Protecting Or Removing Protective Groups, E.g., Carboxyl Group Protection, Etc. Patents (Class 530/335)
  • Patent number: 9334302
    Abstract: The present invention relates to a method of removing an Fmoc group, including a step of mixing a compound represented by the formula (I): HS-L-COOH??(I) wherein L is a C1-8 alkylene group optionally having substituent(s), an amino group-containing compound protected by an Fmoc group, and a base to give a reaction mixture containing a compound represented by the formula (II): Fm—S-L-COOH??(II) wherein Fm is a 9-fluorenylmethyl group, and L is as mentioned above, and an amino group-containing compound, and a step of removing the compound represented by the formula (II) by washing the obtained reaction mixture with a basic aqueous solution. According to the present invention, a removal method of Fmoc group, which can remove a dibenzofulvene derivative as a byproduct with ease, can be provided.
    Type: Grant
    Filed: June 16, 2014
    Date of Patent: May 10, 2016
    Assignee: AJINOMOTO CO., INC.
    Inventor: Daisuke Takahashi
  • Patent number: 9051364
    Abstract: A composition includes D-peptides or antibodies to at least one of to prevent a disease and to treat the disease, wherein the D-peptides interact with an amyloid peptide and the antibodies bind to both the D-peptide and the amyloid peptide.
    Type: Grant
    Filed: November 17, 2009
    Date of Patent: June 9, 2015
    Assignees: FORSCHUNGSZENTRUM JUELICH GMBH, HEINRICH-HEINE-UNIVERSITAET
    Inventors: Dieter Willbold, Carsten Korth, Andreas Mueller-Schiffmann, Susanne Aileen Funke
  • Publication number: 20140343227
    Abstract: The invention relates to a method for homogeneous solution phase peptide synthesis (HSPPS) of a N-terminal peptide fragment PEP-N and a C-terminal peptide fragment C-PEP, with C-PEP carrying a specific diketopiperazine (DKP) comprising C-terminal protecting group, which contains a handle group HG, with HG being connected to the C-terminus of the peptide fragmcnt; thereby this specific DKP comprising C-terminal protecting group can be selectively cleaved from the peptide as a conventionally used C-terminal protecting group. By the use of this DKP and HG comprising C-terminal protecting group, certain process steps in convergent peptide synthesis based on a combination of HSPPS and solid phase peptide synthesis (SPPS) can be avoided.
    Type: Application
    Filed: June 20, 2014
    Publication date: November 20, 2014
    Inventors: Fernando Albericio, Michèle Cristau, Matthieu Giraud, Miriam Gongora Benitez, Judit Tulla-Puche
  • Patent number: 8871903
    Abstract: Methods to synthesize self-assembling peptides embedded with complex organic electronic subunits are provided.
    Type: Grant
    Filed: October 22, 2012
    Date of Patent: October 28, 2014
    Assignee: The Johns Hopkins University
    Inventors: John D. Tovar, Allix M. Sanders
  • Patent number: 8865863
    Abstract: The invention relates to a method for producing peptoidic, peptidic and chimeric peptidic-peptoidic dendrimers by multiple iterative multi-component reactions (MCR), in particular Ugi or Passerini multi-component reactions, to compounds produced in this way and to the use thereof.
    Type: Grant
    Filed: April 14, 2011
    Date of Patent: October 21, 2014
    Assignee: Leibniz-Institut fur Pflandzenbiochemie
    Inventors: Ludger A. Wessjohann, Michael Henze, Oliver Kreye, Daniel Garcia Rivera
  • Patent number: 8859732
    Abstract: The present invention provides a protecting reagent that can be removed in a high yield even under acidic conditions and can afford a resulting product at a high purity in an organic synthesis reaction such as peptide synthesis and the like. The inventive protecting reagent is particular benzylic compound having only one hydroxyl group substituted by an organic group having an aliphatic hydrocarbon group having a carbon number of not less than 14.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: October 14, 2014
    Assignee: Ajinomoto Co., Inc.
    Inventor: Daisuke Takahashi
  • Publication number: 20140275481
    Abstract: Systems and processes for performing solid phase peptide synthesis are generally described. Solid phase peptide synthesis is a known process in which amino acid residues are added to peptides that have been immobilized on a solid support. In certain embodiments, the inventive systems and methods can be used to perform solid phase peptide synthesis quickly while maintaining high yields. Certain embodiments relate to processes and systems that may be used to heat, transport, and/or mix reagents in ways that reduce the amount of time required to perform solid phase peptide synthesis.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 18, 2014
    Inventors: Mark David Simon, Bradley L. Pentelute, Andrea Adamo, Patrick Louis Heider, Klavs F. Jensen
  • Patent number: 8802819
    Abstract: The invention relates to a method for homogeneous solution phase peptide synthesis (HSPPS) of a N-terminal peptide fragment PEP-N and a C-terminal peptide fragment C-PEP, with C-PEP carrying a specific diketopiperazine (DKP) comprising C-terminal protecting group, which contains a handle group HG, with HG being connected to the C-terminus of the peptide fragment; thereby this specific DKP comprising C-terminal protecting group can be selectively cleaved from the peptide as a conventionally used C-terminal protecting group. By the use of this DKP and HG comprising C-terminal protecting group, certain process steps in convergent peptide synthesis based on a combination of HSPPS and solid phase peptide synthesis (SPPS) can be avoided.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: August 12, 2014
    Assignee: Lonza Ltd.
    Inventors: Fernando Albericio, Michèle Cristau, Matthieu Giraud, Miriam Gongora Benitez, Judit Tulla-Puche
  • Patent number: 8784777
    Abstract: A solid phase peptide synthesis method for synthesizing a peptidyl contrast agent is disclosed. In one example, the method includes synthesizing an amino-chelator loaded resin, coupling of the amino-chelator loaded resin to the C-terminus and/or backbone of a peptide, cleaving the amino-chelator-peptide from a resin, and chelating a lanthanide metal to the amino-chelator-peptide.
    Type: Grant
    Filed: November 29, 2010
    Date of Patent: July 22, 2014
    Assignee: Case Western Reserve University
    Inventors: Mark D. Pagel, Byunghee Yoo
  • Patent number: 8729229
    Abstract: The present invention relates to processes for preparing a polypeptide or pharmaceutically acceptable salt thereof comprising L-tyrosine, L-alanine, L-glutamate, and L-lysine. The polypeptide or pharmaceutically acceptable salt thereof is preferably glatiramer acetate.
    Type: Grant
    Filed: March 18, 2010
    Date of Patent: May 20, 2014
    Assignee: Sandoz AG
    Inventors: Anup Kumar Ray, Hiren Kumar V. Patel, Johannes Ludescher, Mariappan Anbazhagan, Mahendra R. Patel, Ingolf Macher
  • Patent number: 8703912
    Abstract: A dibenzofulvene amine adduct is removed by contacting a reaction mixture containing the dibenzofulvene amine adduct, which is obtained by reacting, for deprotection, an amino acid compound protected with an Fmoc group with an amine compound containing a nitrogen atom which is bonded to at least one hydrogen atom, with carbon dioxide, and removing the carbonate of the dibenzofulvene amine adduct. Alternatively, a dibenzofulvene amine adduct is removed by mixing a reaction mixture during a deprotection reaction of the amino acid compound protected with an Fmoc group, or after the reaction with an amine compound containing a nitrogen atom which is bonded to at least one hydrogen atom to give a mixture containing the dibenzofulvene amine adduct, contacting the mixture with carbon dioxide, and removing the carbonate of the dibenzofulvene amine adduct.
    Type: Grant
    Filed: February 4, 2011
    Date of Patent: April 22, 2014
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yuji Nishiuchi, Terutoshi Kimura
  • Publication number: 20140088291
    Abstract: The present invention provides a production method of peptide, which includes the following step (1). (1) removing N-terminal Fmoc group of N-Fmoc C-protected amino acid or N-Fmoc C-protected peptide wherein a C-terminal carboxy group is protected by an anchor group derived from an anchor soluble in halogenated solvents or ether solvents, insoluble in polar solvents and having a molecular weight of not less than 300, with a non-nucleophilic organic base in a halogenated solvent or ether solvent to give a C-protected amino acid or C-protected peptide, neutralizing with an acid, adding N-Fmoc amino acid or N-Fmoc peptide, a condensing agent and a condensation accelerator to the reaction solution after neutralization, and condensing the N-terminal of the C-protected amino acid or C-protected peptide with N-Fmoc amino acid or N-Fmoc peptide to give an N-Fmoc C-protected peptide.
    Type: Application
    Filed: November 26, 2013
    Publication date: March 27, 2014
    Applicant: AJINOMOTO CO., INC.
    Inventor: Daisuke TAKAHASHI
  • Patent number: 8664357
    Abstract: According to the present invention, there is provided a process for the preparation of a first compound selected from peptides, oligonucleotides and peptide nucleic acids. The process comprises synthesizing the first compound and then separating the first compound formed in step (i) from a second compound, which is a reaction by-product of the synthesis of the first compound and/or an excess of a reagent used for the synthesis of a first compound by a process of diafiltration. The membrane used for the diafiltration process is stable in organic solvents and provides a rejection for the first compound which is greater than the rejection for the second compound.
    Type: Grant
    Filed: August 7, 2009
    Date of Patent: March 4, 2014
    Assignee: Imperial Innovations Limited
    Inventors: Andrew Guy Livingston, Ludmila Georgieva Peeva, Sheyung Wang Jerry So, Renato Campos Vasconceles, Robin John Leatherbarrow, Edward William Tate, Piers Robert James Gaffney
  • Patent number: 8652484
    Abstract: The present invention relates to methods and compositions for pretargeting delivery of therapeutic agents. In preferred embodiments, the pretargeting method comprises: a) administering a bispecific antibody with a first binding site for a disease-associated antigen and a hapten on a targetable construct; b) administering a targetable construct comprising at least one therapeutic agent. In preferred embodiments, the bispecific antibody is made by the dock-and-lock (DNL) technique. In a more preferred embodiment, the targetable construct comprises one or more SN-38 moieties.
    Type: Grant
    Filed: December 11, 2012
    Date of Patent: February 18, 2014
    Assignee: Immunomedics, Inc.
    Inventors: William J. McBride, Christopher A. D'Souza, Chien-Hsing Chang, David M. Goldenberg
  • Publication number: 20140046022
    Abstract: Particular compounds having a fluorene skeleton are superior in broad utility and stability, as a protecting reagent for liquid phase synthesis of amino acids and/or peptides.
    Type: Application
    Filed: September 16, 2013
    Publication date: February 13, 2014
    Applicant: Ajinomoto Co., Inc.
    Inventor: Daisuke Takahashi
  • Publication number: 20140005121
    Abstract: This invention relates to oligopeptides having general formula (I). The invention also relates to the process of preparation thereof, wherein the said compounds are selective anti-cancer agents over a panel of human cancer cell lines. Further, this invention relates that said anti-cancer peptides are prepared by a novel method.
    Type: Application
    Filed: January 23, 2012
    Publication date: January 2, 2014
    Applicant: Council of Scientific & Industrial Research
    Inventors: Tushar Kanti Chakraborty, Praveen Kumar Gajula, Dulal Panda, Jayant Asthana
  • Patent number: 8592142
    Abstract: Methods for analyzing, selecting, characterizing or classifying compositions of a co-polymer, e.g., glatiramer acetate are described. The methods entail analysis of pyro-glutamate in the composition, and, in some methods, comparing the amount of pyro-glutamate present in a composition to a reference standard.
    Type: Grant
    Filed: December 10, 2012
    Date of Patent: November 26, 2013
    Assignee: Momenta Pharmaceuticals, Inc.
    Inventors: Xiangping Zhu, Zachary Shriver, Yanjie Jiang, Corinne Bauer, James Eric Anderson, Peter James Ahern
  • Patent number: 8551951
    Abstract: The invention provides pharmaceutical compositions and method for inhibiting growth of prostatic adenocarcinoma, stomach cancer, breast cancer, endometrial, ovarian or other cancers of epithelial secretion, or benign prostate hyperplasia (BPH). In one embodiment the pharmaceutical composition includes human rHuPSP94, antigenic portions thereof, and functionally equivalent polypeptides thereof. In another embodiment, the pharmaceutical composition includes a mixture of human rHuPSP94, antigenic portions thereof, and functionally equivalent polypeptides thereof and an anticancer drug which may be administered in an appropriate dosage form, dosage quantity and dosage regimen to a patient suffering from, for example of prostatic adenocarcinoma, stomach cancer, breast cancer, endometrial, ovarian or other cancers of epithelial secretion, benign prostate hyperplasia, or (BPH) gastrointestinal cancer.
    Type: Grant
    Filed: January 22, 2010
    Date of Patent: October 8, 2013
    Assignee: Aenorasis SA Pharmaceuticals and Medical Devices
    Inventors: Seema Garde, Chandra J. Panchal, Madhulika Baijal-Gupta, Jennifer Fraser, Salam Kadhim
  • Patent number: 8546534
    Abstract: The present invention provides a particular branched chain-containing aromatic compound. The branched chain-containing aromatic compound of the present invention is easily-soluble in isopropyl acetate superior in liquid-separation operability, and can be used for a production method of peptide and the like, which provides a final product simply by extraction separation, without crystallization and isolation of each intermediate in each step.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: October 1, 2013
    Assignee: Ajinomoto Co., Inc.
    Inventor: Daisuke Takahashi
  • Patent number: 8536305
    Abstract: The present invention relates to an improved process for preparing a polypeptide or pharmaceutically acceptable salt thereof comprising L-tyrosine, L-alanine, L-glutamate, and L-lysine. The polypeptide or pharmaceutically acceptable salt thereof is preferably glatiramer acetate.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: September 17, 2013
    Assignee: Sandoz AG
    Inventors: Anup K Ray, Hiren V Patel, Johannes Ludescher, Mariappan Anbazhagan, Mahendra R Patel, Ingolf Macher
  • Publication number: 20130203960
    Abstract: The invention relates to a method for producing peptoidic, peptidic and chimeric peptidic-peptoidic dendrimers by multiple iterative multi-component reactions (MCR), in particular Ugi or Passerini multi-component reactions, to compounds produced in this way and to the use thereof.
    Type: Application
    Filed: April 14, 2011
    Publication date: August 8, 2013
    Applicant: LEIBNIZ-INSTITUT FUR PFLANZENBIOCHEMIE
    Inventors: Ludger A. Wessjohann, Michael Henze, Oliver Kreye, Daniel Garcia Rivera
  • Patent number: 8492341
    Abstract: A peptide sequence of the form: X(Lys,Arg)XXXXX(Arg,Lys)X, wherein Lys and Arg are replaceable and X is preferably one or more of the following amino acids: hydrophobic amino acid residues (eg Pro, Leu, Met, Ile), basic amino acid residues or threonine; and wherein the sequence is capable of engaging A? and ameliorating its SOD activity and/or metal ion binding.
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: July 23, 2013
    Assignee: Alzyme Pty Ltd.
    Inventors: Ralph Martins, Trevor Payne
  • Patent number: 8329391
    Abstract: Methods for analyzing, selecting, characterizing or classifying compositions of a co-polymer, e.g., glatiramer acetate are described. The methods entail analysis of pyro-glutamate in the composition, and, in some methods, comparing the amount of pyro-glutamate present in a composition to a reference standard. In some cases, the methods entail treating the co-polymer with pyro-glutamate aminopeptidase to cleave N-terminal pyro-glutamate residues.
    Type: Grant
    Filed: March 20, 2009
    Date of Patent: December 11, 2012
    Assignee: Momenta Pharmaceuticals, Inc.
    Inventors: Xiangping Zhu, Zachary Shriver, Yanjie Jiang, Corinne Bauer, James Eric Anderson, Peter James Ahern
  • Patent number: 8314208
    Abstract: A method is disclosed for carrying out peptide synthesis comprising deprotecting an Fmoc-protected amino acid with piperazine while applying microwave irradiation to the deprotection reaction.
    Type: Grant
    Filed: February 10, 2006
    Date of Patent: November 20, 2012
    Assignee: CEM Corporation
    Inventor: Jonathan M. Collins
  • Patent number: 8247534
    Abstract: The present invention addresses a novel method of preparing radiofluorinated peptide-based compounds and introducing those compounds into an automated radiosynthesis apparatus with the aid of microwave activation. The present invention further relates to obtaining radiopharmaceutical kits utilizing microwave activation technology for the preparation of obtaining peptide based compounds as well as a method for the use of preparing a peptide based compound.
    Type: Grant
    Filed: December 12, 2007
    Date of Patent: August 21, 2012
    Assignee: GE Healthcare AS
    Inventor: Lorenzo Williams
  • Patent number: 8217142
    Abstract: The invention relates to improved liquid phase processes for the preparation of the 21 residue protein component, (Lys-Leu4)4-Lys, of the pulmonary surfactant KL-4. These process are amenable to large scale synthesis and one process employs a method of saponifying an ester which reduces the inherent racemization of the ?-carbon.
    Type: Grant
    Filed: September 30, 2008
    Date of Patent: July 10, 2012
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Ahmed F. Abdel-Magid, Urs Eggmann, Cynthia Anne Maryanoff, Adrian Thaler, Frank J. Villani
  • Patent number: 8207299
    Abstract: The invention relates to novel citrulline peptides derived from fibrin ? and ? chains which are recognizable by specific citrulline antiprotein autoantibodies (AAPC) of a rheumatoid arthritis (PR) and to the use thereof for detecting the presence of said specific PR AAPC in a biological sample.
    Type: Grant
    Filed: November 3, 2005
    Date of Patent: June 26, 2012
    Assignee: Biomerieux
    Inventors: Guy Serre, Mireille Sebbag
  • Patent number: 8188216
    Abstract: A library of macrocyclic compounds of the formula (I) where part (A) is a bivalent radical, a —(CH2)y— bivalent radical or a covalent bond; where part (B) is a bivalent radical, a —(CH2)z— bivalent radical, or a covalent bond; where part (C) is a bivalent radical, a —(CH2)t- bivalent radical, or a covalent bond; and where part (T) is a -Y-L-Z- radical wherein Y is CH2 or CO, Z is NH or O and L is a bivalent radical. These compounds are useful for carrying out screening assays or as intermediates for the synthesis of other compounds of pharmaceutical interest. A process for their preparation of these compounds in a combinatorial manner, is also disclosed.
    Type: Grant
    Filed: October 7, 2004
    Date of Patent: May 29, 2012
    Assignee: Tranzyme Pharma Inc.
    Inventors: Pierre Deslongchamps, Yves Dory, Gilles Berthiaume, Luc Ouellet, Ruoxi Lan
  • Patent number: 8153761
    Abstract: An instrument and associated method are disclosed for the accelerated synthesis of peptides by the solid phase method. The instrument includes a microwave cavity, a microwave source in communication with the cavity, a column in the cavity formed of a material that is transparent to microwave radiation, a solid phase peptide support resin in the column, respective filters for maintaining the solid phase support resin in the column, a first passageway for adding starting compositions to the column, a second passageway for removing compositions from the column, and a third passageway for circulating compositions from the column into the third passageway and back to the column.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: April 10, 2012
    Assignee: CEM Corporation
    Inventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
  • Patent number: 8138304
    Abstract: Neural regeneration peptide consisting of a sequence comprised in the sequence of REGRRAAPGRAGG(SEQ ID NO:1).
    Type: Grant
    Filed: May 5, 2006
    Date of Patent: March 20, 2012
    Assignee: Neuren Pharmaceuticals Limited
    Inventors: Frank Sieg, Margaret Anne Brimble, Victoria Justine Muir
  • Publication number: 20120059149
    Abstract: [Summary] [Problem] Provision of a novel compound which is easily-soluble in isopropyl acetate superior in liquid-separation operability, and can be used for a production method of peptide and the like, that provides a final product simply by extraction-layer-separating, without crystallization and isolation of each intermediate in each step. [Solving Means] It has been found that the above-mentioned problems can be solved by a particular branched chain-containing aromatic compound.
    Type: Application
    Filed: August 30, 2011
    Publication date: March 8, 2012
    Applicant: AJINOMOTO CO. INC.
    Inventor: Daisuke TAKAHASHI
  • Publication number: 20120052090
    Abstract: An object of the present invention is to provide an HIV antibody-inducing peptide antigen that can be used without problems for HIV, which is highly prone to mutation, and is effective in developing an antibody or a vaccine having excellent specificity and binding activity even for the three-dimensional structure of a neutralization target, i.e. the mechanism by which HIV invades a target cell; a method for synthesizing the same; a vaccine comprising the peptide antigen, or an HIV three-dimensional structure-recognizing antibody induced by the peptide antigen; and a preventive and/or therapeutic agent for HIV infection comprising the peptide antigen, the vaccine, or the HIV three-dimensional structure-recognizing antibody as an active ingredient.
    Type: Application
    Filed: May 14, 2010
    Publication date: March 1, 2012
    Applicant: National University Corporation Tokyo Medical and Dental University
    Inventors: Hirokazu Tamamura, Toru Nakahara, Wataru Nomura
  • Patent number: 8071328
    Abstract: A sensitive bioluminescent assay to detect proteases including caspases, trypsin and tryptase is provided.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: December 6, 2011
    Assignee: Promega Corporation
    Inventors: Martha O'Brien, Keith V. Wood, Dieter Klaubert, William Daily
  • Patent number: 8058393
    Abstract: An instrument and method for accelerating the solid phase synthesis of peptides are disclosed. The method includes the steps of deprotecting a protected first amino acid linked to a solid phase resin by admixing the protected linked acid with a deprotecting solution in a microwave transparent vessel while irradiating the admixed acid and solution with microwaves, activating a second amino acid, coupling the second amino acid to the first acid while irradiating the composition in the same vessel with microwaves, and cleaving the linked peptide from the solid phase resin by admixing the linked peptide with a cleaving composition in the same vessel while irradiating the composition with microwaves.
    Type: Grant
    Filed: August 28, 2009
    Date of Patent: November 15, 2011
    Assignee: CEM Corporation
    Inventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
  • Patent number: 8058235
    Abstract: Methods of making copolymers are described.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: November 15, 2011
    Assignee: Momenta Pharmaceuticals, Inc.
    Inventors: Claire Coleman, John Schaeck, Alicia Thompson
  • Publication number: 20110245460
    Abstract: According to the present invention, there is provided a process for the preparation of a first compound selected from peptides, oligonucleotides and peptide nucleic acids. The process comprises synthesising the first compound and then separating the first compound formed in step (i) from a second compound, which is a reaction by-product of the synthesis of the first compound and/or an excess of a reagent used for the synthesis of a first compound by a process of diafiltration. The membrane used for the diafiltration process is stable in organic solvents and provides a rejection for the first compound which is greater than the rejection for the second compound.
    Type: Application
    Filed: August 7, 2009
    Publication date: October 6, 2011
    Applicant: IMPERIAL INNOVATIONS LIMITED
    Inventors: Andrew Guy Livingston, Ludmila Georgieva Peeva, Sheyung Wang Jerry So, Renato Campos Vasconceles, Robin John Leatherbarrow, Edward William Tate, Piers Robert James Gaffney
  • Patent number: 8008434
    Abstract: The invention relates to a process for the preparation of at least one solid phase bound peptide. PNA or a chimera.
    Type: Grant
    Filed: May 25, 2005
    Date of Patent: August 30, 2011
    Assignee: Deutsches Krebsforschungszentrum Stiftung des Offentlichen Rechts
    Inventors: Ole Brandt, Anette Jacob, Jörg Hoheisel
  • Patent number: 7977119
    Abstract: Methods and compositions for generating mixtures of product molecules from an initial chemical array are provided. In the subject methods, a chemical array of surface immobilized first moieties is subjected to cleavage conditions such that a composition of solution phase first moieties is produced. The resultant composition of solution phase first moieties is then contacted with one or more reactants to produce a mixture of product molecules that are different from the first moieties. Also provided are the arrays employed in the subject methods and kits for practicing the subject methods.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: July 12, 2011
    Assignee: Agilent Technologies, Inc.
    Inventors: Mel N. Kronick, Eric M. Leproust
  • Publication number: 20110160433
    Abstract: The present invention provides a protecting reagent that can be removed in a high yield even under acidic conditions and can afford a resulting product at a high purity in an organic synthesis reaction such as peptide synthesis and the like. The inventive protecting reagent is particular benzylic compound having only one hydroxyl group substituted by an organic group having an aliphatic hydrocarbon group having a carbon number of not less than 14.
    Type: Application
    Filed: December 22, 2010
    Publication date: June 30, 2011
    Applicant: AJINOMOTO CO., INC.
    Inventor: Daisuke TAKAHASHI
  • Patent number: 7960340
    Abstract: The present invention relates generally to a molecular framework having a cyclic structure. More particularly, the present invention provides cyclic proteins and derivatives thereof in which particular turns and other elements of the molecular structure are held in defined orientations with respect to each other. The cyclic proteins of the present invention provide a molecular framework for the introduction of particular amino acids or heterologous amino acid sequences to facilitate the presentation of biological activities associated with these heterologous amino acid sequences. The molecular framework of the present invention may be naturally cyclic or may be a cyclized derivative of a linear molecular or may be a linear derivative of a cyclized molecule. The present invention contemplates the use of the molecular framework with or without particular amino acids inserted or substituted thereon for the treatment of or prophylaxis of disease conditions in animals, mammals (including humans) and plants.
    Type: Grant
    Filed: March 1, 2010
    Date of Patent: June 14, 2011
    Assignee: The University of Queensland
    Inventors: David J. Craik, Norelle Lee Daly, Clement Waim-Kunduane Waine
  • Patent number: 7951773
    Abstract: Disclosed is a process for preparing a compound of formula (I) by protecting the secondary amide nitrogen atom in the compound of formula (III) to obtain (IV) wherein PGN is a suitable nitrogen protecting group, ring-closing the compound of formula (IV) by cyclizing it in the presence of a suitable catalyst in a suitable organic solvent to obtain (V), and then deprotecting the resulting compound of formula (V) to obtain (I), as outlined in the following scheme. The compounds of formula (I) are active agents for the treatment of hepatitis C viral (HCV) infections or are intermediates useful for the preparation of anti-HCV agents.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: May 31, 2011
    Assignee: Boehringer Ingelheim International GmbH
    Inventor: Chutian Shu
  • Patent number: 7939628
    Abstract: An instrument and process for accelerating the solid phase synthesis of peptides is disclosed. The method includes the steps of deprotecting a protected first amino acid linked to a solid phase resin by admixing the protected linked acid with a deprotecting solution in a microwave transparent vessel while irradiating the admixed acid and solution with microwaves, then activating a second amino acid by adding the second acid and an activating solution to the same vessel while irradiating the vessel with microwaves, then coupling the second amino acid to the first acid while irradiating the composition in the same vessel with microwaves, and cleaving the linked peptide from the solid phase resin by admixing the linked peptide with a cleaving composition in the same vessel while irradiating the composition with microwaves.
    Type: Grant
    Filed: September 26, 2005
    Date of Patent: May 10, 2011
    Assignee: CEM Corporation
    Inventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
  • Publication number: 20110104063
    Abstract: A solid phase peptide synthesis method for synthesizing a peptidyl contrast agent is disclosed. In one example, the method includes synthesizing an amino-chelator loaded resin, coupling of the amino-chelator loaded resin to the C-terminus and/or backbone of a peptide, cleaving the amino-chelator-peptide from a resin, and chelating a lanthanide metal to the amino-chelator-peptide.
    Type: Application
    Filed: November 29, 2010
    Publication date: May 5, 2011
    Inventors: Mark D. Pagel, Byunghee Yoo
  • Patent number: 7897724
    Abstract: The present invention relates to an improved process for the preparation of N6-(aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-?-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1?6)-disulfide of formula (1), which involves assembling a peptide chain comprising of six amino acids and a thioalkyl carboxylic acid in a required sequence on a solid support to obtain a peptide bound resin of formula (2), capping the free amino groups after each coupling, cleaving Dde group in the peptide of formula (2) from the solid support to obtain peptide-solid support of formula (3), guanylating the peptide of formula (3) at ?-lysine-NH2 in an organic solvent to obtain peptide-solid support of formula (4), cleaving and deprotecting all groups in the peptide of formula (4) from the solid support to obtain peptide-amide formula (5), oxidizing the SH-peptide of formula (5) with an appropriate oxidizing agent to obtain the crude peptide-amide of formula (1) and purifying the crude peptide-amide of formula (1)
    Type: Grant
    Filed: March 27, 2007
    Date of Patent: March 1, 2011
    Assignee: USV, Ltd.
    Inventors: Divya Lal Saksena, Shrikant Mishra, Chandrakesan Muralidharan, Nilesh Patil, Nikhil Umesh Mohe, Mandar Ravindra Maduskar
  • Patent number: 7834141
    Abstract: Specially designed non-mammalian GnRH analogs resistant to degradation by the tumor tissue enzymes, post-proline peptidases as well as endopeptidases, are disclosed. The GnRH analogs are further defined as analogs of chicken II GnRH, salmon GnRH, or herring GnRH, but can include any non-mammalian GnRH analog with similar amino acid structure. These non-mammalian analogs incorporate D-arginine, D-leucine, D-tBu-Serine or D-Trp or other similar amino acids at position 6 and ethylamide or aza-Gly-amide or similar amides at position 10. These analogs demonstrate preferential binding to tumor cell GnRH receptors that is greater relative to the binding of the mammalian analogs to the tumor cell GnRH receptor. These non-mammalian GnRH analogs may be used in pharmaceutical preparations, and it specifically in various treatments as an anti-tumor, anti-proliferation, anti-metastatic and/or an apoptotic agent.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: November 16, 2010
    Inventors: Theresa Siler-Khodr, Gabriel S. Khodr
  • Patent number: 7803774
    Abstract: Compounds that modulate natural ? amyloid peptide aggregation are provided. The modulators of the invention comprise a peptide, preferably based on a ? amyloid peptide, that is comprised entirely of D-amino acids. Preferably, the peptide comprises 3-5 D-amino acid residues and includes at least two D-amino acid residues independently selected from the group consisting of D-leucine, D-phenylalanine and D-valine. In a particularly preferred embodiment, the peptide is a retro-inverso isomer of a ? amyloid peptide, preferably a retro-inverso isomer of A?17-21. In certain embodiments, the peptide is modified at the amino-terminus, the carboxy-terminus, or both. Preferred amino-terminal modifying groups alkyl groups. Preferred carboxy-terminal modifying groups include an amide group, an acetate group, an alkyl amide group, an aryl amide group or a hydroxy group.
    Type: Grant
    Filed: November 15, 2004
    Date of Patent: September 28, 2010
    Assignee: Praecis Pharmaceuticals, Inc.
    Inventors: Mark A. Findeis, Kathryn Phillips, Gary L. Olsen, Christopher Self
  • Publication number: 20100234564
    Abstract: The present invention relates to methods and intermediates for chemical synthesis of polypeptides and proteins, and more particularly to methods and intermediates for chemically ligating a peptide fragment containing N-terminal N-methyl-cysteine (SEQ ID NO: 1) with another peptide fragment having C-terminal thioester to generate a ?-(methylamino)-thioester intermediate that spontaneously rearranges to form an amide bond. Furthermore, the invention relates to methods of converting N-methyl-thiazolidine to N-methyl-cysteine (SEQ ID NO: 1) of polypeptides and proteins. The invention also relates to methods of synthesizing peptide-thioester from peptide-acid fluoride.
    Type: Application
    Filed: August 27, 2008
    Publication date: September 16, 2010
    Inventors: Zheng Xin Dong, John S. Eynon
  • Patent number: 7786259
    Abstract: The present invention provides a process for preparing an immobilized peptide derivative of formula (Vb): comprising reacting a functionalized solid support comprising Sub-L wherein Sub is a solid support and L is a cleavable linker, with H—[NH—A—C(O)]—O(tBu), then reacting the immobilized product with compound of the formula RHN—A—C(O)OH, wherein the RHN—A—C(O) group is the residue of a N-protected ?-amino acid, in the presence of a coupling agent, to yield an immobilized peptide derivative of the formula (Vb).
    Type: Grant
    Filed: July 13, 2007
    Date of Patent: August 31, 2010
    Assignee: The Curators of the University of Missouri
    Inventor: William G. Gutheil
  • Publication number: 20100184952
    Abstract: Method of removing dibenzofulvene and/or a dibenzofulvene amine adduct from a reaction mixture obtained by reacting an amino acid compound protected with an Fmoc group with an amine for deprotection, include stirring and partitioning the reaction mixture in a hydrocarbon solvent and a polar organic solvent, and removing a resulting hydrocarbon solvent layer in which the dibenzofulvene and/or the dibenzofulvene amine adduct is dissolved. The hydrocarbon solvent may have a carbon number of at least 5; the polar organic solvent may be free from organic amide solvents; and the polar organic solvent may immiscible with the hydrocarbon solvent.
    Type: Application
    Filed: January 25, 2010
    Publication date: July 22, 2010
    Applicant: AJINOMOTO CO., INC
    Inventor: Daisuke TAKAHASHI
  • Patent number: RE46707
    Abstract: The present disclosure provides variants of C-type natriuretic peptide (CNP), pharmaceutical compositions comprising CNP variants, and methods of making CNP variants. The CNP variants are useful as therapeutic agents for the treatment of diseases responsive to CNP, including but not limited to bone-related disorders, such as skeletal dysplasias (e.g., achondroplasia), and vascular smooth muscle disorders (e.g., restenosis and arteriosclerosis).
    Type: Grant
    Filed: January 23, 2015
    Date of Patent: February 13, 2018
    Assignee: BioMarin Pharmaceutical Inc.
    Inventors: Daniel J. Wendt, Shinong Long, Sianna Castillo, Christopher P. Price, Mika Aoyagi-Scharber, Michel Claude Vellard, Augustus O. Okhamafe