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 administration to a subject in need thereof a compound of general formula (I): 
       
         
           
           
               
               
           
         
         in which: 
         Cy represents a group chosen from: 
       
       
         
           
           
               
               
           
         
         W is chosen from a hydrogen atom or a halogen atom, Y is chosen from a hydrogen atom or a hydroxyl function and Z is a carbon atom or a bond (Cy is then a noradamantyl nucleus), 
         wherein, when Cy is an adamantyl nucleus, 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 general formula (I) is such that R 1  is an optionally substituted phenyl radical and/or X is —CH 2 — and/or R 2  is a hydrogen atom and/or W represents a Br 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 . The method as claimed in  claim 3 , characterized in that said compound of general formula (I) is defined by general formula (I′): 
       
         
           
           
               
               
           
         
         where X is either a bond or —CO—. 
       
     
     
         5 . The method as claimed in  claim 1 , characterized in that said compound of general formula (I) is chosen from:
 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)methyl)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)methyl)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)adamantylamine   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 74: N-(3-bromobenzyl)-2-methylpropan-2-amine   Compound 75: N-(3-bromobenzyl)-2,4,4-trimethylpentan-2-amine   Compound 76: 2-(3-bromobenzylamino)-3-hydroxy-2-methylpropanoic acid   Compound 77: 2-(3-bromobenzylamino)-2-(hydroxymethyl)propane-1,3-diol   Compound 78: N-(3-bromobenzyl)cyclohexanamine   Compound 79: 4-(3-bromobenzylamino)cyclohexanol   Compound 80: N-(3-fluorobenzyl)cyclohexylamine   Compound 81: 4-(3-fluorobenzylamino)cyclohexanol   Compound 82: (1-(3-bromobenzylamino)cyclopentyl)methanol   Compound 83: 1-(3-bromobenzylamino)cyclopentanecarboxylic acid   Compound 84: N-(3-bromobenzyl)bicyclo[2.2.1]heptan-2-amine   Compound 85: 2-(3-bromobenzylamino)bicyclo[2.2.1]heptane-2-carboxylic acid   Compound 86: N-(3-bromobenzyl)noradamantylamine   Compound 87: N-(3-bromobenzyl)-1-hydroxy-2-adamantylamine   Compound 88: N-(3-bromobenzyl)-N-((benzo[d][1,3]dioxol-6-yl)methyl)(3-bromophenyl)methanamine   Compound 89: 2-(3-bromobenzylamino)-2-(4-hydroxybenzyl)propanoic acid   Compound 90: 2-(3,4-dihydroxybenzyl)-2-(3-bromobenzylamino)propanoic acid   Compound 91: 2-(3-bromobenzylamino)-2-phenylbutanoic acid   Compound 92: 2-(3-bromobenzylamino)-2,2-diphenylacetic acid   Compound 93: methyl 2-(3-bromobenzylamino)-2-methyl-3-phenylpropanoate   Compound 94: methyl 3-(3-bromobenzylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate   Compound 95: N-(3-bromobenzyl)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine   Compound 96: N-(3-bromobenzyl)benzo[d][1,3]dioxol-5-amine   Compound 97: 2-(3-bromobenzylideneamino)-2-(3,4-dihydroxyphenyl)propanoic acid   Compound 98: N-benzyl(3-bromophenyl)methanamine   Compound 99: bis(3-bromobenzyl)amine   Compound 100: N-(3-fluorobenzyl)(3-bromophenyl)methanamine   Compound 101: N-(3-bromobenzyl)(1-methyl-1H-indol-2-yl)methanamine   Compound 102: N-(3-bromobenzyl)-1-phenylethanamine   Compound 103: N-(3-bromobenzyl)-1-(3-bromophenyl)ethanamine   Compound 104: N-(3-bromobenzyl)-1-(pyridin-2-yl)ethanamine   Compound 105: N-(3-bromobenzyl)quinuclidin-3-amine   Compound 106: (1R*,5S*)—N-(3-bromobenzyl)bicyclo[3.3.1]nonan-9-amine   Compound 107: N-(3-bromobenzyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-amine   Compound 108: N-(1-(3-bromophenyl)ethyl)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 136: 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 149: 2-(3-bromobenzylideneamino)-N-phenylbenzamide   Compound 150: 2-(3-bromobenzylamino)-N-phenylbenzamide   Compound 151: 2-(3-fluorobenzylideneamino)-N-phenylbenzamide   Compound 152: (E)-2-((furan-2-yl)methyleneamino)-N-phenylbenzamide   Compound 153: (E)-2-((furan-3-yl)methyleneamino)-N-phenylbenzamide   Compound 154: (E)-2-((5-methylfuran-2-yl)methyleneamino)-N-phenylbenzamide   Compound 155: (E)-2-(5-fluoro-2-nitrobenzylideneamino)-N-phenylbenzamide   Compound 156: (E)-2-(4-fluorobenzylideneamino)-N-phenylbenzamide   Compound 157 (E)-2-(2-fluorobenzylideneamino)-N-phenylbenzamide   Compound 158: (E)-2-((1-methyl-1H-indol-2-yl)methyleneamino)-N-phenylbenzamide   Compound 159: (E)-2-(5-bromo-2-hydroxybenzylideneamino)-N-phenylbenzamide   Compound 160: 2-(2-fluorobenzylamino)-N-phenylbenzamide   Compound 161: (E)-2-(2-(5-methylthiophen-2-yl)vinyl)-N-phenylbenzamide   Compound 191: N-cinnamyl-2-adamantylamine   Compound 192: N-(3-nitrobenzyl)-2-adamantylamine   
     
     
         6 . A compound of general formula (I): 
       
         
           
           
               
               
           
         
         in which: 
         Cy represents a group chosen from: 
       
       
         
           
           
               
               
           
         
         W is chosen from a hydrogen atom or a halogen atom, Y is chosen from a hydrogen atom or a hydroxyl function and Z is a carbon atom or a bond (Cy is then a noradamantyl nucleus), 
         wherein, when Cy is an adamantyl nucleus, 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 substitute with a phenyl or pyridine radical; 
         and the pharmaceutically acceptable salts thereof, 
         except for compounds 1, 6, 8, 11, 18, 29, 30, 34, 74, 78, 98, 100, 113, 114, 116, 121, 122, 124, 128, 135, 145 and 161 in Table 1 of the specification. 
       
     
     
         7 . 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 administration to a subject in need thereof a compound which is a benzodiazepine derivative of general formula (II): 
       
         
           
           
               
               
           
         
         where 
         A and B represent a carbon atom or a nitrogen atom with the proviso that, if A=N then B=C, and if A=C then B=N; 
         R 3  is chosen from a hydrogen or halogen atom; a C 1 -C 6  alkyl radical, a C 1 -C 6  alkoxy radical or a C 1 -C 6  acyloxy radical, these radicals being optionally substituted with a C 1 -C 6  alkoxy radical; an aryloxy radical or a heteroaryloxy radical; 
         R 4  either represents a bond or is chosen from a hydrogen atom, a C 1 -C 3  acyloxy radical, a C 1 -C 3  alkoxy radical or a phenyl; 
         R 5  either represents a bond or is chosen from a hydrogen atom; a C 1 -C 3  alkyl radical; a C 1 -C 3  alkoxy radical; a C 1 -C 3  acyloxy radical or a phenyl radical which is optionally substituted with an —OH function and/or a halogen atom, a C 1 -C 3  alkyl radical, a C 1 -C 3  alkoxy radical, a C 1 -C 3  acyloxy radical, an —NO 2  or —CF 3  function, or a radical 
       
       
         
           
           
               
               
           
         
         wherein R 4  and R 5  cannot simultaneously represent a bond and that, when one of the two is a bond, then A and B are linked by a double bond; and 
         that, when B is a carbon atom, R 5  can also form, with the hydrogen atom borne by the carbon adjacent to B, a ring of 5 or 6 atoms, optionally substituted with a phenyl radical, optionally interrupted with a nitrogen, sulfur or oxygen atom; and also the pharmaceutically acceptable salts thereof. 
       
     
     
         8 . The method as claimed in  claim 7 , characterized in that said compound of general formula (II) is such that R 3  is a bond and/or R 4  represents a hydrogen atom and/or R 5  represents a phenyl radical and/or, when A is a carbon atom, then R 4  is a phenyl radical, and/or, when B is a carbon atom, then R 5  is a phenyl radical. 
     
     
         9 . The method as claimed in  claim 7 , characterized in that said compound of general formula (II) is chosen from:
 Compound 162: 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one   Compound 163: 7-bromo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one   Compound 164: 7-bromo-5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one   Compound 165: 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one   Compound 166: 4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one   Compound 167: 4,5-dihydro-7-methoxy-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one   Compound 168: Ethyl 4-oxo-2-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carboxylate   Compound 169: 5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one   Compound 170: 7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one   Compound 171: 7-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one   Compound 172: 4-(2-hydroxyphenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 173: 4-(5-bromo-2-hydroxyphenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 174: 4-(5-fluoro-2-hydroxyphenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 175: 8-bromo-3-phenyl-3,3a,5,10-tetrahydrobenzo[b]pyrrolo[2,3-e][1,4]diazepin-4(2H)-one   Compound 176: 4-m-tolyl-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 177: 4-(3-methoxyphenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 178: 4-(3-nitrophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 179: 4-(3-chlorophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 180: 4-(3-bromophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 181: 4-(3-(trifluoromethyl)phenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 182: 7-bromo-4-m-tolyl-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 183: 7-bromo-4-(3-methoxyphenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 184: 7-bromo-4-(3-nitrophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 185: 7-bromo-4-(3-chlorophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 186: 7-bromo-4-(3-bromophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 187: 7-bromo-4-(3-(trifluoromethyl)phenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one   Compound 193: 7-bromo-5-phenyl-4-propionyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one   
     
     
         10 . A compound which is a benzodiazepine derivative of general formula (II): 
       
         
           
           
               
               
           
         
         where 
         A and B represent a carbon atom or a nitrogen atom with the proviso that, if A=N then B=C, and if A=C then B=N; 
         R 3  is chosen from a hydrogen or halogen atom; a C 1 -C 6  alkyl radical, a C 1 -C 6  alkoxy radical or a C 1 -C 6  acyloxy radical, these radicals being optionally substituted with a C 1 -C 6  alkoxy radical; an aryloxy radical or a heteroaryloxy radical; 
         R 4  either represents a bond or is chosen from a hydrogen atom, a C 1 -C 3  acyloxy radical, a C 1 -C 3  alkoxy radical or a phenyl; 
         R 5  either represents a bond or is chosen from a hydrogen atom; a C 1 -C 3  alkyl radical; a C 1 -C 3  alkoxy radical; a C 1 -C 3  acyloxy radical or a phenyl radical which is optionally substituted with an —OH function and/or a halogen atom, a C 1 -C 3  alkyl radical, a C 1 -C 3  alkoxy radical, a C 1 -C 3  acyloxy radical, an —NO 2  or —CF 3  function, or a radical 
       
       
         
           
           
               
               
           
         
         wherein R 4  and R 5  cannot simultaneously represent a bond and that, when one of the two is a bond, then A and B are linked by a double bond; and 
         that, when B is a carbon atom, R 5  can also form, with the hydrogen atom borne by the carbon adjacent to B, a ring of 5 or 6 atoms, optionally substituted with a phenyl radical, optionally interrupted with a nitrogen, sulfur or oxygen atom; 
         and also the pharmaceutically acceptable salts thereof, 
         except for compounds 162, 163, 164, 165, 166, 167, 169, 170, 171 and 193 in Table 2 of the specification. 
       
     
     
         11 . A pharmaceutical composition comprising the compound as claimed in  claim 6  or  10 . 
     
     
         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 , characterized in that said composition is intended to be administered orally, aerially, parenterally or locally. 
     
     
         14 . The method as claimed in any one of  claims 1  or  7  wherein the poisoning is ricin poisoning. 
     
     
         15 . The method as claimed in  claim 14 , characterized in that said compound is chosen from compounds 1, 3, 5, 9, 15, 19, 24, 28, 34, 36, 39, 59, 65, 67, 68, 69, 75, 86, 89, 105, 106, 109, 110, 111, 112, 117, 118, 122, 128, 131, 138, 139, 140, 142, 143, 148, 154, 161 and 193 in Tables 1 and 2 of the specification. 
     
     
         16 . The method as claimed in  claim 14 , characterized in that the compound of general formula (I) is defined by general formula (I.1): 
       
         
           
           
               
               
           
         
         in which: 
         Cy represents a group chosen from: 
       
       
         
           
           
               
               
           
         
         Z is a carbon atom or a bond (Cy is then a noradamantyl nucleus), 
         wherein when Cy is an adamantyl nucleus, the nitrogen atom 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 , characterized in that said compound of general formula (I.1) is chosen from compounds 1, 3, 5, 9, 15, 19, 24, 28, 34, 36, 39, 59, 65, 86, 109, 110, 111, 112, 138, 139, 140, 142, 143 and 148 in Table 1 of the specification. 
     
     
         18 . The method as claimed in  claim 14 , characterized in that 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 , characterized in that said compound of general formula (I.2) is chosen from compounds 68, 69, 122 and 128 in Table 1 of the specification. 
     
     
         20 . The method as claimed in  claim 14 , characterized in that 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 , characterized in that said compound of general formula (I.3) is chosen from compounds 117 and 118 in Table 1 of the specification. 
     
     
         22 . The method as claimed in  claim 14 , characterized in that the compound of general formula (I) is defined by general formula (I.4): 
       
         
           
           
               
               
           
         
         in which Y is O or S, 
         and the pharmaceutically acceptable salts thereof. 
       
     
     
         23 . The method as claimed in  claim 22 , characterized in that said compound of general formula (I.3) is chosen from compounds 154 and 161 in Table 1 of the specification. 
     
     
         24 . The method as claimed in any one of  claims 1  or  7  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 a group: 
       
       
         
           
           
               
               
           
         
       
       to which the nitrogen atom 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 chosen from compounds 5, 9, 39, 110, 111, 112, 139 and 140 in Table 1 of the specification. 
     
     
         27 . A compound of general formula (I.1) 
       
         
           
           
               
               
           
         
         and the pharmaceutically acceptable salts thereof,
 in which: 
 Cy represents a group chosen from: 
 
       
       
         
           
           
               
               
           
         
         
           Z is a carbon atom or a bond (Cy is then a noradamantyl nucleus), 
           wherein when Cy is an adamantyl nucleus, the nitrogen atom 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.