Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/303)
  • Patent number: 6407245
    Abstract: Substituted thiopyridines of the general formula I where n is 1 or 2; R1 is chlorine, C1-C3-fluoroalkyl, nitro or methylsulfonyl; R2 is a C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl radical, in each case unsubstituted or substituted by halogen, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, di-(C1-C4-alkylamino)carbonyl, cyano or nitro, a C3-C8-cycloalkyl radical, or a C1-C4-alkyl-enephenyl, phenyl or naphthyl radical which is unsubstituted or substituted in the phenyl moiety by halogen, C1-C3-alkyl, C1-C3-alkoxy, trifluoromethyl, cyano or nitro.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: June 18, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Joachim Gebhardt, Heinz Isak, Michael Rack, Joachim Rheinheimer, Peter Schäfer
  • Patent number: 6323222
    Abstract: Compound of formula (I): wherein: n represents 0 or 1, R1 represents hydrogen, arylalkyl, alkyl, acyl, alkoxycarbonyl, arylalkoxycarbonyl or trifluoroacetyl, R2 represents alkyl, X represents oxygen, chlorine, OR3, SR4 or NOR5, R3 represents hydrogen, alkyl, acyl, alkoxycarbonyl or arylalkoxycarbonyl, R4 represents hydrogen, alkyl or aryl, R5 represents hydrogen or optionally substituted alkyl, represents a single or double bond, Ar represents aryl or heteroaryl, its isomers and addition salts thereof with a pharmaceutically acceptable acid, and medicinal products containing the same which are useful as facilitators of memory and cognition and antalgic agents.
    Type: Grant
    Filed: May 2, 2000
    Date of Patent: November 27, 2001
    Assignee: Adir et Compagnie
    Inventors: Sylvain Rault, Olivier Renault, Jean Guillon, Patrick Dallemagne, Pierre Renard, Bruno Pfeiffer, Pierre Lestage, Marie-Cécile Lebrun
  • Patent number: 6316631
    Abstract: This invention relates to a process for converting 2,4-dichloropyridines into 2-aryloxy-4-chloropyridines, comprising reacting a compound of formula (I), wherein R1 is (C1-C4)alkyl; R2 is methyl or ethyl; and R3, R4 and R5 are selected, independently, from (C1-C4)alkyl and (C1-C4)alkoxy; or a pharmaceutically acceptable salt thereof; comprising reacting a compound of formula (II), wherein R1 and R2 are defined as above, with a compound of formula (III), wherein R3, R4 and R5 are defined as above, in the presence of a base that is capable of deprotonating the compound of formula (III), optionally in the presence of an organometallic halide or oxide and a suitable solvent, and then optionally converting the resulting compound of formula (I) into a pharmaceutically acceptable salt of such compound.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: November 13, 2001
    Assignee: Pfizer Inc.
    Inventors: Yuhpyng L. Chen, Sally Gut Ruggeri
  • Patent number: 6310006
    Abstract: The invention relates to novel compounds of formula I: wherein R, A, B and X have the meaning given in claim 1; and the agronomically acceptable salts or N-oxides thereof, and to herbicidal compositions containing such compounds as active ingredients.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: October 30, 2001
    Assignee: American Cyanamid Company
    Inventors: Thomas Maier, Stefan Scheiblich, Helmut S. Baltruschat
  • Patent number: 6306839
    Abstract: The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with (derivatised) hydroxyalkyl substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.
    Type: Grant
    Filed: September 16, 1999
    Date of Patent: October 23, 2001
    Assignee: Dow AgroSciences LLC
    Inventors: Emily J. Canada, Robert P. Gajewski, Christopher S. Galka, Neil V. Kirby, Irene M. Morrison, Jeannie R. Phillips, Mary E. Pieczko, Brent J. Rieder, Chrislyn M. Carson, Zhengyu Huang
  • Patent number: 6271379
    Abstract: Intermediates useful for the synthesis of huperzine A represented by the structures below, and methods for their synthesis, wherein: R1 is lower alkyl, benzyl, or substituted benzyl; X is a suitable leaving group; Y is an electron withdrawing group that can subsequently be converted into an amino group; one broken line is present as a carbon—carbon bond and the other broken line is absent, where the broken line forms an unconjugated carbon—carbon double bond, which double bond may be endocyclic whereby n is 3 or the double bond may be exocyclic whereby n is 2.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: August 7, 2001
    Assignee: Georgetown University
    Inventors: Werner Tückmantel, Alan P. Kozikowski
  • Publication number: 20010006805
    Abstract: The present invention relates to 3-substituted and 2,3-disubstituted pyridine compounds which are useful as intermediates in the synthesis of pyridylsulfonylurea herbicides. The invention also relates to arylation of alcohols using a pyridinediazonium salt. More particularly the arylation process of the instant invention relates to the synthesis of 2,3-disubstituted pyridine compounds via anhydrous diazotization of 3-aminopyridines to form a diazonium salt intermediate that is then reacted with the appropriate alcohol to produce the desired product. The invention additionally relates to pyridine-3-diazonium salt intermediates.
    Type: Application
    Filed: January 22, 2001
    Publication date: July 5, 2001
    Inventor: Dean Kent Hoglen
  • Patent number: 6248892
    Abstract: 2-, 3- or 4-arylpyridines are prepared by reacting a halopyridine with an aryl Grignard compound, where the halogen is chlorine or bromine, in the presence of a palladium catalyst of the formula (IV)
    Type: Grant
    Filed: July 1, 1999
    Date of Patent: June 19, 2001
    Assignee: Clariant GmbH
    Inventors: Antje Noerenberg, Steffen Haber, Andreas Meudt
  • Patent number: 6175011
    Abstract: A process for the preparation of arylamides of heteroaromatic carboxylic acids of the formula: in which each An is nitrogen or CRn (n=1-5), with the proviso that at least one of the ring members is nitrogen and that two nitrogen atoms are not bonded directly to one another; R1 to R5, if present, independently of one another are hydrogen, C1-4-alkyl or aryl, also one of the substituents R1 to R5 can be a group of the formula —OR, in which R is an optionally substituted aromatic or heteroaromatic radical; R6 is hydrogen or C1-4-alkyl; and R7 is an optionally substituted aromatic or heteroaromatic radical. The amides are obtained from the corresponding heteroaromatic halogen compounds, the corresponding aromatic amines and carbon monoxide in the presence of a palladium diphosphine complex. Compounds of this class, especially those in which one of the substituents R1 to R5 is an aryloxy group, are important herbicides.
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: January 16, 2001
    Assignee: Lonza AG
    Inventors: Jean-Paul Roduit, Georges Kalbermatten
  • Patent number: 6166047
    Abstract: Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines, such as (3-(3-pyridyloxy)propyl)methylamine and (3-(5-bromo(3-pyridyloxy))propyl)methylamine.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: December 26, 2000
    Inventors: Gary Maurice Dull, Grayland Page Dobson, Jared Miller Wagner
  • Patent number: 6143899
    Abstract: A process for the preparation of 2-hydroxy-6-trifluoromethylpyridine which comprises reacting 2-fluoro-6-trifluomethylpyridine or a mixture of 2-fluoro-6-trifluoromethylpyridine and 2-chloro-6-trifluoromethylpyridine with an alkali metal hydroxide at a temperature of from 50.degree. C. to 160.degree. C. and acidifying the product so formed.
    Type: Grant
    Filed: September 3, 1999
    Date of Patent: November 7, 2000
    Assignee: Zeneca Limited
    Inventors: Alexander Pai-Yung Fung, David Dale Friese, Erwin Michael Seidel, Alan John Whitton, Alastair lain Currie Stewart, Jennifer Ann White, Raymond Vincent Heavon Jones, John Desmond Hunt
  • Patent number: 6133447
    Abstract: 2-chloro-3-hydroxypyridine is prepared by reacting 3-hydroxypyridine with aqueous sodium hypochlorite.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: October 17, 2000
    Assignee: Novartis Crop Protection, Inc.
    Inventors: Dominik Faber, Denis Blaser, Thierry Bourquard, Andrea Rolf Sting, Dean Kent Hoglen
  • Patent number: 6121454
    Abstract: A process is provided for the preparation of compounds of formula I, ##STR1## useful in the preparation of compounds such as Omeprazole, Lansoprazole and Pantoprazole, wherein R.sup.1 =H or CH.sub.3, R.sup.2 =H or CH.sub.3, R.sup.3 =Alkoxy (1-4C), OCH.sub.2 CF.sub.3, Cyano, Hydrogen, Halogen, Acetoxy or Aryloxy, any electron withdrawing group or salts (organic or inorganic) of electron donating groups, R=Alkoxy, Hydroxy, Halogen, Activated ester, Tosylate, Mesylate, Thiol or Xanthyl, wherein the process for the preparation of compound of formula I employs a free radical reaction to functionalize the 2-position.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: September 19, 2000
    Assignee: PDi-Research Laboratories, Inc.
    Inventors: Michel Zoghbi, Liquin Chen
  • Patent number: 6090817
    Abstract: (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-.alpha. release.
    Type: Grant
    Filed: September 1, 1998
    Date of Patent: July 18, 2000
    Assignee: Novartis AG
    Inventor: Paul W. Manley
  • Patent number: 6054583
    Abstract: This invention relates to a process for preparing 2-substituted pyridines via metal halogen exchange with sec-butyllithium on optionally substituted 2-bromo or 2-iodopyridines. The resulting lithopyridine intermediate is reacted with an electrophile to provide the desired 2-substituted pyridine. The substitution of sec-butyllithium for n-butyllithium in such a process results in an enhanced yield and purity of the desired 2-substituted pyridine.
    Type: Grant
    Filed: May 5, 1999
    Date of Patent: April 25, 2000
    Assignee: Rohm and Haas Company
    Inventors: Martha Jean Kelly, Damian Gerard Weaver
  • Patent number: 6048823
    Abstract: A pyridone derivative represented by the general formula: ##STR1## {wherein R is an alkyl group or a haloalkyl group, R.sup.1 is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, an amino group, an alkoxycarbonylamino group, an alkylcarbonylamino group or the like, R.sup.2 is a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group, R.sup.19 is a hydrogen atom, a halogen atom, a cyano group or the like, Q is a phenyl group which may be substituted or a condensed hetero ring which may be substituted}, a herbicide containing it and an intermediate for its production, are provided.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: April 11, 2000
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yoshihiro Ito, Atsushi Shibayama, Yoshihiro Yamaji, Ryo Hanai, Sota Uotsu, Hideo Sadohara
  • Patent number: 6020524
    Abstract: A compound of the following formula ##STR1## wherein M is an alkali metal or alkaline earth metal atom and a process for the preparation of the compound is provided.
    Type: Grant
    Filed: March 29, 1999
    Date of Patent: February 1, 2000
    Assignee: ZENECA Limited
    Inventors: Alfred Glyn Williams, Gordon Richard Munns, Paul Anthony Worthington
  • Patent number: 6015569
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: January 18, 2000
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 6008161
    Abstract: Herbicidal 2-(hetero)aryloxy-6-arylpyridines and 2-Aryl-4-(hetero)aryloxypyrimidinesNew herbicidal pyridine and pyrimidine derivatives of general formula (1), ##STR1## wherein Z represents a nitrogen atom or a C--H group; A represents an optionally substituted aryl group or an optionally substituted 5- or 6-membered nitrogen-containing heteroaromatic group; n represents an integer from 0 to 2 and R.sup.1 or each R.sup.1 independently represents a hydrogen atom or an optionally substituted alkyl, alkoxy, alkylthio or dialkylamino group; m represents an integer from 0 to 5 and R.sup.1 or each R.sup.1 independently represents a hydrogen or a halogen atom or an optionally substituted alkyl, haloalkyl, haloalkoxy, alkoxy, alkylthio group or a nitro, cyano or a halosulphonyl group; and X represents an oxygen or sulphur atom.
    Type: Grant
    Filed: July 14, 1998
    Date of Patent: December 28, 1999
    Assignee: American Cyanamid Company
    Inventors: Axel Kleemann, Helmut Siegfried Baltruschat, Thekla Haselwander, Thomas Maier, Stefan Scheiblich
  • Patent number: 5973159
    Abstract: 2-Hydroxy-6-trifluoromethylpyridine is prepared by reacting 2-chloro-6-trifluoromethylpyridine with an aqueous alkali metal hydroxide in a sealed vessel at a temperature of at least 140.degree. C. under autogenous pressure.
    Type: Grant
    Filed: February 23, 1998
    Date of Patent: October 26, 1999
    Assignee: Zeneca Limited
    Inventors: Ian Andrew Lilley, Raymond Vincent Heavon Jones, Stephen Martin Brown
  • Patent number: 5942623
    Abstract: The invention relates to a process for the preparation of 2-(pyrid-2-yloxymethyl)phenylacetates of formula (I) useful as intermediates for agricultural pesticides, which comprises reacting a 2-pyridine of formula (II), wherein L is a leaving group and A, D and m are as defined in the description with a compound MO--CH.sub.2 R where M is a metal atom and R is the residue of a metal salt of phenylacetic acid. It also includes the compounds MO--CH.sub.2 R, a process for their preparation and a "one-pot" process for the preparation of 2-(pyrid-2-yloxymethyl) phenylacetates from 3-isochromanone.
    Type: Grant
    Filed: February 19, 1998
    Date of Patent: August 24, 1999
    Assignee: ZENECA Limited
    Inventors: Alfred Glyn Williams, Gordon Richard Munns, Paul Anthony Worthington
  • Patent number: 5932731
    Abstract: The present invention provides a process for preparing an aromatic or heteroaromatic thiol represented by the formula (2), the process comprising hydrolyzing an aromatic or heteroaromatic halogenated methyl sulfide represented by the formula (1)Ar.paren open-st.SCH.sub.3-m X.sub.m).sub.n (1)Ar.paren open-st.SH).sub.n (2)wherein Ar is an aromatic or heteroaromatic ring which has no substituent or which has an optional substituent or substituents, X is a halogen atom, m is an integer of 1 to 3 and n is 1 or 2.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: August 3, 1999
    Assignee: Sumitomo Seika Chemicals Co., Ltd.
    Inventors: Hiroshi Goda, Mikio Yamamoto, Jun-ichi Sakamoto, Hitoshi Karino
  • Patent number: 5922880
    Abstract: The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: July 13, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5919930
    Abstract: Process for cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates.In a process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates under palladium catalysis in the presence of at least one water-soluble complex ligand, the reaction medium comprises an aqueous and an organic phase and the palladium is added in the form of a palladium compound soluble in the organic phase.Polycyclic aromatic compounds can thus be prepared economically and in very good yields and simultaneously very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: July 6, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5869506
    Abstract: The present invention provides a fluoropropene compound represented by Formula I: ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl group or other groups, Z represents an oxygen atom or other groups, R.sup.2, R.sup.3, and R.sup.4 each independently represent a C.sub.1 -C.sub.3 alkyl group or other groups, r represents an integer of 0 to 2, and X represents a halogen atom or other groups.
    Type: Grant
    Filed: January 30, 1997
    Date of Patent: February 9, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Izumi, Hiroshi Ikegami, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
  • Patent number: 5849920
    Abstract: A trifluoromethylpyridine of the formula Ib ##STR1## where the substituents have the following meanings: R.sup.1 is chlorine or fluorine;R.sup.2 is halogen; andR.sup.3 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, said groups being optionally substituted with 1 to 6 halogen atoms, C.sub.3 -C.sub.6 -cycloalkyl which is optionally substituted with 1 to 3 C.sub.1 -C.sub.3 -alkyl radicals, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.6 -alkyl, 3-oxetanyl, carboxyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -dialkylaminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.4 -alkenylaminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.4 -alkynylaminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkyl-C.sub.3 -C.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: December 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Peter Schafer, Cyrill Zagar
  • Patent number: 5817825
    Abstract: A process for the preparation of 1-hydroxy-2-pyridones is described in which a pyrone is reacted with a hydroxyl-ammonium salt in the presence of basic compounds, solvents and organic acids or salts thereof.
    Type: Grant
    Filed: October 12, 1995
    Date of Patent: October 6, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Anuschirwan Peyman, Dieter Bernd Reuschling, Adolf Heinz Linkies
  • Patent number: 5783522
    Abstract: Substituted 2-phenylpyridines I ##STR1## R.sup.1,R.sup.3 =H, halogen, alkyl, haloalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, OH, haloalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, SH, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, CHO, CN, CO.sub.2 H, alkoxycarbonyl, alkoxyalkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, CONH.sub.2, alkyl-aminocarbonyl, dialkylaminocarbonyl, pyrrolidinyl-carbonyl piperidylcarbonyl, morpholinylcarbonyl, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, alkylcarbonylamino, haloalkylcarbonylamino, alkylsulfonylamino;R.sup.2 =halogen, CN, NO.sub.2, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio; orR.sup.1 +R.sup.2 or R.sup.2 +R.sup.3 =trimethylene or tetramethylene chain;R.sup.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: July 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Hartmann Koenig, Ralf Klintz, Peter Muenster, Harald Rang, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5726314
    Abstract: Novel quaternary pyridinium compounds useful in inhibiting acetylcholinesterase in mammals of the general structure: ##STR1## or pharmaceutically acceptable salts thereof, where R.sub.5 is pentafluorophenyl, phenyl monosubstituted with K, phenyl disubstituted with K, phenyl trisubstituted with K, or naphthyl; R.sub.6 is H, C.sub.1-6 alkyl, phenyl, pentafluorophenyl, phenyl mono, di, or trisubstituted with K, C.sub.1-6 alkyl with an attached phenyl group, C.sub.1-6 alkyl with an attached phenyl group mono, di, or trisubstituted with K; K is halogen, COOH, OH, CN, NO.sub.2, NH.sub.2, C.sub.1-6 alkyl, C.sub.1-6 fluorinated alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylamine, C.sub.1-6 alkyl--O--CO--, C.sub.1-6 alkyl--CO--NH--, C.sub.1-6 alkyl--NH--CO--NH--, C.sub.1-6 alkyl--NH--CO--O--, C.sub.1-6 alkyl--NH--CO--, or (C.sub.1-6 alkyl).sub.2 N--CO--; X is OH, C.sub.1-6 alkyl--NH--CO--O--, (C.sub.1-6 alkyl).sub.2 --N--CO--O--, C.sub.1-6 fluoroalkyl--NH--CO--, or (C.sub.1-6 fluoroalkyl).sub.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: March 10, 1998
    Assignee: Georgia Tech Research Corp.
    Inventors: James C. Powers, Jerry J. Buccafusco, Kenneth M. Starks
  • Patent number: 5723450
    Abstract: The invention relates to compounds of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, halogen, an aliphatic radical or an aromatic radical, X is O, S or optionally substituted imino, Y is a bond or an optionally substituted bivalent hydrocarbon radical and Z is optionally substituted cycloalkyl or cycloalkenyl. The invention furthermore relates to processes for their preparation and their use as pesticides, in particular as insecticides, acaricides and fungicides.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: March 3, 1998
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies, Volkmar Wehner, Rainer Preuss, Wolfgang Schaper, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter Lummen, Werner Bonin
  • Patent number: 5714615
    Abstract: Methods for using novel quaternary pyridinium compounds in inhibiting acetylcholinesterase in mammals, specifically using the quaternary pyridinium compounds in the prophylaxis and treatment of organophosphate poisoning and mammalian dementia by mimicking or opposing the actions of the natural neurotransmitter acetylcholine.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: February 3, 1998
    Assignee: Georgia Tech Research Corporation
    Inventors: James C. Powers, Jerry J. Buccafusco, Kenneth M. Starks
  • Patent number: 5698550
    Abstract: Compounds of the formula ##STR1## wherein R is an optionally substituted heteroaryl group such as 2-chromanyl, 2-pyridyl or 5-fluoro-2-benzothiazoyl;X is O, S or (CH.sub.2).sub.m ;R.sup.1 is phenyl or pyridyl, optionally substituted by one or more (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkoxy, carboxy or ?(C.sub.1 -C.sub.3)alkoxy!carbonyl groups;n is 0, 1 or 2;m is 1 or 2;Y and Y.sup.1 are taken together and are oxygen, or Y and Y.sup.1 are taken separately, Y is hydrogen and Y.sup.1 is hydroxy or an in vivo hydrolyzable acyloxy group;Z is CH.sub.2, NR.sup.2, O or S; andR.sup.2 is hydrogen or (C.sub.1 -C.sub.3)alkyl;are useful in the treatment of asthma, arthritis and related diseases mediated by leukotrienes.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: December 16, 1997
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Anthony Marfat, Lawrence S. Melvin, Jr.
  • Patent number: 5686608
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5686460
    Abstract: The present invention relates to the carbocyclic diarylmethylene derivatives of formula (I): ##STR1## and to their use in therapeutics, especially as drugs with anti-inflammatory and analgesic properties.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: November 11, 1997
    Assignee: Laboratoires UPSA
    Inventors: Eric Nicolai, Michele Launay, Dominique Potin, Jean-Marie Teulon
  • Patent number: 5650417
    Abstract: Substituted pyridines, their preparation, and their use as pesticides and fungicides.The invention relates to compounds of the formula ##STR1## and to salts thereof in which 1, 2, 3 or 4 of the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are an aliphatic, alicyclic or araliphatic radical bonded by a --O--CH.sub.2 -- or --O--CO--, and the remaining ones of these radicals are H, halogen or an aliphatic or aromatic radical, X is O, S or optionally substituted imino, Y is a bond or a bivalent radical and Z is an aromatic radical or optionally substituted cycloalkyl or cycloalkenyl. The invention furthermore relates to processes for their preparation and to their use as pesticides, in particular as insecticides, acaricides and fungicides.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: July 22, 1997
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Dieter Bernd Reuschling, Adolf Heinz Linkies, Volkmar Wehner, Rainer Preuss, Wolfgang Schaper, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter Lummen, Werner Bonin
  • Patent number: 5646286
    Abstract: This invention involves a coupling reaction involving an organo-metallic catalyst, preferably a palladium catalyst involving reacting 2-halo-3-hydroxy-6-hydroxymethylpyridine, acrylic acid or its alkali metal salt and benzyl or a phenylalkyl derivative in presence of a dipolar aprotic solvent producing none other than the expected 2-propenoate-3-benzyl or phenylalkylether-6-hydroxymethyl-pyridine product. Said products are converted into medicaments useful for treating psoriasis.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 8, 1997
    Assignee: SmithKline Beecham plc
    Inventors: Peter William Sheldrake, Laurence Charles Powling, Peter William Bickle
  • Patent number: 5629428
    Abstract: 3-Chloropyridines, process for their preparation, and their use in liquid-crystal mixturesA 3-chloropyridine of the formula (I) ##STR1## in which the symbols have the following meaning: R.sup.1 and R.sup.2, independently of one another, are, for example, H or straight-chain or branched alkyl, A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are identical or different and are, for example, 1,4-phenylene, pyrazine-2,5-diyl or trans-1,4-cyclohexylene, M.sup.1, M.sup.2, M.sup.3 and M.sup.4 are identical or different and are, for example, --O-- or --CO--O--, R.sup.3, R.sup.4, R.sup.6 and R.sup.7, independently of one another are, for example, H or straight-chain or branched alkyl, M.sup.5 is, for example, --O--CO-- or a single bond, k, l, m, n, o, p, q and r are zero or one, with the proviso that the sum k+m+p+r is less than 4 and greater than zero, can advantageously be employed as a component in ferroelectric liquid-crystal mixtures.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: May 13, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Dietmar Jungbauer, Javier Manero
  • Patent number: 5625071
    Abstract: N-pyridinesulfonyl-N'-pyrimidinyl- and -triazinyl-ureas of formula I ##STR1## wherein R.sub.1 is hydrogen or fluorine;or R.sub.1 together with R.sub.3 is a C.sub.2 -C.sub.4 alkylene chain;R.sub.3 is hydrogen, fluorine or C.sub.1 -C.sub.3 alkyl;R.sub.2 is hydrogen, fluorine or C.sub.1 -C.sub.3 alkyl;R.sub.4 is hydrogen, fluorine, chlorine or C.sub.1 -C.sub.3 alkyl;R.sub.5 is hydrogen, fluorine, chlorine, C.sub.1 -C.sub.3 alkyl, or C.sub.1 -C.sub.3 alkyl substituted by fluorine or chlorine;R.sub.a is hydrogen or halogen, or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio radical each of which may be unsubstituted or mono- or poly-substituted by halogen;R.sub.b is hydrogen or a C.sub.1 -C.sub.4 alkyl radical;X is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkoxy mono- to tri-substituted by halogen;Y is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl mono- to tri-substituted by halogen, C.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: April 29, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Werner F ory
  • Patent number: 5599816
    Abstract: Antibacterial compounds having the formula ##STR1## and the pharmaceutically acceptable salts, esters and amides thereof, selected preferred examples of which include those compounds whereinA is.dbd.CR.sup.6 --;R.sup.1 is cycloalkyl of from three to eight carbon atoms or substituted phenyl;R.sup.2 is selected from the group consisting of ##STR2## R.sup.3 is halogen; R.sup.4 is hydrogen, loweralkyl, a pharmaceutically acceptable cation, or a prodrug ester group;R.sup.5 is hydrogen, loweralkyl, halo(loweralkyl), or --NR.sup.13 R.sup.14 ; andR.sup.6 is halogen, loweralkyl, halo(loweralkyl), hydroxy-substituted loweralkyl, loweralkoxy(loweralkyl), loweralkoxy, or amino(loweralkyl),as well as pharmaceutical compositions containing such compounds and the use of the same in the treatment of bacterial infections.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 4, 1997
    Assignee: Abbott Laboratories
    Inventors: Daniel T. Chu, Qun Li, Curt S. Cooper, Anthony K. L. Fung, Cheuk M. Lee, Jacob J. Plattner, Zhenkun Ma, Wei-Bo Wang
  • Patent number: 5563274
    Abstract: A process of preparing optically active alpha-chlorocarboxylic esters having the formula: ##STR1## from an optically active alpha-hydroxy carboxylic ester having the formula: ##STR2## in which process, an alpha-hydroxy carboxylate of formula II is brought into contact with phosgene and a compound chosen from amides, lactams and ureas, wherein R.sub.1 is an optionally substituted hydrocarbyl residue and R is preferably a methyl group.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: October 8, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Pascal Metivier, Genevieve Padilla, Harivelo Rajoharison
  • Patent number: 5550236
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Rainer Wingen, Javier Manero
  • Patent number: 5534634
    Abstract: Process for preparing trifluoroethyl sulfur compounds from thiolates and 1-chloro-2,2,2-trifluoroethane. The invention relates to the preparation of trifluoroethyl sulfur compounds of the formula RSCH.sub.2 CF.sub.3 by reacting 1-chloro-2,2,2-trifluoroethane CH.sub.2 Cl--CF.sub.3 in a polar aprotic solvent with salts of thiols of the formula RSH, where R can be an alkyl or aryl radical or a heterocyclic radical.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: July 9, 1996
    Assignee: Hoechst AG
    Inventors: Wolfgang Appel, Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
  • Patent number: 5530145
    Abstract: Novel anticholesteremic compounds capable of reducing blood cholesterol levels. Also included in this invention are (i) intermediates from which the abovementioned anticholesteremic compounds can be prepared, and (ii) methods for preparing both the intermediates and the anticholesteremic compounds.
    Type: Grant
    Filed: December 6, 1994
    Date of Patent: June 25, 1996
    Assignee: Syn-Tech Chem & Pharm Co., Ltd.
    Inventors: Hui-Po Wang, On Lee, Chin-Tsai Fan
  • Patent number: 5500429
    Abstract: This invention relates to 1-aryl-3-pyridinyl-2-propene-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: March 19, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Robert J. Dinerstein, Michael L. Edwards, David M. Stemerick, Keith A. Diekema
  • Patent number: 5491239
    Abstract: A method for halogenating an aromatic compound, which comprises reacting the aromatic compound of the formula (I): ##STR1## wherein X is a hydroxyl group, an amino group or an acylamino group, each of Z.sub.1 and Z.sub.2 is a hydrogen atom or a halogen atom, one of R and Y is a hydrogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and Q is a nitrogen atom or --C(T).dbd. (wherein T is a hydrogen atom, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group), with a halogenating agent to obtain a 3-halogenoaromatic compound of the formula (II): ##STR2## wherein one of R' and Y' is a halogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and X, Z.sub.1, Z.sub.2 and Q are as defined above.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: February 13, 1996
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Rikuo Nasu, Motohiko Hamaguchi, Hayato Ariyoshi
  • Patent number: 5486615
    Abstract: Methods of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs employ a dioxane intermediate as the immediate precursor to the DE ring intermediate. Novel intermediates are also disclosed.
    Type: Grant
    Filed: August 10, 1994
    Date of Patent: January 23, 1996
    Assignee: North Carolina State University
    Inventor: Daniel L. Comins
  • Patent number: 5484761
    Abstract: Disclosed are certain 5-methoxypyridinyloxypyridazines, compositions thereof which are herbicidal and methods of using such compositions for controlling undesired plants.Intermediates useful in preparing the pyridinyloxypyridazines are also disclosed.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: January 16, 1996
    Assignee: Monsanto Company
    Inventor: Michael S. South
  • Patent number: 5445763
    Abstract: A 3-fluoropyridine of the formula (I) ##STR1## in which the symbols have the following meanings: R.sup.1 and R.sup.2, independently of one another, are, for example, H or straight-chain or branched alkyl, A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are identical or different and are, for example, 1,4-phenylene, pyrazine-2,5-diyl or trans-1,4-cyclohexylene, M.sup.1, M.sup.2, M.sup.3 and M.sup.4 are identical or different and are, for example, --O-- or --CO--O--, R.sup.3, R.sup.4, R.sup.6 and R.sup.7, independently of one another are, for example, H or straight-chain or branched alkyl, M.sup.5 is for example, --O--CO-- or a single bond, k, l, m, n, o, p, q and r are zero or one, with the proviso that the sum k+m+p+r is less than 4 and greater than zero, can advantageously be employed as a component in ferroelectric liquid-crystal mixtures.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: August 29, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Anke Kaltbeitzel
  • Patent number: 5380862
    Abstract: A process for the preparation of isomer-free 2,5-dichloropyridine comprising alkoxylating 2-chloro-pyridine or 2-bromo-pyridine in the presence of a base at elevated temperatures, chlorinating with gaseous chlorine the alkoxylated product at ambient temperatures in an aqueous suspension in the presence of an auxiliary base, a small amount of a catalyst and optionally a small amount of an emulsifier, treating the isomer reaction mixture with a Vielsmeyer-Haack reagent, subjecting 2,5- and 2,3-dichloropyridine mixture to water vapor distillation and crystallizing the crystalline product from an alcohol-water mixture.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: January 10, 1995
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Stefan Sendelbach, Wolfgang Weiss, Winfried Orth, Hans W. Kleffner, Albrecht Laufer
  • Patent number: RE37087
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I in which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: March 6, 2001
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles