Racemization Per Se Or With Resolution Of Optical Isomers Patents (Class 564/302)
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Patent number: 5276195Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.Type: GrantFiled: July 14, 1993Date of Patent: January 4, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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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: 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: 5214209Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 25, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5210310Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 11, 1993Assignee: Aldrich Chemical Co., Inc.Inventor: Herbert C. Brown
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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: 5183939Abstract: A new process for the racemization of optically active 1-aryl-alkylamines of the formula (I) ##STR1## in which Ar represents optionally substituted aryl andR represents alkyl,which is characterized in that compounds of the formula (I) which largely have the R- or S-configuration at the carbon atom marked by * are reacted with metal alkoxides in dimethyl sulphoxide, optionally in the presence of appropriate alcohols, at temperatures between 0.degree. C. and 200.degree. C.Type: GrantFiled: November 21, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventors: Johannes R. Jansen, Martin Littmann
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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
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Patent number: 5087700Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: February 11, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5087753Abstract: Process for recovering .alpha.-aminoalcohols by extraction from aqueous solutions, in which process an aromatic aldehyde is added at elevated pH to an aqueous solution of an aminoalcohol in an at least equimolar amount in respect of the aminoalcohol, the resulting mixture is converted with formation of the Schiff base of the aldehyde and the aminoalcohol and the aqueous solution is subsequently extracted using a water-immiscible organic solvent, upon which the Schiff base in the resulting extract is hydrolized and the .alpha.-aminoalcohol or a salt thereof is recovered.Type: GrantFiled: September 19, 1990Date of Patent: February 11, 1992Assignee: Stamicarbon B.V.Inventors: Wilhelmus H. J. Boesten, Catharina H. M. Schepers, Mathieu J. A. Roberts
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Patent number: 5047585Abstract: The invention relates to a process for racemizing an optically active N-benzylidene amino-acid amide, characterized in that a solution of the N-benzylidene amino-acid amide is mixed in a water-miscible organic solvent with at least 0.05 mole strong base per liter solution.The invention further relates to a process for preparing an L-amino acid by enzymatic separation of the corresponding DL-amino-acid amide with an enzyme preparation from Pseudomonas putida, in which process also uncoverted D-amino-acid amide is left behind in solution, characterized in that benzaldehyde is added to the solution, during which addition a precipitate of D-N-benzylidene amino-acid amide is being formed, this precipitate is subsequently, after being separated off, dissolved in an acetone-water mixture, 0.08-0.15 mole KOH/liter solution is subsequently added, the resulting solution is stirred for 1-20 hours at 20.degree.-60.degree. C.Type: GrantFiled: April 3, 1989Date of Patent: September 10, 1991Assignee: Stamicarbon B.V.Inventors: Wilhelmus H. J. Boesten, Hans E. Schoemaker, Bernardus H. N. Dassen
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Patent number: 5039801Abstract: The invention provides an improved method for obtaining optically active amines, carbamates, and isocyanates by thermal fragmentation of optically active ureas through refluxing the ureas in C.sub.3 -C.sub.7 alcohol solution with or without catalytic amounts of alkali metal.Type: GrantFiled: August 28, 1987Date of Patent: August 13, 1991Assignee: The United States of America as represented by the Department of Health & Human ServicesInventors: Arnold Brossi, Bernhard Schonenberger
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Patent number: 5011995Abstract: Asymmetric hydrogenation of prochiral N-aliphatic ketimines to give optically active secondary amines at a temperature from -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 10.sup.7 Pa, with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY].sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or a diene ligand, Y is a chiral diphosphine the secondary phosphine group of which are attached through 2-4 C atoms and which, together with the Ir atom, forms a 5-membered, 6-membered or 7-membered ring, or Y is a chiral diphosphinite the phosphinite groups of which are attached via 2 C atoms and which, together with the Ir atom, forms a 7-membered ring, Z is Cl, Br or I and A.sup.- is the anion of an oxygen acid or complex acid, and, if appropriate, with the addition of an ammonium chloride, bromide or iodide or an alkali metal chloride, bromide or iodide.Type: GrantFiled: July 19, 1988Date of Patent: April 30, 1991Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Gerardo Ramos, Felix Spindler
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Patent number: 5011989Abstract: 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: October 3, 1988Date of Patent: April 30, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito
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Patent number: 5001251Abstract: An optically active amine compound and a method for preparing same are provided which compound has the structure ##STR1## in the form of its R-(+) enantiomer or S-(-) enantiomer, wherein R and R.sup.1 are independently H, lower alkyl or halogen, R.sup.2 is H or lower alkyl and R.sup.3 is lower alkyl, the optically active amine is useful in the optical resolution of DL-3-acylthio-2-methylpropanoic acid wherein acyl is acetyl or benzoyl. The optically active D-(+)-3-acylthio-2-methylpropanoic acids are used as intermediated for preparing antihypertensive agents, such as captopril.Type: GrantFiled: January 15, 1988Date of Patent: March 19, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Patrick A. MacManus, Peter Walsh, Adrian J. Kilbane
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Patent number: 4996361Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature from -40.degree. to 80.degree. C., under a hydrogen pressure of 10.sup.6 to 10.sup.8 Pa and with the addition of catalytic amounts of a rhodium compound of the formula III or IIIa ##STR1## in which X is 2 olefin ligands or a diene ligand, Y is a chiral diphosphine in which the secondary phosphine groups are linked by 2-4 C atoms and which, together with the Rh atom, forms a 5-membered, 6-membered or 7-membered ring, or Y is a chiral disphosphinite in which the phosphinite groups are linked via 2 C atoms and which, together with the Rh atom, forms a 7-membered ring, Z is Cl, Br or I and A.sup.- is the anion of an oxygen acid or complex acid.Type: GrantFiled: July 30, 1987Date of Patent: February 26, 1991Assignee: The University of British ColumbiaInventors: William R. Cullen, Michael D. Fryzuk, Brian R. James, Guo-Jun Kang, James P. Kutney, Roberto Spogliarich, Ian S. Thorburn
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Patent number: 4994615Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature of -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 6.10.sup.6 Pa with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY.sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or one diene ligand, Y is a chiral diphosphine, the secondary phosphine groups of which are linked by 2-4 C atoms and which, together with the Ir atom, forms a 5-, or 6- or 7-ring, or Y is a chiral diphosphinite, the phosphinite groups of which are linked via 2 C atoms and which together with the Ir atom forms a 7-ring, Z is Cl, Br or I and A.sup.63 is the anion of an oxygen acid or complex acid, and if appropriate with the addition of an ammonium or alkali metal chloride, bromide or iodide.Type: GrantFiled: July 29, 1987Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Felix Spindler, Benoit Pugin
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Patent number: 4990666Abstract: A process for racemization of optically active amino alcohols by subjecting the amino alcohol to hydrogen under moderate temperature and pressure conditions while in contact with Raney cobalt.Type: GrantFiled: February 4, 1987Date of Patent: February 5, 1991Assignee: W. R. Grace & Co.-Conn.Inventor: Stephen G. Harsy
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Patent number: 4952730Abstract: The invention relates to a process for inverting the configuration at the optically active carbon atom (*) in compounds of the formula I ##STR1## in which A denotes a carbocyclic or heterocyclic aromatic radical and R denotes an aliphatic, cycloaliphatic or araliphatic hydrocarbon radical, by formylation, treating the resulting compounds with a strong acid or an acid halide and cleaving the oxazolinium derivatives thus obtained, by acid or alkaline hydrolysis, if appropriate via the stage of the N-formyl compound, and to oxazolinium derivatives of the formula III defined herein and formed as intermediate products.Type: GrantFiled: May 27, 1986Date of Patent: August 28, 1990Assignee: Hoechst AktiengesellschaftInventors: Hans-Jurgen Leuchs, Werner Mohler, Hanns-Eberhard Erle
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Patent number: 4945181Abstract: The present invention provides a process for the preparation of thamphenicol (I) from D,L-threo-1-(p-methylsulphonylphenyl)-2-aminopropane-1, 3-diol hydrochloride (V) and intermediates thereof. The process comprises conversion to a corresponding benzal compound followed by hydrolysis to D,L-threo-aminodiol.Type: GrantFiled: December 1, 1986Date of Patent: July 31, 1990Assignee: Boehringer Mannheim GmbHInventors: Helmut Dick, Wolf-Dietrich Gradel, Mathias Weber
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Patent number: 4918229Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMBe.sub.2 wherein R is an organo group, R* is a chiral organo group attached to boron, B is boron and Me is methyl.Type: GrantFiled: July 29, 1988Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4886914Abstract: The present invention relates to a process for the preparation of alpha alkyl amino aldehydes of formula ##STR1## in which R is alkyl or aralkyl possibly substituted, characterized in that N,O-dimethylhydroxylamine is reacted, in a basic medium, on a blocked amine ester of an amino acid of formula ##STR2## and in that the product obtained is reduced with the aid of a hydride such as the double hydride of lithium-aluminum.Type: GrantFiled: July 30, 1985Date of Patent: December 12, 1989Assignee: SanofiInventors: Bertrand Castro, Jean Fehrentz
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Patent number: 4859771Abstract: An economical, one-pot process for resolution-racemization of primary amines with .alpha.-hydrogens via selective crystallization of diastereomeric chiral sulfonic acid salts and the subsequent in situ racemization of the other enantiomer by the catalytic addition of aromatic aldehydes, and a key process intermediate thereof.Type: GrantFiled: January 19, 1989Date of Patent: August 22, 1989Assignee: Merck & Co., Inc.Inventors: Paul J. Reider, Edward J. J. Grabowski
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Patent number: 4803303Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: April 17, 1987Date of Patent: February 7, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
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Patent number: 4777291Abstract: The present invention provides a process for the epimerization of (+)-N-methyl-3-(2-methylphenoxy)- 3-phenylpropylamine to its racemic form with an anion forming compound in a suitable solvent.Type: GrantFiled: February 27, 1985Date of Patent: October 11, 1988Assignee: Eli Lilly and CompanyInventor: Jerry W. Misner
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Patent number: 4542159Abstract: There are prepared compounds of the formula: ##STR1## wherein X is the group >C.dbd.O or >CH(OH), Y is the group ##STR2## R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, R.sub.3 is hydrogen or a hydroxy group and R.sub.1 is the adamantyl group or a saturated or single unsaturated C.sub.3 to C.sub.16 cycloalkyl group where the C.sub.3 to C.sub.16 cycloalkyl group can be substituted by a C.sub.1 -C.sub.4 alkyl group or a halogen atom and their salts. The compounds are useful in dilating the peripheral blood vessels and in lowering blood pressure.Type: GrantFiled: May 15, 1979Date of Patent: September 17, 1985Assignee: Degussa AkteinsellschaftInventors: Jurgen Engel, Axel Kleemann, Klaus Posselt, Fritz Stroman, Klaus Thiemer
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Patent number: 4533745Abstract: Amino ketone enantiomers and their direct preparation are disclosed. The ketone may be reduced to yield carbinol enantiomer which has pharmaceutical activity.Type: GrantFiled: December 8, 1980Date of Patent: August 6, 1985Assignee: Merck & Co., inc.Inventor: David E. McClure
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Patent number: 4339603Abstract: There is provided a process for racemizing an undesirable, optically active compound for conversion to levamisole, namely, l-N-(2-amino-2-phenethyl)-2-methoxyethylamine, by converting the latter to optically active l-(2-methoxyethyl)-4-phenyl-2-imidazolidone, which is next converted to the corresponding optically inactive imidazolidone derivative, which derivative is hydrolyzed to the optically inactive racemate, dl-N-(2-amino-2-phenethyl)-2-methoxyethylamine. The latter can be resolved to obtain the d and l components of the racemate, the d component being utilized directly in levamisole synthesis and the l component being again subjected to the above procedure.Type: GrantFiled: January 8, 1979Date of Patent: July 13, 1982Assignee: American Cyanamid CompanyInventors: Sivaraman Raghu, Arnold Zweig
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Patent number: 4252744Abstract: A process for the preparation of racemic phenylethylamine which comprises contacting an optical antipode therefore, e.g., L(-) or D(+)-1-phenylethylamine with sodium amide or sodium hydride.Type: GrantFiled: June 15, 1976Date of Patent: February 24, 1981Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunter Bison, Kurt Breideneichen, Walter Heinzelmann, Wolfgang Wolfes