US2010249183A1PendingUtilityA1

Therapeutic use of n-(arylalkyl)-1h-pyrrolopyridine-2-carboxamide derivatives

Assignee: SANOFI AVENTISPriority: Jul 22, 2005Filed: Jun 15, 2010Published: Sep 30, 2010
Est. expiryJul 22, 2025(expired)· nominal 20-yr term from priority
A61P 31/12A61P 31/22A61P 9/10A61P 3/10A61P 43/00A61P 27/02A61P 25/24A61P 29/00A61P 25/00A61P 1/00A61P 1/18A61P 13/00A61P 1/04A61P 11/06A61P 15/08A61P 17/00A61P 17/04A61P 1/14A61P 13/02A61P 15/00A61P 13/10A61P 17/06A61P 13/12A61P 11/00C07D 471/04A61K 31/437
44
PatentIndex Score
0
Cited by
0
References
0
Claims

Abstract

The invention concerns therapeutic use of compounds of general formula (I), wherein n, the pyrrolopyridine ring, X 1 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and W are as defined herein.

Claims

exact text as granted — not AI-modified
1 . A method for treating pain, inflammation, urological disorder, gynecological disorder, gastrointestinal disorder, respiratory disorder, psoriasis, pruritus, dermal, ocular or mucous irritation, herpes or zona, comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         n is equal to 0, 1, 2 or 3; 
         the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; 
         X is chosen from a halogen atom and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5  or aryl group, the aryl being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; 
         Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom or a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5,  aryl-C 1 -C 6 -alkylene or aryl group, the aryl and the aryl-C 1 -C 6 -alkylene being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; and wherein
 R 1  and R 2  represent, independently of each other, a hydrogen atom or a 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 group; or R 1  and R 2  together forming, with the nitrogen atom that bears them, an azetidine, pyrrolidine, piperidine, azepine, morpholine, thiomorpholine, piperazine, homopiperazine group, this group being optionally substituted with a 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 group; 
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a C 1 -C 6 -alkyl, aryl-C 1 -C 6 -alkylene or aryl group; 
 R 5  represents a C 1 -C 6 -alkyl or aryl group; and 
 
         W represents a fused bicyclic group of formula: 
       
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein
 A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N;
 the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a 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, aryl-C 1 -C 6 -alkylene, oxo or thio group; and 
 the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein 
 
 R 6  represents a hydrogen atom or 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 1 -C 6 -alkylene or aryl group; 
 R 7  represents a hydrogen atom or a 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 1 -C 6 -alkylene, C 1 -C 6 -alkyl-C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-(CO)—, C 1 -C 6 -fluoroalkyl-C(O)—, C 3 -C 7 -cycloalkyl-C(O)—, aryl-C(O)—, aryl-C 1 -C 6 -alkylene-C(O)—, 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-S(O) 2 — or aryl-C 1 -C 6 -alkylene-S(O) 2 — or aryl group; 
 
         the sulfur atom(s) of the heterocycle A possibly being in oxidized form; 
         the nitrogen atom(s) of the heterocycle A possibly being in oxidized form; and 
         the nitrogen atom in position 4, 5, 6 or 7 of the pyrrolopyridine may be in oxidized form. 
       
     
     
         2 . The method according to  claim 1 , wherein in compound of formula (I) n is equal to 1 or 2. 
     
     
         3 . The method according to  claim 1 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a hydrogen or halogen atom and a C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, or aryl group; and
 wherein 
 R 1  and R 2  are hydrogen atoms. 
   
     
     
         4 . The method according to  claim 1 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a halogen atom, a C 1 -C 6 -fluoroalkyl or aryl group.   
     
     
         5 . The method according to  claim 1 , wherein in compound of formula (I) Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom. 
     
     
         6 . The method according to  claim 1 , wherein in compound of formula (I) W is chosen from indolinyl, indolyl, isoindolyl, isoindolinyl, benzofuranyl, dihydrobenzofuranyl, benzothiophenyl, dihydrobenzothiophenyl, benzoxazolyl, dihydrobenzoxazolinyl, isobenzofuranyl, dihydroisobenzofuranyl, benzimidazolyl, dihydrobenzimidazolyl, indazolyl, benzothiazolyl, isobenzothiazolyl, dihydroisobenzothiazolyl, benzotriazolyl, quinolyl, dihydroquinolyl, tetrahydroquinolyl, isoquinolyl, dihydroisoquinolyl, tetrahydroisoquinolyl, benzoxazinyl, dihydrobenzoxazinyl, benzothiazinyl, dihydrobenzothiazinyl, cinnolinyl, quinazolinyl, dihydroquinazolinyl, tetrahydroquinazolinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl, tetrahydrobenz[b]azepinyl, tetrahydrobenz[c]azepinyl, tetrahydrobenz[d]azepinyl, tetrahydrobenzo[b][1,4]diazepinyl, tetrahydrobenzo[e][1,4]diazepinyl, tetrahydrobenzo[b][1,4]oxazepinyl or tetrahydrobenzo[b][1,4]thiazepinyl groups;
 and wherein   the carbon or nitrogen atom(s) of said group W being optionally substituted as defined in the general formula (I) according to  claim 1 .   
     
     
         7 . The method according to  claim 1 , wherein in compound of formula (I) W represents a fused bicyclic group of formula: 
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein 
         A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N; 
         the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a C 1 -C 6 -alkyl or an oxo group; or 
         the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein
 R 6  represents a hydrogen atom; and 
 R 7  represents a hydrogen atom or a C 1 -C 6 -alkyl group. 
 
       
     
     
         8 . The method according to  claim 1 , wherein in compound of formula (I) W is chosen from indolyl, benzimidazolyl, tetrahydroquinolyl, quinolyl or benzothiazolyl. 
     
     
         9 . A method for treating depression in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         n is equal to 0, 1, 2 or 3; 
         the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; 
         X is chosen from a halogen atom and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5  or aryl group, the aryl being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; 
         Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom or a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5 , aryl-C 1 -C 6 -alkylene or aryl group, the aryl and the aryl-C 1 -C 6 -alkylene being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; and wherein
 R 1  and R 2  represent, independently of each other, a hydrogen atom or a 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 group; or R 1  and R 2  together forming, with the nitrogen atom that bears them, an azetidine, pyrrolidine, piperidine, azepine, morpholine, thiomorpholine, piperazine, homopiperazine group, this group being optionally substituted with a 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 group; 
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a C 1 -C 6 -alkyl, aryl-C 1 -C 6 -alkylene or aryl group; 
 R 5  represents a C 1 -C 6 -alkyl or aryl group; and 
 
         W represents a fused bicyclic group of formula: 
       
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein
 A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N;
 the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a 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, aryl-C 1 -C 6 -alkylene, oxo or thio group; and 
 the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein 
 
 R 6  represents a hydrogen atom or 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 1 -C 6 -alkylene or aryl group; 
 R 7  represents a hydrogen atom or a 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 1 -C 6 -alkylene, C 1 -C 6 -alkyl-C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-(CO)—, C 1 -C 6 -fluoroalkyl-C(O)—, C 3 -C 7 -cycloalkyl-C(O)—, aryl-C(O)—, aryl-C 1 -C 6 -alkylene-C(O)—, 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-S(O) 2 — or aryl-C 1 -C 6 -alkylene-S(O) 2 — or aryl group; 
 
         the sulfur atom(s) of the heterocycle A possibly being in oxidized form; 
         the nitrogen atom(s) of the heterocycle A possibly being in oxidized form; and 
         the nitrogen atom in position 4, 5, 6 or 7 of the pyrrolopyridine may be in oxidized form. 
       
     
     
         10 . The method according to  claim 9 , wherein in compound of formula (I) n is equal to 1 or 2. 
     
     
         11 . The method according to  claim 9 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a hydrogen or halogen atom and a C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 -C 1 -C 6 -alkyl, or aryl group; and
 wherein 
 R 1  and R 2  are hydrogen atoms. 
   
     
     
         12 . The method according to  claim 9 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a halogen atom, a C 1 -C 6 -fluoroalkyl or aryl group.   
     
     
         13 . The method according to  claim 9 , wherein in compound of formula (I) Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom. 
     
     
         14 . The method according to  claim 9 , wherein in compound of formula (I) W is chosen from indolinyl, indolyl, isoindolyl, isoindolinyl, benzofuranyl, dihydrobenzofuranyl, benzothiophenyl, dihydrobenzothiophenyl, benzoxazolyl, dihydrobenzoxazolinyl, isobenzofuranyl, dihydroisobenzofuranyl, benzimidazolyl, dihydrobenzimidazolyl, indazolyl, benzothiazolyl, isobenzothiazolyl, dihydroisobenzothiazolyl, benzotriazolyl, quinolyl, dihydroquinolyl, tetrahydroquinolyl, isoquinolyl, dihydroisoquinolyl, tetrahydroisoquinolyl, benzoxazinyl, dihydrobenzoxazinyl, benzothiazinyl, dihydrobenzothiazinyl, cinnolinyl, quinazolinyl, dihydroquinazolinyl, tetrahydroquinazolinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl, tetrahydrobenz[b]azepinyl, tetrahydrobenz[c]azepinyl, tetrahydrobenz[d]azepinyl, tetrahydrobenzo[b][1,4]diazepinyl, tetrahydrobenzo[e][1,4]diazepinyl, tetrahydrobenzo[b][1,4]oxazepinyl or tetrahydrobenzo[b][1,4]thiazepinyl groups;
 and wherein   the carbon or nitrogen atom(s) of said group W being optionally substituted as defined in the general formula (I) according to  claim 1 .   
     
     
         15 . The method according to  claim 9 , wherein in compound of formula (I) W represents a fused bicyclic group of formula: 
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein 
         A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N; 
         the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a C 1 -C 6 -alkyl or an oxo group; or 
         the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein
 R 6  represents a hydrogen atom; and 
 R 7  represents a hydrogen atom or a C 1 -C 6 -alkyl group. 
 
       
     
     
         16 . The method according to  claim 9 , wherein in compound of formula (I) W is chosen from indolyl, benzimidazolyl, tetrahydroquinolyl, quinolyl or benzothiazolyl. 
     
     
         17 . A method for treating diabetes in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         n is equal to 0, 1, 2 or 3; 
         the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; 
         X is chosen from a halogen atom and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5  or aryl group, the aryl being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; 
         Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom or a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, cyano, C(O)NR 1 R 2 , nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, SO 2 NR 1 R 2 , NR 3 COR 4 , NR 3 SO 2 R 5,  aryl-C 1 -C 6 -alkylene or aryl group, the aryl and the aryl-C 1 -C 6 -alkylene being optionally substituted with one or more substituents chosen from a halogen and a 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 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro or cyano group; and wherein
 R 1  and R 2  represent, independently of each other, a hydrogen atom or a 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 group; or R 1  and R 2  together forming, with the nitrogen atom that bears them, an azetidine, pyrrolidine, piperidine, azepine, morpholine, thiomorpholine, piperazine, homopiperazine group, this group being optionally substituted with a 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 group; 
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a C 1 -C 6 -alkyl, aryl-C 1 -C 6 -alkylene or aryl group; 
 R 5  represents a C 1 -C 6 -alkyl or aryl group; and 
 
         W represents a fused bicyclic group of formula: 
       
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein
 A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N;
 the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a 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, aryl-C 1 -C 6 -alkylene, oxo or thio group; and 
 the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein 
 
 R 6  represents a hydrogen atom or 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 1 -C 6 -alkylene or aryl group; 
 R 7  represents a hydrogen atom or a 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 1 -C 6 -alkylene, C 1 -C 6 -alkyl-C(O)—, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkylene-(CO)—, C 1 -C 6 -fluoroalkyl-C(O)—, C 3 -C 7 -cycloalkyl-C(O)—, aryl-C(O)—, aryl-C 1 -C 6 -alkylene-C(O)—, 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-S(O) 2 — or aryl-C 1 -C 6 -alkylene-S(O) 2 — or aryl group; 
 
         the sulfur atom(s) of the heterocycle A possibly being in oxidized form; 
         the nitrogen atom(s) of the heterocycle A possibly being in oxidized form; and 
         the nitrogen atom in position 4, 5, 6 or 7 of the pyrrolopyridine may be in oxidized form. 
       
     
     
         18 . The method according to  claim 17 , wherein in compound of formula (I) n is equal to 1 or 2. 
     
     
         19 . The method according to  claim 17 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a hydrogen or halogen atom and a C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxyl, C 1 -C 6 -fluoroalkoxyl, nitro, NR 1 R 2 , C 1 -C 6 -thioalkyl, —S(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, or aryl group; and
 wherein 
 R 1  and R 2  are hydrogen atoms. 
   
     
     
         20 . The method according to  claim 17 , wherein in compound of formula (I) the pyrrolopyridine nucleus is a pyrrolo[3,2-b]pyridine group, a pyrrolo[3,2-c]pyridine group, a pyrrolo[2,3-c]pyridine group or a pyrrolo[2,3-b]pyridine group; and
 X is chosen from a halogen atom, a C 1 -C 6 -fluoroalkyl or aryl group.   
     
     
         21 . The method according to  claim 17 , wherein in compound of formula (I) Z 1 , Z 2 , Z 3 , Z 4  and Z 5  represent, independently of each other, a hydrogen or halogen atom. 
     
     
         22 . The method according to  claim 17 , wherein in compound of formula (I) W is chosen from indolinyl, indolyl, isoindolyl, isoindolinyl, benzofuranyl, dihydrobenzofuranyl, benzothiophenyl, dihydrobenzothiophenyl, benzoxazolyl, dihydrobenzoxazolinyl, isobenzofuranyl, dihydroisobenzofuranyl, benzimidazolyl, dihydrobenzimidazolyl, indazolyl, benzothiazolyl, isobenzothiazolyl, dihydroisobenzothiazolyl, benzotriazolyl, quinolyl, dihydroquinolyl, tetrahydroquinolyl, isoquinolyl, dihydroisoquinolyl, tetrahydroisoquinolyl, benzoxazinyl, dihydrobenzoxazinyl, benzothiazinyl, dihydrobenzothiazinyl, cinnolinyl, quinazolinyl, dihydroquinazolinyl, tetrahydroquinazolinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl, tetrahydrobenz[b]azepinyl, tetrahydrobenz[b]azepinyl, tetrahydrobenz[b]azepinyl, tetrahydrobenzo[b][1,4]diazepinyl, tetrahydrobenzo[e][1,4]diazepinyl, tetrahydrobenzo[b][1,4]oxazepinyl or tetrahydrobenzo[b][1,4]thiazepinyl groups; and wherein the carbon or nitrogen atom(s) of said group W being optionally substituted as defined in the general formula (I) according to  claim 1 . 
     
     
         23 . The method according to  claim 17 , wherein in compound of formula (I) W represents a fused bicyclic group of formula: 
       
         
           
           
               
               
           
         
         bonded to the nitrogen atom via positions 1, 2, 3 or 4; wherein 
         A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N; 
         the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom and a C 1 -C 6 -alkyl or an oxo group; or 
         the nitrogen atom(s) of A being optionally substituted with R 6  when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R 7  in the other cases; wherein
 R 6  represents a hydrogen atom; and 
 R 7  represents a hydrogen atom or a C 1 -C 6 -alkyl group. 
 
       
     
     
         24 . The method according to  claim 17 , wherein in compound of formula (I) W is chosen from indolyl, benzimidazolyl, tetrahydroquinolyl, quinolyl or benzothiazolyl.

Join the waitlist — get patent alerts

Track US2010249183A1 — get alerts on status changes and closely related new filings.

We store only your email — no account needed. See our privacy policy.