Alpha N, Beta S - Acids Or Salts Thereof Patents (Class 562/557)
  • Publication number: 20100247461
    Abstract: Disclosed are certain complexes of AFC compounds and binding agents. Such complexes are useful, among other things, in the treatment of inflammatory diseases or disorders.
    Type: Application
    Filed: January 20, 2010
    Publication date: September 30, 2010
    Applicant: Signum Biosciences, Inc.
    Inventors: Michael Voronkov, Jeffry B. Stock, Maxwell Stock, Seung-Yub Lee, Eduardo Perez, Joel S. Gordon
  • Publication number: 20100197934
    Abstract: The present invention provides a simple industrial process for producing an L- or D-optically active ?-methylcysteine derivative or its salt, which is a useful pharmaceutical intermediate, from readily available, inexpensive raw materials. In a process for producing an L- or D-optically active ?-methylcysteine derivative or its salt, a racemic N-carbamoyl-?-methylcysteine derivative or its salt is D-selectively cyclized with hydantoinase to produce a D-5-methyl-5-thiomethylhydantoin derivative or its salt and an N-carbamoyl-?-methyl-L-cysteine derivative or its salt, which are then subjected to deprotection of the amino group and the sulfur atom, and hydrolysis.
    Type: Application
    Filed: April 9, 2010
    Publication date: August 5, 2010
    Applicant: KANEKA CORPORATION
    Inventors: Takahiro Ohishi, Hirokazu Nanba, Masanobu Sugawara, Masashi Izumida, Tatsuya Honda, Kohei Mori, Satohiro Yanagisawa, Nobuo Nagashima, Kenji Inoue
  • Patent number: 7767850
    Abstract: A novel mixed salt of S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine is disclosed. The novel mixed salt, S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine maleate hydrochloride, may be produced to form crystals that may be arranged as generally orderly packed agglomerates, which are particularly useful in making pharmaceutical compositions. Such pharmaceutical compositions are also described, as well as methods to make crystalline S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine maleate hydrochloride, and methods of treating conditions characterized by an overexpression on nitric oxide from the inducible isoform of nitric oxide synthase using the S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine maleate hydrochloride.
    Type: Grant
    Filed: December 5, 2008
    Date of Patent: August 3, 2010
    Assignee: Pfizer Inc.
    Inventors: Lyle Brostrom, Ann Czyzewski, Vahid Zia, Ahmad Sheikh
  • Patent number: 7732470
    Abstract: Derivative compounds of 11-nonyloxy-undec-8(Z)-eonic acid that mimic epoxide metabolites are provided. Also provided are compositions comprising a therapeutically effective amount of the derivative compounds. The present invention further provides methods for the use of such compositions for the treatment of renal or cardiovascular disease and/or related conditions.
    Type: Grant
    Filed: February 29, 2008
    Date of Patent: June 8, 2010
    Assignees: Medical College of Georgia Research Institute, Board of Regents, The University of Texas System
    Inventors: John D. Imig, John R. Falck
  • Patent number: 7572937
    Abstract: The present invention relates to a sequence for the preparation of amino acids, for example alpha amino acids, in particular methionine, by making use of an amidocarbonylation reaction and reuse of the catalyst.
    Type: Grant
    Filed: May 14, 2005
    Date of Patent: August 11, 2009
    Assignee: Evonik Degussa GmbH
    Inventors: Martin Hateley, Thomas Hauhlner, Christoph Weckbecker, Klaus Huthmacher, Dieter Buss
  • Patent number: 7538193
    Abstract: S-nitrosohemoglobin can liberate NO by transfer to a low molecular weight thiol in the circulatory system, allowing the delivery of NO to the tissues. The effect of administering isolated S-nitrosohemoglobin and low molecular weight thiol to a mammal is to increase delivery of oxygen and NO.
    Type: Grant
    Filed: April 9, 2007
    Date of Patent: May 26, 2009
    Assignee: Duke University
    Inventor: Jonathan S. Stamler
  • Publication number: 20090105328
    Abstract: An Amino Acid Compound is described. The Amino Acid Compound may comprise an Amino Acid and one of a Nitrate and a Nitrite. The Amino Acid may be one of Aspartic Acid, Cysteine, Glycine, Lysine, Methionine, Proline, Tyrosine, and Phenylalanine.
    Type: Application
    Filed: December 17, 2008
    Publication date: April 23, 2009
    Inventors: Ronald Kramer, Alexander Nikolaidis
  • Publication number: 20080319072
    Abstract: The present invention is directed to compositions and methods of treating bacterial, viral, fungal diseases; inflammation or inflammatory-related disorders; pain; and skin conditions. The composition comprises an organic solvent extract, which is prepared by the method comprising the steps of: (a) mixing methionine with water, (b) adding an aqueous hypochlorite solution to the methionine solution and mixing, (c) adding a water-immiscible organic solvent to (b) and mixing, and (d) separating the organic solvent phase from the water phase to obtain the organic solvent extract. The present invention is also directed to a method for preparing the organic solvent extract.
    Type: Application
    Filed: September 3, 2008
    Publication date: December 25, 2008
    Inventor: Christopher Torrence
  • Patent number: 7462599
    Abstract: The present invention provides novel physiological substrates of mammalian glutaminyl cyclase (QC, EC 2.3.2.5), new effectors of QC and the use of such effectors and pharmaceutical compositions comprising such effectors for the treatment of diseases that can be treated by modulation of QC-activity, e.g. diseases selected from the group consisting of duodenal cancer with or w/o Heliobacter pylori infections, colorectal cancer, Zolliger-Ellison syndrome, Familial British Dementia and Familial Danish Dementia.
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: December 9, 2008
    Assignee: Probiodrug AG
    Inventors: Stephan Schilling, Torsten Hoffmann, André Johannes Niestroj, Hans-Ulrich Demuth, Ulrich Heiser
  • Publication number: 20080268123
    Abstract: The invention relates to compounds of O-alkylated sulphur-containing amino acids or peptides that provide an onion flavour to consumables and flavour compositions, and to consumables and flavour compositions comprising such compounds.
    Type: Application
    Filed: October 11, 2006
    Publication date: October 30, 2008
    Applicant: GIVAUDAN SA
    Inventors: Thomas Frank Hofmann, Andreas Dunkel
  • Patent number: 7439390
    Abstract: The present invention relates to a sequence for the preparation of amino acids, for example alpha-amino acids, in particular methionine, by making use of an amidocarbonylation reaction in the presence of a cobalt carbonyl catalyst and separating the catalyst in the form of a Co(N-amino acid)2 compound.
    Type: Grant
    Filed: May 14, 2005
    Date of Patent: October 21, 2008
    Assignee: Degussa AG
    Inventors: Martin Hateley, Thomas Häussner, Christoph Weckbecker, Klaus Huthmacher, Dieter Buss
  • Publication number: 20080153889
    Abstract: Derivative compounds of 11-nonyloxy-undec-8(Z)-eonic acid that mimic epoxide metabolites are provided. Also provided are compositions comprising a therapeutically effective amount of the derivative compounds.
    Type: Application
    Filed: February 29, 2008
    Publication date: June 26, 2008
    Inventors: John D. Imig, John R. Falck
  • Patent number: 7361786
    Abstract: The present invention relates to ligands of the general formula (I). In addition, a process for the production thereof and the use thereof are demonstrated.
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: April 22, 2008
    Assignee: Degussa AG
    Inventors: Armin Boerner, Jens Holz, Axel Monsees, Thomas Riermeier, Renat Kadyrov, Carsten A. Schneider, Uwe Dingerdissen, Karlheinz Drauz
  • Publication number: 20070260041
    Abstract: A method for the preparation of an allylic sulfide comprises contacting an activated sulfenyl compound of Formula (I) with a thiol of Formula (II) for a period of time sufficient to form an intermediate of Formula (III), and contacting the intermediate of Formula (III) with a thiophilic agent, in a polar solvent, to induce a [2,3]-sigmatropic rearrangement therein and thereby form an allylic sulfide of Formula (IV), with concomitant loss of a sulfur atom to the thiophilic agent, wherein in Formulas (I, II, II, and IV), X is S or SO2; Y is an aryl group, a substituted-aryl group, a heteroaryl group , or a substituted heteroaryl group; R1, R2, R3, R4, and R5 are each independently H, a hydrocarbon moiety or a substituted hydrocarbon moiety; and R is an organic moiety.
    Type: Application
    Filed: May 1, 2007
    Publication date: November 8, 2007
    Inventors: David Crich, Franck Brebion, Venkataramanan Krishnamurthy
  • Patent number: 7285676
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. A method of preparing a 2-alkyl amino acid involves reacting cysteine (or a salt or an ester thereof) and an aryl carboxylic acid to form a thiazoline ring, stereospecifically alkylating the thiazoline ring, and hydrolyzing the thiazoline ring to obtain a 2-alkylcysteine (or related compound). The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine, a 2-alkyl cysteine, or a cysteine ester.
    Type: Grant
    Filed: March 21, 2005
    Date of Patent: October 23, 2007
    Assignee: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Bhanu M. Chanda
  • Patent number: 7115769
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. In one embodiment, the present invention provides methods of preparing 2-alkylcysteine derivatives. In another embodiment, the method comprises forming a 2-alkylcysteine derivative from a cysteine derivative in the presence of a phase transfer catalyst. In particular, the present invention provides methods for preparing 2-methylcysteine derivatives. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In one aspect, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine. The present invention also relates to the preparation of 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-alkyl-thiazole-4-carboxylic acids, such as 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-thiazole-4-carboxylic acid.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: October 3, 2006
    Assignee: Genzyme Corporation
    Inventors: Rayomand H. Gimi, Mukund S. Chorghade
  • Patent number: 7102013
    Abstract: Method of making an alpha-amino acid compound having the structure of Formula 32: comprising treating under hydrolyzing conditions a hydantoin compound having the structure of Formula 33: where the substituents are described herein.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: September 5, 2006
    Assignee: Pharmacia Corporation
    Inventors: Ronald Keith Webber, Richard C. Durley, Alok K. Awasthi, Arija A. Bergmanis, Kam F. Fok, Scott S. Ganser, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Brian S. Hickory, Pamela T. Manning, Michael Mao, Alan E. Moormann, Barnett S. Pitzele, Michelle A. Promo, Richard R. Schartman, Jeffrey A. Scholten, Jeffrey S. Snyder, Mihaly V. Toth, Mahima Trivedi, Sofya Tsymbalov, Foe Siong Tjoeng
  • Patent number: 7030214
    Abstract: Ureins are obtained by reaction, in basic medium, between an N?-(aryloxycarbonyl)diamino acid and a compound containing a free amino group. The chirality of the compounds is outstandingly well preserved.
    Type: Grant
    Filed: September 4, 2001
    Date of Patent: April 18, 2006
    Assignee: Solvay (Societe Anonyme)
    Inventors: Roland Callens, Georges Blondeel, Marc Anteunis, Frank Becu
  • Patent number: 6995281
    Abstract: Methods of selectively removing counterions from compounds are disclosed. Compounds derived from the methods, such as the compound S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine zwitterion with between zero and up to 2 molar equivalents of hydrochloride are also disclosed.
    Type: Grant
    Filed: March 10, 2004
    Date of Patent: February 7, 2006
    Assignee: Pfizer, Inc.
    Inventor: Christine Moore
  • Patent number: 6992067
    Abstract: Compounds of the formula I, in which R1, R2, R3, R4, R5, and R6 have the meanings given in the description, and their physiologically acceptable salts. The compounds are suitable for use, for example, as hypolipidemics.
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: January 31, 2006
    Assignee: Aventis Pharma Deutschland GmbH
    Inventors: Heiner Glombik, Werner Krame, Stefanie Flohr, Wendelin Frick, Hubert Heuer, Gerhard Jaehne, Andreas Lindenschmidt, Hans-Ludwig Schäfer
  • Patent number: 6974800
    Abstract: The present invention relates to pharmaceutical formulations of an inhibitor of carboxypeptidase U (CPU) and a thrombin inhibitor in admixture with a pharmaceutically acceptable adjuvant, diluent or carrier, as well as a kit of parts, a method for treatment and use of the formulations for the treatment of a condition in which inhibition of CPU and/or inhibition of thrombin are required or desired.
    Type: Grant
    Filed: May 3, 2000
    Date of Patent: December 13, 2005
    Assignee: AstraZeneca AB
    Inventors: Tommy Abrahamsson, Viveca Nerme, Magnus Polla
  • Patent number: 6927236
    Abstract: The present invention relates to compounds of the formula which are formed during fermentation by the microorganism Coniochaeta ellipsoidea Udagawa, DSM 13856, or by one of its mutations and/or variants, and chemically derivatized if appropriate. The invention furthermore relates to a process for preparing compounds of the formula (I), and to their use as pharmaceuticals. In addition, the invention relates to the use of a compound of the formula (VI) for producing a pharmaceutical for the treatment and prophylaxis of degenerative neuropathics or of Alzheimer's disease.
    Type: Grant
    Filed: September 19, 2002
    Date of Patent: August 9, 2005
    Assignee: Aventis Pharma Deutschland GmbH.
    Inventors: Laszlo Vertesy, Klaus Ehrlich, Michael Kurz, Marian Paul Segeth, Luigi Toti
  • Patent number: 6914158
    Abstract: The present invention relates to amidino compounds and salts and prodrugs thereof. In another embodiment the present invention also provides a use of the present compounds in therapy, particular as nitric oxide synthase inhibitors. In a further embodiment, the present invention provides methods of making the amidino compounds.
    Type: Grant
    Filed: April 1, 2004
    Date of Patent: July 5, 2005
    Assignee: Pharmacia Corporation
    Inventors: Ronald Keith Webber, Richard C. Durley, Alok K. Awasthi, Arija A. Bergmanis, Kam F. Fok, Scott S. Ganser, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Brian S. Hickory, Pamela T. Manning, Michael Mao, Alan E. Moormann, Barnett S. Pitzele, Michelle A. Promo, Richard R. Schartman, Jeffrey A. Scholten, Jeffrey S. Snyder, Mihaly V. Toth, Mahima Trivedi, Sofya Tsymbalov, Foe Siong Tjoeng
  • Patent number: 6903220
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. A method of preparing a 2-alkyl amino acid involves reacting cysteine (or a salt or an ester thereof) and an aryl carboxylic acid to form a thiazoline ring, stereospecifically alkylating the thiazoline ring, and hydrolyzing the thiazoline ring to obtain a 2-alkylcysteine (or related compound). The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine, a 2-alkyl cysteine, or a cysteine ester.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: June 7, 2005
    Assignee: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Bhanu M. Chanda
  • Patent number: 6861532
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. A method of preparing a 2-alkylcysteine involves condensing cysteine with an aryl nitrile to form a 2-arylthiazoline-4-carboxylic acid, followed by alkylating the 2-arylthiazoline-4-carboxylic acid at the 4-position. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: March 1, 2005
    Assignee: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Bhanu M. Chanda, Joseph Cherian
  • Publication number: 20040267049
    Abstract: A process by which high-quality crystals of methionine in the form of granules or thick plates having high bulk density can be stably produced. The process for production of methionine comprises the step of hydrolyzing 5-(2-methylmercaptoethyl)hydantoin into a metal salt of methionine by the use of at least one metal compound selected from the group consisting of metal hydroxides, metal carbonates, and metal bicarbonates, the step of neutralizing the metal salt of methionine under pressurizing with carbon dioxide to crystallize methionine, the step of separating the resulting mixture into methionine and a filtrate, and the step of recycling the filtrate to the step of hydrolysis of 5-(2-methylmercaptoethyl)-hydantoin, wherein the content of methionine polymers and/or salts thereof in the aqueous solution used in the crystallization step in terms of methionine polymers is adjusted to 8 wt % or below based on the amount of methionine to be formed.
    Type: Application
    Filed: April 27, 2004
    Publication date: December 30, 2004
    Inventors: Toru Kawabe, Toshimichi Okubo, Tadashi Umezawa, Masayuki Sato, Takeomi Koga
  • Publication number: 20040225150
    Abstract: Methods of selectively removing counterions from compounds are disclosed. Compounds derived from the methods, such as the compound S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine zwitterion with between zero and up to 2 molar equivalents of hydrochloride are also disclosed.
    Type: Application
    Filed: March 10, 2004
    Publication date: November 11, 2004
    Inventor: Christine Moore
  • Patent number: 6797284
    Abstract: Phytopharmaceutical food products which contain plant extracts and aminoacids and which can be used in order to reduce tobacco smoke addiction.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: September 28, 2004
    Inventor: Ursula Mariah Rothlin
  • Patent number: 6794515
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. In one embodiment, the present invention relates to a method of preparing 2-alkylcysteine comprising condensing cysteine with an aryl nitrile to form a 2-arylthiazoline-4-carboxylic acid, forming a 2-arylthiazoline-4-amide using an amine group comprising at least one substituted or unsubstituted alkyl group that comprises one or more chiral carbon atoms, and alkylating at the 4-position of the thiazoline ring to form a 2-aryl-4-alkyl-thiazoline-4-amide. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In one embodiment, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: September 21, 2004
    Assignee: Genzyme Corporation
    Inventors: Rayomand H. Gimi, Mukund S. Chorghade, Sunil V. Mhaskar
  • Publication number: 20040122099
    Abstract: The instant invention provides a process for the preparation of S-(2-aminoethyl)-2-methyl-L-cysteine comprised of the steps of (i) esterification of 2-methyl-L-cysteine; (ii) alkylation of the cysteine ester of step (i) to provide an N-protected S-(2-aminoethyl)-2-methyl-L-cysteine ester; and (iii) hydrolysis of the intermediate of step (ii) to provide the title compound in a salt free state.
    Type: Application
    Filed: October 29, 2003
    Publication date: June 24, 2004
    Inventor: Peter Guillaume Marie Wuts
  • Publication number: 20040087654
    Abstract: A compound of formula (I): namely (2S)-2-amino-4-{[2-(etha-nimidoylamino)ethyl]thio}butanoic acid, compound with prosphoric acid, or a solvate or physiologically functional derivative thereof, is useful as a relatively non-hygroscopic selective inhibitor of inducible nitric oxice synthase.
    Type: Application
    Filed: November 11, 2003
    Publication date: May 6, 2004
    Inventors: David Box, David Colclough, Iain Gillies, Michael Simon Loft, Rebecca Moore
  • Publication number: 20040006224
    Abstract: A method of preparing a 2-alkyl amino acid involves the aziridination of an alkylacrylate and the opening of the aziridine ring by addition of a side chain. This method can result in the preparation of enantiomeric excess of a 2-alkyl amino acid. The invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine, a 2-alkyl cysteine, or a cysteine ester.
    Type: Application
    Filed: May 15, 2003
    Publication date: January 8, 2004
    Applicant: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Bhanu M. Chanda
  • Patent number: 6673942
    Abstract: The present invention relates to a process for the resolution of DL-racemic mixtures of compounds which crystalize in the form of a conglumerate. Both, the D and L-enantiomers are obtained according to the invention in a industrially feasable process by adding chiral enantioselective polymers to the supersaturated solution of the racemat to inhibit crystalization of one enantiomer. Next a DL-racemic mixture of said compound is suspended in about twice the amount of the crystallized enantiomer. Consequently, the opposite enantiomer could be recovered by said suspension by physical separation.
    Type: Grant
    Filed: July 23, 2002
    Date of Patent: January 6, 2004
    Assignees: Degussa AG, Yeda Research and Development Co., Ltd.
    Inventors: Matthias Kottenhahn, Guenter Knaup, Karlheinz Drauz, Meir Lahav, David Zbaida
  • Publication number: 20030236434
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. In one embodiment, the present invention relates to a method of preparing 2-alkylcysteine comprising condensing cysteine with an aryl nitrile to form a 2-arylthiazoline-4-carboxylic acid, forming a 2-arylthiazoline-4-amide using an amine group comprising at least one substituted or unsubstituted alkyl group that comprises one or more chiral carbon atoms, and alkylating at the 4-position of the thiazoline ring to form a 2-aryl-4-alkyl-thiazoline-4-amide. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In one embodiment, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine.
    Type: Application
    Filed: May 15, 2003
    Publication date: December 25, 2003
    Applicant: Genzyme Corporation
    Inventors: Rayomand H. Gimi, Mukund S. Chorghade, Sunil V. Mhaskar
  • Publication number: 20030236435
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. In one embodiment, the present invention relates to a method of preparing a 2-alkylcysteine comprising condensing cysteine with an aryl nitrile to form a 2-arylthiazoline-4-carboxylic acid, esterifying the 2-arylthiazoline-4-carboxylic acid using a substituted or unsubstituted alcohol group comprising one or more chiral carbons, and alkylating at the 4-position of the thiazoline ring to form a 2-aryl-4-alkyl-thiazoline-4-carboxylic acid ester. The chiral templates present in the thiazoline carboxylic acid ester can provide face selectivity, and consequently desired stereochemistry, during the delivery of an alkyl group to the 4-position of the thiazoline ring. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring.
    Type: Application
    Filed: May 15, 2003
    Publication date: December 25, 2003
    Applicant: Genzyme Corporation
    Inventors: Rayomand H. Gimi, Mukund S. Chorghade, Sunil V. Mhaskar
  • Patent number: 6627732
    Abstract: The present invention provides a glutathione derivative having a dramatically enhanced hematopoiesis promoting effect in the living body represented by the formula (I): where A represents H or a C1-C20 acyl group; R1 represents a C1-C26 alkyl group or a C3-C26 alkenyl group; and R2 represents H, a C1-C26 alkyl group or a C3-C26 alkyl group, with the proviso that compounds are excluded in which R1 is a C1-C10 alkyl group or a C3-C10 alkenyl group, and simultaneously R2 is H, a C1-C10 alkyl group or a C3-C10 alkenyl group. The present invention also provides a salt of the glutathione derivative, or a colloidal composition that enables the safe and effective development of the effects of the glutathione derivative in the living body.
    Type: Grant
    Filed: October 16, 2000
    Date of Patent: September 30, 2003
    Assignee: Teijin Limited
    Inventors: Kiyoyuki Sakon, Yoshimitsu Naniwa, Mitsuru Kobayashi, Daishiro Miura, Hiroshi Imai, Atsushi Imaizumi
  • Patent number: 6599940
    Abstract: One aspect of the present invention relates to 2-hydroxymethylglutamic acid and congeners thereof. A second aspect of the invention relates to a method of synthesizing 2-hydroxymethylglutamic acid and congeners thereof.
    Type: Grant
    Filed: September 13, 2001
    Date of Patent: July 29, 2003
    Assignee: Georgetown University
    Inventor: Alan P. Kozikowski
  • Patent number: 6586474
    Abstract: The present invention relates to amidino compounds and salts and prodrugs thereof. In another embodiment the present invention also provides a use of the present compounds in therapy, particular as nitric oxide synthase inhibitors. In a further embodiment, the present invention provides methods of making the amidino compounds.
    Type: Grant
    Filed: March 23, 2001
    Date of Patent: July 1, 2003
    Assignee: Pharmacia Corporation
    Inventors: Ronald Keith Webber, Richard C. Durley, Alok K. Awasthi, Arija A. Bergmanis, Kam F. Fok, Scott S. Ganser, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Brian S. Hickory, Pamela T. Manning, Michael Mao, Alan E. Moormann, Barnett S. Pitzele, Michelle A. Promo, Richard R. Schartman, Jeffrey A. Scholten, Jeffrey S. Snyder, Mihaly V. Toth, Mahima Trivedi, Sofya Tsymbalov, Foe Siong Tjoeng
  • Patent number: 6548700
    Abstract: A process for precipitating cystine from a solution in sulfuric acid, includes forming a mixture of a solution of cystine in aqueous sulfuric acid and of an aqueous solution of a base by simultaneous metering the cystine solution and the aqueous base solution into a mixing container. The metering takes place in such a way that the mixture in the container has a pH between 1.0 and 7.0 and a temperature between 30° C. and the boiling point of the mixture.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: April 15, 2003
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Wolfgang Döring, Jürgen Stohrer
  • Patent number: 6531608
    Abstract: This invention relates to the synthesis of certain complexes of cysteine, N-acetylcysteine, N-(2-mercaptopropionyl)glycine, and L-2-oxothiazolidine-4-carboxylate and to the nutritional use of these and other related individual or complexed thiol-contributing glutathione predecessors. Clinical uses for these molecules and complexes in the beneficial modification of various physiological conditions and functions associated with aging, chronic glaucoma, diabetes mellitus, insulin resistance, macular degeneration, neurodegenerative diseases and vasoconstriction are described in particular.
    Type: Grant
    Filed: June 11, 2002
    Date of Patent: March 11, 2003
    Assignee: Chronorx, LLC.
    Inventors: Don C. Pearson, Kenneth T. Richardson
  • Patent number: 6495606
    Abstract: The present invention relates to novel amidino compounds of formula (I), or a salt, solvate, or physiologically functional derivative thereof; wherein R1 is selected from C1-4 alkyl, C3-4 cycloalkyl, C1-4 hydroxyalkyl, and C1-4 haloalkyl; to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use as selective inhibitors of inducible nitric oxide synthase.
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: December 17, 2002
    Assignee: SmithKline Beecham Corporation
    Inventors: Paul John Beswick, Savvas Kleanthous, Robert John Young
  • Patent number: 6417395
    Abstract: The invention concerns a method for preparing methionine aminoamide. The invention also concerns the preparation of methionine without co-production of salts, from an aqueous solution containing essentially methionine aminonitrile by producing during a first step aminoamide followed by two complementary steps.
    Type: Grant
    Filed: July 12, 2001
    Date of Patent: July 9, 2002
    Assignee: Aventis Animal Nutrition S.A.
    Inventors: Hervé Ponceblanc, Olivier Favre-Bulle, Georges Gros
  • Patent number: 6403830
    Abstract: The present invention relates to S-[2-[(1-Iminoethyl)amino]ethyl]-2-methyl-L-cysteine, or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: March 23, 2001
    Date of Patent: June 11, 2002
    Assignee: Pharmacia Corporation
    Inventors: Ronald Keith Webber, Richard C. Durley, Alok K. Awasthi, Arija A. Bergmanis, Scott S. Ganser, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Brian S. Hickory, Alan E. Moormann, Barnett S. Pitzele, Michelle A. Promo, Richard R. Schartman, Jeffrey S. Snyder, Mahima Trivedi, Sofya Tsymbalov
  • Patent number: 6372912
    Abstract: Process for the hydrolytic ring cleavage of thiazolidine derivatives to give 2-aminomercaptan derivatives and carbonyl compounds, which comprises bringing an aqueous solution of the thiazolidine derivative into contact with an acidic cation exchanger in the H+ form, giving a solution L1 which contains the carbonyl compound and eluting the cation exchanger with a suitable eluent, giving a solution L2 which contains the 2-aminomercaptan derivative.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: April 16, 2002
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Wolfgang Döring, Günther Karl Staudinger
  • Patent number: 6355689
    Abstract: The present invention relates to novel amidino compounds of formula (I), or a salt, solvate, or physiologically functional derivative thereof; wherein R1 is selected from C1-4 alkyl, C3-4 cycloalkyl, C1-4 hydroxyalkyl, and C1-4 haloalkyl; to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use as selective inhibitors of inducible nitric oxide synthase.
    Type: Grant
    Filed: November 29, 2000
    Date of Patent: March 12, 2002
    Assignee: SmithKline Beecham Corporation
    Inventors: Paul John Beswick, Savvas Kleanthous, Robert John Young
  • Publication number: 20010034369
    Abstract: Novel compounds, their salts and compositions related thereto having activity against mammalian integrins are disclosed. The compounds are useful in vitro or in vivo for preventing or treating thrombotic or restenotic disorders.
    Type: Application
    Filed: May 15, 2001
    Publication date: October 25, 2001
    Inventors: Robert M. Scarborough, Mark Smyth, Ting Su, Matthew J. Fisher, Joseph A. Jakubowski, John J. Masters, Jeffry Bernard Franciskovich
  • Patent number: 6306840
    Abstract: The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: October 23, 2001
    Assignee: Biogen, Inc.
    Inventors: Steven P. Adams, Ko-Chung Lin, Wen-Cherng Lee, Alfredo C. Castro, Craig N. Zimmerman, Charles E. Hammond, Yu-Sheng Liao
  • Patent number: 6251868
    Abstract: The present invention provides a method for preventing or treating a human immunodeficiency virus (HIV) infection, including a new or an asymptomatic infection as well as AIDS, comprising administering to a mammal in need thereof a HIV infection preventing or treating effective amount of a &ggr;-L-glutamnyl-L-cysteine ester compound of formula (I): wherein R is a straight chain, branched or cyclic hydrocarbon group having 1-10 carbon atoms, or a straight chain or branched hydrocarbon group having 1-5 carbon atoms substituted with an aromatic group; or the oxidized dimer obtained by dehydrogenation between two &ggr;-L-glutamyl-L-cysteine esters having formula (I).
    Type: Grant
    Filed: April 30, 1998
    Date of Patent: June 26, 2001
    Assignees: Teijin Limited, Thomas Jefferson University
    Inventors: Satoshi Kubota, Roger J. Pomerantz, Shigehisa Kitahara
  • Patent number: 6239111
    Abstract: The present invention discloses the use, in the manufacture of a preventive and therapeutic drug of a brain disease, of a compound represented by formula (1): CH2═CH—CH2—S(O)n—R  (1) [wherein R represents a hydrogen atom, an alkyl group, an alkenyl group, a substituted alkyl group, a substituted alkenyl group, an alkylthio group, an alkenylthio group, a phenyl group, a substituted phenyl group, a heterocyclic group, or a group derived from an amino acid or an oligopeptide by deletion of one hydrogen atom, and which group may have a protective group; and n is 0, 1, or 2], a glycoside thereof, or a salt of the compound or the glycoside. The drug of the present invention for ameliorating brain diseases, inhibiting reduction of brain neurons and promoting branching of neurites, is useful for the prevention and treatment of brain diseases such as dementia in association with degeneration and sloughing of brain neurons.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: May 29, 2001
    Assignee: Wakunaga Pharmaceutical Co., Ltd.
    Inventors: Toru Moriguchi, Hiromichi Matsuura, Hiroshi Saito
  • Patent number: 6147257
    Abstract: A process for the preparation of S-alkylcysteines of formula ##STR1## wherein R is a lower or branched C.sub.1 -C.sub.4 alkyl group; by S-alkylation of cysteines with dialkylcarbonates.
    Type: Grant
    Filed: February 3, 1999
    Date of Patent: November 14, 2000
    Assignee: Zambon Group S.p.A.
    Inventors: Pietro Allegrini, Giuseppe Barreca, Elena Rossi