7-amino Cephalosporanic Acid Per Se Or Salt Thereof (i.e., 7-aca Or Salt Thereof) Patents (Class 540/219)
  • Publication number: 20150025053
    Abstract: The cephalosporin compound of formula (I) is disclosed, which exhibits antibiotic activity against Gram-negative (e.g., Pseudomonas aeruginosa) and Gram-positive (e.g., methicillin-resistant Staphylococcus aureus) bacteria. Methods of manufacturing the compound of formula (I), and uses of the compound in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.
    Type: Application
    Filed: July 17, 2014
    Publication date: January 22, 2015
    Inventors: Yong He, Yu Gui Gu, Ning Yin
  • Publication number: 20130164221
    Abstract: Provided herein are methods for detecting, quantifying, differentiating, diagnosing and imaging pathogenic bacteria or condition associated therewith using substrates for bacterial enzymes. Fluorescent, luminescent or colorimetric signals emitted by substrates or enzyme products in the presence of the bacteria are compared to controls to detect and locate the pathogenic bacteria. Provided is a method for screening therapeutic agents to treat the pathophysiological conditions by measuring a signal emitted from the substrates or products in the presence and absence of the potential therapeutic agent and a diagnostic method for detecting a mycobacterial infection in a subject by contacting biological samples with a substrate and imaging for signals emitted from a mycobacterial beta-lactamase product. Also provided are fluorogenic substrates or substrates comprising a colored dye or a chemical reagent effective to induce a color or pH change.
    Type: Application
    Filed: December 4, 2012
    Publication date: June 27, 2013
    Inventors: Jeffrey D. Cirillo, James C. Sacchettini, Jianghong Rao, Hexin Xie
  • Publication number: 20110112059
    Abstract: The present invention provides photosensitizer compounds for use in detecting beta-lactamase activity. Methods and kits that utilize the photosensitizer compounds of the invention for the detection of, quantitation of, and classification or typing of microbial beta-lactamases.
    Type: Application
    Filed: May 5, 2009
    Publication date: May 12, 2011
    Applicant: The General Hospital Corporation
    Inventors: Tayyaba Hasan, Ulysses W. Sallum, Sarika Verma
  • Publication number: 20100261897
    Abstract: The present invention relates to a process for the production of cephalosporin antibiotic intermediate of formula (I). More particularly relates to the preparation of the compound of formula (I) using a solvent medium selected from the group consisting of decalin (decahydronapthalene), hexane, cyclohexene, tetralin, petroleum ether, wherein X represents HI, HCI, H2SO4 and the like. The compound of formula (I) is an important intermediate in the preparation of Cefepime.
    Type: Application
    Filed: January 16, 2006
    Publication date: October 14, 2010
    Inventors: Udayampalayam Palanisamy Senthilkumar, Kanagaraj Suresh Kumar, Singaravel Mohan
  • Publication number: 20100261700
    Abstract: Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition. Additionally provided are pharmaceutical compositions for treatment or prevention of bacterial infections and methods of treatment of such infections.
    Type: Application
    Filed: April 9, 2010
    Publication date: October 14, 2010
    Inventors: Larry SUTTON, Sophia Yu, Kenneth R. Fountain
  • Publication number: 20100228015
    Abstract: This invention relates to novel homotopic prodrugs and medicaments and methods for their preparation, testing and use. In one embodiment, the homotopic prodrug has the general formula wherein is a biologically-active moiety comprising a carboxylic acid functional group, and Rb is a homotopically-symmetrical alcohol bonded to the biologically-active moiety through the carboxylic acid functional group to form an ester linkage, as well as optical isomers, enantiomers, pharmaceutically acceptable salts, biohydrolyzable amides, esters, and imides thereof and combinations thereof.
    Type: Application
    Filed: April 23, 2010
    Publication date: September 9, 2010
    Inventors: Mitchell A. deLong, Jill M. McFadden, Susan M. Royalty, Eric J. Toone, Jeffrey D. Yingling
  • Publication number: 20090227544
    Abstract: The present invention provides novel bisphosphonate conjugates, pharmaceutical compositions comprising bisphosphonate conjugates and methods of using such analogs in the treatment of bone cancer, bone-related diseases, bone infection, bone inflammation, and diseases of the soft tissues surrounding bones.
    Type: Application
    Filed: March 30, 2009
    Publication date: September 10, 2009
    Applicant: MBC PHARMA, INC.
    Inventors: Alexander Karpeisky, Shawn Zinnen
  • Patent number: 6518420
    Abstract: A process in the isolation of 7-aminocephalosporanic acid (7-ACA) from an alkaline, neutral or slightly acidic medium in the presence of an additive, e.g. selected from the group comprising organic carboxylic acid esters, polymeric glycols, polyacryls, amines and polyamines, melaminformaldehyde resins or amino acids and esters thereof to obtain 7-ACA agglomerates and or rosettes.
    Type: Grant
    Filed: November 7, 2001
    Date of Patent: February 11, 2003
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Petr Nadenik, Helmut Wagner
  • Patent number: 6458948
    Abstract: A method of preparing carboxylic acid derivatives comprising mixing a quaternary ammonium salt having a particular triazine ring in the molecules thereof, a carboxylic acid compound and a compound having a nucleophilic functional group, to condense the carboxylic acid with the compound having the nucleophilic functional group. The invention further provides a condensing agent comprising the quaternary ammonium salt. The condensation is conducted under mild conditions to form carboxylic acid derivatives and, particularly, amide compounds or ester compounds maintaining high yields.
    Type: Grant
    Filed: December 11, 2000
    Date of Patent: October 1, 2002
    Assignee: Tokuyama Corporation
    Inventors: Fumiaki Iwasaki, Shohei Tani, Munetaka Kunishima, Keiji Terao, Michiko Miharu, Naoki Hirano, Masako Saijyo
  • Patent number: 6420554
    Abstract: A process for preparing a 3-cephem compound represented by the formula (3), the process comprising the steps of reacting a &bgr;-lactam compound represented by the formula (1) with a phosphorus halide compound in the presence of an organic base to give an imino-&bgr;-lactam compound represented by the formula (2), adding a phenol to the same reaction system to cause decomposition due to reaction with an alcohol and simultaneously to remove the protection of carboxylic acid ester, giving a 3-cephem compound represented by the formula (3) or a salt thereof where R1, R2, R3 and X are as defined above.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: July 16, 2002
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Yutaka Kameyama, Takae Yamada, Dal Soo Suh
  • 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: 5604222
    Abstract: An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one of the formula: ##STR1## wherein R is: hydrogen; C.sub.1 -C.sub.3 alkyl; halomethyl; cyanomethyl; phenyl; substituted phenyl; phenoxy, benzyloxy- or substituted benzyl; a group of the formula R.sub.2 --O--wherein R.sub.2 is t-butyl, 2,2,2-trichloroethyl, benzyl or substituted benzyl; a group of the formula R.sub.3 --(O).sub.n --CH.sub.2 wherein R.sub.3 is phenyl or substituted phenyl. The 2-chlorosulfinylazetidin-4-one is prepared by reacting a penicillin sulfoxide ester of the general formula ##STR2## wherein R and R.sub.1 have the meanings defined above with an N-chloro halogenating agent in an inert organic solvent. The reaction is carried out in the presence of an acid scavenging amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures thereof.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: February 18, 1997
    Assignee: Lupin Laboratories, Ltd.
    Inventors: Niranjan L. Gupta, Ramanathan Sankaran, Sakina Sitabkhan
  • Patent number: 5594131
    Abstract: The present invention provides a process for the preparation of stable, crystalline cephalosporin intermediates of the formula ##STR1## wherein X is HI, HCl or H.sub.2 SO.sub.4 which are substantially free of the .DELTA..sup.2 isomer, and which are convertible into broad-spectrum cephalosporin antibiotics.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: January 14, 1997
    Assignee: Bristol-Myers Squibb COmpany
    Inventors: Gary M. F. Lim, John M. Roubie
  • Patent number: 5536830
    Abstract: A process for converting cephalosporin p-nitrobenzyl ester (Formula I) to the corresponding cephalosporin free acid (Formula II) comprising treating the cephalosporin p-nitrobenzyl ester with a metal selected from the group consisting of iron, magnesium, aluminum, and tin, and with hydrochloric acid in a mixture of water and a water-miscible organic solvent. Preferably, the metal is iron in the form of a fine powder, and the reaction is carried out at a temperature in the range of 30.degree.-50.degree. C.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 16, 1996
    Assignee: Ranbaxy Laboratories, Ltd.
    Inventors: Jag M. Khanna, Yatendra Kumar, Rakesh K. Arora, Neera Tiwari, Shailendra K. Singh
  • Patent number: 5405955
    Abstract: New compounds are disclosed having the general formulas (1) and (2): ##STR1## Also described is a process for preparing the compounds of formulas (1) and (2). Further described is a process for preparing a cephalosporin derivative having formula (5): ##STR2## by converting the compound of formula (1) to the compound of formula (2) and then converting the compound of formula (2) to the compound of formula (5).
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: April 11, 1995
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Osamu Sakanaka, Shouhei Yasuda, Shinjiro Sumi, Katsufumi Sebata, Katsuharu Iinuma, Ken Nishihata
  • 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: 5109132
    Abstract: A process is provided for the preparation of 3-methylene and 3-halomethylene cepham derivatives via 3-phosphoniomethyl-3-cephem derivatives, which in turn can be prepared from 3-halomethyl-3-cephem derivatives. The preparation can be carried out with or without isolating the intermediate phosphonium cephem compounds. The 3-methylene and 3-halomethylene cepham derivatives and in particular the 1-oxo and 1,1-dioxo cepham compounds are also prepared by reducing a 3-halomethyl-3-cepham derivative with activated metal, preferably zinc or magnesium.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: April 28, 1992
    Assignee: Gist-Brocades N.V.
    Inventors: Jan Verweij, Jan J. De Koning, Hendrik A. Witkamp
  • Patent number: 5066800
    Abstract: A novel process and intermediates used therein for linking a cephalosporin compound to a quinolone are disclosed. According to the disclosed process, the 2-carboxylic acid moiety of the cephalosporin compound is treated with an organic base. The resulting salt is then reacted with a quinolone compound which has been activated using a haloformate. The reaction is run in a non-aqueous organic solvent. 4-Dimethylaminopyridine is used to promote the reaction between the cephalosporin salt and the activated quinolone.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: November 19, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Masami Okabe
  • Patent number: 4870168
    Abstract: There is disclosed a process for the production of certain 3-hydrocarbyl-3-cephem derivatives wherein the hydrocarbyl group is selected from 1-alkenyl and conjugated and unconjugated 1-polyalkenyl, 1-alkynl, carbocyclic and heterocyclic aryl, and carbocyclic and heterocyclic arylmethyl and, in the case of the 1-alkenyl and conjugated 1-polyalkenyl derivatives, with substantially complete stereospecificity, by coupling a 3-triflyloxy cephem with a hydrocarbyltributylstannane in the presence of bis(dibenzylideneacetonyl)-palladium, a phosphine, and a metal halide such as, for example, zinc chloride. The 3-unsaturated alkyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: September 26, 1989
    Assignee: Bristol-Myers Company
    Inventors: Stephen R. Baker, Vittorio Farina, Chester Sapino, Jr.
  • Patent number: 4855419
    Abstract: The present invention relates to a method for producing novel 4-[1-oxoalkyl]-2,5-oxazolidinediones, (4-1 OOD), and their use in a stereoselective method of producing beta-lactam-containing compounds which include several biologically active compounds such as the well-known families of penicillin and cephalosporin antibiotics. The method of the present invention involves generally the reaction of the above-described 4-[1-oxoalkyl]-2,5-oxazolidinediones so produced with a thiol amine having a geometry amenable to forming the precursor of the desired beta-lactam-containing compound or, in one scheme, forming the beta-lactam-containing compound itself directly. This is done either by direct reaction of the 4-1 OOD with a thiol amine (which by one pathway proceeds directly to the beta-lactam-containing compound) or by first converting the 4-1 OOD to its 2-[1-oxoalkyl]-2-amino acid form before its reaction with the thiol amine; and then forming the beta lactam by action of cyanogen).
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 8, 1989
    Assignee: University of Cincinnati
    Inventors: Richard A. Day, John Wallace
  • Patent number: 4820832
    Abstract: A process for preparing 7.beta.-acylamino (or 7.beta.-protected amino)-3-H-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters and the corresponding cephalosporins is provided. 7.beta.-Acylamino (or 7.beta.-protected amino)-3-halo (or 3-sulfonyl ester)-1-carba(dethia)-3-cephem carboxylic acid esters and the corresponding cephalosporins are reduced with Pd(O) and a tetra-C.sub.2 -C.sub.6 alkyl stannane and, when a 3-sulfonyloxy ester is reduced, the process is carried out in the presence of an alkali metal halide. 3-Sulfonyloxy-3-cephem esters such as 3-mesylate, 3-tosylate and 3-triflate are employed.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: April 11, 1989
    Assignee: Eli Lilly and Company
    Inventors: Gwendolyn K. Cook, John H. McDonald, III
  • Patent number: 4772682
    Abstract: The invention relates to intermediates useful in the preparation of antimicrobial compounds, the intermediates being of the formula: ##STR1## wherein R.sup.A is --SCN or --S.sup..sym. (R.sup.3).sub.2, whereinR.sup.3 is lower alkyl, andR.sup.B is carboxy or --COO.sup..crclbar.,or a salt thereof, with the proviso that when R.sup.A is --SCN, then R.sup.B is carboxy and that when R.sup.A is --S.sup..sym. (R.sup.3).sub.2, then R.sup.B is --COO.sup..sym..
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: September 20, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4767851
    Abstract: An improved process is disclosed for the preparation of 7-amino and 7-substituted amino-desacetoxycephalosporins in which the corresponding 6-substituted amino penicillin sulphoxide is heated in the presence of an acidic substance which causes expansion of the penam ring in the reactant to the .DELTA..sup.3 cephem ring in the product in the presence of a silicon containing compound. The process comprises adding sulphamide or a silylsulphamide or a silylsulphamoyl to the reaction or utilizing a silylsulphamide or silylsulphamoyl as the silicon containing compound.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: August 30, 1988
    Assignee: Gema, S.A.
    Inventor: Alberto Palomo-Coll
  • Patent number: 4703118
    Abstract: The present invention provides a process for preparing a 3-iodomethyl cephalosporin by treating a bis(trialkylsilyl)-7-amino-4-carboxylic acid-3-substituted cephalosporin derivative with a trialkylsilyl iodide derivative.
    Type: Grant
    Filed: April 8, 1985
    Date of Patent: October 27, 1987
    Assignee: Eli Lilly and Company
    Inventors: Gary E. Lord, Robert M. Metzler, David D. Wirth
  • Patent number: 4699979
    Abstract: This invention provides novel cephalosporin intermediates, 7.beta.-amino-3-[(Z)-1-propen-1-y1]-3-cephem-4-carboxylic acid and esters thereof having the general formula ##STR1## wherein the configuration of the 3-propenyl group is Z sometimes referred to as cis- and R is hydrogen or a conventional carboxy-protected group, or a physiologically hydrolyzable esterifying group, and acid addition salts thereof and the metal salts of the foregoing substance wherein R is hydrogen. These compounds are useful as intermediates for preparation of orally active cephalosporins.
    Type: Grant
    Filed: March 25, 1986
    Date of Patent: October 13, 1987
    Assignee: Bristol-Meyers Company
    Inventors: Hideaki Hoshi, Jun Okumura, Takayuki Naito, Yoshio Abe, Shimpei Aburaki
  • Patent number: 4695628
    Abstract: A process for the preparation of 6-amino-pencillanic acid-1,1-dioxide without protecing either the amino group or the carboxy group during oxidation, by oxidation of 6-amino-penicillanic acid or 6-amino penicillanic acid sulfoxide with an alkali metal permanganate in an aqueous medium.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: September 22, 1987
    Assignee: Gist-Brocades N.V.
    Inventors: Jacobus J. Bos, Rinze Cuperus, Rudolf Wielinga
  • Patent number: 4694079
    Abstract: 7-[(D)-2-Amino-2-(4-hydroxyphenyl)acetamido]-3-[(Z)-1-propenyl]ceph-3-em-4- carboxylic acid in the form of its crystalline dimethylformamide solvate (1/1.5) has been provided.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: September 15, 1987
    Assignee: Bristol-Myers Company
    Inventor: Leonard B. Crast, Jr.
  • Patent number: 4684641
    Abstract: 7.alpha.-Hydroxyamino-7.beta.-[2-substituted-2-(acylamino)acetamido]-cephal osporin antibiotics, pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, a method of treating susceptible infections therewith, and intermediates therefor.
    Type: Grant
    Filed: June 27, 1985
    Date of Patent: August 4, 1987
    Assignee: Pfizer Inc.
    Inventors: Colin W. Greengrass, David W. T. Hoople, Thomas T. Howarth
  • Patent number: 4670431
    Abstract: A compound having the partial structure (A): ##STR1## wherein n is 1 or 2.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: June 2, 1987
    Assignee: Beecham Group p.l.c.
    Inventor: Peter H. Milner