O-Alkylated oximes and pharmaceutical composition thereof

Compounds of general formula ##STR68## wherein R.sup.1 is a member selected from the group consisting of unsubstituted phenyl or phenyl substituted by at least one halogen atom;

• R.sup.2 is a member selected from the group consisting of hydrogen or alkyl having up to 3 carbon atoms;
• R.sup.3 is a member selected from the group consisting of hydrogen or hydroxy or nicotinoyloxy;
• R.sup.4 and R.sup.5 are members independently selected from the group consisting of hydrogen, halogen and methyl;
• and
• X is nitrogen;
• and physiologically acceptable acid addition salts thereof.

Compounds of general formula ##STR69## wherein R.sup.1 is a member selected from the group consisting of

• (a1) an unsubstituted at most binuclear aryl group having from 6 to 10 carbon atoms;
• and
• (a2) a group as in (a1) but substituted by from 1 to 3 equal or different radicals selected from the group consisting of alkyl, halogenoalkyl, alkoxy, dialkylamino each having up to 4 carbon atoms in the alkyl moiety, halogen, phenyl, carboxyl, cyano, nitro and hydroxy groups,
• (b) a 5- to 6-membered heteroaromatic ring containing one heteroatom which is selected from nitrogen, oxygen and sulfur atoms and such rings anellated to a benzene nucleus and the nonheteroatoms of the ring are carbon atoms;
• R.sup.2 is a member selected from the group consisting of hydrogen, alkyl having up to 3 carbon atoms, phenyl, cycloalkyl having up to 6 carbon atoms in the ring and cycloalkyl bearing a hydrocarbon bridging radical having up to 2 carbon atoms;
• R.sup.3 is a member selected from the group consisting of alkanoyloxy of one to six carbon atoms and nicotinoyloxy;
• and
• R.sup.4 and R.sup.5 are the same or different and each is a member selected from the group consisting of hydrogen, halogen, alkyl, and halogenoalkyl each having up to 3 carbon atoms, and nitro;
• and
• X is nitrogen or methine;
• and physiologically acceptable acid addition salts thereof.

Compounds of general formula:

• ##STR70## wherein R.sup.1 is a member selected from the group consisting of:
• (a1) an unsubstituted at most binuclear aryl group having 6 to 10 carbon atoms,
• (a2) a group as in (a1) but substituted by from 1 to 3 equal or different radicals selected from the group consisting of alkyl, halogenoalkyl, alkoxy, dialkylamino each having up to 4 carbon atoms in the alkyl moiety, halogen, phenyl, carboxyl, cyano, nitro and hydroxy groups,
• R.sup.2 is a member selected from the group consisting of hydrogen, alkyl having up to 3 carbon atoms, phenyl, cycloalkyl having up to 6 carbon atoms in the ring and cycloalkyl bearing a hydrocarbon bridging radical having up to 2 carbon atoms;
• and
• R.sup.3 is hydrogen, hydroxy, alkanoyloxy or nicotinoyloxy;
• and
• R.sup.4 and R.sup.5 are the same or different and each is a member selected from the group consisting of hydrogen, halogen, alkyl, and halogenoalkyl each having up to 3 carbon atoms, and nitro;
• and
• X is nitrogen or methine;
• and
• physiologically acceptable acid addition salts thereof.