Back to results
US 2014/0235612 A1Published application
Azabenzimidazole Compounds
AssigneePfizer Inc.
InventorsThomas Allen Chappie, Patrick Robert Verhoest, Nandini Chaturbhai Patel, Matthew Merrill Hayward
Life of this patent
Estimating the term…
Abstract
The present invention is directed to compounds of formula I: or a pharmaceutically acceptable salt thereof, wherein the substituents are as defined herein.
Claims28
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 optionally 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;
- R6 and R7 are each represented by a substituent independently 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;
- wherein said (C1-C6)alkyl, (C3-C10)cycloalkyl, (C6-C10)aryl, and (5- to 10-membered)heteroaryl are 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 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;
- 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.
13 more elements
A compound of formula Ia:
- or a pharmaceutically acceptable salt thereof, wherein:
- b is represented by an integer selected from 0, 1, 2, or 3;
- each R2, if present, is represented by a substituent independently selected from the group consisting of fluoro, chloro, cyano, methyl, trifluoromethyl, methylthio, methoxy, and trifluoromethoxy;
- R6 and R7 are each independently selected from the group consisting of hydrogen, (C1-C6)alkyl, —(CH2)m—(C3-C10)cycloalkyl, and —(CH2)m-(5- to 10-membered)heteroaryl;
- wherein said (C1-C6)alkyl, (C3-C10)cycloalkyl, and (5- to 10-membered)heteroaryl are optionally substituted with one to three 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, hydroxy, and cyano;
- or R6 and R7 taken together with the nitrogen to which they are attached form a (4 to 6-membered)heterocycloalkyl, in which up to three carbon atoms of said heterocycloalkyl are optionally substituted 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,
- wherein R4 and R5 are each independently selected from the group consisting of hydrogen and (C1-C6)alkyl;
- and m is represented by an integer selected from 0, 1, or 2.
5 more elements
A method of treating a patient suffering from a disease or condition mediated by the PDE4B isoform, comprising administering to said patient in need of said treatment a therapeutically effective amount of a compound of formula I or a pharmaceutically acceptable salt thereof.
(canceled)
Dependencies are inferred from the claim text.