Of Benzene Ring Containing Compounds Patents (Class 564/304)
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Patent number: 6323368Abstract: A process for preparing a substantially single enantiomer of tramadol, or a pharmaceutically-acceptable salt thereof, proceeds by means of a classical salt resolution using a substantially single enantiomer of O,O-di-p-toluoyltartaric acid as a resolving agent.Type: GrantFiled: November 30, 1999Date of Patent: November 27, 2001Assignee: Darwin Discovery, Ltd.Inventor: Graham Evans
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Patent number: 6310248Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of: a) enantioselectively reducing the carbonyl function in a compound of formula (II): wherein R1, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulphamoyl or halogen, to form an enantiomerically enriched compound of formula (IIIa) or (IIIb): wherein R1, R2 and R3 are as defined above; b) subjecting the compound of formula (IIIa) or (IIIb) to a sigmatropic rearrangement to form a corresponding enantiomerically enriched compound of formula (IVa) or (IVb): wherein R1, R2 and R3 are as defined above; c) subjecting the compound of formula (IVa) or (IVb) to a Baeyer-Virliger oxidation to form a corresponding enantiomerically enriched compound of the general formula (Va) or (Vb): wherein R1, R2 and R3 are as defined above; d) converting the compoType: GrantFiled: December 22, 2000Date of Patent: October 30, 2001Assignee: Pharmacia ABInventors: Pher G. Andersson, Christian Hedberg
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Patent number: 6265614Abstract: Intermediates having the formula wherein BI is —CH2OH or —CH2ORP, and RP is an alcohol protecting group; a is 1, 2, or 3; TI is —OH or QI is phenyl, naphthyl ohr heteroaryl having 1-3 substituents; Ra and Rc are the same, and are H, or are selected from alkyl, cycloalkyl and aryl groups, the groups being optionally substituted with one or more substituents selected from alkyl cycloalkyl, aryl, or —OH; or Ra and Rc together with the C—N—C chain to which they are bound, form a 5-7 membered ring; Rb and Rd are the same, and are H, or are selected from alkyl, cycloalkyl and aryl groups, the groups being optionally substituted with one or more substituents selected from alkyl, cycloalkyl, aryl, or —OH; and D is a directing group capable of directing lithiation alpha to a nitrogen atom of a nitrogen compound having D as a substituent bound to the nitrogen atom when the nitrogen compound is reacted with s-butyl lithium, are disclosedType: GrantFiled: October 13, 2000Date of Patent: July 24, 2001Assignee: Schering CorporationInventors: Anantha R. Sudhakar, Suhan Tang
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Patent number: 6235927Abstract: A diastereomer complex obtained via a process for the separation of enantiomers is disclosed, wherein separation can be rapidly effected such that enantiomers are obtained with high e.e. values. The process pets the separation of mixtures of enantiomers in which more than one resolving agent is used, of which at least one resolving agent is optically active, and which yields a diastereomer complex containing at least two resolving agents in optically active form. The process provides for, inter alia, a diastereomer complex having at least three compounds of which at least two compounds are resolving agents in optically active form, and at least one compound is an onantiomer in optically active form. Also provided is a diastereomer complex having at least three compounds of which at lea one compound is a resolving agent in optically active form, and at least two compounds which are enantiomers in optically active form.Type: GrantFiled: October 22, 1997Date of Patent: May 22, 2001Assignee: DSM N.V.Inventors: Ton R. Vries, Hans Wijnberg, Erik Van Echten, Lumbertus A. Hulshof, Quirinus B. Broxterman
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Patent number: 6225463Abstract: The object of the present invention is the development of new chiral auxiliaries for improved &bgr;-lactam formation that control both the diastereoselectivity of &bgr;-lactam formation and which can be removed without destruction of the sensitive azetidinone ring, providing valuable intermediates for coupling to the C-13 hydroxyl group of anti-tumor taxanes, such as paclitaxel. Further, the object of the present invention is enantiomerically pure (S)-(−)-1-(p-methoxy-phenyl)propyl-1-amine.Type: GrantFiled: December 15, 1998Date of Patent: May 1, 2001Assignees: Pharmachemie B.V., Cancer Research Campaign Technology Ltd.Inventors: Dick de Vos, Stephen Brown, Allan M. Jordan, Nicholas J. Lawrence, Alan Th. McGown
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Patent number: 6222072Abstract: A novel process for producing an optically active amine is provided. The optically active amine is adapted for use as an intermediate in synthesizing physiologically active compounds such as pharmaceuticals and agricultural chemicals, as a functional material such as a liquid crystal, and as a starting material in synthesizing fine chemicals. The process comprises the step of reacting an imine with a hydride reagent in the presence of an optically active metal compound and an alcohol compound and/or carboxylic acid compound.Type: GrantFiled: November 6, 1998Date of Patent: April 24, 2001Assignee: Mitsui Chemicals Inc.Inventors: Teruaki Mukaiyama, Kiyoaki Sugi, Takushi Nagata, Toru Yamada
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Patent number: 6218575Abstract: An improved process for preparing adrenaline, or an addition salt thereof, on an industrial scale, with asymmetric hydrogenation as a key step and a special sequence of successive steps, using [Rh(COD)Cl]2 as catalyst and a chiral, bidentate phosphine ligand such as (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphinomethyl)-N-methylaminocarbonylpyrrolidine as the catalyst system.Type: GrantFiled: July 26, 2000Date of Patent: April 17, 2001Assignee: Boehringer Ingelheim Pharma KGInventors: Franz Dietrich Klingler, Lienhard Wolter
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Patent number: 6184381Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.Type: GrantFiled: September 29, 1998Date of Patent: February 6, 2001Assignees: Japan Science & Technology Corp., NKK Corp., Takeda Chemical Industries, Asahi Kasei Kogyo Kabushiki Kaisha, Takasago Intl. Corp.Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
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Patent number: 6162949Abstract: Improved processes for preparation of the (S)-oxetines in high enantiomeric purity centers on resolution using simulated moving bed chromatography of a racemic precursor early in the oxetine synthesis. Resolution is effected with high enantiomeric purity, and subsequent reactions of the desired enantiomer performed with high optical specificity to maintain enantiomeric purity. The undesired enantiomer may be racemized and recycled to the resolution phase to avoid loss.Type: GrantFiled: February 22, 1999Date of Patent: December 19, 2000Assignee: UOP LLCInventor: Mark J. Gattuso
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Patent number: 6118025Abstract: The invention concerns a method for preparing an optically active alcohol of formula (I) in which the carbon atom indicated by the symbol * can have the configuration (R) or (S) and X represents a non-substituted amino group or a mono- or di-(C.sub.1 -C.sub.4)alkylamino group optionally salified from corresponding ketones by catalytic hydrogenation in the presence of a rhodium complex.Type: GrantFiled: December 27, 1999Date of Patent: September 12, 2000Assignee: Sanofi-SynthelaboInventors: Francine Agbossou, Marc Devocelle, Jean-Robert Dormoy, Andre Mortreux
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Patent number: 6040479Abstract: The present invention is concerned with an improved process for the resolution of racemic 2-(o-chlorophenyl)-2-methylaminocyclohexanone (ketamine).Type: GrantFiled: November 10, 1998Date of Patent: March 21, 2000Assignees: Goedecke Aktiengesellschaft, Cu Chemie Uetikon GmbHInventors: Klaus Steiner, Stefan Gangkofner, Jean-Marie Grunenwald
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Patent number: 6034278Abstract: The invention concerns a new method for producing optically active 1-phenylethylamines, wherein (a) racemic 1-phenylethylamines are reacted with (S)-(-)-N-phenylcarbamate lactic acid in the presence of an aliphatic or aromatic hydrocarbon and in the presence of a lower aliphatic alcohol, wherein the reaction components are measured so that for every mole of racemic amine, between 0.25 and 0.5 mole of (S)-(-)-N-phenylcarbamate lactic acid are present, the reaction mixture is then concentrated at a liquid-phase temperature of up to 40.degree. C.Type: GrantFiled: December 17, 1998Date of Patent: March 7, 2000Assignee: Bayer AktiengesellschaftInventors: Walter Merz, Martin Littmann, Udo Kraatz, Christoph Mannheims
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Patent number: 5962737Abstract: Stereospecific synthesis of the racemic threo isomers of 2-nitro-1-phenylpropanols by reacting a benzaldehyde derivative with nitroalkane in the presence of a tertiary amine and reducing 2-nitro-1-phenylpropanols with, for example, lithium aluminum hydride to 2-amino-1-phenylpropanols is described. Also described are phase transfer resolution of racemic mixtures of 2-amino-1-phenylpropanol and its derivatives into their optically pure isomers by reacting a racemic mixture with the mono alkali metal salt of a tartaric acid ester in a two phase system of a hydrocarbon and water. The specification further describes therapeutically useful optically pure isomers of threo-2-amino-1-(dialkoxy or alkoxy) phenylpropanols and acid addition salts thereof.Type: GrantFiled: January 8, 1997Date of Patent: October 5, 1999Inventor: Daniel David West
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Patent number: 5889186Abstract: Improved processes for preparation of the (S)-oxetines in high enantiomeric purity centers on resolution using simulated moving bed chromatography of a racemic precursor early in the oxetine synthesis. Resolution is effected with high enantiomeric purity, and subsequent reactions of the desired enantiomer performed with high optical specificity to maintain enantiomeric purity. The undesired enantiomer may be racemized and recycled to the resolution phase to avoid undesired losses.Type: GrantFiled: December 16, 1994Date of Patent: March 30, 1999Assignee: UOPInventor: Mark J. Gattuso
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Patent number: 5885787Abstract: In accordance with a novel process, (R)-amines of the formula ##STR1## in which R.sup.1, R.sup.2 and n have the meanings given in the description, can be prepared by reacting reating N-acyl-amines of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and n have the meanings given in the description,with lipases which are suitable for cleaving the (R)-enantiomers of N-acyl-amines of the formula (II), in the presence of water and optionally in the presence of an organic diluent, at a pH of between 3.0 and 10.0 and at temperatures of between 0.degree. C. and 80.degree. C.Type: GrantFiled: August 25, 1997Date of Patent: March 23, 1999Assignee: Bayer AktiegesellschaftInventors: Hauke Smidt, Andreas Fischer, Peter Fischer, Rolf D. Schmid, Uwe Stelzer
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Patent number: 5874620Abstract: The invention provides a process for the separation of (RR,SS) 2-dimethylaminomethyl-1-(3-methoxyphenyl) cyclohexanol hydrochloride ?(RR,SS)-Tramadol!, from a mixture consisting of (RR,SS) Tramadol and (RS,SR)-2-dimethylaminomethyl-1-(3-methoxyphenyl) cyclohexanol ?(RS,SR)-Tramadol!, which process includes combining the mixture with an electrophilic reagent, the reagent selectively reacting with the hydroxyl group of (RS,SR)-Tramadol, leaving most of the (RR,SS) Tramadol intact, and precipitating the remaining, practically pure (RR,SS) Tramadol from the mixture.Type: GrantFiled: August 14, 1997Date of Patent: February 23, 1999Assignee: Chemagis, Ltd.Inventors: Ori Lerman, Joseph Kaspi, Dov Brenner
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Patent number: 5863952Abstract: The single enantiomers of formula (I) and salts thereof ##STR1## are calcium channel antagonists useful in the treatment of ischaemic conditions e.g., stroke.Type: GrantFiled: July 11, 1997Date of Patent: January 26, 1999Assignee: SmithKline Beecham plcInventors: Barry Sidney Orlek, John David Harling
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Patent number: 5856579Abstract: A process for optical resolution of a racemic substituted benzylamine is provided that involves reacting the racemic substituted benzylamine in a solvent with an optically active N-acyl-phenylalanine, -aspartic acid, or -glutamic acid, and separating the diastereomers formed by making use of the difference in the mutual solubilities of the two diastereomer salts which are generated therein.Type: GrantFiled: October 15, 1996Date of Patent: January 5, 1999Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Toyoto Hijiya, Teruo Yonekawa
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Patent number: 5808156Abstract: Process for the production of the isomers (R) and (S)-.alpha.-methyl-3-(trifluoromethyl)benzeneethanamine, the second being useful as intermediate in the synthesis of the anorexic drug dexfenfluramine (INN), which comprises carrying out a stereospecific reductive amination of 1-(3-trifluoromethyl)phenyl-2-propanone with (R) or (S)-.alpha.-methylbenzylamine under a hydrogen atmosphere in the presence of a catalyst and debenzylating the resulting diastereoisomer (R),(R) or (S),(S)-N-(1-phenylethyl)-.alpha.-methyl-3-(trifluoromethyl)benzeneethanam ine by treatment with hydrogen and a catalyst.Type: GrantFiled: July 31, 1997Date of Patent: September 15, 1998Assignee: Alfa Chemicals Italiana S.p.A.Inventors: Vincenzo Cannata, Barbara Galbiati, Tiziano Ferrario
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Patent number: 5728885Abstract: A method of preparing the enantiomers of O-demethyltramadol and the use of the enantiomers as pain-killing drugs are described.Type: GrantFiled: January 17, 1997Date of Patent: March 17, 1998Assignee: Gruenenthal GmbHInventors: Helmut Buschmann, Werner Winter, Ivars Graudums, Peter Jansen, deceased, Wolfgang Werner Alfred Strassburger, Elmar Josef Friederichs
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Patent number: 5723668Abstract: A method of separating the racemate of tramadol is disclosed.Type: GrantFiled: December 31, 1996Date of Patent: March 3, 1998Assignee: Gruenenthal GmbHInventors: Helmut Buschmann, Werner Winter, Ivars Graudums, Peter Jansen, deceased
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Patent number: 5679857Abstract: L-amino acid amides are converted to the corresponding D-amino acid amides. An amide formed from an L-amino acid and an optically active (S)-.alpha.-alkylbenzylamine is subjected to dehydration condensation with an aryl aldehyde to form a Schiff's base, which is racemized at the amino acid moiety in the presence of a base to yield an N-allylidene-D-amino acid-(S)-amide. The less-soluble diastereomer N-allylidene-D-amino acid-(S)-amide is crystallized from the reaction mixture and recovered by means of solid/liquid separation. The N-allylidene form is readily hydrolyzed into the amino acid-(S)-amide and the starting aldehyde.Type: GrantFiled: November 16, 1995Date of Patent: October 21, 1997Assignee: Ajinomoto Co., Inc.Inventors: Toyoto Hijiya, Chiaki Mochizuki, Tadashi Takemoto
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Patent number: 5639913Abstract: Novel derivatives of 1-aminoindan and their salts are described. Optically active 1-aminoindan derivatives are prepared by reacting a N-benzyl analog of the desired compound with an enantiomer of mandelic acid.Type: GrantFiled: September 13, 1996Date of Patent: June 17, 1997Assignee: Teva Pharmaceutical Industries, Ltd.Inventors: Ramy Lidor, Eliezer Bahar
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Patent number: 5545745Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or .alpha.-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedi methanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.Type: GrantFiled: January 20, 1995Date of Patent: August 13, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Charles M. Zepp
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Patent number: 5510519Abstract: Disclosed are optically active secondary amine compounds and salts thereof having the general formula (I): ##STR1## a process for the preparation of the optically active secondary amine compounds and salts thereof, and the use of such compounds. Such compounds exhibit a high resolution power and hence are useful agents for optical resolution.Type: GrantFiled: December 13, 1993Date of Patent: April 23, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Junko Kudo, Toshio Nishioka
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Patent number: 5476964Abstract: Benzyl alcohols having a chiral center at the benzylic carbon can be conveniently racemized by treatment with solid acids which are strongly acidic cation exchange materials. Racemization may be effected generally in the range from 20.degree.-150.degree. C. in aqueous or partly aqueous systems in combination with a water-miscible organic solvent to improve solubility of the alcohol. Similar racemizations may be effected for benzyl ethers and esters. This process is valuable for recycling of unwanted enantiomers obtained in the resolution of racemic mixtures.Type: GrantFiled: November 21, 1994Date of Patent: December 19, 1995Assignee: UOPInventor: David W. House
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Patent number: 5461175Abstract: A method for separating enantiomers of a derivative of an aryloxipropanolamine is disclosed, characterized in that the derivative is contacted with a chiral solid-phase chromatography material containing molecular imprints of an optically pure enantiomer of the derivative to be separated.Type: GrantFiled: July 8, 1994Date of Patent: October 24, 1995Inventors: Lutz Fischer, Ralf Muller, Klaus Mosbach, Bjorn Ekberg
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Patent number: 5449694Abstract: (-)-Ritodrine, that is (-)-erythro-1-(p-hydroxyphenyl)-2-[2-(p-hydroxyphenyl)ethylamino]-1-propan ol or a salt thereof substantially free from the (+)-isomer is disclosed. The compound has a strong suppressive effect on uterine contraction in comparison with (.+-.)-ritodrine and (+)-ritodrine and has the same level of toxicity as these compounds, so that it can be used as a therapeutic agent of threatened premature birth and threatened abortion as well as a therapeutic agent of dysmenorrhea having a high safety.Type: GrantFiled: March 1, 1994Date of Patent: September 12, 1995Assignee: Meiji Seika Kabushiki KaishaInventors: Naoki Yamazaki, Yoshimasa Fukuda, Yoshiaki Shibazaki, Tetsutarou Niizato, Isao Kosugi, Shin Yoshioka
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Patent number: 5442117Abstract: A process for obtaining a substantially pure enantiomer of an hydrocarbyl amine is described. The process utilizes first an enantiomerically enriched mixture the of hydrocarbyl amine obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with an inorganic acid producing a salt that has the following properties:1) has at least one eutectic point;2) a composition that is not at the eutectic point; and3) a eutectic composition that is closer to the racemiccomposition than is the eutectic composition of saidhydrocarbyl, or be a solid where the salt is a liquid. A substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and the hydrocarbyl amine enriched in the other enantiomer.Type: GrantFiled: December 13, 1993Date of Patent: August 15, 1995Assignee: Albemarle CorporationInventors: G. Patrick Stahly, Thanikavelu Manimaran
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Patent number: 5399765Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate using ditoluoyltartaric acid.Type: GrantFiled: May 23, 1994Date of Patent: March 21, 1995Assignee: Sepracor, Inc.Inventors: Yun Gao, Charles M. Zepp
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Patent number: 5391735Abstract: The present invention relates to a new process for the preparation of 3-substituted derivatives of 1-amino-2-hydroxy-propane in the form of single diastereoisomers, to certain of these diastereoisomers, and to compounds which are intermediates in the new process of the invention.Type: GrantFiled: April 12, 1994Date of Patent: February 21, 1995Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Piero Melloni, Arturo D. Torre, Ettore Lazzari, Giuseppe Mazzini
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Patent number: 5321154Abstract: (.+-.)-2-(4-Isobutylphenyl)-propionic acid can be resolved into optically active isomers easily and with high yields. The method is characterized by the use of the optically active amine of the following general formula (I) or (II) as a resolving agent.Type: GrantFiled: July 31, 1992Date of Patent: June 14, 1994Assignee: Nagase & Company, Ltd.Inventor: Hiroyuki Nohira
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Patent number: 5298660Abstract: Disclosed are optically active secondary amine compounds and salts thereof having the general formula (I): ##STR1## a process for the preparation of the optically active secondary amine compounds and salts thereof, and the use of such compounds. Such compounds exhibit a high resolution power and hence are useful agents for optical resolution.Type: GrantFiled: April 6, 1992Date of Patent: March 29, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Junko Kudo, Toshio Nishioka
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Patent number: 5292893Abstract: A process is provided for catalytically reducing imines, oximes, hydrazones and related compounds. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, to provide chiral amine reaction products which are enriched in one enantiomer. Catalytic asymmetric reduction can also be carried out using an achiral precatalyst in combination with aThe U.S. Government has rights in this invention pursuant to NIH Grant Number GM 34917.Type: GrantFiled: November 14, 1991Date of Patent: March 8, 1994Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Christopher A. Willoughby
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Patent number: 5292933Abstract: The invention relates to a novel process for the resolution of an acid mixture (hereinafter: threo acid mixture) containing (+)-threo-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl)-propionic acid [hereinafter: (+)-threo acid]and (-)-threo-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl)-propionic acid [hereinafter: (-)-threo acid].Type: GrantFiled: April 9, 1991Date of Patent: March 8, 1994Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Kalman Harsanyi, Elemer Fogassy, Maria cs, Tibor Gizur, Zsuzsanna Aracs nee Tischler, Katalin Berki, Laszlo Toke, Zsuzsanna Martonffy nee Jaszay
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Patent number: 5284966Abstract: Intermediates for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers are described. The final compounds are useful intermediates for the synthesis of antibiotics like Chloramphenicol, Thiamphenicol and Florfenicol.Type: GrantFiled: December 18, 1992Date of Patent: February 8, 1994Assignee: Zambon Group S.p.A.Inventors: Marco Villa, Claudio Giordano, Silvia Cavicchioli, Silvio Levi
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Patent number: 5281750Abstract: The present invention relates to chiral supports and to their use in the asymmetric synthesis, deracemization and optical inversion of organic chiral compounds. In particular, the supports are used in combination with thermal equilibration of a species having a reactive achiral portion. Preferably, these supports are obtained by the copolymerization of at least one chiral unit and at least one functionalizing unit or by the polymerization of at least one chiral unit which is a source of said functionalizing unit. Optionally, a crosslinking agent is utilized. By utilizing these supports and thermal equilibration, excess enantiomers can be produced.Type: GrantFiled: November 16, 1992Date of Patent: January 25, 1994Assignee: Rhone-Poulenc ChimieInventors: Robert Jacquier, Monique Calmes, Jacques Daunis
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Patent number: 5281722Abstract: The pure enantiomers of alpha-lipoic acid are obtained by formation of the diastereomeric salt pairs with the optical antipodes of alpha-methylbenzylamine in solution.Type: GrantFiled: November 12, 1992Date of Patent: January 25, 1994Assignee: Degussa AGInventors: Gottfried Blaschke, Ursula Scheidemantel, Horst Bethge, Roland Moller, Thomas Beisswenger, Klaus Huthmacher
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Patent number: 5280093Abstract: The present invention relates to chiral polymers and to their uses for operations of asymmetric synthesis, deracemization and optical inversion.These polymers are characterized in that they comprise:a chiral unita functionalizing unitan optional crosslinking unitApplication to chiral organic synthesis.Type: GrantFiled: April 14, 1993Date of Patent: January 18, 1994Assignee: Rhone-Poulenc ChimieInventors: Robert Jacquier, Monique Calmes, Jacques Daunis
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Patent number: 5274118Abstract: A process for the preparation of (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof which comprisesa) acylating an optically active amine with 2-methyl-4,4,4-trifluorobutanoic acid or a reactive derivative thereof to afford a butyramide;b) separating (R)-diastereomeric butyramide from (S)-diastereomeric butyramide; andc) converting the (R)-diastereomeric butyramide into the desired (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof. The product may be acylated with a carboxylic acid of formula III ##STR1## wherein U is carboxy, or a reactive derivative thereof to afford (R)-4-[5-(N-[4,4,4-trifluoro-2-methylbutyl]carbamoyl)-1-methylindol-3-yl-m ethyl]-3-methoxy-N-o-tolylsulphonylbenzamide. The indole is useful as a leukotriene antagonist, for example in the treatment of asthma or allergic rhinitis.Type: GrantFiled: December 4, 1991Date of Patent: December 28, 1993Assignee: Imperial Chemical Industries PLCInventors: Robert T. Jacobs, Andrew G. Brewster, George J. Sependa
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Patent number: 5266599Abstract: (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylam ine of formula ##STR1## is a medicament of use in gastroenterology.Type: GrantFiled: August 19, 1992Date of Patent: November 30, 1993Assignee: Jouveinal S.A.Inventors: Gilbert G. Aubard, Alain P. Calvet, Agnes Grouhel, Henri Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois J. Roman
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Patent number: 5250571Abstract: The present invention provides (S)-norfluoxetine and pharmaceutically acceptable salts thereof capable of inhibiting the uptake of serotonin.Type: GrantFiled: April 21, 1992Date of Patent: October 5, 1993Assignee: Eli Lilly and CompanyInventors: Ray W. Fuller, David Mitchell, David W. Robertson, Gregory A. Stephenson, David T. Wong
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Patent number: 5250572Abstract: The present invention provides (R)-norfluoxetine and pharmaceutically acceptable salts thereof capable of selectively occupying 5HT.sub.1c receptors.Type: GrantFiled: April 21, 1992Date of Patent: October 5, 1993Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 5227526Abstract: In a process for resolving 3-dimethylamino-2-methylpropiophenone (3-DAMP) material, a methanol solution containing a mixture of both 1- and d-enantiomers of 3-DAMP is formed. To this solution, ditoluyl-(L)-tartaric acid or ditoluyl-(D)-tartaric acid is added, so as to precipitate either the 1- or d-enantiomer of 3-DAMP as a salt. The precipitate then is isolated as a salt of a substantially pure enantiomer of 3-DAMP.Type: GrantFiled: June 16, 1992Date of Patent: July 13, 1993Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John R. Duchek
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Patent number: 5223646Abstract: Improved process for producing an optically active atenolol useful as a .beta.-adrenergic blocker for the treatment of angina pectoris, arrhythmia and hypertension, which comprising reacting a phenol compound with an optically active epihalohydrin to give an intermediate, optically active glycidyl ether compound, followed by reacting the intermediate with isopropylamine, and purification method of the optically active atenolol in high yield by means of forming a salt of atenolol with a Br nsted's acid whereby the salt of optically active atenolol having high optical purity can be separated from the salt of racemic atenolol by solid-liquid separation method.Type: GrantFiled: April 21, 1992Date of Patent: June 29, 1993Assignee: Daiso Company, Ltd.Inventors: Yoshikazu Takehira, Nobuaki Saragai, Kazuhiro Kitaori
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Patent number: 5202484Abstract: A four step process for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers is described. The final compounds are useful intermediates for the synthesis of antibiotics like Chloramphenicol, Thiamphenicol and Florfenicol. The starting products generally are discard products in the synthesis of said antibiotics.Type: GrantFiled: October 19, 1990Date of Patent: April 13, 1993Assignee: Zambon Group S.p.A.Inventors: Marco Villa, Claudio Giordano, Silvia Cavicchioli, Silvio Levi
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Patent number: 5200561Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.Type: GrantFiled: October 7, 1991Date of Patent: April 6, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
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Patent number: 5166397Abstract: This invention relates to a process for producing an optically active cyclobutylamine which comprises reacting a racemic modification of cyclobuthylamine represented by the following general formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 represent each a hydrogen atom or a protecting group; with an optically active N-acylphenylglycine to thereby give two corresponding diastereomeric salts, crystallizing the more difficultly soluble diastereomeric salt and isolating the corresponding optically active cyclobutylamine from the diastereomeric salt thus crystallized. The optically active substances of the compound of the above general formula [I] are useful as, for example, an intermediate in the synthesis of 9-[(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutyl]guanine which is expected as an antiviral agent.Type: GrantFiled: September 10, 1991Date of Patent: November 24, 1992Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kazuhisa Narita, Masashi Nagai, Hideo Sugimura, Yukihiro Sagawa, Akira Shiozawa
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Patent number: 5144077Abstract: The invention relates to a process for working up to crystallization mother liquor which is obtained in the resolution of the racemate of 1-(4-chlorophenyl)-ethylamine of the formula (I) with S-(-)-N-phenylcarbamoyllactic acid of the formula (II) by removing the ethanol from the ethanolic crystallization mother liquor by distillation in a 1st step and stirring the residue which remains with tert.-butyl methyl ether or toluene in a second step and it being possible to employ the resulting crystalline salt of (R/S)-1-(4-chlorophenyl)-ethylamine and (S)-(-)-N-phenylcarbamoyllactic acid directly again for the resolution of the racemate. The (S)-form of the amine is mainly present in the mother liquor and can be racemised and added to the resolution of the racemate again.Type: GrantFiled: November 26, 1991Date of Patent: September 1, 1992Assignee: Bayer AktiengesellschaftInventors: Johannes R. Jansen, Hans-Joachim Knops
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Patent number: 5120853Abstract: The optically active benzylamine derivatives of the present invention are very useful for use as the asymmetric ligand of an asymmetric reducing agent. By using the optically active amine-boron complex prepared from the compound of the present invention, optically active products can be obtained in a specifically high optical yield. Moreover, the separation and recovery of the reaction products and asymmetric ligand can be easily achieved.Type: GrantFiled: February 8, 1991Date of Patent: June 9, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito