Alpha Nitrogen Patents (Class 562/575)
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Patent number: 5336805Abstract: Process for preparing an a-amino acid having the general formula (1) of ##STR1## where R represents an aryl group or a substituted aryl, cycloalkyl or alkyl group, in which process glyoxylic acid, or a precursor or derivative thereof, is contacted in the presence of sulphamic acid with an unsaturated compound chosen from the group of aromatics, cycloalkenes and alkenes. By applying the process higher efficiencies are obtained.The acid obtained as reaction product can be esterified and amidated without prior isolation.Type: GrantFiled: August 12, 1992Date of Patent: August 9, 1994Assignee: DSM N.V.Inventors: Wilhelmus H. J. Boesten, Nicolaas A. de Heij
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Patent number: 5292942Abstract: A process is described for the preparation of aqueous solutions of betaines of the formula ##STR1## in which: R.sup.1 is an alkyl radical having 6 to 22 carbon atoms or is a radical of the formula R'CONH(CH.sub.2).sub.z --, in which R' has the meaning of R.sup.1 and z is 2, 3 or 4, R.sup.2 is an alkyl radical having 1 to 4 carbon atoms or is a radical of the formula --(CH.sub.2).sub.m --OH, in which m is 1, 2 or 3, R.sup.3 is an alkyl radical having 1 to 4 carbon atoms or is a radical of said formula --(CH.sub.2).sub.m --OH and y is 1, 2 or 3. The aqueous betaine solutions are prepared by quaternization of the corresponding tertiary amines with an .omega.-halocarboxylic acid and with an alkali metal hydroxide in the aqueous phase. The quaternization is carried out continuously in two or three stirred tanks arranged in a cascade, defined process characteristics being maintained in each tank. Using the novel process, aqueous betaine solutions are obtained in high yield and purity in a simple manner.Type: GrantFiled: April 2, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Rudolf Aigner, Guillermo Maier, Rainer Muller, Hubert Seitz
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Patent number: 5283339Abstract: Metallated compounds can be used to extract or precipitate proteins from solution. The compounds can be polymers, such as polyalkylene glycols, which can be mono- or bimetallated or smaller bis-metal chelates, such as ethylenebis(oxyethylenenitrilo)tetraacetic acid. The monometallated polymers are preferred in the extraction process whereas the bimetallated compounds are preferred in the precipitation process. In addition, new PEG compounds which are capable of chelating a variety of metals are described. Both mono- and bi-metallated forms are set forth. The new metallated compounds are very effective in extracting or precipitating proteins from solution.Type: GrantFiled: August 5, 1992Date of Patent: February 1, 1994Assignee: California Institute of TechnologyInventors: Frances H. Arnold, Gerald E. Wuenschell
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Patent number: 5281749Abstract: A process for reducing the residual content of free alkylating agent in aqueous solutions of amphoteric or zwitterionic surface-active agents by aftertreatment with ammonia, an amino acid containing 2 to 8 carbon atoms, or an oligopeptide.Type: GrantFiled: May 28, 1992Date of Patent: January 25, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Guenter Uphues, Uwe Ploog, Klaudia Bischof, Kenan Kenar, Pavel Sladek
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Patent number: 5281750Abstract: The present invention relates to chiral supports and to their use in the asymmetric synthesis, deracemization and optical inversion of organic chiral compounds. In particular, the supports are used in combination with thermal equilibration of a species having a reactive achiral portion. Preferably, these supports are obtained by the copolymerization of at least one chiral unit and at least one functionalizing unit or by the polymerization of at least one chiral unit which is a source of said functionalizing unit. Optionally, a crosslinking agent is utilized. By utilizing these supports and thermal equilibration, excess enantiomers can be produced.Type: GrantFiled: November 16, 1992Date of Patent: January 25, 1994Assignee: Rhone-Poulenc ChimieInventors: Robert Jacquier, Monique Calmes, Jacques Daunis
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Patent number: 5280093Abstract: The present invention relates to chiral polymers and to their uses for operations of asymmetric synthesis, deracemization and optical inversion.These polymers are characterized in that they comprise:a chiral unita functionalizing unitan optional crosslinking unitApplication to chiral organic synthesis.Type: GrantFiled: April 14, 1993Date of Patent: January 18, 1994Assignee: Rhone-Poulenc ChimieInventors: Robert Jacquier, Monique Calmes, Jacques Daunis
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Patent number: 5268368Abstract: A stable rapidly dissolving lyophilized composition of cyclophosphamide and an amino acid selected from the group consisting of glycine, valine and serine is provided which contains an amount of water which is equimolar to the amount of amino acid and the amount of cyclophosphamide in said composition; the composition is preferably prepared from a solution containing at least 2% (W/V) of the amino acid and having a pH in the range of 5.0 to 7.0.Type: GrantFiled: May 17, 1991Date of Patent: December 7, 1993Assignee: Erbamont, Inc.Inventor: Nageswara R. Palepu
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Patent number: 5258550Abstract: This invention relate to a process for producing glycine by reacting glycolonitrile, carbon dioxide and ammonia in the presence of water, comprising subjecting first water, glycolonitrile, carbon dioxide and ammonia to a pre-reaction at 80.degree.-120.degree. C. for 0.5-1 hour and then to the main reaction at 150.degree.-200.degree. C. and a process further comprising recycling the remaining mother liquor having separated the glycine from the reaction solution obtained by the above process to the system comprising water, glycolonitrile, carbon dioxide and ammonia to carry out the aforesaid pre-reaction and/or main reaction.Type: GrantFiled: July 8, 1991Date of Patent: November 2, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Kenji Fujiwara, Nobutaka Ueda, Yuuji Matsuu, Hiroshi Kato, Atsuhiko Hiai
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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: 5202479Abstract: A process for preparing glycine which comprises the steps of reacting glycolonitrile, carbon dioxide gas, ammonia and water to obtain a reaction solution containing glycine, concentrating this reaction solution in two steps, recycling a gaseous phase portion formed in a primary concentration step to a reaction zone, and recycling to the reaction zone, a mother liquor left after glycine crystals have been separated from a concentrate obtained in a secondary concentration step.Type: GrantFiled: February 1, 1991Date of Patent: April 13, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kenji Fujiwara, Nobutaka Ueda, Yuji Matsuu, Hiroshi Kato, Atsuhiko Hiai
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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: 5155264Abstract: Desclosed is a process for preparing glycine in a high yield, which comprises reacting a carboxymethyl quaternary ammonium chloride represented by the following structural formula (I):Cl(R.sub.3 NCH.sub.2 COOH) (I)wherein R represents an alkyl group having 1 to 4 carbon atoms,with an aminomethanol derivative represented by the following structural formula (II): ##STR1## wherein R.sub.1 represents a hydrogen atom or a CH.sub.2 OH group, in a solvent.Type: GrantFiled: June 17, 1991Date of Patent: October 13, 1992Assignee: Hakko Tsusho CO., Ltd.Inventor: Ming F. Chen
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Patent number: 5153358Abstract: A novel process for the preparation of .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids is disclosed. These .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids are useful as intermediates for the preparation of enzyme inhibitors (for example, renin inhibitors) and other peptides or amino acid derivatives or analogs.Type: GrantFiled: January 30, 1991Date of Patent: October 6, 1992Assignee: Abbott LaboratoriesInventor: Thomas M. Zydowsky
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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: 5132428Abstract: A process for enantioselectively alkylating, at the asterisked carbon atom, a single enantiomer of a glycine derivative having the general formula ZCOCH(R)NY wherein Z is a moiety derived from a chiral sultam, R is hydrogen or C.sub.1 to C.sub.10 alkyl and Y is one or more groups rendering the nitrogen atom unreactive towards alkylating agents comprises:(i) reacting the glycine derivative with an enolising agent to produce the corresponding enolate of the glycine derivative, and(ii) thereafter reacting the enolate of the glycine derivative with an alkylating agent of formula R.sup.1 X to generate a single enantiomer of a product of formula ZCOC(R)(R.sup.1)NY where R.sup.1 is selected from C.sub.1 to C.sub.10 alkyl, C.sub.1 to C.sub.20 aralkyl, C.sub.2 to C.sub.10 alkenyl or substituted derivatives thereof and X is Cl, Br or I. The product of the process can be treated with first acid and then base to generate the enantiomerically pure alpha-amino acid of formula HO.sub.2 CC(R)(R.sup.1)NH.sub.Type: GrantFiled: November 5, 1990Date of Patent: July 21, 1992Assignee: BP Chemicals LimitedInventor: Wolfgang W. R. E. J. von Oppolzer
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Patent number: 5120873Abstract: Betaines are produced in solid form by reacting a tert-amine with a haloalkanoate salt when the reaction is conducted in a liquefied gas as the solvent. In a preferred embodiment, the tert-amine is an N-alkyldimethylamine, the haloalkanoate is sodium chloroacetate, and the liquefied gas is carbon dioxide.Type: GrantFiled: July 1, 1991Date of Patent: June 9, 1992Assignee: Ethyl CorporationInventors: Jeffrey W. Perine, Joe D. Sauer, Kim R. Smith, James E. Borland
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Patent number: 5105008Abstract: Betaines are produced in solid form by reacting a tert-amine with an alkyl haloalkanoate and hydrolyzing the resultant quaternary ammonium ester when the tert-amine/alkyl haloalkanoate reaction is conducted in a liquefied gas as the solvent and the hydrolysis is conducted in a liquefied gas solvent or a polar aprotic solvent in which the betaine is substantially insoluble. In a preferred embodiment, the tert-amine is an N-alkyldimethylamine, the haloalkanoate is ethyl chloroacetate, and the liquefied gas is carbon dioxide.Type: GrantFiled: July 1, 1991Date of Patent: April 14, 1992Assignee: Ethyl CorporationInventors: Joe D. Sauer, Kim R. Smith, James E. Borland, Jeffrey W. Perine
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Patent number: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Patent number: 5082930Abstract: This invention relates to bifunctional coupling agents useful in forming conjugates with biologically useful molecules, such as antibodies. These conjugates can be complexed with radionuclide metal ions to provide materials useful for in vivo diagnostic and therapeutic applications.Type: GrantFiled: November 23, 1988Date of Patent: January 21, 1992Assignee: Mallinckrodt Medical, Inc.Inventors: Robert A. Nicolotti, Richard T. Dean
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Patent number: 5081293Abstract: Betaines are produced in solid form by reacting the corresponding quaternary ammonium ester with a base, such as sodium hydroxide, in a polar aprotic solvent in which the betaine is substantially insoluble, the ester being the product obtained by reacting a tert-amine, such as an N-alkyldimethylamine, with an alkyl haloalkanoate. The haloalkanoate is preferably a compound corresponding to the formula X(CH.sub.2).sub.n COOZ in which X is chloro, bromo, or iodo; Z is an alkyl group containing 1-6 carbons; and n is an integer of 1-6. A preferred solvent for use in the process is 2-butanone.Type: GrantFiled: February 8, 1991Date of Patent: January 14, 1992Assignee: Ethyl CorporationInventors: James E. Borland, Jeffrey W. Perine, Joe D. Sauer, Kim R. Smith
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Patent number: 5079380Abstract: A process for producing glycinonitrile under substantially adiabatic reaction conditions by reacting in a tubular reactor hydrogen cyanide, formaldehyde and ammonia. The excess ammonia is flashed off and the remaining solution volatiles are evaporated and condensed to product. The resulting glycinonitrile can be saponified to the alkali metal glycinate, from which glycine can be prepared.Type: GrantFiled: May 23, 1990Date of Patent: January 7, 1992Assignee: W. R. Grace & Co.-Conn.Inventor: Jon C. Thunberg
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Patent number: 5075498Abstract: Betaines are produced in solid form by reacting a tert-amine with a haloalkanoate salt when the reaction is conducted in a polar aprotic solvent in which the betaine is substantially insoluble. In a preferred embodiment, the tert-amine is an N-alkyldimethylamine, the haloalkanoate is sodium chloroacetate, and the solvent is ethyl acetate.Type: GrantFiled: February 8, 1991Date of Patent: December 24, 1991Assignee: Ethyl CorporationInventors: Jeffrey W. Perine, Kim R. Smith, Joe D. Sauer, James E. Borland
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Patent number: 5072041Abstract: The invention relates to new pure D- or L-N-hydroxy-alpha-amino acids and the derivatives thereof, including optically active N-hydroxy-phenylglycine amide, which has antibiotic and antitumor activity.Type: GrantFiled: November 1, 1989Date of Patent: December 10, 1991Assignee: Stamicarbon B.V.Inventors: Johan Kamphuis, Wilhelmus H. J. Boesten
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Patent number: 5068351Abstract: The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which n is 1 or 2, R denotes hydrogen or an organic radical, R.sup.1 denotes an organic radical, R.sup.2 and R.sup.3 are identical or different and denote hydrogen or an organic radical, and R.sup.4 and R.sup.5, together with the atoms bearing them, form a monocyclic, bicyclic or tricyclic heterocyclic ring system having 5 to 15 carbon atoms, which process comprises reacting compounds of the formula II defined in the description with compounds of the formula IV defined in the description, in the presence of phosphinic anhydrides of the formula III, where appropriate eliminating radicals which have been introduced to protect other functional groups and, where appropriate, esterifying free carboxyl groups in a manner known per se.Type: GrantFiled: July 27, 1990Date of Patent: November 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Volker Teetz, Hans Wissmann, Hansjorg Urbach
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Patent number: 5066647Abstract: A stable rapidly dissolving lyophilized composition of cyclophosphamide and alanine is provided.Type: GrantFiled: September 17, 1990Date of Patent: November 19, 1991Assignee: Erbamont, Inc.Inventors: Nageswara R. Palepu, Julie A. Hutt
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Patent number: 5055591Abstract: The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which n is 1 or 2, R denotes hydrogen or an organic radical, R.sup.1 denotes an organic radical, R.sup.2 and R.sup.3 are identical or different and denote hydrogen or an organic radical, and R.sup.4 and R.sup.5, together with the atoms bearing them, form a monocyclic, bicyclic or tricyclic heterocyclic ring system having 3 to 15 carbon atoms, which process comprises reacting compounds of the formula II defined in the description with compounds of the formula III defined in the description, in the presence of alkanephosphonic anhydrides, where appropriate eliminating radicals which have been introduced to protect other functional groups and, where appropriate, esterifying free carboxyl groups in a manner known per se.Type: GrantFiled: March 23, 1988Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Hansjorg Urbach, Rainer Henning, Hans Wissmann, Volker Teetz
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Patent number: 5043424Abstract: A peptide or protein is modified by reacting a phosphoric acid ester represented by the following general formula (I) with a peptide or protein: ##STR1## wherein R.sub.1 means a linear or branched, C.sub.1-36 alkyl or C.sub.2-36 alkenyl group whose hydrogen atom or atoms may be substituted by the corresponding number of fluorine atom(s) or a phenyl group substituted by at least one linear or branched C.sub.1-15 alkyl group, R.sub.2 denotes a C.sub.2-3 alkylene group, m stands for a number of 0-30, and M is a hydrogen atom, an alkali metal ion, an alkaline earth metal ion, an ammonium ion, an alkylamine residue or an alkanolamine residue.Type: GrantFiled: October 21, 1988Date of Patent: August 27, 1991Assignee: Kao CorporationInventors: Akira Matsunaga, Nobutaka Horinishi, Junya Wakatsuki, Takashi Imamura, Tomihiro Kurosaki
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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: 4988789Abstract: An improved process for preparing glycine hydrochloride in a high purity and high yield employing water as the solvent.Type: GrantFiled: January 5, 1990Date of Patent: January 29, 1991Assignee: Sandoz Ltd.Inventor: Jerome Linder
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Patent number: 4986976Abstract: Glycine and sodium sulfate decahydrate are separated from a starting aqueous solution containing glycine, sodium sulfate, and impurities, by forming a slurry which is a solid mixture of glycine and sodium sulfate decahydrate, followed by separation of the mixed crystals.Type: GrantFiled: April 11, 1989Date of Patent: January 22, 1991Assignee: W. R. Grace & Co.-Conn.Inventor: Jon C. Thunberg
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Patent number: 4968839Abstract: A process for synthetically producing N,N-Dimethyl Glycine, commonly referred to as DMG, through the neutralization of N,N-dimethyl glycine sodium salt with sulfuric acid wherein the N,N-dimethyl glycine sodium salt is prepared by reacting formaldehyde, sodium bisulfite, dimethyl amine, and sodium cyanide followed by agitation with caustic soda beads. Through the preparation and intermediate steam distillation and isolation of N,N-Dimethylamino acetonitrile. The nitrile solution is subjected to caustic hydrolysis then is subsequently neutralized leaving DMG in methanol extraction solvent. The methanol is removed in an azeotropic distillation step to produce DMG in a high yield, low cost and excellent quality.Type: GrantFiled: August 16, 1989Date of Patent: November 6, 1990Assignee: Foodscience CorporationInventor: C. Wayne Noell
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Patent number: 4962231Abstract: A pure D- or L-alanine enantiomer is prepared by reacting an optically active chloropropionic acid with ammonia in water or a water/alcohol mixture at from 50.degree. to 110.degree. C.Type: GrantFiled: June 10, 1988Date of Patent: October 9, 1990Assignee: BASF AktiengesellschaftInventors: Axel Paul, Peter Tonne, Eckhard Roske, Hardo Siegel
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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: 4925978Abstract: A new process of synthesis of optically active .alpha.-amino acids is described through nitrosation in a non-aqueous, aprotic system, of the corresponding N-carbamyl derivatives followed by decomposition of the thus obtained N-nitroso derivatives in aqueous acidic medium. The process, which is of a general applicability, leads to a remarkable increase in the reaction yields, due to the suppression of the main side reaction leading to the corresponding .alpha.-hydroxy-acid. Some N-nitroso intermediates, which can be recovered from the process of the invention, are also described.Type: GrantFiled: April 14, 1988Date of Patent: May 15, 1990Assignee: Eniricerche S.p.A.Inventors: Sandro Di Gioacchino, Antonio Paolinelli, Luciano Re
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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: 4855493Abstract: Amine-carboxyboranes (boron analogues of amino acids) which demonstrate sificant antitumor and antihyperlipidemic (cholesterol and /or triglyceride lowering) activities are disclosed.Type: GrantFiled: July 7, 1986Date of Patent: August 8, 1989Assignee: The United States of America, as represented by the Secretary of the ArmyInventors: Bernard F. Spielvogel, Andrew T. McPhail, Iris H. Hall
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Patent number: 4837332Abstract: Amino acid salt having at least one unblocked amino group and comprising at least one cation which has a nitrogen cationic atom is reacted with 1-(tertiary-alkoxycarbonyl)imidazole in the liquid phase and in the presence of essentially inert organic solvent having a dielectric constant at 25.degree. C. of at least about 4, to produce N-(tertiary-alkoxycarbonyl)-blocked amino acid salt.Type: GrantFiled: March 7, 1986Date of Patent: June 6, 1989Assignee: PPG Industries, Inc.Inventor: Chih-Yueh Chou
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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: 4804500Abstract: Amino acids can be produced from suitable tertiary and secondary amines by dealkylation using an alkali metal hydroxide.Type: GrantFiled: March 19, 1986Date of Patent: February 14, 1989Assignee: Monsanto CompanyInventors: William H. Miller, Terry M. Balthazor
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Patent number: 4801742Abstract: Formylating the amino nitrogen of an alkali metal salt of an amino carboxylic acid, by reacting the salt with an alkyl formate in an alkanol solvent. In one embodiment, the alkyl formate is added to the reaction as such; in another embodiment, the alkyl formate is formed in situ by reaction of carbon monoxide with the alkanol solvent in the presence of the alkali metal salt of the amino carboxylic acid. The process provides a new class of compounds, the alkali metal salts of N-formyl-aspartic acids.Type: GrantFiled: July 17, 1987Date of Patent: January 31, 1989Assignee: W. R. Grace & Co.-Conn.Inventors: Jennifer M. Quirk, Charles G. Carter, Robert J. Kupper
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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: 4789757Abstract: The amine nitrogen of an amino carboxylic acid is formylated by reacting the amino carboxylic acid with formamide.Type: GrantFiled: July 17, 1987Date of Patent: December 6, 1988Assignee: W. R. Grace & Co.-Conn.Inventor: Charles G. Carter
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Patent number: 4762829Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.Type: GrantFiled: October 23, 1986Date of Patent: August 9, 1988Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
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Patent number: 4746380Abstract: The invention relates to a new explosive compound which is an associated compound of ammonium nitrate and glycine and also includes explosive composition containing this compound.The compound ANGC is prepared by a crystallization process preferably effected by cooling a melt or saturated solution containing ammonium nitrate and glycine.ANGC is especially advantageous as an ingredient of low water content emulsion explosive compositions.Type: GrantFiled: May 26, 1987Date of Patent: May 24, 1988Assignee: Imperial Chemical Industries PLCInventors: John Cooper, Vladmir Sujansky
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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: 4710574Abstract: Disclosed is the hydrocarboxylation of defined enamides with CO and a compound ROH to make amino acids or amido esters, either of which can be hydrolyzed to .alpha.-amino acids.Type: GrantFiled: November 16, 1983Date of Patent: December 1, 1987Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, James D. Burrington
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Patent number: 4684483Abstract: An N-substituted amino acids can be prepared by the steps of: bringing together under reaction condition glyoxal and a source of sulfur dioxide in an aqueous medium to produce a sulfonated intermediate; and introducing into said medium a nitrogen compound selected from the group consisting of ammonia, a primary amine, and a secondary amine, into said medium containing said intermediate to produce said N-substituted amino acid.Type: GrantFiled: September 23, 1985Date of Patent: August 4, 1987Assignee: Monsanto CompanyInventors: Thomas J. Richard, William H. Miller
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Patent number: 4677224Abstract: The device for carrying out the continuous process for synthesizing an .alpha.-amino acid incorporates: (a) a vessel (10) for feeding .alpha.-amino-nitrile, or one of its salts; (b) a connecting pipe (12), in which a pump (14) is mounted, connecting the feed vessel (10) to (c) a catalysis column (16) containing a carbonyl-containing polymeric resin (18) which is insoluble in basic aqueous medium; (d) a connecting pipe (20) from the catalysis column (16) to (e) a hydrolysis reactor (22), acting simultaneously as a reservoir for the .alpha.-amino acid salt formed, and equipped with (f) means for feeding hydroxide ions, comprising a feed vessel (24), a pipe (26) and a pump (28); and (g) a pipe (30) for drawing off the .alpha.-amino acid salt formed.Type: GrantFiled: June 3, 1985Date of Patent: June 30, 1987Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Auguste Commeyras, Jacques Taillades, Jean Brugidou, Louis Mion, Regine Sola, Robert Pascal, Monique Lasperas, Alain Rousset
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Patent number: 4667054Abstract: This invention relates to a process for producing optically active valine, characterized by optically resolving DL-valine hydrochloride in a solvent containing an amine salt, a sulfonic acid or a carboxylic acid and isolating optically active valine after the decomposition of the obtained optically active valine hydrochloride.Type: GrantFiled: January 30, 1986Date of Patent: May 19, 1987Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshinobu Miyazawa, Noriko Ooishi, Shigeru Aoki, Yasuhisa Tashiro