Halogen Attached Directly To The Diazine Ring By Nonionic Bonding Patents (Class 544/334)
  • Patent number: 5723473
    Abstract: A fungicidal compound of formula (I): ##STR1## wherein A is hydrogen, halogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; and one of R.sup.1 and R.sup.2 is optionally substituted isoquinoline while the other is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halogen or cyano.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: March 3, 1998
    Assignee: Zeneca Limited
    Inventor: Brian Leslie Pilkington
  • Patent number: 5723611
    Abstract: A compound of formula (VIII): ##STR1## in which Alk is a (C.sub.1 -C.sub.4)alkyl group, R.cndot. is hydrogen or a protecting group cleavable by hydrolysis and R is hydrogen, a protecting group cleavable by reduction or a heterocycle of structure (IX): ##STR2## in which Hal is a halogen atom and X, Y and Z are each --CH.dbd. or one of them is a nitrogen atom and the others are --CH.dbd., and its salts, R.cndot. being other than hydrogen if R is hydrogen or a group of structure (IX).
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 3, 1998
    Assignee: Sanofi
    Inventors: Marco Baroni, Tiziano Croci, Marco Landi, Umberto Guzzi, Dino Nisato
  • Patent number: 5723612
    Abstract: Process for the preparation of pure 4,6-dichloropyrimidine by reaction of 4,6-dihydroxypyrimidine with an excess of phosphorus oxychloride at 20.degree. C. up to reflux temperature, in the presence of a trialkylamine as acid scavenger and catalyst.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: March 3, 1998
    Assignee: DSM Chemie Linz GmbH
    Inventors: Wolfgang Huber, Franz Thomas Schwarz, Ferdinand Heu
  • Patent number: 5719285
    Abstract: Polychloropyrimidines, in particular 4,6-dichloropyrimidine and 2,4,6-trichloropyrimidine, are obtained in a particularly advantageous manner from polyhydroxypyrimidines or tautomeric keto compounds thereof and excess phosphorus oxychloride in the presence of a tertiary amine if, in this reaction,a) 0.75 to 1.5 mol of phosphorus trichloride and 0.7 to 1.
    Type: Grant
    Filed: August 11, 1995
    Date of Patent: February 17, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Guido Steffan
  • Patent number: 5712393
    Abstract: The present invention provides a compound of formula (1) ##STR1## in which: R.sub.4 represents a hydrogen atom, a halogen atom or a nitro group;R.sub.6 represents a hydrogen atom or a straight or branched (C.sub.1 -C.sub.6) alkyl group;R.sub.7 represents a chlorine atom or a hydroxyl group; andZ represents: a phenyl group optionally substituted with one or more halogen atoms, straight or branched (C.sub.1 -C.sub.4)alkyl groups, straight or branched (C.sub.1 -C.sub.4)alkoxy groups, or trifluoromethyl, formyl, --CH.sub.2 OR, --CH.sub.2 OCOR, --CH.sub.2 CONRR', --CH.sub.2 ONCOR, --COOR, nitro, --NHR, --NRR' or --NHCOR groups, wherein R and R' are each, independently, a hydrogen atom or a (C.sub.1 -C.sub.7) alkyl group; a heterocyclic group optionally substituted as defined above for phenyl; or a cyclo(C.sub.5 -C.sub.8)alkyl group; additionally, when R.sub.
    Type: Grant
    Filed: November 24, 1995
    Date of Patent: January 27, 1998
    Assignee: Synthelabo
    Inventors: Jean Michel Altenburger, Gilbert Lassalle
  • Patent number: 5712418
    Abstract: The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting groupAA is an amino acid residue andX is H or a protecting group useful,and the first amino and peptide have a free amino group and a blocked carboxy end.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: January 27, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
  • Patent number: 5712394
    Abstract: Process for preparing 2,4,6-trichloropyrimidine, characterized in that, in a first reaction step, barbituric acid is reacted, optionally in the presence of a catalyst, with phosphorus oxychloride and subsequently, in a second reaction step, with phosphorus pentachloride or with reactants forming the latter, in particular phosphorus trichloride and chlorine.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: January 27, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Hansmann, Stefan Ehrenberg, Frank-Michael Stohr
  • Patent number: 5707995
    Abstract: Compounds of formula (I) in which X.sup.1 and X.sup.2 each represents oxygen; S(O).sub.n, n being 0, 1 or 2; or CO, CH.sub.2 or NR, R being hydrogen or alkyl; R.sup.1 and R.sup.10 are each hydrogen or halogen; R.sup.2 and R.sup.9 are each hydrogen, halogen, cyano, nitro, alkyl, halo-alkyl, alkoxy, alkylthio, amino, mono- or di-alkylamino, alkoxyalkyl, haloalkoxyalkyl or alkoxycarbonyl; R.sup.3 and R.sup.8 are each hydrogen, chlorine, alkyl, haloalkyl, haloalkenyl, halo-alkynyl, haloalkoxy, haloalkoxycarbenyl, haloalkylthio, haloalkoxyalkyl, haloalkylsulphinyl, or haloalkylsulphonyl, nitro or cyano; R.sup.4 and R.sup.7 are each hydrogen, halogen, alkyl or alkoxy; R.sup.5 is hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulphonyl or phenyl; and R.sup.6 is hydrogen or, when R.sup.5 is hydrogen, alkyl; provided that either each phenyl is unsubstituted or at least one of R.sup.3 and R.sup.8 is not hydrogen, have useful pesticidal activity.
    Type: Grant
    Filed: July 24, 1995
    Date of Patent: January 13, 1998
    Assignee: American Cyanamid Company
    Inventors: David Munro, Royston Davis, Janet Anne Day, Jacqueline Anne Wilkin, William W. Wood
  • Patent number: 5698694
    Abstract: A process for preparation of substituted phthalides, heterocyclic phthalides and derivatives thereof by reacting an aromatic carboxylic acid mono- or di-anion with a reactive derivative of a pyrimidine carboxylic acid.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: December 16, 1997
    Assignee: Sandoz Ltd.
    Inventors: Takeo Hokama, Ian S. Cloudsdale, Werner Langer, Hermann Schneider
  • Patent number: 5688795
    Abstract: The present invention relates to novel .alpha..sub.1 -adrenoceptor antagonists of Formula I: ##STR1## in which: p is 0 or 1;t is 0, 1 or 2;X is O, S or NR.sup.6 (in which R.sup.6 is hydro or (C.sub.1-6)alkyl);Y and Z are independently CH or N;R.sup.1 is hydro, hydroxy, halo, nitro, amino, cyano, (C.sub.1-4)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C.sub.1-6)alkyl, (C.sub.3-6)cycloalkyl, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl (C.sub.1-4)alkyl, heteroaryl (C.sub.1-4)alkyl, (C.sub.1-6)alkyloxy, (C.sub.3-6)cycloalkyloxy, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl (C.sub.1-4)alkyloxy or heteroaryl (C.sub.1-4)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano);R.sup.2 is hydro, hydroxy, halo, cyano, (C.sub.1-6)alkyl or (C.sub.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: November 18, 1997
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jurg Roland Pfister, David Ernest Clarke, Todd Richard Elworthy, David John Morgans, Jr., David Bruce Repke, Eric Brian Sjorgren, Helen Yen-hui Wu
  • Patent number: 5686608
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5681957
    Abstract: Unsubstituted or substituted 2-fluoro-pyrimidines can be prepared by reaction of the underlying 2-amino-pyrimidines with diazotization agents, mixtures of HF and H.sub.2 O containing 30-70% by weight of HF, based on the total of HF and H.sub.2 O, serving as reaction medium. The reaction medium can also contain diluents and/or inorganic salts, preferably fluorides.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: October 28, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Wolters, Guido Steffan, Alexander Klausener
  • Patent number: 5677453
    Abstract: 4,6-Dichloropyrimidines are obtained by the reaction of 4,6-dihydroxypyrimidines with excess phosphoryl chloride in a particularly advantageous manner when no base is added, during and/or after the reaction 0.75 to 1.5 mol of phosphorus trichloride and 0.7 to 1.3 mol of chlorine are added per equivalent of exchanged hydroxyl groups so that an excess of phosphorus trichloride with respect to chlorine is always present, and finally phosphorus trichloride and phosphoryl chloride are separated off. This process can be carried out in a particularly simple manner and also continuously.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: October 14, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Cramm, Volker Kass, Guido Steffan
  • Patent number: 5646309
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are employed as intermediates in the synthesis of aminochroman compounds useful in the treatment of CNS disorders.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 8, 1997
    Assignee: Astra Aktiebolag
    Inventors: Eva Maria Hammarberg, Lars George Johansson, Lars-Gunnar Larsson, Rolf Noreen, Lucy Anna Renyi, Svante Bertil Ross, Daniel Dungan Sohn, Bjorn Eric Svensson, Seth-Olov Thorberg
  • Patent number: 5604181
    Abstract: Herbicidal compounds of formula (I) and salts thereof, where A is --N.dbd. or --CH.dbd.; X is --OH, --OR.sup.10, --SH, --SR.sup.10, --SCN, NH.sub.2, --NHacyl, --CH.sub.2 OH, --CH.sub.2 OR.sup.9 or --CN; R.sup.1 and R.sup.2, which may be the same or different, each represent alkyl, alkoxy, haloalkyl, haloalkoxy, halo, alkylamino or dialkylamino; R.sup.3 is --CN, --COOR.sup.5, --CONR.sup.6 R.sup.7, --CSNH.sub.2, --CHO, --CH.dbd.Z, --CH(Oalkyl).sub.2, --CH.sub.2 OH, --CH.sub.2 OR.sup.9, --COSR.sup.4a, --CS.sub.2 R.sup.4a, or a substituted or unsubstituted 5- or 6-membered heterocyclic group linked via a ring carbon atom which is between two ring heteroatoms; R.sup.4 and R.sup.4a, which may be the same or different, are each H, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl or heteroaryl group; R.sup.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: February 18, 1997
    Assignee: Agrevo UK Limited
    Inventors: Thomas L. Hough, Peter S. Gates
  • Patent number: 5595994
    Abstract: The present invention relates to novel heteroarylpiperidines of formula (I): ##STR1## in which Hal is a halogen atom, Alk is a C.sub.1-4 alkyl group and one of X, Y and Z is a nitrogen atom while the others are .dbd.CH--, and their salts. These compounds are useful as 5-HT.sub.3 agonists.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 21, 1997
    Assignee: Sanofi
    Inventors: Marco Baroni, Tiziano Croci, Marco Landi, Umberto Guzzi, Dino Nisato
  • Patent number: 5591853
    Abstract: A 2-halo-pyrimidine-4-carboxylic acid of formula: ##STR1## wherein X is a halogen atom, for example, 2-chloro-pyrimidine-4-carboxylic acid. A 2-substituted-pyrimidine-4-carboxylic acid derivative of formula: ##STR2## wherein R.sub.1 is a halogen atom, NH.sub.2 --, HO-- or a C.sub.1 -C.sub.4 alkoxy group and R.sub.2 is a C.sub.1 -C.sub.4 alkoxy group or a halogen atom with the proviso that, if R.sub.1 is a HO-- group, R.sub.2 is not a halogen atom and with the proviso that, if R.sub.2 is a halo group, R.sub.1 is not an amino group. A 2-substituted-pyrimidine-4-carboxylic acid derivative of formula III wherein R.sub.1 is a HO-- group and R.sub.2 is an ethoxy group.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: January 7, 1997
    Assignee: Lonza Ltd.
    Inventors: Andreas Kiener, Rainer Gl ockler, Gerhard Stucky
  • Patent number: 5565474
    Abstract: The present invention relates to new 1-heteroarylazetidines and new 1-heteroarylpyrrolidines endowed with 5-HT.sub.3 agonist activity of formula (I): ##STR1## in which A is --CH=CH--; R is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, cyano, carboxamido, trifluoromethyl, a vinyl group, a formyl group, a carboxyl group in free, salt or esterified form, hydroxyl, hydroxymethyl, mercapto, amino, mono- or di-(C.sub.1-4 alkyl)amino, aminomethyl, mono- or di(C.sub.1-4 alkyl)aminomethyl, 1-piperido, 1-pyrrolidino, 1-piperazino or 4-(C.sub.1-4 alkyl)-1-piperazino, where R may replace any one of the hydrogen atoms of the heteroaryl nucleus;R.sub.1 is hydrogen or a methyl group;R.sub.2 and R.sub.3, which are identical or different, are hydrogen or C.sub.1-4 alkyl;n is 1 or 2; m is 0 or 1; and m+n.gtoreq.2;and addition salts with inorganic or organic acids of the compounds of formula (I).
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: October 15, 1996
    Assignee: SANOFI
    Inventors: Marco Baroni, Umberto Guzzi, Antonina Giudice, Marco Landi, Vivian Mazza
  • Patent number: 5559081
    Abstract: Herbicidal sulfonamides of the formula: ##STR1## and salts thereof, where: A represents a substituted or unsubstituted benzene ring, or a 5- or 6-membered substituted or unsubstituted heteroaromatic ring; Q is --O--, --S-- or a group --CXX'--; X and X', which may be the same or different, are each hydrogen, halogen, cyano, an optionally-substituted alkyl group, or a group --OR.sup.a, --SR.sup.a, or --COR.sup.b ; or one of X and X' represents hydroxy and the other is as defined above; or X and X' together represent .dbd.O or .dbd.S; R.sup.a is an optionally-substituted alkyl, aryl or acyl group; R.sup.b is an optionally-substituted alkyl or aryl group, or a group --OR.sup.c or --NR.sup.c R.sup.d ; R.sup.c and R.sup.d, which may be the same or different, are each hydrogen, or an optionally-substituted alkyl or aryl group; Y is nitrogen or a group CR.sup.9 ; R.sup.1 is an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, benzoheterocyclyl or amino group; R.sup.
    Type: Grant
    Filed: May 6, 1994
    Date of Patent: September 24, 1996
    Assignee: Agrevo UK Limited
    Inventors: Peter S. Gates, Graham P. Jones, David E. Saunders
  • Patent number: 5550236
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Rainer Wingen, Javier Manero
  • Patent number: 5536442
    Abstract: The invention relates to liquid crystal compounds having a terminal structure in accordance with formula 1, 2, 3 or 4:--A.sup.3 --OCF.sub.3 1--A.sup.2 --Q--CHF.sub.2 2--3,5-difluoro-1,4-phenylene-X.sup.1 3--3-fluoro-1,4-phenylene-X.sup.2 4wherein A.sup.2, A.sup.3, X.sup.1 and X.sup.2 and are defined herein. The invention further relates liquid crystal phases containing the above components as well as electrooptical displays containing same.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 16, 1996
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Hans A. Kurmeier, Eike Poetsch, Herbert Plach, Ulrich Finkenzeller, Ekkehard Bartmann, Joachim Krause, Bernhard Scheuble, Dieter Dorsch, Georg Weber
  • Patent number: 5536837
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like, R.sup.3 and R.sup.4 represent independently an alkyl group, alkoxy group, or the like, and X and Y represent independently a methyne group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: July 16, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihisa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5525724
    Abstract: A process for the preparation of chloropyrimidines of the formula ##STR1## in which the substituents may be alkyl, cycloalkyl, aryl or radicals containing heteroatoms, but in which at least one of the substituents R.sup.1 to R.sup.4 must be Cl, which involves:reacting a hydroxy-pyrimidine or its tautomeric keto form with phosphoryl chloride in the presence of an amine or amine hydrochloride;recovering phosphoryl chloride after the reaction by adding phosphorus pentachloride and distilling the phosphoryl chloride; andseparating the chloropyrimidine from the amine hydrochloride by addition of a solvent which will dissolve the chloropyrimidine but not the amine hydrochloride and removing the amine hydrochloride.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: June 11, 1996
    Assignee: Huels Aktiengesellschaft
    Inventor: Artur Hunds
  • Patent number: 5523404
    Abstract: A process for preparing 5-chloro-4-hydroxypyrimidines, 2-chloro enamines as intermediates in this process and their use The invention relates to a process for preparing compounds of the formula ##STR1## in which R.sup.1 is optionally substituted alkyl, cycloalkyl, aryl or benzyl, in which a chloroacetic ester is converted with ammonia or an ammonium salt into the corresponding chloro enamine and the latter is condensed in the presence of a base with formamide. The invention furthermore relates to 2-chloro enamines as intermediates in the process.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: June 4, 1996
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventor: Frank Zurmuhlen
  • Patent number: 5519139
    Abstract: There is disclosed a novel 4-aminopyrimidine derivative containing an optionally esterified carboxyl group at the 5-position which has potent fungicidal activity as well as insecticidal and miticidal activity. The compound is useful as agricultural fungicides, insecticides and miticides.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: May 21, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toshikazu Ohtsuka, Moriyasu Masui, Takami Takeda, Michio Masuko, Katsuaki Ohba
  • Patent number: 5502063
    Abstract: The present invention relates to novel heteroarylpiperidines of formula (I): ##STR1## in which Hal is a halogen atom, Alk is a C.sub.1 -C.sub.4 alkyl group and X, Y and Z are each --CH.dbd. and their salts, to a process for their preparation and to their use as drugs active as 5-HT.sub.3 agonists.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: March 26, 1996
    Assignee: Sanofi
    Inventors: Marco Baroni, Tiziano Croci, Marco Landi, Umberto Guzzi, Dino Nisato
  • Patent number: 5493024
    Abstract: 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds having an aryl moiety in the 4-position that is an optionally substituted pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moiety and aryl moieties in the 3-position and the N-position that are optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moieties, such as N-(4-chlorophenyl)-4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-p yridinyl)-1H-pyrazole-1-carboxamide, were prepared and found to possess insecticidal utility. 1,2-Diarylethanone compounds were converted to 1,2-diaryl-2-propen-1-one compounds by treatment with bis(dimethylamino)methane, the 1,2-diaryl-2-propen-1-one compounds were converted to 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds by treatment with hydrazine, and the 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds were converted to the insecticidal subject compounds by treatment with an aryl isocyanate.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: February 20, 1996
    Assignee: DowElanco
    Inventors: Kevin L. McLaren, Mark B. Hertlein, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
  • Patent number: 5480580
    Abstract: Optical active compounds which are chemically stable, are not colored, have a good optical stability, and which give a liquid crystal composition having a large spontaneous polarization when the compound is incorporated, are provided. The optical active compound have an asymmetric carbon atom fixed by a .delta.-valerolactone ring and the permanent dipole moment derived from the carboxylic group is fixed by the .delta.-valerolactone ring and two alkyl groups which can be regarded as a part of a measogen.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: January 2, 1996
    Assignee: Mitsubishi Rayon Company Ltd.
    Inventors: Keiichi Sakashita, Yoshitaka Kageyama, Tetsuya Ikemoto
  • Patent number: 5470975
    Abstract: Novel A-II receptor antagonists have the formula ##STR1## and its isomer ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined herein.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: November 28, 1995
    Assignee: E.R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5466692
    Abstract: This invention relates to substituted pyridopyrimidinones of general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently H, lower alkyl containing 1 to 6 carbon atoms, hydroxyalkyl containing 1 to 6 carbon atoms, formyl, carbonylalkyl containing 1 to 6 carbon atoms, carboxy, or carboxyalkyl containing 1 to 6 carbon atoms; R.sup.3 and R.sup.4 are independently H, lower alkyl containing 1 to 6 carbon atoms, hydroxy; R.sup.3a and R.sup.4a are H, and when taken together with R.sup.3 and R.sup.4 respectively comprise a carbonyl; with the proviso that at least one of the groups R1 and R.sup.2 must be hydroxyalkyl, formyl, carbonylalkyl containing 1 to 6 carbon atoms, carboxy, or carboxyalkyl containing 1 to 6 carbon atoms; or R.sup.3 and R.sup.4 must be hydroxy or taken together with R.sup.3a and R.sup.4a respectively must comprise a carbonyl; n is 0 to 3; Ar.sup.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: November 14, 1995
    Assignee: American Home Products Corporation
    Inventor: John W. Ellingboe
  • Patent number: 5444060
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like, R.sup.3 and R.sup.4 represent independently an alkyl group, alkoxy group, or the like, and X and Y represent independently a methyne group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: August 22, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihasa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5439910
    Abstract: Compounds having formula (I) ##STR1## wherein R.sup.1, R.sup.2 and A are defined as in the specification. The compounds are useful as fungicides.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: August 8, 1995
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, John M. Clough, Paul A. Worthington, Brian L. Pilkington, Ian R. Matthews
  • Patent number: 5411934
    Abstract: The present invention provides a novel alkanoic acid amide derivative of the formula, ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group or an alkoxyalkoxy group, R.sup.2 is a group of -SO.sub.2 R or a hydroxyl group, R.sup.5 is an alkyl group, R.sup.3 is an alkyl group, a cycloalkyl group, a cycloalkenyl group or a phenyl group, R.sup.4 is a hydrogen atom or an alkyl group, X and Y may be the same or different and are an alkoxy group, an alkylamino group or a dialkylamino group, and Z is a methine group or a nitrogen atom) and its salt, a process for preparing the same and a herbicidal composition containing the same as an effective ingredient.This compound kills annual and perennial weeds grown in paddy fields and upland fields at a small dose, and is safe to a useful crop plant.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: May 2, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
  • Patent number: 5410057
    Abstract: The present invention relates to new 1-heteroarylazetidines and new 1-heteroarylpyrrolidines endowed with 5-HT.sub.3 agonist activity of formula (IV): ##STR1## The substituents A, R', R.sub.1 and P, and the variables n and m, are as herein described.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 25, 1995
    Assignee: Sanofi
    Inventors: Marco Baroni, Umberto Guzzi, Antonina Giudice, Marco Landi, Vivian Mazza
  • Patent number: 5405960
    Abstract: Triarylborane derivatives corresponding to the formula (1) ##STR1## in which R either represents a group --CR.sub.1 R.sub.2 R.sub.3 where R.sub.1, R.sub.2 and R.sub.3 are each, independently of one another, a (C.sub.1 -C.sub.2)alkyl or aryl group, or represents a group --CH.sub.2 OR.sub.4 where R.sub.4 is a (C.sub.1 -C.sub.2)alkyl or benzyl group, or represents a group --Si(R.sub.5).sub.3 where R.sub.5 is a (C.sub.1 -C.sub.2)alkyl or aryl group, R being in the 1 or 2 position of the tetrazole ring, their preparation and their use as synthesis intermediates.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: April 11, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Guy Rossey, Michel Magnat
  • Patent number: 5401763
    Abstract: Arylacetic ester derivative-based compounds having the general formula (I): ##STR1##
    Type: Grant
    Filed: February 3, 1994
    Date of Patent: March 28, 1995
    Assignee: Ministero Dell `Universita` e Della Ricerca Scientifica e Technologica
    Inventors: Giovanni Camaggi, Lucio Filippini, Raul Riva, Isabella Venturini, Giampaolo Zanardi, Carlo Garavaglia, Ernesto Signorini, Mario Ferri
  • Patent number: 5399292
    Abstract: Fluoro-substituted phenyl-cyclohexylacetylenes have the formula: ##STR1## wherein R signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group can be replaced by oxygen and/or one or more hydrogen atoms can be replaced by fluorine atoms, with the proviso that two oxygen atoms are not directly adjacent;A.sup.1 represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;A.sup.2 signifies trans-1,4-cyclohexylene or 1,4-phenylene which is optionally substituted with fluorine;Z.sup.1 signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;Z.sup.2 signifies a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: March 21, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Martin Schadt
  • Patent number: 5391819
    Abstract: Disclosed herein is a process of making chiral 2-aryl-1,4-butanediamine derivatives useful as neurokinin-A antagonists of Formula 7 ##STR1##
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: February 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Paul E. Finke, Jeffrey J. Hale, Malcolm Maccoss, Sander G. Mills
  • Patent number: 5384407
    Abstract: A compound of the formula ##STR1## V, W, Y, and Z are each independently C--H, oxygen, nitrogen, or sulfur; T is C--H or nitrogen;n is 0 or 1;R.sup.4 is hydrogen or one, two or three substituents independently selected from C.sub.1 -C.sub.4 -alkyl, halo-substituted C.sub.1 -C.sub.4 -alkyl, hydroxy-substituted C.sub.1 -C.sub.4 -alkyl, halogen, hydroxy, C.sub.1 -C.sub.4 -alkoxy, mercapto, amino, mono-(C.sub.1 -C.sub.4 -alkyl)amino, di-(C.sub.1 -C.sub.4 -alkyl)amino, formamido, mono-(C.sub.1 -C.sub.4 -alkyl)amido, di-(C.sub.1 -C.sub.4 -alkyl)amido, cyano, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, carboxyl, aminomethyl, mono-(C.sub.1 -C.sub.4 -alkyl)aminomethyl, di-(C.sub.1 -C.sub.4 -alkyl)aminomethyl, wherein free hydroxy and amino groups may be protected.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: January 24, 1995
    Assignee: Warner-Lambert Company
    Inventors: Edgardo Laborde, Mel Schroeder
  • Patent number: 5380699
    Abstract: The present invention provides novel herbicidal pyridines characterized by having in the 3- or 5-position an aliphatic or aromatic 1-ketone.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: January 10, 1995
    Assignee: Rohm and Haas Company
    Inventors: Len F. Lee, Yuen-Lung L. Sing, Sai C. Wong
  • Patent number: 5371224
    Abstract: Process for preparing 2,5-dibromopyrimidine A process for preparing 2,5-dibromopyrimidine comprises reacting 5-bromo-2-chloropyrimidine with a solution of hydrogen bromide in a non-aqueous acid at a temperature of between 0.degree. and 120.degree. C.The process can be carried out at low cost and gives high yields.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: December 6, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Rainer Wingen
  • Patent number: 5364865
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## Y is a bond or lower alkylene; R.sub.2 and R.sub.3 are independently hydrogen, lower-alkyl or halogen;R.sub.4 is ##STR3## R.sub.5 is hydrogen, lower-alkyl or halogen; R.sub.6 is hydrogen, lower-alkyl or halogen;R.sub.7 is hydrogen or lower-alkyl;R.sub.8 is hydrogen, lower-alkyl, or trifluoromethyl;R.sub.9 is lower-alkyl;R.sub.10 is lower-alkyl, trifluoromethyl or difluoromethyl;or pharmaceutically acceptable acid addition salts thereof are useful as antiviral agents.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: November 15, 1994
    Assignee: Sterling Winthrop Inc.
    Inventor: Guy D. Diana
  • Patent number: 5354500
    Abstract: Use of optically active carboxylic esters of oxygen-containing heterocycles as doping substances in liquid crystal mixtures and liquid crystal mixtures containing them.Optically active 1,3-dioxolane-4-carboxylic esters and oxirane-2-carboxylic esters of the general formula (I)R(--A.sup.1).sub.j (--M.sup.1).sub.k (--A.sup.2).sub.l (--M.sup.2).sub.m (--A.sup.3).sub.n --X--Acin whichR.sup.1 is, for example, (C.sub.1 -C.sub.16)-alkyl or (C.sub.1 -C.sub.16)-alkoxy,A.sup.1, A.sup.2, A.sup.3 are, for example, phenyl or pyrimidine-2, 5-diyl,M.sup.1, M.sup.2 are, for example, CO--O, CH.sub.2 --CH.sub.2,j, l are 0, 1, 2,k, m are 0, 1,n is 0, 1, 2,X is O, S andAc is ##STR1## in which R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 for example, H or methyl, are particularly suitable doping substances for liquid crystalline mixtures, since they induce a high spontaneous polarization and effect a substantial decrease in the melting point.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: October 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hemmerling, Ingrid Muller, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 5352787
    Abstract: 5-Trifluoromethyl-uracil is obtained by chlorinating thymine under mild conditions, further chlorinating the resulting 2,4-dichloro-5-methyl-pyrimidine under drastic conditions to give 2,4-dichloro-5-trichloromethylpyrimidine, reacting the latter with a fluorinating agent to give 2,4-fluorinated and/or -chlorinated 5- trifluoromethylpyrimidines and subjecting these to hydrolysis. The novel chemical compounds 2,4-dichloro- 5-trichloromethylpyrimidine and 2,4-difluoro-5-trifluoromethylpyrimidine are obtained in the course of this process.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: October 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • Patent number: 5346902
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein Y is a specified small group or single atom and R.sup.1 and R.sup.2 are selected from a wide range of specified substituents.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: September 13, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine
  • Patent number: 5342837
    Abstract: Fungicidal compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heterocyclyloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted aryloxy, optionally substituted heterocyclyloxy, nitro halo cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.sup.3).sub.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: August 30, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Ian R. Matthews
  • Patent number: 5334333
    Abstract: The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices comprised of such electrooptical components, as well as novel processes of making the same.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: August 2, 1994
    Assignee: Elf Atochem North America, Inc.
    Inventor: Frederick J. Goetz
  • Patent number: 5326762
    Abstract: Amides of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently heteroaryl, X-substituted heteroaryl, X-substituted phenyl, N-substituted triazinyl or N-substituted imidazolyl;and in addition, one of R.sub.1 and R.sub.2 can be as defined above and the other can be phenyl;R.sub.3 is an alkyl chain of 2 to 25 carbon atoms, saturated or unsaturated; an alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; an alkyl chain as defined interrupted by one or more groups independently selected from the group consisting of --O--, --S--, --SO--, --SO.sub.2 --, --NH--, --N(lower alkyl)--, --C(O)--, phenylene, X-substituted phenylene, heteroarylene and X-substituted heteroarylene; or an interrupted alkyl chain as defined substituted by one or more substituents selected form the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl;R.sub.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: July 5, 1994
    Assignee: Schering Corporation
    Inventors: John Clader, Sundeep Dugar, Timothy Kogan, Bradley Tait, Wayne Vaccaro
  • Patent number: 5324710
    Abstract: Compounds of the formula I or their salts ##STR1## in which R.sup.1 to R.sup.6, W, X, a and b are as defined in claim 1 and L is a heterocyclic or isocyclic aromatic radical having 5 to 6 ring atoms, which can be condensed with an aromatic or non-aromatic 5- or 6-membered ring, where the radical can be unsubstituted or substituted, and a, b and c independently of one another are 0 or 1, are suitable as herbicides, plant growth regulators and fungicides. They can be prepared by the processes defined herein, it being possible in some cases to use novel intermediates.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: June 28, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Oswald Ort, Lothar Willms, Klaus Bauer, Hermann Bieringer, Arno Schulz, Burkhard Sachse, Peter Braun
  • Patent number: 5317005
    Abstract: Herbicidal pyrimidine and triazine derivatives of the formula: ##STR1## and salts thereof, where: X represents --CH.dbd. or --N.dbd.;Y is a substituted or unsubstituted alkyl or amino group;R.sup.1 represents a substituted or unsubstituted alkyl, cycloalkyl, phenyl or heterocyclyl group;R.sup.2 represents hydrogen, halogen or alkyl; andR.sup.4 and R.sup.5, which may be the same or different, each represent hydrogen, alkyl, alkoxy, amino, alkylamino, dialkylamino or halogen.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: May 31, 1994
    Assignee: Schering Agrochemicals Limited
    Inventor: Graham P. Jones