Racemization Or Optical Resolution Patents (Class 548/498)
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Patent number: 7998538Abstract: 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: GrantFiled: December 14, 2004Date of Patent: August 16, 2011Assignee: California Institute of TechnologyInventors: Leslie Frederick Greengard, Mark Brongersma, David A. Boyd
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Publication number: 20080261944Abstract: 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: ApplicationFiled: June 8, 2005Publication date: October 23, 2008Inventors: Stefania Colarusso, Immacolata Conte, Joerg Habermann, Frank Narjes, Simona Ponzi
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Publication number: 20070249704Abstract: 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: ApplicationFiled: April 19, 2007Publication date: October 25, 2007Inventor: Marco Fachini
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Publication number: 20040210060Abstract: 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: ApplicationFiled: May 7, 2004Publication date: October 21, 2004Applicant: SOLVAY S.A.Inventors: Thierry Delplanche, Roland Callens
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Patent number: 6013830Abstract: 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: GrantFiled: March 30, 1998Date of Patent: January 11, 2000Assignee: Sepracor Inc.Inventors: Chris Hugh Senanayake, Roger P. Bakale, Qun Kevin Fang, Paul Timothy Grover, Donald L. Heefner, Richard F. Rossi, Stephen Alan Wald
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Patent number: 5994560Abstract: 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: GrantFiled: August 29, 1996Date of Patent: November 30, 1999Assignee: Hoechst Celanese Corp.Inventors: Hyun Nam Yoon, Mengshi Lu, Naoya Ogata
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Patent number: 5892112Abstract: 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: GrantFiled: January 21, 1994Date of Patent: April 6, 1999Assignees: Glycomed Incorporated, The University of FloridaInventors: Daniel E. Levy, Damian Grobelny, Cho Tang, Kevin R. Holme, Richard E. Galardy, Gregory S. Schultz, Asaad Nematalia, John H. Musser
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Patent number: 5329014Abstract: 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: GrantFiled: July 31, 1991Date of Patent: July 12, 1994Assignee: Ajinomoto Co., Inc.Inventors: Toru Shinohara, Masaru Otani
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Patent number: 4978759Abstract: 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: GrantFiled: July 2, 1986Date of Patent: December 18, 1990Assignee: Sanofi, S.A. and Institut National de la Sante et de la Recherche MedicaleInventors: Patrick Jouin, Dino Nisato, Bertrand Castro
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Patent number: 4918196Abstract: 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: GrantFiled: February 21, 1986Date of Patent: April 17, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masaharu Doya, Toshio Kondo, Hideo Igarashi, Takako Uchiyama
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Patent number: 4904654Abstract: 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: GrantFiled: July 26, 1989Date of Patent: February 27, 1990Assignee: Merck & Co., Inc.Inventors: Jiunn H. Lin, Steven M. Pitzenberger, Harri G. Ramjit, Edgar H. Ulm
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Patent number: 4874752Abstract: 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: GrantFiled: November 8, 1988Date of Patent: October 17, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada
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Patent number: 4772599Abstract: 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: GrantFiled: March 13, 1987Date of Patent: September 20, 1988Assignee: A/S FerrosanInventor: Frank Watjen
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Patent number: 4718994Abstract: 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: GrantFiled: June 14, 1985Date of Patent: January 12, 1988Assignee: Latviisky Gosudarstvenny Universaitet Imeni P. StuchkiInventors: Andrei K. Zhagars, Voldemar Y. Grinshtein, Sniedzite A. Ozola, Andris K. Zitsmanis, Avgust K. Arens
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Patent number: 4713470Abstract: 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: GrantFiled: May 22, 1985Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Stanley B. Mirviss
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Patent number: 4610827Abstract: 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: GrantFiled: July 10, 1984Date of Patent: September 9, 1986Assignee: Ajinomoto Co., Inc.Inventors: Toshihide Yukawa, Toru Ikeda, Shinichi Kishimoto, Katsumi Sugiyama
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Patent number: 4602096Abstract: 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: GrantFiled: August 12, 1985Date of Patent: July 22, 1986Assignee: Degussa AktiengesellschaftInventors: Michael Karrenbauer, Axel Kleemann
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Patent number: 4588818Abstract: 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: GrantFiled: November 7, 1984Date of Patent: May 13, 1986Assignee: Ajinomoto Co., Inc.Inventors: Tetsuya Kaneko, Toshio Kitahara, Toyokazu Kaneko
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Patent number: 4540792Abstract: 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: GrantFiled: March 7, 1983Date of Patent: September 10, 1985Assignees: Centre National de la Recherche Scientifique, Institut National de la Sante et de la Reserche MedicaleInventors: Auguste Commeyras, Aldo Previero, Martine Pugniere
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Patent number: 4519955Abstract: .alpha.-(S)-amino acid..alpha.-phenylethanesulfonate compounds and methods of optical resolution of .alpha.-amino acids and .alpha.-phenylethanesulfonic acids are described.Type: GrantFiled: March 2, 1984Date of Patent: May 28, 1985Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ichiro Chibata, Shigeki Yamada, Chikara Hongo, Ryuzo Yoshioka
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Patent number: 4481362Abstract: 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: GrantFiled: May 17, 1983Date of Patent: November 6, 1984Assignee: Ube Industries, Inc.Inventors: Mamoru Nakai, Tokio Ohshima, Tomio Kimura, Tetsuo Omata, Noritada Iwamoto
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Patent number: 4440936Abstract: 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: GrantFiled: January 18, 1982Date of Patent: April 3, 1984Assignee: The Procter & Gamble CompanyInventor: Dennis P. Riley
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Patent number: 4408050Abstract: 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: GrantFiled: December 18, 1981Date of Patent: October 4, 1983Assignee: American Hoechst CorporationInventors: Helen H. Ong, James A. Profitt
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Patent number: 4379941Abstract: 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: GrantFiled: January 8, 1982Date of Patent: April 12, 1983Assignee: UOP Inc.Inventor: David W. House