7-position Substituent Contains Hetero Ring Patents (Class 514/206)
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Patent number: 5264430Abstract: Derivatives of 2-spirocyclopropyl cephalosporin sulfone of the structural formula I ##STR1## are provided which are useful as potent elastase inhibitors.Type: GrantFiled: April 8, 1991Date of Patent: November 23, 1993Assignee: SynPhar Laboratories, Inc.Inventors: Samarendra N. Maiti, David Czajkowski, Paul Spevak, Kazuo Adachi, Ronald G. Micetich
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Patent number: 5262410Abstract: Cephalosporin compounds having a 3-position substituent of the formula (I) are described:--CH.sub.2 --S--Q--(Y).sub.n --Pwherein Q is a 5- or 6-membered heterocyclic ring, P is a benzene ring substituted by groups R.sup.1 and R.sup.2 which are ortho with respect to one another, wherein R.sup.1 is hydroxy or an in vivo hydrolysable ester thereof and R.sup.2 is hydroxy, an in vivo hydrolysable ester thereof, carboxy, sulpho, hydroxymethyl, methanesulphonamido or ureido; or P is a group of the formula (II) or (III): ##STR1## wherein M is oxygen or a group NR.sup.3 wherein R.sup.3 is hydrogen or C.sub.1-4 alkyl; said ring P being further optionally substituted; and --(Y).sub.n -- is a bond or various linking groups or --(Y)--.sub.n may be such so that rings Q and P are fused.The use of such compounds as antibacterial agents is described as are processes for their preparation and intermediates therefor.Type: GrantFiled: August 5, 1991Date of Patent: November 16, 1993Assignee: ICI PharmaInventors: Frederic H. Jung, Annie A. Olivier
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Patent number: 5258377Abstract: Derivatives of 2-spirocyclopropyl 4-acylcephem sulfones of the formula (I) ##STR1## are provided which are useful as potent elastase inhibitors and hence are useful in the prevention, control and treatment of inflammatory conditions, especially arthritis and emphysema.Type: GrantFiled: April 8, 1991Date of Patent: November 2, 1993Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Samarendra N. Maiti, Narender A. V. Reddy, David Czajkowski, Paul Spevak, Charles Fiakpui, Ronald G. Micetich
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Patent number: 5244890Abstract: Cephem compounds having the following formula are disclosed: ##STR1## R.sup.1 =amino or protected amino R.sup.2 =an organic group ##STR2## R.sup.6 =lower alkyl R.sup.7, R.sup.8 .dbd.OH or protected OHY.dbd.N or CHThe compounds are useful as antimicrobial agents.Type: GrantFiled: May 20, 1992Date of Patent: September 14, 1993Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hideaki Yamanaka, Yoshiki Yoshida, Jiro Goto, Takeshi Terasawa, Shinya Okuda, Kazuo Sakane
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Patent number: 5244892Abstract: Novel cephem compounds represented by a formula [I] and pharmacologically admissible salts or capable of physiologically hydrolyzable nontoxic esters thereof are disclosed. ##STR1## [wherein R.sup.1 indicates a straight-chain or branched lower alkyl group, which may be substituted by carboxyl group which may be protected, trityl group, hydrogen atom or fluorine-substituted lower alkyl group, R.sup.2 indicates a hydrogen atom, metal atom, protective group for carboxyl group or ester residue producible hydrolyzable ester in vivo, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be identical or different, indicate hydrogen atoms, halogen atoms, straight-chain or branched lower alkyl groups, which may be substituted, mercapto groups, which may be substituted, lower alkylamino groups, hydroxyl groups, which may be protected, lower alkoxy groups, lower alkanoyl groups, lower alkoxycarbonyl groups, or lower alkylenedioxy groups, which may be substituted, being maybe formed with R.sup.3 and R.sup.4, R.sup.Type: GrantFiled: October 11, 1991Date of Patent: September 14, 1993Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Seigo Suzue, Kikoh Obi, Tatsuhiro Saito, Keiji Hirai, Hideyuki Fukuda
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Patent number: 5242913Abstract: Certain 7-beta-[2-(2-amino-4-thiazolyl)-(Z)-2-(chloromethylene)acetamido]-3-[(subs tituted)methyl]-ceph-3-em-4-carboxylic acids, pharmaceutically-acceptable salts thereof and conventional in vivo hydrolyzable esters thereof are valuable as broad spectrum antibacterial agents, particularly useful for the treatment of bacterial infections in man and other mammals.Type: GrantFiled: October 11, 1991Date of Patent: September 7, 1993Assignee: Pfizer Inc.Inventor: Susumu Nakanishi
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Antibiotic C-7 catechol-substituted cephalosporin compounds, compositions, and method of use thereof
Patent number: 5234920Abstract: The present invention relates to new cephalosporins of the formula ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or carboxy, with the proviso that both cannot be the same;R.sup.3 is hydrogen or acetyl; andR.sup.4 is a radical selected from the group consisting of ##STR2## in which n is 1 or 2, R.sup.5 is hydrogen or acetyl, and R.sup.6 is hydrogen, a lower C.sub.1-3 alkyl, or a radical selected from the group consisting of ##STR3## in which n and R.sup.5 are as defined above. In another aspect, this invention relates to processes for the preparation of the compounds of Formula I, to pharmaceutical compositions containing at least one compound of Formula I, and to intermediates in their preparation.Type: GrantFiled: January 6, 1992Date of Patent: August 10, 1993Assignee: Bristol-Myers Squibb CompanyInventors: Takaaki Okita, Hajime Kamachi, Shinji Masuyoshi, Kiyoto Imae -
Patent number: 5225406Abstract: The present invention relates to a compound having the formula: ##STR1## wherein R is a hydrogen atom, a carboxyl-protecting group or a negative charge and Q is a hydrogen atom, a halogen atom, a hydroxyl group, an acetoxy group, a carbamoyloxy group, an azide group, a substituted or unsubstituted quarternary ammonio group or a substituted or unsubstituted heterocyclic thio group having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, or a non-toxic salt or physiologically hydrolyzable non-toxic ester thereof; a process for producing it; and an antibacterial agent comprising it as an active ingredient.Further, the present invention also relates to a compound having the formula: ##STR2## wherein R.sup.3 is a hydrogen atom or an amino-protecting group, and each of R.sup.4 and R.sup.5 which may be the same or different is a hydrogen atom or a carboxyl-protecting group, or a salt thereof; and a process for producing it.Type: GrantFiled: September 3, 1991Date of Patent: July 6, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Koji Yamada, Norikazu Otake, Fumio Nakano, Akira Asai, Satoru Kuroyanagi, Yoshiharu Tanaka, Moriaki Ishikawa, Ryosuke Ushijima
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Patent number: 5223496Abstract: Cephalosporin compounds of Formulas II ##STR1## where R is hydrogen or a pharmaceutical cation, in which case R.sub.1 is not present, orR is hydrogen or a chemical bond when R.sub.1 is an acid addition salt anion, and R.sub.2 is (a) hydrogen, (b) a duplicate of the formula I compound to form a dimer, (c) an aminocarbonylmethyl, or (d) an --SR.sub.3 group where R.sub.3 is alkyl, cyclohexyl, phenyl, chloro-substituted phenyl, nitro-substituted phenyl, benzyl or furfuryl, have been found to be valuable as antibiotics for treating warm-blooded animals to combat pathogenic bacterial infections which cause diseases such as the commonly known "shipping fever".Type: GrantFiled: April 23, 1992Date of Patent: June 29, 1993Assignee: The Upjohn CompanyInventors: Alexander R. Cazers, K. Thomas Koshy, Prem S. Jaglan, Robert J. Yancey, Jr., Terry J. Gilbertson, Thomas S. Arnold, David B. Johnson, Catherine L. Gatchell
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Patent number: 5219848Abstract: Cephalosporin antibiotics having a 3-position substituent of the formula: ##STR1## are described, wherein X is --CO--, --SO.sub.2 -- or --COCH.sub.2 --; Y is --CO--, --SO.sub.2 -- or --CH.sub.2 --; Q is a benzene, pyridine or naphthalene ring, R.sup.1 and R.sup.2 are ortho with respect to each other and are independently hydroxy or of the formula O--M wherein M is a moiety and the O--M bond is cleavable in vivo and ring Q may be further substituted by a variety of atoms and groups. Processes for their preparation and use are described.Type: GrantFiled: August 10, 1990Date of Patent: June 15, 1993Assignees: ICI Pharma, Imperial Chemical Industries PLCInventors: Laurent F. A. Hennequin, David M. Hollinshead
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Patent number: 5214037Abstract: A novel thioalkylthio cephalosporin antibiotic compound of formula I: ##STR1## wherein Acyl is C.sub.1 -C.sub.12 acyl; Het is optionally substituted monocyclic heteroaromatic group containing one or more hetero atoms; R.sup.1 is a single bond or C.sub.1 -C.sub.4 alkylene; R.sub.2 is a straight or branched C.sub.1 -C.sub.4 alkylene; X is a sulfur atom or sulioxide group; and Y is a hydrogen atom or methoxy group, or a pharmaceutically acceptable salt or an amino-, carboxy- and/or hydroxy-protected derivative thereof, a formulation containing the same and a method for treating bacterial infections.Type: GrantFiled: July 12, 1991Date of Patent: May 25, 1993Assignee: Shionogi & Co., Ltd.Inventors: Tadatoshi Kubota, Masaharu Kume
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Patent number: 5202315Abstract: The present invention relates to new cephalosporin compounds of the formula(I), pharmaceutically acceptable non-toxic salts thereof, and physiologically hydrolyzable esters and solvates thereof, which have potent and broad antibacterial activities ##STR1## wherein R.sup.1 is a C.sub.1.about.4 alkyl, C.sub.3.about.4 alkenyl, C.sub.3.about.4 alkynyl group, or --C(R.sup.a)(R.sup.b)CO.sub.2 H.sub.1 wherein R.sup.a and R.sup.b are the same or different, and each is a hydrogen atom or a C.sub.1.about.4 alkyl group, or R.sup.a and R.sup.b form a C.sub.3.about.7 cycloalkyl group with the carbon atom to which they are linked;R.sup.2 is a C.sub.1.about.4 alkyl, C.sub.3.about.4 alkenyl or C.sub.3.about.4 cycloalkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted phenyl group;R.sup.3 is hydrogen or a C.sub.1.about.4 alkyl group; andQ is N or CH.The invention further relates to a process for preparing said compounds, and to pharamaceutical compositions containing said compounds.Type: GrantFiled: March 15, 1990Date of Patent: April 13, 1993Assignee: Lucky, Ltd.Inventors: Yong Z. Kim, Hun S. Oh, Jae H. Yeo, Jong C. Lim, Won S. Kim, Chan S. Bang, Hyeon J. Yim
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Patent number: 5200404Abstract: A compound of the formula (II): ##STR1## and pharmaceutically acceptable salts an in vivo hydrolysable esters are described as is their preparation and use as antibacterial agents.Type: GrantFiled: March 18, 1991Date of Patent: April 6, 1993Assignee: ICI PharmaInventor: Frederick H. Jung
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Patent number: 5196414Abstract: The present invention provides compounds of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.6 haloalkyl;A and A' are independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, amino, a 5-6 membered organic heterocycle containing 1, 2, or 3 hetero atoms selected from nitrogen or sulfur, C.sub.1 -C.sub.6 alkoxy, or phenyl; or A and A' taken together form a group of the formulae ##STR2## wherein X is hydrogen, halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, nitro, or carboxy; and Y is nitrogen or carbon; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions and methods or treatment using the above compounds.Type: GrantFiled: January 18, 1991Date of Patent: March 23, 1993Assignee: Eli Lilly and CompanyInventor: Robert J. Ternansky
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Patent number: 5147871Abstract: There are presented anti-bacterial cephalosporins having broad antimicrobial activity of the formula ##STR1## wherein R.sub.1 is an antibiotically active quinolonyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkoxy, amino, lower alkylthio and amido; R.sub.3 is selected from the group consisting of hydrogen, and acyl group, and m is 0, 1 or 2 and the readily hydrolysable esters or salts of these compounds and hydrates of the compounds of formula I or of their esters or salts.Type: GrantFiled: December 5, 1991Date of Patent: September 15, 1992Assignee: Hoffmann La-Roche, Inc.Inventors: Harry A. Albrecht, Ka-Kong Chan, Dennis D. Keith, Rudolf L. Then, Manfred Weigele
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Patent number: 5143910Abstract: Antibacterial hydroxyarylpiperazinocephalosporins of the formula: ##STR1## wherein R.sup.1 is amino or acylamino; R.sup.2 is H or methoxy; R.sup.3 is alkyl; R.sup.4 is --(P--C--Q).sub.n --, where P and Q each are H, alkyl or OH, or P and Q combine to form oxo, and n is 0 or 4; R.sup.5 is substituted or unsubstituted hydroxyaryl; R.sup.6 has a negative charge and is COO, or an anion in combination with an optionally protected carboxy; and X is O, S or S.fwdarw.O; an antibacterial preparation containing the same; a method for killing bacteria and preventing or treating bacterial infection by using the same; and syntheses of the cephalosporins are provided.Type: GrantFiled: August 23, 1990Date of Patent: September 1, 1992Assignee: Shionogi & Co., Ltd.Inventors: Hiroshi Onoue, Toshiro Konoike, Hiroyuki Ishitobi
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Patent number: 5134138Abstract: An antibacterial 3-vic-dihydroxyaroylmethylpyridiniothiomethyl cephalosporin (I) and its salts represented by the following formula: ##STR1## (wherein, R.sup.1 is amino group or acylamino; R.sup.2 is hydrogen or methoxy; R.sup.3 is hydrogen atom or substituent; R.sup.4 is vic-dihydroxyaryl; R.sup.5 is straight or branched lower alkylene; R.sup.6 is hydrogen, a carboxy-protecting group or combined with Y a negative charge; X is --O--, --S-- or sulfinyl; and Y is a counter-ion of pyridinio or combined with R.sup.6 a negative charge),a disinfecting and treating method of bacterial infection using it, and synthetic methods thereof are provided.Type: GrantFiled: July 9, 1990Date of Patent: July 28, 1992Assignee: Shionogi & Co., Ltd.Inventors: Hiroshi Onoue, Kyoji Minami, Koji Ishikura
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Patent number: 5134137Abstract: Cephalosporin compounds of Formulas II ##STR1## where R is hydrogen or a pharmaceutical cation, in which case R.sub.1 is not present, orR is hydrogen or a chemical bond when R.sub.1 is an acid addition salt anion, and R.sub.2 is (a) hydrogen, (b) a duplicate of the formula I compound to form a dimer, (c) an aminocarbonylmethyl, or (d) an --SR.sub.3 group where R.sub.3 is alkyl, cyclohexyl, phenyl, chloro-substituted phenyl, nitro-substituted phenyl, benzyl or furfuryl, have been found to be valuable as antibiotics for treating warm-blooded animals to combat pathogenic bacterial infections which cause diseases such as the commonly known "shipping fever".Type: GrantFiled: May 9, 1990Date of Patent: July 28, 1992Assignee: The Upjohn CompanyInventors: Alexander R. Cazers, K. Thomas Koshy, Prem S. Jaglan, Robert J. Yancey, Jr., Terry J. Gilbertson, Thomas S. Arnold, David B. Johnson, Catherine L. Gatchell
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Patent number: 5126336Abstract: This invention relates to novel cephalosporin derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen, a straight, branched, or cyclic lower alkyl group having up to six carbon atoms or a radical of the formula ##STR2## in which R.sup.3 and R.sup.4 are each independently hydrogen, methyl or ethyl, or R.sup.3 and R.sup.4, taken together with the carbon atom to which they are attached, may be a cycloalkylidene ring containing from 3 to 5 carbon atoms;R.sup.2 is a radical selected from the group consisting of ##STR3## wherein R.sup.5 is hydrogen or acetyl; R.sup.6, R.sup.7 and R.sup.8 each are independently C.sub.1-5 alkyl; n is 1 or 2; and y is 1 to 5.In another aspect, this invention relates to compounds of formula I and their nontoxic pharmaeutically acceptable salts, physiologically hydrolyzable esters or solvates.Representative compounds of this invention were selected for testing and were shown to display potent antibacterial activity.Type: GrantFiled: August 23, 1990Date of Patent: June 30, 1992Assignee: Bristol-Myers Squibb CompanyInventors: Kiyoto Imae, Hajime Kamachi, Shinji Masuyoshi, Seiji Iimura, Takayuki Naito
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Patent number: 5114933Abstract: Cephalosporin compounds having a 3-position substituent of the formula (I) are described:--CH.sub.2 --Y--Q (I)wherein Y is a bond or a linking group --NR.sup.4 --Y'--, --O--Y'--, 13 S--Y'-- wherein R.sup.4 is hydrogen, various optionally substituted alkyl groups, alkenyl, alkanoyl or alkanesulphonyl, and Y' is a bond or various optionally substituted alkylene groups; and Q is a benzene ring (optionally fused to a further benzene ring so forming a naphthyl group or optionally fused to a 5 or 6 membered heterocyclic aromatic group containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur), said benzene ring being substituted by groups R.sup.1 and R.sup.2 which are ortho with respect to one another, wherein R.sup.1 is hydroxy or an in vivo hydrolyzable ester thereof and R.sup.2 is hydroxy, and in vivo hydrolyzable ester thereof, carboxy, sulpho, hydroxymethyl, methanesulphonamido or ureido; or Q is a group of the formula (II) or (III): ##STR1## wherein M is oxygen or a group NR.sup.3 wherein R.Type: GrantFiled: November 23, 1987Date of Patent: May 19, 1992Assignee: ICI PharmaInventors: Alain M. Bertrandie, Thomas G. C. Bird, Frederic H. Jung
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Patent number: 5104866Abstract: A water-soluble antibiotic composition which comprises crystals of a cephem compound of the following formula: ##STR1## wherein R.sup.1 is a residue of an aliphatic hydrocarbon which may have suitable substituent(s), andR.sup.2 is a heteronio (lower)alkyl, or an acid addition salt thereof, and a pharmaceutically acceptable carbonic acid salt.And a salt of new cephem compound derived from the above-mentioned cephem compound.Type: GrantFiled: July 25, 1990Date of Patent: April 14, 1992Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Kazuo Sakane, Nobuyoshi Yasuda, Shintaro Nishimura
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Patent number: 5091382Abstract: Cephalosporin derivatives of the general formula ##STR1## pharmaceutical preparations active against bacterial infections which contain such cephalosporin derivatives, processes for the preparation of the cephalosporin derivatives, use of the cephalosporin derivatives for the preparation of a pharmaceutical for combating bacterial infections, and starting products for the preparation of cephalosporin derivatives.Type: GrantFiled: July 13, 1990Date of Patent: February 25, 1992Assignee: Hoechst AktiengesellschaftInventors: Friedhelm Adam, Walter Durckheimer, Karl-Heinz Scheunemann, Dieter Isert, Gerhard Seibert
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Patent number: 5089491Abstract: A 3-propenylcephem derivative of the following formula: ##STR1## wherein R.sub.1 represents a fluoro-substituted lower alkyl group or a cyano-substituted lower alkyl group, and A represents a cyclic or an acylic ammonio group, or a pharmaceutically acceptable salt thereof, exhibiting excellent anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria; Process for the preparation thereof; Anti-bacterial composition; Intermediate for the 3-propenylcephem derivative; and Process for the preparation of the intermediate.Type: GrantFiled: January 11, 1990Date of Patent: February 18, 1992Assignee: Eisai Co., Ltd.Inventors: Takashi Kamiya, Toshihiko Naito, Shigeto Negi, Yuuki Komatu, Yasunobu Kai, Takaharu Nakamura, Isao Sugiyama, Yoshimasa Machida, Seiichiro Nomoto, Kyosuke Kitoh, Kanemasa Katsu, Hiroshi Yamauchi
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Patent number: 5089490Abstract: Cephem derivatives of the general formula ##STR1## in which the R.sub.2 O group is in the syn-position, a process for their manufacture and pharmaceutical formulations which are active against bacterial infections and contain these compounds.Type: GrantFiled: August 23, 1990Date of Patent: February 18, 1992Assignee: Hoechst AktiengesellschaftInventors: Walter Durckheimer, Dieter Bormann, Eberhard Ehlers, Elmar Schrinner, Rene Heymes
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Patent number: 5084453Abstract: The present invention relates to a compound having the formula: ##STR1## wherein R is a hydrogen atom, a carboxyl-protecting group or a negative charge and Q is a hydrogen atom, a halogen atom, a hydroxyl group, an acetoxy group, a carbamoyl group, an azide group, a substituted or unsubstituted quarternary ammonio group or a substituted or unsubstituted heterocyclic thio group having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, or a non-toxic salt or physiologically hydrolyzable non-toxic ester thereof; a process for producing it; and an antibacterial agent comprising it as an active ingredient.Further, the present invention also relates to a compound having the formula: ##STR2## wherein R.sup.3 is a hydrogen atom or an amino-protecting group, and each of R.sup.4 and R.sup.5 which may be the same or different is a hydrogen atom or a carboxyl-protecting group, or a salt thereof; and a process for producing it.Type: GrantFiled: October 13, 1988Date of Patent: January 28, 1992Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Koji Yamada, Norikazu Otake, Fumio Nakano, Akira Asai, Satoru Kuroyanagi, Yoshiharu Tanaka, Moriaki Ishikawa, Ryosuke Ushijima
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Patent number: 5081116Abstract: A 7-[2-(2-amino-4-thiazolyl)-2-(hydroxyimino)-acetamido]-3-(1,3-dithiolan-2- yl)-3-cephem-4-carboxylic acid derivative is provided which can be represented by the general formula: ##STR1## wherein A represents a hydrogen atom, a 1-acetoxyethyl group, a 1-cyclohexylacetoxyethyl group or a pivaloyloxy-methyl group.Type: GrantFiled: April 5, 1990Date of Patent: January 14, 1992Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Noriaki Nagano, Masato Satoh, Masauki Komiya, Toshio Okazaki, Tetsuya Maeda, Tadao Shibanuma
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Patent number: 5075298Abstract: A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms and cycloalkyl of 3 to 6 carbon atoms, all optionally substituted with at least one member of the group consisting of optionally esterified or salified carboxy, alkoxy carbonyl, carbamoyl, dimethylcarbamoyl, amino, alkylamino, dialkylamino, halogen, alkoxy and alkylthio of 1 to 4 carbon atoms, aryl, heterocyclic aryl, arylthio and heterocyclic arylthio optionally substituted by alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of ##STR2## and A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4 and an organic amine or A is selected from the group consisting of the residue of an easily cleavable ester group or --COOA is --COO-- and the wavy line indicates --CH.sub.2 --R.sub.Type: GrantFiled: October 31, 1988Date of Patent: December 24, 1991Assignee: Roussel UclafInventors: Jozsef Aszodi, Alain Bonnet, Jean-Francois Chantot
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Patent number: 5075299Abstract: Novel cephalosporin compounds represented by formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group which may optionally have a substituent; each of R.sup.2 and R.sup.3 independently represents a hydrogen atom or hydroxy group; and A represents a hydrogen atom or a residue of nucleophilic compound, and pharmacologically acceptable salts or esters thereof exhibit a potent antibacterial activity against gram positive and gram negative bacteria.Type: GrantFiled: August 7, 1989Date of Patent: December 24, 1991Assignee: Meiji Seika Kaisha, Ltd.Inventors: Kenji Sakagami, Katsuyoshi Iwamatsu, Kunio Atsumi, Seiji Shibahara
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Patent number: 5073550Abstract: Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di-(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.Type: GrantFiled: August 28, 1990Date of Patent: December 17, 1991Assignee: Hoffmann-La Roche Inc.Inventor: Erwin Gotschi
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Patent number: 5073551Abstract: Cephalosporin compounds represented by the general formula ##STR1## in which R.sup.1 is a hydrogen atom or a protective group for the amino group,R.sup.2 is a hydrogen atom or a protective group for the hydroxyl group,R.sup.3 is a hydrogen atom, a salt-forming cation or a protective group for the carboxyl group, andR.sup.4 is a hydrogen atom, a halogen atom or a lower alkyl group,and their pharmacologically acceptable salts, process for their production and use of the same compounds as medicaments, particularly as antibiotic agents.Type: GrantFiled: March 24, 1989Date of Patent: December 17, 1991Assignee: Sagami Chemical Research CenterInventors: Takeo Kobori, Daiei Tunemoto
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Patent number: 5064824Abstract: Cephalosporin antibiotics having a 3-position substituent of the formula: ##STR1## are described; wherein R.sup.1 is hydrogen or certain substituted alkyl groups, Z is CH or N, R.sup.2 and R.sup.3 are hydroxy or in vivo hydrolysable esters thereof, (R.sup.12).sub.n represents various optional substituents and X=Y is an olefin, oxime, azo or related group. Processes for their preparation and use are described.Type: GrantFiled: May 5, 1989Date of Patent: November 12, 1991Assignee: Imperial Chemical Industries PLCInventors: David G. Acton, David H. Davies, Jeffrey P. Poyser
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Patent number: 5061794Abstract: A compound having the formula: ##STR1## wherein R is a straight chain or branched chain lower alkyl, cyclic lower alkyl, lower alkenyl (except for 1-carboxy-1-vinyl), lower alkynyl, aralkyl, phenyl or 2-pyrrolidon-3-yl group which may be substituted, and Q is ##STR2## (wherein R.sup.1 is a hydrogen atom or an acetyl group, R.sup.2 is a hydrogen atom, a carboxyl group or a carboxymethyl group, Y is a sulfur atom or an oxygen atom, Z is a sulfur atom, an oxygen atom or an imino group which may be substituted by a lower alkyl group); or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: July 10, 1989Date of Patent: October 29, 1991Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Koji Yamada, Fumio Nakano, Norikazu Otake, Akira Asai, Satoru Kuroyanagi, Yoshiharu Tanaka, Moriaki Ishikawa, Ryosuke Ushijima, Ryuji Mitomo
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Patent number: 5057511Abstract: Cephalosporin compounds having a 3-position substituent of the formula (I) are described:--CH.sub.2 --S--Q--(y).sub.n --Pwherein Q is a 5- or 6-membered heterocyclic ring, P is a benzene ring substituted by groups R.sup.1 and R.sup.2 which are ortho with respect to one another, wherein R.sup.1 is hydroxy or an in vivo hydrolysable ester thereof and R.sup.2 is hydroxy, an in vivo hydrolysable ester thereof, carboxy, sulpho, hydroxymethyl, methanesulphonamido or ureido; or P is a group of the formula (II) or (III): ##STR1## wherein M is oxygen or a group NR.sup.3 wherein R.sup.3 is hydrogen or C.sub.1-4 alkyl; said ring P being further optionally substituted; and --(Y).sub.n -- is a bond or various linking groups or --(Y)--.sub.n may be such so that rings Q and P are fused.The use of such compounds as antibacterial agents is described as are processes for their preparation and intermediates therefor.Type: GrantFiled: December 15, 1987Date of Patent: October 15, 1991Assignee: ICI PharmaInventors: Frederic H. Jung, Annie Olivier
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Patent number: 5055572Abstract: Acyl derivatives of the formula ##STR1## in which R is an acyl group, excluding those acyl groups of the formula ##STR2## in which A is a group of the formulae --NHCO--, --NHCONHCO--, --NHCOCH.dbd.CH--, ##STR3## wherein R.sup.6 is hydrogen or lower alkyl; R.sup.1 and R.sup.2 are hydrogen or a protecting group, X is hydrogen, halogen, lower alkoxy, nitro or --OR.sup.2, n is 1 or 2, R.sup.4 and R.sup.5 are hydrogen or together represent an additional bond and Z is a direct bond or carbonyl (where R.sup.4 and R.sup.5 both represent hydrogen) or a group of the formula --O--B-- (where R.sup.4 and R.sup.5 together represent an additional bond) in which B is a straight-chain, branched or cyclic lower alkylene;and wherein R.sup.3 is a substituted bicyclic group of the formulae ##STR4## wherein R.sup.7 and R.sup.Type: GrantFiled: April 8, 1988Date of Patent: October 8, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Andre Furlenmeier, Erwin Gotschi, Paul Hebeisen, Werner Hofheinz, Helmut Link
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Patent number: 5055462Abstract: Cephalosporin antibiotics having a 3-position substituent of the formula:--CH.sub.2 NR.sup.1 --Y--A--Z--Qare described, wherein R.sup.1 is hydrogen or certain optionally substituted alkyl groups; Y is --CO-- or --SO.sub.2 --; A is optionally substituted phenylene or heterocyclylene; Z is a linking group and Q is a catechol or related ring system. Processes for their preparation and use are described.Type: GrantFiled: May 10, 1989Date of Patent: October 8, 1991Assignees: Imperial Chemical Industries plc, ICI PharmaInventors: Gareth M. Davies, Colin J. Strawson, Jean J. Lohmann
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Patent number: 5036064Abstract: Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.Type: GrantFiled: August 9, 1988Date of Patent: July 30, 1991Assignee: Hoffmann-La Roche Inc.Inventor: Erwin Gotschi
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Patent number: 5028601Abstract: Cephalosporin compounds of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and are a hydrogen atom or a lower alkyl group of 1-5 carbon atoms and A is a hydrogen atom or a nucleophilic compound residue or pharmacologically acceptable salts thereof have excellent antibacterial activity against Gram positive and Gram negative microorganisms.Type: GrantFiled: April 21, 1988Date of Patent: July 2, 1991Assignees: Meiji Saika Kaisha, Ltd., Zaidanhojin Biseibutsu Kagaku KenkyukaiInventors: Shinichi Kondo, Takashi Tsuruoka, Katsuyoshi Iwamatsu, Kiyoaki Katano, Satoru Nakabayashi, Hiroko Ogino, Takashi Yoshida, Masaji Sezaki
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Patent number: 5026695Abstract: A compound of the formula ##STR1## in which R.sup.1 is a group of the formula: ##STR2## wherein R.sup.4 is lower alkyl and R.sup.5 is amino or a protected amino group, R.sup.2 lower alkoxymethyl, lower alkylthiomethyl or lower alkenylthiomethyl, R.sup.3 is carboxy or a protected carboxy group, and A is lower alkylene which may have a substituent selected from the groups consisting of amino, a protected amino group, hydroxy, oxo and a group of the formula:.dbd.N.about.OR.sup.6, wherein R.sup.6 is hydrogen, lower alkenyl, lower alkynyl, lower alkyl, or lower alkyl substituted by one or more substituent(s) selected from carboxy, a protected carboxy group, amino, a protected amino group and a heterocyclic group, and a pharmaceutically acceptable salt thereof, its preparation and its utility as an antimicrobial agent.Type: GrantFiled: January 5, 1990Date of Patent: June 25, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Takashi Masugi, Hideaki Yamanaka, Kohji Kawabata
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Patent number: 5017569Abstract: Cephalosporin compounds having a 3-position substituent of the formula (I) are described:--CH.sub.2 --Y--Q (I)wherein Y is a linking group --NR.sup.4 CO--Y'--, --NR.sup.4 SO.sub.2 --Y'--, --OCO--Y;-- or --SCO--Y'-- wherein R.sup.4 is hydrogen, various optionally substituted alkyl groups or alkenyl and Y' is a bond or various optionally substituted alkylene or alkenylene groups; and Q is a benzene ring (optionally fused to a further benzene ring so forming a naphthyl group or optionally fused to a 5 or 6 membered heterocyclic aromatic group containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur), said benzene ring (or in the case of naphthyl either benzene ring) being substituted by groups R.sup.1 and R.sup.2 which are ortho with respect to one another, wherein R.sup.1 is hydroxy or an in vivo hydrolyzable ester thereof and R.sup.Type: GrantFiled: November 6, 1987Date of Patent: May 21, 1991Assignee: ICI PharmaInventors: Alain M. Bertrandie, Thomas G. C. Bird, Frederic H. Jung, Jean-Jacques M. Lohmann
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Patent number: 5001121Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: June 20, 1989Date of Patent: March 19, 1991Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 4988687Abstract: A compound having the formula: ##STR1## wherein R is a vinyl, phenyl or aralkyl group which may be substituted; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: September 1, 1989Date of Patent: January 29, 1991Assignee: Banyu Pharmaceutical Company, Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima
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Patent number: 4987129Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: --A--OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is --A--OR.sub.4, and R.sub.Type: GrantFiled: July 21, 1988Date of Patent: January 22, 1991Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4978752Abstract: Crystals of 7.beta.-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3- (1-imidazo[1,2-b]pyridazinium)methyl-3-cephem-4-carboxylate hydrochloride or a solvate thereof, which are stable and improved in solubility in water, are useable for an excellent antibacterial agent.Type: GrantFiled: November 22, 1988Date of Patent: December 18, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Yoshiharu Maeda, Yukio Mizuno, Akira Nakatani, Mitsuhisa Yamano
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Patent number: 4971963Abstract: An antibacterial agent is provided which is a cephem compound of the formula: ##STR1## wherein R.sup.1 is an acyl group; R.sup.2 is a carboxy group which may be esterified; R.sup.3 is a hydrogen atom, a lower alkyl group or cyano group; R.sup.4 is a hydrogen atom or a lower alkyl group, or R.sup.4 together with R.sup.3 is a methylene chain having 2 or 3 carbon atoms; R.sup.5 is a hydrogen atom or a lower alkyl group; A is an optionally substituted bivalent aromatic heterocyclic group which is bonded to a ring-constituting carbon atom with the adjacent sulfur atom; Y is a binding arm, sulfur or oxygen atom, --NH--, --CONH-- or --NHCO--; Z is a binding bond or --NH--; m is an integer of 0 to 4 and n is an integer of 0 to 6, or a pharmacologically acceptable salt thereof.Type: GrantFiled: March 15, 1989Date of Patent: November 20, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michiyuki Sendai, Shoji Kishimoto
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Patent number: 4971962Abstract: The present invention relates to novel cephalosporin compounds having high antimicrobial activity, which are shown by the formula(I), and to a process for preparing them ##STR1## wherein R.sup.1 is a hydrogen atom or an amino protecting group;R.sup.2 is acetoxy; andR.sup.3 is a hydrogen atom or a carboxyl protecting group (wherein when R.sup.2 contains quaternary ammonium, r.sup.2 and R.sup.3 may form a zwitter ion).The present invention also relates to the non-toxic and pharmaceutically acceptable salts of the cephalosporin compounds of the formula (I). Also described are compositions containing the antibiotics according to the present invention.Type: GrantFiled: May 11, 1989Date of Patent: November 20, 1990Assignee: Lucky, Ltd.Inventors: Hun S. Oh, Yong Z. Kim, Jae H. Yeo, Jong C. Lim, Won S. Kim, Soon H. An, Chan S. Bang, Hyeon J. Yim
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Patent number: 4971961Abstract: This invention provides cephalosporin compounds represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 are same or different hydrogen atom or a lower alkyl group of 1 to 5 carbon atoms; R.sup.3 is a lower alkyl group which may optionally be substituted with a halogen atome (or atoms), an alkenyl group, or a cycloalkylmethyl group of 3 to 6 carbon atoms; and A is hydrogen atom or residue of a nucleophilic compound and pharmacologically acceptable salts thereof. These compounds have broad-spectrum antibacterial activity against Gram-positive and -negative bacteria including Pseudomonas aeruginosa, as well as against a great variety of .beta.-lactamase-producing strains.Type: GrantFiled: November 2, 1988Date of Patent: November 20, 1990Assignee: Meiji Seika Kaisha, Ltd.Inventors: Kaysuyoshi Iwamatsu, Kenji Sakagami, Kunio Atsumi, Takashi Yoshida, Seiji Shibahara, Takashi Tsuruoka, Shinichi Kondo
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Patent number: 4966900Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a lower alkyl group; M is a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; R' and R" are independently a hydrogen atom or a protective group; A is a mercapto group substituted by a substituted or unsubstituted polycyclic nitrogen-containing heterocyclic ring or a group represented by the following formula (a):--OOCNR.sub.3 R.sub.4 (a)where R.sub.3 and R.sub.4 are independently a hydrogen atom or a lower alkyl group, provided that R.sub.1 and R.sub.2 are both hydrogen atoms, both R.sub.3 and R.sub.4 being hydrogen atoms are excluded,or its pharmaceutically acceptable salt, and a method for preparing the same , medicinal composition for microbism therapy containing the same and intermediates for synthesis of the same.Type: GrantFiled: July 20, 1987Date of Patent: October 30, 1990Assignees: Sankei Pharmaceutical Company Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4963542Abstract: Disclosed 2-(syn)-hydroxyimino-acetamide derivatives of the formula: ##STR1## wherein Y is hydrogen, hydroxyl, an acyloxy, carbamoyloxy, a quaternary ammonium or a nitrogen-containing heterocyclic ring-substituted thio group; or pharmaceutically acceptable salts or esters thereof are useful as antibacterial agents. Also disclosed are processes for producing them.Type: GrantFiled: May 17, 1989Date of Patent: October 16, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuo Numata, Isao Minamida, Susumu Tsushima
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Patent number: 4954624Abstract: New process for the production of the pentahydrate of ceftazidime of formula ##STR1## characterized in that the ester group of the compound of formula ##STR2## or an acid addition salt thereof, is cleaved by the sole use of aqueous hydrochloric acid, and the resulting ceftazidime is either crystallized directly from the reaction mixture as the pentahydrate by adding a base, or first of all the dihydrochloride of the ceftazidime is isolated by adding acetone and/or ethanol or another anti-solvent which is miscible with water, and this is converted into the pentahydrate by known methods.Type: GrantFiled: June 29, 1989Date of Patent: September 4, 1990Assignee: Sandoz Ltd.Inventor: Bernhard C. Prager
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Patent number: RE33948Abstract: Antibacterially active and animal growth-promoting novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents the radical ##STR2## Y representing N or CR.sup.9, or Y--R.sup.7 representing ##STR3## Z representing O, S, or NR.sup.10, and R.sup.2 represents hydrogen or a protective group.Type: GrantFiled: August 29, 1989Date of Patent: June 2, 1992Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger