Glutamic Acid Per Se Or Salt Thereof Patents (Class 562/573)
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Patent number: 5981564Abstract: The invention relates to new paclitaxel derivatives showing an increased solubility in water. More particularly, the invention relates to glutarylpaclitaxel, glutarylpaclitaxel 6-aminohexanol glucuronide and to different amino acid derivatives of the glutarylpaclitaxel, all of which possess the cytotoxicity activity of the parent compound, paclitaxel. Also disclosed are fluorescent derivatives of paclitaxel for determining a concentration of paclitaxel in a medium or for detecting apoptotic cancer cells.Type: GrantFiled: July 1, 1998Date of Patent: November 9, 1999Assignee: Universite LavalInventors: Michel Page, Renee Paradis, Cyrille Bicamumpaka
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Patent number: 5907059Abstract: The invention provides a process for the preparation of monosodium glutamate from a fermentatively prepared solution containing monoammonium glutamate, the process comprising: a) contacting the solution containing monoammonium glutamate salt with a basic anion exchange resin of at least medium strength to split the salt, whereby glutamate anions attach to the anion exchanger and ammonia is released in the solution; b) subjecting the ammonia-containing solution to distillation, to recover volatile ammonia therefrom; c) contacting the glutamate-containing anion exchange resin with a sodium base solution to regenerate the basic anion exchanger and to directly form monosodium glutamate salt in solution; and d) crystallizing monosodium glutamate salt directly from the monosodium glutamate-containing solution, wherein the crystallized salt has a purity of at least 98%.Type: GrantFiled: February 10, 1998Date of Patent: May 25, 1999Assignees: Amylum Belgium N.V., A.E. Staley Manufacturing CompanyInventors: Pierre Cami, Aharon Eyal
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Patent number: 5837872Abstract: This invention relates to an improved process for preparing selected N-acyl-aminodiacids such as lauroyl glutamic acid.Type: GrantFiled: November 13, 1995Date of Patent: November 17, 1998Assignee: Hoechst Celanese CorporationInventors: David M. Brown, Mohammad A. Khadim, Narayan D. Sadanani, April Yeager
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Patent number: 5770625Abstract: The present invention provides a compound having the structure: ##STR1## wherein R.sub.1 is hydrogen or a branched or unbranched, substituted or unsubstituted aminoalkyl having from two to twenty atoms in the chain, R.sub.2 is hydrogen, methyl, or a branched or unbranched, substituted or unsubstituted alkyl having from two to twenty atoms in the chain; when R.sub.2 is methyl, R.sub.3 is either hydrogen or a substituted or unsubstituted aryl; and R.sub.4 is methyl, a branched or unbranched, substituted or unsubstituted alkyl, alkenyl, alkynyl, alkenynyl, or cycloalkyl having from two to twenty atoms in the chain, or a substituted or unsubstituted aryl group.The invention also concerns a method of preparing the compound from the venom, venom sacs or venom glands of the wasp Philanthus triangulun F. Additionally, the invention provides a method of chemically synthesizing the compound.Type: GrantFiled: July 14, 1994Date of Patent: June 23, 1998Assignee: The Trustees of Columbia University in the City of New YorkInventors: Koji Nakanishi, Amira T. Eldefrawi, Mohyee E. Eldefrawi, Peter N. R. Usherwood
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Patent number: 5559092Abstract: A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.Type: GrantFiled: May 19, 1993Date of Patent: September 24, 1996Assignee: Chesebrough-Pond's USA Co. Division of Conopco, Inc.Inventors: Walter T. Gibson, Gillian E. Westgate
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Patent number: 5536815Abstract: The present invention is directed to the use of a cyclopropylmethyl derivative as a protecting group for compounds containing an amino group, carboxy group, amido group, mercapto group or hydroxy group and to the compounds formed having the cyclopropylmethyl moiety as the protecting group.Type: GrantFiled: March 31, 1994Date of Patent: July 16, 1996Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Hann-Guang Chao
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Patent number: 5492895Abstract: This invention relates to peptide aldehyde analogs that inhibit the thrombin or Factor Xa. The compounds are thought useful for preventing or treating conditions in mammal characterized by abnormal thrombosis.Type: GrantFiled: February 14, 1994Date of Patent: February 20, 1996Assignee: Corvas International, Inc.Inventors: George P. Vlasuk, Thomas R. Webb, Daniel A. Pearson, Matthew M. Abelman
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Patent number: 5428063Abstract: This invention encompasses pharmaceutical compositions in the dietary supplement for treating or preventing fatty infiltration, the first stage of cirrhosis of the liver comprising and administering of not less than 1500 mg of betaine per kg of body weight per day. Dietary supplementation of betaine was shown to completely protect against liver fatty infiltration in rats exposed to prolonged ethanol intake as well as carbon tetrachloride. Hepatic levels of SAM were also elevated, which suggests the mechanism for the protection of the liver.Type: GrantFiled: April 11, 1994Date of Patent: June 27, 1995Assignee: Board of Regents of the University of NebraskaInventors: Anthony J. Barak, Dean J. Tuma, Harriet C. Beckenhauer
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Patent number: 5279744Abstract: A method for purification of an amino acid which comprises contacting an amino acid solution containing impurities with an ion exchange resin to selectively adsorb the amino acid onto the resin, eluting and recovering the adsorbed amino acid whereby the resin is contacted with the amino acid solution in countercurrent continuous multiple steps during adsorption and an eluent is contacted with the adsorbed resin in countercurrent continuous multiple steps during elution.Type: GrantFiled: September 24, 1991Date of Patent: January 18, 1994Assignee: Ajinomoto Co., Inc.Inventors: Hisao Itoh, Katsumi Toide, Masao Ikeda
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Patent number: 5236907Abstract: The present invention relates to an ocular hypotensive treatment of glaucoma which comprising employing 20-substituted-PGs or 20-substituted15-keto-PGs effective as an ocular hypotensive agent; these compounds exhibit no or little side effect such as transient ocular hypertensive response, hyperemia of conjunctiva or of iris, dacryops, lema, closed eye and the like.Type: GrantFiled: October 11, 1991Date of Patent: August 17, 1993Assignee: R-Tech Ueno Ltd.Inventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 5187270Abstract: This invention pertains to amino acids attached to a solid support in a racemization free manner and to a method of covalently linking amino acids to solid supports for use in solid phase peptide syntheses.Type: GrantFiled: January 6, 1989Date of Patent: February 16, 1993Assignee: Millipore CorporationInventor: Michael S. Bernatowicz
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5066828Abstract: This invention relates to certain conjugates of folates and antifolates with difluoroglutamic acid which are useful in the treatment of patients suffering from certain neoplastic diseases including leukemia, melanomas, carcinomas, sarcomas and mixed neoplasias.Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Philippe Bey, H. Michael Kolb
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Patent number: 4942248Abstract: Tertiary-butyl and tertiary-amyl esters of 1H-benzotriazole-1-carboxylic acids are useful blocking agents for blocking the amino or imino groups of amino acids. The six-membered ring of the blocking agent may be unsubstituted or substituted with one or more minor substituents.Type: GrantFiled: December 1, 1988Date of Patent: July 17, 1990Assignee: PPG Industries, Inc.Inventor: Paul M. Novy
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Patent number: 4929755Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and H.sub.2 O or an organic hydroxyl compound to produce an N-acyl-.alpha.-amino acid or ester, respectively, the improvement comprising using as the .alpha.-enamide reactant, an .alpha.-enamide which has a chiral center that is essentially all L or D, thereby producing a reaction mixture containing diastereomeric N-acyl-.alpha.-amino acids or esters having two chiral centers, said mixture having essentially no enantiomeric pairs.Type: GrantFiled: December 19, 1986Date of Patent: May 29, 1990Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4912228Abstract: An improvement in the process of extraction of amino acids from aqueous solutions in which the amino acids are extracted with quaternary ammonium extractants. A pretreatment of the amino acid containing aqueous solution with a tertiary amine prior to extraction of the amino acids with the quaternary ammonium extractant, removes some impurities or poisons present therein, leaving the amino acids in the aqueous solution for subsequent extraction with a water insoluble quaternary ammonium extractant. After extraction with the quaternary extractant, the organic phase is stripped of amino acid and the stripped organic is subjected to an acidic scrub before returning to the quaternary extraction stage.Type: GrantFiled: August 4, 1988Date of Patent: March 27, 1990Assignee: Henkel Research CorporationInventors: Thomas J. Stierman, Phillip L. Mattison
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Patent number: 4721803Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and an organic hydroxyl compound to produce a N-acyl-.alpha.-amino acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric N-acyl-.alpha.-amino acid esters having two chiral centers.Type: GrantFiled: October 29, 1985Date of Patent: January 26, 1988Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4720573Abstract: A process for the synthesis of glutamic acid intermediate from an acrylate, amide and syngas by reacting them in the presence of a catalyst comprising a cobalt-containing compound, a bis-phosphine ligand and a solvent at a pressure of at least 500 psi and a temperature of at least 50.degree. C. and thereafter extracting the glutamic acid.Type: GrantFiled: July 31, 1986Date of Patent: January 19, 1988Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4675196Abstract: A process for the total or partial elimination of aspartic acid and glutamic acid from a protein hydrolyzate or a mixture of aminoacids is described, which consists of passing the hydrolyzate or mixture of aminoacids in solution on an anion exchange resin and then washing with water or eluting the aminoacids from the resin. Aspartic acid and glutamic acid are at least partially separated from the other aminoacids because of their affinity for the resin which is greater than the affinity of the other aminoacids. The resulting mixtures of aminoacids may be used as such or may be further adjusted by addition of valine, leucine, isoleucine, and arginine to give products valuable in clinical nutrition.Type: GrantFiled: February 28, 1984Date of Patent: June 23, 1987Assignee: Pierral S.p.A.Inventors: Carlo Villa, Alvise P. G. Vecchiolino, Alberto Mangia
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Patent number: 4602096Abstract: N-acetyl-D(L)-.alpha.-aminocarboxylic acids are thermally racemized by melting, adding a small amount of acetic anhydride to the melt and heating to a temperature between the melting temperature and about 210.degree. C. and subsequently quenching the melt with an aqueous alkali metal hydroxide or ammonia solution. The residence time needed for complete racemization depends on the heating temperature of the melt in the manner that the higher the heating temperature the shorter the residence time.Type: GrantFiled: August 12, 1985Date of Patent: July 22, 1986Assignee: Degussa AktiengesellschaftInventors: Michael Karrenbauer, Axel Kleemann
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Patent number: 4540792Abstract: This invention relates to a process for the preparation of free L .alpha.-amino acids by the complete conversion of their D antipodes taken individually or possibly in racemic mixtures.The process according to the present invention is characterized in that the D antipodes of an ester of said .alpha.-amino acid is racemized in the presence of a chemical catalyst formed by at least one aromatic aldehyde corresponding to the general formula: ##STR1## wherein: Ar represents an aromatic ring optionally containing a heteroatom, such as nitrogen, andB represents a basic function,to produce a mixture in dynamic equilibrium of the two forms D and L of said ester, the ester which is present in the L form is hydrolyzed enzymatically and irreversibly to produce the corresponding stereostable L .alpha.-amino acid, said stages of chemical racemization and of enzymatic hydrolysis being carried out under identical reaction conditions, and the free L .alpha.-amino acid is recovered.Type: GrantFiled: March 7, 1983Date of Patent: September 10, 1985Assignees: Centre National de la Recherche Scientifique, Institut National de la Sante et de la Reserche MedicaleInventors: Auguste Commeyras, Aldo Previero, Martine Pugniere
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Patent number: 4459423Abstract: A process for producing efficiently and economically without using strong acids nor strong bases, .alpha.-amino acids from .alpha.-amino acid amides by hydrolyzing .alpha.-amino acid amides in an aqueous medium in the presence of ammonia. If necessary, the resultant hydrolyzate liquid from which .alpha.-amino acid has been removed may be reused.Type: GrantFiled: March 5, 1982Date of Patent: July 10, 1984Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masaharu Doya, Takako Uchiyama
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Patent number: 4436910Abstract: Aqueous solutions of sodium salts of .alpha.-aminocarboxylic acids practically free of foreign salts are produced by saponifying the corresponding hydantoin at a temperature between 110.degree. C. and 180.degree. C. with a mixture, in each case based on the hydantoin, of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or hydroxide, separating off the precipitated calcium carbonate after the end of the saponification and concentrating the aqueous sodium salt solution remaining to drive off the ammonia contained therein.Type: GrantFiled: February 10, 1982Date of Patent: March 13, 1984Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Bernd Lehmann, Jurgen Martens
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Patent number: 4243814Abstract: A process for the chemical catalytic hydrolysis of an .alpha.-aminonitrile or of one of the salts thereof, characterized in that an aqueous solution containing at least one carbonyl derivative is reacted with the said .alpha.-amine nitrile or with one of the salts thereof in the presence of hydroxide ions.Type: GrantFiled: December 1, 1977Date of Patent: January 6, 1981Inventors: Robert Pascal, Monique Lasperas nee Marnier, Alain Rousset, Auguste Commeyras, Jacques Taillades, Louis Mion
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Patent number: 4220590Abstract: New optically active bis phosphine compounds which are usful in optically active catalysts. Such catalysts are particularly useful in catalytic asymmetric hydrogenation.Type: GrantFiled: July 31, 1978Date of Patent: September 2, 1980Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky, Billy D. Vineyard