1-thia-5-aza-bicyclo(4.2.0)octane (including Unsaturated; E.g., Cepham, Etc.) Patents (Class 540/215)
  • Patent number: 10026991
    Abstract: Provided are a manufacturing method for an amino-substituted phosphazene compound including reacting a fluorinated phosphazene compound and an amine compound in presence of a compound having a fluorine trapping function; and synthesizing a compound obtained by substituting the amine compound for the fluorinated phosphazene compound, a manufacturing method for an electrolyte solution for a nonaqueous secondary battery using this, and a manufacturing method for a nonaqueous secondary battery.
    Type: Grant
    Filed: December 30, 2016
    Date of Patent: July 17, 2018
    Assignee: FUJIFILM Corporation
    Inventor: Yoshinori Kanazawa
  • Patent number: 9920014
    Abstract: The present invention provides novel bisbenzimidazole compounds and methods of using the compounds as antibacterial agents.
    Type: Grant
    Filed: September 19, 2014
    Date of Patent: March 20, 2018
    Assignees: THE FLORIDA INTERNATIONAL UNIVERSITY BOARD OF TRUSTEES, CLEMSON UNIVERSITY
    Inventors: Nihar Ranjan, Dev P. Arya, Fenfei Leng
  • Patent number: 9006421
    Abstract: Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.
    Type: Grant
    Filed: March 14, 2014
    Date of Patent: April 14, 2015
    Assignee: Cubist Pharmaceuticals, Inc.
    Inventors: Jan-Ji Lai, Pradip M. Pathare, Laxma Kolla, Adrien F. Soret
  • Patent number: 8883772
    Abstract: Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Compounds of the invention include those of formula: and pharmacologically acceptable salts thereof where variables Z, Y, M, y, n, R, R4, R5, R1 and R2 are as defined in the specification. M most generally represents a chemical moiety which is in conjugation with the nitrogen of the core beta-lactam ring system of the compound, such that one or more reactive species, e.g., electrophilic or nucleophilic sites are generated on modification of M which is initiated by cleavage of the beta-lactam ring. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition.
    Type: Grant
    Filed: October 9, 2008
    Date of Patent: November 11, 2014
    Assignee: Sopharmia, Inc.
    Inventors: Larry Sutton, Sophia Yu
  • Publication number: 20140274958
    Abstract: Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Inventors: Jan-Ji Lai, Pradip M. Pathare, Laxma Kolla, Adrien F. Soret
  • Publication number: 20140221331
    Abstract: The present invention relates generally to methods and compounds for regulating the release of nitric oxide in the vicinity of biofilm-forming microorganisms to regulate programmed cell death in the microorganisms and thereby promote dispersal of microorganism from biofilms and/or inhibit biofilm formation or development. More particularly, the invention relates to the use of compounds to provide spatial and temporal control over nitric oxide release.
    Type: Application
    Filed: May 16, 2012
    Publication date: August 7, 2014
    Applicants: UNIVERSITY OF WOLLONGONG, NEWSOUTH INNOVATIONS PTY LIMITED
    Inventors: Nicolas Barraud, Bharat Gangadhar Kardak, Michael John Kelso, Staffan Kjelleberg, Scott Rice
  • Publication number: 20130131006
    Abstract: The present invention relates to a method for inhibiting the induction of cell death by inhibiting the synthesis or secretion of AGE-albumin in cells of the mononuclear phagocyte system, to an AGE-albumin synthesis inhibitor, and to a pharmaceutical composition comprising the AGE-albumin synthesis inhibitor for preventing or treating degenerative disease and autoimmune disease. The AGE-albumin of the present invention is synthesized and secreted in human microglia or human macrophages in an Alzheimer's model, stroke model, Parkinson's disease model and rheumatoid arthritis model. The AGE-albumin synthesis and secretion are caused by oxidative stress. The expression of RAGE increases in first-order human neurons or cartilage cells to which AGE-albumin is administered, whereupon a MAPK signaling pathway is activated and the expression of Bax increases to induce an increase in calcium in mitochondria, thus finally inducing cell death.
    Type: Application
    Filed: April 28, 2011
    Publication date: May 23, 2013
    Applicant: Gachon University of Industry-Academic Cooperation Foundation
    Inventors: Bong Hee Lee, Kyung Hee Byun
  • Patent number: 8299051
    Abstract: Inhibitors of the enzyme beta-lactamase of formula (I): are provided. 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: Grant
    Filed: May 11, 2009
    Date of Patent: October 30, 2012
    Assignee: Southern Methodist University
    Inventors: John D. Buynak, Anjaneyulu Sheri, Sundar Ram Reddy Pagadala
  • 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
  • Patent number: 7932283
    Abstract: The present invention relates to N-cyclopropyl-sulfonylamide derivatives of formula (I) wherein the substituents are cyclic groups, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions:
    Type: Grant
    Filed: April 5, 2007
    Date of Patent: April 26, 2011
    Assignee: Bayer Cropscience AG
    Inventors: Hans-Georg Schwarz, Sandra Gassmann, Karl-Heinz Kuck, Peter Dahmen, Ulrike Wachendorff-Neumann, Stéphane Carbonne, Stéphanie Gary, Christopher Steele, Alain Villier, Jean-Pierre Vors
  • Publication number: 20110040086
    Abstract: The invention relates to novel antimicrobial agents that are based on ?-lactam derivatives and are produced by reacting previously known ?-lactam derivatives with polyphenol oxidase substrates under the influence of free radicals and by forming salts of any ?-lactam derivatives with polyhexamethylene biguanide hydrogen carbonate. Said novel compounds are suitable as an antibiotic.
    Type: Application
    Filed: January 31, 2008
    Publication date: February 17, 2011
    Applicant: DRITTE PATENTPORTFOLIO BETEILIGUNGSGESELLSCHAFT MB
    Inventors: Wolf-Dieter Juelich, Ulrike Lindequist, Annett Mikolasch, Sabine Witt, Frieder Schauer, Roland Ohme
  • 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: 7728025
    Abstract: A glucokinase activator is provided; and a remedy and/or a preventive for diabetes, or a remedy and/or a preventive for diabetes such as retinopathy, nephropathy, neurosis, ischemic cardiopathy, arteriosclerosis, and further a remedy and/or a preventive for obesity are provided. A glucokinase activator characterized by containing a 2-heteroaryl-substituted benzimidazole derivative of a general formula (I-0) or its pharmaceutically-acceptable salt: [in the formula, X represents a carbon atom or a nitrogen atom; X1, X2, X3 and X4 each independently represent a carbon atom or a nitrogen atom; the ring A represents a 5- or 6-membered nitrogen-containing aromatic hetero ring of a formula (II): (in the formula, X represents a carbon atom or a nitrogen atom); R1 represents an aryl, etc.; R2 represents a hydroxy, etc.; R3 represents a —C1-6 alkyl, etc.; R4 represents a —C1-6 alkyl, etc.; X5 represents —O—, etc.
    Type: Grant
    Filed: December 28, 2004
    Date of Patent: June 1, 2010
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Katsumasa Nonoshita, Makoto Ishikawa, Hiroshi Nakashima, Daisuke Tsukahara, Yoshio Ogino, Fumiko Sakai, Yoshikazu Nagae, Keisuke Arakawa, Teruyuki Nishimura
  • Publication number: 20100016208
    Abstract: Photoactivatable antimicrobial compounds and methods for the use thereof in the treatment of infections are provided.
    Type: Application
    Filed: November 15, 2006
    Publication date: January 21, 2010
    Applicant: THE GENERAL HOSPITAL CORPORATION
    Inventors: Tayyaba Hasan, Gerald J. Nau
  • Publication number: 20100009954
    Abstract: Inhibitors of the enzyme beta-lactamase are provided. 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: Application
    Filed: May 11, 2009
    Publication date: January 14, 2010
    Inventors: John D. Buynak, Anjaneyulu Sheri, Sundar Ram Reddy Pagadala
  • Patent number: 7622577
    Abstract: Provided is a process for preparing a compound of formula 1 or its salt, which comprises reacting a compound represented by the following formula 4 with acetaldehyde in a mixed solvent comprising water, isopropanol, and methylenechloride in a volume ratio of 1:3-6:11-14 in the presence of a first base to stereospecifically prepare a compound represented by the following formula 3?; and reacting the compound of the formula 3? with an anhydrous compound represented by the following formula 2 in the presence of a second base: wherein R1 is a hydrogen or an amino protecting group, R2 is a hydrogen or a carboxyl protecting group, and R3 is a hydrogen or an amino protecting group consisting of phenylacetyl group, wherein when R3 is a phenylacetyl group, R2 is not a hydrogen in formula 3?; and wherein, when at least one of R2 and R3 is a protecting group, all such protecting groups are removed from formula 3?, thereby producing a compound represented by formula 6 prior to reacting it with the compound o
    Type: Grant
    Filed: October 30, 2004
    Date of Patent: November 24, 2009
    Assignee: CJ Cheiljedang Corporation
    Inventors: Dae Won Seo, In Hwa Chung, Ki Bong Lee, In Kyu Lee
  • Patent number: 7592447
    Abstract: A process for the production of intermediates having a formula IA that can be used for the synthesis of cephalosporins, such as cefepime of formula V. The intermediates of formula IA are produced by desilyation of a compound of formula II wherein R4 is a silyl-protecting group, with a protic solvent to obtain a compound of formula III, and reacting the compound of formula III with an organic base of formula IV wherein R2 and R3 together represent a C4-alkylene group, and with the adjacent nitrogen atom form a saturated 5-membered heterocycle, and R1 represents a methyl group, to obtain the compound of formula 1A.
    Type: Grant
    Filed: December 22, 2004
    Date of Patent: September 22, 2009
    Assignee: Sandoz AG
    Inventors: Johannes Ludescher, Hubert Sturm, Katja Vorndran
  • Publication number: 20090227544
    Abstract: The present invention provides novel bisphosphonate conjugates, pharmaceutical compositions comprising bisphosphonate conjugates and methods of using such analogs in the treatment of bone cancer, bone-related diseases, bone infection, bone inflammation, and diseases of the soft tissues surrounding bones.
    Type: Application
    Filed: March 30, 2009
    Publication date: September 10, 2009
    Applicant: MBC PHARMA, INC.
    Inventors: Alexander Karpeisky, Shawn Zinnen
  • Patent number: 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
  • Publication number: 20090131394
    Abstract: Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition. Additionally provided are pharmaceutical compositions for treatment or prevention of bacterial infections and methods of treatment of such infections.
    Type: Application
    Filed: October 9, 2008
    Publication date: May 21, 2009
    Inventors: Larry Sutton, Sophia Yu
  • Patent number: 7507812
    Abstract: An industrially advantageous process for producing 3-chloromethyl-3-cephem derivative crystals. The process for 3-chloromethyl-3-cephem derivative production comprises: a first step in which a thiazolineazetidinone derivative (1) is reacted with a sulfonyl halide (2) in the presence of an acid in a solvent to obtain an azetidinone derivative (3); a second step in which the azetidinone derivative (3) is reacted with a chlorinating agent in an organic solvent to obtain a chlorinated azetidinone derivative (4); and a third step in which the chlorinated azetidinone derivative (4) is reacted with an alcoholate (5) at a pH of 8 or lower in a solvent comprising an alcohol and an ether and a 3-chloromethyl-3-cephem derivative (6) is recovered in the form of crystals.
    Type: Grant
    Filed: September 6, 2004
    Date of Patent: March 24, 2009
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Nobuo Matsumoto, Hiroshi Kawakabe, Yasuko Manabe
  • 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: 7459551
    Abstract: The present invention provides a method for preparing a ?-lactam compound of the following Formula (3), which comprises the step of reacting a compound of the following Formula (1) with a trialkyl phosphite represented by the formula (R5O)3P (wherein R5 represents an ethyl group, etc.) in an amount of 2 to 5 moles per mole of the compound and the step of heating the resulting reaction mixture in a diluent, wherein said method is characterized by having the step of completely removing unreacted trialkyl phosphite from the reaction mixture prior to the step of heating. (wherein X represents S, etc., Y represents N, etc., n represents 0 or 1, R1 represents an optionally substituted alkyl group containing 1 to 10 carbon atoms, etc., R2 and R3 each represent an optionally substituted alkyl or heterocyclic group, etc., and R4 represents an alkenyloxy group containing 1 to 6 carbon atoms, etc., provided that R1 and R2 may together form a ?-lactam ring, etc.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: December 2, 2008
    Assignee: Asubio Pharma Co., Ltd.
    Inventor: Akira Kaneko
  • Publication number: 20080177061
    Abstract: The invention relates to methods of identifying genes involved in cognitive impairment and compositions for treating cognitive impairment.
    Type: Application
    Filed: March 3, 2008
    Publication date: July 24, 2008
    Inventors: Michela Gallagher, Pauline Kay Lund, Jeffrey D. Rothstein
  • 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: 7355041
    Abstract: A salt of PACA with an amidine and its use in the production of cefprozil.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: April 8, 2008
    Assignee: Sandoz GmbH
    Inventors: Julia Greil, Johannes Ludescher, Siegfried Wolf
  • 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: 7230097
    Abstract: A process for preparation of 7-[D-?-amino-?-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid viz. Cefprozil of formula (I) in high purity, substantially free of impurities, which comprises preparation of mixed acid anhydride by selecting the sequence and temperature of addition of the reagents and its subsequent condensation with a protected 7-APCA; followed by hydrolysis, isolation and purification to give Cefprozil of formula (I) in the form of a monohydrate.
    Type: Grant
    Filed: March 15, 2004
    Date of Patent: June 12, 2007
    Assignee: Lupin Ltd.
    Inventors: Om Dutt Tyagi, Dnyandev Ragho Rane, Tushar Kumar Srivastava, Krishnarao Tukaram Sirsath
  • Patent number: 7157574
    Abstract: A chlorinated azetidinone derivative expressed by Formula (1) and an alcoholate are allowed to react in a solvent containing at least one of alcohols and an ether at a pH of 8 or less. Thus a 3-chloromethyl-3-cephem derivative expressed by Formula (2) is prepared. In the formulas, R1 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic residue, and R2 and R3 each represent a substituted or unsubstituted aromatic hydrocarbon group.
    Type: Grant
    Filed: March 25, 2004
    Date of Patent: January 2, 2007
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Nobuo Matsumoto, Hiroshi Kawakabe, Yasuko Manabe
  • Patent number: 7112672
    Abstract: A 3-(Z)-propenyl cephem compound is selectively prepared by reacting a phosphoranylidene cephem compound with acetaldehyde in the presence of a base in a solvent mixture comprising diethyl ether, formula (I), wherein R is a carboxyl protecting group; R1 is hydrogen or R2CH2CO—; and R2 is ethyl, 2-thiophenyl, phenyl, p-hydroxyphenyl or phenoxy
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: September 26, 2006
    Assignee: Hanmi Pharm. Co., Ltd.
    Inventors: Gwan-Sun Lee, Young-Kil Chang, Hong-Sun Kim, Jae-Heon Lee, Chul-Hyun Park, Gha-Seung Park, Cheol-Kyung Kim
  • Patent number: 6949521
    Abstract: Pharmaceutical prodrug compositions are provided comprising azide derivatives of drugs which are capable of being converted to the drug in vivo. Azide derivatives of drugs having amine, ketone and hydroxy substituents are converted in vivo to the corresponding drugs, increasing the half-life of the drugs. In addition azide prodrugs are often better able to penetrate the blood-brain barrier than the corresponding drugs. Especially useful are azide derivatives of cordycepin, 2?-F-ara-ddI, AraA, acyclovir, penciclovir and related drugs. Useful azide prodrugs are azide derivatives of therapeutic alicyclic amines, ketones, and hydroxy-substituted compounds, including aralkyl, heterocyclic aralkyl, and cyclic aliphatic compounds, where the amine or oxygen moiety is on the ring, or where the amine or oxygen moiety is on an aliphatic side chain, as well as therapeutic purines and pyrimidines, nucleoside analogs and phosphorylated nucleoside analogs.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: September 27, 2005
    Assignees: The University of Georgia Research Foundation, Inc., Emory University
    Inventors: Chung K. Chu, Lakshmi P. Kotra, Konstantine Manouilov, Jinfa Du, Raymond Schinazi
  • 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: 6903211
    Abstract: The present invention relates to an improved process for the preparation of cefprozil DMF solvate of formula (I), which is useful for the preparation of cefprozil, comprising: i) reacting a compound of formula (VIII) with acetaldehyde to produce a compound of formula (IX), ii) deesterifying the carboxy protecting group of the compound of formula (IX) using an acid to yield a compound of formula (X), iii) converting the compound of formula (X) to a compound of formula (XI), iv) neutralizing the compound of formula (XI) followed by enzymatic hydrolysis to produce an APCA of formula (V), v) silylating the APCA using a mixture of trimethylsilylchloride and hexamethyldisilazane to produce silylated APCA of formula (XII), and vi) condensing the silylated APCA with a mixed anhydride to produce the DMF solvate compound of formula (I).
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: June 7, 2005
    Assignee: Orchid Chemicals & Pharmaceuticals Limited
    Inventors: Pandurang Balwant Deshpande, Bhausaheb Pandharinath Khadangale, Kumar Gurusamy, Ramesh Athmaram Konda
  • Patent number: 6887992
    Abstract: A 3-cephem derivative crystal which is a clathrate compound comprising p-methoxybenzyl ester of 7-phenylacetamide-3-formyl-3-cephem-4-carboxylic acid and dimethylformamide and a process for preparing the 3-cephem derivative crystal.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: May 3, 2005
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Takashi Moriyoshi, Yasuhiro Uosaki, Yutaka Kameyama, Daisuke Suzuki, Yoshiko Seo
  • Publication number: 20040192909
    Abstract: A salt of PACA with an amidine and its use in the production of cefprozil.
    Type: Application
    Filed: January 30, 2004
    Publication date: September 30, 2004
    Inventors: Julia Greil, Johannes Ludescher, Siefried Wolf
  • Publication number: 20040132707
    Abstract: Catacholate beta-lactam conjugates, methods for producing these compounds, and compositions containing these compounds useful as siderophores or for treatment of bacterial infections are provided.
    Type: Application
    Filed: August 29, 2003
    Publication date: July 8, 2004
    Applicant: Gruenenthal GmbH
    Inventors: Lothar Heinisch, Steffen Wittmann, Ina Scherlitz-Hofmann, Thomas Stoiber, Albrecht Berg, Ute Moellmann
  • Publication number: 20040132992
    Abstract: A 3-(Z)-propenyl cephem compound is selectively prepared by reacting a phosphoranylidene cephem compound with acetaldehyde in the presence of a base in a solvent mixture comprising diethyl ether, formula (I), wherein R is a carboxyl protecting group; R1 is hydrogen or R2CH2CO—; and R2 is ethyl, 2-thiophenyl, phenyl, p-hydroxyphenyl or phenoxy.
    Type: Application
    Filed: October 16, 2003
    Publication date: July 8, 2004
    Inventors: Gwan-Sun Lee, Young-Kil Chang, Hong-Sun Kim, Jae-Heon Lee, Chul-Hyun Park, Gha-Seung Park, Cheol-Kyung Kim
  • Publication number: 20040132993
    Abstract: Disclosed are guanidine and biguanidine derivatives which have anti-viral and anti-bacterial activity. Also disclosed are pharmaceutical compositions containing such compounds as an active ingredient, and anti-viral and anti-bacterial methods utilizing such compounds.
    Type: Application
    Filed: November 25, 2003
    Publication date: July 8, 2004
    Inventor: B. Vithal Shetty
  • Publication number: 20040073023
    Abstract: A 3-cephem derivative crystal which is a clathrate compound comprising p-methoxybenzyl ester of 7-phenylacetamide-3-formyl-3-cephem-4-carboxylic acid and dimethylformamide and a process for preparing the 3-cephem derivative crystal.
    Type: Application
    Filed: October 7, 2003
    Publication date: April 15, 2004
    Inventors: Takashi Moriyoshi, Yasuhiro Uosaki, Yutaka Kameyama, Daisuke Suzuki, Yoshiko Seo
  • 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: 20030191105
    Abstract: A compound of formula 1
    Type: Application
    Filed: December 3, 2002
    Publication date: October 9, 2003
    Inventors: Gerd Ascher, Johannes Ludescher
  • 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
  • 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
  • Publication number: 20030092696
    Abstract: The invention provides compounds of formula (I): 1
    Type: Application
    Filed: July 24, 2002
    Publication date: May 15, 2003
    Inventors: John D. Buynak, Lakshminarayana Vogeti
  • 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
  • Publication number: 20030036650
    Abstract: The present invention relates to novel processes for the preparation of 3-methylenecephams. More specifically, the present invention relates in part to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone derivatives either thermally or with lanthanide metal salt catalysts.
    Type: Application
    Filed: December 31, 2001
    Publication date: February 20, 2003
    Inventors: Robin D.G. Cooper, Anthony G.M. Barrett
  • Patent number: 6495539
    Abstract: Compounds of the formula and the salts, esters and amides thereof wherein Z is S, SO, SO2 or O; each of R1, R2 and R3 is independently H or substituted or unsubstituted alkyl (1-10C), substituted or unsubstituted alkenyl, substituted or unsubstituted acyl (2-11C), substituted or unsubstituted aryl (6-14C), substituted or unsubstituted arylcarbonyl (7-15C), substituted or unsubstituted arylalkyl (7-15C), substituted or unsubstituted pyridyl wherein substituents on any alkyl, alkenyl, or acyl moiety are selected from the group consisting of halo, and RO, wherein R is H or alkyl (1-6C), and substituents on any aryl or pyridyl moiety are selected from the group consisting of halo, and RO, where R is H or alkyl (1-6C), —CN and —CF3; with the proviso that R1 is not H and R1 and R3 are not identical and with the proviso that in formula (1), the B ring may contain one double bond that is located between positions 2 and 3, and in formula (2), the B ring may contain one double bond tha
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: December 17, 2002
    Assignee: Washington University
    Inventors: Scott J. Hultgren, Fredrik Almqvist, Gabriel Soto
  • Patent number: 6458558
    Abstract: A process for the preparation of Cefuroxime acid (I), which comprises the following steps: (1) Extraction of deacetyl 7-glutaryl ACA (II) aqueous solution at acid pH with organic solvents (for example according to the procedures disclosed in U.S. Pat. No. 5,801,241); (2) drying the resulting solution while preventing lactonization of the intermediate; (3) carbamoylation of the hydroxymethyl group at the 3-position by reaction with chlorosulfonyl isocyanate or similar products; (7) extraction of the carbamoyl derivative from step 3 with water at neutral pH; (8) enzymatic hydrolysis of the amide at the 7-position of the cephalosporanic ring with glutaryl acylase; (6) acylation of the amnino group by condensation with 2-furanyl(sin-methoxyimino)acetic acid chloride or mixed anhydride.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: October 1, 2002
    Assignee: Antibioticos S.p.A.
    Inventors: Enrico Siviero, Walter Cabri, Daniele Mario Terrassan
  • Publication number: 20020128469
    Abstract: 1
    Type: Application
    Filed: October 11, 2001
    Publication date: September 12, 2002
    Inventors: Benjamin Gerlach, Johannes Ludescher, Klaus Totschnig