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
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.
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.
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.
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.
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.
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.
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.
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
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.
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.
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