N-(4-Amino-2-butynyl)imides
AssigneeSterling Drug Inc.
InventorWilliam B. Dickinson
Life of this patent
Estimating the term…
Abstract
N-(4-Amino-2-butynyl)imides are prepared from N-propargylimides, paraformaldehyde and the appropriate secondary amine. The compounds are useful as stimulants or depressants of the central nervous system.
Claims8
A compound of the formula ##STR10## wherein A' is a member of the group consisting of divalent alkylene of from two to four carbon atoms and unsubstituted orthophenylene, and N.dbd.B is a basic tertiary amino radical selected from the group consisting of di(lower-alkyl)amino, N-lower-alkyl-N-lower-alkenylamino, di(lower-alkenyl)amino, N-lower-alkyl-N-cycloalkylamino, di(cycloalkyl)amino, N-(phenyl-lower-alkyl)-N-lower-alkylamino, pyrrolidino, piperidino, morpholino, and thiamorpholino.
A compound selected from the group consisting of ##STR11## and non-toxic addition salts thereof, wherein X is (CHR.sub.5).sub.p, p being an integer from 2 to 3, each R.sub.5 being selected from the class consisting of hydrogen and alkyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each hydrogen, m and n are the integer 1, Z is the divalent radical --C.tbd.C--, and Am is an amino group joined to the linking chain at the N atom, the amino group being selected from the class consisting of di-alkyl amino, di-alkenyl amino, (alkyl, alkenyl)amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, said alkyl and alkenyl groups when present having from 1 to 5 carbon atoms.
A process for the preparation of the formula ##STR12## and non-toxic addition salts thereof wherein X is (CHR.sub.5).sub.p, p being an integer from 2 to 3, each R.sub.5 being selected from the group consisting of hydrogen and alkyl, R.sub.1 and R.sub.2 are each hydrogen, m is the integer 1 and Am is an amino group joined to the linking chain at the nitrogen atom, the amino group being selected from the class consisting of di-alkyl amino, d-alkenyl amino, (alkyl, alkenyl) amino, pyrrolidino, piperidino, methyl substituted pyrrolidino having 1 to 2 methyl groups, and morpholino, and alkyl and alkenyl groups when present having from 1 to 5 carbon atoms, the system of reaction of propargyl imide of the formula ##STR13## with formaldehyde and an amine of the formula HAm, R.sub.1, R.sub.2 and Am being as defined above.
Dependencies are inferred from the claim text.