4(Phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain of gastrointestinal disorders

A process for preparing a compound of formula VII:

• comprising:
• reacting a compound of formula VIII
• with a C1-6alkylcarbamate to form the compound of formula VII,
• wherein
• R8 is selected from C1-6alkyl-O—C(═O)—, C6-10aryl-C1-4alkyl, and C2-6heteroaryl-C1-4alkyl, wherein said C1-6alkyl-O—C(═O)—, C6-10aryl-C1-4alkyl, and C2-6heteroaryl-C1-4alkyl are optionally substituted with one or more groups selected from —OR, —Cl, —Br, —I, —F, —CF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen or C1-6alkyl;
• X is selected from halogen, triflate, and sulfonamide;
• and
• R11 is a C1-6alkyl.

A process for preparing a compound of formula X,

• comprising:
• reacting a compound of formula IX,
• with R4—CHO to form the compound of formula X,
• wherein
• R4 is selected from phenyl;
• pyridyl;
• thienyl;
• furyl;
• imidazolyl;
• triazolyl;
• pyrrolyl;
• thiazolyl;
• and N-oxido-pyridyl, wherein said phenyl;
• pyridyl;
• thienyl;
• furyl;
• imidazolyl;
• triazolyl;
• pyrrolyl;
• thiazolyl;
• and N-oxido-pyridyl are optionally substituted with one or more groups selected from C1-6alkyl, halogenated C1-6alkyl, —NO2, —CF3, C1-6 alkoxy, chloro, fluoro, bromo, and iodo;
• R2 is selected from —H, C1-6alkyl and C3-6cycloalkyl, wherein said C1-6alkyl and C3-6cycloalkyl are optionally substituted with one or more groups selected from —OR, —Cl, —Br, —I, —F, —CF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen or C1-6alkyl;
• and
• R3 is selected from —H, C1-6alkyl and C3-6cycloalkyl, wherein said C1-6alkyl and C3-6cycloalkyl are optionally substituted with one or more groups selected from —OR, —Cl, —Br, —I, —F, —CF3, —C(═O)R, —C(═O)OH, —NH2, —SH, —NHR, —NR2, —SR, —SO3H, —SO2R, —S(═O)R, —CN, —OH, —C(═O)OR, —C(═O)NR2, —NRC(═O)R, and —NRC(═O)—OR, wherein R is, independently, a hydrogen or C1-6alkyl.