The Ring Nitrogen Is Shared By A Five-membered Ring Patents (Class 540/302)
  • Patent number: 8884005
    Abstract: The subject of the present invention is a method of the preparation of compounds containing the core skeleton of carbapenem antibiotics, novel intermediate compounds used in this method, a method of the preparation of the intermediate compounds as well as the use of the intermediate compounds in the production of carbapenem antibiotics.
    Type: Grant
    Filed: February 14, 2012
    Date of Patent: November 11, 2014
    Assignee: Instytut Chemi Organicznej Pan
    Inventors: Marek Chmielewski, Bartlomiej Furman, Sebastian Stecko, Irma Panfil, Margarita Jurczak, Paulina Mikolajczyk, Magdalena Soluch
  • Publication number: 20140148595
    Abstract: The subject of the present invention is a method of the preparation of compounds containing the core skeleton of carbapenem antibiotics, novel intermediate compounds used in this method, a method of the preparation of the intermediate compounds as well as the use of the intermediate compounds in the production of carbapenem antibiotics.
    Type: Application
    Filed: February 14, 2012
    Publication date: May 29, 2014
    Applicant: Instytut Chemi Organicznej Pan
    Inventors: Marek Chmielewski, Bartlomiej Furman, Sebastian Stecko, Irma Panfil, Margarita Jurezak, Paulina Mikolajezyk, Magdalena Soluch
  • Publication number: 20140057889
    Abstract: Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-2 or Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which are expressed anti-apoptotic Bcl-2 protein.
    Type: Application
    Filed: October 18, 2013
    Publication date: February 27, 2014
    Applicant: AbbVie Inc.
    Inventors: Milan Bruncko, Hong Ding, George A. Doherty, Steven W. Elmore, Lisa Hasvold, Laura A. Hexamer, Aaron R. Kunzer, Robert A. Mantei, William J. McClellan, Chang H. Park, Cheol-Min Park, Andrew M. Petros, Xiaohong Song, Andrew J. Souers, Gerard M. Sullivan, Zhi-Fu Tao, Gary T. Wang, Le Wang, Xilu Wang, Michael D. Wendt
  • Publication number: 20140057890
    Abstract: Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-2 or Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which are expressed anti-apoptotic Bcl-2 protein.
    Type: Application
    Filed: October 18, 2013
    Publication date: February 27, 2014
    Applicant: AbbVie Inc.
    Inventors: Milan Bruncko, Hong Ding, George A. Doherty, Steven W. Elmore, Lisa Hasvold, Laura A. Hexamer, Aaron R. Kunzer, Robert A. Mantei, William J. McClellan, Chang H. Park, Cheol-Min Park, Andrew M. Petros, Xiaohong Song, Andrew J. Souers, Gerard M. Sullivan, Zhi-Fu Tao, Gary T. Wang, Le Wang, Xilu Wang, Michael D. Wendt
  • Patent number: 8603947
    Abstract: A description is given of (4-haloalkyl-3-thiobenzoyl)cyclohexanediones of the formula (I) and of their use as herbicides. In this formula (I), X, Y, R1, R2, R3, and R4 are radicals such as hydrogen and organic radicals such as alkyl. A and Z are oxygen or alkylene.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: December 10, 2013
    Assignee: Bayer Cropscience AG
    Inventors: Hartmut Ahrens, Dieter Feucht, Elmar Gatzweiler, Isolde Haeuser-Hahn, Christopher Hugh Rosinger
  • Patent number: 8557979
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of ?-methyl carbapenems which are useful as antibacterial agents.
    Type: Grant
    Filed: July 27, 2012
    Date of Patent: October 15, 2013
    Assignee: FOB Synthesis, Inc.
    Inventors: Woo-Baeg Choi, Ewa Kowalik
  • Publication number: 20130172313
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment.
    Type: Application
    Filed: December 13, 2012
    Publication date: July 4, 2013
    Applicant: FOB SYNTHESIS, INC.
    Inventor: FOB Synthesis, Inc.
  • Publication number: 20130102017
    Abstract: Chromogenic or fluorescent carbapenems according to formula I, wherein Ar is a mono or disubstituted carbocyclic aromatic group or an optionally mono or disubstituted heterocyclic aromatic group, are useful compounds for the detection of bacterial carbapenemase.
    Type: Application
    Filed: July 4, 2011
    Publication date: April 25, 2013
    Inventors: Hans Rudolf Pfaendler, Gregor Golz
  • Publication number: 20120296084
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of ?-methyl carbapenems which are useful as antibacterial agents.
    Type: Application
    Filed: July 27, 2012
    Publication date: November 22, 2012
    Applicant: FOB Synthesis, Inc.
    Inventors: Woo-Baeg Choi, Ewa Kowalik
  • Patent number: 8232268
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of ?-methyl carbapenems which are useful as antibacterial agents.
    Type: Grant
    Filed: February 15, 2010
    Date of Patent: July 31, 2012
    Assignee: FOB Synthesis, Inc.
    Inventors: Woo-Baeg Choi, Ewa Kowalik
  • Publication number: 20110288289
    Abstract: The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem.
    Type: Application
    Filed: May 19, 2010
    Publication date: November 24, 2011
    Applicant: SAVIOR LIFETEC CORPORATION
    Inventors: Wei-Hong Tseng, Wen-Hsin Chang, Yuan-Liang Kuo, Chia-Mao Chang
  • Publication number: 20110172200
    Abstract: The present invention relates to a pharmaceutical composition with broad-spectrum of activity against class A, class C and D enzymes comprising an antibiotic and a pharmaceutically effective amount of a compound of Formula (I), compounds of Formula (I), the use of a therapeutically effective amount of one or more compounds of Formula (I) as a broad-spectrum beta-lactamase inhibitor and the use of such a pharmaceutical composition for the treatment of an infection in humans or animals caused by bacteria.
    Type: Application
    Filed: January 28, 2009
    Publication date: July 14, 2011
    Applicant: LEK PHARMACEUTICALS D. D.
    Inventors: Andrej Prezelj, Uros Urleb, Gregr Vilfan
  • Publication number: 20110166118
    Abstract: The present invention relates to a compound of Formula (I) in particular compounds of formula (Ia), the use of a therapeutically effective amount of one or more compounds of formula (I) or (Ia) as a broad-spectrum antibiotic and the use of a pharmaceutical composition comprising said compounds for the treatment of bacterial infections in humans or animals.
    Type: Application
    Filed: June 18, 2009
    Publication date: July 7, 2011
    Applicant: LEK PHARMACEUTICALS D.D.
    Inventors: Ivan Plantan, Andrej Prezelj, Uros Urleb, Barbara Mohar, Michel Stephan
  • Patent number: 7919616
    Abstract: The present invention relates to a carbapenem compound represented by formula (Ia) shown below: The carbapenem compound preferably has a crystalline form, and more preferably, the crystalline form has a powder X-ray diffraction pattern with peaks at 15.64, 9.93, 6.83, 6.52, 5.44, 5.01, 4.72, 4.50, 4.33, 4.24, 3.98, 3.85, 3.57, 3.41, 3.31, 3.10 2.76, and 2.67 as d-spacings (?).
    Type: Grant
    Filed: October 31, 2006
    Date of Patent: April 5, 2011
    Assignee: Nippon Soda Co., Ltd.
    Inventor: Satoshi Kajita
  • Publication number: 20100274003
    Abstract: The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.
    Type: Application
    Filed: September 17, 2008
    Publication date: October 28, 2010
    Applicant: Kukje Pharm Ind co. Ltd
    Inventors: Chang-Seob Kim, Dong-Woo Lee, Jae-Woo Lee, Mi-Ran Jung, Young-Cheol Jeong, Si-Min Kim, Young-Ro Choi, Dong-Geun Seo, Ju-Hee Lee, Phil-Sang Ahn
  • Patent number: 7683049
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions, wherein the compounds are generally of the Formulae The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment.
    Type: Grant
    Filed: June 10, 2005
    Date of Patent: March 23, 2010
    Assignee: FOB Synthesis, Inc.
    Inventors: Woo-Baeg Choi, Ewa Kowalik
  • Publication number: 20100063023
    Abstract: Provided is a ?-lactamase antibiotic and a compound of formula I, a process of producing the compound, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
    Type: Application
    Filed: September 9, 2009
    Publication date: March 11, 2010
    Applicant: Wyeth
    Inventors: Tarek Suhayl Mansour, Aranapakam Mudumbai Venkatesan
  • Publication number: 20100016208
    Abstract: Photoactivatable antimicrobial compounds and methods for the use thereof in the treatment of infections are provided.
    Type: Application
    Filed: November 15, 2006
    Publication date: January 21, 2010
    Applicant: THE GENERAL HOSPITAL CORPORATION
    Inventors: Tayyaba Hasan, Gerald J. Nau
  • Patent number: 7632828
    Abstract: The present invention provides ?-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions, wherein the compounds are generally of the Formulae The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of ÿ-methyl carbapenems which are useful as antibacterial agents.
    Type: Grant
    Filed: June 10, 2005
    Date of Patent: December 15, 2009
    Assignee: FOB Synthesis, Inc.
    Inventors: Woo-Baeg Choi, David S. Menaldino, Deog-Il Kim, Martin Bouygues, Michael W. Hager
  • Publication number: 20090143574
    Abstract: The present invention relates to a carbapenem compound represented by formula (Ia) shown below: The carbapenem compound preferably has a crystalline form, and more preferably, the crystalline form has a powder X-ray diffraction pattern with peaks at 15.64, 9.93, 6.83, 6.52, 5.44, 5.01, 4.72, 4.50, 4.33, 4.24, 3.98, 3.85, 3.57, 3.41, 3.31, 3.10 2.76, and 2.67 as d-spacings (?).
    Type: Application
    Filed: October 31, 2006
    Publication date: June 4, 2009
    Applicant: NIPPON SODA CO., LTD.
    Inventor: Satoshi Kajita
  • Patent number: 7538212
    Abstract: The present invention provides a novel intermediate represented by formula (1), (3), or (4) for efficiently producing a 1?-methylcarbapenem compound for oral administration, and a process for producing the intermediate. That is, the present invention provides a process for producing a novel ?-lactam compound represented by formula (4), the process including allowing a ?-lactam compound represented by formula (5) as a starting material to react with a compound represented by formula (6) in the presence of a base to obtain a novel ?-lactam compound represented by formula (1), protecting the hydroxyl group, subsequently performing cyclization in the presence of a strong base, allowing the cyclized compound to react with diphenylphosphoryl chloride to obtain a novel ?-lactam compound represented by formula (3), and eliminating the protecting group therefrom.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: May 26, 2009
    Assignee: Kaneka Corporation
    Inventors: Keita Nishino, Teruyoshi Koga
  • Publication number: 20090118496
    Abstract: The present invention relates to an azetidinone compound extremely useful as a common intermediate for the synthesis of 1?-methylcarbapenem compounds. The present invention provides a crystallization method to obtain a crystal which has a higher quality and a higher stability than a conventional crystal and is excellent in filterability at the time of recovering crystal; an azetidinone compound having a low content of impurity; and an azetidinone compound which has a controlled particle size distribution of crystals and improved handleability and stability. The crystallization is carried out by adding a hydrocarbon solvent to a solution in which an azetidinone compound extremely useful as a common intermediate for the synthesis of 1?-methylcarbapenem compounds is dissolved in the presence of a seed crystal in an amount of 200% by weight or less based on the weight of the azetidinone compound.
    Type: Application
    Filed: April 18, 2007
    Publication date: May 7, 2009
    Applicant: KANEKA CORPORATION
    Inventors: Keita Nishino, Teruyoshi Koga, Masafumi Fukae, Yasuyoshi Ueda
  • Patent number: 7524951
    Abstract: The present invention relates to compounds represented by formula (1) and a process for producing the same. The use of these compounds can realize the production of carbapenem derivatives having potent antimicrobial activity and a wide antimicrobial spectrum in a safe and cost-effective manner.
    Type: Grant
    Filed: December 15, 2003
    Date of Patent: April 28, 2009
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Toshiro Sasaki, Takashi Ando, Yasuo Yamamoto, Takahiro Imai, Dai Kubota, Katsuhiko Noguchi, Nobuyuki Hori, Eiki Shitara, Kunio Atsumi, Shohei Yasuda
  • Patent number: 7468364
    Abstract: Carbapenem compounds represented by the general formula [1] or pharmaceutically acceptable salts thereof: wherein R1 is C1-C3 alkyl or hydroxylated C1-C3 alkyl, R is hydrogen atom or a group which is hydrolyzed in vivo into a carboxy group, and G is a group represented by one of the formulae [G1], [G2], and [G3].
    Type: Grant
    Filed: April 6, 2004
    Date of Patent: December 23, 2008
    Assignee: Dainippon Sumitomo Pharma Co., Ltd.
    Inventors: Makoto Sunagawa, Akira Sasaki, Seiji Hori
  • Patent number: 7459551
    Abstract: The present invention provides a method for preparing a ?-lactam compound of the following Formula (3), which comprises the step of reacting a compound of the following Formula (1) with a trialkyl phosphite represented by the formula (R5O)3P (wherein R5 represents an ethyl group, etc.) in an amount of 2 to 5 moles per mole of the compound and the step of heating the resulting reaction mixture in a diluent, wherein said method is characterized by having the step of completely removing unreacted trialkyl phosphite from the reaction mixture prior to the step of heating. (wherein X represents S, etc., Y represents N, etc., n represents 0 or 1, R1 represents an optionally substituted alkyl group containing 1 to 10 carbon atoms, etc., R2 and R3 each represent an optionally substituted alkyl or heterocyclic group, etc., and R4 represents an alkenyloxy group containing 1 to 6 carbon atoms, etc., provided that R1 and R2 may together form a ?-lactam ring, etc.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: December 2, 2008
    Assignee: Asubio Pharma Co., Ltd.
    Inventor: Akira Kaneko
  • Publication number: 20080076917
    Abstract: The present invention relates to compounds represented by formula (1) and a process for producing the same. The use of these compounds can realize the production of carbapenem derivatives having potent antimicrobial activity and a wide antimicrobial spectrum in a safe and cost-effective manner.
    Type: Application
    Filed: December 15, 2003
    Publication date: March 27, 2008
    Applicant: Meiji Seika Kaisha, Ltd.
    Inventors: Toshiro Sasaki, Takashi Ando, Yasuo Yamamoto, Takahiro Imai, Dai Kubota, Katsuhiko Noguchi, Nobuyuki Hori, Eiki Shitara, Kunio Atsumi, Shohei Yasuda
  • Patent number: 7205291
    Abstract: A compound or its pharmaceutically acceptable salt represented by the following formula: The invention is a carbapenem compound which has a potent antibacterial activity over a broad range of Gram negative and Gram positive bacteria, especially penicillin-resistant Streptococcus pneumoniae (PRSP) which has been isolated at an elevated frequency in recent years and thus causes a serious clinical problem, and Haemophilus influenzae which has acquired resistance against the existing ?-lactam antibiotics over a wide scope due to penicillin-binding protein (PBP) mutations such as ?-lactamase non-producing ampicillin-resistant (BLNAR) Haemophilus influenzae, and has excellent oral absorbability.
    Type: Grant
    Filed: November 1, 2002
    Date of Patent: April 17, 2007
    Assignee: Dainippon Sumitomo Pharma Co., Ltd.
    Inventors: Makoto Sunagawa, Akira Sasaki
  • Patent number: 7148356
    Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.
    Type: Grant
    Filed: March 14, 2005
    Date of Patent: December 12, 2006
    Assignee: Board of Trustees of Michigan State University
    Inventors: Milton R. Smith, III, Robert E. Maleczka
  • Patent number: 7115595
    Abstract: Carbapenem compounds having a substituted phenyl or a substituted thienyl directly attached to the 3-position of carbapenem nucleus as represented by the formula: wherein Ring E is benzene ring or thiophene ring; R1 is optionally OH-substituted C1-3 alkyl; R2 and R3 represent each H, optionally substituted lower alkyl, etc.; R is H, or a group which is hydrolyzed in the living body to regenerate a carboxyl group, etc.; X is O or S; and Y represents H, lower alkyl, etc., or pharmaceutically acceptable salts thereof and medicaments containing said compound as the active ingredient.
    Type: Grant
    Filed: December 25, 2001
    Date of Patent: October 3, 2006
    Assignee: Dainippon Sumitomo Pharma Co., Ltd.
    Inventors: Makoto Sunagawa, Akira Sasaki
  • Patent number: 7045619
    Abstract: A compound of formula (I): wherein R? is hydrogen, optionally substituted (C1-6)alkyl or optionally substituted aryl; R? is hydrogen, optionally substituted (C1-6)alkyl or optionally substituted aryl; or R? and R? together form an optionally substituted 5 or 6 membered heterocyclic ring with or without additional heteroatoms; R1 is (C1-6)alkyl which is unsubstituted or substituted by fluoro, a hydroxy group which is optionally protected by a removable hydroxy protecting group, or by an amino group which is optionally protected by a removable amino protecting group; R2 is hydrogen or methyl; and —CO2R3 is carboxy or a carboxylate anion or the group R3 is a removable carboxy protecting group. This invention also relates to processes for its preparation, intermediates and pharmaceutical compositions comprising compounds of formula (I).
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: May 16, 2006
    Assignee: SmithKline Beecham p.l.c.
    Inventors: Eric Hunt, Steven Coulton, Jeremy David Hinks, Stephen Frederick Moss, Stephen Christopher Martin Fell, Alfred John Eglington, George Burton
  • Patent number: 7041836
    Abstract: The present invention relates to carbapenems and provides a compound of the formula (I): or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4alkyl; R3 is hydrogen or C1-4alkyl; R4 and R5 are the same or different and are selected from hydrogen, halo, cyano, C1-4alkyl, nitro, hydroxy, carboxy, C1-4alkoxy, C1-4alkoxycarbonyl, aminosulphonyl, C1-4alkylaminosulphonyl, di-C1-4-alkylaminosulphonyl, carbamoyl, C1-4alkylcarbamoyl, di-C1-4-alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C1-4alkylamino, di-C1-4alkylamino, C1-4alkanoylamino, C1-4alkanoyl(N—C1-4alkyl)amino, C1-4alkanesulphonamido and C1-4alkylS(O)n— wherein n is zero, one or two: with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to —NR3—. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.
    Type: Grant
    Filed: November 14, 2002
    Date of Patent: May 9, 2006
    Assignee: AstraZeneca UK Limited
    Inventors: Michael John Betts, Gareth Morse Davies, Michael Lingard Swain
  • Patent number: 6908913
    Abstract: An objective of the present invention is to provide carbapenem derivatives which have strong antibiotic activity also against MRSA, PRSP, Influenzavirus, and ?-lactamase producing bacteria and are stable to DHP-1. The carbapenem derivatives according to the present invention are compounds represented by formulae (I) and (II) or pharmaceutically acceptable salts thereof: wherein R1 represents H or methyl, R2 and R3 each independently represent H; halogen; substituted or unsubstituted alkyl; cycloalkyl; substituted or unsubstituted alkylcarbonyl; carbamoyl; substituted or unsubstituted aryl; substituted or unsubstituted alkylthio; morpholinyl; alkylsulfonyl; or formyl, n is 0 (zero) to 4, and Hy represents a substituted or unsubstituted monocyclic or bicyclic heterocyclic group.
    Type: Grant
    Filed: November 22, 2001
    Date of Patent: June 21, 2005
    Assignee: Meiji Seiki Kaisha, Ltd.
    Inventors: Yuko Kano, Yasuo Yamamoto, Takahisa Maruyama, Takehiko Sawabe, Eiki Shitara, Kazuhiro Aihara, Kunio Atsumi, Takashi Ida
  • Patent number: 6867302
    Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: March 15, 2005
    Assignee: Board of Trustees of Michigan State University
    Inventors: Milton R. Smith, III, Robert E. Maleczka
  • Patent number: 6825187
    Abstract: An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1. The compounds according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts thereof: wherein R1 represents H or methyl; R2 and R3 each independently represent H, halogen, lower alkyl or the like; R4 represents optionally substituted lower alkylthio or the like; and R5 represents optionally substituted lower alkyl or the like.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: November 30, 2004
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuko Kano, Takahisa Maruyama, Yasuo Yamamoto, Eiki Shitara, Toshiro Sasaki, Kazuhiro Aihara, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Patent number: 6680313
    Abstract: An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1. The compounds according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts thereof: wherein R1 represents H or methyl; R2 and R3 represent H, a halogen atom, alkyl or the like; and R4 represents substituted lower alkylthio or the like.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: January 20, 2004
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuko Kano, Takahisa Maruyama, Yumiko Sambongi, Kazuhiro Aihara, Kunio Atsumi, Kastuyoshi Iwamatsu, Takashi Ida
  • Patent number: 6677331
    Abstract: Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1.
    Type: Grant
    Filed: August 14, 2002
    Date of Patent: January 13, 2004
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuko Kano, Toshiro Sasaki, Yumiko Sambongi, Kiyoshi Tanabe, Yoshihisa Akiyama, Hideo Kitagawa, Takahisa Maruyama, Hiromasa Takizawa, Takashi Ando, Kazuhiro Aihara, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Patent number: 6531466
    Abstract: A compound of formula (I), salts and metabolically labile esters thereof, wherein R represents optionally substituted aryl or heteroaryl group; A represents a propylene chain or A is a chain of 3 members one of which is selected from an oxygen or sulphur atom or the group NH or a substituted derivative thereof and the other two members are methylene groups, having antibacterial activity, processes for their preparation and to their use in medicine.
    Type: Grant
    Filed: February 13, 2001
    Date of Patent: March 11, 2003
    Assignee: GlaxoSmithKline SpA
    Inventors: Tino Rossi, Daniele Andreotti, Giovanna Tedesco, Luca Tarsi, Emiliangelo Ratti, Aldo Feriani, Domenica Antonia Pizzi, Giovanni Gaviraghi, Stefano Biondi, Gabriella Finizia
  • 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
  • Patent number: 6489318
    Abstract: Disclosed are novel ethylidene derivatives of tricyclic carbapenems of the formula I wherein the ring marked C and X have the meaning as in the description, in the form of pure diastereoisomers and in the form of pure geometric isomers. Novel ethylidene derivatives of tricyclic carbapenems of the formula I are used as inhibitors of the action of the enzyme &bgr;-lactamase and/or as antibiotics in human and veterinary medicine. Also disclosed are pharmaceutical formulations for the treatment of bacterial infections of human and animal organisms comprising as an active ingredient a therapeutically effective amount of an ethylidene derivative of tricyclic carbapenems of the formula I in the form of an acid, a pharmaceutically acceptable salt or ester thereof and optionally in a combination with a &bgr;-lactam antibiotic, and usual pharmaceutically acceptable carriers and auxiliary substances.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: December 3, 2002
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d.
    Inventors: Anton {haeck over (C)}opar, Toma{overscore (z)} {overscore (S)}olmajer, Borut An{haeck over (z)}i{haeck over (c)}, Tadeja Kuzman, Toma{overscore (z)} Mesar, Darko Kocjan
  • Patent number: 6489471
    Abstract: A process of synthesizing a carbapenem compound of formula (6) is disclosed, wherein R represents H or methyl, P and P* independently represent H or protecting groups and each R1 is independently selected from: H, halo, OH, OP wherein P is a protecting group, C1-6 alkyl or C1-6 alkyl substituted with 1-3 of halo, OH, OP, NH2, NHC1-4 alkyl or N(C1-4 alkyl)2, comprising reacting a carbapenem of formula (4′) with a compound of formula (7), wherein R, R1, P and P* are as previously defined and R2 represents acetate, C(O)OR′ or P(O)(OR″)2, wherein R′ and R″ independently represent Clot alkyl, benzyl or aryl, in the presence of a catalyst to produce a compound of formula (6).
    Type: Grant
    Filed: March 5, 2001
    Date of Patent: December 3, 2002
    Assignee: Merck & Co., Inc.
    Inventors: Guy R. Humphrey, Ross A. Miller, Nobuyoshi Yasuda
  • Patent number: 6458780
    Abstract: Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti-microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: October 1, 2002
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuko Kano, Toshiro Sasaki, Yumiko Sambongi, Kiyoshi Tanabe, Yoshihisa Akiyama, Hideo Kitagawa, Takahisa Maruyama, Hiromasa Takizawa, Takashi Ando, Kazuhiro Aihara, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Patent number: 6395894
    Abstract: A process of synthesizing a compound of structural formula 6 is disclosed wherein R1 represents H or a suitable protecting group for an alcohol; R2 represents a benzyl, C1-6 alkyl or aryl; Y represents C1-3 alkyl, O, NH or S; X represents O, NH, or S and R5 represents a carboxy protecting group, comprising reacting a compound of formula 5: wherein R1, R2, R5, X and Y are as previously described with a phosphite or phosphonite reagent to produce a compound of formula 6. Further disclosed is an efficient method for the synthesis of a compound of formula 2: which comprises reacting a 4-acyl-2-azetidinone with a titanium, zirconium or hafnium enolate of a 1-hydroxy-2-butanone derivative.
    Type: Grant
    Filed: April 15, 1999
    Date of Patent: May 28, 2002
    Inventors: Philip J. Pye, Paul J. Reider, Kai Rossen, Ralph P. Volante
  • Patent number: 6346526
    Abstract: Compounds of formula I: as well as pharmaceutically acceptable salts thereof useful as carbapenem antibacterial agents are disclosed wherein X is CH2 or C═O.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: February 12, 2002
    Assignee: Merck & Co., Inc.
    Inventors: Timothy A. Blizzard, Kevin D. Dykstra, Ronald W. Ratcliffe
  • Patent number: 6346525
    Abstract: Compounds of formula I: as well as pharmaceutically acceptable salts thereof and compositions useful as carbapenem antibacterial agents are disclosed.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: February 12, 2002
    Assignee: Merck & Co., Inc.
    Inventors: Timothy A. Blizzard, Ronald W. Ratcliffe, Sherman T. Waddell, Jerry D. Morgan, II
  • Patent number: 6346617
    Abstract: A process for preparation of a compound of formula I: wherein: R1 represents CH3 or H; and P represents a protecting group; comprising reacting a compound of formula IV:  wherein R1 and P and are defined above and R4 represents triflate or SO2F; in the presence of a catalyst and (R3)3SnCH2OP″, wherein each R3 represents C1-4 lower alkyl, and P″ represents H or a protecting group, to yield the compound of formula I.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: February 12, 2002
    Assignee: Merck & Co., Inc.
    Inventors: John Y. Chung, Nobuyoshi Yasuda, Johnnie L. Leazer, Jr., Mark S. Jensen, Kenneth M. Wells, Chunhua Yang
  • Publication number: 20010047094
    Abstract: A compound of formula (1), salts and metabolically labile esters thereof, wherein R represents optionally substituted aryl or heteroaryl group; A represents a propylene chain or A is a chain of 3 members one of which is selected from an oxygen or sulphur atom orthe group NH or a substituted derivative thereof and the other two members are methylene groups, having antibacterial activity, processes for their preparation and to their use in medicine.
    Type: Application
    Filed: February 13, 2001
    Publication date: November 29, 2001
    Applicant: Glaxo Wellcome SpA
    Inventors: Tino Rossi, Daniele Andreotti, Giovanna Tedesco, Luca Tarsi, Emiliangelo Ratti, Aldo Feriani, Domenica Antonia Pizzi, Giovari Gaviraghi, Stefano Biondi, Gabriella Finizia
  • Patent number: 6310056
    Abstract: The carbapenem derivatives represented by the following formula (I) is disclosed.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: October 30, 2001
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yuko Kano, Kazuhiro Aihara, Yumiko Toyooka, Toshiro Sasaki, Hiromasa Takizawa, Kenichi Fushihara, Kazuko Kobayashi, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Patent number: 6310055
    Abstract: The present invention relates to carbapenem antibacterial agents in which the carbapenem nucleus is substituted at the 2 -position with a iodophenoxy linked through a group —Z—CH2—; The compound is further substituted with various substituent groups including at least one cationic group. The compounds are represented by formula I: wherein Z represents trans-ethenediyl or ethynediyl. Pharmaceutical compositions and methods of use are also included.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: October 30, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. Dininno, Kevin D. Dykstra
  • Publication number: 20010025103
    Abstract: An efficient method for the synthesis of a compound of formula 2: 1
    Type: Application
    Filed: April 15, 1999
    Publication date: September 27, 2001
    Inventors: PHILIP J. PYE, PAUL J. REIDER, KAI ROSSEN, RALPH P. VOLANTE
  • Patent number: 6294528
    Abstract: Compounds of formula I: as well as pharmaceutically acceptable salts therefor and compositions useful as carbapenem antibacterial agents are disclosed.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: September 25, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Timothy A. Blizzard, Robert R. Wilkening, Ronald W. Ratcliffe