7-position Substituent Contains Hetero Ring Patents (Class 514/206)
  • Patent number: 5728691
    Abstract: Derivatives of 7-aminoceph-3-em-4-carboxylic acid with 6-fluoroquinolone derivatives in which the cephem and 6-fluoroquinolone moieties are bound to each other through a carboxamido bond as well as the pharmaceutical compositions containing them are described. These compounds possess antibacterial, growth promoting and probiotic activity.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: March 17, 1998
    Assignees: Laboratorios Aranda S.A. De C.V., Judith Marcia Arrieta Munguia
    Inventor: Miguel Angel Corpi Constantino
  • Patent number: 5721229
    Abstract: A dry solid mixture of a hydroxypolycarboxylic acid and a cephalosporin where the hydroxypolycarboxylic acid of the formula ##STR1## where x and y are 0 or 1 and z is 0 to 3, in the weight ration of hydroxypolycarboxylic acid to cephalosporin of at least 1.8. The invention comprises a solution made from the dry solid mixture and a process of treating animals with cephalosporin by including the solution in the water fed to the animals so that the animals can ingest the cephalosporin. A particularly preferred mixture is one of citric acid and cephalexin.
    Type: Grant
    Filed: December 26, 1995
    Date of Patent: February 24, 1998
    Assignee: Veterinary Pharmacy Corporation
    Inventors: Michael A. Strobel, Pat Soderlund
  • Patent number: 5712266
    Abstract: A syn isomer in (R) or (S) form or a mixture thereof of a compound of the formula ##STR1## syn isomer, in the (R) or (S) form or in the form of an (R,S) mixture, in the form of an internal salt or their salts with organic or mineral acids wherein the substituents are defined as in the application having anti-bacterial properties.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: January 27, 1998
    Assignee: Roussel Uclaf
    Inventors: Jozsef Aszodi, Jean-Francois Chantot, Patrick Fauveau, Solange Gouin D'Ambrieres, Daniel Humbert, Christophe Dini
  • Patent number: 5712268
    Abstract: There are described pharmaceutical compositions comprising(a) compounds of the formula ##STR1## in which R signifies lower alkoxycarbonyl, lower alkoxy-carbonylamino, the acyl residue of an .alpha.- or .beta.-amino acid or a residue of the general formulaQ--X--Y-- (a)wherein Q signifies a 3- to 6-membered ring which optionally contains nitrogen, sulphur and/or oxygen and which is optionally bonded with a fused ring, X signifies a direct bond or a linear "spacer" with up to 6 atoms consisting of carbon, nitrogen, oxygen and/or sulphur, of which up to 2 atoms can be nitrogen atoms and 1 atom can be oxygen or sulphur, and Y represents one of the groups --CO--, --CS--, --CONH-- and (where X contains neither sulphur nor carbonyl as a terminal component) --SO.sub.2 --; and in which R.sup.1 and R.sup.2 together signify a group of the formula ##STR2## wherein A represents hydrogen or a residue which is usable in the 3-position of cephalosporin antibiotics, and in which R.sub.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: January 27, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Christian Hubschwerlen, Robert Charnas, Ingrid Heinze, Klaus Gubernator
  • Patent number: 5698547
    Abstract: The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: December 16, 1997
    Assignee: Microcide Pharmaceuticals, Inc.
    Inventors: Burton Christensen, In-Seop Cho, Tomasz Glinka, Scott Hecker, Ving J. Lee, Zhijia J. Zhang
  • Patent number: 5698577
    Abstract: There are described pharmaceutical compositions comprising(a) compounds of the formula ##STR1## in which R signifies lower alkoxycarbonyl, lower alkoxy-carbonylamino, the acyl residue of an .alpha.- or .beta.-amino acid or a residue of the general formulaQ--X--Y-- (a)wherein Q signifies a 3- to 6-membered ring which optionally contains nitrogen, sulphur and/or oxygen and which is optionally bonded with a fused ring, X signifies a direct bond or a linear "spacer" with up to 6 atoms consisting of carbon, nitrogen, oxygen and/or sulphur, of which up to 2 atoms can be nitrogen atoms and 1 atom can be oxygen or sulphur, and Y represents one of the groups --CO--, --CS--, --CONH-- and (where X contains neither sulphur nor carbonyl as a terminal component) --SO.sub.2 --; and in which R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/or oxygen, and R.sup.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: December 16, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Christian Hubschwerlen, Robert Charnas, Ingrid Heinze, Klaus Gubernator
  • Patent number: 5656623
    Abstract: Antimicrobial lactam-quinolone compounds comprising a lactam-containing moiety linked to a quinolone moiety, of the formula: ##STR1## wherein (1) A.sup.1, A.sup.2, A.sup.3, R.sup.1, R.sup.4 and R.sup.6 generally form any of a variety of quinolone, naphthyridine or related cyclic moieties known in the art to have antimicrobial activity; and(2) R.sup.1 or R.sup.3 contain a linking moiety, linking the quinolone moiety to a lactam-containing moiety having the formula: ##STR2## wherein (3) R.sup.10, R.sup.11, R.sup.12, R.sup.13, and R.sup.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: August 12, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Ronald Eugene White, Thomas Prosser Demuth, Jr.
  • Patent number: 5635501
    Abstract: Compound of formula (I) or salts thereof wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents; X is S, SO, SO.sub.2 or CH.sub.2 ; Y is O, S, SO or SO.sub.2 ; n is 0 or 1; m is 1 or 2; and wherein in the (a) ring system the dotted line indicates that one pair of adjacent ring carbon atoms is joined by a C.dbd.C double bond. These compounds have antibacterial activity.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: June 3, 1997
    Assignee: Pfizer Inc.
    Inventors: George Burton, John H. Bateson, Richard L. Elliott, Stephen C. M. Fell
  • Patent number: 5629306
    Abstract: Derivatives of 7-alkylidene cephalosporanic acid sulfone and the pharmaceutically active salts thereof are found to be potent inhibitors of .beta.-lactamase enzymes.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: May 13, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, Brian Bachmann
  • Patent number: 5620968
    Abstract: The invention provides compounds of the formula: ##STR1## wherein the variables are hereinbelow described; and salts thereof. Also, pharmaceutical formulations and methods for treating bacterial infections in man or other animals using the above compounds are disclosed.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: April 15, 1997
    Assignee: Eli Lilly and Company
    Inventor: Ho-Shen Lin
  • Patent number: 5607927
    Abstract: An aminothiazolyl- or aminothiadiazolyl-cephalosporin derivative represented by the following general formula (I) which has a condensed-ring thio group as a 3-positioned substituent group that contains a thiazolylthio group, an oxazolylthio group or a heterocyclic ring thereof as one of the ring components. The compound according to the present invention has excellent activities to inhibit growth of various bacteria, especially Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), and therefore, the antibacterial agent comprising, as an active ingredient, the inventive compound can be used as a therapeutic drug for the treatment of various bacterial infections.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: March 4, 1997
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Masaki Tsushima, Katsuyoshi Iwamatsu, Atsushi Tamura, Seiji Shibahara
  • Patent number: 5605895
    Abstract: The present invention relates to a cephalosporin compound represented by the following general formula (I), its pharmaceutically acceptable non-toxic salt, physiologically hydrolyzable ester, hydrate or solvate, or isomers thereof, which is useful as an antibiotic agent: ##STR1## in which R.sup.1 represents hydrogen or an amino-protecting group,R.sup.2 and R.sup.3 can be identical or different and each represent hydrogen or a hydroxy-protecting group, orR.sup.2 and R.sup.3 together can form a diol-protecting cyclic group,R.sup.4 represents hydrogen or a carboxyl-protecting group,R.sup.5 represents hydrogen, C.sub.1-4 alkyl, alkoxycarbonyl, carboxyl or sulfomethyl,R.sup.6 represents hydrogen, amino or substituted amino, andR.sup.7 represents C.sub.1-4 alkyl, amino or substituted amino, orR.sup.5 and R.sup.6 together with the carbon atoms to which they are attached can form a 3 to 7-membered cyclic group, orR.sup.6 and R.sup.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: February 25, 1997
    Assignee: Lucky, Ltd.
    Inventors: Chan S. Bang, Yong Z. Kim, Jae H. Yeo, Jong C. Lim, Young M. Woo, Hun S. Oh, Duk H. Yang, Sam S. Kim, Se H. Kim, Jae H. Jeon, Tae H. Lee, Sung I. Kim, Mi K. Seo, Jae W. Lee
  • Patent number: 5595986
    Abstract: A stably storable and readily water soluble composition for use in preparing injections and containing Cefditoren, namely a cephalosporin of the formula ##STR1## is now provided, which composition comprises a physical mixture of Cefditoren or a non-toxic salt thereof with a proportion of arginine and/or lysine and/or a non-toxic salt thereof. This new composition of Cefditoren can be stored for long periods of time without discoloration and without undesirable reduction in the antibacterial activity, and the composition can be dissolved completely and quickly in water.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: January 21, 1997
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Makoto Okada, Masaki Takahashi, Kaoru Hosoi, Shokichi Nakajima
  • Patent number: 5593986
    Abstract: The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: January 14, 1997
    Assignee: Microcide Pharmaceuticals, Inc.
    Inventors: Burton G. Christensen, In-Seop Cho, Tomasz W. Glinka, Scott J. Hecker
  • Patent number: 5571804
    Abstract: Cephalosporin compounds of formula (I): ##STR1## wherein: R.sup.1 is a hydrogen or an amino protecting group;R.sup.2 and R.sup.3 are, independently, a hydrogen or a hydroxy protecting group, or form together a cyclic diol protecting group;R.sup.4 and R.sup.5 are, independently, a hydrogen or a carboxyl protecting group;X and Y are a nitrogen and a carbon atom, respectively, or a carbon and a nitrogen atom, respectively;R.sup.6 and R.sup.7 are, independently, a hydrogen or an amino, substituted amino, hydroxy, alkoxy, C.sub.1-4 alkyl, carboxyl or alkoxy carbonyl group, or jointly form a C.sub.3-7 cycloalkyl group together with the carbon to which they are attached, when X and Y are a nitrogen and a carbon, respectively, or R.sup.7 is a hydrogen or an amino group when X and Y are a carbon and a nitrogen, respectively; andQ is .dbd.CH-- or .dbd.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: November 5, 1996
    Assignee: Lucky Limited
    Inventors: Chan S. Bang, Jae H. Yeo, Young M. Woo, Jong C. Lim, Deog H. Yang, Se H. Kim, Jae H. Jeon, Mi K. Seo, Sam S. Kim, Tae H. Lee, Yong Z. Kim, Hun S. Oh
  • Patent number: 5541177
    Abstract: A compound of the formula I is disclosed. ##STR1## R.sup.13 represents hydrogen, NH.sub.2, C1-4 alkyl, C1-4 alkylamino or di(C1-4)alkylamino-;Y represents CH or N;Y" represents (a) CR.sup.y' R.sup.z' with R.sup.y' and R.sup.z' hydrogen, C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl or C.sub.1-6 alkyl substituted with C.sub.3-8 cycloalkyl, or (b) N substituted with OR.sup.14 with R.sup.14 representing H, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted with COOH.Ar represents: ##STR2## One of R.sup.1 and R.sup.2 independently represent H, W as defined below or one of the groups (a) through (d) below, and the other represents H or W. Pharmaceutical compositions and methods of use are also included.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 30, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, James V. Heck
  • Patent number: 5534507
    Abstract: A compound of the formula I is disclosed. ##STR1## R.sup.13 represents hydrogen, NH.sub.2, C1-4 alkyl, C1-4 alkylamino or di(C1-4) alkylamino-;Y represents CH or N;Y" represents (a) CR.sup.y 'R.sup.z ' with R.sup.y ' and R.sup.z ' hydrogen, C1-6 alkyl, C.sub.3-8 cycloalkyl or C.sub.1-6 alkyl substituted with C.sub.3-8 cycloalkyl, or (b) N substituted with OR.sup.14 with R.sup.14 representing H, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted with COOH.Ar represents: ##STR2## One of R.sup.1 and R.sup.2 independently represent H, W as defined below or one of the groups (a) through (d) below, and the other represents H or W. Pharmaceutical editions and methods of use are also included.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 9, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, James V. Heck
  • Patent number: 5534508
    Abstract: Herein disclosed are novel cephem compounds represented by the following general formula (I), and novel antimicrobial, and especially anti-MRSA, agents which contain as an active ingredient at least one of the novel cephem compounds and the physiologically acceptable salts thereof.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: July 9, 1996
    Assignees: Katayama Seiyakusyo Co., Ltd., Ajinomoto Co., Inc.
    Inventors: Sadao Hayashi, Eiji Nakanishi, Yasuyuki Kurita, Masahiko Okunishi
  • Patent number: 5523400
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sup.1 is an acyl group derived from a carboxylic acid, hydrogen, or an amino protecting group;R.sup.2 is hydrogen, hydroxy, lower alkyl-Q.sub.p -, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aralkyl-Q.sub.p -, aryl-Q.sub.p -, aryloxy, aralkoxy or a heterocyclic ring, the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aralkyl, aryl, aryloxy, aralkoxy and the heterocyclic ring being unsubstituted or substituted with at least one group selected from carboxy, amino, nitro, oxo, cycloalkyl, cyano, lower alkyl, lower alkoxy, hydroxy, halogen, --CONR.sup.4 R.sup.5, --N(R.sup.5)COOR.sup.9, R.sup.5 CO--, R.sup.5 OCO-- or R.sup.5 COO-- where R.sup.4 is hydrogen, lower alkyl, or cycloalkyl; R.sup.5 is hydrogen or lower alkyl; R.sup.9 is lower alkyl, lower alkenyl or a carboxylic acid protecting group;Q is --CO-- or --SO.sub.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: June 4, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Chung-Chen Wei, Peter Angehrn
  • Patent number: 5504076
    Abstract: 7.beta.- 2-(aminothiazolyl and thiadiazolyl)-2-oxyiminoacetamido!cephalosporin derivatives having a 3- N-(optionally substituted) aminopyridiniumthiomethyl! substituent have antibacterial activity and are of use in antibacterial therapy. Processes for the preparation of such cephalosporins plus intermediates for use in the preparation thereof, including N-(optionally substituted)amino-thiopyridones, are also described.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: April 2, 1996
    Assignee: Pfizer Inc.
    Inventors: Clive L. Branch, Angela W. Guest, Richard G. Adams
  • Patent number: 5498777
    Abstract: Cephalosporin compounds of the formula I ##STR1## are disclosed. The compounds are useful against MRSA/MRCNS. Compositions and methods of use are also included.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: March 12, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, Mary F. Sasor, Milton L. Hammond
  • Patent number: 5480879
    Abstract: The invention relates to novel derivatives of quinolonecarboxylic acid and naphthyridonecarboxylic acid which are linked to a .beta.-lactam antibiotic, to their salts, to processes for their preparation and to antibacterial agents containing these derivatives.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: January 2, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Wilfried Schrock, Dieter Habich, Andreas Krebs, Thomas Schenke, Thomas Philipps, Klaus Grohe, Rainer Endermann, Klaus-Dieter Bremm, Karl-Georg Metzger
  • Patent number: 5464829
    Abstract: A cephalosporin derivative having a quaternary salt type substituent group at the 3-position, represented by formula (I): ##STR1## wherein X is a carbon atom or a nitrogen atom; Y is a sulfur atom, an oxygen atom or a nitrogen atom substituted with a substituted or unsubstituted lower alkyl group; R.sup.1 is a hydrogen atom, a lower alkyl group or a substituted lower alkyl group; R.sup.2 is a lower alkyl group, a substituted lower alkyl group, a lower alkylene group or a substituted lower alkylene group; and A is an unsaturated six-membered heterocyclic ring containing at least one nitrogen atom, or a pharmaceutically acceptable salt thereof is disclosed. The derivatives have excellent antibacterial activities and can be used as a drug for the treatment of various bacterial infections.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: November 7, 1995
    Assignee: Meiji Seika Kaisha Ltd.
    Inventors: Masaki Tsushima, Yuko Kano, Katsuyoshi Iwamatsu, Atsushi Tamura, Seiji Shibahara
  • Patent number: 5462935
    Abstract: The present invention provides a cephalosporin compound represented by formulas (I-S) and (I-R) ##STR1## wherein: R.sup.1 is a C.sub.1-4 alkyl, C.sub.3-4 alkenyl, C.sub.3-4 cycloalkyl, amino optionally substituted with a C.sub.1-4 alkyl radical, phenyl, or 2-,4- or 6- substituted phenyl group with two or fewer substitutents chosen from C.sub.1-4 alkyl, C.sub.1-3 alkoxy, halogen and hydroxy radicals;R.sup.2 is hydrogen or a C.sub.1-4 alkyl group;R.sup.a and R.sup.b, which should be different from each other, are hydrogen or a C.sub.1-4 alkyl group; andQ is N or CH,and the pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates thereof, which possess potent and broad antibacterial activities. The invention also provides processes for preparing these compounds and to pharmaceutical compositions containing them as active ingredients.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: October 31, 1995
    Assignee: Lucky Limited
    Inventors: Yong Z. Kim, Hun S. Oh, Jae H. Yeo, Jong C. Lim, Chan S. Bang, Won S. Kim, Hyeon J. Yim
  • Patent number: 5461044
    Abstract: As new antibacterial agent are provided cephalosporin derivatives having a general formula (I): ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group or a substituted lower alkyl group, R.sup.2 is a hydrogen atom or an ester-forming group easily cleavable by an esterase present in the digestive tracts, R.sup.3 and R.sup.4 may be the same and each is independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, hydroxyl group, amino group or a lower alkoxy group, and a pharmaceutically acceptable salt thereof.The cephalosporin derivative of formula (I) is useful as an orally or injectably administrable cephalosporin derivative which exhibits in combination a high antibacterial activity and a favorable characteristic capable of giving a high concentration of this compound in blood when administered.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: October 24, 1995
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Masaki Tsushima, Katsuyoshi Iwamatsu, Atsushi Tamura, Seiji Shibahara
  • Patent number: 5455238
    Abstract: A syn isomer in (R) or (S) form or a mixture thereof of a compound of the formula ##STR1## in the form of an internal salt or a non-toxic, pharmaceutically acceptable acid addition salt wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are individually defined in the specification, R.sub.4 is --OH or alkoxy of 1 to 8 carbon atoms, A and A' are individually selected from the group consisting of hydrogen, an equivalent of an alkali metal or alkaline earth metal, magnesium, ammonium and an organic amine, or one or two of --COOA or --COOA' ARE --CO.sub.2 --, the wavy line means --CH.sub.2 R.sub.6 can be in the E or Z position, R.sub.6 in the quaternary ammonium form is selected from the group consisting of ##STR2## X is defined as in the specification with the proviso that when R.sub.3 is --OH or alkoxy of 1 to 8 carbon atoms, at least one R.sub.1, R.sub.2 and R.sub.5 is other than hydrogen having antibacterial properties.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: October 3, 1995
    Assignee: Roussel Uclaf
    Inventors: Jozsef Aszodi, Jean-Francois Chantot, Patrick Fauveau, Solange Gouin D'Ambrieres, Daniel Humbert
  • Patent number: 5455239
    Abstract: A compound of the formula I is disclosed. ##STR1## R.sup.13 represents hydrogen, NH.sub.2, C1-4 alkyl, C1-4 alkylamino or di(C1-4) alkylamino-;Y represents CH or N;Y" represents (a) CR.sup.y' R.sup.z' with R.sup.y' and R.sup.z' hydrogen, C1-6 alkyl, C.sub.3-8 cycloalkyl or C.sub.1-6 alkyl substituted with C.sub.3-8 cycloalkyl, or (b) N substituted with OR.sup.14 with R.sup.14 representing H, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted with COOH.Ar represents: ##STR2## One of R.sup.1 and R.sup.2 independently represent H, W as defined below or one of the groups (a) through (d) below, and the other represents H or W. Pharmaceutical compositions and methods of use are also included.
    Type: Grant
    Filed: August 5, 1993
    Date of Patent: October 3, 1995
    Assignee: Merck & Co. Inc.
    Inventors: Lovji D. Cama, James V. Heck
  • Patent number: 5438053
    Abstract: Novel cephem compounds having, at the 3-position of the cephem nucleus, a group of the formula:--CH.sub.2 --S--A--Y--Bwherein A stands for a further optionally substituted divalent nonionic aromatic heterocyclic group bounded to the adjacent sulfur atom via carbon atom, Y stands for a bond, a sulfur atom, an oxygen atom, NH, CONH, SO.sub.2 NH or a divalent C.sub.1 -C.sub.6 hydrocarbon chain optionally including one or two selected from the group consisting of sulfur atom, oxygen atom, NH group, CONH group and SO.sub.2 NH group in the chain, and B stands for a group of the formula: ##STR1## wherein R.sup.3 stands for H or an optionally substituted lower alkyl, R.sup.4 and R.sup.4 ' each stand for H, OH, an optionally substituted lower alkyl, COOH or CONH, or salts thereof, having excellent antibacterial activities especially against Pseudomonas aeruginosa and keeping effective serum levels over a long period.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: August 1, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Michiyuki Sendai, Kenji Okonogi
  • Patent number: 5438052
    Abstract: Cephalosporin derivatives have the formula ##STR1## wherein Z.sup.1, Z.sup.2, X, Y, P, Q, m, n and p are as defined in the following text. Also described are the readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, and hydrates of compounds of formula I, their esters and salts. Processes are provided for manufacture and pharmaceutical preparations which contain these compounds. Intermediates from the manufacture of these compounds are described, as is the use of the compounds in the control of illnesses and for the manufacture of the aforementioned preparations.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: August 1, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter Angehrn, Andre Furlenmeier, Paul Hebeisen, Werner Hofheinz, Helmut Link
  • Patent number: 5432182
    Abstract: Substituted 4-aminoquinazoline derivatives which are inhibitors of gastric acid secretion. A compound of the invention are the salts of strong acids of 3-butyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: July 11, 1995
    Assignee: SmithKline Beecham Intercredit B.V.
    Inventors: Robert J. Ife, Colin A. Leach
  • Patent number: 5416081
    Abstract: The present invention relates to novel cephalosporin compounds, pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates and isomers thereof which possess potent and broad antibacterial activities. The compounds of the present invention have a (4-amino-1-substituted-alkapyrimidinium-4-yl)thiomethyl group in 3-position of the cephem nucleus and is specifically represented by the following formula(I): ##STR1## wherein: R.sup.1 is a hydrogen atom or a C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl or --C(R.sup.A)(R.sup.B)COOH group wherein R.sup.A and R.sup.B are independently a hydrogen atom or a C.sub.1-4 alkyl group, or form a C.sub.3-7 cycloalkyl group together with the carbon atom to which they are attached;R.sup.2 is an unsubstituted or substituted amino, C.sub.1-4 alkyl or C.sub.3-7 cycloalkyl group; andn is an integer ranging from 2 to 7.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: May 16, 1995
    Assignee: Lucky Limited
    Inventors: Chan S. Bang, Yong Z. Kim, Jae H. Yeo, Jong C. Lim, Hun S. Oh, Young M. Woo, Duk H. Yang, Sam S. Kim, Hyeon J. Yim
  • Patent number: 5416080
    Abstract: A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## in the R or S form or in the form of an R, S mixture wherein the substituents are defined as in the specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-bacterial activity.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: May 16, 1995
    Assignee: Roussel-UCLAF
    Inventors: Jozsef Aszodi, Jean-Francois Chantot, Solange Gouin D'Ambrieres
  • Patent number: 5409917
    Abstract: A method and composition for topically treating acne and acneiform dermal disorders includes applying an amount of a cephalosporin antibiotic effective to treat the acne and acneiform dermal disorders. The antibiotic is blended with a carrier suitable for topical application to dermal tissues. The carrier is selected from the group consisting of an aqueous liquid, an alcohol base, a water soluble gel, a lotion, an ointment, a nonaqueous liquid base, a mineral oil base, a blend of mineral oil and petrolatum, liposomes, a time-release patch, and a liquid-absorbed wipe. The cephalosporin can also be combined with benzoyl peroxide in a gel carrier.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 25, 1995
    Assignees: Marvin S. Towsend, Leonard Bloom
    Inventors: Howard N. Robinson, Neil F. Martin
  • Patent number: 5407930
    Abstract: The present invention relates to a compound represented by the structural formula I: ##STR1## its pharmaceutically acceptable salt or ester, or its crystalline, which is a novel optically active compound useful as a curing agent for bacterial infections, a process for production thereof and a use thereof.
    Type: Grant
    Filed: March 24, 1994
    Date of Patent: April 18, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima, Akira Asai, Satoru Kuroyanagi
  • Patent number: 5407929
    Abstract: 7.beta.-[(Z)-2-(2-Amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-(1,2,3-tria zol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid hydrochloride and its crystalline hydrate, have a potent antibiotic activity, low toxicity and are pharmaceutically stable. They are useful as an active ingredient for clinically useful antibiotic formulations. Methods are disclosed for their production.
    Type: Grant
    Filed: July 27, 1993
    Date of Patent: April 18, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hisanori Takahashi, Yutaka Ide
  • Patent number: 5403835
    Abstract: The present invention relates to a compound represented by the structural formula: ##STR1## or its pharmaceutically acceptable salt or ester, which is a novel optically active compound useful as a curing agent for bacterial infections, a process for production thereof and a use thereof.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: April 4, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima, Akira Asai, Satoru Kuroyanagi
  • Patent number: 5401734
    Abstract: Cephem compounds of the formula: ##STR1## wherein R.sup.1 is amino or a protected amino group,Z is N or CH,R.sup.2 is lower alkyl, mono(or di or tri)halo(lower)alkyl, lower alkenyl, lower alkynyl, phenyl, naphthyl, phenyl(lower)alkyl, carboxy(lower)alkyl or protected carboxy(lower)alkyl, andR is a group of the formula: ##STR2## in which R.sup.3 and R.sup.4 are each lower alkyl,A is lower alkylene, andR.sup.5 is hydroxy or a protected hydroxy group; or pharmaceutically acceptable salts thereof show antimicrobial activities and are useful in the treatment of microbial infections.
    Type: Grant
    Filed: May 20, 1993
    Date of Patent: March 28, 1995
    Assignee: Fujisawa Phamaceutical Co., Ltd.
    Inventors: Hideaki Yamanaka, Yoshiki Yoshida, Jiro Goto, Takeshi Terasawa, Shinya Okuda, Kazuo Sakane
  • Patent number: 5397779
    Abstract: A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## in the R or S form or in the form of an R, S mixture wherein R.sub.1, Rc, Rb, A and A' are defined as in the following specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-bacterial activity.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: March 14, 1995
    Assignee: Roussel-Uclaf
    Inventors: Jozsef Aszodi, Jean-Francois Chantot, Solange G. D'Ambrieres
  • Patent number: 5389627
    Abstract: The present invention relates to novel cephem compounds having the formula: ##STR1## wherein, Q is a carbon or nitrogen atom; X is an oxygen atom, or a nitroalkyl or cyanoimine group, with the proviso that X cannot be an oxygen atom when Q is a carbon atom; R.sub.1 is a hydrogen atom, or a lower alkyl group, or a lower alkyl group which may be substituted by fluoro, or by a carboxylic group or an inorganic cation salt thereof; and R.sub.2 and R.sub.3 independently are a hydrogen atom or a lower alkyl group; or pharmaceutically acceptable salts thereof.The compounds of the present invention have potent antibacterial activities against gram-negative bacteria, especially Pseudomonas, and a longer half-life than conventional cephem compounds.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: February 14, 1995
    Assignee: Cheil Foods & Chemicals
    Inventors: Choong S. Kim, Yang S. Ahn, Kang Y. Jung, Nam H. Lee, Rok L. Yun, Seong Y. Park, Yeo H. Yoon, Keon H. Lee, Chun S. Lyu, Kwang H. Lee
  • Patent number: 5373001
    Abstract: A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## in the R or S form or in the form of a R, S mixture wherein the various substituents are defined as in the specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-bacterial activity.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: December 13, 1994
    Assignee: Roussel Uclaf
    Inventors: Jozsef Aszodi, Jean-Francois Chantot, Solange G. D'Ambrieres
  • Patent number: 5362722
    Abstract: 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 of treatment using the above compounds.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: November 8, 1994
    Assignee: Eli Lilly and Company
    Inventor: Robert J. Ternansky
  • Patent number: 5332731
    Abstract: A new class of cephalosporin derivatives is provided, which is useful as antibacterial agent to be particularly suitable for oral administrations in mammals including man, and which is represented by general formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group; R.sup.2 is a hydrogen atom or an ester-forming group capable of being cleaved easily with an esterase existing in the digestive tracts; n is an integer of zero or 1; Z is a saturated heterocyclic group containing one or two oxygen atoms as the hetero-atoms with or without one or more lower alkyl substituents, or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: July 26, 1994
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuichi Yamamoto, Tsuneo Okonogi, Seiji Shibahara, Shigeharu Inoue
  • Patent number: 5324721
    Abstract: The invention relates to new 3-substituted cephalosporins, a process for their preparation and their use as medicaments, in particular as medicaments having antibacterial activitity.
    Type: Grant
    Filed: September 19, 1991
    Date of Patent: June 28, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Schneider, Rainer Endermann, Karl-Georg Metzger, Klaus-Dieter Bremm
  • Patent number: 5318781
    Abstract: The oral absorption of antibiotics given of administration is significantly enhanced by use of the antibiotic in conjunction with a two-component absorption enhancing system made up of Laureth-12 together with a second component salts of capric acid and caprylic acids. The antibiotic containing two component enhancer system includes Miglyol-812 for optimum absorption.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: June 7, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Navnit Shah, Joel Unowsky
  • Patent number: 5312813
    Abstract: A method of killing microorganisms which form a biofilm on a tissue or implant surfaces in a patient, and which are refractory to a biocide at a dose which is effective to kill the microorganism in planktonic form. The effect of the biocide is potentiated, to an effective killing level, by applying an electric field across the surface containing the biofilm.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: May 17, 1994
    Assignee: University Technologies International
    Inventors: John W. F. Costerton, Antoine E. Khoury, Frank Johnson
  • Patent number: 5292733
    Abstract: The present invention relates to a cephalosporin compound including the pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates thereof of the formula(I) and its isomers: ##STR1## wherein: R.sup.1 is a C.sub.1-4 alkyl, C.sub.3-4 alkenyl, C.sub.3-4 alkynyl or --C(R.sup.3)(R.sup.4)COOH wherein R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, C.sub.1-4 alkyl group, or constitute a C.sub.3-7 cycloalkyl group with the carbon atoms to which R.sup.3 and R.sup.4 are attached;R.sup.2, which may be attached to N.sup.a or N.sup.b, is a C.sub.1-4 alkyl, C.sub.3-4 alkenyl, C.sub.3-7 cycloalkyl, aryl or amino group; andQ.sub.1 and Q.sub.2, which may be the same or different, are CH or N.
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: March 8, 1994
    Assignee: Lucky Limited
    Inventors: Yong Z. Kim, Hun S. Oh, Jae H. Yeo, Jong C. Lim, Won S. Kim, Chan S. Bang, Hyeon J. Yim
  • Patent number: 5281589
    Abstract: Novel semi-synthetic cephalosporin derivatives having a fused pyridiniummethyl at 3-position of the cephem nucleus, pharmaceutically acceptable salts, physiologically hydrolizable esters or solvates thereof are disclosed. Also disclosed is a process for preparing the cephalosporin derivatives which comprises introducing a fused pyridiniummethyl substituent at 3-position of 7-.beta.-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-ca rboxylic acid derivatives. The compounds of the present invention show potent antibacterial activities and a broad spectrum against both gram-positive and gram-negative bacteria.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: January 25, 1994
    Assignee: Cheil Foods & Chemicals, Inc.
    Inventors: Choong S. Kim, Seung H. An, Sung K. Cho, Yang S. Ahn, Kyoung E. Choi, Je H. Kim, Rok L. Yun, Sung Y. Park, Yeo H. Yoon, Chun S. Lyu, Koun H. Lee
  • Patent number: 5275816
    Abstract: 7 .alpha.-formamido cephalosporin derivatives having a 3[N-(optionally substituted)aminothiopyridinium thiomethyl] substituent have anti-bacterial activity and are of use in anti-bacterial therapy. Processes for the preparation thereof and intermediates for use in these processes are also disclosed.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: January 4, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Clive L. Branch, Angela W. Guest, Stephen C. Finch
  • Patent number: 5276024
    Abstract: The invention relates to new 3-substituted cephalosporins, to a process for their preparation and to their use as medicaments, in particular as medicaments having antibacterial activity.The invention relates to compounds of the general formula (I) ##STR1## in which X, Y, R.sup.1 and R.sup.2 have the meaning indicated in the description.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: January 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Schneider, Rainer Endermann, Karl G. Metzger, Klaus-Dieter Bremm
  • Patent number: 5264429
    Abstract: Derivatives of 2-spirocyclopropyl cephalosporin sulfone of the structural formula I ##STR1## are provided which are useful as potent elastase inhibitors.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: November 23, 1993
    Assignee: SynPhar Laboratories, Inc.
    Inventors: Samarendra N. Maiti, David Czajkowski, Paul Spevak, Kazuo Adachi, Ronald G. Micetich