1-oxa-5-aza-bicyclo(4.2.0)octane (including Unsaturated) Patents (Class 540/301)
  • Patent number: 10533019
    Abstract: The present disclosure provides a method for preparing a 7?-alkoxyoxacephem intermediate compound, the method comprising a process (S1) including: reacting a compound represented by a following chemical formula 1 with a halogen compound in an organic solvent to form a reaction product such that unreacted halogen compound remains; and adding metal alkoxide and reducing agent to the reaction product with the unreacted halogen compound remaining, thereby to produce a compound represented by a following chemical formula 2: where R is a Cl, Br, I, halogen derivative, R1 is a carboxyl protecting group including diphenylmethyl, p-methoxybenzyl, p-nitrobenzyl or hydrogen (H), and R2 is an alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: August 22, 2018
    Date of Patent: January 14, 2020
    Assignees: DONGDO CO., LTD., TIANJIN GREENPINE PHARMA CO., LTD.
    Inventor: Dong Chan Kim
  • Publication number: 20130102583
    Abstract: A compound of the formula: wherein X is —N?, —CH?, or the like; W is —CH2— or the like; U is —S— or the like; R1 and R2 are each independently hydrogen, halogen, optionally substituted lower alkyl, or the like; R3 is hydrogen or the like; each R4 is independently hydrogen, halogen, or the like; m is an integer from 0 to 2; Q is a single bond, or the like; G is —C(?O)—, or the like; D is a single bond, —NH—, or the like; and E is a cyclic quaternary ammonium group, or an ester, a protected compound at the amino on the ring in the 7-side chain, a pharmaceutically acceptable salt, or a solvate thereof.
    Type: Application
    Filed: April 4, 2011
    Publication date: April 25, 2013
    Applicant: SHIONOGI & CO., LTD.
    Inventors: Shinya Hisakawa, Yasushi Hasegawa, Toshiaki Aoki, Hiroki Kusano, Masayuki Sano, Jun Sato, Kenji Yamawaki
  • Publication number: 20080177061
    Abstract: The invention relates to methods of identifying genes involved in cognitive impairment and compositions for treating cognitive impairment.
    Type: Application
    Filed: March 3, 2008
    Publication date: July 24, 2008
    Inventors: Michela Gallagher, Pauline Kay Lund, Jeffrey D. Rothstein
  • Patent number: 7396926
    Abstract: Provided are fluorescent substrates for ?-lactamases having the general formula I: in which R is a benzyl, 2-thienylmethyl, or cyanomethyl group; R? is selected from the group consisting of H, physiologically acceptable salts or metal, ester groups, ammonium cations, —CHR2OCO(CH2)nCH3, —CHR2OCOC(CH3)3, acylthiomethyl, acyloxy-alpha-benzyl, deltabutyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, ?-morpholinoethyl, dialkylaminoethyl, and dialkylaminocarbonyloxymethyl, in which R2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO2 and CH2; and Z is a donor fluorescent moiety. Also provided are methods of use of the compound of general formula I.
    Type: Grant
    Filed: January 11, 2002
    Date of Patent: July 8, 2008
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Jianghong Rao
  • Patent number: 7384928
    Abstract: A compound of the formula: (wherein, T is S, SO or O; X is halogen, CN, carbamoyl optionally substituted with lower alkyl, lower alkyl, lower alkoxy, or lower alkylthio; A is substituted lower alkylene (wherein the substituent is optionally substituted mono lower alkyl, optionally substituted lower alkylidene, or optionally substituted lower alkylene); Z+ is an optionally substituted, a cation and an N atom-containing heterocyclic group), ester, amino-protected compound wherein the amino bonds to a thiazole ring at the 7-position, or pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: June 10, 2008
    Assignee: Shionogi & Co., Ltd.
    Inventors: Yasuhiro Nishitani, Yoshinori Yamano
  • Patent number: 7355040
    Abstract: There is provided a process for the preparation of a compound according to Formula (II): which includes the step of cyclizing a compound of Formula (III): wherein R1, R2, R3, R4, X and m have meanings which are given in the description.
    Type: Grant
    Filed: November 22, 2004
    Date of Patent: April 8, 2008
    Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
  • Patent number: 6825344
    Abstract: There is provided a process for the preparation of a compound according to Formula (II): which includes the step of cyclising a compound of Formula (III): wherein R1, R2, R3, R4, X and m have meanings which are given in the description.
    Type: Grant
    Filed: July 30, 2001
    Date of Patent: November 30, 2004
    Assignee: Pfizer Inc.
    Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
  • Patent number: 6803460
    Abstract: A method for the recovery of an N-substituted cephalosporanic acid compound of general formula (I), wherein R2 is selected from the group consisting of adipyl (1,4-dicarboxybutane), succinyl, glutaryl, adipyl, pimelyl, suberyl, 2-carboxyethyithio)acetyl, 3-carboxyethylthio)propionyl, higher alkyl saturated and higher alkyl unsaturated dicarboxylic acids, from a complex mixture comprising in addition to the compound of general formula (I) 6-aminopenicillanic acid (6-APA) and optionally one or more N-substituted penicillanic acid compounds, comprising the steps of: (a) acidifying the complex mixture to a pH below 6.5 and maintaining the mixture below said pH at a temperature of between 10° C. and 150° C.; and/or (b) contacting the complex mixture with a carbon dioxide source; and (c) recovering the cephalosporanic acid compound of formula (I) from the mixture obtained after steps (a) and/or (b).
    Type: Grant
    Filed: September 24, 2002
    Date of Patent: October 12, 2004
    Assignee: DSM IP Assets B.V.
    Inventors: Ilco Adrainus Lambertus Antonius Boogers, Emilius Johannes Albertus Xaverius Van De Sandt, Dick Schipper
  • Patent number: 6552185
    Abstract: A method for the recovery of a compound formula (I) from a complex mixture, comprising the steps of: (a) acidifying the complex mixture to a pH below 6.5 and maintaining the mixture below said pH at a temperature of between 50° C. and 130° C.; and/or (b) contacting the complex mixture with a carbon dioxide source; and (c) subjecting the mixture obtained after steps (a) and/or (b) to chromatography to obtain the compound of formula (I).
    Type: Grant
    Filed: November 16, 2000
    Date of Patent: April 22, 2003
    Assignee: DSM N.V.
    Inventors: Ilco Adrianus Lambertus Antonius Boogers, Emilius Johannes Albertus Xaverius Van De Sandt, Dick Schipper
  • Patent number: 6495539
    Abstract: Compounds of the formula and the salts, esters and amides thereof wherein Z is S, SO, SO2 or O; each of R1, R2 and R3 is independently H or substituted or unsubstituted alkyl (1-10C), substituted or unsubstituted alkenyl, substituted or unsubstituted acyl (2-11C), substituted or unsubstituted aryl (6-14C), substituted or unsubstituted arylcarbonyl (7-15C), substituted or unsubstituted arylalkyl (7-15C), substituted or unsubstituted pyridyl wherein substituents on any alkyl, alkenyl, or acyl moiety are selected from the group consisting of halo, and RO, wherein R is H or alkyl (1-6C), and substituents on any aryl or pyridyl moiety are selected from the group consisting of halo, and RO, where R is H or alkyl (1-6C), —CN and —CF3; with the proviso that R1 is not H and R1 and R3 are not identical and with the proviso that in formula (1), the B ring may contain one double bond that is located between positions 2 and 3, and in formula (2), the B ring may contain one double bond tha
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: December 17, 2002
    Assignee: Washington University
    Inventors: Scott J. Hultgren, Fredrik Almqvist, Gabriel Soto
  • Publication number: 20020058806
    Abstract: There is provided a process for the preparation of a compound according to Formula (II): 1
    Type: Application
    Filed: July 30, 2001
    Publication date: May 16, 2002
    Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
  • Patent number: 6369049
    Abstract: The invention provides new fluorinated cephalosporin antibiotics of Formula I wherein Ra, Rb, Rc, Rd and Re, independently, are H, F or a C1-C6 alkyl-(Z)n— group having at least one fluorine substituent; X is O or S; Y is S, O, or —CH2—; Z is O, S, —SO—, or —SO2—; m and n independently are 0 or 1; and R1 is H, C1-C6-alkyl, phenyl or benzyl, each of which may optionally have up to three substituents selected from halo, C1-C4-alkoxy, phenyl, NO2, C1-C6-alkanoyl, benzoyl, or C1-C6-alkanoyloxy; or a physiologically acceptable salt thereof; and methods of preventing or treating or treating infection, particularly mastitis in ruminants, using these antibiotics.
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: April 9, 2002
    Assignee: Eli Lilly and Company
    Inventor: Karl Robert Dahnke
  • Patent number: 6329363
    Abstract: The invention provides new fluorinated cephalosporin antibiotics and methods of preventing or treating infection, particularly mastitis in ruminants, using these antibiotics, and veterinary and pharmaceutical formulations comprising these antibiotics.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: December 11, 2001
    Assignee: Eli Lilly and Company
    Inventor: Karl Robert Dahnke
  • Patent number: 6255479
    Abstract: A method for preparing an &agr;-oxolactam comprising, reacting a corresponding &agr;-diazolactam with an oxygen donor, in the presence of a transition metal catalyst, to yield the corresponding &agr;-oxolactam.
    Type: Grant
    Filed: December 29, 1998
    Date of Patent: July 3, 2001
    Assignee: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, Akireddy Srinivasa Rao
  • Patent number: 6124278
    Abstract: Compounds based on the benzoxazine ring system that are remarkably more potent than corresponding benzoyl piperidines for enhancing synaptic responses mediated by AMPA receptors are disclosed, as are methods for the preparation thereof, and methods for their use for treatment of subjects suffering from impaired nervous or intellectual functioning due to deficiencies in the number of excitatory synapses or in the number of AMPA receptors. The invention compounds can also be used for the treatment of non-impaired subjects for enhancing performance in sensory-motor and cognitive tasks which depend on brain networks utilizing AMPA receptors and for improving memory encoding.
    Type: Grant
    Filed: April 3, 1998
    Date of Patent: September 26, 2000
    Assignee: The Regents of the University of California
    Inventors: Gary A. Rogers, Peter Johnstrom
  • Patent number: 6077952
    Abstract: A compound of formula (II) or a salt: ##STR1##
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: June 20, 2000
    Assignee: Pfizer Inc.
    Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
  • Patent number: 6020329
    Abstract: .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acy 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; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.
    Type: Grant
    Filed: October 20, 1997
    Date of Patent: February 1, 2000
    Assignee: Pzifer Inc.
    Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
  • Patent number: 6001997
    Abstract: .beta.-Lactam antibiotics of formula (I) or a salt 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; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.2 ; m is 1 or 2; and n is 0, useful in the treatment of bacterial infections.
    Type: Grant
    Filed: January 11, 1999
    Date of Patent: December 14, 1999
    Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
  • Patent number: 5880111
    Abstract: Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, and infectious urinary tract stones, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 9, 1999
    Inventors: Dan Farcasiu, John F. Hartmann, Pal Herczegh, Ferenc J. Sztaricskai
  • Patent number: 5854227
    Abstract: Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, infectious urinary tract stones, and bone cancer, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 29, 1998
    Inventors: John F. Hartmann, Dan Farcasiu
  • Patent number: 5750684
    Abstract: The present invention provides a process for the substitution of an acylamino .beta.-lactam compound at the carbon atom carrying the acylamino group, which process comprises reacting the .beta.-lactam compound with an halogenating agent and a nucleophilic reagent; characterized in that the acylamino group has an acidic group on the carbon atom adjacent the carbonyl group.In particular the process of this invention comprises reacting a .beta.-lactam of partial structure (I): ##STR1## where X represents an acidic group; with an halogenating agent and a nucleophilic reagent.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: May 12, 1998
    Assignee: Beecham Group plc.
    Inventors: Herve Geerlandt, Claudine Grand' Henry
  • Patent number: 5703231
    Abstract: The present invention provides a process for making a compound having a structure according to Formula (I) ##STR1## wherein A.sup.1, A.sup.2 and A.sup.3 are independently carbon or nitrogen and R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are known quinolone substituents; and wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety;or a protected form, salt, pharmaceutically-acceptable salt, biohydrolyzable ester, or solvate thereof;the process comprising reacting one or more organosilicon compounds with a compound having a structure according to Formula (II) ##STR2## wherein A.sup.1, A.sup.2 and A.sup.3, R.sup.1, R.sup.3, R.sup.4 and R.sup.6 as described above; wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety; and X is a leaving group;or a protected form, salt, biohydrolyzable ester, or solvate thereof.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: December 30, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Jared Lynn Randall, Jane Ellen Godlewski
  • Patent number: 5688786
    Abstract: The present invention includes novel compounds 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: June 1, 1995
    Date of Patent: November 18, 1997
    Assignee: Microcide Pharmaceuticals, Inc.
    Inventors: Burton Christensen, Tomasz Glinka, Ving J. Lee, Scott Hecker
  • Patent number: 5608055
    Abstract: A new process is described for the production of 7-alpha-aminoacyl-cephalosporin free from halogen-containing solvents by acylating 7-amino-ceph-3-em-4-carboxylic acid or a derivative thereof in a halogen-free solvent.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 4, 1997
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Jose Diago, Johannes Ludescher
  • Patent number: 5602117
    Abstract: .beta.-lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy of formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; 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 (such as a pharmaceutically acceptable in vivo hydrolysable ester group); R.sup.4 represents up to four substituents selected from alkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, amino, alkylamino, acylamino, dialkylamino, CO.sub.2 R, CONR.sub.2, SO.sub.2 NR.sub.2 (where R is hydrogen or C.sub.1-6 alkyl), aryl and heterocyclyl, which may be the same or different and wherein any R.sup.4 alkyl substituent is optionally substituted by any other R.sup.4 substituent; X is S, SO, SO.sub.2, O or CH.sub.2 ; Y is S, SO or SO.sub.2 ; and m is 1 or 2, useful in the treatment of bacterial infections in humans and animals.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: February 11, 1997
    Assignee: Pfizer Inc.
    Inventors: George Burton, Stephen C. M. Fell
  • Patent number: 5580976
    Abstract: A process for preparing a .beta.-lactam compound of the formula (I): ##STR1## which comprises cyclization of an azetidinone derivative of the formula: ##STR2## is provided in which R.sup.1 is hydrogen, alkyl which is optionally substituted, or amino which is optionally substituted; R.sup.2 is a carboxy-protecting group; and X is alkylene which is optionally intervened by --O-- or --S--, and/or which is optionally substituted; and R.sup.3 is aryl which is optionally substituted.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: December 3, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masaharu Kume, Tadatoshi Kubota
  • Patent number: 5563264
    Abstract: A process for preparing a .beta.-lactam compound of the formula (I): ##STR1## which comprises cyclization, in the presence of a catalyst, of an azetidinone derivative of the formula: ##STR2## is provided in which R.sup.1 is hydrogen, alkyl which is optionally substituted, or amino which is optionally substituted; R.sup.2 is a carboxy-protecting group; and X is alkylene which is optionally intervened by --O-- or --S--, and/or which is optionally substituted; and R.sup.3 is aryl which is optionally substituted. The catalyst is preferably a transition metal salt (especially rhodium) or is an acid.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: October 8, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masaharu Kume, Tadatoshi Kubota
  • Patent number: 5525599
    Abstract: The invention provides compounds of the formula ##STR1## wherein X is CH.sub.2, S or O; R.sub.1 is a 3 position substituent such as hydrogen, hydroxy, halo, trifluoromethyl, C.sub.2 F.sub.5, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl, CH.sub.2 O(CO)R', CH.sub.2 O(CO)NH.sub.2, CO.sub.2 R', thio(C.sub.1 -C.sub.6)alkyl, thio(C.sub.1 C.sub.6)alkenyl, oxo(C.sub.1 -C.sub.6)alkyl, phosphine oxide, quaternary ammonium group, substituted or unsubstituted thiazolothio, or oxo(C.sub.1 -C.sub.6)alkenyl;wherein R' is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkenyl;R.sub.2 is hydrogen or a carboxy protecting group;R.sub.3 is ##STR2## (CH.sub.2).sub.n ; wherein R.sub.6 is hydrogen Me, CH.sub.2 F, CF.sub.3, C.sub.2 H.sub.5, CH.sub.2 CH.sub.2 F, CH.sub.2 CF.sub.3, C.sub.2 F.sub.5, CH.sub.2 CO.sub.2 R', CH.sub.2 CONH.sub.2, C(Me).sub.2 CO.sub.2 R', or C(Me).sub.2 CONH.sub.2 ; and n is 0-5;R.sub.4 is ##STR3## wherein Z is O, S, NH, or CH.sub.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: June 11, 1996
    Assignee: Eli Lilly and Company
    Inventor: Ho-Shen Lin
  • Patent number: 5412094
    Abstract: The invention provides complexes of the formula: ##STR1## wherein X is chloro, hydrogen, vinyl, or --CH.sub.3,Z is O;is 0-5;Y is phenyl or 1,4-cyclohexadien-1-yl;R.sub.1 and R.sub.2 are hydrogen or hydroxy, with the proviso that R.sub.1 and R.sub.2 are not both hydrogen andR.sub.3 is --COO.sup.-, --COO(C.sub.1 -C.sub.4 alkyl), --NO.sub.2 or ##STR2## wherein R.sub.4 is C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: May 2, 1995
    Assignee: Eli Lilly and Company
    Inventors: Jane G. Amos, Joseph M. Indelicato, Carol E. Pasini, Susan M. Reutzel
  • Patent number: 5283329
    Abstract: The invention provides compounds of the formula ##STR1## wherein R* is a group of the formula ##STR2## wherein R and R.sup.0 are individually C.sub.1 -C.sub.6 alkyl groups or together form a ring consisting of the nitrogen atom to which they are attached and two to seven carbon atoms, said ring optionally substituted by one or more C.sub.1 -C.sub.6 alkyl and/or C.sub.1 -C.sub.6 substituted alkyl groups;Q and Q' are individually hydrogen, C.sub.1 -C.sub.6 alkyl, or when taken together form a divalent radical of the formula --CH.dbd.CH--CH.dbd.CH--;A and A' together form a group of the formula ##STR3## wherein R.sup.2 is hydrogen or a carboxy-protecting group; X is oxygen; R.sup.1 is hydrogen, hydroxy, halo, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 substituted alkylthio, C.sub.7 -C.sub.12 phenylalkyl, C.sub.7 -C.sub.12 substituted phenylalkyl, phenyl or substituted phenyl; a group of the formula--COR.sup.3wherein R.sup.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: February 1, 1994
    Assignee: Eli Lilly and Company
    Inventor: Leland O. Weigel
  • Patent number: 5262411
    Abstract: There is provided a cephalosporin derivative represented by the general formula (1): ##STR1## wherein R.sup.101, R.sup.102, R.sup.103 and Y.sup.101 are as difined; the general formula (2): ##STR2## wherein R.sup.201, R.sup.202 and R.sup.203 are as defined above; the general formula (3): ##STR3## wherein R.sup.301, R.sup.302, Y.sup.301, Y.sup.302 and A.sup.301 are as defined; or pharmaceutically acceptable salt thereof. The compound is useful as an active ingredient of antimicrobial agent.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: November 16, 1993
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Tetsuhiko Shirasaka, Hiroshi Ishikawa, Koichi Yasumura, Koichiro Jitsukawa, Sachio Toyama, Hidetsugu Tsubouchi, Kimio Sudo, Koichi Tsuji
  • Patent number: 5246926
    Abstract: .beta.-Lactam compounds of the formula (Ia) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido;R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin;CO.sub.2 R.sup.6 is a carboxy group or a carboxylate anion;R.sup.3 is a Y-lactone ring optionally containing an endocyclic double bond, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; and X is S, SO, SO.sub.2, O or CH.sub.2.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: September 21, 1993
    Assignee: Beecham Group p.l.c.
    Inventors: John H. Bateson, George Burton, Stephen C. M. Fell
  • Patent number: 5180719
    Abstract: Antimicrobial quinolonyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: ##STR1## wherein (1) R.sup.3, R.sup.4, and R.sup.5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and(2) A.sup.2, A.sup.2, A.sup.3, R.sup.7, R.sup.8, and R.sup.9 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: January 19, 1993
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventors: Ronald E. White, Thomas P. Demuth, Jr.
  • Patent number: 5169945
    Abstract: The present invention provides a process for protecting an amino group in a compound exposed to nucleophilic reaction conditions in which the imido group used for protection is reacted with a secondary amine to form an acyl group which protects the amino group during exposure to the nucleophilic reaction conditions, after which the acylamino group may be reacted with an acid to reform the imido group so that the compound may then undergo non-nucleophilic manipulations. Also provided is a resolution method in which diasteriometric compounds having the acylamino group as described above are reacted with acid, and as these diasteriomers react at different rates to form the imido group, the reaction may be monitored so as to isolate the desired product at the appropriate point to maximize optical purity.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Eli Lilly and Company
    Inventor: Leland O. Weigel
  • Patent number: 5158946
    Abstract: .beta.-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido;R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin;R.sup.3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group);R.sup.4 is a .gamma.- or .delta.-lactone ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; X is S, SO, SO.sub.2, O or CH.sub.2 ; and Y is O or S.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: October 27, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Brian C. Gasson, Jeremy D. Hinks
  • Patent number: 5134138
    Abstract: 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: Grant
    Filed: July 9, 1990
    Date of Patent: July 28, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiroshi Onoue, Kyoji Minami, Koji Ishikura
  • Patent number: 5112966
    Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.
    Type: Grant
    Filed: October 31, 1985
    Date of Patent: May 12, 1992
    Assignee: Sumitomo Pharmaceuticals Company, Limited
    Inventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
  • Patent number: 5070194
    Abstract: This invention provides a method of producing a .beta.-lactam derivative represented by the formula (I): ##STR1## said method consisting essentially of the step of reacting a .beta.-lactam derivative represented by the formula (II): ##STR2## with a phenol in a reaction system which consists essentially of said .beta.-lactam derivative of formula (II) and said phenol.
    Type: Grant
    Filed: April 5, 1989
    Date of Patent: December 3, 1991
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Nori Saito, Takashi Shiroi, Shigemitsu Nagao, Ryo Kikuchi, Yutaka Kameyama
  • Patent number: 4939250
    Abstract: A process for preparing compounds of the formula I: ##STR1## wherein X is sulphur, oxygen, methylene or sulphinyl (R or S configuration), R.sup.3 is hydrogen or methoxy, R.sup.4 is an optionally substituted (1-4C)alky group, Y is hydrogen or a carboxyl protecting group and Q is an optionally protected amino group or an acylamino group, which comprises reacting a compound of formula (II) ##STR2## with a compound of formula (III) ##STR3## wherein R.sup.4 is as defined above and W and Z represent hydrogen atoms or a group or groups removable to yield the compound of formula (I). The compounds of the formula I are useful intermediates in the preparation of cephalosporin antibiotics.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: July 3, 1990
    Assignee: Imperial Chemical Industries Plc
    Inventors: Frank Lotus, Stephen J. Pegg, Evan W. Snape
  • Patent number: 4888100
    Abstract: A process for photochemically converting 3-exomethylene cephams (or 1-carba(1-dethia)cephams or and 1-oxa(1-dethia)cephams) from the corresponding 3-alkyl-3-cephem (or 1-carba(1-dethia)cephem or 1-oxa(1-dethia)cephem) is provided. Further provided are 3-cephams useful as intermediates to 3-cephem compounds.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: December 19, 1989
    Assignee: Eli Lilly and Company
    Inventors: Larry W. Hertel, John M. Morin, Jr., Robert T. Vasileff
  • Patent number: 4877783
    Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: October 31, 1989
    Assignee: Beecham Group p.l.c.
    Inventor: Peter H. Milner
  • Patent number: 4705852
    Abstract: An antibacterial cephalosporin hydroxamic acid derivative represented by the following formula (I), processes for its preparation, compositions containing the same as an active ingredient, and a method for killing bacteria by contacting with said compound. ##STR1## (wherein, R is acyl; R.sup.1 is hydrogen or methoxy; R.sup.2 is alkylene; R.sup.3 is hydrogen, aliphatic group or a hydroxy-protecting group; R.sup.4 is hydrogen or amino-protecting group; R.sup.5 is hydrogen, light metal atom or carboxy-protecting group; and X is oxygen, sulfur, or sulfinyl).
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: November 10, 1987
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Tsutomu Aoki, Yasuhiro Nishitani
  • Patent number: 4675398
    Abstract: The presence of a copper salt during the oximation of a .beta.-lactam containing compound having glyoxylamino substituents of the formula ##STR1## by reaction with an aminooxy compound having the formulaH.sub.2 N--O--R.sub.a,or a salt or ester thereof, results in a product wherein the ratio of syn isomer to anti isomer is increased.
    Type: Grant
    Filed: August 16, 1985
    Date of Patent: June 23, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Thomas C. Sedergran, Carl F. Anderson
  • Patent number: 4616084
    Abstract: A process for the preparation of a 7-acylamino-3-hydroxy-2-cephem-4-carboxylic acid, 7-acylamino-3-hydroxy-1-dethia-1-oxa-3-cephem-4-carboxylic acid or derivative thereof of the general formula ##STR1## in which R.sup.1 is hydrogen or optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl, heteroaryl, heteroaralkyl, aryloxyalkyl, heteroaryloxyalkyl, alkoxyalkyl, arylthioalkyl, heteroarylthioalkyl, alkylthioalkyl, alkoxy, aryloxy, alkylthio or arylthio,R.sup.2 is hydrogen, a carboxy-protective group or a pharmaceutically useful ester radical, andX is sulphur or oxygen,which comprises:(a) reacting a compound of the formula ##STR2## with (i) a compound of the formula ##STR3## in which R.sup.2 and X have the abovementioned meaning and Y represents diazo (N.sub.2) or hydrogen (H.sub.2) in an inert solvent in the presence of a Lewis acid or proton acid catalyst, or(ii) a compound of the formulaHX--CH.sub.2 --C.tbd.C--COOR.sup.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: October 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Wolfgang Hartwig
  • Patent number: 4609652
    Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: September 2, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Peter H. Milner