Double Bond Between The 2,3-positions Of The Bicyclo Ring System (e.g., 2 Cephem, Etc.) Patents (Class 540/217)
  • Patent number: 10370538
    Abstract: The compositions of the present disclosure provide novel fluorogenic probes for use in the specific imaging and detection of mycobacteria species, and in particular ?-lactam-antibiotic resistant. Specificity for mycobacteria is conferred on these probes by incorporating a moiety that specifically targets the unique trapping mechanism of the DprE1 found in in mycobacteria. Accordingly, only Mycobacteria species that express both a ?-lactamase and DprE1 enable both the activation of the caged fluorescent probe, and the affixing of the released fluorescent probes to the bacteria cells through the functioning reduction-covalent binding mechanism. Advantageously, such a probe is able, at its most sensitive, to allow single mycobacterium detection.
    Type: Grant
    Filed: January 20, 2016
    Date of Patent: August 6, 2019
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Jianghong Rao, Yunfeng Cheng, Jinghang Xie
  • Patent number: 9834681
    Abstract: ?-Lactamase substrates and methods for using the substrates to detect ?-lactamase and to diagnose tuberculosis.
    Type: Grant
    Filed: February 3, 2015
    Date of Patent: December 5, 2017
    Assignees: The Texas A&M University System, The Board of Trustees of the Leland Stanford Junior University
    Inventors: Jianghong Rao, Hexin Xie, Yunfeng Cheng, Jeffrey D. Cirillo
  • Publication number: 20150111853
    Abstract: Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.
    Type: Application
    Filed: October 22, 2014
    Publication date: April 23, 2015
    Inventors: Jan-Ji Lai, Pradip M. Pathare, Laxma Kolla, Adrien F. Soret
  • Patent number: 8906898
    Abstract: Novel solid forms of ceftolozane are described, as well as methods for the preparation and use of these solid forms.
    Type: Grant
    Filed: May 28, 2014
    Date of Patent: December 9, 2014
    Assignee: Calixa Therapeutics, Inc.
    Inventors: You Seok Hwang, Nicole Miller Damour, Lisa Duong, Valdas Jurkauskas, Kristos Adrian Moshos, Sanjay Mudur, Asli Ovat, Joseph Terracciano, Jason Woertink
  • Patent number: 7871997
    Abstract: This invention provides cephalosporin compounds and salts thereof. Such compounds are useful for preparing cross-linked glycopeptide-cephalosporin antibiotics.
    Type: Grant
    Filed: December 19, 2007
    Date of Patent: January 18, 2011
    Assignee: Theravance, Inc.
    Inventors: Paul R. Fatheree, Martin S. Linsell, Daniel Marquess, Daniel D. Long, Jason P. Chinn, Matthew B. Nodwell, Edmund J. Moran, James B. Aggen
  • Patent number: 7638624
    Abstract: The present invention relates to novel chemical compounds, methods for their discovery, and their therapeutic use. In particular, the present invention provides benzodiazepine derivatives and related compounds and methods of using benzodiazepine derivatives and related compounds as therapeutic agents to treat a number of conditions associated with the faulty regulation of the processes of programmed cell death, autoimmunity, inflammation, hyperproliferation, and the like.
    Type: Grant
    Filed: January 3, 2006
    Date of Patent: December 29, 2009
    Assignee: The Regents of the University of Michigan
    Inventor: Gary D. Glick
  • Publication number: 20040087786
    Abstract: The present invention relates to an improved process for the preparation of 3-propenyl cephalosporin DMF solvate, more particularly, the present invention relates to an improved process for the preparation of cefprozil DMF solvate of the formula (I), which is useful for the preparation of cefprozil of the formula (XIV).
    Type: Application
    Filed: December 10, 2002
    Publication date: May 6, 2004
    Applicant: ORCHID CHEMICALS & PHARMACEUTICALS LIMITED
    Inventors: Pandurang Balwant Deshpande, Bhausaheb Pandharinath Khadangale, Kumar Gurusamy, Ramesh Athmaram Konda
  • Publication number: 20030036541
    Abstract: The invention provides compounds of formula I and IV: 1
    Type: Application
    Filed: May 10, 2002
    Publication date: February 20, 2003
    Applicant: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, A. Srinivasa Rao, Greg C. Adam, Sirishkumar D. Nidamarthy, Venkata Ramana Doppalapudi
  • Publication number: 20020120136
    Abstract: High purity cephalosporin compound can be easily prepared in a high yield by a process comprising the steps of: reacting a cephem compound with a 4-hydroxyphenylglycine derivative.
    Type: Application
    Filed: February 25, 2002
    Publication date: August 29, 2002
    Inventors: Gwan-Sun Lee, Jae-Heon Lee, Young-Kil Chang, Hong-Sun Kim, Chul-Hyun Park, Gha-Seung Park, Cheol-Kyung Kim
  • Patent number: 6403789
    Abstract: A halogenating agent of the formula (1) and a method of halogenating hydroxyl group wherein R1 and R2 are the same or different and are each ethyl, propyl, isopropyl, butyl, isobutyl or allyl; X is chlorine atom or bromine atom; and Y is chlorine ion, bromine ion, dichlorophosphate ion, dibromophosphate ion, chlorosulfonate ion, bromosulfonate ion, chlorooxalate ion or bromooxalate ion.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: June 11, 2002
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Daisuke Suzuki, Ryo Kikuchi, Masaru Yasui
  • Patent number: 6194567
    Abstract: A halogenating agent of the formula (1) and a method of halogenating hydroxyl group wherein R1 and R2 are the same or different and are each ethyl, propyl, isopropyl, butyl, isobutyl or allyl; X is chlorine atom or bromine atom; and Y is chlorine ion, bromine ion, dichlorophosphate ion, dibromophosphate ion, chlorosulfonate ion, bromosulfonate ion, chlorooxalate ion or bromooxalate ion.
    Type: Grant
    Filed: October 13, 1999
    Date of Patent: February 27, 2001
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Daisuke Suzuki, Ryo Kikuchi, Masaru Yasui
  • Patent number: 6093813
    Abstract: Cephalosporin derivatives of formula II ##STR1## wherein R.sup.a denotes hydrogen or a silyl group; R.sup.b denotes a group of formula --OR.sup.e, wherein R.sup.e denotes hydrogen or alkyl; and R.sup.c and R.sup.d together denote a bond; in free form or in salt form.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: July 25, 2000
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Gerd Ascher, Johannes Ludescher, Hubert Sturm, Josef Wieser
  • Patent number: 6063917
    Abstract: A process for the production of a compound of formula ##STR1## wherein R.sup.a denotes hydrogen or silyl;R.sup.b denotes a group of formula --OR.sup.e, whereinR.sup.e denotes hydrogen or alkyl; andR.sup.c and R.sup.d together denote a bond;in free form or in salt form,which process comprises the step of spitting, in the presence of ozone, the double bond in position 3 of the ring structure of a compound of formula III ##STR2## wherein R.sub.2 and R.sub.3 are the same or different and independently of each other denote hydrogen or an organic group, and X.sup.- denotes the anion of an inorganic or organic acid and optionally silylating the amine group in position 7 of the ring system.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: May 16, 2000
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Gerd Ascher, Johannes Ludescher, Hubert Sturm, Josef Wieser
  • Patent number: 6013647
    Abstract: This invention relates to new benzoxazinedione derivatives corresponding to the formula I: ##STR1## wherein R.sup.1 =H or carboxyalkyl, R.sup.2 =H, alkyl or phenyl, and R.sup.3 represents different acid groups derived from amino acids, dipeptides and hydrazones or conjugates thereof with active ingredients, e.g. antibiotics. The compounds may be present as free acids, in the form of their salts or as readily cleavable esters. The compounds according to the invention constitute heterocyclically protected catechol derivatives and are effective as siderophores against gram-negative bacterial strains, particularly against Pseudomonads and strains of E. coli and Salmonella. In the form of their conjugates with active ingredients, e.g. antibiotics (as "siderophore-antibiotic conjugates"), they can transport the latter into bacterial cells and can improve or extend the antibacterial effect thereof, sometimes even in relation to bacterial strains which are resistant to other .beta.-lactams.
    Type: Grant
    Filed: March 5, 1998
    Date of Patent: January 11, 2000
    Assignee: Gruenenthal GmbH
    Inventors: Lothar Heinisch, Steffen Wittmann, Ute Moellmann, Rolf Reissbrodt
  • 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: 5801242
    Abstract: The present invention provides processes for making compounds of the structure(Q--L.sup.1)--L--(L.sup.2 --B)wherein(I) Q is a quinolone moiety;(II) B is a lactam moiety; and(III) L, L.sup.1, and L.sup.2 together comprise a linking moiety;comprising the steps of:(1) coupling a compound of Formula (III) with a lactam-containing compound to form an intermediate compound; and(2) cyclizing the intermediate by reaction with an organosilicon compound to give a compound of the formula (Q--L.sup.1)--L--(L.sup.2 --B).Preferably, the process additionally comprises a step prior to the coupling step, wherein protected forms of the compound of Formula (III) and the lactam compound are formed; and deprotection steps after the cyclization step, wherein the protecting groups are removed. Preferred antimicrobial compounds made by these processes are those where the beta-lactam moiety is a penem, a carbapenem, a cephem, or a carbacephem. Also preferred are those compounds where L.sup.1, L, and L.sup.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: September 1, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Jared Lynn Randall, Jane Ellen Godlewski
  • Patent number: 5574153
    Abstract: The invention relates to oxime derivatives of cephalosporanic structure, possessing antibacterial activity.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: November 12, 1996
    Assignee: ACS Dobfar S.p.A.
    Inventors: Maurizio Zenoni, Mario Leone, Riccardo Colombo
  • Patent number: 5552542
    Abstract: This invention relates to a method of producing 3-alkanoyloxymethyl-3-cephem-4-carboxylic acids from 3-hydroxymethyl-3-cephem-4-carboxylic acids in an aqueous medium for a practical, large-scale production. Moreover, the invention provides an ideal intermediate for the process.
    Type: Grant
    Filed: May 10, 1995
    Date of Patent: September 3, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: J. Gregory Reid, Paul R. Brodfuehrer, Patrick R. Smith
  • Patent number: 5281703
    Abstract: The present invention provides methods of making compounds of the structure[Q-L.sup.1 ]-L-[L.sup.2 -B[wherein(I) Q is a quinolone moiety;(II) B is a beta-lactam moiety;(III) L, L.sup.1, and L.sup.2 together comprise a carbamate-containing linking moietycomprising the steps of:(1) Reacting a lactam compound of the formula B-L.sup.4 -H with phosgene to form an intermediate compound of the formula B--L.sup.4 --C(=O)--Cl, where L.sup.4 is oxygen; and(2) Coupling said intermediate compound with a quinolone compound of the formula Q-L.sup.3 -R.sup.44 ; wherein L.sup.3 is nitrogen; R.sup.44 is hydrogen, Si(R.sup.45).sub.3, or Sn(R.sup.45).sub.3 ; and R.sup.45 is lower alkyl.Preferably, the process additionally comprises steps prior to the reacting and coupling steps where esters of the lactam and quinolone compounds are made. Also preferably, the coupling step comprises adding a solution containing the quinolone compound to a solution containing the intermediate compound.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: January 25, 1994
    Assignee: Procter & Gamble Pharmaceuticals, Inc.
    Inventors: Ronald E. White, Thomas P. Demuth, Jr.
  • Patent number: 5081248
    Abstract: A pyridine-N-oxide derivative of the formula: ##STR1## or a salt thereof.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: January 14, 1992
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Yoshiyuki Zama, Takanobu Naitou, Toshiyuki Yamamoto
  • Patent number: 4965358
    Abstract: A new compound called N,N'-carbonyl-bis-(4-ethyl-2,3-dioxo)-piperazine of Formula I ##STR1## A process for the preparation thereof based on the reaction of 4-ethyl-2,3-dioxo-piperazine or a trimethylsilyl derivative thereof with carbonyl chloride or a derivative thereof.The use of the compound of Formula I as an intermediate in the preparation of compounds of Formula II ##STR2## where R is a radical, substituted in alpha position, of a molecule of an acid selected from the group formed by phenylacetic acid, p-hydroxy phenylacetic acid, a 6-(phenylacetamido)-penicillanic acid and a 7-(phenylacetamido)-cephalosporanic acid.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: October 23, 1990
    Assignee: Gema, S. A.
    Inventors: Juan Cabre Castellvi, Jose Diago Meseguer, Asuncion Esteve Bianchini, Carlos E. Lenhardt Padro, Esteve Sans Pitarch
  • Patent number: 4956358
    Abstract: The compounds having a 4,11-dioxo-3-oxa-8(or 7)-thia-1-azatricyclo[7,2,0,0.sup.2,6 ]undecane-2-carboxylic acid skeleton as the base structures, their esters and their salts are useful antibacterial agents.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: September 11, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akira Morimoto, Noriyoshi Noguchi, Nobuo Choh
  • Patent number: 4945159
    Abstract: A method for the formation of intramolecular amide bonds by the action of cyanogen, under mild reaction conditions, in the preparation of cyclic amides, including lactams, in biologically active compounds. A compound containing at least one carboxylic acid group and at least one primary or secondary amino group is reacted with cyanogen to form an intramolecular amide bond. The method has utility in the synthesis of B-lactam antibiotics, such as penicillins, cephalosporins, and their derivatives, in enzyme modification, in cyclization of peptides, and in covalent cross-linking of proteins.
    Type: Grant
    Filed: December 2, 1986
    Date of Patent: July 31, 1990
    Assignee: University of Cincinnati
    Inventor: Richard A. Day
  • Patent number: 4684664
    Abstract: Disclosed herein are derivatives of .beta.-(4-isocyano-1,2,3,4-diepoxycyclopentyl)acrylic acid, the derivatives showing an antibacterial activity, an antifungal activity and an antimycoplasmal activity.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: August 4, 1987
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Katsuhisa Osugi, Isao Ichinose, Eisaku Takahashi, Masato Arahira
  • Patent number: 4666899
    Abstract: Compounds of general formula I ##STR1## (wherein R represents NH.sub.2 -- or an acylated or silylated amino group;R.sup.2 represents a hydrogen, halogen, alkyl, aryl, carboxyl or lower alkoxycarbonyl group;R.sup.3 is hydrogen or a carboxyl blocking group;B is >Sor>S.fwdarw.O (.alpha.- or .beta.-); and the dotted line represents .DELTA..sup.2 or .DELTA..sup.3 unsaturation) and salts, solvates and esters thereof are described.Compounds where R.sup.3 is hydrogen, the dotted line represents .DELTA..sup.3 unsaturation and R is a group of formula ##STR2## (where R.sup.a is an optionally substituted heterocyclic aryl group having one or more hetero atoms selected from S, N and O in the ring, R.sup.b is an optionally substituted aryl group, R.sup.c is hydrogen, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.d is as defined for R.sup.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: May 19, 1987
    Assignee: Glaxo Group Limited
    Inventors: Richard Bell, Paul D. Hallam, Michael W. Foxton
  • Patent number: 4622393
    Abstract: New 3-vinylcephalosporins of the general formula (I), ##STR1## in which n=0 or 1, R.sub.1 is a radical of the general formula (II), ##STR2## in which R.sub.4 is hydrogen or a protective radical and R.sub.5 represents a radical of the general formula (IIa) ##STR3## in which R.sup.a.sub.5 and R.sup.b.sub.5 are hydrogen or alkyl or together form an alkylene radical and R.sup.c.sub.5 is hydrogen or a protective radical, R.sub.2 is hydrogen, a protective radical or a radical which can easily be removed by an enzymatic method, and R.sub.3 is a halogen atom or a radical R'.sub.3 SO.sub.2 O-- or R".sub.3 CO--O--, in which radicals R'.sub.3 and R".sub.3 are substituted or unsubstituted alkyl or phenyl radicals, or alternatively R.sub.1 is a hydrogen atom or a radical of the general formula (II) in which R.sub.4 is defined as above and R.sub.5 is hydrogen, alkyl, vinyl, cyanomethyl or a protective radical, and R.sub.2 is defined as above, or R.sub.1 is hydrogen or a variously substituted acyl radical and R.sub.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: November 11, 1986
    Assignee: Rhone-Poulenc Industries
    Inventors: Daniel Farge, Pierre Le Roy, Claude Moutonnier, Jean-Francois Peyronel