The Ring Nitrogen Is Shared By A Five-membered Ring Patents (Class 540/302)
The five-membered ring contains an additional hetero atom (Class 540/303)
The ring system is 4-aza-bicyclo(3.2.0)heptane (including unsaturated) and has sulfur bonded directly at the 2-position (Class 540/350)
  • Carbapenem antibiotics, compositions containing such compounds and methods of use
    Patent number: 5532261
    Abstract: Compounds are disclosed represented by the formula: ##STR1## wherein Y is: ##STR2## or a pharmaceutically acceptable salt or ester thereof. ##STR3## represents an aromatic 6 membered ring; zero or one of T, U, V and W represents N.sup.+ R.sup.y and the remainder of T, U, V and W are independently selected from C and N, such that one of T, U, V and W represents N.sup.+ R.sup.y or N.Pharmaceutical compositions and methods of use are also included.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: July 2, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Ravindra N. Guthikonda, Laura C. Meurer
  • Process for synthesizing carbapenem intermediates using a rhodium catalyst and lewis acid
    Patent number: 5493018
    Abstract: This invention relates to the synthesis of a bicyclic ketoester compound of the formula 1 obtained by cyclizing a diazo compound of formula 2: in the presence of a rhodium catalyst. ##STR1## By adding an effective amount of a Lewis acid to the cyclization reaction, the reaction selectively produces the 1-beta methyl isomer, and epimerization of the 1-beta methyl compound to the 1-alpha isomer is minimized.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Thomas Meng-Han Liu, Joseph E. Lynch, Ralph P. Volante
  • Tricyclic or tetracyclic carbapenem compounds, their production and use
    Patent number: 5459260
    Abstract: A polycyclic carbapenem compound of the formula (Ia'), (Ib') or (Ic') ##STR1## [wherein COOR.sup.2 is a carboxy group which may be esterified; R.sup.a' is --(CH.sub.2).sub.m --K.sup.a --(CH.sub.2).sub.n --U.sup.a' ; J is O or S; R.sup.b' is --(CH.sub.2).sub.m --K.sup.b --(CH.sub.2).sub.n U.sup.b' ; J' is O, S or CH.sub.2 ; R.sup.c' is --(CH.sub.2).sub.m --K.sup.c --(CH.sub.2).sub.n --U.sup.c', --(CH.sub.2).sub.m --K.sup.d --(CH.sub.2).sub.n --U.sup.d or a pair of groups, one of which is a hydroxy group, with the other being a hydroxzy group or an alkylsulfonylamino group, which may be substituted, in the position ortho to the first-mentioned hydroxy group] or a salt thereof are useful as an antibacterial agent.
    Type: Grant
    Filed: September 22, 1993
    Date of Patent: October 17, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Michiyuki Sendai, Tetsuo Miwa
  • 1-.beta.-methyl-carbapenem, compositions containing same and methods of use
    Patent number: 5451579
    Abstract: A carbapenem antibiotic of the formula I ##STR1## is disclosed. The variable X.sup..crclbar. represents a counterion. Pharmaceutical compositions and methods of use are also disclosed.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: September 19, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Mark L. Greenlee, Frank P. DiNinno, Milton L. Hammond
  • Preparation of 2-aryl carbapenems
    Patent number: 5442056
    Abstract: The present invention is directed to a process of making 2-aryl carbapenems of formula 1 from a compound of formula A.
    Type: Grant
    Filed: May 17, 1994
    Date of Patent: August 15, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Ann E. DeCamp, Edward J. J. Grabowski, Mark A. Huffman, Lyndon C. Xavier, Nobuyoshi Yasuda
  • Preparation of 2-aryl carbapenems via a boronic acid coupling reaction
    Patent number: 5442057
    Abstract: The present invention is directed to a process of making 2-Aryl Carbapenems of Formula 1 from a compound of formula 2.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: August 15, 1995
    Inventors: Ann Decamp, Ulf H. Dolling, Yulan Li, Dale L. Rieger, Nobuyoshi Yasuda, Lyndon C. Xavier
  • Tricyclic carbapenem compounds, methods of preparation and methods of use
    Patent number: 5426104
    Abstract: Compounds of general formula (I) ##STR1## in which R.sub.1 represents a hydrogen atom or a hydroxyl protecting group, R.sub.2 represents a hydrogen atom or a carboxyl protecting group, and R.sub.3 represents the group N(R.sub.4)--CH.dbd.NR.sub.5 wherein R.sub.4 represents a hydrogen atom and R.sub.5 represents a hydrogen atom; and salts, metabolically labile esters and solvates thereof and a process for their production. The compounds of formula (I) are either antibacterial agents and or useful intermediates for the preparation of antibacterial agents.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: June 20, 1995
    Assignee: Glaxo SpA
    Inventors: Alcide Perboni, Daniele Donati, Giorgio Tarzia
  • Process for preparing .beta.-lactam derivative and synthetic intermediate thereof
    Patent number: 5414081
    Abstract: Disclosed is a process for preparing a .beta.-lactam compound represented by the formula: ##STR1## wherein R.sup.1 represents a hydroxy-substituted lower alkyl group or an amino group each of which may be protected; R.sup.2 represents hydrogen atom or an ester residue; X represents a methylene group which may be substituted by a lower alkyl group, sulfur atom or a group represented by the formula: --A--CH.sub.2 -- where A represents sulfur atom, oxygen atom or methylene group; and W represents an active ester residue of hydroxyl group, or a salt thereof, which comprises the steps of treating a 1-aza-3-thia-bicycloalkane compound represented by the formula: ##STR2## wherein R.sup.1, R.sup.2 and X have the same meanings as defined above, or a salt thereof with a base in the presence of a desulfurizing agent and then reacting the resulting compound with an active esterifying agent of hydroxyl group.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: May 9, 1995
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hiroshi Horikawa, Kazuhiko Kondo, Tameo Iwasaki
  • 2-(3-pyridyl)-carbapenem antibacterial agents
    Patent number: 5409920
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: April 25, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Ravindra N. Guthikonda, Frank P. DiNinno
  • Tetracyclic antibiotics and processes for their preparation
    Patent number: 5405844
    Abstract: Tetracyclic antibiotics and processes for their preparation .beta.-Lactam antibiotics of the formula I, and their pharmaceutically tolerable salts ##STR1## where X is (CH.sub.2).sub.0-2, CR(a)R(b), O, SO.sub.0-2 or NR(c),R1, R2 and R3 are a multiplicity of substituents, are outstanding antibiotics with remarkably good antibacterial activity both against gram-positive and against gram-negative microorganisms. They have a high stability to renal dehydropeptidase.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: April 11, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Uwe Gerlach, Rolf Horlein, Norbert Krass, Rudolf Lattrell, Theo Wollmann, Michael Limbert, Astrid Markus
  • Bridged biphenyl carbapenem antibacterial compounds
    Patent number: 5401735
    Abstract: Carbapenems of the formula: ##STR1## are disclosed as useful antibacterial agents.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: March 28, 1995
    Assignee: Merck & Co., Inc.
    Inventor: Frank P. Dininno
  • Tricyclic carbapenem compounds
    Patent number: 5393751
    Abstract: A compound of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a hydrocarbon group which may be substituted; COOR.sup.2 represents a carboxy group which may be esterified; and ring B is a cyclic group which may be substituted or a pharmaceutically acceptable salt thereof are useful as an antibacterial agent.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: February 28, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Michiyuki Sendai, Tetsuo Miwa
  • Bridged biphenyl carbapenem compounds, compositions containing such compounds and methods of use
    Patent number: 5384317
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: January 24, 1995
    Assignee: Merck & Co., Inc.
    Inventor: Frank P. DiNinno
  • (N-pyridiniumphenyl)-carbapenems
    Patent number: 5382575
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: October 7, 1992
    Date of Patent: January 17, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Alan D. Adams, Frank DiNinno, James V. Heck
  • Bridged carbapenem antibacterial compounds
    Patent number: 5374630
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 20, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Frank P. DiNinno
  • Bridged carbapenem compounds, compositions containing such compounds and methods of use
    Patent number: 5372993
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents. Compositions containing such compounds and methods of use are also disclosed.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 13, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Frank P. DiNinno
  • 4-substituted azetidinones as precursors to 2-substituted-3-carboxy carbapenem antibiotics and a method of producing them
    Patent number: 5371215
    Abstract: New 4-substituted azetidinones having the formulae I and II: ##STR1## wherein X is oxygen, sulfur or a moiety of the formula NR.sup.6 where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined hereafter, which are intermediates for the preparation of carbapenem and carbacephem antibacterials and processes for producing such antibacterials through the utilization of an acid mediated ring closure reaction.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: December 6, 1994
    Assignee: American Cyanamid Company
    Inventors: Gregg B. Feigelson, William V. Curran, Carl B. Ziegler
  • 2-substituted alkyl-3-carboxy carbopenems as antibiotics and a method of producing them
    Patent number: 5369102
    Abstract: The invention relates to new 2-substituted alkyl-3-carboxy carbapenems having the formula: ##STR1## with R.sup.1, R.sup.2, R.sup.3, X and Y defined hereafter as antibiotics and beta lactamase inhibitors produced by a novel Michael addition-elimination reaction of a substituted allyl azetidinone in the reaction shown: ##STR2## with R.sup.1, R.sup.2, Q, X and Y defined hereafter.
    Type: Grant
    Filed: July 6, 1993
    Date of Patent: November 29, 1994
    Assignee: American Cyanamid Company
    Inventors: Carl B. Ziegler, Jr., William V. Curran, Gregg Feigelson
  • 2-(heterocyclylheteroaryliumalkyl) phenyl carbapenem antibacterial agents
    Patent number: 5362723
    Abstract: Carbapenems having the formula: ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: November 8, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Thomas N. Salzmann, David A. Muthard
  • 2-(9-fluorenonyl)-carbapenem intermediates
    Patent number: 5356889
    Abstract: Disclosed are carbapenems of the formula ##STR1## which are 2-(9-fluorenonyl)-carbapenems useful as antibacterial agents. Intermediates for preparation of these compounds is also disclosed.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: October 18, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Mark L. Greenlee, Frank P. DiNinno, Lovji D. Cama, James V. Heck
  • Triazolyl and tetrazolyl phenyl substituted carbapenems, compositions containing such compounds and methods of use
    Patent number: 5350746
    Abstract: Triazolyl and tetrazolyl phenyl substituted carbapenems of the formula I are disclosed. ##STR1## One or two of the variables X, Y and Z represent nitrogen atoms. The heteroaryl ting may be charged or uncharged.Pharmaceutical compositions and methods of treatment are also disclosed.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: September 27, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Alan D. Adams, James V. Heck
  • 2-biphenyl-carbapenems
    Patent number: 5350846
    Abstract: Carbapenems of the formula: ##STR1## are useful intermediates to antibacterial agents.
    Type: Grant
    Filed: January 25, 1993
    Date of Patent: September 27, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Thomas N. Salzmann
  • Cationic-2-heteroarylphenyl-carbapenem antibacterial agents
    Patent number: 5342933
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: August 28, 1992
    Date of Patent: August 30, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Susan M. Schmitt, Ravindra N. Guthikonda
  • Optically active pyrrolidine derivative
    Patent number: 5342963
    Abstract: Optically active pyrrolidine derivative represented by the following formula (XI): ##STR1## wherein R.sup.1 represents a benzyl group R.sup.2 represents an alkyl group having 1 to 6 carbon atoms, R.sup.3 represents an alkyl group having 1 to 6 carbon atoms, a benzyl group or an allyl group, R.sup.4 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted with a protected hydroxyl group, a vinyl group, a phenyl group which may be substituted, a benzyl group which may be substituted, and a heterocyclic ring having 1 to 4 nitrogen or/and oxygen atoms, and R.sup.5 represents a hydrogen atom or a methyl group.This compound can be an intermediate for synthesis of carbapenem antibiotic compounds.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: August 30, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kuniya Sakurai, Kunisuke Izawa, Hiroyuki Izawa, Takashi Ineyama, Tomihisa Ohta, Shigeo Nozoe
  • Naphthalene derivatives, processes for preparing the same, and synthetic intermediates therefor
    Patent number: 5342941
    Abstract: Naphthalene derivative of the formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen atom, hydroxy group, cyclo-lower alkyloxy group, substituted or unsubstituted lower alkoxy group, or both combine each other to form lower alkylenedioxy group, R.sup.3 is substituted or unsubstituted nitrogen-containing 6-membered heterocyclic group, and groups of the formulae: --OR.sup.4 and --OR.sup.5 are the same or different and are protected or unprotected hydroxy group, processes for preparing thereof, and synthetic intermediates therefor, these compounds have excellent bronchodilating activity, and are useful in the prophylaxis and treatment of asthma.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: August 30, 1994
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo, Katsuo Ikezawa, Hideo Kikkawa, Shinsuke Yamagata
  • Isoxazolidinyl carbapenem derivative
    Patent number: 5338733
    Abstract: A carbapenem derivative represented by Formula I: ##STR1## wherein R.sup.1 is hydrogen or a hydroxy protecting group; R.sup.2 is substituted or non-substituted lower alkyl; R.sup.3 is hydrogen, an inorganic or organic base, or a carboxy protecting group; and R.sup.4 is a compound represented by any of the following Formulae II through V: ##STR2## wherein R.sup.5 and R.sup.6 are independently substituted or non-substituted lower alkyl.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: August 16, 1994
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Mitsuru Imuta, Koichi Nishi
  • 2-phenanthridinyl carbaphenem antibacterial agent
    Patent number: 5336674
    Abstract: The present invention relates to antibacterial agents of the carbapenem class, in which the 2-position sidechain is characterized by a phenanthridine moiety typically having a substituent attached to the nitrogen of the phenanthridine and substituted at other positions by various neutral substituents. When there is substitution on the nitrogen of the phenathridine moiety that nitrogen is a charged quaternary nitrogen.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: August 9, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. Dininno, Mark L. Greenlee, Thomas A. Rano, Wendy Lee
  • MRSA active 2-phenyl-carbapenems
    Patent number: 5334590
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: August 2, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Ravindra N. Guthikonda
  • 2-phenanthridinyl carbapenem antibacterial agents
    Patent number: 5328904
    Abstract: The present invention relates to antibacterial agents of the carbapenem class, in which the 2-position sidechain is characterized by a phenanthridine moiety, substituted by various neutral substituents.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: July 12, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Mark L. Greenlee, Thomas A. Rano, Wendy Lee
  • Beta-lactams and their production
    Patent number: 5310897
    Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, the same or different, each a hydrogen atom or a lower alkyl group, R.sub.3.sup.0 is a hydroen atom or a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and COZ is a protected thiolcarboxyl group, which is useful as a valuable intermediate in the stereospecific production of 1-alkylcarbapenem compounds.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: May 10, 1994
    Assignee: Sumitomo Pharmaceuticals Co., Ltd.
    Inventors: Makoto Sunagawa, Akira Sasaki, Koshiro Goda
  • 2-(aza-9-fluorenonyl)carbapenem antibacterial agents
    Patent number: 5294610
    Abstract: Carbapenems of the formula ##STR1## wherein a suitably substituted aza-9-fluorenone is attached at the 2-position of the carbapenem are useful antibacterial agents.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: March 15, 1994
    Assignee: Merck & Co. Inc.
    Inventors: Frank P. DiNinno, Ravindra N. Guthikonda
  • Intermediates for preparing cationic-2-heteroaryl-phenyl-carbapenem antibacterial agents
    Patent number: 5292879
    Abstract: Carbapenem compounds of the formula ##STR1## are useful intermediates for preparing antibacterial agents.
    Type: Grant
    Filed: August 28, 1992
    Date of Patent: March 8, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Ravindra N. Guthikonda, Susan M. Schmitt
  • 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds
    Patent number: 5286721
    Abstract: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds of the formula: ##STR1## in which R.sup.1 is carboxy, COO.sup.-- or protected carboxy,R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl,R.sup.8 is hydrogen or lower alkyl,Z is a group of the formula: ##STR2## wherein R.sup.3 is hydrogen; lower alkyl or lower alkenyl, each of which is optionally substituted by the group consisting of lower alkoxy, carbamoyl, hydroxy, halogen, mono(or di)(lower)alkylcarbamoyl, mono(or di)(lower)alkenylcarbamoyl, mono(or bis)[hydroxy(lower)alkyl]carbamoyl, optionally substituted cyclic-aminocarbonyl, acylamino, ureido, optionally substituted heterocyclic-carbonylamino, carbamoyloxy, mono(or di)(lower)alkylcarbamoyloxy, lower alkylthio, halo(lower)alkylthio, optionally substituted heterocyclicthio, optionally substituted heterocyclic group, optionally substituted aryl, and acyl;R.sup.9 is hydrogen or lower alkyl, andR.sup.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: February 15, 1994
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayoshi Murata, Toshiyuki Chiba, Hideo Tsutsumi, Kohji Hattori, Satoru Kuroda, Hiroaki Ohtake, Fumiyuki Shirai
  • Process for making antimicrobial quinolonyl lactams
    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.
  • 2-(N-imidazoliumphenyl)-carbapenems
    Patent number: 5276149
    Abstract: Carbapenems of the formula ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: January 4, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Alan D. Adams, James V. Heck
  • Antimicrobial quinolonyl esters
    Patent number: 5273973
    Abstract: Antimicrobial quinolnyl 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, R.sup.6, R.sup.7, and R.sup.8 form any of a variety of quinolone or napthyridine structures similar to those known in the art to have antimicrobial activity.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: December 28, 1993
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventors: Ronald E. White, Thomas P. Demuth, Jr.
  • Method for removing the protecting group for hydroxy group
    Patent number: 5260438
    Abstract: A method for removing tri-substituted silyl group from .beta.-lactam compound having a tri-substituted silyl group-protecting hydroxy group, which comprises treating with an acid and a fluoride selected from alkali metal fluoride, alkaline earth metal fluoride and hydrogenfluoride of organic or inorganic amine, by which the tri-substituted silyl group can be easily and effectively removed under moderate conditions so that the desired compound can be obtained in high yield at low cost.
    Type: Grant
    Filed: April 27, 1993
    Date of Patent: November 9, 1993
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hiroshi Horikawa, Kazuhiko Kondo, Tameo Iwasaki
  • Process for producing 2-carbon-substituted carbapenem derivatives
    Patent number: 5258509
    Abstract: A process for producing a 2-(unsubstituted or carbon-substituted)-1-carbapen-2-em-3-carboxylic acid derivative, which comprises reacting a 2-trifluoromethanesulfonyloxy-1-carbapen-2-em-3-carboxylic acid derivative or the 1-carbapen-2-em-3-carboxylic acid derivative derived from a 2-oxo-1-carbapenam-3-carboxylic acid derivative and trifluoromethanesulfonic anhydride, and a stannane derivative in an inert solvent in the presence of a palladium compound and a salt.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: November 2, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Yoshiaki Kato, Hiroshi Fukatsu
  • 2-phenyl-carbapenems
    Patent number: 5256777
    Abstract: Carbapenems of the formula ##STR1## are useful intermediates to antibacterial agents.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: October 26, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Ravindra N. Guthikonda
  • Metal ion porphyrin-containing poly(azine)
    Patent number: 5252698
    Abstract: The present invention relates to porphyrin and metal ion-containing monomers and polymers. The monomers ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently selected from H, alkyl having 1 to 6 carbon atoms, phenyl or phenyl substituted with 1 to 3 alkyl groups each having 1 to 6 carbons or with 1 to 3 halogen atoms and A is a metal atom, are used with a diamine or a dialdehyde respectively to produce a porphyrin polymer or a metal ion containing porphyrin polymer. These polymers are useful as electrical conductors and as liquid crystal polymers.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: October 12, 1993
    Assignee: SRI International
    Inventors: Tilak R. Bhardwaj, Susanna C. Ventura, Subhash C. Narang
  • (2-substituted phenyl) carbapenems
    Patent number: 5247074
    Abstract: Carbapenems of the formula: ##STR1## are useful intermediates to antibacterial agents.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: September 21, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. Dininno, Thomas N. Salzmann, Eugene D. Thorsett
  • Process for preparing (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo [1,2-a][1,2,4]triazolium-6-yl)]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carb apenem-3-carboxylate and starting materials thereof
    Patent number: 5241073
    Abstract: Novel and improved simple process for preparing carbapenem compound, (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo [1,2-a][1,2,4]triazolium-6-yl)]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carbap enem-3-carboxylate represented by the following formula: ##STR1## This compound may be prepared by using a mercapto reagent, 6,7-dihydro-6-mercapto-5H-pyrazolo-[1,2-a][1,2,4]triazolium derivative of the following formula: ##STR2## wherein X.sup..crclbar. is an anion charge.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: August 31, 1993
    Assignee: Lederle (Japan)
    Inventors: Satoshi Tamai, Takao Abe, Yunosuke Nagase
  • 2-(substituted-dibenzofuranyl and dibenzothienyl) carbapenem antibacterial agents
    Patent number: 5240920
    Abstract: Carbapenems having the formula: ##STR1## where X is O or S(O).sub.0-2 ; are useful antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: August 31, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Thomas N. Salzmann, Mark L. Greenlee
  • 4-cyclohexenyl azetidinone derivatives
    Patent number: 5225552
    Abstract: Compounds of formula ##STR1## in which R.sub.1 represents a hydrogen atom or a hydroxyl protecting group; R.sub.2 represents a hydrogen atom or a trialkylsilyl group, and --X--Y-- represents the epoxide group (A) or the alkene group (B). ##STR2## wherein R.sub.3 represents a C.sub.1-6 alkyl group optionally substituted by halogen or an optionally substituted phenyl group, useful as intermediates in the preparation of antibacterially active compound.
    Type: Grant
    Filed: March 6, 1992
    Date of Patent: July 6, 1993
    Assignee: Glaxo SpA
    Inventor: Alcide Perboni
  • Intermediates for preparing 2-heteroarylphenyl-carbapenem antibacterial agents
    Patent number: 5220011
    Abstract: Carbapenem intermediates of the formula ##STR1## where: M is a removable protecting group for carboxy, andP' is a removable protecting group for hydroxyare useful intermediates for preparing antibacterial agents.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: June 15, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, Ravindra N. Guthikonda, Susan M. Schmitt
  • 2-benzocoumarinyl-carbapenems
    Patent number: 5216146
    Abstract: Carbapenems of the formula ##STR1## are useful intermediates to antibacterial agents.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: June 1, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Mark L. Greenlee, Thomas A. Rano
  • 2-phenanthridonyl-carbapenems
    Patent number: 5214139
    Abstract: Carbapenems of the formula ##STR1## wherein: P' is a removable protecting group for hydroxy; andM is a removable protecting group for carboxy;are useful intermediates for carbapenem antibiotics.
    Type: Grant
    Filed: April 16, 1991
    Date of Patent: May 25, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Thomas A. Rano, Mark L. Greenlee
  • 2-biphenyl carbapenem intermediates
    Patent number: 5208329
    Abstract: Carbapenems of the formula ##STR1## are useful intermediates to antibacterial agents.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: May 4, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. Dininno, Thomas N. Salzmann
  • 2-(1,2,3-triazolylsubstituted)phenyl carbapenem antibacterial agents
    Patent number: 5208229
    Abstract: Carbapenems having the formula: ##STR1## are useful antibacterial agents.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: May 4, 1993
    Assignee: Merck & Co., Inc.
    Inventor: Susan M. Schmitt
  • 2-phenanthridonyl carbapenem intermediates
    Patent number: 5208328
    Abstract: Carbapenems of the formula ##STR1## wherein: P' is a removable protecting group for hydroxy; and M is a removable protecting group for carboxy; are useful intermediates for carbapenem antibiotics.
    Type: Grant
    Filed: April 16, 1991
    Date of Patent: May 4, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Frank DiNinno, Mark L. Greenlee, Thomas A. Rano