Benzene Ring Containing Patents (Class 564/265)
  • Patent number: 5527828
    Abstract: The invention is the use of nitronyl substituted hindered phenols as antioxidants in therapeutic applications. In the preferred embodiment the compositions have the general formula: ##STR1## Wherein R1 is hydrogen, an alkyl or an aryl and R2 is an alkyl or an aryl; R.sub.3 is an alkyl; and R.sub.4 is an alkyl. Further, the invention relates to novel compositions useful as antioxidants. The novel compounds include: 2,6-di-tert-butyl-4-(N-tert-octyl) nitronyl phenol (DBONP); 2,6-dimethyl-4-(N-tert-octyl) nitronyl phenol (DMONP); N-tert-octylC-phenyl nitrone (OPN).
    Type: Grant
    Filed: April 10, 1995
    Date of Patent: June 18, 1996
    Assignee: Oklahoma Medical Research Foundation
    Inventors: Edward G. Janzen, Allan L. Wilcox, Randall D. Hinton
  • Patent number: 5498793
    Abstract: Process for the production of oximes which comprises ammoximation of a carbonylic compound selected from acetophenone and cyclododecanone with H.sub.2 O.sub.2 and NH.sub.3 in the presence of a catalyst based on silicon, titanium and oxygen and a cocatalyst consisting of amorphous silica.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: March 12, 1996
    Assignee: Enichem S.p.A.
    Inventors: Maria A. Mantegazza, Guido Petrini
  • Patent number: 5466869
    Abstract: A catalytic process for preparing 4-hydroxyacetophenone oxime by reacting 4-hydroxyacetophenone with NH.sub.3 and H.sub.2 O.sub.2 in the liquid phase, in the presence of a catalyst substantially consisting of a titanium-containing molecular sieve such as a highly crystalline substance, containing SiO.sub.2 and having a zeolitic structure.
    Type: Grant
    Filed: October 31, 1994
    Date of Patent: November 14, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Kenneth G. Davenport, Roger A. Sheldon, Joel Le Bars, Werner H. Mueller
  • Patent number: 5462963
    Abstract: The present invention involves photoprotective compositions which are useful for topical application to prevent damage to skin caused by acute or chronic exposure to ultraviolet light comprising chelating agents having the structure: ##STR1## wherein each --R.sup.1 is independently selected from the group consisting of alkyl, aryl, heteroaryl and heterocycle, or the --R.sup.1 's are covalently bonded together to form a cyclic alkyl or heterocyclic ring; --R.sup.2 and --R.sup.3 are --OR.sup.4, in which case there is no bond or a polar bond between --R.sup.2 and the nitrogen covalently bonded to --R.sup.3, each --R.sup.4 being independently selected from the group consisting of hydrogen, alkyl and aryl, except that both --R.sup.4 's are not methyl when both --R.sup.1 's are furyl; or --R.sup.2 is --O-- and is covalently bonded to the nitrogen which is covalently bonded to --R.sup.3, and --R.sup.3 is --O-- (there being a + charge on the nitrogen to which it is bonded) or nil;wherein the .alpha.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: October 31, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Rodney D. Bush, Donald L. Bissett
  • Patent number: 5455272
    Abstract: The invention is the use of nitronyl substituted hindered phenols as antioxidants in therapeutic applications. In the preferred embodiment the compositions have the general formula: ##STR1## Wherein R1 is hydrogen, an alkyl or an aryl and R2 is an alkyl or an aryl; R.sub.3 is an alkyl; and R.sub.4 is an alkyl. Further, the invention relates to novel compositions useful as antioxidants. The novel compounds include: 2,6-di-tert-butyl-4-(N-tert-octyl)nitronyl phenol (DBONP); 2,6-dimethyl-4-(N-tert-octyl)nitronyl phenol (DMONP); N-tert-octyl-C-phenyl nitrone (OPN).
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: October 3, 1995
    Assignee: Oklahoma Medical Research Foundation
    Inventors: Edward G. Janzen, Allan L. Wilcox
  • Patent number: 5407961
    Abstract: The present invention is concerned with antiretroviral (e.g. anti HIV-1) compounds having the formula ##STR1## Pharmaceutical compositions containing said compounds of formula (I-a) or (I-b), and processes of preparing said compounds and compositions.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: April 18, 1995
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Frans M. A. Van den Keybus, Karin J. M. M. Nuyens, Paul A. J. Janssen
  • Patent number: 5374365
    Abstract: A polyphenol compound wherein the aromatic rings are linked by direct bonds or by a divalent link in the ortho position relative to the --OH group and the end aromatic rings contain either oximino substituents or substituted alkylaminomethyl substituents in the ortho position. The compound can be coated onto a metal surface to give improved corrosion resistance. The metal surface can be zinc-coated steel or zinc phosphated steel. The polyphenol compound can be the only coating material or can be incorporated into a surface coating composition such as a paint.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: December 20, 1994
    Assignee: Zeneca limited
    Inventor: John R. Lawson
  • Patent number: 5344980
    Abstract: Novel 4-substituted acetophenone anils and methods for preparing 1,3,5-tris(4'-hydroxyphenyl)benzenes from 4-substituted acetophenones such as 4-hydroxyacetophenones or, from substituted 4-hydroxyacetophenone-anils such as 4-hydroxyacetophenone-anil by reacting the 4-substituted acetophenone or corresponding anil with an aniline derivative.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: September 6, 1994
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, William Basinger
  • Patent number: 5326784
    Abstract: New cycloalkylalkylamines which are sigma-receptor ligands of formule (I) ##STR1## in which: R.sub.1 is H or lower alkyl; X and Y are H, OH, lower alkyl, lower alkoxy, halogen or nitrile; V.sub.1 and V.sub.2 together form a double bond attached to an oxygen atom or to a hydroxyimino radical, or are linked as an ethylenedioxy chain; A represents a valency bond, an oxygen atom, a methylene or an ethylene group; m is equal to 0, 1 or 2; n has the value of an integer from 1 to 5. Psychotropic drug which is also useful in gastroenterology.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: July 5, 1994
    Assignee: Institut de Recherche Jouveinal
    Inventors: Jean-Louis Junien, Alain Calvet, Henri Jacobelli, Francois Roman
  • Patent number: 5312987
    Abstract: Two-step process in the liquid phase for producing oximes at 60.degree.-100.degree. C. and 1.5-5 bars, which comprises:(a) in a primary step, ammoximating a carbonylic compound with H.sub.2 O.sub.2 and NH.sub.3 in the presence of a silicon, titanium and oxygen based catalyst;(b) oximating the residual carbonylic compound with a solution of hydroxylamine, obtained in its turn by oxidizing ammonia with H.sub.2 O.sub.2, having a concentration comprised within the range of from 0.01 to 3%, preferably of from 0.5 to 2% by weight, in such a way as to have a molar ratio of hydroxylamine to the carbonylic compound comprised within the range of from 0.9 to 3, preferably of from 1 to 2.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: May 17, 1994
    Assignee: Enichem Anic S.r.l.
    Inventors: Maria A. Mantegazza, Guido Petrini, Alberto Cesana
  • Patent number: 5266726
    Abstract: Sterically hindered oximes provide polyolefin compositions, including those also containing a phenolic antioxidant, with improved resistance to discoloration during processing at elevated temperatures.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: November 30, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Paul A. Odorisio
  • Patent number: 5227525
    Abstract: A multistep process for the liquid phase ammoximation of carbonyl compounds with H.sub.2 O.sub.2 and NH.sub.3, at 60.degree.-100.degree. C., at 1.5-5 bar and in the presence of a catalyst based on silicon, titanium and oxygen, characterized in that:a) in one or more primary steps, the H.sub.2 O.sub.2 : carbonyl compound molar ratio ranges from 0.9 to 1.15 by mols and the carbonyl component conversion is carried out up to at least 95%;b) in a last (exhaustion) step the H.sub.2 O.sub.2 : carbonyl compound ratio is in a higher range, i.e. from 1.5 to 3.0 by mols.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: July 13, 1993
    Assignee: Enichem Anic s.r.l.
    Inventors: Sergio Tonti, Paolo Roffia, Vittorio Gervasutti
  • Patent number: 5219481
    Abstract: A tetraoximino derivative of a bisphenol, for example the 3,5,3.sup.1,5.sup.1 -tetraoximino methyl derivative of 2,2-bis(4-hydroxyphenyl) propane, can be coated onto a metal surface to give improved corrosion resistance. The metal surface can be zinc coated steel or zinc phosphated steel. The tetraoximino derivative can be the only coating material or can be incorporated into a surface coating composition such as paint.
    Type: Grant
    Filed: April 14, 1992
    Date of Patent: June 15, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: John R. Lawson
  • Patent number: 5210216
    Abstract: Calixarene and oxacalixarene derivatives of the formula IV: ##STR1## wherein m'+m"=0-8n=0-8m'.gtoreq.1/2(m'+m")3.ltoreq.m'+m"+n.ltoreq.8if n=0, m'+m".gtoreq.4R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group;R.sup.15 is H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;X is selected from ##STR2## wherein R.sup.7 and R.sup.8 which may be the same or different are H or hydrocarbyl (including a cycloaliphatic ring formed by R.sup.7 and R.sup.8 together), aryl, hydrocarbylaryl or a substituted derivative thereof; R.sup.9 is --OH, --NH.sub.2, --NHC(O)NH.sub.2 or --NHAr, wherein Ar is aryl or a substituted derivative thereof,n' is 0 or 1.Use of the compounds for sequestration of metals is also described.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: May 11, 1993
    Assignee: Loctite (Ireland) Limited
    Inventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Ciaran McArdle, Michael A. McKervey
  • Patent number: 5190956
    Abstract: Compounds useful as antiviral agents against DNA containing viruses, such as herpes group viruses, are disclosed. The compounds are selected from the group consisting of: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.00 are disclosed. Also disclosed are methods of treating a viral infection using compounds represented by Formula 1.00The compounds of Formula 1.00 are also useful as intermediates to compounds of: ##STR2## Compounds of Formula 1.0 are useful as antiviral agents against the same viruses that the compounds of Formula 1.00 are useful against.
    Type: Grant
    Filed: September 7, 1990
    Date of Patent: March 2, 1993
    Assignee: Schering Corporation
    Inventors: Adriano Afonso, Jay Weinstein, Margaret J. Gentles
  • Patent number: 5177259
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 27, 1991
    Date of Patent: January 5, 1993
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5167696
    Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: December 1, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
  • Patent number: 5141937
    Abstract: Pharmaceutical products containing a 7-diphenylmethylenebicycloheptane or 7-diphenylmethylenebicycloheptene derivative of the formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the stated meanings, or a physiologically tolerated acid addition salt of these compounds, and the use thereof as hypolipidemics are described. In addition, new 7-diphenylmethylenebicycloheptane and -heptene derivatives of the formula Ia ##STR2## in which A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the stated meanings, and the physiologically tolerated acid addition salts thereof, as well as processes for the preparation thereof, are described.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: August 25, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Siegel, Ernold Granzer
  • Patent number: 5142095
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5130486
    Abstract: Isomerization of an unsymmetrical ketoxime ether is effected using at least one Lewis acid selected from titanium chloride, titanium bromide, aluminum chloride, aluminum bromide, boron chloride, and boron bromide as isomerizing agents. Examples of the Lewis acid are titanium tetrachloride, titanium trichloride, aluminum trichloride, aluminum tribromide, boron trichloride, and boron tribromide. The ketoxime ether is preferably an anti-isomer or a syn-isomer of a compound represented by the formula (I) or a mixture of the anti-isomer and the syn-isomer: ##STR1## wherein R.sub.1 represents an aryl group, an aralkyl group or an alkyl group and R.sub.2 and R.sub.3 each represents an aralkyl group or an alkyl group, with a proviso that R.sub.1 and R.sub.2 are not identical.
    Type: Grant
    Filed: December 27, 1990
    Date of Patent: July 14, 1992
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Naoto Konyo, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 5110989
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from alkyl, alkenyl and alkynyl;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof, and an alkylene group which bridges two adjacent carbon atoms of the benzene ring;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.
    Type: Grant
    Filed: July 17, 1990
    Date of Patent: May 5, 1992
    Assignee: ICI Australia Limited
    Inventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Linsay E. Cross
  • Patent number: 5108489
    Abstract: Herbicidal disubstituted naphthalenes of the formula ##STR1## in which A represents optionally branched alkanediyl,R represents hydrogen or in each case optionally substituted alkyl or phenyl,R.sup.1 represents hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 represents hydrogen or halogen,R.sup.3 represents halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,R.sup.4 represents hydrogen or halogen,X represents nitrogen or the group C--R.sup.5, whereR.sup.5 represents hydrogen or halogen,Y represents oxygen or sulphur, andZ represents oxygen, the group N--(O).sub.n --R.sup.
    Type: Grant
    Filed: July 24, 1991
    Date of Patent: April 28, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5097058
    Abstract: New process for the synthesis of the .alpha.-(1-m.ethylethyl)-3,4-dimethoxyacetonitrile of formula (I): ##STR1## which is known as an intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the isobutyryl-3,4-dimethoxybenzene of formula (II): ##STR2## which, by means of the Darzens condensation, gives an epoxyester which, by alkaline hydrolysis and subsequent decarboxylation, gives the .alpha.-(1-methylethyl)-3,4-dimethoxybenzeneacetaldehyde. This product is reacted with hydroxylamine to obtain the corresponding oxime that, by dehydration, gives the nitrile of formula I.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: March 17, 1992
    Assignee: Alfa Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • Patent number: 5095017
    Abstract: 1,2-dihydropyrido[3,4-b]pyrazines are provided which possess antimitotic activity. The compounds have the structure: ##STR1## wherein R is a lower alkyl group and OR.sub.1 is a member selected from the group consisting of aryl-alkyl ethers having from seven to about 20 carbon atoms, alkyl carbamates having from one to about 12 carbon atoms, the alkyl portion of which may be substituted with a halogen atom, e.g., chlorine, fluorine, bromine or iodine; aryl-alkyl carbamates having from about seven to about 20 carbon atoms, aryl carbamates having from about six to about 20 carbon atoms, aryl-alkyl esters having from about 7 to about 20 carbon atoms, aryl esters having from about six to about 20 carbon atoms, alkylthiocarbamates having from about one to about 12 carbon atoms, aryl-alkylthiocarbamates having from about seven to about 20 carbon atoms, and arylthiocarbamates having from about six to about 20 carbon atoms.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: March 10, 1992
    Assignee: Southern Research Institute
    Inventor: Carroll G. Temple, Jr.
  • Patent number: 5089528
    Abstract: Oxime ether derivatives of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl, X is S, SO or SO.sub.2, R.sup.3 is hydrogen, cycloalkyl, phenyl, naphthyl, quinolinyl or phenanthrenyl, these radicals being unsubstituted or substituted, Y is alkylene, alkenylene or alkynylene, and m is 0 or 1.
    Type: Grant
    Filed: November 15, 1989
    Date of Patent: February 18, 1992
    Assignee: Basf Aktiengesellschaft
    Inventors: Horst Wingert, Siegbert Brand, Bernd Wenderoth, Franz Schuetz, Hubert Sauter, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5089635
    Abstract: 13-alkyl-11.beta.-phenyl-gonanes of general formula I ##STR1## wherein A and B together stand for an oxygen atom, a CH.sub.2 group or a second bond between carbon atoms 9 and 10,X is an oxygen atom or the hydroxyimino grouping N.about.OH,R.sub.1 is a straight-chained or branched, saturated or unsaturated alkyl radical with up to 8 carbon atoms, which contains the grouping ##STR2## with X as described above, R.sub.2 is a methyl or ethyl radical in the .alpha. or .beta. position,R.sub.9, R.sub.10, R.sub.11 and R.sub.12 each stand for a hydrogen atom, a hydroxy, alkyl, alkoxy or acyloxy group with 1 to 4 carbon atoms respectively or a halogen atom and R.sub.3 and R.sub.4 have a variety of meanings, have antigestagenic and antiglucocorticoid effects.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: February 18, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Gunter Neef, Sybille Beier, Walter Elger, David Henderson, Eckard Otto, Ralph Rohde
  • Patent number: 5041666
    Abstract: A method is provided for the production of 3,3', 4,4'-tetraaminobiphenyl (TAB) from biphenyl comprising the following steps:1) acetylating the biphenyl in the presence of an appropriate Friedel-Crafts catalyst to obtain 4,4'-diacetylbiphenyl (DAcB);2) oximating the DAcB to form DAcB dioxime;3) subjecting the dioxime to a double Beckmann rearrangement to obtain N,N-diacetylbenzidine (DiAcBz);4) nitrating the DiAcBz to obtain 3,3'-dinitro-N,N-diacetylbenzidine (DNAcBz)5) removing the acetyl groups of the DNAcBz by basic hydrolysis to form 3,3'-dinitrobenzidine (DNB); and6) reducing the nitrate groups of the DNB to form TAB.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: August 20, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Bennett C. Ward, Wilson B. Ray, Charles B. Hilton, Anthony J. East, Kenneth G. Davenport
  • Patent number: 5039672
    Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications. Exemplary compounds include compounds of the formula ##STR1## wherein Y is ##STR2## X is --O-- or ##STR3## R.sub.1 and R.sub.2 are each independently H, alkyl C.sub.1 -C.sub.6,aryl or arylalkyl (C.sub.1 -C.sub.6);W.sub.1 and W.sub.2 are each independently hydrogen, halogen or nitro; andthe pharmaceutically acceptable base addition salts thereof.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: August 13, 1991
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Eric R. Larson
  • Patent number: 5030755
    Abstract: Disclosed are a process for producing a substituted phenoxyacetaldehyde oxime of the formula: ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises allowing a substituted phenoxyacetaldehyde dialkylacetal of the formula: ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification) to react with hydroxylamine; a process for producing a substituted phenoxyethylamine of the formula: ##STR3## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises reducing a substituted phenoxyacetaldehyde oxime of the formula (II) with hydrogen in the presence of a Raney-nickel catalyst; and a substituted phenoxyacetaldehyde oxime of the formula: ##STR4## (wherein R.sup.1, R.sup.2 and R.sup.6 are as defned in the specification).
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: July 9, 1991
    Assignees: Ube Industries Ltd., Sankyo Co., Ltd.
    Inventors: Kikuo Ataka, Koji Imaoka, Kiyotaka Yoshii, Kenji Hirotsu
  • Patent number: 5017618
    Abstract: Compounds having the formula ##STR1## and their pharmaceutically acceptable acid addition salts, wherein --X-- is --O--, --CH.sub.2 -- or --; .dbd.Y is .dbd.O or a derivatized keto group which is hydrolyzable or enzymatically convertible to a keto group; R is alkyl having from 1 to 12 carbon atoms or aralkyl having from 7 to 20 carbon atoms; and Ar is the 3-aromatic or heterocyclic residue of a 1-alkylamino-2-propanol having an aromatic or heterocyclic substituent at the 3-position and having .beta.-adrenergic blocking properties; are useful as .beta.-adrenergic blocking agents and are of particular interest in the treatment of glaucoma or for lowering intraocular pressure.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: May 21, 1991
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4990665
    Abstract: Diaryinitrones are provided which are useful for near UV photolithography.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: February 5, 1991
    Assignee: MicroSi, Inc.
    Inventors: Bruce F. Griffing, Paul R. West
  • Patent number: 4990494
    Abstract: Described are 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes defined according to the generic structure: ##STR1## wherein R.sub.1 is selected from the group consisting of: (i) cyanide having the structure: ##STR2## (ii) hydroxylamino methyl having the structure: ##STR3## and wherein R.sub.2 is C.sub.1 -C.sub.5 lower alkyl, uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations. Also described are processes for preparing such 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes by means of reacting an alkyl benzyl halide with isopropyl cyanide in the presence of a basic catalyst such as sodamide.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: February 5, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Eleanor Fox
  • Patent number: 4985402
    Abstract: Described are 2-methyl-1-nitrilo- or 2-methyl-1-hydroxylamino-3-(methoxyphenyl) propanes defined according to the generic structure: ##STR1## wherein R.sub.1 is selected from the group consisting of: (i) cyanide having the structure: ##STR2## (ii) hydroxylaminomethyl having the structure: uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations. Also described are processes for preparing such 2-methyl-1-nitrillo- or 2-methyl-1-hydroxylamino-3-(methoxyphenyl) propanes by means of reacting a methoxy benzyl halide with ethyl cyanide in the presence of a basic catalyst such as sodamide.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: January 15, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, De Virgilio John J.
  • Patent number: 4978788
    Abstract: A composition for use in extracting copper values from aqeous solutions of metal salts which comprises one more o-hydroxyaryloximes containing at least 5 aliphatic or alicyclic carbon atoms which are strong metal extractants which, in 0.2 molar solution in an aliphatic hydrocarbon solution loaded with 50% of the theoreticl uptake of copper, will be in equilibrium with 0.1 molar solution of copper as copper perchlorate at a pH less than 1; and one or more branched chain aliphatic or aromatic-aliphatic alcohols containing 14 to 30 carbon atoms or aliphatic or aliphatic-aromatic esters containing 10 to 30 carbon atoms, wherein the ratio of the number of methyl carbon atoms to the number of non-methyl carbon atoms is higher than 1:5, and which is selected from the group consisting of highly branched isohexadecyl alcohol, highly branched isooctadecyl alcohol and a diester of 2,2,4-trimethyl-1,3-pentanediol; and wherein the weight ratio of A to B is in the range 10:1 to 1:3.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: December 18, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Raymond F. Dalton, John L. Leng
  • Patent number: 4968842
    Abstract: The invention concerns a catalytic process for the manufacture of oximes by ammoximation of the corresponding carbonyl compounds, characterized in that the catalyst is a solid composition consisting of silicon, titanium and oxygen, chemically combined with each other, and in that the titanium amount, expressed as TiO.sub.2, ranges from 1 to 95% by weight, the XR diffractogam of said composition being a smooth-trend line (halo), typical of the amorphous solids.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: November 6, 1990
    Assignee: Montedipe, S.p.A.
    Inventors: Mario Padovan, Fausto Genoni, Giuseppe Leofanti, Guido Petrini, Paolo Roffia, Alberto Cesana
  • Patent number: 4959503
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: September 25, 1990
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 4946865
    Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: August 7, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Shigeko Nakamura
  • Patent number: 4929756
    Abstract: A process for preparing an oxime, which comprises reacting a ketone or an aldehyde with nitrogen monoxide and hydrogen in the presence of a platinum group metal catalyst to form the corresponding oxime.
    Type: Grant
    Filed: June 1, 1989
    Date of Patent: May 29, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventor: Kiyoji Kuma
  • Patent number: 4922017
    Abstract: A process for preparing an aromatic aldoxime, such as benzaldehyde oxime, by reacting the corresponding, .alpha.,.alpha.-dihalide, such as benzal chloride, with a hydroxylamine salt in the presence of an excess of an aqueous base sufficient to maintain the product oxime in solution. Organic impurities may be phase separated from the reaction mixture. Thereafter, the aqueous solution containing product oxime is neutralized to separate an oxime phase, which may be recovered by decanting or solvent extraction.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: May 1, 1990
    Assignee: Allied-Signal Inc.
    Inventor: Chempolil T. Mathew
  • Patent number: 4906768
    Abstract: A process for producing an oxime derivative, which comprises protecting the hydroxyimino group of an oxime compound with a protecting agent, subjecting the protected oxime compound to a given reaction, and thereafter deprotecting the reaction product, wherein a 2-alkenylating agent is used as the protecting agent.
    Type: Grant
    Filed: February 11, 1988
    Date of Patent: March 6, 1990
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshiro Yamada, Jiro Tsuji, Kuniaki Goto
  • Patent number: 4894478
    Abstract: The invention relates to a process of producing ketoximes, characterized in that a secondary alcohol, corresponding to the desired ketoxime, is partially oxidated in the liquid phase with O.sub.2, an oxidated mixture being thereby formed, which contains an excess of unreacted alcohol, the ketone corresponding to said alcohol, and H.sub.2 O.sub.2, and that said oxidated mixture is directly reacted with NH.sub.3 in the liquid phase (without isolating the alcohol, the ketone and H.sub.2 O.sub.2) in the presence of an ammoximation catalyst.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: January 16, 1990
    Assignee: Montedipe S.p.A.
    Inventors: Paolo Roffia, Giuseppe Paparatto, Alberto Cesana, Giorgio Tauszik
  • Patent number: 4855499
    Abstract: A novel process for the prevention of the formation of chlorinated by-products during the Beckmann rearrangement of 4-hydroxyacetophenone oxime to APAP by the addition of an inorganic iodide such as potassium iodide to the Beckmann rearrangement reactor is disclosed.
    Type: Grant
    Filed: November 6, 1987
    Date of Patent: August 8, 1989
    Assignee: Hoechst Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4845129
    Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: July 4, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
  • Patent number: 4816487
    Abstract: New 1-(2-hydroxylaryl)-alkane-1-on-oximes, procedure for their preparation, and their applicability to pharmaceutical preparations. One purpose is to develop 1-(2-hydroxyaryl)-alkane-1-on-oximes with desirable pharmacological properties. The new compounds of Formula I ##STR1## are characterised by pharmacologically valuable properties, in particular by anti-asthmatic, anti-anaphylactic, antiphlogistic, antihypertensive, spasmolytic, antirheumatic, and antithrombotic, potentials and are applicable in human and veterinary medicine to therapy of asthma bronchiale and other allergic diseases, various kinds of inflammatory and rheumatic diseases, and thrombosis.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: March 28, 1989
    Assignee: Humboldt-Universitaet zu Berlin
    Inventors: Tankred Schewe, Hartmut Kuehn, Joerg Beger, Grupe, Renate, Rapoport, Samuel M., Hans-Joachim Binte, deceased, Juergen Slapke
  • Patent number: 4808750
    Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: February 28, 1989
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, B. Clifford Gerwick, III
  • Patent number: 4801735
    Abstract: Compounds are described of the following formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-12 alkyl or C.sub.2-12 alkenyl, at least one of R.sup.1 and R.sup.2 being C.sub.1-12 alkyl or C.sub.2-12 alkenyl; X.sup.1 and X.sup.2 are each hydrogen or a protecting group; and Y is(a) --(CH.dbd.CH).sub.n Z in which n is 1, 2 or 3 and Z is --CHO, --CH.sub.2 OH, --COR.sup.3, --(CH.sub.2).sub.m --COR.sup.3 or --(CH.sub.2).sub.p CH.dbd.CH(CH.sub.2).sub.q --COR.sup.3 in which m is an integer of 1 to 12, p is an integer of 1 to 4, q is an integer of 1 to 10 and R.sup.3 is (i) --OH or (ii) --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are each hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholino, pyrrolidinyl or piperidino ring,(b) --CH.dbd.NR.sup.6 in which R.sup.6 is (i) --OH, (ii) C.sub.1-12 alkyl optionally substituted by --OH, --COOH or --NR.sup.7 R.sup.8 where R.sup.7 and R.sup.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: January 31, 1989
    Assignee: Lilly Industries Limited
    Inventors: Mark A. W. Finch, John R. Harris
  • Patent number: 4794198
    Abstract: The invention concerns a catalytic process for the manufacture of oximes by reaction, in the liquid phase, of the corresponding carbonylic compounds with NH.sub.3 and H.sub.2 O.sub.2, in which process the catalyst is substantially consisting of a crystalline material with a zeolitic structure containing silicon and titanium, subjected, before use, to an activating treatment with H.sub.2 O.sub.2.
    Type: Grant
    Filed: June 8, 1987
    Date of Patent: December 27, 1988
    Assignee: Montedipe S.p.A.
    Inventors: Paolo Roffia, Mario Padovan, Giuseppe Leofanti, Maria A. Mantegazza, Giordano De Alberti, Giorgio R. Tauszik
  • Patent number: 4792616
    Abstract: Novel diaryl ethers of the formula ##STR1## wherein A is CR.sup.3 or N and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, n and R.sup.6 are as defined hereinafter, processes for their preparation, herbicidal compositions which contain these compounds as the active ingredient as well as the use of these compounds or compositions for the control of weeds is disclosed.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: December 20, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Paul Winternitz, Ren/e/ Zurfl/u/ h
  • Patent number: 4790870
    Abstract: This invention relates to aryloxy optionally oxo-substituted indane or tetralin derivatives having herbicidal activity and to the use of such compounds to control the growth of noxious plants, i.e., weeds.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: December 13, 1988
    Assignee: PPG Industries, Inc.
    Inventors: David A. Hunt, James A. Schwindeman
  • Patent number: 4788130
    Abstract: Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group].
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: November 29, 1988
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Yasuo Oshiro, Hiraki Ueda, Kazuyuki Nakagawa