Halogen In Acid Moiety Patents (Class 560/47)
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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: 4360690Abstract: 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: GrantFiled: June 12, 1981Date of Patent: November 23, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: 4354033Abstract: 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: GrantFiled: August 31, 1981Date of Patent: October 12, 1982Assignee: Council of Scientific & Industrial ResearchInventors: Nanduri Bhanumati, Pralhad B. Sattur
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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: 4347188Abstract: 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: GrantFiled: June 30, 1980Date of Patent: August 31, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Osamu Kirino, Toshiro Kato, Shigeo Yamamoto
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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: 4324904Abstract: 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: GrantFiled: December 19, 1979Date of Patent: April 13, 1982Assignee: The Upjohn CompanyInventors: Thomas A. Hylton, Jerry A. Walker
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Patent number: 4321368Abstract: 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: GrantFiled: May 1, 1980Date of Patent: March 23, 1982Assignee: Mallinckrodt, Inc.Inventor: George B. Hoey
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Patent number: 4316860Abstract: 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: GrantFiled: May 15, 1980Date of Patent: February 23, 1982Assignee: Ciba-Geigy CorporationInventor: Michael Marky
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Patent number: 4313956Abstract: 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: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: 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: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4310677Abstract: 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: GrantFiled: December 17, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Dietrich Mangold
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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: 4309350Abstract: 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: GrantFiled: January 24, 1980Date of Patent: January 5, 1982Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, Reimund Walser
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Patent number: 4308394Abstract: 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: GrantFiled: June 8, 1979Date of Patent: December 29, 1981Assignee: Bayer AktiengesellschaftInventors: Karl-Ernst Shuster, Hans Rudolph, Wolfram Mayer, Hans J. Rosenkranz
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Patent number: 4306074Abstract: 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: GrantFiled: May 27, 1980Date of Patent: December 15, 1981Assignee: BASF AktiengesellschaftInventors: Peter Tonne, Heinz-Guenter Oeser, Dietrich Mangold
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Patent number: 4288621Abstract: The present invention relates to halo-substituted 2,2 dimethylcyclopropaneamides, useful as intermediates for the preparation of imidates having pesticidal properties.Type: GrantFiled: June 2, 1980Date of Patent: September 8, 1981Assignee: Zoecon CorporationInventors: Gustave K. Kohn, Ted A. Baer
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Patent number: 4272546Abstract: 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: GrantFiled: October 22, 1979Date of Patent: June 9, 1981Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4272529Abstract: 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: GrantFiled: April 3, 1980Date of Patent: June 9, 1981Assignee: Simes S.p.A.Inventors: Cesare Casagrande, Giorgio Ferrari
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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: 4270015Abstract: 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: GrantFiled: July 14, 1980Date of Patent: May 26, 1981Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4268685Abstract: 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: GrantFiled: March 12, 1980Date of Patent: May 19, 1981Assignee: Neopharmed S.p.A.Inventor: Alberto Reiner
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Patent number: 4266069Abstract: 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: GrantFiled: December 19, 1979Date of Patent: May 5, 1981Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4255313Abstract: 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: GrantFiled: April 20, 1979Date of Patent: March 10, 1981Assignee: Gulf Oil CorporationInventors: Patricia A. Antonoplos, William J. Heilman
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Patent number: 4251417Abstract: 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: GrantFiled: April 25, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: Wai Y. Chow, William J. Heilman
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Patent number: 4251419Abstract: 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: GrantFiled: April 5, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: William J. Heilman, Daniel J. Hurley
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Patent number: 4251418Abstract: 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: GrantFiled: April 27, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: Wai Y. Chow, S. Paul Thackaberry
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Patent number: 4251420Abstract: 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: GrantFiled: April 23, 1979Date of Patent: February 17, 1981Assignee: Gulf Oil CorporationInventors: Patricia A. Antonoplos, William J. Heilman
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Patent number: 4250324Abstract: 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: GrantFiled: November 18, 1977Date of Patent: February 10, 1981Inventors: Marvin L. Beasley, Norman G. Rhode
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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: 4246425Abstract: 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: GrantFiled: March 8, 1979Date of Patent: January 20, 1981Assignee: Ihara Chemical Industry Co., LimitedInventors: Wataro Koike, Masami Takayama, Hideaki Ohashi, Chihiro Yazawa
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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: 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: 4242523Abstract: 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: GrantFiled: August 20, 1979Date of Patent: December 30, 1980Assignee: Akzona IncorporatedInventors: Paul K. Battey, Manfred Bergfeld, Peter Hope
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Patent number: 4242123Abstract: 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: GrantFiled: November 30, 1978Date of Patent: December 30, 1980Assignee: Monsanto CompanyInventors: John P. Chupp, Jimmy W. Worley
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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: 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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Substituted 3-carbalkoxy 4-alkylamino-azobenzene compound as disperse dyestuffs for synthetic fibers
Patent number: 4234482Abstract: 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: GrantFiled: July 8, 1975Date of Patent: November 18, 1980Assignee: Produits Chimiques Ugine Kuhlmann Service Propriete IndustrielleInventors: Claude M. H. E. Brouard, Jean-Pierre H. Stiot -
Patent number: 4225725Abstract: 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: GrantFiled: October 20, 1975Date of Patent: September 30, 1980Assignee: Mallinckrodt, Inc.Inventor: George B. Hoey
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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: 4219660Abstract: 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: GrantFiled: June 24, 1977Date of Patent: August 26, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Pius A. Wehrli
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Patent number: 4218555Abstract: 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: GrantFiled: November 1, 1978Date of Patent: August 19, 1980Assignee: Gulf Oil CorporationInventors: Patricia A. Antonoplos, Clarence D. Bertino, William J. Heilman
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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: 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: 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: 4198431Abstract: 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: GrantFiled: February 2, 1978Date of Patent: April 15, 1980Assignee: Hokuriku Pharmaceutical Co., Ltd.Inventor: Hideo Kato
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Patent number: 4189595Abstract: 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: GrantFiled: August 30, 1978Date of Patent: February 19, 1980Assignees: Nissan Chemical Industries, Ltd., Sagami Chemical Research CenterInventors: Ryozo Sakoda, Kazuo Nagano, Yumiko Ando, Genichi Tsuchihashi, Katsuyuki Ogura
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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: 4183942Abstract: 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: GrantFiled: October 23, 1978Date of Patent: January 15, 1980Assignee: FMC CorporationInventor: John F. Engel