Sunovion Pharmaceuticals Inc.

Stefan G Koenig

Roger P Bakale

Surendra Singh

Harold Scott Wilkinson

Charles P Vandenbossche

Hang Zhao

H Scott Wilkinson

Zhengxu Han

Mark A Varney

Thomas Wessel

Judy Caron

Xiping Su

Karim Lalji

Surendra P Singh

Scott H Wilkenson

This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.

Preparation of chiral amides and amines

One aspect of the present invention relates to pharmaceutical compositions containing two or more active agents that when taken together can be used to treat, e.g., menopause, mood disorders, anxiety disorders, or cognitive disorders. The first component of the pharmaceutical composition is a sedative eszopiclone. The second component of the pharmaceutical composition is trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine. The present invention also relates to a method of treating menopause, perimenopause, mood disorders, anxiety disorders, and cognitive disorders.

Process for preparation of trans 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1Napthalenamine

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Shrewsbury, MA, United States of America

Stefan G Koenig