IP Library › Granted Patent US 12,319,669
Granted Patent B2
US 12,319,669 · App. 18/477,050 · Granted Jun 3, 2025

GLP-1 receptor agonists and uses thereof

Inventors: Gary Erik Aspnes (Biberach an der Riss, DE); Scott W. Bagley (Voluntown, CT); John M. Curto (Mystic, CT); Matthew S. Dowling (Old Lyme, CT); David Edmonds (Basel, CH); Mark E. Flanagan (Gales Ferry, CT); Kentaro Futatsugi (Sharon, MA); David A. Griffith (Sudbury, MA); Kim Huard (Berkeley, CA); Gajendra Ingle (New Haven, CT); Wenhua Jiao (Salem, CT); Chris Limberakis (Pawcatuck, CT); Alan M. Mathiowetz (Waltham, MA); David W. Piotrowski (Waterford, CT); Roger B. Ruggeri (Waterford, CT)
Assignee: Pfizer Inc.
C07D401/14A61K31/4545A61K31/496A61P1/00A61P1/16A61P3/00A61P3/04A61P3/10A61P9/10A61P13/12A61P15/00A61P15/10A61P17/06A61P19/02A61P19/06A61P25/02A61P25/16A61P25/18A61P25/28A61P25/30A61P43/00C07D405/14C07D413/14C07D471/04C07D487/04
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Quick Facts
Patent No.
US 12,319,669
App. No.
18/477,050
Granted
Jun 3, 2025
Kind
B2
Abstract

Provided herein are 6-carboxylic acids of benzimidazoles and 4-aza-, 5-aza-, 7-aza- and 4,7-diaza-benzimidazoles as GLP-1R agonists, processes to make said compounds, and methods comprising administering said compounds to a mammal in need thereof.

Claims (21)

1. A method for treating a disease or disorder in a human comprising administering to the human a compound that is 2-[(4-{6-[(4-cyano-2-fluorophenyl)methoxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-{[(2S)-oxetan-2-yl]methyl}-1H-benzimidazole-6-carboxylic acid or 2-[(4-{6-[(4-cyano-2-fluorophenyl)methoxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-{[(2R)-oxetan-2-yl]methyl}-1H-benzimidazole-6-carboxylic acid, or a pharmaceutically acceptable salt thereof, wherein the disease or disorder is selected from the group consisting of Type 1 diabetes (T1D), Type 2 diabetes mellitus (T2DM), pre-diabetes, idiopathic T1D, latent autoimmune diabetes in adults (LADA), early-onset T2DM (EOD), youth-onset atypical diabetes (YOAD), maturity onset diabetes of the young (MODY), malnutrition-related diabetes, gestational diabetes, hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, a kidney disease, and diabetic retinopathy.

2. The method of claim 1 wherein the disease or disorder is T1D or idiopathic T1D.

3. The method of claim 1 wherein the disease or disorder is selected from the group consisting of T2DM, pre-diabetes, LADA, EOD, YOAD, MODY, malnutrition-related diabetes, gestational diabetes, diabetic neuropathy, diabetic nephropathy, and diabetic retinopathy.

4. The method of claim 1 wherein the disease or disorder is T2DM.

5. The method of claim 1 wherein the disease or disorder is selected from the group consisting of hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, and a kidney disease.

6. A method for treating a disease or disorder in a human comprising administering to the human a compound that is 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid, or a pharmaceutically acceptable salt thereof, wherein disease or disorder is selected from the group consisting of T1D, T2DM, pre-diabetes, idiopathic T1D, LADA, EOD, YOAD, MODY, malnutrition-related diabetes, gestational diabetes, hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, kidney disease, and diabetic retinopathy.

7. The method of claim 6 wherein the compound is 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid.

8. The method of claim 6 wherein the compound is a pharmaceutically acceptable salt of 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid.

9. The method of claim 6 wherein the compound is 2-amino-2-(hydroxymethyl)propane-1,3-diol salt (tris salt) of 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid.

10. The method of claim 6 wherein the disease or disorder is T1D or idiopathic T1D.

11. The method of claim 6 wherein the disease or disorder is selected from the group consisting of T2DM, pre-diabetes, LADA, EOD, YOAD, MODY, malnutrition-related diabetes, gestational diabetes, diabetic neuropathy, diabetic nephropathy, and diabetic retinopathy.

12. The method of claim 6 wherein the disease or disorder is T2DM.

13. The method of claim 6 wherein the disease or disorder is selected from the group consisting of hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, and a kidney disease.

14. The method of claim 8 wherein the disease or disorder is T1D or idiopathic T1D.

15. The method of claim 8 wherein the disease or disorder is selected from the group consisting of T2DM, pre-diabetes, LADA, EOD, YOAD, MODY, malnutrition-related diabetes, gestational diabetes, diabetic neuropathy, diabetic nephropathy, and diabetic retinopathy.

16. The method of claim 8 wherein the disease or disorder is T2DM.

17. The method of claim 8 wherein the disease or disorder is selected from the group consisting of hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, and a kidney disease.

18. The method of claim 9 wherein the disease or disorder is T1D or idiopathic T1D.

19. The method of claim 9 wherein the disease or disorder is selected from the group consisting of T2DM, pre-diabetes, LADA, EOD, YOAD, MODY, malnutrition-related diabetes, gestational diabetes, diabetic neuropathy, diabetic nephropathy, and diabetic retinopathy.

20. The method of claim 9 wherein the disease or disorder is T2DM.

21. The method of claim 9 wherein the disease or disorder is selected from the group consisting of hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, and a kidney disease.

Continuity (7)
Continuation 18049052 · Oct 24, 2022
Continuation 17085534 · Oct 30, 2020
Continuation 16861646 · Apr 29, 2020
Continuation 16220184 · Dec 14, 2018
Continuation 15839901 · Dec 13, 2017
Provisional Application 62435533 · Dec 16, 2016
Related Publication 20240034725A1 · Feb 1, 2024
References Cited (11)
US 10208019B2 · Aspnes et al. · 2019 [cited by applicant]
US 10669259B2 · Aspnes et al. · 2020 [cited by applicant]
US 10851081B2 · Aspnes et al. · 2020 [cited by applicant]
US 11512070B2 · Aspnes et al. · 2022 [cited by applicant]
US 20040127504A1 · Cowart et al. · 2004 [cited by applicant]
US 20080280933A1 · Efremov et al. · 2008 [cited by applicant]
US 20090264426A1 · Sakuraba et al. · 2009 [cited by applicant]
US 20130123237A1 · Anand et al. · 2013 [cited by applicant]
US 20180170908A1 · Aspnes et al. · 2018 [cited by applicant]
WO 2002074752 · 2002 [cited by applicant]
WO 2011143365 · 2011 [cited by applicant]