Phenyl Alanines Patents (Class 562/445)
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Patent number: 5525631Abstract: A composition which comprises a pharmaceutically acceptable carrier and an active ingredient, such active ingredient comprising L-DOPA ethyl ester derived from its crystaline form in an amount which is at least 97%, by weight, of the active ingredient, and L-DOPA in an amount which is less than 1% by weight of such active ingredient is provided by this invention. This invention also provides a process for preparing such a composition. Further, this invention provides a method of treating a patient suffering from Parkinson's disease which comprises administering to a patient a pharmaceutical composition comprising a therapeutically effective amount of L-DOPA ethyl ester derived from its crystaline form and a pharmaceutically acceptable carrier.Type: GrantFiled: July 18, 1994Date of Patent: June 11, 1996Assignees: The Yissum Research Development Company of the Hebrew University of Jerusalem, Teva Pharmaceutical Industries, Ltd.Inventors: Isaac Milman, Alexander Veinberg, Daphne Atlas, Eldad Melamed
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Patent number: 5514716Abstract: This disclosure relates to a novel class of hydroxamic and carboxylic acid based matrix metalloproteinase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of matrix metalloproteinase induced diseases.Type: GrantFiled: February 25, 1994Date of Patent: May 7, 1996Assignee: Sterling Winthrop, Inc.Inventors: Madhusudhan R. Gowravaram, Jeffrey Johnson, Ewell R. Cook, Robert C. Wahl, Alan M. Mathiowetz, Bruce E. Tomczuk, Ashis K. Saha
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Patent number: 5503776Abstract: An N-acylamino acid compound represented by the general formula (1):R--CO--(NH--X--CO).sub.n --OR.sup.1 (1)wherein (NH--X--CO) is an amino acid residue, X in (NX--X--CO) is variable with the kind of amino acid to be used, R--CO is a saturated or an unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid is disclosed, which is obtained by causing an N-hydroxysuccinimide ester to react with an amino acid or a peptide.The compound excels in antioxidizing power, emulsifying power, antibacterial power, chelating power, infrared absorbing power, and humidity-retaining power.Type: GrantFiled: December 21, 1994Date of Patent: April 2, 1996Assignees: National Food Research Institute Ministry of Agriculture, Forestry and Fisheries, CCI CorporationInventors: Hironobu Murase, Tsutomu Kunieda, Akihiko Nagao, Junji Terao
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Patent number: 5496927Abstract: This invention relates to analogs of peptidase substrates in which the amide group containing the scissile amide bond of the substrate peptide has been replaced by an activated electrophilic ketone moiety. These analogs of the peptidase substrates provide specific enzyme inhibitors for a variety of proteases, the inhibition of which will have useful physiological consequences in a variety of disease states.Type: GrantFiled: May 25, 1994Date of Patent: March 5, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: H. Michael Kolb, Joseph P. Burkhart, Michel J. Jung, Fritz E. Gerhart, deceased, Eugene L. Giroux, Bernhard Neises, Daniel G. Schirlin
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Patent number: 5472980Abstract: A method for administering pyruvate is disclosed which comprises administering a therapeutically effective amount of a pyruvate precursor to a mammal in the form of pyruvamide or a pyruvyl-amino acid. The pyruvyl-amino acid is preferably selected from the group comprising pyruvyl-glycine, pyruvyl-alanine, pyruvyl-leucine, pyruvyl-valine, pyruvyl-isoleucine, pyruvyl-phenylalanine, pyruvyl-proline and pyruvyl-sarcosine, and their amides and esters as well as their salts. Associated with the administration of a pyruvate precursor to a mammal in accordance with this invention are improved insulin resistance, lower fasting insulin levels, and reduced fat gain. Novel methods of synthesizing several pyruvate precursors are also disclosed.Type: GrantFiled: August 4, 1994Date of Patent: December 5, 1995Assignee: Abbott LaboratoriesInventor: Robert H. Miller
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Patent number: 5466864Abstract: The present invention provides crystals of L-phenylalanine monomethyl sulfate which have low solubility compared to L-tyrosine and D-phenylalanine. The L-phenylalanine monomethylsulfate crystals are obtained by subjecting a solution containing monomethyl sulfuric acid and phenylalanine to crystallization.Further, the present invention also provides a process for recovering L-phenylalanine from a water layer by neutralizing the esterified reaction, extracting an ester of L-phenylalanine therefrom with an organic solvent, and recovering remaining L-phenylalanine in the water layer as L-phenylalanine monomethylsulfate. L-phenylalanine monomethyl sulfate is obtained by esterifying L-phenylalanine and methanol in the presence of sulfuric acid, neutralizing the esterified solution with a base in the presence of water, extracting the produced L-phenylalanine methyl ester from the neutralized solution with an organic solvent, and then crystallized the resultant water layer under acidic condition.Type: GrantFiled: February 2, 1994Date of Patent: November 14, 1995Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Toyoto Hijiya, Teruo Yonekawa, Chiaki Mochizuki
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Patent number: 5463116Abstract: Stable crystals of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine may be produced by treating this compound with a solvent at a temperature of at least 10.degree. C. and forming crystals in the solvent at a temperature of at least 10.degree. C. For example, crystals may be formed by crystallization out of solution, or may be formed from solid particles of the compound suspended in a solvent. Crystals formed in this way have different melting point, infra red spectrum and X-ray diffraction patterns from previously known forms of the compound and have enhanced processability, e.g., stability to grinding.Type: GrantFiled: February 2, 1994Date of Patent: October 31, 1995Assignee: Ajinomoto Co., Inc.Inventors: Michito Sumikawa, Yoshihito Koguchi, Takao Ohgane, Yasuo Irie, Satoji Takahashi
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Patent number: 5455229Abstract: The present invention is a method for minimizing and containing injury caused when tissue is subject to ischemia and reperfusion. The method comprises administering certain derivatized tripeptide arginal compounds concurent with, or immediately after, reestablishing blood flow to the ischemic tissue. The method is particularly useful for minimizing and containing damage to the heart during evolving myocardial infarction.Type: GrantFiled: December 23, 1992Date of Patent: October 3, 1995Assignee: Eli Lilly and CompanyInventors: Richard A. Hahn, Brian R. MacDonald, Robert T. Shuman, Gerald F. Smith
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Patent number: 5444049Abstract: A compound of formula (I): ##STR1## in which: R.sub.1 represents hydrogen or acyl, alkyl, benzyl, alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, 5-[(dimethyl)amino]naphthylsulfonyl, alkoxycarbonylmethyl or carboxymethyl,R.sub.2 represents hydrogen or phenyl, substituted or unsubstituted benzyl, 3-thienylmethyl, 2-pyridylmethyl, diphenylmethyl, fluorenyl, naphthylmethyl, benzocyclobutyl, (dicyclopropylmethyl)methyl, indanyl or (C.sub.3 -C.sub.7 cycloalkyl)methyl,R'.sub.2 represents hydrogen or benzylor alternativelyR.sub.2 and R'.sub.2 together represent C.sub.6 H.sub.5 --CH.dbd.,R.sub.3 represents substituted alkyl or guanidinophenyl, amidinophenyl, aminophenyl, guanidinobenzyl, amidinobenzyl, aminobenzyl or cycloalkyl,R.sub.4 and R.sub.5 each represent hydrogen or alkyl, or ##STR2## forms a boronic ester of pinanediol, A represents any one of the groups as defined in the description.Medicinal products.Type: GrantFiled: February 22, 1994Date of Patent: August 22, 1995Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Christine Lila, Michel Laubie, Tony Verbeuren, Serge Simonet, Alain Rupin, Bernard Portevin
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Patent number: 5432262Abstract: Mixture containing .alpha.-L-aspartyl-L-phenylalanine methyl ester and 3-benzyl-6-carboxymethyl-2,5-dioxopiperazine are brought into contact with hydrochloric acid in an aqueous solvent to precipitate .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride and 3-benzyl-6-carboxymethyl-2,5-dioxopiperazine, which are then separated from each other by classification.Type: GrantFiled: January 12, 1993Date of Patent: July 11, 1995Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Katsumi Sugiyama
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Patent number: 5420297Abstract: A substance P antagonistic peptide of the following formula is disclosed: ##STR1##Type: GrantFiled: April 21, 1992Date of Patent: May 30, 1995Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masaaki Matsuo, Daijiro Hagiwara, Hiroshi Miyake
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Patent number: 5411964Abstract: A phenylalanine-glycine compound of formula (I): ##STR1## wherein R represents a residue of an antitumor substance, or a salt or ester thereof, a process for preparation thereof, and a pharmaceutical composition containing the same are described. The novel conjugate of the phenylalanine-glycine compound and the antitumor substance exhibits superior antitumor activity in comparison with the case wherein an antitumor substance is administered alone or as a mixture with phenylalanine.Type: GrantFiled: March 15, 1993Date of Patent: May 2, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Koichi Niimura, Takako Kawabe, Takao Ando, Kenichi Saito
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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: 5389680Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: October 18, 1993Date of Patent: February 14, 1995Assignee: Monsanto CompanyInventor: Peter G. Ruminski
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Patent number: 5380713Abstract: This invention relates to novel arginine aldehydes, their salts and hydrates, which compounds selectively exhibit serine proteases inhibitory activity, are highly stable in aqueous solutions, and are useful for anti-trypsin and anti-thrombin activity.Type: GrantFiled: April 11, 1994Date of Patent: January 10, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Neelakantan Balasubramanian, Denis R. St. Laurent
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Patent number: 5359124Abstract: New .beta.-phenylisoserine derivative of formula (I), its preparation and its use as intermediate in the synthesis of taxol or of its derivatives.Type: GrantFiled: August 21, 1992Date of Patent: October 25, 1994Inventors: Jean-Pierre Duchesne, Michel Mulhauser
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Patent number: 5359128Abstract: The invention comprises compositions and methods for the treatment of psoriasis.Type: GrantFiled: February 11, 1993Date of Patent: October 25, 1994Inventor: Izhak Blank
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Patent number: 5354885Abstract: A composition which comprises a pharmaceutically acceptable carrier and an active ingredient, such active ingredient comprising L-DOPA ethyl ester in an amount which is at least 97%, by weight, of the active ingredient, and L-DOPA in an amount which is less than 1% by weight of such active ingredient is provided by this invention. This invention also provides a process for preparing such a composition. Further, this invention provides a method of treating a patient suffering from Parkinson's disease which comprises administering to a patient a pharmaceutical composition comprising a therapeutically effective amount of L-DOPA ethyl ester and a pharmaceutically acceptable carrier.Type: GrantFiled: December 24, 1992Date of Patent: October 11, 1994Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem, Teva Pharmaceutical Industries Ltd.Inventors: Isaac Milman, Alexander Veinberg, Daphne Atlas, Eldad Melamed
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Patent number: 5312826Abstract: Disclosed are a dicarboxylic acid compound represented by the formula (I): ##STR1## wherein R represents hydrogen atom, a lower alkyl group, phenyl group or hydroxyl group; R.sup.1 represents a straight or branched alkyl group having 1 to 10 carbon atoms or a lower alkyl group substituted by a group selected from aryl group, a sulfur- or nitrogen-containing heterocyclic monocyclic group and a cycloalkyl group having 4 to 8 carbon atoms; R.sup.2 represents a substituted or unsubstituted aryl group, a cycloalkyl group having 4 to 8 carbon atoms or a sulfur-containing or nitrogen-containing heterocylcic group; X represents sulfur atom, oxygen atom or a substituted or unsubstituted imino group; Y.sup.1 represents imino group, oxygen atom or sulfur atom and Y.sup.2 represents nitrogen atom, or Y.sup.1 represents a vinylene group and Y.sup.2 represents a group: --CH.dbd.Type: GrantFiled: June 19, 1992Date of Patent: May 17, 1994Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ken-ichi Nunami, Tameo Iwasaki, Kazuo Matsumoto, Koji Yano, Isao Yamaguchi
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Patent number: 5300653Abstract: A method is provided for the separation of at least one aromatic amino acid from an aqueous solution of mixed amino acids including the aromatic amino acid. The aqueous solution is brought into contact with a strongly acidic gel-type cation exchange resin which has been converted into a salt with an alkali metal or an alkaline earth metal, whereby the aromatic amino acid is selectively sorbed by the cation exchange resin. The aromatic amino acid thus sorbed can then be desorbed from the ion exchange resin, preferably with water.Type: GrantFiled: December 23, 1992Date of Patent: April 5, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shohei Nozaki, Naohiro Murata, Kiyoo Miyazaki
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Patent number: 5288901Abstract: There are provided important pyrroline and glycine intermediates, methods for the preparation of said intermediates and the use thereof in the manufacture of arylpyrrole insecticidal agents.Type: GrantFiled: April 8, 1992Date of Patent: February 22, 1994Assignee: American Cyanamid CompanyInventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
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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: 5258398Abstract: This invention relates to novel diaminoalkanoic acid derivatives that inhibit platelet aggregation and thrombus formation in mammalian blood thereby being useful in the prevention and treatment of thrombosis associated with disease states such as myocardial infarction, stroke, peripheral arterial disease and disseminated intravascular coagulation, to pharmaceutical compositions including such compounds, and to their use in inhibiting thrombus formation and platelet aggregation in mammals.Type: GrantFiled: December 16, 1991Date of Patent: November 2, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Scott I. Klein, Bruce F. Molino
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Patent number: 5254726Abstract: A method for synthesizing no-carrier-added (NCA) aryl [.sup.18 F] fluoride substituted aromatic aldehyde compositions bearing an electron donating group is described. The method of the present invention includes the step of reacting aromatic nitro aldehydes having a suitably protected hydroxyl substitutent on an electron rich ring. The reaction isThe U.S. Government has rights in this invention pursuant to Contract Number DE-AC02-76CH00016, between the U.S. Department of Energy and Associated Universities Inc.Type: GrantFiled: June 7, 1991Date of Patent: October 19, 1993Assignee: The United States of America as represented by the Department of EnergyInventors: Yu-Shin Ding, Joanna S. Fowler, Alfred P. Wolf
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Patent number: 5242903Abstract: Renin-inhibiting peptides of the formula ##STR1## in which X represents a group of the formula ##STR2## represents hydroxyl, alkoxy having up to 8 carbon atoms, benzyloxy or a group of the formula --NR.sup.4 R.sup.5,A, B, D and E are identical or different and in each caserepresent a direct bond,represent a radical of the formula ##STR3## in which Z denotes oxygen, sulphur or the methylene grouprepresents a grouping of the formula ##STR4## m represents a number 0, 1 or 2, and L represents a group of the formula --CH.sub.2 --NR2R.sub.3and physiologically acceptable salts thereof.Type: GrantFiled: October 2, 1991Date of Patent: September 7, 1993Assignee: Bayer AktiengesellschaftInventors: Wolfgang Bender, Gunther Kinast, Andreas Knorr, Johannes-Peter Stasch
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Patent number: 5238958Abstract: The present invention is novel substituted .alpha.-amino acids, pharmaceutical compositions, methods of use, and preparations therefore having utility for treating disorders which benefit from blockade of aspartate and glutamate receptors.Type: GrantFiled: April 23, 1990Date of Patent: August 24, 1993Assignee: Warner-Lambert CompanyInventors: Graham Johnson, Thomas C. Malone, Perry M. Novak
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Patent number: 5206413Abstract: A method for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester (.alpha.-APM), substantially free from acid ion contamination, is disclosed which comprises the steps of contacting a solution of a mineral acid salt or an organic sulfonic acid salt of .alpha.-APM in an aqueous solvent with an anion exchange resin in free base form, separating the resin from the thus-produced solution of .alpha.-APM; and isolating the .alpha.-APM therefrom, preferably with regeneration and recycling the resin.Type: GrantFiled: June 14, 1990Date of Patent: April 27, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masanobu Ajioka, Takeshi Oura, Chojiro Higuchi, Toshio Katoh, Akihiro Yamaguchi
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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: 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: 5140011Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in claim 1, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.Type: GrantFiled: March 29, 1990Date of Patent: August 18, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Quirico Branca, Hans P. Marki, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
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Patent number: 5130472Abstract: The present invention relates to a new process for the preparation of Erbstatin and Erbstatin analogs, which can be represented by the following formula (I) ##STR1## wherein R is hydrogen, a lower alkyl or a lower alkanoyl group;n is an integer of 1 to 3;A is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --;R.sub.1 is hydrogen or a lower alkyl group, andR.sub.2 is a hydrogen or halogen atom.Type: GrantFiled: November 2, 1990Date of Patent: July 14, 1992Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Franco Buzzetti, Angelo Crugnola, Paolo Lombardi
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Patent number: 5118815Abstract: A method for crystallization of an amino acid characterized by allowing a surfactant and/or an alcohol to exist upon crystallization.Type: GrantFiled: October 15, 1990Date of Patent: June 2, 1992Assignee: Ajinomoto Co., Inc.Inventors: Yoshinari Shiroshita, Ryuta Toyomasu, Masura Saeki
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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: 5095006Abstract: Renin-inhibiting peptides of the formula ##STR1## in which X represents a group of the formula ##STR2## represents hydroxyl, alkoxy having up to 8 carbon atoms, benzyloxy or a group of the formula --NR.sup.4 R.sup.5,A, B, D and E are identical or different and in each caserepresent a direct bond,represent a radical of the formula ##STR3## in which Q1 denotes oxygen, sulphur or the methylene grouprepresent a grouping of the formula ##STR4## m represents a number 0, 1 or 2, and L represents a group of the formula --CH.sub.2 NR.sup.2 R.sup.3and physiologically acceptable salts thereof.Type: GrantFiled: July 13, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Wolfgang Bender, Gunther Kinast, Andreas Knorr, Johannes-Peter Stasch
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Patent number: 5055451Abstract: Thiol protease inhibitors are disclosed having the formula: ##STR1## or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein:n is 0 or 1;m is 0, 1 or 2;X is H or an N-protecting group;each Y is independently an optionally protected .alpha.-amino acid residue;R is an optionally protected .alpha.-amino acid side chain that is H or CH.sub.3 or that is bonded to the .alpha.-carbon atom to which it is attached by a methylene, methine or phenyl radical; andR' is optionally substituted aryl.Type: GrantFiled: December 7, 1987Date of Patent: October 8, 1991Assignee: Syntex Inc.Inventors: Alexander Krantz, Heinz W. Pauls, Roger A. Smith, Robin W. Spencer
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Patent number: 5041644Abstract: New peptide derivatives .beta.-chloro-L-(Z)-dehydroglutamic acid are described which display antibacterial activity.Type: GrantFiled: June 27, 1988Date of Patent: August 20, 1991Assignee: Merck & Co., Inc.Inventors: Yoshiharu Morita, Ryoichi Ando, Junko Takashima, Louis Chaiet
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Patent number: 5023268Abstract: Compounds related to 3-phenoxy (or phenylthio) cyclopentanecarbonylamino acid, processes for their preparation, and treating agents for cerebral edema containing the compounds as active ingredients are described. The compounds are represented by the following formula: ##STR1## The compounds of the present invention and their non-toxic salts have a potent inhibitory effect on the development of cerebral edema.Type: GrantFiled: September 8, 1989Date of Patent: June 11, 1991Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Tadao Okegawa, Yoshinobu Arai
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Patent number: 4994605Abstract: A method for crystallizing alpha-L-aspartyl-L-phenylalanine methyl ester (APM) is disclosed. The APM is crystallized from a C.sub.1 -C.sub.3 -alcohol/water solution (30-80:70-20 (v/v)). The ester crystallized by (i) concentrating the solution, (ii) cooling the solution, (iii) adjusting the water:alcohol ratio, or (iv) a combination thereof.Type: GrantFiled: April 25, 1989Date of Patent: February 19, 1991Assignee: Ajinomoto Co., Inc.Inventors: Shinichi Kishimoto, Katsumi Sugiyama
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Patent number: 4956489Abstract: The invention relates to the preparation of water-soluble L-tyrosine derivatives having the formula ##STR1## where R.sub.1 is a L-malyl, L-lactyl, L-glutamyl or L-aspartyl group, R.sub.2 is a --OH, --OM, methoxy, ethoxy or amino group and M is an alkaline metal, by enzymatic condensation of an acid selected among L-malic, L-lactic, L-glutamic and L-aspartic acids, with a L-tyrosine derivatives selected among the ethyl and methyl esters and the amide of L-tyrosine. The enzyme is obtained from a culture of Micrococcus casealyticus. The compounds where R.sub.1 is a L-malyl or L-lactyl group are new. Said L-tyrosine derivatives are useful in cosmetic and pharmaceutical compositions, such as tanning and sun compositions.Type: GrantFiled: October 14, 1988Date of Patent: September 11, 1990Assignee: BioeuropeInventors: Daniel H. Auriol, Francois B. Paul, Pierre F. Monsan
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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: 4925945Abstract: The present invention provides compounds of the general formula: ##STR1## wherein A is an amine-substituted aromatic radical and X is a hydrocarbon radical containing up to 10 carbon atoms.The present invention also provides a process for the preparation of these compounds.Furthermore, the present invention is concerned with the use of the compounds for introducing SH groups into tyrosine.Type: GrantFiled: March 22, 1989Date of Patent: May 15, 1990Assignee: Boehringer Mannheim GmbHInventors: Christian Klein, Peter Kirch
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Patent number: 4925651Abstract: The use of 2-radiohalogenotyrosine derivatives of the formula I ##STR1## in which X denotes a radioactive halogen, in particular fluorine-18, bromine-75 or iodine-123, and R denotes hydrogen or methyl, in particular of 2-fluoro(18)-tyrosine and -methyltyrosine (II) for emission-tomographic measurement of protein synthesis in vivo, in particular for the purposes of cerebral diagnosis, by means of SPECT and, in particular, by means of PET, provides, in view of the particularly high incorporation rate, especially of II, the possibility of quantitative kinetic evaluation and is thus of great interest, specifically in the framework of tumor diagnosis.Type: GrantFiled: December 7, 1988Date of Patent: May 15, 1990Assignee: Kernforschungsanlage Juelich Gesellschaft mit beschrankter HaftungInventors: Heinz H. Coenen, Peer Kling, Gerhard Stoecklin
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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: 4879398Abstract: A process for making 2,6-disubstituted tyrosine by the noble metal coupling of a disubstituted aromatic halide or diazonium salt with an amino-protected 2-aminoacrylic acid to form a (Z)-.beta.-(disubstituted phenyl)-.alpha.-acylaminoacrylate, and asymmetrically hydrogenating the acrylate to produce the 2,6-disubstituted tyrosine.Type: GrantFiled: December 31, 1987Date of Patent: November 7, 1989Assignee: Monsanto CompanyInventors: Daniel P. Getman, Roy A. Periana, Dennis P. Riley
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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: RE34878Abstract: A compound of D-phenylalanine derivative for hypoglycemic use, represented by the general formula ##STR1## R.sup.1 is selected from hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 12 carbon atoms, aralkyl of 6 to 12 carbon atoms, ##STR2## --CH.sub.2 CO.sub.2 R.sup.3, --CH(CH.sub.3)--OCO--R.sup.3, and --CH.sub.2 --OCO--C(CH.sub.3).sub.3 ; R.sup.2 is selected from groups comprising aryl of 6 to 12 carbon atoms, a hetero six-membered ring, a hetero five-membered ring, cycloalkyl, or cycloalkenyl, any of which groups may have one or more substituents; and R.sup.3 is selected from hydrogen and alkyl of 1 to 5 carbon atoms; the salts thereof, and precursors which can be converted thereto in the human or animal body.Some of the compounds are novel per se.Type: GrantFiled: November 23, 1993Date of Patent: March 14, 1995Assignee: Ajinomoto Co., Inc.Inventors: Shigeshi Toyoshima, Yoshiko Seto, Hisashi Shinkai, Koji Toi, Izumi Kamashiro