IP Library › Granted Patent US 9,539,244
Granted Patent B2
US 9,539,244 · App. 14/824,971 · Granted Jan 10, 2017

FXR (NR1H4) binding and activity modulating compounds

Inventors: Olaf Kinzel (Heidelberg, DE); Christoph Steeneck (Dossenheim, DE); Claus Kremoser (Heidelberg, DE)
Assignee: GILEAD SCIENCES, INC.
A61K31/42A61K31/422A61K31/4439C07D261/08C07D413/12C07D413/14
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Quick Facts
Patent No.
US 9,539,244
App. No.
14/824,971
Granted
Jan 10, 2017
Kind
B2
Abstract

The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists of FXR. The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds and to a process for the synthesis of said compounds.

Claims (18)

1. A method for treatment of a disease mediated by FXR, wherein the disease is selected from the group consisting of chronic intrahepatic cholestatic disease; chronic extrahepatic cholestatic disease; liver fibrosis; obstructive inflammatory disorders of the liver; chronic inflammatory disorders of the liver; liver cirrhosis; liver steatosis; hepatitis: liver failure; liver ischemia; chemotherapy associated steatohepatitis (CASH); acute liver failure; inflammatory bowel disease; lipid and lipoprotein disorders; Type II Diabetes; Type I Diabetes, Non-Alcoholic Fatty Liver Disease (NAFLD); Non-Alcoholic Steatohepatitis (NASH); obesity; metabolic syndrome; dyslipidemia; acute myocardial infarction; acute stroke; thrombosis; atherosclerosis; a non-malignant hyperproliferative disorder; a malignant hyperproliferative disorder; hepatocellular carcinoma; colon adenoma; polyposis; colon adenocarcinoma; breast cancer; pancreatic adenocarcinoma; Barrett's esophagus; Primary Biliary Cirrhosis (PBC); and Primary Sclerosing Cholangitis (PSC), the method comprising administering to a patient in need thereof a compound according to the Formula (1).

2. The method according to claim 1 , wherein the disease is selected from the group consisting of chronic intrahepatic cholestatic disease; chronic extrahepatic cholestatic disease; liver fibrosis; obstructive inflammatory disorders of the liver; chronic inflammatory disorders of the liver; liver cirrhosis; liver steatosis; hepatitis; liver failure; liver ischemia; chemotherapy associated steatohepatitis (CASH); acute liver failure; and inflammatory bowel disease.

3. The method according to claim 1 , wherein the disease is selected from the group consisting of lipid and lipoprotein disorders; Type II Diabetes; Type I Diabetes, Non-Alcoholic Fatty Liver Disease (NAFLD); Non-Alcoholic Steatohepatitis (NASH); obesity; metabolic syndrome; dyslipidemia; acute myocardial infarction; acute stroke; thrombosis; and atherosclerosis.

4. The method according to claim 1 , wherein the disease is selected from the group consisting of a non-malignant hyperproliferative disorder; a malignant hyperproliferative disorder; hepatocellular carcinoma; colon adenoma; polyposis; colon adenocarcinoma; breast cancer; arcinoma; and Barrett's esophagus.

5. The method according to claim 1 , wherein the disease is Non-Alcoholic Steatohepatitis (NASH).

6. The method according to claim 1 , wherein R-A is of a formula selected from the group consisting of

7. The method according to claim 1 , wherein Q is

8. The method according to claim 1 , wherein Z is

9. The method according to claim 1 , comprising administering to a patient in need thereof a compound selected from the group consisting of

10. A method for treatment of a disease mediated by FXR, wherein the disease is selected from the group consisting of chronic intrahepatic cholestatic disease; chronic extrahepatic cholestatic disease; liver fibrosis; obstructive inflammatory disorders of the liver; chronic inflammatory disorders of the liver; liver cirrhosis; liver steatosis; hepatitis; liver failure; liver ischemia; chemotherapy associated steatohepatitis (CASH); acute liver failure; inflammatory bowel disease; lipid and lipoprotein disorders; Type II Diabetes; Type I Diabetes, Non-Alcoholic Fatty Liver Disease (NAFLD); Non-Alcoholic Steatohepatitis (NASH); obesity; metabolic syndrome; dyslipidemia; acute myocardial infarction; acute stroke; thrombosis; atherosclerosis; a non-malignant hyperproliferative disorder; a malignant hyperproliferative disorder; hepatocellular carcinoma; colon adenoma; polyposis; colon adenocarcinoma; breast cancer; pancreatic adenocarcinoma; Barrett's esophagus; Primary Biliary Cirrhosis (PBC); and Primary Sclerosing Cholangitis (PSC), the method comprising administering to a patient in need thereof a compound according to the Formula (2).

11. The method according to claim 10 , wherein the disease is selected from the group consisting of lipid and lipoprotein disorders; Type II Diabetes; Type I Diabetes, Non-Alcoholic Fatty Liver Disease (NAFLD); Non-Alcoholic Steatohepatitis (NASH); obesity; metabolic syndrome; dyslipidemia; acute myocardial infarction; acute stroke; thrombosis; and atherosclerosis.

12. The method according to claim 10 , wherein the disease is Non-Alcoholic Steatohepatitis (NASH).

13. A method for treatment of a disease mediated by FXR, the method comprising administering to a patient in need thereof a compound according to the Formula (3)

or a pharmaceutically acceptable salt thereof.

14. The method according to claim 13 , wherein the disease is selected from the group consisting of lipid and lipoprotein disorders; Type II Diabetes; Type I Diabetes, Non-Alcoholic Fatty Liver Disease (NAFLD); Non-Alcoholic Steatohepatitis (NASH); obesity; metabolic syndrome; dyslipidemia; acute myocardial infarction; acute stroke; thrombosis; and atherosclerosis.

15. The method according to claim 13 , wherein the disease is Non-Alcoholic Steatohepatitis (NASH).

16. The method according to claim 1 , wherein the chronic intrahepatic cholestatic disease is Primary Biliary Cirrhosis (PBC).

17. The method according to claim 1 , wherein the chronic intrahepatic cholestatic disease is Primary Sclerosing Cholangitis (PSC).

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2016
From: PHENEX PHARMACEUTICALS AG
To: GILEAD SCIENCES, INC.
Reel/Frame 040522/0081 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2016
From: KINZEL, OLAF; STEENECK, CHRISTOPH; KREMOSER, CLAUS
To: PHENEX PHARMACEUTICALS AG
Reel/Frame 040499/0791 →
Priority Claims (1)
EP 11005722 · Jul 13, 2011 · regional
Continuity (3)
Continuation 14232118
Provisional Application 61507153 · Jul 13, 2011
Related Publication 20150342930A1 · Dec 3, 2015