IP Library Granted Patent US 12,472,180
Granted Patent B2
US 12,472,180 · App. 17/904,537 · Granted Nov 18, 2025

Combinations for treatment of NAFLD/NASH and related diseases

Inventors: Neeta Balkrishan Amin (Cambridge, MA); Arthur James Bergman (Salem, CT); Roberto Arnaldo Calle (Marlborough, MA); William Paul Esler (Clinton, CT); Albert Myung Kim (Newton, MA); Jeffrey Allen Pfefferkorn (Acton, MA); Patrick Robert Verhoest (Newton, MA)
Assignee: Pfizer Inc.
A61K31/506A61K31/438A61P1/16A61P3/00C07B2200/13
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Quick Facts
Patent No.
US 12,472,180
App. No.
17/904,537
Granted
Nov 18, 2025
Kind
B2
Abstract

A method for treating fatty liver disease and related diseases or disorders with a therapeutically effective amount of a composition comprising from about 25 mg to about 1200 mg of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof, and from about 5 mg to about 40 mg of 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof.

Claims (23)

1 . A method for treating a disease or condition selected from fatty liver, nonalcoholic fatty liver disease, nonalcoholic steatohepatitis, nonalcoholic steatohepatitis with liver fibrosis, nonalcoholic steatohepatitis with cirrhosis, and nonalcoholic steatohepatitis with cirrhosis and with hepatocellular carcinoma or with a metabolic-related disease, the method comprising the steps of:

administering to a human in need thereof a therapeutically effective amount of a composition comprising from about 5 mg to about 1200 mg of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof, and from about 5 mg to about 60 mg of 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof.

2 . A method for treating a disease or condition selected from fatty liver; alcoholic fatty liver disease; alcoholic steatohepatitis; alcoholic steatohepatitis with liver fibrosis; alcoholic steatohepatitis with cirrhosis; and alcoholic steatohepatitis with cirrhosis and with hepatocellular carcinoma or with a metabolic-related disease, the method comprising the steps of:

administering to a human in need thereof a therapeutically effective amount of a composition comprising from about 5 mg to about 1200 mg of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof, and from about 5 mg to about 60 mg of 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof.

3 . A method for treating a cardiovascular disease or condition selected from atherosclerosis, stroke, myocardial infarction, aortic vascular disease, cerebral vascular disease, renal vascular disease, heart failure, atrial fibrillation, or coronary heart disease, the method comprising the steps of:

administering to a human in need thereof a therapeutically effective amount of a composition comprising from about 5 mg to about 1200 mg of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof, and from about 5 mg to about 60 mg of 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof.

4 . A method for treating a metabolic disease or condition selected from obesity, dyslipidemia, type 2 diabetes mellitus, glycemic control in patients with type 2 diabetes mellitus, conditions of impaired glucose tolerance (IGT), conditions of impaired fasting plasma glucose, metabolic syndrome, syndrome X, hyperglycemia, hyperinsulinemia, insulin resistance, or impaired glucose metabolism, the method comprising the steps of:

administering to a human in need thereof a therapeutically effective amount of a composition comprising from about 5 mg to about 1200 mg of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof, and from about 5 mg to about 60 mg of 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof.

5 . The method according to claim 1 , wherein the ratio of the of S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof to 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof is about 1:1, about 5:1, about 10:1, about 15:1, about 20:1, or about 30:1.

6 . The method according to claim 1 , wherein the therapeutically effective amount of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof is about 5 mg, about 10 mg, about 15 mg, about 20 mg, about 25 mg, about 50 mg, about 75 mg, about 100 mg, about 150 mg, about 200 mg, about 225 mg, about 300 mg, about 400 mg, about 450 mg, about 600 mg or about 1200 mg; and the therapeutically effective amount of the 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof is about 5 mg, about 10 mg, about 15 mg, about 20 mg, about 40 mg, about 50 mg, or about 60 mg.

7 . The method of claim 6 , wherein the therapeutically effective amount of (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide or a pharmaceutically acceptable salt thereof is about 300 mg.

8 . The method of claim 7 , wherein the therapeutically effective amount of the 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof is about 10 mg.

9 . The method of claim 7 , wherein the therapeutically effective amount of the 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof is about 15 mg.

10 . The method of claim 7 , wherein the therapeutically effective amount of the 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid or a pharmaceutically acceptable salt thereof is about 20 mg.

11 . The method according to claim 1 , wherein the composition is administered once a day.

12 . The method according to claim 1 , wherein the composition is administered twice a day.

13 . The method according to claim 1 , wherein the (S)-2-(5 ((3ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidine-5-carboxamide is a crystalline solid of structure:

or a pharmaceutically acceptable salt thereof.

14 . The method of claim 13 , wherein the crystalline solid has a powder x-ray diffraction pattern comprising 2-theta values of (CuKα radiation, wavelength of 1.54056 Å) 5.3±0.2, 7.7±0.2, and 15.4±0.2.

15 . The method of claim 13 , wherein the crystalline solid has a powder x-ray diffraction pattern comprising 2-theta values of (CuKα radiation, wavelength of 1.54056 Å) 6.5±0.2, 9.3±0.2, and 13.6±0.2.

16 . The method according to claim 1 , wherein the 4-(4-(1-Isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid is a crystalline solid of structure:

or a pharmaceutically acceptable salt thereof.

17 . The method of claim 16 , wherein the crystalline solid is 2-amino-2-(hydroxymethyl) propane-1,3-diol salt of 4-(4-(1-isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypyridin-2-yl)benzoic acid.

Assignments (1)
ASSIGNEE ADDRESS CORRECTION Recorded Mar 20, 2023
From: PFIZER INC.
To: PFIZER INC.
Reel/Frame 063119/0087 →
Continuity (2)
Provisional Application 62980664 · Feb 24, 2020
Related Publication 20230218616A1 · Jul 13, 2023
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