6-Phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives
AssigneeN.V. Organon
InventorsJiaqiang Cai, Zoran Rankovic, Philip Jones, David Bennett, Iain Cumming, Jonathan Gillespie
Life of this patent
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Abstract
The present invention relates to 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives having the general Formula I wherein each of the substituents is given the definition as set forth in the specification and claims, pharmaceutical compositions comprising the same as well as to the use of these derivatives for the preparation of a medicament for the treatment of cathepsin S and/or cathepsin K related diseases such as osteoporosis, atherosclerosis, inflammation and immune disorders, such as rheumatoid arthritis, and chronic pain, such as neuropathic pain.
Claims19
A 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivative having the general Formula I
- wherein
- R is an optional ortho- or meta-substituent selected from halogen and (C1-4)-alkyloxy;
- R1 is (C1-4)alkyl, (C1-4)alkyloxy, halogen or CF3;
- R2 is H, (C1-4)alkyl, (C1-4)alkyloxy or halogen;
- R3 is H or (CH2)n—NR5R6;
- R4 is H or (C1-6)alkyl, optionally substituted with COOR7 or NR8R9;
- R5 and R6 are independently H, (C3-8)cycloalkyl, quinuclidin-3-yl, (C2-6)alkenyl or (C1-6)alkyl, optionally substituted with halogen, CF3, (C3-8)cycloalkyl, (C6-10)aryl, a 5- or 6-membered heteroaryl group, OH, (C1-6)alkyloxy, (C6-10)aryloxy, COOR10, CONR11,R12, NR13R14 or NR13SO2(C1-4)alkyl;
- or
- R5 and R6 together with the nitrogen to which they are bound form a 4-8 membered saturated heterocyclic ring, optionally further comprising 1 or more heteroatoms selected from O, S, SO2 and NR15, the ring being optionallly substituted with oxo, (C1-4)alkyl, (C3-8)cycloalkyl, NR16,R17 or CONR18,R19;
- R7 is H or (C1-4)alkyl;
- R8 and R9 are independently H, (C1-4)alkyl (optionally substituted with di(C1-4)-alkylamino) or (C3-8)cycloalkyl;
- or
- R8 and R9 form together with the nitrogen to which they are bound a 4-8-membered saturated heterocyclic ring, optionally further comprising a heteroatom selected from O and S;
- R10 is H or (C1-4)alkyl;
- R11 and R12 are independently H or (C1-4)alkyl;
- or
- R11 and R12 together with the nitrogen to which they are bound form a 4-8 membered saturated heterocyclic ring, optionally further comprising a heteroatom selected from O and S;
- R13 and R14 are independently H or (C1-4)alkyl;
- or
- R13 and R14 together with the nitrogen to which they are bound form a 4-8 membered saturated heterocyclic ring, optionally further comprising a heteroatom selected from O and S;
- R15 is H, (C1-4)alkyl (optionally substituted with OH, (C1-4)alkyloxy, di(C1-4)-alkylamino, or CONR21,R22), phenyl, pyridyl, COR20 or CONR21,R22;
- R16 and R17 are independently H or (C1-4)alkyl;
- or
- R16 and R17 together with the nitrogen to which they are bound form a 4-8 membered saturated heterocyclic ring, optionally further comprising a heteroatom selected from O and S;
- R18 and R19 are independently H or (C1-4)alkyl;
- R20 is H, (C1-4)alkyl, (C3-8)cycloalkyl, (C1-4)alkyloxy or furyl;
- R21 and R22 are independently H or (C1-4)alkyl;
- or
- R21 and R22 together with the nitrogen to which they are bound form a 4-8 membered saturated heterocyclic ring, optionally further comprising a heteroatom selected from O and S;
- and
- n is 0 or 1;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.