IP Library Granted Patent US 8,354,425
Granted Patent B2
US 8,354,425 · App. 12/840,659 · Granted Jan 15, 2013

Azabicyclic carboxamide derivatives, preparation thereof and therapeutic use thereof

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Quick Facts
Patent No.
US 8,354,425
App. No.
12/840,659
Granted
Jan 15, 2013
Kind
B2
Abstract

The disclosure relates to compounds of formula (I): wherein X 1 , X 2 , X 3 , X 4 , Z 1 , Z 2 , Z 3 , Z 4 , Ra, Rb, n, Y, and W are as defined in the disclosure, or a salt thereof, or a hydrate or solvate thereof, and to processes for the preparation of these compounds and the therapeutic use thereof.

Claims (126)

1. A compound of formula (I):

wherein:

X 1 , X 2 , X 3 and X 4 represent, independently of each other, a nitrogen atom or a group C—R 1 ;

wherein when one from among X 1 , X 2 , X 3 and X 4 represents a nitrogen atom, the others correspond to a group C—R 1 ;

Z 1 , Z 2 , Z 3 and Z 4 represent, independently of each other, a nitrogen atom, a carbon atom or a group C—R 2 ,

wherein at least one from among Z 1 , Z 2 , Z 3 and Z 4 corresponds to a nitrogen atom and one from among Z 1 , Z 2 , Z 3 and Z 4 , corresponding to a carbon atom, being bonded to the nitrogen atom of the amide or of the thioamide of formula (I);

Ra and Rb form, together with the carbon atoms that bear them, a 5-membered ring, this ring comprising a nitrogen atom and carbon atoms, this ring being partially saturated or unsaturated and being optionally substituted with one or more substituents R 3 ;

W represents an oxygen or sulfur atom;

n is equal to 0, 1, 2 or 3;

Y represents an aryl or a heteroaryl optionally substituted with one or more groups chosen from a halogen atom, a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 6 -alkylene-O—, C 1 -C 6 -fluoroalkoxy, cyano, C(O)NR 4 R 5 , nitro, NR 4 R 5 , C 1 -C 6 -thioalkyl, thiol, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 4 R 5 , NR 6 C(O)R 7 , NR 6 SO 2 R 8 , C(O)NR 4 R 5 , OC(O)NR 4 R 5 , —Si—(C 1 -C 6 -alkyl) 3 , —SF 5 , aryl-C 1 -C 5 -alkylene or aryl, heteroaryl-C 1 -C 5 -alkylene or heteroaryl; the groups C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 6 -alkylene-O— being optionally substituted with a hydroxyl group, C 1 -C 6 -alkoxy and NR 4 R 5 , the aryl and heteroaryl groups being optionally substituted with one or more substituents R 9 , which may be identical to or different from each other;

R 1 is chosen from a hydrogen atom, a halogen atom, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, aryloxy-C 1 -C 6 -alkyl, heteroaryloxy-C 1 -C 6 -alkyl, aryl-C 1 -C 3 -alkylenoxy-C 1 -C 6 -alkyl, heteroaryl -C 1 -C 3 -alkylenoxy-C 1 -C 6 -alkyl, arylthio-C 1 -C 6 -alkyl, heteroarylthio-C 1 -C 6 -alkyl, aryl-C 1 -C 3 -alkylene-thio-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 3 -alkylene-thio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, C 1 -C 6 -fluoroalkoxy, cyano, C(O)NR 4 R 5 , nitro, NR 4 R 5 , C 1 -C 6 -thioalkyl, C 3 -C 7 -cycloalkylthio, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-thio, —S(O)—C 1 -C 6 -alkyl, —S(O)—C 3 -C 7 -cycloalkyl, —S(O)—C 1 -C 3 -alkylene-C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl-S(O) 2 —, C 1 -C 6 -fluoroalkyl-S(O) 2 —, C 3 -C 7 -cycloalkyl-S(O) 2 —, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-S(O) 2 —, SO 2 NR 4 R 5 , —Si—(C 1 -C 6 -alkyl) 3 , —SF 5 , NR 6 C(O)R 7 , NR 6 SO 2 R 8 , C(O)NR 4 R 5 , OC(O)NR 4 R 5 , aryl, heteroaryl, aryl-C 1 -C 5 -alkylene, heteroaryl-C 1 -C 5 -alkylene, aryloxy, arylthio, heteroaryloxy and heteroarylthio; the heteroaryl or aryl groups being optionally substituted with one or more substituents R 9 , which may be identical to or different from each other;

R 2 represents a hydrogen atom, a halogen atom or a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-O—, hydroxyl, thiol or C 1 -C 6 -fluoroalkoxy;

R 3 represents, when it is borne by a carbon atom, a hydrogen atom, a hydroxyl group, thiol, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl -C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl -C 1 -C 3 -alkylenoxy, C 1 -C 6 -alkoxy-C 1 -C 3 -alkylene, C 3 -C 7 -cycloalkyloxy-C 1 -C 3 -alkylene, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy-C 1 -C 3 -alkylene, C(O)NR 4 R 5 , C(O)O—C 1 -C 6 -alkyl, CO 2 H, or an oxo or thio group; the groups C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, C 1 -C 6 -alkoxy-C 1 -C 3 -alkylene, C 3 -C 7 -cycloalkyloxy-C 1 -C 3 -alkylene, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy-C 1 -C 3 -alkylene optionally being substituted with a hydroxyl group, C 1 -C 6 -alkoxy or NR 4 R 5 ;

or

R 3 represents, when it is borne by a nitrogen atom, a hydrogen atom or a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, aryl-C(O)—, C 1 -C 6 -alkyl-C(O)—, C 3 -C 7 -cycloalkyl-C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-C(O)—, C 1 -C 6 -fluoroalkyl-C(O)—, aryl-S(O), C 1 -C 6 -alkyl-S(O)—, C 1 -C 6 -fluoroalkyl-S(O)—, aryl-S(O) 2 —, C 1 -C 6 -alkyl-S(O) 2 —, C 1 -C 6 -fluoroalkyl-S(O) 2 —, C 3 -C 7 -cycloalkyl-S(O) 2 —, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-S(O) 2 —, C 1 -C 6 -alkyl-O—C(O)—, aryl-C 1 -C 3 -alkyl-O—C(O)—, C 3 -C 7 -cycloalkyl-O—C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-O—C(O)—, C 1 -C 6 -fluoroalkyl-O—C(O)—, aryl-O—C(O)—, heteroaryl-O—C(O)—, heteroaryl or aryl; the heteroaryl and aryl groups being optionally substituted with one or more substituents R 9 ; the groups C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, optionally being substituted with a hydroxyl group, C 1 -C 6 -alkoxy or NR 4 R 5 ;

R 4 and R 5 represent, independently of each other, a hydrogen atom or a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, aryl-C 1 -C 5 -alkylene or aryl, or R 4 and R 5 together form, with the nitrogen atom that bears them, an azetidine, pyrrolidine, piperidine, azepine, morpholine, thiomorpholine, piperazine or homopiperazine group; the group NR 4 R 5 being optionally substituted with a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, aryl-C 1 -C 6 -alkylene, aryl, heteroaryl, aryl-S(O) 2 —, C 1 -C 6 -alkyl-S(O) 2 —, C 1 -C 6 -fluoroalkyl-S(O) 2 , C 3 -C 7 -cycloalkyl-S(O) 2 —, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-S(O) 2 —, aryl -C(O)—, C 1 -C 6 -alkyl-C(O)—, C 3 -C 7 -cycloalkyl-C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-C(O)—, C 1 -C 6 -fluoroalkyl-C(O)—, hydroxyl, C 1 -C 6 -alkyloxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, C 1 -C 6 -fluoroalkyl, aryloxy-C 1 -C 6 -alkylene, aryloxy, heteroaryloxy-C 1 -C 6 -alkylene or heteroaryloxy;

R 6 and R 7 represent, independently of each other, a hydrogen atom or a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, aryl-C 1 -C 6 -alkylene or aryl; the aryl group being optionally substituted with one or more substituents chosen from a halogen atom and a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, C 1 -C 6 -fluoroalkoxy, nitro and cyano;

or R 6 and R 7 together form a 4- to 7-membered lactam comprising the nitrogen atom and the C(O) group that bear them;

R 8 represents a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, aryl-C 1 -C 6 -alkylene or aryl; the aryl group being optionally substituted with one or more substituents chosen from a halogen atom, a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, C 1 -C 6 -fluoroalkoxy, nitro or cyano;

or R 6 and R 8 together form a 4- to 7-membered sultam comprising the nitrogen atom and the S(O) 2 group that bear them; and

R 9 represents a halogen atom, a group C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylenoxy, or C 1 -C 6 -fluoroalkoxy; these groups being optionally substituted with a group OH, C 1 -C 6 -alkoxy or NR 4 R 5 ; or alternatively R 9 represents a nitro group, cyano or NR 4 R 5 ;

the sulfur atom(s) of the compound of formula (I) optionally being in oxidized form;

the nitrogen atom(s) of the compound of formula (I) optionally being in oxidized form;

or an acid-addition salt thereof.

2. The compound of formula (I) according to claim 1 , wherein:

X 1 , X 2 , X 3 and X 4 represent, independently of each other, a group C—R 1 ; R 1 is as defined in formula (I) according to claim 1 ;

or an acid-addition salt thereof.

3. The compound of formula (I) according to claim 1 , wherein:

among X 1 , X 2 , X 3 and X 4 , one from among X 3 and X 4 represents a nitrogen atom, and the others represent, independently of each other, a group C—R 1 ; R 1 being as defined in formula (I) according to claim 1 ;

or an acid-addition salt thereof.

4. The compound of formula (I) according to claim 1 , wherein:

R 1 is chosen from a hydrogen atom, a halogen atom, a group C 1 -C 6 -fluoroalkyl and —Si(C 1 -C 6 -alkyl) 3 ,

or an acid-addition salt thereof.

5. The compound of formula (I) according to claim 1 , wherein n is equal to 1;

or an acid-addition salt thereof.

6. The compound of formula (I) according to claim 1 , wherein:

Y represents a phenyl, optionally substituted with one or more groups chosen from a halogen atom and a group C 1 -C 6 -alkyl or C 1 -C 6 -fluoroalkyl; or alternatively Y represents a pyridyl or a thiazolyl;

or an acid-addition salt thereof.

7. The compound of formula (I) according to claim 1 , wherein:

W represents an oxygen atom;

or an acid-addition salt thereof.

8. The compound of formula (I) according to claim 1 , wherein:

the group:

is chosen from the groups:

one from among Z 1 , Z 2 , Z 3 and Z 4 corresponding to a nitrogen atom and optionally being in oxidized form;

these groups being optionally substituted with R 2 and R 3 as defined in formula (I) according to claim 1 ;

R 2 represents a hydrogen atom;

R 3 represents, when it is borne by a carbon atom, a hydrogen atom or an oxo group;

R 3 represents, when it is borne by a nitrogen atom, a hydrogen atom or a group C 1 -C 6 -alkyl or C 1 -C 6 -alkyl-C(O)—;

or an acid-addition salt thereof.

9. The compound of formula (I) according to claim 1 , wherein:

the group:

is chosen from the groups:

one from among Z 1 , Z 2 , Z 3 and Z 4 corresponding to a nitrogen atom and optionally being in oxidized form;

these groups being optionally substituted with R 2 and R 3 as defined in the formula (I);

R 2 represents a hydrogen atom;

R 3 represents, when it is borne by a carbon atom, a hydrogen atom or an oxo group;

R 3 represents, when it is borne by a nitrogen atom, a hydrogen atom or a group C 1 -C 6 -alkyl or C 1 -C 6 -alkyl-C(O)—;

or an acid-addition salt thereof.

10. The compound of formula (I) according to claim 1 , wherein:

either X 1 , X 2 , X 3 and X 4 represent, independently of each other, a group C—R 1 ; or,

among X 1 , X 2 , X 3 and X 4 , one from among X 3 and X 4 represents a nitrogen atom, and the others represent, independently of each other, a group C—R 1 ;

R 1 is chosen from a hydrogen atom, a halogen atom and a group C 1 -C 6 -fluoroalkyl or —Si(C 1 -C 6 -alkyl) 3 ;

n is equal to 1;

Y represents a phenyl, optionally substituted with one or more groups chosen from a halogen atom, a group C 1 -C 6 -alkyl or C 1 -C 6 -fluoroalkyl; or alternatively Y represents a pyridyl or a thiazolyl;

W represents an oxygen atom;

the group:

is chosen from the groups:

one from among Z 1 , Z 2 , Z 3 and Z 4 corresponding to a nitrogen atom and optionally being in oxidized form;

these groups being optionally substituted with R 2 and R 3 as defined in formula (I) according to claim 1 ;

R 2 represents a hydrogen atom;

R 3 represents, when it is borne by a carbon atom, a hydrogen atom or an oxo group;

R 3 represents, when it is borne by a nitrogen atom, a hydrogen atom or a group C 1 -C 6 -alkyl or C 1 -C 6 -alkyl-C(O)—;

or an acid-addition salt thereof.

11. A compound selected from the group consisting of:

N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide;

N-(2,3-dihydro-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide;

N-(1H-pyrrolo[3,2-b]pyrid-6-yl)-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-fluoro-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trimethylsilyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trimethylsilyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-c]pyrid-5-yl)-5-fluoro-1-[(3-fluorophenyl]methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(7-Oxy-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(1-Methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[[(3-trifluoromethyl)phenyl]-methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-6-trifluoromethyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trimethylsilyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-methylphenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-6-trimethylsilyl-1-[(3-methyl phenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trifluoromethyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-fluoro-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(pyrid-3-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trimethylsilyl-1-[(thiazol-2-yl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trimethylsilyl-1-[(thiazol-2-yl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-fluoro-1-[(thiazol-2-yl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trifluoromethyl-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-trimethylsilyl-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trimethylsilyl-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-6-fluoro-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(pyrid-4-yl)methyl)]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide;

N-(2-Oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide;

N-(1-Methyl-1H-pyrrolo[2,3-b]pyrid-5-yl)-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide;

N-(1H-pyrrolo[2,3-b]pyrid-5-yl)-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide;

N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-fluoro-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide; and

N-(1-Methyl-1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(pyrid-4-yl)methyl)]-1H-indole-2-carboxamide;

or an acid-addition salt thereof.

12. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 , or a pharmaceutically acceptable salt thereof; in combination with at least one pharmaceutically acceptable excipient.

13. A pharmaceutical composition comprising a compound of formula (I) according to claim 8 , or a pharmaceutically acceptable salt thereof; in combination with at least one pharmaceutically acceptable excipient.

14. A pharmaceutical composition comprising a compound of formula (I) according to claim 11 , or a pharmaceutically acceptable salt thereof; in combination with at least one pharmaceutically acceptable excipient.

Assignments (2)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2011
From: DUBOIS, LAURENT; EVANNO, YANNICK; MACHNIK, DAVID; MALANDA, ANDRE
To: SANOFI-AVENTIS
Reel/Frame 025924/0273 →