Compounds Which Have a Protective Activity with Respect to the Action of Toxins and of Viruses with an Intracellular Mode of Action

A compound of general formula (I):

• in which:
• Cy represents:
• Y is chosen from a hydrogen atom or a hydroxyl function and Z is a carbon atom or a bond,
• wherein the chain
• is attached thereto in position 1 or 2,
• p represents 0 or 1;
• X represents either:
• a bond;
• an optionally unsaturated, optionally branched, C1-C6 alkyl chain which is optionally substituted with a phenyl radical, an acid function and/or a C1-C3 alkyl ester radical;
• said chain being optionally interrupted with an oxygen atom;
• —CO—, —O—CO—, —CO—NH— or
• R1 represents a radical containing 1 to 21 carbon atoms, which is optionally branched and/or cyclic, and saturated or unsaturated, in which one or more of the carbon atoms can be replaced with a nitrogen, oxygen and/or sulfur atom;
• said radical being optionally monosubstituted or disubstituted with a halogen atom, a —COOH, —OH or —NO2 function, a C1-C3 alkyl radical, a C1-C3 alkoxy radical or a C1-C3 acyloxy radical;
• R2 either represents a bond or is chosen from a hydrogen atom, an optionally unsaturated, optionally branched, C1-C3 alkyl radical, a C2-C4 acyl radical or the radical
• wherein, when R2 is a bond, then the nitrogen atom bearing R2 and X or the adjacent carbon atom (when p=1) are linked by a double bond,
• wherein X, R1 and R2 can form, with the adjacent nitrogen atom, an imidazole, oxazole, triazole or benzimidazole ring, which is optionally partially saturated, such as in particular dihydroimidazole, optionally substituted with a phenyl or pyridine radical;
• and the pharmaceutically acceptable salts thereof,
• with the proviso that the compound of general formula (I) excludes the following compounds:
• Compound 1:
• N-benzyladamantylamine;
• Compound 6:
• N-(3-hydroxybenzyl)adamantylamine;
• Compound 8:
• N-(3-methoxybenzyl)adamantylamine;
• Compound 11:
• N-(4-nitrobenzyl)adamantylamine;
• Compound 18:
• N-((pyridin-4-yl)methyl)adamantylamine;
• Compound 29:
• N-phenethyladamantylamine;
• Compound 30:
• N-(3-phenylpropyl)adamantylamine;
• Compound 34:
• N-benzyl-2-adamantylamine;
• Compound 113:
• (E)-N-(3-bromobenzylidene)adamantyiamine;
• Compound 114:
• (E)-N-(3-fluorobenzylidene)adamantylamine;
• Compound 116:
• (E)-N-benzylideneadamantylamine;
• Compound 121:
• N-1-adamantylbenzamide;
• Compound 122:
• N-2-adamantylbenzamide;
• Compound 124:
• N-adamantyl benzenesulfonamide;
• Compound 128:
• N-2-adamantyl benzenesulfonamide;
• Compound 135:1-(adamantyl)-2,5-dihydrooxazole;
• and
• Compound 145:
• adamantylamino-4-phenyl-1H-1,2,3-triazole.

A compound of general formula (I.1)

• and the pharmaceutically acceptable salts thereof,
• in which:
• Cy represents:
• Z is a carbon atom or a bond,
• wherein the nitrogen atom of formula I.1 is attached thereto in position 1 or 2,
• R1 represents a phenyl ring, optionally substituted with an —OCH3 radical in the para-position with respect to the carbon atom bonded to the —CH2—NH-Cy chain;
• said ring being alternatively optionally substituted with a halogen atom in the meta-position with respect to the carbon atom bonded to the —CH2—NH-Cy chain, and in this case, said ring optionally bears a second substitution in the para-position with respect to said halogen atom, said second substitution being chosen from —NO2 and —OCH3;
• an indole, imidazole or furan ring substituted with a methyl radical;
• a benzo(1,3)dioxolo ring, a naphthalenyl ring or a phenanthrenyl ring.