IP Library Granted Patent US 9,346,825
Granted Patent B2
US 9,346,825 · App. 14/480,202 · Granted May 24, 2016

Fused bicyclic oxazolidinone CETP inhibitor

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Quick Facts
Patent No.
US 9,346,825
App. No.
14/480,202
Granted
May 24, 2016
Kind
B2
Abstract

Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis.

Claims (36)

1. A method of treating a disease or condition which is hypercholesterolemia or familial-hypercholesterolemia in a patient in need of such treatment comprising the administration of a therapeutically effective amount of a compound having Formula Ia,

or a pharmaceutically acceptable salt thereof;

wherein the dashed line in the ring in Formula Ia is an optional double bond when x is 0;

wherein R 1 is CF 3 , F, or —N(CH 3 ) 2 ;

R 5 is H or CH 3 ;

D 1 is N or CR 2 , wherein R 2 is H or —CH(CH 3 ) 2 ;

D 2 is N or CR 3 , wherein R 3 is H or CH 3 ;

D 3 is N or CR 4 , wherein R 4 is H or CH 3 ;

A 1 is phenyl, pyridyl, thienyl, furyl, cyclohexenyl, or cyclopentenyl,

wherein A 1 is optionally substituted with 1-3 groups which are each independently F, Cl, —OCH 3 , isopropyl, —CN, —CH 3 , or CF 3 , and optionally one substituent group Z;

Z is A 3 , —CH 2 CH 2 CO 2 R 8 , —CH 2 CH 2 -(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl), or —CH 2 CH 2 -(5-amino-1,3,4-oxadiazol-2-yl);

R 8 is H or —CH 3 ,

A 3 is phenyl, cyclobutyl, or pyridyl, wherein A 3 is optionally substituted with 1 group —CH 3 , and is optionally substituted with 1 group -(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl), -(5-amino-1,3,4-oxadiazol-2-yl), or —CO 2 R in which R is H or —CH 3 ;

A 2 is phenyl, which is substituted with 1-2 substituent groups which are each independently CF 3 , CH 3 , F, or Cl; and

a is 0;

to said patient.

2. The method of claim 1 , wherein the method comprises the administration of the compound

or a pharmaceutically acceptable salt thereof to said patient.

3. The method of claim 1 , wherein the method comprises the administration of the compound

or a pharmaceutically acceptable salt thereof to said patient.

4. The method of claim 1 , wherein the method comprises the administration of the compound

or a pharmaceutically acceptable salt thereof to said patient.

5. The method of claim 1 , wherein the method comprises the administration of the compound

or a pharmaceutically acceptable salt thereof to said patient.

6. The method of claim 1 , wherein the method comprises the administration of the compound

or a pharmaceutically acceptable salt thereof to said patient.

7. The method of claim 2 , wherein the disease or condition is hypercholesterolemia.

8. The method of claim 3 , wherein the disease or condition is hypercholesterolemia.

9. The method of claim 4 , wherein the disease or condition is hypercholesterolemia.

10. The method of claim 5 , wherein the disease or condition is hypercholesterolemia.

11. The method of claim 6 , wherein the disease or condition is hypercholesterolemia.

12. The method of claim 2 , wherein the disease or condition is familial hypercholesterolemia.

13. The method of claim 3 , wherein the disease or condition is familial hypercholesterolemia.

14. The method of claim 4 , wherein the disease or condition is familial hypercholesterolemia.

15. The method of claim 5 , wherein the disease or condition is familial hypercholesterolemia.

16. The method of claim 6 , wherein the disease or condition is familial hypercholesterolemia.

Assignments (2)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2016
From: SHAO, PENGCHENG PATRICK; SUN, WANYING; KATIPALLY, RAVATHI REDDY; VACHAL, PETR; YE, FENG; LIU, JIAN; SHA, DEYOU
To: MERCK SHARP & DOHME CORP.
Reel/Frame 037530/0950 →