Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
  • Patent number: 5134148
    Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: July 28, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5099025
    Abstract: A process for the preparation of 2-chloro-5-methylpyridine of the formula ##STR1## which comprises reacting 3-methyl-pyridine-1-oxide of the formula ##STR2## with a chlorinating agent of the formula ##STR3## in which R.sup.1 represents alkyl, halogenoalkyl, cycloalkyl, optionally substituted aryl, NR.sup.2 R.sup.3 or OR.sup.4 in whichR.sup.2 and R.sup.3 individually represent alkyl, cycloalkyl or aryl or together represent alkanediyl or oxaalkanediyl andR.sup.4 represents alkyl, cycloalkyl or optionally substituted aryl,in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -20.degree. C. and +150.degree. C.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: March 24, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Kaufmann, Klaus Jelich
  • Patent number: 5091068
    Abstract: A process for the preparation of 3-trichloromethylpyridine of the formula ##STR1## which comprises reacting 3-methyl-pyridine hydrogen sulphate of the formula ##STR2## with elemental chlorine which exposure to at least one of visible and ultraviolet light at a temperature between about 70.degree. C. and 150.degree. C.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: February 25, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Jelich, Hans Lindel
  • Patent number: 5087699
    Abstract: A 3,4-pyridine-dithiol compound having formula (I): ##STR1## wherein X is chlorine or a trifluoromethyl group; and a method of producing the above 3,4-pyridine-dithiol compound having formula (I) by allowing a polyhalogenide pyridine compound having formula (II) to react with a hydrosulfide in a polar organic solvent in the presence of sulfur, and an iron powder or an iron salt: ##STR2## wherein X is chlorine or a trifluoromethyl group.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: February 11, 1992
    Assignee: Ricoh Company, Ltd.
    Inventor: Kazukiyo Nagai
  • Patent number: 5087764
    Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: February 11, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Hafung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 5079361
    Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5076830
    Abstract: The present invention provides indan-1,3-dione derivatives, including derivatives represented by the following formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a group represented by ##STR2## wherein E represents a (substituted) phenyl group or a (substituted) pyridyl group; Y represents a hydroxyl group; and Z represents a halogen atom, a (substituted) alkylsulfonyloxy group or a (substituted) phenylsulfonyloxy group, or Y and Z are bonded to represent --O--; and A represents a (substituted) 1,3-butadienylene group or a (substituted) 1,3-azabutadienylene group, and a herbicidal composition containing the same as an active ingredient.The compound of the formula (I) shows high herbicidal activity against gramineous weeds, cyperaceous weeds, etc. but shows markedly low phytotoxicity against crops.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
  • Patent number: 5073637
    Abstract: 2,3-Difluoro-5-(trifluoromethyl)pyridine is prepared by contacting a 2,3-dihalo-5-(trifluoromethyl) pyridine with an effective amount of KF or CsF in a polar aprotic solvent (diluent) at an elevated temperature under substantially anhydrous conditions with removal of the difluoropyridine products essentially as they are formed. The starting material may optionally be added as the reaction proceeds to minimize decomposition. The reaction is also optionally conducted in the presence of an acid scavenger and/or a crown ether or other phase-transfer catalyst.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical
    Inventors: John C. Little, Charles A. Wilson
  • Patent number: 5073636
    Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical Company
    Inventors: Paula L. Humphreys, Thomas J. Dietsche
  • Patent number: 5047171
    Abstract: A liquid crystal compound suitable as a material for ferroelectric liquid crystal display elements and a liquid crystal composition containing the same are provided, which liquid crystal compound is an optically active-2,5-diphenylpyridine expressed by the formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 is 1-20C alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy and the other is an optically active group; and X and Y each independently represent H, halogen or CN and at least one of X and Y is H.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: September 10, 1991
    Assignee: Chisso Corporation
    Inventors: Kouji Ohno, Shinichi Saito, Hiromichi Inoue
  • Patent number: 5036074
    Abstract: The invention concerns new pyridine derivatives of the formula ##STR1## wherein X signifies a group ##STR2## and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the significances given in the description, and their N-oxides, N-amino salts, copper complexes and acid addition salts, processes for the manufacture of these substances, fungicidal compositions which contain these substances as the active ingredient and the use of such substances and compositions for the control of fungi in agriculture and in horticulture.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: July 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Isenring, Beat Zehnder, Hugo Ziegler
  • Patent number: 5026864
    Abstract: A process for the preparation of 2-chloro-5-amino-methyl-pyridine of the formula ##STR1## comprising reacting 2-chloro-5-chloromethyl-pyridine of the formula ##STR2## with excess ammonia, optionally in the presence of a diluent, at a temperature between about -50.degree. C. and +50.degree. C.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: June 25, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 5002694
    Abstract: Nitrogen-containing heterocyclic compounds of the formula II ##STR1## wherein R.sup.1 and R.sup.2 in each case denote an alkyl group having 1 to 15 C atoms, wherein one or more CH.sub.2 groups may also be replaced by a grouping selected from the group comprising --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --CH.dbd.CH--, --CH--halogen and --CHCN--, or else by a combination of two suitable groupings, two heteroatoms not being directly linked to each other,m denotes 0 or 1,Ar denotes 1,4-phenylene, 4,4'-biphenylyl or 2,6-naphthylene, wherein one or more CH groups are in each case replaced by N,Z denotes --C--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CHCN--, --CHCNCH.sub.2 --, --CH.dbd.CH or a single bond, andA denotes unsubstituted 1,4-cyclonexylene or 11,4-cyclohexylene substituted in position 1 or position 4 by CN,with the proviso that if A=unsubstituted 1,4-cyclonexylene, Z denotes --CHCNCH.sub.2 -- or --CH.sub.2 CHCN-- and/or at least one CH.sub.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: March 26, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • 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: 4973698
    Abstract: 2,3-Difluoro-5-(trifluoromethyl)pyridine is prepared by contacting a 2,3-dihalo-5-(trifluoromethyl) pyridine with an effective amount of KF or CsF in a polar aprotic solvent (diluent) at an elevated temperature under substantially anhydrous conditions with removal of the difluoropyridine products essentially as they are formed. The starting material may optionally be added as the reaction proceeds to minimize decomposition. The reaction is also optionally conducted in the presence of an acid scavenger and/or a crown ether or other phase-transfer catalyst.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: November 27, 1990
    Assignee: The Dow Chemical Company
    Inventors: John C. Little, Charles A. Wilson
  • 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: 4968807
    Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: November 6, 1990
    Assignee: The Dow Chemical Company
    Inventors: Paula L. Humphreys, Thomas J. Dietsche
  • Patent number: 4960897
    Abstract: Disclosed herein is an N-[2-(pyridyl)propyl]-N-substituted sulfonamide represented by the following general formula (I): ##STR1## wherein J represents a phenyl group which may be substituted or benzo-condensed, A represents --CH.sub.2 --, --CH.dbd.CH--, --O-- or --N(r)-- (wherein r represents an alkyl group having 1 to 4 carbon atoms), b represents 0 or 1, R represents an alkyl group, alkenyl group, alkynyl group, alkoxy group, fluoroalkyl group or formyl group, D represents a hydroxyl group, E represents a halogen atom, an alkylsulfonyloxy group or a benzenesulfonyloxy group which may be substituted, or D and E represent --O-- in combination, and V represents a pyridyl group which may be substituted, a herbicide containing said N-[2-(pyridyl)propyl]-N-substituted sulfonamide as an active ingredient and a 1-(halogenomethyl)vinylpyridine as an intermediate thereof.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: October 2, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Manabu Katsurada, Toyohiko Shike, Emiko Mikami, Osamu Ikeda
  • Patent number: 4898455
    Abstract: There is described compounds of the formula ##STR1## wherein X stands for CH and Y stands for N or X stands for N and Y stands for CH; A.sup.1 and A.sup.2 signify single covalent bonds or one of the groups A.sup.1 and A.sub.2 also signifies trans-1,4-cyclohexylene, cis-4-cyano-trans-1,4-cyclohexylene or 1,4-phenylene optionally substituted with halogen or methyl; ring B represents trans-1,4-cyclohexylene, 1,4-phenylene optionally substituted with halogen or methyl or, when A.sup.2 signifies a single covalent bond, also cis-4-cyano-trans-1,4-cyclohexylene; R.sup.1 denotes an optionally halogen-substituted alkyl or alkenyl group in which optionally one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are replaced by --O--, --COO-- and/or --OOC--; R.sup.2 signifies an optionally halogen-substituted alkyl or alkenyl group in which optionally one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are replaced by --O--, --COO-- and/or --OOC-- or R.sup.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: February 6, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Alfred Germann, Stephen Kelly, Martin Schadt
  • Patent number: 4897488
    Abstract: In the preparation of 2-chloro-5-methylpyridine of the formula ##STR1## by reacting 3-methylpyridine 1-oxide with phosphorus oxychloride, the improvement which comprises carrying out the reaction in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -50.degree. C. and +50.degree. C.
    Type: Grant
    Filed: January 4, 1989
    Date of Patent: January 30, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Gallenkamp, Hans-Joachim Knops
  • 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: 4880936
    Abstract: An optically active compound represented by formula (I): ##STR1## wherein R represents a straight chain alkyl group having from 2 to 12 carbon atoms; R' represents a straight chain alkyl or alkoxy group having from 1 to 20 carbon atoms; C represents an asymmetric carbon atom; A represents ##STR2## and X and Y each represents a hydrogen atom or a fluorine atom, provided that X and Y do not simultaneously represent a fluorine atom. The compound (I) reduces a temperature dependence of the threshold voltage of a nematic liquid crystal composition when added thereto in a small amount.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: November 14, 1989
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Makoto Sasaki, Kiyohumi Takeuchi, Haruyoshi Takatsu
  • Patent number: 4876349
    Abstract: The compounds of the formula ##STR1## wherein X and Y are independently --CH.sub.2 -- or >C(CH.sub.3).sub.2 ; Z is --CHR.sup.8 --, >Co, >CR.sup.8 OR.sup.7 , --CHR.sup.8 --CHR.sup.8 --, --CHOR.sup.7 --CH.sub.2 --, --CO--CHOR.sup.7 or --CHOR.sup.7 --CHOR.sup.7 --R.sup.1 is a 5- or 6-membered, monocyclic heterocyclic group which optionally can be C-substituted by halogen, lower-alkyl, lower-alkoxy, acyloxy, nitro, hydroxy, amino, lower-alkylamino or di-lower-alkylamino and/or which can be substituted on a ring --NH-- group by lower-alkyl; R.sup.2 and R.sup.3 are independently hydrogen, lower-alkyl, trifluoromethyl or halogen and one of R.sup.2 and R.sup.3 always is trifluoromethyl or lower-alkyl; R.sup.4 and R.sup.5 are independently hydrogen, alkyl, alkoxy or halogen; R.sup.6 is hydrogen, lower-alkyl or --OR.sup.7 ; R.sup.7 is hydrogen, lower-alkyl or acyl; R.sup.8 is hydrogen or lower-alkyl; and R.sup.7 and R.sup.8 can be the same or different from one another.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: October 24, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Ekkehard Weiss
  • Patent number: 4865763
    Abstract: A novel liquid crystalline, halogen-containing heterocyclic compound having a characteristic that even when its S.sub.c * phase is supercooled, no other smectic phases appear, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group of 2 to 18 carbon atoms; X represents --N.dbd. or --CH.dbd.; Y represents F or Cl; n represents an integer of 0 to 10; and a symbol * represents an asymmetric carbon atom.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: September 12, 1989
    Assignee: Chisso Corporation
    Inventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Kazutoshi Miyazawa, Shinichi Saito
  • Patent number: 4840953
    Abstract: 9-(Substituted thio)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives of the formula: ##STR1## wherein n is 0 or 1, R is --COR.sup.1, --CONR.sup.4 R.sup.5 or --CH.sub.2 R.sup.6, R.sup.1 is C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allythio, styryl, phenoxymethyl, thienylmethyl, C.sub.6 -C.sub.10 aryl optionally substituted, benzyl optionally substituted or 5- or 6-membered heterocyclic group optionally substituted, R.sup.2 and R.sup.3 each is hydrogen, C.sub.1 -C.sub.5 alkyl, carboxy, C.sub.2 -C.sub.5 alkoxycarbonyl or benzyloxycarbonyl optionally substituted, R.sup.4 and R.sup.5 each is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl or phenyl optionally substituted, and R.sup.8 is pyridyl or phenyl optionally substituted) being useful as antiulcer agents are provided through several routes.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: June 20, 1989
    Assignee: Shionogi & Co., Ltd.
    Inventors: Shigeru Matsutani, Yukio Mizushima, Masami Doteuchi, Yasunobu Ishihara
  • 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: 4814458
    Abstract: This invention relates to a novel process for preparing 4-acetyl-1-methyl-7-pyridyl-5,6,7,8-tetrahydro-3(2H)-isoquinolinone characterized by condensing 2-acetyl-4-pyridyl cyclohexanone with acetoacetamide. This compound is useful as pharmaceuticals, particularly cardiotonics.
    Type: Grant
    Filed: February 2, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nobuyuki Fukazawa, Tatsuo Kaiho, Hiroyuki Yamashita
  • Patent number: 4798894
    Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: January 17, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4797490
    Abstract: 6-Fluoro-7-pyridylquinolone carboxylic esters and acids having antibacterial activity are prepared by coupling of a 2-fluorophenyl-metallic compound with a pyridyl bromide or iodide in the presence of a transition metal catalyst, nitrating and hydrogenating the pyridyl-2-fluorophenyl compound formed, introducing a substituent on the nitrogen of the amine formed, and cyclizing after reacting with a dialkyl or dibenzyl ethoxymethylene malonate to form a 6-fluoro-7-pyridyl-1,4-dihydroquinol-4-one 3-carboxylate, and hydrolyzing to the corresponding acid.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: January 10, 1989
    Assignee: Pfizer Inc.
    Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
  • Patent number: 4782161
    Abstract: Fluoropyridine compounds, including 3- and 5-fluoropyridines, are prepared in an improved process by contacting chloropyridine compounds with hydrogen fluoride in the vapor phase in the presence of an activated carbon catalyst having large diameter pores. Thus, 2,3-difluoro-5-(trifluoromethyl)pyridine is prepared by contacting 3-chloro-2-fluoro-5-(trifluoro-methyl)pyridine with excess hydrogen fluoride at about 500.degree. C. in the presence of an activated carbon catalyst having an average pore diameter of about 100 Angstroms.
    Type: Grant
    Filed: October 21, 1987
    Date of Patent: November 1, 1988
    Assignee: The Dow Chemical Company
    Inventors: Michael A. DesJardin, Craig B. Murchison
  • Patent number: 4778896
    Abstract: A process for the preparation of 5-chloromethylpyridines of the formula (I) ##STR1## in which R.sup.1 represents chlorine or nitro,R.sup.2 represents chlorine, andn represents the number 0 to 1, comprising chlorinating 5-methylpyridine of the formula (II) ##STR2## in which R.sup.1, R.sup.2 and n have the abovementioned meanings, at temperatures between 0.degree. C. and 100.degree. C., if appropriate in the presence of acid acceptors and if appropriate in the presence of inert diluents.
    Type: Grant
    Filed: August 17, 1987
    Date of Patent: October 18, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Bernd Gallenkamp
  • Patent number: 4772416
    Abstract: A novel phenylpyridine derivative which exhibits a positive dielectric anisotropy and is useful as a component of liquid crystal materials and also has a broad temperature range of liquid crystal phases, a high clearing point and a superior compatibility with other liquid crystal compounds or liquid crystal compositions, and a composition containing the derivative are provided. The phenylpyridine derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbon atoms, X represents H or F; Y represents F, --CN or an alkyl group or an alkoxy group of 1 to 10 carbon atoms; and m represents 0 or 1.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: September 20, 1988
    Assignee: Chisso Corporation
    Inventors: Yasuyuki Goto, Kazunori Nigorikawa, Toyoshiro Isoyama
  • Patent number: 4771059
    Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## X.sup.-, wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: September 13, 1988
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4767790
    Abstract: Compounds of formula I ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, cycloalkylalkyl or optionally substituted phenyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, formyl, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring show therapeutic acitivity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: August 30, 1988
    Assignee: The Boots Company plc
    Inventors: James E. Jeffery, Antonin Kozlik, Eric C. Wilmshurst
  • Patent number: 4765924
    Abstract: A novel liquid crystalline, halogen-containing heterocyclic compound having a characteristic that even when its S.sub.c * phase is supercooled, no other smectic phases appear, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group of 2 to 18 carbon atoms; X represents --N.dbd. or --CH.dbd.; Y represents F or Cl; n represents an integer of 0 to 10; and a symbol * represents an asymmetric carbon atom.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: August 23, 1988
    Assignee: Chisso Corporation
    Inventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Kazutoshi Miyazawa, Shinichi Saito
  • Patent number: 4753947
    Abstract: Novel pyridine and pyrazine derivatives of the formula ##STR1## wherein R.sup.4 is 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl-4-oxide or 2-pyrazinyl-1,4-dioxide, and R, R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, processes for their preparation, fungicidal compositions containing said compounds, and methods for the use of such compounds or compositions for combatting fungi in agriculture and in horticulture are disclosed. Novel starting materials and fungicidal active substances of the formula ##STR2## wherein R.sup.4' is 3-pyridyl or 2-pyrazinyl, and R and R.sup.1" as hereinafter set forth, which are used for the preparation of the compounds of formula I, and their N-oxides, as well as fungicidal compositions containing these compounds as the active substance, are also described.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: June 28, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Franz Dorn, Francois Montavon, Milos Suchy
  • Patent number: 4746680
    Abstract: Compounds of formula I ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, cycloalkylalkyl or optionally substituted phenyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, formyl, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring show therapeutic activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: May 24, 1988
    Assignee: The Boots Company p.l.c.
    Inventors: James E. Jeffery, Antonin Kozlik, Eric C. Wilmshurst
  • Patent number: 4746756
    Abstract: Disclosed are fluorinated squaraine compounds of the following formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents.
    Type: Grant
    Filed: August 21, 1986
    Date of Patent: May 24, 1988
    Assignee: Xerox Corporation
    Inventors: Peter M. Kazmaier, Giuseppa Baranyi, Rafik O. Loutfy
  • Patent number: 4745193
    Abstract: Fluoromethylpyridines of the formula: ##STR1## wherein the group F.sub.n H.sub.3-n C-- may be ortho, meta or para to the ring nitrogen atom, n is 1, 2 or 3, m is 1 to 4, X is Cl, Br, I or F and, when m is 2, 3 or 4 the substituents represented by X may be the same or different, at least one X being ortho or para to the F.sub.n H.sub.3-n C-- group, are prepared by reacting a compound of the formula: ##STR2## wherein Y is Cl, Br, I or F and m is 1 to 4, with potassium fluoride in a polar aprotic solvent under substantially anhydrous conditions. These fluoromethylpyridines are useful as intermediates for herbicides. 3,4,5-trifluoro-2-trifluoromethylpyridine and 2,6-difluoro-3-difluoromethylpyridine are novel compunds.
    Type: Grant
    Filed: May 9, 1986
    Date of Patent: May 17, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael S. Howarth, Edward G. Scovell, David J. Watson
  • Patent number: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4727148
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrochloride, and heating the brominated product in the presence or absence of any added base or hydrogen acceptor to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinearcarboxylic acids.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: February 23, 1988
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Venkataraman Ramachandran
  • Patent number: 4719298
    Abstract: A novel method of chlorinating the alkyl side chains of a nitrogen containing heterocyclic comprising reacting an alkyl substituted heterocycle with trichloroisocyanuric acid at temperatures of 20.degree. to 200.degree. C. to obtain the same in high yields.
    Type: Grant
    Filed: April 18, 1986
    Date of Patent: January 12, 1988
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Gunter E. Jeromin, Winfried Orth, Werner Fickert
  • Patent number: 4713456
    Abstract: A process for the preparation of a 5-acylpyrimidine of the formula ##STR1## in which R is an organic radical comprising reacting a methyl ketone of the formulaR--CO--CH.sub.3in a first stage with a formylating reagent in the presence of a base to form an enolketone of the formulaR--CO--CH.dbd.CH--OR.sup.10in which R.sup.10 represents hydrogen or a base radical, thereafter reacting the enolketone in 2nd and 3rd stages with formamidine or a formamidine salt, and with an amino-formylating agent, and, in a 4th stage heating to cyclize the compound formed.The end products, some of which are new, are intermediates for making herbicides.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: December 15, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Graham Holmwood
  • Patent number: 4713460
    Abstract: Novel 2,3-bis((poly)chloromethyl)pyridines and 3,6-dichloro--2-(polychloromethyl)pyridines were obtained by vapor phase chlorination of 2,3-lutidine. Chlorination at about 350.degree. C. using a 14.4 sec. residence time and a chlorine to 2,3-lutidine mole ratio of about 6.8, for example, produced 2-(chloromethyl)-3-(dichloromethyl) pyridine, 3-(chloromethyl)-2-(dichloromethyl)pyridine, 2,3-bis(dichloromethyl)pyridine, 6-chloro-2,3-bis(dichloromethyl)pyridine, 3-(dichloromethyl)-2-(trichloromethyl)pyridine, 6-chloro-3-(dichloromethyl-2-(trichloromethyl)pyridine, 6-chloro-2-(dichloromethyl)-3-(trichloromethyl)pyridine, and 3,6-dichloro-2-(trichloromethyl)pyridine. The compounds are useful as starting materials for herbicides and pharmaceutical agents.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Michael A. DesJardin, Thomas J. Dietsche, Jon A. Orvik
  • Patent number: 4699984
    Abstract: Shown is the process which comprises heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-dimethylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Also shown are the 3-step synthesis of 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid from 2-fluorobenzaldehyde and the five step synthesis of 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolin ecarboxylic acid, a highly potent antibacterial agent, starting with 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Other intermediates shown in said five step synthesis include 3-(2,6-dimethyl-4-pyridinyl)-4-fluorobenzeneamine and diethyl 4-fluoro-3-(2,6-dimethyl-4-pyridinyl)anilinomethylenemalonate.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: October 13, 1987
    Assignee: Sterling Drug Inc.
    Inventor: Baldev Singh
  • Patent number: 4681945
    Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.
    Type: Grant
    Filed: September 7, 1984
    Date of Patent: July 21, 1987
    Assignee: The Dow Chemical Company
    Inventors: Paula L. Humphreys, Thomas J. Dietsche
  • Patent number: 4675328
    Abstract: Polycyclic salts of the formulaA-XN+CH.sub.2 --(Y).sub.n --(CH.sub.2).sub.p --(Z).sub.q --L--(T).sub.r --M IwhereinA.sup.- is the anion of a strong organic or inorganic acid;XN.sup.+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R.sup.1, R.sup.2 and R.sup.3 ;n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15;Y is CH.sub.2, C(H,OH) or C(O):Z is O, S, CH.sub.2, C(O), NQ.sup.1, SO.sub.2, C(O)O, OC(O), C(O)N(Q.sup.1) or N(Q.sup.1)C(O);L is p-phenylene substituted by R.sup.4 ; andM is phenyl substituted by R.sup.5 and R.sup.6,T has one of the meanings given above, for Z or is C(CH.sub.3).sub.2, C.sub.2 H.sub.4, C(Q.sup.2).dbd.C(Q.sup.3), C.tbd.C, CH.sub.2 C(O), C(O)CH.sub.2, CH.sub.2 O or OCH.sub.2,R.sup.1 is a group Ar, Ar-C.sub.1-4 -alkyl, ArO or ArC(O),Ar is phenyl substituted by R.sup.7, R.sup.8 and R.sup.9 ;R.sup.2 and R.sup.3 individually are H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.6 H.sub.
    Type: Grant
    Filed: January 15, 1986
    Date of Patent: June 23, 1987
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Jean-Marie Cassal, Albrecht Edenhofer, Henri Ramuz
  • Patent number: 4672125
    Abstract: A method is disclosed for preparing a chlorinated .beta.-methylpyridine by chlorinating a .beta.-methylpyridine compound with PCl.sub.5 in the presence of phenylphosphonic dichloride.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: June 9, 1987
    Assignee: The Dow Chemical Company
    Inventors: Trevor E. Gray, Charles B. Grant, Thomas J. Dietsche