US 7,592,365 B2
Substituted pyrroles, compositions containing same, method for making same and use thereof
Baptiste Ronan, Clamart (France); Michel Tabart, La Norville (France); Catherine Souaille, Choisy le Roi (France); Fabrice Viviani, Louvres (France); Eric Bacque, Gif sur Yvette (France); Jean-Philippe Letallec, Paris (France); and Pascal Desmazeau, Tigery (France)
Assigned to Aventis Pharma S.A., Antony (France)
Filed on Aug. 01, 2007, as Appl. No. 11/832,208.
Application 11/832208 is a continuation of application No. PCT/FR2006/000286, filed on Feb. 08, 2006.
Claims priority of application No. 05 01354 (FR), filed on Feb. 10, 2005.
Prior Publication US 2008/0167368 A1, Jul. 10, 2008
Int. Cl. A61K 31/4025 (2006.01); A61K 31/166 (2006.01); C12N 9/99 (2006.01); C07C 233/57 (2006.01); C07D 207/34 (2006.01)
U.S. Cl. 514—423  [514/613; 435/184; 548/537; 564/189] 20 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
in which:
1) A and Ar are independently selected from the group consisting of: aryl, heteroaryl, heterocyclyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, cycloalkyl, and substituted cycloalkyl;
2) L is selected from the group consisting of: NH, CO—NH, NH—CO, NH—SO2, SO2NH, NH—CH2, CH2—NH, CH2—CO—NH, NH—CO—CH2, NH—CH2—CO, CO—CH2—NH, NH—CO—NH, NH—CS—NH, NH—CO—O, O—CO—NH, CH2—NH—CO —NH, NH—CO—NH—CH2, and NH—CO—CH2—CO—NH;
3) Ra is selected from the group consisting of H, alkyl and cycloalkyl;
4) R1 ) is selected from the group consisting of: H, R, COR, and SO2R, in which R is chosen from H, OR″4, NR″5R″6, (C1-C6)alkyl, cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl, in which R″4 is chosen from H, phenyl, and alkyl, and in which R″5and R″6 are independently selected from the group consisting of H, R OR″4, (C1-C6)alkyl, cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl or alternatively R″5 and R″6 are linked to each other to form a 5- to 8-membered saturated ring containing from 0 to 3 heteroatoms chosen from O, S and N;
5) R2 and R5 are independently selected from the group consisting of: H, halogen, R′2, CN, O(R′2), OC(O)(R′2), OC(O)N(R′2)(R′3), OS(O2)(R′2), N(R′2)(R′3), N═C(R′2)(R′3), N(R′2)C(O)(R′3), N(R′2)C(O)O(R′3), N(R′4)C(O)N(R′2)(R′3), N(R′4)C(S)N(R′2)(R′3), N(R′2)S(O2)(R′3), C(O)(R′2), C(O)O(R′2), C(O)N(R′2)(R′3), C(═N(R′3))(R′2), C(═N(OR′3))(R′2), S(R′2), S(O)(R′2), S(O2)(R′2), S(O2)O(R′2), and S(O2)N(R′2)(R′3); in which each R′2, R′3, R′4 is independently selected from the group consisting of H, alkyl, alkylene, alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted alkylene, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, and substituted heterocyclyl; in which, when R′2 and R′3 are each different from H and simultaneously present on R2 or on R3, they may be linked to each other to form a ring containing from 0 to 3 heteroatoms chosen from O, S and N;
or a pharmaceutically acceptable salt thereof.