Chalcogen Bonded Directly To Ring Carbon Of The Hetero Ring Patents (Class 549/62)
  • Patent number: 4477678
    Abstract: Novel thioether compounds are disclosed which are useful as flavoring materials to enhance or impart meat-like flavors to foodstuffs. These compounds have the general formula ##STR1## where X can be, under specified conditions, --CH.sub.2 --, oxygen, or sulfur, Y can be oxygen or sulfur and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrogen or 1 to 3 carbon alkyl groups.
    Type: Grant
    Filed: January 4, 1983
    Date of Patent: October 16, 1984
    Assignee: P.F.W. Beheer B.V.
    Inventors: Steven van den Bosch, Dirk K. Kettenes, Kris B. de Ross, Gerben Sipma, Jan Stoffelsma
  • Patent number: 4463177
    Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).
    Type: Grant
    Filed: November 26, 1982
    Date of Patent: July 31, 1984
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 4438282
    Abstract: Sulfides prepared by reacting a sulfoxide with a hydrazine or hydroxylamine derivative or a quaternary salt thereof are useful starting materials for the preparation of drugs, pesticides and dyes.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: March 20, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hartmut Lardon, Guenther Seybold
  • Patent number: 4434293
    Abstract: The novel compounds cis-3-hydroxy-4-mercaptotetrahydrothiophene (I) and octahydrodithieno(3,4-b:3',4'e) 1,4-dithin (II) are prepared from 1,4-dithiothreitol and 1,4-dithioerythritol respectively. (I) has utility as an antibacterial agent. (II) has utility as an odorant.
    Type: Grant
    Filed: August 5, 1981
    Date of Patent: February 28, 1984
    Assignee: American Hoechst Corporation
    Inventor: Robert A. Sanchez
  • Patent number: 4433154
    Abstract: Bis(carboxamide) derivatives being useful as histamine H.sub.2 receptor antagonists or anti-peptic ulcer agents are provided from certain dicarboxylic acid derivatives.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: February 21, 1984
    Assignee: Shionogi & Company, Limited
    Inventor: Kentaro Hirai
  • Patent number: 4422955
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: December 27, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4421761
    Abstract: Thiophene derivatives of the formula ##STR1## wherein X, Y and Z are as herein defined, said compounds being useful as fungicides, are described.
    Type: Grant
    Filed: January 27, 1981
    Date of Patent: December 20, 1983
    Assignees: Hokko Chemical Industry Co. Ltd., Ube Industries, Ltd.
    Inventors: Shigeki Nagai, Takashi Yorie, Hisao Sugiura, Toru Hibi, Katsumi Sato, Takuo Wada, Masahiko Miyahara
  • Patent number: 4412856
    Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • Patent number: 4369322
    Abstract: The known synthesis for the production of aromatic substituted acetonitriles by reaction of aromatic substances with cyanogen chloride in the gas phase is improved by feeding the starting materials in gaseous form and separated from each other into the reactor. The process can be used to synthesize in general aromatic and especially hetero-aromatic substituted acetonitrile.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: January 18, 1983
    Assignee: Degussa AG
    Inventors: Peter Schalke, Axel Kleemann
  • Patent number: 4346041
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: August 24, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4344893
    Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: August 17, 1982
    Assignee: The Boots Company Limited
    Inventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
  • Patent number: 4331680
    Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: May 25, 1982
    Assignee: The Boots Company
    Inventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
  • Patent number: 4328169
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of an alkylene oxide derivative and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.
    Type: Grant
    Filed: October 27, 1980
    Date of Patent: May 4, 1982
    Assignee: Emery Industries, Inc.
    Inventor: Allen L. Hall
  • Patent number: 4309554
    Abstract: 3-(2-Thiophenesulfonyl)-2-halopropanenitriles of the formula ##STR1## wherein R is H, C.sub.1-4 alkyl, Br or Cl and X is Br or Cl. The compounds have antimicrobial utility.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: January 5, 1982
    Assignee: The Dow Chemical Company
    Inventor: Christian T. Goralski
  • Patent number: 4302461
    Abstract: Antiinflammatory 5-substituted-2,3-diarylthiophenes, such as 2,3-bis(4-fluorophenyl)-5-(trifluoromethylthio)thiophene, useful for treating arthritis and related diseases.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: November 24, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Saul C. Cherkofsky
  • Patent number: 4298613
    Abstract: Heterocyclic sulfenamides, such as N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-trifluoromethyl)ph enyl]-3-nitro-2-pyridinesulfenamide, are useful as miticides, insecticides, fungicides and ovicides.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: November 3, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gerald E. Lepone
  • Patent number: 4289894
    Abstract: Compounds of the formula: ##STR1## are disclosed wherein R is C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.3 to C.sub.8 cycloalkyl, phenyl, halophenyl, naphthyl, benzyl, indanyl, phenacyl, p-nitrophenacyl, xylyl or acetoxymethyl; R.sup.1 is phenyl, benzyl or phenyl or benzyl substituted by halo, nitro, dialkylamino, alkoxy or trifluoromethyl, lower alkyl or allyl; and X is halo. The compounds are intermediates in the manufacture of penicillins.
    Type: Grant
    Filed: March 6, 1979
    Date of Patent: September 15, 1981
    Assignee: Chinoin Gyogyszer es Vegylszeti Termekek Gyara R.T.
    Inventors: Magda Huhn, Eva Somfai, Gabor Szabo, Gabor Resovszki, Zoltan Gneth
  • Patent number: 4254266
    Abstract: Fluorinated-alkyl sulfides represented by [R.sub.f (CH.sub.2).sub.n S].sub.z Q where R.sub.f is fluoroalkyl, n is 2 or 3, z is 1 or 2, and Q is an aryl, alkylaryl, alkyl heterocyclic or heterocyclic radical, are useful as surfactants or as intermediates for the preparation of salt-type, quaternary-salt, or amphoteric surfactants.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: March 3, 1981
    Assignee: Pennwalt Corporation
    Inventors: Sameeh S. Toukan, Murray Hauptschein
  • Patent number: 4252739
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: February 24, 1981
    Assignee: Emery Industries, Inc.
    Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
  • Patent number: 4250326
    Abstract: A method of reducing the content of a haloethynyl-containing impurity in a synthetic dihaloethenylcyclopropanecarboxylate by treatment with a phosphite under condition allowing the haloethynyl-containing impurity and phosphite to chemically interact, and thereafter recovering the dihaloethenylcyclopropanecarboxylate from the reaction mixture is disclosed.
    Type: Grant
    Filed: October 22, 1979
    Date of Patent: February 10, 1981
    Assignee: FMC Corporation
    Inventor: Morris L. Fishman
  • Patent number: 4233333
    Abstract: Compounds of the formula ##STR1## wherein X is oxygen or sulfur;R.sub.1 is hydrogen, methyl or ethyl; andR.sub.2 is methyl or ethyl;and non-toxic, physiologically acceptable salts thereof formed with an inorganic or organic base. The compounds as well as their salts are useful as sweetening agents.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: November 11, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Gunter Trummlitz, Ernst Seeger, Wolfhard Engel
  • Patent number: 4230872
    Abstract: Novel 9-substituted or unsubstituted thienyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives, useful as antitumor agents as well as processes for their preparation and novel intermediates are disclosed.
    Type: Grant
    Filed: May 11, 1978
    Date of Patent: October 28, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael J. Klaus, Beverly A. Pawson
  • Patent number: 4214091
    Abstract: A novel antibiotic No. 2-200 represented by the formula ##STR1## which has a broad antimicrobial spectrum and a process for producing the same by cultivating an antibiotic No. 2-200 producing microorganism of the genus Nocardia, and recovering by isolation the antibiotic No. 2-200 accumulated in the culture.
    Type: Grant
    Filed: September 21, 1978
    Date of Patent: July 22, 1980
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hideo Oishi, Takao Noto, Yoshiharu Nawata, Hiroshi Okazaki, Hiroshi Sasaki, Kunio Ando, Haruki Ogawa
  • Patent number: 4174405
    Abstract: Substituted thiophenes of the following formula, some of which are new compounds, are useful in controlling certain pests, particularly mites: ##STR1## wherein A, Y and Z are various substituents such as phenyl and substituted phenyl.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: November 13, 1979
    Assignee: Uniroyal, Inc.
    Inventors: Douglas I. Relyea, Winchester L. Hubbard, Robert E. Grahame, Jr.
  • Patent number: 4165322
    Abstract: A process for producing a lactone-substituted aniline wherein an alpha-halo-gamma-butyrolactone is reacted with an aniline in the presence of water at a temperature between 80.degree. and 160.degree. C. Thus, 3-(N-2,6-dimethylphenylamino)-gamma-butyrolactone is prepared by reacting an alpha-halo-gamma-butyrolactone with 2,6-dimethylaniline in the presence of water and an inert organic solvent at a temperature between 80.degree. and 160.degree. C. This process is advantageously combined with a subsequent acylation step to provide a continuous means for making materials such as 3-(N-chloroacetyl-N-2,6-dimethylphenylamino)-gamma-butyrolactone.
    Type: Grant
    Filed: November 1, 1977
    Date of Patent: August 21, 1979
    Assignee: Chevron Research Company
    Inventor: Richard N. Reynolds, Jr.