernst Kysela
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Patent number: 4511730Abstract: This invention relates to carbamates of beta-hydroxyethylsulfoxides which are useful as cosurfactants in enhanced oil recovery, surfactants and biocides, and as hydraulic fluids when of sufficiently low molecular weight.Type: GrantFiled: August 17, 1982Date of Patent: April 16, 1985Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4505859Abstract: 2-Haloethylamides are prepared by reaction of 2-oxazolidinone or C.sub.1-6 alkyl or phenyl derivatives thereof with an acid halide.Type: GrantFiled: October 9, 1981Date of Patent: March 19, 1985Assignee: The Dow Chemical CompanyInventor: Graham S. Poindexter
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Patent number: 4474806Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.Type: GrantFiled: May 10, 1982Date of Patent: October 2, 1984Assignee: Merck & Co., Inc.Inventors: Thomas R. Beattie, Shu S. Yang
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Patent number: 4448773Abstract: Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,R.sub.1 is 2-furyl, 2-tetrahydrofuryl, alkenyl, cyclopropyl, .beta.-alkoxyethyl, hydroxymethyl, triazolylmethyl, imidazolylmethyl, pyrazolylmethyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyloxy, dialkylaminosulfinyloxy, phosphoric or thiophosphoric esters or amides, or alkylcarbonyloxy,R.sub.7 is hydrogen or optionally-substituted methyl or ethyl, andR.sub.8 is alkyl optionally substituted by alkoxy,are microbicidally, in particular fungicidally, active. Preferred compounds are those in which Ar is 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl or .alpha.-naphthyl, each of which is further substituted by azido, and each of R.sub.7 and R.sub.8 is methyl.Type: GrantFiled: April 22, 1982Date of Patent: May 15, 1984Assignee: Ciba-Geigy CorporationInventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
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Process for the preparation of N,O-disubstituted urethanes useful for the preparation of isocyanates
Patent number: 4430505Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.Type: GrantFiled: October 15, 1980Date of Patent: February 7, 1984Assignee: Bayer AktiengesellschaftInventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann -
Patent number: 4375477Abstract: Beta-monofluoromethyl beta-alanine, beta-difluoromethyl beta-alanine and pharmaceutically acceptable esters and amides derived from the acid group, amides derived from the amine group, and salts thereof are novel compounds which inhibit .gamma.-aminobutyric acid transaminase (GABA-T).Type: GrantFiled: July 21, 1980Date of Patent: March 1, 1983Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michael Jung, Fritz Gerhart
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Patent number: 4361438Abstract: Compounds having the formula ##STR1## in which X and Y are halogen; R is cyano, halogen, thio-C.sub.1 -C.sub.4 alkyl, phenyl, pyridyl, hydroxy, or OR.sub.1 ; R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 mono- or di-alkylcarbamyl, C.sub.2 -C.sub.6 alkoxyalkyl, phenylcarbamyl, C.sub.1 -C.sub.6 alkanoyl or C.sub.1 -C.sub.6 haloalkanoyl; and n is: (a) 1 or 2 if R is thioalkyl, cyano or phenyl; and (b) 2 if R is otherwise as defined, are herbicides.Type: GrantFiled: January 21, 1981Date of Patent: November 30, 1982Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4353828Abstract: Fluorinated alkenylamines of the Formula V ##STR1## wherein n represents 0, 1, 2 or 3; R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl and Y represents (a), when n represents O, CH.sub.2 F, (b), when n represents 1, CH.sub.2 F or CHF.sub.2, or (c) when n represents 2 or 3, CH.sub.2 F, CHF.sub.2 or CF.sub.3 are novel process intermediates. They are obtained by hydrolysis and subsequent reduction of the corresponding alkenyl fluorinated methyl ketimine magnesium halides, which are novel compounds resulting from reaction of the corresponding alkenyl magnesium halides with the corresponding fluorinated acetonitriles. The fluorinated alkenylamines of Formula V are oxidized while the amino group is protected to provide, after removal of the amine protecting group, the corresponding fluorinated methyl aminoalkanoic acids which are useful pharmacological or anti-bacterial agents.Type: GrantFiled: July 21, 1980Date of Patent: October 12, 1982Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Fritz Gerhart, Viviane Van Dorsselaer
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Patent number: 4335138Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.Type: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
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Patent number: 4326071Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.Type: GrantFiled: September 28, 1977Date of Patent: April 20, 1982Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4304922Abstract: Production of urethanes by the oxycarbonylation reaction of N,N'-disubstituted ureas and organic compounds containing at least one hydroxyl group with carbon monoxide in the presence of molecular oxygen and/or organic nitro compounds and a catalyst system comprising (a) a noble metal and/or noble metal compound of the eighth subgroup of the periodic system of elements and (b) a compound of an element and/or elements of the third to fifth main group and/or first to eighth subgroup of the periodic system of elements characterized in that said compounds are capable of undergoing Redox reactions under the reaction conditions.Type: GrantFiled: February 27, 1980Date of Patent: December 8, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gunter Stammann
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Patent number: 4297501Abstract: A process for producing urethanes by reacting primary amines, carbon monoxide and organic hydroxyl compounds in the presence of molecular oxygen and/or organic nitro compounds as oxidizing agents and a catalyst system comprising a noble metal and/or a compound of a noble metal of the 8th subgroup of the Periodic System of Elements and a compound capable of undergoing Redox reactions under reaction conditions of the 3rd to 5th main group and/or 1st to 8th subgroup of the Periodic System of Elements.Type: GrantFiled: February 27, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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Patent number: 4289892Abstract: Active hydrogen-containing fluorochemical is used as a foam stabilizer for polyurethane foams. For example, rigid or flexible polyurethane foams with high or low density and uniform cellular structure are prepared using fluoroaliphatic radical-substituted poly(oxyalkylene) polyols as foam stabilizers.Type: GrantFiled: April 30, 1979Date of Patent: September 15, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fredrich A. Soch
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Patent number: 4266070Abstract: A process for the production of urethanes is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst comprising a member selected from the group consisting of carbonyls of Co, Mo, Ti, Rh, Fe, Ni and mixtures thereof. Urethane yields and selectivities are further improved by conducting the reaction in the additional presence of an organic compound containing at least one C.dbd.N or C.dbd.C group. When such unsaturated organic compounds are employed, the catalyst can additionally comprise iridium carbonyl.Type: GrantFiled: May 25, 1979Date of Patent: May 5, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4260781Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group, and a metal reactant comprising at least one member selected from the group consisting of compounds and complexes of Group VIII of the Periodic Table.Type: GrantFiled: May 25, 1979Date of Patent: April 7, 1981Assignee: Halcon Research and Development Corp.Inventor: Robert J. Harvey
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4247712Abstract: There is disclosed methods and compositions for inhibiting or preventing the growth of microorganisms in aqueous systems wherein the growth is inhibited or prevented by the presence of an effective amount of a 2-chloro-3-oxobutyramide derivative.Type: GrantFiled: November 8, 1979Date of Patent: January 27, 1981Assignees: Givaudan Corporation, Hoffmann-La Roche Inc.Inventors: Harold A. Brandman, Milton Manowitz, David L. Coffen
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Patent number: 4242520Abstract: A process for the production of carbamates is provided which comprises contacting an organic primary or secondary amine with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of a catalyst for the reaction and in the presence of at least one member selected from the group consisting of disulfides of the formulaR.sup.1 --S--S--R.sup.2wherein R.sup.1 and R.sup.2 comprise members selected from the group consisting of alkyl, aryl, cycloalkyl, alkaryl, aralkyl, heterocyclic, alkenyl, alkynyl, alkanoyl, aranoyl, halogenated derivatives of the foregoing groups, and derivatives of the foregoing groups in which one or more carbon atoms is replaced by an oxygen atom.Type: GrantFiled: January 29, 1979Date of Patent: December 30, 1980Assignee: Halcon Research & Development CorporationInventor: David Moy
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Patent number: 4239904Abstract: A process for the preparation of urethanes by reacting a tertiary amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: December 16, 1980Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4171449Abstract: N,N-dichloro-N-acyl compounds, such as N,N-dichlorocarbamates, sulfonamides and amidosulfonamides selectively react with conjugated dienes to yield the corresponding 1,4-adducts, i.e. N-chloro-N-chlorocrotyl compounds. The N-chloro group of these adducts can be selectively reduced by aqueous sodium sulfite. Both the original and the reduced adducts are novel compositions useful as biologically active compounds and vulcanizing agents. The bis-N-chlorocrotyl carbamates and their N-chloro derivatives are particularly claimed compositions.Type: GrantFiled: March 30, 1978Date of Patent: October 16, 1979Assignee: Exxon Research & Engineering Co.Inventors: Francis A. Daniher, Alexis A. Oswald
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Patent number: 4146557Abstract: N,N-dichloro-N-acyl compounds, such as N,N-dichlorocarbamates, sulfonamides and amidosulfonamides selectively react with conjugated dienes to yield the corresponding 1,4-adducts, i.e. N-chloro-N-chlorocrotyl compounds. The N-chloro group of these adducts can be selectively reduced by aqueous sodium sulfite. Both the original and the reduced adducts are novel compositions useful as biologically active compounds and vulcanizing agents. The N-chlorocrotyl sulfonamides and their N-chloro derivatives are particularly claimed compositions.Type: GrantFiled: May 21, 1975Date of Patent: March 27, 1979Assignee: Exxon Research & Engineering Co.Inventors: Francis A. Daniher, Alexis A. Oswald
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Patent number: 4134918Abstract: Novel halomethyl derivatives of amines of the following general structure: ##STR1## WHEREIN Y is FCH.sub.2 --, F.sub.2 CH-- or F.sub.3 C--; Z is .beta.-methylthioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, or ##STR2## WHEREIN N IS 2 OR 3 AND R.sub.1 is hydrogen or lower alkyl of from 1 to 4 carbon atoms with the proviso that when R.sub.1 is other than hydrogen, n is 2; and each of R.sub.a and R.sub.b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; with the provisos that when Z is .beta.-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R.sub.b is hydrogen, when Z is .beta.-methylthioethyl, Y is other than F.sub.Type: GrantFiled: September 6, 1977Date of Patent: January 16, 1979Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4119789Abstract: The flame resistance of synthetic fibers and solid polymers are improved by treatment with a halogen containing amide having the formula ##STR1## wherein R is lower alkoxy; lower alkoxy carbonyl; ##STR2## X is chlorine or bromine; m is 0 or 1; n is 1-6; and y is 1-13.Type: GrantFiled: June 21, 1976Date of Patent: October 10, 1978Assignee: National Distillers and Chemical CorporationInventors: Harry Braus, Jay R. Woltermann
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Patent number: 4105792Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: May 25, 1976Date of Patent: August 8, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4083848Abstract: Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group - containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed.Type: GrantFiled: January 3, 1977Date of Patent: April 11, 1978Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masumi Itoh, Takashi Kamiya, Daijiro Hagiwara
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Patent number: 4081440Abstract: A penicillin sulfoxide ester is reacted with an N-chloro halogenating agent at a temperature of from about 75.degree. C. to about 135.degree. C. to produce a novel 2-chlorosulfinylazetidin-4-one intermediate. The intermediate can be treated with stannic chloride to produce a 3-exomethylenecepham sulfoxide.Type: GrantFiled: April 2, 1976Date of Patent: March 28, 1978Assignee: Eli Lilly and CompanyInventor: Stjepan Kukolja