7-position Substituent Contains Hetero Ring Patents (Class 540/227)
  • Patent number: 9981943
    Abstract: The present invention relates to a process for preparing compound 1 that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compound 1 and substituted derivatives thereof.
    Type: Grant
    Filed: March 19, 2015
    Date of Patent: May 29, 2018
    Assignee: Mycovia Pharmaceuticals, Inc.
    Inventors: William J. Hoekstra, Christopher M. Yates, Mark Behnke, Asaf Alimardanov, Scott A. David, Douglas Franklin Fry
  • Publication number: 20140011994
    Abstract: A method for treating cefotiam hydrochloride, comprises the following steps: step 1), dissolving the raw material cefotiam hydrochloride in water, treating it with an acidic salt, then cooling it, and filtering the precipitate to obtain an aqueous filtrate; step 2), adding a water-immiscible solvent to the above aqueous solution for extraction, and then separating the organic phase containing impurities to obtain an aqueous solution containing cefotiam hydrochloride; step 3) adding to the aqueous solution a poor solvent of cefotiam hydrochloride and controlling the temperature for recrystallization, washing the educed crystals by centrifugation, and drying them to obtain purified cefotiam hydrochloride. The cefotiam content of the refined cefotiam hydrochloride obtained by the method of the present invention is not less than 86%, the content of polymeric impurities is less than 0.3%, and the content of insoluble microparticles in the injection prepared therefrom is quite low.
    Type: Application
    Filed: April 14, 2011
    Publication date: January 9, 2014
    Applicant: HAINANLINGKANG PHARMACEUTICAL CO., LTD.
    Inventor: Linggang Tao
  • Patent number: 8557978
    Abstract: This invention provides cross-linked glycopeptide-cephalosporin compounds and pharmaceutically acceptable salts thereof which are useful as antibiotics. This invention also provides pharmaceutical compositions containing such compounds; methods for treating bacterial infections in a mammal using such compounds; and processes and intermediates useful for preparing such compounds.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: October 15, 2013
    Assignee: Theravance, Inc.
    Inventor: Daniel D. Long
  • Patent number: 8470809
    Abstract: The present invention relates to novel polymorph of Ceftiofur sodium as a crystalline product. The present invention also provides a process for the preparation of novel polymorphs of crystalline Ceftiofur sodium of formula (I).
    Type: Grant
    Filed: October 13, 2010
    Date of Patent: June 25, 2013
    Assignee: Orchid Chemicals & Pharmaceuticals Limited
    Inventors: Sureshkumar Kanagaraj, Sivakumar Balasubramanian, Senthilkumar Udayampalayam Palanisamy
  • Patent number: 8431562
    Abstract: Polymorphs of Ceftiofur sodium as a crystalline product and a process for the preparation of polymorphs of crystalline Ceftiofur sodium of formula (I).
    Type: Grant
    Filed: August 20, 2009
    Date of Patent: April 30, 2013
    Assignee: Orchid Chemicals & Pharmaceuticals Limited
    Inventors: Senthilkumar Udayampalayam Palanisamy, Sivakumar Balasubramanian, Manimaran Arasappan, Meenakshi Sundaram Soma Sundaram, Sureshkumar Kanagaraj, Mohan Singaravel
  • Publication number: 20120329770
    Abstract: The present invention relates to cephalosporin derivatives having ?-lactamase inhibitory activity. The compounds are useful in preventing or treating bacterial resistance to an antibiotic, e.g. a ?-lactam antibiotic. Disclosed herein are compounds that are inhibitors of class B metallo-?-lactamases, as well as class A, C, and D serine ?-lactamases. In some preferred embodiments, the compounds are 3?-thiobenzoate derivatives of a cephalosporin. Pharmaceutical compositions, methods, uses, kits and commercial packages comprising the compounds are also disclosed.
    Type: Application
    Filed: February 25, 2011
    Publication date: December 27, 2012
    Inventors: Gary Igor Dmitrienko, Ahmad Ghavami, Valerie Joy Goodfellow, Jarrod W. Johnson, Anthony Paul Krismanich, Laura Marrone, Thammaiah Viswanatha, Sundaramma Viswanatha
  • Patent number: 8212024
    Abstract: The present invention relates to novel polymorph of Ceftiofur sodium as a crystalline product. The present invention also provides a process for the preparation of crystalline Ceftiofur sodium of formula (I).
    Type: Grant
    Filed: October 12, 2006
    Date of Patent: July 3, 2012
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Udayampalayam Palanisamy Senthilkumar, Kanagaraj Suresh Kumar, Singaravel Mohan, Lakshminarayanan Arunkumar, Bakthavachalam Ananthan
  • Patent number: 8178521
    Abstract: The present invention relates to cefazolin sodium pentahydrate crystal and a method for assembly and preparation of the crystal molecule. The cefazolin sodium pentahydrate crystal molecule contains five water molecules, orthorhombic system, space group of C222(1), in which sodium ion is bonded to the cefazolin molecule with a coordinate bond. The method for assembly and preparation of cefazolin sodium pentahydrate crystal molecule are: adding a solvent to a reactor equipped with a jacket, adding cefazolin acid and a sodium salt, heating until the reaction solution is clear, stirring continuously, adjusting pH, upon the completion of the reaction, transferring the liquid into a jacketed crystallizer, adding crystal seeds or nucleating spontaneously, controlling cooling, slowly adding a antisolvent.
    Type: Grant
    Filed: September 15, 2006
    Date of Patent: May 15, 2012
    Assignees: Tianjin University, Shenzhen Gosun Pharmaceutical Co., Ltd.
    Inventors: Jingkang Wang, Yuxin Qian, Meijing Zhang, Jiehua Wu, Zhan'ao Yang
  • Patent number: 8148632
    Abstract: Example solar cells and methods for making and using the same are disclosed. An example solar cell may include an electron conductor layer, a quantum dot layer, a bifunctional ligand layer coupling the electron conductor layer and the quantum dot layer, and a hole conductor layer coupled to the quantum dot layer. The bifunctional ligand layer may include an antibiotic, and in some cases, a cephalosporin-based antibiotic.
    Type: Grant
    Filed: July 14, 2009
    Date of Patent: April 3, 2012
    Assignee: Honeywell International Inc.
    Inventors: Bogdan Serban, Mihai N. Mihaila, Viorel Georgel Dumitru, Cazimir Bostan, Stephan Dan Costea, Mircea Bercu
  • Publication number: 20120040380
    Abstract: The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a ?-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a ?-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a ?-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a ?-lactmase or instructions for using the components in an assay.
    Type: Application
    Filed: June 22, 2011
    Publication date: February 16, 2012
    Applicant: LIFE TECHNOLOGIES CORPORATION
    Inventors: SCHUYLER BOON CORRY, WILLIAM LOUIS DOWNEY, BRIAN FILANOSKI, KYLE RICHARD GEE, I. LAWRENCE GREENFIELD, JAMES DAVID HIRSCH, IAIN JOHNSON, ALEKSEY RUKAVISHNIKOV
  • Publication number: 20110244486
    Abstract: Methods, assays and compositions for the diagnosis and treatment of diabetes, in which the glutamate transporters and/or receptors expressed in pancreatic islet cells are used as therapeutic targets or tools for the identification or treatment of individuals suffering from or susceptible to diabetes.
    Type: Application
    Filed: November 20, 2009
    Publication date: October 6, 2011
    Inventors: Carla Perego, Eliana Sara Di Cairano, Alberto Davalli, Franco Folli
  • Publication number: 20110059933
    Abstract: The present invention relates to novel polymorph of Ceftiofur sodium as a crystalline product. The present invention also provides a process for the preparation of novel polymorphs of crystalline Ceftiofur sodium of formula (I).
    Type: Application
    Filed: October 13, 2010
    Publication date: March 10, 2011
    Applicant: ORCHID CHEMICALS & PHARMACEUTICALS LIMITED
    Inventors: Sureshkumar KANAGARAJ, Sivakumar BALASUBRAMANIAN, Senthilkumar UDAYAMPALAYAM PALANISAMY
  • Patent number: 7833998
    Abstract: The treatment of neurological disorders using cephalosporin sulfoxide-containing and/or cephalosporin sulfone-containing compositions and pharmaceutical compositions including oral dosage forms that include cephalosporin sulfoxide and/or sulfone-containing compositions are described.
    Type: Grant
    Filed: August 24, 2004
    Date of Patent: November 16, 2010
    Assignee: Revaax Pharmaceuticals, LLC
    Inventors: Gary A. Koppel, Michael O. Chaney
  • Patent number: 7741478
    Abstract: Compounds of general formula (II), wherein R1 represents R4 represents hydrogen or —CHO group, R5 represents hydrogen or trityl, R2 represents hydrogen or methoxy group, R3 represents —CH?CH2 or and M represents a dialkyl or dicycloalkyl ethylenediamine group selected from N,N?-diisobutylethylenediamine, N,N?-dicyclohexylethylenediamine, and N,N?-dicyclopentylethylenediamine, are useful in a process to make cephalosporin antibiotics of formula (I) wherein R represents hydrogen or pharmaceutically acceptable esters or alkali metals salts.
    Type: Grant
    Filed: July 4, 2005
    Date of Patent: June 22, 2010
    Assignee: Orchid Chemicals & Pharmaceuticals Limited
    Inventors: Udayampalayam Palanisamy Senthilkumar, Venu Sanjeevi Lakshmipathi, Gnanaprakasam Andrew, Ramasubbu Chandrasekaran, Dindigala Nagender Rao, Gaddam Om Reddy
  • 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
  • Publication number: 20090299056
    Abstract: The present invention relates to cefazolin sodium pentahydrate crystal and a method for assembly and preparation of the crystal molecule. The cefazolin sodium pentahydrate crystal molecule contains five water molecules, orthorhombic system, space group of C222(1), in which sodium ion is bonded to the cefazolin molecule with a coordinate bond. The method for assembly and preparation of cefazolin sodium pentahydrate crystal molecule are: adding a solvent to a reactor equipped with a jacket, adding cefazolin acid and a sodium salt, heating until the reaction solution is clear, stirring continuously, adjusting pH, upon the completion of the reaction, transferring the liquid into a jacketed crystallizer, adding crystal seeds or nucleating spontaneously, controlling cooling, slowly adding a antisolvent.
    Type: Application
    Filed: September 15, 2006
    Publication date: December 3, 2009
    Inventors: Jingkang Wang, Yuxin Qian, Meijing Zhang, Jiehua Wu, Zhan'ao Yang
  • Patent number: 7511135
    Abstract: A process for preparation of ceftiofur of formula (I) having purity greater than 97% is disclosed.
    Type: Grant
    Filed: October 27, 2003
    Date of Patent: March 31, 2009
    Assignee: Lupin Limited
    Inventors: Om Dutt Tyagi, Santosh Kumar Richhariya, Rajesh Kumar Ramchandra Pawar, Yuvaraj Atmaram Chavan
  • Publication number: 20090075967
    Abstract: The present application describes deuterium-enriched ceftriaxone, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
    Type: Application
    Filed: August 22, 2008
    Publication date: March 19, 2009
    Applicant: PROTIA, LLC
    Inventor: Anthony W. Czarnik
  • 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
  • Patent number: 7452990
    Abstract: A novel 4-halo-2-oxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics wherein X is chlorine or bromine; R is hydrogen, C1-4 alkyl group, an easily removable hydroxyl protective group, —CH2COOR5, or —C(CH3)2COOR5, wherein R5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV1), wherein X, R and R5 are as defined above, with N,N-dimethylformiminium chloride chlorosulphate of formula (VII) in an organic solvent at a temperature ranging from ?30° C. to ?15° C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: November 18, 2008
    Assignee: Lupin Limited
    Inventors: Debashish Datta, Muralikrishna Dantu, Brijkishore Mishra, Pollepeddi Lakshmi Narayana Sharma
  • Publication number: 20080200670
    Abstract: An improved process for preparation of ceftriaxone sodium of formula (II), is disclosed.
    Type: Application
    Filed: January 11, 2008
    Publication date: August 21, 2008
    Applicant: Lupin Limited (Research Park)
    Inventors: Debashish Datta, Muralikrishna Dantu, Pollepeddi Lakshmi Narayana Sharma, Brijkishore Mishra
  • Publication number: 20080176825
    Abstract: The treatment of neurological disorders using cefazolin compositions and pharmaceutical compositions including oral dosage forms that include cefazolin compositions are described.
    Type: Application
    Filed: August 24, 2004
    Publication date: July 24, 2008
    Inventors: Gary A. Koppel, Michael O. Chaney
  • 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
  • Patent number: 7384928
    Abstract: A compound of the formula: (wherein, T is S, SO or O; X is halogen, CN, carbamoyl optionally substituted with lower alkyl, lower alkyl, lower alkoxy, or lower alkylthio; A is substituted lower alkylene (wherein the substituent is optionally substituted mono lower alkyl, optionally substituted lower alkylidene, or optionally substituted lower alkylene); Z+ is an optionally substituted, a cation and an N atom-containing heterocyclic group), ester, amino-protected compound wherein the amino bonds to a thiazole ring at the 7-position, or pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: June 10, 2008
    Assignee: Shionogi & Co., Ltd.
    Inventors: Yasuhiro Nishitani, Yoshinori Yamano
  • Patent number: 7339055
    Abstract: A process for the preparation of cephalosporin antibiotic of the formula (I) which comprises: (i) activating the compound of formula (III) as acid halide in an organic solvent (ii) treating the reaction mass obtained from step (i) with water (iii) separating the organic layer containing the reactive derivative of formula (III) and condensing it with 7-amino cephalosporin derivative by maintaining the pH in the range 5.0-10.0 using an inorganic base of the formula (XV), and iv) cyclizing the compound of formula (XVI) with thiourea in the presence of solvent and salt of organic or inorganic acid at a temperature in the range of ?50 to +50° C. to produce compound of formula (I).
    Type: Grant
    Filed: August 23, 2004
    Date of Patent: March 4, 2008
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Pandurang Balwant Deshpande, Udayampalayam Palanisamy Senthilkumar, Velladurai Hero
  • Patent number: 7335767
    Abstract: A process for preparation of ceftiofur sodium of formula (Ib) possessing high stability and having purity of more than 97% and substantially free of impurities, is disclosed. The process comprises: i) reacting cefotaxime or its salts or its esters of formula (VI) wherein R3 is hydrogen, an alkali or alkaline earth metal, or an easily hydrolysable ester, with thiofuroic acid, employed in a molar proportion of 1.5 to 3.0 moles per mole of compound (VI), in the presence of acetonitrile as solvent and in the presence of large excess of methanesulfonic acid, employed in molar proportions of 12 to 18 moles per mole of compound (VI), and at a temperature of between ?5° C. to 30° C.
    Type: Grant
    Filed: October 27, 2003
    Date of Patent: February 26, 2008
    Assignee: Lupin Limited
    Inventors: Om Dutt Tyagi, Santosh Kumar Richhariya, Rajesh Kumar Ramchandra Pawar
  • Patent number: 7098329
    Abstract: An improved process for the preparation of ceftriaxone sodium comprising the steps of: i) reacting the 3-cephem derivative of formula (II) ?with halo acid derivative of formula (III) ?wherein X represents halogen and Y represent halogen in the presence of silylating agent and methylene chloride at ?25 to 10° C., to produce (IV), ii) quenching the reaction by pouring the reaction mixture into water or in a aqueous solution of sodium carbonate, iii) preparing sodium salt solution of (IV) by adding sodium carbonate and separating the organic layer, iv) cyclizing the sodium salt of (IV) in the aqueous solution with thiourea at a temperature in the range of 0 to 30° C., v) adjusting the pH to 1.5 to 2.5 to precipitate the ceftriaxone free acid, vi) converting the ceftriaxone free acid to sodium salt using sodium-2-ethyl hexanoate in water and vii) precipitating and isolating the ceftriaxone sodium.
    Type: Grant
    Filed: June 16, 2004
    Date of Patent: August 29, 2006
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Pandurang Balwant Deshpande, Prabhat Kumar Sahoo, Anandam Vempali, Srinivasu Ghanta
  • 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: 6906187
    Abstract: There is described a process for the preparation of 3-disubstituted cepham-4-carboxylic acid derivatives of formula I wherein R? is 4-methoxybenzyl, X is the residue of a thioether and Z is a residue of a nucleophilic compound, such as 2-furoylthio, acetoxy or 1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-ylthio, by reaction of a functional derivative of ?-(2-chloroacetamido)thiazol-4-yl-?-methoxyiminoacetic acid with 7?-amino-3-methylenecepham-4-carboxylic acid 4-methoxybenzyl ester, subsequent treatment of the obtained 4-methoxybenzyl 7?-[?-(2-chloroacetamido)thiazol-4-yl-?-methoxyimino]acetamido-3-methylenecepham-4-carboxylate with a S-chloromercaptan of formula X—S—Cl, such as methanesulfenyl chloride, and final treatment of the corresponding 4-methoxybenzyl 7?-[?-(2-chloroacetamido)thiazol-4-yl-?-methoxyimino]acetamido-3-thio-3-chloromethylcepham-4-carboxylate thus obtained of formula V wherein R? and X are as defined above, with a compound of formula M-Z, in which M is an alkaline metal
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: June 14, 2005
    Assignee: Miat S.p.A.
    Inventor: Giordano Lesma
  • 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: 20040176590
    Abstract: There is described a process for the preparation of 3-disubstituted cepham-4-carboxylic acid derivatives of formula I 1
    Type: Application
    Filed: February 27, 2003
    Publication date: September 9, 2004
    Inventor: Glordano Lesma
  • Patent number: 6787649
    Abstract: A process which comprises (i) acylating a compound of formula II with a compound of formula IV to obtain a compound of formula I and (ii) deformylating said compound of formula I to obtain a compound of formula III
    Type: Grant
    Filed: February 12, 2003
    Date of Patent: September 7, 2004
    Assignee: Sandoz GmbH
    Inventors: Peter Kremminger, Johannes Ludescher, Siegfried Wolf
  • Patent number: 6777549
    Abstract: A process for the production of a compound of formula comprising i) silylating a compound of formula then reacting a resulting with a compound of formula R′BS—X′  IVB wherein R′B is hydrogen or trialkysilyl and X′ is as defined above, in the presence of a compound of formula wherein R2, R3 and R4 independently of each another are aryl or alkyl, and R5 is alkyl, perfluorinated alkyl, or aryl; and isolating the desired product.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: August 17, 2004
    Assignee: Sandoz GmbH
    Inventors: Benjamin Gerlach, Johannes Ludescher, Klaus Totschnig
  • Publication number: 20040132996
    Abstract: A process for preparation of ceftiofur sodium of formula (Ib) 1
    Type: Application
    Filed: October 27, 2003
    Publication date: July 8, 2004
    Applicant: LUPIN LIMITED
    Inventors: Om Dutt Tyagi, Santosh Kumar Richhariya, Rajesh Kumar Ramchandra Pawar
  • 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: 6713625
    Abstract: The present invention provides a process for the preparation of Cefditoren of the formula (I) which comprises acylating 7-amino-cephem carboxylic acids of the general formula (IV) where R3 is hydrogen or trimethylsilyl with thioester derivatives of the formula (II) wherein R1 represents C1-C4 alkyl or phenyl in an organic solvent in the presence of an organic base at a temperature in the range of −10° C. to 30° C.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: March 30, 2004
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Pandurang Balwant Deshpande, Parven Kumar Luthra
  • Publication number: 20040023943
    Abstract: A cephem compound (particularly its crystal) represented by the formula [I], wherein X is CH3COOH, CH3CH2COOH or CH3CN, and n is 0 to 5, is useful as an antibacterial agent (particularly anti-MRSA agent) and shows superior quality such as high solid stability, possible long-term stable preservation and the like.
    Type: Application
    Filed: January 29, 2003
    Publication date: February 5, 2004
    Inventors: Tomoyasu Ishikawa, Shohei Hashiguchi, Yuji Iizawa
  • Publication number: 20030225265
    Abstract: The present invention provides a process for the preparation of Cefditoren of formula (I) 1
    Type: Application
    Filed: May 23, 2002
    Publication date: December 4, 2003
    Inventors: Pandurang Balwant Deshpande, Parven Kumar Luthra
  • Publication number: 20030216567
    Abstract: The present invention relates to a new method for the preparation of Ceftiofur acid of formula (I), 1
    Type: Application
    Filed: July 30, 2002
    Publication date: November 20, 2003
    Applicant: ORCHID CHEMICALS AND PHARMACEUTICALS LIMITED
    Inventors: Pandurang Balwant Deshpande, Praven Kumar Luthra, Pratik Ramesh Sathe, Sivakumaran Sundaravadivelan, Praveen Nagesh Ganesh
  • Patent number: 6642377
    Abstract: A production process which comprises subjecting a basic antibiotic.oxalate (II) to salt-exchange with an alkali earth metal salt (III) of an inorganic acid: wherein the ring A means the basic antibiotic; R10 means a protected functional group used in organic synthesis; Ak—E means the alkali earth metal; and B means the inorganic acid, respectively.
    Type: Grant
    Filed: January 14, 2002
    Date of Patent: November 4, 2003
    Assignee: Eisai Co., Ltd.
    Inventors: Akio Kayano, Hiroyuki Chiba, Taiju Nakamura, Shin Sakurai, Hiroyuki Ishizuka, Hiroyuki Saito, Yuuki Komatsu, Manabu Sasho, Nobuaki Sato, Shigeto Negi
  • 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
  • Patent number: 6610845
    Abstract: The present invention provides new thioester derivatives of thiazolyl acetic acid of the general formula (I), wherein, R1 represents H, trityl, CH3, CRaRbCOOR2 (Ra and Rb independently of one another represents hydrogen or methyl and R2 represents H or C1-C4 alkyl). also, the invention provides a method by which the said thioester derivatives can be prepared by reacting thiazolyl acetic acid of the general formula (IV) with 1,2,5,6 tetrahdro-2-methyl-5,6 dioxo-1,2,4-triazin-3-thiol of the formula (VI) in a solvent, in presence of an organic base and with the help of Vilsmeier reagent of the formula (V). The so obtained thioester derivatives are reacted with 7-amino-cephem carboxylic acids of the general formula (III) to produce cephalosporin antibiotic compounds having the general formula (II).
    Type: Grant
    Filed: January 4, 2002
    Date of Patent: August 26, 2003
    Assignee: Orchid Chemicals & Pharmaceuticals Limited, India
    Inventors: Pandurang Balwant Deshpande, Pramod Narayan Deshpande, Shanmugam Srinivasan, Parven Kumar Luthra, Gautam Kumar Das
  • Publication number: 20030153748
    Abstract: A process and intermediates in the production of cefotiam (hexetil).
    Type: Application
    Filed: February 12, 2003
    Publication date: August 14, 2003
    Inventors: Peter Kremminger, Johannes Ludescher, Siegfried Wolf
  • 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: 6576761
    Abstract: 1. A process for preparing a 3-alkenylcephem compound or 3-norcephem compound of the formula (3) characterized in that an alkenyl halide of the formula (2), a nickel catalyst, a metal up to −0.3 (V/SCE) in standard oxidation reduction potential and a compound of a metal having a higher standard oxidation reduction potential than the metal are caused to act on a 3-cephem compound of the formula (1) in a solvent wherein R1 is a hydrogen atom or the like, R2 is a hydrogen atom or the like, R3 is a hydrogen atom or carboxylic acid protective group, and X is a halogen atom or the like, R4—Y  (2) wherein R4 is 1-alkenyl having or not having a substituent, and Y is a halogen atom wherein R1, R2 and R3 are as defined above, and R5 is a hydrogen atom or 1-alkenyl having or not having a substituent.
    Type: Grant
    Filed: February 7, 2002
    Date of Patent: June 10, 2003
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hideo Tanaka, Yutaka Kameyama
  • 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: 6555680
    Abstract: The present invention relates to a process for the preparation of sodium salt of Ceftiofur as given in Formula I, directly from its amine salt using sodium base.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: April 29, 2003
    Assignee: Orchid Chemicals & Pharmaceuticals Ltd.
    Inventors: Pandurang Balwant Deshpande, Pramod Narayan Deshpande, Milind Ramkrishna Kulkarni, Parven Kumar Luthra
  • Patent number: 6552186
    Abstract: The present invention provides processes for the production of a compound of formula I wherein X, R1 and R2 are substituents conventional in cephalosporin chemistry; especially a compound of formula I is ceftrixone, cefotaxime; e.g., in the form of a salt.
    Type: Grant
    Filed: October 11, 2001
    Date of Patent: April 22, 2003
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventors: Benjamin Gerlach, Johannes Ludescher, Klaus Totschnig