Halogen Attached Directly To The Diazine Ring By Nonionic Bonding Patents (Class 544/313)
  • Patent number: 5318945
    Abstract: Thiocarboxylic acid derivatives useful as herbicides or plant growth regulators are of the general formula I ##STR1## where R.sup.1 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl or cycloalkenyl, unsubstituted or substituted alkenyl or alkynyl or unsubstituted or substituted phenyl;R.sup.2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.6, where R.sup.6 is hydrogen or, together with R.sup.3, forms a C.sub.3 - or C.sub.4 -alkylene chain or C.sub.3 - or C.sub.4 -alkenylene chain in which a methylene group is replaced with oxygen;R.sup.3 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio or R.sup.3 is bonded to R.sup.6 as stated above to give a 5-membered or 6-membered ring;R.sup.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: June 7, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Baumann, Thomas Saupe, Joachim Rheinheimer, Uwe J. Vogelbacher, Matthias Bratz, Norbert Meyer, Matthias Gerber, Karl-Otto Westphalen, Uwe Kardorff, Andreas Landis, Helmut Walter
  • Patent number: 5314893
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is an amino substituted pyrimidinone or a pyrimidinedione including pharmaceutically acceptable salts are useful as antiviral agents.
    Type: Grant
    Filed: January 25, 1993
    Date of Patent: May 24, 1994
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
  • Patent number: 5286861
    Abstract: The present invention relates to a novel process for preparing uracil derivatives useful as intermediates in the synthesis of uridines having antiviral or antitumor activity or useful as coadjuvants in antiviral therapy, characterized by converting a compound of the formula II into its mesylate derivative of the formula III which is the reduced to give the desired compound of the formula I: ##STR1## in which R.sub.1 is H, halogen, alkyl, aryl or aralkyl.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: February 15, 1994
    Assignee: Farmitalia Carlo Erba S.r.l.
    Inventors: Angelo Bedeschi, Walter Cabri, Ilaria Candiani, Tiziano Martinengo
  • Patent number: 5284820
    Abstract: Herbicidal substituted cycloalkenes of the formula ##STR1## in which A is a straight-chain or branched, optionally substituted alkanediyl group,X is O, S, N--R.sup.8 or CR.sup.9 R.sup.10,Y is O, S, NH or N-alkyl,Z is N or R.sup.11, andR.sup.1 to R.sup.11 represent various organic radicals.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: February 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mark-Wilhelm Drewes, Peter Muller, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5276151
    Abstract: A synthesis of 1,3-dioxolane nucleosides that includes condensing a 2-0-protected-5-0-acylated-1,3-dioxolane with a purine or pyrimidine base in the presence of a titanium containing Lewis acid to provide predominately the desired .beta.-isomer in the C1'-position of a 1,3-dioxolane nucleoside.A process for the resolution of a racemic mixture of 1,3-dioxolane nucleoside enantiomers is also disclosed that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: January 4, 1994
    Assignee: Emory University
    Inventor: Dennis C. Liotta
  • Patent number: 5272152
    Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: December 21, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, Val S. Goodfellow
  • Patent number: 5270318
    Abstract: A compounds of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, halogen, haloalkyl, alkoxy, alkenoxy, alkoxyalkyl, haloalkoxy, alkylthio, cyano, nitro, amino, NR.sup.4 R.sup.5, hydroxy, acylamino, --CO.sub.2 R.sup.3, --O(CH.sub.2).sub.m CO.sub.2 R.sup.3, phenyl, phenoxy, benzyl or benzyloxy, the phenyl group or phenyl moiety of the benzyl group being optionally substituted in the ring; or R.sup.1 and R.sup.2 when taken together form a 5- or 6-membered ring; m is 1 or 2; R.sup.3 and R.sup.5 are hydrogen or C.sub.1-4 alkyl; R.sup.4 is C.sub.1-4 alkyl; n is 0 or 1; X is oxygen or sulphur; Y is hydrogen when n is 0; or Y is oxygen or sulphur when n is 1; are useful as nematicides.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: December 14, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael D. Turnbull
  • Patent number: 5270289
    Abstract: The invention relates to new substituted .alpha.-pyrimidinyloxy(thio)- and .alpha.-triazinyloxy(thio)carboxylic acid derivatives of general formula I ##STR1## in which A, R.sup.1-3, X and Y have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: December 14, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Christoph Harde, Erhard Nordhoff, Anita Kruger, Gabriele Kruger, Gerhard Tarara, Peter Wegner, Nikolaus Heinrich, Clemens Kotter, Gerhard Johann, Richard Rees
  • Patent number: 5264440
    Abstract: Compounds having the formula (I): ##STR1## in which any two of K, L and M are nitrogen and the other is CE; X and Y are independently hydrogen, halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.2-4 alkynyloxy, phenyl, benzyloxy, cyano, isocyano, isothiocyanato, nitro, NR.sup.1 R.sup.2, NR.sup.1 OR.sup.2,N.sub.3, NHCOR.sup.1, NR.sup.1 CO.sub.2 R.sup.2, NHCONR.sup.1 R.sup.2, N.dbd.CHNR.sup.1 R.sup.2, NHSO.sub.2 R.sup.1, OR.sup.1, OCOR.sup.1, OSO.sub.2 R.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, SO.sub.2 OR.sup.1, SO.sub.2 NR.sup.1 R.sup.2, COR.sup.1, CR.sup.1 .dbd.NOR.sup.2, CHR.sup.1 CO.sub.2 R.sup.2, CO.sub.2 R.sup.1, CONR.sup.1 R.sup.2, CSNR.sup.1 R.sup.2, CH.sub.3 O.sub.2 C.C:CH.OCH.sub.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: November 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Ian T. Streeting, Rex Cheetham
  • Patent number: 5262385
    Abstract: A compounds represented by the formula ##STR1## wherein X represents a fluorine atom,W represents an oxygen atom, sulfur atom or group --OCH.sub.2 --,Z.sup.1 and Z .sup.2 each represent a nitrogen atom or group CH, but when Z.sup.1 is a nitrogen atom, Z.sup.2 represents a nitrogen atom or group CH and when Z.sup.1 is a group CH, Z.sup.2 represents a nitrogen atom,R.sup.1 and R.sup.2 each independently represent either a hydrogen atom, halogen atom or mono- or dilower alkyl-substituted amino, or a lower alkyl, lower alkoxy or lower alkylthio each of which may be substituted with a halogen atom,R.sup.3 and R.sup.4 form together with the carbon atoms to which they bind respectively a 5- to 8-membered carbon ring.
    Type: Grant
    Filed: July 23, 1991
    Date of Patent: November 16, 1993
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Atsushi Goh, Sachio Kudo, Yorio Kumamoto, Michi Watanabe, Takako Takahashi, Takako Aoki, Norishige Toshima, Keiji Endo, Hideshi Mukaida, Shinji Kawaguchi, Rika Higurashi
  • Patent number: 5262386
    Abstract: Pyrimidinyl- and triazinyl-salicylamides of the formula I ##STR1## in which the meanings of the radicals are described in claim 1, and the salts of compounds of the formula I which have a free hydroxycarbonyl group have a herbicidal and plant-growth regulating action. They are suitable as active substances in weed killers and in compositions for positively influencing the growth of crop plants.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: November 16, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Christoph Luthy, Raymond Fisher
  • Patent number: 5252576
    Abstract: Disclosed are a central nervous system depressant which comprises a 1-amino-5-halogenouracil represented by the formula ##STR1## wherein X represents a halogen atom, or a pharmaceutically acceptable salt thereof as an active ingredient;a 1-amino-5-halogenouracil represented by the formula ##STR2## wherein X' represents chlorine, bromine or iodine, or a salt thereof; and a process for preparing a 1-amino-5-halogenouracil represented by the above shown formula [I] from a pyrimidine derivative represented by the formula ##STR3## wherein X represents a halogen atom and R represents a protective group.
    Type: Grant
    Filed: January 17, 1991
    Date of Patent: October 12, 1993
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Shinji Sakata, Masahiro Imaizumi
  • Patent number: 5250536
    Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, halogen, haloalkyl, alkoxy, alkenoxy, alkoxyalkyl, haloalkoxy, alkylthio, cyano, nitro, amino, NR.sup.5 R.sup.6, hydroxy, acylamino, --CO.sub.2 R.sup.4, --O(CH.sub.2).sub.m CO.sub.2 R.sup.4, phenyl, phenoxy, benzyl or benzyloxy, the phenyl group or phenyl moiety of the benzyl group being optionally substituted in the ring; or R.sup.2 and R.sup.3 when taken together form a 5- or 6-membered ring; m is 1 or 2; R.sup.4 and R.sup.6 are hydrogen or C.sub.1-4 alkyl; R.sup.5 is C.sub.1-4 alkyl; n is 0, 1 or 2; are useful as nematicides.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: October 5, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael D. Turnbull
  • Patent number: 5248776
    Abstract: An asymmetric process for the preparation of enantiomerically pure .beta.-L-(-)-1,3-oxathiolane-nucleosides that includes the initial preparation of the key chiral intermediates (2R,5R) and (2R,5S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane from 1,6-thioanhydro-L-gulose. The 2R,5(R,S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane is condensed with a desired heterocyclic base, typically a purine or pyrimidine base, to provide the product nucleoside. The synthesis can be used to prepare the pharmaceutically important compound, .beta.-L-(-)-1-[(2.beta.,4.beta.)-2-(hydroxymethyl)-4-(1,3-thioxolane)]cyt osine (.beta.-L-(-)BCH-189).
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: September 28, 1993
    Assignee: University of Georgia Research Foundation, Inc.
    Inventors: Chung K. Chu, Lak-Shin Jeong, J. Warren Beach
  • Patent number: 5246938
    Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, halogen, haloalkyl, alkoxy, alkenoxy, alkoxyalkyl, haloalkoxy, alkylthio, cyano, nitro, amino, NR.sup.5 R.sup.6, hydroxy, acylamino, --CO.sub.2 R.sup.4, --O(CH.sub.2).sub.m CO.sub.2 R.sup.4, phenyl, phenoxy, benzyl or benzyloxy, the phenyl group or phenyl moiety of the benzyl group being optionally substituted in the ring; or R.sup.2 and R.sup.3 when taken together form a 5 - or 6-membered ring; m is 1 or 2; R.sup.4 and R.sup.6 are hydrogen or C.sub.1-4 alkyl; R.sup.5 is C.sub.1-4 alkyl; n is 0, 1 or 2; provided that when n is 0, R.sup.1, R.sup.2 and R.sup.3 are not all hydrogen, or when n is 0 and R.sup.2 is hydrogen, R.sup.1 and R.sup.3 are not both methyl, or when n is 0 and R.sup.2 and R.sup.3 are both hydrogen, R.sup.1 is not methyl; are useful as nematicides.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: September 21, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Turnbull, John Finney
  • Patent number: 5246931
    Abstract: A compound of the formula: ##STR1## wherein A is a purin-9-yl group, a heterocyclic isostere of a purin-9-yl group, a pyrimidin-1-yl group or a heterocyclic isostere of a pyrimidin-1-yl group; E is hydrogen, --CH.sub.2 OH or --OH; and G and D are independently selected from hydrogen, C.sub.1 to C.sub.10 alkyl, --OH, --CH.sub.2 OH, --CH.sub.2 OR.sub.20 wherein R.sub.20 is C.sub.1 to C.sub.6 alkyl, --CH.sub.2 OC(O)R.sub.21 wherein R.sub.21 is C.sub.1 to C.sub.10 alkyl, --CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23) wherein R.sub.22 is the side chain of any of the naturally occurring amino acids and R.sub.23 is hydrogen or --C(O)CH(R.sub.24)(NH.sub.2) wherein a R.sub.24 is the side chain of any of the naturally occurring amino acids, --CH.sub.2 SH, --CH.sub.2 Cl, --CH.sub.2 F, --CH.sub.2 Br, --CH.sub.2 I, --C(O)H, --CH.sub.2 CN, --CH.sub.2 N.sub.3, --CH.sub.2 NR.sub.1 R.sub.2, --CO.sub.2 R.sub.1, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OR.sub.20 wherein R.sub.20 is as defined above, --CH.sub.2 CH.sub.2 OC(O)R.sub.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: September 21, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventors: Daniel W. Norbeck, Jacob J. Plattner, Terry J. Rosen, David L. Garmaise, Richard J. Pariza, Steven M. Hannick, Thomas J. Sowin
  • Patent number: 5237063
    Abstract: Substituted trifluoro- and chlorodifluoromethoxypyrimidines of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each, independently of one another, hydrogen, halogen or haloalkyl, and R.sup.1 and/or R.sup.2 are also trifluoromethoxy or chlorodifluoromethoxy, and n is 0 or 1, are prepared as described.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: August 17, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Hans-Josef Wolf
  • Patent number: 5225550
    Abstract: It is possible, by using symmetrical formaldehyde acetals of the formula ##STR1## in which the substituents R.sup.1 -R.sup.3 have the specified meanings, advantageously to introduce the substituent ##STR2## into nitrogen-containing heterocyclic systems to form acyclic nucleoside analogs.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: July 6, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerhard Jahne
  • Patent number: 5206245
    Abstract: Fungicidal compounds having the formula (I): ##STR1## in which any two of K, L and M are nitrogen and the other is CE; X and Y are independently hydrogen, halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.2-4 alkynyloxy, phenyl, benzyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, NR.sup.1 R.sup.2, NR.sup.1 OR.sup.2, N.sub.3, NHCOR.sup.1, NR.sup.1 CO.sub.2 R.sup.2, NHCONR.sup.1 R.sup.2, N.dbd.CHNR.sup.1 R.sup.2, NHSO.sub.2 R.sup.1, OR.sup.1, OCOR.sup.1, OSO.sub.2 R.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, SO.sub.2 OR.sup.1,SO.sub.2 NR.sup.1 R.sup.2, COR.sup.1, CR.sup.1 .dbd.NOR.sup.2, CHR.sup.1 CO.sub.2 R.sup.2, CO.sub.2 R.sup.1, CONR.sup.1 R.sup.2, CSNR.sup.1 R.sup.2, CH.sub.3 O.sub.2 C.C:CH.OCH.sub.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: April 27, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Ian T. Streeting, Rex Cheetham, Paul J. de Fraine
  • Patent number: 5204466
    Abstract: The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: April 20, 1993
    Assignee: Emory University
    Inventors: Dennis C. Liotta, Woo-Baeg Choi
  • Patent number: 5194438
    Abstract: .alpha.-Arylacrylates substituted by a heterocyclic radical and of the general formula I ##STR1## where R.sup.1 is alkoxy or alkylthio R.sup.2 is alkyl, Het is pyridyl, pyridone, quinolyl, pyrimidinyl, pyrimidinone, the heterocyclic ring system being unsubstituted or substituted, A is carbonyloxy, oxygen or sulfur, and n is 0 or 1, and their plant-tolerated acid addition salts and metal complexes, and the N-oxides of the heterocyclic compounds, and fungicides containing these compounds.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: March 16, 1993
    Assignee: Basf Aktiengesellschaft
    Inventors: Franz Schuetz, Thomas Kuekenhoehner, Jochen Wild, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5183492
    Abstract: The invention is concerned with compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the significances given in the description, as well as enol ethers and salts thereof and their manufacture. The compounds have herbicidal properties and are accordingly suitable as active ingredients of weed control compositions. The invention is also concerned with weed control compositions containing one or more of such substances and with the use of the substances or compositions for the control of weeds.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: February 2, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Milos Suchy, Paul Winternitz, Martin Zeller
  • Patent number: 5182282
    Abstract: Novel 4-benzyl-1H-indoles of the formula ##STR1## in all diastereoisomeric forms and mixtures thereof having anti-arhythmic activity.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: January 26, 1993
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Jacques Guillaume, Gilles Hamon
  • Patent number: 5178663
    Abstract: Disclosed is a 3-alkoxyalkanoic acid compound represented by the following formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a halo-lower alkyl group or a cyano-lower alkyl group; R.sup.2 represents hydrogen atom or a lower alkyl group; R.sup.3 represents a lower alkyl group or a cycloalkyl group; or R.sup.2 and R.sup.3 are mutually bonded to represent a cycloalkyl group; R.sup.4 represents hydrogen atom, a lower alkyl group or a lower alkynyl group; R.sup.5 represents a lower alkoxy group, a lower alkyl group, a halogen atom or a halo-lower alkyl group; R.sup.6 represents a lower alkoxy group or a lower alkyl group; andX represents oxygen atom or sulfur atom,or an alkali addition salt thereof, processes for preparing the same and herbicides containing the same as an active ingredient(s).
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: January 12, 1993
    Assignee: UBE Industries, Ltd.
    Inventors: Katsumasa Harada, Takaaki Abe, Yuji Akiyoshi, Hiroshi Shiraishi, Kaoru Yamamoto
  • Patent number: 5169856
    Abstract: The present invention relates to unsaturated carboxylic acid amide derivatives of the formula ##STR1## wherein ring A stands for an optionally substituted aromatic ring; R.sup.1 stands for a hydrogen atom or an optionally substituted hydrocarbon residue or forms an optionally substituted carbocyclic ring with the adjacent group --CH.dbd.C-- together with two carbon atoms constituting the ring A; R.sup.2 stands for a hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group; R.sup.3 stands for an optionally substituted hydrocarbon residue; and n denotes an integer ranging from 2 to 6, and salts thereof, as well as the production thereof.The compounds of the present invention act on the central nervous system of mammals and has a strong anti-cholinesterase activity, which can be used for the prophylaxis and therapy of, for example, senile dementia, Alzheimer's diseases, Huntington's chorea, et., and are useful as medicines.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: December 8, 1992
    Assignee: Takeda Chemical Industries, Inc.
    Inventors: Giichi Goto, Akinobu Nagaoka
  • Patent number: 5169430
    Abstract: A compound having the structural formula ##STR1## wherein: R is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, formyl, C.sub.2 -C.sub.6 alkanoyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl, or alkali metal;X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxy, cyano, or halogen;Y is hydrogen, halogen, or C.sub.1 -C.sub.4 dialkylamino;R.sup.1 is hydrogen, C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkoxy or C.sub.3 -C.sub.8 hydroxyalkyl;R.sup.2 is hydrogen, C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, halo substituted C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.4 alkoxy, hydroxy C.sub.1 -C.sub.4 alkyl, cyano C.sub.1 -C.sub.4 alkyl, 2,3-epoxypropyl, 2,2-dialkoxyethyl, alkoxyalkyl, phenyl, aralkyl, C.sub.1 -C.sub.4 acyl, C.sub.1 -C.sub.4 carbalkoxyalkyl, C.sub.1 -C.sub.4 carbalkoxyalkyl substituted by C.sub.1 -C.sub.
    Type: Grant
    Filed: August 9, 1991
    Date of Patent: December 8, 1992
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Richard J. Strunk, Allyn R. Bell
  • Patent number: 5167693
    Abstract: Herbicidal substituted azines of the formula ##STR1## in which m represents the numbers 0, 1, 2 or 3,A represents nitrogen or a C-X group where X represents hydrogen or halogen,Q represents oxygen or sulphur,R.sup.1 and R.sup.2 are identical or different and represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy-alkyl, alkoxy, halogenoalkoxy, alkylthio, alkylamino or dialkylamino,R.sup.3 represents amino, hydroxyl, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl-amino or alkylsulphonylamino,R.sup.4 represents hydrogen or alkyl andZ represents N--R.sup.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: December 1, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mark W. Drewes, Rolf Kirsten, Wolfgang Kramer, Bernd W. Kruger, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5166206
    Abstract: Substituted pyrimidines, pyrimidinones and pyridopyrimidines of formula (I) are as angiotensin II antagonists useful in the treatment of hypertension, ocular hypertension and certain CNS ailments: ##STR1## wherein K is --N(R.sup.8a)--C(.dbd.M) or --N.dbd.C(R.sup.8b) where M is O or NR.sup.22.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: November 24, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Eric E. Allen, William J. Greenlee, Malcolm MacCoss, Arthur A. Patchett
  • Patent number: 5162326
    Abstract: Novel pyrimidinedione derivatives of the formula (I): ##STR1## wherein R.sup.1 is hydrogen or a hydrocarbon residue which may be substituted; R.sup.2 is hydrogen, halogen, nitro, optionally substituted amino, formyl or a hydrocarbon residue which may be substituted; R.sup.3 is a hydrocarbon residue which may be substituted; R.sup.4 is hydrogen, halogen or nitro; R.sup.5 is a residue capable of forming an anion or a residue convertible into an anion; X is a direct bond or a spacer having one atomic length and containing an oxygen, nitrogen or sulfur atom; Y is a direct bond or a spacer having atomic length of two or less between the phenylene group and the phenyl group; n is an integer of 1 or 2; and the pharmaceutically acceptable salts thereof have potent angiotensin II antagonistic activity and hypotensive activity, thus being useful as therapeutic agents for treating circulatory system diseases such as hypertensive diseases, heart diseases, strokes, etc.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: November 10, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takehiko Naka, Kohei Nishikawa
  • Patent number: 5151426
    Abstract: Methods and compositions for preventing or treating human immunodeficiency virus (HIV) infections characterized by 2-substituted-5-substituted-1,3-oxathiolanes.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: September 29, 1992
    Assignee: BioChem Pharma Inc.
    Inventors: Bernard Belleau, Nghe Nguyen-Ba
  • Patent number: 5149810
    Abstract: A pyrimidinone compound of formula (IIIA) or (VA): ##STR1## wherein R.sup.13 is hydrogen, halogen or cyano and R.sup.14 is halo or haloalkyl with the proviso that (a) when R.sup.13 is cyano, R.sup.14 is other than chlorine; (b) R.sup.13 and R.sup.14 are not both halo; (c) when R.sup.13 is halo R.sup.14 is other than monofluoromethyl; and (d) when R.sup.13 is hydrogen R.sup.14 is not halo or a halomethyl group; ##STR2## wherein R.sup.10 is hydrogen or C.sub.1-4 alkyl; R.sup.15 is cyano and R.sup.16 is R.sup.6 is defined in relation to formula (V) or R.sup.15 is hydrogen or halogen other than fluorine and R.sup.16 is pentafluoroethyl or difluoromethyl. These compounds are useful as intermediates in the preparation of insecticidal compounds.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: September 22, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Trevor R. Perrior, David J. Tapolczay, Alan J. Whittle
  • Patent number: 5145856
    Abstract: Compounds having the formula (I): ##STR1## in which any two of K, L and M are nitrogen and the other is CE; X and Y are independently hydrogen, halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.2-4 alkynyloxy, phenyl, benzyloxy, cyano, isocyano, isothiocyanato, nitro, NR.sup.1 R.sup.2, NR.sup.1 OR.sup.2, N.sub.3, NHCOR.sup.1, NR.sup.1 CO.sub.2 R.sup.2, NHCONR.sup.1 R.sup.2, N.dbd.CHNR.sup.1 R.sup.2, NHSO.sub.2 R.sup.1, OR.sup.1, OCOR.sup.1, OSO.sub.2 R.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, SO.sub.2 OR.sup.1, SO.sub.2 NR.sup.1 R.sup.2, COR.sup.1, CR.sup.1 .dbd.NOR.sup.2, CHR.sup.1 CO.sub.2 R.sup.2, CO.sub.2 R.sup.1, CONR.sup.1 R.sup.2, CSNR.sup.1 R.sup.2, CH.sub.3 O.sub.2 C.C:CH.OCH.sub.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: September 8, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Ian T. Streeting, Rex Cheetham
  • Patent number: 5145960
    Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is a pyrimidine base or an analog thereof and R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## wherein X.sub.7 is hydrogen, alkyl, substituted alkyl or aryl.
    Type: Grant
    Filed: August 7, 1991
    Date of Patent: September 8, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, Joseph A. Tino
  • Patent number: 5143917
    Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration ()CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: September 1, 1992
    Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KG
    Inventor: Henrich H. Paradies
  • Patent number: 5139563
    Abstract: Compounds of formula I ##STR1## wherein A is nitrogen or a group CR.sup.5 ;each of R.sup.1, R.sup.2 and R.sup.5 is, independently, hydrogen, halogen, formyl, cyano, carboxy, azido or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, alkylthio, alkenylthio, alkynylthio, arylthio, alkylcarbonyl, alkoxycarbonyl, amino, aminoxy or dialkyliminoxy; andR is ##STR2## in which R.sup.3 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic or aryl, or COR.sup.8, R.sup.8 being hydroxy, alkoxy, carboxy, alkoxycarbonyl, amino or mono- or di- alkylamino; andR.sup.4 is a group COR.sup.6 wherein R.sup.6 is hydrogen, halogen, hydroxy, or optionally substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, alkylthio, alkenylthio, alkynylthio, arylthio, aminoxy, dialkyliminoxy or amino, or R.sup.6 is a group OR.sup.7 in which R.sup.7 is an optionally substituted heterocyclic ring; or ##STR3## each of R.sup.9 and R.sup.
    Type: Grant
    Filed: May 30, 1990
    Date of Patent: August 18, 1992
    Assignee: Shell Research Limited
    Inventors: David P. Astles, Andrew Flood, Alastair McArthur, Trevor W. Newton, John E. Spencer, David C. Hunter
  • Patent number: 5133973
    Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration (CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: July 28, 1992
    Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KG
    Inventor: Henrich Paradies
  • Patent number: 5134145
    Abstract: This invention is related to a novel class of aryl pyrimidine derivatives having insecticidal, miticidal and nematocidal activity at low concentration. The class of compounds is represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X and Z have the significance given in the description.Pesticidal compositions, methods of controlling pests and methods for preparing the compounds are within the scope of the invention.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: July 28, 1992
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./Ltee
    Inventors: Walter G. Brouwer, Ethel E. Felauer, Paul T. McDonald
  • Patent number: 5129938
    Abstract: A herbicidal pyrimidine derivative having the formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y.sub.1, Y.sub.2, Y.sub.3, X and Z are defined as in the specification.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: July 14, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Naonori Hirata, Kazuo Saitoh, Hideyuki Shibata
  • Patent number: 5127935
    Abstract: Disclosed herein is uracil derivatives having a haloalkyl group at the 5-position and a phenyl group at the 2-position which has a specific substituent, which are represented by the formula (I) and showing penetrative translocation activity and a very high herbicidal activity, in which as compared with the conventional herbicidal compounds, the said uracil derivatives can be applied for either soil treatment or foliage treatment, thereby producing a quick and high herbicidal effect even at a very low dosage against a large variety of weeds including perennial weeds, and have the property to residual effect for an appropriate period of time.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: July 7, 1992
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Jun Satow, Kenzou Fukuda, Kaoru Itoh, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
  • Patent number: 5118808
    Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration (CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: June 2, 1992
    Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KG
    Inventor: Henrich H. Paradies
  • Patent number: 5116404
    Abstract: The present invention provides novel uracil derivatives and pesticides which contain the novel uracil derivatives as an active ingredient, and exhibit preventing and controlling effects against harmful living things, especially agricultural insect pests, sanitary insect pests, stored product insect pests, house insect pests and veterinary insect pests at a very low drug-concentration.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: May 26, 1992
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Shigeru Ishii, Kazunari Nakayama, Kazuo Yagi, Jun Satow, Kenzou Fukuda, Kaoru Itoh, Toshiyuki Umehara, Masaki Kudo, Yoichi Inoue, Tsutomu Nawamaki, Shigeomi Watanabe
  • Patent number: 5112835
    Abstract: 6-substitutted acyclopyrimidine nucleoside derivatives represented by the following general formula I: ##STR1## wherein R.sup.1 represents a hydrogen or halogen atom or a group of alkyl, alkenyl, alkynyl, alkylcarbonyl, arylcarbonyl, arylcarbonylalkyl, arylthio or aralkyl; R.sup.2 represents a group of arylthio, alkylthio, cycloalkylthio, aryl sulfoxide, alkyl sulfoxide, cycloalkyl sulfoxide, alkenyl, alkynyl, aralkyl, arylcarbonyl, arylcarbonylalkyl or aryloxy; R.sup.3 represents a hydroxyalkyl group of which alkyl portion may contain an oxygen atom; X represents an oxygen or sulfur atom or amino group; Y represents an oxygen or sulfur atom; and A represents .dbd.N-- or --NH-- or pharmaceutically acceptable salts thereof, processes for their preparation and antiviral agents containing them as active ingredients.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: May 12, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tadashi Miyasaka, Hiromichi Tanaka, Erik D. A. De Clercq, Masanori Baba, Richard T. Walker, Masaru Ubasawa
  • Patent number: 5104878
    Abstract: A compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from hydrogen, halogen, haloalkyl, alkoxy or nitro, provided that R.sup.1 and R.sup.2 are not both nitro; R.sup.3 and R.sup.4 are independently selected from hydrogen, halogen, alkyl or cycloalkyl; R.sup.5 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.6 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.7 is hydrogen, halogen, hydroxyalkyl, cyano, nitro, alkoxy, --S(O).sub.n R.sup.10, NR.sup.11 R.sup.12, haloalkyl or formyl; R.sup.8 is hydrogen, halogen, NR.sup.11 R.sup.12, alkyl, cycloalkyl or S(O).sub.n R.sup.10 ; and R.sup.9 is oxygen or sulphur; where n is 0, 1 or 2; and R.sup.10 is alkyl, haloalkyl or cycloalkyl; and R.sup.11 and R.sup.12 are independently selected from hydrogen, alkyl or cycloalkyl or R.sup.11 and R.sup.12 together with the nitrogen to which they are attached form a heterocyclic group; provided that when R.sup.
    Type: Grant
    Filed: April 9, 1990
    Date of Patent: April 14, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Alan J. Whittle, Trevor R. Perrior, Raymond L. Sunley
  • Patent number: 5100458
    Abstract: Salicylic acid derivatives of the formula I ##STR1## where A is unsubstituted or substituted phenyl, an unsubstituted or substituted five-membered heteroaromatic structure having from two to four nitrogen atoms or having two nitrogen atoms and in addition a sulfur or oxygen atom, or unsubstituted or substituted naphthyl, n is 0, 1 or 2, X and Y are each nitrogen or a methine group and R.sup.1 to R.sup.4 have the meanings stated in the description, processes and intermediates for their preparation, and their use as herbicides and bioregulators.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Eicken, Joachim Rheinheimer, Uwe J. Vogelbacher, Karl-Otto Westphalen, Bruno Wuerzer, Wilhelm Rademacher, Klaus Grossmann
  • Patent number: 5089044
    Abstract: The invention relates to new substituted pyrimidinyloxy(thio)- and triazinyloxy(thio)acrylic acid derivative of general formula I ##STR1## in which A, G, R.sup.1-3, X and Y have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: February 18, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Christoph Harde, Erhard Nordhoff, Anita Kruger, Gabriele Kruger, Gerhard Tarara, Peter Wegner, Nikolaus Heinrich, Clemens Kotter, Gerhard Johann, Richard Rees
  • Patent number: 5085685
    Abstract: Carboxylic acid derivatives of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;R.sup.3 is hydrogen, hydroxyl, cyano, nitro, formyl, halogen, unsubstituted or substituted amino, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.6 -alkynyloxy;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl;R.sup.5 is unsubstituted or substituted five-membered hetaryl or isoxazolinyl or --CR.sup.6 .dbd.NOR.sup.7 ;R.sup.6 is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl or phenyl;R.sup.7 is unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl or phenyl;A is oxygen or sulfur;X is nitrogen or methine .dbd.CR.sup.8 --;R.sup.8 is one of the radicals R.sup.3, or R.sup.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: February 4, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Rheinheimer, Karl Eicken, Uwe J. Vogelbacher, Wolfgang Rohr, Thomas Kuekenhoehner, Karl O. Westphalen, Bruno Wuerzer
  • Patent number: 5084084
    Abstract: Disclosed herein is uracil derivatives having a haloalkyl group at the 6-position and a phenyl group at the 3-position which has a specific substituent, which are represented by the formula (I) and showing penetrative translocation activity and a very high herbicidal activity, in which as compared with the conventional herbicidal compounds, the said uracil derivatives can be applied for either soil treatment or foliage treatment, thereby producing a quick and high herbicidal effect even at a very low dosage against a large variety of weeds including perennial weeds, and have the property to residual effect for an appropriate period of time.
    Type: Grant
    Filed: January 9, 1991
    Date of Patent: January 28, 1992
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Jun Satow, Kenzou Fukuda, Kaoru Itoh, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
  • Patent number: 5064818
    Abstract: Insecticidal, acaricidal and nematocidal pyrimidinyl(thiono)(thio)-phosphoric(phosphonic) acid (amide) esters of the formula ##STR1## in which R represents hydrogen, or represents an optionally substituted radical selected from the group consisting of alkyl, alkoxy, alkylthio, dialkylamino, cycloalkyl and aryl,R.sup.1 represents hydrogen, aklyl or halogen,R.sup.2 represents alkyl,R.sup.3 represents alkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino or aryl andX represents oxygen or sulphur.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: November 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Jurgen Hartwig, Benedikt Becker
  • Patent number: 5059690
    Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is a purine or pyrimidine base or an analog thereof and R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## wherein X.sub.7 is hydrogen, alkyl, substituted alkyl or aryl.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: October 22, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, Joseph A. Tino
  • Patent number: 5057518
    Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration (CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: October 15, 1991
    Assignee: Medice Hem.-Pharm. Fabrik Putter GmbH & Co. KG
    Inventor: Henrich H. Paradies