The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Sep. 29, 1992

Filed:

May. 07, 1990
Applicant:
Inventors:

James R Behling, Lindenhurst, IL (US);

Payman Farid, Deerfield, IL (US);

Ish Khanna, Vernon Hills, IL (US);

John R Medich, Des Plaines, IL (US);

Mike Prunier, Vernon Hills, IL (US);

Mike G Scaros, Arlington Heights, IL (US);

Richard M Weier, Lake Bluff, IL (US);

Assignee:

G. D. Searle & Co., Chicago, IL (US);

Attorneys:
Primary Examiner:
Int. Cl.
CPC ...
C07D / ;
U.S. Cl.
CPC ...
546219 ; 546242 ;
Abstract

A process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives of the formula: ##STR1## wherein R is hydrogen, alkyl of 1 to 13 carbon atoms, and aralkyl wherein alkyl is a lower alkyl of 2 to 6 carbon atoms, and aryl is phenyl, unsubstituted or substituted with lower alkyl of 1 to 6 carbon atoms, halo, lower alkoxy of 1 to 4 carbon atoms or thio lower alkyl of 1 to 4 carbon atoms by the steps of: treating L-sorbose with 2,2-dimethoxypropane to yield 1,2:4,6-di-O-(1-methylethylidene)-.alpha.-L-sorbanose; treating the compound with sulfuric acid in a solvent to produce 1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; consecutively treating with sulfonyl chloride and with an amine to yield 6-(substituted amino)-6-deoxy-1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; adsorbing the compound on an ion exchange resin and hydrogenating to produce compounds of the above formula.


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