IP Library Granted Patent US 9,877,957
Granted Patent B2
US 9,877,957 · App. 15/508,557 · Granted Jan 30, 2018

Tetrahydroisoquinoline derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2

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Quick Facts
Patent No.
US 9,877,957
App. No.
15/508,557
Granted
Jan 30, 2018
Kind
B2
Abstract

The present invention relates to a compound represented by formula I: and pharmaceutically acceptable salts thereof. The compounds of formula I are inhibitors of diacylglyceride O-acyltransferase 2 (“DGAT2”) and may be useful in the treatment, prevention and suppression of diseases mediated by DGAT2. The compounds of the present invention may be useful in the treatment of hepatic steatosis, diabetes mellitus, obesity, hyperlipidemia, hypercholesterolemia, atherosclerosis, cardio renal diseases such as chronic kidney diseases and heart failure and related diseases and conditions.

Claims (344)

1. A compound having structural Formula I:

or a pharmaceutically acceptable salt thereof wherein:

L is

(1) —CH 2 —, or

(2) —C(O)—;

M is

(1) —N(R 4 )—,

(2) *—N(R 4 )—(C 1-3 )alkylene wherein the alkylene is unsubstituted or substituted by (C 1-3 )alkyl, hydroxy(C 1-3 )alkyl, or morpholinyl,

(3) *—N(R 4 )—C(O)—,

(4) *—N(R 4 )—C(O)-heterocyclyl-, wherein the heterocyclyl is a 4- to 6-membered monocyclic ring containing 1-2 heteroatoms selected from the group consisting of N, O, and S,

(5) *—N(R 4 )—(C 3-6 )cycloalkyl-,

(6) *—N(R 4 )—(C 1-2 )alkyl-(C 3-6 )cycloalkyl-, or

(7)

wherein * indicates the point of attachment to group L;

X is

(1) —O—, or

(2) —NH—;

R 1 is

(1) (C 1-6 )alkyl,

(2) halo(C 1-8 )alkyl, or

(3) (C 3-6 )cycloalkyl-;

ring A is

(1) 4- to 6-membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S,

(2) aryl,

(3) fused phenyl,

(4) 5- or 6-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S, or

(5) fused 8- to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S;

R 2 is

(1) (C 1-6 )alkyl,

(2) halo(C 1-6 )alkyl,

(3) (C 1-6 )alkoxy,

(4) halo(C 1-6 )alkoxy,

(5) cyano,

(6) aryl,

(7) 5- or 6-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, or S,

(8) fused 8- to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S,

(9) oxo,

(10) (C 3-6 )cycloalkyl, or

(11) halo;

R 3 is

(1) (C 1-6 )alkyl,

(2) halo(C 1-6 )alkyl,

(3) (C 1-6 )alkoxy,

(4) halo(C 1-6 )alkoxy,

(5) —CO 2 (C 1-6 )alkyl,

(6) halo, or

(7) hydroxy;

R 4 is

(1) hydrogen, or

(2) (C 1-3 )alkyl;

m is 0, 1, 2, or 3; and

n is 0, 1 or 2.

2. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein L is —CH 2 —.

3. The compound of claim 2 or a pharmaceutically acceptable salt thereof wherein M is *—N(R 4 )—C(O)—, or *—N(R 4 )—C(O)-heterocyclyl-, wherein the heterocyclyl is a 5- to 6-membered monocyclic ring containing 1-2 heteroatoms selected from the group consisting of N, O, and S; wherein * indicates the point of attachment to group L.

4. The compound of claim 3 or a pharmaceutically acceptable salt thereof wherein X is —NH—.

5. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein L is —C(O)—.

6. The compound of claim 5 or a pharmaceutically acceptable salt thereof wherein M is —N(R 4 )—; *—N(R 4 )—(C 1-3 )alkylene wherein the alkylene is unsubstituted or substituted by (C 1-3 )alkyl, hydroxy(C 1-3 )alkyl or morpholinyl; *—N(R 4 )—(C 3-6 )cycloalkyl-; *—N(R 4 )—(C 1-2 )alkyl-(C 3-6 )cycloalkyl- or

wherein * indicates the point of attachment to group L.

7. The compound of claim 6 or a pharmaceutically acceptable salt thereof wherein X is —NH—.

8. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein ring A is ring A is 5- or 6-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S or fused 8- to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S.

9. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein ring A is pyrazolyl, isoquinolinyl, quinolinyl, imidazolyl, 1H-benzo[d]imidazolyl, imidazo[1,2-a]pyrimidinyl, imidazo[1,2-a]pyridinyl, benzo[c][1,2,5]oxadiazolyl, imidazo[2,1-b]thiazolyl, pyridinyl, 1,7-naphthyridinyl, imidazo[2,1-b][1,3,4]thiadiazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, pyrazolo[1,5-a]pyridinyl, 6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazolyl, 1H-benzo[d][1,2,3]triazolyl, 1,4,5,6-tetrahydrocyclopenta[c]pyrazolyl, 1H-1,2,3-triazolyl, pyrimidinyl, 1H-1,2,4-triazolyl, oxazolyl, or 1,2,5-oxadiazolyl.

10. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein ring A is aryl or fused phenyl.

11. The compound of claim 1 , which is

1

methyl 3-(2-(tert-butylcarbamoyl)-8-((1-(4-(trifluoromethyl)phenyl)piperidine-4-

carboxamido)methyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)benzoate;

2

N-(tert-butyl)-5-(3-(trifluoromethoxy)phenyl)-8-((3-(trifluoromethyl)-1H-pyrazole-5-

carboxamido)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide;

3

methyl 3-(8-((3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxamido)methyl)-2-(tert-

butylcarbamoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)benzoate;

4

N-(tert-butyl)-5-(3-methoxyphenyl)-8-((3-(trifluoromethyl)-1H-pyrazole-5-

carboxamido)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide;

5

N-((2-(tert-butylcarbamoyl)-5-(3-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-8-

yl)methyl)isoquinoline-1-carboxamide;

6

N 2 -(tert-butyl)-N 8 -(2-(5-chloro-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

7

N 2 -(tert-butyl)-N 8 -(2-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

8

N 2 -(tert-butyl)-N 8 -(2-(5-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

9

N 8 -(2-(1H-benzo[d]imidazol-2-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

10

N 2 -(tert-butyl)-N 8 -(isoquinolin-4-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

11

N 2 -(tert-butyl)-N 8 -(quinolin-8-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

12

N 2 -(tert-butyl)-N 8 -(isoquinolin-5-ylmethyl)-5-(3-(trifluoromethy)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

13

N 2 -(tert-butyl)-N 8 -(2-(6-methoxy-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethoxy)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

14

N 2 -(tert-butyl)-N 8 -(2-(5-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

15

N 2 -(tert-butyl)-N 8 -((2-methylimidazo[1,2-a]pyridin-3-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

16

N2-(tert-butyl)-N 8 -(quinolin-5-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

17

N 8 -(benzo[c][l,2,5]oxadiazol-5-ylmethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

18

N 2 -(tert-butyl)-N 8 -(2-(imidazo[2,l-b]thiazol-6-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

19

N 2 -(tert-butyl)-N 8 -(isoquinolin-1-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

20

N 2 -(tert-butyl)-N 8 -(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

21

R)-N 2 -(tert-butyl)-N 8 -(2-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

22

N 2 -(tert-butyl)-N 8 -(isoquinolin-1-ylmethyl)-5-(3-(trifluoromethoxy)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

23

N 2 -(tert-butyl)-N 8 -(2-(imidazo[1,2-a]pyridin-2-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

24

N 8 -((1,7-naphthyridin-8-yl)methyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

25

N 2 -(tert-butyl)-N 8 -(2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

26

N 2 -(tert-butyl)-N 8 -(quinolin-4-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

27

N 2 -(tert-butyl)-N 8 -((3-cyanoisoxazol-4-yl)methyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

28

N 2 -(tert-butyl)-N 8 -((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-5-)3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

29

N 2 -(tert-butyl)-N 8 -(2-(thiazol-4-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide:

30

N 2 -(tert-butyl)-N 8 -(pyrazolo[1,5-a]pyridin-3-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

31

N 2 -(tert-butyl)-N 8 -(2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

32

N 2 -(tert-butyl)-N 8 -((5-methyl-2-phenylthiazol-4-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

33

N 2 -(tert-butyl)-N 8 -((3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

34

N 8 -(2-(1H-benzo[d][1,2,3]triazol-1-yl)ethyl)-N 2 -(tert-butyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

35

N 2 -(tert-butyl)-N 8 -((1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

36

N 2 -(tert-butyl)-N 8 -(2-morpholino-2-(pyridin-2-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

37

N 2 -(tert-butyl)-N 8 -(2-(5-phenyl-1H-1,2,3-triazol-1-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

38

N 2 -(tert-butyl)-N 8 -(2-(4-methyl-6-(trifluoromethyl)pyrimidin-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

39

N 2 -(tert-butyl)-N 8 -((4-phenylthiazol-5-yl)methyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

40

N 2 -(tert-butyl)-N 8 -(2-(trifluoromethyl)phenethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

41

N 2 -(tert-butyl)-N 8 -((2,4-dimethylthiazol-5-yl)methyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

42

N 8 -(2-(1H-1,2,4-triazol-5-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

43

N 2 -(tert-butyl)-N 8 -(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

44

N 8 -(2-(1H-pyrazol-1-yl)propyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

45

N 2 -(tert-butyl)-N 8 -(2-(oxazol-2-yl)propyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

46

N 2 -(tert-butyl)-N 8 -(2-(isoxazol-5-yl)propyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

47

N 2 -(tert-butyl)-N 8 -(2-(5-methyl-4H-1,2,4-triazol-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

48

N 8 -(2-(1H-1,2,4-triazol-1-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

49

N 2 -(tert-butyl)-N 8 -(2-(imidazo[1,2-a]pyrimidin-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

50

N 2 -(tert-butyl)-N 8 -(2-(3,5-dimethylisoxazol-4-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

51

N 2 -(tert-butyl)-N 8 -((6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

52

N 2 -(tert-butyl)-N 8 -(4-(trifluoromethyl)phenethyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

53

N 8 -(4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-N 2 -(tert-butyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

54

N 2 -(tert-butyl)-N 8 -(2-(imidazo[1,2-a]pyridin-3-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

55

N 2 -(tert-butyl)-N 8 -(imidazo[1,2-a]pyrimidin-2-ylmethyl)-5-(3-

(trifluoromethoxy)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

56

N 2 -(tert-butyl)-N 8 -(2-(2-methyl-1H-imidazol-1-yl)ethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

57

N-(tert-butyl)-8-(2-phenylpiperidine-1-carbonyl)-5-(3-(trifluoromethoxy)phenyl)-3,4-

dihydroisoquinoline-2(1H)-carboxamide;

58

N 2 -(tert-butyl)-N 8 -(2-(6-chloro-1H-benzo[d]imidazol-2-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

59

N 8 -(2-(6-methoxy-1H-benzo[d]imidazol-2-yl)ethyl)-N 2 -(2,2,2-trifluoroethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

60

N 2 -(tert-butyl)-N 8 -(2-(5-methyl-4H-1,2,4-triazol-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

61

N 8 -(2-(1H-1,2,4-triazol-1-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

62

N 8 -(1-(4H-1,2,4-triazol-3-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

63

N 2 -(tert-butyl)-N 8 -(1-(pyridin-2-yl)cyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

64

N 2 -(tert-butyl)-N 8 -(1-(imidazo[2,1-b][1,3,4]thiadiazol-6-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

65

N 2 -(tert-butyl)-N 8 -((1R)-2-phenylcyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

67

N 2 -(tert-butyl)-N 8 -((4-methyl-1,2,5-oxadiazol-3-yl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

68

N 2 -(tert-butyl)-N 8 -((1-methyl-1H-imidazol-2-yl)methyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

69

N 2 -(tert-butyl)-N 8 -(((1R,2R)-2-phenylcyclopropyl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

70

N 8 -(2-(1H-1,2,4-triazol-5-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

71

N 8 -(2-(4H-1,2,4-triazol-4-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

72

N 8 -(1-(1,3,4-thiadiazol-2-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

73

N 2 -(tert-butyl)-N 8 -(1-(3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)ethyl)-5-(3-

(trifluoromethoxy)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

74

N 2 -(tert-butyl)-N 8 -(imidazo[2,1-b]thiazol-6-ylmethyl)-5-(3-(trifluoromethoxy)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

75

N 2 -(tert-butyl)-N 8 -((6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)methyl)-5-(3-

(trifluoromethoxy)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

76

N 8 -(2-(1H-1,2,3-triazol-1-yl)ethyl)-N 2 -(tert-butyl)-5-(3-(trifluoromethoxy)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

77

N 2 -(tert-butyl)-N 8 -(2-(oxazol-5-yl)propyl)-5-(3-(trifluoromethoxy)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

78

N 2 -(tert-butyl)-N 8 -(2-(pyridin-3-yl)propyl)-5-(3-(trifluoromethoxy)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide;

79

N 2 -(tert-butyl)-N 8 -(pyrazolo[1,5-a]pyridin-7-ylmethyl)-5-(3-(trifluoromethoxy)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

80

N 2 -(tert-butyl)-N 8 -((3-(pyridin-2-yl)isoxazol-5-yl)methyl)-5-(3-

(trifluoromethoxy)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide; or

81

N 2 -(tert-butyl)-N 8 -(pyrazolo[1,5-a]pyridin-3-ylmethyl)-5-(3-(trifluoromethoxy)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 , which is

1

(R)-N 2 -(tert-butyl)-N 8 -(2-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide;

2

(S)-N 2 -(tert-butyl)-N 8 -(2-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

3

N 2 -(tert-butyl)-N 8 -((1R)-2-phenylcyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide,

4

N 2 -(tert-butyl)-N 8 -((1S,2R)-2-phenylcyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide,

5

N 2 -(tert-butyl)-N 8 -((1R,2S)-2-phenylcyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide,

6

N 2 -(tert-butyl)-N 8 -(((1R,2R)-2-phenylcyclopropyl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

7

N 2 -(tert-butyl)-N 8 -(((1S,2S)-2-phenylcyclopropyl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

8

N 2 -(tert-butyl)-N 8 -(imidazo[1,2-a]pyridin-3-ylmethyl)-5-(3-(trifluoromethyl)phenyl)-

3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 , which is

1

(R/S)-N 2 -(tert-butyl)-N 8 -(2-hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

2

N 2 -(tert-butyl)-N 8 -((trans)-2-phenylcyclopropyl)-5-(3-(trifluoromethyl)phenyl)-3,4-

dihydroisoquinoline-2,8(1H)-dicarboxamide,

3

N 2 -(tert-butyl)-N 8 -(((trans)-2-phenylcyclopropyl)methyl)-5-(3-

(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2,8(1H)-dicarboxamide,

or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising of the compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

15. A method of treating atherosclerosis, hepatic steatosis, atherosclerosis, type-2 diabetes mellitus, obesity, hyperlipidemia, or hypercholesterolemia in a patient in need of treatment comprising the administration to the patient of a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

16. The method according to claim 15 for treating atherosclerosis.

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 Mar 28, 2017
From: IMBRIGLIO, JASON; LONDON, CLARE; LU, ZHIJIAN; TATA, JAMES; XIONG, YUSHENG; YOU, MING; YOUM, HYE WON
To: MERCK SHARP & DOHME CORP.
Reel/Frame 041759/0833 →