The Additional Chalcogen Is Bonded Directly To The Ring Nitrogen Patents (Class 540/355)
  • Publication number: 20150148326
    Abstract: The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.
    Type: Application
    Filed: January 29, 2015
    Publication date: May 28, 2015
    Inventors: Matthew F. Brown, Mark J. Mitton-Fry, Seungil Han, Manjinder Lall, Mark Plummer, Hud Lawrence Risley, Veerabahu Shanmugasundaram, Jeremy Starr
  • Publication number: 20150045340
    Abstract: The present invention relates to novel ?-lactam compounds, their preparation and use. In particular, this invention relates to novel ?-lactam compounds which are amidine substituted monobactam derivatives useful as antimicrobial agents and their preparation.
    Type: Application
    Filed: January 23, 2013
    Publication date: February 12, 2015
    Applicant: AiCuris GmbH & Co. KG
    Inventors: Burkhard Klenke, Irith Wiegand, Guido Schiffer, Heike Broetz-Oesterhelt, Samarendra N. Maiti, Jehangir Khan, Andhe Reddy, Zhixiang Yang, Mostafa Hena, Guofeng Jia, Ou Ligong, Hong Liang, Judy Yip, Chuanjun Gao, Sabiha Tajammul, Rahim Mohammad, Ganguli Biswajeet
  • Patent number: 8927707
    Abstract: It discloses a process for refining Aztreonam, comprising the steps of 1) treating Aztreonam material with an alkali metal alkoxylate or an alkali earth metal alkoxylate under heating in the presence of a suitable solvent or a mixture of solvents, followed by adjusting the pH value with a suitable acid and cooling down to precipitate Aztreonam, which provides a primary purified Aztreonam; 2) adsorbing Aztreonam with strongly basic ion exchange resin, followed by eluting the resin and collecting the eluate, to provide a secondary purified Aztreonam after concentration under reduced pressure; 3) adjusting the pH value with a suitable acid to allow crystallization, followed by centrifuging and washing the resultant crystals, to provide a tertiary purified Aztreonam after drying. The refined Aztreonam product has a purity of no less than 99.2%, mostly no less than 99.5%, with little residue on ignition and significantly low content of heavy metals.
    Type: Grant
    Filed: March 17, 2011
    Date of Patent: January 6, 2015
    Assignee: Hainan Lingkang Pharmaceutical Co., Ltd.
    Inventor: Linggang Tao
  • Patent number: 8901293
    Abstract: New monobactam antibiotics compounds which contain an 3-amino-azetidin-2-one ring and are active against gram-negative bacteria, wherein the compounds include the compound 2-(2-amino-thiazol-4-yl)-2-[(Z)-(1H,4H-1,5-dihydroxy-4-oxo-pyridin-2-yl)methoxyimino]-N-[3(S)-1-oxysulfonyl-2,2-dimethyl-4-oxo-azetidin-3-yl]acetamide.
    Type: Grant
    Filed: December 7, 2006
    Date of Patent: December 2, 2014
    Assignee: Basilea Pharmaceutica AG
    Inventors: Eric Desarbre, Bérangére Gaucher, Malcolm G. P. Page, Patrick Roussel
  • Publication number: 20140275007
    Abstract: Disclosed herein are oxamazin monobactam compounds and their use as antibiotics resistant to degradation by ?-lactamases. Also disclosed are pharmaceutical compositions containing the compounds and methods of synthesis.
    Type: Application
    Filed: March 14, 2013
    Publication date: September 18, 2014
    Inventors: Tomasz Glinka, Scott Hecker, Olga Rodny
  • Publication number: 20130296549
    Abstract: It discloses a process for refining Aztreonam, comprising the steps of 1) treating Aztreonam material with an alkali metal alkoxylate or an alkali earth metal alkoxylate under heating in the presence of a suitable solvent or a mixture of solvents, followed by adjusting the pH value with a suitable acid and cooling down to precipitate Aztreonam, which provides a primary purified Aztreonam; 2) adsorbing Aztreonam with strongly basic ion exchange resin, followed by eluting the resin and collecting the eluate, to provide a secondary purified Aztreonam after concentration under reduced pressure; 3) adjusting the pH value with a suitable acid to allow crystallization, followed by centrifuging and washing the resultant crystals, to provide a tertiary purified Aztreonam after drying. The refined Aztreonam product has a purity of no less than 99.2%, mostly no less than 99.5%, with little residue on ignition and significantly low content of heavy metals.
    Type: Application
    Filed: March 17, 2011
    Publication date: November 7, 2013
    Inventor: Linggang Tao
  • Publication number: 20130274238
    Abstract: Use of a monobactam antibiotic of formula (I) wherein the oxyimino group i.e. >C?N—O— has Z-orientation, or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the treatment of a bacterial infection in combination with a carbapenem antibiotic or a pharmaceutically acceptable salt thereof.
    Type: Application
    Filed: June 12, 2013
    Publication date: October 17, 2013
    Inventors: Eric Desarbre, Malcolm G.P. Page
  • Publication number: 20130252935
    Abstract: The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.
    Type: Application
    Filed: February 27, 2013
    Publication date: September 26, 2013
    Applicant: PFIZER INC.
    Inventors: Matthew F. Brown, Mark J. Mitton-Fry, Seungil Han, Manjinder Lall, Mark Plummer, Hud Lawrence Risley, Veerabahu Shanmugasundaram, Jeremy Starr
  • Publication number: 20130231323
    Abstract: Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.
    Type: Application
    Filed: September 6, 2011
    Publication date: September 5, 2013
    Applicant: DUKE UNIVERSITY
    Inventors: Pei Zhou, Eric J. Toone
  • Patent number: 8404671
    Abstract: The invention relates to heterosubstituted N-thiolated beta-lactams, compositions comprising these compounds, methods for their production, and methods of use as antibiotics to inhibit the growth of bacteria. In one embodiment, the compounds have the structure shown in formula (A) or formula (B) or formula (C): wherein the R groups are as defined in the specification. The antibacterial agents of the invention can be administered to a human or animal to treat or inhibit bacterial infection, such as that of Staphylococcus species, including methicillin-resistant Staphylococcus aureus (MRSA).
    Type: Grant
    Filed: November 22, 2010
    Date of Patent: March 26, 2013
    Assignee: University of South Florida
    Inventors: Edward Turos, Praveen Ramaraju
  • Publication number: 20120302542
    Abstract: The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.
    Type: Application
    Filed: November 29, 2011
    Publication date: November 29, 2012
    Inventors: Matthew F. Brown, Mark J. Mitton-Fry, Seungil Han, Manjinder Lall, Mark Plummer, Hud Lawrence Risley, Veerabahu Shanmugasundaram, Jeremy Starr
  • Patent number: 8110678
    Abstract: This invention is the design and synthesis of a caprolactone monomer which bears a pendant protected carboxyl group. This monomer has been copolymerized with caprolactone in varying ratios. After polymerization, the protecting group can be removed and an antibiotic can be attached as a new pendant group. The bioactivity of the antibiotic-bound poly(caprolactone) polymer is described.
    Type: Grant
    Filed: May 10, 2007
    Date of Patent: February 7, 2012
    Assignee: University of South Florida
    Inventors: Edward Turos, Michelle Leslie
  • Patent number: 7846920
    Abstract: The invention relates to heterosubstituted N-thiolated beta-lactams, compositions comprising these compounds, methods for their production, and methods of use as antibiotics to inhibit the growth of bacteria. In one embodiment, the compounds have the structure shown in formula (A) or formula (B) or formula (C): wherein the R groups are as defined in the specification. The antibacterial agents of the invention can be administered to a human or animal to treat or inhibit bacterial infection, such as that of Staphylococcus species, including methicillin-resistant Staphylococcus aureus (MRSA).
    Type: Grant
    Filed: September 7, 2007
    Date of Patent: December 7, 2010
    Assignee: University of South Florida
    Inventors: Edward Turos, Praveen Ramaraju
  • Publication number: 20100144699
    Abstract: Use of a monobactam antibiotic of formula (I) wherein the oxyimino group i.e. >C?N—O— has Z-orientation, or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the treatment of a bacterial infection in combination with a carbapenem antibiotic or a pharmaceutically acceptable salt thereof.
    Type: Application
    Filed: March 19, 2008
    Publication date: June 10, 2010
    Inventors: Eric Desarbre, Malcolm G.P. Page
  • Publication number: 20100056478
    Abstract: A pharmaceutically composition, comprising a combination of an antibiotically active compound of the formula (I): with a ?-lactamase inhibitor of one of the formulae (II) to (XIII) are active against Gram-negative bacteria, in particular such bacteria which have become resistant against antibiotics such as aztreonam, carumonam and tigemonam. Optionally the compositions may comprise another ?-lactamase inhibitor of one of the formulae (II) to (XIII), particularly of formula (V) or formula (VI).
    Type: Application
    Filed: December 7, 2006
    Publication date: March 4, 2010
    Inventors: Eric Desarbre, Bérangère Gaucher, Malcolm G.P. Page, Patrick Roussel
  • Publication number: 20100016274
    Abstract: Described herein are substituted 2-(azetidin-2-on-1-yl)alkanoic acids, alkanedioic acids and 2-hydroxyalkyl alkanoic acids, and 2-acyl alkanoic acids, and derivatives thereof, that are capable of modulating activity at the cannabinoid-1 (CB1) and/or cannabinoid-2 (CB2) receptor. Also described herein are methods for treating mammals in need of relief from disease states associated with and responsive to modulation of the CB1 and/or CB2 receptor activity.
    Type: Application
    Filed: September 14, 2007
    Publication date: January 21, 2010
    Inventors: Gary A. Koppel, Michael O. Chaney
  • Patent number: 7601832
    Abstract: A simplified process for the one-pot preparation of aztreonam, using azetidine and TAEM as starting materials, without the intermediary separation of t-butyl-aztreonam is provided.
    Type: Grant
    Filed: May 9, 2006
    Date of Patent: October 13, 2009
    Assignee: Sicor, Inc.
    Inventor: Domenico Fimognari
  • Publication number: 20090069286
    Abstract: The present application describes deuterium-enriched aztreonam, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
    Type: Application
    Filed: September 3, 2008
    Publication date: March 12, 2009
    Applicant: PROTIA, LLC
    Inventor: Anthony W. Czarnik
  • Patent number: 7501404
    Abstract: Compounds are provided which have the structure Wherein A, B, C, D, m, Y, Ra, Rc, Rd, and Rd? are as described herein, and which are useful as inhibitors of tryptase, thrombin, trypsin, Factor Xa, Factor VIIa, Factor XIa, and urokinase-type plasminogen activator and may be employed in preventing and/or treating asthma, chronic asthma, allergic rhinitis, and thrombotic disorders.
    Type: Grant
    Filed: April 4, 2006
    Date of Patent: March 10, 2009
    Assignee: DAIMED
    Inventors: Thomas Bannister, Cassandra Celatka, Nizal S. Chandrakumar, Hongfeng Deng, Zihong Guo, Lei Jin, Tsvetelina Lazarova, Jian Lin, Scott T. Moe, Pamela Nagafuji, Manuel Navia, Amy Ripka, Michael J. Rynkiewicz, Kerry L. Spear, James E. Stickler, Roger Xie
  • Publication number: 20090042819
    Abstract: The invention describes novel organic nitric oxide donor salts of a antimicrobial compounds, and novel compositions and kits comprising at least one organic nitric oxide donor salt of an antimicrobial compound, and, optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating bacterial infections; (b) treating viral infections; (c) treating fungal infections; and (d) treating lesions. In one embodiment the antimicrobial compounds of the invention are aztreonam, ciprofloxacin, doripenam, duramycin and tobramycin. The organic nitric oxide donors that form salts are preferably organic nitrates, organic nitrites, nitrosothiols, thionitrites and heterocyclic nitric oxide donors. The heterocyclic nitric oxide donors are preferably furoxans, sydnonimines, oxatriazole-5-ones and/or oxatriazole-5-imines.
    Type: Application
    Filed: February 16, 2006
    Publication date: February 12, 2009
    Applicant: NitroMed, Inc.
    Inventors: James L. Ellis, David S. Garvey, Chia-En Lin
  • Publication number: 20090018091
    Abstract: The invention describes compositions and kits comprising at least one nitric oxide enhancing group antimicrobial compound, or pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitric oxide enhancing antimicrobial compound, and, optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating bacterial infections; (b) treating viral infections; (c) treating fungal infections; and (d) treating lesions. The antimicrobial compounds of the invention are preferably tobramycin, aztreonam, ciprofloxacin and doripenam. The nitric oxide enhancing antimicrobial compounds are substituted with at least one heterocyclic nitric oxide donor group and/or at least one nitroxide group. The nitric oxide enhancing groups are nitroxides and/or heterocyclic nitric oxide donors. The heterocyclic nitric oxide donors are furoxans, sydnonimines, oxatriazole-5-ones and/or oxatriazole-5-imines.
    Type: Application
    Filed: August 2, 2006
    Publication date: January 15, 2009
    Applicant: NITROMED, INC.
    Inventors: James L. Ellis, David S. Garvey
  • Patent number: 7452991
    Abstract: The invention relates to the ? polymorph of Aztreonam, which contains less than 2.5% by weight residual solvent and to a process of making said polymorph. In the process of the invention, a polymorph of Aztreonam is dissolved in an absolute C1-6 alcohol in the presence of a base to form a solution, an acid is added to the solution, and the solution is stirred efficiently.
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: November 18, 2008
    Assignee: Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság
    Inventors: Viktor Gyollai, Csaba Szabo, Claude Singer, Ehud Amir
  • Publication number: 20080281094
    Abstract: The invention provides highly functionalised spiro-fused lactams of en formula (I) having a cyclohexane moiety with the desired number of protected or un-protected functional groups or carbonated structures, which are introduced with high stereo and regioselectivity, as well as processes for their obtention. These compounds are useful for the synthesis of abroad range of bioactive molecules, such as condoritols and aminoinositols and their analogues.
    Type: Application
    Filed: May 10, 2005
    Publication date: November 13, 2008
    Applicant: LABORATORIOS DEL DR. ESTEVE, S.A.
    Inventors: Pedro Noheda Marin, Manuel Bernabe Pajares, Sergio Maroto Quintana, Nuria Tabares Cantero, Raul Benito Arenas
  • Publication number: 20080167285
    Abstract: The invention relates to heterosubstituted N-thiolated beta-lactams, compositions comprising these compounds, methods for their production, and methods of use as antibiotics to inhibit the growth of bacteria. The antibacterial agents of the invention can be administered to a human or animal to treat or inhibit bacterial infection, such as that of Staphylococcus species, including methicillin-resistant Staphylococcus aureus (MRSA).
    Type: Application
    Filed: September 7, 2007
    Publication date: July 10, 2008
    Inventors: Edward Turos, Praveen Ramaraju
  • Patent number: 7262293
    Abstract: The present invention relates to the L-lysine salt of aztreonam and methods for making the L-lysine salt of aztreonam.
    Type: Grant
    Filed: July 1, 2004
    Date of Patent: August 28, 2007
    Assignee: Corus Pharma
    Inventors: Viktor Gyollai, Csaba Szabo, Claude Singer, Istvan Bodi
  • Patent number: 7214364
    Abstract: A method and a composition for treatment of pulmonary bacterial infections caused by gram-negative bacteria suitable for treatment of infection caused by Escherichia coli, Klebsiella pneumoniae, Klebsiella oxytoca, Pseudomonas aeruginosa, Haemophilus influenzae, Proteus mirabilis, Enterobacter species, Serratia marcescens as well as those caused by Burkholderia cepacia, Stenotrophomonas maltophilia, Alcaligenes xylosoxidans, and multidrug resistant Pseudomonas aeruginosa, using a concentrated formulation of aztreonam lysinate delivered as an aerosol or dry powder formulation.
    Type: Grant
    Filed: July 3, 2003
    Date of Patent: May 8, 2007
    Assignee: Corus Pharma, Inc.
    Inventor: Alan Bruce Montgomery
  • Patent number: 7026472
    Abstract: The subject invention concerns N-thiolated ?-lactam compounds of formula A, wherein R1 is a hydrocarbon group having 1–8 carbon atoms; R3 is an organothio group; and R4 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, or heterocycloalkenyl, and analogs and pharmaceutically acceptable salts, esters and amides thereof. The subject invention also concerns methods for inducing tumor cell death or inhibiting tumor cell proliferation, and methods for inducing DNA damage, inhibiting DNA replication, activating p38 MAP kinase, or activating caspase cascade activation, or releasing cytochrome C from mitochondria into the cytoplasm in a tumor cell. Methods for treating cancer using N-thiolated ?-lactam compounds, as well as pharmaceutical compositions comprising the same are further disclosed.
    Type: Grant
    Filed: May 6, 2003
    Date of Patent: April 11, 2006
    Assignee: University of South Florida
    Inventors: Q. Ping Dou, Edward Turos, David M. Smith
  • Patent number: 6946458
    Abstract: The invention relates generally to novel N-thiolated ?-lactams. More specially, the invention relates to the use of these novel antibacterial agents in the treatment or inhibition of methicillin-resistant Staphylococcus aureaus.
    Type: Grant
    Filed: November 5, 2002
    Date of Patent: September 20, 2005
    Assignee: University of South Florida
    Inventor: Edward Turos
  • Patent number: 6916803
    Abstract: The present invention relates to novel Syn isomers of racemates and optical isomers of 3-(heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids of the following formula: and their use in treating infections caused by gram-negative pathogenic bacteria.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: July 12, 2005
    Assignee: Pantherix, Ltd.
    Inventors: Ronald George Micetich, Samarendra Maiti, Charles Fiakpui, George Thomas, Andhe V. Narender Reddy, Sameeh M. Salama, Rajeshwar Singh
  • Publication number: 20040019203
    Abstract: The present invention relates to novel Syn isomers of racemates and optical isomers of 3-(heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids of formula (I) and its use in treating the infections caused by gram-negative pathogenic bacteria.
    Type: Application
    Filed: February 27, 2003
    Publication date: January 29, 2004
    Inventors: Ronald George Micetich, Samarendra Maiti, Charles Fiakpui, George Thomas, Andhe V. Narender Reddy, Sameeh M. Salama, Rajeshwar Singh
  • Publication number: 20030191108
    Abstract: The invention relates generally to novel N-thiolated &bgr;-lactams. More specially, the invention relates to the use of these novel antibacterial agents in the treatment or inhibition of methicillin-resistant Staphylococcus aureaus.
    Type: Application
    Filed: November 5, 2002
    Publication date: October 9, 2003
    Inventor: Edward Turos
  • Patent number: 6617451
    Abstract: Cis-&bgr;-lactam compounds having structure (II) are described herein which are prepared by enantioselective acylation of the free amine in the presence of Penicillin G Amidase.
    Type: Grant
    Filed: December 13, 2001
    Date of Patent: September 9, 2003
    Assignee: Eli Lilly and Company
    Inventors: Kathy Sue Crichfield, John Eric Hart, Radhe Krishan Vaid, Daniel Edward Verral
  • Patent number: 6562962
    Abstract: A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reacted with a &bgr;-lactam.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: May 13, 2003
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 6495568
    Abstract: Compounds of formula (I): or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity, wherein the broken line represents an optional bond; A is C or CH; B is CH2, O or absent; R1 and R2 are each independently selected from hydrogen, C1 to C6 alkyl optionally substituted with C1 to C4 alkoxy or phenyl, and C1 to C6 alkenyl; or, together with the carbon atom to which they are attached, form a C3 to C6 cycloalkyl group which optionally incorporates a heteroatom linkage selected from O, SO, SO2 and NR6 or which is optionally benzo-fused; R3 is hydrogen, halo, R7 or OR7; R4 is hydrogen, C1 to C4 alkyl, C1 to C4 alkoxy, trifluoromethyl or halo; R6 is hydrogen or C1 to C4 alkyl; R7 is an optionally substituted monocyclic or bicyclic ring system; m is 1 or 2; and n is 0, 1 or 2; with the proviso that B is not O when A is C; are MMP inhibitors useful in the treatment of, inter alia, tissue ulceration, wound repair and skin di
    Type: Grant
    Filed: October 12, 2001
    Date of Patent: December 17, 2002
    Assignee: Warner-Lambert Company
    Inventors: Kevin Neil Dack, Gavin Alistair Whitlock
  • Patent number: 6476015
    Abstract: Substituted monocyclic &bgr;-lactam compounds that are N-1-thiolated monolactams, and which exhibit wide-ranging antibacterial activities, having a single 4-membered azetidinone ring in which: the N-1 nitrogen atom of the azetidinone ring is bonded to sulfur but is not sulfonated, of the formula: wherein R1-5 are independently hydrogen, alkyl, heteroalkyl, aryl, heteroaryl, alkenyl, or alkynyl; X is H, C, or O; and n=0-3. Chemical synthesis of these compounds by a [2+2]-imine-acid chloride cycloaddition, and methods for subsequent derivatization, are also disclosed. The compounds and compositions disclosed herein are useful as antibacterial and antibiotic agents.
    Type: Grant
    Filed: July 24, 2000
    Date of Patent: November 5, 2002
    Assignee: University of South Florida
    Inventors: Edward Turos, Edward T. Carpenter, Timothy Long, Daniel V. Lim, Sonja S. Dickey
  • Patent number: 6437119
    Abstract: Processes for preparing compounds having two or three antibiotic functionalities using quinolone derivatives, &bgr;-lactams and vancomycin and the like as the starting materials and chloride linking agents; and the novel compounds prepared by these processes, are disclosed.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: August 20, 2002
    Inventor: William Lawrence Truett
  • Patent number: 6387931
    Abstract: Compounds of formula (I): or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity, wherein the broken line represents an optional bond; A is C or CH; B is CH2, O or absent; R1 and R2 are each independently selected from hydrogen, C1 to C6 alkyl optionally substituted with C1 to C4 alkoxy or phenyl, and C1 to C6 alkenyl; or, together with the carbon atom to which they are attached, form a C3 to C6 cycloalkyl group which optionally incorporates a heteroatom linkage selected from O, SO, SO2 and NR6 or which is optionally benzo-fused; R3 is hydrogen, halo, R7 or OR7; R4 is hydrogen, C1 to C4 alkyl, C1 to C4 alkoxy, trifluoromethyl or halo; R6 is hydrogen or C1 to C4 alkyl; R7 is an optionally substituted monocyclic or bicyclic ring system; m is 1 or 2; and n is 0, 1 or 2; with the proviso that B is not O when A is C; are MMP inhibitors useful in the treatment of, inter alia, tissue ulceration, wound repair and skin di
    Type: Grant
    Filed: October 12, 2001
    Date of Patent: May 14, 2002
    Assignee: Pfizer INC
    Inventors: Kevin Neil Dack, Gavin Alistair Whitlock
  • Patent number: 6335324
    Abstract: Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: January 1, 2002
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Gregory S. Bisacchi, William A. Slusarchyk, Uwe Treuner, James C. Sutton, Robert Zahler, Steven Seiler, David R. Kronenthal, Michael E. Randazzo, Mark D. Schwinden, Zhongmin Xu, Zhongping Shi
  • Patent number: 5994340
    Abstract: New 2-oxo-1-azetidine sulfonic acid derivatives with an aminoalkyl substituted "anti" (E-isomer) oxyimino group in the acylamino substituent at the 3 position of the monobactam ring. These compounds are potent inhibitors of bacterial .beta.-lactamases. These compounds can be used in combination with .beta.-lactam antibiotics to increase the effectiveness of the .beta.-lactam antibiotics in fighting infection caused by .beta.-lactamase producing bacteria.
    Type: Grant
    Filed: August 29, 1997
    Date of Patent: November 30, 1999
    Assignee: SynPhar Laboratories, Inc.
    Inventors: Samarendra N. Maiti, Oludotun A. Phillips, Eduardo L. Setti, Andhe V. Narender Reddy, Ronald G. Micetich, Fusahiro Higashitani, Chieko Kunugita, Koichi Nishida, Tatsuya Uji
  • Patent number: 5916887
    Abstract: In accordance with the present invention, there are provided 4-substituted-3-(2-amino-2-cycloalkyl methyl)-acetamido azetidin-2-one derivatives of the formula: ##STR1## wherein n is 1, 2 or 3; in which R.sub.1, R.sub.2 and R.sub.3 are as defined herein, and salts thereof, which exhibit excellent cysteine proteinase inhibitory activity and which can be used for treatment of different diseases such as muscular dystrophy, myocardial infarction, bone resorption, arthritis, cancer metastasis, pulmonary emphysema, septic shock, cerebral ischemia, memory function, Alzheimer and cataract, malaria, glomerular basement membrane degradation, bacterial infection, inflammatory diseases, parasitic infections, and viral infections.
    Type: Grant
    Filed: September 22, 1997
    Date of Patent: June 29, 1999
    Assignee: National Research Council of Canada
    Inventors: Rajeshwar Singh, Nian E. Zhou, Enrico O. Purisima, Ronald G. Micetich
  • Patent number: 5888998
    Abstract: A compound of formula (I) ##STR1## wherein R.sub.1 is selected from the group consisting of 2-thienyl, 2-furyl, 2-pyrrolyl, 1-methyl-2-pyrrolyl, 2-amino-1-thiazolyl and 5-isothiazolyl;R.sub.2 is selected from the group consisting of: ##STR2## and M is hydrogen or a pharmaceutically acceptable cation; wherein the oxyimino fragment (.dbd.N--OR.sub.2) in formula (I) is in the `anti` orientation.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: March 30, 1999
    Assignees: Synphar Laboratories, Inc., Taiho Pharmaceutical Co., Ltd.
    Inventors: Samarendra N. Maiti, Eduardo L. Setti, Oludotun A. Phillips, Andhe V. Narender Reddy, Ronald G. Micetich, Rajeshwar Singh, Fusahiro Higashitani, Chieko Kunugita, Koichi Nishida, Tatsuya Uji
  • Patent number: 5760219
    Abstract: Pyridyl substituted .beta.-lactam compounds used in preparing taxane derivatives having a 3' pyridyl substituted C13 side chain.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: June 2, 1998
    Assignee: Florida State University
    Inventors: Robert A. Holton, Kasthuri Rengan
  • Patent number: 5670638
    Abstract: The azetidines of the present invention have the formula I ##STR1## wherein R.sup.1 is hydrogen or bromine,R.sup.2 is hydrogen or bromine, wherein at least one of R.sup.1 or R.sup.2 is bromine,R.sup.3 is hydrogen; Me.sub.2 --C.dbd.C--COOR.sup.4 wherein R.sup.4 is hydrogen, methyl, benzyl or some other carboxy-protective group, andX is bromine or nitroxy group (--ONO.sub.2).According to the invention 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3-dibromo-4-oxo-azetidines are prepared by reacting derivatives of protected penicillanic acid 1,1-dioxides with DBN reactant (1,5-diazabicyclo/3.4.
    Type: Grant
    Filed: July 8, 1994
    Date of Patent: September 23, 1997
    Assignee: PLIVA farmaceutska
    Inventor: Irena Lukic
  • Patent number: 5318963
    Abstract: Antibacterial activity has been found in compounds of the formula.Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof, wherein: A is a bond or alkylene;Q completes a 5- or 6-membered saturated or unsaturated (including aromatic) heterocyclic ring having one or two, heteroatoms in the ring selected from nitrogen, ##STR2## sulfur or oxygen; X is attached to an available carbon atom in the heterocyclic ring and is hydrogen or oxo;Y is attached to an available carbon atom in the heterocyclic ring and is hydrogen, amino, hydroxyl, halogen, carboxamide, nitrile, or carboxyl, except that Y is not carboxyl when the bicyclic ring completed by Q is 2-quinolyl, 3-quinolyl, or quinoxalyl;and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: June 7, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Peter H. Ermann, Henner Straub
  • Patent number: 5290929
    Abstract: Antibacterial activity is exhibited by novel compounds having the formula ##STR1## where R.sub.1, R.sub.2, and M are as defined herein and X is --(CH.sub.2).sub.n -- wherein n is 0, 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: March 1, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William H. Koster, Joseph E. Sundeen, Henner Straub, Peter Ermann, Uwe D. Treuner, Kent Amsberry, Michael Fakes, Sailesh A. Varia
  • Patent number: 5254681
    Abstract: There is described a process for preparing monobactames of formula: ##STR1## where R=acyl, and their pharmaceutically acceptable salts, starting from ethyl (S)-3-hydroxybutanoate through the reaction intermediate (3S, 4R)-3-hydrazino-4-methyl-2-oxo-1-azetidine sulfonic acid or a salt thereof. This intermediate is new and therefore represents a further object of the present invention.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: October 19, 1993
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Giuseppe Guanti, Luca Banfi, Enrica Narisano, Giorgio Cevasco
  • Patent number: 5250525
    Abstract: The invention relates to novel 4-oxo-azetidine-2-sulfonic acids and their salts or the formula I ##STR1## wherein: R.sup.1 =hydrogen, halogen, phenylacetamido;R.sup.2 =hydrogen, halogen, phenylacetamido, phenoxyacetamido, phthalimido, 5-methyl-3-o-chlorophenyl-isoxazole-4-carboxamido;R.sup.3 =hydrogen, alkali metal, alkaline earth metal, quaternary ammonium group;R.sup.4 =hydrogen, SO.sub.2 O.sup.-+ NBu.sub.4 -n, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.3, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 -Ph, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 --C.sub.6 H.sub.4 --NO.sub.2 -p, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 --C.sub.6 H.sub.4 --CH.sub.3 -m.The products (I) may be used as intermediates in the synthesis of beta-lactamic antibiotics or as components in antimicrobial preparations.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: October 5, 1993
    Assignee: Pliva Handels GmbH
    Inventors: Mice Kovacevic, Zorica Mandic, Mirjana Tomic, Zinka Brkic, Jure J. Herak, Irena Lukic
  • Patent number: 5250676
    Abstract: Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; whereinR.sub.1 is said nucleophile;R is hydrogen, or protected amino,R.sub.2 is R.sub.4 as defined herein below;R.sub.3 is a leaving group; andR.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula--CH.sub.2 --CH.sub.2 --R.sub.6whereinR.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; orR.sub.6 is a group of the formula--COOR.sub.7or--COSR.sub.7in whichR.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: October 5, 1993
    Assignee: University of Notre Dame du Lac
    Inventors: Catherine M. Gasparski, Marvin J. Miller, Min Teng
  • Patent number: 5237059
    Abstract: A compound capable of generating an acid by light irradiation selected from the group consisting of oxime sulfonic acid esters of formula (I): ##STR1## wherein R.sup.1 is an alkyl group, each of R.sup.2 and R.sup.3 is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group and a cyano group, and R.sup.2 and R.sup.3 may optionally combine to form a ring; and N-hydroxyimidesulfonic acid esters of formula (II): ##STR2## wherein R.sup.1 is an alkyl group, and A is a group selected from the group consisting of a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group and a substituted or unsubstituted alkenylene group, wherein the compound capable of generating an acid by light irradiation is useful as an image-forming materials, etc. and has high reactivity to light of from the near ultraviolet region to the visible region.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: August 17, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kan Wakamatsu, Yuichi Wakata
  • Patent number: 5229381
    Abstract: New substituted azetidinones of the general formula (A') which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: July 20, 1993
    Assignee: Merck & Co., Inc.
    Inventors: James B. Doherty, Conrad P. Dorn, Paul E. Finke, William K. Hagmann, Malcolm MacCoss, Shrenik K. Shah