3-position Substituent Contains Sulfur Patents (Class 540/226)
  • Patent number: 9703202
    Abstract: A surface treatment liquid that can effectively prevent pattern collapse of, in particular, a silicon pattern and a surface treatment process using the surface treatment liquid. The surface treatment liquid contains a water repellent agent and an acid imide. The surface treatment process includes exposing a surface of a substrate to the surface treatment liquid to thereby hydrophobize the substrate surface.
    Type: Grant
    Filed: March 18, 2016
    Date of Patent: July 11, 2017
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Daijiro Mori, Akira Kumazawa
  • Patent number: 9120861
    Abstract: The present invention provides methods for adding functional hydrophobic, charge, polar, and other structural groups on antimicrobial compounds for enhancing the physicochemical properties of the antimicrobial compounds, thereby creating novel antimicrobial analogs with enhanced functions.
    Type: Grant
    Filed: October 16, 2009
    Date of Patent: September 1, 2015
    Assignee: Mississippi State University
    Inventor: James Leif Smith
  • Publication number: 20150112057
    Abstract: The present invention relates to a crystalline form of an intermediate for cefoperazone of formula (1) and to a process for the preparation thereof by enzymatic condensation of a 3?-thiosubstituted ?-lactam nucleus with a phenylglycine derivative.
    Type: Application
    Filed: June 21, 2012
    Publication date: April 23, 2015
    Applicant: DSM Sinochem Pharmaceuticals Netherlands B.V.
    Inventors: Harold Monro Moody, Claudia Cusan, Edwin Gerard Ijpeij
  • Publication number: 20140322739
    Abstract: The present invention relates to compounds for and a method of detecting beta-lactamase activity in a sample. The sample is contacted with a nanoparticulate tag. The nanoparticulate tag comprises a metal or a combination of metals, or it comprises a nanotube of a metal, boron nitride and/or carbon. The respective metal is capable of forming one of a covalent bond, a coordinative bond and a non-covalent interaction with a thio or a seleno group. The sample is contacted with a compound of one of general formulas (I)-(III) and (VII)-(IX). At least one beta-lactam moiety of the compound is cleaved by the beta-lactamase activity in the sample. As a result a cleavage moiety Z-A-Z, Z-A-Z—R15, Z-A-Z—R16, Z-A-Z—R17, Z-A-Z—R18 or Z-G-N(R8)R9 is released that is immobilized on the surface of the nanoparticulate tag by a covalent bond via a Z atom. The presence of beta-lactamase activity is determined based on the presence of the cleavage moiety immobilized onto the surface of the nanoparticulate tag.
    Type: Application
    Filed: July 8, 2014
    Publication date: October 30, 2014
    Inventors: Bengang Xing, Xianfeng Huang, Tingting Jiang, Rongrong Liu
  • Patent number: 8859761
    Abstract: It discloses a novel process for refining cefamandole nafate, comprising: 1) adsorbing cefamandole nafate with strongly acidic ion exchange resin, followed by eluting the resin and collecting the eluate, to provide a primary purified cefamandole acid after concentration under reduced pressure; 2) neutralizing the primary purified cefamandole acid with an aqueous solution of sodium hydroxide or an aqueous solution of basic salt of sodium, followed by adjusting the pH value and filtrating out the insoluble substances with heating, thereby providing a secondary purified aqueous solution of cefamandole nafate; and 3) adding ethanol in a volume ratio between ethanol and water of 4:6 into the aqueous solution, to allow recrystallization under controlling the temperature, to provide a tertiary purified cefamandole nafate. The refined cefamandole nafate product has a purity of no less than 99.5%, mostly no less than 99.6%, with significantly low content of heavy metals.
    Type: Grant
    Filed: March 17, 2011
    Date of Patent: October 14, 2014
    Assignee: Hainan Lingkang Pharmaceutical Co., Ltd.
    Inventor: Linggang Tao
  • Publication number: 20140200342
    Abstract: The present invention relates to a process for the preparation of 3?-thiosubstituted cephalosporins by enzymatic condensation of a nucleus with a phenylglycine derivative. Furthermore the present invention relates to a crystalline form of a compound of general formula (1) wherein R2 is OH and X is S and R1 is a radical of formula (2a) with R3 is CH3.
    Type: Application
    Filed: June 21, 2012
    Publication date: July 17, 2014
    Applicant: DSM Sinochem Pharmaceuticals Netherlands B.V.
    Inventors: Harold Moody, Claudia Cusan, Gerard Ijpeij
  • Publication number: 20140128359
    Abstract: The invention relates to N-heterocyclic substituent-containing antibiotics, their preparation, and their use. Disclosed are sodium and potassium salts of 7-(?-((N,N?-diisopropylamidino)thio)acetylamino)-3-(((1,2,5,6-tetrahydro-2-methyl-5,6-diox o-1,2,4-triazin-3-yl)thio)methyl) cephalosporanic acid as presented by the general structure (I), their preparation, and their use. The antibiotics of the invention can be used to treat diseases caused by Gram-positive or Gram-negative bacteria such as septicaemia, gastrointestinal tract infection, and urinary tract infection. They have increased half-life in blood and lowered toxicity. They can reduce the frequency of drug use and lower medical treatment costs. They have improved stability and can be stored at ambient temperatures. The method of the invention is simple, and it produces high purity products which can meet the requirements of clinical use.
    Type: Application
    Filed: November 2, 2012
    Publication date: May 8, 2014
    Applicants: GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTI, GUANGZHOU BAIYUNSHAN PHARMACEUTICAL CO., LTD. GUANGZHOU BAIYUNSHAN PHARMACEUTICAL FACTORY
    Inventors: Mao Chen, Shaoxuan Zhu, Xuebin Liu, Lizhen Zheng, Liwei Lin, Shuwen Xu, Yuping Wang, Wei Yang, Yunfeng Li, Fang Ye, Xiaona Zhang
  • Publication number: 20130303754
    Abstract: It discloses a novel process for refining cefamandole nafate, comprising: 1) adsorbing cefamandole nafate with strongly acidic ion exchange resin, followed by eluting the resin and collecting the eluate, to provide a primary purified cefamandole acid after concentration under reduced pressure; 2) neutralizing the primary purified cefamandole acid with an aqueous solution of sodium hydroxide or an aqueous solution of basic salt of sodium, followed by adjusting the pH value and filtrating out the insoluble substances with heating, thereby providing a secondary purified aqueous solution of cefamandole nafate; and 3) adding ethanol in a volume ratio between ethanol and water of 4:6 into the aqueous solution, to allow recrystallization under controlling the temperature, to provide a tertiary purified cefamandole nafate. The refined cefamandole nafate product has a purity of no less than 99.5%, mostly no less than 99.6%, with significantly low content of heavy metals.
    Type: Application
    Filed: March 17, 2011
    Publication date: November 14, 2013
    Applicant: HAINAN LINGKANG PHARMACEUTICAL CO., LTD.
    Inventor: Linggang Tao
  • Patent number: 8373063
    Abstract: A solar cell is disclosed that includes an electron conductor layer and a quantum dot layer. The quantum dot layer may include a plurality of quantum dots. A bridge layer may be coupled to the electron conductor layer and to the quantum dot layer. The bridge layer may include an antibiotic, a sulfur-containing amino acid, a vitamin, and/or a vitamin analogue. In some cases, a hole conductor layer may be coupled to the quantum dot layer.
    Type: Grant
    Filed: March 26, 2009
    Date of Patent: February 12, 2013
    Assignee: Honeywell International Inc.
    Inventors: Bogdan Serban, Mihai N. Mihaila, Cazimir Bostan, Viorel Georgel Dumitru
  • Patent number: 7893254
    Abstract: A process for preparing 7-amino-3-[(E/Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (1) and an alkali metal salt thereof, said acid and said salt being improved in the content of 7-amino-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (2) or an alkali metal salt thereof, the process being characterized in that an aqueous solution of an alkali metal salt of 7-amino-3-[(E/Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid of the formula (1) is treated with a high porous polymer and/or active carbon as added thereto.
    Type: Grant
    Filed: June 3, 2005
    Date of Patent: February 22, 2011
    Assignees: Otsuka Chemical Co., Ltd., Meiji Seika Kaisha Ltd.
    Inventors: Yoichi Nishioka, Masahiro Ito, Yutaka Kameyama
  • Patent number: 7759483
    Abstract: A 3-alkenylcephem compound of the formula (1) wherein R1 is benzyl or phenoxymethyl, R2, R3 and R4 are alike or different and are each a hydrogen atom, C1-10 alkyl, C4-8 cycloalkyl or aryl C1-3 alkyl substituted or unsubstituted with C1-4 alkyl, R2 and R3, when taken together, form a group —(CH2)lXm(CH2)n— substituted or unsubstituted with C1-4 alkyl at an optional position, X is an oxygen atom or group —N(R5)—, l is 0 to 3, m is 0 or 1, n is an integer of 2 to 4, R5 is a hydrogen atom or C1-4 alkyl.
    Type: Grant
    Filed: June 2, 2005
    Date of Patent: July 20, 2010
    Assignee: Otsuka Chemical Co., Ltd.
    Inventors: Yoichi Nishioka, Koichi Sorajo, Yutaka Kameyama
  • Patent number: 7700581
    Abstract: Disclosed herein are a cephalosporin compound of formula I, wherein R1 is selected from the following groups: wherein R2 is selected from the following groups: the preparation and uses thereof. A method of preparing the cephalosporin compound as disclosed herein comprises reacting a starting cephalosporin comprising a C7 amino group and a C3 thio-methyl moiety substituted with an N-containing heterocyclic group with bromoacetyl bromide and then with a N,N?-bissubstituted thiourea. Methods of treating an infectious disease are also disclosed, comprising administering to a patient in need thereof the pharmaceutical composition disclosed herein.
    Type: Grant
    Filed: January 31, 2007
    Date of Patent: April 20, 2010
    Assignee: Guangzhou Baiyunshan Pharmaceutical Co., Ltd.
    Inventors: Mao Chen, Shaoxuan Zhu, Xuebin Liu, Chun Luo, Shuwen Xu, Lizhen Zheng, Fang Ye, Chenglong Yi, Xiaona Zhang
  • Patent number: 7544797
    Abstract: Provided is a process for preparing a compound of formula 1 or its salt, which includes reacting a compound of formula 2 with a compound of formula 3 in the presence of a base.
    Type: Grant
    Filed: October 30, 2004
    Date of Patent: June 9, 2009
    Assignee: CJ Cheiljedang Corporation
    Inventors: Dae Won Seo, In Hwa Chung, Ki Bong Lee, In Kyu Lee
  • Patent number: 7488724
    Abstract: The invention provides compounds of formula (I): wherein: R1-R4 and A have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting ?-lactamase enzymes, for enhancing the activity of ?-lactam antibiotics, and for treating ?-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula (I), and intermediates useful for the synthesis of compounds of formula (I).
    Type: Grant
    Filed: May 10, 2005
    Date of Patent: February 10, 2009
    Assignee: Southern Methodist University Foundation for Research
    Inventors: John D. Buynak, Lakshminarayana Vogeti
  • Patent number: 7459550
    Abstract: The present invention relates to an improved process for the preparation of Cefditoren of formula (I), the said process comprising the steps of: i) converting the compound of formula (II) to a compound of the formula (III) using TPP and sodium iodide in the presence of THF, water, and base; ii) reacting the compound of formula (III) with 4-methyl-5-formyl-thiazole to produce a compound of formula (IV); iii) deesterifying the compound of the formula (IV) to yield compound of formula (V); iv) converting the compound of formula (V) to compound of formula (VI) in the presence of a base and solvent; v) converting the compound of formula (VI) into compound of formula (VII) by enzymatic hydrolysis; and vi) reacting compound of formula (VII) with compound of formula (VIII) in the presence of solvent and base to produce compound of formula (I).
    Type: Grant
    Filed: July 3, 2004
    Date of Patent: December 2, 2008
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Kumar Sahoo Prabhat, Anandam Vempali, Sivakumaran Sundaravadivelan, Nagesh Ganesh Praveen, Manikrao Waghdare Vittal, Balawant Deshpande Pandurang, Kumar Luthra Parven, Ramesh Sathe Pratik
  • Publication number: 20080182836
    Abstract: Disclosed herein are a cephalosporin compound comprising a C3 thio-methyl moiety substituted with an N-containing heterocyclic group, and a C7 thiourea acetamido group, the preparation and uses thereof. A method of preparing the cephalosporin compound as disclosed herein comprises reacting a starting cephalosporin comprising a C7 amino group and a C3 thio-methyl moiety substituted with an N-containing heterocyclic group with bromoacetyl bromide and then with a N,N?-bissubstituted thiourea. Methods of treating an infectious disease are also disclosed, comprising administering to a patient in need thereof the pharmaceutical composition disclosed herein.
    Type: Application
    Filed: January 31, 2007
    Publication date: July 31, 2008
    Inventors: Mao Chen, Shaoxuan Zhu, Xuebin Liu, Chun Luo, Shuwen Xu, Lizhen Zheng, Fang Ye, Chenglong Yi, Xiaona Zhang
  • Patent number: 7396926
    Abstract: Provided are fluorescent substrates for ?-lactamases having the general formula I: in which R is a benzyl, 2-thienylmethyl, or cyanomethyl group; R? is selected from the group consisting of H, physiologically acceptable salts or metal, ester groups, ammonium cations, —CHR2OCO(CH2)nCH3, —CHR2OCOC(CH3)3, acylthiomethyl, acyloxy-alpha-benzyl, deltabutyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, ?-morpholinoethyl, dialkylaminoethyl, and dialkylaminocarbonyloxymethyl, in which R2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO2 and CH2; and Z is a donor fluorescent moiety. Also provided are methods of use of the compound of general formula I.
    Type: Grant
    Filed: January 11, 2002
    Date of Patent: July 8, 2008
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Jianghong Rao
  • Publication number: 20080009474
    Abstract: Orally bioavailable prodrugs of sulopenem, e.g., and solvates and hydrates thereof, preparation thereof, formulation thereof, and use to treat and prevent infection in mammals such as humans. This abstract is not limiting to the invention.
    Type: Application
    Filed: June 28, 2007
    Publication date: January 10, 2008
    Inventors: Katherine E. BRIGHTY, Anthony Marfat, Dale G. McLeod, John P. O'Donnell
  • Patent number: 7071329
    Abstract: Cephalosporins may be conveniently prepared by a process in which a benzathinium salt of formula (V) wherein: Z is benzathine; and X and R2 are as defined in the specification, is reacted with thiourea. The resulting product may be crystallized as a sodium salt, as an internal salt, or as a pharmaceutically acceptable salt.
    Type: Grant
    Filed: August 12, 2004
    Date of Patent: July 4, 2006
    Assignee: ACS Dobfar S.p.A.
    Inventors: Riccardo Monguzzi, Antonio Manca, Leonardo Marsili, Maurizio Zenoni
  • Patent number: 6916801
    Abstract: The invention provides compounds of formula (I): wherein: R1-R4 and A have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting ?-lactamase enzymes, for enhancing the activity of ?-lactam antibiotics, and for treating ?-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula (I), wherein R1 and R2 are each independently hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkenyl, (C3-C8)cycloalkyl, (C1-C10)alkoxy, (C1-C10)alkanoyl, (C1-C10)alkanoyloxy, (C1-C10)alkoxycarbonyl, aryl, heterocycle, halo, cyano, nitro, —COORe, —C(?O)NRfRg, —OC(?O)NRfRg, NRfRg, or —S(O)nRh; R3 is hydrogen, halo, aryl, heteroaryl, —S(O)nRh, or —CH?CHC(?O)NRmRp; R4 is hydrogen; A is thio, sulfinyl, or sulfonyl; and intermediates useful for the synthesis of compounds of formula (I).
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: July 12, 2005
    Assignee: Alamx, LLC
    Inventors: John D. Buynak, Lakshminarayana Vogeti
  • Patent number: 6803461
    Abstract: The present invention relates to a process for preparation of 7-amino-3-[2-(furylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid (I) by the condensation of 7-aminocephalosporanic acid (II) with furyl-2-carbonylthiol (III) in the presence of borontrifluoride or its complex, in an organic solvent or mixture of solvents at 0-50° C.
    Type: Grant
    Filed: August 1, 2002
    Date of Patent: October 12, 2004
    Assignee: Orchid Chemicals and Pharmaceuticals Limited
    Inventors: Pramod Narayan Deshpande, Bhausaheb Pandharinath Khadangale, Surulichamy Senthil Kumar, Gautam Kumar Das
  • Patent number: 6800756
    Abstract: The present invention relates to preparation of Ceftiofur acid of formula (I), and its pharmaceutically acceptable salts. The process includes the steps of (i) condensing an activated derivative of wherein the activated derivative is selected from acid halides, mixed anhydrides and active amides, and wherein X represents halogen atom selected from chlorine and bromine, with silylated derivative of wherein R represents p-methoxybenzyl, p-nitrobenzyl or diphenylmethyl in the presence of a solvent at −40° C. to 0° C. to produce (ii) cyclising (V) with thiourea in the presence of water miscible solvent and sodium acetate at room temperature to produce cephalosporin (iii) deesterifying (VI) to produce (I) using anisole/trifluoroacetic acid, phenol/trifluoroacetic acid or formic acid at 0° C. to 10° C. and, if desired, (iv) converting (I), to its pharmaceutically acceptable salt.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: October 5, 2004
    Assignee: Orchid Chemicals and Pharmaceuticals, Ltd.
    Inventors: Pandurang Balwant Deshpande, Praven Kumar Luthra, Pratik Ramesh Sathe, Sivakumaran Sundaravadivelan, Praveen Nagesh Ganesh
  • Publication number: 20040181056
    Abstract: A process for preparing cephalosporanic acid derivatives comprises the steps of enzymatically converting a 3-thiolated cephalosporin C compound of formula III:— 1
    Type: Application
    Filed: March 19, 2004
    Publication date: September 16, 2004
    Applicant: Bioferma Murcia S.A.
    Inventors: Alvaro Sanchez-Ferrer, Jose Aniceto Lopez-Mas, Francisco Garcia-Carmona
  • Publication number: 20040175783
    Abstract: A process for preparing cephalosporanic acid derivatives comprises the steps of enzymatically converting a 3-thiolated cephalosporin C compound of formula III:— 1
    Type: Application
    Filed: March 19, 2004
    Publication date: September 9, 2004
    Applicant: Bioferma Murcia S.A.
    Inventors: Alvaro Sanchez-Ferrer, Jose Aniceto Lopez-Mas, Francisco Garcia-Carmona
  • Publication number: 20040087787
    Abstract: The present invention provides novel thioester derivatives of thiazolyl acetic acid of the general formula (I), also, the invention provides a method for preparation of the thioester derivatives and reaction of the thioester derivatives with cephem carboxylic acids to produce cephalosporin antibiotic compounds having general formula (II).
    Type: Application
    Filed: September 12, 2003
    Publication date: May 6, 2004
    Inventors: Pandurang Balwant Deshpande, Parven Kumar Luthar
  • Patent number: 6723716
    Abstract: The present invention relates to a cephem prodrug having formula III or formula IV: or a pharmaceutically acceptable salt thereof, wherein R′1 is selected from the group consisting of hydrogen and —C(O)CH(NH2)CH3 and R′2 is selected from the group consisting of hydrogen and an acyl group that is cleaved by an enzyme found in mammals, with the proviso that, when either R′1 or R′2 is hydrogen, the other is not. A, B, L, G, E, and J are each independently nitrogen or carbon such that the respective rings are selected from the group consisting of provided that the group —CH2—S—CH2CH2NHR′2 is attached only to a carbon atom of said heterocyclic group, and Q is selected from the group consisting of nitrogen and —CX, wherein X is selected from the group consisting of hydrogen and chlorine.
    Type: Grant
    Filed: September 21, 2000
    Date of Patent: April 20, 2004
    Assignee: Essential Therapeutics, Inc.
    Inventors: Scott J. Hecker, Aesop Cho, Tomasz W. Glinka, Trevor Calkins, Ving J. Lee
  • Patent number: 6683176
    Abstract: The present invention relates to novel processes for the preparation of 3-methylenecephams. More specifically, the present invention relates to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone derivatives with organometallic catalysts of the formula III. MEx(H2O)y  (III) wherein: M is Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, or In; E is O[SO2(C1-C6 polyfluoroalkyl)], N[SO2(C1-C6 polyfluoroalkyl)]2, or C[SO2(C1-C6 polyfluoroalkyl)]3; x is 3; y is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.
    Type: Grant
    Filed: December 31, 2001
    Date of Patent: January 27, 2004
    Inventors: Robin D. G. Cooper, Anthony G. M. Barrett
  • Publication number: 20030208065
    Abstract: A process for the purification of cefixime via a novel tert.octylamine salt of a cefixime intermediate which may be crystalline and which may be produced in a one pot reaction from 7-amino-3-vinyl-ceph-3-em-4-carboxylic acid.
    Type: Application
    Filed: September 30, 2002
    Publication date: November 6, 2003
    Inventors: Martin Decristoforo, Johannes Ludescher, Hubert Sturm, Werner Veit
  • Publication number: 20030166922
    Abstract: The present invention relates to a novel cephalosporin compound in which thiomethylthio chain is introduced into C-3 position of cephem ring and pharmaceutically acceptable non-toxic salt, physiologically hydrolysable ester, hydrate, solvate or isomer thereof. The present invention also relates to a pharmaceutical composition containing the compound and to a process for preparing the compound.
    Type: Application
    Filed: November 21, 2002
    Publication date: September 4, 2003
    Inventors: Yang-Rae Cho, Chang-Seok Lee, Seong-Ho Oh, Eun-Jung Ryu, Kyoung-Sook Paek, Ha-Sik Youn, Yong-Jin Jang, Geun-Tae Kim
  • Publication number: 20030162763
    Abstract: The present invention relates to a novel cephalosporin compound and pharmaceutically acceptable non-toxic salt, physiologically hydrolysable ester, hydrate, solvate or isomer thereof, to a pharmaceutical composition containing the compound and to a process for preparing the compound.
    Type: Application
    Filed: November 21, 2002
    Publication date: August 28, 2003
    Inventors: Chang-Seok Lee, Seong-Ho Oh, Eun-Jung Ryu, Seong-Baek Lee, Ha-Sik Youn, Yong-Jin Jang, Geun-Tae Kim, Hyang-Sook Lee
  • Publication number: 20030135041
    Abstract: The present invention provides an improved process for the preparation of 7-amino-3-[2-(furylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid represented by formula (I) 1
    Type: Application
    Filed: January 4, 2002
    Publication date: July 17, 2003
    Applicant: ORCHID CHEMICALS & PHARMACEUTICALS LIMITED, INDIA
    Inventors: Pramod Narayan Deshpande, Bhausaheb Pandharinath Khadangale, Surulichamy Senthil Kumar, Gautam Kumar Das
  • Publication number: 20030130502
    Abstract: The present invention relates to a process for preparation of 7-amino-3-[2-(furylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid (I) by the condensation of 7-aminocephalosporanic acid (II) with furyl-2-carbonylthiol (III) in the presence of borontrifluoride or its complex, in an organic solvent or mixture of solvents at 0-50° C.
    Type: Application
    Filed: August 1, 2002
    Publication date: July 10, 2003
    Applicant: Orchid Chemicals and Pharmaceuticals Limited
    Inventors: Pramod Narayan Deshpande, Bhausaheb Pandharinath Khadangale, Surulichamy Senthil Kumar, Gautam Kumar Das
  • Patent number: 6583133
    Abstract: Disclosed are cephalosporin derivatives of the general formula wherein R is an organic residue with a molecular weight not exceeding 400 bonded to the adjacent sulphur atom via carbon and consisting of carbon, hydrogen, and optional oxygen, sulfur, nitrogen and/or halogen atoms; R1 is hydrogen, lower alkyl or phenyl; and A is a secondary, tertiary or quaternary nitrogen atom bound directly to the propenyl group and being substituted by an organic residue with a molecular weight not exceeding 400 and consisting of carbon, hydrogen, and optional oxygen, sulfur, nitrogen and/or halogen atoms, as well as readily hydrolyzable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula I and of their esters and salts.
    Type: Grant
    Filed: June 22, 1999
    Date of Patent: June 24, 2003
    Assignee: Basilea Pharmaceutica AG
    Inventors: Peter Angehrn, Erwin Götschi, Ingrid Heinze-Krauss, Hans G. F. Richter
  • Patent number: 6555679
    Abstract: The present invention relates to a process for preparing sodium salt of cephalosporins from their corresponding hydrohalide salt, which is neutralized with trimethylsilylating agent for the first time.
    Type: Grant
    Filed: October 3, 2001
    Date of Patent: April 29, 2003
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Pandurang Balwant Deshpande, Bhausaheb Pandarinath Khadangale
  • Patent number: 6531465
    Abstract: A compound of formula wherein Ac, R1 and R2 have various meanings, a process for a preparation thereof and its use as a pharmaceutical, i.e. as antibacterial agent.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: March 11, 2003
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Gerd Ascher, Johannes Ludescher
  • Patent number: 6476220
    Abstract: A process is disclosed for the preparation of 7-amino-3-(2-furanylcarbonylthiomethyl)-3-cephem-4-carboxylic acid (also known as Furaca). The process comprises of the steps of reacting 7-aminocephalosporanic acid with a mixture of 2-thiofuric acid and Boron Trifluoride in a solvent and precipitating Furaca as a solid.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: November 5, 2002
    Assignee: Aurobindo Pharma Limited
    Inventors: Uthira Kumar, Meenakshisunderam Sivakumaran, Vijay Kumar Handa
  • Patent number: 6458949
    Abstract: A novel process for the preparation of ceftiofur, a cephalosporin antibiotic useful in the treatment of bovine respiratory disease using a novel bromo or chloro intermediate. the process comprises of the steps of cyclizing a new bromo or chloro intermediate with thiourea in the presence of selected solvents to produce ceftiofur of high purity. A process to prepare such novel bromo and chloro intermediate comprising of the steps of condensing silylated Furaca with 4-(bromo or chloro)-2 methoxyamino-3-oxobutyric acid or its acid halide is also described.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: October 1, 2002
    Assignee: Aurobindo Pharma Limited
    Inventors: Vijay Kumar Handa, Meenakshisunderam Sivakumaran, Ramesh Dandala, Venkataiah Sunku
  • Patent number: 6448393
    Abstract: 3-Halogenomethylcephem compound of the formula (2) or its salt is obatined by deprotecting with phenol derivative a carboxylic acid protecting group at the 4-position of 7-amino-3-halogenomethylcephem compound of the formula (1) or its salt Further 3-thiomethylcephem compound of the formula (4) or its salt is prepared by reacting 3-halogenomethylcephem compound of the formula (2) or its salt with thiol compound or its salt of the formula (3) wherein X1, R1, R2 and M are as defined in the specification.
    Type: Grant
    Filed: April 14, 2000
    Date of Patent: September 10, 2002
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventor: Yutaka Kameyama
  • 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: 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: 6407091
    Abstract: The invention provides compounds of formula I and IV: wherein R1-R11 and A have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting &bgr;-lactamase enzymes, for enhancing the activity of &bgr;-lactam antibiotics, and for treating &bgr;-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula I and IV, and novel intermediates useful for the synthesis of compounds of formula I and IV. The A can be, for example, thio, sulfinyl, or sulfonyl.
    Type: Grant
    Filed: April 13, 2000
    Date of Patent: June 18, 2002
    Assignee: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, A. Srinivasa Rao, Greg C. Adam, Sirishkumar D. Nidamarthy, Venkata Ramana Doppalapudi
  • Publication number: 20020065412
    Abstract: A process is disclosed for the preparation of 7-amino-3-(2-furanylcarbonylthiomethyl)-3-cephem-4-carboxylic acid of the formula 1
    Type: Application
    Filed: July 9, 2001
    Publication date: May 30, 2002
    Inventors: Uthira Kumar, Meenakshisunderam Sivakumaran, Vijay Kumar Handa
  • Patent number: 6329363
    Abstract: The invention provides new fluorinated cephalosporin antibiotics and methods of preventing or treating infection, particularly mastitis in ruminants, using these antibiotics, and veterinary and pharmaceutical formulations comprising these antibiotics.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: December 11, 2001
    Assignee: Eli Lilly and Company
    Inventor: Karl Robert Dahnke
  • Patent number: 6303592
    Abstract: Derivatives of 7-alkylidene cephalosporanic acid sulfone and the pharmaceutically active salts thereof are found to be potent inhibitors of &bgr;-lactamase enzymes.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: October 16, 2001
    Assignee: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, Brian Bachmann
  • Patent number: 6294668
    Abstract: The present invention relates to cephalosporin derivatives of the general formula where R1 is halogen, lower alkyl, phenyl, benzyl, styryl, naphthyl or heterocyclyl; the lower alkyl, phenyl, benzyl, styryl, naphthyl and heterocyclyl being optionally substituted by at least one of halogen, hydroxy, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted phenyl, amino, lower alkylamino, di-lower alkylamino, carboxy, lower alkylcarboxy, carbamoyl or lower alkylcarbamoyl; R4, R5 independently are hydrogen, lower alkyl or phenyl; X is S, O, NH or CH2; n is 0,1 or 2; m is 0 or 1; s is 0 or 1; R2 is hydrogen, hydroxy, —CH2—CONHR6, lower alkyl-Qr, cycloalkyl-Qr, lower alkoxy, lower alkenyl, cycloalkenyl-Qr, lower alkynyl, aralkyl-Qr, aryl-Qr, aryloxy, aralkoxy, a heterocyclic ring or a heterocyclyl-Qr, the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aralkyl, aryl, aryloxy, aralkoxy and the heterocyclic
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: September 25, 2001
    Assignee: Hoffman-La Roche Inc.
    Inventors: Peter Angehrn, Ingrid Heinze-Krauss, Hans G. F. Richter
  • Patent number: 6294527
    Abstract: An antibacterial compound wherein represents benzene ring, pyridine ring, pyrazine ring or 5-membered aromatic neterocycle (having one oxygen or sulfur atom as ring-constituting atom), there being no R4 where  represents 5-membered aromatic heterocycle; X and Y respectively represent hydrogen atom or CXY represents C═N—OR5 wherein R5 represents hydrogen atom, halo C1-C6 alkyl or C3-C7 cycloalkyl; R1 represents phenyl, furyl, thienyl, thiazolyl (which may be substituted by amino group), tetrazolyl or thiadiazolyl, R2, R3 and R4 respectively represent hydrogen atom, halogen, hydroxyl group, nitro, C1-C6 alkoxy, trifluoromethyl, isothiuronium C1-C6 alkyl, amino C1-C6 alkyl, halo C1-C6 alkyl, morpholino, piperidino or piperazinyl.
    Type: Grant
    Filed: July 20, 1999
    Date of Patent: September 25, 2001
    Assignee: Zenyaku Kogyo Kabushiki Kaisha
    Inventors: Hideaki Hanaki, Hiroaki Yamazaki, Yoshio Tsuchida, Hideki Sato, Keiichi Hiramatsu, Seiichiro Kawashima
  • Patent number: 6288223
    Abstract: There can be produced, at a high selectivity and in a high yield, the Z-isomer of a 7-N-unsubstituted or substituted-amino-3-[2-(4-substituted or unsubstituted-thiazol-5-yl) vinyl]-3-cephem-4-carboxylic acid or an ester thereof having the general formula (IV) wherein R1 denotes a hydrogen atom, a mono-valent amino-protecting group or a 2-(2-N-protected or unprotected aminothiazol-4-yl)- 2-alkoxyiminoacetyl group, R2 denotes a hydrogen atom, or R1 and R2 as taken together mean one di-valent amino-protecting group, R3 denotes a hydrogen atom, pivaloyloxymethyl group or a carboxyl-protecting group and R8 denotes an alkyl group and so on, by a process comprising reacting a 7-N-unsubstituted or substituted-amino-3-[(tri-substituted-phosphoranylidene) methyl]-3-cephem-4-carboxylic acid or an ester thereof having the general formula (I) wherein R1, R2 and R3 each have the same meanings as defined above, and R4 denotes a lower alryl group or an aryl group, with
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: September 11, 2001
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Yumiko Okada, Masamichi Sukegawa, Tatsuo Watanabe, Hiroyuki Iwasawa, Yasushi Murai, Katsuharu Iinuma
  • Publication number: 20010011085
    Abstract: The present invention relates to cephem-derivatives and to a process for their preparation, having proper substituents at C-2 position, i.e. heterocyclylthio or acyloxy group. They are potent protease inhibitors, in particular human leucocyte elastase (HLE) inhibitors.
    Type: Application
    Filed: August 14, 1997
    Publication date: August 2, 2001
    Inventors: MARCO ALPEGIANI, PIERLUIGI BISSOLINO, MASSIMILIANO PALLADINO, ETTORE PERRONE
  • Patent number: 6235897
    Abstract: Process of depleting 7-amino-3-[(E)-2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid in Z/E mixtures of 7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid a) by subjecting an amine salt of a Z/E mixture of 7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid to crystallization and converting this amine salt into 7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid, or b) by subjecting the Z/E mixture to chromatography.
    Type: Grant
    Filed: March 25, 1997
    Date of Patent: May 22, 2001
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Johannes Ludescher, Harald Summer, Siegfried Wolf
  • Patent number: 6169180
    Abstract: The invention relates to a new economical and simple process, using a new intermediate compound, for the production of 3′-substituted 7-amino-3-propenyl-4-cephem-carboxylic acid derivatives of formula wherein R is hydrogen, a negative charge or a silyl protecting group, Ro is hydrogen or methoxy, R1 is hydrogen or a silyl protecting group and X is the radical of a nucleophile, and their acid addition salts.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: January 2, 2001
    Assignee: Biochemie Gesellschaft
    Inventors: Johannes Ludescher, Hubert Sturm, Josef Wieser