Methionine Per Se Or Salt Thereof Patents (Class 562/559)
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Patent number: 5990349Abstract: A process for the preparation of methionine or a salt of methionine by reaction of the components 3-methylmercaptopropionaldhyde, hydrogen cyanide, ammonia and carbon dioxide or components from which the above-mentioned components can be prepared, optionally in the presence of water, to 5-(2-methylmercaptoethyl)-hydantoin and further reaction thereof to methionine or the salt thereof, characterised in that the reaction of the components is initiated by means of at least one premixture in such a way that a first mixture is formed containing at least the predominant proportion (at least 5/10) of the 3-methylmercaptopropionaldeyde and at least 1/10 of the hydrogen cyanide component or corresponding quantities of components from which these components can be prepared, and less than 5/10 of one of the components ammonia, carbon dioxide or of the components from which ammonia or carbon dioxide can be prepared, and in that this first mixture is combined with the other component(s) for the reactive conversion to 5-(2Type: GrantFiled: March 9, 1998Date of Patent: November 23, 1999Assignee: Degussa AktiengesellschaftInventors: Friedhelm Geiger, Baudouin Halsberghe, Hans-Joachim Hasselbach, Klaus Hentschel, Klaus Huthmacher, Martin Korfer, Sven-Peter Mannsfeld, Herbert Tanner, Ferdinand Theissen, Jose Vanrobaeys, Klaus Willigerodt
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Patent number: 5965539Abstract: Compounds which inhibit prenyl transferases, particularly farnysyltransferase and geranylgeranyl transferase I, processes for preparing the compounds, pharmaceutical compositions containing the compounds, and methods of use.Type: GrantFiled: January 11, 1996Date of Patent: October 12, 1999Assignee: Univeristy of PittsburghInventors: Said Sebti, Andrew Hamilton
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Patent number: 5945563Abstract: Methionine is produced in an improved yield while reducing the load of waste water disposal by a process including the steps of:(A) adding at least one compound selected from potassium carbonate, potassium bicarbonate and potassium hydroxide to a solution containing 5-(.beta.-methylmercaptoethyl)hydantoin, (B) saturating the resulting solution with carbon dioxide gas and separating deposited methionine while leaving a first filtrate behind,(C) transferring part or whole of the first filtrate to step (D),(D) heating the transferred filtrate, adding a water-miscible solvent to it and saturating it with carbon dioxide gas to deposit methionine and potassium bicarbonate, and separating these deposits while leaving a second filtrate behind, and(E) returning the second filtrate to step (A) if desired.Type: GrantFiled: October 27, 1997Date of Patent: August 31, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuharu Imi, Tetsuya Shiozaki
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Patent number: 5834434Abstract: Peptidomimetics of the formula C.beta.X where C is cysteine, X is any naturally occuring amino acid, and .beta. is a hydrophobic spacer, most notably 2-phenyl-4-aminobenzoic acid. These compounds are effective inhibitors of p2lras farnesyltrasferase, block Ras-dependent oncogenic signalling and inhibit human tumor growth in vivo in animal models. Pro-drugs made by functionalizing terminal amino and carboxylic acid groups of peptides and peptidomimetics are also disclosed. Such functionalized derivatives demonstrate increased cell uptake. Other structural modifications are also disclosed.Type: GrantFiled: May 30, 1995Date of Patent: November 10, 1998Assignee: University of PittsburghInventors: Said M. Sebti, Andrew Hamilton
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Patent number: 5770769Abstract: A process for the preparation of methionine or a salt of methionine by reaction of the components 3-methylmercaptopropionaldhyde, hydrogen cyanide, ammonia and carbon dioxide or components from which the above-mentioned components can be prepared, optionally in the presence of water, to 5-(2-methylmercaptoethyl)-hydantoin and further reaction thereof to methionine or the salt thereof, characterised in that the reaction of the components is initiated by means of at least one premixture in such a way that a first mixture is formed containing at least the predominant proportion (at least 5/10) of the 3-methylmercaptopropionaldeyde and at least 1/10 of the hydrogen cyanide component or corresponding quantities of components from which these components can be prepared, and less than 5/10 of one of the components ammonia, carbon dioxide or of the components from which ammonia or carbon dioxide can be prepared, and in that this first mixture is combined with the other component(s) for the reactive conversion to 5-(2Type: GrantFiled: December 18, 1996Date of Patent: June 23, 1998Assignee: Degussa AktiengesellschaftInventors: Friedhelm Geiger, Baudouin Halsberghe, Hans-Joachim Hasselbach, Klaus Hentschel, Klaus Huthmacher, Martin Korfer, Sven-Peter Mannsfeld, Herbert Tanner, Ferdinand Theissen, Jose Vanrobaeys, Klaus Willigerodt
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Patent number: 5763395Abstract: The invention concerns compositions containing a lanthionine containing bacteriocin such as nisin which are stabilized by the presence of a thioether stabilizing agent against degradation.Type: GrantFiled: February 9, 1995Date of Patent: June 9, 1998Assignee: Ambi Inc.Inventors: Peter Blackburn, Jon de la Harpe
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Patent number: 5756803Abstract: A process for the condensation of an aldehyde with hydrogen cyanide in the presence of a buffer is disclosed. The buffer advantageously allows the condensation reaction to occur at a pH equal to or above 4.0 and in the absence of amines.Type: GrantFiled: April 24, 1996Date of Patent: May 26, 1998Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Claude Casse, Frederic Kress, Philippe Morel
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Patent number: 5756761Abstract: A process for improving the solubility of hydrophobic amino acids in which hot saturated aqueous solutions of at least two different amino acids are first combined. A first step includes making a hot saturated aqueous solution of a first and hydrophobic amino acid having a low solubility in water. A second step includes making a hot saturated aqueous solution of a second and hydrophilic amino acid having a high solubility in water. Then the two hot saturated aqueous solutions are mixed to prepare a combined hot solution mixture, and dried. The resulting product is an amino acid food supplement which is blended into animal feed. The preferred amino acids are tryptophan and lysine, when the animal is a domestic farm animal. A preferred ratio is where the concentration of tryptophan is greater than 50 grams per liter and the concentration of lysine is greater than 300 grams per liter.Type: GrantFiled: June 5, 1995Date of Patent: May 26, 1998Assignee: Archer Daniels Midland CompanyInventors: Daniel Dueppen, Thomas Binder, Mark Matlock
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Patent number: 5686472Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: October 27, 1993Date of Patent: November 11, 1997Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, S. Jane deSolms, Ta Jyh Lee, deceased
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Patent number: 5672745Abstract: The direct saponification of methionine nitrile obtained from methylmercaptopropionaldehyde, prussic acid and ammonia gives low yields, catalyst and educt losses and unwanted side-products. The aim of the invention is therefore to provide a method which can be carried out without isolating the intermediate products, in particular continuously, and with low losses. The ketone used is recovered in high yields after amide saponification since this liberates the ketone from side-products. In order to recover the ammonia, it is necessary for the ammonia to be substantially freed of ketone, the mixture of ammonia, ketone and water obtained being separated under pressure in a separation column. When the amide is saponified at .gtoreq.160.degree. C., amide concentrations of less than 25% by wt. are preferred. Methionine nitrile is produced by treatment with at least 4 equivalents of .gtoreq.50% by wt. ammonia at between 40.degree. and 80.degree. C./or between 5 and 60 min.Type: GrantFiled: May 23, 1995Date of Patent: September 30, 1997Assignee: Degussa AktiengesellschaftInventors: Hans-Albrecht Hasseberg, Klaus Huthmacher, Stephan Rautenberg, Heinrich Petsch, Horst Weigel
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Patent number: 5635484Abstract: A peptide, produced by propionibacteria, has a molecular weight of between 300 and 1200 daltons and is inhibitory to gram-negative bacteria. The peptide can be produced by purification of a propionibacteria metabolite mixture, by chemical synthesis, or by a host transformed with a recombinant vector, and is useful in preventing and treating bacterial infections.Type: GrantFiled: November 9, 1993Date of Patent: June 3, 1997Assignee: The State of Oregon Acting by and through the Oregon State Board of Higher Education on Behalf of Oregon State UniversityInventors: James W. Ayres, William E. Sandine, George H. Weber
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Patent number: 5631031Abstract: Disclosed are water-insoluble, calcium or magnesium salts of alpha amino acids and a process for their preparation. The process comprises the steps of reacting an alpha-amino-protected alkyl ester of an amino acid with a metal base, thereby forming a water-soluble amino acid salt, followed by reacting the water-soluble salt with either a calcium or magnesium salt, resulting in the formation of a water-insoluble salt of the amino acid. The water-insoluble salts can be used as feed supplements for ruminant animals and to supplement food products for human consumption.Type: GrantFiled: June 13, 1994Date of Patent: May 20, 1997Inventor: Thomas L. Meade
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Patent number: 5602098Abstract: Peptidomimetics of the formula C-AMBA-X where C is cysteine, X is, for example, methionine or phenylalanine and AMBA is a hydrophobic spacer, notably 3-aminomethylbenzoic acid. These compounds are effective inhibitors of p21 ras farnesyltransferase. Other modifications including alternative spacers for AMBA, and replacement of the A.sub.1 A.sub.2 X component of known CA.sub.1 A.sub.2 X tetrapeptides by a non-peptide aryl or heterocyclic component are also disclosed as are various phosphonylated and arylated derivatives of peptides and peptidomimetics. Pro-drugs made by functionalizing terminal amino and carboxylic acid groups of peptides and peptidomimetics are also disclosed. Such functionalized derivatives demonstrate increased cell uptake. Other structural modifications are also referred to.Type: GrantFiled: May 18, 1993Date of Patent: February 11, 1997Assignee: University of PittsburghInventors: Said Sebti, Andrew Hamilton, Churl M. Seong
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Patent number: 5508271Abstract: A method for treating neurological dysfunctions associated with AIDS or ARC comprising the administration of methylcobalamin, alone or in combination with methionine. Substantial increases in the number of T4+ T-lymphocytes, T8+ T-lymphocytes, or the ratio of T4+ to T8+ T-lymphocytes is also observed with this treatment.Type: GrantFiled: July 7, 1993Date of Patent: April 16, 1996Assignee: BiogenesysInventor: Michael Rabinoff
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Patent number: 5481026Abstract: The invention relates to new optically active amino acid derivatives of the general formula (I) ##STR1## in which n, R, R.sub.1, R.sub.2, R.sub.3, X and A have the meaning given in the description, which amino acid derivatives contain sulphoxide or sulphone groups, to two basic synthetic routes for the preparation from sulphur-containing amino acids, to the polymerization of these monomers and to the use of the polymers as optically active adsorbents for chromatographic resolution of racemates to give the enantiomers.Type: GrantFiled: July 1, 1994Date of Patent: January 2, 1996Assignee: Bayer AktiengesellschaftInventors: Michael Grosse-Bley, Bruno Bomer, Rolf Grosser, Walter Lange, Franz-Peter Hoever, Dieter Arlt
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Patent number: 5463120Abstract: A process for the crystallization of DL-methionine from a crystallization medium comprising DL-methionine and an aluminium salt of an organic acid.Type: GrantFiled: July 22, 1994Date of Patent: October 31, 1995Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Jean Giraud, Daniel LeClaire
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Patent number: 5455234Abstract: Mammalian hair growth is reduced by applying to the skin an inhibitor of a cysteine synthetic pathway enzyme.Type: GrantFiled: March 16, 1994Date of Patent: October 3, 1995Inventors: Gurpreet S. Ahluwalia, Douglas Shander
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Patent number: 5411757Abstract: In the present invention, L-amino acids comprise the medical food which provides a source of protein-equivalent of free purified L-amino acids in a palatable powdered form which can be incorporated into a liquid beverage or into proprietary low-protein solid food products without adversely affecting the organoleptic qualities of these foods. The mixture can act to deliver a protein-equivalent in heretofore unavailable and, thereby, novel ways.Type: GrantFiled: August 31, 1993Date of Patent: May 2, 1995Inventors: Neil R. M. Buist, Annie P. Prince
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Patent number: 5395824Abstract: A prophylactic or therapeutic agent for malignant hypercalcemia, bone Paget's disease and osteoporosis is disclosed, which contains as an active ingredient a dipeptide derivative represented by formula:R.sup.1 NH--CH(R.sup.2)--CO--NH--CH(R.sup.3)--R.sup.4 (I)wherein R.sup.1 represents an aliphatic acyl group, a halogen-substituted aliphatic acyl group, or benzyloxycarbonyl group; R.sup.2 represents a lower alkyl group or an aralkyl group; R.sup.3 represents a lower alkyl group, an aralkyl group, or methylthioethyl group; R.sup.Type: GrantFiled: October 30, 1992Date of Patent: March 7, 1995Assignee: Suntory LimitedInventors: Naoki Higuchi, Masayuki Saitoh, Shinjiro Niwata, Yoshinobu Kiso, Yasuhiro Hayashi
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Patent number: 5344767Abstract: A method of preparing a high specificity .sup.35 S-sulfide comprises preparing a reducing mixture comprising hydrochloric acid, hydriodic acid and hypophosphorus acid, substantially removing any sulfate present in the mixture, admixing the reducing mixture with a composition comprising an .sup.35 S-sulfate corresponding to a desired .sup.35 S-sulfide to obtain the .sup.35 S-sulfide, and recovering the .sup.35 S-sulfide from the admixture. The thus prepared .sup.35 S-sulfides are applicable to the synthesis of high specificity .sup.35 S amino acids and derivatives thereof by sulfhydrylation, e.g., in the presence of an enzyme and a .sup.35 S-sulfide or sulfhydric acid and the O-acetylated amino acid. The labeled amino acid may be separated from the reaction mixture by reverse phase chromatography.Type: GrantFiled: June 29, 1992Date of Patent: September 6, 1994Assignee: Commissariat a l'Energie AtomiqueInventors: Claude Boullais, Jean-Pierre Noel, Michel Riva
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Patent number: 5340828Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: September 30, 1991Date of Patent: August 23, 1994Assignee: Merck & Co., Inc.Inventors: Samuel L. Graham, S. Jane deSolms
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Patent number: 5194625Abstract: A compound of the formula:AN/xSwherein A represents an amino acid, N represents an .alpha.-keto acid, S represents a lower alcohol or acetone; and x ranges from 0.1 to 3.Type: GrantFiled: December 13, 1989Date of Patent: March 16, 1993Assignee: Ajinomoto Co., Inc.Inventors: Toshiya Tanabe, Shin-ichi Kishimoto
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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: 5166425Abstract: A compound of the formula: ##STR1## wherein R and R' each is hydrogen or a protecting group, or acid addition salts thereof, useful as a selective insecticide.Type: GrantFiled: May 28, 1991Date of Patent: November 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadahiko Tsushima, Shoichi Ishihara
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Patent number: 5149692Abstract: The invention concerns novel renin-inhibitory peptides which are useful for treating renin-associated hypertension, congestive heart failure, hyperaldosteronism, glaucoma, and diseases caused by retroviruses including HTLV-I, -II, -III. Processes for preparing the peptides, novel intermediates useful in the preparation thereof, compositions containing them, and methods of using them are included. Also included is a diagnostic method which uses the compounds to determine the presence of renin-associated hypertension, congestive heart failure, or hyperaldosteronism.Type: GrantFiled: December 21, 1989Date of Patent: September 22, 1992Assignee: Warner-Lambert CompanyInventors: Annette M. Doherty, Harriet W. Hamilton, Bruce A. Steinbaugh
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Patent number: 5110797Abstract: Peptide compounds of formula (I): ##STR1## wherein A is hydrogen or an amino-protecting group; X is a member selected from the group consisting of Gly, Glu, Tyr, Asp, Phe, Ile, Ala, Pro, Leu, Hyp, Val, His, Arg, Ser, Thr, Pyr, Trp, 5-HTP, Cys, Met, .tau.-Glu, .beta.-Asp; Y is a (CH.sub.2).sub.3-6 or (CH.sub.2).sub.3-6 having an hydroxy group; R is an hydroxy group or an oxygen atom with a carboxy-protecting group; are useful as neurotropic agents.Type: GrantFiled: April 29, 1988Date of Patent: May 5, 1992Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kazuharu Ienaga, Kunihiko Higashiura
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Patent number: 5026909Abstract: A method according to the invention comprises mixing the starting biologically active organic compound, an inorganic vehicle and a catalyst in the form of a platinum-group metal, followed by reacting the resulting mixture with an isotope of hydrogen at a temperature of 373-523 K. and cooling the reaction mixture to a temperature of 288-303 K. and isolation of the desired product therefrom. The invention can be useful, for example, in medical and biological studies.Type: GrantFiled: March 22, 1989Date of Patent: June 25, 1991Inventors: Jury A. Zolotarev, Dmitry A. Zaitsev, Vadim J. Tatur, Nikolai F. Myasoedov
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Patent number: 4960932Abstract: An aqueous solution of an alkali metal salt of methionine, which can be used as an additive in feedstuffs, is made by hydrolysis of methionine amide with an alkali metal hydroxide.Type: GrantFiled: October 3, 1988Date of Patent: October 2, 1990Assignee: A.E.C.Inventors: Claude Gillonnier, Rene Moisson
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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: 4886889Abstract: Disclosed is a process for recovery of amino acids from aqueous mixtures. In particular, it relates to a treatment of said amino acid containing aqueous mixture prior to extraction of the amino acid with a water immiscible organic solution containing a water insoluble extractant for said amino acid. The overall process of the invention which includes the pretreatment and extraction, also includes optional methods of recovering said extracted amino acid from the water immiscible organic solution. Accordingly, the invention also relates to a process for recovery of the amino acid by stripping of the amino acid from the organic solution and precipitation of the amino acid.Type: GrantFiled: May 16, 1986Date of Patent: December 12, 1989Assignee: Henkel CorporationInventors: Phillip L. Mattison, Ronald P. Wirth, Michael J. Virnig, LeRoy Krbechek
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Patent number: 4886888Abstract: Amino acids can be purpified and/or concentrated by extracting aqueous mixtures such as fermentation broths by contacting an aqueous mixture containing amino acids with an organic solution containing a water insoluble extractant selected from the group consisting of:1. A quaternary ammonium ion having the formula: ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are aliphatic, each having from 1 to 22 carbon atoms, and together have a minimum of 25 carbon atoms, and where at least three of the four R groups are at least a C.sub.4.2. A quaternary phosphonium ion having the formula: ##STR2## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above. 3. A tertiary sulfonium ion having the formula: ##STR3## where R.sub.1, R.sub.2 and R.sub.3 each are aliphatic with from 1 to 22 carbon atoms, and together have a minimum of 24 carbons and where at least two of these groups are at least a C.sub.6.4. An organic boride ion having the formula: ##STR4## where R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: December 22, 1986Date of Patent: December 12, 1989Assignee: Henkel CorporationInventors: Francis W. Tuominen, Ronald R. Swanson, Phillip L. Mattison, Kenneth D. MacKay, Bradley W. Glorvigen
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Patent number: 4837371Abstract: An aqueous solution containing amino acids of which the solubility in water at isoelectric point is low, can be highly concentrated by means of semipermeable membranes in the presence of a water-soluble organic solvent while increasing the solubility by adjusting a pH.Type: GrantFiled: September 3, 1987Date of Patent: June 6, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shinji Ogawa, Seiya Iguchi, Hiroshi Kimura, Yoh Ohmori
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Patent number: 4827029Abstract: L-amino acids present in cleavage solutions obtained in the acylase-catalyzed cleavage of N-acetyl-D,L-amino acids are isolated by use of a strongly acidic ion exchanger in H+ form. First, the mother liquor from a previous treatment cycle is fed to the ion exchanger, and then the cleavage solution and finally the wash water and the discharge from the ion exchanger which is pH-controlled is analyzed into an "effluent water fraction", an "N-acetyl-D-amino acid fraction" and an "L-amino acid fraction". The last fraction is adjusted by addition of fresh cleavage solution to a pH of between 4.0 and 6.0, and from the mixture which is thus obtained the L-amino acid is isolated by crystallization. The mother liquor which is obtained is recycled back into a subsequent treatment cycle.Type: GrantFiled: January 21, 1988Date of Patent: May 2, 1989Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Kurt Klostermann, Wolfgang Leuchtenberger, Rudi E. Moerck, Michael Karrenbauer
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Patent number: 4789686Abstract: A concentrated aqueous solution of the sodium salt of methionine, which is practically free from inorganic salts, is produced from the medium resulting from the hydrolysis of 5-(.beta.-mercaptoethyl)hydantoin.Type: GrantFiled: July 14, 1987Date of Patent: December 6, 1988Assignee: AEC-Sociate de Chimie Organique et BiologiqueInventor: Jean Giraud
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Patent number: 4777289Abstract: A process for the preparation of alkylthioalkanoate salts by reaction of an alkali metal alkylmercaptide with a lactone in the presence of an aprotic polar organic solvent. Preferably, the alkali metal mercaptide is prepared by reaction of an alkylmercaptan and an alkali metal phenate.Type: GrantFiled: May 8, 1986Date of Patent: October 11, 1988Assignee: Monsanto CompanyInventor: Dennis A. Ruest
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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: 4709016Abstract: A new class of chemical reagents called release tags which comprise signal, release and reactivity groups is disclosed and a release tag involving a pentafluorobenzoyl signal group, a methionylamide release group, and an active ester reactivity group is used to analyze the hormone, thyroxine, in serum, involving quantitation of the released signal group by gas chromatography with electron capture detection.Type: GrantFiled: February 1, 1982Date of Patent: November 24, 1987Assignee: Northeastern UniversityInventor: Roger W. Giese
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Patent number: 4678806Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## the amido ester moiety of which is in the L-configuration, and pharmaceutically acceptable salts thereof are disclosed.Type: GrantFiled: September 2, 1986Date of Patent: July 7, 1987Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Wasyl Halczenko, George Hartman, Steven M. Pitzenberger
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Patent number: 4661606Abstract: Amino acids can be purified and/or concentrated by extracting aqueous mixtures such as fermentation broths by contacting an aqueous mixture containing amino acids with an organic solution containing a water insoluble extractant.Type: GrantFiled: June 6, 1984Date of Patent: April 28, 1987Assignee: Henkel CorporationInventors: Francis W. Tuominen, Ronald R. Swanson, Phillip L. Mattison, Kenneth D. MacKay, Bradley W. Glorvigen
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Patent number: 4638086Abstract: The racemization of optically active aminoacids (including their N-acyl derivatives) by heating with carboxylic acids takes place particularly readily with carboxylic acids of low volatility. Only catalytic quantities of acid are needed; it is advantageous to use equimolar quantities or an excess, which serves as a diluent. A reaction mixture from an enzymatic racemate resolution can be heated directly for the purpose of racemization, after separation of the L-aminoacid and the water.Type: GrantFiled: September 25, 1984Date of Patent: January 20, 1987Assignee: Hoechst AktiengesellschaftInventor: Susanne Grabley
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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: 4536596Abstract: A method for the extraction of certain amino acids from aqueous solutions by contacting said solutions with various dithiophosphinates in conjunction with a polar diluent is disclosed.Type: GrantFiled: May 14, 1984Date of Patent: August 20, 1985Assignee: American Cyanamid CompanyInventors: Christos Savides, John H. Bright
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Patent number: 4519955Abstract: .alpha.-(S)-amino acid..alpha.-phenylethanesulfonate compounds and methods of optical resolution of .alpha.-amino acids and .alpha.-phenylethanesulfonic acids are described.Type: GrantFiled: March 2, 1984Date of Patent: May 28, 1985Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ichiro Chibata, Shigeki Yamada, Chikara Hongo, Ryuzo Yoshioka
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Patent number: 4518801Abstract: The invention is directed to a process for the hydrolysis of 5-(.beta.-methylmercaptoethyl)-hydantoin by reaction at elevated temperature and pressure in an aqueous alkaline medium. There are obtained alkali methioninate solutions from which there can be separated methionine.Type: GrantFiled: September 7, 1984Date of Patent: May 21, 1985Inventors: Rudolf Bolze, Friedhelm Geiger, Manfred Spindler, Herbert Tanner
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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: 4391988Abstract: Aqueous sodium methioninate solutions having a low content of sodium carbonate can be recovered from the crude hydrolysis mixture resulting from the saponification of 5-(.beta.-methylmercaptoethyl)-hydantoin with 1.1 to 6 equivalents of sodium hydroxide and/or sodium carbonate by distilling off the water from the crude hydrolysis mixture until the sodium methioninate content is 40 to 65 weight percent, and after cooling to at most room temperature separating off the precipitated sodium carbonate.Type: GrantFiled: February 10, 1982Date of Patent: July 5, 1983Assignee: Degussa AktiengesellschaftInventors: Manfred Spindler, Herbert Tanner, Friedhelm Geiger, Friedrich Bittner, Jurgen Martens
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Patent number: 4391987Abstract: Aqueous sodium methioninate solutions having a low content of sodium carbonate can be recovered from the crude hydrolysis mixture resulting from the saponification of 5-(.beta.-methylmercaptoethyl)hydantoin with 1.1 to 6 equivalents of sodium hydroxide and/or sodium carbonate by cooling the crude hydrolysis mixture to a temperature below 10.degree. C., separating off the precipitated sodium carbonate and concentrating the sodium methioninate solution remaining to 40 to 65 weight percent.Type: GrantFiled: February 10, 1982Date of Patent: July 5, 1983Assignee: Degussa AktiengesellschaftInventors: Manfred Spindler, Herbert Tanner, Friedhelm Geiger, Friedrich Bittner, Jurgen Martens
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Patent number: 4380646Abstract: A process is disclosed for the prparation of an acylated aminocarboxylic acid which comprises contacting an aminocarboxylic acid, its alkali metal or alkaline earth metal salt with a low alkyl carboxylic acid ester of the formulaR.sub.1 -CO-O-R.sub.2,wherein R.sub.1 represents hydrogen or a straight-chain or branched or cyclic hydrocarbon moiety of 1 to 30 carbon atoms, which can be substituted if desired, and wherein R.sub.2 represents a straight-chain, branched or cyclic hydrocarbon moiety of 1 to 8 carbon atoms in the presence of an alkali metal or alkaline earth metal alcoholate.Type: GrantFiled: January 29, 1981Date of Patent: April 19, 1983Assignee: Dynamit Nobel AktiengesellschaftInventor: Giselher Franzmann