Sulfur Or Selenium Patents (Class 562/556)
  • Patent number: 4978759
    Abstract: The process described makes it possible to obtain optically pure 4-amino-3-hydroxycarboxylic acids by means of a series of stereoselective steps. The starting material is an alpha-amino acid in the L or D configuration, with which Meldrum's acid is reacted. The resulting pyrrolone derivative is reduced prior to opening of the pyrrolidine ring. The invention also relates to the new products obtained by the said process and to the pyrrolone derivatives obtained as intermediates.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: December 18, 1990
    Assignee: Sanofi, S.A. and Institut National de la Sante et de la Recherche Medicale
    Inventors: Patrick Jouin, Dino Nisato, Bertrand Castro
  • Patent number: 4956504
    Abstract: The present invention relates to novel Spergualin-related compounds represented by the general formula [I] ##STR1## (wherein X is ##STR2## R is --H or --CH.sub.2 OH; R.sub.1 is --H, ##STR3## R.sub.2 is a residue obtained by removing, from an amino acid or peptide, the hydroxyl group of the carboxyl group and, when R.sub.1 is a group other than --H, R.sub.2 is same as R.sub.1), or a pharmacologically acceptable salt thereof. Said compounds or salts thereof have an immuno-modulating action.
    Type: Grant
    Filed: April 1, 1987
    Date of Patent: September 11, 1990
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Tomio Takeuchi, Tetsushi Saino, Masao Yoshida, Katsutoshi Takahashi, Teruya Nakamura, Hamao Umezawa, deceased
  • Patent number: 4937243
    Abstract: Novel compounds of the formula (I), processes for their preparation and their use as collagenase inhibitors are described: ##STR1## in which R.sub.1 is hydroxy; alkoxy; aryloxy; aralkyloxy; --NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are hydrogen or alkyl, or R.sub.6 and R.sub.7 together with the N-atom to which they are bonded form a 5- to 7-membered ring with an optional heteroatom; --NHCH(R.sub.8)COR.sub.9 where R.sub.8 is hydrogen; alkyl optionally substituted by hydroxy, alkoxy, --NR.sub.6 R.sub.7, quanidine, CO.sub.2 H, CONH.sub.2, SH, or S-alkyl; or CH.sub.2 -AR where Ar is optionally substituted aryl; and R.sub.9 is hydroxy, alkoxy or --NR.sub.6 R.sub.7.R.sub.2 is hydrogen or acyl.R.sub.3 is C.sub.3-6 alkyl.R.sub.4 is hydrogen; alkyl; --CH.sub.2 R.sub.10 where R.sub.10 is optionally substituted phenyl or heteroaryl; or --CH(R.sub.12)O--R.sub.11 where R.sub.11 is hydrogen; alkyl; or --CH.sub.2 Ph where Ph is optionally substituted phenyl; and R.sub.12 is hydrogen or alkyl.R.sub.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: June 26, 1990
    Assignee: Beecham Group p.l.c.
    Inventors: Roger E. Markwell, Stephen A. Smith, Ian Hughes
  • Patent number: 4918223
    Abstract: N-acylated mercapto-.alpha.-amino acids of the general formula ##STR1## are prepared by reacting a nitrile of the general formulaR.sub.1 -CN (II)at a temperature between 0.degree. C. and 100.degree. C. in water or in a mixture of water and an organic solvent which is at least partially miscible with water, in the presence of a base with a mercapto-.alpha.-amino acid of the general formula ##STR2## and subsequently releasing the N-acylated mercapto-.alpha.-amino acid of general formula (I) with an acid. Mercapto-.alpha.-amino acids can be selectively acylated on the amino group in this manner in a relatively simple manner.
    Type: Grant
    Filed: August 9, 1988
    Date of Patent: April 17, 1990
    Assignee: Degussa Aktiengesellschaft
    Inventors: Hans-Peter Krimmer, Karlheinz Drauz
  • Patent number: 4918224
    Abstract: Salts of N-acetyl cysteine and N-acetyl homocysteine are prepared by reacting acetonitrile with cysteine or homocysteine in an aqueous or aqueous-organic medium adjusted to a pH in the range of 8 to 10 with a base supplying the cation of the salt. The reaction is carried out at a temperature in the range of 0.degree. C. to the boiling temperature of the reaction mixture.
    Type: Grant
    Filed: August 9, 1988
    Date of Patent: April 17, 1990
    Assignee: Degussa Akteingesellschaft
    Inventors: Hans-Peter Krimmer, Karlheinz Drauz
  • Patent number: 4906665
    Abstract: Novel hydroxyalkylcysteine derivatives of the following formula (I) and an expectorant comprising the same are disclosed. ##STR1## wherein n represents an integer of 5 to 24. The expectorant is stabile, has little side effects and toxicity, and exhibits an excellent expectorant effect.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: March 6, 1990
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Yoshikuni Itoh, Hiroyuki Mizuno, Chikako Kiyohara, Susumu Sato, Tatsuhiko Katori
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4874803
    Abstract: The present invention comprises reaction products resulting from the reaction of hydrazido-substituted or certain amino-substituted polymer stabilizers and cyclic dianhydrides, as well as the use of such products. The polymer stabilizers of the invention are useful for protecting a large variety of synthetic polymeric organic materials from the degradative effects of heat, light and oxygen. Some of the modifiers are flame retardants and many are metal deactivators in addition to their primary activity.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: October 17, 1989
    Assignee: Pennwalt Corporation
    Inventors: Arthur L. Baron, Terry N. Myers, Jerome Wicher
  • Patent number: 4852989
    Abstract: This invention relates to bleaching compounds and compositions that provide effective and efficient surface bleaching of textiles over a wide range of bleach solution temperatures. The bleaching compounds of the invention yield a peroxyacid with a polar amide link in the hydrophobic chain when used in the bleaching compositions. In a preferred embodiment, the bleaching compositions of the invention are also detergent compositions.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: August 1, 1989
    Assignee: The Procter & Gamble Company
    Inventors: Michael E. Burns, Frederick E. Hardy
  • 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: 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: 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: 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: 4780469
    Abstract: A (fused) benz(thio)amide of the formula: ##STR1## wherein B represents(i) a carbocyclic ring of from 4 to 8 members being unreplaced or replaced one, two or three of optional carbon atom(s) by oxygen, nitrogen and/or sulphur atom(s) or(ii) a divalent group of the formula: ##STR2## R.sup.1 represents a group of formula: ##STR3## (iv) a straight or branched alkyl, alkenyl, or alkynyl of from 1 to 20 carbon atoms,R.sup.4 represents(i) when B represents a closed ring, a group of the formula: ##STR4## (ii) when B does not represent a ring, a group of formula: ##STR5## with the proviso that compounds of formula: ##STR6## wherein A' is a vinylene or an ethylene group optionally substituted by straight or branched alkyl groups of from 1 to 4 carbon atom(s);R.sup.4' is--(CH.sub.2).sub.n --COOR.sup.8andR.sup.1' is(i) a group of the formula: ##STR7## or (ii) a group of the formula: ##STR8## are excluded, wherein A, R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, U, n, m, p, q, R.sup.5', and R.sup.
    Type: Grant
    Filed: August 20, 1985
    Date of Patent: October 25, 1988
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
  • 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: 4769325
    Abstract: 2-(Allenyl)penicillins antibiotics and intermediates thereto are disclosed. A process for making the 2-(allenyl)penicillins and the starting materials for the process are also disclosed.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: September 6, 1988
    Inventors: Jack E. Baldwin, Amit Basak
  • Patent number: 4758594
    Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.
    Type: Grant
    Filed: May 19, 1986
    Date of Patent: July 19, 1988
    Assignee: Schering Corporation
    Inventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
  • Patent number: 4737300
    Abstract: The invention relates to material containing aldosemarcaptals of the formula I ##STR1## wherein n can be an integer from 2 to 6, and wherein R.sup.1 and R.sup.2 are identical or different, and in each case are C.sub.1 -C.sub.18 -alkyl, which is unsubstituted, substituted or interrupted by --O-- or --S--, or are --(CH.sub.2).sub.r --CO--N(C.sub.1 -C.sub.17 -alkyl).sub.2, r being 1 or 2, or are phenyl, benzyl or --(CH.sub.2).sub.r --CO--O--R.sup.3, in which r can be 1 or 2 and R.sup.3 is an alkali metal or C.sub.1 -C.sub.14 -alkyl; also wherein R.sup.1 and R.sup.2 are --CH.sub.2 --CH(OH)--R.sup.4, in which R.sup.4 is hydrogen, or C.sub.1 -C.sub.16 -alkyl, unsubstituted or substituted by --OH, or --CH.sub.2 --Y--(C.sub.1 -C.sub.15 -alkyl), in which Y is --O-- or --S--; or wherein R.sup.1 and R.sup.2 together form --(CH.sub.2).sub.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4736055
    Abstract: Oxime sulfonates of formula I ##STR1## wherein Y is a polymerizable unsaturated group or epoxide group or an --OH, --NHR.sup.5, --COOH, COOR.sup.6, --COCl, --CH.sub.2 Hal, --SO.sub.2 Cl or --NCO group, Z is an (x+y)-valent connecting member, R.sup.1 and R.sup.2 are monovalent organic radicals, m is 0 or 1, x is 1 or 2 and y is 1 or 2, can be converted into polymers which can be thermally or photochemically dissociated to form free sulfonic acid groups. Said polymers can therefore be used as photoresists which can be developed with aqueous alkalis.
    Type: Grant
    Filed: April 11, 1986
    Date of Patent: April 5, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Dietliker, Werner Rutsch, Godwin Berner, Max Hunziker, Christopher G. Demmer
  • Patent number: 4727062
    Abstract: Described are 3-halovinylglycines and their amino acid dipeptide and oligopeptide conjugates, a new class of efficient antibacterial agents, pharmaceutical compositions containing them as active ingredients, and methods of synthesis. The compounds are thought to interfere in bacterial cell wall synthesis.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: February 23, 1988
    Assignee: Merck & Co., Inc.
    Inventors: David Taub, Robert H. Abeles, Arthur A. Patchett
  • 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: 4720578
    Abstract: The invention relates to a non-ionic surfactant having the formula:CF.sub.3 (CF.sub.2).sub.m --Y--(CH.sub.2 CH.sub.2 O).sub.n --CHR.sub.1 --CHR.sub.2 --CHR.sub.3 --COOMand to the process for the preparation and use of said surfactants. The process involves reacting an alcohol ether, CF.sub.3 (CF.sub.2).sub.m --Y--(CH.sub.2 CH.sub.2 O).sub.n H, with a metal hydroxide, MOH, to produce the corresponding intermediate salt,CF.sub.3 (CF.sub.2).sub.m --Y--(CH.sub.2 CH.sub.2 O).sub.n M,and reacting said salt with a butyrolactone, ##STR1## to produce the corresponding carboxypropylated product shown above, wherein Y is oxygen or --SO.sub.2 N'--R where R is lower alkyl; R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen or C.sub.1 to C.sub.4 alkyl; M is a sodium, potassium or lithium cation; n is an integer having a value of from 2 to 50 and m is an integer having a value of from 3 to 25.
    Type: Grant
    Filed: July 23, 1986
    Date of Patent: January 19, 1988
    Assignee: GAF Corporation
    Inventor: Kou-Chang Liu
  • Patent number: 4710574
    Abstract: Disclosed is the hydrocarboxylation of defined enamides with CO and a compound ROH to make amino acids or amido esters, either of which can be hydrolyzed to .alpha.-amino acids.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: December 1, 1987
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, James D. Burrington
  • Patent number: 4695588
    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: March 16, 1978
    Date of Patent: September 22, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Janos Kollonitsch, Arthur A. Patchett
  • Patent number: 4684483
    Abstract: An N-substituted amino acids can be prepared by the steps of: bringing together under reaction condition glyoxal and a source of sulfur dioxide in an aqueous medium to produce a sulfonated intermediate; and introducing into said medium a nitrogen compound selected from the group consisting of ammonia, a primary amine, and a secondary amine, into said medium containing said intermediate to produce said N-substituted amino acid.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: August 4, 1987
    Assignee: Monsanto Company
    Inventors: Thomas J. Richard, William H. Miller
  • Patent number: 4684644
    Abstract: The present invention is directed to a class of basic monocarboxyamide derivatives of actagardine. Actagardine (INN) is an antibiotic substance produced by actinoplanes strains such as Actinoplanes Sp. ATCC 31048 and Actinoplanes Sp. ATCC 31049 which are described in U.S. Pat. No. 4,022,884. Actagardine shows antimicrobial in vitro and in vivo activity against gram-positive organisms. Its complete chemical structure is not yet known but there is only information on its chemical functions and main fragments. In particular, it has been found that actagardine has two carboxylic functions and a primary amino function and can therefore be represented as follows: ##STR1## The compounds of the invention are monoamide derivatives at one of the carboxy functions of actagardine.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: August 4, 1987
    Assignee: Gruppo Lepetit S.p.A.
    Inventors: Adriano Malabarba, Bruno Cavalleri
  • 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: 4649215
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which R.sup.1 represents a C.sub.1-3 -alkyl radical or a C.sub.1-3 -hydroxyalkyl radical of which the hydroxy group may be in esterified form,R.sup.2 represents an optionally unsaturated aliphatic radical having from 5 to 15 carbon atoms,R.sup.3 represents hydroxy, alkoxy or an optionally substituted amino group, and-X- represents a single bond, a methylene group or an optionally N-acylated primary aminomethylene groupwherein the O-atom of the hydroxy group is in the transconfiguration relative to the S-atom, are effective as leucotriene-antagonists since they eliminate the contractions of smooth muscles caused by leucotrienes and are therefore suitable for the treatment of allergic, especially asthmatic, conditions.
    Type: Grant
    Filed: June 25, 1985
    Date of Patent: March 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas von Sprecher, Ivan Ernest, Alan J. Main, Andreas Beck
  • Patent number: 4633014
    Abstract: Substituted 3-hydrazinopropionates comprising compounds of the general fola: ##STR1## wherein R.sup.1, R.sup.2 =H, an alkyl, a substituted alkyl, hydroxycarbonyl, alkoxycarbonyl, an aryl, an aralkyl, an unsaturated alkyl, a substituted aryl or a substituted aralkyl: ##STR2## wherein R.sup.7, R.sup.8 =H, an alkyl, an unsaturated alkyl, an aralkyl, an aryl, a substituted alkyl,R.sup.9 =OH, an alkoxy, an aralkoxy, an alkyl, an unsaturated alkyl, an aryl, a substituted aryl, an aralkyl;R.sup.4 is --C.tbd.N, --COR.sup.10, wherein R.sup.10 =OR.sup.11, NR.sup.12 R.sup.13, where R.sup.11 is H, an alkyl, an aralkyl and an alkali metal, R.sup.11 and R.sup.12 are each H, an alkyl, an aralkyl, an aryl;R.sup.5, R.sup.6 = an alkyl, an aryl, an aralkyl.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: December 30, 1986
    Assignee: Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr
    Inventors: Gunar A. Bremanis, Ivars Y. Kalvinsh, Irene B. Antsena, Edmund Y. Lukevits, Maris M. Veveris, Valeryans Y. Kauss, Peter T. Trapentsier, Edvards E. Liepinsh
  • Patent number: 4629736
    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.
    Type: Grant
    Filed: September 28, 1984
    Date of Patent: December 16, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Shin-ichi Tsukamoto, Yoshinobu Nagano, Kimio Katsuda
  • Patent number: 4622420
    Abstract: A simple method for making EDTA, ED3A or DTPA analogs from amide derivatives of alpha amino acids is disclosed. These EDTA, ED3A or DTPA analogs are useful chelating agents, and preferably are useful as bifunctional chelating agents which may be attached to biological molecules and which form physiologically stable chelates with a variety of metal ions.
    Type: Grant
    Filed: February 5, 1985
    Date of Patent: November 11, 1986
    Assignee: The Regents of the University of California
    Inventors: Claude F. Meares, Simon M. Yeh, David G. Sherman
  • Patent number: 4619944
    Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.2 R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: October 28, 1986
    Assignee: USV Pharmaceutical Corporation
    Inventors: Raymond D. Youssefyeh, Howard Jones
  • Patent number: 4613691
    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.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: September 23, 1986
    Assignee: Stauffer Chemical Company
    Inventors: Stanley B. Mirviss, Mark W. Empie
  • Patent number: 4609673
    Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: September 2, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
  • 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: 4585892
    Abstract: .alpha.-Alkylated, acyclic .alpha.-aminocarboxylic acids of the formula ##STR1## where * represents a center of asymmetry, R.sup.1 is a lower alkyl, allyl, benzyl or substituted benzyl group and R.sup.2 is a lower alkyl, methoxymethyl, lower alkylmercaptoethyl, phenyl, phenyl substituted with alkyl or alkoxy, benzyl, or benzyl substituted with alkyl, alkoxy or halo are produced by an enantio-selective plural step process from the corresponding .alpha.-aminocarboxylic acid monomethyl or monoethyl amide. A particular advantage of the new process is that there can be produced from one educt-enantiomer, i.e. from an (S)- or an (R)-.alpha.-aminocarboxylic acid, selectively depending on the reaction conditions used the two enantiomeric forms of the desired .alpha.-alkyl-.alpha.-aminocarboxylic acid.
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: April 29, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Dieter Seebach, Reto Naef
  • Patent number: 4581452
    Abstract: A process for preparing a 5-perfluoroalkyl-dihydrouracil derivative of the general formula ##STR1## wherein R.sub.f represents a perfluoroalkyl group, each of R.sup.1 and R.sup.2 represents a hydrogen atom, or an alkyl, cycloalkyl, aryl, aralkyl or heterocyclic group, and Y is an oxygen or sulfur atom, which comprises (a) reacting a compound of the general formula ##STR2## wherein X represents a halogen atom or hydroxyl group, with a urea derivative of the general formula ##STR3## provided that when X is a hydroxyl group and at least one of R.sup.1 and R.sup.2 is a hydrogen atom, said reaction is carried out in the presence of a condensing agent, or (b) cyclizing a compound of the general formula ##STR4## and a novel intermediate compound of the above formula (IV).
    Type: Grant
    Filed: August 26, 1983
    Date of Patent: April 8, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami, Makoto Fujita
  • Patent number: 4571430
    Abstract: Novel homocysteine thiolactone bifunctional chelating agents useful for chelating radionuclides to produce a radiodiagnostic agent for use in vivo imaging and a method for producing this chelating agent.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: February 18, 1986
    Assignee: Medi-Physics, Inc.
    Inventors: Edmund F. Byrne, Glen L. Tolman
  • Patent number: 4564472
    Abstract: A radioactive diagnostic agent which comprises a physiologically active substance and a radioactive metallic element combined with a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.3 alkyl or phenyl. The agent is characteristic in having a high stability even after being administered into a human body and showing the substantially the same behavior as the physiologically active substance itself in a human body.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: January 14, 1986
    Assignee: Nihon Medi-Physics Co., Ltd.
    Inventors: Nobuo Ueda, Susumu Kondo, Masaaki Hazue
  • Patent number: 4552893
    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, amino or ##STR2## R.sub.2 is hydroxyl, amino, --NHCH.sub.2 CO.sub.2 H, ##STR3## or --NHCH.sub.2 CONH.sub.2 ; and X is --CO.sub.2 H, --CH.sub.2 OH or ##STR4## with the proviso that when m is 0, R.sub.1 is hydrogen, or a pharmaceutically acceptable salt 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: March 7, 1983
    Date of Patent: November 12, 1985
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Thomas W. Ku
  • Patent number: 4550200
    Abstract: D,L-Homocystine is obtained by introducing molecular oxygen into an aqueous solution of the disodium salt of D,L-homocysteine having a concentration between 0.8 and 1.2 moles/l and an initial pH between 7.0 and 8.0 in the presence of a catalytic amount of iron(III) ions until there is no longer an increase in pH and subsequently adjusting the pH to about 5.3 with stirring.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: October 29, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Michael Karrenbauer, Axel Kleemann, Theodor Lussling, Fritz Schafer
  • Patent number: 4550199
    Abstract: D,L-Homocystine is obtained by treating an aqueous solution of the disodium salt of D,L-homocysteine having a concentration between 0.4 and 1.6 moles/l and an initial pH between 7.0 and 8.0 under vigorous stirring with at least the equivalent amount of an aqueous solution of hydrogen peroxide and after the end of the oxidation adjusting the pH to about 5.3. The hydrogen peroxide solution can be employed with a concentration between 20 and 60 weight percent.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: October 29, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Michael Karrenbauer, Axel Kleemann, Theodor Lussling, Fritz Schafer
  • Patent number: 4536596
    Abstract: A method for the extraction of certain amino acids from aqueous solutions by contacting said solutions with various dithiophosphinates in conjunction with a polar diluent is disclosed.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: August 20, 1985
    Assignee: American Cyanamid Company
    Inventors: Christos Savides, John H. Bright
  • 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: 4529818
    Abstract: A process for producing alkali metal aminobutyrate or alkali metal aminobutyrate-alkali metal bisulfide complex by contacting an aqueous alkali metal hydroxide with NMP and optionally alkali metal bisulfide in a stirred reactor under reaction conditions to produce a predominantly one-phase system and maintaining these reaction conditions while passing the one-phase system through a disrupted flow tube reactor to complete the reaction. Dehydrating the reaction product in a two-stage dehydration process using a higher temperature in the second stage.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: July 16, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Afif M. Nesheiwat, Fred T. Sherk
  • Patent number: 4529721
    Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: July 16, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
  • Patent number: 4528397
    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.
    Type: Grant
    Filed: March 29, 1983
    Date of Patent: July 9, 1985
    Assignee: Sanraku-Ocean Co., Ltd.
    Inventors: Norio Shibamoto, Takeo Yoshioka, Yasuo Fukagawa, Tomoyuki Ishikura
  • 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: 4517123
    Abstract: Pharmaceutically active compounds and pharmaceutically acceptable salts thereof having the following formulae ##STR1## wherein A is a straight or branched chain alkylene group containing 1 to 3 carbon atoms; and R.sup.7 and R.sup.8 is each a lower alkyl group. These compounds are useful as the active component of pharmacological preparations.
    Type: Grant
    Filed: May 4, 1982
    Date of Patent: May 14, 1985
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Tadashi Iso, Masayuki Oya