Cyano Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/286)
  • 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: 4999362
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is an alkoxycarbonyl group, acetyl, benzoyl, cyano, nitro or aminocarbonyl;R.sub.2 is an optionally substituted aryl or hetaryl group;R.sub.3 is an alkoxycarbonyl group;.phi. is a thio residue such as alkylthio, cycloalkylthio, arylthio, heteroarylthio, aminoalkylthio,are described.Compounds I are useful in human therapy as antihypertensive, antiulcer, antithrombotic, antiischaemic agents.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: March 12, 1991
    Assignee: Boehringer Biochemia Robin S.p.A.
    Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sergio Tognella
  • Patent number: 4999432
    Abstract: Fluoropyridine compounds having a fluoro substituent in at least one of the 2-, 4-, and 6-positions are prepared by treatment of an appropriate 2-, 4-, or 6-chloropyridine compound with excess hydrogen fluoride in a dipolar, aprotic solvent at an elevated temperature and super-atmospheric pressure. Thus, 3,5-dichloro-2,4,6-trifluoropyridine is prepared by heating a mixture of pentachloropyridine, N-methyl-2-pyrrolidinone, and hydrogen fluoride at about 220.degree. C. and about 900 kiloPascals of pressure.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: March 12, 1991
    Assignee: DowElanco
    Inventors: David D. Friese, Jerry M. Elledge
  • Patent number: 4997837
    Abstract: Certain trans-6-[[(substituted)pyridin-3-yl]-alkyl- and alkenyl]tetrahydro-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: March 5, 1991
    Assignee: Warner-Lambert Company
    Inventors: Alexander W. Chucholowski, Mark W. Creswell, Bruce D. Roth, Drago R. Sliskovic
  • Patent number: 4996320
    Abstract: A pyridine-compound is reacted with fluorine together with a Bronsted acid-compound or Lewis acid to form a N-fluoropyridinium salt which is very active to other compounds but is very selective for the preparation of a desired product and this product is very useful for a fluorine-introducing agent which makes it useful for the preparation of fluoro-compounds such as thyroid inhibitor.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: February 26, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa
  • Patent number: 4988713
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is a cyano, nitro, acetyl, benzoyl or alkoxycarbonyl group;R.sub.2 is an optionally substituted phenyl or heteroaryl group;R.sub.3 is an alkoxycarbonyl group;R.sub.4 is an alkyl group, optionally substituted by hydroxy, amino, phenyl, heterocyclic group; an optionally substituted phenyl group or an heterocyclic group.Compounds I are useful in human therapy as agents able to interact with CA.sup.++ -dependent systems and as anti-tumor agents.
    Type: Grant
    Filed: September 7, 1989
    Date of Patent: January 29, 1991
    Assignee: Boehringer Biochemia Robin S.p.A.
    Inventors: Marco Frigerio, Carmelo A. Gandolfi, Odoardo Tofanetti, Sergio Tognella
  • Patent number: 4985583
    Abstract: New cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H, an unsubstituted or substituted alkyl group with 1-15 C atoms, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by at least one grouping from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, --SO-- and --SO.sub.2 --, F, Cl, Br, CN or R.sup.3 --(A.sup.3).sub.p --Z.sup.2 --,A.sup.1 is --A--, --A.sup.4 --Z.sup.3 --A-- or --A--Z.sup.3 --A.sup.4 --,A is a 1,4-cyclohexylene group which is substituted in the 1- and/or 4-position by unsubstituted or substituted alkyl or fluorinated alkyl with in each case 1-5 C atoms, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by one grouping from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, --SO-- and --SO.sub.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: January 15, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause, Andreas Wachtler, Reinhard Hittich, Bernhard Scheuble, Georg Weber, Hans-Adolf Kurmeier
  • 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: 4978384
    Abstract: There are disclosed novel 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds useful as herbicides, and as intermediates which provide herbicides.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: December 18, 1990
    Assignee: Monsanto Company
    Inventor: Len F. Lee
  • 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
  • Patent number: 4968796
    Abstract: Disclosed is a process for the preparation of a sulphonylisothiourea of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, and Z are as defined herein, which comprises reacting a sulphonic acid amide of the formulaR.sup.1 --SO.sub.2 --NH.sub.2, (II)or a metal salt thereof, with an N-heteroaryl-iminodithiocarbonic acid S,S-diester of the formula ##STR2## at a temperature between about 20.degree. C. and 200.degree. C. Intermediates and a process for their preparation are also disclosed.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Jochem Riebel
  • Patent number: 4963687
    Abstract: A process for producing a cyanopyridine which comprises reacting the corresponding methylpyridine, ammonia and an oxygen-containing gas in the presence of a catalyst comprising a vanadium oxide, a chromium oxide, a boron oxide and optionally a phosphorus oxide and/or molybdenum oxide held on silica is disclosed. According to the present invention, the reactivity of the raw material and the yield of the reaction product are high.
    Type: Grant
    Filed: April 24, 1989
    Date of Patent: October 16, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masao Saito, Kengo Tsukahara, Koichiro Yamada, Hisasi Imai
  • Patent number: 4962113
    Abstract: Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group;R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group;l is 0 or 1;R.sup.5 is a phenylene group or an alkylene group which may be substituted;R.sup.11 is an alkyl group or aryl group;X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3;U is a group of the formula: ##STR4## wherein R.sup.
    Type: Grant
    Filed: July 26, 1988
    Date of Patent: October 9, 1990
    Assignee: Takeda Chemical Industries, Ltd
    Inventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
  • Patent number: 4959474
    Abstract: A novel class of 2,4-diamino-6-(2,5-dialkoxybenzyl)-5-methyl[2,3-d]-pyrimidines is described. These compounds are antibacterial agents, active against certain Streptococcus species. They are also active antiproliferative agents.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: September 25, 1990
    Assignee: Burroughs Wellcome Co.
    Inventor: Eugene M. Grivsky
  • 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: 4954632
    Abstract: 3-(2-Phenethyl)-1-carbamoyloxypyridinium halide is an intermediate for the preparation of the antihistamine azatadine.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: September 4, 1990
    Assignee: SmithKline Beecham Corporation
    Inventors: Raymond E. Dagger, Linda A. Motyka
  • Patent number: 4939260
    Abstract: A process for producing aromatic or heterocyclic nitriles, which comprises reacting an alkyl-substituted aromatic hydrocarbon or an alkyl-substituted heterocyclic compound with ammonia and oxygen in the presence of a catalyst composition comprising (a) at least one composite oxide selected from the group consisting of a binary composite oxide comprising titanium and silicon, a binary composite oxide comprising titanium and zirconium and a ternary composite oxide comprising titanium, silicon and zirconium, and (b) an oxide of at least one metal selected from the group consisting of vanadium, molybdenum, tungsten, chromium, antimony, bismuth, phosphorus, niobium, iron, nickel, cobalt, manganese and copper.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: July 3, 1990
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Akira Inoue, Mitsuaki Ikeda, Kunio Sano, Sadao Terui, Toshihide Kanzaki
  • Patent number: 4935548
    Abstract: Compounds are described of the formula ##STR1## wherein R.sub.1 represents a formyl or nitrile group or a group OCH.sub.2 A where A represents hydroxy, C.sub.1-4 alkoxy or D(CH.sub.2).sub.n NR.sub.7 R.sub.8 (where R.sub.7 and R.sub.8 independently represent hydrogen or C.sub.1-4 alkyl and n is 2 or 3);R.sub.2 and R.sub.3 independently represent a C.sub.1-6 straight or branched alkyl chain or alkoxy group;R.sub.4 represents a C.sub.1-4 alkyl group;R.sub.5 represents a straight or branched chain C.sub.1-13 alkyl group or a C.sub.5-8 cycloalkyl group which may be substituted by a C.sub.1-3 alkyl substituent;R.sub.6 represents a halogen atom or a straight or branched C.sub.1-3 alkyl group.The compounds represented by formula (I) reduce intracellular calcium ion concentration by limiting transmembranal calcium ion influx and thus may be useful for the treatment of cardiovascular disorders such as hypertension.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: June 19, 1990
    Assignee: Glaxo S.p.A
    Inventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Alan D. Borthwick
  • Patent number: 4931564
    Abstract: Cyanopyridines of the formula ##STR1## are prepared by reacting acrolein and an alkanal ##STR2## or its acetal or ketone of the formula ##STR3## where R.sup.1, R.sup.2 and R.sup.3 may be identical or different and are each hydrogen, alkyl of 1 to 6 carbon atoms or aryl and R.sup.4 is alkyl and n is 0-11, with ammonia in the presence of a zeolite as a catalyst. The reaction is preferably carried out in the gas phase.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: June 5, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz
  • Patent number: 4931561
    Abstract: A heteroaromatic nitrile is prepared in high conversion and yield by catalytically reacting an alkyl-substituted heteroaromatic compound with molecular oxygen and ammonia in the presence of a catalyst having the following composition:Mo(P).sub.x (A).sub.y (B).sub.z (O).sub.w (I)wherein x, y, z and w represent atomic ratios of phosphorus, an element A defined below, an element B defined below and oxygen to molybdenum, respectively and(i) x and z are both 0 (zero), y is from 0.1 to 5, and A is at least one element selected from the group consisting of cerium and tungsten, or(ii) x is from 0.1 to 7, y is from 0 to 5, z is from 0 to 5, A is at least one element selected from the group consisting of cerium, manganese and tungsten, and B is at least one element selected from the group consisting of thallium, titanium, niobium and aluminum, or(iii) x is from 0.5 to 7, y is from 0 to 5, z is from 0.01 to 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: June 5, 1990
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Shinkichi Shimizu, Takayuki Shoji, Kanji Kono, Toru Nakaishi
  • Patent number: 4931456
    Abstract: Nicotinic derivatives. They have the formula: ##STR1## with R.sup.1, R.sup.2, which are identical or different,=H, alkyl (C.sub.1 -C.sub.18) optionally substituted phenyl, pyridyl;Y=H, hal, alkyl or alkoxy or C.sub.1 -C.sub.4 ; n=integer from 1 to 3.Agricultural fungal compounds.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: June 5, 1990
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Claude Lambert, Regis Pepin, Marie-Pascale Latorse
  • Patent number: 4923993
    Abstract: The process of the invention relates to the reaction of hydrazones of formula II ##STR1## with .alpha.-chloro- or .alpha.-bromoarylonitrile or .alpha.-chloro- or .alpha.-bromoacrylates of formula III ##STR2## to 1-amino-2-cyano-1,4-dihydropyridines or 1-amino-1,4-dihydropyridine-2-carboxylic acid esters of formula IV ##STR3## which are converted into pyridine derivatives of formula I ##STR4## by treatment with an acid, with removal of R.sub.4 R.sub.5 NH. Y is --CN or --COOR.sub.3 and R.sub.1 to R.sub.5 may be alkyl.
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Adrian Waldner
  • Patent number: 4920225
    Abstract: Optically active compounds of formula 1 ##STR1## wherein R.sub.1 is H or lower alkyl;R.sub.2 and R.sub.6 are each independently lower alkyl, aryl, or arylalkyl;R.sub.3 is CN, NO.sub.2, CO.sub.2 R.sub.5, CONHR.sub.5, SO.sub.2 R.sub.5, or P(O)(OR.sub.5).sub.2, where R.sub.5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl;R.sub.4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO.sub.2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF.sub.3, OCH.sub.2 F, or OCF.sub.3 ;are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: April 24, 1990
    Assignee: Laboratoires Syntex S.A.
    Inventor: Gilles Genain
  • Patent number: 4920136
    Abstract: For promoting livestock production, the novel substituted pyridylethanolamines of the formula ##STR1## in which R.sup.1 represents CN, --COOR.sup.8 or --CONR.sup.9 R.sup.10,R.sup.2 represents optionally substituted alkyl,R.sup.3 represents hydrogen, alkyl or alkenyl,R.sup.4 represents hydrogen or optionally substituted alkyl or alkenyl, orR.sup.3 and R.sup.4 represent, together with the nitrogen atom to which they are bonded, an optionally substituted heterocyclic radical,R.sup.5 represents OH, acyloxy or alkoxy,R.sup.6 represents hydrogen or alkyl,R.sup.7 represents hydrogen, alkyl, cycloalkyl, substituted alkyl, optionally substituted aralkyl, aryl or heterocyclyl,R.sup.6 and R.sup.7 can, together with the nitrogen atom to which they are bonded, represent an optionally substituted heterocyclic radical,R.sup.8 represents alkyl, andR.sup.9 and R.sup.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: April 24, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer
  • Patent number: 4918087
    Abstract: Pyridines of formula I ##STR1## wherein R.sub.1 is acetyl, benzoyl, cyano, nitro, alkoxycarbonyl or aminocarbonyl groups; R.sub.2 is an optionally substituted aryl or a heterocyclic group; and .phi. is a sulphurated residue such as alkylthio, cycloakylthio, arylthio, heteroarylthio, aminoalkylthio.Compounds I are useful in therapy in cardiovascular field.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: April 17, 1990
    Assignee: Boehringer Biochemia Robin S.P.A.
    Inventors: Carmelo A. Gandolfi, Marco Frigerio, Odoardo Tofanetti, Sergio Tognella
  • Patent number: 4918086
    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 akylthio, 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: July 27, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Laurenz Gsell
  • Patent number: 4913837
    Abstract: Heterocyclic compounds of the formula IR.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.n -R.sup.2Iwherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are defined in claim 1, can be used as components of liquid-crystalline phases.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: April 3, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: George W. Gray, Kenneth J. Toyne, David Lacey, Michael P. Burrow, Rudolf Eidenschink, Andreas Wachtler, Georg Weber
  • Patent number: 4908452
    Abstract: A facile and mild process for the preparation of nitriles from reagent sensitive primary carboxamides is described. The process utilizes a (carboxysulfamoyl)ammonium hydroxide compound as the dehydrating agent. It is useful for preparing nitriles which have present other groups which are sensitive to the more conventional methods of dehydration or to other methods of nitrile synthesis. Some novel nitriles prepared by the new method are also described.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 13, 1990
    Assignee: Merck & Co., Inc.
    Inventor: David A. Claremon
  • 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
  • Patent number: 4897484
    Abstract: A process is described for the preparation of compounds of the formula ##STR1## in which R and X are as defined in claim 1. The compounds of the formula (1) are valuable intermediates in the synthesis of triarylmethane dyes and triarylmethanelactones.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: January 30, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Claus D. Weis, Peter Sutter
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4888427
    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: April 7, 1987
    Date of Patent: December 19, 1989
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4885303
    Abstract: Circulation active tetrahydropyridines of the formula ##STR1## in which R.sup.1 represents a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical which has up to 20 carbon atoms and can be interrupted in the chain by an oxygen atom or a sulphur atom and/or can be substituted by halogen, cyano, hydroxyl, acyloxy, nitro or nitrooxy, or by a phenyl, phenoxy, phenylthio or phenylsulphonyl group which is optionally substituted by halogen, cyano, dialkylamino with in each case 1 or 2 carbon atoms per alkyl group, alkoxy with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, trifluoromethyl or nitro, or by an .alpha.-, .beta.- or .gamma.
    Type: Grant
    Filed: January 4, 1988
    Date of Patent: December 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Meyer, Eckhard Schwenner, Andreas Knorr
  • Patent number: 4882341
    Abstract: The invention relates to amino substituted propenoates and their use against fungi.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Ian T. Kay
  • Patent number: 4879060
    Abstract: 2-phenylpyridine derivatives represented by the general formula: ##STR1## wherein when Y is R--, Z is one of R--, RO--, ##STR2## when Y is RO--, Z is one of straight chain pentyl, ##STR3## and when Y is one of Z is one of R--, RO-- and --CN; when Y is --CN, Z is one of RO--, ##STR4## and R is a straight chain alkyl group from 1 to 12 carbon atoms, are disclosed. The 2-phenylpyridine derivatives in accordance with the invention are particularly well-suited for use in nematic liquid crystal compositions for reducing the steepness and response time of the liquid crystal compositions in a liquid crystal display device.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: November 7, 1989
    Assignee: Seiko Epson Kabushiki Kaisha
    Inventors: Yoshio Shionozaki, Hiroshi Mukai, Tsuyoshi Obikawa, Shuhei Yamada
  • Patent number: 4876348
    Abstract: Disclosed is a process comprising (1) dehydrocyclization of 2-methylglutaronitrile over Pt or Pd based catalysts to make a mixture containing 3-methylpyridine and lesser amounts of 3-methylpiperidine and (2) reacting such a mixture with NH.sub.3 and O.sub.2 over certain oxide catalysts containing P, V and Mo to obtain 3-cyanopyridine.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: October 24, 1989
    Assignee: The Standard Oil Company
    Inventors: Robert DiCosimo, James D. Burrington, Dev D. Suresh
  • Patent number: 4868181
    Abstract: 1,4-Dihydropyridine derivatives which combine both calcium agonist and alpha.sub.1 -antagonist activity are useful in treating congestive heart failure. These derivatives are compounds having the formula: ##STR1## wherein Ar, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined in the specification.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: September 19, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alexander L. Johnson, Philip Ma, Petrus B. M. W. M. Timmermans, Ruth R. Wexler
  • Patent number: 4863938
    Abstract: Pyridine derivatives of the formula ##STR1## their tautomers and their salts, in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n have the meanings given in the claims, can be used as active ingredients in medicaments and are manufactured in a manner known per se.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: September 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg von Sprecher, Peter Waldmeier
  • Patent number: 4863939
    Abstract: The growth of livestock is promoted by the new compounds of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, halogen, halogenoalkyl, hydroxyl, cyano, alkoxycarbonyl, aminocarbonyl, mono- and dialkylaminocarbonyl, alkoxy, halogenoalkoxy, halogenoalkylthio or NHSO.sub.2 -alkyl,R.sup.2 represents hydrogen, hydroxyl, alkoxy or the --NR.sup.11 R.sup.12 radical,R.sup.3 represents the radicals mentioned in the case of R.sup.1R.sup.4 represents hydroxyl, acyloxy or alkoxy,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen or alkyl,R.sup.7 represents hydrogen or alkyl,R.sup.8 represents hydrogen or alkyl,X represents C.sub.1 -C.sub.10 -alkylene or a direct bond,Y represents oxygen or a direct bond,R.sup.9 represents hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by hydroxyl, alkoxy, acyloxy or the --NR.sup.13 R.sup.14 radical, or represents the COR.sup.15 radical or the O--Z--R.sup.16 radical,Z represents C.sub.1 -C.sub.10 -alkylene, C.sub.1 -C.sub.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: September 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
  • Patent number: 4861799
    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 simultaneously 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: September 30, 1987
    Date of Patent: August 29, 1989
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4851396
    Abstract: Nicotinic acid derivatives They are of formula: ##STR1## with: Z=OR, with R=optionally substituted C.sub.1 -C.sub.18 -alkyl, C.sub.2 -C.sub.18 -alkenyl, C.sub.2 -C.sub.5 -alkynyl, phenyl or phenoxy;Y=H, hal, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy andn=1 to 3.Fungicidal products for agricultural use.
    Type: Grant
    Filed: May 18, 1987
    Date of Patent: July 25, 1989
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Claude Lambert, Regis Pepin
  • Patent number: 4845113
    Abstract: Compounds of formula I ##STR1## wherein R is hydrogen or lower alkyl; R.sub.1 is acetyl, benzoyl, cyano, nitro, carboxy, alkoxycarbonyl or aminocarbonyl groups; R.sub.2 is an optionally substituted aryl or hetaryl residue; R.sub.3 is a carboxy or alkoxycarbonyl group; A is a cyclopropyl group or a group of formula --CH.dbd.CH-- and R.sub.4 is a phenyl or heteroaryl group, optionally mono, di or tri-substituted, are useful in radical scavenging therapy.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: July 4, 1989
    Assignee: Boehringer Biochemia Robin S.p.A.
    Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Ernesto Menta, Sergio Tognella
  • Patent number: 4843163
    Abstract: 3-(2-Phenethyl)-1-carbamoyloxypyridinium halide is an intermediate for the preparation of the antihistamine azatadine.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: June 27, 1989
    Assignee: SmithKline Beckman Corporation
    Inventors: Raymond E. Dagger, Linda A. Motyka
  • Patent number: 4834904
    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: December 24, 1986
    Date of Patent: May 30, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 4829076
    Abstract: The invention relates to new substituted dihydropyridine derivatives of the general formula (I), ##STR1## wherein R.sup.1 and R.sup.6 are as defined herein after, the racemic and optically active variants as well as mixtures thereof, furthermore the acid addition salts of these compounds, pharmaceutical compositions containing the same and a process for the preparation thereof.The compounds of the general formula (I) can be advantageously applied for the treatment of pathologically severe hypertensions, their toxicity is low and they possess an advantageous therapeutic index.
    Type: Grant
    Filed: September 16, 1987
    Date of Patent: May 9, 1989
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Geza Szilagyi, Eva Bozo, Laszlo Czollner, Laszlo Jaszlits, Gyorgy Rabloczky, Jozsef Borsi, Istvan Elekes, Gyongyi Nagy nee Csokas, Andras Varro, ZSuzanne Lang nee Rihmer, Gyorgy Cseh, Gyula Horvath, Ilona Bodi
  • Patent number: 4826531
    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 or --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: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4826530
    Abstract: There are disclosed novel 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds useful as herbicides, and as intermediates which provide herbicides.
    Type: Grant
    Filed: June 15, 1987
    Date of Patent: May 2, 1989
    Assignee: Monsanto Company
    Inventor: Len F. Lee
  • Patent number: 4826987
    Abstract: The present invention relates to compounds of formula I ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: May 2, 1989
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 4820839
    Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
  • Patent number: RE33478
    Abstract: Certain novel pyridinyloxyphenoxy alkanoic acids, pyridinylthiophenoxy alkanoic acids, derivatives thereof and related compounds are described. More specifically, these novel compounds bear a fluorine substituent in the 3-position of the pyridinyl group and in the 5-position the substituent is selected from chlorine, CF.sub.3, CF.sub.2 Cl or CF.sub.2 H. These novel compounds exhibit surprising preemergent and postemergent activity in the control of grassy weeds.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: December 11, 1990
    Assignee: The Dow Chemical Company
    Inventors: Howard Johnston, Lillian H. Troxell