Additional Carbon Bonded Directly To The Additional Chalcogen Patents (Class 540/360)
  • Patent number: 9963444
    Abstract: A compound is represented as Formula I, a tautomer thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. Compounds of Formula I are inhibitors of N-acylethanolamine hydrolyzing acid amidase (NAAA). The present technology is directed to compounds, compositions, and methods to inhibit N-acylethanolamine hydrolyzing acid amidase and to treat N-acylethanolamine hydrolyzing acid amidase mediated conditions in a subject.
    Type: Grant
    Filed: May 13, 2015
    Date of Patent: May 8, 2018
    Assignee: Northeastern University
    Inventors: Michael Malamas, Alexandros Makriyannis, Kumara Vadivel Subramanian, Kyle M. Whitten, Nikolai M. Zvonok, Jay Matthew West, Michael Mccormack, Spiro Pavlopoulos
  • Publication number: 20120142911
    Abstract: The present invention relates to the synthesis of intermediates which are useful in TTX synthesis and to the preparation thereof.
    Type: Application
    Filed: June 11, 2010
    Publication date: June 7, 2012
    Inventors: Pedro Noheda Marín, Luis Miguel Lozano Gordillo, Nuria Tabares Cantero, Raúl Benito Arenas, David Herrero
  • Patent number: 7906502
    Abstract: Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: March 15, 2011
    Assignee: AstraZeneca AB
    Inventors: Susanne Alenfalk, Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Ingemar Starke
  • Patent number: 7893048
    Abstract: Compounds of formula (I): (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: February 22, 2011
    Assignee: AstraZeneca AB
    Inventors: Susanne Alenfalk, Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Malin Lemurell, Ingemar Starke
  • Patent number: 7871998
    Abstract: Compounds of formula (I): (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Grant
    Filed: December 21, 2004
    Date of Patent: January 18, 2011
    Assignee: AstraZeneca AB
    Inventors: Susanne Alenfalk, Mikael Dahlström, Fana Hunegnaw, Staffan Karlsson, Malin Lemurell, Ann-Margret Lindqvist, Tore Skjäret, Ingemar Starke
  • Patent number: 7863265
    Abstract: Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Grant
    Filed: June 19, 2006
    Date of Patent: January 4, 2011
    Assignee: AstraZeneca AB
    Inventors: Susanne Alenfalk, Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Malin Lemurell, Ann-Margret Lindqvist, Tore Skjaret, Ingemar Starke
  • Patent number: 7842684
    Abstract: The present invention provides 2-azetidinone derivatives, or pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof, comprising formula (I): wherein the substituents are as herein defined. The compounds possess cholesterol absorption inhibitory activity and are accordingly of value in the treatment of disease states associated with hyperlipidaemic conditions.
    Type: Grant
    Filed: April 25, 2007
    Date of Patent: November 30, 2010
    Assignee: AstraZeneca AB
    Inventors: Malin Lemurell, Ingemar Starke
  • Publication number: 20100216761
    Abstract: The invention is directed to novel azetidinones selected from 2-(S)-[4-(((2-(Dimethylamino)ethyl)ethylamino)carbonyl)phenoxy]-3,3-diethyl-N-[1-(R)-(4-(trifluoromethoxy)phenyl)butyl]-4-oxo-1-azetidin ecarboxamide, 2-(S)-[4-(((2-(Dimethylamino)ethyl)ethylamino)carbonyl)phenoxy]-3,3-diethyl-N-[1-(R)-(4-(trifluoromethyl)phenyl)butyl]-4-oxo-1-azetidinecarboxamide, and analogs thereof, and pharmaceutically acceptable salts thereof, and their use in the treatment of diseases associated with an excess of elastase, including emphysema, bronchial inflammation, chronic bronchitis, cystic fibrosis, acute respiratory distress syndrome, rheumatoid arthritis, osteoarthritis; glomerulonephritis, spondylitis, lupus, psoriasis, atherosclerosis, sepsis, septicemia, shock, myocardial infarction, reperfusion injury, and periodontitis.
    Type: Application
    Filed: October 1, 2008
    Publication date: August 26, 2010
    Inventors: James B. Doherty, Paul E. Finke, Richard A. Mumford, Kelly M. Treonze
  • Publication number: 20100216759
    Abstract: Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Application
    Filed: June 19, 2006
    Publication date: August 26, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Susanne Alenfalk, Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Malin Lemurell, Ann-Margret Lindqvist, Tore Skjaret, Ingemar Starke
  • Publication number: 20100168075
    Abstract: The application relates to novel 2-azetidinone derivatives of formula (I) and pharmaceutically acceptable salts, solvates and prodrugs thereof. The compounds are cholesterol absorption inhibitors and are useful in the treatment of hyperlipidaemic conditions, including atherosclerosis, Alzheimers' disease and cholesterol associated tumours. The application also relates to pharmaceutical formulations comprising such compounds and to processes for their preparation.
    Type: Application
    Filed: June 21, 2006
    Publication date: July 1, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Mikael Dahlstrom, Fana Hunegnaw, Malin Lemurell, Peter Nordberg, Tore Skjaret, Ingemar Starke
  • Publication number: 20100152156
    Abstract: The invention relates to novel 2-azetidinone derivatives of formula (I) and to pharmaceutically acceptable salts, solvates and prodrugs thereof. The compounds are cholesterol absorption inhibitors, useful in the treatment of hyperlipidaemic conditions. The invention also relates to processes for their manufacture and to pharmaceutical compositions containing them.
    Type: Application
    Filed: June 21, 2006
    Publication date: June 17, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Peter Nordberg, Ingemar Starke
  • Publication number: 20100137273
    Abstract: Compounds of formula (I): (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.
    Type: Application
    Filed: June 21, 2006
    Publication date: June 3, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Susanne Alenfalk, Mikael Dahlstrom, Fana Hunegnaw, Staffan Karlsson, Malin Lemurell, Ingemar Starke
  • Publication number: 20100048529
    Abstract: The invention relates to compounds of formula (I) and pharmaceutically acceptable salts, solvates, and prodrugs thereof, and to their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia. The invention also relates to processes for their manufacture and pharmaceutical compositions containing them.
    Type: Application
    Filed: June 21, 2006
    Publication date: February 25, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Mikael Dahlstrom, Staffan Karlsson, Malin Lemurell, Peter Nordberg, Ingemar Starke
  • Publication number: 20100048530
    Abstract: The invention relates to 2-azetidinone derivatives of formula (I), including pharmaceutically acceptable salts, solvates and prodrugs thereof. The compounds inhibit cholesterol absorption and are useful in the treatment of hyperlipidaemic conditions. The invention also relates to processes for their manufacture and to pharmaceutical compositions containing them.
    Type: Application
    Filed: June 21, 2006
    Publication date: February 25, 2010
    Applicant: ASTRAZENECA AB
    Inventors: Mikael Dahlstrom, Staffan Karlsson, Peter Nordberg, Tore Skjaret, Ingemar Starke
  • Publication number: 20090137796
    Abstract: The present invention relates to a stereoselective synthesis of novel ?-lactam dimers as useful precursors for the preparation of paclitaxel, docetaxel, and analogues thereof. More particularly, the new ?-lactams are prepared from readily available and enantiomerically pure chiral auxiliaries. The ?-lactams are then reacted with a suitably protected taxane to produce diastereomerically enriched side chain-bearing taxanes. Finally, the chiral auxiliary is cleaved and protecting groups are removed to provide the desired taxane.
    Type: Application
    Filed: November 3, 2006
    Publication date: May 28, 2009
    Applicant: BIOXEL PHARMA INC.
    Inventors: Mettilda Lourdusamy, Gaétan Caron
  • Publication number: 20090131395
    Abstract: The invention relates to a chemical genus of 4-biphenyl-1-phenylazetidin-2-ones useful in the treatment of hypercholesterolemia and other disorders. The compounds have the general formula I: Pharmaceutical compositions and methods for treating cholesterol- and lipid-associated diseases are also disclosed.
    Type: Application
    Filed: May 5, 2006
    Publication date: May 21, 2009
    Applicant: MICROBIA, INC.
    Inventors: Stephen Antonelli, Regina Lundrigan, Eduardo J. Martinez, Wayne C. Schairer, John J. Talley, Timothy C. Barden, JingJing Yang, Daniel P. Zimmer
  • Publication number: 20090088566
    Abstract: The present invention discloses the usage of Poly-3-hydroxybutyrates P(3HB) in preparation of ?-lactam compounds and the method for the preparation of ?-lactam compounds of formula (I) using Poly-3-hydroxybutyrates P(3HB) as followed: wherein: R is R1, R2, R3 are lower linear or branched C1-C4 alkyl. It is convenient to synthesize the said compound of formula (I) with the present method. Compared with the previous ones, the present method has less steps and higher yields.
    Type: Application
    Filed: October 16, 2006
    Publication date: April 2, 2009
    Inventors: Weichuan Lu, Qian Zhang, Xin Cheng
  • Publication number: 20090069285
    Abstract: 2-azetidinone derivatives and pharmaceutical compositions containing them. The compounds are useful in the treatment of hyperlipidemic conditions, atherosclerosis, Alzheimers' disease and cholesterol associated tumours.
    Type: Application
    Filed: April 25, 2007
    Publication date: March 12, 2009
    Applicant: ASTRAZENECA AB
    Inventors: Malin Lemurell, Ingemar Starke
  • Patent number: 7501404
    Abstract: Compounds are provided which have the structure Wherein A, B, C, D, m, Y, Ra, Rc, Rd, and Rd? are as described herein, and which are useful as inhibitors of tryptase, thrombin, trypsin, Factor Xa, Factor VIIa, Factor XIa, and urokinase-type plasminogen activator and may be employed in preventing and/or treating asthma, chronic asthma, allergic rhinitis, and thrombotic disorders.
    Type: Grant
    Filed: April 4, 2006
    Date of Patent: March 10, 2009
    Assignee: DAIMED
    Inventors: Thomas Bannister, Cassandra Celatka, Nizal S. Chandrakumar, Hongfeng Deng, Zihong Guo, Lei Jin, Tsvetelina Lazarova, Jian Lin, Scott T. Moe, Pamela Nagafuji, Manuel Navia, Amy Ripka, Michael J. Rynkiewicz, Kerry L. Spear, James E. Stickler, Roger Xie
  • Patent number: 7179907
    Abstract: The present invention provides methods for identifying (3-amino-2-oxo-azetidin-1-yl) acetic acid derivatives with anti-PBP2a activity. The method involves the selection of RNA biocatalysts that promote the formation of (3-amino-2-oxo-azetidin-1-yl) acetic acid derivatives with anti-PBP2a activity from component reactants. The invention also provides novel (3-amino-2-oxo-azetidin-1-yl) acetic acid derivatives with anti-PBP2a activity identified by these methods. The invention also provides RNA biocatalysts that are capable of catalyzing the formation of (3-amino-2-oxo-azetidin-1-yl) acetic acid derivatives from component reactants.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: February 20, 2007
    Inventors: Bruce Eaton, Theodore M. Tarasow, Dan Nieuwlandt, Torin Dewey
  • Patent number: 7129350
    Abstract: A process for the preparation of 3-cyclic-ether-substituted cephalosporins of formula I wherein the group CO2R1 is a carboxylic acid or a carboxylate salt and R2 has the formula: wherein A1 and A2 have the meanings given in the specification by reacting compound of formula II: wherein R2 is as defined above and R3 is para-nitrobenzyl or allyl with a compound R2 L wherein R2 is as defined above; and L is di-(C1-6 alkyl)phosphorothioate in the presence of a solvent and a base.
    Type: Grant
    Filed: February 11, 2004
    Date of Patent: October 31, 2006
    Assignee: Pfizer, Inc.
    Inventors: Juan C. Colberg, Maurizio Zenoni, Giovanni Fogliato, Alessandro Donadelli
  • Patent number: 7045515
    Abstract: Novel ?-lactam compounds represented by the following formula (I) or pharmaceutically acceptable salts thereof which are useful as serum cholesterol-lowering agents: (I) wherein A1, A3 and A4 represent each hydrogen, halogen C1-5 alkyl, C1-5 alkoxy, —COOR1, a group represented by the following general formula (b): (b) wherein R1 represents hydrogen or C1-5 alkyl, or a group represented by the following general formula (a): (a) wherein R2 represents —CH2OH, —CH2OC(O)—R1 or —CO2—R1; R3 represents —OH or —OC(O)—R1; R4 represents —(CH2)kR5(CH2)1- wherein K and 1 are each 0 or an integer of 1 or above provided k+1 is an integer of not more than 10; and R5 represents a single bond, —CH?CH—, —OCH2—, carbonyl or —CH(OH)—; provided that at least one of A1, A3 and A4 is a group represented by the above formula (a); A2 represents C1-5 alkyl, C1-5 alkoxy, C1-5 alkenyl, C1-5 hydroxyalkyl or C1-5 carbonylalkyl; and n, p, q and r are each an integer of 0, 1 or 2.
    Type: Grant
    Filed: February 20, 2002
    Date of Patent: May 16, 2006
    Assignee: Kotobuki Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Tomiyama, Masayuki Yokota, Atsushi Noda, Akira Ohno
  • Patent number: 6900312
    Abstract: The present discovery consists in new thiazole-substituted ?-lactams of general formula (I), as well as the method for their preparation. R1, R2, R3, R4, R5, R6, R7, and R8 are, independently from each other, a hydrogen atom, a halogen, a hydroxy, amino, nitro, or thiol group, an optionally substituted alkyl, heteroalkyl, aryl, aralkyl, cycloalkyl, cycloaralkyl, heterocycloalkyl, heteroaralkyl, or heteroaryl rest.
    Type: Grant
    Filed: July 16, 2002
    Date of Patent: May 31, 2005
    Assignee: Priaton GmbH
    Inventors: Juergen Kolb, Alexander Doemling
  • Patent number: 6730782
    Abstract: Taxane derivatives having an amino substituted C13 side chain.
    Type: Grant
    Filed: February 25, 2002
    Date of Patent: May 4, 2004
    Assignee: Florida State University
    Inventors: Robert A. Holton, Hossain Nadizadeh, Kasthuri Rengan, Chunlin Tao
  • Publication number: 20030100548
    Abstract: 1 Compounds of formula (I) wherein Z is —CH2SR and R represents hydrogen or —COCH3, are useful as metalloproteinase inhibitors, especially as inhibitors of MMP 13.
    Type: Application
    Filed: September 20, 2002
    Publication date: May 29, 2003
    Inventors: Bernard Christophe Barlaam, Nicholas John Newcombe, Howard Tucker, David Waterson
  • Patent number: 6569847
    Abstract: This invention relates to substituted azetidin-2-ones and to pharmaceutical compositions containing such compounds. Their use in medicine as inhibitors of cysteine proteases, particularly the cathepsins is also described. The invention includes a compound of formula (I), Y represents —C(O)— or —S(O2)—; R represents an allyl (ie CH2═CHCH2—) group or a radical. R1 represents —OCOR5, —OR5, —SR5, —S(O)R5, or —S(O)2R5; R2 represents a radical. R3 represents —OR5 or R5; or a pharmaceutically acceptable salt, hydrate or solvate thereof.
    Type: Grant
    Filed: October 5, 2001
    Date of Patent: May 27, 2003
    Assignee: NAEJA Pharmaceuticals Inc.
    Inventors: Rajeshwar Singh, Andhe V. Narender Reddy, Jadwiga Kaleta, Ronald G. Micetich, Mark Whittaker, Philip Huxley
  • Patent number: 6562962
    Abstract: A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reacted with a &bgr;-lactam.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: May 13, 2003
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 6407228
    Abstract: A simple and efficient method is proposed for the preparation of a &bgr;-lactam compound such as 1-phenyl-4-ethoxy-2-azetidinone which can be produced by mixing an isocyanate compound such as phenyl isocyanate and a vinyl ether compound such as ethyl vinyl ether and heating the mixture at a moderate temperature under a superatmospheric pressure of up to 12000 atmospheres.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: June 18, 2002
    Assignee: Japan as represented by Director General of Agency of Industrial Science and Technology
    Inventors: Yoichi Taguchi, Akihiro Oishi, Isao Shibuya, Tohru Tsuchiya
  • Patent number: 6310201
    Abstract: Novel &bgr;-lactams finding utility as intermediates in the preparation of sidechain-bearing taxes such as tall and tall derivatives. The present invention also relates to novel methods of coupling &bgr;-lactams to form such sidechain-bearing taxes, and to novel sidechain-bearing taxes.
    Type: Grant
    Filed: June 11, 1999
    Date of Patent: October 30, 2001
    Assignee: Bristol-Myers Squibb Company
    Inventors: John K. Thottathil, Ivan D. Trifunovich, David J. Kucera, Wen-Sen Li
  • Patent number: 6239125
    Abstract: A compound of formula 1: wherein Y is S or O; R1 is C1-6 alkyl; (C0-6 alkyl)aryl; (C0-6 alkyl)Het; or R1 is an amino acid analog or dipeptide analog of the formula: wherein R2 is H, C1-10 alkyl; or an amide or ester group; A is C6-10 aryl, Het or CH—R3 wherein R3 is C1-6 alkyl or (C0-4 alkyl)aryl; and Z is H, C1-6 alkyl, or an acyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5 is alkyl, cycloalkyl, carboxyl group; an aryl; Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7 wherein R7 is lower alkyl or phenyl(lower alkyl); or a therapeutically acceptable acid addition salt thereof which compounds are useful in the treatment of HCMV infections.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: May 29, 2001
    Assignee: Boehringer Ingelheim (Canada) Ltd.
    Inventors: Eric Malenfant, Jeffrey O'Meara, Robert Déziel, William W. Ogilvie
  • Patent number: 6221860
    Abstract: This invention relates to methods for treating diseases or disorders mediated by lipid inflammatory mediators, arachidonic acid, its metabolites and/or platelet activating factor (PAF), which method comprises administration to a mammal in need thereof of an effective Coenzyme A independent transacylase (CoA-IT) inhibiting amount of a triphenylmethylazetidinone. This invention also relates to a method of treating or reducing inflammation in a mammal in need thereof, which comprises administering to said mammal an effective amount of a triphenylmethylazetidinone.
    Type: Grant
    Filed: November 8, 1999
    Date of Patent: April 24, 2001
    Assignee: SmithKline Beecham Corporation
    Inventors: William E. Bondinell, James David Winkler
  • Patent number: 6194569
    Abstract: Processes for the preparation of [S-(R,S)]-N-[1,3-benzodioxol-5-yl)butyl]-3,3-diethyl-2[4-[4-methyl-1-piperazinyl)carbonyl]phenoxy]-4-oxo-l-azetidine carboxamide, a useful inhibitor of human leukocyte elastase (HLE), are described. The process including (a) contacting a compound of formula (II): with a compound of formula (III): in a first polar solvent system in the presence of an aqueous base and a phase transfer catalyst, to form the title compound, or a salt form thereof.
    Type: Grant
    Filed: August 30, 1999
    Date of Patent: February 27, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Patrick J. Sheeran, Luigi Anzalone, Hui-Yin Li, Joseph M. Fortunak, Louis Storace
  • Patent number: 6187916
    Abstract: A process for the preparation of a taxane derivative of the formula in which R2 represents an RO—, RS— or RR′N— in which R represents an unsubstituted or substituted straight chain or branched alkyl, alkenyl or alkynyl, or cycloalkyl, saturated heterocyclic, cycloalkenyl, unsaturated heterocyclic, aryl or heterocyclic aromatic; R′ is a hydrogen or R defined above; R and R′ can be connected to form together with the nitrogen a cyclic structure; Y is oxygen or sulfur; R3 represents an unsubstituted or substituted straight chain or branched alkyl, alkenyl or alkynyl radical, an unsubstituted or substituted cycloalkyl, cycloalkenyl or an unsubstituted or substituted aryl; which comprises reacting a &bgr;-lactam of the formula in which R311 represents a radical R3 defined above or a protected R3 whenever R3 includes one or more active hydrogens; with a baccatin III derivative of the formula: in which M is an alkali metal
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 13, 2001
    Assignee: Research Foundation of State University of New York
    Inventor: Iwao Ojima
  • Patent number: 6071899
    Abstract: Azetidinone derivatives of formula (I) in which R.sup.1 and R.sup.2, which may be the same or different, is each selected from hydrogen or C.sub.(1-8) alkyl; R.sup.3 is C.sub.(1-8) alkyl or C.sub.(3-8) cycloalkyl each of which may be optionally substituted; X is a linker group; Y is an aryl group; and n is 0, 1 or 2; and excluding benzyl (4-methylthio-2-oxo-azetidin-1-yl)acetate are inhibitors of the enzyme Lp PLA2 and are of use in therapy, in particular treating atherosclerosis.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: June 6, 2000
    Assignee: SmithKline Beecham p.l.c.
    Inventors: Deirdre Mary Bernadette Hickey, Dashyant Dhanak, Colin Andrew Leach, Robert John Ife, David Graham Tew
  • Patent number: 6008347
    Abstract: The present invention provides novel cis-N-iminomethyl-3,4-disubstituted-2-azetidinones, and their use in the preparation of N-acyl-2-azetidinones, intermediates in the semi-synthesis of taxol and taxol derivatives.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: December 28, 1999
    Assignee: Bristol-Myers Squibb Company
    Inventors: Allan W. Rey, Purushotham Vemishetti, Roberto Droghini
  • Patent number: 5998612
    Abstract: A method of preparing intermediates for carbapenem antibiotics characterized by treating a N-deprotected acetoxy conpound of the formula: ##STR1## in the presence of a Lewis acid or a silylating agent to yeild an intermediate; and cyclizing the intermediate in the presence of rhodium (II) acetate to form a bicyclic ketoester.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: December 7, 1999
    Inventors: Paul J. Reider, Edward J. J. Grabowski
  • Patent number: 5990102
    Abstract: Compounds of formula (I) in which R.sup.1 and R.sup.2, which may be the same or different, is each selected from hydrogen, halogen or C.sub.(1-8) alkyl; R.sup.3 is aryl or aryl C.sub.(1-4) alkyl which may be optionally substituted; X is a linker group; Y is an optionally substituted aryl group; and n is 0, 1 or 2; are inhibitors of the enzyme Lp-PLA.sub.2 and thereof of use in treating atherosclerosis.
    Type: Grant
    Filed: November 21, 1997
    Date of Patent: November 23, 1999
    Assignee: SmithKline Beecham p.l.c.
    Inventors: Deirdre Mary Bernadette Hickey, Dashyant Dhanak, Colin Andrew Leach, Robert John Ife, David Graham Tew
  • Patent number: 5952321
    Abstract: New substituted azetidinones of the general Formula (I) which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described, wherein n is
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: September 14, 1999
    Assignee: Merck & Co., Inc.
    Inventors: James Doherty, Conrad Dorn, Philippe Durette, Paul Finke, Malcolm Maccoss, Sander Mills, Shrenik Shah, Soumya Sahoo, William Hagmann, Scott Polo
  • Patent number: 5916887
    Abstract: In accordance with the present invention, there are provided 4-substituted-3-(2-amino-2-cycloalkyl methyl)-acetamido azetidin-2-one derivatives of the formula: ##STR1## wherein n is 1, 2 or 3; in which R.sub.1, R.sub.2 and R.sub.3 are as defined herein, and salts thereof, which exhibit excellent cysteine proteinase inhibitory activity and which can be used for treatment of different diseases such as muscular dystrophy, myocardial infarction, bone resorption, arthritis, cancer metastasis, pulmonary emphysema, septic shock, cerebral ischemia, memory function, Alzheimer and cataract, malaria, glomerular basement membrane degradation, bacterial infection, inflammatory diseases, parasitic infections, and viral infections.
    Type: Grant
    Filed: September 22, 1997
    Date of Patent: June 29, 1999
    Assignee: National Research Council of Canada
    Inventors: Rajeshwar Singh, Nian E. Zhou, Enrico O. Purisima, Ronald G. Micetich
  • Patent number: 5866691
    Abstract: Novel .beta.-lactam monomers bearing various functional groups are prepared. The novel .beta.-lactam monomers can be joined into oligomeric compounds such as via preferred phosphate linkages including phosphodiester and phosphorothioate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen bonding. The oligomeric compounds are useful as diagnostic and research reagents.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: February 2, 1999
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Vasulinga Ravikumar, Venkatraman Mohan
  • Patent number: 5843939
    Abstract: 3-Bromo- and 3,3-dibromo-4-oxo-1-azetidines of the formula I ##STR1## wherein R.sub.1 is hydrogen or bromo,R.sub.2 is hydrogen or bromo,R.sub.3 is hydrogen, ##STR2## wherein R.sub.4 is hydrogen, methyl, benzyl or some other protective group,R.sub.5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring,Y is a halo atom,X is a halo atom, alkoxy group, nitroxy group are provided along with processes for the preparation thereof and the use thereof.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: December 1, 1998
    Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo
    Inventor: Irena Lukic
  • Patent number: 5808056
    Abstract: The present invention relates to the process for the preparation of the substituted azetidinone having the formula: ##STR1## comprising a convergent synthesis wherein the azetidinone portion of the molecule is coupled to the lower benzodioxole portion via a base catalyzed addition to an isocyanate.
    Type: Grant
    Filed: October 23, 1996
    Date of Patent: September 15, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Joseph S. Amato, Raymond Cvetovich, Frederick W. Hartner
  • Patent number: 5728827
    Abstract: This invention provides a process for preparing azetidinones useful as intermediates in the synthesis of penems and as hypocholesterolemic agents, particularly for azetidinones substituted in the C-3 and C-4 positions and optionally substituted at the ring nitrogen, comprising reacting a .beta.-(substituted-amino)amide, a .beta.-(substituted-amino)acid ester, or a .beta.-(substituted-amino)thiolcarbonic acid ester with a silylating agent and a cyclizing agent.
    Type: Grant
    Filed: January 4, 1996
    Date of Patent: March 17, 1998
    Assignee: Schering Corporation
    Inventors: Tiruvettipuram Kannapan Thiruvengadam, Timothy McAllister, Chou-Hong Tann
  • Patent number: 5688785
    Abstract: Substituted azetidinone hypocholesterolemic agents of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein: Ar.sup.1 is aryl or R.sup.3 -substituted aryl;Ar.sup.2 is aryl or R.sup.4 -substituted aryl;R.sup.1 is selected from the group consisting of--(CH.sub.2).sub.q --, wherein q is 2, 3, 4, 5 or 6;--(CH.sub.2).sub.e --Z--(CH.sub.2).sub.r --, wherein Z is --O--, --C(O)--, phenylene, --NR.sup.10 -- or --S(O).sub.0-2 --, e is 0-5 and r is 0-5, provided that the sum of e and r is 1-6;--(C.sub.2 --C.sub.6 alkenylene)--; and--(CH.sub.2).sub.f --V--(CH.sub.2).sub.g --, wherein V is C.sub.3 -C.sub.6 cycloalkylene, f is 1-5 and g is 0-5, provided that the sum of f and g is 1-6;R.sup.2 is --(lower alkylene)--COR.sup.5 or --(CH.dbd.CH)--COR.sup.5 ;R.sup.3 and R.sup.4 are independently selected from the group consisting of 1-3 substituents independently selected from the group consisting of lower alkyl, --OR.sup.6, --O(CO)R.sup.6, --O(CO)OR.sup.9, --O(CH.sub.2).sub.1-5 OR.sup.6, --O(CO)NR.sup.6 R.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: November 18, 1997
    Assignee: Schering Corporation
    Inventor: Wayne D. Vaccaro
  • Patent number: 5633246
    Abstract: Sulfur-substituted azetidinone hypocholesterolemic agents of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein: Ar.sup.1 is aryl, R.sup.10 -substituted aryl or heteroaryl;Ar.sup.2 is aryl or R.sup.4 -substituted aryl;Ar.sup.3 is aryl or R.sup.5 -substituted aryl;X and Y are --CH.sub.2 --, --CH(lower alkyl)-- or --C(dilower alkyl)--;R is --OR.sup.6, --O(CO)R.sup.6, --O(CO)OR.sup.9 or --O(CO)NR.sup.6 R.sup.7 ; R.sup.1 is hydrogen, lower alkyl or aryl; or R and R.sup.1 together are .dbd.O;q is 0 or 1; r is 0, 1 or 2; m and n are 0-5; provided that the sum of m, n and q is 1-5;R.sup.4 is selected from lower alkyl, --OR.sup.6, --O(CO)R.sup.6, --O(CO)OR.sup.9, --O(CH.sub.2).sub.1-5 OR.sup.6, --O(CO)NR.sup.6 R.sup.7, --NR.sup.6 R.sup.7, --NR.sup.6 (CO)R.sup.7, --NR.sup.6 (CO)OR.sup.9, --NR.sup.6 (CO)NR.sup.7 R.sup.8, --NR.sup.6 SO.sub.2 R.sup.9, --COOR.sup.6, --CONR.sup.6 R.sup.7, --COR.sup.6, --SO.sub.2 NR.sup.6 R.sup.7, S(O).sub.0-2 R.sup.9, --O(CH.sub.2).sub.1-10 --COOR.sup.6, --O(CH.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: May 27, 1997
    Assignee: Schering Corporation
    Inventors: Brian A. McKittrick, Sundeep Dugar, Duane A. Burnett
  • Patent number: 5624920
    Abstract: Sulfur-substituted azetidinone hypocholesterolemic agents of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein: Ar.sup.1 is aryl or R.sup.10 -substituted aryl;Ar.sup.2 is aryl or R.sup.4 -substituted aryl;Ar.sup.3 is aryl or R.sup.5 -substituted aryl;X and Y are --CH.sub.2 --, --CH(lower alkyl)-- or --C(dilower alkyl)--;R is --OR.sup.6, --O(CO)R.sup.6, --O(CO)OR.sup.9 or --O(CO)NR.sup.6 R.sup.7 ; R.sup.1 is hydrogen, lower alkyl or aryl; or R and R.sup.1 together are .dbd.O;q is 0 or 1; r is 0, 1 or 2; m and n are 0-5; provided that the sum of m, n and q is 1-5;R.sup.4 is selected from lower alkyl, --OR.sup.6, --O(CO)R.sup.6, --O(CO)OR.sup.9, --O(CH.sub.2).sub.1-5 OR.sup.6, --O(CO)NR.sup.6 R.sup.7, --NR.sup.6 R.sup.7, --NR.sup.6 (CO)R.sup.7, --NR.sup.6 (CO)OR.sup.9, --NR.sup.6 (CO)NR.sup.7 R.sup.8, --NR.sup.6 SO.sub.2 R.sup.9, --COOR.sup.6, --CONR.sup.6 R.sup.7, --COR.sup.6, --SO.sup.2 NR.sup.6 R.sup.7, S(O).sub.0-2 R.sup.9, --O(CH.sub.2).sub.1-10 --COOR.sup.6, --O(CH.sub.2).sub.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: April 29, 1997
    Assignee: Schering Corporation
    Inventors: Brian A. McKittrick, Sundeep Dugar, Duane A. Burnett
  • Patent number: 5591737
    Abstract: New substituted azetidinones of the general Formula (I) which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described. ##STR1## wherein R.sub.4 is (a) ##STR2## or (b) ##STR3## where R.sub.x is carboxy C.sub.1-6 alkyl, benzyloxycarbonylC.sub.1-3 alkyl, or t-butoxycarbonylC.sub.1-3 alkyl,whereinQ is a covalent bond or ##STR4## wherein R.sub.5 and R.sub.6 are each individually C.sub.1-3 alkyl or hydrogen,Y is ##STR5## or a covalent bond.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: January 7, 1997
    Assignee: Merck & Co., Inc.
    Inventors: James B. Doherty, Conrad P. Dorn, Philippe L. Durette, Paul E. Finke, Malcolm Maccoss, Sander G. Mills, Shrenik K. Shah, Soumya P. Sahoo, Jeffrey J. Hale, Thomas J. Lanza, William K. Hagmann
  • Patent number: 5585373
    Abstract: A derivative of 3-(7'-oxo-1'-aza-4'-oxabicyclo[3.2.0 ]hept-3'-yl)propionic acid represented by the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group optionally having one or more cycloalkyl groups, a lower acyl group, a benzoyl group optionally having one or more substituents or a benzyl group optionally having one or more substituents, R.sub.2 is a hydrogen atom or a carboxyl-protecting group, R.sub.3 is a hydroxyl group, an azido group, a benzenesulfonyloxy group optionally having one or more substituents, a lower alkylsulfonyloxy group optionally having one or more substituents, a tri-substituted silyloxy group or an amino group optionally having one or more substituents, provided that when R.sub.1 and R.sub.2 are hydrogen atoms, R.sub.3 is not an amino group, and a salt thereof.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: December 17, 1996
    Assignee: Taiho Pharmaceutical Co., Ltd
    Inventors: Zhang Z. Ping, Zhen J. Sheng, Zhang Q. Rong, Zhang J. Liang, Singh Rajeshwar, Tomohiro Yamashita, Toshiyuki Toko, Hiroshi Matsumoto
  • Patent number: 5580976
    Abstract: A process for preparing a .beta.-lactam compound of the formula (I): ##STR1## which comprises cyclization of an azetidinone derivative of the formula: ##STR2## is provided in which R.sup.1 is hydrogen, alkyl which is optionally substituted, or amino which is optionally substituted; R.sup.2 is a carboxy-protecting group; and X is alkylene which is optionally intervened by --O-- or --S--, and/or which is optionally substituted; and R.sup.3 is aryl which is optionally substituted.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: December 3, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masaharu Kume, Tadatoshi Kubota
  • Patent number: 5574156
    Abstract: A .beta.-lactam of the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, alkyl, acyl, acetal, ethoxyethyl, or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; and the enantiomers and diastereomers thereof.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: November 12, 1996
    Assignee: Florida State University
    Inventor: Robert A. Holton