Resolution Per Se Of Optical Isomers Patents (Class 564/303)
  • Patent number: 4945181
    Abstract: 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: Grant
    Filed: December 1, 1986
    Date of Patent: July 31, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Helmut Dick, Wolf-Dietrich Gradel, Mathias Weber
  • Patent number: 4931525
    Abstract: In the chromatographic separation of a mixture of antipodes of optically active chemicals by passing a solution of such mixture over an optically active adsorbent to effect adsorption, and then eluting the adsorbed material, the improvement which comprises employing as the adsorbent particles of an optically active and cross-linked polymer containing the repeating structural unit ##STR1## in which R.sup.1 represents hydrogen or methyl, andR.sup.2 represents one of the stereoisomers of the eight possible stereoisomeric forms of each of the optically active radicals of the formulae ##STR2## Improved separation results. The pure monomers are also new.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: June 5, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Schwartz, Rolf Grosser, Karl-Erwin Piejko, Bruno Bomer, Dieter Arlt
  • Patent number: 4859771
    Abstract: 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: Grant
    Filed: January 19, 1989
    Date of Patent: August 22, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Paul J. Reider, Edward J. J. Grabowski
  • Patent number: 4827036
    Abstract: Novel pseudo-aminosugars, or 5-amino-1-hydroxymethyl-1,2,3,4-cyclohexanetetrol, their production and use.These pseudo-aminosugars exhibit excellent .alpha.-glucosidase inhibitory activity and are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.
    Type: Grant
    Filed: April 9, 1982
    Date of Patent: May 2, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yukihiko Kameda, Satoshi Horii
  • Patent number: 4814477
    Abstract: A new family of compounds known as dioxaphosphorinanes having the formula: ##STR1## wherein, M represents a hydrogen atom, a metal ion or an ammonium ion; R1 and R2, individually, represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms or a nitro group or, together, represent a methylene dioxy group; and R3 and R4, individually, represents a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydrogen atom so long as only one of the groups R3 and R4 represents a hydrogen atom or, together, represent a cyclohexyl group.A method for preparing these dioxaphosphorinanes by reacting phosphoryl chloride with a substituted 1-phenyl-1,3-dihydroxypropane is described. Also described is a method for resolving the new dioxaphosphorinanes into their optical isomers by reacting them with an optically active amino-compound.
    Type: Grant
    Filed: June 19, 1987
    Date of Patent: March 21, 1989
    Assignee: Oce-Nederland B.V.
    Inventors: Hans Wijnberg, Wolter T. Hoeve
  • Patent number: 4803303
    Abstract: 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: Grant
    Filed: April 17, 1987
    Date of Patent: February 7, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
  • Patent number: 4777291
    Abstract: 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: Grant
    Filed: February 27, 1985
    Date of Patent: October 11, 1988
    Assignee: Eli Lilly and Company
    Inventor: Jerry W. Misner
  • Patent number: 4497960
    Abstract: The invention declares new chiral, optically active compounds of the general formula ##STR1## wherein a 5 or 6 membered lactol ring (E), with X and Y meaning (CR.sup.1 R.sup.2).sub.n, with n=0 to 2 and R.sup.1, R.sup.2 =H, lower alkyl or aryl in any combination which does not impair the anomeric selectivity of I in forming acetals, is fused in a stereospecific manner to a bicyclo[2.2.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: February 5, 1985
    Inventor: Christian Noe
  • Patent number: 4463176
    Abstract: A process for resolving a racemic modification of .beta.-adrenergic aryl- or hetaryl-oxypropanolamines such as (.+-.)-2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy] benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivatives by reaction with a chiral aralkylisocyanate; separation into the individual diastereomers; and facile regeneration of the starting amine by cleavage of the intermediate urea compound using hydrazine. This final step is improved by the addition of an .alpha.-keto carboxylic acid, such as pyruvic acid, which functions as a scavenger of nucleophilic by-products.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: July 31, 1984
    Assignee: Mead Johnson & Company
    Inventors: Ronald D. Dennis, Terence M. Dolak, William E. Kreighbaum
  • Patent number: 4340751
    Abstract: (.+-.)-2-Amino-1-butanol and/or (.+-.)-mandelic acid are optically resolved with a high resolution efficiency and high optical purities by preferentially crystallizing out one of the pair of less soluble enantiomeric salts (or optical antipodes), namely (+)-2-amino-1-butanol-(+)-mandelic acid salt and (-)-2-amino-1-butanol-(-)-mandelic acid salt.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: July 20, 1982
    Assignee: Hiroyuki Nohira
    Inventors: Hiroyuki Nohira, Hiroshi Fujii, Masami Yajima, Rieko Fujimura
  • Patent number: 4330484
    Abstract: Racemic malic acid can be fractionally crystallized, as a diastereomeric salt pair, from alcoholic solution or aqueous-alcoholic solution by using an optical antipode of 2-amino-butan-1-ol.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: May 18, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Wilfried Berning, Hardo Siegel
  • Patent number: 4269788
    Abstract: Cyclohexadiene derivatives of the formula ##STR1## wherein R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are as hereinafter set forth, are described. The compounds of formula I are useful as analgesic agents.
    Type: Grant
    Filed: October 4, 1979
    Date of Patent: May 26, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter M. Muller, Rudolf Pfister, Rene Urban