IP Library › Granted Patent US 11,976,064
Granted Patent B2
US 11,976,064 · App. 17/738,074 · Granted May 7, 2024

Toll-like receptor agonists

Inventors: Omar Ahmad (Cambridge, MA); Andrew Fensome (Harvard, MA); Erik Alphie LaChapelle (Uncasville, CT); Ethan Lawrence Fisher (Chester, CT); Rayomand J. Unwalla (Bedford, MA); Jun Xiao (East Lyme, CT); Lei Zhang (Auburndale, MA)
Assignee: Pfizer Inc.
C07D471/04A61K31/437
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Quick Facts
Patent No.
US 11,976,064
App. No.
17/738,074
Granted
May 7, 2024
Kind
B2
Abstract

The present invention relates to imidazo-pyridinyl compounds, or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer, in a subject.

Claims (34)

1. A method for the treatment of cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of:

2-((4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-(ethoxymethyl)-7,8-dihydrocyclopenta[b]imidazo[4,5-d]pyridin-1(6H)-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

3-(4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)-2-(methoxymethyl)-2-methylpropan-1-ol;

(R)-3-(4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)-2-(methoxymethyl)-2-methylpropan-1-ol;

(S)-3-(4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)-2-(methoxymethyl)-2-methylpropan-1-ol;

2-((4-amino-6,7-dimethyl-2-(2,2,2-trifluoroethyl)-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-ethylpropane-1,3-diol;

2-((4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-methylpropane-1,3-diol; and

2-((4-amino-2-pentyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

or a pharmaceutically acceptable salt thereof,

wherein the cancer is basal cell carcinomas, ovarian cancer, melanoma, non-muscular invasive bladder cancer, breast cancer, or head and neck cancer.

2. The method of claim 1 , wherein the cancer is non-muscular invasive bladder cancer.

3. The method of claim 1 , wherein the compound is 2-((4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-methylpropane-1,3-diol, or a pharmaceutically acceptable salt thereof.

4. The method of claim 3 , wherein the cancer is non-muscular invasive bladder cancer.

5. The method of claim 1 , wherein the compound is 2-((4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)methyl)-2-methylpropane-1,3-diol.

6. The method of claim 5 , wherein the cancer is non-muscular invasive bladder cancer.

7. The method of claim 1 , wherein the compound is administered with at least one additional therapeutic agent.

8. A method for the treatment of cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of:

2-((4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-butyl-7,8-dihydrocyclopenta[b]imidazo[4,5-d]pyridin-1(6H)-yl)methyl)-2-methylpropane-1,3-diol;

2-((4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol; and

2-((4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol;

or a pharmaceutically acceptable salt thereof,

wherein the cancer is basal cell carcinomas, ovarian cancer, melanoma, non-muscular invasive bladder cancer, breast cancer, or head and neck cancer.

9. The method of claim 8 , wherein the cancer is non-muscular invasive bladder cancer.

10. The method of claim 8 , wherein the compound is administered with at least one additional therapeutic agent.

11. The method of claim 1 , wherein the compound is 2-((4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol, or a pharmaceutically acceptable salt thereof.

12. The method of claim 1 , wherein the compound is 2-((4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol.

13. The method of claim 1 , wherein the compound is 2-((4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol, or a pharmaceutically acceptable salt thereof.

14. The method of claim 1 , wherein the compound is 2-((4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl)-2-methylpropane-1,3-diol.

Assignments (1)
ASSIGNEE ADDRESS CORRECTION Recorded Mar 20, 2023
From: PFIZER INC.
To: PFIZER INC.
Reel/Frame 063119/0087 →