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)
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Naphthyridinyloxy(or thio)phenoxy propanoic acids, derivatives thereof and methods of herbicidal use
Patent number: 4533381Abstract: 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: GrantFiled: September 17, 1984Date of Patent: August 6, 1985Assignee: The Dow Chemical CompanyInventor: James A. Turner -
Patent number: 4517190Abstract: 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: GrantFiled: June 9, 1983Date of Patent: May 14, 1985Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Baldev Singh
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Patent number: 4517191Abstract: 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: GrantFiled: September 29, 1983Date of Patent: May 14, 1985Assignee: Sterling Drug Inc.Inventors: Mark P. Wentland, Denis M. Bailey
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Patent number: 4477449Abstract: 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: GrantFiled: March 1, 1983Date of Patent: October 16, 1984Assignee: Warner-Lambert CompanyInventor: Joseph P. Sanchez
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Naphthyridinyloxy(or thio)phenoxy propanoic acids, derivatives thereof and methods of herbicidal use
Patent number: 4472193Abstract: 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: GrantFiled: July 6, 1982Date of Patent: September 18, 1984Assignee: The Dow Chemical CompanyInventor: James A. Turner -
Patent number: 4448962Abstract: 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: GrantFiled: October 14, 1981Date of Patent: May 15, 1984Assignee: Kyorin Seiyaku Kabushiki KaishaInventors: Tsutomu Irikura, Seigo Suzue, Akira Ito, Hiroshi Koga
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Patent number: 4426387Abstract: 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: GrantFiled: April 7, 1982Date of Patent: January 17, 1984Assignee: John Wyeth & Brother Ltd.Inventors: John L. Archibald, Terrence J. Ward
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Patent number: 4416817Abstract: 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: GrantFiled: November 18, 1981Date of Patent: November 22, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Taisuke Matsuo, Michihiko Ochiai
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Patent number: 4415580Abstract: 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: GrantFiled: August 2, 1982Date of Patent: November 15, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Baldev Singh
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Patent number: 4397784Abstract: 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: GrantFiled: January 4, 1982Date of Patent: August 9, 1983Assignee: Abbott LaboratoriesInventor: Daniel T. Chu
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Patent number: 4382937Abstract: 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: GrantFiled: February 24, 1982Date of Patent: May 10, 1983Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Shinichi Nakamura
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Patent number: 4365063Abstract: 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: GrantFiled: August 31, 1981Date of Patent: December 21, 1982Assignee: American Home Products CorporationInventors: Theodore S. Sulkowski, James L. Bergey, Albert A. Mascitti
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Patent number: 4359578Abstract: 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: GrantFiled: August 23, 1979Date of Patent: November 16, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4352803Abstract: 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: GrantFiled: May 18, 1981Date of Patent: October 5, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4350817Abstract: 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: GrantFiled: October 5, 1981Date of Patent: September 21, 1982Assignee: American Home Products CorporationInventors: Anthony C. Scotese, Arthur A. Santilli
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Patent number: 4347362Abstract: 1-alkyl-4-amino-3-(3-aminotriazolo)-1,8-naphthyridine-2-ones are antihypertensive agents.Type: GrantFiled: October 8, 1981Date of Patent: August 31, 1982Assignee: American Home Products CorporationInventor: Stanley C. Bell
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Patent number: 4347355Abstract: 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: GrantFiled: December 1, 1980Date of Patent: August 31, 1982Assignee: Abbott LaboratoriesInventor: Daniel T. Chu
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Patent number: 4341784Abstract: 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: GrantFiled: September 15, 1980Date of Patent: July 27, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4324893Abstract: 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: GrantFiled: February 28, 1980Date of Patent: April 13, 1982Assignee: American Home Products CorporationInventors: Anthony C. Scotese, Arthur A. Santilli
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Patent number: 4321384Abstract: 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: GrantFiled: February 27, 1981Date of Patent: March 23, 1982Assignee: American Home Products CorporationInventors: Theodore S. Sulkowski, James L. Bergey, Albert A. Mascitti
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Patent number: 4304914Abstract: 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: GrantFiled: July 7, 1980Date of Patent: December 8, 1981Assignee: USV Pharmaceutical CorporationInventors: James R. Shroff, Bernard Loev
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Patent number: 4303661Abstract: 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: GrantFiled: October 17, 1980Date of Patent: December 1, 1981Assignee: American Home Products CorporationInventor: Stanley C. Bell
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Patent number: 4293695Abstract: 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: GrantFiled: September 29, 1980Date of Patent: October 6, 1981Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Yoshiaki Tanaka, Isao Hayakawa
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Patent number: 4264602Abstract: 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: GrantFiled: July 21, 1976Date of Patent: April 28, 1981Assignee: Sandoz, Inc.Inventor: Goetz E. Hardtmann
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Patent number: 4229456Abstract: 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: GrantFiled: October 23, 1978Date of Patent: October 21, 1980Assignee: Merck & Co., Inc.Inventors: William A. Bolhofer, Edward J. Cragoe, Jr., Jacob M. Hoffman, Jr.
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Patent number: 4207418Abstract: 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: GrantFiled: October 5, 1978Date of Patent: June 10, 1980Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4195087Abstract: 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: GrantFiled: December 6, 1977Date of Patent: March 25, 1980Assignee: Abic, Ltd.Inventor: Chaim Simonovitch
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Patent number: 4183935Abstract: 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: GrantFiled: June 13, 1978Date of Patent: January 15, 1980Assignee: BASF AktiengesellschaftInventors: Fritz Binnig, Ludwig Friedrich, Hans P. Hofmann, Horst Kreiskott, Claus Mueller, Manfred Raschack
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Patent number: 4182880Abstract: 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: GrantFiled: December 13, 1978Date of Patent: January 8, 1980Assignee: Koei Chemical Co., Ltd.Inventors: Nanao Watanabe, Haruhito Akimoto
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Patent number: 4176183Abstract: Novel naphthyridines having a 3-amino-2-OR-propoxy substituent are disclosed. The compounds have .beta.-adrenergic blocking and immediate onset antihypertensive activities.Type: GrantFiled: July 17, 1978Date of Patent: November 27, 1979Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello
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Patent number: 4137317Abstract: 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: GrantFiled: November 14, 1977Date of Patent: January 30, 1979Assignee: Abbott LaboratoriesInventors: Gerald Y. Paris, Denis G. Cimon, David L. Garmaise
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Patent number: 4128649Abstract: 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: GrantFiled: June 29, 1977Date of Patent: December 5, 1978Assignee: Sandoz, Inc.Inventor: Goetz E. Hardtmann