Monoamine oxidase B inhibitors, processes for their preparation and use thereof
AssigneesLaboratoires Mayoly Spindler, Michel Seman
InventorsMichel Seman, Suzanne Bernard, Rene Milcent, Catherine Paillat
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Abstract
Novel monoamine oxidase B inhibitors of formula (I), wherein R.sub.1 .dbd.H, an optionally substituted benzyloxy or phenylethoxy group; p=0-3; R.sub.3 .dbd.H, a CN, OH, CCH group, a C.sub.1 -C.sub.3 alkoxy-carbonyl group, or a C.sub.1 -C.sub.3 alkylated cyanomethyl group; R.sub.2 .dbd.H or a C.sub.1 -C.sub.3 alkyl group; n=0 or 1; if n=0, R.sub.4 is a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group, while if n=1, y=1 and R.sub.4 is a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group or a phenyl group. The invention also concerns processes for the preparation of said novel inhibitors and the therapeutic use thereof. ##STR1##
Claims13
A method of selectively inhibiting monoamine oxidase B activity in a human or an animal, which method comprises administering to said human or said animal an effective amount of a compound of formula (I):
- ##STR8## in which:
- R.sub.1 represents a hydrogen atom, a benzyloxy group or a phenylethoxy group whose phenyl ring is optionally substituted;
- p is an integer from 0 to 3;
- R.sub.3 represents a hydrogen atom, a CN group, a hydroxyl group, a CCH group, a (C.sub.1 -C.sub.3 alkoxy) carbonyl group or a C.sub.1 -C.sub.3 alkylated cyanomethyl group;
- R.sub.2 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group;
- n is equal to 0 or 1, in which case:
- if n=0, R.sub.4 represents a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group;
- whereas
- if n=1, y=1 and R.sub.4 represents a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group or a phenyl group.
A compound selected from the group consisting of compounds having the following specific formulae:
- ##STR9## in which:
- R.sub.1 represents a hydrogen atom, a benzyloxy group or a phenylethoxy group whose phenyl ring is optionally substituted, provided that R.sub.1 is different from a hydrogen atom in the specific formula (I-e);
- p is an integer from 0 to 3;
- and
- R.sub.3 represents a CN group, an OH group, a CCH group, a (C.sub.1 -C.sub.3 alkoxy) carbonyl group or a C.sub.1 -C.sub.3 alkylated cyanomethyl group.
A process for the preparation of a compound of formula (I-d) ##STR10## which comprises:
- reacting an aromatic aldehyde of formula:
- ##STR11## in which:
- R.sub.1 represents a hydrogen atom, a benzyloxy or phenylethoxy group whose phenyl ring is optionally substituted, and a hydrazine of formula:
- NH.sub.2 --NH--(CH.sub.2).sub.p --R.sub.3 in which:
- p is an integer from 0 to 3;
- R.sub.3 represents a CN group, an OH group, a CCH group, a (C.sub.1 --C.sub.3 alkoxy)carbonyl group or a C.sub.1 --C.sub.3 alkylated cyanomethyl group to form a condensation product;
- and
- acylating the condensation product to form a compound of formula (I-d).
A process for the preparation of a compound of specific formula (I-e) ##STR12## which comprises:
- reacting an aromatic aldehyde of formula:
- ##STR13## in which:
- R.sub.1 represents a benzyloxy or phenylethoxy group whose phenyl ring is optionally substituted;
- and:
- a hydrazine of formula:
- NH.sub.2 --NH--(CH.sub.2).sub.p --R.sub.3 in which:
- p is an integer from 0 to 3;
- R.sub.3 represents a CN group, an OH group, a CCH group, a (C.sub.1 --C.sub.3 alkoxy)carbonyl group or a C.sub.1 --C.sub.3 alkylated cyanomethyl group;
- or a hydrazine of formula:
- NH.sub.2 --NH--CO--CH.sub.3 to form a condensation product;
- and
- acylating the condensation product or alkylating the condensation product using a reagent of formula:
- Hal--(CH.sub.2).sub.p --C.tbd.Z in which:
- p is an integer from 0 to 3;
- Hal represents a halogen atom;
- Z represents a CH group or a nitrogen atom, or by a reagent of formula:
- Br--(CH.sub.2).sub.p --COO--(C.sub.1 -C.sub.3 alkyl) in which p is an integer from 0 to 3 to form a compound of formula (I-e).
Dependencies are inferred from the claim text.