Alpha N, Beta S - Acids Or Salts Thereof Patents (Class 562/557)
  • Patent number: 4847282
    Abstract: Water-soluble acetylcysteine salts, useful as mucolytic agents, consisting of reaction products of acetylcysteine with at least one basic amino-acid, the latter being preferably selected from the group comprising arginine, lysine, histidine, ornithine and glycine.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: July 11, 1989
    Assignee: Galephar
    Inventor: Arthur M. Deboeck
  • Patent number: 4845114
    Abstract: N-(trans-p-hydroxy-cyclohexyl)-(2-amino-3,5-dibromo)benzylamine salts possessing mucolytic activity, and having the general formula: ##STR1## wherein R is the anion of a mono or dicarboxylic amino acid chosen from the group consisting of .alpha.-mercaptopropionylglycine, S-benzoyl-.alpha.-mercaptopropionylglycine, S-thenoyl-.alpha.-mercaptopropionylglycine, acetyl-L-cysteine, carboxymethyl-L-cysteine, thiazolidinemonocarboxylic acid and thiazolidinedicarboxylic acid, and n is 1 if said amino acid is monocarboxylic, n is 1 or 2 if said amino acid is dicarboxylic.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: July 4, 1989
    Assignee: Erregierre Industria Chimica Spa
    Inventor: Egidio Molinari
  • Patent number: 4837371
    Abstract: 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: Grant
    Filed: September 3, 1987
    Date of Patent: June 6, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shinji Ogawa, Seiya Iguchi, Hiroshi Kimura, Yoh Ohmori
  • Patent number: 4837332
    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.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: June 6, 1989
    Assignee: PPG Industries, Inc.
    Inventor: Chih-Yueh Chou
  • Patent number: 4837361
    Abstract: The present invention in one aspect relates to a process for the simultaneous removal of NO.sub.x and SO.sub.2 from a fluid stream comprising mixtures thereof and in another aspect relates to the separation, use and/or regeneration of various chemicals contaminated or spent in the process and which includes the steps of:(A) contacting the fluid stream at a temperature of between about 105.degree. and 180.degree. C.
    Type: Grant
    Filed: November 18, 1987
    Date of Patent: June 6, 1989
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Shih-Ger Chang, David K. Liu, Elizabeth A. Griffiths, David Littlejohn
  • Patent number: 4808572
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: a is an integer of from 1 to 7,R.sup.o represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted at the terminal carbon atom by a free or acylated hydroxy group, by a halogen atom having an atomic number of at most 17, or by methoxy, or represents C.sub.1-3 -perfluoroalkyl,R.sup.2 represents an optionally unsaturated aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene or alternatively, if R.sup.1 represents a halogenated radical and/or B represents phenylene or ethylene, a single bond or vinylene,B represents a single bond, ethynylene or phenylene,R.sup.3 represents hydroxy, C.sub.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: February 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Werner Breitenstein, Andreas von Sprecher, Robert W. Lang, Konrad Oertle
  • Patent number: 4801742
    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.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: January 31, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Jennifer M. Quirk, Charles G. Carter, Robert J. Kupper
  • Patent number: 4801579
    Abstract: Novel cystine compounds of the general formula I are proposed wherein the independently of one another each represent a, preferably natural, L-amino acid, in particular glycine, alanine, proline, threonine, serine, valine, arginine, lysine or ornithine; the R.sub.1 independently of one another each stand for an acyl group of an organic acid with 2 to 5 carbon atoms, preferably for acetyl-, propionyl-, succinyl- or hydroxysuccinyl- or for a, preferably natural, L-amino acid which via its carboxylic group is linked amide-like to the amino group of the amino acid AS, the amino acids indicated as preferred for AS also being preferred for the amino acids of R.sub.1, or the two R.sub.1 together form the acyl group of an organic dicarboxylic acid, preferably the succinic or malic group; and the R.sub.2 independently of one another each are an alkoxy group with 1 to 4 carbon atoms, preferably methoxy or ethoxy, the hydroxy group, where in case of the meaning of R.sub.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: January 31, 1989
    Assignees: Bleiberger Bergwerks Union, Pfrimmer & Co. Pharmazeutische Werke Erlangen GmbH & Co. KG
    Inventors: Naderer Rainer, Buxbaum Lothar, Langer Klaus
  • Patent number: 4777289
    Abstract: A process for the preparation of alkylthioalkanoate salts by reaction of an alkali metal alkylmercaptide with a lactone in the presence of an aprotic polar organic solvent. Preferably, the alkali metal mercaptide is prepared by reaction of an alkylmercaptan and an alkali metal phenate.
    Type: Grant
    Filed: May 8, 1986
    Date of Patent: October 11, 1988
    Assignee: Monsanto Company
    Inventor: Dennis A. Ruest
  • Patent number: 4775662
    Abstract: The compounds represented by the formula (I) ##STR1## wherein n is 1 or 2; m is 0, 1 or 2; p is 9, 10, 11, 12 or 13; X is hydrogen or hydroxyl; R is hydroxyl or amino; R.sub.1 is hydrogen, amino or ##STR2## and R.sub.2 is hydroxyl, amino, ##STR3## with the proviso that when m is 0, R.sub.1 is hydrogen or pharmaceutically acceptable salts thereof have been found to be leukotriene antagonists and useful in the treatment of diseases in which leukotrienes are a factor, such as asthma.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: October 4, 1988
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Thomas W. Ku
  • Patent number: 4769491
    Abstract: From the aqueous solution containing cysteine obtained by the enzymatic method or fermentative method, cystine is produced in a high yield by oxidizing the cysteine in the presence of dimethyl sulfoxide.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: September 6, 1988
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shyoichiro Miyahara, Toshiaki Kamiguchi, Tooru Miyahara, Hashimukai Tadashi, Nitta Kazunari
  • Patent number: 4769486
    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.
    Type: Grant
    Filed: August 26, 1987
    Date of Patent: September 6, 1988
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Tsuneo Harada, Kiyotaka Oyama
  • Patent number: 4736060
    Abstract: Method for optical resolution of DL-cysteine by (1) reacting DL-cysteine with formaldehyde to prepare DL-thiazolidine-4-carboxylic acid (DL-TCA), (2) forming diastereomer salts of D-TCA and of L-TCA by reacting DL-TCA with an optically active 1-(1-naphthyl)ethylamine, (3) separating said diastereomer salts by difference of the solubilities thereof in a solvent, (4) recovering D-TCA from said diastereomer salt of D-TCA and finally obtain D-cysteine, and recovering L-TCA from said diastereomer salt of L-TCA and finally obtain L-cysteine.
    Type: Grant
    Filed: August 1, 1986
    Date of Patent: April 5, 1988
    Assignee: Nippon Rikagakuyakuhin Co., Ltd.
    Inventors: Keizo Tomuro, Yoshiharu Tamura, Yoko Morimoto, Shigeyoshi Katoh
  • Patent number: 4733010
    Abstract: Hydrochloric acid is added to a solution containing L-cysteine, L-cystine, L-serine and an inorganic salt until it contains at least 15% by weight of hydrochloric acid. The solution is held at a temperature of at least 20.degree. C. so that the L-cystine and the inorganic salt may form a solid, and the solid is removed from the solution. The solution is cooled to a temperature not exceeding 10.degree. C., so that crystallization may take place to form the monohydrate of L-cysteine hydrochloride. The monohydrate is separated from the L-serine in the solution.
    Type: Grant
    Filed: June 9, 1987
    Date of Patent: March 22, 1988
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shyoichiro Miyahara, Toshiaki Kamiguchi, Tadashi Hashimukai, Kazunari Nitta
  • Patent number: 4724140
    Abstract: Compositions for the hydration of keratinic substances constituted by amino acid sulfoxides. A particular product is methionine sulfoxide. Important application in cosmetology where these products are incorporated in aqueous and organic solutions and oily or other emulsions. These products play a hydrating role in skin application and act as a softening agent on the hair.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: February 9, 1988
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Philippe Potin, Marie-Claude Martini
  • Patent number: 4721803
    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.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: January 26, 1988
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4678806
    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.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: July 7, 1987
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Wasyl Halczenko, George Hartman, Steven M. Pitzenberger
  • Patent number: 4677224
    Abstract: 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: Grant
    Filed: June 3, 1985
    Date of Patent: June 30, 1987
    Assignee: Centre National de la Recherche Scientifique (CNRS)
    Inventors: Auguste Commeyras, Jacques Taillades, Jean Brugidou, Louis Mion, Regine Sola, Robert Pascal, Monique Lasperas, Alain Rousset
  • Patent number: 4661510
    Abstract: Novel .alpha.-allenic-.alpha.-amino acids which are enzyme inhibitors of the suicide or k.sub.cat type are disclosed herein.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: April 28, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Alexander Krantz, Arlindo L. Castelhano
  • Patent number: 4638086
    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.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: January 20, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Susanne Grabley
  • Patent number: 4621151
    Abstract: Disclosed is a method of optical resolution of DL-cysteine utilizing optically active mandelic acid. The method facilitates commercial production of optically active cysteine, particularly L-cysteine which is in great demand.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: November 4, 1986
    Assignee: Hiroyuki Nohira
    Inventors: Hiroyuki Nohira, Keiko Ueda
  • Patent number: 4595687
    Abstract: Sparsomycin derivatives of the formula ##STR1## wherein X and Y are each independently an oxo or an imino group; n is 0 or the integer 1 or 2; R.sub.1 is a hydrogen or 1 to 4 carbon alkyl group; R.sub.2 is a hydrogen, a 1 to 4 carbon alkyl, a 2 to 5 carbon acyl or a benzoyl group; and R is a 1 to 6 carbon alkyl, 3 to 8 carbon alkenyl, cyanomethyl carboxymethyl, carbalkoxymethyl wherein the alkoxy moiety is a 1 to 4 carbon alkoxy group, nitromethyl, alkylcarbonylmethyl wherein the alkyl moiety is a 1 to 4 carbon alkyl group, pyridyl, furanyl, or furfuryl group or a phenyl or benzyl group optionally substituted by a methylenedioxy or one to two halogen, 1 to 4 carbon alkyl, 1 to 4 carbon alkoxy, 1 to 4 carbon alkylthio, hydroxy, nitro or cyano groups or a pharmaceutically acceptable acid addition salt thereof. Also described are their use as antiprotozoals and antibacterials.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: June 17, 1986
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Douglas W. Beight, Gary A. Flynn
  • Patent number: 4594188
    Abstract: An enkephalin-degrading aminopentidase enzyme is inhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salt thereof, wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, carboxyalkyl, halo substituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl;R.sub.3 is hydroxy, alkoxy, (substituted alkyl)oxy, arylalkoxy, (heteroaryl)alkoxy or --NY.sub.1 Y.sub.2, wherein Y.sub.1 and Y.sub.2 are each independently hydrogen, alkyl, aryl, or arylalkyl or Y.sub.1 is hydrogen and Y.sub.2 is substituted alkyl or (heteroaryl)alkyl;A.sub.1 is glycyl, alanyl, leucyl, phenylalanyl, arginyl, sarcosyl, seryl, asparagyl, lysyl, glutamyl, histidyl, tryptophyl, cysteinyl, methionyl, threonyl, tyrosyl, leucyl, valyl, aspartyl, prolyl, norleucyl, norvalyl, or ##STR2## wherein n.sub.6 is an integer of 2 to 15; A.sub.2, A.sub.3, A.sub.4 and A.sub.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: June 10, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, Eric M. Gordon
  • Patent number: 4551548
    Abstract: The subject matter of the invention is a process for the recovery of S-(carboxymethyl)-(R)-cysteine and S-(carboxymethyl)-(S)-cysteine from a mixture of the two enantiomers. The mixture to be separated is dissolved in water in the presence of sufficient ammonia that the ammonium salt solution formed has a pH between 6 and 9. Then there is brought about in the solution of ammonium salt a state of supersaturation by the addition of seeding crystals of the ammonium salt of one of the two enantiomers, insofar as the starting material contains one of the two enantiomers in excess, the ammonium salt of this enantiomer, the ammonium salt of one of the two enantiomers is brought to crystallization and separated off. Subsequently by addition of seeding crystals of the ammonium salt of the other enantiomers to the remaining mother liquor the ammonium salt of this enantiomer is likewise brought to crystallization and separated off.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: November 5, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Jurgen Martens, Horst Weigel
  • Patent number: 4540792
    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.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: September 10, 1985
    Assignees: Centre National de la Recherche Scientifique, Institut National de la Sante et de la Reserche Medicale
    Inventors: Auguste Commeyras, Aldo Previero, Martine Pugniere
  • Patent number: 4535167
    Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co. Inc.
    Inventor: Roger M. Freidinger
  • Patent number: 4533747
    Abstract: The compounds represented by the formula (I) ##STR1## wherein m is 0, 1 or 2; p is 9, 10, 11, 12 or 13; R.sub.1 ' is hydrogen, ##STR2## and R.sub.2 ' is amino, --NHCH.sub.2 CO.sub.2 R.sub.3 ', ##STR3## --NHCH.sub.2 CONH.sub.2 or --OR.sub.3 ' wherein R.sub.3 ' is an alkyl radical containing one to six carbon atoms with the proviso that when m is 0, R.sub.1 ' is hydrogen are chemical intermediates in the synthesis of leukotriene antagonists of the formula (II) ##STR4## wherein m and p, are described above and R.sub.1 is hydrogen, amino or ##STR5## R.sub.2 is hydroxyl, amino, --NHCH.sub.2 CO.sub.2 H, ##STR6## --NHCH.sub.2 CONH.sub.2 ; and X is ##STR7## --CO.sub.2 H or --CH.sub.2 OH which are useful in the treatment of diseases in which leukotrienes are a factor, such as asthma.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: August 6, 1985
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Thomas W. Ku
  • Patent number: 4523012
    Abstract: The subject matter of the invention are S-substituted 2-azido-3-mercapto-propionic acid esters of the general formula ##STR1## in which R.sup.1 is a methyl or ethyl group and R.sup.2 is an unsubstituted or substituted alkyl group, a cycloalkyl group, an unsubstituted or substituted aromatic or heteroaromatic group or a benzyl group, and a process for their production by reaction of a methyl or ethyl ester of 2-chloroacrylic acid with a corresponding thiol to form an S-substituted 2-chloro-3-mercapto-propionic acid ester and subsequently exchanging the chlorine atom with an azido group as well as use of the compounds of formula (I) as intermediate products in the production of D,L-cysteine or derivatives of D,L-cysteine.
    Type: Grant
    Filed: January 12, 1983
    Date of Patent: June 11, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Franz Effenberger, Thomas Beisswenger
  • Patent number: 4519955
    Abstract: .alpha.-(S)-amino acid..alpha.-phenylethanesulfonate compounds and methods of optical resolution of .alpha.-amino acids and .alpha.-phenylethanesulfonic acids are described.
    Type: Grant
    Filed: March 2, 1984
    Date of Patent: May 28, 1985
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Ichiro Chibata, Shigeki Yamada, Chikara Hongo, Ryuzo Yoshioka
  • Patent number: 4459423
    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.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: July 10, 1984
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masaharu Doya, Takako Uchiyama
  • Patent number: 4453008
    Abstract: DL-cystein is produced by reacting a .beta.-halogenoalanine with a trithiocarbonate to obtain the mono(aminocarboxyethyl) ester of trithiocarbonate and then subjecting the ester to acid decomposition. The above process requires mild reaction conditions, is easy to carry out its reactions and can afford DL-cystein with high yield. It is thus an excellent production process of DL-cystein from the industrial viewpoint.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: June 5, 1984
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ryuichi Mita, Masaharu Ohoka, Chojiro Higuchi, Toshio Katoh, Nobuyuki Kawashima, Akihiro Yamaguchi, Shousuke Nagai, Takao Takano
  • Patent number: 4443435
    Abstract: Novel, transient prodrug forms of biologically active agents containing mercapto groups have (i) the structural formula (I): ##STR1## wherein X is O, S, or NR.sup.5 ;R.sup.1 S is the residue of any biologically active agent R.sup.1 SH;R.sup.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 17, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4436910
    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.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: March 13, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Bernd Lehmann, Jurgen Martens
  • Patent number: 4430509
    Abstract: To separate the racemate (R,S)-cysteine, the racemate is condensed in an inert solvent with an enantiomerically enantiomeric monosaccharide of the group of aldoses having 4 to 7 carbon atoms to form the corresponding 2-substituted thiazolidin-4-carboxylic acid and the mixture of diastereomers obtained separated from each other. Subsequently, the isolated unitary diastereomers are reacted in an inert solvent with a carbonyl reagent to split the ring and the enantiomerically pure cysteine in each case is isolated as such or as the corresponding cystine.
    Type: Grant
    Filed: January 25, 1983
    Date of Patent: February 7, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Horst Bethge, Karlheinz Drauz, Axel Kleemann, Jurgen Martens, Horst Weigel
  • Patent number: 4394520
    Abstract: A method, composition and compounds useful in said compositions for treating the skin and scalp characterized by an excessive secretion of sebum to improve the condition thereof by reducing said excessive secretion of sebum includes topically applying to a human having skin and/or a scalp so characterized a cosmetic composition containing as an active ingredient a derivative of cysteine or cysteamine. The composition contains about 0.1-5 weight percent of said derivative and also contains as a carrier for the active ingredient, water, a mixture of water and a lower alkanol, a lower alkanol, a mixture of a lower alkanol and a cosmetic resin, a reducing agent, a neutralizing agent or a vegetable oil.
    Type: Grant
    Filed: December 31, 1979
    Date of Patent: July 19, 1983
    Assignee: Societe Anonyme dite: L'Oreal
    Inventor: Gregoire Kalopissis
  • Patent number: 4382031
    Abstract: A process is disclosed for producing d-biotin from L or DL-cystine ester via novel intermediates.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: May 3, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Hsi L. Lee, Milan R. Uskokovic
  • Patent number: 4339600
    Abstract: Compounds for alleviating or reducing angiotensin related hypertension in hypertensive mammals comprising angiotensin converting enzyme inhibitors selected from a group of mercaptoacyl aminoacids.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: July 13, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, David W. Cushman
  • Patent number: 4332813
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: June 1, 1982
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4325961
    Abstract: Novel substituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acids and esters thereof are disclosed. The novel compounds have biological activity including decarboxylase inhibition.
    Type: Grant
    Filed: June 1, 1977
    Date of Patent: April 20, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Janos Kollonitsch, Arthur A. Patchett
  • Patent number: 4320056
    Abstract: A process is disclosed for producing d-biotin from L or DL-cystine ester via novel intermediates.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: March 16, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Hsi L. Lee, Milan R. Uskokovic
  • Patent number: 4315846
    Abstract: This application relates to novel metal salts of N-substituted alkylenebisdithiocarbamic acids and their use as agricultural fungicides.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: February 16, 1982
    Assignee: Tokyo Organic Chemical Industries, Ltd.
    Inventors: Masuo Kuchikata, Hiroshi Tsuyuki, Toshio Furukawa, Yoshihiro Nitta, Hiroshi Kuyama
  • Patent number: 4311645
    Abstract: A chemical synthesis of an SRS-A active compound from the reaction product of 1-halo-2-octyne and the ether of 2-penten-4-yn-1-ol including intermediates in the synthesis, some of which being antagonists of SRS-A useful for treating allergic reactions.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: January 19, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4305958
    Abstract: This invention relates to the compounds: N-(mercaptoacy)-cysteine represented by the following formula wherein Z is selected from the group consisting of CH.sub.3 --CH<, (CH.sub.3).sub.2 C<, (CH.sub.2).sub.2 < and CH.sub.2 <, acting as agents for the liquefaction of sputum, intermediate therefor and a process for manufacture thereof.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: December 15, 1981
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Tadashi Fujita, Masayuki Oya, Hideo Takashina, Tadashi Iso
  • Patent number: 4296127
    Abstract: Novel compounds are prepared by reacting essential or semi-essential amino acids with nitrogen-free analogues thereof, particularly alpha-keto and/or alpha-hydroxy analogues. The mixed salt reaction products are precursors of essential and semi-essential amino acids in the body, and mixtures of the salts are useful in the treatment of renal and hepatic disorders characterized by protein intolerance leading to deficiencies of various essential and semi-essential amino acids in the body. They may also be useful in the treatment of nitrogen wasting disorders and protein malnutrition. The novel compounds are generally far more palatable and soluble in aqueous solutions than the individual essential or semi-essential amino acids, nitrogen-free analogues thereof, or simple mixtures of these.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: October 20, 1981
    Assignee: The Johns Hopkins University
    Inventor: Mackenzie Walser
  • Patent number: 4284557
    Abstract: A process is disclosed for producing d-biotin from L or DL-cystine ester via novel intermediates.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: August 18, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Hsi L. Lee, Milan R. Uskokovic
  • Patent number: 4276374
    Abstract: A silver halide photographic emulsion containing the compound represented by the formula (I):R.sub.1 --(X--R.sub.3).sub.m --X--R.sub.2 (I)wherein R.sub.1 and R.sub.2 each represents an alkyl group containing 1 to 5 carbon atoms substituted with two or more substituents selected from --OH, --NHR.sub.4, --COOR.sub.4, --CONH.sub.2, --SO.sub.3 H, --COOM, or --SO.sub.3 M, R.sub.3 represents an alkylene group containing 1 to 4 carbon atoms which may be substituted by --OH, R.sub.4 represents a hydrogen atom or an alkyl group containing 1 to 5 carbon atoms, X represents a sulfur or oxygen atom, provided at least one X is a sulfur atom, m represents 0 or an integer of 1 to 4, and M represents an alkali metal atom.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: June 30, 1981
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroyuki Mifune, Nobuaki Miyasaka, Yoshiharu Fuseya
  • Patent number: 4255446
    Abstract: S-Substituted derivatives of N-(2-mercapto-2-methylpropanoyl)-cysteine which have the formula ##STR1## are useful as a medicine for suppressing liver disorders.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: March 10, 1981
    Assignee: Santen Pharmaceutical Co. Ltd.
    Inventors: Jun-ichi Iwao, Masayuki Oya, Takehisa Chiba
  • Patent number: 4250183
    Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: February 10, 1981
    Assignee: BYK Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4243679
    Abstract: S-(3-methyl-2-butenyl)cysteine ##STR1## or a pharmaceutically acceptable salt thereof. The compound is an expectorant and can be applied in the form of capsules or dragees, solutions, syrups or suppositories.
    Type: Grant
    Filed: April 19, 1979
    Date of Patent: January 6, 1981
    Inventors: Jorge D. Adsara, Silvano Casadio, Jose M. B. Ribalta, Leonida Bruseghini
  • Patent number: 4204064
    Abstract: A method, composition and compounds useful in said compositions for treating the skin and scalp characterized by an excessive secretion of sebum to improve the condition thereof by reducing said excessive secretion of sebum includes topically applying to a human having skin and/or a scalp so characterized a cosmetic composition containing as an active ingredient a derivative of cysteine or cysteamine. The composition contains about 0.1-5 weight percent of said derivative and also contains as a carrier for the active ingredient, water, a mixture of water and a lower alkanol, a lower alkanol, a mixture of a lower alkanol and a cosmetic resin, a reducing agent, a neutralizing agent or a vegetable oil.
    Type: Grant
    Filed: January 24, 1978
    Date of Patent: May 20, 1980
    Assignee: L'Oreal
    Inventor: Gregoire Kalopissis