Halogen Patents (Class 562/456)
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Patent number: 4382954Abstract: Compounds represented by the formula ##STR1## wherein R and R.sup.1 are independently hydrogen or lower alkyl; R.sup.2 is lower alkenyl, lower alkynyl or --CH.sub.2 X wherein X is halogen, hydroxyl, lower alkoxy, lower alkylthio or a furanyl ring; and Z is hydroxyl, lower alkoxy or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl possess fungicidal activity. Moreover, some of the compounds of this invention also possess herbicidal activity.Type: GrantFiled: January 27, 1982Date of Patent: May 10, 1983Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4375550Abstract: This invention relates to the hydrogenation of halogen-substituted aromatic nitro compounds and in particular provides a novel catalyst for use in such processes.In more detail a catalyst suitable for use in the hydrogenation of halogen-substituted aromatic nitro compounds substantially without simultaneous dehalogenation comprises one or more metals from the group consisting of platinum, palladium, rhodium, iridium, ruthenium and osmium supported on or impregnated into a carrier material comprising carbon activated with phosphoric acid or a salt thereof.Type: GrantFiled: August 27, 1981Date of Patent: March 1, 1983Assignee: Johnson, Matthey & Co., LimitedInventors: Alfred J. Bird, Gordon G. Ferrier
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Patent number: 4375478Abstract: Described are compounds of the formula ##STR1## wherein Y and Z independently of one another denote hydrogen, halo or trihalomethyl, with the proviso that Y and Z cannot both be hydrogen, R is hydrogen or loweralkyl, n is 5 to 19, and pharmaceutically acceptable salts thereof.The compounds are active hypocholesterolemic agents.Type: GrantFiled: March 2, 1982Date of Patent: March 1, 1983Assignee: Abbott LaboratoriesInventors: Bruce W. Horrom, Herman H. Stein
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Patent number: 4374266Abstract: Ammonium salts of fluorophthalamic acids characterized by the formula ##STR1## wherein n is 1 or 2, are prepared by the steps of (A) reacting a chlorophthalic anhydride of the formula ##STR2## where n is as defined previously, with potassium fluoride or cesium fluoride to form a fluorophthalic anhydride of the formula ##STR3## where n is as previously defined, and (B) reacting the fluorophthalic anhydride with ammonium to form an ammonium salt of a fluorophthalamic acid.Type: GrantFiled: December 29, 1980Date of Patent: February 15, 1983Assignee: Occidental Chemical CorporationInventors: Michael J. Fifolt, Arthur M. Foster
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Patent number: 4374267Abstract: Fluorophthalamic acids characterized by the formula ##STR1## wherein n is 1 or 2, are prepared by the steps of(A) reacting a chlorophthalic anhydride of the formula ##STR2## where n is as defined previously, with potassium fluoride or cesium fluoride to form a fluorophthalic anhydride of the formula ##STR3## where n is as previously defined, and (B) reacting the fluorophthalic anhydride with ammonia to form an ammonium salt of a fluorophthalamic acid, and(C) acidifying the ammonium salt to form a fluorophthalamic acid.Type: GrantFiled: December 29, 1980Date of Patent: February 15, 1983Assignee: Occidental Chemical CorporationInventors: Michael J. Fifolt, Arthur M. Foster
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4359428Abstract: Fluorinated anthranilic acid and anthranilonitrile, and a novel process for their preparation by reacting 2,6-difluorobenzonitrile with ammonia and, if the acid is required, hydrolyzing the resulting 6-fluoroanthranilonitrile with a basic compound.The two novel end products are valuable intermediates for the preparation of compounds which are useful for controlling various animal pests and plant pests.Type: GrantFiled: November 5, 1981Date of Patent: November 16, 1982Assignee: BASF AktiengesellschaftInventors: Peter Jacobs, Heinz-Guenter Oeser
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Patent number: 4350822Abstract: Novel para-[aryl(alkyl or alkenyl)amino]benzoic acids, esters, pharmaceutically acceptable salts and pharmaceutical compositions thereof and a method of lowering serum lipid levels in mammals therewith.Type: GrantFiled: March 15, 1979Date of Patent: September 21, 1982Assignee: American Cyanamid CompanyInventors: Jay D. Albright, Thomas G. Miner, Robert G. Shepherd
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Patent number: 4333951Abstract: Novel 2-amino-6-biphenylacetic acids, esters, and metal salts are provided of the formula: ##STR1## wherein R represents hydrogen or lower alkyl, R.sup.1 represents fluoro, chloro, bromo, lower-alkyl or amino; R.sup.2 represents lower-alkyl, lower-alkoxy, fluoro, chloro, bromo, amino or trifluoromethyl; n is 0-3 and m is 0-2, and the pharmaceutically acceptable salts thereof. The compounds exhibit muscle relaxant activity, and are also useful as anti-inflammatory agents.Type: GrantFiled: July 2, 1980Date of Patent: June 8, 1982Assignee: A. H. Robins Company, Inc.Inventor: David A. Walsh
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Patent number: 4331808Abstract: Chemiluminescent-labeled conjugates of the formula: ##STR1## wherein R is hydrogen or straight chain alkyl containing 1-4 carbon atoms, n=2-6 and L(CO-- is a specifically bindable ligand, such as an antigenic protein or polypeptide, a hapten or an antibody, or a binding analog thereof, bound through an amide bond; and intermediates produced in the synthesis of such conjugates. The labeled conjugates are useful as reagents in specific binding assays for determining ligands or their specific binding partners in liquid media.Type: GrantFiled: October 5, 1979Date of Patent: May 25, 1982Assignee: Miles Laboratories, Inc.Inventors: Robert T. Buckler, Hartmut R. Schroeder
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Patent number: 4328230Abstract: There are described compounds of formula I, ##STR1## in which R.sub.5 to R.sub.8 may be a variety of substituents, or an adjacent pair of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a chain--COCH.dbd.C(COOH)NRh--,or one of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a group of formula II, ##STR2## in which Ra, Rb and Rc have the same significances as R.sub.5, R.sub.6, R.sub.7 and R.sub.8,X is an optionally interrupted or substituted hydrocarbon chain,Rg and Rh, which may be the same or different are each alkyl, alkenyl, phenyl-alkyl, alkanoyl, benzoyl or phenylalkanoyl,or Rg and R.sub.8 and/or Rh and Rc in formula II, together form a chain --(CH.sub.2).sub.n --, and n is 2, 3 or 4.There are also described processes for making the compounds and pharmaceutical, e.g. anti-allergic, compositions containing the compounds.Type: GrantFiled: March 5, 1979Date of Patent: May 4, 1982Assignee: Fisons LimitedInventors: Roger C. Brown, Hugh Cairns, Anthony R. Payne
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Patent number: 4322439Abstract: The invention relates to .omega.-[2-(N-lower alkyl-benzamido)-phenyl]-alkanoic acids, their use and preparation, and medicaments containing them.Type: GrantFiled: September 21, 1979Date of Patent: March 30, 1982Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventors: Kurt Klemm, Uwe Kruger, Erich Rapp, Horst Wolf, Ekkehard Kraas
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Patent number: 4318919Abstract: Tetrachlorophthalamic acids of the formula ##STR1## in which R.sup.1 represents a trihalogenomethyl, trihalogenomethoxy or trihalogenomethylmercapto group,R.sup.2 represents hydrogen, halogen or a lower alkyl or lower alkoxy group, orR.sup.1 together with R.sup.2, in the o-position relative to each other, denote --O--CF.sub.2 --O--CF.sub.2 --,--O--CF.sub.2 --O--or --O--CF.sub.2 --CFX--O--, whereinX represents hydrogen, chlorine or fluorine, andR.sup.3 represents hydrogen, halogen or a lower alkyl, lower alkoxy, lower alkylmercapto or aryloxy group, the aryloxy being optionally substitutedwhich possess activity against bacteria, particularly those which attack plants.Type: GrantFiled: July 18, 1980Date of Patent: March 9, 1982Assignee: Bayer AktiengesellschaftInventors: Engelbert Kuhle, Peter Kraus, Albrecht Marhold
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Patent number: 4310545Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: November 13, 1979Date of Patent: January 12, 1982Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4297509Abstract: This invention relates to a process of preparing alkali metal salts of 3-amino-2,5-dichlorobenzoic acid by the catalytic hydrogenation of alkali metal salts of 3-nitro-2,5-dichlorobenzoic acid in the presence of molybdenum-promoted Raney nickel catalyst.Type: GrantFiled: March 25, 1980Date of Patent: October 27, 1981Assignee: Union Carbide CorporationInventor: Bertrand A. Chiasson
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Patent number: 4283532Abstract: Disclosed is a process for the preparation of o-(2,6-dichloroanilino)phenylacetic acid (Diclofenac) or its pharmacologically acceptable acid addition salt, which comprises hydrolyzing an N,N-disubstituted-o-(2,6-dichloroanilino)phenylacetamide derivative with an alkali. Also a novel intermediate for use in the preparation of Diclofenac, that is, an N,N-disubstituted-o-halogenophenylacetamide in which the halogen is iodine or bromine, is disclosed.Type: GrantFiled: August 7, 1979Date of Patent: August 11, 1981Assignee: Ikeda Mohando Co., Ltd.Inventor: Fujio Nohara
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Patent number: 4271188Abstract: Compounds having hypolipidaemic activity which are substituted aralkylanilines, their preparation and pharmaceutical compositions containing them.Type: GrantFiled: December 17, 1979Date of Patent: June 2, 1981Assignee: Beecham Group LimitedInventor: Richard M. Hindley
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Patent number: 4267355Abstract: Stereospecific synthesis of ##STR1## (R-configuration at C.sup.2) by reaction of ##STR2## (S-configuration at C.sup.2) with ##STR3## at elevated temperature in the presence of a base, e.g., R-(-)-(2-(N-benzoyl-3-chloro-4-fluoroanilino)propionic acid isopropylester) from S-(-)-isopropyl lactate mesylate and 3-chloro-4-fluoroaniline followed by benzoylation. The compounds are very active herbicides against broad-leafed weeds (R=H) or wild oats (R=(thio)benzoyl).Type: GrantFiled: November 1, 1976Date of Patent: May 12, 1981Assignee: Shell Oil CompanyInventors: Richard M. Scott, Geoffrey D. Armitage
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Patent number: 4263320Abstract: Hypoglycemic phenylpropynylamino benzoic acids and the pharmaceutically-acceptable salts thereof, a method for lowering serum sugars and hypoglycemic compositions useful for the treatment of diabetes.Type: GrantFiled: June 4, 1979Date of Patent: April 21, 1981Assignee: The Dow Chemical CompanyInventors: Donald P. Matthews, Eugene R. Wagner, Roger D. McDermott
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Patent number: 4260633Abstract: Novel diastereomeric esters of amino acids, novel intermediates therefor, synthesis thereof, and the use of said esters for the control of pests.Type: GrantFiled: April 21, 1980Date of Patent: April 7, 1981Assignee: Zoecon CorporationInventors: Richard J. Anderson, Karen G. Adams, Clive A. Henrick
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Patent number: 4256639Abstract: Process for the preparation of the 2-(2,6-dichloroanilino)-phenylacetic acid which comprises, as a basic step, the heating of a mixture containing a pyridic base, an organic or inorganic acid and 4,5,6,7-tetrahydro-N-(2,6-dichlorophenyl)-isatin or its O-acyl or O-alkyl derivatives.Type: GrantFiled: June 5, 1979Date of Patent: March 17, 1981Assignee: Aziende Chimiche Riunite Angelini FrancescoInventor: Leandro Baiocchi
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Patent number: 4250192Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent alipahtic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.Type: GrantFiled: April 25, 1979Date of Patent: February 10, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Gerhard Baschang
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Patent number: 4250183Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.Type: GrantFiled: December 15, 1978Date of Patent: February 10, 1981Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4249021Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity.Type: GrantFiled: February 26, 1979Date of Patent: February 3, 1981Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
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Patent number: 4246429Abstract: Novel .alpha.-amino-phenylacetic acid derivatives, said phenyl having at least one substituent other than hydrogen, are useful as herbicidal, algicidal and plant growth regulatng agents.Type: GrantFiled: April 9, 1979Date of Patent: January 20, 1981Assignee: Janssen Pharmaceutica, N.V.Inventor: Georges Van Daele
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Patent number: 4243609Abstract: The present invention relates to certain ring-fluorinated 4-(hexadecyl-amino) N-substituted benzamide compounds as hypolipidemic and antiatherosclerotic agents together with their pharmacologically acceptable acid-addition and cationic salts. The amino functions of the benzamide groups are selected from the groups consisting of loweralkanesulfonylamino, phenylsulfonylamino, loweralkanoylamino, benzoylamino and carboxyalkylamino.Type: GrantFiled: February 2, 1978Date of Patent: January 6, 1981Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4243678Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.Type: GrantFiled: December 15, 1978Date of Patent: January 6, 1981Assignee: Byk Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4243606Abstract: The present invention relates to new N-substituted anilines which correspond to the general formula: ##STR1## in which R.sub.1 represents an alkyl radical or substituted alkyl radical, R.sub.2 represents a hydrogen atom, an alkyl radical or substituted alkyl radical, R.sub.3 represents a cyano, carbamoyl, carboxy or carbalkoxy radical and R.sub.4 represents a hydrogen or halogen atom or an alkyl or alkoxy radical. These compounds are valuable intermediates for the preparation of coloring materials, especially as coupling compounds for the synthesis of azo dyes.Type: GrantFiled: September 30, 1977Date of Patent: January 6, 1981Assignee: Produits Chimiques Ugine KuhlmannInventors: Paul M. C. Bourdauducq, Claude M. H. E. Brouard, Claude L. E. Moerel, Jean-Pierre H. Stiot
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Patent number: 4243819Abstract: Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: February 16, 1978Date of Patent: January 6, 1981Assignee: Zoecon CorporationInventors: Clive A. Henrick, Barbara A. Garcia
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Patent number: 4242522Abstract: An o-(N-allyl-2,6-dichloroanilino)phenylacetic acid derivative represented by the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, individually represent a hydrogen atom, a halogen atom or an alkyl group; Y represents a hydroxyl group, an alkoxyl group, a --OM.sup.1 group in which M.sup.1 is an alkali metal atom, a --OM.sub.1/2.sup.2 group in which M.sup.2 is an alkaline earth metal atom, an amino group having the formula --NR.sup.5 R.sup.6 in which R.sup.5 and R.sup.6, which may be the same or different, individually represent a hydrogen atom or an alkyl group, or a hydroxylamino group,and processes for preparing the same.Type: GrantFiled: September 17, 1979Date of Patent: December 30, 1980Assignees: Nissan Chemical Industries, Ltd., Sagami Chemical Research CenterInventors: Genichi Tsuchihashi, Katsuyuki Ogura, Ryozo Sakoda, Isao Hashiba, Shuichi Fukushima
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Patent number: 4239901Abstract: Pyrazol-1-ylphenylacetic acids of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different and denote a hydrogen atom or a halogen atom,R.sup.4 denotes a hydrogen atom or an alkyl group,A B denotes a carbon-carbon single or double bond, and their salts are pharmacologically active and are useful as medicaments. Medicament compositions are produced therefrom. Their functional carboxylic acid derivatives and other new intermediates are used in their preparation.Type: GrantFiled: October 12, 1977Date of Patent: December 16, 1980Assignee: Byk Gulden Lomberg Chemische Fabrik GmbHInventor: Georg Rainer
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Patent number: 4234483Abstract: Azo compounds of the formula: ##STR1## are provided where A is a diazotizable aromatic hydrocarbon and X is hydrogen or lower alkyl. The compounds dye synthetic fibers, particularly nylon and polyester, and wool in strong yellow to red hues of outstanding brightness and build-up. The dyeings have excellent fastness properties.Type: GrantFiled: August 11, 1976Date of Patent: November 18, 1980Assignee: American Color & Chemical CorporationInventors: Raouf Botros, Ivan E. Riggle
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Patent number: 4226802Abstract: Synthesis of 2-(4-trifluoromethylphenylamino)-3-methylbutanoic acid and lower alkyl esters thereof, optionally ortho substitution on the phenylamino group, novel intermediates thereof, which are useful intermediates in the synthesis of pesticides.Type: GrantFiled: October 29, 1979Date of Patent: October 7, 1980Assignee: Zoecon CorporationInventors: Richard J. Anderson, Ted A. Baer
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Patent number: 4224050Abstract: Chloroacetanilides are disclosed having the general formula: ##STR1## wherein R.sup.1 =H, or alkyl with 1-5 carbon atoms, or X;X=alkenyl, and preferably ##STR2## in which the various R.sup.2, which may be equal to or different from each other, are H or an alkyl with 1-3 carbon atoms;A=alkylene, optionally substituted, of the formula: ##STR3## in which the various R.sup.2, which may be equal to or different from each other, have the meanings specified above; andY=H; alkyl with 1-5 carbon atoms; alkenyl with 2-5 carbon atoms; alkinyl with 2-5 carbon atoms; phenyl; cycloalkyl with 3-8 carbon atoms; halogen; ##STR4## wherein R=H; alkyl with 1-5 carbon atoms; alkenyl or alkinyl with 2-5 carbon atoms; cycloalkyl with 3-8 carbon atoms; phenyl;The chloroacetanilide derivatives are useful in combatting infestations of infesting monocotyledons and dicotyledons during pre-emergence, by spreading the chloroacetanilide derivative on the soil adjacent thereto in quantities ranging from 0.25 kg/ha upwards.Type: GrantFiled: February 7, 1978Date of Patent: September 23, 1980Assignee: Montedison S.p.A.Inventors: Roberto Colle, Franco Gozzo, Giovanni Camaggi, Giorgio Siddi
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Patent number: 4223039Abstract: There are provided compounds of the general formula ##STR1## in which Ar represents a phenyl group which is unsubstituted or substituted by a halogen atom or a lower alkyl group, or represents a thienyl group, R.sub.1 represents a hydrogen or halogen atom or, when the Ar--CO-- grouping is in the meta-position with respect to the nitrogen atom, a lower alkyl group, R.sub.2 represents a hydrogen atom, or a lower alkyl or an acyl group, and R.sub.3 represents a hydrogen atom, a lower alkyl or a phenyl group and a physiologically acceptable salt thereof.The compounds of the general formula I and their salts have therapeutic utility, especially as analgesics.Type: GrantFiled: March 14, 1979Date of Patent: September 16, 1980Assignee: Metabio JoullieInventors: Francis E. E. Rose, Christian J. M. Warolin, Pierre Muller, Paul M. P. Fabiani, Bernard Gaudilliere
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Patent number: 4221815Abstract: Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.Type: GrantFiled: January 2, 1976Date of Patent: September 9, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Werner Pfaff
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Patent number: 4218475Abstract: Substituted or unsubstituted benzylaminobenzene alkanoic or alkenoic acids are disclosed as hypolipidemic agents and especially as hypocholesterolemic agents; along with a method of use and pharmaceutical compositions thereof.Type: GrantFiled: October 26, 1978Date of Patent: August 19, 1980Assignee: The Dow Chemical CompanyInventors: Eugene R. Wagner, Donald P. Matthews, Alfred A. Renzi
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Patent number: 4217304Abstract: A process for the reduction of aromatic nitro compounds to amino compounds in the liquid phase using iron as reducing agent, which comprises carrying out the reduction continuously such that the reducing iron, based on the amount of nitro compound present in the reactor, is present in an amount substantially in excess of the stoichiometric amount, and effecting the continuous removal of the reaction products such that the substantial excess of reducing iron is also constantly present in the reactor during the reduction.Type: GrantFiled: December 20, 1978Date of Patent: August 12, 1980Assignee: Ciba-Geigy AGInventors: Bernhard Albrecht, Hans Frey, Vinzenz Habermacher, Paul Havalda, Georg Halfter
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Patent number: 4207341Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy,Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, andR.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical,or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.Type: GrantFiled: July 1, 1976Date of Patent: June 10, 1980Assignee: Boehringer-Mannheim GmbHInventors: Manfred Hubner, Hans Kuhnle, Ernst-Christian Witte, Ruth Heerdt, Rudi Weyer, Volker Hitzel
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Patent number: 4204970Abstract: Lubricant compositions containing polymer alkylated aromatic amino acids as antioxidants and a process for the preparation of these amino acids comprising hydrolysis of cyclic keto amides formed from an intramolecular acylation of an imide of an aromatic amine.Type: GrantFiled: December 7, 1978Date of Patent: May 27, 1980Assignee: Standard Oil Company (Indiana)Inventors: Richard J. Lee, Samuel W. Harris
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Patent number: 4205085Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: March 9, 1978Date of Patent: May 27, 1980Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4204428Abstract: A system for detecting thermal breakdown of organic resin coatings is described which can be used for locating failure occurring in electrical apparatus based on the use of a minor amount of a chemical tagging material. The chemical tag can be readily extracted from particulate generated by the thermal breakdown of the organic resin coating by extracting the particulate with an organic solvent and analyzing the extract in a gas chromatograph using an electron capture detector. Useful results have been found when employing certain halogenated aromatic organic compounds, such as N-alkyl tetrahalophthalimides, which can be employed in the particulating resin at concentrations of as little as 0.01% by weight.Type: GrantFiled: February 9, 1978Date of Patent: May 27, 1980Assignee: General Electric CompanyInventors: Jimmy L. Webb, Woodfin V. Ligon
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Patent number: 4191840Abstract: Anti-allergic agents of aromatic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of .alpha.-naphthyl, .beta.-napthtyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals;and pharmaceutically acceptable salts thereof.Type: GrantFiled: February 7, 1979Date of Patent: March 4, 1980Assignee: American Home Products CorporationInventors: John H. Sellstedt, Charles J. Guinosso, Albert J. Begany
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Patent number: 4188343Abstract: Improved process for preparing anthranylaldehyde derivatives of formula: ##STR1## (Z.sup.1 and Z.sup.2 each represents hydrogen atom, a halogen atom, methyl group or trifluoromethyl group.) is provided.The process comprises steps of (1) protecting aldehyde group of a o-halogenobenzaldehyde with a specific alkylamine derivative, then (2) reacting the thus protected compound with a corresponding aniline derivative, and finally, (3) treating the thus obtained product with an acid.The anthranylaldehyde derivatives, i.a. N-(2,6-dichlorophenyl)anthranylaldehyde is useful as an intermediate for preparation of the corresponding anilinophenylacetic acids which are anti-inflammatory and analgesic agents.Type: GrantFiled: December 27, 1978Date of Patent: February 12, 1980Assignee: Nissan Chemical Industries, Ltd.Inventors: Ryozo Sakoda, Isao Hashiba, Kazuo Nagano
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Patent number: 4187316Abstract: Compounds of the following general formula and salts thereof are irreversible inhibitors of .gamma.-aminobutyric acid transaminase: ##STR1## wherein R.sub.1 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, the radical ##STR2## wherein R.sub.4 is hydrogen, a straight or branched alkyl group having from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, the group-NR.sub.5 R.sub.6wherein each of R.sub.5 and R.sub.6 is hydrogen or a straight or branched alkyl group having from 1 to 4 carbon atoms, or ##STR3## wherein R.sub.7 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and R.sub.3 is hydrogen or bromine.Type: GrantFiled: January 12, 1978Date of Patent: February 5, 1980Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung
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Patent number: 4185115Abstract: Novel para-[aryl(alkyl or alkenyl)amino]benzoic acids, esters, pharmaceutically acceptable salts and pharmaceutical compositions thereof and a method of lowering serum lipid levels in mammals therewith.Type: GrantFiled: March 12, 1975Date of Patent: January 22, 1980Assignee: American Cyanamid CompanyInventors: Jay D. Albright, Thomas G. Miner, Robert G. Shepherd
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Patent number: 4178385Abstract: A method for treating hyperlipidemia in primates using the compound 4-((4-fluorophenylmethyl)amino)benzoic acid, a pharmaceutically-acceptable salt or an ester thereof.Type: GrantFiled: March 3, 1978Date of Patent: December 11, 1979Assignee: The Dow Chemical CompanyInventors: Eugene R. Wagner, Alfred A. Renzi
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Patent number: 4172098Abstract: Halobenzenes are manufactured by (a) a one-vessel reaction of anilines with halogenating agents to give haloanilines, followed by reaction of the mixture thus obtained with alkanols and nitrosylating agents in the presence of water and acid at not less than 35.degree. C. or (b) the corresponding reaction of a haloaniline which has been manufactured in the above manner or by some other method and has been isolated from its reaction mixture. The products are starting materials for the manufacture of drugs, dyes and pesticides.Type: GrantFiled: November 15, 1977Date of Patent: October 23, 1979Assignee: BASF AktiengesellschaftInventors: Horst Scheuermann, Ulrich Jersak, Helmut Gorth
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Patent number: 4168312Abstract: New quinolone derivatives of the Formula I ##STR1## wherein R.sup.1 and R.sup.2 are each H, F, Cl, Br, CF.sub.3 or CH.sub.3 O or a physiologically acceptable acid addition salt thereof possess pharmacological properties including thrombocyte aggregation inhibiting action.Type: GrantFiled: November 8, 1977Date of Patent: September 18, 1979Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Erich Schacht, Hans Dahm, Reinhard Lissner
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Patent number: 4161537Abstract: Isovaleric acid ester derivatives and the optical isomers thereof expressed by the general formula I: ##STR1## wherein, R.sub.1 represents hydrogen, methyl group or chlorine atom, andR.sub.2 represents hydrogen or cyano group.Type: GrantFiled: November 30, 1977Date of Patent: July 17, 1979Assignee: Dainippon Jochugiki Kabushiki KaishaInventors: Yoshio Katsuda, Minoru Nakajima, Toshio Fujita