Introduction Of -c(=x)- Group, Wherein X Is Chalcogen, Onto Nitrogen (e.g., Carboxamide Formation, Etc.) Patents (Class 540/316)
  • 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: 5801242
    Abstract: The present invention provides processes for making compounds of the structure(Q--L.sup.1)--L--(L.sup.2 --B)wherein(I) Q is a quinolone moiety;(II) B is a lactam moiety; and(III) L, L.sup.1, and L.sup.2 together comprise a linking moiety;comprising the steps of:(1) coupling a compound of Formula (III) with a lactam-containing compound to form an intermediate compound; and(2) cyclizing the intermediate by reaction with an organosilicon compound to give a compound of the formula (Q--L.sup.1)--L--(L.sup.2 --B).Preferably, the process additionally comprises a step prior to the coupling step, wherein protected forms of the compound of Formula (III) and the lactam compound are formed; and deprotection steps after the cyclization step, wherein the protecting groups are removed. Preferred antimicrobial compounds made by these processes are those where the beta-lactam moiety is a penem, a carbapenem, a cephem, or a carbacephem. Also preferred are those compounds where L.sup.1, L, and L.sup.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: September 1, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Jared Lynn Randall, Jane Ellen Godlewski
  • Patent number: 5532232
    Abstract: Compounds of the formula ##STR1## wherein L, M, R, T and X are set forth in the description, as well as hydrates or solvates thereof, which inhibit thrombin-induced platelet aggregation and clotting of fibrinogen in plasma, are described. The compounds of formula I are prepared by amidination or, depending on whether L is NH or O, by amide formation or esterification.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: July 2, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jean Ackermann, David Banner, Klaus Gubernator, Paul Hadvary, Kurt Hilpert, Klaus Muller, Ludvik Labler, Gerard Schmid, Thomas B. Tschopp, Hans P. Wessel, Beat Wirz
  • Patent number: 5281703
    Abstract: The present invention provides methods of making compounds of the structure[Q-L.sup.1 ]-L-[L.sup.2 -B[wherein(I) Q is a quinolone moiety;(II) B is a beta-lactam moiety;(III) L, L.sup.1, and L.sup.2 together comprise a carbamate-containing linking moietycomprising the steps of:(1) Reacting a lactam compound of the formula B-L.sup.4 -H with phosgene to form an intermediate compound of the formula B--L.sup.4 --C(=O)--Cl, where L.sup.4 is oxygen; and(2) Coupling said intermediate compound with a quinolone compound of the formula Q-L.sup.3 -R.sup.44 ; wherein L.sup.3 is nitrogen; R.sup.44 is hydrogen, Si(R.sup.45).sub.3, or Sn(R.sup.45).sub.3 ; and R.sup.45 is lower alkyl.Preferably, the process additionally comprises steps prior to the reacting and coupling steps where esters of the lactam and quinolone compounds are made. Also preferably, the coupling step comprises adding a solution containing the quinolone compound to a solution containing the intermediate compound.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: January 25, 1994
    Assignee: Procter & Gamble Pharmaceuticals, Inc.
    Inventors: Ronald E. White, Thomas P. Demuth, Jr.
  • Patent number: 5194604
    Abstract: Disclosed herein are processes for preparing a compound of the formula ##STR1## in which a novel compound of the formula ##STR2## is reacted with a beta lactam of the formula ##STR3## by treatment with a base, wherein the symbols are as defined in the specification.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: March 16, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Theodor Denzel, Christopher M. Cimarusti, Janak Singh, Richard H. Mueller
  • Patent number: 5126335
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof: ##STR1## wherein X is hydrogen or a group NHR.sup.1, wherein R.sup.1 is hydrogen or an amino protecting group, and R is an optionally substituted 5-membered or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from oxygen, sulphur or nitrogen, are useful in the treatment of bacterial infections in humans and animals.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: June 30, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Roger J. Ponsford, Andrew V. Stachulski
  • Patent number: 5015736
    Abstract: A new compound called N,N'-carbonyl-bis-(4-ethyl-2,3-dioxo)-piperazine of Formula I ##STR1## A process for the preparation thereof based on the reaction of 4-ethyl-2,3-dioxo-piperazine or a trimethylsilyl derivative thereof with carbonyl chloride or a derivative thereof.The use of the compound of Formula I as an intermediate in the preparation of compounds of Formula II ##STR2## where R is a radical, substituted in alpha position, of a molecule of an acid selected from the group formed by phenylacetic acid, p-hydroxy phenylacetic acid, a 6-(phenylacetamido)-penicillanic acid and a 7-(phenylacetamido)-cephalosporanic acid.
    Type: Grant
    Filed: November 15, 1989
    Date of Patent: May 14, 1991
    Assignee: Gema, S.A.
    Inventors: Juan Cabre Castellvi, Jose Diago Meseguer, Asuncion Esteve Bianchini, Carlos E. Lenhardt Padro, Esteve Sans Pitarch
  • Patent number: 4965358
    Abstract: A new compound called N,N'-carbonyl-bis-(4-ethyl-2,3-dioxo)-piperazine of Formula I ##STR1## A process for the preparation thereof based on the reaction of 4-ethyl-2,3-dioxo-piperazine or a trimethylsilyl derivative thereof with carbonyl chloride or a derivative thereof.The use of the compound of Formula I as an intermediate in the preparation of compounds of Formula II ##STR2## where R is a radical, substituted in alpha position, of a molecule of an acid selected from the group formed by phenylacetic acid, p-hydroxy phenylacetic acid, a 6-(phenylacetamido)-penicillanic acid and a 7-(phenylacetamido)-cephalosporanic acid.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: October 23, 1990
    Assignee: Gema, S. A.
    Inventors: Juan Cabre Castellvi, Jose Diago Meseguer, Asuncion Esteve Bianchini, Carlos E. Lenhardt Padro, Esteve Sans Pitarch
  • Patent number: 4954489
    Abstract: Compounds of formula (I) and their salts and esters: ##STR1## wherein X is hydrogen or a group NHR.sup.1, wherein R.sup.1 is hydrogen or an amino protecting group, and R is optionally substituted C.sub.5-8 cycloalkyl or cycloalkenyl, are useful in the treatment of bacterial infections.
    Type: Grant
    Filed: April 5, 1989
    Date of Patent: September 4, 1990
    Assignee: Beecham Group p.l.c.
    Inventors: Roger J. Ponsford, Andrew V. Stachulski
  • Patent number: 4945159
    Abstract: A method for the formation of intramolecular amide bonds by the action of cyanogen, under mild reaction conditions, in the preparation of cyclic amides, including lactams, in biologically active compounds. A compound containing at least one carboxylic acid group and at least one primary or secondary amino group is reacted with cyanogen to form an intramolecular amide bond. The method has utility in the synthesis of B-lactam antibiotics, such as penicillins, cephalosporins, and their derivatives, in enzyme modification, in cyclization of peptides, and in covalent cross-linking of proteins.
    Type: Grant
    Filed: December 2, 1986
    Date of Patent: July 31, 1990
    Assignee: University of Cincinnati
    Inventor: Richard A. Day
  • Patent number: 4918067
    Abstract: The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof: ##STR1## wherein R.sup.1 is a 5 or 6 membered sulphur and/or nitrogen containing heterocyclic group substituted by an optionally protected amino group, with the proviso that R.sup.1 is not 2-aminothiazol-4-yl, and R is hydrogen; optionally substituted C.sub.1-12 alkyl; optionally substituted C.sub.2-12 alkenyl or alkynyl; carbocyclyl; aryl or heterocyclyl.These compounds have antibacterial properties, and therefore are of use in the treatment of bacterial infections in humans and animals caused by a wide range of organizations.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: April 17, 1990
    Assignee: Beecham Group p.l.c.
    Inventors: Brian C. Gasson, Michael J. Pearson
  • Patent number: 4837317
    Abstract: The 6-[D(-)-alpha(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-alphaphenylace tamido]penicillanic acid and the salts thereof are prepared by synthetizing the novel intermediates, thioesters of D(-)-alpha-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-alpha-phenylacet ic acid, with mercaptoheterocycles and by converting them into the desired compound by reaction with 6-amino-penicillanic acid.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: June 6, 1989
    Assignee: Biochimica Opos S.p.A.
    Inventor: Luigi Ratti
  • Patent number: 4816452
    Abstract: The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof: ##STR1## wherein R.sup.1 is hydrogen or an amino protecting group and R is substituted methyl; optionally substituted C.sub.2-12 alkyl, alkenyl or alkynyl; carbocyclyl; aryl or heterocyclyl. These compounds have antibacterial properties, and therefore are of use in the treatment of bacterial infections in humans and animals caused by a wide range of organisms.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: March 28, 1989
    Assignee: Beecham Group P.L.C.
    Inventors: Michael J. Pearson, Richard L. Elliott
  • Patent number: 4711956
    Abstract: The invention relates to penicillin derivatives of Formula I, and a method of synthesis; the derivatives having high antimicrobial activity against gram-positive and gram-negative microorganisms. ##STR1## R is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen and a hydroxyl group;R.sub.2 is selected from the group consisting of hydrogen, an alkaline metal, and a carboxy protective group;R.sub.3 is selected from the group consisting of hydrogen, a lower alkyl, and a phenyl residue;R.sub.4, R.sub.5, and R.sub.6 are each selected from the group consisting of hydrogen, a halogen, a lower alkyd, and a lower alkoxy group;A is selected from the group consisting of oxygen and a N-(lower alkyl) residue; andn is 0 or 1.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: December 8, 1987
    Assignee: TPO "Pharmachim"
    Inventors: Ivanka A. Atanassova, Marieta A. Haimova, Vesselina B Chavdarova, Anton I. Nakov, Nedelcho G. Petkov, Ruska S. Avramova
  • Patent number: 4704457
    Abstract: A compund having the formula ##STR1## can be prepared by coupling a compound having the formula ##STR2## or a salt thereof, with a compound having the formula ##STR3## to yield a compound having the formula ##STR4## and oxidizing that compound to yield the desired compound; wherein R is hydrogen or an amino protecting group;R.sub.1 is hydrogen, methly or ethyl;M.sup..sym. is an inorganic cation or a substituted ammonium ion; andM.sub.1.sup..sym. is hydrogen, an organic cation, or a substituted ammonium ion.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: November 3, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jerome L. Moniot, Christopher M. Cimarusti, Rita T. Fox
  • Patent number: 4610822
    Abstract: Improved process for the preparation of 6-substituted penicillanic acids, in particular 6[D(-)-.alpha.-(4-alkyl-2,3-dioxo-]-piperazinocarbonylamino)phenylacetamid o]penicillanic acids, and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: September 9, 1986
    Assignee: American Cyanamid Company
    Inventors: Donald C. Boop, Karel F. Bernady
  • Patent number: RE33778
    Abstract: Substituted 1,3-dithietane-2-carboxylic acid derivatives useful as intermediates for the preparation of highly effective penicillin and cephalosporin derivatives and the preparation thereof.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: December 24, 1991
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Masaru Iwanami, Tetsuya Maeda, Yoshinobu Nagano, Masaharu Fujimoto, Noriaki Nagano, Atsuki Yamazaki, Kasaharu Tamazawa, Kiyoshi Murase, Tadao Shibanuma