1,3,4-thiadiazoles (including Hydrogenated) Patents (Class 548/136)
  • Patent number: 5158943
    Abstract: A sulfur-containing hetrocyclic compound of the formula (I) ##STR1## wherein the ring A is an optionally substituted benzene ring, R is a hydrogen atom or an optionally substituted hydrocarbon residue, B is a carboxyl group which may be esterified or amidated, X is --CH(OH)-- or --CO--, and n is an integer of 0, 1 or 2, or its salt, which is useful in the prevention or treatment of osteoporosis.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: October 27, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Iwao Yamazaki
  • Patent number: 5155122
    Abstract: The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: October 13, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Michael D. Mullican, Gary P. Shrum, Paul C. Unangst, Michael W. Wilson
  • Patent number: 5147443
    Abstract: The invention relates to the use of 2,5-substituted 1,3,4-thiadiazoles of the formula ##STR1## in which R.sup.1 stands for straight-chain or branched halogenoalkyl,R.sup.2 stands for straight-chain or branched alkyl andn stands for the numbers 1 or 2,as microbicides for protecting industrial materials.
    Type: Grant
    Filed: September 26, 1991
    Date of Patent: September 15, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Diehr, Karl-Heinz Kuck, Wilfried Paulus, Hans-Georg Schmitt
  • Patent number: 5143642
    Abstract: The invention relates to a liquid-crystalline medium for electrooptical display elements based on the ECB effect, containing two components A and B which themselves comprise one or more individual compounds, component A having clearly negative dielectric anistropy and giving the liquid-crystalline phase a dielectric anistrophy of .ltoreq.-0.3, and component B having pronounced nematogeneity and a viscosity of not more than 30 mPa.s at 20.degree. C.
    Type: Grant
    Filed: January 11, 1991
    Date of Patent: September 1, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Thomas Geelhaar, Reinhard Hittich, Ulrich Finkenzeller, Bernhard Rieger, Georg Weber
  • Patent number: 5138064
    Abstract: Novel 3-pyrrolidinylthio-1-azabiycyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof have antimicrobial activity and are useful as medicaments in the treatment of infectious diseases caused by pathogenic microorganisms.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: August 11, 1992
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Kohji Hattori, Takashi Nakajima
  • Patent number: 5135938
    Abstract: Leukotriene antagonist thiadiazoles have been prepared.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: August 4, 1992
    Assignee: SmithKline Beecham Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Irene Uzinskas
  • Patent number: 5132316
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-2 alkyl, C.sub.1 -2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups;a group ##STR2## in which Y represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-2 alkyl group, Y being optionally C-substituted by a methyl group; ora group ##STR3## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.3 and the other is nitrogen or CR.sub.4 where R.sub.3 and R.sub.4 are independently selected from hydrogen and methyl; and each of p and q independently represents an integer of 2 to 4.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: July 21, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
  • Patent number: 5120733
    Abstract: A compound of the formula: ##STR1## (wherein R is phenoxy optionally substituted by a halogen, methoxy, or methyl group, ##STR2## one of A and B is ##STR3## and the other is >CH.sub.2 ;R.sup.1 is hydrogen or C.sub.1 -C.sub.5 alkyl;Z.sup.1 is phenyl, benzyl, or isoxazolyl each optionally substituted by a halogen, methoxy, or methyl group; Z.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, or phenyl optionally mono-, di-, or tri-substituted by a halogen, methoxy, or methyl group; or Z.sup.1 and Z.sup.2 taken together with the adjacent nitrogen atom may form 5-membered heterocyclic group; Z.sup.3 is C.sub.1 -C.sub.5 hydroxyalkyl, di(C.sub.1 -C.sub.5 alkyl) sulfamoyl, 6-membered heterocyclic group, phenyl, benzyl, or phenylsulfonyl each phenyl moiety of the last three members being optionally substituted by a halogen, methoxy, or methyl group; Z.sup.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: June 9, 1992
    Assignee: Shionogi and Co. Ltd.
    Inventors: Hiromu Matsumura, Toshisada Yano, Akira Matsushita, Masami Eigyo
  • Patent number: 5102897
    Abstract: The novel 3,5-ditertiarybutyl-4-hydroxyphenylthio-1,3,4-thiadiazoles and oxadiazoles and 3,5-ditertiarybutyl-4-hydroxyphenylmethanone-1,3,4-thiadiazoles and oxadiazoles and related compounds of the present invention are antiinflammatory agents having activity as inhibitors of 5-lipoxygenase, cyclooxygenase or both.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: April 7, 1992
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Catherine R. Kostlan, James B. Kramer, Michael D. Mullican, Jagadish C. Sircar
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5101034
    Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: March 31, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Schmidt, Hans-Joachim Diehr
  • Patent number: 5098600
    Abstract: There is provided a liquid crystal compound represented by the following general formula (I), a liquid crystal composite including at least one kind of above liquid crystal compound and a liquid crystal device in which the liquid crystal composite is disposed between a pair of electrode substrates. ##STR1## In the above formula (I), R.sub.1 is a straight chain alkyl having 1-12 carbon atoms. R.sub.2 is a straight chain or branched chain alkyl, which may have a substituted radical, having 1-18 carbon atoms and in which one or more than two methylene, which do not adjoin, may be substituted by --Y--, ##STR2## --CH.dbd.CH--, or --C.vertline.C--. Y is O or S. A is --A.sub.1 -- or --A.sub.1 --A.sub.2 --, and B is --B.sub.1 -- or --B.sub.1 --B.sub.2 --. A.sub.1, A.sub.2, B.sub.1, and B.sub.2 each is selected from ##STR3## and a single bond. Z is hydrogen, halogen, cyano or methyl. X.sub.1 is a single bond when A is a single bond and is --CH.sub.2 O--, ##STR4## in other cases. n is 0 or 1, ##STR5## --OCH.sub.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: March 24, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Shinichi Nakamura, Yoko Yamada, Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano
  • Patent number: 5097038
    Abstract: Herbicidal substituted thiadiazolyloxyacetamides of the formula ##STR1## in which R.sup.1 stands for hydrogen or for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl and aralkyl,R.sup.2 stands for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy and alkinyloxy, orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are bonded form an optionally substituted, saturated or unsaturated heterocycle which can contain further hetero atoms and to which a benzo group can be fused, andR.sup.3 stands for an optionally substituted alkyl radical.Intermediates of the formulas ##STR2## in which R.sup.3 stands for optionally substituted alkyl, andX stands for S or SO.sub.2,are also new.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5096483
    Abstract: Novel herbicidally active 5-chloro-1,3,4-thiadiazol-2-yloxy-acetamides of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent alkyl, alkenyl, alkinyl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxyalkyleneoxy or alkoxy, aralkyl or optionally substituted aryl orR.sup.1 and R.sup.2 conjointly with the nitrogen atom to which they are bonded represent an optionally substituted, saturated or unsaturated heterocyclic ring which can contain further hetero-atoms and to which a benzene radical can be fused.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 5091109
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 respectively denote an alkyl group having 1-16 carbon atoms capable of having a substituent; X.sub.1, X.sub.2 and X.sub.3 respectively denote a single bond, --O--, ##STR2## A.sub.1 and A.sub.2 respectively ##STR3## wherein X.sub.4 and X.sub.5 respectively denote hydrogen, fluorine, chlorine, bromine, --CH.sub.3, --CN or --CF.sub.3 with proviso that X.sub.1 always denotes a single bond when A.sub.1 denotes a single bond; and n is 0 or 1.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: February 25, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shosei Mori, Shinichi Nakamura
  • Patent number: 5091397
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which one of X and Y represents hydrogen and the other represents --CH.sub.2 --Z where Z is a group ##STR2## in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, or three nitrogen atoms, any amino nitrogen being optionally substituted by a C.sub.1-2 alkyl, cyclopropyl or propargyl group, and any ring carbon atom being optionally substituted by a group R.sub.1 ; or a group ##STR3## in which A.sub.1, A.sub.2 and A.sub.3 complete a 5-membered aromtic ring and A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.2 and the other is nitrogen or CR.sub.3, or A.sub.2 is oxygen or sulphur, one of A.sub.1 and A.sub.3 is CR.sub.2 and the other is CR.sub.3 ; and R.sub.1, R.sub.2 and R.sub.3 are independently selected from hydrogen, halogen, CN, OR.sub.4, SR.sub.4, N(R.sub.4).sub.2, NHCOR.sub.4, NHCOOCH.sub.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: February 25, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Harry J. Wadsworth, Michael S. Hadley, Paul A. Wyman, Sarah M. Jenkins
  • Patent number: 5086186
    Abstract: Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with trichloracetyl isocyanate to produce novel N-trichloroacetyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as analgesic and antiinflammatory agents and/or intermediates for such agents.
    Type: Grant
    Filed: May 31, 1990
    Date of Patent: February 4, 1992
    Assignee: Pfizer Inc.
    Inventor: Sarah E. Kelly
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5076961
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of including one or two or more non-neighboring methylene groups which can be replaced with at least one species of --Z--, ##STR2## --CH.dbd.CH-- and --C.tbd.C--, wherein Z denotes --O-- or --S-- and R.sup.3 denotes hydrogen or an alkyl group having 1-5 carbon atoms; A.sup.1 denotes ##STR3## and A.sup.2 denotes any one of ##STR4## The mesomorphic compound is effective for providing a ferroelectric liquid crystal composition showing an improved low-temperature operation characteristic and a decreased temperature-dependence of response speed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: December 31, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Shinichi Nakamura, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shosei Mori
  • Patent number: 5073563
    Abstract: An alkoxycoumarin substituted by a heterocyclic radical, of the formula ##STR1## Het is one of the following heterocyclic radicals: where X is oxygen or sulfur.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: December 17, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz-Frieder Frickel, Thomas Kuekenhoehner, Beatrice Rendenbach-Mueller, Harald Weifenbach, Hans-Juergen Teschendorf
  • Patent number: 5071841
    Abstract: The present invention provides a sulfur-containing heterocyclic compound of the formula (I) ##STR1## wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof.Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof.The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 10, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
  • Patent number: 5064962
    Abstract: Diaminothiophenes of the formula ##STR1## or tautomers thereof, where R.sup.1 and R.sup.2 are each hydrogen or together are ##STR2## where T.sup.1 is hydrogen, alkyl or phenyl, T.sup.2 and T.sup.3 are, independently of one another, alkyl or phenyl, or T.sup.2 and T.sup.3 together with the nitrogen linking them are a heterocyclic radical,R.sup.3 is substituted amino andR.sup.4 is alkanoyl, benzoyl, cyano, nitro or ##STR3## where T.sup.4 is hydrogen, alkyl or phenyl and T.sup.5 is the radical of a primary amine or of an active methylene compound,are prepared as described. The present diaminothiophene compound is useful in the synthesis of dyes, crop protection agents and pharmaceuticals.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: November 12, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Karl-Heinz Etzbach
  • Patent number: 5061804
    Abstract: 3-thio pyrrolidines are intermediates for carbapenams.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: October 29, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Hohji Hattori, Takashi Nakajima
  • Patent number: 5051421
    Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Pier G. Ferrini
  • Patent number: 5051515
    Abstract: There are provided compounds having the general formulae ##STR1## wherein R is a non-fused azole moiety;n is 5, 6, 7 or 8; andR.sup.1 is a substituted, fused or non-fused azole moiety.These compounds have been demonstrated as having antipicornavirus activity.
    Type: Grant
    Filed: March 27, 1989
    Date of Patent: September 24, 1991
    Assignee: SynPhar Laboratories Incorporated
    Inventors: Mohsen Daneshtalab, Ronald G. Micetich, Dai Q. Nguyen, Chan M. Ha, Hiep T. Luu
  • Patent number: 5047554
    Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: September 10, 1991
    Assignee: Pfizer Inc.
    Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
  • Patent number: 5034047
    Abstract: Cyclohexenone derivatives of the general formula I ##STR1## where the substituents have the following meanings: R.sup.1 : substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, phenyl, benzyl or thenyl;R.sup.2 : substituted or unsubstituted C.sub.1 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or phenyl;R.sup.3 : hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.4 -trialkylsilyl, C.sub.1 -C.sub.4 -dialkylphosphonyl, C.sub.1 -C.sub.4 -dialkylthiophosphonyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynyl or substituted or unsubstituted benzoyl- or phenylsulfonyl;R.sup.4 : hydrogen, cyano, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxycarbonyl;A: a substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: July 23, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Kolassa, Juergen Kast, Thomas Kuekenhoehner, Norbert Meyer, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5034151
    Abstract: There is disclosed a mesomorphic compound represented by the following formula (I): ##STR1## wherein A.sub.1 denotes a single bond, ##STR2## denotes ##STR3## X denotes hydrogen, a halogen or cyano group; Y denotes oxygen or sulfur; R.sub.1 and R.sub.2 respectively denotes a linear or branched alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkoxycarbonyloxy group each having 1-18 carbon atoms and each capable of having a substituted of chloro, bromo, cyano, alkoxy or akoxycarbonyl group; and B denotes ##STR4## A ferroelectric liquid crystal composition comprises at least two mesomorphic compounds including at least one mesomorphic compound represented by the formula (I). A ferroelectric liquid crystal device is constituted by disposing the ferroelectric liquid crystal composition between a pair of substrates.
    Type: Grant
    Filed: March 27, 1989
    Date of Patent: July 23, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kenji Shinjo, Akio Yoshida, Takashi Iwaki, Takao Takiguchi, Hiroyuki Kitayama, Kazuharu Katagiri
  • Patent number: 5013854
    Abstract: An improved process for preparing trialkylsilyl ester and acid halide derivatives of carboxylic acids is provided along with novel trialkylsilyl ester intermediates of 2-(2-furyl)-2-methoximinoacetic acid.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: May 7, 1991
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Bunnell
  • Patent number: 5013745
    Abstract: 2-Mercapto-1,3,4-oxadiazoles and 2-mercapto-1,3,4-thiadiazoles of the formula I ##STR1## in which X.sub.1 and X.sub.2 independently of one another are oxygen or sulfur, R.sub.1 is difluoromethyl or 3,4,4-trifluoro-3-butenyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl and R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkenyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkynyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, or phenyl which is unsubstituted or substituted by halogen, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 alkoxy, or wherein, furthermore, R.sub.2 and R.sub.3 together can form the methylene chain (--CH.sub.2 --)n as a constituent of a 5- or 6-membered ring with the heteroatom X.sub.1, in which n is 3 or 4, and processes for the preparation of the compounds of the formula I are described.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: May 7, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ernst Beriger, Wolfgang Eckhardt
  • Patent number: 5001138
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: March 19, 1991
    Assignee: Nihon Tokushu Noyaku Seizo, K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4988380
    Abstract: A process for selectively combating weeds in crops, comprising applying to a locus in which such crops are growing or are to be grown a herbicidally effective amount of a difluoromethyl-thiadiazolyl-oxy-acetamide of the formula ##STR1## in which R.sup.1 stands for hydrogen or for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl and aralkyl,R.sup.2 stands for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy and alkinyloxy, orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are bonded form an optionally substituted, saturated or unsaturated heterocycle which can contain further hetero atoms and to which a benzo group may be fused.Compounds wherein R.sup.1 is C.sub.2 -C.sub.4 -alkyl and R.sup.2 is optionally substituted phenyl are new as are intermediates of the formula ##STR2## in which x is 0 or 2.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 4988718
    Abstract: Fungicidal substituted 4-heterocyclyloximinopyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another in each case represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case unsubstituted or in each case substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an unsubstituted or substituted heterocycle.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Klaus Jelich, Gerd Hanssler
  • Patent number: 4988378
    Abstract: Herbicidal substituted thiadiazolyloxyacetamides of the formula ##STR1## in which R.sup.1 stands for hydrogen or for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl and aralkyl,R.sup.2 stands for an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy and alkinyloxy, orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are bonded form an optionally substituted, saturated or unsaturated heterocycle which can contain further hetero atoms and to which a benzo group can be fused, andR.sup.3 stands for an optionally substituted alkyl radical.Intermediates of the formulas ##STR2## in which R.sup.3 stands for optionally substituted alkyl, andX stands for S or SO.sub.2,are also new.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 4977167
    Abstract: A compound of the formula: ##STR1## (wherein R is phenoxy optionally substituted by a halogen, methoxy, or methyl group, ##STR2## one of A and B is ##STR3## and the other is >CH.sub.2 : R.sup.1 is hydrogen or C.sub.1 -C.sub.5 alkyl; Z.sup.1 is phenyl, benzyl, or isoxazolyl each optionally substituted by a halogen, methoxy, or methyl group; Z.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, or phenyl optionally mono-, di-, or tri-substituted by a halogen, methoxy, or methyl group; or Z.sup.1 and Z.sup.2 taken together with the adjacent nitrogen atom may form 5-membered heterocyclic group; Z.sup.3 is C.sub.1 -C.sub.5 hydroxyalkyl, di(C.sub.1 -C.sub.5 alkyl)sulfamoyl, 6-membered heterocyclic group, phenyl, benzyl, or phenylsulfonyl each phenyl moiety of the last three members being optionally substituted by a halogen, methoxy, or methyl group; Z.sup.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: December 11, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiromu Matsumura, Toshisada Yano, Akira Matsushita, Masami Eigyo
  • Patent number: 4968691
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents a group ##STR2## in which p represents an integer of 2 to 4; r represents an integer of 1 or 2; s represents 0 or 1; and A represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-4 alkyl group, and when (p,r,s) is (2,2,0) or (2,2,1) any A comprising 2 heteroatoms is optionally C-substituted by a methyl group, and when (p,r,s) is (2,1,0), (2,1,1) or (3,1,0) any A comprising 2 heteroatoms is optionally C-substituted by C.sub.1-2 alkyl and any A comprising one heteroatom is optionally C-substituted by a methyl group, and wherein compounds of formula (I) having two asymetric centers have the stereo-chemical configuration in which the group X and the (CH.sub.2).sub.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: November 6, 1990
    Assignee: Beecham Group P.L.C.
    Inventors: Barry S. Orlek, Michael S. Hadley, Howard E. Rosenberg, Harry J. Wadsworth
  • Patent number: 4968342
    Abstract: Herbicidal N-isopropylheteroaryloxyacetanilides of the formula ##STR1## in which A stands for nitrogen or the group C--R.sup.3 whereR.sup.3 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl or alkylsulphonyl,B stands for nitrogen or the group C--R.sup.4 whereR.sup.4 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, or for the group --CY.sub.2 --Z--R.sup.5 whereR.sup.5 stands for alkyl, which is optionally substituted by halogen, alkoxy or alkylthio, or for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio,Y stands for hydrogen or halogen,Z stands for oxygen, sulphur, SO or SO.sub.2,R.sup.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Roland Andree, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 4959379
    Abstract: Fungicidal 7-substituted 2-carboxamido-benzothiazole 3-oxides of the formula ##STR1## in which n stands for the numbers 0, 1, 2 or 3,R.sup.1 stands for hydrogen or optionally substituted alkyl,R.sup.2 stands for hydrogen, hydroxyl, ureido or for an optionally substituted radical from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, aralkoxy, aralkyl, aryl, heterocyclyl and heterocyclylakyl, orR.sup.1 and R.sup.2 together stand for an alkylene chain which is optionally substituted and optionally interrupted by hetero atoms,R.sup.3 stands for halogen, alkyl or halogenoalkyl andR.sup.4 stands for halogen, alkyl or halogenoalykl.The intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: March 21, 1989
    Date of Patent: September 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Wagner, Gerd Hanssler
  • Patent number: 4958043
    Abstract: A composition useful for incorporation into polymer compositions employed for food packaging or the like comprising a bis- or tris-methine compound having the structural formula ##STR1## wherein A is selected from the radicals ##STR2## wherein R' and R" are each selected from chlorine, bromine, fluorine, alkyl, alkoxy, aryl, aryloxy and arylthio;each n is independently 0, 1, 2;R.sub.1 is selected from a large variety of radicals such as cycloalkyl, phenyl, and straight or branched alkyl which may be substituted;R.sub.2 is alkylene or the like;R.sub.3, R.sub.4, and R.sub.5 are each selected from hydrogen and alkyl; andP and Q and P.sup.1 and Q.sup.1 are selected from cyano, carbalkoxy, carbaryloxy, carbaralkyloxy, or the like.The invention compositions are especially useful in combination with molding or fiber-grade condensation polymer; most preferably such polymer having copolymerized therein a total of from 1.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: September 18, 1990
    Assignee: Eastman Kodak Company
    Inventors: Max A. Weaver, Wayne P. Pruett, Samuel D. Hilbert
  • Patent number: 4954518
    Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: September 4, 1990
    Assignee: Toyama Chemical Company, Ltd.
    Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
  • Patent number: 4952580
    Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 28, 1990
    Assignee: FMC Corporation
    Inventors: Anthony J. Martinez, Thomas G. Cullen
  • Patent number: 4952699
    Abstract: 2,5-substituted 1,3,4-thiadiazoles of the general formula ##STR1##The aforementioned compounds are used in amounts of 0.1 to 80 mole percent in mixtures for electrooptical arrangements for the modulation of transmitted and reflected light, as well as for the colored or black-and-white display of numerals, symbols and moving or still pictures. The compounds endow the liquid-crystalline mixtures with an extended phase field of the smectic C phase, negative dielectric anisotropy and the property of forming optically active C phases upon admixture with optically active compounds.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: August 28, 1990
    Assignee: VEB Werk fuer Fernsehelektronik im VEB Kombinat Mikroelektronik
    Inventors: Bak G Yong, Dietrich Demus, Horst Kresse, Annelore Madicke, Gerhard Pelzl, Wolfgang Schafer, Carsten Tschierske, Horst Zaschke
  • Patent number: 4952703
    Abstract: Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with trichloracetyl isocyanate to produce novel N-trichloroacetyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as analgesic and anti-inflammatory agents and/or intermediates for such agents.
    Type: Grant
    Filed: May 25, 1989
    Date of Patent: August 28, 1990
    Assignee: Pfizer Inc.
    Inventor: Sarah E. Kelly
  • Patent number: 4952599
    Abstract: Novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by one or more halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups; C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl, di(C.sub.3 -C.sub.8)cycloalkyl-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 phenylalkyl or C.sub.1 -C.sub.4 phenylalkyl which is substituted in the phenyl nucleus by one or more members selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or C.sub.1 -C.sub.4 haloalkyl; or is C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
  • Patent number: 4943584
    Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
  • Patent number: 4943583
    Abstract: The invention is concerned with novel compounds of the formula ##STR1## wherein R.sup.1 signifies optionally substituted phenyl or pyridyl, R.sup.2 signifies substituted phenyl, X signifies oxygen, sulfur or NR.sup.3, Y signifies oxygen or sulfur and R.sup.3 signifies methyl, halomethyl or 2-propynyl, and their manufacture, pest control compositions which contain said compounds as the active ingredient and the use of the active substances or compositions for the control of pests.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: July 24, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Christoph Luthy
  • Patent number: 4929743
    Abstract: Herbicidally active novel 4,5-disubstituted 1,3-thiazol-2-yloxyacetamides of the formula ##STR1## in which R.sup.1 is fluorine or chlorine,R.sup.2 is alkyl or halogenoalkyl, andR.sup.3 and R.sup.4 each independently is alkyl, alkenyl, alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxyalkyleneoxy, alkoxy, aralkyl or optionally substituted aryl, orR.sub.3 and R.sub.4, conjointly with the nitrogen atom to which they are bonded form an optionally substituted, heterocyclic ring which can contain further hetero-atoms.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Gunther Beck, Erich Klauke, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 4927822
    Abstract: There are described compounds of formula I, ##STR1## in which Y is S, O or NR.sub.9,n is 0 or 1,R.sub.9 is hydrogen or alkyl C 1 to 10,R.sub.3 is hydrogen, alkyl C 1 to 10, cycloalkyl C3 to 10, CF.sub.3, SR.sub.10, a 5 or 6 membered heterocyclic group containing one or more S, O or N atoms, NR.sub.4 R.sub.5, phenyl or phenylalkyl C7 to 12, the phenyl, phenylalkyl and heterocyclic groups optionally being fused to a further phenyl group, the heterocyclic group and any phenyl group optionally being substituted by alkyl C 1 to 6, halogen, alkoxy C 1 to 6, nitro, nitrile, CF.sub.3, SR.sub.6, NR.sub.7 R.sub.11 or hydroxy,R.sub.6, R.sub.7 and R.sub.11, which may be the same or different, are each hydrogen or alkyl C 1 to 10,R.sub.4 and R.sub.5, which may be the same or different, are each hydrogen, alkyl C 1 to 10 or phenyl,R.sub.10 is alkyl C 1 to 10,X.sub.1 is S or O, andA is a chain comprising from 2-16 atoms, which chain carries an O or S containing substitutent at a position 2-6 atoms away from the group C=X.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: May 22, 1990
    Assignee: Fisons plc
    Inventors: Roger C. Brown, John Dixon, David H. Robinson
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4914206
    Abstract: The present invention provides lankacidin derivatives of the formula ##STR1## and procedures for the production thereof. The lankacidin derivatives [1] show excellent antimicrobial activities and thus can be used for prophylaxis and treatment of infectious disease in animals.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: April 3, 1990
    Assignee: Takeda Chemical Industries, LTD.
    Inventors: Isao Minamida, Naoto Hashimoto