Racemization Or Optical Resolution Patents (Class 548/498)
  • Patent number: 7998538
    Abstract: The present disclosure relates to methods and systems that provide heat, via at least Photon-Electron resonance, also known as excitation, of at least a particle utilized, at least in part, to initiate and/or drive at least one catalytic chemical reaction. In some implementations, the particles are structures or metallic structures, such as nanostructures. The one or more metallic structures are heated at least as a result of interaction of incident electromagnetic radiation, having particular frequencies and/or frequency ranges, with delocalized surface electrons of the one or more particles. This provides a control of catalytic chemical reactions, via spatial and temporal control of generated heat, on the scale of nanometers as well as a method by which catalytic chemical reaction temperatures are provided.
    Type: Grant
    Filed: December 14, 2004
    Date of Patent: August 16, 2011
    Assignee: California Institute of Technology
    Inventors: Leslie Frederick Greengard, Mark Brongersma, David A. Boyd
  • Publication number: 20080261944
    Abstract: The present invention relates to indole compounds of the formula (I): wherein R1, R2, R3, R4, A, E and X are as defined herein, and pharmaceutically acceptable salts thereof, useful in the prevention and treatment of hepatitis C infections.
    Type: Application
    Filed: June 8, 2005
    Publication date: October 23, 2008
    Inventors: Stefania Colarusso, Immacolata Conte, Joerg Habermann, Frank Narjes, Simona Ponzi
  • Publication number: 20070249704
    Abstract: The present invention is directed to a process for preparing Fluvastatin Sodium salt by basic hydrolysis of its alkyl ester. The reaction is performed in conditions suitable to allow a selective hydrolysis of the desired syn isomer, while the unwanted anti isomer is removed by extraction, thus reducing its content in the final product; this diastereomer is the main impurity of Fluvastatin sodium salt and its ester precursor.
    Type: Application
    Filed: April 19, 2007
    Publication date: October 25, 2007
    Inventor: Marco Fachini
  • Publication number: 20040210060
    Abstract: Process for the separation of enantiomers comprising at least one free functional group, in which process a reagent based on an enantiopure amino acid is reacted in basic medium with a mixture comprising enantiomers.
    Type: Application
    Filed: May 7, 2004
    Publication date: October 21, 2004
    Applicant: SOLVAY S.A.
    Inventors: Thierry Delplanche, Roland Callens
  • Patent number: 6013830
    Abstract: Processes for preparing a single enantiomer of an .alpha.,.alpha.-disubstituted-.alpha.-hydroxy acetic acid, especially cyclohexylphenylglycolic acid (CHPGA), is disclosed. The processes employ cyclic 1,2-aminoalcohols as chiral auxiliaries by forming diastereomeric esters of aminoalcohols or diastereomeric amides of oxazolidines. ##STR1## Intermediates useful in the process are also disclosed.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: January 11, 2000
    Assignee: Sepracor Inc.
    Inventors: Chris Hugh Senanayake, Roger P. Bakale, Qun Kevin Fang, Paul Timothy Grover, Donald L. Heefner, Richard F. Rossi, Stephen Alan Wald
  • Patent number: 5994560
    Abstract: Described herein is a novel process to resolve a racemic compound into its optically active isomers without need for chemical transformation such as salt formation. The process advantageously utilizes polymers containing chiral moieties in their repeat units as well as exhibiting critical solution temperature behavior in a suitable solvent. An embodiment describes the resolution of tryptophan.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: November 30, 1999
    Assignee: Hoechst Celanese Corp.
    Inventors: Hyun Nam Yoon, Mengshi Lu, Naoya Ogata
  • Patent number: 5892112
    Abstract: Synthetic mammalian matrix metalloprotease inhibitors are disclosed that are useful for treating or preventing diseases wherein said diseases are caused by unwanted mammalian matrix metalloprotease activity and include skin disorders, keratoconus, restenosis, rheumatoid arthritis, wounds, cancer, angiogenesis and shock.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: April 6, 1999
    Assignees: Glycomed Incorporated, The University of Florida
    Inventors: Daniel E. Levy, Damian Grobelny, Cho Tang, Kevin R. Holme, Richard E. Galardy, Gregory S. Schultz, Asaad Nematalia, John H. Musser
  • Patent number: 5329014
    Abstract: Optically active tryptophan of high purity can be obtained in high yields from a tryptophan fermentation broth, using crystallization of optically active tryptophan hydrochloride in combination with concurrent neutralization crystallization. According to the present invention, optically active tryptophan from a tryptophan containing fermentation broth, is carried out by (a) removing cells from the fermentation broth, adding hydrochloric acid, or a mixture of hydrochloric acid and an inorganic salt which contains chloride ions, to the cell-free broth to effect crystallization, (b) separating optically active tryptophan hydrochloride, (c) dissolving the optically active tryptophan hydrochloride, and (d) subjecting the resulting solution and an alkali solution to concurrent neutralization crystallization, maintaining a pH of the crystallization solution in the range of from 3 to 8.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: July 12, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toru Shinohara, Masaru Otani
  • 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: 4918196
    Abstract: A process for optically isomerizing an optically active alpha-amino acid amide comprising heating a D-alpha-amino acid amide or an L-alpha-amino acid amide in the presence of a strongly basic compound; and a process for producing an L-alpha-amino acid, which comprises(1) subjecting a D,L-alpha-amino acid amide or a mixture of a major amount of a D-alpha-amino acid amide and a minor amount of an L-alpha-amino acid amide to the action of a microorganism having the ability to hydrolyze the L-alpha-amino acid to obtain a hydrolyzate containing the L-alpha-amino acid and D-alpha-amino acid,(2) separating the L-alpha-amino acid from the hydrolyzate and recovering the remaining D-alpha-amino acid amide.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: April 17, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masaharu Doya, Toshio Kondo, Hideo Igarashi, Takako Uchiyama
  • Patent number: 4904654
    Abstract: A metabolite of the known anxiolytic agent, 7-chloro-5,6-dihydro-3-(5-isopropyl-1,2,4-oxadiazol-3-yl)-5-methyl-6-oxo-4 H- imidazo[1,5a][1,4]benzodiazepine is a 2-hydroxy derivative of the isopropyl moiety and is itself an anxiolytic agent.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: February 27, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Jiunn H. Lin, Steven M. Pitzenberger, Harri G. Ramjit, Edgar H. Ulm
  • Patent number: 4874752
    Abstract: A novel benzoquinone derivative of the general formula: ##STR1## [wherein R.sub.1 and R.sub.2 are the same or different and each is methyl or methoxy; n is an integer of 0 to 21; m is 0 or 1, Z is a group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen or an alkyl group which may optionally be substituted or, R.sub.3 and R.sub.4 together with the adjacent nitrogen atom form a morpholino group), a group of the formula: --COR.sub.5 (wherein R.sub.5 is an .alpha.-amino acid residue or a substituted or unsubstituted glucosamine residue), a group of the formula: ##STR3## (wherein R.sub.6 is a divalent hydrocarbon group of 1 to 3 carbon atoms), a group of the formula: ##STR4## (wherein R.sub.6 has the same meaning as defined above) or a group of the formula: --CH.dbd.CH).sub.l COR.sub.7 (wherein l is an integer of 1 to 4 and R.sub.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: October 17, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada
  • Patent number: 4772599
    Abstract: New benzodiazepine derivatives of the general formula ##STR1## wherein X.sup.1 and X.sup.2 independently are ##STR2## wherein R.sup.1 is C.sub.1-3 -alkyl, C.sub.3-5 -cycloalkyl, C.sub.1-3 -alkoxymethyl, C.sub.1-3 -hydroxyalkyl, or aryl,R.sup.4 is hydrogen, andR.sup.5 is C.sub.1-6 -alkyl, or wherein R.sup.4 and R.sup.5 together form a 2-4 membered alkylene chain.The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: September 20, 1988
    Assignee: A/S Ferrosan
    Inventor: Frank Watjen
  • Patent number: 4718994
    Abstract: A method for perparing hydroxy compounds of the aromatic and heteroaromatic series of the general formula: ##STR1## wherein when R.sub.1 .dbd.--COOH, --CH.sub.2 CH(NH.sub.2)COOH then R.sub.2 .dbd.--OH, --H, --COOH; R.sub.3 .dbd.--H, --OH; R.sub.4, R.sub.5 .dbd.--H with no connecting bond; R.sub.6 .dbd.--OH; and when R.sub.1,R.sub.6,R.sub.3 .dbd.--H, R.sub.2 .dbd.--OH; then R.sub.4 .dbd.>NH; R.sub.5 .dbd.--CR.sub.7 .dbd.CHR.sub.4, where R.sub.7 .dbd.--CH.sub.2 --CH.sub.2 --NH.sub.2, --CH.sub.2 --CH(NH.sub.2)COOH, consists in that aromatic and heteroaromatic compounds of the general formula ##STR2## wherein when R.sub.1 .dbd.--COOH, --CH.sub.2 CH(NH.sub.2)COOH, then R.sub.2 .dbd.--OH, --H, --COOH; R.sub.3 .dbd.--H, --OH; R.sub.4,R.sub.5 .dbd.--H with no connecting bond; and when R.sub.1,R.sub.2,R.sub.3 .dbd.--H, then R.sub.4 .dbd.>NH; R.sub.5 .dbd.--CR.sub.7 .dbd.CHR.sub.4, where R.sub.7 .dbd.--CH.sub.2 --CH.sub.2 --NH.sub.2, --CH.sub.2 --CH(NH.sub.2)COOH.
    Type: Grant
    Filed: June 14, 1985
    Date of Patent: January 12, 1988
    Assignee: Latviisky Gosudarstvenny Universaitet Imeni P. Stuchki
    Inventors: Andrei K. Zhagars, Voldemar Y. Grinshtein, Sniedzite A. Ozola, Andris K. Zitsmanis, Avgust K. Arens
  • Patent number: 4713470
    Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxy-aromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.
    Type: Grant
    Filed: May 22, 1985
    Date of Patent: December 15, 1987
    Assignee: Stauffer Chemical Company
    Inventor: Stanley B. Mirviss
  • Patent number: 4610827
    Abstract: A method for optical resolution of a DL-amino acid comprising reacting the DL-amino acid with an optically active N-acyl aspartic acid in a solvent or mixture of solvents, and separating the resulting two diasteromeric salts by way of the difference between their solubilities in the solvent or mixture of solvents. The difference in solubility may be enhanced by cooling, concentration, addition of a solubility-decreasing organic solvent, pH adjustment or salting out.
    Type: Grant
    Filed: July 10, 1984
    Date of Patent: September 9, 1986
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toshihide Yukawa, Toru Ikeda, Shinichi Kishimoto, Katsumi Sugiyama
  • Patent number: 4602096
    Abstract: N-acetyl-D(L)-.alpha.-aminocarboxylic acids are thermally racemized by melting, adding a small amount of acetic anhydride to the melt and heating to a temperature between the melting temperature and about 210.degree. C. and subsequently quenching the melt with an aqueous alkali metal hydroxide or ammonia solution. The residence time needed for complete racemization depends on the heating temperature of the melt in the manner that the higher the heating temperature the shorter the residence time.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: July 22, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Michael Karrenbauer, Axel Kleemann
  • Patent number: 4588818
    Abstract: A method for recovery of optically active tryptophane, which comprises filtering a solution of optically active tryptophane containing impurities through a semi-permeable membrane; adding a lower alcohol or a ketone to the filtrate; maintaining the solution containing the lower alcohol or ketone at an alkaline pH and a temperature higher than the .alpha./.beta. crystalline transition point; adding acid to the solution, thereby causing crystals of optically active tryptophane to form in the solution; and separating the crystals from the solution containing impurities, is disclosed. This method avoids the use of resins in the purification steps.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: May 13, 1986
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tetsuya Kaneko, Toshio Kitahara, Toyokazu Kaneko
  • 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: 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: 4481362
    Abstract: Biochemical optical resolution of DL-tryptophanes in which DL-tryptophane amides are interacted with the culture products, or their treated products, of a microorganism capable of producing amidase is described. L-tryptophane amides in racemic DL-tryptophane amides are asymmetrically hydrolyzed to form optically active L-tryptophanes at a high yield and almost all D-tryptophane amides remain without being subjected to hydrolysis. The resultant D-tryptophane amides are readily hydrolyzed, after separating L-tryptophanes, to form optically active D-tryptophanes at a high yield.
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: November 6, 1984
    Assignee: Ube Industries, Inc.
    Inventors: Mamoru Nakai, Tokio Ohshima, Tomio Kimura, Tetsuo Omata, Noritada Iwamoto
  • Patent number: 4440936
    Abstract: The chiral phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane, when complexed to Rh(I), functions as a superior chiral hydrogenation catalyst. The chiral phosphine ligand is more stereochemically rigid than previous compounds; consequently, virtually optically pure materials can be produced from the chiral hydrogenation of prochiral compounds using the catalyst of this invention. This catalyst is especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.
    Type: Grant
    Filed: January 18, 1982
    Date of Patent: April 3, 1984
    Assignee: The Procter & Gamble Company
    Inventor: Dennis P. Riley
  • Patent number: 4408050
    Abstract: Novel spiro[indoline-3,4'-piperidine]s and related compounds and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants and tranquilizers. Also described is a novel method of preparing indoline rings.
    Type: Grant
    Filed: December 18, 1981
    Date of Patent: October 4, 1983
    Assignee: American Hoechst Corporation
    Inventors: Helen H. Ong, James A. Profitt
  • Patent number: 4379941
    Abstract: Racemic amino acids can be readily resolved by conversion to their diastereomeric esters of an optically active 2-isopropyl-5-methylcyclohexanol and separating the diastereomers by chromatography. It has been observed that the separation of the diastereomeric esters is relatively insensitive to the support or the solvent used as eluant. Thus, satisfactory separation occurs under a broad variety of conditions. The optically active amino acid can be obtained by base catalyzed hydrolysis of the purified diastereomer with high optical purity.
    Type: Grant
    Filed: January 8, 1982
    Date of Patent: April 12, 1983
    Assignee: UOP Inc.
    Inventor: David W. House