Chalcogen And -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To Ring Carbons Of The Bicyclo Ring System (e.g., 4-oxo-naphthyridine -3-carboxylic Acid, Etc.) Patents (Class 546/123)
  • Patent number: 4533381
    Abstract: Novel 2-naphthyridinyloxy(or thio)phenoxy propanoic acid compounds of the formula ##STR1## represents a 6 membered nitrogen containing an aromatic ring which forms a 1,5-, 1,6-, 1,7- or 1,8-naphthyridinyl moiety with the adjoining pyridine ring, said naphthyridinyl moiety optionally substituted at the 6 position of the naphthyridinyl moiety with a chloro, bromo, iodo, CF.sub.3, or fluoro atom;A represents 0 or S; andagriculturally acceptable salts, esters, ethers, and amides thereof, are useful as fungicides and herbicides, particularly effective against grassy weeds.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: August 6, 1985
    Assignee: The Dow Chemical Company
    Inventor: James A. Turner
  • Patent number: 4517190
    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: June 9, 1983
    Date of Patent: May 14, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4517191
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or formyl; and R' and R" are hydrogen or lower-alkyl, are useful as antibacterial agents or as intermediates, and are prepared from the corresponding compounds unsubstituted in the 1-position.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: May 14, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Mark P. Wentland, Denis M. Bailey
  • Patent number: 4477449
    Abstract: Certain substituted 1,4-dihydro-4-oxo-7-(3-thiazolidinyl or 4-thiomorpholinyl)-1,8-naphthyridine-3-carboxylic acids and derivatives are disclosed as antibacterial agents.
    Type: Grant
    Filed: March 1, 1983
    Date of Patent: October 16, 1984
    Assignee: Warner-Lambert Company
    Inventor: Joseph P. Sanchez
  • Patent number: 4472193
    Abstract: Novel 2-naphthyridinyloxy(or thio)phenoxy propanoic acid compounds of the formula ##STR1## wherein ##STR2## represents a 6 membered nitrogen containing an aromatic ring which forms a 1,5-, 1,6-, 1,7- or 1,8-naphthyridinyl moiety with the adjoining pyridine ring, said naphthyridinyl moiety optionally substituted at the 6 position of the naphthyridinyl moiety with a chloro, bromo, iodo, CF.sub.3, or fluoro atom;A represents O or S; andagriculturally acceptable salts, esters, ethers, and amides thereof, are useful as fungicides and herbicides, particularly effective against grassy weeds.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: September 18, 1984
    Assignee: The Dow Chemical Company
    Inventor: James A. Turner
  • Patent number: 4448962
    Abstract: This invention relates to new compounds of value as antibacterial agents. More particularly, it relates to quinoline carboxylic acid derivatives, the hydrates and the acid or alkali addition salts thereof.
    Type: Grant
    Filed: October 14, 1981
    Date of Patent: May 15, 1984
    Assignee: Kyorin Seiyaku Kabushiki Kaisha
    Inventors: Tsutomu Irikura, Seigo Suzue, Akira Ito, Hiroshi Koga
  • Patent number: 4426387
    Abstract: The invention concerns compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O,S,--CR.sup.7 .dbd.CR.sup.8 --, --N.dbd.CR.sup.8 -- and --N.dbd.N--; R.sup.4, R.sup.5 and R.sup.6, and R.sup.7 and R.sup.8 when present, each represent hydrogen or defined substituents and additionally either R.sup.4 and R.sup.5 when adjacent or R.sup.6 and R.sup.8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R.sup.1, R.sup.2, R.sup.3 and R.sup.9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is .dbd.O, .dbd.S or .dbd.NH; Y is --O-- or a direct bond and Z is --CO-- or --CH.sub.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: January 17, 1984
    Assignee: John Wyeth & Brother Ltd.
    Inventors: John L. Archibald, Terrence J. Ward
  • Patent number: 4416817
    Abstract: Novel 3-methoxy-2-oxoazetidine derivatives, which are shown by the following formula ##STR1## wherein R.sub.1 is amino, acylated amino or protected amino, are of value as intermediates for the synthesis of useful compounds represented by the formula ##STR2## wherein R.sub.1 has the same meaning as defined above, as drugs in the treatment of bacterial infections.
    Type: Grant
    Filed: November 18, 1981
    Date of Patent: November 22, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Taisuke Matsuo, Michihiko Ochiai
  • 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: 4397784
    Abstract: New .beta.-lactams of the general structure: ##STR1## wherein X=O or S; R represents H, loweralkyl, acyl, aryl, or arylloweralkyl; R' is hydrogen, loweralkoxy, loweralkoxyalkyl, loweralkyl, phenylthio or loweralkylmercapto; R" is hydrogen or loweralkyl; and the broken line represents an optional double bond, and certain esters thereof. All compounds are effective antibacterials.
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: August 9, 1983
    Assignee: Abbott Laboratories
    Inventor: Daniel T. Chu
  • Patent number: 4382937
    Abstract: A 1,8-naphthyridine compound of the formula ##STR1## wherein R is a vinyl or 2-fluoroethyl group, andR.sub.1 and R.sub.2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms,and the esters thereof and salts thereof. For example, 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyr idine-3-carboxylic acid and nontoxic salts thereof, which are covered by the aforesaid compound, are useful as an antibacterial agent.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: May 10, 1983
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Shinichi Nakamura
  • Patent number: 4365063
    Abstract: 1,4,5,6,7,8-Hexahydro-2-alkyl-4-pentafluorophenyl-5-oxo-1,7-naphthyridine-3 -carboxylic acid esters and pharmaceutically acceptable salts thereof are useful antihypertensive agents.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: December 21, 1982
    Assignee: American Home Products Corporation
    Inventors: Theodore S. Sulkowski, James L. Bergey, Albert A. Mascitti
  • Patent number: 4359578
    Abstract: This invention relates to 1,8-naphthyridine compounds of the formula ##STR1## wherein X is a halogen atom especially fluorine atom,R.sub.1 is an ethyl group or a vinyl group, andR.sub.2 is a hydrogen atom or a lower alkyl group, their salts and processes for the preparation of them.The 1,8-naphthyridine compounds and their salts are useful as antibacterial agents and intermediates thereof.
    Type: Grant
    Filed: August 23, 1979
    Date of Patent: November 16, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4352803
    Abstract: This invention relates to 1,8-naphthyridine compounds of the formula ##STR1## wherein X is a halogen atom especially fluorine atom,R.sub.1 is an ethyl group or a vinyl group, andR.sub.2 is a hydrogen atom or a lower alkyl group, their salts and processes for the preparation of them.The 1,8-naphthyridine compounds and their salts are useful as antibacterial agents and intermediates thereof.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: October 5, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4350817
    Abstract: 4-Amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives are anti-secretory agents for use in the treatment of peptic ulcer disease.4-Cl, Br or I naphthyridine derivatives are disclosed as intermediates.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: September 21, 1982
    Assignee: American Home Products Corporation
    Inventors: Anthony C. Scotese, Arthur A. Santilli
  • Patent number: 4347362
    Abstract: 1-alkyl-4-amino-3-(3-aminotriazolo)-1,8-naphthyridine-2-ones are antihypertensive agents.
    Type: Grant
    Filed: October 8, 1981
    Date of Patent: August 31, 1982
    Assignee: American Home Products Corporation
    Inventor: Stanley C. Bell
  • Patent number: 4347355
    Abstract: New .beta.-lactams of the general structure: ##STR1## wherein R represents H or an acyl moiety known from the penicillin or cephalosporin art, R' is hydrogen, loweralkoxy, loweralkoxyalkyl, loweralkyl, phenylthio or loweralkylmercapto R" is loweralkyl, the broken line represents an optional double bond, and acyloxymethyl esters thereof. All compounds are effective antibacterials.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: August 31, 1982
    Assignee: Abbott Laboratories
    Inventor: Daniel T. Chu
  • Patent number: 4341784
    Abstract: The present invention provides a 1,8-naphthyridine compound of the formula ##STR1## wherein R is hydrogen, methyl, ethyl or propyl, and a nontoxic pharmaceutically acceptable salt thereof, and a process for preparing a 1,8-naphthyridine compound of the above formula which comprises(A) reacting a compound of the formula ##STR2## wherein Y is halogen, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkylsulfonyloxy or arylsulfonyloxy, and R.sub.1 is hydrogen or lower alkyl,with a compound of the formula ##STR3## wherein R.sub.2 is hydrogen or a protective group for the amino group, and R is as defined above,and when a reaction product in which R.sub.1 is lower alkyl and/or R.sub.2 is the amino protective group is obtained, treating it with an acid or base, and/or reductively cleaving it,(B) decomposing a compound of the formula ##STR4## wherein A .crclbar. is a fluorine-containing anion, and R.sub.1 and R.sub.2 are as defined above,and when a reaction product in which R.sub.
    Type: Grant
    Filed: September 15, 1980
    Date of Patent: July 27, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4324893
    Abstract: 4-Amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives are anti-secretory agents for use in the treatment of peptic ulcer disease.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: April 13, 1982
    Assignee: American Home Products Corporation
    Inventors: Anthony C. Scotese, Arthur A. Santilli
  • Patent number: 4321384
    Abstract: 1,4,5,6,7,8-hexahydro-2-alkyl-4-aryl-5-oxo-1,7-naphthyridine-3-carboxylic acid esters and pharmaceutically acceptable salts thereof are useful antihypertensive agents.
    Type: Grant
    Filed: February 27, 1981
    Date of Patent: March 23, 1982
    Assignee: American Home Products Corporation
    Inventors: Theodore S. Sulkowski, James L. Bergey, Albert A. Mascitti
  • Patent number: 4304914
    Abstract: Compounds of the formula ##STR1## wherein each of R, R.sub.1 and R.sub.2 is independently H, alkyl, alkenyl, alkoxy, halo, hydroxy, trifluoromethyl, amino, alkylamino, cyano and nitro;R.sub.3 is carbalkoxy, carboxamide alkanoyl, trifluoromethyl and cyano; andAr is heteroaryl or ##STR2## wherein R.sub.4 and R.sub.5 have the same meaning as each of R, R.sub.1 and R.sub.2 ; and acid addition salts thereof have cardiotonic and hypertensive activity.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: December 8, 1981
    Assignee: USV Pharmaceutical Corporation
    Inventors: James R. Shroff, Bernard Loev
  • Patent number: 4303661
    Abstract: 1,6-Naphthyridine derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl of 1 to 3 carbon atoms, halo, or trifluoromethyl;R.sup.3 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable metal or amine cation; andn is one of the integers 1, 2 or 3;or a pharmaceutically acceptable salt thereof and pharmaceutical compositions containing those compounds are useful as antiallergy agents effective prophylactically to relieve the symptoms manifest in atopic immediate sensitivity in mammals.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: December 1, 1981
    Assignee: American Home Products Corporation
    Inventor: Stanley C. Bell
  • Patent number: 4293695
    Abstract: 2,3,5,8-Tetrahydrofuro- and 5,8-dihydrofuro[3,2-b]-1,8-naphthyridine compounds of the formula (I) ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 6 carbon atoms and M represents a hydrogen atom, an alkali metal or an alkaline earth metal having anti-bacterial activity.
    Type: Grant
    Filed: September 29, 1980
    Date of Patent: October 6, 1981
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Yoshiaki Tanaka, Isao Hayakawa
  • Patent number: 4264602
    Abstract: Anti-allergic 4-hydroxy-3-nitro-pyrido[2,3-b]pyridines-2(1H)-ones are prepared by reacting a 3,4-dihydro-1,3-dioxo-1H-pyrido[2,3-d][1,3]oxazine (a 3-azaisatoic anhydride) with the carbanion resulting from the reaction of nitro acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: July 21, 1976
    Date of Patent: April 28, 1981
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4229456
    Abstract: Organic chemical compounds based upon the naphthyridine molecule are disclosed which have potent gastric secretion inhibitory properties. The naphthyridinone is substituted with a substituted amino alkyl group at the 1-position, and variously substituted at the remaining positions. The compounds have profound effects on the inhibition of gastric secretions in the gastro-intestinal tract, and compositions for such uses are also disclosed.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: October 21, 1980
    Assignee: Merck & Co., Inc.
    Inventors: William A. Bolhofer, Edward J. Cragoe, Jr., Jacob M. Hoffman, Jr.
  • Patent number: 4207418
    Abstract: 1:1 and 1:2 molar salts of 1,2-ethanediamine and nalidixic acid are prepared by reacting 1,2-ethanediamine with one or two molar equivalents of nalidixic acid. Also shown are aqueous solutions of the 1:1 equimolar salt and their preparation from the corresponding 1:2 molar salt.
    Type: Grant
    Filed: October 5, 1978
    Date of Patent: June 10, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4195087
    Abstract: The present invention deals with derivatives of naphthyridine, process for their preparation and their utility, inter alia, as anti-bacterides and as feed-additives.
    Type: Grant
    Filed: December 6, 1977
    Date of Patent: March 25, 1980
    Assignee: Abic, Ltd.
    Inventor: Chaim Simonovitch
  • Patent number: 4183935
    Abstract: Bispidine derivatives of the formula ##STR1## where R.sup.1 is H or C.sub.6 H.sub.5, R.sup.2 is H, Cl or CF.sub.3, R.sup.3 is H, F or Cl and X is 0 or 1, and drugs which contain these compounds. The compounds are prepared by condensing N-monobenzylbispidine with appropriately substituted phenylethyl halides or by a Mannich reaction of N-benzylpiperid-4-one with appropriately substituted phenylalkylamines, followed by reduction. They exhibit mainly anti-arrhythmic action.
    Type: Grant
    Filed: June 13, 1978
    Date of Patent: January 15, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz Binnig, Ludwig Friedrich, Hans P. Hofmann, Horst Kreiskott, Claus Mueller, Manfred Raschack
  • Patent number: 4182880
    Abstract: 1,8-Naphthyridine compounds and a process for preparing chelated 1,8-naphthyridine derivatives and 1,8-naphthyridine derivatives which are pharmacautically useful compounds. Chelated 1,8-naphthyridine derivatives of the general formula [I]: ##STR1## wherein X and Y are independently a lower alkyl group, are prepared by subjecting a compound of the general formula [II]: ##STR2## wherein X and Y are as defined above and R is a lower alkyl group, to ring-closing condensation in the presence of boron trifluoride and/or a boron trifluoride complex at an elevated temperature, and 1,8-naphthyridine derivatives of the general formula [III]: ##STR3## wherein X and Y are as defined above, are prepared by treating the chelated 1,8-naphthyridine derivatives with water and/or an alcohol. The desired products can be readily obtained in high yields. The chelated compounds are novel compounds.
    Type: Grant
    Filed: December 13, 1978
    Date of Patent: January 8, 1980
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Nanao Watanabe, Haruhito Akimoto
  • Patent number: 4176183
    Abstract: Novel naphthyridines having a 3-amino-2-OR-propoxy substituent are disclosed. The compounds have .beta.-adrenergic blocking and immediate onset antihypertensive activities.
    Type: Grant
    Filed: July 17, 1978
    Date of Patent: November 27, 1979
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • Patent number: 4137317
    Abstract: Triglycerides carrying an anti-bacterial drug moiety in the 2-position and a hydrocarbon acyl moiety in the 1- and 3-positions exhibit excellent anti-bacterial properties without causing the side effects often associated with oral antibiotics when used by themselves.
    Type: Grant
    Filed: November 14, 1977
    Date of Patent: January 30, 1979
    Assignee: Abbott Laboratories
    Inventors: Gerald Y. Paris, Denis G. Cimon, David L. Garmaise
  • Patent number: 4128649
    Abstract: Anti-allergic 4-hydroxy-pyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acids and esters are prepared by reacting a 3,4-dihydro-1,3-dioxo-1H-pyrido[2,3-d][1,3]oxazine (a 3-azaisatoic anhydride) with an alkali metal salt of a malonic ester.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: December 5, 1978
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann