Gruppo Lepetit

Emilio Toia

Amedeo Omodei-Sale

Giulio Galliani

Leonard J Lerner

Amedeo Omodie Sale

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.

Naphth[1,2-d]imidazoles

3H-naphth[1,2-d]imidazole derivatives of formula ##STR1## wherein R stands for hydrogen, methyl or ethyl, R.sub.1 represents hydrogen, methyl or ethyl, R.sub.2 represents hydrogen, methyl, ethyl, phenyl or substituted phenyl, the symbol R.sub.3 stands for a phenyl radical optionally substituted and R.sub.4 and R.sub.5, each independently, may represent hydrogen, halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkoxy or halo-(C.sub.1 -C.sub.4)alkoxy, are described. Also described is the process for preparing the novel compounds, their use as antiinflammatory agents and the pharmaceutical compositions containing them.

Antiinflammatory 3H-naphtho(1,2-d)imidazoles

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.

Novel tricyclic compounds containing two ring notrogen atoms and represented by the following formula I ##STR1## wherein: A is one of the groups --CH.sub.2 --; --CH.dbd.CH--; and --CH.sub.2 --CH.sub.2 --; R is hydrogen, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, cyclo(C.sub.3-6 alkyl)oxy, hydroxy, benzyloxy, halo, sulfamoyl, cyano, trifluoromethyl or nitro; R.sub.1 is hydrogen, lower alkoxy or halo; or R and R.sub.1 taken together are methylenedioxy; the sequence ##STR2## is one of the following moieties: ##STR3## WHEREIN R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen, methyl, carboxy, carbo(lower alkoxy), carbamyl, mono- or di-(lower alkyl) carbamyl or hydroxymethyl; provided that when the sequence ##STR4## is one of the moieties a) and b) wherein R.sub.2 is hydrogen or lower alkyl, A is not --CH.dbd.CH--; when the sequence ##STR5## is one of the moieties (a) and (b) wherein R.sub.2 is hydrogen, A is not --CH.sub.2 --; and when the sequence ##STR6## is one of the moieties (c) and (d) wherein R.sub.3 is hydrogen and when both R and R.sub.1 are hydrogen, A is not --CH.dbd.CH--; and the salts thereof with a non-toxic pharmaceutically-acceptable acid. The compounds of the invention have antireproductive activity.

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Milan, Italy

Emilio Toia