Chalcogens Bonded Directly At 2- And 5-positions Of The Oxazole Ring Patents (Class 548/227)
  • Patent number: 4695567
    Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: September 22, 1987
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
  • Patent number: 4689336
    Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]-furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: August 25, 1987
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4686295
    Abstract: This invention relates to new compounds of the formula ##STR1## wherein A is a hydroxy, lower alkoxy, lower alkenoxy, diloweralkylamino lower alkoxy, acylamino lower alkoxy, acyloxy, lower alkoxy, aryloxy, arloweralkyloxy, amino, loweralkylamino, diloweralkylamino, aryloweralkylamino, hydroxyamino, or substituted aryloxy, or substituted arloweralkoxy wherein the substituent is methyl, halo or methoxy;R.sub.1, R.sub.2, and R.sub.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: August 11, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Raymond D. Youssefyeh, Jerry W. Skiles, John T. Suh, Howard Jones
  • Patent number: 4663341
    Abstract: This invention relates to N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 5, 1987
    Assignee: Rohm and Haas Company
    Inventor: Richard M. Jacobson
  • Patent number: 4604132
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A, B and D are selected from CH and N;E is selected from oxygen and sulfur;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, phenyl, substituted phenyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;R.sup.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: August 5, 1986
    Assignee: ICI Australia Limited
    Inventors: Richard J. Conway, Keith G. Watson, Graeme J. Farquharson
  • Patent number: 4578388
    Abstract: The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino). N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido) groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: March 25, 1986
    Assignee: SmithKline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4565820
    Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]-furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: January 21, 1986
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4539323
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 8 carbon atoms or arylmethyl; orR.sub.1 and R.sub.2, together with each other, are --(CH.sub.2).sub.4 or --(CH.sub.2).sub.5 --; andR.sub.3 and R.sub.4, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 4 carbon atoms or arylmethyl; orR.sub.3 and R.sub.4, together with each other, are --CH.sub.3 -- or --CH.sub.2 --CH.sub.2 --;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful for the treatment of cardiovascular diseases, especially hypertension.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: September 3, 1985
    Assignee: Boehringer Ingelheim KG
    Inventors: Anton Mentrup, Ernst-Otto Renth, Kurt Schromm, Wolfgang Hoefke, Wolfram Gaida
  • Patent number: 4499101
    Abstract: The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. Two compounds of this invention are N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea and N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-cyanoguanidine.
    Type: Grant
    Filed: February 4, 1983
    Date of Patent: February 12, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4465504
    Abstract: An N-(2,2,2-trifluoroethyl)-N-alkyl-azolyloxyacetic acid amides of the formula ##STR1## in which R and R.sup.1 have the meaning given in the description, a process for the production of which is described, find use as herbicides. The intermediate products of the general formulae ##STR2## in which R.sup.1 in each case has the same meaning as in formula (I), for the preparation of the compounds (I) are also new.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: August 14, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Volker Mues, Bernd Baasner, Hermann Hagemann, Ludwig Eue, Robert Schmidt
  • Patent number: 4459239
    Abstract: Chloroformates of alkyl esters of C-alkyl or C-haloalkyl tartronic acids of the general formula: ##STR1## in which: R represents an alkyl or haloalkyl group having from 1 to 5 carbon atoms, andR.sup.1 represents an alkyl group having from 1 to 5 carbon atoms,may be prepared by reaction of phosgene in an inert solvent with the corresponding ester of the C-alkyl-tartronic acid of the desired compound at a temperature of from 0.degree. to 20.degree. C. in the presence of at least a stoichiometric amount of a tertiary amine.
    Type: Grant
    Filed: January 11, 1982
    Date of Patent: July 10, 1984
    Assignee: Montedison S.p.A.
    Inventors: Vincenzo Di Toro, Franco Gozzo, Pier M. Boschi
  • Patent number: 4458078
    Abstract: The invention relates to novel intermediates for the preparation of peptides of pharmacological activity, said intermediates being of the formulas: ##STR1## wherein R.sub.2.sup.
    Type: Grant
    Filed: May 13, 1982
    Date of Patent: July 3, 1984
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Yoshihiko Kitaura, Osamu Nakaguchi, Keiji Hemmi, Matsuhiko Aratani, Hidekazu Takeno, Satoshi Okada, Hirokazu Tanaka, Masashi Hashimoto, Yoshio Kuroda, Eiko Iguchi, Masanobu Kohsaka, Hatsuo Aoki, Hiroshi Imanaka
  • Patent number: 4430337
    Abstract: Hypoglycemic oxazolidine-2,4-diones, substituted at the 5-position with a (C.sub.5 -C.sub.9) unsaturated monocyclic, saturated bicyclic or unsaturated bicyclic hydrocarbon radical; methods for their preparation; and method for their use in the treatment of hyperglycemic mammals.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: February 7, 1984
    Assignee: Pfizer Inc.
    Inventor: Gerald F. Holland
  • Patent number: 4372963
    Abstract: Bisamidines carrying one unsaturated nitrogen heterocyclo-containing substituent, representative of which i; 1-[N'-(2-(5-methyl-4-imidazolyl)methylthio)ethyl)guanidino]-8-[N'-methylgu anidino]octane, are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: March 27, 1981
    Date of Patent: February 8, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4293691
    Abstract: A method for preparing image-forming color couplers containing a thioether group at the coupling active position is disclosed which comprises reacting a compound of the formula A-H where A is a cyan, magenta or yellow coupler residue in which a hydrogen atom at the coupling off position is removed with a disulfide of the formula (IIa) or (IIb): ##STR1## where R is a straight chain, branched chain or cyclic alkyl group, a cyclic alkenyl group, or an aralkyl group or a ##STR2## group, B is Y, -D-Y or ##STR3## where D is an oxygen atom or >N--R.sub.4, R.sub.4 is a hydrogen atom, an alkyl group or an aryl group, Y is a straight chain, branched chain or cyclic alkyl group, a straight chain, branched chain or cyclic alkenyl group, an aralkyl group, an aryl group, or a heterocyclic group, Q is a non-metallic atomic group necessary for completing a 5- or 6-membered nitrogen-containing heterocyclic group and R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: August 10, 1979
    Date of Patent: October 6, 1981
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuo Furutachi, Nobuo Seto
  • Patent number: 4267344
    Abstract: N-Substituted N-carboxyanhydrides of .alpha.-amino acids, useful in peptide syntheses, and peptide synthesis process using such compounds, are disclosed. The N-substituent is penta(lower alkoxy)benzyl, or optionally substituted 9-xanthyl, 9-thioxanthyl or 9-selenoxanthyl.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: May 12, 1981
    Assignee: Proteinkemisk Institut. tilknyttet Akademiet for de tekniske Videnskaber
    Inventors: John B. Halstrom, Karoly G. Kovacs
  • 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: 4251665
    Abstract: Amino resins, e.g., urea-formaldehyde and melamine-formaldehyde thermosetting resin systems, are cured with thermally-decomposable adducts of aromatic sulfonic acids and oxa-azacyclopentanes. The resin products cured with these adducts provide surface coatings having superior water resistance properties. The cured compositions can include other conventional ingredients capable of co-reacting with the amino resins, such as polyols, polyacids, alkyd resins, polyester resins, epoxies, acrylics and the like, to provide compositions curable to products having a wide range of properties.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: February 17, 1981
    Assignee: King Industries, Inc.
    Inventor: Leonard J. Calbo
  • Patent number: 4244969
    Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.
    Type: Grant
    Filed: February 13, 1975
    Date of Patent: January 13, 1981
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
  • Patent number: 4221584
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R.sup.5 and R.sup.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Stephen D. Ziman