Oxygen Containing Reactant Patents (Class 530/406)
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Patent number: 6001364Abstract: Provided by this invention are defined compositions of hetero-polyoximes of defined structure comprising a baseplate structure having a plurality of oxime bonds, wherein each oxime bond links a specifically active molecule to the baseplate. Also provided are novel baseplates having a plurality of oxime forming complementary reactive groups and novel specifically reactive molecules having an oxime forming complementary reactive group. Also provided by this invention are methods of preparing these novel compositions of matter by chemoselectively ligating via oxime bond formation a complementary orthogonal reactive group on the baseplate to a complementary reactive orthogonal group on a specifically active molecule. Methods of using these defined compositions of matter as well as pharmaceutical compositions comprising these defined compositions of matter and methods of their use are also provided by this invention.Type: GrantFiled: August 31, 1993Date of Patent: December 14, 1999Assignee: Gryphon SciencesInventors: Keith Rose, Robin E. Offord
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Patent number: 5998588Abstract: The combination of the capabilities of stimuli-responsive components such as polymers and interactive molecules to form site-specific conjugates which are useful in a variety of assays, separations, processing, and other uses is disclosed. The polymer chain conformation and volume can be manipulated through alteration in pH, temperature, light, or other stimuli. The interactive molecules can be biomolecules like proteins or peptides, such as antibodies, receptors, or enzymes, polysaccharides or glycoproteins which specifically bind to ligands, or nucleic acids such as antisense, ribozymes, and aptamers, or ligands for organic or inorganic molecules in the environment or manufacturing processes.Type: GrantFiled: August 30, 1996Date of Patent: December 7, 1999Assignee: University of WashingtonInventors: Allan S. Hoffman, Patrick S. Stayton
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Patent number: 5985265Abstract: Provided herein are methods and compositions relating to the attachment of water soluble polymers to proteins. Provided are novel methods for N-terminally modifying proteins or analogs thereof, and resultant compositions, including novel chemically modified G-CSF compositions and related methods of preparation. Also provided is chemically modified consensus interferon.Type: GrantFiled: June 20, 1997Date of Patent: November 16, 1999Assignee: Amgen Inc.Inventors: Olaf B. Kinstler, Nancy E. Gabriel, Christine E. Farrar, Randolph B. DePrince
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Patent number: 5965714Abstract: Disclosed and claimed are a method for the covalent attachment of poly- and oligosaccharides to protein molecules via hydrogen peroxide depolymerization of the polysaccharide units, followed by attachment of the depolymerized polysaccharide chain to the amino acid groups of a protein of interest through a linker molecule, and products therefrom, and methods for using the products.Type: GrantFiled: October 2, 1997Date of Patent: October 12, 1999Assignee: Connaught Laboratories, Inc.Inventor: Robert P. Ryall
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Patent number: 5962414Abstract: Composition and method for suppression and inhibition of carcinogenesis comprising a modified Bowman-Birk inhibitor (BBI) comprising an active chymotrypsin inhibitory site, and a deactivated trypsin inhibitory site. The modified Bowman-Birk Inhibitor has been prepared by specifically acetylating a lysine residue with acetic anhydride.Type: GrantFiled: November 26, 1997Date of Patent: October 5, 1999Inventor: Yehudith Birk
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Patent number: 5939535Abstract: A novel protein adduct is disclosed which is associated with the presence of alcohol liver disease. The adduct is a hybrid product of malondialdehyde and acetaldehyde which act synergistically to bind hepatic proteins. The adduct is highly immunogenic and fluorescent. Methods of detection are also disclosed including monoclonal and polyclonal antibodies.Type: GrantFiled: April 8, 1997Date of Patent: August 17, 1999Assignee: The Board of Regents of the University of NebraskaInventors: Geoffrey M. Thiele, Thomas L. McDonald, Dean J. Tuma, Lynell W. Klassen, Michael F. Sorrell
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Patent number: 5919455Abstract: Branched, substantially non-antigenic polymers are disclosed. Conjugates prepared with the polymers and biologically active molecules such as proteins and peptides demonstrate extended circulating life in vivo. Substantially fewer sites on the biologically active material are used as attachment sites. Methods of forming the polymer, conjugating the polymers with biologically active moieties and methods of using the conjugates are also disclosed.Type: GrantFiled: March 20, 1997Date of Patent: July 6, 1999Assignee: Enzon, Inc.Inventors: Richard B. Greenwald, Anthony J. Martinez
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Patent number: 5871954Abstract: Novel oxy- and thio-substituted fatty acid analog substrates of myristoylating enzymes are provided which contain an oxygen or sulfur in place of a methylene group in a carbon position from 4 to 13 in the fatty acid chain of a C.sub.13 -C.sub.14 fatty acid or alkyl ester thereof.Type: GrantFiled: July 15, 1993Date of Patent: February 16, 1999Assignee: Washington UniversityInventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon
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Patent number: 5849599Abstract: A method for making a preconjugate which includes immunogenic species of a polymorphic analyte. The method is carried out by reacting an activated binding moiety, and a polymorphic analyte at room temperature for between about 10 hours and about 60 hours. The attaching reaction results in an excess of the preconjugate which includes the immunogenic species of the polymorphic analyte. The preconjugate can be used to make an immunoreactive conjugate useful as a developer antigen in a competitive inhibition immunoassay for the polymorphic analyte.Type: GrantFiled: February 7, 1997Date of Patent: December 15, 1998Assignee: Beckman Instruments, Inc.Inventors: Chan S. Oh, Anthony K. Cheng, Josephine M. Michael, Thomas S. Dobashi
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Patent number: 5846537Abstract: The present invention provides modified avidin and streptavidin compounds that have suitable blood clearance kinetics for use in a two-step approach to deliver a molecule to a target site. In particular, to hasten SA's blood clearance carbohydrate moieties are covalently bonded to SA. To prolong Avid's blood clearance, Avid is deglycosylated and/or neutralized by alkylation of its lysine amino acids. In a two-step approach, biotinylated compounds are used to deliver radionuclides, cytotoxic drugs, MRI agents, fluorochromes and other agents suitable for imaging and therapy to target-bound modified streptavidin or avidin conjugated antibodies or other targeting agents.Type: GrantFiled: June 7, 1995Date of Patent: December 8, 1998Assignee: University of RochesterInventor: Scott F. Rosebrough
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Patent number: 5681567Abstract: The present invention is directed to methods of preparing high purity polyalkylene oxide carboxylic acids. The methods include reacting a polyalkylene oxide such as polyethylene glycol with a t-butyl haloacetate in the presence of a base followed by treatment with an acid such as trifluoroacetic acid. The resultant polymer carboxylic acids are of sufficient purity so that expensive and time containing purification steps required for pharmaceutical grade polymers are avoided.Type: GrantFiled: August 13, 1996Date of Patent: October 28, 1997Assignee: Enzon, Inc.Inventors: Anthony J. Martinez, Richard B. Greenwald
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Patent number: 5677423Abstract: A process for removing .beta.-hydroxy groups from .beta.-hydroxy-containing compounds is disclosed. The process involves the use of a retro-aldol-promoting reagent selected from the group of trimethylamine-N-oxide, triethylamine-N-oxide, trimethylamine-N-oxide-hydrate, and trimethylamine-hydrate and requires dissolution of the substrate in an aprotic solvent and reaction under elevated temperatures. The process is broadly applicable to a variety of substrates including complex cyclic peptides, linear peptides, and non-peptides.Type: GrantFiled: December 10, 1996Date of Patent: October 14, 1997Assignee: Eli Lilly and CompanyInventor: Michael J. Rodriguez
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Patent number: 5677432Abstract: A compound useful for forming immunoconjugates used in the detection of organophosphate pesticides is provided. The compound has the formula ##STR1## wherein X is selected from the group consisting of R--O--, R--S-- and R--NH--, where R is an optionally substituted aromatic or heterocyclic group, or an optionally substituted alkyl or alkenyl group;Y is O or S;R.sup.1 is H or alkyl; andR.sup.2 is a group of the formula --(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 10, or branched chain alkylene, or a group of the formula R.sup.3 --O--R.sup.4 wherein R.sup.3 and R.sup.4 are both or straight or branched chain alkylene;or a salt or ester thereof.Type: GrantFiled: August 19, 1994Date of Patent: October 14, 1997Assignee: The Horticulture and Food Research Institute of New Zealand LimitedInventors: William Thomas Jones, Hans Wynberg, Wolter Ten Hoeve
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Patent number: 5672662Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.Type: GrantFiled: October 2, 1995Date of Patent: September 30, 1997Assignee: Shearwater Polymers, Inc.Inventors: J. Milton Harris, Antoni Kozlowski
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Patent number: 5663074Abstract: This invention is directed to novel nucleophilic polysubstituted aryl acridinium conjugates and the methods for preparation thereof. The novel nucleophilic polysubstituted aryl acridinium conjugates are useful in biological assays, including novel assays for the determination of Vitamin B.sub.12, folate, cortisol, estradiol, and thromboxane B.sub.2.Type: GrantFiled: March 17, 1993Date of Patent: September 2, 1997Assignee: Chiron Diagnostics CorporationInventor: Say-Jong Law
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Patent number: 5659015Abstract: This invention relates to a method of producing peracetyloxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reagent combination, to directly produce the peracetyl oxazoline. This method may be used for the activation of oligosaccharides, wherein an oligosaccharide containing a reducing GlcNAc terminus is activated by the formation of an oxazolide at the terminal GlcNAc, and then coupled with a bifunctional spacer to provide an oligosaccharide-spacer conjugate. The activated oligosaccharide-spacer conjugate is then coupled to a protein, such as granulocyte colony stimulating factor or .gamma.-interferon, providing a neoglycoprotein conjugate. The invention provides a method for forming neoglycoprotein conjugates which may improve biological and physiochemical properties of the protein. For example, serum lifetime or efficiency of drug delivery of the peptide to a target organ or cell may be improved.Type: GrantFiled: October 13, 1992Date of Patent: August 19, 1997Inventors: Marcelo Colon, Jeffrey T. Davis, James R. Rasmussen, Marianne Borowski, Barbara Y. Wan, Shirish Hirani
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Patent number: 5650234Abstract: Several poly(ethylene glycol) mixed carbonates and their preparation are closed. These carbonates are synthesized by conversion of polyethylene glycol first to the chloroformate then by reaction with the hydroxyl group of N-hydroxybenzotriazole or 2-hydroxypyrimidine or N-hydroxy-2-pyrrolidinone. These mixed carbonate analogs smoothly react with amino groups in aminoglycans and protein and amino containing surfaces to form stable, hydrolysis resistant carbamate linkages.Type: GrantFiled: September 9, 1994Date of Patent: July 22, 1997Assignee: Surface Engineering Technologies, Division of InnerDyne, Inc.Inventors: Eric Kurt Dolence, Chen-Ze Hu, Ray Tsang, Clifton G. Sanders, Shigemasa Osaki
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Patent number: 5631221Abstract: A polypeptide having a molecular weight of 40,000.+-.5,000 daltons and an isoelectric point of 9.5.+-.0.5 is prepared from a cedar pollen. The polypeptide which induces pollenosis can be suitably used as desensitization agent because it induces immunoglobulin antibody which is effective for desensitization, but does not substantially induce immunoglobulin E antibody, a major factor causative of side effects including anaphylaxis shock. Therefore, the polypeptide can be advantageously used in the treatment, prevention and/or diagnosis of pollenosis.Type: GrantFiled: December 14, 1994Date of Patent: May 20, 1997Assignee: Kabushiki Kaisha Hayashibara Sibutsu Kagaku KenkyujoInventors: Keizo Kohno, Manami Sawatani, Masashi Kurimoto
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Patent number: 5623057Abstract: A novel conjugate vaccine comprising partially hydrolyzed, highly purified, capsular polysaccharide (Ps) from Streptococcus pneumoniae bacteria (pneumococci, Pn) linked to an immunogenic carrier protein, is produced by a new process. The conjugate is useful in the prevention of pneumococcal infections. Vaccines comprising a mixture of from one to ten different pneumococcal polysaccharide-immunogenic protein (Pn-Ps-PRO) conjugates induce broadly protective recipient immune responses against the cognate pathogens from which the polysaccharide components are derived. Young children and infants younger than 2 years old, normally unable to mount a protective immune response to the Pn-Ps alone, exhibit protective immune responses upon vaccination with these Pn-Ps-PRO conjugates.Type: GrantFiled: May 20, 1994Date of Patent: April 22, 1997Assignee: Merck & Co., Inc.Inventors: Stephen Marburg, Richard L. Tolman, Peter J. Kniskern, William J. Miller, Arpi Hagopian, Charlotte C. Ip, John P. Hennessey, Jr., Dennis J. Kubek, Pamela D. Burke
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Patent number: 5618927Abstract: The invention concerns a process for the reactivation of denatured protein, in which the protein is incubated with a solution of Tris base or/and a salt of Tris at a concentration of at least 400 mmol/l and at a pH at which the protein to be treated can take up its native conformation.Type: GrantFiled: July 2, 1992Date of Patent: April 8, 1997Assignee: Boehringer Mannheim GmbHInventors: Dorothea Ambrosius, Rainer Rudolph
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Patent number: 5616505Abstract: Novel tethered hapten intermediates and related conjugates based on 3-phenyl-1-adamantaneacetic acid, as well as methods for making and using such conjugates. Haptens based on the above core structure may be substituted at any position on the phenyl ring, especially at the para position. Using tethered intermediates, immunogens, tracers, solid supports and labeled oligonucleotides are all described; as are methods for using the intermediates to prepare the conjugates, methods of using the conjugates to make and purify anitbodies, as assay tracers, and in nucleic acid hybridization assays. Kits containing haptenated oligonucleotides and anti-hapten conjugates are also described.Type: GrantFiled: March 24, 1995Date of Patent: April 1, 1997Assignee: Abbott LaboratoriesInventor: Philip G. Mattingly
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Patent number: 5587461Abstract: The invention relates to novel aromatic acids, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.Type: GrantFiled: September 30, 1994Date of Patent: December 24, 1996Assignee: Ciba-Geigy CorporationInventor: Jui Y. Chang
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Patent number: 5578308Abstract: A detoxified B. pertussis toxin or antigenic preparation is described, which is characterized by stability to reversion to toxicity upon storage at 4.degree.-8.degree. C. and at temperatures above 23.degree. C. Also provided are methods for producing detoxified pertussis toxin and vaccines containing same.Type: GrantFiled: November 14, 1994Date of Patent: November 26, 1996Inventors: Carine Capiau, Jean Petre
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Patent number: 5571689Abstract: A method for acylating peptides and proteins with the CoA-ester of diheteroatom substituted C.sub.13 to C.sub.14 myristic acid analogs catalyzed by N-myristoyltransferase is presented. In the analogs, two non-adjacent methylene groups, which are normally at positions 3-13, are replaced with oxygen or sulfur atoms.Type: GrantFiled: March 28, 1994Date of Patent: November 5, 1996Assignee: Washington UniversityInventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon, George W. Gokel
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Patent number: 5502197Abstract: A pyridinoline composition in which pyridinoline is derivatized specifically at its aliphatic hydroxyl group by a selected chemical group is disclosed. In various embodiments, the composition may be used as a standard for HPLC or immunoassay of pyridinoline, a pyridinoline immunogen for producing anti-pyridinoline antibodies, and a solid-phase reagent for use in an immunoassay kit. Also disclosed are methods for making and using the composition.Type: GrantFiled: April 28, 1994Date of Patent: March 26, 1996Assignee: Metra Biosystems, Inc.Inventors: Yuri Daniloff, Simon P. Robins, Brian J. Evans, David A. Pratt, Robert Lungard
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Patent number: 5480790Abstract: A water-soluble protein conjugate modified by saccharides is covalently bound to a carbohydrate backbone via a saccharide group. Such protein conjugates modified by saccharides can be produced in a simple way by polymerizing a vinylsaccharide and conjugating in a known way the poly(vinylsaccharide) obtained in this way with the protein, which is preferably an enzyme. The protein conjugates according to the present invention are stable over long time periods at a high enzymatic activity and also in aqueous solution and are thus particularly suitable for use in test kits.Type: GrantFiled: April 4, 1991Date of Patent: January 2, 1996Assignees: Boehringer Mannheim GmbH, Gesellschaft fur Biotechnologische Forschung mbHInventors: Wilhelm Tischer, Joachim Klein, Rolf-Joachim Muller, Stephan Engelke
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Patent number: 5468486Abstract: A method for the treatment of the symptoms of fescue toxicosis in mammals comprising injecting a subject mammal with a vaccine which includes from about 5 .mu.g to about 1 mg of a protein-alkaloid conjugate per mL of a physiologically acceptable carrier. There is also provided a vaccine for the treatment of the symptoms of fescue toxicosis and a compound for preparing that vaccine.Type: GrantFiled: March 3, 1994Date of Patent: November 21, 1995Assignee: The University of Tennessee Research CorporationInventors: Bradford B. Reddick, Kimberly D. Gwinn, Jack W. Oliver
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Patent number: 5464767Abstract: Immunoassay methods and reagents for the quantification of total doxepins (i.e., E-doxepin, Z-doxepin, E-desmethyldoxepin, and Z-desmethyldoxepin) in a test sample are disclosed. The quantification of total doxepins is accomplished in an immunoassay employing antibodies and labeled reagents prepared with doxepin derivatives of the Formula II: ##STR1## wherein Y-Z can be C=CH or N-CH.sub.2, R.sub.1 is a linking group, R.sub.2 can be H or CH.sub.3, and Q can be a detectable moiety or an immunogenic carrier material. The antibody reagent comprises antibodies which are capable of binding to total doxepins and which are produced with one or more immunogens prepared from the doxepin derivative of Formula II, and the labeled reagent is also prepared from the doxepin derivative of Formula II.Type: GrantFiled: April 12, 1994Date of Patent: November 7, 1995Assignee: Abbott LaboratoriesInventors: Maciej Adamczyk, Jeffrey R. Fishpaugh, Donald Johnson, Robert E. Hruska
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Patent number: 5444154Abstract: The present invention relates to a series of novel crosslinked polymers. The compounds of the present invention are prepared by the reaction of chloracetic acid with a pendant hydroxyl group which is present on a polyoxyalkylene polymer, followed by the reaction of the halo-ester with a protein or amino acid to give a crosslinked protein compound. In a preferred embodiment the polyoxyalkylene glycol has been prepared by the reaction of both ethylene oxide and propylene oxide. In a more preferred embodiment, the ethylene oxide is at the terminal portion of the molecule and the propylene oxide is in the center. The proteins of the present invention plate out on the surface of hair skin and once dry act as humectants, trapping moisture to the hair. This results in hair which is fuller, has less static and is cosmetically more appealing. This combination of properties makes these polymers ideally suited for use in personal care applications.Type: GrantFiled: June 15, 1994Date of Patent: August 22, 1995Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5441867Abstract: Pre-activated stable protein reagents are provided. The reagents can be made by reaction of the protein and a heterobifunctional linker and have extended stability especially after lyophilisation. The reagents can be used in assay kits to form conjugates with proteins e.g. antibodies or polynucleotides e.g. oligonucleotides probes.Type: GrantFiled: January 7, 1992Date of Patent: August 15, 1995Assignee: Zeneca LimitedInventors: Andrew J. Garman, John R. Parker
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Patent number: 5439972Abstract: Water-soluble compounds derived from a homopolymer or copolymer of maleic anhydride, and applications of the said compounds to supporting biological moleculesWater-soluble compound derived from a homopolymer or copolymer of maleic anhydride having available anhydride functional groups and hydrolyzed anhydride functional groups, wherein the hydrolyzed anhydride functional groups consist of carboxyl functional groups and functional groups derived from carboxyl functional groups carrying a residue of a compound corresponding to the formula I:C.sub.x H.sub.y A.sub.z O.sub.tin which:- A is the nitrogen atom of a primary, secondary or tertiary amine functional group or the sulfur atom of a thiol functional group,- x, z and t, independently of each other, are non-zero integers, and- y is a non-zero integer, not less than 5 when A is a nitrogen atom and not less than 4 when A is a sulfur atom.Type: GrantFiled: October 12, 1994Date of Patent: August 8, 1995Assignee: Bio MerieuxInventors: Marie-Helene Charles, Thierry Delair, Monique Jaubert, Bernard F. Mandrand
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Patent number: 5440023Abstract: A method for making a valproic acid derivative comprising a functionalized spacer arm attached to a .delta. carbon atom of a valproic acid molecule is disclosed. The method proceeds by attaching a spacer arm joined to an inorganic moiety to a valproic acid precursor to make an alkylated compound, derivatizing the alkylated compound in a liquid medium to make the valproic acid derivative, and then separating the valproic acid derivative from the liquid medium. The valproic acid derivative can be used to make an immunoreactive valproic acid conjugate.Type: GrantFiled: September 18, 1992Date of Patent: August 8, 1995Assignee: Beckman Instruments, Inc.Inventors: Anthony K. Cheng, Thomas S. Dobashi
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Patent number: 5399672Abstract: The invention relates to a novel process for preparing immunoconjugates consisting of haptens which are sparingly soluble or insoluble in aqueous solution and proteins/polypeptides using special solvents, in particular diethylene glycol monoalkyl ethers.Type: GrantFiled: November 23, 1993Date of Patent: March 21, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Mohammad Jalalian, Arnulf Heubner, Bernd Reckmann
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Patent number: 5380825Abstract: This invention relates to a method for the immunoassay of AZT (3'-azido-3'-deoxythymidine), also known as zidovudine, in biological fluids such as serum, semen, plasma and urine, as well as other body fluids. The invention also includes (1) various novel analogs of AZT useful in preparing immunogens for antibodies to AZT and in preparing labeled AZT, (2) immunogens for antibodies to AZT, (3) monoclonal and polyclonal antibodies to AZT, (4) labeled AZT analogs and (5) diagnostic test kits for the immunoassay.Type: GrantFiled: June 17, 1991Date of Patent: January 10, 1995Assignee: Sigma Chemical CompanyInventors: Kenneth J. Stenglein, Dennis M. Murray
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Patent number: 5370872Abstract: The present invention relates to a method of producing an E. coli vaccine and to the vaccine produced thereby. The method involves purifying lipopolysaccharide from E. coli expressing complete O-polysaccharide sidechains;isolating the O-polysaccharide region of the lipopolysaccharide molecule by hydrolysis in dilute acetic acid and purifying it essentially free of lipid A; and covalently coupling lipid A-free O-polysaccharide via at least one hydroxyl or carboxyl group of the polysaccharide to a carrier protein. Polyvalent vaccines are prepared by combining two or more monovalent vaccines for different serotypes prepared according to the present invention. The present also relates to conjugates used in the vaccines. The conjugates of the present invention are the O-polysaccharide region of an E. coli lipoplysaccharide molecule covalently coupled to a carrier protein.Type: GrantFiled: August 12, 1991Date of Patent: December 6, 1994Assignee: Swiss Serum and Vaccine Institute BerneInventors: Stanley J. Cryz, Emil P. Furer
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Patent number: 5362852Abstract: A process is disclosed for site-directed chemical modification of peptides and proteins that consists of two steps; (a) selective oxidation of a 2-hydroxyethylamine moiety, --CH(NH.sub.2)--CH(OH)--, in the peptide or protein to generate an aidehyde, and (b) reaction of the new aldehyde with a second reagent to form a product in which the native biological properties of the peptide are augmented by new and useful properties conferred by the second reagent. Additionally, the invention pertains to certain specified types of product formed by the above process.Type: GrantFiled: September 27, 1991Date of Patent: November 8, 1994Assignee: Pfizer Inc.Inventor: Kieran F. Geoghegan
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Patent number: 5360897Abstract: An immunogenic conjugate which is the reductive amination product of an immunogenic capsular polymer fragment having at least one reducing group and derived from a bacterial capsular polymer of a bacterial pathogen, and a bacterial toxin or toxoid. The invention also relates to methods for the preparation of the conjugates, a vaccine containing the conjugates which elicits effective levels of anti-capsular polymer antibodies in humans. Also disclosed are methods for inducing active immunization against systemic infection in young mammals caused by bacterial pathogens comprising the administration of an immunogenic amount of the above-described conjugate. In a preferred embodiment, the capsular polymer fragment prior to conjugation has at least one aldehyde group at each end of the fragment. The final conjugate made with such capsular polymers has a lattice or network structure, and provides extremely high levels of anti-capsular polymer antibodies in infants.Type: GrantFiled: January 9, 1992Date of Patent: November 1, 1994Assignee: The University of RochesterInventors: Porter W. Anderson, Ronald J. Eby
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Patent number: 5342770Abstract: The present invention provides a conjugate in essentially pure form comprising a sugar linked to a protein through a peptide linker, wherein said sugar has a reducing terminal and is free of carboxyl groups, and wherein the reducing terminal of said sugar is linked to the peptide linker. The present invention further provides a conjugate in essentially pure form comprising a sugar linked to an enzyme through a peptide linker, wherein said sugar has a reducing terminal and is free of carboxyl groups, and wherein the reducing terminal of said sugar is linked to the peptide linker. The present invention additionally provides a conjugate in essentially pure form comprising a sugar linked to lysozyme through a peptide linker, wherein said sugar has a reducing terminal and is free of carboxyl groups, and wherein the reducing terminal of said sugar is linked to the peptide linker.Type: GrantFiled: May 11, 1993Date of Patent: August 30, 1994Assignee: Chisso CorporationInventor: Nobuyuki Yamasaki
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Patent number: 5334379Abstract: This invention pertains to immunogenic conjugates comprising a carbohydrate containing antigen or other antigen bound to or genetically fused with a cytokine, lymphokine, hormone or growth factor having immunomodulating activity, wherein the cytokine, lymphokine, hormone or growth factor is capable of modifying immunogenicity of the carbohydrate containing antigen. The cytokine or lymphokine can be an interleukin or an interferon. The immunogenic conjugate can be used in vaccine and co-vaccine formulations.Type: GrantFiled: July 16, 1990Date of Patent: August 2, 1994Assignee: American Cyanamid CompanyInventors: Subramonia Pillai, Ronald Eby
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Phencyclidine derivatives and protein and polypeptide phencyclidine derivative conjugates and labels
Patent number: 5331109Abstract: The present invention is directed to novel PCP derivatives which are synthesized for the covalent attachment to antigens or receptors (proteins or polypeptides) for the preparation of antibodies or receptors to PCP and PCP analogue metabolites. The resulting novel antigens may be used for the production of antibodies or receptors using standard methods. Once generated, the antibodies and the novel derivatives which are covalently attached to proteins, polypeptides or labels may be used in the immunoassay process.Type: GrantFiled: April 6, 1992Date of Patent: July 19, 1994Assignee: Biosite Diagnostics IncorporatedInventor: Kenneth F. Buechler -
Patent number: 5328991Abstract: Proteins, referred to as modified human T cell reactive feline proteins, which have reduced ability to bind immunoglobulin E from cat allergic individuals and substantially unaltered ability to stimulate T cells from cat allergic individuals (relative to affinity purified T cell reactive feline protein) and a method of making such proteins. The modified human T cell reactive feline proteins are useful in desensitization treatment of cat allergic individuals.Type: GrantFiled: February 28, 1991Date of Patent: July 12, 1994Assignee: Immulogic Pharmaceutical Corp.Inventor: Mei-chang Kuo
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Patent number: 5324844Abstract: Poly(ethylene glycol)-N-succinimide carbonate and its preparation are disclosed. Polyethylene glycol (PEG) is converted into its N-succinimide carbonate derivative. This form of the polymer reacts readily with amino groups of proteins in aqueous buffers. The modified proteins have PEG-chains grafted onto the polypeptide backbone by means of stable, hydrolysis-resistant urethane (carbamate) linkages.Type: GrantFiled: January 8, 1992Date of Patent: June 28, 1994Assignee: Enzon, Inc.Inventor: Shmuel Zalipsky
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Patent number: 5320840Abstract: Pharmaceutical compositions for continuous release of a physiologically active substance in which the physiologically active substance comprises a polypeptide covalently conjugated to a water soluble polymer show particularly desirable release characteristics. Polypeptides for use in the pharmaceutical compositions include G-CSF and solution stable derivatives thereof, human calcitonin and interleukin-2. The material of the composition may be a polylactide or biodegradable hydrogel derived from an amphipathic block copolymer.The compositions enable a therapeutically effective polypeptide to be continuously released over a prolonged period of time following a single administration of the pharmaceutical composition to a patient.Type: GrantFiled: July 22, 1991Date of Patent: June 14, 1994Assignee: Imperial Chemical Industries PLCInventors: Roger Camble, David Timms, Anthony J. Wilkinson
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Patent number: 5302703Abstract: The present invention is directed to novel THC derivatives which are synthesized for the covalent attachment to antigens (proteins or polypeptides) for the preparation of antibodies or receptors to the THC metabolites. The resulting novel antigens may be used for the production of antibodies or receptors using standard methods. Once generated, the antibodies or receptors and the novel derivatives which are covalently attached to proteins, polypeptides or labels may be used in the immunoassay process.Type: GrantFiled: March 17, 1993Date of Patent: April 12, 1994Assignee: Biosite Diagnostics IncorporatedInventors: Kenneth F. Buechler, Si S. Moi
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Patent number: 5302701Abstract: This present invention is directed to an artificial functional polypeptide represented by the following structural formula [I]:X--(Y)m--Z [I]wherein X represents a polypeptide having cell-adhesive activity like that of human FN, Y represents a spacer, Z represents a polypeptide having fibroblast growth promoting activity like that of FGF, and m is 1 or 0. This polypeptide is particularly useful for pharmaceutical purposes.Type: GrantFiled: October 13, 1992Date of Patent: April 12, 1994Assignee: Takara Shuzo Co., Ltd.Inventors: Hidetaka Hashi, Fusao Kimizuka, Ikunoshin Kato, Mika Hatai, Yoshihito Yaoi
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Patent number: 5275814Abstract: A protein conjugate or mixture useful in immunotherapy composed of a biological response modifier (BRM) and an allergen is disclosed. In use the protein conjugate or mixture is combined with a pharmaceutically acceptable carrier. Cytokines, bacterial, fungal and viral immunopotentiators and thymus hormones are disclosed as suitable BRM's for use in the invention.Type: GrantFiled: July 10, 1991Date of Patent: January 4, 1994Assignee: Allergy Immuno Technologies, Inc.Inventor: Aristo Wojdani
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Patent number: 5272257Abstract: A method for preparing phycobiliprotein/amine-reactive dye conjugates is disclosed in which the conjugates so prepared overcome the energy transfer/fluorescent quenching dilemma encountered in the use of prior art conjugates. A phycobiliprotein, for example, phycoerythrin or allophycocyanin, is conjugated with an amine-reactive dye, for example, Texas Red or carboxyfluorescein succinimidyl ester, in the presence of a selective salt which causes a hydrophobic intramolecular rearrangement of the phycobiliprotein thereby exposing more hydrophobic sites for binding to the amine-reactive dye. The conjugates prepared according to the invention are useful in multiple color fluorescence assays without requiring the use of multiple exciting sources.Type: GrantFiled: September 3, 1992Date of Patent: December 21, 1993Assignee: Coulter CorporationInventor: Ravinder K. Gupta
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Patent number: 5264209Abstract: Provided are PEGylated "interleukin-6" derivatives (PEG IL-6) having an extended plasma half-life, as well as enhanced in-vivo IL-6 biological activities.Methods for producing the modified glycosylated and unglycosylated IL-6 proteins or polypeptides, as well as, for their use in treating hematopoietic disorders and difficiencies, particularly acute thrombocytopenia, are also provided.Type: GrantFiled: December 21, 1990Date of Patent: November 23, 1993Assignee: Kirin-Amgen, Inc.Inventors: Toshihumi Mikayama, Toshihiko Kadoya, Makoto Kakitani, Hideo Inoue
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Patent number: 5262526Abstract: A fluorescent compound, which is readily capable of forming a stable complex with a rare-earth metal ion having fluorescence with satisfactory intensity even in an aqueous system and long fluorescence lifetime when formed a complex with the rare-earth metal ion, a complex of the fluorescent compound and the rare-earth metal ion, and a labelled reagent made therefrom, together with a specific binding assay using said labelling agent.A fluorescent compound expressed by the following formula A, typically exemplified by 2,15-diaza[3,3](2,9)-1,10-phenanthrolinophane-N.sup.2,N.sup.15 -diacetic acid.Type: GrantFiled: December 20, 1991Date of Patent: November 16, 1993Assignees: Dojindo Laboratories, Mochida Pharmaceutical Co., Ltd.Inventors: Kazumi Sasamoto, Daikichi Horiguchi, Masahiro Nobuhara, Hiroshi Mochizuki
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Patent number: 5252714Abstract: A new polyethylene glycol derivative (PEG) having the property of not being destroyed by water and also being able to retain reactivity in water and selectively react with amine groups. Also provided is a process for modifying organic or polymer surfaces in water by connecting PEG derivatives to exposed amine groups which provides a process whereby there is efficient linking to organic or polymer surfaces in water by use of the PEG derivatives.Type: GrantFiled: November 28, 1990Date of Patent: October 12, 1993Assignee: The University of Alabama in HuntsvilleInventors: J. Milton Harris, M. R. Sedaghat-Herati