The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/344)
  • Patent number: 4939157
    Abstract: Substituted pyridine-N-oxides of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 is phenyl or substituted phenyl, salts thereof which are physiologically tolerated by plants, and fungicides containing them.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: July 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Ernst Buschmann, Manfred Lauer, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 4931458
    Abstract: Heterocyclic compounds of the formula ##STR1## wherein X is --CH.dbd.CH--; R.sup.1 is the group Ar--R.sup.2 or --CH.dbd.CH--C(CH.sub.3).dbd.CH--R.sup.21 ; Ar is phenyl, pyridyl, furyl or thienyl; R.sup.2 is --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3, lower-alkylsulphonyl or formyl; R.sup.21 is --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3 or formyl; R.sup.3 is hydrogen or lower-alkyl; and R.sup.4 is hydrogen, hydroxy, amino, lower-alkyl amino, di-(lower alkyl)amino or lower alkyl; with at least one ring of the molecule being heterocyclic, as well as salts of such compounds are useful in rodenticidal compositions containing a bait to eliminate rodents.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: June 5, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Harald Weiser
  • Patent number: 4923884
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: May 8, 1990
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • 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: 4880937
    Abstract: An alcohol compound is produced by reducing a carboxylic acid or an ester thereof with an alcohol in the presence of a solid catalyst. The catalyst includes a hydrous metal oxide belonging to Group IV of the Periodic Table.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: November 14, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
  • 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: 4837327
    Abstract: Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: June 6, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4833164
    Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: May 23, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Douglas G. Batt
  • Patent number: 4812460
    Abstract: The present invention discloses 3-[2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)ethenyl]pyridine and its use in treating inflammation, particularly chronic inflammatory diseases such as arthritis, and allergic disorders.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 14, 1989
    Assignee: Boehringer Ingelheim Pharmaceutical, Inc.
    Inventor: Edward S. Lazer
  • 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: 4794188
    Abstract: Compounds of the formula:Ar.sub.1 -X-Ar-Z-(R).sub.n'and salts thereof, whereinAr.sub.1 is a nitrogen, sulfur or oxygen heterocyclic ring;Ar is a phenyl ring or a nitrogen, oxygen or sulfur heterocyclic ring;Ar and Ar.sub.1 may be fully substituted or less than fully substituted with H, CH.sub.3, lower alkyl, aryl, aralkyl, halo, hydroxy, lower alkoxy, CF.sub.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: December 27, 1988
    Assignee: USV Pharmaceutical Corporation
    Inventors: John H. Musser, Utpal R. Chakraborty
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4789745
    Abstract: The present invention provides novel .omega.-(3-pyridynl) oxa-, thia-, and aza- alkanoic acids and esters thereof, which are useful as thromboxane A.sub.2 (TXA.sub.2) inhibitors and as such represent potent pharmacological agents.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: December 6, 1988
    Assignee: The Upjohn Company
    Inventor: Chiu-Hong Lin
  • Patent number: 4778818
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: October 18, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4767865
    Abstract: The present invention provides novel 3'-pyridinylalkenylindole-2-carboxylic acids and derivatives thereof of the formula I and II ##STR1## which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: August 30, 1988
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Chiu-Hong Lin
  • 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: 4745120
    Abstract: The present invention relates to new pyridines substituted in the 3-position, of the formula ##STR1## and to a process for their preparation. The compounds bring about specific inhibition of thromboxane synthetase and can thus be used as medicaments.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: May 17, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Wess, Wilhelm Bartmann, Gerhard Beck, Hans-Hermann Lau
  • Patent number: 4743606
    Abstract: The present invention discloses 3-[2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)ethenyl]pyridine and its use in treating inflammation, particularly chronic inflammatory diseases such as arthritis, and allergic disorders.
    Type: Grant
    Filed: March 25, 1986
    Date of Patent: May 10, 1988
    Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventor: Edward S. Lazer
  • Patent number: 4736037
    Abstract: 2-Halo-pyridine of the formula: ##STR1## wherein X is Cl or Br; Ar is phenyl or substituted phenyl of the formula ##STR2## in which n is 0, 1, 2 or 3; R is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenoxy, C.sub.1-4 alkylthio, halogen, OH or C.sub.6 H.sub.5 ; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: April 5, 1988
    Assignee: Lacer, S.A.
    Inventors: Ricardo D. Matas, Jose M. C. Puigmarti, Jose M. Repolles, Jorge S. Sera
  • Patent number: 4699652
    Abstract: The invention is directed to fungicidal pyridine derivatives and their N-amino salts and acid addition salts, said pyridine derivatives having the formula ##STR1## wherein R is mono-, di- or trisubstituted phenyl, wherein the substituents are the same or different and are selected from the group consisting of 1 to 3 halogen, 1 or 2 C.sub.1-3 -alkyl, 1 or 2 C.sub.1-3 -alkoxy and 1 or 2 trifluoromethyl moieties; R.sup.1 is hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl or C.sub.2-6 -alkynyl; R.sup.2 is hydrogen; R.sup.3 is selected from the group consisting of --CO--R.sup.4, --C(OR.sup.5).dbd.CHR.sup.6, --CH(R.sup.4)OR.sup.5, --C(R.sup.4).dbd.NOR.sup.7 and ##STR2## R.sup.4 is hydrogen or C.sub.1-5 -alkyl; R.sup.5 is C.sub.1-4 -alkyl; R.sup.6 and R.sup.7 are hydrogen or C.sub.1-4 -alkyl; n is 2 or 3; or R.sup.2 taken together with R.sup.4 is equal to the group --CH.dbd.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: October 13, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Beat Zehnder
  • Patent number: 4692528
    Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p-MeC.sub.6 H.sub.4 SO.sub.3 and MeSO.sub.3 --.
    Type: Grant
    Filed: June 11, 1985
    Date of Patent: September 8, 1987
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Ashokkumar B. Shenvi
  • Patent number: 4692184
    Abstract: There are disclosed novel 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds useful as herbicides, and as intermediates which provide herbicides.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: September 8, 1987
    Assignee: Monsanto Company
    Inventor: Len F. Lee
  • Patent number: 4678790
    Abstract: Novel pyridine, pyrazine and pyrimidine derivatives of the formula ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as hereinafter set forth, and acid addition salts thereof, processes for their preparation, fungicidal compositions containing these compounds as the active ingredient as well as the use of such compounds or compositions for the control of fungi in agriculture and in horticulture are disclosed.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: July 7, 1987
    Assignee: Hoffman-La Roche Inc.
    Inventors: Franz Dorn, Albert Pfiffner, Beat Zehnder
  • Patent number: 4677206
    Abstract: There is described a photographic system wherein development of an exposed photosensitive element with an aqueous alkaline photographic developing composition is effected in the presence of a compound which releases a quaternary in alkaline environment. Photographic products and processes utilizing such compounds are also disclosed.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: June 30, 1987
    Assignee: Polaroid Corporation, Patent Dept.
    Inventor: John M. Dolphin
  • Patent number: 4677128
    Abstract: (Arylthio)pyridylalkanol derivatives of the formula: ##STR1## in which: Ar denotes an optionally substituted aryl radical,R denotes a hydrogen atom or an optionally substituted alkyl radical, an optionally substituted aryl radical or an optionally substituted aralkyl radical,R.sub.1 denotes an alkyl radical, and n equals 0, 1, 2, 3 or 4.
    Type: Grant
    Filed: February 26, 1985
    Date of Patent: June 30, 1987
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Pierre Place, Claude Anding, Jean-Claude Debourge
  • 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: 4603208
    Abstract: Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.
    Type: Grant
    Filed: February 10, 1983
    Date of Patent: July 29, 1986
    Assignee: Kuraray Co., Ltd.
    Inventors: Takashi Onishi, Shigeaki Suzuki, Fumio Mori, Tetsuo Takigawa, Yoshiji Fujita, Masao Mizuno, Takashi Nishida
  • Patent number: 4598080
    Abstract: The invention relates to new pyridine derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms,and acid addition and quaternary ammonium salts thereof.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they inhibit the microsomal monooxigenase enzyme system of the liver. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: July 1, 1986
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt
    Inventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolcs Szebereneyi, Laszlo Szporny, Sandor Gorog, Istvan Hajdu
  • Patent number: 4593131
    Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: June 3, 1986
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4567184
    Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen, alkyl, carboxy, alkylcarboxy, arylcarboxy, alkyl carbalkoxy, alkanoyl, formyl, nitrile, amino, amino alkyl, alkylamine, carboxamide, halo, trihalomethyl, hydroxy, alkoxy, aryloxy, nitro, sulfonyl, sulfonamide, thio, alkylthio, or R.sub.1 and R.sub.2 can be taken together to form a phenyl ring;B is C or N, in which N can be in any position of the ring;X is O, S, NR.sub.4, CH.sub.2 Z, CH.dbd.N, CH.dbd.CH, C.tbd.C, CH.sub.2 ZCH.sub.2, C.dbd.O, C.dbd.CR or WC.dbd.O;Y is CHCH.sub.2, C.dbd.CH, C--CH.sub.2, CHCHR.sub.5, CHC(R.sub.5).sub.2 or CC(R.sub.5).sub.2 ;R.sub.3 is O, OH, OR.sub.4, SH, SR.sub.4, NH, HNR.sub.4 or N(R.sub.4).sub.2 ; andM is an integer from 0 to 10; wherein Z is O, S or NR.sub.4 ; R.sub.4 is H, alkyl or aryl;W is O, S or NR.sub.4 ; and R.sub.5 is H, alkyl or fluoro have antiinflammatory and antiallergic activities.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: January 28, 1986
    Assignee: USV Pharmaceutical Corporation
    Inventors: John H. Musser, Utpal R. Chakraborty
  • Patent number: 4556661
    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 27, 1982
    Date of Patent: December 3, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Franz Dorn, Francois Montavon, Milos Suchy
  • Patent number: 4551460
    Abstract: Pyrido[2,1-b]quinazoline derivatives of the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as hereinafter set forth, are described. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions as well as for the treatment of vascular disorders involving thrombosis.
    Type: Grant
    Filed: March 2, 1983
    Date of Patent: November 5, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Jefferson W. Tilley
  • Patent number: 4537963
    Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3,2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.3.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p--MeC.sub.6 H.sub.4 SO.sub.3 -- and MeSO.sub.3 --.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ashokkumar B. Shenvi
  • Patent number: 4535084
    Abstract: A series of 4-(2-hydroxyethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable acid addition salts, having immunoregulatory activity are disclosed. Preferred compounds include 4-(2-hydroxyethylthiomethyl)pyridine itself, as well as 4-(2-hydroxy-1-propylthiomethyl)pyridine, 4-(3-hydroxy-2-butylthiomethyl)pyridine, the acetate esters corresponding to the above compounds, and 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine.
    Type: Grant
    Filed: March 18, 1983
    Date of Patent: August 13, 1985
    Assignee: Pfizer Inc.
    Inventors: Joseph G. Lombardino, Charles A. Harbert
  • Patent number: 4525360
    Abstract: The present invention relates to novel phenylindene derivatives having interesting pharmacodynamic properties which make them useful as psychopharmacologicals in the treatment especially of psychoses such as schizophrenia, having a low degree of undesired side effects such as cataleptic effects, methods for the preparation of said phenylindene derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.
    Type: Grant
    Filed: October 5, 1983
    Date of Patent: June 25, 1985
    Assignee: Kefalas A/S
    Inventor: Jens K. Perregaard
  • Patent number: 4512995
    Abstract: 3-[2-aryloxy-3-hydroxy-3-phenyl or 3-t-butylprop-1-enyl]pyridine and derivatives thereof are disclosed. These compounds are useful as fungicides, especially agricultural fungicides.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: April 23, 1985
    Assignee: Chevron Research Company
    Inventor: Allan F. Rose
  • Patent number: 4510148
    Abstract: Compounds of the formula ##STR1## wherein R is thienyl, mono-, di- and trihalothienyl, furyl, 2-benzothiazolyl, pyridyl or chloropyridyl and their pharmaceutically acceptable salts are useful agents for combating fungal infections in animals, including humans.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: April 9, 1985
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Kelvin Cooper
  • Patent number: 4477673
    Abstract: The invention relates to compounds of the formula I ##STR1## wherein R' is bound in the 4- or 5-position, R and R' are --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5, --CH.sub.2 --X, --CH.sub.2 P.sup..sym. (Y).sub.3 X.sup..crclbar., --CH.sub.2 P(O)(C.sub.1-3 alkoxy).sub.2 or --CH.dbd.CH.sub.2, R" is C.sub.1-10 alkyl, X is a halogen atom, X.sup..crclbar. is the anion corresponding to X and Y is phenyl or phenyl which is substituted by a C.sub.1 -C.sub.5 alkyl group. These compounds can be obtained by a novel simple process in good to very good yield by co-cyclotrimerizing nitriles R"--CN with alkynes HC.dbd.C--Z (Z is --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH or --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5), in the presence of a cobalt(I) catalyst, dehydrating the resultant pyridines either to compounds of the formula I, in which R and R" are --CH.dbd.CH.sub.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: October 16, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Jurgen Kaschig
  • Patent number: 4469873
    Abstract: A new composition of matter is revealed, characterized by the general formula: ##STR1## wherein x and y are integers of from 0 to 20 such that the sum of x plus y is an integer of from 8 to 20 and M is an anion of an organic or mineral acid having a valance of z.This composition of matter is useful for the preparation of cationic polymeric surfactants, flocculants and coagulants.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: September 4, 1984
    Assignee: Texaco Inc.
    Inventor: Edward C. Y. Nieh
  • Patent number: 4438122
    Abstract: 1-Phenoxy-2-pyridinyl(pyrimidinyl)-alkanols of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents a nitrogen atom or the CH group,Y represents halogen, alkyl, cycloalkyl, alkoxy, halogenoalkyl, alkylthio, or an optionally substituted phenyl, phenoxy, phenylalkoxy or phenylalkyl radical, andn represents 0 or an integer from 1 to 5, the Y's being selected independently of one another when n is 2, 3, 4 or 5,in the form of the free base, a salt or a metal salt complex thereof, which possess fungicidal properties.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: March 20, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Graham Holmwood, Paul-Ernst Frohberger, Wilhelm Brandes, Volker Paul
  • Patent number: 4431812
    Abstract: Pyridinecarbinols of the formula ##STR1## where R.sup.1 is hydrogen or alkyl, R.sup.2 is alkyl or alkenyl, and R.sup.3, R.sup.4 and R.sup.5 are hydrogen, chlorine, bromine, fluorine or alkyl, plant-physiologically tolerated addition salts of these compounds with acids, and fungicides containing these compounds.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: February 14, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4429162
    Abstract: The instant invention relates to compounds of the formula ##STR1## wherein each R.sub.f is independently straight or branched chain perfluoroalkyl of 2 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms;each R.sub.1 is independently straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, or alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substituent, hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, chloro, bromo, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms, and R.sub.2 and R.sub.3 additionally may, together with the carbon atoms to which they are attached, form a fused benzo ring;R.sub.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: January 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Thomas W. Cooke, Robert A. Falk
  • Patent number: 4426524
    Abstract: Disclosed and exemplified are insecticidal and acaricidal optionally substituted furylbenzyl, thienylbenzyl, pyrazinylbenzyl, or pyridinzylbenzyl esters of the pyrethroid acids, novel pyrethroid alcohols and other intermediates, and compositions, a method of use and a process for preparation of the esters.
    Type: Grant
    Filed: January 21, 1982
    Date of Patent: January 17, 1984
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4420434
    Abstract: The instant invention relates to the use of ion-pair complexes derived from anionic perfluoroalkyl sulfonates, carboxylates, phosphates and phosphonates and cationic perfluoroalkyl surfactants. Such complexes are capable of reducing the surface tension of aqueous solutions dramatically even at extremely low concentrations, and are useful as wetting, spreading and leveling agents and are especially preferred as components in so-called aqueous film forming foam compositions for fighting polar and non-polar solvent and fuel fires.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: December 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk
  • Patent number: 4414217
    Abstract: 3,5-Di(t-butyl)-4-hydroxyphenyl and 3,5-di(t-butyl)-4-hydroxybenzoyl-substituted pyridines have pharmacological activity as antiinflammatory agents.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: November 8, 1983
    Assignee: Riker Laboratories, Inc.
    Inventor: George G. I. Moore
  • Patent number: 4408043
    Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: October 4, 1983
    Assignee: Nalco Chemical Company
    Inventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
  • Patent number: 4404377
    Abstract: Heterocyclic/aromatic fluorinated compounds of the formula ##STR1## are disclosed. The cationic compounds are useful as surfactants.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: September 13, 1983
    Assignee: Nalco Chemical Company
    Inventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
  • Patent number: 4382942
    Abstract: Novel 3-(1,2,5,6-tetrahydropyridin-3-yl)-phenols of the formula ##STR1## wherein X is selected from the group consisting of hydrogen and an acyl of an organic carboxylic acid of 2 to 7 carbon atoms, Y is selected from the group consisting of hydrogen and --OX, R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms optionally substituted with --OH, cycloalkylalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 3 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted on the alkyl with --OH with the proviso that when R is hydrogen, X is hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic agonist and/or antagonist properties and their preparation.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: May 10, 1983
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Jacques Guillaume, Claude Dumont