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:
Jun. 26, 2012

Filed:

Mar. 23, 2010
Applicants:

Tom Thomas Puthiaparampil, Bangalore, IN;

Thomas Kanathkunn David, Bangalore, IN;

Muppala Sarveswara Raju, Bridgewater, NJ (US);

Inventors:

Tom Thomas Puthiaparampil, Bangalore, IN;

Thomas Kanathkunn David, Bangalore, IN;

Muppala Sarveswara Raju, Bridgewater, NJ (US);

Assignee:

Rock Creek Pharmaceuticals, Inc., Gloucester, MA (US);

Attorney:
Primary Examiner:
Assistant Examiner:
Int. Cl.
CPC ...
C07D 401/00 (2006.01); A61K 31/44 (2006.01);
U.S. Cl.
CPC ...
Abstract

Anatabine is obtained by reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine. The resulting anatabine is substantially free from contaminants and displays good stability. In an alternative embodiment, the benzylhydrylidene-pyridin-3-yl-methyl-amine may be used in the synthesis of other alkaloids such as anabasine, nornicotine, N-methylanabasine, and anabaseine.


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