With Phosphorus Containing Material Patents (Class 530/340)
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Patent number: 8877892Abstract: We describe methods that allow either carbodiimides or other carboxyl-reactive substances to be mixed with solutions of carboxylic acids or phosphates or amines or combinations thereof, so as to form a homogeneous mixture which is then dried, preferably in a freeze drying process. The mixture is then contacted with an entity, which preferably involves the dissolution of the mixture with a buffered solution of the entity, so as to initiate a conjugation reaction between the entity and a component in the mixture.Type: GrantFiled: March 15, 2011Date of Patent: November 4, 2014Assignee: Innova Biosciences LimitedInventors: Nicholas Gee, Annamaria Draghi
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Patent number: 8765673Abstract: The present invention provides methods for promoting wound healing and/or reducing scar formation, by administering to an individual in need thereof one or more of the heat shock protein 20-derived polypeptides disclosed herein.Type: GrantFiled: January 4, 2012Date of Patent: July 1, 2014Assignee: Arizona Board of RegentsInventors: Colleen Brophy, Alyssa Panitch, Catherine Parmiter, Elizabeth Furnish, Padmini Komalavilas
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Patent number: 8410247Abstract: Water soluble reagents and methods for the formation of an amide bond between a phosphinothioester and an azide in an aqueous medium. The phosphinothioester is generated using a water-soluble phosphinothiol reagent. This reaction allows formation of an amide bond between a wide variety of chemical species including amino acids, peptides or protein fragments in an aqueous solution. Of particular interest, this reaction allows for the formation of an amide bond in a physiological setting. In a specific embodiment, this invention provides reagents and methods for peptide ligation in an aqueous medium. The reaction eliminates the need for a cysteine residue and is traceless leaving no residual atoms in the ligated peptide product.Type: GrantFiled: August 24, 2009Date of Patent: April 2, 2013Assignee: Wisconsin Alumni Research FoundationInventors: Ronald T. Raines, Annie Tam, Matthew B. Soellner
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Patent number: 7871786Abstract: The present invention relates to diagnosing abnormal cell proliferation in biological samples and screening for drugs which inhibit, reduce or abolish cell growth, especially tumorigenic cell growth, by detecting a phosphovariant isoform of a guanine nucleotide exchange factor biomarker, such as the novel GEF-H1S.Type: GrantFiled: September 11, 2008Date of Patent: January 18, 2011Assignee: Sugen, Inc.Inventors: Tod R. Smeal, Marinella G. Callow, Bahija Jallal, Sergey Zozulya, Mikhail L. Gishizky
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Publication number: 20100048866Abstract: Water soluble reagents and methods for the formation of an amide bond between a phosphinothioester and an azide in an aqueous medium. The phosphinothioester is generated using a water-soluble phosphinothiol reagent. This reaction allows formation of an amide bond between a wide variety of chemical species including amino acids, peptides or protein fragments in an aqueous solution. Of particular interest, this reaction allows for the formation of an amide bond in a physiological setting. In a specific embodiment, this invention provides reagents and methods for peptide ligation in an aqueous medium. The reaction eliminates the need for a cysteine residue and is traceless leaving no residual atoms in the ligated peptide product.Type: ApplicationFiled: August 24, 2009Publication date: February 25, 2010Inventors: Ronald T. Raines, Annie Tam, Matthew B. Soellner
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Patent number: 7642339Abstract: The invention is related to phosphorus substituted anti-viral inhibitory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.Type: GrantFiled: July 18, 2005Date of Patent: January 5, 2010Assignee: Gilead Sciences, Inc.Inventors: Kleem Chaudhary, Melissa Fleury, Choung U. Kim, Darren J. McMurtrie, Xiaoning C. Sheng
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Patent number: 7494654Abstract: The present invention provides for methods of treating cardiovascular diseases in a mammal. The methods include a step of administering an effective amount of a botulinum toxin directly to a blood vessel of a mammal thereby treating a cardiovascular disease.Type: GrantFiled: June 16, 2004Date of Patent: February 24, 2009Assignee: Allergan, Inc.Inventors: Gregory F. Brooks, Stephen Donovan
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Patent number: 7439329Abstract: The present invention relates to diagnosing abnormal cell proliferation in biological samples and screening for drugs which inhibit, reduce or abolish cell growth, especially tumorigenic cell growth, by detecting a phosphovariant isoform of a guanine nucleotide exchange factor biomarker, such as the novel GEF-H1S.Type: GrantFiled: July 2, 2003Date of Patent: October 21, 2008Assignee: Sugen, Inc.Inventors: Tod R. Smeal, Marinella G. Callow, Bahija Jallal, Sergey Zozulya, Mikhail L. Gishizky
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Publication number: 20080213827Abstract: The present invention provides a process for producing a dipeptide or a dipeptide derivative by using a protein having the activity to form the dipeptide or dipeptide derivative from one or more kinds of amino acids or amino acid derivatives, or a culture of cells having the ability to produce the protein or a treated matter of the culture as a enzyme source, which comprise; allowing the enzyme source, one or more kinds of amino acids or amino acid derivatives and ATP to be present in an aqueous medium; allowing the dipeptide or dipeptide derivative to form and accumulate in the medium; and recovering the dipeptide or dipeptide derivative from the medium.Type: ApplicationFiled: June 24, 2005Publication date: September 4, 2008Inventors: Shin-ichi Hashimoto, Hajime Ikeda, Kazuhiko Tabata
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Patent number: 7342095Abstract: The subject invention concerns compositions and methods for blocking cancer cell growth or proliferation and/or inducing cancer cell death. Compositions of the present invention are peptidomimetics that inhibit STAT function. Peptidomimetics of the invention include compounds of the formula RY*L (where Y* represents phosphotyrosine), with the R group at the Y-1 position. Peptidomimetics of the invention disrupt Stat3 activation and function. Peptidomimetics of the invention significantly inhibit tumor cell growth and induce tumor cell death.Type: GrantFiled: February 20, 2004Date of Patent: March 11, 2008Assignee: University of South FloridaInventors: James Turkson, Richard Jove, Said M. Sebti, Andrew D. Hamilton
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Patent number: 7223399Abstract: The present invention provides for methods of treating cardiovascular diseases in a mammal. The methods include a step of administering an effective amount of a botulinum toxin directly to a blood vessel of a mammal thereby treating a cardiovascular disease.Type: GrantFiled: February 1, 2006Date of Patent: May 29, 2007Assignee: Allergan, Inc.Inventors: Gregory F. Brooks, Stephen Donovan
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Patent number: 7026167Abstract: The present invention relates to a method of applying mass spectrometry to analyzing peptides or proteins, especially in the proteome setting. More particularly, the invention relates to a mass spectrometry-based method for detection of protein/peptide phosphorylation wherein the side chains of glutamic acid and/or aspartic acid residues of said peptides or proteins are chemically modified as to improve the selectivity/efficiency of identification of the phosphorylated protein/peptide.Type: GrantFiled: December 26, 2002Date of Patent: April 11, 2006Assignee: University of Virginia Patent FoundationInventors: Donald F. Hunt, Forest M. White, Scott Ficarro
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Patent number: 6972320Abstract: Methods and reagents for the formation of amide bonds between an activated carboxylic acid derivative and an azide useful in the synthesis of peptides, proteins and derivatized or labeled amino acids, peptide or proteins. The method involves the formation of a phosphinothioester which reacts with an azide resulting in amide formation. The invention provides phosphinothiol reagents which convert activated carboxylic acid derivatives to phosphinothioesters which then react with azides to form an amide bond. The methods and reagents of the invention can be used for stepwise synthesis of peptides on solid supports or for the ligation to two or more amino acids, two or more peptide or two or more protein fragments.Type: GrantFiled: May 11, 2001Date of Patent: December 6, 2005Assignee: Wisconsin Alumni Research FoundationInventors: Ronald T. Raines, Laura L. Kiessling, Bradley L. Nilsson
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Patent number: 6482797Abstract: The invention relates to peptide derivatives that can be used as selective inhibitors of the N-terminal site of human angiotensin-converting enzyme. The derivatives comprise the amino acid sequence with the following formula: -Asp-Phe-&PSgr;(PO2CH2)-Ala-Xaa′- (I) wherein: &PSgr;(PO2CH2) indicates that the peptide bond (CONH) between Phe and Ala has been replaced by the phosphonic bond PO2CH2, and Xaa′ represents an amino acid residue. They can be used in pharmaceutical formulations, particularly to protect haematopoietic strain cells of patients undergoing aggressive chemotherapy or radiotherapy treatment.Type: GrantFiled: January 30, 2001Date of Patent: November 19, 2002Assignees: Commissariat A l'Energie Atomique, Institut National de la Sante et de la Recherche Medicale InsermInventors: Vincent Dive, Joël Cotton, Philippe Cuniasse, Athanasios Yiotakis, Pierre Corvol, Annie Michaud, Marie-Thérèse Chauvet, Joël Menard, Eric Ezan
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Patent number: 6369194Abstract: The invention relates to compounds of formula where R is a structural diversity element selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, peptidyl, heteroatom-substituted alkyl, cycloalkyl, and amines; and Nu is a structural diversity element derived from a nucleophile, NuH, selected from the group consisting of amines, amino acids, peptide, water, hydrogen sulfide, alcohols, and thiols. The invention also relates to arrays and combinatorial libraries of such compounds, and to a method of preparing such compounds.Type: GrantFiled: November 9, 1998Date of Patent: April 9, 2002Assignee: Yale UniversityInventor: Harry H. Wasserman
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Patent number: 6204361Abstract: The present invention relates to a process for forming an N-&agr;-amino protected amino acid fluoride in situ by reacting an N-&agr;-amino protected amino acid with an ionic fluoride salt in the presence of a peptide coupling agent. It is also directed to the use of the amino acid fluoride thus formed in peptide synthesis.Type: GrantFiled: November 25, 1998Date of Patent: March 20, 2001Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Dumitru Ionescu
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Patent number: 5854391Abstract: A method for synthesizing glycosylated peptides employs a blocked carbohydrate donor and a blocked peptide acceptor. The carbohydrate donor includes an acid labile phosphite leaving group attached to the anomeric carbon. The blocked peptide acceptor includes an unprotected hydroxyl group susceptible to electrophilic attack. Serine hydroxyl is preferred. The reaction is initiated by the addition of a Lewis acid so as to activate the acid labile phosphite leaving group on the carbohydrate donor. The substitution reaction may be conducted at -78.degree. C. in a solvent such as Et.sub.3 N which favors the formation of glycosylated peptide products.Type: GrantFiled: March 18, 1993Date of Patent: December 29, 1998Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Hirosato Kondo
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Patent number: 5834588Abstract: The invention is directed to systematic synthetic and testing strategies for .alpha.-keto acids, esters and amides. The method of synthesis comprises (A) reacting (cyanomethylene)triphenylphosphorane with a carbonyl compound selected from carboxylic acids (RCOOH) and acyl chlorides (RCOCl) to make a cyano keto phosphorane, (B) oxidizing said phosphorane and (C) reacting the oxidized product with a nucleophile (NuH) to make the product .alpha.-keto acid, ester or amide. Systematic synthesis and testing are achieved by a modular approach in which arrays of molecules are generated by variation of R and Nu.Type: GrantFiled: July 14, 1995Date of Patent: November 10, 1998Assignee: Yale UniversityInventors: Harry H. Wasserman, Wen-Bin Ho
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Patent number: 5830985Abstract: A process for preparing polyaspartic acid by polycondensation of fine-particle aspartic acid at temperatures above 150.degree. C. in the presence of acidic catalysts, wherein first contact between the acidic catalysts and the fine-particle aspartic acid takes place in the reaction zone where the polycondensation takes place.Type: GrantFiled: February 12, 1997Date of Patent: November 3, 1998Assignee: BASF AktiengesellschaftInventors: Matthias Kroner, Gunnar Schornick, Hans-Jacob Feindt, Thomas Meyer, Alfons Ludwig, Udo Metzmann
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Patent number: 5777077Abstract: A method for removing an allyl protecting group from an allyl-protected derivative of a biologically relevant amino acid is disclosed. One relevant aspect of the method is the use of soluble organometallic catalyst, such as an organopalladium catalyst. Preferably, soluble tetrakistriphenylphosphine palladium (0) is used. The allyl deprotection method now disclosed is suitable for use on an instrument for automated peptide synthesis. Methods of preparing the soluble organometallic catalyst are also disclosed, as are soluble catalyst compositions.Type: GrantFiled: February 20, 1997Date of Patent: July 7, 1998Assignee: PerSeptive Biosystems, Inc.Inventors: Fernando Albericio, Steven A. Kates
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Patent number: 5698675Abstract: This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: ##STR1## and N-oxides thereof and salts thereof.Type: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Assignee: Research Corporation Tech., Inc.Inventor: Louis A. Carpino
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Patent number: 5665603Abstract: A method of forming a thiohydantoin from an N-protected amino acid is described. The method employs a phosphate compound selected from the group consisting of(R.sub.1 O)(R.sub.2 O)P(.dbd.O)X and(R.sub.1 O)(R.sub.2 O)P(.dbd.O)--O--P(.dbd.O)(OR.sub.3)(OR.sub.4)to form acylphosphate moieties from the carboxyl groups of internal aspartic acid and glutamic acid residues and an acylphosphate moiety at a C-terminal carboxyl. The later acylphosphate, unlike the internal acylphosphates, spontaneously cyclizes to an oxazolone, which is less reactive with nucleophilic reagents. R.sub.1 and R.sub.2 are each alkyl, aryl, or alkaryl groups which are the same or different and which may be covalently linked to each other; R.sub.3 and R.sub.4 are each alkyl, aryl, or alkaryl groups which are the same or different and which may be covalently linked to each other; and X is a leaving group, such as chlorine or bromine, which is substantially unreactive towards thiohydantoins.Type: GrantFiled: July 8, 1994Date of Patent: September 9, 1997Assignee: The Perkin-Elmer CorporationInventors: Victoria L. Boyd, MeriLisa Bozzini, Robert J. DeFranco
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Patent number: 5644028Abstract: A process for producing peptide derivatives of formula (1) or salts thereof: ##STR1## which comprises condensation of peptide derivative of formula (2): ##STR2## with carboxylic acid of formula (3): ##STR3## or condensation of a peptide derivative of formula (4): ##STR4## with a protected amino acid of formula (5'): ##STR5## wherein R.sup.1 and R.sup.2 are a lower alkyl group or hydrogen atom, R.sup.3 is a lower alkyl group, X is a methylthiomethyl, methanesulfonylmethyl, carbamoylmethyl, or a lower alkyl group, Ar is an aryl or heteroaryl group, and A.sup.4 is Ar--O--CH.sub.2 --CO. The peptide derivatives and salts thereof are useful as the human immunodeficiency virus (HIV) protease inhibitors.Type: GrantFiled: December 28, 1994Date of Patent: July 1, 1997Assignee: Japan Energy CorporationInventors: Tsutomu Mimoto, Sumitsugu Kisanuki, Osamu Takahashi, Yoshiaki Kiso
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Patent number: 5644029Abstract: This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: ##STR1## and N-oxides thereof and salts thereof.Type: GrantFiled: June 6, 1995Date of Patent: July 1, 1997Assignee: Research Corporation Technologies, Inc.Inventor: Louis A. Carpino
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Patent number: 5306781Abstract: Activated carboxylic acid modified polyethylene membranes useful in the C-terminal sequencing of a peptide are disclosed. The membranes comprise activated carboxylic acid modified polyethylene having a linker coupled to an amide linkage to the surface carboxyl radicals of the membrane. Activation is accomplished by reaction of the carboxylic acid modified polyethylene membrane with DCC, CDI, EDC, BOP, DICD or 2-fluoro-1-methyl pyridine.Type: GrantFiled: March 26, 1993Date of Patent: April 26, 1994Assignee: City of HopeInventor: Jerome M. Bailey
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Patent number: 5191065Abstract: A process for the preparation of tripeptides of the general formula IU-A-B-C-OH Iin which U denotes hydrogen or a urethane protective group and A, B and C denote amino acids, by reaction of a compound of the general formula IIU'-B-OH IIin which U' is a urethane protective group which can be eliminated by hydrogenolysis, with a compound of the general formula IIIH-C-OR IIIin which R denotes alkyl, by the PPA method, elimination of U', and reacting the resulting compound of the formula IVH-B-C-OR IVwith a compound of the formula VU-A-OH Vin the presence of propylphosphonic anhydride, and finally eliminating R enzymatically.Type: GrantFiled: July 8, 1991Date of Patent: March 2, 1993Assignee: Hoechst AktiengesellschaftInventors: Hans-Wolfram Flemming, Manfred Rukwied, Manfred Schmidt
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Patent number: 5068351Abstract: The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which n is 1 or 2, R denotes hydrogen or an organic radical, R.sup.1 denotes an organic radical, R.sup.2 and R.sup.3 are identical or different and denote hydrogen or an organic radical, and R.sup.4 and R.sup.5, together with the atoms bearing them, form a monocyclic, bicyclic or tricyclic heterocyclic ring system having 5 to 15 carbon atoms, which process comprises reacting compounds of the formula II defined in the description with compounds of the formula IV defined in the description, in the presence of phosphinic anhydrides of the formula III, where appropriate eliminating radicals which have been introduced to protect other functional groups and, where appropriate, esterifying free carboxyl groups in a manner known per se.Type: GrantFiled: July 27, 1990Date of Patent: November 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Volker Teetz, Hans Wissmann, Hansjorg Urbach
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Patent number: 5055591Abstract: The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which n is 1 or 2, R denotes hydrogen or an organic radical, R.sup.1 denotes an organic radical, R.sup.2 and R.sup.3 are identical or different and denote hydrogen or an organic radical, and R.sup.4 and R.sup.5, together with the atoms bearing them, form a monocyclic, bicyclic or tricyclic heterocyclic ring system having 3 to 15 carbon atoms, which process comprises reacting compounds of the formula II defined in the description with compounds of the formula III defined in the description, in the presence of alkanephosphonic anhydrides, where appropriate eliminating radicals which have been introduced to protect other functional groups and, where appropriate, esterifying free carboxyl groups in a manner known per se.Type: GrantFiled: March 23, 1988Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Hansjorg Urbach, Rainer Henning, Hans Wissmann, Volker Teetz
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Patent number: RE37686Abstract: This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: and N-oxides thereof and salts thereof.Type: GrantFiled: December 3, 1998Date of Patent: April 30, 2002Assignee: Research Corporation Technologies, Inc.Inventor: Louis A. Carpino
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Patent number: RE38073Abstract: This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: and N-oxides thereof and salts thereof.Type: GrantFiled: June 30, 1999Date of Patent: April 8, 2003Assignee: Research Corporations Technologies, Inc.Inventor: Louis A. Carpino