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1. WO2020115045 - DÉRIVÉS DE 1H-BENZO[D]IMIDAZOLE SUBSTITUÉS AYANT UNE ACTIVITÉ MULTIMODALE DIRIGÉE CONTRE LA DOULEUR ET DES ÉTATS PATHOLOGIQUES ASSOCIÉS À LA DOULEUR

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

[ EN ]

CLAIMS

1 . A compound of formula (I):


wherein

RI is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted Ci-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, and a group of the following formula (A):


wherein

Wi is carbon or nitrogen;

R7 and R7' are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl and substituted or unsubstituted C2-6 alkynyl; and

Re is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, and ORs·, wherein

Re’ is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, and substituted or unsubstituted C2-6 alkynyl;

Rr is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, and substituted or unsubstituted C2-6 alkynyl;

R2 is selected from the group consisting of halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, and substituted or unsubstituted C2-6 alkynyl;

R3 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, and substituted or unsubstituted heterocyclyl; wherein when the alkyl is substituted the substituents are selected from the group consisting of hydrogen, halogen, C1-6 alkyl, and substituted or unsubstituted heterocyclyl;

R4 is selected from the group consisting of halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, and substituted or unsubstituted C2-6 alkynyl;

R5, R5', R5” and R5” are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl and substituted or unsubstituted C2-6 alkynyl;

alternatively, R5 and R5· and/or R5 " and Rs- taken together with the carbon atom to which they are attached may form a substituted or unsubstituted cycloalkyl;

X is selected from the group consisting of a bond, [Chhjp- and NR6; wherein

p is 0, 1 or 2; and

R6 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, and [ChblqNR^Re”; wherein

R^ and R6- are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl and substituted or unsubstituted C2-6 alkynyl; and

q is 1 , 2, or 3;

m is 1 or 2;

n is 1 or 2;

wherein when one of Ri or Rr is halogen and the other is hydrogen, m is 1 and n is 1 , then at least one of R5, Rs·, Rs- and R5 is a substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl or substituted or unsubstituted C2- 6 alkynyl;

wherein the compound of formula (I) is optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.

2. Compound according to claim 1 , wherein R2 is substituted or unsubstituted C1-6 alkyl.

3. Compound according to claim 1 or 2 wherein R4 is substituted or unsubstituted C1-6 alkyl.

4. Compound according to any one of claims 1 to 3 wherein R3 is selected from hydrogen and unsubstituted C1-6 alkyl.

5. Compound according to claim any one of claims 1 to 4 wherein Ri is a group of formula (A):


wherein

Wi is carbon or nitrogen;

R7 and R7 are independently selected from the group consisting of hydrogen and substituted or unsubstituted Ci-6 alkyl; and

Re is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted Ci-6 alkyl and ORs·, wherein

Re’ is selected from the group consisting of hydrogen, halogen, and substituted or unsubstituted Ci-6 alkyl.

6. Compound according to claim 5 wherein Wi is nitrogen.

7. Compound according to claim 5 or 6, wherein R7 and R7· are unsubstituted Ci-6 alkyl.

8. Compound according to any one of claims 1 to 7 wherein said compound is selected from the group consisting of:

6-Bromo-2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazole;

[2] 5-bromo-2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazole;

[3] 2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazole;

[4] 5-bromo-2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazole;

[5] 5-bromo-1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazole;

[6] 5-bromo-2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)propyl)-1 -methyl-1 H- benzo[d]imidazole;

[7] 5-bromo-2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-6- fluoro-1 /-/-benzo[d]imidazole;

[8] 5-bromo-1 -ethyl-6-fluoro-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazole;

[9] 6-bromo-1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazole;

[10] 5-Bromo-2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl- 1 H-benzo[d]imidazole;

[1 1 ] 5-bromo-2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl- 1 H-benzo[d]imidazole;

[12] 5-BiOmo-2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl- 1 H-benzo[d]imidazole;

[13] 5-bromo-2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl- 1 H-benzo[d]imidazole;

[14] 1 -(2-(1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-6-yl)-N,N-dimethyl-4-phenylpiperidin-4-amine;

[15] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-/V,/V-dimethyl-4-phenylpiperidin-4-amine;

[16] 3-(4-(dimethylamino)-1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-1 /-/-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[17] 3-(4-(dimethylamino)-1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-1 /-/-benzo[d]imidazol-6-yl)piperidin-4-yl)phenol;

[18] 1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)-/V,/V-dimethyl-4-phenylpiperidin-4-amine;

[19] 3-(4-(dimethylamino)-1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 - yl)butyl)-1 /-/-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[20] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-/V-methyl-4-phenylpiperidin-4-amine;

[21 ] 3-(1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-4-(methylamino)piperidin-4-yl)phenol;

[22] 3-(4-(dimethylamino)-1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -methyl-1 /-/-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[23] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)-/V,/V-dimethyl-4-phenylpiperidin-4-amine;

[24] 3-(4-(dimethylamino)-1 -(1 -methyl-2-(1 -(4-methyl-1 ,4-diazepan-1 - yl)butyl)-1 H-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[25] 3-(1 -(2-(1 -(1 ,4-diazepan-1 -yl)butyl)-1 -ethyl-1 /-/-benzo[d]imidazol-5-yl)- 4-(dimethylamino)piperidin-4-yl)phenol;

[26] 3-(4-(dimethylamino)-1 -(1 -ethyl-2-(1 -(piperazin-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[27] 1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)-4-(3-methoxyphenyl)-/V,/V-dimethylpiperidin-4- amine;

[28] 1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)-4-(4-methoxyphenyl)-/V,/V-dimethylpiperidin-4- amine;

[29] 3-(4-(dimethylamino)-1 -(1 -methyl-2-(1 -(4-methyl-1 ,4-diazepan-1 - yl)propyl)-1 /-/-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[30] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-4-(3-methoxyphenyl)-/V,/V-dimethylpiperidin-4- amine;

[31 ] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-4-(4-methoxyphenyl)-/V,/V-dimethylpiperidin-4- amine;

[32] 1 -(2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)-4-(4-methoxyphenyl)-/V,/V-dimethylpiperidin-4- amine;

[33] L/1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)-/V1 ,/V2-dimethylethane-1 ,2-diamine;

[34] (R)-3-(4-(Dimethylamino)-1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 - yl)butyl)-1 H-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[35] (S)-3-(4-(dimethylamino)-1 -(1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 - yl)butyl)-1 H-benzo[d]imidazol-5-yl)piperidin-4-yl)phenol;

[36] 1 -(2-((R)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-4-(4-methoxyphenyl)-N,N-dimethylpiperidin-4- amine;

[37] 1 -(2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)-4-(4-methoxyphenyl)-N,N-dimethylpiperidin-4- amine;

[38] (1 S,4s)-N4-(2-((R)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 - ethyl-1 H-benzo[d]imidazol-5-yl)-N1 ,N1 -dimethyl-1 -phenylcyclohexane- 1 ,4-diamine;

[39] (1 R,4s)-N4-(2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 - ethyl-1 H-benzo[d]imidazol-5-yl)-N1 ,N1 -dimethyl-1 -phenylcyclohexane- 1 ,4-diamine;

[40] 1 -((2-(1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-6-yl)methyl)-N,N-dimethyl-4-phenylpiperidin-4- amine;

[41 ] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4- amine;

[42] 1 -((1 -ethyl-2-(1 -(4-methyl-1 ,4-diazepan-1 -yl)butyl)-1 H- benzo[d]imidazol-5-yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4- amine;

[43] 1 -((2-(1 -(1 ,4-diazepan-1 -yl)butyl)-1 -ethyl-1 /-/-benzo[d]imidazol-5- yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4-amine;

[44] 1 -((1 -ethyl-2-(1 -(piperazin-1 -yl)butyl)-1 /-/-benzo[d]imidazol-5- yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4-amine;

[45] 3-(4-(dimethylamino)-1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-1 /-/-benzo[d]imidazol-5-yl)methyl)piperidin-4-yl)phenol;

[46] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4- amine;

[47] 3-(4-(dimethylamino)-1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -methyl-1 /-/-benzo[d]imidazol-5-yl)methyl)piperidin-4- yl)phenol;

[48] 3-(4-(dimethylamino)-1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)propyl)-1 -ethyl-1 /-/-benzo[d]imidazol-5-yl)methyl)piperidin-4- yl)phenol;

[49] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[50] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[51 ] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[52] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[53] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[54] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[55] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[56] 1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[57] 4-(4-(dimethylamino)-1 -((2-(1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-6-fluoro-1 /-/-benzo[d]imidazol-5-yl)methyl)piperidin-4- yl)phenol;

[58] 1 -((2-((S)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-N,N-dimethyl-4-phenylpiperidin-4- amine;

[59] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-N,N-dimethyl-4-phenylpiperidin-4- amine;

[60] 3-(4-(dimethylamino)-1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-1 /-/-benzo[c/]imidazol-5-yl)methyl)piperidin-4-yl)phenol;

[61 ] 3-(4-(dimethylamino)-1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -ethyl-1 H-benzo[c/]imidazol-5-yl)methyl)piperidin-4-yl)phenol;

[62] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[c/]imidazol-5-yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4- amine;

[63] 1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[c/]imidazol-5-yl)methyl)-/V,/V-dimethyl-4-phenylpiperidin-4- amine;

[64] 3-(4-(Dimethylamino)-1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -methyl-1 /-/-benzo[c/]imidazol-5-yl)methyl)piperidin-4-yl);

[65] 3-(4-(dimethylamino)-1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 - yl)butyl)-1 -methyl-1 H-benzo[c/]imidazol-5-yl)methyl)pipericlin-4- yl)phenol;

[66] 1 -((2-((R)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[67] 1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[68] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[69] 1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(3-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[70] 1 -((2-((S)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(4-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[71] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-fluorophenyl)-/V,/V- dimethylpiperidin-4-amine;

[72] 1 -((2-((S)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[73] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[74] 1 -((2-((S)-1 -((3S,5R)-3,5-Dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[75] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -ethyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[76] 1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[77] 1 -((2-((R)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(3-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine;

[78] 1 -((2-((S)-1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[d]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine; and

[79] 1 -((2-((/? -1 -((3S,5R)-3,5-dimethylpiperazin-1 -yl)butyl)-1 -methyl-1 H- benzo[c/]imidazol-5-yl)methyl)-4-(4-methoxyphenyl)-/V,/V- dimethylpiperidin-4-amine.

9. Process for the preparation of a compound of formula (I) according to claim 1 :


said process comprising:

treating a compound of formula (V):


with a compound of formula (VI):


wherein

Ri , Rr, R2, R3, R4, R5-5 , X, W, m and n have the same meaning as indicated in any one of claims 1 to 7; and LG is a leaving group.

10. Process for the preparation of a compound of formula (I) according to claim 1 :


said process comprising:

treating a compound of formula (II):


with a compound of formula (VII):


wherein

Ri, Rr, R2, R3, R4, R5-5 , X, W, m and n have the same meaning as indicated in any one of claims 1 to 7.

1 1. Use of a compound selected from


wherein

Ri, Rr, R2, R3, R4, R5-5”, X, m and n have the same meaning as indicated in any one of claims 1 to 7 and LG is a leaving group for the manufacture of a compound according to claim 1.

12. Compound according to any one of claims 1 to 8 for use as a medicament.

13. Compound according to any one of claims 1 to 8, for use in the treatment and/or prophylaxis of diseases and/or disorders mediated by the subunit a2d, especially the a2d-1 subunit of voltage-gated calcium channels and the m-opioid receptor.

14. Compound for use according to claim 13, where the disease or disorder is pain, especially neuropathic pain, inflammatory pain, and chronic pain or other pain conditions involving allodynia and/or hyperalgesia, depression, anxiety and attention-deficit-/hyperactivity disorder.

15. A pharmaceutical composition comprising a compound of general formula (I) according to any one of claims 1 to 8 or a pharmaceutically acceptable salt, isomer, prodrug or solvate thereof, and at least a pharmaceutically acceptable carrier, additive, adjuvant or vehicle.