Warner-lambert Company

Mcneil-ppc, Inc.

James L Caffrey

Anthony R Booth

William T Sherman

Michael Forster

Peter Raven

Patricia Gwirtz

Thomas Yorio

The present invention provides stereoscopically-pure diastereomers of Formula I:  In a preferred embodiment, the stereoisomers of the present invention are of Formula II, depicted below: R, Rand Rare independently H, OH, OCH, CHOH, NHCONH, NH, halogen or CF, and Ris pyridine, or an amine which may be substituted with hydrogen, lower alkyl, lower alkylenearyl, lower alkylenephenyl, lower alkylenehydroxyphenyl, lower alkyleneamine, lower alkyleneaminoaryl, lower alkylaminohydroxyphenyl, or a similar functional group. Ris hydrogen, hydroxyl or methyl; Ris hydrogen, lower alkyl, lower alkylenaryl, lower alkylenephenyl, lower alkylenehydroxyphenyl, lower alkyleneamine, lower alkyleneaminoaryl, lower alkylaminohydroxyphenyl, and the like. For both Formula I and Formual II, the first carbon on the side chain progressing from the ring is preferably in the R-configuration. The second carbon atom on the side chain of Formula II, which is attached to R, may or may not be a chiral center. However, when the second carbon atom is a chiral center, it is preferably in the S-configuration. The present invention contemplates each stereoisomer of Formula I and II in substantially-pure form. The present invention also provides methods of relieving nasal, sinus and bronchial congestion and of treating attention deficit hyperactivity disorder and obesity. The present stereoisomers may also be used to induce pupil dilation. These methods include administering to a mammal a composition containing a therapeutically effective amount of a stereoscopically-pure stereoisomer of Formula I or II with a pharmaceutically acceptable excipient.

Stereoisomers with high affinity for adrenergic receptors

The present invention provides pharmaceutical compositions which include (&minus;)-pseudoephedrine and a pharmaceutically acceptable carrier, wherein the (&minus;)-pseudoephedrine is substantially-free of (&plus;)-pseudoephedrine. In another embodiment, the present invention provides methods of relieving nasal and bronchial congestion and of inducing pupil dilation which include administering a pharmaceutically effective amount of (&minus;)-pseudoephedrine to a mammal. The (&minus;)-pseudoephedrine used in the present methods is substantially free of (&plus;)-pseudoephedrine and also substantially free of side effects caused by administration of (&plus;)-pseudoephedrine.

(&minus;)-Pseudoephedrine as a sympathomimetic drug

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Burelson, TX, United States of America

James L Caffrey