Of Side Chain Or Sulfur Containing Group Patents (Class 530/336)
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Patent number: 8981049Abstract: Improved methods of native chemical ligation are provided. The methods involve reacting a thioacid (e.g. a peptide thioacid) with an aziridinyl compound (e.g. an aziridinyl peptide) under mild conditions without the use of protecting groups, and without requiring that a cysteine residue be present in the ligation product. Initial coupling of the thioacid and the aziridinyl compound yields a ligation product which contains an aziridinyl ring. Subsequent opening of the aziridinyl ring (e.g. via a nucleophilic attack) produces a linearized and modified ligation product.Type: GrantFiled: November 13, 2012Date of Patent: March 17, 2015Assignee: Washington State UniversityInventor: Philip Garner
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Patent number: 8895696Abstract: Methods for building peptide chains containing sulfonyl modified amines at the N-terminus, or, within amino acid side chains, of a growing peptide in a solid-phase peptide synthesis are described. Further, compositions having a sulfonyl modified amine attached to the N-terminus, or within an amino acid side chain, of a polypeptide containing three or more amino acid residues are described.Type: GrantFiled: August 28, 2012Date of Patent: November 25, 2014Assignee: The University of ToledoInventors: Steven J. Sucheck, Rommel S. Talan, Partha Karmakar
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Patent number: 8729009Abstract: The present invention concerns new thiolysine and selenolysine compounds that can be used as building blocks for peptides and proteins, providing ligation handles for site- and chemoselective modification of said peptides and proteins. In particular, the invention provides. In particular, the invention provides (the use of) the compounds 5-thiolysine (also referred to as ?-thiolysine); 4-thiolysine (also referred to as ?-thiolysine); 5-selenolysine (also referred to as ?-selenolysine) and 4-selenolysine (also referred to as ?-selenolysine). The positioning of the thiol or selenol group at the respective carbon atom allows for a very efficient intramolecular transfer reaction to take place after conjugation with a selected ligand, and the thiol or selenol group may subsequently be removed using reported procedures, thereby restoring the native lysine structure, or be used as an additional conjugation handle. The methodology is fast and gives well-defined material.Type: GrantFiled: May 12, 2010Date of Patent: May 20, 2014Assignee: Stichting Het Nederlands Kanker InstituutInventors: Huib Ovaa, Farid El Oualid
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Patent number: 8729229Abstract: 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: GrantFiled: March 18, 2010Date of Patent: May 20, 2014Assignee: Sandoz AGInventors: Anup Kumar Ray, Hiren Kumar V. Patel, Johannes Ludescher, Mariappan Anbazhagan, Mahendra R. Patel, Ingolf Macher
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Patent number: 8592142Abstract: 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: GrantFiled: December 10, 2012Date of Patent: November 26, 2013Assignee: Momenta Pharmaceuticals, Inc.Inventors: Xiangping Zhu, Zachary Shriver, Yanjie Jiang, Corinne Bauer, James Eric Anderson, Peter James Ahern
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Patent number: 8551951Abstract: 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: GrantFiled: January 22, 2010Date of Patent: October 8, 2013Assignee: Aenorasis SA Pharmaceuticals and Medical DevicesInventors: Seema Garde, Chandra J. Panchal, Madhulika Baijal-Gupta, Jennifer Fraser, Salam Kadhim
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Patent number: 8536305Abstract: 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: GrantFiled: September 27, 2007Date of Patent: September 17, 2013Assignee: Sandoz AGInventors: Anup K Ray, Hiren V Patel, Johannes Ludescher, Mariappan Anbazhagan, Mahendra R Patel, Ingolf Macher
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Patent number: 8435956Abstract: The present invention provides compositions and methods for protecting cells and tissues from damage associated with therapeutic treatments of cancers and other diseases and conditions where reactive oxygen species are produced. The present invention also provides compositions useful as research reagents.Type: GrantFiled: May 11, 2012Date of Patent: May 7, 2013Assignee: Percitus Biosciences, LLCInventor: James P. Thomas
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Patent number: 8329391Abstract: 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: GrantFiled: March 20, 2009Date of Patent: December 11, 2012Assignee: Momenta Pharmaceuticals, Inc.Inventors: Xiangping Zhu, Zachary Shriver, Yanjie Jiang, Corinne Bauer, James Eric Anderson, Peter James Ahern
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Publication number: 20120157563Abstract: A solid phase peptide synthesis method is disclosed. The method includes the steps of deprotecting an amino group in its protected form that is protected with a protecting group that includes an ?,?-unsaturated sulfone; washing the deprotected acid in a solvent selected from the group consisting of water, alcohol, and mixtures of water and alcohol; coupling the deprotected acid to a resin-based peptide or a resin-based amino acid; and washing the coupled composition in a solvent selected from the group consisting of water, alcohol, and mixtures of water and alcohol.Type: ApplicationFiled: February 1, 2012Publication date: June 21, 2012Applicant: CEM CORPORATIONInventor: Jonathan M. Collins
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Publication number: 20120135913Abstract: The present invention concerns new thiolysine and selenolysine compounds that can be used as building blocks for peptides and proteins, providing ligation handles for site- and chemoselective modification of said peptides and proteins. In particular, the invention provides. In particular, the invention provides (the use of) the compounds 5-thiolysine (also referred to as ?-thiolysine); 4-thiolysine (also referred to as ?-thiolysine); 5-selenolysine (also referred to as ?-selenolysine) and 4-selenolysine (also referred to as ?-selenolysine). The positioning of the thiol or selenol group at the respective carbon atom allows for a very efficient intramolecular transfer reaction to take place after conjugation with a selected ligand, and the thiol or selenol group may subsequently be removed using reported procedures, thereby restoring the native lysine structure, or be used as an additional conjugation handle. The methodology is fast and gives well-defined material.Type: ApplicationFiled: May 12, 2010Publication date: May 31, 2012Inventors: Huib Ovaa, Farid El Oualid
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Patent number: 8058393Abstract: 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: GrantFiled: August 28, 2009Date of Patent: November 15, 2011Assignee: CEM CorporationInventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
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Patent number: 8058235Abstract: Methods of making copolymers are described.Type: GrantFiled: July 20, 2011Date of Patent: November 15, 2011Assignee: Momenta Pharmaceuticals, Inc.Inventors: Claire Coleman, John Schaeck, Alicia Thompson
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Patent number: 7994280Abstract: A novel compound of formula I is devised.Type: GrantFiled: October 18, 2005Date of Patent: August 9, 2011Assignee: Lonza AGInventors: Stéphane Varray, Oleg Werbitzky, Thomas Zeiter
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Publication number: 20110172392Abstract: The present invention provides a method for producing a peptide, characterized in that it comprises converting an —SH group of a peptide comprising an amino acid residue having the —SH group to an —OH group, wherein said method comprises the following steps (a) to (c): (a) allowing an —SH group in a peptide to react with a methylating agent to convert the —SH group to an —SMe group; (b) allowing the —SMe group obtained in the step (a) to react with a cyanizing agent to produce a reaction intermediate; and (c) converting the reaction intermediate obtained in the step (b) to a peptide comprising an amino acid residue having an —OH group under more basic conditions than the conditions in the step (b).Type: ApplicationFiled: July 30, 2008Publication date: July 14, 2011Applicant: OTSUKA CHEMICAL CO., LTD.Inventors: Yasuhiro Kajihara, Izumi Sakamoto, Yuri Nambu, Kazuhiro Fukae, Hiroaki Asai
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Patent number: 7939628Abstract: 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: GrantFiled: September 26, 2005Date of Patent: May 10, 2011Assignee: CEM CorporationInventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
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Patent number: 7897724Abstract: 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: GrantFiled: March 27, 2007Date of Patent: March 1, 2011Assignee: USV, Ltd.Inventors: Divya Lal Saksena, Shrikant Mishra, Chandrakesan Muralidharan, Nilesh Patil, Nikhil Umesh Mohe, Mandar Ravindra Maduskar
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Publication number: 20100210566Abstract: An azapeptide derivative of growth hormone releasing peptide (GHRP) of Formula I: A-(Xaa)a-N(RA)—N(RB)—C(O)-(Xaa?)b-B which binds to CD 36.Type: ApplicationFiled: June 18, 2008Publication date: August 19, 2010Applicant: INSERM (Institut National de la Sante et de la Recherche Medicale)Inventors: Huy Ong, Sylvain Chemtob, William Lubell, Florian Sennlaub, Damien Boeglin, Caroline Proulx, Zohreh Sajjadi, David Sabatino
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Publication number: 20100081788Abstract: The present invention provides for an efficient process for making Pramlinitide, as well as novel intermediates for the making of the same.Type: ApplicationFiled: September 3, 2009Publication date: April 1, 2010Applicant: ScinoPharm Taiwan Ltd.Inventors: Tsung Yu Hsiao, Jin Guc Ding
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Patent number: 7678766Abstract: The invention concerns a novel method for preparing an intermediate polyanion for preparing cyclosporin derivatives by treating a cyclosporin with a hexamethyldisilazane metal salt, optionally in the presence of a metal halide. The treated cyclosporin has one or several free hydroxy groups and/or non-methylated nitrogen atoms in position ? and/or any other acid group capable of deprotonation which are optionally deprotonated or in protected form.Type: GrantFiled: May 9, 2007Date of Patent: March 16, 2010Assignee: Aventis Pharma S.A.Inventor: Christian Viskov
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Publication number: 20100022749Abstract: According to the present invention, there is provided a range of new conotoxin derivatives and methods for synthesizing these analogues and other intramolecular dicarba bridge-containing peptides, including dicarba-disulfide bridge-containing peptides.Type: ApplicationFiled: May 20, 2009Publication date: January 28, 2010Applicants: MONASH UNIVERSITY, POLYCHIP PHARMACEUTICALS PTY LTD.Inventors: Andrea Robinson, Jomana Elaridi
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Patent number: 7645858Abstract: A method for synthesizing a given peptide or its derivative which contains a proline residue or a proline derivative, at proximity to, or at, the C-terminal end of said peptide is provided. The method comprises a) synthesizing on a first resin a C-terminal portion of said peptide, or its derivative, comprising at least three successive amino acid residues or their derivatives, by successive coupling of selected amino acids, small peptides or their derivatives; b) cleaving the C-terminal portion from said first resin; c) reattaching said C-terminal portion to a second resin which is generally suitable for the synthesis of peptides but is unsuitable for the formation of peptides having a proline residue positioned at the C-terminal end of said peptide; and d) coupling selected amino acids, small peptides or derivatives to the C-terminal portion.Type: GrantFiled: July 30, 2004Date of Patent: January 12, 2010Assignee: Almac Sciences (Scotland) LimitedInventor: Andrew Smith Johnstone Stewart
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Patent number: 7608687Abstract: A compound comprised of a hydrophilic polymer covalently yet reversibly linked to a amine-containing ligand through a dithiobenzyl linkage is described.Type: GrantFiled: September 19, 2007Date of Patent: October 27, 2009Assignee: Alza CorporationInventor: Samuel Zalipsky
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Patent number: 7592307Abstract: A conjugate comprised of a hydrophilic polymer covalently yet reversibly linked to a amine-, hydroxy- or carboxyl-containing ligand is described. The resulting conjugate is capable of releasing the parent amine, hydroxy, or carboxyl-containing compound via thiol-mediated cleavage. The system allows for delivery of various amino-, hydroxy-, or carboxy-containing drugs in the form of their thiolytically cleavable macromolecular conjugates.Type: GrantFiled: June 6, 2007Date of Patent: September 22, 2009Assignee: Alza CorporationInventors: Samuel Zalipsky, Radwan Kiwan
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Patent number: 7582728Abstract: An instrument and method 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: GrantFiled: June 23, 2008Date of Patent: September 1, 2009Assignee: CEM CorporationInventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
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Publication number: 20090215986Abstract: A solution phase synthetic method for preparing basic tripeptides of the formula Gly-Xaa-Gly-X which have in various biological properties such as stimulating protein production when used as additives in a bioreactor. The basic tripeptides of the invention may be produced on gram or kilogram scale.Type: ApplicationFiled: March 25, 2009Publication date: August 27, 2009Inventors: David Epstein, Marian F. Kruszynski, Christopher Marsh, Albert Schmidt
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Patent number: 7563865Abstract: 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: GrantFiled: September 26, 2005Date of Patent: July 21, 2009Assignee: CEM CorporationInventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
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Patent number: 7495072Abstract: The subject invention provides an improved process for obtaining a mixture of polypeptides having nonuniform amino acid sequences, where each polypeptide consists essentially of alanine, glutamic acid, tyrosine and lysine where the resulting mixture of polypeptides comprises less than 0.3% brominated tyrosine and less than 1000 ppm metal ion impurities.Type: GrantFiled: September 9, 2005Date of Patent: February 24, 2009Assignee: Teva Pharmaceutical Industries, Ltd.Inventor: Ben-Zion Dolitzky
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Patent number: 7488794Abstract: A method for producing a S-nitrosylated species is provided. The method comprises: (a) providing a deoxygenated, alkaline aqueous solution comprising a thiol and a nitrite-bearing species; (b) acidifying the solution by adding acid to the solution while concurrently mixing the solution (e.g., by vigorously stirring the solution) to produce the S-nitrosylated species; and (c) isolating the S-nitrosylated species. The nitrite-bearing species can be, for example, an inorganic nitrite, such as an alkali metal nitrite, or an organic nitrite, such as an alkyl nitrite (e.g., ethyl nitrite, amyl nitrite, isobutyl nitrite or t-butyl nitrite). The thiol is preferably a thiol-containing polysaccharide, a thiol-containing lipoprotein, a thiol-containing amino acid or a thiol-containing protein, and more preferably a thiol-containing polysaccharide such as thiolated cyclodextrin. In many preferred embodiments, the S-nitrosylated species is insoluble in the acidified solution, precipitating upon formation.Type: GrantFiled: June 30, 2004Date of Patent: February 10, 2009Assignee: Boston Scientific Scimed, Inc.Inventors: Robert A. Herrmann, David Knapp
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Patent number: 7425608Abstract: Method of making metallopeptides is provided, for use in biological, pharmaceutical and related applications. The metallopeptides are made of peptides, peptidomimetics and peptide-like constructs, and include a metal ion-binding region thereof which includes at least one orthogonal sulfur-protecting group, in which the peptide, peptidomimetic or construct is conformationally fixed on deprotection of the sulfur and complexation of the metal ion-binding region with a metal ion while the peptide, peptidomimetic or construct is cleavably bound to solid phase.Type: GrantFiled: September 7, 2005Date of Patent: September 16, 2008Assignee: Palatin Technologies, Inc.Inventors: Shubh D. Sharma, Yi-Qun Shi
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Publication number: 20080171849Abstract: A novel method for side chain cyclisation of peptides by means of lactamization is provided.Type: ApplicationFiled: September 20, 2005Publication date: July 17, 2008Inventors: Matthieu Giraud, Oleg Werbitzky, Michaela Williner
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Patent number: 7393920Abstract: 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: GrantFiled: June 23, 2003Date of Patent: July 1, 2008Assignee: CEM CorporationInventors: Jonathan McKinnon Collins, Joseph Joshua Lambert, Michael John Collins
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Publication number: 20080026995Abstract: The invention relates to conjugates comprising all or part of the amino acid sequences of at least one peptide derived from an extracellular loop of the P-170 protein. The peptide may be covalently attached to spacers which may be polyethyleneglycol (PEG), polyglycine, polylysine or any polymer chain suitable for human use and is coupled at its free end to a phospholipids, e.g., phosphatidylethanolamine or any other chemically suitable phospholipid.Type: ApplicationFiled: October 18, 2006Publication date: January 31, 2008Applicant: AC IMMUNE SAInventors: Pierre-Francois Tosi, Claudie Madoulet, Yves-Claude Nicolau, David T. Hickman
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Patent number: 7301006Abstract: Methods and protected amino acids useful as building blocks (protected monomers) for the synthesis of peptides and proteins that are selectively modified at one or more side-chain hydroxyl groups. Azide-bearing protecting groups allow the selective deprotection of side-chain hydroxyl groups of amino acids after synthesis of a peptide. Reaction conditions for removal of the azide-bearing protecting group can be selected which are substantially orthogonal to those that will remove ?-amino protecting groups typically employed in peptide synthesis, such that hydroxyl groups protected with the azide-bearing protecting group remain protected during synthesis of the peptide chain. Various protecting groups which are readily available can be used for protecting potentially reactive side chain groups of amino acids in the peptide or protein to be modified.Type: GrantFiled: July 16, 2003Date of Patent: November 27, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Travis G. Young, Laura L. Kiessling
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Patent number: 7285622Abstract: A compound comprised of a hydrophilic polymer covalently yet reversibly linked to a amine-containing ligand through a dithiobenzyl linkage is described.Type: GrantFiled: January 14, 2005Date of Patent: October 23, 2007Assignee: Alza CorporationInventor: Samuel Zalipsky
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Patent number: 7276248Abstract: Conjugates of a hydrophobic moiety, such as a lipid, linked through a cleavable dithiobenzyl linkage to a therapeutic agent are described. The dithiobenzyl linkage is susceptible to cleavage by mild thiolysis, resulting in release of the therapeutic agent in its original form. The linkage is stable under nonreducing conditions. The conjugate can be incorporated into liposomes for administration in vivo and release of the therapeutic agent in response to endogeneous in vivo reducing conditions or in response to administration of an exogeneous reducing agent.Type: GrantFiled: August 12, 2005Date of Patent: October 2, 2007Assignee: ALZA CorporationInventors: Samuel Zalipsky, Alberto A. Gabizon
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Patent number: 7247701Abstract: Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.Type: GrantFiled: September 14, 2005Date of Patent: July 24, 2007Assignee: University of Southern CaliforniaInventors: Nicos A. Petasis, Xin Yao
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Patent number: 7238368Abstract: A conjugate comprised of a hydrophilic polymer covalently yet reversibly linked to a amine-, hydroxy- or carboxyl-containing ligand is described. The resulting conjugate is capable of releasing the parent amine, hydroxy, or carboxyl-containing compound via thiol-mediated cleavage. The system allows for delivery of various amino-, hydroxy-, or carboxy-containing drugs in the form of their thiolytically cleavable macromolecular conjugates.Type: GrantFiled: November 26, 2003Date of Patent: July 3, 2007Assignee: ALZA CorporationInventors: Samuel Zalipsky, Radwan Kiwan
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Patent number: 7226905Abstract: The invention concerns a novel method for preparing an intermediate polyanion for preparing cyclosporin derivatives by treating a cyclosporin with a hexamethyldisilazane metal salt, optionally in the presence of a metal halide. The treated cyclosporin has one or several free hydroxy groups and/or non-methylated nitrogen atoms in position ? and/or any other acid group capable of deprotonation which are optionally deprotonated or in protected form.Type: GrantFiled: December 22, 2000Date of Patent: June 5, 2007Assignee: Aventis Pharma S.A.Inventor: Christian Viskov
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Patent number: 7192713Abstract: The present invention provides novel stabilized crosslinked compounds having secondary structure motifs, libraries of these novel compounds, and methods for the synthesis of these compounds libraries thereof. The synthesis of these novel stabilized compounds involves (1) synthesizing a peptide from a selected number of natural or non-natural amino acids, wherein said peptide comprises at least two moieties capable of undergoing reaction to promote carbon-carbon bond formation; and (2) contacting said peptide with a reagent to generate at least one crosslinker and to effect stabilization of a secondary structure motif. The present invention, in a preferred embodiment, provides stabilized p53 donor helical peptides. Additionally, the present invention provides methods for disrupting the p53/MDM2 binding interaction comprising (1) providing a crosslinked stabilized ?-helical structure; and (2) contacting said crosslinked stabilized ?-helical structure with MDM2.Type: GrantFiled: May 18, 2000Date of Patent: March 20, 2007Assignee: President and Fellows of Harvard CollegeInventors: Gregory L. Verdine, Christian E. Schafmeister
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Patent number: 7138489Abstract: The present invention is a method for producing a peptide or a protein in which a side chain contains a modified amino acid residue, which comprises chemically producing a peptide fragment containing an amino acid residue having a modified side chain using an weak acid-cleavable resin, producing a peptide fragment containing no amino acid residue having a modified side chain using a genetic recombination method or/and an enzymatic method, and condensing the resulting two kinds of peptide fragments and, according to the present invention, a peptide or a protein containing modification such as acylation, glycosylation and phosphorylation can be obtained effectively and at high quality.Type: GrantFiled: April 10, 2003Date of Patent: November 21, 2006Assignee: Daiichi Asubio Pharma Co., Ltd.Inventors: Yoshiharu Minamitake, Masaru Matsumoto, Tomohiro Makino
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Patent number: 7094580Abstract: A method of perlecan isolation (from the EHS tumor) which produces “clean” (i.e. substantially “pure”) perlecan is disclosed. Clean perlecan is thus produced in sufficient quantities for use in a number of different in vitro and in vivo assays. In addition, this isolation method exploits a newly discovered aggregating property of a ˜220 kDa heparan sulfate proteoglycan (HSPG) observed during gel filtration chromatography, which allows it to be effectively separated from non-aggregating perlecan. The method employs specific cation exchange, anion exchange, molecular sieve chromatography and immobilized GAG affinity chromatography. It is demonstrated that there are no other contaminating proteins in the perlecan and HSPG preparations, and that the perlecan core protein is intact. Improved, clean perlecan based, rodent models of fibrillar amyloid protein deposition, accumulation and/or persistence in tissues are disclosed.Type: GrantFiled: December 18, 2002Date of Patent: August 22, 2006Assignee: University of WashingtonInventors: Gerardo Castillo, Alan D. Snow
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Patent number: 7049399Abstract: A process for the preparation of a polypeptide designated in the present invention as 1, composed of the following amino acid units in the structure, namely: L-alanine, L-glutamic acid, L-lysine and L-tyrosine randomly arranged in the polypeptide 1, or pharmaceutically acceptable salts thereof, comprising the steps of: (a) polymerization of a mixture of the N-carboxyanhydrides of L-alanine, L-tyrosine, a protected L-glutamate and a protected L-lysine to obtain protected copolymer 6 or salt thereof; (b) deprotection of the protected copolymer 6 (or salt thereof) to produce polypeptide 1 or a pharmaceutically acceptable salt thereof in one single step; (c) separation and purification of the polypeptide 1 (or a pharmaceutically acceptable salt) to obtain a purified polypeptide 1Type: GrantFiled: December 24, 2002Date of Patent: May 23, 2006Assignee: Apotex Pharmachem Inc.Inventors: Elena Bejan, Gamini Weeratunga, Stephen E. Horne
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Patent number: 7045503Abstract: Novel metal binding ligands are disclosed that may be coupled to peptides for use in methods of diagnosis and therapy. Peptides containing the ligands are produced using a method wherein ligand introduction or cyclization can be conducted at any point during the synthesis of the peptide. Such peptide derivatives are readily labeled with radiometals, such as isotopes of rhenium or technetium, while retaining their ability to tightly bind specific peptide receptors.Type: GrantFiled: October 2, 2000Date of Patent: May 16, 2006Assignee: Immunomedics, Inc.Inventors: William J. McBride, Gary L. Griffiths
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Patent number: 7019113Abstract: An process for the reversible modification of membrane interaction of a compound is described. Modification of membrane interaction can be used to facilitate delivery of molecules to cells in vitro and in vivo. The described modifiers, which are used to reversibly inactivate the membrane active compounds, can also be utilized as cross-linkers or to reverse the charge of a molecule.Type: GrantFiled: May 23, 2003Date of Patent: March 28, 2006Assignee: Mirus Bio CorporationInventors: David B. Rozema, Darren Wakefield, Jon A. Wolff, Kirk Ekena, James E. Hagstrom
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Patent number: 6995136Abstract: A peptide factor, its analogs and methods of using such peptide factor derived from murine epidermal growth factor peptide is disclosed wherein the peptide factor is modified to protect it from proteolytic degradation and the peptide binds to laminin receptors.Type: GrantFiled: April 21, 1999Date of Patent: February 7, 2006Assignee: The Queen's University of BelfastInventors: John Nelson, Brian Walker, Neil McFerran, Patrick Harriott
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Patent number: 6946542Abstract: Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.Type: GrantFiled: April 1, 2003Date of Patent: September 20, 2005Assignee: University of Southern CaliforniaInventors: Nicos A. Petasis, Xin Yao
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Patent number: 6921636Abstract: The invention provides apparatus and methods for determining the nucleotide sequence of target nucleic acids using hybridization to arrays of oligonucleotides. The invention further provides apparatus and methods for identifying the amino acid sequence of peptides that bind to biologically active macromolecules, by specifically binding biologically active macromolecules to arrays of peptides or peptide mimetics.Type: GrantFiled: November 16, 2000Date of Patent: July 26, 2005Assignee: Metrigen, Inc.Inventor: Thomas M. Brennan
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Patent number: 6906171Abstract: The synthesis of peptides comprising disulphide bridges is challenging since it is difficult to ensure that the correct cysteine residues combine to form the desired disulphide bridges. The present invention describes novel protection techniques useful in the preparation of peptides. Described is a process for the deprotection of an Acm-, MBzl- and/or tBu-protected thiol which comprises reacting said protected thiol with an acid in the presence of an oxidising agent at a temperature sufficient to effect deprotection and generation of disulphide bonds.Type: GrantFiled: January 18, 2002Date of Patent: June 14, 2005Assignee: Amersham Health ASInventor: Alan Cuthbertson
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Patent number: 6849270Abstract: A compound comprised of a hydrophilic polymer covalently yet reversibly linked to a amine-containing ligand through a dithiobenzyl linkage is described.Type: GrantFiled: February 21, 2003Date of Patent: February 1, 2005Assignee: Alza CorporationInventor: Samuel Zalipsky