Additional Chalcogen Attached Directly Or Indirectly To The Diazine Ring By Nonionic Bonding Patents (Class 544/318)
  • Patent number: 5089513
    Abstract: The invention concerns a thiazole of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted aryl of up to 10 carbon atoms;A is a direct link to X, or is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;R.sup.2 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, substituted (1-4C)alkyl or (2-6C)alkanoyl;Q is optionally substituted thiazolyl;or a pharmaceutically-acceptable salt thereof.The invention also concerns processes for the manufacture of a thiazole of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said thiazole.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: February 18, 1992
    Assignees: ICI Pharma, Imperial Chemical Industries PLC
    Inventors: Thomas G. C. Bird, Graham C. Crawley, Martin P. Edwards, Philip N. Edwards, Jean-Marc M. M. Girodeau, John F. Kingston
  • 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: 5085686
    Abstract: Salicylaldehyde derivatives and salicyclic acid derivatives of the formula I ##STR1## where A is an unsubstituted or substituted phenyl radical, an unsubstituted or substituted 5-membered heteroaromatic radical having from 2 to 4 nitrogen atoms or two nitrogen atoms and additionally one sulfur or oxygen atom or an unsubstituted or substituted thienyl, pyridyl, naphthyl, quinolyl, indazolyl or benzotriazolyl radical, X is oxygen or sulfur, and the radicals R.sup.1 and R.sup.4 have the means given in the specification, processes and intermediates for their production, and their use as herbicides and bioregulators.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: February 4, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe J. Vogelbacher, Karl Eicken, Joachim Rheinheimer, Norbert Goetz, Albrecht Harreus, Gerhard Paul, Karl-Otto Westphalen, Bruno Wuerzer
  • 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: 5079361
    Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5075020
    Abstract: Compounds suitable for use as extreme pressure (EP)/anti-wear (AW) agents in lubricating oil compositions, which compounds have the formula:R.sup.1 --S--X--S--S--R (I)whereinR.sup.1 is either R--S-- or hydrogen,R is independently either hydrocarbyl or substituted hydrocarbyl, andX comprises a heterocyclic ring having six atoms of which two are nitrogen atoms.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: December 24, 1991
    Assignee: BP Chemicals (Additives) Limited
    Inventor: Sean P. O'Connor
  • Patent number: 5075446
    Abstract: The synthesis of 1-(tetrahydro-2-furyl) pyrimidine derivatives in good yields by the reaction of trimethylsilylated pyrimidine bases with 2-acetoxytetrahydrofuran using a catalytic amount of cesium chloride in acetonitrile under mild conditions is described.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: December 24, 1991
    Assignee: Korea Advanced Institute of Science & Technology
    Inventors: Yong H. Kim, Chun H. Lee
  • Patent number: 5071860
    Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
  • Patent number: 5066658
    Abstract: The present invention relates to substituted hydroxyureas. These compounds inhibit the enzyme 5-lipoxygenase. In addition, certain of the compounds also inhibit the enzyme-cyclooxygenase. The compounds are useful for treating asthma, allergies, arthritis, posoriasis, ischemia, dermatitis, inflammation and/or broncho-constriction and/or inflammatory diseases of the eye.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: November 19, 1991
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: James P. Demers, Richard B. Sulsky
  • Patent number: 5066800
    Abstract: A novel process and intermediates used therein for linking a cephalosporin compound to a quinolone are disclosed. According to the disclosed process, the 2-carboxylic acid moiety of the cephalosporin compound is treated with an organic base. The resulting salt is then reacted with a quinolone compound which has been activated using a haloformate. The reaction is run in a non-aqueous organic solvent. 4-Dimethylaminopyridine is used to promote the reaction between the cephalosporin salt and the activated quinolone.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: November 19, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Masami Okabe
  • Patent number: 5057143
    Abstract: Salicyclic acid derivatives and their sulfur analogs of the formula I ##STR1## where R.sup.1 to R.sup.5, X, Y and Z have the meanings given in the disclosure and claims, agents containing the salicyclic acid derivatives, and their use as herbicides.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: October 15, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Rheinheimer, Karl Eicken, Peter Plath, Gerhard Paul, Albrecht Harreus, Karl-Otto Westphalen, Bruno Wuerzer, Klaus Grossmann, Wilhelm Rademacher, Johann Jung
  • Patent number: 5034050
    Abstract: Derivatives of 4-((aryloxy)phenoxy)alkenols, their preparation and use as active herbicides for the postemergent control of grassy weeds and especially the control of said weeds in the presence of corn plants are disclosed.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: July 23, 1991
    Assignee: DowElanco
    Inventors: James A. Turner, Paul S. Zorner, Wendy S. Jacks
  • Patent number: 5032168
    Abstract: Disclosed herein are derivatives of 4-((aryloxy)phenoxy)fluoroalkanoic acid and their use as active herbicides for the pre- and postemergent control of grassy weeds, especially in the presence of broadleaf crops.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: July 16, 1991
    Assignee: DowElanco
    Inventor: James A. Turner
  • Patent number: 5032592
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 5030726
    Abstract: The present invention relates to polymerizable cyclic urea derivatives which can be thermally split to give rise to an isocyanate group; and to a polymer having cyclic urea pendant groups, which can be cured by heating without any additional curing agent such as an isocyanate blocked with a volatile lower molecular weight material, so that volatile material is not released in a thermal curing process.
    Type: Grant
    Filed: December 29, 1989
    Date of Patent: July 9, 1991
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Tsuboniwa Noriyuki, Urano Satoshi, Umemoto Hirotoshi, Sakamoto Hiroyuki, Tobinaga Kenshiro, Tsuchiya Yasuyuki
  • Patent number: 5028711
    Abstract: Benzopyran derivatives of the general formula I ##STR1## are disclosed. The compounds are therapeutic active compounds.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 2, 1991
    Assignee: Beiersdorf Aktiengesellschaft
    Inventors: Wolfgang Stenzel, Theo Schotten, Ben Armah
  • Patent number: 5021581
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted aryl or optionally substituted heteroaryl; Y is oxygen, sulphur or NR.sup.4 ; R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl; X is halogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy, nitro or cyano; and n is 0 or an integer of 1 to 4; provided that when Y is oxygen, n is O and R.sup.1 is unsubstituted phenyl at least one of R.sup.2 and R.sup.3 is other than hydrogen or methyl.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: June 4, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Vivienne M. Anthony
  • Patent number: 5019151
    Abstract: A 2-phenoxypridimine derivative having the formula: ##STR1## wherein X is a halogen atom or ##STR2## wherein X.sup.1 is a halogen atom, a lower alkyl group or a lower alkoxy group and k is 0, 1, or 2; R.sup.1 is a hydrogen atom, a benzyl group, --(CH.sub.2).sub.m R.sup.3 is a cyano group, a formyl group, a dialkylamino group, a phenyl group, a pyridyl group, a trimethylsilyl group, a naphthyl group, an alkoxycarbonyl group, a benzoyl group, an alkylthio group, a phenylthio group, an alkylsulfonyl group or a benzyloxy group and m is 1, 2, or ##STR3## wherein R.sup.4 is a hydrogen atom or a lower alkyl group, R.sup.5 is a lower alkyl group or ##STR4## wherein X.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, n is 0 or 1, provided that when R.sup.5 is an alkyl group, n is 1; and R.sup.2 is a chlorine atom or a methoxy group, provided that when R.sup.1 is a hydrogen atom or a benzyl group, X is ##STR5## and R.sup.2 is a methoxy group, when R.sup.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: May 28, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi, Takayoshi Takehi
  • Patent number: 5015285
    Abstract: Aromatic carboxylic acid derivatives of the formula ##STR1## in which the radical ##STR2## is a substituted or unsubstituted quinoline, naphthalene, benzofuran, thiophene or pyridine radical,R.sup.1 is hydrogen, alkylidenaminoxy, unsubstituted or substituted cycloalkylidenaminoxy, succinyliminoxy, unsubstituted or substituted alkenyloxy, alkynyloxy, azolyl, alkylsulfonylamino, alkoxycarbonylalkyloxy, N-azolylalkyloxy, unsubstituted or substituted alkoxy, unsubstituted or substituted phenylalkoxy, hydroxyl or the radical O.sup..crclbar. M.sup..sym., M.sup..sym. being one equivalent of an alkali metal, alkaline earth metal or organic ammonium ion,R.sup.2 and R.sup.3 are alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio,X is oxygen or sulfur,Y and Z are nitrogen or the methine group, andR.sup.4 and R.sup.5 are hydrogen, halogen, alkyl, haloalkyl, nitro, alkoxy, unsubstituted or substituted alkenyloxy, acylamino, alkylamino, dialkylamino or arylamino, and their use for controlling the growth of unwanted plants.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: May 14, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Rheinheimer, Peter Plath, Karl Eicken, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5010200
    Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 -OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: April 23, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward McDonald, Roger Salmon, Alan J. Whittle, Michael G. Hutchings
  • Patent number: 5002694
    Abstract: Nitrogen-containing heterocyclic compounds of the formula II ##STR1## wherein R.sup.1 and R.sup.2 in each case denote an alkyl group having 1 to 15 C atoms, wherein one or more CH.sub.2 groups may also be replaced by a grouping selected from the group comprising --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --CH.dbd.CH--, --CH--halogen and --CHCN--, or else by a combination of two suitable groupings, two heteroatoms not being directly linked to each other,m denotes 0 or 1,Ar denotes 1,4-phenylene, 4,4'-biphenylyl or 2,6-naphthylene, wherein one or more CH groups are in each case replaced by N,Z denotes --C--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CHCN--, --CHCNCH.sub.2 --, --CH.dbd.CH or a single bond, andA denotes unsubstituted 1,4-cyclonexylene or 11,4-cyclohexylene substituted in position 1 or position 4 by CN,with the proviso that if A=unsubstituted 1,4-cyclonexylene, Z denotes --CHCNCH.sub.2 -- or --CH.sub.2 CHCN-- and/or at least one CH.sub.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: March 26, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble
  • Patent number: 4999042
    Abstract: Compounds of the fomrula (I): ##STR1## and sterioisomers thereof, wherein X is halogen, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino nitro, nitride, trifluoromethyl, -OR.sup.1, -SR.sup.1, -CO.sub.2 R.sup.2, -CONR.sup.3 R.sup.4, -COR.sup.5, -CR.sup.6 .dbd.NR.sup.7, -N.dbd.CR8R.sup.9, -SOR.sup.10 or -SO.sub.2 R.sup.11 ; W, Y and Z, which may be the same or different, are any of the atoms or groups listed for X above and, in addition, may be hydrogen atoms; or any two of the groups W, X, Y and Z, in adjacent positions on the phenyl ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 is alkyl, or cycloalkyl optionally containing a heteroatom in the cycloalkyl ring, alkenyl, acyl, aryl, heteroaryl, aralkyl or heteroarylalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, R.sup.9, R.sup.10 and R.sup.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: March 12, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Christopher R. A. Godfrey, Thomas E. Wiggins
  • Patent number: 4996216
    Abstract: Phenoxyalkyl-substituted heteroaromatics of the general formulae Ia and Ib ##STR1## where A is an unsubstituted or substituted heteroaromatic radical having 6 ring members and 1, 2 or 3 nitrogen atoms in the ring, R.sup.1 is hydrogen, halogen or C.sub.1 -C.sub.3 -alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl, Q.sub.a is an unsubstituted or substituted azole radical and Q.sub.b is a substituted or unsubstituted heteroaromatic radical which has a five-membered ring,and their use for combating pests.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: February 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Leyendecker, Hans-Juergen Neubauer, Uwe Kardorff, Christoph Kuenast, Peter Hofmeister, Wolfgang Krieg
  • Patent number: 4988459
    Abstract: Optically active oxirane-2-carboxylic acid esters with a mesogenic molecular component suitable as dopants in liquid-crystal mixtures. They result in liquid-crystalline ferroelectric phases with short switching times and in electroclinic phases with large electroclinic coefficients. A further advantage lies in the fact that they induce a helix with a very small pitch so that they are also suitable for helix compensation in LC mixtures.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: January 29, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Jurgen Gay, Hans-Rolf Dubal, Claus Escher, Wolfgang Hemmerling, Ingrid Muller, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 4985066
    Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein R.sup.1 is a formyl group, a dimethoxymethyl group or --COOR.sup.4 (wherein R.sup.4 is a hydrogen atom, a lower alkyl group, a benzyl group, an alkali metal atom, an alkaline earth metal atom or an organic ammonium group), R.sup.2 is a chlorine atom, a methyl group, a methoxy group or a difluoromethoxy group, R.sup.3 is a methyl group or a methoxy group, X is a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group, a nitro group or a cyano group, and n is 1 or 2.
    Type: Grant
    Filed: November 24, 1989
    Date of Patent: January 15, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasuhumi Toyokawa, Takeshige Miyazawa, Ikuo Kajiwara, Satoru Takahashi
  • Patent number: 4983610
    Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I)Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 1-oxo-4,5-diphenyl-2H-pyrimidin-1-yl.
    Type: Grant
    Filed: February 13, 1990
    Date of Patent: January 8, 1991
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4973599
    Abstract: Compounds of the formula ##STR1## wherein n is a integer of 0 to 2; R.sub.1 ' and R.sub.2 ' are, independently, hydrogen, halogen, trifluoromethyl, lower alkoxy or lower alkyl; and X is pyrimidinyl, thiazolyl or ##STR2## wherein R is hydrogen, lower alkyl, aryl or ar-lower alkyl; provided that at least one or R.sub.1 ' and R.sub.2 ' is other than hydrogen,and their pharmaceutically acceptable acid addition salts, and an anti-inflammatory method utilizing a compound of the formula ##STR3## wherein n is an integer of 0 to 2; R.sub.1 and R.sub.2 are, independently, hydrogen, halogen, trifluoromethyl, nitro, amino, lower alkylamino, di-lower-alkylamino, lower alkoxy or lower alkyl; and X is pyrimidinyl, thiazolyl or ##STR4## wherein R is hydrogen, lower alkyl, aryl or ar-lower alkyl; and their pharmaceutically acceptable acid addition salts, are described.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: November 27, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Norman W. Gilman, Wen Y. Chen
  • Patent number: 4973354
    Abstract: Disclosed are pyrimidine derivatives of the formula (I) and optical isomers thereof and a herbicide containing one or more of them as an active ingredient. ##STR1## where W is O or S; X is a lower alkyl group or a lower alkoxycarbonyl group; R is H, an optionally substituted lower alkyl group, an optionally substituted lower alkenyl group, an optionally substituted lower alkynyl group, an alkyali metal, an alkaline earth metal or an optionally substituted ammonium cation; R.sup.1 and R.sup.2 each are a halogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkoxy group; n is 3 to 5; m is 0 to 2; and is a single bond or a double bond.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: November 27, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Masataka Hatanaka, Junichi Watanabe, Yasuo Kondo, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
  • Patent number: 4968690
    Abstract: The new compound 3-deazaneplanocin A has been discovered to have potent anti-viral, anti-tumor activity and differentiating activity. A simple method for preparing 3-deazaneplanocin A has been developed involving nucleophilic substitution, which method can also be used to prepare a great variety of carbocyclic nucleosides.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: November 6, 1990
    Assignee: United States Government as represented by the Secretary of the Dept. of Health and Human Services
    Inventors: Victor E. Marquez, John S. Driscoll, Mu-Ill Lim, Christopher K. Tseng, Alberto Haces, Robert I. Glazer
  • Patent number: 4968340
    Abstract: A herbicidal alkanoic acid derivative of the formula: ##STR1## wherein R is ##STR2## wherein R.sup.3 is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkyl group, a cycloalkyl group, an alkylthioalkyl group, a hydroxyalkyl group, a hydroxyl group, a cyano group, an acyloxyalkyl group, a thienyl group, a naphthyl group, a dihydronaphthyl group or ##STR3## wherein R.sup.8 is a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group or --S(O).sub.n R.sup.9 wherein R.sup.9 is an alkyl group, and n is an integer of from 0 to 2, m is an integer of from 0 to 2, each of R.sup.2 and R.sup.4 which may be the same or different is a hydrogen atom or an alkyl group, or R.sup.2 and R.sup.4 form together with the adjacent carbon atom a 3-, 4-, 5- or 6-membered ring which may contain an oxygen atom and may be substituted by one or two alkyl groups, each of R.sup.5 and R.sup.6 which may be the same or different is a hydrogen atom or an alkyl group, R.sup.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: November 6, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Koichiro Kaku, Nobuhide Wada, Akira Takeuchi, Yasufumi Toyokawa, Takeshige Miyazawa, Ryo Yoshida, Kazuhiko Sugiyama
  • Patent number: 4968688
    Abstract: Compounds of the formula: ##STR1## and stereoisomers thereof where W is pyridyl or pyrimidinyl linked to A by any one of its ring carbon atoms. A is an oxygen atom or S(O).sub.n where n is 0, 1 or 2; X, Y and Z are, for example, hydrogen, halogen, hydroxy or alkyl; and R.sup.1 and R.sup.2 are optionally substituted alkyl but with certain provisos. The compounds are useful as plant fungicides.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: November 6, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher Godfrey
  • Patent number: 4962109
    Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 --OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.
    Type: Grant
    Filed: June 13, 1988
    Date of Patent: October 9, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward McDonald, Roger Salmon, Alan J. Whittle
  • Patent number: 4960777
    Abstract: Heteroaryloxy-.beta.-carboline derivatives of general Formula I ##STR1## wherein R.sup.1 is an optionally substituted heteroaryl residue,R.sup.2 is hydrogen, lower alkyl or lower alkoxyalkyl,X is a COOR.sup.3 -group wherein R.sup.3 means H or lower alkyl, or represents a CONR.sup.4 R.sup.5 -group wherein R.sup.4 and R.sup.5 mean respectively hydrogen or lower alkyl, R.sup.4 and R.sup.5 being capable of forming, together with the nitrogen atom, a 5- to 6-membered heterocycle, or means an oxadiazolyl residue of the formula ##STR2## wherein R.sup.6 means hydrogen, lower alkyl or cycloalkyl, are valuable pharmaceuticals.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: October 2, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David Stephens, Mogens Engelstoft, John B. Hansen
  • Patent number: 4956366
    Abstract: Substituted thienoimidazole derivatives, a process for the preparation thereof, pharmaceutical compositions containing them, and the use thereof as inhibitors of gastric acid secretion, as gastroprotectives and as medicaments for intestinal inflammationsThe invention relates to compounds of the formula ##STR1## in which A represents ##STR2## T denotes --S--, --SO-- or --SO.sub.2 --, R.sup.1 to R.sup.10, X, Y and Z have the meanings indicated in the description, to a process for the preparation thereof, to pharmaceutical compositions containing them, and to the use thereof as inhibitors of gastric acid secretion, as gastroprotectives and as medicaments for intestinal inflammations.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: September 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hildegard Nimmesgern, Klaus Weidmann, Hans-Jochen Lang, Robert Rippel, Andreas W. Herling
  • Patent number: 4956369
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 and R.sub.3, which are the same or different, are alkoxycarbonyl, acetyl, cyano, nitro, benzoyl or amino-carbonyl groups,R.sub.2 is differently substituted aryl or heteroaryl group;R.sub.4 is a C.sub.1 -C.sub.12 alkyl group optionally substituted by amino, alkoxyl, amine, etc. groups; alkenyl, or alkinyl groups; optionally substituted aryl or heteroaryl groups.Compounds I are useful as antihypertensives in human therapy.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: September 11, 1990
    Assignee: Boehringer Biochemia Robin S.p.A.
    Inventors: Marco Frigerio, Carmelo A. Gandolfi, Sergio Tognella
  • Patent number: 4946845
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.
    Type: Grant
    Filed: November 25, 1988
    Date of Patent: August 7, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: D. V. Krishna Murthy, Michael C. Venuti, John M. Young
  • Patent number: 4940712
    Abstract: 2-Amino and 2-thio-4-substituted-5-(hydroxy or alkoxy)-pyrimidines, which may be 6-substituted, and derivatives thereof are disclosed. The compounds are inhibitors of leukotriene synthesis and are, therefore, useful for the treatment of pulmonary, inflammatory, dermatological, allergic and cardiovascular diseases. The compounds are also cytoprotective and therefore, useful in the treatment of peptic ulcers.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: July 10, 1990
    Assignee: Pfizer Inc.
    Inventors: Frederick J. Walker, Lawrence S. Melvin
  • Patent number: 4933348
    Abstract: This invention relates to novel heterocyclic compounds structurally characterized by containing a specific heterocyclic group and by the presence of --CH.sub.2 --S-- directly bound to the specific heterocyclic group. These heterocyclic compounds are useful as medicines, particularly as antagonists of SRS-A (slow reacting substance of anaphylaxis).
    Type: Grant
    Filed: August 4, 1988
    Date of Patent: June 12, 1990
    Inventors: Toshiyasu Mase, Ryuji Tsuzuki, Hiromu Hara, Kiyoshi Murase, Kenichi Tomioka
  • Patent number: 4931560
    Abstract: Compounds of the formula ##STR1## in which: R.sub.1 and R.sub.2 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy orC.sub.1 -C.sub.3 haloalkoxy; R.sub.3 is hydrogen; C.sub.1 -C.sub.4 alkyl; or C.sub.1 -C.sub.4 alkyl substituted by halogen, hydroxy or by cyano; cyclopropyl; or cyclopropyl mono- to tri-substituted by methyl and/or by halogen; and R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl orC.sub.3 -C.sub.6 cycloalkyl mono-to tri-substituted by methyl and/or by halogen, have valuable microbicidal and insecticidal properties. The novel active ingredients can be used in plant protection for preventing an attack on cultivated plants by phytopathogenic microorganisms or by harmful insects, and for controlling these pests.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: June 5, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4929726
    Abstract: A method of preparation of substituted halogenodiazines which are useful as intermediates in the synthesis of novel unfused heterobicyclic compounds, and the products thereof.The reaction consists of the addition of an organolithium reagent with subsequent dehydrogenation of the addition product. The reaction takes place in one reaction vessel, without isolation of the substituted halogenodihydrodiazine intermediate. The reactions proceed at moderate temperature and in a short amount of time, which decreases the probability of side reactions and increases yield. Furthermore, the workup step is conducted under two-phase conditions to prevent hydrolysis of the substituted halogenodiazine to a substituted hydroxydiazine. The method is easy, efficient and results in a high yield of product.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: May 29, 1990
    Assignee: Georgia State University Foundation, Inc.
    Inventors: Lucjan Strekowski, Maria Mokrosz, Donald B. Harden
  • Patent number: 4927450
    Abstract: N-(2,2-Dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-pyrimidinylureas, N-(2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-triazolylureas and N-(2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-triazinylureas of the formula ##STR1## wherein R.sup.1 is hydrogen, halogen, nitro, 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, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy,R.sup.2 and R.sup.3 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.4 is hydrogen, methyl or ethyl,W is oxygen or sulfur, andA is a radical ##STR2## in which formulae the substituents E.sup.1, E.sup.2, X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.61, Y.sup.8, Y.sup.81, Z.sup.3 and Z.sup.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: May 22, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Fory, Willy Meyer
  • Patent number: 4923989
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;R.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl; andn is selected from the integers 1 and 2.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: May 8, 1990
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graeme J. Farquharson
  • Patent number: 4921632
    Abstract: Liquid Crystal compounds represented by the following formula are disclosed. ##STR1## wherein R and R' are independently selected from alkyl groups containing 1.about.20 carbon atoms; X is --O--, --O--CO--O-- or direct bond; A.sub.1 and A.sub.2 are independently cyclic groups (such as phenylene and biphenylene), said cyclic groups may be substituted with 1.about.4 fluorine, chlorine or bromine atoms, or 1 or 2 substituent groups selected from the group consisting of cyano, nitro and trifluoromethyl groups; Y is --CO--O--, --O--CO--, --C.tbd.C--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --CH.sub.2 S--, --SCH.sub.2 -- or direct bond; and * represents asymmetric atom providing optical activity.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: May 1, 1990
    Assignees: NEC Corporation, Sanyo Chemical Industries, Ltd.
    Inventors: Toyokazu Nakamura, Yuzi Kato, Shohei Naemura, Chizuka Tani, Masahiro Satoh, Kunikiyo Yoshio, Hiroshi Kishiki, Hiroshi Hoshino
  • Patent number: 4918213
    Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
  • Patent number: 4915868
    Abstract: Optically active esters of 1-acylproline of the general formula ##STR1## in which at least one of the radicals R.sup.1 and R.sup.2 is a mesogenic radical, are suitable as dopes in ferroelectric liquid-crystal mixtures. Proline derivatives in which only the R.sup.1 radical is mesogenic are preferred.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: April 10, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Gunther, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 4914116
    Abstract: A nitrogen-containing heterocyclic compounds are representable by the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.4 is a hydrogen atom, a halogen atom or a methyl group and l is an integer of 1 or 2);R.sub.2 is a hydrogen atom or a methyl group;R.sub.3 is an alkyl group, an alkoxy group, an alkenyl group or an alkenyloxy group, all of which may have optionally one or more substituents;A is either one of the following groups: ##STR3## (in which R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are, the same or different, each a hydrogen atom or a methyl group, R.sub.10 is a hydrogen atom, a halogen atom or a lower alkyl group and m is an integer of 1 to 4); andX is an oxygen atom or a sulfur atom,which is useful as an insecticidal agent.
    Type: Grant
    Filed: April 10, 1989
    Date of Patent: April 3, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
  • Patent number: 4913838
    Abstract: An optically active liquid crystal compound having specific features suitable to a display mode utilizing ferroelectric chiral smectic phases and particularly having a large spontaneous polarization value, and a chiral liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 represents an alkyl group of 2 to 18 carbon atoms; R.sup.2 represents an alkyl group or alkoxy group each of 1 to 20 carbon atoms, hydrogen atom, a halogen atom or cyano group; A represents --COO-- or --OCO--; B and C each represent a single bond, ##STR2## wherein X represents hydrogen atom, a halogen atom or cyano group; and l, m and n each represent 0 or 1.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: April 3, 1990
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Takashi Inukai, Hiromichi Inoue, Shinichi Saito, Kouji Ohno
  • Patent number: 4908368
    Abstract: Novel heterocyclic compounds shown by the general formula ##STR1## or the pharmaceutically acceptable salts thereof useful as medicament in particular as antagonist of slow reacting substance of anaphylaxis(SRS-A).
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: March 13, 1990
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 4906752
    Abstract: Liquid-crystal 5-phenylpyrmidine derivatives having S.sub.c or S.sup.*.sub.c phases and a process for preparing them. The new liquid-crystal 5-phenylpyrimidine derivatives have an S.sub.c or S.sup.*.sub.c phase and are described by the general formula (I) ##STR1## in which the symbols have the following meaning: R.sup.1 and R.sup.2 denote identical or different, straight-chain or branched alkyl or alkenyl groups having from k to 16 carbon atoms, with or without an asymmetric carbon atom, in which one or more non-adjacent --CH.sub.2 -- groups can be replaced by --O-- and /or --S----A and --B each denote ##STR2## in which the radicals R.sup.1, R.sup.2, in each case, are situated at the phenylene part of --A, --B andm and n denote 0 or 1, but m and n do not simultaneously denote 1, with the following provisos:(a) if m=n=0, k is 8, and in R.sup.2 the --CH.sub.2 -- group adjacent to the phenyl nucleus is replaced by --O--;(b) if m=1 and n=0, k is 2, and(c) if m=0 and n=1, k is 2 and in R.sup.2 the --CH.sub.
    Type: Grant
    Filed: July 12, 1989
    Date of Patent: March 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ingrid Muller, Hans-Rolf Dubal, Claus Escher, Wolfgang Hemmerling, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 4904409
    Abstract: An optically active compound having characteristics necessary for realizing liquid crystal compositions provided with suitable characteristics, particularly a negative temperature characteristic and a very high twistability, and a liquid crystal composition containing the compound are provided, which optically active compound is expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 are 1-20 C alkyl or alkoxy or H; l, m and n are 0 or 1; X is F, Cl, Br or CN; and ##STR2## each independently represent ##STR3## wherein Y is H, halogen or CN.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: February 27, 1990
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Ohno Kouji, Naoyuki Yoshida, Masakazu Kaneoya