Lysine Per Se Or Salt Thereof Patents (Class 562/562)
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Patent number: 5719292Abstract: The invention provides a process for preparing a coupler compound having a thioether group at the coupling site comprising reacting in the presence of a base (a) a coupler compound having at least one hydrogen at the coupling site with (b) a mixed disulfide comprising either a tetrazole group or an oxadiazole group linked to one sulfur atom and an alkyl or aryl group linked to the other sulfur atom.Type: GrantFiled: March 27, 1997Date of Patent: February 17, 1998Assignee: Eastman Kodak CompanyInventor: Joan C. Potenza
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Patent number: 5710247Abstract: A method is provided for preparing decapeptide and undecapeptide derivatives of LHRH by solution phase peptide chemistry as well as intermediate peptides useful in the same method.Type: GrantFiled: March 19, 1996Date of Patent: January 20, 1998Assignee: Abbott LaboratoriesInventors: Kenneth W. Funk, Edwin O. Lundell, Robert B. Miller, Jane L. Chang, Vimal Kishore, James J. Napier, Michael A. Staeger
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Patent number: 5710246Abstract: A method is provided for preparing decapeptide and undecapeptide derivatives of LHRH by solution phase peptide chemistry as well as intermediate peptides useful in the same method.Type: GrantFiled: March 19, 1996Date of Patent: January 20, 1998Assignee: Abbott LaboratoriesInventors: Kenneth W. Funk, Edwin O. Lundell, Robert B. Miller, Jane L. Chang, Vimal Kishore, James J. Napier, Michael A. Staeger
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Patent number: 5684178Abstract: Lysine derivatives, the salts of the derivatives, their optical isomers of D or L configuration, or their mixtures, the derivatives containing an N.sup..epsilon. -alkoxy or N.sup..epsilon. -alkenoxycarbonyl group of formula: ##STR1## in which: R represents a linear or branched C.sub.13 -C.sub.24 alkyl radical, the C.sub.16 radical being branched, or a linear or branched C.sub.8 -C.sub.24 alkenyl radical. The lysine derivatives are used in cosmetic, pharmaceutical hygiene or food compositions.Type: GrantFiled: November 2, 1994Date of Patent: November 4, 1997Assignee: L'OrealInventors: Michel Philippe, Thierry Bordier
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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: 5565610Abstract: A crystalline salt of lysine hydrochloride, succinic acid or alkali metal salt, wherein the molar ratio of lysine to succinic ion calculated as succinic acid is between about 3 and 10. The salt has the appearance of ordinary table salt crystals.Type: GrantFiled: October 20, 1995Date of Patent: October 15, 1996Assignee: Board of Trustees operating Michigan State UniversityInventors: Kris A. Berglund, Hasan Alizadeh
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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: 5527959Abstract: A crystalline salt of lysine hydrochloride, succinic acid or alkali metal salt, wherein the molar ratio of lysine to succinic ion calculated as succinic acid is between about 3 and 10. The salt has the appearance of ordinary table salt crystals.Type: GrantFiled: January 23, 1995Date of Patent: June 18, 1996Assignee: Board of Trustees operating Michigan State UniversityInventors: Kris A. Berglund, Hasan Alizadeh
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Patent number: 5420316Abstract: A carboxylic acid is made by contacting an organic compound having at least one olefinic bond with ozone to form a mixture of ozonization products; contacting the mixture of ozonization products with oxygen to form a mixture of oxidation products; contacting the mixture of oxidation products with oxygen in the presence of an effective amount of a catalyst selected from the group consisting of a manganese-exchanged X-zeolite, a manganese-exchanged Y-zeolite, a manganese-exchanged A-zeolite, or a combination thereof to form said carboxylic acid.Type: GrantFiled: February 10, 1994Date of Patent: May 30, 1995Assignee: Henkel CorporationInventor: Louis Rebrovic
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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: 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: 5254730Abstract: Amino acids and amino acid derivatives bearing isotopic hydrogen labels at both the .alpha.- and .beta.-positions are produced when N-substituted azomethine derivatives of carboxylic acids and carboxylic acid derivatives are hydrogenated over metal catalysts in isotopically-enriched protic solvents with molecular hydrogen.Type: GrantFiled: January 14, 1992Date of Patent: October 19, 1993Inventor: James L. Kilgore
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Patent number: 5227007Abstract: Disclosed is a process for producing crystals of a salt of an acidic amino acid and a basic amino acid, which comprises adding a water-miscible solvent to an aqueous solution of the salt to prepare a solution 90% or more saturated or supersaturated with the salt, heating the resultant solution under reflux until the formation of crystals stops, adding gradually a water-miscible solvent to the solution under reflux to form crystals of the salt, and recovering the crystals from the resultant mixture.Type: GrantFiled: September 30, 1991Date of Patent: July 13, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tadao Tateba, Michio Shiomi
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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: 5122538Abstract: We have found a new and useful process to generate peroxy acid sanitizing and bleaching compositions at the point-of-use, the process comprising introducing hydrogen peroxide and a carboxylic acid into a reactor at about 0.1 to 10 moles of hydrogen peroxide per mole of acid, and contacting the hydrogen peroxide and carboxylic acid in the presence of a sulfonic acid resin and in the substantial abssence of active metal ions which forms an aqueous peroxy acid composition at a concentration from about up to 20 wt %. Using this process, warewashing, laundry sanitizing and bleach, and hard surface sanitizing compositions can be produced.Type: GrantFiled: July 23, 1990Date of Patent: June 16, 1992Assignee: Ecolab Inc.Inventors: Keith D. Lokkesmoe, Thomas R. Oakes
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Patent number: 5089492Abstract: Acylamino carboxylic acid derivatives corresponding to the formula I ##STR1## in which the groups R.sup.1, R.sup.2, R.sup.3, Z.sup.1 and Z.sup.2 represent functional groups specified in the claims. The acylamino carboxylic acid derivatives have valuable pharmacological properties which, in particular, favorably influence nitrogen metabolism. The compounds are useful as active ingredients in pharmaceutical and/or dietetic compositions for treatment or prevention of nitrogen metabolism disturbances in large mammals caused, for example, by liver or kidney damage.Type: GrantFiled: May 24, 1990Date of Patent: February 18, 1992Assignees: Kali-Chemie AG, Pfrimmer Kabi GmbH & Co. KGInventors: Klaus Gerling, Henning Heinemanmn, Andreas Meier, Klaus Langer
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Patent number: 4948594Abstract: In solid form, copper complex salts of the formula: ##STR1## wherein "n" is from 1 to 5, and "Z" is an anion and "y" is the number required to electrostatically balance the set.Type: GrantFiled: August 22, 1989Date of Patent: August 14, 1990Assignee: Zinpro CorporationInventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
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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: 4900561Abstract: In solid form copper complex salts of the formula: ##STR1## wherein "n" is from 1 to 5, and "Z" is an anion and "y" is the number required to electrostatically balance the set.Type: GrantFiled: January 3, 1989Date of Patent: February 13, 1990Assignee: Zinpro CorporationInventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
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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: 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: 4835309Abstract: L-lysine is recovered using an ion exchange resin. A liquid solution containing L-lysine and possibly impurities is contacted with the resin and is then soaked in elutant for at least about 15 minutes. The elution of L-Lysine from the resin is then continued.Type: GrantFiled: April 14, 1988Date of Patent: May 30, 1989Assignee: Eastman Kodak CompanyInventors: Mark D. Jaffari, Jeffrey T. Mahar, Richard L. Bachert
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Patent number: 4822890Abstract: A method for the production of substantially 100% pure N.alpha.-urethane protected amino acids is disclosed. This method eliminates the formation of di-peptide and tri-peptide contaminants. Reaction of blocking reagents at the carboxylate site on a protected peptide is prevented by the application of labile amino acid esters. Subsequent removal of the ester yields, in ultra-high purity, the N.alpha.-protected amino acid. The substantially 100% pure N.alpha.-urethane protected amino acid are also disclosed.Type: GrantFiled: June 24, 1986Date of Patent: April 18, 1989Assignee: Hoffmann-La Roche Inc.Inventor: David R. Bolin
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Patent number: 4705892Abstract: An improved process for preparing .alpha.,.omega.-diamino acids, such as D,L-homolysine, 2,8-diaminooctanoic acid, ornithine, lysine, or the like, comprising reaction of phthalic anhydride and an amino alcohol in a hydrocarbon solvent; treatment of the resulting phthalimide--N--(CH.sub.2).sub.n --OH derivative, without isolation thereof, with phosphorus tribromide or phosphorous pentachloride; alkylation of diethyl acetamidomalonate with the phthalimide--N--(CH.sub.2).sub.n --chloride or --bromide of the previous step, in the presence of, particularly, sodium hydride/dimethylformamide; standard acid hydrolysis and decarboxylation; selective protection via copper(II) chelation, N-specific acylation with benzyl chloroformate, and decomposition of the amino acid-copper(II) complex with alkaline thioacetamide; standard t-butoxycarbonyl acylation; and deprotection to obtain the desired .alpha.,.omega.-diamino acids.Type: GrantFiled: October 16, 1986Date of Patent: November 10, 1987Assignee: Merck & Co., Inc.Inventors: Joshua S. Boger, Linda S. Payne
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Patent number: 4699927Abstract: Water-soluble valproic acid salts, consisting of reaction products of valproic acid with at least one basic amino-acid, the latter being preferably selected from the group comprising arginine, lysine, histidine, ornithine and glycine.Type: GrantFiled: May 16, 1986Date of Patent: October 13, 1987Assignee: PharlyseInventor: Arthur M. Deboeck
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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: 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: 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: 4296127Abstract: Novel compounds are prepared by reacting essential or semi-essential amino acids with nitrogen-free analogues thereof, particularly alpha-keto and/or alpha-hydroxy analogues. The mixed salt reaction products are precursors of essential and semi-essential amino acids in the body, and mixtures of the salts are useful in the treatment of renal and hepatic disorders characterized by protein intolerance leading to deficiencies of various essential and semi-essential amino acids in the body. They may also be useful in the treatment of nitrogen wasting disorders and protein malnutrition. The novel compounds are generally far more palatable and soluble in aqueous solutions than the individual essential or semi-essential amino acids, nitrogen-free analogues thereof, or simple mixtures of these.Type: GrantFiled: April 18, 1979Date of Patent: October 20, 1981Assignee: The Johns Hopkins UniversityInventor: Mackenzie Walser
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Patent number: 4256917Abstract: A novel crystalline form of anhydrous L-lysine monohydrochloride has been found. The novel crystals do not become agglomerated or hardened when packaged. The crystals are formed when the corresponding dihydrate crystals having a sodium content equal to or less than 4 ppm* are dried in a chamber maintained at a temperature equal to or greater than 115.degree. C.*Na/L-Lys.Type: GrantFiled: December 10, 1976Date of Patent: March 17, 1981Assignee: Ajinomoto Company, LimitedInventors: Yoshikazu Takayanagi, Katsuo Iizumi, Masashi Miyazawa, Nobuyuki Yamaya, Hajime Tamura
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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: 4234744Abstract: Aminoacid hydrochlorides or diaminoacid dihydrochlorides are produced by first reacting a halocarboxylic acid ester with an alkali metal cyanate in the presence of an alcohol to form the corresponding mono- or diurethane and then saponifying this to the corresponding mono- or dihydrochloride. The new process is relatively versatile in its use and above all opens up an elegant synthesis route for lysine.Type: GrantFiled: December 17, 1979Date of Patent: November 18, 1980Assignee: Deutsche Gold- und Silber Scheideanstalt vormals RoesslerInventors: Franz Effenberger, Karlheinz Drauz
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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
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Patent number: 4169207Abstract: An optically active lysine alkyl ester.dihydrochloride is racemized by heating at 100.degree. C. to 250.degree. C. under an atmosphere of hydrogen. By combining this process with asymmetric hydrolysis of racemic lysine alkyl ester with enzymes, racemic lysine alkyl ester can be converted all to L-lysine.Type: GrantFiled: June 19, 1978Date of Patent: September 25, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Motoo Hazama, Gohu Suzukamo
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Patent number: 4140717Abstract: A process is described for directly mono-brominating or mono-chlorinating .alpha.,.alpha.-dialkoxyalkyl or .alpha.,.alpha.-dialkoxycycloalkyl ketoximes in the .beta.-position. Particularly described is the direct chlorination of 2,2-dimethoxycyclohexanone oxime to produce 3-chloro-2,2-dimethoxycyclohexanone oxime, a useful intermediate in the preparation of L-lysine.Type: GrantFiled: September 2, 1977Date of Patent: February 20, 1979Assignee: Allied Chemical CorporationInventors: Bryce C. Oxenrider, Milorad Rogic
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Patent number: 4111933Abstract: In the process for preparing an organic compound of the formulaA' -- Xin whichX is an amino group, a hydroxyl group or a carboxyl group, andA' is the remainder of the molecule, from an organic compound of the formulaA -- Xin whichA is the remainder of the molecule which can undergo reaction to form A', by converting A -- X into a compound of the formulaA -- Z -- COORin whichZ is --NH--, --O-- or a direct C--C bond, andR is a radical of the formula ##STR1## IN WHICH Y is a direct C--C single bond, the --CH.dbd.CH-- group or an arylene group,R.sup.1 to R.sup.4 each independently is hydrogen, halogen or an alkyl, aryl, aralkyl, alkoxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl or cycloalkylaminocarbonyl radical, orR.sup.1 + r.sup.2 and R.sup.3 + R.sup.4 each independently completes a 5- or 6-membered carbocyclic ring, orR.sup.1 and R.sup.Type: GrantFiled: April 28, 1977Date of Patent: September 5, 1978Assignee: Bayer AktiengesellschaftInventors: Heiner Eckert, Ivar Ugi, Hans-Joachim Kabbe