Novel synthesis of optically active m-acyloxy-.alpha.-[(methylam

Details Novel synthesis of optically active m-acyloxy-.alpha.-[(methylam Novel synthesis of optically active m-acyloxy-.alpha.-[(methylam

1975-02-10

1976-06-29

Drezin, Norman A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2605707, C07D21302

Patent

active

039667499

ABSTRACT:
Optically and therapeutically active compounds of the formula: ##SPC1##
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 ##EQU1## group, 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 using optically active m-hydroxy-.alpha.-[(methylamino)-methyl]benzyl alcohol (phenylephrine).
The compounds prepared by the process of this invention find therapeutic applicaton 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 opthalmology.
Upon administration, these compounds will enzymatically "cleave," thus releasing optically active phenylephrine (m-hydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol, the therapeutically active moiety thereof.

REFERENCES:
patent: 3542874 (1970-11-01), Keizer et al.
patent: 3641152 (1972-02-01), Shavel, Jr. et al.
patent: 3825583 (1974-07-01), Hussain et al.
Elderdield, "Heterocyclic Compounds," vol. 5, p. 391, (1957).
Morrison et al., Organic Chemistry, p. 593, (1959).

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