Nitro Bonded To Carbon In Acid Moiety Patents (Class 560/20)
  • Patent number: 4474806
    Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Beattie, Shu S. Yang
  • Patent number: 4457872
    Abstract: A novel 2-hydroxyoxanilic acid derivative shown by the following formula ##STR1## or a salt thereof. This compound possesses an immunoregulatory action and is useful as an antiallergic agent, an antiasthmatic, an antirheumatic, a carcinostatic agent, a therapeutic agent for autoimmune disease, and a suppressant of rejection at the tissue transplantation and skin graft.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: July 3, 1984
    Assignee: Yamanouchi Pharmaceutical Co.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka, Yoso Numasaki
  • Patent number: 4454338
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and antithrombin agents. Having strong anti-C1 (C1r, C1s) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula ##STR2## with 6-amidino-2-naphthol and, if necessary, can be transformed into pharmaceuticlly acceptable acid addition salts thereof.
    Type: Grant
    Filed: September 9, 1981
    Date of Patent: June 12, 1984
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
  • Patent number: 4440941
    Abstract: Compounds of the structure ##STR1## wherein: Q is oxygen, sulfur or imino.X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkysulfinyl, and alkylsulfonyl and may be the same or different;R.sub.1 is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylalkanoyl, or cycloalkylcarbonyl,n is an integer from 1 to 4 inclusive,R.sub.2 and R.sub.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: April 3, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, Paul R. Menard, Howard Jones
  • Patent number: 4439618
    Abstract: Optically active methyl esters of arylpropionic acids are prepared by reaction of the corresponding vinylaromatic compounds with carbon monoxide and methyl alcohol in the presence of a palladium catalyst system consisting of a palladium compound associated with optically active diphenyl-neomenthylphosphine and with trifluoroacetic acid, at substantially atmospheric pressure and at a temperature comprised between 20.degree. and 80.degree. C. There is dealt with particular regioselective and enantioselective catalysis conditions.The products obtained consist of esters of arylpropionic acids or of the corresponding acids obtainable from them, and are useful intermediates in the synthesis of organic compounds, particularly of pharmaceutical products.
    Type: Grant
    Filed: August 5, 1982
    Date of Patent: March 27, 1984
    Assignee: Montedison S.p.A.
    Inventors: Giuseppe Cometti, Gian P. Chiusoli
  • Patent number: 4426536
    Abstract: Esters of phenylacetic acids are prepared in a single step by hydrolysis of 2,2,2-trichloro-1-phenylethanes in inorganic basic media.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: January 17, 1984
    Assignee: Eli Lilly and Company
    Inventor: Roger L. Robey
  • Patent number: 4424394
    Abstract: Arylacetic acids and their esters, of the formula Ar(CH.sub.2 -COOR).sub.n (where Ar=aryl, R is H or a hydrocarbon radical, and n is 1 or 2) are manufactured by carbonylation of halomethylaryl compounds Ar(CH.sub.2 C).sub.n (where X is Cl, Br or I) with carbon monoxide and a catalyst m.sup.+ ?Fe(O).sub.3 NO!.sup.- (where M is an alkali metal, ammonium or one equivalent of an alkaline earth metal) in the presence of stoichiometric amounts of an inorganic base or of an alcoholate of an alcohol ROH.
    Type: Grant
    Filed: November 8, 1979
    Date of Patent: January 3, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Kurt Schneider, Rudolf Kummer, Kurt Schwirten, Hans-Dieter Schindler, deceased, Maria E. Schindler, heir-at-law, Ute Lang, heir-at-law, Rainer Schindler, heir-at-law
  • Patent number: 4422870
    Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: December 27, 1983
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4423064
    Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: December 27, 1983
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4419124
    Abstract: The herbicidal 4-trifluoromethyl-3'-nitrogen-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4419123
    Abstract: The herbicidal-4-trifluoromethyl-3'-carbon-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4419122
    Abstract: The herbicidal 4-trifluoromethyl-3'-oxygen-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4415744
    Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promotion catalyst which comprises the adduct of:(a) an alumina-silica-metal oxide combination represented by the formula:(Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.cwherein M is a metal cation selected from the group consisting of the lanthanides or rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al.sub.2 O.sub.3, SiO.sub.2, and M.sub.2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and(b) a catalytically effective amount of sulfur trioxide.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: November 15, 1983
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-Bo Wang
  • Patent number: 4410718
    Abstract: Carboxylic acid-containing compounds are esterified by reacting at elevated temperatures with organic esters of trichloroacetic acid in the presence of an initiator.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: October 18, 1983
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4405642
    Abstract: A method for the treatment or prophylaxis of cardiac disorders in a mammal, comprising administering to such mammal a short-acting .beta.-blocking compound of the formula: ##STR1## wherein X is an ester-containing group; R may be lower alkyl, aralkyl or an ester-containing group; R.sub.1 may be lower alkyl; and Ar may be substituted or unsubstituted aromatic; or a pharmaceutically acceptable salt thereof. Novel compounds possessing short acting .beta.-adrenergic blocking activity are also disclosed.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: September 20, 1983
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung-tsam Kam, Paul W. Erhardt, Robert J. Borgman, John P. O'Donnell
  • Patent number: 4398035
    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: October 3, 1980
    Date of Patent: August 9, 1983
    Assignee: The Upjohn Company
    Inventor: Jerry A. Walker
  • Patent number: 4395565
    Abstract: A process for the preparation of aromatic urethans by reaction between aromatic amines and alkyl carbonates, said reaction being carried out in the presence of a catalyst composed of an alcoholate of an alkali metal or an alkaline earth metal. The reaction is caused to take place at a temperature which is variable from +50.degree. C. and +150.degree. C., in the liquid phase and with a molar ratio of the carbonate to the amine of from 10:1 to 1:10.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: July 26, 1983
    Assignee: Anic S.p.A.
    Inventors: Ugo Romano, Giancarlo Fornasari, Sandro Di Gioacchino
  • Patent number: 4390721
    Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: June 28, 1983
    Assignee: Allen & Hanburys Limited
    Inventor: Stanley M. Roberts
  • Patent number: 4387058
    Abstract: Novel phenyl and naphthyl esters of 2-(1-oxo-alkoxy)ethyl carbamic acids are prepared. The compounds are useful as pharmacological and agricultural agents.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: June 7, 1983
    Assignee: The Dow Chemical Company
    Inventor: Chester E. Pawloski
  • Patent number: 4380636
    Abstract: Carboxylic acid-containing compounds are esterified by reacting at elevated temperatures with an organic ester of trichloroacetic acid and an electrophilic halide in the presence of an initiator.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: April 19, 1983
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4376784
    Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: March 15, 1983
    Assignee: ICI Australia Limited
    Inventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
  • Patent number: 4374293
    Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: February 15, 1983
    Assignee: The Standard Oil Co.
    Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
  • 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: 4368135
    Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: January 11, 1983
    Assignee: BBC, Brown, Boveri & Company, Ltd.
    Inventor: Maged A. Osman
  • Patent number: 4361494
    Abstract: New anisotropic compounds suitable for use in LC-display devices are disclosed and claimed. The new compounds are cyclohexyl cyclohexylmethyl ethers of formula (1): ##STR1## in which X and Y are respectively hydrogen, alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group, halogen, or cyclic radical of formula (1a) or (1b): ##STR2## in which R.sup.1 and R.sup.2 represent hydrogen alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group or halogen, and Z.sup.1 and Z.sup.2 represent simple covalent bonds or grounds of the formulas --COO--, --OOC--, --CH.sub.2 O-- or --OCH.sub.2, with the requirement that only one of the groups X, Y can be a cyclicradical or formula (1a) or (1b). Also disclosed and claimed are LC-mixtures containing these compounds and methods for their synthesis.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: November 30, 1982
    Assignee: BBC Brown, Boveri, & Company, Limited
    Inventors: Maged A. Osman, Laszlo Revesz
  • Patent number: 4360689
    Abstract: New .alpha.-halobenzyl esters, intermediates for .alpha.-cyanobenzyl pyrethroid esters, are prepared by treating a benzaldehyde derivative with a pyrethroid acid halide. The resulting .alpha.-halobenzyl ester is treated with a water-soluble compound capable of generating cyanide ions (CN.sup.-) to give the corresponding .alpha.-cyanobenzyl esters.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: November 23, 1982
    Assignee: Shell Oil Company
    Inventor: Charles H. Tieman
  • Patent number: 4349452
    Abstract: Anisotropic compounds of the formula (1) ##STR1## wherein X and Y are each hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, N-monoalkaylamine having 1 to 12 carbon atoms in the alkyl group, halogen, cyano, nitro, or a cyclic radical of the formula ##STR2## wherein R is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.12 alkyl, or C.sub.1 -C.sub.12 alkoxy, Z.sup.1 is a --COO-- group or a --OOC-- group and Z.sup.2 may be the same as Z.sup.1 or a single convalent bond, with the proviso that:(a) only one of the groups X and Y is a cyclic radical, and(b) neither of the groups X or Y is hydrogen, bromine, or poperidino when the other is hydrogen, have low .DELTA.n-values without a greay tendency to form smectic phases and are useful in preparing liquid crystal devices.
    Type: Grant
    Filed: July 15, 1980
    Date of Patent: September 14, 1982
    Assignee: Merck Patent GmbH
    Inventors: Maged A. Osman, Laszlo Revesz
  • Patent number: 4344961
    Abstract: Novel carboxylic acid esters of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are identical or different and each is hydrogen, halogen or alkyl or alkenyl of up to 5 carbon atoms,Y is 3-(2,2-dihalogenovinyl)-2,2-dimethyl-cyclopropyl or a radical of the formula ##STR2## where R.sup.4 is unbranched or branched alkyl, alkenyl or alkynyl of up to 4 carbon atoms or is an alicyclic radical of 3 to 7 carbon atoms,R.sup.5 is halogen, alkyl or alkoxy of up to 5 carbon atoms, trihalomethyl, cyano or nitro anda is from 0 to 3 andZ is a radical of the formula ##STR3## where X is oxygen, sulfur or --CH.sub.2 --,R.sup.6, R.sup.7 and R.sup.8 are halogen or alkyl, alkoxy or haloalkyl of up to 5 carbon atoms andb, c and d are from 0 to 3, their preparation and their use in insect and arachnid control.
    Type: Grant
    Filed: February 9, 1981
    Date of Patent: August 17, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd-Ulrich Schwarz, Karl Kiehs, Heinrich Adolphi
  • Patent number: 4340765
    Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: July 20, 1982
    Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
  • Patent number: 4336396
    Abstract: This invention relates to a process for the preparation of 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-phenol esters (I) and their salts with organic and inorganic acids comprising the reaction of thymol with a salt of an 1-halo-dimethylaminoethane to obtain ethylamine-N,N-dimethyl-2-(thymyloxy) (II), the subsequent reaction of (II) with an acylating agent according to the Friedel and Kraft reaction to obtain 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-1-acyl-benzene (III) and the oxidation of (III) to obtain the products (I) which, if desired, may be transformed in their salts with organic or inorganic acids.This process allows to obtain the products (I) in high quality and quantity without isolating any intermediate product.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: June 22, 1982
    Assignee: Blasinachim S.p.A.
    Inventors: Claudio Giordano, Aldo Belli
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4335054
    Abstract: Compounds of the formula I ##STR1## in which p, m, Z, R, R' and Y are as defined in claim 1, can be obtained in a simple and economical manner by a novel process which comprises reacting a halide of the formula ##STR2## with the corresponding acrylic acid derivative, in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I), and functional derivatives prepared therefrom, are useful for the preparation of photocrosslinkable polymers, which can in particular be employed as (so-called) photoresists.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4332734
    Abstract: New homopolymerizable or copolymerizable 3,3-disubstituted furan dione compounds are described of the formula ##STR1## wherein X is a reactive moiety and Y and R are unreactive moieties.
    Type: Grant
    Filed: December 9, 1980
    Date of Patent: June 1, 1982
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Michael J. Mullins
  • Patent number: 4324903
    Abstract: A process for the preparation of new malonic esters of the formula: ##STR1## wherein R is a substituted or unsubstituted C.sub.1 to C.sub.6 alkyl, a substituted or unsubstituted aromatic ring, a heterocyclic ring, a cycloalkyl group, or a fused ring system; R.sup.1 is hydrogen, lower alkyl, aralkyl, aralkyl substituted by halogen or alkyl or a substituted aromatic, cycloaliphatic or heterocyclic ring; and X is halogen.
    Type: Grant
    Filed: June 21, 1976
    Date of Patent: April 13, 1982
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RT.
    Inventors: Magda Huhn, Eva Somfai, Gabor Szabo, Gabor Resovszki, Livia Gneth nee Zalantai
  • 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: 4316044
    Abstract: Isovaleric acid derivatives having the formula ##STR1## wherein typical representations of X is halophenyl, R.sub.1 is hydrogen or cyano, R.sub.2 is hydrogen or lower alkyl, and Y is halophenyl. These derivatives possess insecticidal and acaricidal properties. The process for their preparation is described.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: Nippon Soda Company Limited
    Inventors: Keiichi Ishimitsu, Isamu Kasahara, Tomio Yamada, Michihiko Matsuda, Hidemitsu Takahashi, Shuichi Soma
  • Patent number: 4316046
    Abstract: A process for the preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted with an aryliodoso carboxylate in liquid medium to form the desired aryl carboxylate. Promoters can be employed to increase the rate of reaction and improve selectivity to the aryl carboxylate.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventor: Lawrence C. Costa
  • 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: 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: 4304728
    Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: December 8, 1981
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4301044
    Abstract: Zwitterionic surfactant compounds are made readily biodegradable in the environment by the inclusion of a biochemically and/or hydrolytically labile chemical linkage located between the cationic and anionic charge centers of the compounds and anywhere from the second to the tenth atom distant from the cationic charge center. The biodegradable linkage is preferably an ester or amide. The alkoxylated zwitterionic surfactants herein exhibit outstanding particulate soil removal performance and are also effective in removing oily soils from fabrics, in addition to being readily biodegradable. Also described are detergent compositions containing the zwitterionic surfactants, and, optionally containing cosurfactants and detergent builders.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: November 17, 1981
    Assignee: The Procter & Gamble Company
    Inventors: George E. Wentler, Joseph McGrady, Eugene P. Gosselink, William A. Cilley
  • Patent number: 4296254
    Abstract: The disclosure herein pertains to the preparation of N-(alkoxymethyl)- and other N-methylene ether-substituted 2-haloacetamides from other N-methylene ether-substituted 2-haloacetamides and the appropriate alcohol by a transetherification process.
    Type: Grant
    Filed: March 25, 1980
    Date of Patent: October 20, 1981
    Assignee: Monsanto Company
    Inventors: Robert E. Middlebrook, George R. Harvey, John P. Chupp
  • Patent number: 4291061
    Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: September 22, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Elmar Sturm, Robert Nyfeler
  • Patent number: 4291176
    Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.
    Type: Grant
    Filed: August 24, 1977
    Date of Patent: September 22, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • Patent number: 4289894
    Abstract: Compounds of the formula: ##STR1## are disclosed wherein R is C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.3 to C.sub.8 cycloalkyl, phenyl, halophenyl, naphthyl, benzyl, indanyl, phenacyl, p-nitrophenacyl, xylyl or acetoxymethyl; R.sup.1 is phenyl, benzyl or phenyl or benzyl substituted by halo, nitro, dialkylamino, alkoxy or trifluoromethyl, lower alkyl or allyl; and X is halo. The compounds are intermediates in the manufacture of penicillins.
    Type: Grant
    Filed: March 6, 1979
    Date of Patent: September 15, 1981
    Assignee: Chinoin Gyogyszer es Vegylszeti Termekek Gyara R.T.
    Inventors: Magda Huhn, Eva Somfai, Gabor Szabo, Gabor Resovszki, Zoltan Gneth
  • Patent number: 4288612
    Abstract: Deposit control additives for internal combustion engines are provided which maintain cleanliness of intake systems withcut contributing to combustion chamber deposits. The additives are hydrocarbylpoly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) chain of 2-5 carbon oxyalkylene units bonded through an oxycarbonyl group to a nitrogen atom of a diamine.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: September 8, 1981
    Assignee: Chevron Research Company
    Inventors: Robert A. Lewis, Lewis R. Honnen
  • Patent number: 4283414
    Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: August 11, 1981
    Assignee: ICI Australia Limited
    Inventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
  • Patent number: 4278598
    Abstract: Novel photographic dye release compounds have the structure: ##STR1## wherein R.sup.1 is an aromatic group containing 5-7 members in the ring to which Nu and E are attached; R.sup.2 and R.sup.3 are bivalent organic groups containing from 1-3 atoms in the bivalent linkage which are alkylene, oxyalkylene or thiaalkylene; Nu is a nucleophilic group which is a hydrazine, an hydroxyamino, an hydroxy, a sulfonamido, a primary amino or alkali-labile precursors for said nucleophilic groups; E is an electrophilic group which is a carbonyl or a sulfonyl; Q is a bivalent group providing a mono atom linkage between E and X.sub.2 and is amino providing a mono atom nitrogen linkage, an oxygen atom, a sulfur atom or a selenium atom, provided that Nu and E are positioned on a ring of said aromatic group to provide for intramolecular formation of a 5- to 7-membered ring between Nu and E displacing Q--X.sub.2 from E; one of X.sup.1 or Q--X.sub.
    Type: Grant
    Filed: September 1, 1976
    Date of Patent: July 14, 1981
    Assignee: Eastman Kodak Company
    Inventors: Gerald C. Hinshaw, Paul B. Condit
  • Patent number: 4271187
    Abstract: A compound of the formula ##STR1## possesses antihypertensive activity. Also provided are methods for the preparation of the compounds as well as pharmaceutical formulations and methods for their use as antihypertensive agents.
    Type: Grant
    Filed: September 18, 1979
    Date of Patent: June 2, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Joseph G. Atkinson, Clarence S. Rooney, Yves Girard, Edward L. Engelhardt