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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Patent number: 4965273Abstract: There are disclosed new naphthyridine- and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids.Type: GrantFiled: December 1, 1988Date of Patent: October 23, 1990Assignee: Bristol-Myers CompanyInventors: Abraham Weber, Daniel Bouzard, Munir Essiz, Pierre Di Cesare, Jean-Pierre Jacquet, Philippe Remuzon
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Patent number: 4962108Abstract: Novel quinoline-, naphthyridine-, and benzoxazine-carboxylic acid derivatives with bridged sidechains useful as antibacterial agents are described. Methods for their preparation, formulation, and use in treatment of bacterial infections is also described.Type: GrantFiled: December 9, 1988Date of Patent: October 9, 1990Assignee: Warner-Lambert CompanyInventors: Marland P. Hutt, Jr., John S. Kiely
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Patent number: 4962112Abstract: Naphthyridine and quinoline compounds having the formula: ##STR1## wherein A is CH or N; Z is an amine having the formula: ##STR2## R is o,p-difluorophenyl or p-fluorophenyl; and R.sub.1 is hydrogen or a carboxy protecting group. The compounds of the invention have antibacterial activity and improved solubility and pharmacokinetic properties.Type: GrantFiled: February 26, 1988Date of Patent: October 9, 1990Assignee: Abbott LaboratoriesInventors: Terry J. Rosen, Daniel T. Chu
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Patent number: 4956465Abstract: As novel intermediates for antibacterials, the quinolone- and 1,8-naphthyridine-4-one-carboxylic acids which are C-bonded in the 7-position of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.3, or an acid amide group --CONR.sup.4 R.sup.5, where R.sup.3 stands for C.sub.1 -C.sub.4 -alkyl,X.sup.2 stands for hydrogen, nitro, alkyl having 1 to 3 carbon atoms and halogen, in particularR.sup.1 can be alkyl having 1-4 carbon atoms, vinyl, halogenoalkyl, hydroxyalkyl, cycloalkyl having 1-6 carbon atoms or optionally substituted phenyl,R.sup.2 stands for hydrogen, alkyl having 1-3 carbon atoms which is optionally substituted by halogen, alkoxy having 1-2 carbon atoms or nitro, phenyl and for a radical ##STR2## and Z.sup.1 and Z.sup.2 can each be hydrogen or various organic radicals or together form a ring,and salts and esters thereof.Type: GrantFiled: October 3, 1988Date of Patent: September 11, 1990Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe, Uwe Petersen
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Patent number: 4954507Abstract: There are disclosed new naphthyridine- and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids.Type: GrantFiled: December 19, 1988Date of Patent: September 4, 1990Assignee: Bristol-Myers CompanyInventors: Abraham Weber, Daniel Bouzard, Munir Essiz, Pierre Di Cesare, Jean-Pierre Jacquet, Philippe Remuzon
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Patent number: 4950602Abstract: The present invention relates to inhibitors of lactate dehydrogenase that can cross the blood brain barrier and there is described herein the preparation of several analogues of nicotinamide-adenine-dinucleotide (NAD.sup.+) pyruvate adduct, of which 3(-4-(reduced 3-pyridine aldehyde-adenine dinucleotide))-pyruvate (RAP) and similar compounds appear to have a very high affinity for lactate dehydrogenase; one of which (RAP) was shown to strongly inhibit lactate production in rat brain extracts.Type: GrantFiled: February 20, 1987Date of Patent: August 21, 1990Assignee: Cornell Research Foundation, Inc.Inventor: Arthur J. L. Cooper
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Patent number: 4929613Abstract: The novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
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Patent number: 4920120Abstract: Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: December 9, 1988Date of Patent: April 24, 1990Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Susan E. Hagen, John S. Kiely
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Patent number: 4916141Abstract: The novel (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1, 8-n phthyridine-3-carboxylic acid, lower alkyl esters and pharmaceutically acceptable salts thereof are described as well as a method for its manufacture, formulation, and use in treating bacterial infections.Type: GrantFiled: March 28, 1989Date of Patent: April 10, 1990Assignee: Warner-Lambert CompanyInventor: Joseph P. Sanchez
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Patent number: 4916131Abstract: 1-Substituted naphthyridines and pyrido-pyrazines are disclosed which are useful in treating allergic reactions, inflammation, peptic ulcers and hyperproliferative skin diseases and in suppressing the immune response in mammals. Pharmaceutical compositions and methods of treatment employing such compounds are also disclosed.Type: GrantFiled: July 20, 1988Date of Patent: April 10, 1990Assignee: Schering CorporationInventors: David J. Blythin, Marvin I. Siegel, Sidney R. Smith
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Patent number: 4908056Abstract: This invention relates to novel heterocyclic carbonyl sulfonamides which are particularly useful as agricultural chemicals.Type: GrantFiled: February 17, 1989Date of Patent: March 13, 1990Assignee: E. I. Du Pont De Nemours and CompanyInventor: Chi-Ping Tseng
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Patent number: 4880814Abstract: The present invention includes compounds represented by the formula: ##STR1## wherein R.sub.1 is a hydroxy, a C.sub.1 to C.sub.6 alkoxy, benzoxy, or an alkylcarbonyloxymethoxy group, or R.sub.3 together with R.sub.1 forms a group of the formula --Y--NH-- where Y is oxygen or sulfur; or R.sub.3 is hydrogen; A is nitrogen or CR.sub.2, where R.sub.2 is hydrogen, or halogen, or R.sub.2 together with R forms a group of the formula --X--CH.sub.2 --CH(R.sub.6)-- or --X--CH.sub.2 --CH.dbd.CH.sub.2, wherein X is CH.sub.2, O, S, NH, or NCH.sub.3, and R.sub.6 is hydrogen, alkyl, or C.sub.1 -C.sub.3 haloalkyl; or R is (1) a C.sub.1 to C.sub.4 alkyl, (2) lower cycloalkyl, (3) alkylamino, (4) haloalkyl, (5) an aromatic heterocyclic ring or (6) a substituted phenyl group; and Z is a carbocyclic group;or a pharmaceutically acceptable salt thereof. The compounds of the present invention are useful as antibacterial agents.Type: GrantFiled: November 13, 1987Date of Patent: November 14, 1989Assignee: Abbott LaboratoriesInventors: Daniel T. Chu, Terry J. Rosen, Curt S. Cooper
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Patent number: 4861779Abstract: Antibacterial compounds have the formula ##STR1## wherein R.sup.1 is hydrogen, a pharmaceutically acceptable cation, or alkyl; A is CH, CF, CCl or N; Y is alkyl, haloalkyl, cyclopropyl, vinyl, methoxy, N-methylamino, p-fluorophenyl, p-hydroxyphenyl or p-aminophenyl; or A is carbon and is taken together with Y and the carbon and nitrogen to which A and Y are attached to form a five to seven membered ring which is optionally substituted; and R.sup.2 is a bridged-diazabicycloalkyl group.Type: GrantFiled: August 19, 1986Date of Patent: August 29, 1989Assignee: Pfizer Inc.Inventors: Martin R. Jefson, Paul R. Mc Guirk
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Patent number: 4859776Abstract: A process for the preparation of enantiomerically homogeneous aminopyrrolidinyl naphthyridine carboxylic acids and quinolone carboxylic acids, and for the preparation of intermediates that are useful in the production of these carboxylic acids. The compounds are useful as anti-bacterials.Type: GrantFiled: March 11, 1988Date of Patent: August 22, 1989Assignee: Abbott LaboratoriesInventors: Daniel T. Chu, Terry J. Rosen
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Patent number: 4851418Abstract: Novel quinolone and naphthyridine antibacterial agents are herein described having improved in vivo activity both orally and subcutaneously where the 7-side chain of such compounds contain an .alpha.-amino acid; also described are its corresponding optical isomers, methods of preparation as well as compositions and methods of treating infections diseases.Type: GrantFiled: July 20, 1988Date of Patent: July 25, 1989Assignee: Warner-Lambert CompanyInventor: Joseph P. Sanchez
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Patent number: 4840954Abstract: New 6,7-disubstituted-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carb oxy lic acids of the formula (I) ##STR1## in which X represents halogen or nitro and A represents ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined hereinbelow are disclosed as well as their usefulness as antibacterial agents.Type: GrantFiled: December 31, 1985Date of Patent: June 20, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4822801Abstract: Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: October 20, 1986Date of Patent: April 18, 1989Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Thomas F. Mich, Joseph P. Sanchez
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Patent number: 4820716Abstract: 7-(1-Pyrrolidinyl)-3-quinolonecarboxylic acid derivatives of the formula ##STR1## in which A is CH, CCl, CF or N,R.sup.1 is hydroxyl, hydroxymethyl or mercapto andR.sup.2 is hydrogen, alkyl, having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,with the proviso that, when R.sup.1 is hydroxy, A is not CF or N, or pharmaceutically acceptable hydrates, or salts thereof, are useful as antibacterials and animal feed utilization promoters.Type: GrantFiled: February 12, 1987Date of Patent: April 11, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4778801Abstract: A compound of the formula ##STR1## wherein X is hydrogen, halogen or nitro; Ar is phenyl or naphthyridinyl which may optionally be substituted; and either one of Z.sup.1 and Z.sup.2 is hydrogen and the other is lower alkanoyloxy or hydroxy, each of Z.sup.1 and Z.sup.2 is lower alkoxy, or Z.sup.1 and Z.sup.2 combinedly represent hydroxyimino or oxo; and a salt thereof, act on the central nervous system but are weak in adverse effects such as hypnotic and muscle relaxant effects.Type: GrantFiled: June 29, 1987Date of Patent: October 18, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Giichi Goto, Yoshiaki Saji
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Patent number: 4777175Abstract: Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: September 15, 1986Date of Patent: October 11, 1988Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Doma, Thomas F. Mich, Jeffrey B. Nichols
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Patent number: 4775686Abstract: 1-Substituted naphthyridines and pyrido-pyrazines are disclosed which are useful in treating allergic reactions, inflammation, peptic ulcers and hyperproliferative skin diseases and in suppressing the immune response in mammals. Pharmaceutical compositions and methods of treatment employing such compounds are also disclosed.Type: GrantFiled: December 18, 1986Date of Patent: October 4, 1988Assignee: Schering CorporationInventors: David J. Blythin, Marvin I. Siegel, Sidney R. Smith
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Patent number: 4771054Abstract: Novel quinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: August 15, 1986Date of Patent: September 13, 1988Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Thomas F. Mich, Jeffrey B. Nichols
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Patent number: 4771055Abstract: Novel, orally active antibacterial agents are described and characterized as 7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo -3-quinoline carboxylic acids or corresponding 1,8-naphthyridine derivatives as well as methods for their manufacture.Type: GrantFiled: April 21, 1987Date of Patent: September 13, 1988Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
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Patent number: 4764518Abstract: The present invention relates to novel antibacterial agents, corresponding to the following general formula I ##STR1## in which: Q represents an aromatic ring,X represents a hydrogen atom or a linear or branched alkyl group,Y represents a linkage or an alkyl group,Z represents a hydrogen atom, an alkyl, aralkyl or heteroalkyl group.These compounds constitute anti-bacterial agents with multiple pharmacological activity.Type: GrantFiled: June 13, 1986Date of Patent: August 16, 1988Assignee: PanmedicaInventors: Claude Laruelle, Marcel Lepant, Bernard Raynier
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Patent number: 4760081Abstract: The present invention describes 1,6-naphthyridine derivatives of the general formula: ##STR1## wherein R.sup.1 is an unsubstituted or substituted aromatic or heteroaromatic ring, R.sup.2 is a straight-chained or branched alkyl radical containing up to four carbon atoms or a benzyl radical, R.sup.3 is a hydrogen atom, a straight-chained or branched alkyl radicals or an alkoxycarbonyl radical containing up to four carbon atoms, R.sup.4 is a straight-chained or branched alkyl radical containing up to four carbons and R.sup.5 is a carboxyl group or a straight-chained, branched or cyclic alkoxycarbonyl radical which contains up to 17 carbon atoms and optionally also contains an oxygen, sulphur or nitrogen atom; as well as the pharmacologically acceptable salts thereof, which are useful for treating diseases of the blood vessels.Type: GrantFiled: January 28, 1987Date of Patent: July 26, 1988Assignee: Goedecke AktiengesellschaftInventors: Gerhard Satzinger, Johannes Hartenstein, Karl Mannhardt, Jurgen Kleinschroth, Hartmut Osswald, Gunter Weinheimer, Edgar Fritschi
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Patent number: 4751228Abstract: The present invention provides 1,6-naphthyridine derivatives of formula ##STR1## wherein R.sup.1 is an unsubstituted or substituted aromatic or heteroaromatic ring or an unsubstituted or substituted condensed aromatic or heterocyclic ring system, R.sup.2 is a straight-chained or branched alkyl radical containing up to 4 carbon atoms, a benzyl radical or a straight-chained or branched, substituted or unsubstituted aminoalkyl radical containing up to 8 carbon atoms, R.sup.3 is a hydrogen atom, a straight-chained or branched alkyl radical or an alkoxycarbonyl radical, in each case containing up to 4 carbon atoms, R.sup.4 is a straight-chained or branched hydrocarbon radical containing up to 21 carbon atoms, which can also contain oxygen, sulphur, nitrogen or halogen atoms and is optionally substituted by carbocyclic or heterocyclic ring systems, or is an amino, cyano, formyl, halogenomethyl or dihalomethyl radical and R.sup.Type: GrantFiled: January 28, 1987Date of Patent: June 14, 1988Assignee: Goedecke AktiengesellschaftInventors: Jorgen Kleinschroth, Karl Mannhardt, Johannes Hartenstein, Gerhard Satzinger, Dieter Muster, Wolfgang Steinbrecher, Bernd Wagner, Hartmut Osswald
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Patent number: 4738968Abstract: The present invention relates to a 1,8-naphthyridine derivative of the formula ##STR1## wherein X is a fluorine or chlorine atom, and R is a hydrogen atom, or a methyl or ethyl group;and esters thereof and salts thereof are processes for preparation thereof. These compounds show excellent anti-bacterial activity and are useful antibacterial agents.Type: GrantFiled: February 12, 1986Date of Patent: April 19, 1988Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Jun-ichi Matsumoto, Junji Nakano, Katsumi Chiba, Shinichi Nakamura
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Patent number: 4735949Abstract: Disubstituted 7-pyrrolidinoquinoline- and -naphthyridine-3-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.Type: GrantFiled: June 22, 1987Date of Patent: April 5, 1988Assignee: Warner-Lambert CompanyInventors: John M. Domagala, Susan E. Prugh, Joseph P. Sanchez, Marjorie S. Solomon
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Patent number: 4711901Abstract: The present invention describes 1,6-naphthyridine derivatives of the general formula: ##STR1## wherein R.sup.1 is an unsubstituted or substituted aromtic or heteroaromatic ring, R.sup.2 is a straight-chained or branched alkyl radical containing up to four carbon atoms or a benzyl radical, R.sup.3 is a hydrogen atom, a straight-chained or branched alkyl radical or an alkoxycarbonyl radical containing up to four carbon atoms, R.sup.4 is a straight-chained or branched alkyl radical containing up to four carbons and R.sup.5 is a carbonyl group or a straight-chained, branched or cyclic alkoxycarbonyl radical which contains up to 17 carbon atoms and optionally also contains an oxygen, sulphur or nitrogen atom; as well as the pharamacologically acceptable salts thereof, which are useful for treating diseases of the blood vessels.Type: GrantFiled: July 30, 1986Date of Patent: December 8, 1987Inventors: Gerhard Satzinger, Johannes Hartenstein, Karl Mannhardt, Jurgen Kleinschroth, Hartmut Osswald, Gunter Weinheimer, Edgar Fritschi
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Patent number: 4704459Abstract: This invention relates to a process for industrially producing a 1-substituted aryl-1,4-dihydro-4-oxonaphthyridine derivative and a salt thereof which are useful as an antibacterial agent, and also to intermediates therefor and processes for producing the intermediates.Type: GrantFiled: January 17, 1986Date of Patent: November 3, 1987Assignee: Toyama Chemical Co., Ltd.Inventors: Yozo Todo, Tetsuo Yamafuji, Katsuyuki Nagumo, Isao Kitayama, Hideyoshi Nagaki, Mikako Miyajima, Yoshinori Konishi, Hirokazu Narita, Shuntaro Takano, Isamu Saikawa
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Patent number: 4698341Abstract: New 1,6-naphthyridinone derivatives of the formula I ##STR1## are herein described wherein R.sup.1 represents an unsubstituted or substituted aromatic or heteroaromatic ring;R.sup.2 is hydrogen, a straight-chained or branched alkyl, alkoxyalkyl, or a substituted or unsubstituted aminoalkyl group with up to ten carbon atoms;R.sup.3 is hydrogen, a straight-chained or branched alkyl group, or an alkoxycarbonyl radical with up to four carbon atoms;R.sup.4 is hydrogen, or a morpholinoethyl group;R.sup.5 is a straight-chained or branched alkyl group with up to four carbon atoms, or an amino group; andR.sup.6 is a carboxyl group, or an alkyl- or alkyloxyalkyl carbonyl radical, containing up to 12 carbon atoms and optionally interrupted by an oxygen, sulphur, or nitrogen atom;as well as optionally the pharmacologically acceptable salts thereof; processes for the preparation of these derivatives and their use in the control of vascular diseases.Type: GrantFiled: July 11, 1985Date of Patent: October 6, 1987Assignee: Godecke AktiengesellschaftInventors: Gerhard Satzinger, Johannes Hartenstein, Karl Mannhardt, Jurgen Kleinschroth, Manfred Herrmann, Edgar Fritschi, Horst-Dietmar Tauschel, Bernd Wagner, Gunter Wolf
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Patent number: 4696694Abstract: A pyridine derivative having the formula: ##STR1## wherein one of A, B, D and E is oxygen, sulfur, --SO--, --SO.sub.2 --, --NR.sup.3 --, ##STR2## or .dbd.CH-- with the rest being all carbon atoms; X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthioalkyl, tetrahydrothiopyranyl, hydroxyl, CF.sub.3, phenyl or pyridyl; n is an integer of from 0 to 6,; W is oxygen or sulfur; R is hydrogen, di-lower alkylimino, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl, C.sub.4 or C.sub.5 oxacycloalkyl, C.sub.2 -C.sub.5 mono-, di- or tri-haloalkenyl, C.sub.2 -C.sub.5 haloalkynyl, glycidyl, furfuryl, alkylthioalkyl, C.sub.3 -C.sub.6 cycloalkyl or a cation R.sup.1 is C.sub.1 -C.sub.4 alkyl, R.sup.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or R.sup.1 and R.sup.Type: GrantFiled: July 7, 1986Date of Patent: September 29, 1987Assignee: Nissan Chemical Industries Ltd.Inventors: Tatsuo Numata, Masataka Hatanaka, Junichi Watanabe, Takasi Ikai, Tsutomu Nawamaki, Kenji Hattori
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Patent number: 4670444Abstract: The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1, 4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specification. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.Type: GrantFiled: May 29, 1984Date of Patent: June 2, 1987Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4665079Abstract: Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: January 23, 1985Date of Patent: May 12, 1987Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Domagala, Thomas F. Mich, Jeffrey B. Nichols
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Patent number: 4663457Abstract: 1-cyclopropyl-6,7-dihalo-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and their esters, which are useful as intermediates for the preparation of compounds which are useful as anti-bacterial agents.Type: GrantFiled: August 13, 1985Date of Patent: May 5, 1987Assignee: Warner-Lambert CompanyInventors: Thomas F. Mich, Joseph P. Sanchez, John M. Domagala, Ashok K. Trehan
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Patent number: 4649144Abstract: The present invention relates to a 1,8-naphthyridine derivative of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each hydrogen or lower alkyl having 1 to 5 carbon atoms; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.Type: GrantFiled: July 20, 1984Date of Patent: March 10, 1987Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Jun-ichi Matsumoto, Teruyuki Miyamoto, Hitoshi Uno, Shinichi Nakamura
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Patent number: 4638067Abstract: Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: August 12, 1985Date of Patent: January 20, 1987Assignee: Warner-Lambert Co.Inventors: Townley P. Culbertson, John M. Domagala, Thomas F. Mich, Jeffrey B. Nichols
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Patent number: 4621088Abstract: The present invention relates to new N-acyl derivatives of amino acids.These derivatives correspond to the general formula I below: ##STR1## in which A represents a linear or branched, saturated hydrocarbon radical containing from 1 to 6 carbon atoms or a saturated ring containing 6 carbon atoms,X represents a --COOH radical, a --COOAlkyl radical (alkyl from C.sub.1 to C.sub.4), a hydrogen atom or a --CH.sub.3 group when Y is --COOH or --COOAlkyl,Y represents a --COOH radical, a --COOAlkyl radical (alkyl from C.sub.1 to C.sub.4), an --NH.sub.2 group, an --SH group, an --SCH.sub.3 group, a --NH--CH(.dbd.NH)--NH.sub.2 group, a substituted or unsubstituted phenyl group, an indolin-3-yl group or a 5-hydroxyindolin-3-yl group, andQ represents an optionally substituted aromatic ring or an optionally substituted heterocycle containing 1 or 2 nitrogen atoms.Drugs having an antiallergic action.Type: GrantFiled: May 23, 1985Date of Patent: November 4, 1986Assignee: PanmedicaInventors: Claude Laruelle, Marcel Lepant, Bernard Raynier
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Patent number: 4620007Abstract: The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1,4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specifications. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.Type: GrantFiled: December 11, 1985Date of Patent: October 28, 1986Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4618678Abstract: 4-(2,3-dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-1,7-na phthyridine-3-carboxylic acid 2-(2,3-dichlorophenoxy)ethyl ester and pharmaceutically acceptable salts thereof are useful antihypertensive agents.Type: GrantFiled: December 17, 1985Date of Patent: October 21, 1986Assignee: American Home Products CorporationInventors: Theodore S. Sulkowski, Paul J. Silver, Albert A. Mascitti
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Patent number: 4616019Abstract: Naphthyridine compounds having the formula: ##STR1## wherein Z is an amine or an aliphatic heterocyclic group, R is a phenyl group or an aromatic heterocyclic group and R.sub.1 is hydrogen or a carboxy protecting group. The compounds of the invention have antibacterial activity.Type: GrantFiled: October 4, 1985Date of Patent: October 7, 1986Assignee: Abbott LaboratoriesInventor: Daniel T. Chu
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Patent number: 4596873Abstract: 1,4,5,6,7,8-Hexahydro-2-alkyl-4-aryl-5-oxo-1,7-naphthyridine-3-carboxylic acid aromatic esters and pharmaceutically acceptable acid addition salts thereof are useful antihypertensive agents.Type: GrantFiled: July 29, 1985Date of Patent: June 24, 1986Assignee: American Home Products CorporationInventors: Theodore S. Sulkowski, Paul J. Silver, Albert A. Mascitti
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Patent number: 4571396Abstract: Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: March 11, 1985Date of Patent: February 18, 1986Assignee: Warner-Lambert CompanyInventors: Marland P. Hutt, Thomas F. Mich, Townley P. Culbertson
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Patent number: 4567186Abstract: 3-Z-5-Q-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where Z is hydrogen or cyano, and Q is 2(or 3)-furanyl, 2(or 3)-thienyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two methyl substituents, are useful as cardiotonic agents and corresponding compounds where Z is carboxy are useful as intermediates. Also shown as intermediates are 5-(Q-CO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Q is defined as above. Processes for preparing said compounds (I and II) are shown.Type: GrantFiled: January 14, 1985Date of Patent: January 28, 1986Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Baldev Singh
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Patent number: 4560508Abstract: 4-Cyano-2-azetidinone derivatives represented by the formula ##STR1## wherein R.sup.1 is an amino group which may be acylated or protected, X is a hydrogen atom or a methoxy group and W is a hydrogen atom or a sulfo group, and methods of producing the same, for example, as represented by ##STR2## wherein R.sup.2 is an acylated or protected amino group, Y is a halogen atom or a group having the formula --OCOR.sup.3, --SCOR.sup.3 or --S(O).sub.n --R.sup.3 (R.sup.3 being a hydrocarbyl group and n an integer 1 or 2), R.sup.4 is an amino group which may be acylated or protected and X is as defined above. Compounds [I] are useful as advantageous intermediates for the synthesis of optically active 4-substituted-2-azetidinone derivatives, and, when W=SO.sub.3 H, [I] are also useful as antimicrobial agents and as beta-lactamase inhibitors.Type: GrantFiled: December 20, 1982Date of Patent: December 24, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Taisuke Matsuo, deceased, Michihiko Ochiai, Shoji Kishimoto
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Patent number: 4559347Abstract: 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: October 11, 1984Date of Patent: December 17, 1985Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Baldev Singh
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Patent number: 4552882Abstract: The present invention relates to new derivatives of 7-(1-pyrrolyl)-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 7-(1-pyrrolyl)-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid of general formula I: ##STR1## in which: X represents a carbon atom or a nitrogen atom, andR represents a hydrogen atom or a fluorine atom, as well as their physiologicaly acceptable alkali metal salts or alkaline earth metal salts. The derivatives of the present invention are advantageously used as antimicrobial agents, espcially as anti-bacterial and anti-fungal agents.Type: GrantFiled: June 20, 1984Date of Patent: November 12, 1985Assignee: Provesan, SAInventor: Jose Esteve-Soler
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Patent number: 4551534Abstract: 7-(Substituted)-1,4,5,6,7,8-hexahydro-2-alkyl-4-aryl-5-oxo-1,7-naphthyridin e-3-carboxylic acid esters and pharmaceutically acceptable acid addition salts thereof are useful antihypertensive agents.Type: GrantFiled: March 30, 1984Date of Patent: November 5, 1985Assignee: American Home Products CorporationInventors: Theodore S. Sulkowski, Paul J. Silver, Albert A. Mascitti, Reinhold H. W. Bender
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Patent number: 4550105Abstract: Disclosed are compounds of the general formula: ##STR1## wherein R.sub.1 is amino, an acylated amino or a protected amino group, X is hydrogen or methoxy, and R' is hydrogen, R or R.sup.4 wherein R is an organic residue attached to the azetidine ring through a carbon atom therein and R.sub.4 is azido, a halogen, an amino group which may optionally be acylated or a group of the formula --OR.sub.5, ##STR2## or --S--S--R.sub.5 wherein R.sub.5 is an organic residue and n is 0, 1 or 2, and pharmaceutically acceptable salts and esters thereof.The compounds have antimicrobial and/or .beta.-lactamase-inhibitory activity and are of value as drugs for human beings and domesticated animals.Type: GrantFiled: December 3, 1981Date of Patent: October 29, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Taisuke Matsuo, Shoji Kishimoto, Michihiko Ochiai
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Patent number: RE32975Abstract: The invention provides 4-pyridone-3-carboxylic acids and derivatives thereof together with a method for their preparation. Also included in the invention are compositions containing said 4-pyridone-3-carboxylic acids and derivatives and the use of said compounds and compositions as antibacterial and/or antifungal agents or for animal growth promotion or improved feed utilization.Type: GrantFiled: May 14, 1985Date of Patent: July 4, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger