Process for the preparation of optically-active carbazole deriva

Details Process for the preparation of optically-active carbazole deriva Process for the preparation of optically-active carbazole deriva

1987-05-13

1989-04-25

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546269, 546272, C07D40112, C07D20982

Patent

active

048249637

ABSTRACT:
A process for the preparation of S- or R-carbazole derivatives of the general formula: ##STR1## in which R is an unsubstituted or substituted amino radical and pharmacologically acceptable salts, by either reacting R-(-)-epichlorohydrin (for the S-carbazole derivative); or reacting an S-epoxide derivative of the general formula: ##STR2## in which R.sub.1 is the residue of a substituted sulphonic acid derivative (for the R-carbazole derivative); with 4-hydroxycarbazole and then with ammonia or a substituted amine of the general formula RH, and recovering the compound or converting it to a pharmacologically acceptable salt.
The new R-(+)- and S-(-)-carbozole derivatives provided by the inventive process have unexpected beta blocking and vasodilatory properties and are useful in pharmaceutical compositions. R-(+)-carbazole derivatives are also useful for the treatment of glaucoma.

REFERENCES:
patent: 4085136 (1978-04-01), Tucker
patent: 4202978 (1980-05-01), Fahrenholtz et al.
patent: 4411913 (1983-10-01), Payne et al.
patent: 4503067 (1985-03-01), Weidemann et al.
McClure et al., J. Am. Chem. Soc., vol. 101, #13, pp. 366-3668, (1979).

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