PROCESS FOR PREPARING BICYCLIC COMPOUNDS

1 . A process for preparing compounds of formula (IA) starting from compounds of formula (I) by a coupling reaction catalysed by copper between compounds of formula (I) and a reactive derivative of the upper residue —NR″ 2 R″ 3

wherein

R is aryl or heteroaryl, each of which may be substituted by 1 to 4 groups selected from:

 halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, —C(O)R 5 , nitro, —NR 6 R 7 , cyano, and a group R 8 ;

R 1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C1-C6 alkoxy, halogen, NR 6 R 7 or cyano;

R 5 is C1-C4 alkyl, —OR 6 or —NR 6 R 7 ;

R 6 is hydrogen or C1-C6 alkyl;

R 7 is hydrogen or C1-C6 alkyl;

R 8 is a 5-6 membered heterocycle, which may be saturated or may contain one to three double bonds, and which may be substituted by 1 or more R 11 groups;

R 9 is C1-C6 alkyl that may be substituted by one or more groups selected from: C3-C7 cycloalkyl, C1-C6 alkoxy, haloC1-C6 alkoxy, hydroxyl and haloC1-C6 alkyl;

R 11 is C3-C7 cycloalkyl, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, or C(O)NR 6 R 7 ;

X is halogen;

R″ corresponds to R;

R″ 1 corresponds to R 1 ;

R 2 is hydrogen, C3-C7 cycloalkyl, or a group R 9 ;

R 3 is C3-C7 cycloalkyl or a group R 9 ; or

R 2 and R 3 together with N form a 5-14 membered heterocycle, which may be substituted by 1 to 3 R 10 groups;

R″ 4 is hydrogen;

R″ 5 corresponds to R 5 ;

R″ 6 corresponds to R 6 ;

R″ 7 corresponds to R 7 ;

R″ 8 corresponds to R 8 ;

R″ 9 corresponds to R 9 ;

R 10 is a group R 8 , C3-C7 cycloalkyl, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, C(O)NR 6 R 7 or phenyl which may be substituted by 1 to 4 R 11 groups; and

R″ 11 corresponds to R 11 .

2 . A process, according to claim 1 , for preparing the following compounds:

3-Methyl-4-[6-methyl-4-(3-thiazol-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl]-benzonitrile;

1-(2,4-Bis-trifluoromethyl-phenyl)-6-methyl-4-(3-thiazol-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine;

4-[6-Methyl-4-(3-thiazol-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl]-3-trifluoromethyl-benzonitrile;

6-Methyl-1-(2-methyl-4-trifluoromethoxy-phenyl)-4-(3-thiazol-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine;

1-(4-Methoxy-2-methyl-phenyl)-6-methyl-4-(3-thiazol-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine;

1-(2,4-Bis-trifluoromethyl-phenyl)-6-methyl-4-(3-morpholin-4-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine;

1-(2,4-Bis-trifluoromethyl-phenyl)-6-methyl-4-(3-pyridin-2-yl-pyrazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine;

4-[1,3′]Bipyrazolyl-1′-yl-1-(2,4-bis-trifluoromethyl-phenyl)-6-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine.

3 . A process for preparing compounds of formula (I) according to the following Scheme 1:

wherein R, R 1 , X are defined as in claim 1 , and Lg is a leaving group selected among the reactive derivatives of an alkylsulphonic acid;

step f stands for the formation of a reactive derivative of the hydroxy pyridine of compounds (VII); and

step g stands for nucleophilic displacement of the reactive derivative of compounds (VIII) to give the halogenated compounds (I).

4 . An intermediate compound of formula (VII)

wherein:

R is aryl or heteroaryl each of which may be substituted by 1 to 4 groups selected from:

 halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, —C(O)R 5 , nitro, —NR 6 R 7 , cyano, and a group R 8 ;

R 1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C1-C6 alkoxy, halogen, NR 6 R 7 or cyano;

R 5 is C1-C4 alkyl —OR 6 or —NR 6 R 7 ;

R 6 is hydrogen or C1-C6 alkyl;

R 7 is hydrogen or C1-C6 alkyl;

R 8 is a 5-6 membered heterocycle, which may be saturated or may contain one to three double bonds, and which may be substituted by 1 or more R 11 groups; and

R 11 is C3-C7 cycloalkyl, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, or C(O)NR 6 R 7 .

5 . A process for the preparation of compounds (IV) starting from compounds of formula (II) and comprising the following steps according to Scheme 2:

wherein R is defined as in claim 1 , Rg is a reactive group selected from: halogen and a reactive derivative of an alkylsulphonic acid;

step a stands for alkylation of the suitable aryl or heteroayl amine of formula (II) with a reactive derivative of butyrronitrile in presence of a base by heating; and

step b stands for the formation of the pyrrolidinone moiety of compounds (IV) which will form the cycle B present in the final compounds (I), by cyclisation of compounds (III), acid catalised and by heating to give the desired compounds (IV).

6 . A process for preparing compounds of formula (IVB) according to claim 3 in which step a and step b are performed continuously without isolating intermediate (III), according to the following Scheme 3

7 . An intermediate compound of formula (IVB)

wherein:

R is aryl or heteroaryl each of which may be substituted by 1 to 4 groups selected from:

 halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, —C(O)R 5 , nitro, —NR 6 R 7 , cyano, and a group R 8 ;

R 5 is C1-C4 alkyl, —OR 6 or —NR 6 R 7 ;

R 6 is hydrogen or C1-C6 alkyl;

R 7 is hydrogen or C1-C6 alkyl;

R 8 is a 5-6 membered heterocycle, which may be saturated or may contain one to three double bonds, and which may be substituted by 1 or more R 11 groups;

R 11 is C3-C7 cycloalkyl, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, or C(O)NR 6 R 7 ; and

Rg is a reactive group selected from: halogen and a reactive derivative of an alkylsulphonic acid.

8 . A process for the preparation of compounds (VII) starting from compounds of formula (IV) and comprising the following steps:

wherein R and R 1 , are defined as in claim 1 , and

step c stands for a Michael addition of compounds (IV) to a butynoate derivative by heating;

step d stands for cyclisation in basic conditions to give the aromatic compounds (VI); and

step e stands for salt formation by addition of the suitable acid to the compounds (VI).

9 . A process for preparing of compounds (VII), according to claim 8 , starting from compounds of formula (IV) in which compounds (IV) are replaced by compounds (IVB) according to the following Scheme 5:

and

step c′ stands for a basic treatment of compounds (IVB) with a suitable base.

10 . Compound of formula (IX) or a pharmaceutically acceptable salt thereof.

11 - 16 . (canceled)

17 . A pharmaceutical composition comprising the compound according to claim 10 or a pharmaceutically acceptable salt thereof in admixture with one or more physiologically acceptable carriers or excipients.

18 . A method for the treatment of a condition mediated by CRF (corticotropin-releasing factor), comprising administration of an effective amount of a compound according to claim 10 or a pharmaceutically acceptable salt thereof to a mammal in need of treatment thereof.

19 . A method, according to claim 17 , wherein the condition mediated by CRF is depression or anxiety.

20 . A method, according to claim 17 , wherein the condition mediated by CRF is IBS (irritable bowel disease) or IBD (inflammatory bowel disease.