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

Abstract

The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.

1 . A method for the prevention and/or treatment of poisonings with at least one toxin with an intracellular mode of action or with at least one virus that uses the internalization pathway for infecting mammalian eukaryotic cells comprising administering to a subject in need thereof 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, C 1 -C 6  alkyl chain which is optionally substituted with a phenyl radical, an acid function and/or a C 1 -C 3  alkyl ester radical; said chain being optionally interrupted with an oxygen atom;   —CO—, —O—CO—, —CO—NH— or   
 
       
         
           
           
               
               
           
         
         R 1  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 —NO 2  function, a C 1 -C 3  alkyl radical, a C 1 -C 3  alkoxy radical or a C 1 -C 3  acyloxy radical; 
         R 2  either represents a bond or is chosen from a hydrogen atom, an optionally unsaturated, optionally branched, C 1 -C 3  alkyl radical, a C 2 -C 4  acyl radical or the radical 
       
       
         
           
           
               
               
           
         
         wherein, when R 2  is a bond, then the nitrogen atom bearing R 2  and X or the adjacent carbon atom (when p=1) are linked by a double bond, 
         wherein X, R 1  and R 2  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. 
       
     
     
         2 . The method as claimed in  claim 1 , characterized in that said compound of and/or R 2  is a hydrogen atom. 
     
     
         3 . The method as claimed in  claim 1 , characterized in that said compound of general formula (I) is such that R 1  is the radical:
 in which:   
       
         
           
           
               
               
           
         
         R 3  is chosen from a saturated or unsaturated cyclic radical containing 5 or 6 carbon atoms; a saturated or unsaturated bicyclic radical containing 9 or 10 carbon atoms; a saturated or unsaturated tricyclic radical containing 14 carbon atoms; a saturated or unsaturated heterocyclic radical containing 5 atoms; a saturated or unsaturated heterocyclic radical containing 6 atoms; a saturated or unsaturated biheterocyclic radical containing 9 or 10 atoms; said radicals being optionally substituted with at least one halogen atom, —NO 2 , —OH or one C 1 -C 3  alkyl radical; and 
         R 4  is chosen from —CO—O—, —N═CH— or —NH—CH 2 —. 
       
     
     
         4 . (canceled) 
     
     
         5 . The method as claimed in  claim 1 , characterized in that said compound of general formula (I) is selected from the group consisting of
 Compound 1: N-benzyladamantylamine;   Compound 2: N-(2-bromobenzyl)adamantylamine;   Compound 3: N-(3-bromobenzyl)adamantylamine;   Compound 4: N-(4-bromobenzyl)adamantylamine;   Compound 5: N-(3-fluorobenzyl)adamantylamine;   Compound 6: N-(3-hydroxybenzyl)adamantylamine;   Compound 7: N-(2-methoxybenzyl)adamantylamine;   Compound 8: N-(3-methoxybenzyl)adamantylamine;   Compound 9: N-(4-methoxybenzyl)adamantylamine;   Compound 10: N-(2-nitrobenzyl)adamantylamine;   Compound 11: N-(4-nitrobenzyl)adamantylamine;   Compound 12: N-(4-carbethoxybenzyl)adamantylamine;   Compound 13: 4-bromo-2-((1-adamantylino)methyl)phenol;   Compound 14: N-(2-bromo-5-nitrobenzyl)adamantylamine;   Compound 15: N-[(2-methoxy-5-bromo)benzyl]adamantylamine;   Compound 16: N-((pyridin-2-yl)methyl)adamantylamine;   Compound 17: N-((pyridin-3-yl)methyl)adamantylamine;   Compound 18: N-((pyridin-4-yl)methyl)adamantylamine;   Compound 19: N-((5-methylfuran-2-yl)methy)adamantylamine;   Compound 20: N-((5-methylthiophen-2-yl)methyl)cyclohexanamine;   Compound 21: N-[(3-furyl)methyl]adamantylamine;   Compound 22: N-((1-methyl-1H-imidazol-5-yl)methy)adamantylamine;   Compound 23: N-[(5-N-methylimidazolyl)methyl]adamantylamine;   Compound 24: Benzo[d][1,3]dioxol-4-yl)methyl)adamantylamine;   Compound 25: N-((5-nitrobenzo[d][1,3]dioxol-6-yl)methyl)adamantylamine;   Compound 26: N-((quinolin-3-yl)methyl)adamantylamine;   Compound 27: N-((quinolin-4-yl)methyl)adamantylamine;   Compound 28: N-((1-methyl-1H-indol-2-yl)methyl)adamantylamine;   Compound 29: N-phenethyladamantylamine;   Compound 30: N-(3-phenylpropyl)adamantylamine;   Compound 31: N-(2-(benzyloxy)ethyl)adamantylamine;   Compound 32: N-cinnamyladamantylamine;   Compound 33: N-methyl(3-bromobenzyl)adamantylamine;   Compound 34: N-benzyl-2-adamantylamine;   Compound 35: N-(2-bromobenzyl)-2-adamantylamine;   Compound 36: N-(3-bromobenzyl)-2-adamantylamine;   Compound 37: N-(4-bromobenzyl)adamantylannine;   Compound 38: N-(2-fluorobenzyl)-2-adamantylamine;   Compound 39: N-(3-fluorobenzyl)-2-adamantylamine;   Compound 40: N-(4-fluorobenzyl)-2-adamantylamine;   Compound 41: N-(3-hydroxybenzyl)-2-adamantylamine;   Compound 42: N-(2-methoxybenzyl)-2-adamantylamine;   Compound 43: N-(3-methoxybenzyl)-2-adamantylamine;   Compound 44: N-(4-methoxybenzyl)-2-adamantylamine;   Compound 45: N-(2-nitrobenzyl)-2-adamantylamine;   Compound 46: N-(4-nitrobenzyl)-2-adamantylamine;   Compound 47: N-(4-carbethoxybenzyl)-2-adamantylamine;   Compound 48: 4-bromo-2-((2-adamantylamino)methyl)phenol;   Compound 49: N-(2-bromo-5-nitrobenzyl)-2-adamantylamine;   Compound 50: N-(5-bromo-2-methoxybenzyl)-2-adamantylamine;   Compound 51: N-(5-fluoro-2-nitrobenzyl)-2-adamantylamine;   Compound 52: N-(2,5-difluorobenzyl)-2-adamantylamine;   Compound 53: N-((pyridin-2-yl)methyl)-2-adamantylamine;   Compound 54: N-((pyridin-3-yl)methyl)-2-adamantylamine;   Compound 55: N-((pyridin-4-yl)methyl)-2-adamantylamine;   Compound 56: N-((5-methylfuran-2-yl)methyl)-2-adamantylamine;   Compound 57: N-((5-methylthiophen-2-yl)methyl)-2-adamantylamine;   Compound 58: N-((furan-3-yl)methyl)-2-adamantylamine;   Compound 59: N-((1-methyl-1H-imidazol-5-yl)methyl)-2-adamantylamine;   Compound 60: N-[(5-N-methylimidazolyl)methyl]-2-adamantylamine;   Compound 61: Benzo[d][1,3]dioxol-4-yl)methyl)-2-adamantylamine;   Compound 62: N-((5-nitrobenzo[d][1,3]dioxol-6-yl)methyl)-2-adamantylamine;   Compound 63: N-((quinolin-3-yl)methyl)-2-adamantylamine;   Compound 64: N-((quinolin-4-yl)methyl)-2-adamantylamine;   Compound 65: N-((1-methyl-1H-indol-2-yl)methyl)-2-adamantylamine;   Compound 66: N-(1-(3-bromophenyl)ethyl)-2-adamantylamine;   Compound 67: N-benzhydryl-2-adamantylamine;   Compound 68: N-(2-(benzyloxy)ethyl)-2-adamantylamine;   Compound 69: N-(phenylpropyl)-2-adamantylamine;   Compound 70: N-(1-phenylethyl)-2-adamantylamine;   Compound 71: N-(1-(pyridin-2-yl)ethyl)-2-adamantylamine;   Compound 72: N-(2-adamantylmethyl)-1-(adamantyl)ethanamine;   Compound 73: N-methyl(3-bromobenzyl)-2-adamantylamine;   Compound 86: N-(3-bromobenzyl)noradamantylamine;   Compound 87: N-(3-bromobenzyl)-1-hydroxy-2-adamantylamine;   Compound 109: N-(3-fluorobenzyl)noradamantylamine;   Compound 110: N-(3-bromobenzyl)adamantylamine hydrochloride salt;   Compound 111: N-(5-bromo-2-methoxybenzyl)adamantylamine hydrochloride salt;   Compound 112: N-(2-bromobenzyl)-2-adamantylamine hydrochloride salt;   Compound 113: (E)-N-(3-bromobenzylidene)adamantylamine;   Compound 114: (E)-N-(3-fluorobenzylidene)adamantylamine;   Compound 115: (E)-N-((1-methyl-1H-indol-2-yl)methylene)adamantylamine;   Compound 116: (E)-N-benzylideneadamantylamine;   Compound 117: (E)-N-(3-bromobenzylidene)adamantylamine;   Compound 118: (E)-N-(3-fluorobenzylidene)adamantylamine;   Compound 119: (E)-N-(3-bromobenzylidene)noradamantylamine;   Compound 120: (E)-N-((1-methyl-1H-indol-2-yl)methylene)noradamantylamine;   Compound 121: N-1-adamantylbenzamide;   Compound 122: N-2-adamantylbenzamide;   Compound 123: phenyl N-adamantylcarbamate;   Compound 124: N-adamantyl benzenesulfonamide;   Compound 125: N-adamantyl-N-(3-bromobenzyl)acetamide;   Compound 126: phenyl N-2-adamantylcarbamate;   Compound 127: N-adamantyl-N-(3-bromobenzyl)benzamide;   Compound 128: N-2-adamantyl benzenesulfonamide;   Compound 129: 1-(adamantyl)-3-phenylurea;   Compound 131: 1-(adamantyl)-1-(3-bromobenzyl)-3-phenylurea;   Compound 132: 1-(2-adamantyl)-3-phenylurea;   Compound 134: 1-(adamantyl)-2,5-dihydro-1H-imidazole;   Compound 135: 1-(adamantyl)-2,5-dihydrooxazole;   Compound 136: 1-(adamantyl)-1-phenyl-4,5-dihydro-1H-imidazole;   Compound 137: 1-(adamantyl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazole;   Compound 138: N-(3-chlorobenzyl)adamantylamine;   Compound 139: N-(3-chlorobenzyl)-2-adamantylamine;   Compound 140: N-(3-iodobenzyl)-2-adamantylamine;   Compound 141: N-(2,2-diphenylethyl)-2-adamantylamine;   Compound 142: N-(naphthalen-1-ylmethyl)-2-adamantylamine;   Compound 143: N-(phenanthren-9-ylmethyl)-2-adamantylamine;   Compound 144: 4-((adamantylamino)methyl)benzoic acid;   Compound 145: adamantylamino-4-phenyl-1H-1,2,3-triazole;   Compound 146: adamantylamino-4-phenyl-1H-1,2,3-triazole;   Compound 147: 2-(adamantylamino-1H-1,2,3-triazol-4-yl)pyridine;   Compound 148: N-(2-bromo-5-nitrobenzyl)adamantylamine;   Compound 191: N-cinnamyl-2-adamantylamine; and   Compound 192: N-(3-nitrobenzyl)-2-adamantylamine.   
     
     
         6 . 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, C 1 -C 6  alkyl chain which is optionally substituted with a phenyl radical, an acid function and/or a C 1 -C 3  alkyl ester radical; said chain being optionally interrupted with an oxygen atom;   
 
       
         
           
           
               
               
           
         
         
           —CO—, —O—CO—, —CO—NH— or 
         
         R 1  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 —NO 2  function, a C 1 -C 3  alkyl radical, a C 1 -C 3  alkoxy radical or a C 1 -C 3  acyloxy radical; 
         R 2  either represents a bond or is chosen from a hydrogen atom, an optionally unsaturated, optionally branched, C 1 -C 3  alkyl radical, a C 2 -C 4  acyl radical or the radical 
       
       
         
           
           
               
               
           
         
         wherein, when R 2  is a bond, then the nitrogen atom bearing R 2  and X or the adjacent carbon atom (when p=1) are linked by a double bond, 
         wherein X, R 1  and R 2  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. 
       
     
     
         7 - 10 . (canceled) 
     
     
         11 . A pharmaceutical composition comprising the compound as claimed in  claim 6 . 
     
     
         12 . The pharmaceutical composition as claimed in  claim 11 , further comprising at least one pharmaceutically acceptable vehicle. 
     
     
         13 . The pharmaceutical composition as claimed in  claim 11 , wherein the composition is formulated to be administered orally, aerially, parenterally or locally. 
     
     
         14 . The method as claimed in  claim 1 , wherein the poisoning is ricin poisoning. 
     
     
         15 . The method as claimed in  claim 14 , wherein said compound is selected from the group consisting of:
 Compound 1: N-benzyladamantylamine;   Compound 3: N-(3-bromobenzyl)adamantylamine;   Compound 5: N-(3-fluorobenzyl)adamantylamine;   Compound 9: N-(4-methoxybenzyl)adamantylamine;   Compound 15: N-[(2-methoxy-5-bromo)benzyl]adamantylamine;   Compound 19: N-((5-methylfuran-2-yl)methy)adamantylamine;   Compound 24: Benzo[d][1,3]dioxol-4-yl)methyl)adamantylamine;   Compound 28: N-((1-methyl-1H-indol-2-yl)methyl)adamantylamine;   Compound 34: N-benzyl-2-adamantylamine;   Compound 36: N-(3-bromobenzyl)-2-adamantylamine;   Compound 39: N-(3-fluorobenzyl)-2-adamantylamine;   Compound 59: N-((1-methyl-1H-imidazol-5-yl)methyl)-2-adamantylamine;   Compound 65: N-((1-methyl-1H-indol-2-yl)methyl)-2-adamantylamine;   Compound 67: N-benzhydryl-2-adamantylamine;   Compound 68: N-(2-(benzyloxy)ethyl)-2-adamantylamine;   Compound 69: N-(phenylpropyl)-2-adamantylamine;   Compound 75: N-(3-bromobenzyl)-2,4,4-trimethylpentan-2-amine;   Compound 86: N-(3-bromobenzyl)noradamantylamine;   Compound 109: N-(3-fluorobenzyl)noradamantylamine;   Compound 110: N-(3-bromobenzyl)adamantylamine hydrochloride salt;   Compound 111: N-(5-bromo-2-methoxybenzyl)adamantylamine hydrochloride salt;   Compound 112: N-(2-bromobenzyl)-2-adamantylamine hydrochloride salt;   Compound 117: (E)-N-(3-bromobenzylidene)adamantylamine;   Compound 118: (E)-N-(3-fluorobenzylidene)adamantylamine;   Compound 122: N-2-adamantylbenzamide;   Compound 128: N-2-adamantyl benzenesulfonamide;   Compound 131: 1-(adamantyl)-1-(3-bromobenzyl)-3-phenylurea;   Compound 138: N-(3-chlorobenzyl)adamantylamine;   Compound 139: N-(3-chlorobenzyl)-2-adamantylamine;   Compound 140: N-(3-iodobenzyl)-2-adamantylamine;   Compound 142: N-(naphthalen-1-ylmethyl)-2-adamantylamine;   Compound 143: N-(phenanthren-9-ylmethyl)-2-adamantylamine; and   Compound 148: N-(2-bromo-5-nitrobenzyl)adamantylamine.   
     
     
         16 . The method as claimed in  claim 14 , wherein the compound of general formula (I) is defined by general formula (I.1): 
       
         
           
           
               
               
           
         
         in which: 
         Cy represents: 
       
       
         
           
           
               
               
           
         
         
           Z is a carbon atom or a bond, 
           wherein the nitrogen atom in formula I.1 is attached thereto in position 1 or 2, 
         
         R 1  represents: a phenyl ring, optionally substituted with an —OCH 3  radical in the para-position with respect to the carbon atom bonded to the —CH 2 —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 —CH 2 —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 —NO 2  and —OCH 3 ; an indole, imidazole or furan ring substituted with a methyl radical; a benzo(1,3)dioxolo ring, a naphthalenyl ring or a phenanthrenyl ring; 
         and the pharmaceutically acceptable salts thereof. 
       
     
     
         17 . The method as claimed in  claim 16 , wherein said compound of general formula (I.1) is selected from the group consisting of:
 Compound 1: N-benzyladamantylamine;   Compound 3: N-(3-bromobenzyl)adamantylamine;   Compound 5: N-(3-fluorobenzyl)adamantylamine;   Compound 9: N-(4-methoxybenzyl)adamantylamine;   Compound 15: N-[(2-methoxy-5-bromo)benzyl]adamantylamine;   Compound 19: N-((5-methylfuran-2-yl)methy)adamantylamine;   Compound 24: Benzo[d][1,3]dioxol-4-yl)methyl)adamantylamine;   Compound 28: N-((1-methyl-1H-indol-2-yl)methyl)adamantylamine;   Compound 34: N-benzyl-2-adamantylamine;   Compound 36: N-(3-bromobenzyl)-2-adamantylamine;   Compound 39: N-(3-fluorobenzyl)-2-adamantylamine;   Compound 59: N-((1-methyl-1H-imidazol-5-yl)methyl)-2-adamantylamine;   Compound 65: N-((1-methyl-1H-indol-2-yl)methyl)-2-adamantylamine;   Compound 86: N-(3-bromobenzyl)noradamantylamine;   Compound 109: N-(3-fluorobenzyl)noradamantylamine;   Compound 110: N-(3-bromobenzyl)adamantylamine hydrochloride salt;   Compound 111: N-(5-bromo-2-methoxybenzyl)adamantylamine hydrochloride salt;   Compound 112: N-(2-bromobenzyl)-2-adamantylamine hydrochloride salt;   Compound 138: N-(3-chlorobenzyl)adamantylamine;   Compound 139: N-(3-chlorobenzyl)-2-adamantylamine;   Compound 140: N-(3-iodobenzyl)-2-adamantylamine;   Compound 142: N-(naphthalen-1-ylmethyl)-2-adamantylamine;   Compound 143: N-(phenanthren-9-ylmethyl)-2-adamantylamine; and   Compound 148: N-(2-bromo-5-nitrobenzyl)adamantylamine.   
     
     
         18 . The method as claimed in  claim 14 , wherein the compound of general formula (I) is defined by general formula (I.2): 
       
         
           
           
               
               
           
         
         in which X represents —(CH 2 ) 2 —O—CH 2 —, —(CH 2 ) 3 —, —CO— or —SO 2 —, 
         and the pharmaceutically acceptable salts thereof. 
       
     
     
         19 . The method as claimed in  claim 18 , wherein said compound of general formula (I.2) is selected from the group consisting of:
 Compound 68: N-(2-(benzyloxy)ethyl)-2-adamantylamine;   Compound 69: N-(phenylpropyl)-2-adamantylamine;   Compound 122: N-2-adamantylbenzamide; and   Compound 128: N-2-adamantyl benzenesulfonamide.   
     
     
         20 . The method as claimed in  claim 14 , wherein the compound of general formula (I) is defined by general formula (I.3): 
       
         
           
           
               
               
           
         
         in which W represents a halogen atom, 
         and the pharmaceutically acceptable salts thereof. 
       
     
     
         21 . The method as claimed in  claim 20 , wherein said compound of general formula (I.3) is
 Compound 117: (E)-N-(3-bromobenzylidene)adamantylamine; or   Compound 118: (E)-N-(3-fluorobenzylidene)adamantylamine.   
     
     
         22 - 23 . (canceled) 
     
     
         24 . The method as claimed in  claim 1 , wherein the poisoning is from diphtheria toxin. 
     
     
         25 . The method as claimed in  claim 24 , characterized in that the compound of general formula (I) is defined by general formula (I.5): 
       
         
           
           
               
               
           
         
         in which: 
         Cy represents 
       
       
         
           
           
               
               
           
         
       
       to which the nitrogen atom of formula I.5 is attached in position 1 or 2,
 W and W′ are, independently of one another, chosen from a hydrogen atom, a halogen atom and a C 1 -C 3  alkoxy radical, 
 and the pharmaceutically acceptable salts thereof. 
 
     
     
         26 . The method as claimed in  claim 25 , characterized in that said compound of general formula (I) is selected from the group consisting of the compounds:
 Compound 5: N-(3-fluorobenzyl)adamantylamine;   Compound 9: N-(4-methoxybenzyl)adamantylamine;   Compound 39: N-(3-fluorobenzyl)-2-adamantylamine;   Compound 110: N-(3-bromobenzyl)adamantylamine hydrochloride salt;   Compound 111: N-(5-bromo-2-methoxybenzyl)adamantylamine hydrochloride salt;   Compound 112: N-(2-bromobenzyl)-2-adamantylamine hydrochloride salt;   Compound 139: N-(3-chlorobenzyl)-2-adamantylamine; and   Compound 140: N-(3-iodobenzyl)-2-adamantylamine.   
     
     
         27 . 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, 
         R 1  represents a phenyl ring, optionally substituted with an —OCH 3  radical in the para-position with respect to the carbon atom bonded to the —CH 2 —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 —CH 2 —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 —NO 2  and —OCH 3 ; an indole, imidazole or furan ring substituted with a methyl radical; a benzo(1,3)dioxolo ring, a naphthalenyl ring or a phenanthrenyl ring.