Allyl amine MAO inhibitors

A compound of the formula:

• ##STR17## wherein:
• (a) X is fluorine and Y is hydrogen,
• (b) Y is fluorine and X is hydrogen, or
• (c) X is fluorine and Y is fluorine;
• Ra is R or --AR, wherein:
• R is phenyl;
• phenyl monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, C.sub.1 -C.sub.6 alkylcarbonyl, benzoyl, or phenyl;
• 1- or 2-naphthyl;
• 1-, 2-, or 3-indenyl;
• 1-, 2-, or 9-fluorenyl;
• 1-, 2-, or 3-piperidinyl;
• 2- or 3-pyrrolyl;
• 2- or 3-thienyl;
• 2- or 3-furanyl;
• 2- or 3-indolyl;
• 2- or 3-thianaphtenyl;
• or 2- or 3-benzofuranyl;
• A is a divalent radical of the formula:
• ##STR18## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4;
• --(CH.sub.2).sub.p --D--(CH.sub.2).sub.q --, wherein D is oxygen or sulfur, p is an integer from 2 to 4, and q is an integer from 0 to 2, provided that p+q cannot be greater than 4;
• or --(CH.sub.2).sub.r CH.dbd.CH(CH.sub.2).sub.s --, wherein r is an integer from 1 to 3 and s is an integer from 0 to 2, provided that r+s cannot be greater than 3;
• and
• Q is hydroxy or a leaving group.

A method for treating depression which comprises administering to a depressed patient an effective amount of a compound of the formula:

• ##STR19## wherein:
• (a) X is fluorine and Y is hydrogen,
• (b) Y is fluorine and X is hydrogen, or
• (c) X is fluorine and Y is fluorine;
• R is phenyl;
• phenyl monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, C.sub.1 -C.sub.6 alkylcarbonyl, benzoyl, or phenyl;
• 1- or 2-naphthyl;
• 1-, 2-, or 3-indenyl;
• 1-, 2-, or 9-fluorenyl;
• 1-, 2-, or 3-piperidinyl;
• 2- or 3-pyrrolyl;
• 2- or 3-thienyl;
• 2- or 3-furanyl;
• 2- or 3-indolyl;
• 2- or 3-thianaphtenyl;
• or 2- or 3-benzofuranyl;
• R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, benzyl, or phenethyl;
• and
• A is a divalent radical of the formula:
• ##STR20## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4;
• --(CH.sub.2).sub.p --D--(CH.sub.2).sub.q --, wherein D is oxygen or sulfur, p is an integer from 2 to 4, and q is an integer from 0 to 2, provided that p+q cannot be greater than 4;
• or --(CH.sub.2).sub.r CH.dbd.CH(CH.sub.2).sub.s --, wherein r is an integer from 1 to 3 and s is an integer from 0 to 2, provided that r+s cannot be greater than 3;
• or a non-toxic, pharmaceutically acceptable acid addition salt thereof.

A pharmaceutical composition comprising:

• (a) a compound of the formula:
• ##STR21## wherein:
• (a) X is fluorine and Y is hydrogen,
• (b) Y is fluorine and X is hydrogen, or
• (c) X is fluorine and Y is fluorine;
• R is phenyl;
• phenyl monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, C.sub.1 -C.sub.6 alkylcarbonyl, benzoyl, or phenyl;
• 1- or 2-naphthyl;
• 1-, 2-, or 3-indenyl;
• 1-, 2-, or 9-fluorenyl;
• 1-, 2-, or 3-piperidinyl;
• 2- or 3-pyrrolyl;
• 2- or 3-thienyl;
• 2- or 3-furanyl;
• 2- or 3-indolyl;
• 2- or 3-thianaphtenyl;
• or 2- or 3-benzofuranyl;
• R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, benzyl, or phenethyl;
• and A is a divalent radical of the formula:
• ##STR22## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4;
• --(CH.sub.2).sub.p --D--(CH.sub.2).sub.q --, wherein D is oxygen or sulfur, p is an integer from 2 to 4, and q is an integer from 0 to 2, provided that p+q cannot be greater than 4;
• or --(CH.sub.2).sub.r CH.dbd.CH(CH.sub.2).sub.s --, wherein r is an integer from 1 to 3 and s is an integer from 0 to 2, provided that r+s cannot be greater than 3;
• or a non-toxic, pharmaceutically acceptable acid addition salt thereof
• (b) a pharmaceutically acceptable carrier.