US Patent No. 9,120,788

AZABENZIMIDAZOLE COMPOUNDS


Patent No. 9,120,788
Issue Date September 01, 2015
Title Azabenzimidazole Compounds
Inventorship Thomas Allen Chappie, Carlisle, MA (US)
Patrick Robert Verhoest, Newton, MA (US)
Nandini Chaturbhai Patel, Waltham, MA (US)
Matthew Merrill Hayward, Old Lyme, CT (US)
Assignee Pfizer Inc., New York, NY (US)

Claim of US Patent No. 9,120,788

1. A compound of formula I:

or a pharmaceutically acceptable salt thereof, wherein:
R1 is represented by a substituent selected from the group consisting of (C3-C10)cycloalkyl, a (4- to 10-membered)heterocycloalkyl, (C6-C10)aryl, and a (5- to 10-membered) heteroaryl; wherein said (C3-C10)cycloalkyl, (C6-C10)aryl and (5- to 10-membered)heteroaryl are substituted with (R2)b; and said (4- to 10-membered)heterocycloalkyl is optionally substituted at one to five carbon atoms with a substituent independently
selected from the group consisting of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy, and cyano, and optionally substituted at each available nitrogen with (C1-C6)alkyl;

R2 is represented by a substituent independently selected from the group consisting of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio; —C(O)NR4R5, hydroxy, and cyano;

R3, if present, at each occurrence is represented by a substituent independently selected from the group consisting of halogen,
(C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy, and cyano;

R4 and R5 are each represented by a substituent independently selected from the group consisting of hydrogen, (C1-C6)alkyl, and (C3-C6)cycloalkyl;

one of R6 and R7 is represented by a substituent selected from the group consisting of hydrogen, (C1-C6)alkyl, —(CH2)m—(C3-C10)cycloalkyl, —(CH2)m-(4- to 10-membered)-heterocycloalkyl, —(CH2)m—(C6-C10)aryl, and —(CH2)m-(5- to 10-membered)heteroaryl and the other is represented by a substituent selected from the group consisting of (C1-C6)alkyl, —(CH2)m—(C3-C10)cycloalkyl, —(CH2)m-(4- to 10-membered)-heterocycloalkyl, —(CH2)m—(C6-C10)aryl, and —(CH2)m-(5- to 10-membered)heteroaryl; wherein:

i) said R6 and R7 (C1-C6)alkyl substituent is optionally substituted with one to five substituents independently selected from the group consisting
of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, and cyano;

ii) said R6 and R7 (C3-C10)cycloalkyl substituent is optionally substituted with one to five substituents independently selected from the group consisting
of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy and cyano;

iii) said R6 and R7 (C6-C10)aryl substituent is optionally substituted with one to five substituents independently selected from the group consisting
of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy and cyano;

iv) said R6 and R7 (5- to 10-membered)heteroaryl substituent is optionally substituted with one to five substituents independently selected from
the group consisting of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy, and cyano; and

v) said R6 and R7 (4- to 10-membered)heterocycloalkyl substituent is optionally substituted at one to five carbon atoms with a substituent independently
selected from the group consisting of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy, and cyano, and optionally substituted at each available nitrogen with (C1-C6)alkyl; or R6 and R7 taken together with the nitrogen to which they are attached form a (4- to 10-membered)heterocycloalkyl, wherein said (4- to
10-membered) heterocycloalkyl is optionally substituted at one to five carbon atoms with a substituent independently selected
from the group consisting of halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C1-C6)alkylthio, —C(O)NR4R5, hydroxy, and cyano;

a is represented by an integer selected from 0, 1, 2 or 3;
b is represented by an integer selected from 0, 1, 2, 3, 4 or 5; and
m is represented by an integer selected from 0, 1, 2 or 3.