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US 4,229,449 AGranted
Substituted morpholine derivatives and compositions
AssigneeFarmitalia Carlo Erba S.p.A.
InventorsPiero Melloni, Arturo D. Torre, Giovanni C. Carniel, Alessandro Rossi
Life of this patent
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Abstract
Substituted morpholine derivatives, such as, for instance, the compound 2-[.alpha.-(2-methoxy-phenoxy)-benzyl]-morpholine are disclosed. The claimed compounds are active on the central nervous system, and may be used as antidepressant agents.
Claims9
A compound having the following formula (I) ##STR34## wherein n and n.sub.1 are independently 1, 2 or 3;
- each of the groups R and R.sub.1, which may be the same or different, is hydrogen;
- halogen;
- halo-C.sub.1 -C.sub.6 -alkyl;
- hydroxy;
- C.sub.1 -C.sub.6 alkoxy;
- C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by one or more substituents chosen from the group consisting of hydroxy, C.sub.1 -C.sub.6 alkoxy ##STR35## wherein R.sub.5 and R.sub.6 are independently hydrogen or C.sub.1 -C.sub.6 alkyl and ##STR36## where R.sub.5 and R.sub.6 are as defined above;
- phenyl-C.sub.1 -C.sub.6 -alkyl or phenyl-C.sub.1 -C.sub.6 -alkoxy in which the phenyl groups may be unsubstituted or substituted by one or more substituents chosen from the group consisting of C.sub.1 -C.sub.6 alkyl, halogen, C.sub.1 -C.sub.6 alkoxy, hydroxy, halo-C.sub.1 -C.sub.6 -alkyl and ##STR37## wherein R.sub.5 and R.sub.6 are as defined above;
- R.sub.3 is hydrogen;
- C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by one or more substituents chosen from the group consisting of halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, ##STR38## and ##STR39## where R.sub.5 and R.sub.6 are as defined above;
- C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl-C.sub.1 -C.sub.4 -alkyl in which the phenyl group may be unsubstituted or substituted by one or more substituents chosen from the group consisting C.sub.1 -C.sub.6 alkyl, halogen, halo-C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 alkoxy and ##STR40## where R.sub.5 and R.sub.6 are as defined above;
- C.sub.3 -C.sub.7 cycloalkyl unsubstituted or substituted by one or more C.sub.1 -C.sub.6 alkyl, halogen, halo-C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 alkoxy;
- and ##STR41## where R.sub.5 and R.sub.6 are as defined above;
- R.sub.2 and R.sub.4, taken together, from the --CH.sub.2 --CH.sub.2 -- radical, as well as the pharmaceutically acceptable salts thereof
10 more elements
A compound having the following formula (I) ##STR42## wherein n and n.sub.1 are independently 1, 2 or 3;
- each of the groups R and R.sub.1 which may be the same or different is hydrogen;
- halogen;
- halo-C.sub.1 -C.sub.6 -alkyl;
- hydroxy;
- C.sub.1 -C.sub.6 alkoxy;
- C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by one or more hydroxy or C.sub.1 -C.sub.6 alkoxy groups;
- phenyl-C.sub.1 -C.sub.6 -alkyl or phenyl-C.sub.1 -C.sub.6 -alkoxy in which the phenyl group may be unsubstituted or substituted by one or more substituents chosen from the group consisting of C.sub.1 -C.sub.6 alkyl, halogen, C.sub.1 -C.sub.6 -alkoxy, hydroxy and halo-C.sub.1 -C.sub.6 alkyl;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by one or more halogen, hydroxy or C.sub.1 -C.sub.6 alkoxy groups C.sub.2 -C.sub.4 alkenyl;
- C.sub.2 -C.sub.4 alkynyl;
- phenyl-C.sub.1 -C.sub.4 -alkyl in which the phenyl group may be substituted or substituted by one or more C.sub.1 -C.sub.6 alkyl, halogen, halo-C.sub.1 -C.sub.6 alkyl, hydroxy and C.sub.1 -C.sub. 6 alkoxy groups;
- or C.sub.3 -C.sub.7 cycloalkyl unsubstituted or substituted by one or more C.sub.1 -C.sub.6 alkyl, halogen, halo-C.sub.1 -C.sub.6 alkyl, hydroxy and C.sub.1 -C.sub.6 alkoxy groups;
- R.sub.2 and R.sub.4, taken together, form the radical --CH.sub.2 --CH.sub.2 --, as well as the pharmaceutically acceptable salts thereof.
9 more elements
A compound having the following formula (I) ##STR43## wherein n and n.sub.1 are, independently, 1 or 2;
- each of the groups R and R.sub.1 is, independently, hydrogen, methoxy, ethoxy, chlorine, trifluoromethyl;
- R.sub.2 and R.sub.4, taken together, form the radical --CH.sub.2 --CH.sub.2 --, R.sub.3 is hydrogen, methyl or isopropyl as well as the pharmaceutically acceptable salts thereof.
A compound selected from the group consisting of:
- 2-(.alpha.-phenoxy-benzyl)-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-benzyl]-morpholine;
- 2-[.alpha.-(3-methoxy-phenoxy)-benzyl]-morpholine;
- 2-[.alpha.-(4-methoxy-phenoxy)-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-benzyl]-morpholine;
- 2-[.alpha.-(4-chloro-phenoxy)-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-2-methoxy-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-2-methoxy-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-4-ethoxy-benzyl]-morpholine;
- 2-[.alpha.-(4-chloro-phenoxy)-4-ethoxy-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-4-ethoxy-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-2-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-2-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-4-trifluoromethyl-benzyl]-morpholine;
- 2-[.alpha.-(4-ethoxy-phenoxy)-4-trifluoromethyl-benzyl]-morpholine;
- 2-[.alpha.-(2-methoxy-phenoxy)-3,4-dichloro-benzyl]-morpholine;
- 2-[.alpha.-(2-ethoxy-phenoxy)-3,4-dichloro-benzyl]-morpholine,
- as well as the pharmaceutically acceptable salts thereof.
19 more elements
A compound selected from the group consisting of:
- 4-methyl-2-[.alpha.-(2-methoxy-phenoxy)-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-ethoxy-phenoxy)-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-methoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-ethoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-ethoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 4-methyl-2-[.alpha.-(2-methoxy-phenoxy)-4-trifluoromethyl-benzyl]-morpholin e;
- 4-methyl-2-[.alpha.-(2-ethoxy-phenoxy)-4-trifluoromethyl-benzyl]-morpholine
- as well as the pharmaceutically acceptable salts thereof.
6 more elements
A compound selected from the group consisting of:
- 4-isopropyl-2-[.alpha.-(2-methoxy-phenoxy)-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-ethoxy-phenoxy)-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-methoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-ethoxy-phenoxy)-3-chloro-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-ethoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine;
- 4-isopropyl-2-[.alpha.-(2-methoxy-phenoxy)-4-trifluoromethyl-benzyl]-morpho line;
- 4-isopropyl-2-[.alpha.-(2-ethoxy-phenoxy)-4-trifluoromethyl-benzyl]-morphol ine,
- as well as the pharmaceutically acceptable salts thereof.
6 more elements
2-[.alpha.-(2-methoxy-phenoxy)-benzyl]-morpholine and the pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.