US 12,378,230 B2
GLP-1 receptor agonists and uses thereof
Gary Erik Aspnes, Biberach an der Riss (DE); Scott W. Bagley, Voluntown, CT (US); John M. Curto, Mystic, CT (US); David James Edmonds, Riehen (CH); Mark E. Flanagan, Gales Ferry, CT (US); Kentaro Futatsugi, Sharon, MA (US); David A. Griffith, Sudbury, MA (US); Kim Huard, Berkeley, CA (US); Yajing Lian, Waterford, CT (US); Chris Limberakis, Pawcatuck, CT (US); Allyn T. Londregan, Barrington, RI (US); Alan M. Mathiowetz, Waltham, MA (US); David W. Piotrowski, Waterford, CT (US); and Roger B. Ruggeri, Waterford, CT (US)
Assigned to Pfizer Inc., New York, NY (US)
Filed by Pfizer Inc., New York, NY (US)
Filed on Oct. 9, 2023, as Appl. No. 18/483,311.
Application 17/171,385 is a division of application No. 16/436,311, filed on Jun. 10, 2019, granted, now 10,934,279, issued on Mar. 2, 2021.
Application 18/483,311 is a continuation of application No. 17/171,385, filed on Feb. 9, 2021, abandoned.
Claims priority of provisional application 62/851,206, filed on May 22, 2019.
Claims priority of provisional application 62/846,944, filed on May 13, 2019.
Claims priority of provisional application 62/684,696, filed on Jun. 13, 2018.
Prior Publication US 2024/0059679 A1, Feb. 22, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/12 (2006.01); C07C 53/06 (2006.01); C07C 53/10 (2006.01); C07C 215/40 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 405/12 (2013.01) [C07C 53/06 (2013.01); C07C 53/10 (2013.01); C07C 215/40 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 471/04 (2013.01); C07B 2200/13 (2013.01)] 20 Claims
 
1. A method for treating a disease or disorder in a human comprising administering to the human a compound, wherein the disease or disorder is selected from the group consisting of Type 2 diabetes mellitus (T2DM), pre-diabetes, 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, arthritis, osteoporosis, Parkinson's Disease, Alzheimer's Disease, addiction, addiction to alcohol abuse, addiction to drug abuse, sleep apnea, hyperglycemia, insulin resistance, hepatic insulin resistance, impaired glucose tolerance, diabetic neuropathy, diabetic nephropathy, kidney disease, diabetic retinopathy, adipocyte dysfunction, visceral adipose deposition, obesity, eating disorders, weight gain from use of other agents, excessive sugar craving, dyslipidemia, hyperinsulinemia, nonalcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), fibrosis, NASH with fibrosis, cirrhosis, hepatocellular carcinoma, and metabolic syndrome; and wherein the compound is
2-({4-[2-(4-chloro-2-fluorophenyl)-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[2-(4-chloro-2-fluorophenyl)-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-7-fluoro-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[2-(4-chloro-2-fluorophenyl)-2-methyl-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[2-(4-chloro-2-fluorophenyl)-7-fluoro-2-methyl-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[(2S)-2-(4-chloro-2-fluorophenyl)-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[(2S)-2-(4-chloro-2-fluorophenyl)-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-7-fluoro-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid;
2-({4-[(2S)-2-(4-chloro-2-fluorophenyl)-2-methyl-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid; or
2-({4-[(2S)-2-(4-chloro-2-fluorophenyl)-2-methyl-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-7-fluoro-1-[(2S)-oxetan-2-ylmethyl]-1H-benzimidazole-6-carboxylic acid,
or a pharmaceutically acceptable salt thereof.