Nitro Or Nitroso Patents (Class 562/434)
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Patent number: 4994494Abstract: Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: December 14, 1989Date of Patent: February 19, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: John R. Regan, Joseph G. Bruno, Kent W. Neuenschwander, Donald E. Kuhla
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Patent number: 4990660Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.Type: GrantFiled: December 21, 1988Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Ulrich Eichenauer
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Patent number: 4956490Abstract: There is disclosed a continuous, non-isolation process for preparing benzylpyruvic acids and benzylpyruvic esters. The benzylpyruvic acids and esters obtained are useful as intermediates to prepare carboxyalkyl dipeptide compounds which are used as angiotension converting enzyme (ACE) inhibitors to treat hypertension.Type: GrantFiled: March 9, 1989Date of Patent: September 11, 1990Assignee: Merck & Co., Inc.Inventors: James W. McManus, John F. Genus
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Patent number: 4933367Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.Type: GrantFiled: March 12, 1987Date of Patent: June 12, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
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Patent number: 4925978Abstract: A new process of synthesis of optically active .alpha.-amino acids is described through nitrosation in a non-aqueous, aprotic system, of the corresponding N-carbamyl derivatives followed by decomposition of the thus obtained N-nitroso derivatives in aqueous acidic medium. The process, which is of a general applicability, leads to a remarkable increase in the reaction yields, due to the suppression of the main side reaction leading to the corresponding .alpha.-hydroxy-acid. Some N-nitroso intermediates, which can be recovered from the process of the invention, are also described.Type: GrantFiled: April 14, 1988Date of Patent: May 15, 1990Assignee: Eniricerche S.p.A.Inventors: Sandro Di Gioacchino, Antonio Paolinelli, Luciano Re
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Patent number: 4921939Abstract: Substituted guanidines and ethanamidines are provided as high potency sweetening agents.Type: GrantFiled: March 3, 1987Date of Patent: May 1, 1990Assignee: Universite Claude Bernard -Lyon 1Inventors: Claude Nofre, Jean M. Tinti, Farroudja Ouar Chatzopoulos
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Patent number: 4908386Abstract: The present invention provides compounds of general formula (I) ##STR1## wherein Ar represents an unsubstituted or substituted phenyl gorup;R.sup.1 and R.sup.2 each represents a hydrogen atom or a C.sub.1-3 alkyl group;X represents a bond or a C.sub.1-7 alkylene, C.sub.2-7 alkenylene or C.sub.2-7 alkynylene chain;Y represents a bond or a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain;Q represents a substituted phenyl or pyridyl ring;and physiologically acceptable salts and solvates thereof useful as stimulants of .sub.2 -adrenoreceptors and particularly in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.Type: GrantFiled: December 20, 1988Date of Patent: March 13, 1990Assignee: Glaxo Group LimitedInventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell, David Middlemiss, Charles Willbe
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Patent number: 4877895Abstract: Sweetening agents, characterized in that they conform to the following formula: ##STR1## wherein: A is an imino (.dbd.N--), iminium (.dbd.N.sup.+ <), methylene (.dbd.C<) group, the iminium group being able to be salified by a physiologically acceptable anion;m and n are number equal to 1 or 2;B:when n=1, represents H, CN, OCH.sub.3, NO.sub.2, SO.sub.2 R, SOR, SO.sub.2 NHR, SO.sub.2 NR.sub.2, wherein R is an alkyl, cycloalkyl or aryl group having up to 10 carbon atoms;when n=2, represents H, CN, OCH.sub.3 ;X:represents CN, NO.sub.2, when B is H, CN, OCH.sub.3 ;represents CN, NO.sub.2, COCH.sub.3, CHO, Cl, CF.sub.3, F, H, when B is NO.sub.2, SO.sub.2 R, SOR, SO.sub.2 NHR, SO.sub.2 NR.sub.2 ;M is a hydrogen atom or a physiologically acceptable organic or inorganic cation.Type: GrantFiled: March 4, 1986Date of Patent: October 31, 1989Assignee: Universite Claude Bernard - Lyon 1Inventors: Claude Nofre, Jean M. Tinti, Farroudja O. Chatzopoulos
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Patent number: 4876376Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.Type: GrantFiled: December 15, 1987Date of Patent: October 24, 1989Assignee: Rhone-Poulenc Specialistes ChimiquesInventors: Michael Desbois, Camille Disdier
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Patent number: 4866204Abstract: A method is disclosed for preparing a substituted cyclic carboxylic acid from a corresponding substituted cyclic hydrocarbon. The hydrocarbon is oxidized in oxygen or air in a liquid phase in an organic solvent under alkaline conditions, in the presence of a catalyst selected from the group consisting of metal tetraphenylporphins, metal acetylacetonates, metal phthalocyanines and mixtures thereof. The oxidation is capable of proceeding generally at room temperature and atmospheric pressure.Type: GrantFiled: February 16, 1988Date of Patent: September 12, 1989Assignee: Nobel Chemicals ABInventor: Nils A. Svensson
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Patent number: 4859206Abstract: This invention encompasses compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently are hydrogen, C.sub.1-4 alkyl, or C.sub.2-4 hydroxyalkyl; one of R.sup.3 to R.sup.7 is --SO.sub.3 H or --COOH; and the remaining of R.sup.3 to R.sup.7 independently are hydrogen, chlorine, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or --NR.sup.8 R.sup.9, where R.sup.8 and R.sup.9 independently are hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkoxy, or where --NR.sup.8 R.sup.9 is piperidine, morpholine, piperazine, or pyrrolidone; or a water soluble salt thereof; hair dye preparation containing these compounds, and methods for dyeing hair using such preparation.Type: GrantFiled: February 26, 1988Date of Patent: August 22, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Edgar Lieske, Horst Hoeffkes, Norbert Maak
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Patent number: 4855480Abstract: Compounds of the formula ##STR1## in which Y is hydrogen, lower alkyl, or an alkali metal or alkaline earth metal, and Z is selected from hydrogen, a hydrogen halide complex or a tri(lower)alkylmethoxycarbonyl group, their use as herbicides and herbicidal compositions thereof are disclosed.Type: GrantFiled: June 29, 1988Date of Patent: August 8, 1989Assignee: FMC CorporationInventors: Natesan Murugesan, Mariano Guiducci
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Patent number: 4853398Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.Type: GrantFiled: April 13, 1987Date of Patent: August 1, 1989Assignee: Eli Lilly and CompanyInventors: F. P. Carr, Robert D. Dillard, Doris E. McCullough
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Patent number: 4835306Abstract: This invention is a process for the preparation of a 3-amino-4-hydroxybenzoic acid which comprises(a) contacting a p-halobenzoic acid with nitric acid in an acidic reaction medium under conditions such that a 3-nitro-4-halobenzoic acid is prepared;(b) contacting the 3-nitro-4-halobenzoic acid with an alkali metal hydroxide in a reaction medium under conditions such that the halo moiety is replaced with a hydroxide moiety, to prepare a 3-nitro-4-hydroxybenzoic acid, or salt thereof; and(c) reducing the 3-nitro-4-hydroxybenzoic acid under conditions such that a 4-hydroxy-3-aminobenzoic acid is prepared.Type: GrantFiled: February 10, 1986Date of Patent: May 30, 1989Assignee: The Dow Chemical CompanyInventor: Zenon Lysenko
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Patent number: 4832697Abstract: This invention encompasses compounds of the formula: ##STR1## wherein: one of R.sup.1 or R.sup.2 is nitro and the other is --SO.sub.3 H or COOH; andone of R.sup.3 or R.sup.4 is hydrogen and the other is --NR.sup.5 R.sup.6, where R.sup.5 and R.sup.6 independently are hydrogen, C.sub.1-4 alkyl, or C.sub.2-4 hydroxyalkyl;or a water soluble salt thereof; hair dye preparations containing the above compounds as substantive hair dyes; and methods for dyeing hair using such preparations.Type: GrantFiled: February 26, 1988Date of Patent: May 23, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Edgar Lieske, Norbert Maak
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Patent number: 4806682Abstract: Sulfonium and sulfoxonium salts of the formula ##STR1## wherein X and Y are independently a hydrogen atom, a halogen atom, a trihalomethyl group, a nitro group, an alkyl group or a cyano group; Z is a halogen atom, a trihalomethyl group, an alkyl group, cyano group or --S(O).sub.m R, wherein m is 0, 1 or 2 and R is an alkyl group; A is a halogen atom, a nitro group or a cyano group; B is a negatively charged organic substituent; n is 0 or 1, each R.sup.1 is independently an alkyl group, an aryl group or --N(R.sup.2).sub.2 wherein R.sup.2 is an alkyl group or an aryl group; S is sulfur; and N is nitrogen, and compositions containing these salts exhibit herbicidal activity.Type: GrantFiled: December 22, 1986Date of Patent: February 21, 1989Assignee: Rohm and Haas CompanyInventor: Roy Y. Yih
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Patent number: 4804760Abstract: A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3,R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, andX.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkyl-sulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical,comprising reacting an aminoacrylate of the formulain whichX.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group,W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical,Z is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, andR.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.Type: GrantFiled: April 28, 1987Date of Patent: February 14, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe
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Patent number: 4804756Abstract: A method for preparing 5,6-dialkoxy-4-alkyl-quinazolinones is described. The 5,6-dialkoxy-4-alkyl-quinazolinones are active cardiotonic agents.Type: GrantFiled: March 28, 1988Date of Patent: February 14, 1989Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Robert A. Mallory, Jeffery B. Press
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Patent number: 4762840Abstract: Novel pyrimido[2,1-b]benzothiazoles of the formula ##STR1## wherein R and R.sub.3 are individually selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms or taken together with the carbon to which they are attached form a cycloalkyl of 3 to 6 carbon atoms, R.sub.1 is selected from the group consisting of hydroxy, alkoxy of 1 to 12 carbon atoms, cycloalkyl of 7 to 12 carbon atoms, and ##STR2## R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms or taken together with the nitrogen form piperidino or morpholino, R.sub.Type: GrantFiled: July 31, 1986Date of Patent: August 9, 1988Assignee: Roussel UclafInventors: David A. Rowlands, Julian M. C. Golec, Saroop S. Matharu, Peter W. Hairsine
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Patent number: 4751244Abstract: The present invention is directed to compounds of the general formula I and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sup.1 =HO or HOOC(CH.sub.2).sub.x CHR.sup.2 NH--;R.sup.2 =H, lower alkyl, benzyl or --CH.sub.2 OH;x=0 or 1;A=--(CH.sub.2).sub.n -- or ##STR2## n=1 to 5; and Y=H, Cl or OCH.sub.3Z=H or Clm=0 or 1R=lower alkyl;with the proviso that where R.sup.1 =OH, Y is H or Cl and m is 1, n is 4 or 5.The present invention is also directed to an antisickling pharmaceutical carrier and an antisickling agent of the general formula (I) (without the proviso) and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 30, 1987Date of Patent: June 14, 1988Assignees: Merck & Co., Inc., The University of PittsburghInventors: Donald J. Abraham, Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr.
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Patent number: 4751304Abstract: A method for preparing 5,6-dialkoxy-4-alkyl-quinazolinones is described. The 5,6-dialkoxy-4-alkyl-quinazolinones are active cardiotonic agents.Type: GrantFiled: September 26, 1984Date of Patent: June 14, 1988Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Robert A. Mallory, Jeffery B. Press
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Patent number: 4736057Abstract: This invention concerns novel (4-substituted-2-phenylcyclohexyl)alkenoic and alkanoic acid derivatives of the formula I wherein one of Ra and Rb is hydrogen, hydroxy, (1-6C)alkyl, (1-6C)alkoxy, (3-6C)alkenyloxy or phenyl(1-4C)alkoxy and the other of Ra and Rb is hydrogen, (1-6C)alkyl, (1-6C)alkoxy or (3-6C)alkenyloxy; or Ra and Rb together form a (2-4C)alkylenedioxy or oxo group; benzene ring X optionally bears a substituent selected from halogeno, (1-6C)alkyl, (1-6C)alkoxy, hydroxy, (2-6C)alkanoyloxy, (1-6C)alkanoylamino, trifluoromethyl and nitro; n is 3-5; Y is ethylene or vinylene; and in the cyclohexane ring, the substituents at positions 1 and 2 have cis- or trans-relative stereochemistry; and the pharmaceutically acceptable salts, (1-6C)alkyl esters and (1-6C)alkanesulphonamides thereof. The compounds of formula I possess valuable pharmacological properties of use in medicines.Type: GrantFiled: November 9, 1984Date of Patent: April 5, 1988Assignee: Imperial Chemical Industries PLCInventors: Allen J. Guildford, Ralph W. Turner
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Patent number: 4727180Abstract: Polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides, and esters, such as methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepro panoate, are useful as antihypertensive agents.Type: GrantFiled: January 4, 1985Date of Patent: February 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul E. Aldrich, Gilbert H. Berezin
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Patent number: 4727183Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.Type: GrantFiled: October 31, 1986Date of Patent: February 23, 1988Assignee: American Home Products CorporationInventors: George C. Buzby, Jr., Michael W. Winkley, Ronald J. McCaully
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Patent number: 4670434Abstract: This invention relates to compounds of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein the various substituents are defined herein. These compounds are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents in mammals.Type: GrantFiled: November 14, 1985Date of Patent: June 2, 1987Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4649212Abstract: The invention relates to novel phenoxyphenylamino acid derivatives of the formula I ##STR1## wherein X is hydrogen, chlorine, fluorine or bromine,R.sup.1 is hydrogen, nitroso, or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkylcarbonyl or C.sub.2 -C.sub.4 alkenylcarbonyl, each of which is unsubstituted or substituted by one or more halogen atoms,Q is a straight chain or branched aliphatic radical of 1 to 5 carbon atoms ##STR2## in which A', E', G', L' and M' are hydrogen or C.sub.1 -C.sub.4 alkyl, or two adjacent substituents A', E', G', L' and M' together are also a bond between the two carbon atoms to which they are attached; A, E, G, L and M are hydrogen or one or two of A, E, G, L and M are also --OR.sup.2, --SR.sup.3, --COOR.sup.4, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl substituted by --OR.sup.5, --SR.sup.6 or --COOR.sup.7, where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are hydrogen or C.sub.1 -C.sub.4 alkyl; a, b, c and d are 0 or 1; or R.sup.Type: GrantFiled: April 4, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventor: Dieter Durr
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Patent number: 4639518Abstract: The synthesis of 5,6-dioxy substituted quinazolinediones is described. The novel quinazolinediones are useful as cardiotonic agents.Type: GrantFiled: September 24, 1984Date of Patent: January 27, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Stanley C. Bell, Donald W. Combs, Robert Falotico, Alfonso J. Tobia
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Patent number: 4634769Abstract: A process for the preparation of 8-halo-5,6-dialkoxyquinazoline-2,4-diones and their metal salts is described. The diones are active cardiotonic agents.Type: GrantFiled: September 25, 1984Date of Patent: January 6, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Robert A. Mallory, Jeffrey B. Press, Harvey M. Werblood
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Patent number: 4614806Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.Type: GrantFiled: February 11, 1985Date of Patent: September 30, 1986Assignee: American Home Products CorporationInventors: George C. Buzby, Jr., Michael W. Winkley, Ronald J. McCaully
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Patent number: 4609756Abstract: In the preparation of a cinnamic acid by reacting the corresponding benzaldehyde with ketene in the presence of a catalyst, the improvement which comprises using as the catalyst an iron and/or zinc salt of a mono- or di-carboxylic acid with 2 to 20 carbon atoms containing free carboxylic acid and/or anhydride, and then splitting the reaction product in the temperature range from 100.degree. to 250.degree. C. with an acid or basic catalyst.Type: GrantFiled: October 4, 1985Date of Patent: September 2, 1986Assignee: Bayer AktiengesellschaftInventors: Alfons Dorlars, Heinz U. Blank, Herbert Nordt, deceased, Viktor Trescher
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4594440Abstract: Crude phenoxybenzoic acid herbicide, e.g., acifluorfen, having one or more undesirable isomer/by-product impurities associated therewith is separated therefrom employing an inert solvent which is selective for the isomers/other by-products.Type: GrantFiled: July 25, 1983Date of Patent: June 10, 1986Assignee: Rhone:Pulenc, Inc.Inventors: Thomas J. Giacobbe, Grace Tsien
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Patent number: 4585879Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.Type: GrantFiled: February 11, 1985Date of Patent: April 29, 1986Assignee: American Home Products CorporationInventors: Michael W. Winkley, Ronald J. McCaully
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4567004Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.Type: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4499299Abstract: Compounds which antagonize the slow-reacting substance of anaphylaxis or components thereof, e.g., leukotrienes, in warm blooded animals as well as intermediates and methods for their preparation, pharmaceutical compositions and methods for their administration. The compounds are diphenyl carboxylic acids with particular linking groups between the individual phenyl rings and the carboxylic acid moiety. Particular utilities are to relieve asthma and inflammation in man.Type: GrantFiled: December 6, 1982Date of Patent: February 12, 1985Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Alvin K. Willard
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Patent number: 4477556Abstract: A photopolymerizable coating composition comprising(1) a nongaseous, ethylenically unsaturated, polymerizable compound,(2) a specified acidic o-nitroaromatic compound, and(3) an organic, radiation-sensitive, free-radical generating system which is useful for making a positive or negative polymeric image on a substrate.Type: GrantFiled: August 18, 1982Date of Patent: October 16, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas E. Dueber, William J. Nebe
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Patent number: 4476315Abstract: Nitroarylacetic acid esters are prepared by reacting a nitroaromatic compound which is devoid of halogen on the aromatic ring carrying a nitro group with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base so that the ester undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-substituent functions as a leaving group. Nitrobenzene acetic acids and their esters are useful intermediates for the synthesis of pharmaceuticals.Type: GrantFiled: December 23, 1982Date of Patent: October 9, 1984Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4450173Abstract: A short-acting .beta.-blocking compound of the formula ##STR1## wherein Ar may be substituted or unsubstituted aromatic, Y may be a straight or branched carbon chain or aralkyl, R may be lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, and x is an integer from 1 to about 3; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 21, 1982Date of Patent: May 22, 1984Assignee: American Hospital Supply CorporationInventors: Paul W. Erhardt, Robert J. Borgman
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Patent number: 4443626Abstract: Novel 2,3-dihydro-indene derivatives having remarkable anti-inflammatory effects and represented by the following formula ##STR1## wherein R.sup.1 and R.sup.2 are each a hydrogen atom, halogen atom, nitro group, lower alkyl group or lower alkyloxy group with the proviso that R.sup.1 and R.sup.2 do not take a hydrogen atom at the same time, and n is an integer of 2-4.Type: GrantFiled: June 7, 1982Date of Patent: April 17, 1984Assignee: Hisamitsu Pharmaceutical Co., Inc.Inventors: Kanji Noda, Akira Nakagawa, Kenji Yamagata, Yoichi Nakashima, Masayoshi Tsuji, Tetsuo Aoki, Hiroyuki Ide
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Patent number: 4423064Abstract: 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: GrantFiled: June 29, 1981Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4421929Abstract: Novel tetracarboxylic acids are described of the formula ##STR1## wherein Ar, R.sub.1 and R.sub.2 are named substituents, and both n's are zeros or ones.Type: GrantFiled: December 2, 1981Date of Patent: December 20, 1983Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4415744Abstract: 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: GrantFiled: October 21, 1981Date of Patent: November 15, 1983Assignee: Monsanto CompanyInventors: Ignatius Schumacher, Kang-Bo Wang
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Patent number: 4407823Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein n is an integer of 2 to 5; ##STR2## R.sub.1 is hydrogen, halogen, trifluoromethyl, nitro or amino; R.sub.2 and R.sub.3 each independently is hydrogen or lower alkyl; or together form an ethylene group;X.sub.1 represents two hydrogen atoms or an oxo group; andY.sub.1 is cyano, hydroxyamidocarbonyl, carbamoyl, 5-tetrazolyl or carboxyl;and for derivatives wherein Y is carboxyl, salts thereof with physiologically compatible bases, esters thereof from physiologically acceptable alcohols and amides thereof from physiologically acceptable amines have valuable pharmacological activity, e.g., as antiinflammatory agents.Type: GrantFiled: November 5, 1979Date of Patent: October 4, 1983Assignee: Schering AktiengesellschaftInventors: Gerald Kirsch, Joachim-Friedrich Kapp, Clemens Rufer
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Patent number: 4401828Abstract: This process relates to the oxidation of phenoxytoluenes to phenoxybenzoic acids utilizing a hydrogen peroxide activated, bromide promoted cobalt catalyst which can be performed at atmospheric pressure and at moderate temperatures. These phenoxybenzoic acids can then be esterified and selectively nitrated to give the corresponding 2-nitro-5-substituted)phenoxybenzoic acid esters. Alternatively the acids can be nitrated and then esterified.Type: GrantFiled: September 10, 1979Date of Patent: August 30, 1983Assignee: Rohm and Haas CompanyInventor: Charles M. Tanger
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Patent number: 4398035Abstract: 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: October 3, 1980Date of Patent: August 9, 1983Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4394305Abstract: Compounds which are carboxylic acids, or their salt, ester or amide derivatives, having an oxyalkylene amine oxide substituent at the alpha-carbon atom are disclosed. The compounds are useful as detergent surfactants which provide outstanding cleaning, particularly of oily soils, under cold water laundering conditions. Detergent compositions containing the compounds also preferably contain other surfactants, builders, and detergent adjunct materials.Type: GrantFiled: March 17, 1981Date of Patent: July 19, 1983Assignee: The Procter & Gamble CompanyInventor: Eugene P. Gosselink
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Patent number: 4390702Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.Type: GrantFiled: December 29, 1980Date of Patent: June 28, 1983Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek