Chalcogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/288)
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Patent number: 5411936Abstract: 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: GrantFiled: January 19, 1993Date of Patent: May 2, 1995Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5401856Abstract: 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: GrantFiled: February 28, 1994Date of Patent: March 28, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Roger A. Grey, Diandre Armstead
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Patent number: 5401747Abstract: 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: GrantFiled: May 31, 1994Date of Patent: March 28, 1995Assignee: Research Triangle InstituteInventors: Monroe E. Wall, Mansukh C. Wani, Allan W. Nicholas, Govindarajan Manikumar
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Patent number: 5366956Abstract: 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: GrantFiled: March 1, 1993Date of Patent: November 22, 1994Assignee: Shell Research LimitedInventors: Christopher J. Foster, Terence Gilkerson, Richard Stocker
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Patent number: 5354500Abstract: 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: GrantFiled: April 17, 1992Date of Patent: October 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hemmerling, Ingrid Muller, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
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Patent number: 5336772Abstract: 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: GrantFiled: December 26, 1991Date of Patent: August 9, 1994Assignee: Onoda Cement Co., Ltd.Inventors: Yukinori Saiki, Kazunori Nukui
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Patent number: 5334577Abstract: 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: GrantFiled: December 4, 1990Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Wenderoth, Siegbert Brand, Franz Schuetz, Thomas Kuekenhoehner, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5318946Abstract: 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: GrantFiled: November 27, 1991Date of Patent: June 7, 1994Assignee: American Cyanamid CompanyInventors: Michael E. Condon, Michael A. Guaciaro
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Patent number: 5308520Abstract: 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: GrantFiled: July 31, 1989Date of Patent: May 3, 1994Assignee: The Lubrizol CorporationInventors: Joseph W. Pialet, Paul E. Adams
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Patent number: 5308826Abstract: 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: GrantFiled: April 22, 1993Date of Patent: May 3, 1994Assignee: Zeneca LimitedInventors: Hsiao-Ling M. Chin, Yi Q. Wei, Nhan H. Nguyen
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Patent number: 5286867Abstract: 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: GrantFiled: April 20, 1992Date of Patent: February 15, 1994Assignee: Hoechst AktiengesellschaftInventors: Gerhard Lohaus, Walter Spiess, Georg Pawlowski
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Patent number: 5278133Abstract: 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: GrantFiled: December 11, 1992Date of Patent: January 11, 1994Assignee: Imperial Chemical Industries plcInventor: Michael P. Prisbylla
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Patent number: 5258519Abstract: 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: GrantFiled: December 10, 1991Date of Patent: November 2, 1993Assignee: Glaxo Inc.Inventors: Thomas N. Wheeler, Terrence P. Kenakin
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Patent number: 5254571Abstract: 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: GrantFiled: September 25, 1992Date of Patent: October 19, 1993Assignee: Smith Kline & French Laboratories Ltd.Inventors: William J. Coates, Sean T. Flynn
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Patent number: 5245040Abstract: 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: GrantFiled: October 16, 1991Date of Patent: September 14, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
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Patent number: 5238908Abstract: 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: GrantFiled: August 9, 1990Date of Patent: August 24, 1993Assignee: Rohm and Haas CompanyInventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
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Patent number: 5223520Abstract: 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: GrantFiled: March 27, 1992Date of Patent: June 29, 1993Assignee: Ciba-Geigy CorporationInventors: Odd Kristiansen, Laurenz Gsell, Peter Maienfisch
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Patent number: 5221792Abstract: 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: GrantFiled: February 4, 1992Date of Patent: June 22, 1993Assignee: Agrimont S.p.A.Inventors: Giovanni Camaggi, Giovanni Meazza, Ciro Preziuso
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Patent number: 5216169Abstract: 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: GrantFiled: September 18, 1990Date of Patent: June 1, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Shigeru Yamazaki
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Patent number: 5212314Abstract: 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: GrantFiled: June 16, 1992Date of Patent: May 18, 1993Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 5205855Abstract: 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: GrantFiled: September 6, 1990Date of Patent: April 27, 1993Assignees: Suntory Limited, Shionogi & Co., Ltd.Inventors: Harukazu Fukami, Naoki Higuchi, Naoko Kawaguchi, Masaki Hashimoto, Kinya Ide, Toshio Takahashi
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Patent number: 5198439Abstract: 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: GrantFiled: April 27, 1992Date of Patent: March 30, 1993Assignee: Imperial Chemical Industries PLCInventors: David A. Roberts, Arnold H. Ratcliffe, Robert H. Bradbury
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Patent number: 5187176Abstract: 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: GrantFiled: October 9, 1991Date of Patent: February 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
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Patent number: 5182401Abstract: 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: GrantFiled: May 2, 1991Date of Patent: January 26, 1993Assignee: Bayer AktiengesellschaftInventor: Klaus Grohe
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Patent number: 5177089Abstract: 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: GrantFiled: July 25, 1990Date of Patent: January 5, 1993Assignee: Eisai Co., Ltd.Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
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Patent number: 5155135Abstract: 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: GrantFiled: December 6, 1989Date of Patent: October 13, 1992Assignee: Shell Internationale Research Maatschappij, B.V.Inventors: Martin Anderson, Antony G. Brinnand, Pieter A. Verbrugge
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Patent number: 5152825Abstract: 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: GrantFiled: September 27, 1990Date of Patent: October 6, 1992Assignee: Shell International Research Maatschappij B.V.Inventors: Terence Gilkerson, Robert W. Shaw
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Patent number: 5153209Abstract: 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: GrantFiled: June 13, 1991Date of Patent: October 6, 1992Assignee: Glaxo Inc.Inventors: Thomas N. Wheeler, Terrence P. Kenakin, Joel E. Shaffer
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Patent number: 5132314Abstract: 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: GrantFiled: October 25, 1991Date of Patent: July 21, 1992Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Christof Hildenbrand, Jean-Claude Gehret
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Patent number: 5125956Abstract: 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: GrantFiled: February 25, 1991Date of Patent: June 30, 1992Assignee: Monsanto CompanyInventors: Donald E. Korte, Len F. Lee
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Patent number: 5126461Abstract: 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: GrantFiled: November 14, 1990Date of Patent: June 30, 1992Assignee: Shell Research LimitedInventors: Mark S. Baird, Ian Bruce
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Patent number: 5118696Abstract: 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: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 5114465Abstract: 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 5-(haloalkyl) carboxamide or 5-(haloalkyl)carbamate substitution, useful as herbicides and herbicide intermediates.Type: GrantFiled: June 17, 1991Date of Patent: May 19, 1992Assignee: Monsanto CompanyInventors: Robert D. Bryant, Shridhar G. Hegde, Len F. Lee
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Patent number: 5112386Abstract: 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: GrantFiled: December 30, 1988Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventors: Anthony Vivienne, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 5100460Abstract: 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: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5089168Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: May 16, 1989Date of Patent: February 18, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 5079366Abstract: 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: GrantFiled: October 4, 1989Date of Patent: January 7, 1992Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5079361Abstract: 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: GrantFiled: September 9, 1988Date of Patent: January 7, 1992Assignee: Celltech LimitedInventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
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Patent number: 5076830Abstract: 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: GrantFiled: May 15, 1990Date of Patent: December 31, 1991Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
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Patent number: 5051431Abstract: 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: GrantFiled: August 9, 1990Date of Patent: September 24, 1991Assignee: Glaxo Inc.Inventors: Thomas N. Wheeler, Terrence P. Kenakin, Joel E. Shaffer
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Patent number: 5049571Abstract: 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: GrantFiled: January 24, 1990Date of Patent: September 17, 1991Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 5043449Abstract: 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: GrantFiled: February 8, 1990Date of Patent: August 27, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 5039807Abstract: 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: GrantFiled: March 22, 1989Date of Patent: August 13, 1991Assignee: Imperial Chemical Industries PLCInventors: Trevor R. Perrior, David J. Tapolczay
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Patent number: 5028732Abstract: 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: GrantFiled: March 13, 1986Date of Patent: July 2, 1991Assignee: Rohm and Haas CompanyInventors: Ann H. Beaulieu, Roy Y. Yih
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Patent number: 5008276Abstract: 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: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 5008391Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.Type: GrantFiled: July 7, 1989Date of Patent: April 16, 1991Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 4992452Abstract: 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: GrantFiled: May 1, 1989Date of Patent: February 12, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
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Patent number: 4985449Abstract: 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: GrantFiled: June 13, 1989Date of Patent: January 15, 1991Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4980469Abstract: 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: GrantFiled: August 30, 1989Date of Patent: December 25, 1990Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Klaus-Helmut Muller
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Patent number: 4973429Abstract: 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: GrantFiled: February 15, 1989Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventors: Gero Decher, Bernd Tieke, Christian Bosshard, Peter Gunter