Bispiperidines as antithrombotic agents

Compounds of formula:

• in which:
• i) either R1 is chosen from:
• C1-C4 alkyl, C3-C12 mono- or bicyclic cycloalkyl, C2-C4 alkenyl or C2-C4 alkynyl groups, these groups optionally being substituted with groups chosen from halogens and the hydroxyl group;
• mono-, bi- or tricyclic C6-C14 aryl groups,
• heteroaryl groups chosen from pyridyl, thienyl, furyl, quinolyl, benzodioxanyl, benzodioxolyl, benzothienyl, benzofuryl and pyrazinyl groups;
• phenyl (C1-C4)alkyl and naphthyl(C1-C4)alkyl groups optionally substituted on the aryl nucleus,
• the aryl and heteroaryl groups possibly being substituted with one or more groups chosen independently from halogens, C1-C4 alkyl, trifluoromethyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl, C1-C4 alkyloxy, nitro and groups —COOR, —CH2COOR or —O—CH2—COOR, R being a C1-C4 alkyl group,
• the groups of formula:
• in which R4 and R′4 are chosen from C1-C8 alkyl and mono- or polycyclic C3-C12 cycloalkyl groups, these groups optionally being substituted with groups chosen from halogens and the hydroxyl group, R′4 also possibly being hydrogen, or alternatively R4 and R′4 together form a tetramethylene or pentamethylene group, these last two groups themselves possibly being substituted, in particular with a C6-C14 aryl or (C6-C14)aryl(C1-C4)alkyl residue;
• the groups of formula:
• in which m=1 to 4 and R5 is chosen from phenyl, methoxyphenyl, indolyl, benzodioxolyl, benzodioxanyl, benzothienyl and benzofuryl groups,
• and R2 is hydrogen,
• ii) or R1 is hydrogen and R2 is chosen from the groups of formula:
• —NH—CO—R6,
• R6 being chosen from C1-C4 alkoxy, C3-C7 cycloalkoxy, benzyloxy, methoxyphenyl, dimethoxyphenyl, benzodioxolyl and benzodioxanyl groups,
• and the groups of formula:
• —NH—SO2—R7,
• R7 being chosen from:
• C1-C5 alkyl groups optionally substituted with one or more groups chosen from halogens, hydroxyl groups and the trifluoromethyl group;
• C2-C5 alkenyl groups;
• mono- or bicyclic C3-C12 cycloalkyl groups;
• mono-, bi- or tricyclic C6-C14 aryl groups;
• heteroaryl groups chosen from pyridyl, furyl, thienyl, quinolyl, benzodioxanyl, benzodioxolyl, isoxazolyl, benzodioxinyl, benzothienyl, thiazolyl, pyrazolyl, benzofuryl and benzothiazolyl groups;
• phenyl(C1-C4)alkyl and naphthyl(C1-C4)alkyl groups;
• and the groups of formula:
• in which n=1, 2 or 3 and B is chosen from —CH2—, O or S and —NH—,
• the aryl or heteroaryl groups optionally being substituted with one or more groups chosen independently from halogens, C1-C4 alkyl, C3-C7 cycloalkyl, trifluoromethyl, C1-C4 alkylthio, C1-C4 alkyloxy, C1-C4 alkylsulfonyl, nitro, di((C1-C4)alkyl)amino and groups —COOR, —CH2—COOR or —O—CH2COOR, R being a C1-C4 alkyl group, phenyl and naphthyl groups and heteroaryl groups chosen from thienyl, furyl and pyridyl groups,
• iii) R3 is chosen from a hydrogen atom, a C1-C4 alkyl group and a phenyl (C1-C4) alkyl group;
• iv) A is chosen from groups —NH—CHR10—, —NH—CHR10—CH2— and
• with p=1 or 2,
• R10 being chosen from hydrogen, a C1-C4 alkyl group and a C6-C14 aryl group,
• v) and Z1 and Z2 are hydrogen or an amine-protecting group, and the addition salts thereof with pharmaceutically acceptable acids.