Lower-alkyl 4,6,7,8,8a-9-hexahydro-6,9-ethanothieno[3,2-f]indoli

Details Lower-alkyl 4,6,7,8,8a-9-hexahydro-6,9-ethanothieno[3,2-f]indoli Lower-alkyl 4,6,7,8,8a-9-hexahydro-6,9-ethanothieno[3,2-f]indoli

1979-10-26

1981-07-28

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D51322, C07D51318

Patent

active

042811309

ABSTRACT:
Compounds of tropane (8-azabicyclo[3.2.1]octane) series having an aromatic substituent in the 2-position and a carboalkoxy group in the 3-position are prepared by reacting a tropane-3-carboxylate having a double bond in the 2,3-position with an aryl Grignard reagent. Transformations of the substituent on nitrogen are subsequently effected. Compounds where the 3-carboalkoxy group is in the exo configuration possess hypoglycemic activity, and those where the 3-carboalkoxy group is in the endo configuration possess narcotic antagonist activity.

REFERENCES:
patent: 3813404 (1977-05-01), Clarke
patent: 4172201 (1979-10-01), Jarque et al.
patent: 4179565 (1979-12-01), Jarque et al.
patent: 4179567 (1979-12-01), Clarke et al.
Clarke et al., J. Med. Chem. 21, 1243 (1978).
Clarke et al., J. Org. Chem. 43, 4589 (1978).
Clarke et al., Chem. Abs 90, 39081k (1978).
Kan-Fan et al., Acta. Chem. Scand. 27, 1039 (1973).

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