Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: The amine nitrogen of an amino carboxylic acid is formylated by reacting the amino carboxylic acid with formamide.

Abstract: A 6-keto-prostaglandin E.sub.1 derivative of the formula: ##STR1## (wherein R.sup.1 represents an amino acid or amino alcohol residue, R.sup.2 represents a single bond or an alkylene group of from 1 to 4 carbon atoms, R.sup.3 represents (i) an alkyl group of from 1 to 8 carbon atoms, (ii) a cycloalkyl group of from 4 to 7 carbon atoms, which may be unsubstituted or substituted by at least one alkyl group of from 1 to 8 carbon atoms or (iii) a phenyl or phenoxy group, which may be unsubstituted or substituted by chlorine, trifluoromethyl or alkyl of from 1 to 3 carbon atoms, provided that when R.sup.2 represents a single bond R.sup.3 does not represent phenoxy)cyclodextrin clathrates thereof and non-toxic salts thereof possess selective cytoprotective activity.

Abstract: A method for racemizing an optically active amino acid, which comprises heating the optically active amino acid in an aqueous solution under an alkaline condition in the presence of an alkali metal salt.

Abstract: .alpha.-Vinyl-.alpha.-aminocarboxylic acids of the general formula: ##STR1## where * indicates a center of asymmetry and R is hydrogen, deuterium, lower alkyl, allyl, benzyl, or benzyl substituted 1 to 3 times by alkyl, alkoxy, fluorine or chlorine and produced enantioselectively from L-methionine by a multistep process.

Abstract: A process for the recovery in substantially pure form of an amino acid represented by the formula ##STR1## from an aqueous production mixture by a low pressure temperature gradient chromatographic process is described.

Abstract: 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.

Abstract: Compounds having the formula: ##STR1##are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents and cytoprotective agents.

Abstract: ACE inhibitors containing amino acid esters of thiopropanoyl-L-3,4-dehydroproline are disclosed.

Abstract: Novel substituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acids and esters thereof are disclosed. The novel compounds have biological activity including decarboxylase inhibition.

Abstract: Adamantyl phenyl .beta.-alanines having the structure: ##STR1## wherein R is phenyl or substituted phenyl and one of R.sup.1 and R.sup.2 is NH.sub.2 and the other is CO.sub.2 H, are disclosed herein.

Abstract: The invention relates to a process for producing N-protected-.alpha.L-aspartyl-L-phenylalanine methyl ester, which comprises esterifying L-phenylalanine with methanol in the presence of a strong acid catalyst, adding, to the resulting solution, an aqueous alkaline solution to neutralize the acid catalyst and a water-immiscible organic solvent to extract the free L-phenylalanine methyl ester thus formed, collecting the organic layer, and reacting the L-phenylalanine methyl ester dissolved in said collected organic layer with N-protected-L-aspartic anhydride.

Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## the amido ester moiety of which is in the L-configuration, and pharmaceutically acceptable salts thereof are disclosed.

Abstract: A regioselective process for the preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester is disclosed. A controlled aqueous coupling reaction between .beta.-methyl-L-aspartate-N-carboxyanhydride and L-phenylalanine produces the aspartyl methyl ester of .alpha.-L-aspartyl-L-phenylalanine which is subsequently hydrolyzed and selectively esterified without isolation. The hydrochloride salt of .alpha.-L-aspartyl-L-phenylalanine methyl ester, which is selectively precipitated from the esterification mixture, can be neutralized to .alpha.-L-aspartyl-L-phenylalanine methyl ester.

Abstract: The present invention relates to a spherical amino acid having an average particle size of about 1 mm or below and a process for the preparation thereof.

Abstract: A process for preparing an N-acylphenylalanine represented by the formula (II): ##STR1## wherein R.sub.3 and R.sub.4 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, hydroxy or methylenedioxy group, and R denotes a methyl or phenyl group, which comprises catalytically reducing an N-acyl-.beta.-phenylserine represented by the formula (I): ##STR2## wherein R.sub.1 and R.sub.2 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, benzyloxy or methylenedioxy group, and R has the same meaning as defined in the formula (II), in the presence of a reducing catalyst or both reducing catalyst and acid, in a solvent.

Abstract: An absorption promoter is disclosed which interacts with hydrophobic amino acid residues of polypeptide derivative medications and substantially increases the absorption of that medication administered orally or rectally. The promoter and medication can be compounded into unit dosages in capsule, tablet, or suppository form, or combined into elixir solutions, suspensions, etc. The absorption promoters are phenylalanine derivatives which may be prepared through conventional N-acylation techniques.

Abstract: Novel .alpha.-allenic-.alpha.-amino acids which are enzyme inhibitors of the suicide or k.sub.cat type are disclosed herein.

Abstract: The invention relates to a process for the preparation of DL-.beta.-aryl-amino acids of the general Formula ##STR1## wherein R, R.sub.1 and R.sub.2 stand for hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro or C.sub.1-4 dialkylamino; wherebyin the case of monosubstituted derivatives R and R.sub.1 are hydrogen and R.sub.2 has the same meaning as stated above and can be attached to position 2, 3 or 4 related to the methylene group;in the case of disubstituted derivatives R is hydrogen and R.sub.1 and R.sub.2 have the same meaning as stated above and are attached to positions 2,3; 2,4; 2,5; 2,6; 3,4 or 3,5 related to the methylene group;in the case of trisubstituted derivatives R, R.sub.1 and R.sub.2 have the same meaning as stated above and are attached to positions 2,3,4; 2,3,5; 2,3,6; 3,4,5 or 3,4,6 related to the methylene group.

Abstract: A process for the extraction of aromatic (e.g., phenyl-containing) amino acids from an aqueous phase (solution) containing them, comprising combining the aqueous phase with a tenside of the formulaR--U--SO.sub.3 XwhereinR is alkyl or cycloalkyl each of 4-18 carbon atoms; or phenyl or naphthyl, each optionally substituted by alkyl groups, and having up to 18 carbon atoms total.U is a carbon-to-sulfur bond or an oxygen atom, andX is an alkali metal ion;acidifying the aqueous phase to a pH value of 2.0-2.5; andextracting the aqueous phase with an alcohol, a ketone, or a carboxylic acid alkyl ester, each containing 4-6 carbon atoms.

Abstract: A glycinamide derivative of the general formula I: ##STR1## wherein: R is a linear or ramified alkyl group C.sub.5 -C.sub.18, a linear or ramified alkenyl group C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9, C.sub.10, C.sub.11, C.sub.12, C.sub.13, C.sub.14, C.sub.15, C.sub.16, C.sub.17 or C.sub.18, a linear or ramified alkynyl group C.sub.4 -C.sub.10, a linear or ramified acyl group C.sub.4 -C.sub.18, a linear or ramified alkyl group C.sub.1 -C.sub.10, substituted by a phenoxy group, by a hydroxy radical, by an acetoxy radical, by a carboxy radical, by a linear or ramified alkoxycarbonyl group C.sub.1 -C.sub.4, by a carbonyl radical, by a carboxaldehyde group, by an acetal or cetal group, by one or more phenyl groups, by one or more phenyl groups substituted by a halogen atom such as fluorine, chlorine or bromine,R.sub.1 represents hydrogen, a linear or ramified alkyl group C.sub.1, C.sub.2, C.sub.3, C.sub.4, C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9 or C.sub.10, a linear or ramified acyl group C.sub.1 -C.

Abstract: The racemization of optically active aminoacids (including their N-acyl derivatives) by heating with carboxylic acids takes place particularly readily with carboxylic acids of low volatility. Only catalytic quantities of acid are needed; it is advantageous to use equimolar quantities or an excess, which serves as a diluent. A reaction mixture from an enzymatic racemate resolution can be heated directly for the purpose of racemization, after separation of the L-aminoacid and the water.

Abstract: There are described new optically active 3,4-bis-(diphenylphosphino)-pyrrolidines of the formula ##STR1## wherein Ph is a phenyl group and R is hydrogen, an alkyl group, an arylalkyl group or an acyl group, rhodium complexes containing a compound of formula (I) as its chiral ligands, said rhodium complexes having the formula[RH(en).sub.2 A].sup.+ X.sup.- (II),where (en).sub.2 is two molecules of a monoolefin or one molecule of a diolefin, A is an optically active compound of formula (I) and X.sup.- is a tetrafluoroborate, hexafluorophosphate or a perchlorate ion, and use of the rhodium complexes as catalysts for the homogeneous asymmetric hydrogenation of unsubstituted or .beta.-substituted .alpha.-acylamino-acrylic acids.

Abstract: Fatty acid derivatives represented by the general formula ##STR1## and salts thereof. The compounds of this invention have excellent fibrinolytic action and a highly improved solubility.

Abstract: Amino acids can be easily prepared by reducing unsaturated hydantoins to the corresponding saturated hydantoins by hydrogenating the unsaturated hydantoin using either Raney Nickel catalyst in the presence of more than a stoichiometric amount of caustic or by using zinc and hydrochloric acid followed by hydrolyzing the resultant composition with at least 3 molar equivalents of an alkali metal hydroxide to produce a racemate of an alpha amino acid. The amino acid in suitable derivative form can then be resolved particularly using a two-phase solvent system. The residual isomer of the amino acid remaining after the resolution process can then be racemized using either pyridoxal-5-phosphate or an aliphatic acid in combination with an aldehyde or a ketone. By these procedures, it is possible to obtain high yields of amino acids.

Abstract: Disclosed herein is a process for producing an N-acyl-substituted or unsubstituted phenylalanine comprising hydrolyzing a 2-substituted-4-substituted or unsubstituted benzylidene-5-oxazolone with alkali, adjusting pH of the reaction solution containing its hydrolysis product with acid at 5-9 and reducing the resultant reaction solution catalytically in the presence of a palladium or platinum reducing catalyst.In accordance with the process of the present invention, time duration required for effecting the reduction can be shortened markedly in comparison with the reduction in an aqueous strong alkaline solution. Moreover, the catalyst recovered after completion of the reduction can be used repeatedly without any additional treatment and without any observed lowering in its activity. Accordingly, the reduction using the recovered catalyst may proceed in practically the same time as in the case of using a fresh catalyst.

Abstract: A method for inhibiting the action of enkephalinases in a mammal to thereby elicit an analgesic effect in said mammal is described.Novel compounds and compositions useful for accomplishing the method of the invention are also described.

Abstract: Biologically active drugs, e.g. catecholamine hormones, are coupled to carrier molecules, e.g. monodisperse peptides to produce conjugate molecules. The conjugate molecules retain biological activity, but the pharmacokinetic, pharmacodynamic and/or potency properties of the drug is modified. The drug is coupled to the carrier via a spacer moiety which not only serves to covalently link the drug to the carrier, but also insulates the biologically active portion of the drug, i.e., the pharmacophore, from degradation during the coupling process. The carrier preferably consists of a monodisperse peptide in which the sequence of amino acid residues is carefully preselected and controlled.

Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein: R.sub.1 and R.sub.2 are independently H, OH, lower alkyl, lower alkoxy, aryloxy, heteroaryloxy, heteroaryl lower alkoxy, aryl, heteroaryl, aryl-lower alkyl, aryl-lower alkoxy, halogenated aryl-lower alkoxy, lower alkenyl, lower alkynyl, lower alkenoxy, lower alkynoxy, halogen or trifluoromethyl;A is H, aryl, lower alkyl, aryl-lower alkyl or heteroaryl; andB is ##STR2## n=0-6, wherein D is H, CONR.sub.3 R.sub.4, CO.sub.2 H, CO.sub.2 R.sub.5, CH.sub.2 OH or CH.sub.2 OR.sub.6,whereinR.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently H, lower alkyl, aryl, aryl-lower alkyl or heteroaryl;E is H, OH, lower alkyl, aryl or heteroaryl; andF is ##STR3## wherein G is the same as R.sub.1 and R.sub.2, useful for the treatment of allergy, asthma and inflammatory conditions.

Abstract: 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.

Abstract: An aminocarboxylic acid derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrogen atom or an alkyl group which may have a substituent, and Y represents --NH-- or --S--, provided that when Y represents --NH--, at least one of R.sub.1 and R.sub.2 represents an alkyl group which may have a substituent. These compounds have excellent inhibitory activity on dipeptidase in animals, and are useful for administration in combination with carbapenem antibiotics.

Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.

Abstract: .alpha.-(S)-amino acid..alpha.-phenylethanesulfonate compounds and methods of optical resolution of .alpha.-amino acids and .alpha.-phenylethanesulfonic acids are described.

Abstract: A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.

Abstract: Serine derivatives are synthesized by the condensation of an alkali metal salt of a glycine derivative and a carbonyl compound in the presence of a phase transfer catalyst.

Abstract: Amino acid fractions of different composition are obtained at different times by fractional filtration after neutralization of the hydrolysates. Tyrosine-rich and leucine-rich fractions are specifically treated and lead to the recovery of L-tyrosine, L-cystine, L-leucine and L-phenyl-alanine.

Abstract: Novel .alpha.-difluoromethyl tyrosines and esters thereof are disclosed. The novel compounds have useful pharmacological activity.

Abstract: New 3-N-acyl derivatives of 3-amino-2-hydroxy-4-phenylbutanoic acid are provided, which exhibit analgesic activity and are affective to enhance the morphine analgesia.

Abstract: A membrane for concentrating amino acids is made of a polyvinyl chloride composition containing 30 to 70 wt % of trialkyl phosphate and 2 to 20 wt % of halogenated hydrocarbon. This membrane is interposed between two amino acid solutions of the same concentration, one containing a salt that promotes the permeation of the amino acid, so that the amino acid permeates the membrane to become concentrated.

Abstract: 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.

Abstract: Aminoacid and peptide derivatives of the formula:A--NH--R.sub.1 --CO].sub.x [NH--R.sub.2 --CO].sub.y NH--R.sub.4 --COOHin which A, R.sub.1, R.sub.2, x and y have the meanings specified in claim 1 for formula I, and R4 is a residue of an .alpha.-aminoacid which, when A is 4-allyloxy-3-chloro-phenylacetyl and x and y are 0, contains at least 2 carbon atoms, and their physiologically acceptable salts and lower alkyl ester.These compounds and 4-allyloxy-3-chloro-phenylacetylglycine have anti-inflammatory activity and pharmaceutical compositions containing them are described.

Abstract: Provided is a method of increasing the purity of amphoteric compound compositions. The method is: (a) providing an amount of a crude amphoteric compound composition, (b) using a portion of the crude composition to prepare in solution a cationic salt of the amphoteric compound, (c) using another portion of the crude composition to prepare in solution an anionic salt of the amphoteric compound, (d) mixing together the solutions wherein a precipitate is formed, and (e) collecting the precipitate which is an amphoteric compound composition of higher purity than the crude composition.

Abstract: Aqueous solutions of sodium salts of .alpha.-aminocarboxylic acids practically free of foreign salts are produced by saponifying the corresponding hydantoin at a temperature between 110.degree. C. and 180.degree. C. with a mixture, in each case based on the hydantoin, of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or hydroxide, separating off the precipitated calcium carbonate after the end of the saponification and concentrating the aqueous sodium salt solution remaining to drive off the ammonia contained therein.

Abstract: Novel prodrugs of methyldopa which are [(alkoxycarbonyl)oxy]alkyl esters of methyldopa are disclosed. Also, pharmaceutical compositions containing these compounds are disclosed. Upon administration to warm-blooded animals, these prodrugs liberate methyldopa along with innocuous side products.

Abstract: Compounds of the formula: ##STR1## wherein: X is fluorine, chlorine, or bromine;R is the group R.sub.2 as defined below;R.sub.1 is a group of the formula: ##STR2## or the group R.sub.2 as defined below; wherein R.sub.2 is: ##STR3## wherein R.sub.3 is hydrogen, (C.sub.1 -C.sub.4)alkyl, or (C.sub.1 -C.sub.4)alkoxy, andR.sub.4 is (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy;or a (C.sub.1 -C.sub.8)alkyl ester thereof; or a non-toxic pharmaceutically acceptable salt thereof, inhibit MAO in vivo and can be administered either alone or in combination with an aromatic L-amino acid decarboxylase inhibitor for the treatment of depression.

Abstract: The present invention relates to L-phenylalanine 1/2 sulfate and its use in the purification of L-phenylalanine from fermentation broths. When the salt is crystallized from a fermentation broth of L-phenylalanine or a solution produced during an intermediate process of recovering L-phenylalanine from the fermentation broth, impurities derived from the fermentation broth are easily removed.

Abstract: Amino acid fractions of different composition are obtained at different times by fractional filtration after neutralization of the hydrolysates. Tyrosine-rich and leucine-rich fractions are specifically treated and lead to the recovery of L-tyrosine, L-cystine, L-leucine and L-phenyl-alanine.