Chalcogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/288)
  • Patent number: 5411936
    Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,x is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: May 2, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5401856
    Abstract: A cyclocarbonylation process for making pyrrolidones under mild temperature and pressure conditions is disclosed. In the process, an allylic amine reacts with carbon monoxide in the presence of a rhodium carbonyl catalyst and an amount of a pyridine promoter effective to enhance the yield of pyrrolidone obtained in the process compared with the yield obtained in the absence of the promoter. The process can be used to make N-methyl-2-pyrrolidone from N-methylallylamine.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: March 28, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Roger A. Grey, Diandre Armstead
  • Patent number: 5401747
    Abstract: A method for synthesizing camptothecin and camptothecin analogs using a novel hydroxyl-containing tricyclic intermediate and the camptothecin analogs produced by the process. The camptothecin analogs are effective inhibitors of topoisomerase. I and show antileukemic and anti-tumor activity.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: March 28, 1995
    Assignee: Research Triangle Institute
    Inventors: Monroe E. Wall, Mansukh C. Wani, Allan W. Nicholas, Govindarajan Manikumar
  • Patent number: 5366956
    Abstract: Herbicidal compounds ##STR1## in which Q represents a group --C(O)--C(CN).dbd.CH--NR.sup.1 R.sup.2, R.sup.1 and R.sup.2 each independently represents alkyl, or together represent alkylene optionally interrupted by oxygen, m is O or m is an integer from 1 to 3 and the or each Y independently represents halogen or alkyl and n is O or n is an integer from 1 to 5 and the or each X independently represents halogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, haloalkylthio, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cyano, nitro, alkylsulphonyl, alkysulphinyl, sulphonamido, or phenyl optionally substituted by alkyl, haloalkyl, alkoxy or halogen.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: November 22, 1994
    Assignee: Shell Research Limited
    Inventors: Christopher J. Foster, Terence Gilkerson, Richard Stocker
  • Patent number: 5354500
    Abstract: Use of optically active carboxylic esters of oxygen-containing heterocycles as doping substances in liquid crystal mixtures and liquid crystal mixtures containing them.Optically active 1,3-dioxolane-4-carboxylic esters and oxirane-2-carboxylic esters of the general formula (I)R(--A.sup.1).sub.j (--M.sup.1).sub.k (--A.sup.2).sub.l (--M.sup.2).sub.m (--A.sup.3).sub.n --X--Acin whichR.sup.1 is, for example, (C.sub.1 -C.sub.16)-alkyl or (C.sub.1 -C.sub.16)-alkoxy,A.sup.1, A.sup.2, A.sup.3 are, for example, phenyl or pyrimidine-2, 5-diyl,M.sup.1, M.sup.2 are, for example, CO--O, CH.sub.2 --CH.sub.2,j, l are 0, 1, 2,k, m are 0, 1,n is 0, 1, 2,X is O, S andAc is ##STR1## in which R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 for example, H or methyl, are particularly suitable doping substances for liquid crystalline mixtures, since they induce a high spontaneous polarization and effect a substantial decrease in the melting point.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: October 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hemmerling, Ingrid Muller, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 5336772
    Abstract: N-fluoropyridinium salts of the following formula are prepared by reacting a pyridine compound with a Br nsted acid and fluorine, wherein the reaction solvent contains a greater than equimolar amount of the pyridine compound relative to an amount of the Br nsted acid. ##STR1## The method can produce N-fluoropyridinium salts with a high yield.
    Type: Grant
    Filed: December 26, 1991
    Date of Patent: August 9, 1994
    Assignee: Onoda Cement Co., Ltd.
    Inventors: Yukinori Saiki, Kazunori Nukui
  • Patent number: 5334577
    Abstract: Oxime ether derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl, Het is pyridyl, quinolyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, quinoxalinyl, isoxazolyl, benzoxazolyl or benzothiazolyl, the heterocyclic ring system being unsubstituted or substituted, and X is oxygen or sulfur, their plant-tolerated acid addition salts, metal complexes and N-oxides, and fungicides containing these compounds.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wenderoth, Siegbert Brand, Franz Schuetz, Thomas Kuekenhoehner, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5318946
    Abstract: 2-(Heteroaryloxyphenoxy)alkylsulfonate compounds which are effective for the selective control of grass weed species in the presence of crops are described. Also described are a method for the selective herbicidal use of the compounds and a method for their preparation.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: June 7, 1994
    Assignee: American Cyanamid Company
    Inventors: Michael E. Condon, Michael A. Guaciaro
  • Patent number: 5308520
    Abstract: Various heterocyclic compounds have been discovered that impart improved fuel economy and friction modification to lubricant and fuel compositions. These heterocyclic compounds of the invention preferably contain nitrogen and may be further reacted with hydrocarbyl carboxylic acid acylating reactants or hydrocarbyl phenolic reactants to give higher molecular materials. These higher molecular weight materials have higher oil-solubility and impart dispersancy properties to lubricant and fuel compositions.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: May 3, 1994
    Assignee: The Lubrizol Corporation
    Inventors: Joseph W. Pialet, Paul E. Adams
  • Patent number: 5308826
    Abstract: 4-substituted pyridyl-3-carbinols of the formula ##STR1## wherein R is hydrogen, or an acyl, alkyl or carbamyl group exhibit desirable preemergent and postemergent herbicidal activity. Also disclosed are herbicidal compositions comprising such compounds and; a method of controlling undesirable vegetation employing such compounds. The compounds wherein AR is hydroxyl serve as useful intermediates for the production of the alpha-benzyl substituted compounds as well as exhibiting herbicidal activity.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: May 3, 1994
    Assignee: Zeneca Limited
    Inventors: Hsiao-Ling M. Chin, Yi Q. Wei, Nhan H. Nguyen
  • Patent number: 5286867
    Abstract: 1-Sulfonyloxy-2-pyridones of the formula I ##STR1## show good radiation sensitivity over a wide spectral range and are therefore valuable as photoactive compounds in radiation-sensitive mixtures.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: February 15, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Lohaus, Walter Spiess, Georg Pawlowski
  • Patent number: 5278133
    Abstract: Compounds having the formula ##STR1## in which: R is hydrogen, 2-halo, 2-(C.sub.1 -C.sub.4 alkyl), 2-trifluoromethyl, 2-(C.sub.1 -C.sub.4 alkoxy), 4-fluoro or, 2,6-dihalo;R.sub.1 is halo, cyano, C.sub.1 -C.sub.4 alkyl, or trifluoromethyl, and if R is 2-halo, 2-methyl, 2-methoxy or 2,6-dihalo, then R.sub.1 may also be hydrogen; andR.sub.2 is halo,are herbicides.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: January 11, 1994
    Assignee: Imperial Chemical Industries plc
    Inventor: Michael P. Prisbylla
  • Patent number: 5258519
    Abstract: Compounds of the following formula (I): ##STR1## where R.sup.1 and R.sup.2 are alkyl or cycloalkyl, which may be substituted, R.sup.4 is aryl such as phenyl which may be substituted, L is a direct bond or an oxygen containing linking group, R is a hydrogen, alkyloxy, alkyl, halogen or haloalkyl and Het is a pyridinyl or pyridazinyl group. The compounds can be used antihypertensives or myocardial relaxants. Also part of the invention are pharmaceutical compositions, intermediates and methods of synthesis.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: November 2, 1993
    Assignee: Glaxo Inc.
    Inventors: Thomas N. Wheeler, Terrence P. Kenakin
  • Patent number: 5254571
    Abstract: This invention relates to phenylpyridone derivatives which have bronchodilator and anti-allergic activities. A compound of the invention is 6-(2-propoxyphenyl)-1,2-dihydro-2-oxopyridine-3-carboxamide.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: October 19, 1993
    Assignee: Smith Kline & French Laboratories Ltd.
    Inventors: William J. Coates, Sean T. Flynn
  • Patent number: 5245040
    Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
  • Patent number: 5238908
    Abstract: This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure ##STR1## wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R.sup.1, R.sup.2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: August 24, 1993
    Assignee: Rohm and Haas Company
    Inventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
  • Patent number: 5223520
    Abstract: Compounds of formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl and R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl or --CH.sub.2 CH.sub.2 COOR.sub.7, or R.sub.3 and R.sub.4 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --CH.sub.2 OCH.sub.3, --CN, --COOR.sub.7 or ##STR3## R.sub.6 is hydrogen, chlorine, methyl or nitro, R.sub.7 and R.sub.8 are each methyl or ethyl, A is an unsubstituted or mono- to tetra-substituted, aromatic or non-aromatic, monocyclic or bicyclic, heterocyclic radical, one or two substituents being selected from the group consisting of C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, halocyclopropy, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl, C.sub.2 -C.sub.3 haloalkynyl, C.sub.1 -C.sub.3 haloalkoxy, C.sub.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: June 29, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Odd Kristiansen, Laurenz Gsell, Peter Maienfisch
  • Patent number: 5221792
    Abstract: There are described compounds exhibiting a herbicidal action of general formula: ##STR1## in which: R ##STR2## (where, R.sup.9 =alkyl, phenyl, substituted phenyl, naphthyl, cycloalkyl; R.sup.8 =alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, substituted phenyl, aralkyl, cycloalkyl;R.sup.2, R.sup.3, R.sup.4, R.sup.5 =H, alkyl, haloalkyl;R.sup.6 =--OR.sup.11, (where: R.sup.11 =H, alkaline or alkaline earth metal;R.sup.1 =phenyl, substituted phenyl, aralkyl, cycloalkyl, the --OR.sup.18 group (where R.sup.18 =alkyl, phenyl, substituted phenyl, aralkyl, substituted aralkyl), the ##STR3## group (where X=O, S and Y=phenyl, substituted phenyl, heterocycle, alkyl, haloalkyl, cycloalkyl, --R.sup.19 --X.sup.1 --R.sup.20, --X--R.sup.21, --R.sup.22 --X.sup.1 --R.sup.23 --X.sup.2 --R.sup.24, --NR.sup.25 R.sup.26, wherein: R.sup.19 =alkyl C.sub.1 -C.sub.16, aralkyl; R.sup.20 =alkyl C.sub.1 -C.sub.16, haloalkyl, alkenyl, alkynyl, cycloalkyl, phenylalkyl C.sub.7 -C.sub.13, phenyl; R.sup.21 =alkyl C.sub.1 -C.sub.
    Type: Grant
    Filed: February 4, 1992
    Date of Patent: June 22, 1993
    Assignee: Agrimont S.p.A.
    Inventors: Giovanni Camaggi, Giovanni Meazza, Ciro Preziuso
  • Patent number: 5216169
    Abstract: A 3-hydroxypyridineazomethine dye represented by general formula (I) ##STR1## wherein R.sub.1 represents an aliphatic group, an aromatic group, or a heterocyclic group; R.sub.2 represents an aliphatic group, an aromatic group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkenyloxy group, an amino group, an acyl group, an ester group, an amido group, a carbamoylamino group, a sulfamoylamino group, a sulfamido group, an imido group, a ureido group, an aliphatic or an aromatic sulfonyl group, an aliphatic or an aromatic thio group, a hydroxyl group, a cyano group, a carboxy group, or a halogen atom; R.sub.3 represents an aryl group; Y represents a bivalent linking group containing at least one of amide bond and ester bond; n represents 0, 1 or 2; where n is 2, the two R.sub.2 groups may be the same group or atom or may be mutually different groups or atoms, or the two R.sub.2 groups may form a ring; where n is 1 or more, R.sub.1 and R.sub.2 may form a ring; and at least one of R.sub.1 and R.sub.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: June 1, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Shigeru Yamazaki
  • Patent number: 5212314
    Abstract: This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.
    Type: Grant
    Filed: June 16, 1992
    Date of Patent: May 18, 1993
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
  • Patent number: 5205855
    Abstract: A compound of the formula: ##STR1## wherein Q.sup.1 is CH or N; R is H or C.sub.1 -C.sub.5 alkyl; X is H, halogen, CF.sub.3, or NO.sub.2 ; Y is H or halogen; Z is --O-- or --NH--; A is ##STR2## wherein Q.sup.2, and Q.sup.3 are each CH or N; R.sup.1 and R.sup.2 are each H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, or C.sub.2 -C.sub.6 alkoxycarbonyl; R.sup.3, R.sup.4, and R.sup.5 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.6 is H, halogen, or C.sub.1 -C.sub.5 alkyl; R.sup.7, R.sup.8, R.sup.9, and R.sup.10 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.11 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.2 -C.sub.6 alkenyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.15 aryloxyalkyl, or C.sub.7 -C.sub.15 aralkyl; R.sup.12 and R.sup.13 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.14 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.10 aryl, or C.sub.7 -C.sub.15 aralkyl; or R.sup.13 and R.sup.14 taken together form C.sub.3 -C.sub.4 alkylene, V.sup.1 and V.sup.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: April 27, 1993
    Assignees: Suntory Limited, Shionogi & Co., Ltd.
    Inventors: Harukazu Fukami, Naoki Higuchi, Naoko Kawaguchi, Masaki Hashimoto, Kinya Ide, Toshio Takahashi
  • Patent number: 5198439
    Abstract: The invention concerns pharmaceutically useful novel compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: March 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David A. Roberts, Arnold H. Ratcliffe, Robert H. Bradbury
  • Patent number: 5187176
    Abstract: Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
  • Patent number: 5182401
    Abstract: A process for the preparation of a 3-amino-2-(het)aroyl-acrylic acid derivative fo the formula ##STR1## in which Y represents a nitrile, or an ester group, --COOR.sub.1, or an acetyl group, whereR.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, andR denotes optionally substituted alkyl, cyclopropyl, alkoxy, phenyl or amino,A represents nitrogen or C--R.sub.2, whereR.sub.2 denotes hydrogen, methyl, halogen, nitro, methoxy or cyano,X.sub.1 and X.sub.2 are identical or different and denote halogen, andX.sub.3 denotes hydrogen, halogen or nitro andX.sub.4 denotes halogen, nitro, methoxy or methylthio, which comprises reacting a 3-dialkylamino-2-(het)aroyl-acrylic acid derivative of the formula ##STR2## in which R.sub.3 and R.sub.4 are the same or different and represent an alkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which they are bonded, form a ring,with a primary amine of the formula R--NH.sub.2 in the presence of at least one equivalent of an acid HX in a solvent or in excess acid.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: January 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 5177089
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: January 5, 1993
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5155135
    Abstract: This invention provides benzamide compounds of general formula ##STR1## wherein each of A and B independently represents a hydrogen or halogen atom, X represents an oxygen or a sulphur atom, n is 0, 1, 2, 3 or 4, each Z moiety independently represents a halogen atom or a C.sub.1-6 alkyl group, and Y represents a C.sub.1-6 haloalkyl group, a C.sub.1-6 haloalkoxy group, a group of formula ##STR2## wherein P is 0, 1 or 2, each Z' moiety independently represents a halogen atom or a C.sub.1-6 alkyl group, Y' represents a C.sub.1-6 haloalkyl, C.sub.1-6 haloalkoxy, nitro or cyano group and Q represents N or C-H, or, when n is 2 or 3, Y may also be a halogen atom; processes for their preparation; and their use as pesticides.
    Type: Grant
    Filed: December 6, 1989
    Date of Patent: October 13, 1992
    Assignee: Shell Internationale Research Maatschappij, B.V.
    Inventors: Martin Anderson, Antony G. Brinnand, Pieter A. Verbrugge
  • Patent number: 5152825
    Abstract: Compounds of the general formula ##STR1## in which R.sup.1 and R.sup.2 each independently represents an alkyl group, Z represents a nitrogen atom or a group CH unsubstituted or substituted by a substituent X, m is 0 or an integer from 1 to 4, the or each Y represents a halogen atom, n is 0 or an integer from 1 to 5, and the or each X represents a halogen atom or a group selected from alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cyano, nitro, alkylsulphonyl, alkylsulphinyl, and sulphonamido, have been found to have herbicidal activity.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: October 6, 1992
    Assignee: Shell International Research Maatschappij B.V.
    Inventors: Terence Gilkerson, Robert W. Shaw
  • Patent number: 5153209
    Abstract: Pyridones of formula (I) for treating congestive heart failure: ##STR1## wherein: R.sup.1 and R.sup.2 are a variety of phenyl substituents, L is a divalent alkylene linking group. Pharmaceutical composition, methods for their use in treating cardiovascular conditions, processes used in synthesis and intermediates used in such processes.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: October 6, 1992
    Assignee: Glaxo Inc.
    Inventors: Thomas N. Wheeler, Terrence P. Kenakin, Joel E. Shaffer
  • Patent number: 5132314
    Abstract: Anthelmintically active compounds of formula I are described ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 thioalkyl, C.sub.1 -C.sub.2 haloalkyl, nitro, C.sub.1 -C.sub.2 alkoxy, or the group SO.sub.n R in which R is C.sub.1 -C.sub.2 alkyl or phenyl and n is 0, 1 or 2;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 alkoxy;R.sub.3 is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sub.4 is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.5 alkyl;R.sub.6 is hydrogen, halogen or C.sub.1 -C.sub.5 alkyl;R.sub.7 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, nitro, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 alkoxy;R.sub.8 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 alkoxy;R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: July 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Christof Hildenbrand, Jean-Claude Gehret
  • Patent number: 5125956
    Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: June 30, 1992
    Assignee: Monsanto Company
    Inventors: Donald E. Korte, Len F. Lee
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5118696
    Abstract: Novel 5-acyl-2-(1H)pyrdinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-pentanedione in an inert organic solvent.
    Type: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
  • Patent number: 5114465
    Abstract: 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 5-(haloalkyl) carboxamide or 5-(haloalkyl)carbamate substitution, useful as herbicides and herbicide intermediates.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: May 19, 1992
    Assignee: Monsanto Company
    Inventors: Robert D. Bryant, Shridhar G. Hegde, Len F. Lee
  • Patent number: 5112386
    Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur, A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 --S(O).sub.n R.sup.3 groups; any two of the groups, A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: May 12, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony Vivienne, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5089168
    Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: February 18, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 5079366
    Abstract: The invention provides novel amino acids and peptides containing them which comprise a dihydropyridine.revreaction.pyridinium salt-type redox system and which provide site-specific and sustained delivery of pharmacologically active peptides to the brain. These new amino acids contain a redox system appended directly or via an alkylene bridge to the carbon atom adjacent to the carboxyl carbon and may be incorporated into a peptide chain at a variety of positions, including non-terminal positions.
    Type: Grant
    Filed: October 4, 1989
    Date of Patent: January 7, 1992
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • 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: 5076830
    Abstract: The present invention provides indan-1,3-dione derivatives, including derivatives represented by the following formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a group represented by ##STR2## wherein E represents a (substituted) phenyl group or a (substituted) pyridyl group; Y represents a hydroxyl group; and Z represents a halogen atom, a (substituted) alkylsulfonyloxy group or a (substituted) phenylsulfonyloxy group, or Y and Z are bonded to represent --O--; and A represents a (substituted) 1,3-butadienylene group or a (substituted) 1,3-azabutadienylene group, and a herbicidal composition containing the same as an active ingredient.The compound of the formula (I) shows high herbicidal activity against gramineous weeds, cyperaceous weeds, etc. but shows markedly low phytotoxicity against crops.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
  • Patent number: 5051431
    Abstract: Pyridones of formula (I) for treating congestive heart failure: ##STR1## wherein: R.sup.1 and R.sup.2 are a variety of phenyl substituents, L is a divalent alkylene or amide containing alkylene linking group. Pharmaceutical composition, methods for their use in treating cardiovascular conditions, processes used in synthesis and intermediates used in such processes.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: September 24, 1991
    Assignee: Glaxo Inc.
    Inventors: Thomas N. Wheeler, Terrence P. Kenakin, Joel E. Shaffer
  • Patent number: 5049571
    Abstract: There are disclosed novel 1-nitro-2,2-diaminoethylene derivatives of formula I ##STR1## wherein X is chlorine, fluorine, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkyl; unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkoxy, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkylthio, unsubstituted or halogen-substituted alkylsulfinyl, unsubstituted or halogen-substituted alkylsulfonyl; or also nitro, cyano, thiocyanato, C.sub.3 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 haloalkynyl, hydroxy, C.sub.1 -C.sub.5 alkoxycarbonyl, amino, C.sub.1 -C.sub.4 dialkylamino, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkylcarbamoyl or C.sub.1 -C.sub.5 alkylcarbonyloxy,n is an integer from 0 to 4,R.sub.1 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.7 cycloalkyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl,R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, benzyl or pyridinylmethyl, or R.sub.2 and R.sub.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: September 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Laurenz Gsell
  • Patent number: 5043449
    Abstract: This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.
    Type: Grant
    Filed: February 8, 1990
    Date of Patent: August 27, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
  • Patent number: 5039807
    Abstract: A compound of formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are independently selected from hydrogen, halogen, lower alkyl optionally substituted by halogen, lower alkoxy optionally substituted by halogen and lower alkenyl optionally substituted by halogen;R.sup.3 is halogen, amino, mono- or di(lower alkyl)-amino, lower alkyl substituted by halogen, lower alkoxy optionally substituted by halogen and lower alkenyl optionally substituted by halogen provided that R.sup.3 is not monochloro or monobromo-methyl;R.sup.6 is oxygen or sulphur;R.sup.7 and R.sup.10 are independently selected from hydrogen, halogen, lower alkyl optionally substituted by halogen, lower alkoxy optionally substituted by halogen, and lower thioalkoxy optionally substituted by halogen; andR.sup.
    Type: Grant
    Filed: March 22, 1989
    Date of Patent: August 13, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Trevor R. Perrior, David J. Tapolczay
  • Patent number: 5028732
    Abstract: Compounds having the formula ##STR1## wherein Q is substituted phenyl or substituted pyridyl; Y is nitro, cyano, or halogen; R is a group of the formula --(CHR.sup.1).sub.m --A--(CH.sup.2)--.sub.n --R.sup.3 wherein R.sup.1 and R.sup.2, independently of each other and in each (CHR.sup.1) and (CHR.sup.2) group, are hydrogen, unsubstituted or substituted alkyl, alkoxy, or alkylthio; A is --N(R.sup.1)--, --N(O)--, --O--, --S--, --S(O)--, --S(O).sub.2 --, --C(O)--, --C(O)B--, or --N(H)S(O).sub.2 --; B is alkylene, --O--, --S--, or --N(R.sup.4)--; R.sup.3 is cyano, halogen, or C(O)Z; R.sup.4 is hydrogen or unsubstituted or substituted alkyl; Z is hydrogen, unsubstituted or substituted alkyl, --N(R.sup.4).sub.2, --OR.sup.5, --SR.sup.5, or --N(R.sup.4)SO.sub.2 R.sup.6 ; R.sup.5 is hydrogen, unsubstituted or substituted alkyl, or an agronomically-acceptable cation; R.sup.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: July 2, 1991
    Assignee: Rohm and Haas Company
    Inventors: Ann H. Beaulieu, Roy Y. Yih
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 5008391
    Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: April 16, 1991
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Barnett, Thomas M. Wilson
  • Patent number: 4992452
    Abstract: Novel 5-acyl-2-(1H)-pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-pentanedione in an inert organic solvent.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: February 12, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
  • Patent number: 4985449
    Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultanously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N-- or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: January 15, 1991
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4980469
    Abstract: A process for the preparation of an oxyguanidine of the formula ##STR1## in which R.sup.1 is an organic radical,R.sup.2, R.sup.3 and R.sup.4 each is hydrogen or an organic or inorganic substituent,X is N or CH,Y is N or CR.sup.3, andZ is N or CR.sup.4,comprising reacting ##STR2## in which R.sup.5 is optionally substituted alkyl or aralkyl, or its hydrogen halide, with a hydroxylamine derivative of the formulaH.sub.2 N--O--R.sup.1 (III)at a temperature between about 0.degree. C. and 150.degree. C. New isothioureas of the formula ##STR3## are also shown.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: December 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Klaus-Helmut Muller
  • Patent number: 4973429
    Abstract: A material in the form of a film is described which contains, in an orientated arrangement which does not display point symmetry, compounds of formula I ##STR1## wherein X is .dbd.CH-- or .dbd.N--, R.sup.1 is C.sub.12 -C.sub.30 -alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 -alkyl, R.sup.3 is --NO.sub.2, --CN, --CF.sub.3, --COCF.sub.3, --SO.sub.2 CH.sub.3 or --SO.sub.2 CF.sub.3, R.sup.4 is hydrogen or is defined in the same way as R.sup.3, R.sup.5 is hydrogen or --NR.sup.6 R.sup.7 and R.sup.6 and R.sup.7 independently of one another are hydrogen or C.sub.1 -C.sub.30 -alkyl, it also being possible for any of the alkyl radicals to be partially fluorinated or perfluorinated.The compounds of formula I can be arranged in Langmuir-Blodgett layer systems. Such systems can be used for example for the manufacture of opto-electronic units.
    Type: Grant
    Filed: February 15, 1989
    Date of Patent: November 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Gero Decher, Bernd Tieke, Christian Bosshard, Peter Gunter