Intermediates useful in the synthesis of optically active m-acyloxy-.alpha.-[(methylamino)methyl]benzyl alcohols
US4158005A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 9, 1977 |
| Grant date | Jun 12, 1979 |
| Priority date | — |
| Expiry date | May 9, 1997 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D263/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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 t…
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