Patent WO-2008012418-A1 (WO)
Title: N-(aminoheteroaryl)-1h-indole-2-carboxamide derivatives, preparation thereof and therapeutic use thereof
Inventor: DUBOIS LAURENT
IPC: A61P15/00
Filed: 2007-07-20
Abstract: The invention relates to compounds of general formula (I): in which X<SUB>1</SUB> is a hydrogen or halogen atom or a (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>3</SUB>)-alkylene, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkyl, cyano, C(O)NR<SUB>1</SUB>R<SUB>2</SUB>, nitro, (C<SUB>1</SUB>-C<SUB>6</SUB>)-thioalkyl, -S(O)-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, -S(O)<SUB>2</SUB>-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, SO<SUB>2</SUB>NR<SUB>1</SUB>R<SUB>2,</SUB> aryl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted; X<SUB>2</SUB> is a hydrogen or halogen atom or a (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>3</SUB>)-alkylene, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkyl, (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkoxyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene-O-, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkoxyl, cyano, C(O)NR<SUB>1</SUB>R<SUB>2</SUB>, (C<SUB>1</SUB>-C<SUB>6</SUB>)-thioalkyl, -S(O)-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, -S(O)<SUB>2</SUB>-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, SO<SUB>2</SUB>NR<SUB>1</SUB>R<SUB>2</SUB>, aryl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted; X<SUB>3</SUB> and X<SUB>4</SUB> are, independently of one another, a hydrogen or halogen atom or a (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>3</SUB>)-alkylene, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkyl, (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkoxyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene-O-, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkoxyl, cyano, C(O)NR<SUB>1</SUB>R<SUB>2</SUB>, nitro, NR<SUB>1</SUB>R<SUB>2</SUB>, (C<SUB>1</SUB>-C<SUB>6</SUB>)-thioalkyl, -S(O)-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, -S(O)<SUB>2</SUB>-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyl, SO<SUB>2</SUB>NR<SUB>1</SUB>R<SUB>2</SUB>, NR<SUB>3</SUB>COR<SUB>4</SUB>, NR<SUB>3</SUB>SO<SUB>2</SUB>R<SUB>5</SUB>, aryl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted; Z<SUB>1</SUB>, Z<SUB>2</SUB>, Z<SUB>3</SUB> and Z<SUB>4</SUB> are, independently of one another, a nitrogen atom or a C(R<SUB>6</SUB>) group; n is equal to 0, 1, 2 or 3; Y is an optionally substituted aryl or heteroaryl; Ra and Rb are, independently of one another, a hydrogen atom or a (C<SUB>1</SUB>-C<SUB>6</SUB>)<SUB>-</SUB>alkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>3</SUB>)-alkylene, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkyl, hydroxyl, (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkoxyl, (C<SUB>3</SUB>-C<SUB>7</SUB>)-cycloalkyl-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkylene-O-, (C<SUB>1</SUB>-C<SUB>6</SUB>)-fluoroalkoxyl, aryl or heteroaryl group, wherein Ra and Rb may be optionally substituted; in the form of a base or an addition salt with an acid, and also in the form of a hydrate or of a solvate. Process for the preparation thereof and therapeutic use.