Naphth[1,2-d]imidazoles

Details Naphth[1,2-d]imidazoles Naphth[1,2-d]imidazoles

1981-01-30

1982-11-23

Fan, Jane T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

424267, 424250, 4242484, 544137, 544369, 544139, 544370, 546198, 546271, C07D40306

Patent

active

043606741

ABSTRACT:
Naphth[1,2-d]imidazoles and naphth[2,1-d]oxazoles of formula ##STR1## wherein R and R.sub.1 are hydrogen, halogen, alkyl or alkoxy, R.sub.2 is hydrogen or halogen and A is one of the following moieties ##STR2## wherein R.sub.3 is alkyl, cycloalkyl, or a --(CH.sub.2).sub.n NR.sub.5 R.sub.6 group in which n is 1,2 or 3, R.sub.5 is hydrogen or alkyl, R.sub.6 is alkyl or R.sub.5 and R.sub.6 taken together with the adjacent nitrogen atom are a 4- to 7-membered saturated hetero ring which may contain a further hetero atom and optionally may be substituted, e.g., with phenyl or substituted phenyl, R.sub.4 is hydrogen, alkyl, cycloalkyl or a --(CH.sub.2).sub.n NR.sub.5 R.sub.6 group, provided that one of R.sub.3 and R.sub.4 is a --(CH.sub.2).sub.n --NR.sub.5 R.sub.6 group, and R.sub.7 is --(CH.sub.2).sub.n --NR.sub.5 R.sub.6, or a pharmaceutically-acceptable acid addition salt thereof. They are made by contacting a corresponding naphth[1,2-d]imidazole or a naphth[2,1-d]oxazole wherein one of R.sub.3 and R.sub.4 or R.sub.7 is a --(CH.sub.2).sub.n X group wherein X is the residue of a reactive ester with an appropriate amine of the formula HNR.sub.5 R.sub.6 in the presence of an acid acceptor. The new compounds are useful as CNS-depressant agents.

REFERENCES:
patent: 4173634 (1979-11-01), Krapche et al.
Malmberg et al., J. Amer. Chem. Soc. 70, pp. 2415-2417, 1948.
Morgan et al., J. Chem. Soc. 115, p. 1140 (1969).
Cook et al., Ann. N.Y., Acad. Sci. 1957, pp. 66 & 740.
Maffii, J. Pharm. and Pharmacol, 1959, 11 pp. 129-139.
Morpurgo, Drug Research, 21, p. 127, (1971).

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