Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/303)
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Patent number: 6407245Abstract: 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: GrantFiled: February 26, 2001Date of Patent: June 18, 2002Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Joachim Gebhardt, Heinz Isak, Michael Rack, Joachim Rheinheimer, Peter Schäfer
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Patent number: 6323222Abstract: 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: GrantFiled: May 2, 2000Date of Patent: November 27, 2001Assignee: Adir et CompagnieInventors: Sylvain Rault, Olivier Renault, Jean Guillon, Patrick Dallemagne, Pierre Renard, Bruno Pfeiffer, Pierre Lestage, Marie-Cécile Lebrun
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Patent number: 6316631Abstract: 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: GrantFiled: March 4, 1999Date of Patent: November 13, 2001Assignee: Pfizer Inc.Inventors: Yuhpyng L. Chen, Sally Gut Ruggeri
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Patent number: 6310006Abstract: 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: GrantFiled: May 13, 1998Date of Patent: October 30, 2001Assignee: American Cyanamid CompanyInventors: Thomas Maier, Stefan Scheiblich, Helmut S. Baltruschat
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Patent number: 6306839Abstract: 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: GrantFiled: September 16, 1999Date of Patent: October 23, 2001Assignee: Dow AgroSciences LLCInventors: 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
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Patent number: 6271379Abstract: 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: GrantFiled: March 8, 2000Date of Patent: August 7, 2001Assignee: Georgetown UniversityInventors: Werner Tückmantel, Alan P. Kozikowski
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Publication number: 20010006805Abstract: 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: ApplicationFiled: January 22, 2001Publication date: July 5, 2001Inventor: Dean Kent Hoglen
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Patent number: 6248892Abstract: 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: GrantFiled: July 1, 1999Date of Patent: June 19, 2001Assignee: Clariant GmbHInventors: Antje Noerenberg, Steffen Haber, Andreas Meudt
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Patent number: 6175011Abstract: 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: GrantFiled: March 30, 1999Date of Patent: January 16, 2001Assignee: Lonza AGInventors: Jean-Paul Roduit, Georges Kalbermatten
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Patent number: 6166047Abstract: 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: GrantFiled: April 2, 1998Date of Patent: December 26, 2000Inventors: Gary Maurice Dull, Grayland Page Dobson, Jared Miller Wagner
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Patent number: 6143899Abstract: 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: GrantFiled: September 3, 1999Date of Patent: November 7, 2000Assignee: Zeneca LimitedInventors: 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
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Patent number: 6133447Abstract: 2-chloro-3-hydroxypyridine is prepared by reacting 3-hydroxypyridine with aqueous sodium hypochlorite.Type: GrantFiled: February 17, 1999Date of Patent: October 17, 2000Assignee: Novartis Crop Protection, Inc.Inventors: Dominik Faber, Denis Blaser, Thierry Bourquard, Andrea Rolf Sting, Dean Kent Hoglen
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Patent number: 6121454Abstract: 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: GrantFiled: April 21, 1998Date of Patent: September 19, 2000Assignee: PDi-Research Laboratories, Inc.Inventors: Michel Zoghbi, Liquin Chen
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Patent number: 6090817Abstract: (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: GrantFiled: September 1, 1998Date of Patent: July 18, 2000Assignee: Novartis AGInventor: Paul W. Manley
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Patent number: 6054583Abstract: 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: GrantFiled: May 5, 1999Date of Patent: April 25, 2000Assignee: Rohm and Haas CompanyInventors: Martha Jean Kelly, Damian Gerard Weaver
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Patent number: 6048823Abstract: 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: GrantFiled: August 3, 1998Date of Patent: April 11, 2000Assignees: 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
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Patent number: 6020524Abstract: 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: GrantFiled: March 29, 1999Date of Patent: February 1, 2000Assignee: ZENECA LimitedInventors: Alfred Glyn Williams, Gordon Richard Munns, Paul Anthony Worthington
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Patent number: 6015569Abstract: 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: GrantFiled: November 17, 1997Date of Patent: January 18, 2000Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 6008161Abstract: 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: GrantFiled: July 14, 1998Date of Patent: December 28, 1999Assignee: American Cyanamid CompanyInventors: Axel Kleemann, Helmut Siegfried Baltruschat, Thekla Haselwander, Thomas Maier, Stefan Scheiblich
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Patent number: 5973159Abstract: 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: GrantFiled: February 23, 1998Date of Patent: October 26, 1999Assignee: Zeneca LimitedInventors: Ian Andrew Lilley, Raymond Vincent Heavon Jones, Stephen Martin Brown
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Patent number: 5942623Abstract: 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: GrantFiled: February 19, 1998Date of Patent: August 24, 1999Assignee: ZENECA LimitedInventors: Alfred Glyn Williams, Gordon Richard Munns, Paul Anthony Worthington
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Patent number: 5932731Abstract: 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: GrantFiled: December 22, 1997Date of Patent: August 3, 1999Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Mikio Yamamoto, Jun-ichi Sakamoto, Hitoshi Karino
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Patent number: 5922880Abstract: 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: GrantFiled: May 20, 1997Date of Patent: July 13, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
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Patent number: 5919930Abstract: 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: GrantFiled: July 26, 1995Date of Patent: July 6, 1999Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5869506Abstract: 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: GrantFiled: January 30, 1997Date of Patent: February 9, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Izumi, Hiroshi Ikegami, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
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Patent number: 5849920Abstract: 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: GrantFiled: July 14, 1997Date of Patent: December 15, 1998Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Peter Schafer, Cyrill Zagar
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Patent number: 5817825Abstract: 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: GrantFiled: October 12, 1995Date of Patent: October 6, 1998Assignee: Hoechst AktiengesellschaftInventors: Anuschirwan Peyman, Dieter Bernd Reuschling, Adolf Heinz Linkies
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Patent number: 5783522Abstract: 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: GrantFiled: January 11, 1996Date of Patent: July 21, 1998Assignee: BASF AktiengesellschaftInventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Hartmann Koenig, Ralf Klintz, Peter Muenster, Harald Rang, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
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Patent number: 5726314Abstract: 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: GrantFiled: September 30, 1996Date of Patent: March 10, 1998Assignee: Georgia Tech Research Corp.Inventors: James C. Powers, Jerry J. Buccafusco, Kenneth M. Starks
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Patent number: 5723450Abstract: 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: GrantFiled: September 12, 1994Date of Patent: March 3, 1998Assignee: Hoechst Schering AgrEvo GmbHInventors: 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
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Patent number: 5714615Abstract: 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: GrantFiled: February 8, 1994Date of Patent: February 3, 1998Assignee: Georgia Tech Research CorporationInventors: James C. Powers, Jerry J. Buccafusco, Kenneth M. Starks
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Patent number: 5698550Abstract: 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: GrantFiled: June 14, 1993Date of Patent: December 16, 1997Assignee: Pfizer Inc.Inventors: James F. Eggler, Anthony Marfat, Lawrence S. Melvin, Jr.
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Patent number: 5686608Abstract: 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: GrantFiled: April 24, 1995Date of Patent: November 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5686460Abstract: 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: GrantFiled: October 7, 1996Date of Patent: November 11, 1997Assignee: Laboratoires UPSAInventors: Eric Nicolai, Michele Launay, Dominique Potin, Jean-Marie Teulon
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Patent number: 5650417Abstract: 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: GrantFiled: September 12, 1994Date of Patent: July 22, 1997Assignee: Hoechst Schering AgrEvo GmbHInventors: 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
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Patent number: 5646286Abstract: 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: GrantFiled: May 26, 1995Date of Patent: July 8, 1997Assignee: SmithKline Beecham plcInventors: Peter William Sheldrake, Laurence Charles Powling, Peter William Bickle
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Patent number: 5629428Abstract: 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: GrantFiled: May 10, 1994Date of Patent: May 13, 1997Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Dietmar Jungbauer, Javier Manero
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Patent number: 5625071Abstract: 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: GrantFiled: May 26, 1995Date of Patent: April 29, 1997Assignee: Ciba-Geigy CorporationInventor: Werner F ory
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Patent number: 5599816Abstract: 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: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Abbott LaboratoriesInventors: Daniel T. Chu, Qun Li, Curt S. Cooper, Anthony K. L. Fung, Cheuk M. Lee, Jacob J. Plattner, Zhenkun Ma, Wei-Bo Wang
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Patent number: 5563274Abstract: 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: GrantFiled: December 3, 1993Date of Patent: October 8, 1996Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Pascal Metivier, Genevieve Padilla, Harivelo Rajoharison
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Patent number: 5550236Abstract: 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: GrantFiled: April 24, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Javier Manero
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Patent number: 5534634Abstract: 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: GrantFiled: September 29, 1994Date of Patent: July 9, 1996Assignee: Hoechst AGInventors: Wolfgang Appel, Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
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Patent number: 5530145Abstract: 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: GrantFiled: December 6, 1994Date of Patent: June 25, 1996Assignee: Syn-Tech Chem & Pharm Co., Ltd.Inventors: Hui-Po Wang, On Lee, Chin-Tsai Fan
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Patent number: 5500429Abstract: 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: GrantFiled: November 17, 1993Date of Patent: March 19, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: Robert J. Dinerstein, Michael L. Edwards, David M. Stemerick, Keith A. Diekema
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Patent number: 5491239Abstract: 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: GrantFiled: November 2, 1993Date of Patent: February 13, 1996Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Motohiko Hamaguchi, Hayato Ariyoshi
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Patent number: 5486615Abstract: 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: GrantFiled: August 10, 1994Date of Patent: January 23, 1996Assignee: North Carolina State UniversityInventor: Daniel L. Comins
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Patent number: 5484761Abstract: 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: GrantFiled: October 11, 1994Date of Patent: January 16, 1996Assignee: Monsanto CompanyInventor: Michael S. South
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Patent number: 5445763Abstract: 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: GrantFiled: June 7, 1993Date of Patent: August 29, 1995Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Anke Kaltbeitzel
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Patent number: 5380862Abstract: 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: GrantFiled: August 23, 1993Date of Patent: January 10, 1995Assignee: Rutgerswerke AktiengesellschaftInventors: Stefan Sendelbach, Wolfgang Weiss, Winfried Orth, Hans W. Kleffner, Albrecht Laufer
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Patent number: RE37087Abstract: 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: GrantFiled: June 20, 1991Date of Patent: March 6, 2001Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles