Halogen In Acid Moiety Patents (Class 560/47)
  • Patent number: 4371547
    Abstract: 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: Grant
    Filed: August 21, 1981
    Date of Patent: February 1, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
  • Patent number: 4360690
    Abstract: 1-Aryl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 represents a hydrogen atom, a cyano radical or an alkyl, alkenyl or alkinyl radical within each case up to 7 carbon atoms, andR.sup.2 represents a phenyl radical which is substituted by halogen and/or optionally halogen-substituted phenoxy, with the proviso that the radical R.sup.2 in total contains at least one fluorine substituent,R.sup.3 and R.sup.4, which can be identical or different, represents a fluorine, chlorine or bromine atom or a methyl radical,R.sup.5 represents a hydrogen or halogen atom or a methyl or methoxy radical, andR.sup.6 represents a hydrogen or halogen atom, a cyano nitro or amino radical or an optionally halogen-substituted radical selected from C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 alkylthio,or whereinthe two radicals R.sup.5 and R.sup.6 together represent an optionally halogen-substituted C.sub.1 or C.sub.
    Type: Grant
    Filed: June 12, 1981
    Date of Patent: November 23, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
  • Patent number: 4354033
    Abstract: Anthranilic acid esters having the generic formula: ##STR1## have been discovered. In the above formula (I) R.sub.1, R.sub.2 and R.sub.3 represent any of hydrogen, chlorine, methoxy and methyl groups and X represents a straight or branched alkyl chain comprising 1 to 4 carbon atoms. These esters are anti-inflaments, blood platelet aggregation inhibitors and prostaglandin synthetase inhibitors.The compounds of the above formula (I) may be prepared by reacting alkali metal salt of a compound of the formula (II): ##STR2## in which R.sub.1, R.sub.2, R.sub.3 and X are the same as before with the compound of formula (III): ##STR3## in which R.sub.3 has the same meaning as before and z represents a chlorine or a bromine radical.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: October 12, 1982
    Assignee: Council of Scientific & Industrial Research
    Inventors: Nanduri Bhanumati, Pralhad B. Sattur
  • Patent number: 4350822
    Abstract: 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: Grant
    Filed: March 15, 1979
    Date of Patent: September 21, 1982
    Assignee: American Cyanamid Company
    Inventors: Jay D. Albright, Thomas G. Miner, Robert G. Shepherd
  • Patent number: 4347188
    Abstract: A fungicidal composition which comprises as an active ingredient a N-benzoylanthranilate compound of the formula, ##STR1## wherein X is a hydrogen or 3-halogen atom or a 3-methoxy, 4-methoxy, 2,4-dimethoxy, 3,4-dimethoxy, 3-halo-4-methoxy, 3,4-methylenedioxy or 3,5-dimethoxy group and R is a hydrogen atom or a C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.4 alkenyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl or N,N-di-C.sub.1 -C.sub.2 alkylamino C.sub.1 -C.sub.4 alkyl group and an inert carrier, and their preparation and use as a fungicide.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: August 31, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Osamu Kirino, Toshiro Kato, Shigeo Yamamoto
  • Patent number: 4333951
    Abstract: 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: Grant
    Filed: July 2, 1980
    Date of Patent: June 8, 1982
    Assignee: A. H. Robins Company, Inc.
    Inventor: David A. Walsh
  • Patent number: 4324904
    Abstract: The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula ##STR1## and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD.sub.50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: April 13, 1982
    Assignee: The Upjohn Company
    Inventors: Thomas A. Hylton, Jerry A. Walker
  • Patent number: 4321368
    Abstract: Ethylene is polymerized in the vapor phase in a stirred bed reactor. The reactor employed is vertically aligned and has a centrally positioned cored draft tube therein. An auger circulates polymer solids through the draft tube while coolant is circulated there through to remove the heat of polymerization.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: March 23, 1982
    Assignee: Mallinckrodt, Inc.
    Inventor: George B. Hoey
  • Patent number: 4316860
    Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup.61 is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: February 23, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Michael Marky
  • Patent number: 4313956
    Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: February 2, 1982
    Assignee: INTERx Research Corp.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4311706
    Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: January 19, 1982
    Assignee: INTERx Research Corporation
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4310677
    Abstract: Alkyl anthranilates are prepared by reacting an isatin with an alkanol and hydrogen peroxide in the presence of an alkali metal alkanolate.The alkyl anthranilates obtainable by the process of the invention are valuable starting materials for the preparation of pesticides, dyes and drugs.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Dietrich Mangold
  • Patent number: 4310545
    Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: January 12, 1982
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4309350
    Abstract: The (+), (-) and (.+-.) forms of the compounds of formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, andR.sup.2 is a hydrogen or methyl group or R.sup.1 and R.sup.2 together form a methylenedioxy group;R.sup.3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (d):(a) m-phenoxybenzyl,(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-m-phenoxybenzyl(d) 3-4-methylenedioxy-benzyl,and R.sup.4 and R.sup.5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.The compounds of formula I in which R.sup.3 is one of groups (a) to (d) are extremely active as insecticides (except when R.sup.1 is an amino group). The compounds also possess the property of contact repellency to insects.
    Type: Grant
    Filed: January 24, 1980
    Date of Patent: January 5, 1982
    Assignee: Commonwealth Scientific and Industrial Research Organization
    Inventors: George Holan, Reimund Walser
  • Patent number: 4308394
    Abstract: Compounds added to initiate photopolymerization of monomers to produce polymeric coatings include compounds of the formula ##STR1## wherein Ar is phenyl or naphthyl,R is hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogen, dialkylamino with 1-4 carbon atoms in each alkyl group, carboxyl, or alkoxycarbonyl with 1-4 carbon atoms in the alkoxy group,X is alkyl having 3 to 6 carbon atoms or alkyl having 6 to 72 carbon atoms interrupted by at least one member selected from the group consisting of ##STR2## and the precursor of X being a polyol having 3 to 6 hydroxyls and having a hydroxyl number of from 100 to 1850,R.sub.1 is hydrogen or methyl,n is a number with a value from about 2 to about 5, andn+m is a number with a value from about 3 to about 6.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: December 29, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Ernst Shuster, Hans Rudolph, Wolfram Mayer, Hans J. Rosenkranz
  • Patent number: 4306074
    Abstract: A mixture of an alkyl 3-chloroanthranilate and an alkyl 6-chloroanthranilate, with a particular molar ratio of the components, is prepared by (a) reacting 3-chlorophthalic anhydride with ammonia, an alkali metal hydroxide and an alkali metal hypochlorite or (b) converting 3-chlorophthalic anhydride to 3-chlorophthalimide followed by reaction of the latter with an alkali metal hydroxide and an alkali metal hypochlorite, and, finally, esterifying the mixture of 5-chloroisatoic anhydride and 8-chloroisatoic anhydride, obtained by method (a) or method (b), with an alkanol.The compounds obtainable by the process of the invention are valuable starting materials for the preparation of dyes, crop protection agents and scents.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: December 15, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Tonne, Heinz-Guenter Oeser, Dietrich Mangold
  • Patent number: 4288621
    Abstract: The present invention relates to halo-substituted 2,2 dimethylcyclopropaneamides, useful as intermediates for the preparation of imidates having pesticidal properties.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: September 8, 1981
    Assignee: Zoecon Corporation
    Inventors: Gustave K. Kohn, Ted A. Baer
  • Patent number: 4272546
    Abstract: This disclosure describes esters of 4-(monoalkylamino)benzoic acids with hydroxyalkanoic acids and derivatives, phenols, or 3-pyridinols useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: October 22, 1979
    Date of Patent: June 9, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4272529
    Abstract: The N-m-trifluoromethylphenylanthranilates of O-alcoxycarbonylphenyl, having the formula ##STR1## wherein R is an alkyl group, preferably comprising 1 to 4 carbon atoms, besides being of low toxicity, are endowed with anti-inflammatory properties and are adapted for the treatment of inflammatory and thrombotic diseases. The method for the preparation of the above compounds comprises reacting the N-m-trifluoromethylphenylisatoic anhydride with an alkyl salicylate.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: June 9, 1981
    Assignee: Simes S.p.A.
    Inventors: Cesare Casagrande, Giorgio Ferrari
  • Patent number: 4271188
    Abstract: Compounds having hypolipidaemic activity which are substituted aralkylanilines, their preparation and pharmaceutical compositions containing them.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: June 2, 1981
    Assignee: Beecham Group Limited
    Inventor: Richard M. Hindley
  • Patent number: 4270015
    Abstract: This invention concerns a two-step process for the preparation of ethylene from mixture of carbon monoxide and hydrogen (commonly known as synthesis gas) by reaction of said carbon monoxide/hydrogen mixtures with a carboxylic acid in the presence of one or more ruthenium catalyst complexes to form an ethyl ester of said carboxylic acid coreactant, followed by pyrolysis of said ethyl ester intermediate to ethylene.
    Type: Grant
    Filed: July 14, 1980
    Date of Patent: May 26, 1981
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4268685
    Abstract: Esters of salicylamide with anti-inflammatory and analgesic action are disclosed.These esters have the following general formula: ##STR1## wherein R is a radical of an acid selected among d-2-(6'-methoxy-2'-naphtyl)-propionic acid, 2[[3-(trifluoromethyl)phenyl]-amino]-3-pyridine carboxylic acid, 2- {[3-(trifluoromethyl)-phenyl]-amino}-3-pyridincarboxylic acid, 2-(4-isobutyl-phenyl)-propionic acid, 4-allyloxy-3-chloro-phenylacetic acid, 2-(3-benzoylphenyl)-propionic acid, 2-[(2,3-dimethylphenyl)amino]-benzoic acid and 2[[3-trifluoromethyl)phenyl]-amino]benzoic acid.The process for preparing the subject esters comprises reacting a halide, preferably a chloride of the desired acid, with a solution of salicylamide.
    Type: Grant
    Filed: March 12, 1980
    Date of Patent: May 19, 1981
    Assignee: Neopharmed S.p.A.
    Inventor: Alberto Reiner
  • Patent number: 4266069
    Abstract: The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula ##STR1## and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD.sub.50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: May 5, 1981
    Assignee: The Upjohn Company
    Inventor: Jerry A. Walker
  • Patent number: 4255313
    Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4',4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 20, 1979
    Date of Patent: March 10, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4251417
    Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3',4,4' benzophenonetetracarboxylic acid, an aromatic triamine, and an acetylene-substituted aromatic monoamine. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, William J. Heilman
  • Patent number: 4251419
    Abstract: The products of the invention are vinyl end-capped oligomers which have the structure as shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound which has the structure as shown in FIG. 2. The second precursor is a complex amine salt which has the structure shown in FIG. 5.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: William J. Heilman, Daniel J. Hurley
  • Patent number: 4251418
    Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic such as 3,3', 4,4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a propargyl ester of an amino-substituted aromatic acid such as aminobenzoic acid. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, S. Paul Thackaberry
  • Patent number: 4251420
    Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid, an aromatic triamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4250324
    Abstract: Water-degradable compounds formed from amine-type compounds, aldehydes and aromatic carboxylic acids, the respective components reacting to form a complex ester which upon contact with water slowly degrades to release, at least, the original carboxylic acid.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: February 10, 1981
    Inventors: Marvin L. Beasley, Norman G. Rhode
  • Patent number: 4249021
    Abstract: 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: Grant
    Filed: February 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
  • Patent number: 4246425
    Abstract: 4-Chloro-3,5-diaminophenyl acetates having the formula ##STR1## wherein R represents an alkyl group are useful as curing agent for polyurethane elastomer and intermediates for pharmaceutical and agrochemical compounds and are produced by simultaneously nitrating hydrolyzing 4-chlorobenzylcyanide and esterifying the resulting 4-chloro-3,5-dinitrophenyl acetic acid and then reducing the resulting ester.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: January 20, 1981
    Assignee: Ihara Chemical Industry Co., Limited
    Inventors: Wataro Koike, Masami Takayama, Hideaki Ohashi, Chihiro Yazawa
  • Patent number: 4243609
    Abstract: 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: Grant
    Filed: February 2, 1978
    Date of Patent: January 6, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4243606
    Abstract: 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: Grant
    Filed: September 30, 1977
    Date of Patent: January 6, 1981
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Paul M. C. Bourdauducq, Claude M. H. E. Brouard, Claude L. E. Moerel, Jean-Pierre H. Stiot
  • Patent number: 4242523
    Abstract: An improved process for the preparation of para-nitroso-diphenyl-hydroxylamines is discussed. In the improved process the dimerizing rearrangement of a nitroso benzene is performed in the presence of at least 0.5 mole of a Lewis acid per mole of nitroso compound.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: December 30, 1980
    Assignee: Akzona Incorporated
    Inventors: Paul K. Battey, Manfred Bergfeld, Peter Hope
  • Patent number: 4242123
    Abstract: The disclosure herein relates to herbicidal compositions containing 2'-carboalkoxy-6'-alkyl-2-haloacetanilides and method of use to selectively control undesired vegetation in agricultural crops, e.g., monocotyledons such as wheat, sorghum and rice and dicotyledons such as sugarbeets and soybeans.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: December 30, 1980
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Jimmy W. Worley
  • Patent number: 4242522
    Abstract: 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: Grant
    Filed: September 17, 1979
    Date of Patent: December 30, 1980
    Assignees: Nissan Chemical Industries, Ltd., Sagami Chemical Research Center
    Inventors: Genichi Tsuchihashi, Katsuyuki Ogura, Ryozo Sakoda, Isao Hashiba, Shuichi Fukushima
  • Patent number: 4234483
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: November 18, 1980
    Assignee: American Color & Chemical Corporation
    Inventors: Raouf Botros, Ivan E. Riggle
  • Patent number: 4234482
    Abstract: Azo dyestuffs, insoluble in water, are represented by the formula: ##STR1## wherein A represents the residue of a diazotizable benzene component carrying at least two substituents or the residue of a diazotizable heterocyclic component, R represents alkyl, B represents an unsubstituted or substituted alkyl group, and X represents hydrogen, chlorine, bromine, acylamino, benzoylamino, alkoxycarbonylamino, phenoxycarbonylamino, alkylsulfonylamino or phenylsulfonylamino, the dyestuff molecule being free of groups causing water solubility by formation of ions. These dyestuffs can be used for dyeing of hydrophobic fibers, in particular polyester fibers. Affinity is excellent and there are obtained bright, full-bodied shades very fast to wet tests, sublimation, abrasion and light.
    Type: Grant
    Filed: July 8, 1975
    Date of Patent: November 18, 1980
    Assignee: Produits Chimiques Ugine Kuhlmann Service Propriete Industrielle
    Inventors: Claude M. H. E. Brouard, Jean-Pierre H. Stiot
  • Patent number: 4225725
    Abstract: Esters of certain 2,4,6-triiodobenzoic acid derivatives are useful as X-Ray contrast media. Representative compounds are the ethoxymethyl esters of acetrizoic, iothalamic and iodobenzamic acids.
    Type: Grant
    Filed: October 20, 1975
    Date of Patent: September 30, 1980
    Assignee: Mallinckrodt, Inc.
    Inventor: George B. Hoey
  • Patent number: 4221815
    Abstract: 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: Grant
    Filed: January 2, 1976
    Date of Patent: September 9, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Werner Pfaff
  • Patent number: 4219660
    Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.
    Type: Grant
    Filed: June 24, 1977
    Date of Patent: August 26, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Pius A. Wehrli
  • Patent number: 4218555
    Abstract: Acetylene end-capped polyimide oligomers are prepared by a process including the following sequential steps:1. Preparing an alkanol or ether solution containing substantially 1 molar equivalent of a dialkyl ester of an aromatic tetracarboxylic acid,2. Adding substantially 0.5 to 0.8 molar equivalent of an aromatic diamine to the solution of (1) to form a reaction product between the diacid and the diamine,3. Adding an aminoarylacetylene to the solution of (2) in a quantity sufficient to provide amine groups equivalent to the free carboxylic acid groups present in the product of (2).4. Heating the solution of (3) to vaporize the solvent therefrom, and5. Heating the product of (4) to convert the carboxylic acid groups, the ester groups, and the amino groups thereof to imide groups.The temperature in steps (2) and (3) is maintained below about 50.degree. C. The temperature in steps (4) and (5) is maintained below about 210.degree. C.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: August 19, 1980
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, Clarence D. Bertino, William J. Heilman
  • Patent number: 4218475
    Abstract: 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: Grant
    Filed: October 26, 1978
    Date of Patent: August 19, 1980
    Assignee: The Dow Chemical Company
    Inventors: Eugene R. Wagner, Donald P. Matthews, Alfred A. Renzi
  • Patent number: 4207341
    Abstract: 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: Grant
    Filed: July 1, 1976
    Date of Patent: June 10, 1980
    Assignee: Boehringer-Mannheim GmbH
    Inventors: Manfred Hubner, Hans Kuhnle, Ernst-Christian Witte, Ruth Heerdt, Rudi Weyer, Volker Hitzel
  • Patent number: 4205085
    Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: March 9, 1978
    Date of Patent: May 27, 1980
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4198431
    Abstract: N-(3-trifluoromethylphenyl)anthranilic acid esters represented by the formula (I): ##STR1## wherein R represents an alkyl group having 4 to 8 carbon atoms, are disclosed.The esters are useful as anti-inflammatory agents, particularly for an external application, with reduced toxicity. These esters are of great importance as non-steroid type anti-inflammatory agents for topical administration.
    Type: Grant
    Filed: February 2, 1978
    Date of Patent: April 15, 1980
    Assignee: Hokuriku Pharmaceutical Co., Ltd.
    Inventor: Hideo Kato
  • Patent number: 4189595
    Abstract: Novel compounds of [N-benzyl-o-(2,6-dichloroanilino)phenyl]acetic acid derivatives having the formula ##STR1## wherein X represents H, Cl, Br or a C.sub.1 -C.sub.4 alkyl group and Y is OH, OR or SR and R represents a C.sub.1 -C.sub.4 alkyl group.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: February 19, 1980
    Assignees: Nissan Chemical Industries, Ltd., Sagami Chemical Research Center
    Inventors: Ryozo Sakoda, Kazuo Nagano, Yumiko Ando, Genichi Tsuchihashi, Katsuyuki Ogura
  • Patent number: 4187316
    Abstract: 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: Grant
    Filed: January 12, 1978
    Date of Patent: February 5, 1980
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung
  • Patent number: 4185115
    Abstract: 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: Grant
    Filed: March 12, 1975
    Date of Patent: January 22, 1980
    Assignee: American Cyanamid Company
    Inventors: Jay D. Albright, Thomas G. Miner, Robert G. Shepherd
  • Patent number: 4183942
    Abstract: New insecticidal (.beta.-phenyl-.beta.-substituted-vinyl)cyclopropanecarboxylates in which the .beta.-substituent may be halogen or lower haloalkyl are described and their preparation and insecticidal utility are exemplified.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: January 15, 1980
    Assignee: FMC Corporation
    Inventor: John F. Engel