1-oxa-5-aza-bicyclo(4.2.0)octane (including Unsaturated) Patents (Class 540/301)
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Patent number: 10533019Abstract: 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: GrantFiled: August 22, 2018Date of Patent: January 14, 2020Assignees: DONGDO CO., LTD., TIANJIN GREENPINE PHARMA CO., LTD.Inventor: Dong Chan Kim
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Publication number: 20130102583Abstract: 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: ApplicationFiled: April 4, 2011Publication date: April 25, 2013Applicant: SHIONOGI & CO., LTD.Inventors: Shinya Hisakawa, Yasushi Hasegawa, Toshiaki Aoki, Hiroki Kusano, Masayuki Sano, Jun Sato, Kenji Yamawaki
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Publication number: 20080177061Abstract: The invention relates to methods of identifying genes involved in cognitive impairment and compositions for treating cognitive impairment.Type: ApplicationFiled: March 3, 2008Publication date: July 24, 2008Inventors: Michela Gallagher, Pauline Kay Lund, Jeffrey D. Rothstein
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Patent number: 7396926Abstract: 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: GrantFiled: January 11, 2002Date of Patent: July 8, 2008Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Jianghong Rao
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Patent number: 7384928Abstract: 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: GrantFiled: March 18, 2003Date of Patent: June 10, 2008Assignee: Shionogi & Co., Ltd.Inventors: Yasuhiro Nishitani, Yoshinori Yamano
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Patent number: 7355040Abstract: 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: GrantFiled: November 22, 2004Date of Patent: April 8, 2008Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
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Patent number: 6825344Abstract: 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: GrantFiled: July 30, 2001Date of Patent: November 30, 2004Assignee: Pfizer Inc.Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
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Patent number: 6803460Abstract: 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: GrantFiled: September 24, 2002Date of Patent: October 12, 2004Assignee: DSM IP Assets B.V.Inventors: Ilco Adrainus Lambertus Antonius Boogers, Emilius Johannes Albertus Xaverius Van De Sandt, Dick Schipper
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Patent number: 6552185Abstract: 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: GrantFiled: November 16, 2000Date of Patent: April 22, 2003Assignee: DSM N.V.Inventors: Ilco Adrianus Lambertus Antonius Boogers, Emilius Johannes Albertus Xaverius Van De Sandt, Dick Schipper
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Patent number: 6495539Abstract: 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 thaType: GrantFiled: February 19, 1999Date of Patent: December 17, 2002Assignee: Washington UniversityInventors: Scott J. Hultgren, Fredrik Almqvist, Gabriel Soto
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Publication number: 20020058806Abstract: There is provided a process for the preparation of a compound according to Formula (II): 1Type: ApplicationFiled: July 30, 2001Publication date: May 16, 2002Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
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Patent number: 6369049Abstract: 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: GrantFiled: April 12, 1999Date of Patent: April 9, 2002Assignee: Eli Lilly and CompanyInventor: Karl Robert Dahnke
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Patent number: 6329363Abstract: 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: GrantFiled: November 6, 1998Date of Patent: December 11, 2001Assignee: Eli Lilly and CompanyInventor: Karl Robert Dahnke
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Patent number: 6255479Abstract: 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: GrantFiled: December 29, 1998Date of Patent: July 3, 2001Assignee: Research Corporation Technologies, Inc.Inventors: John D. Buynak, Akireddy Srinivasa Rao
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Patent number: 6124278Abstract: 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: GrantFiled: April 3, 1998Date of Patent: September 26, 2000Assignee: The Regents of the University of CaliforniaInventors: Gary A. Rogers, Peter Johnstrom
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Patent number: 6077952Abstract: A compound of formula (II) or a salt: ##STR1##Type: GrantFiled: June 8, 1999Date of Patent: June 20, 2000Assignee: Pfizer Inc.Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 6020329Abstract: .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: GrantFiled: October 20, 1997Date of Patent: February 1, 2000Assignee: Pzifer Inc.Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 6001997Abstract: .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: GrantFiled: January 11, 1999Date of Patent: December 14, 1999Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 5880111Abstract: 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: GrantFiled: June 7, 1995Date of Patent: March 9, 1999Inventors: Dan Farcasiu, John F. Hartmann, Pal Herczegh, Ferenc J. Sztaricskai
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Patent number: 5854227Abstract: 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: GrantFiled: June 7, 1995Date of Patent: December 29, 1998Inventors: John F. Hartmann, Dan Farcasiu
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Patent number: 5750684Abstract: 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: GrantFiled: August 30, 1991Date of Patent: May 12, 1998Assignee: Beecham Group plc.Inventors: Herve Geerlandt, Claudine Grand' Henry
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Patent number: 5703231Abstract: 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: GrantFiled: November 14, 1996Date of Patent: December 30, 1997Assignee: The Procter & Gamble CompanyInventors: Jared Lynn Randall, Jane Ellen Godlewski
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Patent number: 5688786Abstract: 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: GrantFiled: June 1, 1995Date of Patent: November 18, 1997Assignee: Microcide Pharmaceuticals, Inc.Inventors: Burton Christensen, Tomasz Glinka, Ving J. Lee, Scott Hecker
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Patent number: 5608055Abstract: 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: GrantFiled: June 6, 1995Date of Patent: March 4, 1997Assignee: Biochemie Gesellschaft m.b.H.Inventors: Jose Diago, Johannes Ludescher
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Patent number: 5602117Abstract: .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: GrantFiled: June 1, 1994Date of Patent: February 11, 1997Assignee: Pfizer Inc.Inventors: George Burton, Stephen C. M. Fell
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Patent number: 5580976Abstract: 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: GrantFiled: April 18, 1995Date of Patent: December 3, 1996Assignee: Shionogi & Co., Ltd.Inventors: Masaharu Kume, Tadatoshi Kubota
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Patent number: 5563264Abstract: 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: GrantFiled: April 18, 1995Date of Patent: October 8, 1996Assignee: Shionogi & Co., Ltd.Inventors: Masaharu Kume, Tadatoshi Kubota
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Patent number: 5525599Abstract: 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: GrantFiled: July 21, 1993Date of Patent: June 11, 1996Assignee: Eli Lilly and CompanyInventor: Ho-Shen Lin
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Patent number: 5412094Abstract: 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: GrantFiled: June 28, 1993Date of Patent: May 2, 1995Assignee: Eli Lilly and CompanyInventors: Jane G. Amos, Joseph M. Indelicato, Carol E. Pasini, Susan M. Reutzel
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Patent number: 5283329Abstract: 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: GrantFiled: March 2, 1993Date of Patent: February 1, 1994Assignee: Eli Lilly and CompanyInventor: Leland O. Weigel
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Patent number: 5262411Abstract: 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: GrantFiled: December 28, 1990Date of Patent: November 16, 1993Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Tetsuhiko Shirasaka, Hiroshi Ishikawa, Koichi Yasumura, Koichiro Jitsukawa, Sachio Toyama, Hidetsugu Tsubouchi, Kimio Sudo, Koichi Tsuji
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Patent number: 5246926Abstract: .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: GrantFiled: March 28, 1990Date of Patent: September 21, 1993Assignee: Beecham Group p.l.c.Inventors: John H. Bateson, George Burton, Stephen C. M. Fell
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Patent number: 5180719Abstract: 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: GrantFiled: April 29, 1991Date of Patent: January 19, 1993Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventors: Ronald E. White, Thomas P. Demuth, Jr.
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Patent number: 5169945Abstract: 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: GrantFiled: August 19, 1991Date of Patent: December 8, 1992Assignee: Eli Lilly and CompanyInventor: Leland O. Weigel
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Patent number: 5158946Abstract: .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: GrantFiled: September 14, 1990Date of Patent: October 27, 1992Assignee: Beecham Group p.l.c.Inventors: Brian C. Gasson, Jeremy D. Hinks
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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: 5112966Abstract: 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: GrantFiled: October 31, 1985Date of Patent: May 12, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 5070194Abstract: 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: GrantFiled: April 5, 1989Date of Patent: December 3, 1991Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Nori Saito, Takashi Shiroi, Shigemitsu Nagao, Ryo Kikuchi, Yutaka Kameyama
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Patent number: 4939250Abstract: 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: GrantFiled: May 12, 1987Date of Patent: July 3, 1990Assignee: Imperial Chemical Industries PlcInventors: Frank Lotus, Stephen J. Pegg, Evan W. Snape
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Patent number: 4888100Abstract: 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: GrantFiled: March 15, 1989Date of Patent: December 19, 1989Assignee: Eli Lilly and CompanyInventors: Larry W. Hertel, John M. Morin, Jr., Robert T. Vasileff
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Patent number: 4877783Abstract: .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: GrantFiled: January 24, 1985Date of Patent: October 31, 1989Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner
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Patent number: 4705852Abstract: 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: GrantFiled: June 20, 1986Date of Patent: November 10, 1987Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Tsutomu Aoki, Yasuhiro Nishitani
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Patent number: 4675398Abstract: 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: GrantFiled: August 16, 1985Date of Patent: June 23, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Thomas C. Sedergran, Carl F. Anderson
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Patent number: 4616084Abstract: 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: GrantFiled: July 31, 1984Date of Patent: October 7, 1986Assignee: Bayer AktiengesellschaftInventors: Dieter Habich, Wolfgang Hartwig
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Patent number: 4609652Abstract: .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: GrantFiled: January 24, 1985Date of Patent: September 2, 1986Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner