Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/298)
  • Patent number: 4655816
    Abstract: There are disclosed novel 2,6-substituted-3-pyridinecarboxylic acids, esters, and salts useful as herbicides, and as intermediates which provide herbicides.
    Type: Grant
    Filed: August 27, 1985
    Date of Patent: April 7, 1987
    Assignee: Monsanto Company
    Inventors: Len F. Lee, Maria L. Miller
  • Patent number: 4645766
    Abstract: The present invention relates to certain 1,2-dihydro-2-oxo-6-alkyl-3-pyridine carboxylic acids, carboxylate esters, and methanols, their preparation and their use as antihyperglycemic agents.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: February 24, 1987
    Assignee: The Upjohn Company
    Inventor: Gilbert A. Youngdale
  • Patent number: 4643995
    Abstract: There are disclosed pyridine-2-ethers and pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring corresponding to the formula ##STR1## the pyridine-N-oxides and/or amine oxides thereof and the pharmaceutically acceptable salts thereof. The compounds show analgesic activity.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: February 17, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Jurgen Engel, Vladimir Jakovlev, Bernd Nickel, Klaus Thiemer, Gerhard Scheffler
  • Patent number: 4643849
    Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: February 17, 1987
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanagi, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
  • Patent number: 4631081
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Z is selected from oxygen and the group --YAn wherein Y is selected from C.sub.1 to C.sub.6 alkyl and benzyl and An is an anion;k is zero or the integer 1;n is an integer selected from 3 and 4;X is 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, 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; andR.sup.
    Type: Grant
    Filed: September 27, 1983
    Date of Patent: December 23, 1986
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Richard J. Conway, Peter G. Tucker
  • Patent number: 4610819
    Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 9, 1986
    Assignee: A. H. Robins Company, Inc.
    Inventors: Young S. Lo, Albert D. Cale, Jr.
  • Patent number: 4609734
    Abstract: Process for the production of 2-hydroxypyridines having the formula: ##STR1## from 2-pyridine carboxylic acid-N-oxides having the formula: ##STR2## wherein R is H, a --COOH group, an alkyl group having 1 to 8 carbon atoms or an aryl group and n designates a number between 1 and 4. The N-oxide is converted using lower aliphatic carboxylic acid anhydrides in the presence of a tertiary amine. The conversion product is then hydrolyzed.
    Type: Grant
    Filed: November 8, 1983
    Date of Patent: September 2, 1986
    Assignee: Lonza Ltd.
    Inventor: Daniel Quarroz
  • Patent number: 4588816
    Abstract: The invention is a process for the preparation of (2-(6-substituted)pyridinyloxy)alkanols comprising contacting a 2-(6-substituted)pyridinol with an organic carbonate at a temperature of between about 0.degree. C. and 250.degree. C.
    Type: Grant
    Filed: May 8, 1984
    Date of Patent: May 13, 1986
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4568751
    Abstract: Novel 5-acyl-2-(1H)pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-pentanedione in an inert organic solvent.
    Type: Grant
    Filed: April 29, 1983
    Date of Patent: February 4, 1986
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
  • Patent number: 4560691
    Abstract: 1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar--CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitro and 5-(Ar--CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. Processes for preparing the compounds of formulas I, II and III are shown.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: December 24, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4556414
    Abstract: Selective herbicides based on compounds of the formula: ##STR1## in which: R.sup.1, R.sup.2 and R.sup.3 are H, lower alkyl, alkoxy or alkoxyalkyl;R.sup.4 is a carboxyl radical, optionally in the form of a salt or ester, or a cyano, cyanoalkyl or alkoxyalkyl radical;R.sup.5 and R.sup.6 are H, lower alkyl or cyano or together form a C.sub.2 to C.sub.5 alkylene radical;R.sup.7 is halogen, lower alkyl, lower alkoxy, lower alkenyl, alkenyloxy, nitro, cyano or amino, alkylene-dioxy;n=0 to 5; and ##STR2## is a nitrogen-containing heterocyclic ring containing 2 or 3 units of unsaturation.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: December 3, 1985
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Dominique Ambrosi, de Reinach Hirtzbach Francois
  • Patent number: 4556716
    Abstract: Process for the production of 2-halopyridine derivatives having the formula: ##STR1## wherein X is halogen, R is --COOH or a lower alkyl radical and n is a number between 0 and 4. The corresponding 2-pyridine carboxylic acid-N-oxide derivatives having the formula: ##STR2## are reacted in the presence of an excess of organic anhydrides, tertiary alkylamines and a halogen-producing compound having the formula CH.sub.t X.sub.m, wherein t is 1 or 2, m is 2 or 3 and X is halogen, or having the formula C.sub.2 H.sub.p X.sub.m, wherein p is 3 or 4, m is 2 or 3 and X is halogen. The reaction mixture is adjusted to a pH value of 12 to 13 and the desired product is isolated from the mixture. Compound comprising (i) a 2-pyridine carboxylic acid-N-oxide derivative, (ii) an organic anhydride, (iii) a tertiary amine and (iv) a halogen-producing compound having the formula CH.sub.n X.sub.m. The composition can be used as the starting ingredients for the above process.
    Type: Grant
    Filed: January 11, 1983
    Date of Patent: December 3, 1985
    Assignee: Lonza Ltd.
    Inventor: Daniel Quarroz
  • Patent number: 4555517
    Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, lower alkyl, halo, cyano, hydroxy, amino, lower alkylamino, --CH.sub.2 NH.sub.2, CH.sub.2 OH or COOR"; R' is hydrogen, lower cycloalkyl or lower alkyl; R" is lower alkyl or --CH.sub.2 Ar wherein Ar is phenyl, substituted phenyl, furan or thiophene; R'" is COOR", ##STR2## and x is oxygen or nitrogen; or a pharmaceutically acceptable salt thereof and their use in the treatment of impaired ventricular myocardial contractility.The compounds exhibit cardiotonic activity.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: November 26, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, Diane M. Yamamoto, Cynthia Barcelon-Yang
  • Patent number: 4550205
    Abstract: The invention relates to new diphenyl ethers of the general formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl, alkoxy or alkylthio group having 1-6 carbon atoms, or an alkanoyl group having 1-4 carbon atoms;Y is a nitrogen atom or a group of the formula CH or CCl;Z is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl group having 1-4 carbon atoms, or an alkanoyl group having 1-4 carbon atoms; n is 0-2;R.sub.1 is a hydrogen atom, or an alkyl or alkanoyl group having 1-4 carbon atoms;R.sub.2 and R.sub.3 are equal or different and represent hydrogen atoms or alkyl groups having 1-4 carbon atoms; andA is a group of the general formula ##STR2## wherein R.sub.4 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, or a cation of an alkali metal, alkaline earth metal or an alkylated or non-alkylated ammonium group, andR.sub.5 and R.sub.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: October 29, 1985
    Assignee: Duphar International Research B.V.
    Inventors: Gerard B. Paerels, Cornelis W. Raven
  • Patent number: 4542140
    Abstract: .alpha.-Cyanoacrylic acid lower alkyl esters, and their corresponding amides, characterized by having a heterocyclic containing mercapto radical as one .beta.-substituent and an alkylthio, alkenylthio or a heterocyclic containing mercapto radical as another .beta.-substituent are useful for treating ulcers and for suppressing gastric acid secretion.
    Type: Grant
    Filed: October 20, 1983
    Date of Patent: September 17, 1985
    Assignee: American Home Products Corporation
    Inventors: Jehan Bagli, Tibor Bogri, Bozidar Palameta, Luis E. Borella
  • Patent number: 4535092
    Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are substituents defined in claim 1; wherein R.sup.4 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R.sup.5 as stated below;wherein R.sup.5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R.sup.4 to form an oxycarbonyl group such that together with the --N--CO--C-- part of the molecule it forms an oxazolidinedione group;wherein R.sup.6 is alkyl or halogenoalkyl of up to 4 carbon atoms;and wherein R.sup.7 is 5- or 6- membered saturated or unsaturated heterocyclic which contains one, two or three hetero atoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two substituents defined in claim 1;processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: August 13, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Leslie R. Hughes
  • Patent number: 4524149
    Abstract: 4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: June 18, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4521535
    Abstract: The invention relates to 4-pyridone-3-carboxylic acid derivatives, a process for the preparation thereof and pharmaceutical compositions containing same. The 4-pyridone-3-carboxylic acid derivatives are useful as antibacterial agents and/or as agents having a stimulating activity on the central nervous system.
    Type: Grant
    Filed: April 19, 1982
    Date of Patent: June 4, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Alexander E. Wick
  • Patent number: 4517010
    Abstract: There is provided a new class of derivatives of 2-nitro-5-(substituted-phenoxy) benzoyl compounds that have pre- and post-emergence herbicidal activity. The derivatives include certain substituted phenyl esters, phenyl thioesters; heterocyclic esters; substituted alkyl and alkylthio esters; carbonates and thiocarbonates; benzoyl phosphonates; substituted alkanones and substituted amides.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: May 14, 1985
    Assignee: Rhone-Poulenc Inc.
    Inventor: Robert J. Theissen
  • Patent number: 4515974
    Abstract: Fumaric acid monoesters can be prepared by introducing a hydroxyl compound at a rate corresponding to the progress of the reaction into a solution or a melt of maleic anhydride, which may optionally be substituted, if appropriate in the presence of a cis-trans catalyst. New fumaric acid monoesters can be formed by the process.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 7, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Zecher, Rudolf Merten
  • Patent number: 4507493
    Abstract: The present invention provides a process for the preparation of aryl carboxylic acids and derivatives thereof by the carbonylation of aryl sulfonyl chlorides. The aryl sulfonyl chlorides are reacted with carbon monoxide and water or an alcohol or amine in the presence of a zero-valent metal catalyst consisting essentially of palladium.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: March 26, 1985
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4506092
    Abstract: The present invention provides a process for the preparation of aryl carboxylic acids and derivatives thereof by the carbonylation of triaryl sulfonium salts. The triaryl sulfonium salts are reacted with carbon monoxide and water or an alcohol or amine in the presence of a triaryl phosphine and a zero-valent metal catalyst selected from palladium or rhodium.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: March 19, 1985
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4503061
    Abstract: Certain 2(1H)-pyridinones are cardiotonic agents. Methods for their preparation and use are disclosed.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: March 5, 1985
    Assignee: Warner-Lambert Company
    Inventors: James A. Bristol, Ila Sircar
  • Patent number: 4499275
    Abstract: Novel phenoxypicolinic aldehydes, namely, 6-(4'-difluoromethoxyphenoxy)picolinic aldehyde and 5-fluoro-6-phenoxypicolinic aldehyde.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: February 12, 1985
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kiyomi Ozawa, Shigeru Ishii
  • Patent number: 4497740
    Abstract: New 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine compounds are described having the general formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl or alkenyl radical or the cyclopropylmethyl radical, R.sub.2 is a hydrogen atom, or a lower alkyl or alkenyl radical, n is 0, 1 or 2, R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl, pyridyl or phenyl radical, R.sub.4 is an optionally substituted furyl, thienyl, pyrrolyl or pyridyl radical, R.sub.5 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, lower alkylthio, nitro, trifluoromethyl, cyano, amino, lower mono- or dialkylamino, lower monoalkanoylamino, lower N-alkyl-N-alkanoylamino or lower alkanoyloxy radical, and R.sub.6 is a hydrogen atom, or a lower alkyl or lower alkoxy radical or R.sub.5 and R.sub.6 together denote a methylenedioxy or ethylenedioxy radical. The compounds have pharmacological, for example, analgesic, properties.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: February 5, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
  • Patent number: 4468405
    Abstract: Novel N-aroyl N'-phenyl ureas having halogen substituents in the 3- and 5-positions and haloalkyl, haloalkoxy or haloalkylthio in the 4-position of the N'-phenyl are more active and have a broader spectrum of effectiveness than the known benzoylurea insecticides.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: August 28, 1984
    Assignee: The Dow Chemical Company
    Inventors: Raymond H. Rigterink, Ronald J. Sbragia
  • Patent number: 4465681
    Abstract: Pyridine derivatives of the formula: ##STR1## or pharmaceutically acceptable acid addition salts thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents hydrogen atom or lower alkyl group, or R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a heterocycle, A.sup.1 and A.sup.2 are the same or different and each represents alkylene or hydroxy-substituted alkylene group, Y.sup.1 and Y.sup.2 are the same or different and each represents oxygen or sulfur atom, and Z represents ##STR2## These compounds show pharmacological activities such as potentiating activity for leukocyte phagocytosis, potentiating activity for macrophage phagocytosis, potentiating activity for the production of rosette forming cells in the spleen and anti-adjuvant arthritis activity, and are useful as medicines.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: August 14, 1984
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Takanori Oe, Mineo Tsuruda, Kazuhiro Goto, Masao Hisadome
  • Patent number: 4447613
    Abstract: Pyridyl esters and thiolesters of amino acids, intermediates therefor, synthesis thereof and the use of said esters and thiolesters and compositions for the control of pests.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: May 8, 1984
    Assignee: Zoecon Corporation
    Inventor: Clive A. Henrick
  • Patent number: 4443456
    Abstract: This invention relates to a novel class of amidinourea and amidinothiourea compounds wherein the urea nitrogen atom is substituted by a heterocyclic alkylene group, and their use in pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anesthetic, anti-arrhythmic, antidiarrheal and antiparasitic action.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: April 17, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: George H. Douglas, William L. Studt, Stuart A. Dodson, Harry K. Zimmerman
  • Patent number: 4415580
    Abstract: 1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q"-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: November 15, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • 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: 4412077
    Abstract: 4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III, Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: October 25, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4393213
    Abstract: A process for producing 6-phenoxypicolinic aldehydes, which comprises reacting a 2-halogeno-6-phenoxypyridine represented by the general formula I: ##STR1## where X is a halogen atom, Y is independently an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms substituted by a halogen atom, an alkylthio group of 1 to 4 carbon atoms, a trifluoromethyl group, a fluorine atom or a chlorine atom, Z is a hydrogen atom or a fluorine atom, and n is an integer of 0 to 2, with magnesium metal, and then with a formylating reagent. These compounds are used as intermediates for the synthesis of insecticides.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: July 12, 1983
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kiyomi Ozawa, Shigeru Ishii
  • Patent number: 4390702
    Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: June 28, 1983
    Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.
    Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
  • Patent number: 4374992
    Abstract: The invention concerns the treatment of ulcers and hypersecretion in a mammal using compounds of the formula IAr-A-S-Y Iwhere Ar is phenyl, which may be substituted or cycloalkyl of 5 to 7 carbon atoms, A is saturated or unsaturated lower alkylene which may be substituted by lower alkyl, oxo or hydroxy, S is sulphur and Y is an optionally substituted pyridine, pyridinium, tetrahydropyridine or tetrahydropyridinium radical. Certain novel compounds and pharmaceutical compositions are also claimed.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: February 22, 1983
    Assignee: John Wyeth and Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4374140
    Abstract: The present application discloses certain 2-substituted propoxy-3-cyano-5-hydroxypyridines. The compounds have pharmaceutical activity e.g. as antihypertensives.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: February 15, 1983
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello, Stanley Vickers, Alfred Steuerwald
  • Patent number: 4358594
    Abstract: Compounds are prepared corresponding to the formula ##STR1## wherein Y represents chloro or R'; R represents ##STR2## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkyl sulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro or bromo; n represents an integer of 0 to 2 or X.sub.n represents 3,4-methylenedioxy and R' represents R with the proviso that R and R' can be the same or different. The compounds are useful as intermediates for the preparation of insecticidal substituted pyridine methyl esters of cyclopropane carboxylic acids.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: November 9, 1982
    Assignee: The Dow Chemical Co.
    Inventor: Sudarshan K. Malhotra
  • Patent number: 4319916
    Abstract: A series of novel 1-alkyl-3-acyl-5-substituted-phenyl-4(1H)-pyridinones are herbicides, particularly useful in the culture of cotton.
    Type: Grant
    Filed: August 21, 1980
    Date of Patent: March 16, 1982
    Assignee: Eli Lilly and Company
    Inventor: Riaz F. Abdulla
  • Patent number: 4315858
    Abstract: Novel organic amide compounds which are N-[6-(acylaminophenyl)-1,2-dihydro-2-oxonicotinoyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[acylaminophenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[acylaminophenyl]-1,2-dihydro-2-oxonicotinoyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: February 16, 1982
    Assignee: Warner-Lambert Company
    Inventors: Leonard Doub, Theodore H. Haskell, Thomas F. Mich, Dietrich Schweiss
  • Patent number: 4314063
    Abstract: 1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and C.sub.1-6 -alkyl esters thereof as well as their alkali metal, alkaline earth metal or ammonium salts are described. The foregoing compounds are useful as central nervous system stimulants. Also described are 1-ethyl-6-(2-naphthyl)-4-oxo-1,4,5,6-tetrahydronicotinic acid and C.sub.1-6 -alkyl esters thereof, which are useful as intermediates.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: February 2, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Alexander E. Wick
  • Patent number: 4311698
    Abstract: Novel organic amide compounds which are N-[6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]cephalosporin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 7-aminocephalosporanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.
    Type: Grant
    Filed: January 31, 1980
    Date of Patent: January 19, 1982
    Inventors: Theodore H. Haskell, Thomas F. Mich, Dietrich Schweiss, Townley P. Culbertson
  • Patent number: 4304941
    Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a clay.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: December 8, 1981
    Assignee: Hoechst Roussel Pharmaceuticals, Inc.
    Inventors: Thomas B. K. Lee, Gregory M. Jobin
  • Patent number: 4288440
    Abstract: The present invention relates to certain 6-alkyl-1,2-dihydro-2-oxo-3-substituted pyridine derivatives, their preparation and antihyperglycemic use.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: September 8, 1981
    Assignee: The Upjohn Company
    Inventor: Gilbert A. Youngdale
  • Patent number: 4281133
    Abstract: Substituted phenoxy and phenylthio picolinaldehydes are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2 and Y represents oxygen or sulfur. These compounds are employed as intermediates in the preparation of compounds which have a high degree of insecticidal activity.
    Type: Grant
    Filed: November 29, 1979
    Date of Patent: July 28, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Michael J. Ricks
  • Patent number: 4279913
    Abstract: Novel substituted (3-loweralkylamino-2-R.sub.1 O-propoxy)pyridines, their pharmaceutically acceptable salts, certain intermediates and their preparation are disclosed. These pyridines have pharmaceutically useful properties such as .beta.-adrenergic blocking activity.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: July 21, 1981
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • Patent number: 4278798
    Abstract: 1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and C.sub.1-6 -alkyl esters thereof as well as their alkali metal, alkaline earth metal or ammonium salts are described. The foregoing compounds are useful as central nervous system stimulants. Also described are 1-ethyl-6-(2-naphthyl)-4-oxo-1,4,5,6-tetrahydronicotinic acid and C.sub.1-6 -alkyl esters thereof, which are useful as intermediates.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: July 14, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Alexander E. Wick
  • Patent number: 4278681
    Abstract: Novel organic amide compounds which are N-[6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl] penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(acylaminoacylamino or aminoacylamino)-phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(acylaminoacylamino or aminoacylamino) phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.
    Type: Grant
    Filed: January 31, 1980
    Date of Patent: July 14, 1981
    Assignee: Warner-Lambert Co.
    Inventors: Theodore H. Haskell, Marland P. Hutt, Jr., Ernest D. Nicolaides, Peter W. K. Woo, Gin G. Huang
  • Patent number: 4275069
    Abstract: The present invention relates to certain 6-alkyl-1,2-dihydro-2-oxo-nicotinic acid derivatives, their preparation, and antihyperglycemic use.
    Type: Grant
    Filed: November 28, 1979
    Date of Patent: June 23, 1981
    Assignee: The Upjohn Company
    Inventor: Gilbert A. Youngdale
  • Patent number: 4262001
    Abstract: Substituted pyridine methyl esters of 2-isopropyl-2-(4-chlorophenyl)acetic acid are prepared which correspond to the formula: ##STR1## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano, chloro, fluoro, bromo, or 3,4-methylenedioxy (when n is 2 and both X's are taken together); and R represents hydrogen, cyano or ethynyl. These compounds have been found to exhibit a high degree of insecticidal activity and compositions containing said compounds are so employed.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: April 14, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, John C. Van Heertum
  • Patent number: 4260620
    Abstract: 5-Etherified 2-pyridinecarboxylic acids, e.g. those of the formula ##STR1## or functional derivatives thereof, are hypotensive agents.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: April 7, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Neville Finch, Renat H. Mizzoni