Alkyl, Hydroxyalkyl, Alkoxyalkyl Or Alkanoyloxyalkyl Bonded Directly To 3 Position Patents (Class 540/228)
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Patent number: 10344165Abstract: ?-Lactamase substrates and methods for using the substrates to detect ?-lactamase and to diagnose tuberculosis.Type: GrantFiled: December 4, 2017Date of Patent: July 9, 2019Assignees: The Texas A&M University System, The Board of Trustees of the Leland Stanford Junior UniversityInventors: Jianghong Rao, Hexin Xie, Yunfeng Cheng, Jeffrey D. Cirillo
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Patent number: 9273049Abstract: The invention provides a method for increasing the solubility of nevirapine, including the steps of rendering nevirapine in a gaseous phase; and rendering the gaseous phase in a relatively more soluble solid particulate form. The invention further provides for a crystalline Form-VI (36) of nevirapine having an X-ray diffraction pattern of (2-theta values in degrees) 9.2953, 11.2023, 12.7019, 12.9796, 13.5273, 15.4670, 17.2597, 19.1038, 19.7267, 21.1303, 22.9381, 25.5589, 26.4913, 27.2150, 27.7283, 29.7134, and 33.8343 degrees two theta. The invention further provides for the preparation of microspherical and/or nanospherical Form-V (34) and crystalline Form-VI (36) of nevirapine as well as novel dosage forms including parenteral-, inhalant-, transdermal- and oral dosage forms.Type: GrantFiled: November 9, 2010Date of Patent: March 1, 2016Assignee: North-West UniversityInventors: Wilna Liebenberg, Nicole Stieger
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Patent number: 9006422Abstract: The present invention relates to an improved process for oxidizing 3-hydroxy-methyl-cephem derivatives to the corresponding 3-formyl-cephem derivatives. In particular this oxidation process is for the preparation of 7-[2-(5-amino-[1,2,4]thia-diazol-3-yl)-2-hydroxyimino-acetylamino]-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid derivatives of formula (I) using a combination of a hypervalent iodine oxidizing agent of the type 10-I-3 such as bis(acetoxy)iodo-benzene (BAIB) and a catalyst such as 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO). These compounds of formula (I) are intermediates in the synthesis of ceftobiprole.Type: GrantFiled: May 9, 2011Date of Patent: April 14, 2015Assignee: Basilea Pharmaceutica International Ltd.Inventor: Ivan Joseph Maria Vervest
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Patent number: 8575144Abstract: Inhibitors of the enzyme beta-lactamase are provided comprising compounds of formula (II) wherein R1 or R2 is a pyridyl group and R5 is a group of formula The compounds are adapted to inhibit beta-lactamase as produced by beta-lactam resistant bacterial strains. Methods of treatment of beta-lactam resistant bacterial infections in patients are provided.Type: GrantFiled: September 27, 2012Date of Patent: November 5, 2013Assignee: Southern Methodist UniversityInventors: John D. Buynak, Anjaneyulu Sheri, Sundar Ram Reddy Pagadala
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Publication number: 20130090470Abstract: 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: ApplicationFiled: September 13, 2012Publication date: April 11, 2013Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Schuyler CORRY, William Downey, Brian Filanoski, Kyle Gee, Lawrence Greenfield, James Hirsch, Iain Johnson, Aleksey Rukavishnikov
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Publication number: 20120329770Abstract: 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: ApplicationFiled: February 25, 2011Publication date: December 27, 2012Inventors: Gary Igor Dmitrienko, Ahmad Ghavami, Valerie Joy Goodfellow, Jarrod W. Johnson, Anthony Paul Krismanich, Laura Marrone, Thammaiah Viswanatha, Sundaramma Viswanatha
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Patent number: 8044195Abstract: 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: GrantFiled: April 13, 2010Date of Patent: October 25, 2011Assignee: Theravance, Inc.Inventor: Daniel D. Long
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Publication number: 20110257388Abstract: A compound represented by Formula I, wherein M represents Na+, K+, NH4+, or Cs+; and 1) when Y represents SO42?: when m=1, then n=1; and when m=0.5, then n=1.5; and 2) when Y represents PO42?, when m=1, then n=2. The compound has good solubility and high bioavailability and can be formulated into oral pharmaceutical preparations and pharmaceutical preparations for injections.Type: ApplicationFiled: June 30, 2011Publication date: October 20, 2011Applicant: ZHEJIANG ADAMERCK BIOPHARMLABS INC.Inventors: Youmao QI, Fengqi YE, Qing JIE, Yingbei QI, Fengmin ZHANG, Baochun YU, Tianjian YE, Meiping YU
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Patent number: 7728127Abstract: 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: GrantFiled: August 24, 2007Date of Patent: June 1, 2010Assignee: Theravance, Inc.Inventors: Paul R. Fatheree, Martin S. Linsell, Daniel Marquess, S. Derek Turner
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Publication number: 20090227787Abstract: The present invention provides an improved process for the preparation of Cefixime of formula (I), a cephalosporine antibiotic with an improved quality in regard to color and solubility.Type: ApplicationFiled: December 19, 2005Publication date: September 10, 2009Applicant: LUPIN LIMITEDInventors: Om Dutt Tyagi, Dnyandeo Ragho Rane, Sanjay Mahajan, Yuvraj Atmaram Chavan
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Patent number: 7553962Abstract: 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: GrantFiled: August 24, 2007Date of Patent: June 30, 2009Assignee: Theravance, Inc.Inventors: Paul R. Fatheree, Martin S. Linsell, Daniel Marquess, S. Derek Turner
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Publication number: 20080306256Abstract: The present invention relates to an improved process for the preparation of cephalosporin antibiotics of formula (I). The present invention also provides new salts of compound of formula (II) and a process for the preparation of these new salts, where n=0.5 to 2. The present invention also provides a process for the preparation of compound of formula (I) using the new salts of formula (II).Type: ApplicationFiled: July 4, 2005Publication date: December 11, 2008Applicant: Orchid Chemicals & Pharmaceuticals LimitedInventors: Udayampalayam P. Senthilkumar, Venu S. Lakshmipathi, Gnanaprakasam Andrew, Ramasubbu Chandrasekaran, Dindigala Nagender Rao, Gaddam Om Reddy
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Patent number: 7452990Abstract: 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: GrantFiled: December 26, 2002Date of Patent: November 18, 2008Assignee: Lupin LimitedInventors: Debashish Datta, Muralikrishna Dantu, Brijkishore Mishra, Pollepeddi Lakshmi Narayana Sharma
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Patent number: 7355040Abstract: There is provided a process for the preparation of a compound according to Formula (II): which includes the step of cyclizing a compound of Formula (III): wherein R1, R2, R3, R4, X and m have meanings which are given in the description.Type: GrantFiled: November 22, 2004Date of Patent: April 8, 2008Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
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Patent number: 7339055Abstract: 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: GrantFiled: August 23, 2004Date of Patent: March 4, 2008Assignee: Orchid Chemicals & Pharmaceuticals Ltd.Inventors: Pandurang Balwant Deshpande, Udayampalayam Palanisamy Senthilkumar, Velladurai Hero
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Patent number: 7273935Abstract: A process for the preparation of 3-methylcepham-4-carboxylate of the formula (I). wherein R2 and R3 may be same or different and represent hydrogen, halogen, amino, alkyl, phenacetamido, substituted acetamido, phthalimido with a proviso that both R2 and R3 are not NH2, phenacetamido, phthalimido and the like; R1 represents a lower alkyl, p-methoxybenzyl, p-nitrobenzyl, o-nitrobenzyl, o-methoxybenzyl, o-chlorobenzyl or diphenylmethyl group, or a suitable ester residue which can be deprotected at a latter stage, L represents a leaving group; which comprises cyclizing the compound of formula (III) using a cyclizing agent in the presence of organic or inorganic nitrites and a solvent at a temperature in the range of ?40° C. to +60° C. to obtain compound of formula (I).Type: GrantFiled: August 23, 2004Date of Patent: September 25, 2007Assignee: Orchid Chemicals & Pharmaceuticals, Ltd.Inventors: Pandurang Balwant Deshpande, Udayampalayam Palanisamy Senthilkumar, Andrew Gnanaprakasam, Kanagaraj Sureshkumar
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Patent number: 7071329Abstract: 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: GrantFiled: August 12, 2004Date of Patent: July 4, 2006Assignee: ACS Dobfar S.p.A.Inventors: Riccardo Monguzzi, Antonio Manca, Leonardo Marsili, Maurizio Zenoni
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Patent number: 7045618Abstract: The present invention relates to an improved and cost effective process for the industrial manufacture of cefpodoxime proxetil. More specifically, the present invention relates to the preparation of cefpodoxime proxetil of high purity and yield. The process comprises a) dissolving impure cefpodoxime proxetil or adding a solution containing cefpodoxime proxetil into a polar organic solvent or mixture(s) thereof, optionally reducing the solvent by concentration, and adding into a non-polar organic solvent or mixture(s) thereof to precipitate the solid; and b) dissolving the solid obtained from the above step into water-miscible polar organic solvent, optionally reducing the solvent by concentration, adding it into water to obtain the pure cefpodoxime proxetil.Type: GrantFiled: February 27, 2002Date of Patent: May 16, 2006Assignee: Ranbaxy Laboratories LimitedInventors: Yatendra Kumar, Kaptan Singh, Rakesh Kumar Arora
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Patent number: 6949641Abstract: The novel intermediate compound crystalline 7-[2-(2-fomylaminothiazol-4-yl)-2 -(Z)-(methoxyimino)acetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid-1 -(isopropoxy/crystallization of cefpodoxime proxetil. The crystallization process comprises dissolving or suspending the intermediate in the presence of a nitrile or a ketone or mixtures thereof; at a ratio of 1 gm of the intermediate to 2-15 ml nitrile; or at a ratio of 1 gm of the intermediate to 3-15 ml ketone; in the presence of 5-80 ml water; and thereafter isolating the intermediate in crystalline form and converting the intermediate by splitting off the formyl group from the amino group attached to the thiazolyl group, to obtain the desired product cefpodoxime proxetil, in the form of a diastereoisomeric mixture in a ratio of B/(A+B) of 0.5 to 0.6.Type: GrantFiled: October 31, 2001Date of Patent: September 27, 2005Assignee: Sandoz AGInventors: Julia Greil, Johannes Ludescher, Klaus Totschnig, Siegfried Wolf
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Patent number: 6825344Abstract: There is provided a process for the preparation of a compound according to Formula (II): which includes the step of cyclising a compound of Formula (III): wherein R1, R2, R3, R4, X and m have meanings which are given in the description.Type: GrantFiled: July 30, 2001Date of Patent: November 30, 2004Assignee: Pfizer Inc.Inventors: Desmond John Best, George Burton, Brian Charles Gasson, Neal Frederick Osborne, Graham Walker
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Publication number: 20040210050Abstract: A process for the preparation of highly pure cefuroxime axetil is herein described. The process makes use of a treatment, which allows removing an impurity present in the reagent 1-acetoxyethyl bromide and responsible for the formation of cefuroxime dimeric derivatives. The removal of said impurity makes it easier to recover crystalline, cefuroxime axetil and allows obtaining an exceptional-quality product.Type: ApplicationFiled: June 9, 2004Publication date: October 21, 2004Inventors: Claudio Felisi, Davide Longoni, Marco Alpegiani, Walter Cabri
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Publication number: 20040077850Abstract: An improved method for synthesis of cefuroxime axetil of formula (I) in high purity substantially free of the corresponding 2-cephem(&Dgr;2)-ester of formula (II) and other impurities. The compound produced is valuable as a prodrug ester of the corresponding cephalosporin-4-carboxylic acid derivative i. e. cefuroxime, particularly suitable for oral administration in various animal species and in man for treatment of infections caused by gram-positive and gram-negative bacteria.Type: ApplicationFiled: August 20, 2003Publication date: April 22, 2004Inventors: Vinod Kumar Kansal, Sunil Gurudatt Bhat, Tanguturi Venkata Marutikumar, Yuvaraj Atmaram Chavan, Ramanathan Sankaran
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Publication number: 20040077849Abstract: The present invention relates to an improved process for the preparation of cefadroxil of the formula (I), more particularly, the present invention relates to an improved process for the preparation of cefadroxil having water content in the range of 4-5%.Type: ApplicationFiled: December 5, 2002Publication date: April 22, 2004Applicant: Orchid Chemicals & Pharmaceuticals LimitedInventors: Pramod Narayan Deshpande, Gautam Kumar Das, Rajendra Janardan Sarangdhar, Peter Xavier Tharial
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Patent number: 6683176Abstract: 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: GrantFiled: December 31, 2001Date of Patent: January 27, 2004Inventors: Robin D. G. Cooper, Anthony G. M. Barrett
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Publication number: 20040002601Abstract: A method for producing cephalosporins 7-substituted with an amino-thiazolylacetic group by reacting 7-ACA or its derivatives having the amino group and the carboxyl protected with reactive derivatives of amino-thiazolylacetic acid.Type: ApplicationFiled: January 21, 2003Publication date: January 1, 2004Applicant: ACS DOBFAR S.p.A.Inventors: Maurizio Zenoni, Giovanni Fogliato, Mauro Filippi
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Patent number: 6642377Abstract: 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: GrantFiled: January 14, 2002Date of Patent: November 4, 2003Assignee: Eisai Co., Ltd.Inventors: Akio Kayano, Hiroyuki Chiba, Taiju Nakamura, Shin Sakurai, Hiroyuki Ishizuka, Hiroyuki Saito, Yuuki Komatsu, Manabu Sasho, Nobuaki Sato, Shigeto Negi
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Patent number: 6639068Abstract: Highly pure cefpodoxime proxetil can be prepared by a simple process comprising the step of reacting a cefpodoxime salt with 1-iodoethylisopropylcarbonate in an organic solvent in the presence of a crown ether.Type: GrantFiled: April 24, 2002Date of Patent: October 28, 2003Assignee: Hanmi Pharm. Co., Ltd.Inventors: Gwan-Sun Lee, Young-Kil Chang, Jae-Heon Lee, Chul-Hyun Park, Gha-Seung Park, Keum-Shin Jung
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Patent number: 6610845Abstract: 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: GrantFiled: January 4, 2002Date of Patent: August 26, 2003Assignee: Orchid Chemicals & Pharmaceuticals Limited, IndiaInventors: Pandurang Balwant Deshpande, Pramod Narayan Deshpande, Shanmugam Srinivasan, Parven Kumar Luthra, Gautam Kumar Das
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Patent number: 6602999Abstract: A novel process for the production of an improved amorphous form of cefpodoxime proxetil [(6R-[6&agr;,7&bgr;(Z))]-7-{E(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-1-[[(1-methylethoxy)carboxylic acid-1-[[(1-methylethoxy)carbonyl]oxy]ethyl ester, is described.Type: GrantFiled: May 21, 2002Date of Patent: August 5, 2003Assignee: Ranbaxy Laboratories LimitedInventors: Yatendra Kumar, Rakesh Kumar Arora, Kaptan Singh
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Patent number: 6552186Abstract: 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: GrantFiled: October 11, 2001Date of Patent: April 22, 2003Assignee: Biochemie Gesellschaft m.b.H.Inventors: Benjamin Gerlach, Johannes Ludescher, Klaus Totschnig
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Patent number: 6504025Abstract: Disclosed is a process for the preparation of vinyl-pyrrolidinone cephalosporine derivatives of formula Also disclosed are intermediate compounds of formulas wherein R1 and R2 are as defined herein.Type: GrantFiled: May 17, 2001Date of Patent: January 7, 2003Assignee: Basilea Pharmaceutica AGInventors: Paul Hebeisen, Hans Hilpert, Roland Humm
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Patent number: 6489470Abstract: A process for increasing the diastereoisomeric ratio (B/A+B), wherein B is the more apolar and A is the more polar of two diastereoisomers, of a mixture of diastereoisomers of a compound of formula the diastereoisomers being with respect to the carbon atom marked with a star in formula I, comprising treating a mixture of diastereoisomers of a compound of formula I with alcohol and water and isolating the precipitated compound of formula I in an increased diastereoisomeric ratio (B/A+B) of 0.5 to 0.6.Type: GrantFiled: August 21, 2000Date of Patent: December 3, 2002Assignee: Biochemie Gesellschaft m.b.H.Inventors: Julia Greil, Johannes Ludescher, Klaus Totschnig, Siegfried Wolf
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Publication number: 20020099206Abstract: The object of the invention is to provide cephalosporin crystals which are highly stable for a long period under economical storage conditions. The cephalosporin crystals of the invention are obtainable by crystallizing an oily cephalosporin in a solvent containing an alcohol.Type: ApplicationFiled: January 9, 2002Publication date: July 25, 2002Inventors: Yutaka Kameyama, Takashi Shiroi
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Patent number: 6407091Abstract: 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: GrantFiled: April 13, 2000Date of Patent: June 18, 2002Assignee: Research Corporation Technologies, Inc.Inventors: John D. Buynak, A. Srinivasa Rao, Greg C. Adam, Sirishkumar D. Nidamarthy, Venkata Ramana Doppalapudi
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Patent number: 6388070Abstract: The present invention provides novel thioester derivatives of thiazolyl acetic acid of the general formula (I), wherein, R1 represents H, trityl, CH3, or CRaRbCOOR3, in which Ra and Rb, independently of one another, represents hydrogen or methyl and R3 represents H or C1-C7 alkyl; and R2 represents C1-C4 alkyl or phenyl.Type: GrantFiled: January 5, 2001Date of Patent: May 14, 2002Assignee: Orchid Chemicals & Pharmaceuticals Ltd.Inventors: Pandurang Balwant Deshpande, Parven Kumar Luthra
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Patent number: 6384212Abstract: The present invention relates to a new, simple, and easy process for preparing cephalosporin antibiotics of the following formula (I), such as ceftazidime and cefixime. The process comprises acylating a 7-amino cephalosporanic acid derivative of the following formula (III) with a crystalline aminothiazole compound of the following formula (II): wherein R1 and R2 are the same or different and independently represent H, a C1-4 alkyl or C3-5 cycloalkyl group, R4 represents acetoxymethyl, methylpyridine, or vinyl, X represents chlorine or bromine, and the acid in the acid addition salt represents an inorganic acid, such as hydrochloric acid, or an organic acid, such as formic acid or acetic acid.Type: GrantFiled: May 4, 2000Date of Patent: May 7, 2002Assignee: Hanmi Fine Chemicals Co., Ltd.Inventors: Dae-chul Yoon, Seung Won Yoo, Dong Gyun Shin, Myoung Ki Lee, Mi Soon Park, Yoon Seok Lee, Yoon Seok Song, Ju Cheol Lee, Sang Mi Oh
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Patent number: 6303592Abstract: Derivatives of 7-alkylidene cephalosporanic acid sulfone and the pharmaceutically active salts thereof are found to be potent inhibitors of &bgr;-lactamase enzymes.Type: GrantFiled: March 14, 1997Date of Patent: October 16, 2001Assignee: Research Corporation Technologies, Inc.Inventors: John D. Buynak, Brian Bachmann
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Publication number: 20010011085Abstract: 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: ApplicationFiled: August 14, 1997Publication date: August 2, 2001Inventors: MARCO ALPEGIANI, PIERLUIGI BISSOLINO, MASSIMILIANO PALLADINO, ETTORE PERRONE
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Patent number: 6255480Abstract: Aminothiazole derivatives having the carboxyl activated by means of thioesters, said derivatives being condensable with &bgr;-lactam nuclei to yield &bgr;-lactam antibioticsType: GrantFiled: June 24, 1999Date of Patent: July 3, 2001Assignee: Ortho-McNeil Pharmaceutical, Inc.Inventors: Maurizio Zenoni, Mario Leone, Maurizio Serra, Mauro Filippi
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Substituted amino bicyclic-&bgr;-lactam penam and cepham derivatives as cysteine protease inhibitors
Patent number: 6232305Abstract: The present invention provides substituted amino bicyclic-&bgr;-lactam penam derivatives and substituted amino bicyclic-&bgr;-lactam cepham derivatives and their diastereoisomers of formula I, as well as compositions, methods of making, and methods of using, which exhibit excellent cysteine protease inhibitory activity and which may be used for treatment of different diseases such as cancer (including cancer metastasis), osteoporosis, rheumatoid arthritis.Type: GrantFiled: January 22, 1998Date of Patent: May 15, 2001Assignee: Naeja Pharmaceutical Inc.Inventors: Rajeshwar Singh, Nian Zhou, Deqi Guo, Ronald G. Micetich -
Patent number: 6107481Abstract: A process to prepare the E isomer of a 3-substituted (6R,7R)-7-phenyl-acetamido-ceph-3-em-4-carboxylic acid from a mixture of the E and Z-isomer of either the corresponding tert-butyl or the corresponding 4-methoxybenzyl ester of a 3-substituted (6R,7R)-7-phenylacetamido-ceph-3-em-4-carboxylate, characterized by the application of a compound selected from the group titanium tetrachloride, tin tetrachloride and tellurium tetrachloride.Type: GrantFiled: July 13, 1999Date of Patent: August 22, 2000Assignee: DSM N.V.Inventors: Erik De Vroom, Thomas Van Der Does
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Patent number: 6100393Abstract: Process for purifying 7-substituted aminodeacetoxycephalosporins through the use of filter membranes. A process for purification by ultrafiltration and/or nanofiltration with a cut-off for molecular weights over 10,000 Dalton and preferably over 2000 Dalton is described. For example cephalosporin-G of increased purity, represented by a 6-8% increase in the HPLC titre, with a reduction of 50% in absorbance, is obtained using this technique. The invention makes it possible for the purified products to be used directly in the synthesis of other antibiotic compounds without the need for intermediate isolation.Type: GrantFiled: February 25, 1998Date of Patent: August 8, 2000Assignee: Antibioticos, S.A.Inventors: Juan Francisco Lopez Ortiz, Oscar Ferrero Barruego, Emiliano Gonzalez de Prado, Alejandro Vitaller Alba, Francisco Salto Maldonado
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Patent number: 5998611Abstract: An industrially excellent, novel process for producing cephem compounds which are useful as medicines, particularly, antibiotics and represented by the following formula (III): ##STR1## wherein R.sup.1 means either group represented by the following formula: ##STR2## R.sup.2 denotes a carboxyl group or a carboxyl anion, and R.sup.3 stands for a lower alkyl group, a halogen atom, a lower alkyl group substituted by an aliphatic acyloxy group having 1-6 carbon atoms, or any one of the groups represented by the following formulae: ##STR3## which comprises reacting in water a 3-cephem-4-carboxylate represented by the following formula (I): ##STR4## or a salt thereof with an acid chloride represented by the formula (II), R.sup.1 COCl.Type: GrantFiled: September 25, 1997Date of Patent: December 7, 1999Assignee: Eisai Chemical Co., Ltd.Inventors: Homare Shinohara, Masato Kodama, Kimio Hamamura, Hirofumi Kuroda
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Patent number: 5945532Abstract: This invention relates to reactive derivatives of 2-(2-aminothiazol-4-yl)-2-methoxyimino acetic acid and 1H-tetrazol-1-acetic acid of the following general formula I, ##STR1## wherein ##STR2## as well as to use thereof in the manufacture of cephalosporin antibiotics such as cefotaxime, ceftriaxone and cefazolin.Type: GrantFiled: September 16, 1998Date of Patent: August 31, 1999Assignee: Lupin Laboratories LimitedInventors: Debashish Datta, Vinod George, Bishwa Prakash Rai
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Patent number: 5922861Abstract: An efficient process for de-esterification has been provided for by application of special tetrahalogenides. By applying this process a new compound, viz. cefesone, and especially the E-isomer thereof, has been prepared.Type: GrantFiled: April 1, 1998Date of Patent: July 13, 1999Assignee: Gist-Brocades B.V.Inventors: Erik De Vroom, Thomas Van Der Does
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Patent number: 5869649Abstract: A process for preparing certain cephalosporin antibiotics, namely, cefotaxime, cefetemet, and ceftriaxone sodium comprising acylation of 7-amino-3-cephem-4-carboxylic acid derivatives with 2-mercapto-5-methyl-1,3,4-thiadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-metho xyiminoacetate having the formula: ##STR1##Type: GrantFiled: May 1, 1996Date of Patent: February 9, 1999Assignee: Ranbaxy Laboratories Ltd.Inventors: Jag Mohan Khanna, Vijay Kumar Handa, Ramesh Dandala, Ram Chander Aryan
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Patent number: 5831086Abstract: A process for the production of cefotaxime in acetone/water and its use in the production of a sodium salt of cefotaxime and a crystalline sodium salt of cefotaxime in the form of rounded agglomerates and in the form of needles.Type: GrantFiled: June 20, 1997Date of Patent: November 3, 1998Assignee: Biochemie Gesellschaft m.b.H.Inventors: Ingolf Macher, Gerhard Widschwenter
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Patent number: 5763617Abstract: A syn isomer in (R) or (S) form or a mixture thereof of a compound of the formula ##STR1## syn isomer, in the (R) or (S) form or in the form of an (R,S) mixture, in the form of an integral salt or their salts with organic or mineral acids wherein the substituents are as defined in the application and having antibacterial properties.Type: GrantFiled: December 18, 1996Date of Patent: June 9, 1998Assignee: Roussel UclafInventors: Jozsef Aszodi, Jean-Francois Chantot, Patrick Fauveau, Solange Gouin D'Ambrieres, Daniel Humbert, Christophe Dini
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Patent number: 5760027Abstract: The present invention relates to the use of 7-alkylidene derivatives of cephalosporin esters, such as sulfides, sulfoxides, and sulfones, as inhibitors of human leukocyte elastase. These materials are therefore useful as anti-inflammatory and anti-degenerative agents.Type: GrantFiled: December 6, 1996Date of Patent: June 2, 1998Assignee: Research Corporation Technologies, Inc.Inventors: John D. Buynak, Akireddy Srinivasa Rao, Greg C. Adam
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Patent number: 5710146Abstract: Cephem derivatives of the general formula ##STR1## in which the R.sub.2 O group is in the syn-position, a process for their manufacture and pharmaceutical formulations which are active against bacterial infections and contain these compounds.Type: GrantFiled: July 22, 1994Date of Patent: January 20, 1998Assignee: Hoechst AktiengesellschaftInventors: Walter Durckheimer, Dieter Bormann, Eberhard Ehlers, Elmar Schrinner, Rene Heymes