Nitrogen Attached Directly Or Indirectly To The Lactone Ring By Acyclic Nonionic Bonding Patents (Class 549/321)
  • Patent number: 10189776
    Abstract: The invention relates to a method for the stereoselective preparation of compounds of formula (IV).
    Type: Grant
    Filed: September 16, 2016
    Date of Patent: January 29, 2019
    Assignee: Boehringer Ingelheim International GmbH
    Inventors: Uwe Joerg Ries, Nizar Haddad, Bo Qu
  • Patent number: 9242951
    Abstract: Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.
    Type: Grant
    Filed: June 26, 2013
    Date of Patent: January 26, 2016
    Assignee: THE NATIONAL INSTITUTE FOR BIOTECHNOLOGY IN THE NEGEV LTD.
    Inventors: Michael M. Meijler, Josep Rayo, Neri Amara
  • Publication number: 20150080349
    Abstract: The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
    Type: Application
    Filed: July 10, 2014
    Publication date: March 19, 2015
    Inventors: Helen E. BLACKWELL, Grant D. GESKE, Jennifer C. CAMPBELL
  • Patent number: 8940911
    Abstract: A library of unnatural squarylated homoserine lactones (SHLs) and squarylated lactones that bear potential to modulate biofilm formation in Gram negative bacteria. At low concentrations (˜200 ?M), these small molecules inhibit biofilm formation of E. coli. Moreover, these compounds are not toxic up to 300 ?M and do not significantly attenuate E. coli growth. The SHLs have potential to disperse established biofilm and demonstrate an enhanced reduction (˜50%) of the maximum biofilm thickness by use of SHLs during biofilm growth.
    Type: Grant
    Filed: August 1, 2013
    Date of Patent: January 27, 2015
    Assignee: Syracuse University
    Inventors: Yan-Yeung Luk, Sri Kamesh Narasimhan, Eric Falcone
  • Patent number: 8865920
    Abstract: Provided herein are processes for the preparation of N-acylated amines. In particular, the processes comprise contacting an amine with an acid comprising a carboxylic acid group to form the N-acylated amine.
    Type: Grant
    Filed: March 9, 2011
    Date of Patent: October 21, 2014
    Assignee: Novus International, Inc.
    Inventors: Richard Vonder Embse, Michael Hayes, James C. Peterson
  • Patent number: 8853428
    Abstract: The invention relates to a method for preparing an amino acid, or its salts, from 2-aminobutyrolactone (2ABL), said amino acid fitting the formula I, XCH2CH2CHNH2COOH, wherein X is such that X? represents a nucleophilic ion, according to which N-carboxylation of 2-aminobutyrolactone (2ABL) is achieved with carbon dioxide, and the thereby obtained 2ABL carbamate is reactive with an XH reagent or its salts.
    Type: Grant
    Filed: October 4, 2011
    Date of Patent: October 7, 2014
    Assignee: Adisseo France S.A.S.
    Inventors: Robert Huet, Jean-Michel Joerger, Vivien Henryon
  • Publication number: 20140296466
    Abstract: The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.
    Type: Application
    Filed: March 19, 2014
    Publication date: October 2, 2014
    Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
  • Patent number: 8846125
    Abstract: The present invention relates to enaminocarbonyl compounds with the formula I. The present invention also relates to the use of compounds with the formula I for the modification of the taste of a product and/or preparation for oral administration.
    Type: Grant
    Filed: February 2, 2010
    Date of Patent: September 30, 2014
    Assignee: Instytut Chemii Organicznej, Polska Akademia Nauk
    Inventors: Piotr Krajewski, Agnieszka Woźniak
  • Publication number: 20140275232
    Abstract: A novel small molecule antagonizes two types of acyl homoserine lactone receptors: membrane-bound and cytoplasmic. A focused library of analogs and derivatives of the original antagonist was synthesized. Analog and derivative molecules harbor a range of activities. The novel small molecule and most potent antagonist protects the eukaryote Caenorhabditis elegans from quorum-sensing-mediated killing by the bacterial pathogen Chromobacterium violaceum. The saving of C. elegans demonstrates the use of these molecules as small molecule antimicrobials.
    Type: Application
    Filed: May 28, 2014
    Publication date: September 18, 2014
    Applicant: THE TRUSTEES OF PRINCETON UNIVERSITY
    Inventors: Bonnie L. Bassler, Lee R. Swem, Scott M. Ulrich, Colleen T. O'Loughlin
  • Patent number: 8815943
    Abstract: The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
    Type: Grant
    Filed: February 22, 2011
    Date of Patent: August 26, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Helen E. Blackwell, Grant D. Geske, Jennifer C. O'Neill
  • Publication number: 20140228375
    Abstract: The present invention involves new and original sigma receptors ligands: (Mono-or dialkylaminoalkyl)-?-butyrolactones, their analogues aminotetrahydroturanes, the (1-adamantyl) benzene alkylamines, the N,N Dialkyl ?-[(adamantyl-1)benzyloxy-2] alkylamines and the 3-cyclopentyl adamantyl-amines or alkylamines or-alkyl phenylamines, their enantiomers or diastereoisomers, their pharmaceutically acceptable salts and Quinacrine Me-thylene blue, Asteinizole and their relative analogues with pro-apoptotic and/or anti-apoptotic properties over cellular biochemical mechanisms, with prototypical anti-cancer, antimetastatic and antiviral activities associated with antagonism of the neuropatic pain and, at very low doses, with cytoprotective and cytoregenerative activity against the cytodegenerative diseases.
    Type: Application
    Filed: March 12, 2014
    Publication date: August 14, 2014
    Applicant: Anavex Life Sciences Corp.
    Inventor: Alexandre Vamvakides
  • Patent number: 8703976
    Abstract: The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compound such as Aliskiren. The invention describes preparation of enantiomerically pure 8-aryloctanoic acid of formula I from a chiral compound of formula IV. Friedel-Crafts reaction of this compound of formula IV with a compound of formula III provides compound of formula II which is converted reductively in a few steps into the compound of formula V, a know intermediate in the synthesis of compound of formula I. According to the disclosed process, Aliskiren can be now prepared from commercial starting materials (Guajacol or 2-bromoanisole, cis- or trans-1,4-dichloro-2-butene and 4(S)-benzyl-3-isovaleroyl-oxazolidin-2-one) in less than 8 process steps.
    Type: Grant
    Filed: December 24, 2011
    Date of Patent: April 22, 2014
    Assignee: Milan Soukup
    Inventor: Milan Soukup
  • Publication number: 20140073690
    Abstract: Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.
    Type: Application
    Filed: June 26, 2013
    Publication date: March 13, 2014
    Inventors: Michael M. MEIJLER, Josep RAYO, Neri AMARA
  • Publication number: 20140058021
    Abstract: A composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation; and b) a compound of formula I (Formula I) (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are independently from each other H, C1-C8-alkyl, C4-C8-cycloalkyl, phenyl, C1-C4-alkoxy or halogen; n is 1, 2, 3, or 4; and when n is 1 A is —C(=0)-OR?1, —C(=0)-N(R?2)(R?3), —CN, phenyl, which is unsubstituted or substituted by one or more C1-C8-alkyl, C4-C8-alkoxy, C5-C7-cycloalkyl or halogen, —H or —S02-phenyl; when n is 2 A is —C(=0)-O—Z1—O—C(=0)-, —C(=0)-N(R?1)—Z2—N(R?2)—C(=0)- or piperazine-N,N?-biscarbonyl.
    Type: Application
    Filed: April 25, 2012
    Publication date: February 27, 2014
    Applicant: BASF SE
    Inventors: Walter Fischer, Abdel-Ilah Basbas, Kai-Uwe Schoning, Cinzia Tartarini, Werner Holzl, Bruno Rotzinger
  • Publication number: 20140039195
    Abstract: A library of unnatural squarylated homoserine lactones (SHLs) and squarylated lactones that bear potential to modulate biofilm formation in Gram negative bacteria. At low concentrations (˜200 ?M), these small molecules inhibit biofilm formation of E. coli. Moreover, these compounds are not toxic up to 300 ?M and do not significantly attenuate E. coli growth. The SHLs have potential to disperse established biofilm and demonstrate an enhanced reduction (˜50%) of the maximum biofilm thickness by use of SHLs during biofilm growth.
    Type: Application
    Filed: August 1, 2013
    Publication date: February 6, 2014
    Applicant: SYRACUSE UNIVERSITY
    Inventors: Yan-Yeung Luk, Sri Kamesh Narasimhan, Eric Falcone
  • Publication number: 20130310577
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3-6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Application
    Filed: July 11, 2013
    Publication date: November 21, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Ben DE LANGE, Anna Maria Cornelia Francisca CASTELIJNS, Johannes Gerardus DE VRIES, Andreas Hendrikus Maria DE VRIES, Jeroen Antonius Franciscus BOOGERS
  • Patent number: 8563279
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: October 22, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Franciscus Boogers, Quirinus Bernardus Broxterman
  • Publication number: 20130225841
    Abstract: A method for preparing Aliskiren and intermediate thereof, which comprises the following steps: reacting 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene with magnesium isopropyl chloride and n-BuLi to obtain the compound of formula XXII; reacting the product of methylsulfonylation of the compound of formula XIX with anhydrous LiBr to obtain the compound of formula XXI; obtaining the intermediate of Aliskiren shown as formula XV by reacting the compound of formula XXII with the compound of formula XXI in an ether as the solvent and in the presence of a catalyst containing iron; then reacting the compound of formula XV with the compound of formula VII to obtain the compound of formula XXIII, following removing R1 from the amino group and obtaining Aliskiren shown as formula I.
    Type: Application
    Filed: April 19, 2010
    Publication date: August 29, 2013
    Applicant: Zhejiang Tianyu Pharmaceutical Co., Ltd.
    Inventors: Yongjun Tu, Yi Zhang, Rongde Cheng, Lingchao Peng
  • Patent number: 8501969
    Abstract: Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.
    Type: Grant
    Filed: July 4, 2010
    Date of Patent: August 6, 2013
    Assignee: The National Institute for Biotechnology in the Negev Ltd.
    Inventors: Michael M Meijler, Josep Rayo, Neri Amara
  • Publication number: 20130184279
    Abstract: Compounds of formula Ia and Ib wherein A, B, C, R1 and R14 are described herein.
    Type: Application
    Filed: December 18, 2012
    Publication date: July 18, 2013
    Applicant: Bristol-Myers Squibb Company
    Inventor: Bristol-Myers Squibb Company
  • Publication number: 20130184474
    Abstract: The invention relates to a method for preparing an amino acid, or its salts, from 2-aminobutyrolactone (2ABL), said amino acid fitting the formula I, XCH2CH2CHNH2COOH, wherein X is such that X? represents a nucleophilic ion, according to which N-carboxylation of 2-aminobutyrolactone (2ABL) is achieved with carbon dioxide, and the thereby obtained 2ABL carbamate is reactive with an XH reagent or its salts.
    Type: Application
    Filed: October 4, 2011
    Publication date: July 18, 2013
    Applicant: ADISSEO FRANCE S.A.S.
    Inventors: Robert Huet, Jean-Michel Joerger, Vivien Henryon
  • Publication number: 20130012728
    Abstract: Provided herein are processes for the preparation of N-acylated amines. In particular, the processes comprise contacting an amine with an acid comprising a carboxylic acid group to form the N-acylated amine.
    Type: Application
    Filed: March 9, 2011
    Publication date: January 10, 2013
    Applicant: NOVUS INTERNATIONAL INC.
    Inventors: Richard Vonder Embse, Michael Hayes, James C. Peterson
  • Patent number: 8350061
    Abstract: Bacterial quorum-sensing molecule analogs having the following structures: and methods of reducing bacterial pathogenicity, comprising providing a biological system comprising pathogenic bacteria which produce natural quorum-sensing molecule; providing a synthetic bacterial quorum-sensing molecule having the above structures and introducing the synthetic quorum-sensing molecule into the biological system comprising pathogenic bacteria. Further is provided a method of targeted delivery of an antibiotic, comprising providing a synthetic quorum-sensing molecule; chemically linking the synthetic quorum-sensing molecule to an antibiotic to produce a quorum-sensing molecule-antibiotic conjugate; and introducing the conjugate into a biological system comprising pathogenic bacteria susceptible to the antibiotic.
    Type: Grant
    Filed: November 1, 2011
    Date of Patent: January 8, 2013
    Assignee: Los Alamos National Security, LLC
    Inventors: Rashi S. Iyer, Kumkum Ganguly, Louis A. Silks
  • Patent number: 8343465
    Abstract: A topical cosmetic and dermatological preparation for reducing skin reddening which comprises (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl)-cyclohexane carboxamide and/or (1R,2S,5R)—N-(4-cyanomethyl-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide.
    Type: Grant
    Filed: March 12, 2009
    Date of Patent: January 1, 2013
    Assignee: Beiersdorf AG
    Inventors: Ludger Kolbe, Julia Eckert, Gitta Neufang, Stefanie Knaupmeier
  • Publication number: 20120296100
    Abstract: The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compound such as Aliskiren. The invention describes preparation of enantiomerically pure 8-aryloctanoic acid of formula I from a chiral compound of formula IV. Friedel-Crafts reaction of this compound of formula IV with a compound of formula III provides compound of formula II which is converted reductively in a few steps into the compound of formula V, a know intermediate in the synthesis of compound of formula I. According to the disclosed process, Aliskiren can be now prepared from commercial starting materials (Guajacol or 2-bromoanisole, cis- or trans-1,4-dichloro-2-butene and 4(S)-benzyl-3-isovaleroyl-oxazolidin-2-one) in less than 8 process steps.
    Type: Application
    Filed: December 24, 2011
    Publication date: November 22, 2012
    Applicant: CARBODESIGN LLC
    Inventor: MILAN SOUKUP
  • Patent number: 8273904
    Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: September 25, 2012
    Assignee: Bayer Cropscience AG
    Inventors: Norbert Lui, Jens-Dietmar Heinrich
  • Patent number: 8258320
    Abstract: The present invention generally relates to refreshing, soothing, and cooling compounds that affect sensory processes. More particularly, the present invention pertains to certain N-alkylcarbonyl-amino lactone compounds as described herein; compositions and articles comprising such compounds; and methods of treatment, for example, methods of alleviating the discomforts of irritation, itch, and pain in the skin and in the linings of the oral cavity and upper respiratory tract, for example, in methods of treatment of cough.
    Type: Grant
    Filed: January 18, 2011
    Date of Patent: September 4, 2012
    Inventor: Edward Tak Wei
  • Publication number: 20120184608
    Abstract: The present invention generally relates to refreshing, soothing, and cooling compounds that affect sensory processes. More particularly, the present invention pertains to certain N-alkylcarbonyl-amino lactone compounds as described herein; compositions and articles comprising such compounds; and methods of treatment, for example, methods of alleviating the discomforts of irritation, itch, and pain in the skin and in the linings of the oral cavity and upper respiratory tract, for example, in methods of treatment of cough.
    Type: Application
    Filed: January 18, 2011
    Publication date: July 19, 2012
    Inventor: Edward Tak Wei
  • Publication number: 20120165555
    Abstract: The present invention provides a novel process for opening a lactone and/or a lactam ring. More particularly, the present invention provides a process that employs a novel catalyst in the opening of a lactone ring and/or a lactam ring. Additionally, the present invention also provides a novel deprotection process of any protecting group present in either the lactone ring-containing and/or lactam ring-containing compound and/or in the ring-opened product thereof.
    Type: Application
    Filed: August 11, 2010
    Publication date: June 28, 2012
    Inventors: Megan Alene Foley, Timothy F. Jamison, Oljan Repic
  • Patent number: 8203005
    Abstract: The invention describes a novel technical process and novel intermediates useful for the manufacture of enantiomerically pure 8-aryloctanoic acids of the formula I which are pharmaceutically active compounds as rennin inhibitors.
    Type: Grant
    Filed: October 15, 2010
    Date of Patent: June 19, 2012
    Assignee: Carbo Design LLC
    Inventor: Milan Soukup
  • Patent number: 8198465
    Abstract: The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren. Inter alia, the invention relates to a process for the manufacture of a compound of the formula II, or a salt thereof, and a compound of formula VI or a salt thereof, wherein R3 and R4 as well as Act are as defined in the specification, and processes of manufacturing these. Additionally transformation of compounds (VI) with metallo organic compounds (VII) give rise to the new compounds (VIII) which are direct precursors for the preparation of Aliskiren.
    Type: Grant
    Filed: June 25, 2010
    Date of Patent: June 12, 2012
    Assignee: Novartis AG
    Inventors: Gottfried Sedelmeier, Dominique Grimler, Murat Acemoglu
  • Publication number: 20120135925
    Abstract: Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.
    Type: Application
    Filed: July 4, 2010
    Publication date: May 31, 2012
    Inventors: Michael M. Meijler, Josep Rayo, Neri Amara
  • Publication number: 20120022100
    Abstract: Disclosed are ?-amino-?-hydroxy-?-aryl-alkanoic acid amide compounds of formula (I) and the salts thereof, having renin-inhibiting properties. Also disclosed are pharmaceutical compositions comprising these compounds and methods of administering them for the treatment of hypertension, atherosclerosis, unstable coronary syndrome, congestive heart failure, cardiac hypertrophy, cardiac fibrosis, cardiomyopathy postinfarction, unstable coronary syndrome, diastolic dysfunction, chronic kidney disease, hepatic fibrosis, complications resulting from diabetes, such as nephropathy, vasculopathy and neuropathy, diseases of the coronary vessels, restenosis following angioplasty, raised intra-ocular pressure, glaucoma, abnormal vascular growth, hyperaldosteronism, cognitive impairment, alzheimers, dementia, anxiety states and cognitive disorders.
    Type: Application
    Filed: September 28, 2011
    Publication date: January 26, 2012
    Inventors: Juergen Klaus Maibaum, Daniel K. Baeschlin, Holger Sellner
  • Patent number: 8071790
    Abstract: Bacterial quorum-sensing molecule analogs having the following structures: and methods of reducing bacterial pathogenicity, comprising providing a biological system comprising pathogenic bacteria which produce natural quorum-sensing molecule; providing a synthetic bacterial quorum-sensing molecule having the above structures and introducing the synthetic quorum-sensing molecule into the biological system comprising pathogenic bacteria. Further is provided a method of targeted delivery of an antibiotic, comprising providing a synthetic quorum-sensing molecule; chemically linking the synthetic quorum-sensing molecule to an antibiotic to produce a quorum-sensing molecule-antibiotic conjugate; and introducing the conjugate into a biological system comprising pathogenic bacteria susceptible to the antibiotic.
    Type: Grant
    Filed: September 1, 2009
    Date of Patent: December 6, 2011
    Assignee: Los Alamos National Security, LLC
    Inventors: Rashi Iyer, Kumkum Ganguly, Louis A. Silks
  • Publication number: 20110274803
    Abstract: The present invention relates to enaminocarbonyl compounds with the formula I, in which X denotes O or CH2, Y denotes N and each of R1 and R2 denotes hydrogen, or Y denotes a CH and either R1 or R2 denotes a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, selected (for Y denoting CH and R1 or R2 denoting a C1-4 alkyl) from a group encompassing a mixture of R and S enantiomers enriched in either enantiomer R or enantiomer S, enantiomer R and enantiomer S. The present invention also relates to the use of compounds with the formula I, in which X denotes O or CH2, Y denotes a CH and either R1 or R2 is selected from a group encompassing hydrogen and a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, for the modification of the taste of a product and/or preparation for oral administration.
    Type: Application
    Filed: February 2, 2010
    Publication date: November 10, 2011
    Inventors: Piotr Krajewski, Agnieszka Wozniak
  • Patent number: 8049020
    Abstract: The substituted N-acyl homoserine lactones have the formula (I) wherein R is a saturated or unsaturated straight chain or branched chain aliphatic hydrocarbyl group containing from 5 to 14 carbon atoms; R2 is H or a 1-4C alkyl group; R3 is H or F; and any enantiomer thereof. These compounds exhibit immunosuppressant activity while exhibiting reduced biosensor (autoinducer) activity compared to known N-acyl homoserine lactones.
    Type: Grant
    Filed: May 22, 2007
    Date of Patent: November 1, 2011
    Assignee: The Secretary of State for Defence
    Inventors: David Idris Pritchard, Siri Ram Chhabra
  • Publication number: 20110244531
    Abstract: The invention relates to a process for the preparation of compounds that are important building blocks in convergent synthesis routes to 2(S),4(S),5(S),7(S)-2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoyl amides or pharmaceutically acceptable salts thereof, such as the compound Aliskiren, and to a process for the preparation of these octanoyl amides, comprising reacting said building block.
    Type: Application
    Filed: July 23, 2009
    Publication date: October 6, 2011
    Inventors: Andreas Hendrikus Maria De Vries, Gerardus Karel Maria Verzijl, Petrus Johannes Hermsen, Anna Maria Cornelia Francisca Castelijns
  • Publication number: 20110212860
    Abstract: The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
    Type: Application
    Filed: February 22, 2011
    Publication date: September 1, 2011
    Inventors: Helen E. Blackwell, Grant D. Geske, Jennifer C. Campbell
  • Publication number: 20110137047
    Abstract: The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially rennin inhibitors such as Aliskiren. The invention describes a preparation of enantiomerically pure 8-aryloctanoic acids of general formula I from readily available key intermediate, chiral cis-diacid of formula II, aziridine of formula XI and a monocyclic compound of formula III.
    Type: Application
    Filed: October 15, 2010
    Publication date: June 9, 2011
    Applicant: CarboDesign LLC
    Inventor: Milan Soukup
  • Publication number: 20110105767
    Abstract: The invention describes a novel technical process and novel intermediates useful for the manufacture of enantiomerically pure 8-aryloctanoic acids of the formula I which are pharmaceutically active compounds as rennin inhibitors.
    Type: Application
    Filed: October 15, 2010
    Publication date: May 5, 2011
    Applicant: CarboDesign LLC
    Inventor: Milan Soukup
  • Patent number: 7910622
    Abstract: The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
    Type: Grant
    Filed: March 19, 2008
    Date of Patent: March 22, 2011
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Helen E. Blackwell, Grant D. Geske, Jennifer C. O'Neill
  • Publication number: 20110053890
    Abstract: Bacterial quorum-sensing molecule analogs having the following structures: and methods of reducing bacterial pathogenicity, comprising providing a biological system comprising pathogenic bacteria which produce natural quorum-sensing molecule; providing a synthetic bacterial quorum-sensing molecule having the above structures and introducing the synthetic quorum-sensing molecule into the biological system comprising pathogenic bacteria. Further is provided a method of targeted delivery of an antibiotic, comprising providing a synthetic quorum-sensing molecule; chemically linking the synthetic quorum-sensing molecule to an antibiotic to produce a quorum-sensing molecule-antibiotic conjugate; and introducing the conjugate into a biological system comprising pathogenic bacteria susceptible to the antibiotic.
    Type: Application
    Filed: September 1, 2009
    Publication date: March 3, 2011
    Applicant: Los Alamos National Security, LLC.
    Inventors: Rashi Iyer, Kumkum Ganguly, Louis A. Silks
  • Publication number: 20110021624
    Abstract: Disclosed are a series of ?-amino-N-substituted amide compounds having a structure of the following formula, the pharmaceutically acceptable salts thereof, and the pharmaceutical composition comprising the same. The ?-amino-N-substituted amide compounds or the pharmaceutically acceptable salts thereof according to the present invention have anti-tumor and/or anti-cancer activities in vivo and in vitro, can effectively depress the growth of various tumor cells and/or cancer cells, and thus can be used in preparing drugs for treating tumors and/or cancers.
    Type: Application
    Filed: December 11, 2008
    Publication date: January 27, 2011
    Inventors: Fajun Nan, Jia Li, Jian Ding, Gang Liu, Chuanming Xie, Zehong Miao, Wanyi Tai
  • Publication number: 20110008852
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Application
    Filed: December 19, 2008
    Publication date: January 13, 2011
    Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Boogers, Quirinus Bernardus Broxterman
  • Publication number: 20100305182
    Abstract: The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.
    Type: Application
    Filed: December 17, 2009
    Publication date: December 2, 2010
    Inventors: Helen E. BLACKWELL, Grant D. Geske, Rachel Wezeman
  • Publication number: 20100298559
    Abstract: There is provided a novel optically active dinickel complex and/or a production method of an optically active amine by an asymmetric Mannich reaction using the dinickel complex as a catalyst. An optically active dinickel complex of Formula (I) or Formula (I?): [where R0, R1, R2, R3, R4, R5, R6, and R7 are each independently a hydrogen atom, a halogen atom, a C1-10 alkyl group or a C1-10 alkoxy group, etc., R2 and R3 together form, together with a benzene ring bonded to them, a naphthalene ring, etc. A novel production method of an optically active amine by an asymmetric Mannich reaction using the dinickel complex as a catalyst.
    Type: Application
    Filed: December 10, 2008
    Publication date: November 25, 2010
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Masakatsu Shibasaki, Shigeki Matsunaga, Zhihua Chen
  • Publication number: 20100292261
    Abstract: In the quorum sensing antagonist blocking the communication in bacteria, the method for preventing biofilm formation using this quorum sensing antagonist and the method for reducing the bacterial contamination, the quorum sensing antagonist contains the homoserine lactone moiety and sulfanylethanoyl group, and has a similar chemical structure to that of the autoinducer which is produced by bacteria as a signal, whereby the quorum sensing antagonist can inhibit the formation of biofilm and reduce the bacterial contamination as well.
    Type: Application
    Filed: May 3, 2007
    Publication date: November 18, 2010
    Applicant: SEOUL NATIONAL UNIVERSITY INDUSTRY FOUNDATION
    Inventors: Je-Yong Yoon, Cheol-Jin Kim, Jae-Eun Kim, Hyung-Yeon Park
  • Publication number: 20100286261
    Abstract: The substituted N-acyl homoserine lactones have the formula (I) wherein R is a saturated or unsaturated straight chain or branched chain aliphatic hydrocarbyl group containing from 5 to 14 carbon atoms; R2 is H or a 1-4C alkyl group; R3 is H or F; and any enantiomer thereof. These compounds exhibit immunosuppressant activity while exhibiting reduced biosensor (autoinducer) activity compared to known N-acyl homoserine lactones.
    Type: Application
    Filed: May 22, 2007
    Publication date: November 11, 2010
    Inventors: David Idris Pritchard, Siri Ram Chhabra
  • Publication number: 20100267965
    Abstract: The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren. Inter alia, the invention relates to a process for the manufacture of a compound of the formula II, or a salt thereof, and a compound of formula VI or a salt thereof, wherein R3 and R4 as well as Act are as defined in the specification, and processes of manufacturing these. Additionally transformation of compounds (VI) with metallo organic compounds (VII) give rise to the new compounds (VIII) which are direct precursors for the preparation of Aliskiren.
    Type: Application
    Filed: June 25, 2010
    Publication date: October 21, 2010
    Inventors: Gottfried Sedelmeier, Dominique Grimler, Murat Acemoglu
  • Publication number: 20100190990
    Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:
    Type: Application
    Filed: September 5, 2008
    Publication date: July 29, 2010
    Applicant: Bayer Cropscience AG
    Inventors: Norbert Lui, Jens-Dietmar Heinrich