1,3,4-thiadiazoles (including Hydrogenated) Patents (Class 548/136)
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Patent number: 5158943Abstract: 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: GrantFiled: May 23, 1991Date of Patent: October 27, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Iwao Yamazaki
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Patent number: 5155122Abstract: 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: GrantFiled: August 23, 1991Date of Patent: October 13, 1992Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Michael D. Mullican, Gary P. Shrum, Paul C. Unangst, Michael W. Wilson
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Patent number: 5147443Abstract: 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: GrantFiled: September 26, 1991Date of Patent: September 15, 1992Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Diehr, Karl-Heinz Kuck, Wilfried Paulus, Hans-Georg Schmitt
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Patent number: 5143642Abstract: 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: GrantFiled: January 11, 1991Date of Patent: September 1, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Thomas Geelhaar, Reinhard Hittich, Ulrich Finkenzeller, Bernhard Rieger, Georg Weber
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Patent number: 5138064Abstract: 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: GrantFiled: February 6, 1990Date of Patent: August 11, 1992Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Kohji Hattori, Takashi Nakajima
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Patent number: 5135938Abstract: Leukotriene antagonist thiadiazoles have been prepared.Type: GrantFiled: March 30, 1990Date of Patent: August 4, 1992Assignee: SmithKline Beecham CorporationInventors: John G. Gleason, Ralph F. Hall, Irene Uzinskas
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Patent number: 5132316Abstract: 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: GrantFiled: September 21, 1990Date of Patent: July 21, 1992Assignee: Beecham Group p.l.c.Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
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Patent number: 5120733Abstract: 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: GrantFiled: August 23, 1990Date of Patent: June 9, 1992Assignee: Shionogi and Co. Ltd.Inventors: Hiromu Matsumura, Toshisada Yano, Akira Matsushita, Masami Eigyo
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Patent number: 5102897Abstract: 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: GrantFiled: January 24, 1991Date of Patent: April 7, 1992Assignee: Warner-Lambert CompanyInventors: Diane H. Boschelli, David T. Connor, Catherine R. Kostlan, James B. Kramer, Michael D. Mullican, Jagadish C. Sircar
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Patent number: 5103007Abstract: 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: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5101034Abstract: 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: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5098600Abstract: 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: GrantFiled: December 20, 1990Date of Patent: March 24, 1992Assignee: Canon Kabushiki KaishaInventors: Shinichi Nakamura, Yoko Yamada, Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano
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Patent number: 5097038Abstract: 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: GrantFiled: November 14, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5096483Abstract: 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: GrantFiled: October 29, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 5091109Abstract: 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: GrantFiled: August 8, 1990Date of Patent: February 25, 1992Assignee: Canon Kabushiki KaishaInventors: Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shosei Mori, Shinichi Nakamura
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Patent number: 5091397Abstract: 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: GrantFiled: September 29, 1989Date of Patent: February 25, 1992Assignee: Beecham Group p.l.c.Inventors: Harry J. Wadsworth, Michael S. Hadley, Paul A. Wyman, Sarah M. Jenkins
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Patent number: 5086186Abstract: 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: GrantFiled: May 31, 1990Date of Patent: February 4, 1992Assignee: Pfizer Inc.Inventor: Sarah E. Kelly
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Patent number: 5081245Abstract: 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: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5076961Abstract: 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: GrantFiled: July 6, 1990Date of Patent: December 31, 1991Assignee: Canon Kabushiki KaishaInventors: Shinichi Nakamura, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shosei Mori
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Patent number: 5073563Abstract: 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: GrantFiled: October 5, 1989Date of Patent: December 17, 1991Assignee: BASF AktiengesellschaftInventors: Fritz-Frieder Frickel, Thomas Kuekenhoehner, Beatrice Rendenbach-Mueller, Harald Weifenbach, Hans-Juergen Teschendorf
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Patent number: 5071841Abstract: 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: GrantFiled: December 28, 1989Date of Patent: December 10, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
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Patent number: 5064962Abstract: 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: GrantFiled: February 1, 1990Date of Patent: November 12, 1991Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Karl-Heinz Etzbach
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Patent number: 5061804Abstract: 3-thio pyrrolidines are intermediates for carbapenams.Type: GrantFiled: March 6, 1990Date of Patent: October 29, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Hohji Hattori, Takashi Nakajima
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Patent number: 5051421Abstract: 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: GrantFiled: January 18, 1990Date of Patent: September 24, 1991Assignee: Ciba-Geigy CorporationInventor: Pier G. Ferrini
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Patent number: 5051515Abstract: 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: GrantFiled: March 27, 1989Date of Patent: September 24, 1991Assignee: SynPhar Laboratories IncorporatedInventors: Mohsen Daneshtalab, Ronald G. Micetich, Dai Q. Nguyen, Chan M. Ha, Hiep T. Luu
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Patent number: 5047554Abstract: 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: GrantFiled: January 31, 1990Date of Patent: September 10, 1991Assignee: Pfizer Inc.Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
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Patent number: 5034047Abstract: 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: GrantFiled: August 24, 1990Date of Patent: July 23, 1991Assignee: BASF AktiengesellschaftInventors: Dieter Kolassa, Juergen Kast, Thomas Kuekenhoehner, Norbert Meyer, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5034151Abstract: 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: GrantFiled: March 27, 1989Date of Patent: July 23, 1991Assignee: Canon Kabushiki KaishaInventors: Kenji Shinjo, Akio Yoshida, Takashi Iwaki, Takao Takiguchi, Hiroyuki Kitayama, Kazuharu Katagiri
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Patent number: 5013854Abstract: 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: GrantFiled: February 2, 1989Date of Patent: May 7, 1991Assignee: Eli Lilly and CompanyInventor: Charles A. Bunnell
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Patent number: 5013745Abstract: 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: GrantFiled: September 18, 1989Date of Patent: May 7, 1991Assignee: Ciba-Geigy CorporationInventors: Ernst Beriger, Wolfgang Eckhardt
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Patent number: 5001138Abstract: 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: GrantFiled: May 4, 1989Date of Patent: March 19, 1991Assignee: Nihon Tokushu Noyaku Seizo, K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4988380Abstract: 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: GrantFiled: June 15, 1989Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4988718Abstract: 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: GrantFiled: August 9, 1990Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Klaus Jelich, Gerd Hanssler
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Patent number: 4988378Abstract: 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: GrantFiled: June 15, 1989Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4977167Abstract: 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: GrantFiled: August 17, 1988Date of Patent: December 11, 1990Assignee: Shionogi & Co., Ltd.Inventors: Hiromu Matsumura, Toshisada Yano, Akira Matsushita, Masami Eigyo
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Patent number: 4968691Abstract: 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: GrantFiled: March 7, 1989Date of Patent: November 6, 1990Assignee: Beecham Group P.L.C.Inventors: Barry S. Orlek, Michael S. Hadley, Howard E. Rosenberg, Harry J. Wadsworth
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Patent number: 4968342Abstract: 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: GrantFiled: June 15, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Roland Andree, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4959379Abstract: 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: GrantFiled: March 21, 1989Date of Patent: September 25, 1990Assignee: Bayer AktiengesellschaftInventors: Klaus Wagner, Gerd Hanssler
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Patent number: 4958043Abstract: 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: GrantFiled: April 18, 1988Date of Patent: September 18, 1990Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Wayne P. Pruett, Samuel D. Hilbert
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Patent number: 4954518Abstract: 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: GrantFiled: October 7, 1988Date of Patent: September 4, 1990Assignee: Toyama Chemical Company, Ltd.Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
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Patent number: 4952580Abstract: 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: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen
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Patent number: 4952699Abstract: 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: GrantFiled: June 20, 1988Date of Patent: August 28, 1990Assignee: VEB Werk fuer Fernsehelektronik im VEB Kombinat MikroelektronikInventors: Bak G Yong, Dietrich Demus, Horst Kresse, Annelore Madicke, Gerhard Pelzl, Wolfgang Schafer, Carsten Tschierske, Horst Zaschke
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Patent number: 4952703Abstract: 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: GrantFiled: May 25, 1989Date of Patent: August 28, 1990Assignee: Pfizer Inc.Inventor: Sarah E. Kelly
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Patent number: 4952599Abstract: 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: GrantFiled: July 20, 1988Date of Patent: August 28, 1990Assignee: Ciba-Geigy CorporationInventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
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Patent number: 4943584Abstract: 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: GrantFiled: April 20, 1988Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
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Patent number: 4943583Abstract: 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: GrantFiled: December 1, 1987Date of Patent: July 24, 1990Assignee: Hoffmann-La Roche Inc.Inventor: Christoph Luthy
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Patent number: 4929743Abstract: 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: GrantFiled: June 15, 1988Date of Patent: May 29, 1990Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Gunther Beck, Erich Klauke, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 4927822Abstract: 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: GrantFiled: August 27, 1986Date of Patent: May 22, 1990Assignee: Fisons plcInventors: Roger C. Brown, John Dixon, David H. Robinson
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Patent number: 4920231Abstract: 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: GrantFiled: March 30, 1989Date of Patent: April 24, 1990Assignee: Roussel UclafInventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4914206Abstract: 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: GrantFiled: December 15, 1988Date of Patent: April 3, 1990Assignee: Takeda Chemical Industries, LTD.Inventors: Isao Minamida, Naoto Hashimoto