omega-Dialkylaminoalkyl ethers of 5-endo-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-hydroxyimines with platelet antiaggregating, antiarrhythmic and local anesthetic activities.
1990
: The synthesis of 1,3,3-trhimethyl-5-endo-(1-piperidinyl)- and -5-endo-(4-morpholinyl)-2- oxabicyclo [2.2.2]octan-6-hydroxyimine 3 and 4 starting from 5-endo-bromo-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine+ ++ and excess piperidine or morpholine is described. Compounds 3 and 4 gave a series of omega-dialkylaminoalkyl ethers 5 by reaction as sodium salts with omega-chloroalkyldialkylamines in DMF solution. Some of aminoethers 5 showed in mice an appreciable antiarrhythmic and local anesthetic activity, as well as a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid.
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