Intermediates useful in the synthesis of optically active m-acyloxy-.alpha.-[(methylamino)methyl]benzyl alcohols

Abstract

Optically and therapeutically active compounds of the formula: ##STR1## wherein R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C.sub.1 -C.sub.5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an ##STR2## WHEREIN R is as defined above and R.sub.3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion, are prepared optically active m-hydroxy-.alpha.-[methylamino)methyl]benzyl alcohol (phenylephrine). The compounds prepared by the process of this invention find therapeutic application to warm-blooded animals (e.g., humans) in the management of asthma, nasal congestion and as decongestants, vasoconstrictors, mydriatic agents, and anti-glaucomatous agents in the practice of ophthalmology. Upon administration, these compounds will enzymatically "cleave," thus releasing optically active phenylephrine (m-hydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol, the therapeutically active moiety thereof.

Dependencies are inferred from the claim text.