Mixed Anhydride Synthesis Patents (Class 530/342)
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Patent number: 8455619Abstract: The present invention provides improved methods for the synthesis of polypeptide or peptide-linked compounds via a NCA-based polymerization reaction that produces high product yields in much less time. Such improved methods are achieved by application of a higher temperature and/or reduced pressure to the reaction such that an NCA-containing monomer melts.Type: GrantFiled: November 23, 2009Date of Patent: June 4, 2013Inventor: Keith R. Latham
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Publication number: 20100130723Abstract: The present invention provides improved methods for the synthesis of polypeptide or peptide-linked compounds via a NCA-based polymerization reaction that produces high product yields in much less time. Such improved methods are achieved by application of a higher temperature and/or reduced pressure to the reaction such that an NCA-containing monomer melts.Type: ApplicationFiled: November 23, 2009Publication date: May 27, 2010Applicant: Innovative Technologies, L.C.C.Inventor: Keith R. LATHAM
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Patent number: 6448378Abstract: Disclosed herein are collagen films which rapidly dissolve at 35° C. Also disclosed are methods for the preparation of the collagen films and their use as a vehicle for delivering a dose of therapeutic compound to a specific tissue site.Type: GrantFiled: December 12, 2000Date of Patent: September 10, 2002Inventors: Dale P. DeVore, Richard A. Eiferman, Edwin U. Keates
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Patent number: 6376649Abstract: Methods for the synthesis of &agr;-hydroxy-&bgr;-amino acid and amide derivatives and &agr;-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting a N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-&agr;-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl &agr;-ketoamides and &agr;-hydroxy-&bgr;-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.Type: GrantFiled: December 18, 1998Date of Patent: April 23, 2002Assignee: Corvas International, Inc.Inventors: Joseph E. Semple, Odile E. Levy
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Patent number: 6254986Abstract: A method for modifying a protein or polypeptide is disclosed which includes the steps of dispersing a protein or polypeptide in an essentially non-aqueous medium and peracylating the protein or polypeptide with a cyclic anhydride having a carbon chain substituent selected from the group consisting of alkyl and alkenyl groups. Most preferably, the cyclic anhydride is succinic anhydride, although glutaric anhydride may also be employed. Preferably, the step of peracylating the protein or polypeptide is performed in the presence of an acid catalyst, most preferably &rgr;-toluene sulfonic acid. The resultant modified protein or polypeptide may be employed in numerous applications including drug delivery, absorbable sutures, and thermoplastic films and molded articles.Type: GrantFiled: June 14, 2000Date of Patent: July 3, 2001Assignee: Poly-Med, Inc.Inventors: Shalaby W. Shalaby, Jacqueline M. Allan, Joel T. Corbett
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Patent number: 6197934Abstract: Disclosed herein are collagen films which rapidly dissolve at 35° C. Also disclosed are methods for the preparation of the collagen films and their use as a vehicle for delivering a dose of therapeutic compound to a specific tissue site.Type: GrantFiled: May 22, 1998Date of Patent: March 6, 2001Assignee: Collagenesis, Inc.Inventors: Dale P. DeVore, Richard A. Eiferman, Edwin U. Keates
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Patent number: 6162895Abstract: A method for modifying a protein or polypeptide is disclosed which includes the steps of dispersing a protein or polypeptide in an essentially non-aqueous medium and peracylating the protein or polypeptide with a cyclic anhydride having a carbon chain substituent selected from the group consisting of alkyl and alkenyl groups. Most preferably, the cyclic anhydride is succinic anhydride, although glutaric anhydride may also be employed. Preferably, the step of peracylating the protein or polypeptide is performed in the presence of an acid catalyst, most preferably .rho.-toluene sulfonic acid. The resultant modified protein or polypeptide may be employed in numerous applications including drug delivery, absorbable sutures, and thermoplastic films and molded articles.Type: GrantFiled: September 9, 1999Date of Patent: December 19, 2000Assignee: Poly-Med, Inc.Inventors: Shalaby W. Shalaby, Jacqueline M. Allan, Joel T. Corbett
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Patent number: 5986050Abstract: A method for modifying a protein or polypeptide is disclosed which includes the steps of dispersing a protein or polypeptide in an essentially non-aqueous medium and peracylating the protein or polypeptide with a cyclic anhydride having a carbon chain substituent selected from the group consisting of alkyl and alkenyl groups. Most preferably, the cyclic anhydride is succinic anhydride, although glutaric anhydride may also be employed. Preferably, the step of peracylating the protein or polypeptide is performed in the presence of an acid catalyst, most preferably .rho.-toluene sulfonic acid. The resultant modified protein or polypeptide may be employed in numerous applications including drug delivery, absorbable sutures, and thermoplastic films and molded articles.Type: GrantFiled: December 22, 1997Date of Patent: November 16, 1999Assignee: Poly-Med, Inc.Inventors: Shalaby W. Shalaby, Jacqueline M. Allan, Joel T. Corbett
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Patent number: 5962502Abstract: Derivatives of glutamic and aspartic of formula (I) are described ##STR1## where the compounds are potent receptor antagonists of gastrin at the peripheral level and of cholecystokinin at the level of the central nervous system.Type: GrantFiled: April 8, 1996Date of Patent: October 5, 1999Assignee: Rotta Research Laboratorium S.p.A.Inventors: Francesco Makovec, Walter Peris, Lucio C. Rovati, Luigi A. Rovati
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Patent number: 5786447Abstract: Compounds of the formula I as well as methods for their preparation, their pharmaceutical preparations and their use as analgesics.Type: GrantFiled: May 31, 1995Date of Patent: July 28, 1998Assignee: Astra ABInventors: Peter Schiller, Ralf Schmidt
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Patent number: 5652336Abstract: Polymer-bound mixed carboxylic anhydrides can be prepared under mild conditions by the condensation of carboxylic acids (including N-protected amino acids) with polymer-bound acid chlorides. These mixed anhydrides function as polymeric reagents in the sense that they will react readily with monomeric nucleophiles such as amines to form amide or peptide products, depending on the identities of the mixed anhydride and amine reactants. However, in spite of their reactivity, these polymeric mixed anhydrides exhibit a significant degree of stability under conditions of prolonged storage, which suggests that such compounds have commercial utility as a relatively stable form of highly activated carboxylic acids. The polymeric support can be reactivated and recycled for repeated use in the derivatization process.Type: GrantFiled: March 22, 1996Date of Patent: July 29, 1997Assignee: Indiana University FoundationInventors: Wilmer K. Fife, Daniel F. Shullenberger
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Patent number: 5521097Abstract: A protein or peptide is treated by a vapor containing an organic acid represented by the following general formula CF.sub.3 --(CF.sub.2)n--COOH (n is zero or more integer). The resulting reaction mixture is processed by a mass spectrometer to obtain a mass spectrum to measure a mass of respective chemical species contained in the reaction mixture. Alternatively, the reaction mixture is processed by an amino acid analyzer to determine an amino acid sequence of the protein or peptide from the carboxy-terminal. According to another method, the protein or peptide is treated by an anhydride of the organic acid represented by the following general formula CF.sub.3 --(CF.sub.2)n--COOH (n is zero or more integer). The resulting reaction mixture is processed by a mass spectrometer to obtain a mass spectrum to measure a mass of respective chemical species contained in the reaction mixture to determine an amino acid sequence of the protein or peptide from the carboxy-terminal.Type: GrantFiled: August 18, 1992Date of Patent: May 28, 1996Assignee: Seiko Instruments Inc.Inventors: Toyoaki Uchida, Akira Tsugita, Keiji Takamoto, Kazuo Satake
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Patent number: 5516892Abstract: Polymer-bound mixed carboxylic anhydrides can be prepared under mild conditions by the condensation of carboxylic acids (including N-protected amino acids) with polymer-bound acid chlorides. These mixed anhydrides function as polymeric reagents in the sense that they will react readily with monomeric nucleophiles such as amines to form amide or peptide products, depending on the identities of the mixed anhydride and amine reactants. However, in spite of their reactivity, these polymeric mixed anhydrides exhibit a significant degree of stability under conditions of prolonged storage, which suggests that such compounds have commercial utility as a relatively stable form of highly activated carboxylic acids. The polymeric support can be reactivated and recycled for repeated use in the derivatization process.Type: GrantFiled: April 29, 1994Date of Patent: May 14, 1996Assignee: Indiana University FoundationInventors: Wilmer K. Fife, Daniel F. Shullenberger
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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: 5137872Abstract: Human Growth Hormone-Releasing Factor (hGRF) analogs having the sequence [Pro.sup.0, X.sup.15, Y.sup.27 ]-hGRF(1-A)-B, wherein X is selected from the group consisting of Ala and Gly, Y is selected from the group consisting of Ile, Leu, Val, Nle and Met, A has a value from 29-44, and B is NH.sub.2, OH or COOH are synthesized and administered to animals to stimulate the release of Growth Hormone (GH).Type: GrantFiled: September 18, 1989Date of Patent: August 11, 1992Assignee: Pitman-Moore, Inc.Inventors: James E. Seely, Hsi Meng
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Patent number: 5087616Abstract: A therapeutic composition comprising a chemical conjugatge including a first moiety, other than an immunoglobulin or fragment thereof, such as epidermal growth factor, which preferentially binds to a tumor cell, and is internalized by the cell, and a second moiety linked to the first moiety, and comprising a biodegradable polymeric carrier, such as polyglutamic acid, to which one or more cytotoxic molecules, for instance, daunomycin, are attached. The degradation of the carrier by intracellular enzymes releases a cytotoxic agent, resulting in selective destruction of the tumor cells.Type: GrantFiled: August 6, 1987Date of Patent: February 11, 1992Assignee: Battelle Memorial InstituteInventors: Andre E. Myers, Daniel Bichon
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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