Cyano Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/286)
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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: 4999362Abstract: 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: GrantFiled: April 4, 1989Date of Patent: March 12, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4999432Abstract: 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: GrantFiled: August 28, 1989Date of Patent: March 12, 1991Assignee: DowElancoInventors: David D. Friese, Jerry M. Elledge
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Patent number: 4997837Abstract: 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: GrantFiled: October 6, 1989Date of Patent: March 5, 1991Assignee: Warner-Lambert CompanyInventors: Alexander W. Chucholowski, Mark W. Creswell, Bruce D. Roth, Drago R. Sliskovic
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Patent number: 4996320Abstract: 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: GrantFiled: January 9, 1989Date of Patent: February 26, 1991Assignee: Sagami Chemical Research CenterInventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa
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Patent number: 4988713Abstract: 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: GrantFiled: September 7, 1989Date of Patent: January 29, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Carmelo A. Gandolfi, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4985583Abstract: 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: GrantFiled: April 7, 1987Date of Patent: January 15, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Andreas Wachtler, Reinhard Hittich, Bernhard Scheuble, Georg Weber, Hans-Adolf Kurmeier
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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: 4978384Abstract: 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: GrantFiled: May 1, 1989Date of Patent: December 18, 1990Assignee: Monsanto CompanyInventor: Len F. Lee
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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
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Patent number: 4968796Abstract: 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: GrantFiled: August 17, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventor: Hans-Jochem Riebel
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Patent number: 4963687Abstract: 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: GrantFiled: April 24, 1989Date of Patent: October 16, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masao Saito, Kengo Tsukahara, Koichiro Yamada, Hisasi Imai
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Patent number: 4962113Abstract: 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: GrantFiled: July 26, 1988Date of Patent: October 9, 1990Assignee: Takeda Chemical Industries, LtdInventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
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Patent number: 4959474Abstract: 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: GrantFiled: October 15, 1985Date of Patent: September 25, 1990Assignee: Burroughs Wellcome Co.Inventor: Eugene M. Grivsky
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Patent number: 4956369Abstract: 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: GrantFiled: April 6, 1989Date of Patent: September 11, 1990Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Carmelo A. Gandolfi, Sergio Tognella
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Patent number: 4954632Abstract: 3-(2-Phenethyl)-1-carbamoyloxypyridinium halide is an intermediate for the preparation of the antihistamine azatadine.Type: GrantFiled: February 10, 1989Date of Patent: September 4, 1990Assignee: SmithKline Beecham CorporationInventors: Raymond E. Dagger, Linda A. Motyka
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Patent number: 4939260Abstract: 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: GrantFiled: May 12, 1988Date of Patent: July 3, 1990Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Akira Inoue, Mitsuaki Ikeda, Kunio Sano, Sadao Terui, Toshihide Kanzaki
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Patent number: 4935548Abstract: 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: GrantFiled: October 21, 1988Date of Patent: June 19, 1990Assignee: Glaxo S.p.AInventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Alan D. Borthwick
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Patent number: 4931564Abstract: 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: GrantFiled: December 2, 1988Date of Patent: June 5, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz
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Patent number: 4931561Abstract: 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: GrantFiled: July 25, 1988Date of Patent: June 5, 1990Assignee: Koei Chemical Co., Ltd.Inventors: Shinkichi Shimizu, Takayuki Shoji, Kanji Kono, Toru Nakaishi
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Patent number: 4931456Abstract: 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: GrantFiled: November 14, 1988Date of Patent: June 5, 1990Assignee: Rhone-Poulenc AgrochimieInventors: Claude Lambert, Regis Pepin, Marie-Pascale Latorse
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Patent number: 4923993Abstract: 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: GrantFiled: September 2, 1988Date of Patent: May 8, 1990Assignee: Ciba-Geigy CorporationInventor: Adrian Waldner
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Patent number: 4920225Abstract: 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: GrantFiled: December 22, 1986Date of Patent: April 24, 1990Assignee: Laboratoires Syntex S.A.Inventor: Gilles Genain
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Patent number: 4920136Abstract: 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: GrantFiled: July 13, 1988Date of Patent: April 24, 1990Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer
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Patent number: 4918087Abstract: 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: GrantFiled: March 11, 1988Date of Patent: April 17, 1990Assignee: Boehringer Biochemia Robin S.P.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4918086Abstract: 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: GrantFiled: July 27, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 4913837Abstract: 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: GrantFiled: September 1, 1987Date of Patent: April 3, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: George W. Gray, Kenneth J. Toyne, David Lacey, Michael P. Burrow, Rudolf Eidenschink, Andreas Wachtler, Georg Weber
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Patent number: 4908452Abstract: 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: GrantFiled: December 21, 1987Date of Patent: March 13, 1990Assignee: Merck & Co., Inc.Inventor: David A. Claremon
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Patent number: 4904409Abstract: 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: GrantFiled: September 1, 1988Date of Patent: February 27, 1990Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Ohno Kouji, Naoyuki Yoshida, Masakazu Kaneoya
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Patent number: 4897484Abstract: 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: GrantFiled: December 9, 1987Date of Patent: January 30, 1990Assignee: Ciba-Geigy CorporationInventors: Claus D. Weis, Peter Sutter
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Patent number: 4889865Abstract: 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: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4888427Abstract: 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: April 7, 1987Date of Patent: December 19, 1989Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 4885303Abstract: 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: GrantFiled: January 4, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Meyer, Eckhard Schwenner, Andreas Knorr
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Patent number: 4882341Abstract: The invention relates to amino substituted propenoates and their use against fungi.Type: GrantFiled: September 9, 1988Date of Patent: November 21, 1989Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Kay
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Patent number: 4879060Abstract: 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: GrantFiled: May 22, 1987Date of Patent: November 7, 1989Assignee: Seiko Epson Kabushiki KaishaInventors: Yoshio Shionozaki, Hiroshi Mukai, Tsuyoshi Obikawa, Shuhei Yamada
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Patent number: 4876348Abstract: 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: GrantFiled: October 29, 1985Date of Patent: October 24, 1989Assignee: The Standard Oil CompanyInventors: Robert DiCosimo, James D. Burrington, Dev D. Suresh
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Patent number: 4868181Abstract: 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: GrantFiled: June 30, 1987Date of Patent: September 19, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Alexander L. Johnson, Philip Ma, Petrus B. M. W. M. Timmermans, Ruth R. Wexler
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Patent number: 4863938Abstract: 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: GrantFiled: October 31, 1988Date of Patent: September 5, 1989Assignee: Ciba-Geigy CorporationInventors: Georg von Sprecher, Peter Waldmeier
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Patent number: 4863939Abstract: 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: GrantFiled: July 30, 1987Date of Patent: September 5, 1989Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
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Patent number: 4861799Abstract: 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: GrantFiled: September 30, 1987Date of Patent: August 29, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4851396Abstract: 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: GrantFiled: May 18, 1987Date of Patent: July 25, 1989Assignee: Rhone-Poulenc AgrochimieInventors: Claude Lambert, Regis Pepin
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Patent number: 4845113Abstract: 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: GrantFiled: July 25, 1986Date of Patent: July 4, 1989Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Ernesto Menta, Sergio Tognella
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Patent number: 4843163Abstract: 3-(2-Phenethyl)-1-carbamoyloxypyridinium halide is an intermediate for the preparation of the antihistamine azatadine.Type: GrantFiled: December 2, 1987Date of Patent: June 27, 1989Assignee: SmithKline Beckman CorporationInventors: Raymond E. Dagger, Linda A. Motyka
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Patent number: 4834904Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: December 24, 1986Date of Patent: May 30, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 4829076Abstract: 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: GrantFiled: September 16, 1987Date of Patent: May 9, 1989Assignee: Alkaloida Vegyeszeti GyarInventors: 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
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Patent number: 4826531Abstract: 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: GrantFiled: April 17, 1987Date of Patent: May 2, 1989Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 4826530Abstract: 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: GrantFiled: June 15, 1987Date of Patent: May 2, 1989Assignee: Monsanto CompanyInventor: Len F. Lee
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Patent number: 4826987Abstract: 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: GrantFiled: February 28, 1986Date of Patent: May 2, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
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Patent number: 4820839Abstract: 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: GrantFiled: January 23, 1987Date of Patent: April 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
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Patent number: RE33478Abstract: 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: GrantFiled: October 31, 1988Date of Patent: December 11, 1990Assignee: The Dow Chemical CompanyInventors: Howard Johnston, Lillian H. Troxell