IP Library Granted Patent US 11,884,647
Granted Patent B2
US 11,884,647 · App. 17/072,844 · Granted Jan 30, 2024

Compounds and methods for targeting pathogenic blood vessels

Inventors: Hui Sun (Culver City, CA); Pu Sun (San Jose, CA); Guo Cheng (Los Angeles, CA); Adrian Chichuen Au (Los Angeles, CA); Ming Zhong (Nanjing, CN)
Assignees: The Regents of the University of California; Atengen, Inc.
C07D401/14A61P35/00C07D215/42C07D215/44C07D215/46C07D401/04C07D401/12C07D405/12C07D405/14C07D409/12C07D417/12C07D487/08C07D491/113C07D498/04C07H15/26
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Quick Facts
Patent No.
US 11,884,647
App. No.
17/072,844
Granted
Jan 30, 2024
Kind
B2
Abstract

The disclosure provides compounds, and compositions, including pharmaceutical compositions, kits that include the compounds, and methods of using (or administering) and making the compounds. The disclosure further provides compounds or compositions thereof for use in a method of modulating PLXDC1 (TEM7) and/or PLXDC2 or killing pathogenic blood vessles. The disclosure further provides compounds or compositions thereof for use in a method of treating a disease, disorder, or condition that is mediated, at least in part, by PEDF receptors or by angiogenesis.

Claims (1172)

1. A compound of Formula (I):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof;

wherein

n is 0, 1, 2, 3 or 4;

R 1 is selected from amino, optionally substituted heterocyclyl, optionally substituted cycloheptyl, and optionally substituted heteroaryl;

R 2 is selected from H, halo, alkyl, alkenyl, alkynyl, —OH, alkoxy, —CN, —NO 2 , alkylthio, sulfoxido, sulfonyl, and amino;

R 5 , R 7 and R 8 are each independently selected from H, halo, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, alkylthio, sulfoxido, sulfonyl, carboxy, ester, —CN, —NO 2 , amino, and amido;

R 6 is selected from halo, alkyl, hydroxy, alkoxy, alkylthio, sulfoxido, sulfonyl, carboxy, ester, —CN, —NO 2 , amino, amido, sulfinamido, sulfonamido, heterocyclyl, heteroaryl, poly(ethylene glycol), and methoxypoly(ethylene glycol), or

R 6 and R 7 together with atoms to which they are attached form a cycloalkyl, heterocyclyl, aryl, or heteroaryl; and

each R 9 is independently selected from halo, alkyl, —OH, alkoxy, —CN, and amino;

wherein the compound has at least one of the following:

1) R 2 is selected from C 2-30 alkyl, —OH, C 1-40 alkoxy, C 1-40 alkenoxy, C 1-40 alkynoxy, —NO 2 , alkylthio, sulfoxido, sulfonyl, and amino, where

a) when R 2 is ethyl, then R 6 is not methyl or methoxy, and/or

b) when R 2 is methoxy, then R 6 is not halo, C 1-2 alkyl or C 1-2 alkoxy;

2) R 1 is optionally substituted heteroaryl, optionally substituted bridged heterocyclyl, optionally substituted fused heterocyclyl, or optionally substituted cycloheptyl;

3) R 1 is heterocyclyl substituted with one halo, amino, hydroxy, alkoxy, —CN, —NO 2 , alkyl, carboxy, alkylthio, sulfoxido, sulfonyl, sulfinamido, sulfonamido, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, poly(ethylene glycol), or methoxypoly(ethylene glycol),

where if the substituent is alkyl, the alkyl is further substituted with one substituent selected from halo, amino, alkoxy, —CN, —NO 2 , carboxy, ester, alkylthio, sulfoxido, sulfonyl, sulfinamido, sulfonamido, cycloalkyl, heterocyclyl, poly(ethylene glycol), methoxypoly(ethylene glycol), pyrrolidinyl and piperidinyl; or the alkyl is substituted with at least one —OR 31 , wherein R 31 is poly(ethylene glycol) or methoxypoly(ethylene glycol);

4) R 1 is amino substituted with at least one substituent selected from alkyl, cycloalkyl, heterocyclyl, heteroaryl, poly(ethylene glycol) or methoxypoly(ethylene glycol) and amino,

where the alkyl is substituted with at least one substituent selected from halo, amino, hydroxy, alkoxy, —CN, —NO 2 , amido, carboxy, ester, alkylthio, sulfoxido, sulfonyl, sulfinamido, sulfonamido, cycloalkyl, heterocyclyl, and heteroaryl;

5) R 6 is alkyl substituted with at least one substituent selected from halo, amino, hydroxy, alkoxy, cycloalkoxy, heterocycloalkoxy, aryloxy, heteroaryloxy, poly(ethylene glycol)-oxy, methoxypoly(ethylene glycol)-oxy, —CN, —NO 2 , oxo, amido, carboxy, ester, alkylthio, sulfoxido, sulfonyl, sulfinamido, sulfonamido, heterocyclyl, cycloalkyl, aryl, heteroaryl, poly(ethylene glycol) and methoxypoly(ethylene glycol).

2. The compound of claim 1 , wherein n is 0, 1 or 2.

3. The compound of claim 1 , wherein when R 2 is C 1-6 alkyl, R 6 is not C 1-6 alkyl or C 1-6 alkoxy.

4. The compound of claim 1 , wherein R 1 is an optionally substituted 5- to 9-membered heterocyclyl, an optionally substituted 5- to 7-membered heterocyclyl, or an optionally substituted 5- to 6-membered heterocyclyl.

5. The compound of claim 1 , wherein R 1 is an optionally substituted 5- or 6-membered heteroaryl.

6. The compound of claim 1 , wherein

R 1 is heterocyclyl substituted with at least one substituent selected from oxo, —OH, —OR 28 , —N(R 28 ) 2 , alkyl, aryl, and heterocyclyl,

the alkyl is substituted with at least one substituent selected from —N(R 31 ) 2 , —S(O) 0-2 NR 31 R 31 , —C(O)N(R 31 ) 2 , heterocyclyl, cycloalkyl, pyrrolidinyl, and piperidinyl; or

the alkyl is substituted with at least one —OR 31a wherein R 31a is poly(ethylene glycol) or methoxypoly(ethylene glycol); and

each R 28 and R 31 are independently H or alkyl.

7. The compound of claim 1 , wherein R 1 is heteroaryl or heterocyclyl substituted with a second heterocyclyl; and

the second heterocyclyl is unsubstituted or substituted with one or more substituents selected from —OH, —C(O)Oalkyl, —C(O)NHalkyl, alkyl, aryl, and heterocyclyl; and

wherein the alkyl and heterocyclyl are each unsubstituted or substituted with one or more substituents selected from —OH, alkyl, and aryl.

8. The compound of claim 1 , wherein R 1 is

wherein each s and t is independently 0, 1, 2 or 3, provided that the sum of s and t is 1, 2, 3, or 4;

R 20 is selected from alkyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl; and

R 20a is H, NH 2 , or OH.

9. The compound of claim 1 , wherein R 1 is heterocyclyl, optionally substituted with a sugar moiety.

10. The compound of claim 1 , wherein R 1 is

—NR 3 R 4 , and R 3 is H or alkyl that is unsubstituted or substituted with at least one substituent selected from —OH, —N(R 28 ) 2 , and heteroaryl, and R 4 and R 28 are each independently H or alkyl.

11. The compound of claim 1 , wherein R 1 is selected from

12. The compound of claim 1 , wherein R 1 is selected from

13. The compound of claim 1 , wherein R 1 is selected from

14. The compound of claim 1 , wherein R 1 is selected from

15. The compound of claim 1 , wherein R 1 is selected from

16. The compound of claim 1 , wherein R 2 is selected from C 1-6 alkyl, —NO 2 , —OR 18 , and CN, and R 18 is selected from C 1-16 alkyl, C 1-6 haloalkyl, and C 1-6 aminoalkyl.

17. The compound of claim 16 , wherein R 2 is —O(CH 2 ) m CH 3 , wherein m is an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 12, 13, 14, 15, and 16.

18. The compound of claim 1 , wherein R 2 is amino, substituted with one or more substituents selected from alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, and amino.

19. The compound of claim 18 , wherein the amino substituent is alkyl substituted with at least one substituent selected from —C(O)OH, —OH, phenyl, and pyridyl, and the phenyl and pyridyl are each independently unsubstituted or substituted with halo, alkyl, or —OH.

20. The compound of claim 1 , wherein R 6 is selected from halo, alkyl, —OR 17 , —S(O) 0-2 R 16 , —C(O)OR 15 , —NO 2 , and —C(O)NR 15 R 15 ;

R 15 is selected from H, methyl, ethyl, iPr, —CH 2 CH 2 NEt 2 , and —CH 2 CH 2 OH;

R 16 is methyl; and

R 17 is selected from methyl, trifluoromethyl and butyl.

21. The compound of claim 1 , wherein R 6 is selected from

22. The compound of claim 1 , wherein R 5 , R 7 and R 8 are each H.

23. The compound of claim 1 , wherein n is 1 or 2 and each R 9 is independently halo.

24. The compound of claim 1 , wherein the compound is of Formula (II):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

25. The compound of claim 1 , wherein the compound is of Formula (III):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

26. The compound of claim 1 , wherein the compound is of Formula (IV):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

27. The compound of claim 1 , wherein the compound is of Formula (V):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof,

wherein

each of s, t, u, and v is independently 0, 1, 2, or 3, provided that the sum of s and t is 1, 2, 3 or 4, and the sum of u and v is 1, 2, 3 or 4;

w is 0, 1, 2, or 3;

Z 1 is C or N,

when Z 1 is C, R 20a is selected from H, halo, oxo, —NH 2 , —OH, —CN, —NO 2 , —NHR 28 , —N(R 28 ) 2 , —C(O)R 28 , —C(O)OR 28 , —C(O)OH, —OC(O)R 28 , —S(O) 0-2 R 28 , —NHS(O) 0-2 R 28 , —S(O) 0-2 NHR 28 , —NHS(O) 0-2 NHR 28 , —C(O)NH 2 , —C(O)NHR 28 , —C(O)N(R 28 ) 2 , —NHC(O)R 28 , —OC(O)NHR 28 , —NHC(O)OR 28 , —OC(O)N(R 28 ) 2 , —NR 32 C(O)NH 2 , —NR 32 C(O)NHR 28 , —NR 32 C(O)N(R 28 ) 2 , poly(ethylene glycol), methoxypoly(ethylene glycol), C 1-30 alkyl optionally substituted with OH or —C(O)OH, and C 1-30 heteroalkyl optionally substituted with OH or —C(O)OH, wherein R 32 is H or C 1-4 alkyl, and R 28 is C 1-4 alkyl;

when Z 1 is N, R 20a is absent;

Z 2 is C or N;

Z 3 is CH 2 , CHR 25 , CR 25 R 25 , or NR 25 , O, or S(O) 0-2 and R 25 is selected from H and alkyl.

28. A compound selected from the group consisting of:

1

3-((4-ethylphenyl)sulfonyl)-4-(4- methylpiperazin-1-yl)- 6-(trifluoromethoxy)quinoline

2

3-((4-ethylphenyl)sulfonyl)-4-(piperidin- 1-yl)-6-(trifluoromethoxy)quinoline

3

4-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)morpholine

4

3-((4-ethylphenyl)sulfonyl)-4-(4- methylpiperidin-1-yl)-6- (trifluoromethoxy)quinoline

5

2-(4-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperazin-1-yl)ethan-1-ol

6

3-((4-ethylphenyl)sulfonyl)-4-(4- ethylpiperazin-1-yl)-6- (trifluoromethoxy)quinoline

7

3-((4-ethylphenyl)sulfonyl)-4-(4-methyl- 1,4-diazepan-1-yl)-6- (trifluoromethoxy)quinoline

8

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

9

ethyl 4-(3-((4-ethylphenyl)sulfonyl-6- (trifluoromethoxy)quinolin-4- yl)piperazine-1-carboxylate

10

3-((4-ethylphenyl)sulfonyl)-4-(4-(4- fluorophenyl)piperazin-1-yl)-6- (trifluoromethoxy)quinoline

11

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

12

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl)-4- phenylpiperidin-4-ol

13

3-((4-ethylphenyl)sulfonyl)-4-(4- phenylpiperazin-1-yl)-6- (trifluoromethoxy)quinoline

14

3-((4-ethylphenyl)sulfonyl)-4-(pyrrolidin- 1-yl)-6-(trifluoromethoxy)quinoline

15

1-(3-((4-ethylphenyl)sulfonyl)-6- methoxyquinolin-4-yl)piperidin-4-ol

16

ethyl 4-(3-((4-ethylphenyl)sulfonyl)-6- methoxyquinolin-4-yl)piperazine-1- carboxylate

17

3-((4-ethylphenyl)sulfonyl)-4-(4-(4- fluorophenyl)piperazin-1- yl)-6-methoxyquinoline

18

N-cyclohexyl-3-((4- ethylphenyl)sulfonyl)-6- methoxyquinolin-4-amine

19

3-((4-ethylphenyl)sulfonyl)-N-(4- fluorophenyl)-6-methoxyquinolin- 4-amine

20

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (4-methylpiperazin-1-yl)quinoline

21

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (piperidin-1-yl)quinoline

22

4-(3-((4-ethylphenyl)sulfonyl)-6- methoxyquinolin-4-yl)morpholine

23

3-((4-ethylphenyl)sulfonyl-6-methoxy-4- (4-methylpiperidin-1-yl)quinoline

24

3-((4-ethylphenyl)sulfonyl)-4-(4- ethylpiperazin-1-yl)-6-methoxyquinoline

25

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (pyrrolidin-1-yl)quinoline

26

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (4-phenylpiperazin-1-yl)quinoline

27

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)-6- methoxyquinoline

28

1-(3-((4-ethylphenyl)sulfonyl)-6- methoxyquinolin-4- yl-4-phenylpiperidin-4-ol

29

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (4-methyl-1,4-diazepan-1-yl)quinoline

30

3-((4-ethylphenyl)sulfonyl-4-(4- isopropylpiperazin-1-yl)-6- methoxyquinoline

31

4-(azepan-1-yl)-3-((4- ethylphenyl)sulfonyl)-6- methoxyquinoline

32

3-((4-ethylphenyl)sulfonyl)-6-methyl-4- (4-methylpiperazin-1-yl)quinoline

33

3-((4-ethylphenyl)sulfonyl)-6-methyl-4- (4-methyl-1,4-diazepan-1-yl)quinoline

34

1-(3-((4-ethylphenyl)sulfonyl)-6- methylquinolin-4-yl)piperidin-4-ol

35

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)-6-methyl)quinoline

36

3-((4-ethylphenyl)sulfonyl)-6-methyl-4- (piperidin-1-yl)quinoline

37

3-((4-ethylphenyl)sulfonyl)-6-fluoro-4- (4-methylpiperazin-1-yl)quinoline

38

3-((4-ethylphenyl)sulfonyl)-6-fluoro-4- (4-methyl-1,4-diazepan-1-yl)quinoline

39

1-(3-((4-ethylphenyl)sulfonyl)-6- fluoroquinolin-4-yl)piperidin-4-ol

40

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)-6-fluoroquinoline

41

3-((4-ethylphenyl)sulfonyl-6-fluoro-4- (piperidin-1-yl)quinoline

42

2-(4-(3-((4-ethylphenyl)sulfonyl-6- (trifluoromethoxy)quinolin-4-yl)-1,4- diazepan-1-yl)acetic acid

43

4-([1,4′-bipiperidin]-1yl)-3-((4- methoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

44

1-(3-((4-methoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

45

4-(4-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperazin-1-yl)benzonitrile

46

3-((4-ethylphenyl)sulfonyl)-4-(4- (pyrrolidin-1-yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

47

ethyl)-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidine-4-carboxylate

48

(1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-yl)methanol

49

N-benzyl-3-((4-ethylphenyl)sulfonyl)-N- methyl-6-(trifluoromethoxy)quinolin-4- amine

50

3-((4-ethylphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (trifluoromethoxy)quinolin-4-amine

51

3-((4-ethylphenyl)sulfonyl-4-(1H-1,2,4- triazol-1-yl)-6- (trifluoromethoxy)quinoline

52

8-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)-1,4-dioxa-8-azaspiro[4,5]decane

53

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidine-4-carboxylate acid

54

4-((4-([1,4′-bipiperidin]-1′-yl)-6- (trifluoromethoxy)quinolin-3- yl)sulfonyl)benzonitrile

55

2-(4-([1,4′-bipiperidin]-1′-yl-3-((4- ethylphenyl)sulfonyl)quinolin-6- yl)acetonitrile

56

4-([1,4′-bipiperidin]-1′-yl)-3-((3,4- dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

57

3-((3,4-dimethoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (trifluoromethoxy)quinoline

58

1-(3-((3,4-dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

59

4-([1,4,-bipiperidin]-1′-yl-3-((4- nitrophenyl)sulfonyl-6- (trifluoromethoxy)quinoline

60

4-(4-methyl-1,4-diaxepan-1-yl)-3-((4- nitrophenyl)sulfonyl-6- (trifluoromethoxy)quinoline

61

1-(3-((4-nitrophenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

62

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(4- hydroxypiperidin-1-yl)quinoline-6- carboxylate

63

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)quinoline-6- carboxylate

64

ethyl 4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)quinoline-6- carboxylate

65

3-((4-ethylphenyl)sulfonyl)-4-(4- hydroxypiperidin-1-yl)quinoline-6- carboxylate acid

66

3-((4-ethylphenyl)sulfonyl)-4-(4-methyl- 1,4-diazepan-1-yl)quinoline-6-carboxylate acid

67

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)quinoline-6- carboxylate acid

68

3-((3,4-dimethoxyphenyl)sulfonyl)-N,N- diethyl)l-6-trifluoromethoxy)quinolin-4- amine

69

2-((3-((3,4-dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)amino)ethan-1-ol

70

1-(3-((3,4-dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-3-ol

71

3-((3,4-dimethoxyphenyl)sulfonyl)-N,N- dipropyl-6-(trifluoromethoxy)quinolin-4- amine

72

2,2′-((3-((3,4-dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)azanediyl)bis(ethan-1-ol)

73

2-((3-((3,4-dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)amino)ethan-1-ol

74

N,N-dibutyl-3-((3,4- dimethoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-amine

75

1-(3-((4-ethylphenyl)sulfonyl)-6- nitroquinolin-4-yl)piperidin-4-ol

76

3-((4-ethylphenyl)sulfonyl-4-(4-methyl- 1,4-diazepan-1-yl)-6-nitroquinoline

77

4-([1,4′-bipiperidin]-1′-yl)-3-((4- ethylphenyl)sulfonyl)-6-nitroquinoline

78

N,N-diethyl)l-3-((4-ethylphenyl)sulfonyl)- 6-nitroquinolin-4-amine

79

3-((4-ethylphenyl)sulfonyl)-6-methoxy-4- (1H-1,2,4-triazol-1-yl)quinoline

80

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(1H- 1,2,4-triazol-1-yl)quinoline-6-carboxylate

81

N,N-diethyl)l-3-((4-ethylphenyl)sulfonyl)- 6-(trifluoromethoxy)quinolin-4-amine

82

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-3-ol

83

3-((4-ethylphenyl)sulfonyl)-6-methoxy- N-(4-methylpiperazin-1-yl)quinolin-4- amine

84

ethyl 3-((4-ethylphenyl)sulfonyl)-4-((4- methylpiperazin-1-yl)amino)quinoline-6- carboxylate

85

3-((4-methoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (trifluoromethoxy)quinolin-4-amine

86

3-((4-methoxyphenyl)sulfonyl)-4-(1H- 1,2,4-triazol-1-yl)-6- (trifluoromethoxy)quinoline

87

N,N-dibutyl-3-((4-ethylphenyl)sulfonyl)- 6-(trifluoromethoxy)quinolin-4-amine

88

3-((3,4-dimethoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (trifluoromethoxy)quinolin-4-amine

89

3-((3,4-dimethoxyphenyl)sulfonyl)-4- (1H-1,2,4-triazol-1-yl)-6- (trifluoromethoxy)quinoline

90

N-(4-methylpiperazin-1-yl)-6- (trifluoromethoxy)-3-((4- (trifluoromethoxy)phenyl)sulfonyl)quinolin- 4-amine

91

4-(1H-1,2,4-triazol-1-yl)-6- (trifluoromethoxy)-3-((4- (trifluoromethoxy)phenyl)sulfonyl)quinoline

92

3-((4-butoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (trifluoromethoxy)quinolin-4-amine

93

3-((4-butoxyphenyl)sulfonyl)-4-(1H- 1,2,4-triazol-1-yl)-6- (trifluoromethoxy)quinoline

94

3-((4-methoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6-nitroquinolin-4- amine

95

2-((3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)amino)ethan-1-ol

96

3-((3,4-dimethoxyphenyl)sulfonyl)-6,7- dimethoxy-4-(1H-1,2,4-triazol-1- yl)quinoline

97

3-((4-methoxyphenyl)sulfonyl)-6-nitro-4- (1H-1,2,4-triazol-1-yl)quinoline

98

2-(3-((4-methoxyphenyl)sulfonyl)-4-(1H- 1,2,4-triazol-1-yl)quinolin-6- yl)acetonitrile

99

2-(3-((4-methoxyphenyl)sulfonyl)-4-((4- methylpiperazin-1-yl)amino)quinolin-6- yl)acetonitrile

100

N,N-diethyl)l-2-(4-(3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl)-1,4- diazepan-1-yl)ethan-1-amine

101

N,N-diethyl)l-2-((1-(3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-yl)oxy)ethan-1-amine

102

1′-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl-[1,4′- bipiperidin]-4-ol

103

N,N-diethyl)l-1-(3-((4- ethylphenyl)sulfonyl-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-amine

104

5-((3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)amino)pentan-1-ol

105

3-((4-ethylphenyl)sulfonyl)-N-(piperidin- 1-yl)-6-(trifluoromethoxy)quinolin-4- amine

106

3-((4-ethylphenyl)sulfonyl)-N-(pyridin-4- ylmethyl)-6-(trifluoromethoxy)quinolin- 4-amine

107

3-((4-ethylphenyl)sulfonyl)-N-(pyridin-4- yl)-6-(trifluoromethoxy)quinolin-4-amine

108

3-((4-ethylphenyl)sulfonyl)-4-(1H-pyrrole- 1-yl)-6-(trifluoromethoxy)quinoline

109

3-((4-ethylphenyl)sulfonyl)-4-(1H- pylazol-1-yl)-6- (trifluoromethoxy)quinoline

110

3-((4-ethylphenyl)sulfonyl)-4-(1H-1,2,3- triazol-1-yl)-6- (trifluoromethoxy)quinoline

111

4-((3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy) quinolin-4-yl)amino)butan-1-ol

112

4-(1H-benzo[d][1,2,3]triazol-1-yl)-3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

113

1′-(3-((4-methoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl-[1,4′- bipiperidin]-4-ol

114

4-([1,4′-bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl)-6- nitroquinoline

115

2-(4-([1,4′-bipiperidin]-1yl)-3-((4- methoxyphenyl)sulfonyl)quinolin-6- yl)acetonitrile

116

4-([1,4′-bipiperidin]-1′-yl)-6-butoxy-3- ((3,4-dimethoxyphenyl) sulfonyl)quinoline

117

3-((4-ethylphenyl)sulfonyl)-4-(4-methyl- 1H-imidazol-1-yl)-6- (trifluoromethoxy)quinoline

118

3-((4-ethylphenyl)sulfonyl)-4-(1H- imidazol-1-yl)-6- (trifluoromethoxy)quinoline

119

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl) sulfonyl)-6-(trifluoromethoxy)quinoline

120

4-([1,4′-bipiperidin]-1′-yl)-6- (trifluoromethoxy)-3-((4- (trifluoromethoxy)phenyl)sulfonyl)quinoline

121

4-([1,4′-bipiperidin]-1′-yl)-3-((3,4- dimethoxyphenyl)sulfonyl)-6- (methylthio)quinoline

122

4-([1,4′-bipiperidin]-1′-yl)-3-((3,4- dimethoxyphenyl)sulfonyl)-6,7- dimethoxyquinoline

123

6-butoxy-3-((3,4- dimethoxyphenyl)sulfonyl)-N,N- diethyl)lquinolin-4-amine

124

N,N-dibutyl-3-((3,4- dimethoxyphenyl)sulfonyl)-6- (methythio)quinolin-4-amine

125

3-((4-ethylphenyl)sulfonyl)-4-(1H- tetrazol-1-yl)-6- (trifluorotmethoxy)quinoline

126

N-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)morpholin-4-amine

127

4-(4-ethylphenyl)-1-(3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

128

ethyl 4-(4-(4-ethylphenyl)-4- hydroxypiperidin-1-yl)-3-((4- ethylphenyl)sulfonyl)quinoline-6- carboxylate

129

4-(4-ethylphenyl)-1-(3-((4- methoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

130

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(4- hydroxy-[1,4′-bipiperidin]-1′- yl)quinoline-6-carboxylate

131

ethyl 4-(4-(2-(diethyl)lamino)ethyl)-1,4- diazepan-1-yl)-3-((4- ethylphenyl)sulfonyl)quinoline-6- carboxylate

132

ethyl 4-(4-(2- (diethyl)laminotethoxy)piperidin-1-yl)-3- ((4-ethylphenyl)sulfonyl)quinoline-6- carboxylate

133

ethyl 4-(1H-benzo[d][1,2,3]triazol-1-yl)-3- ((4-ethylphenyl)sulfonyl)quinoline-6- carboxylate

134

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(1H- imidazol-1-yl)quinoline-6-carboxylate

135

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(3- hydroxypiperidin-1-yl)quinoline-6- carboxylate

136

ethyl 4-([1,4′-bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

137

ethyl 4-(3-hydroxypiperidin-1-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

138

ethyl 4-(4-hydroxy-[1,4′-bipiperidin]-1′- yl-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

139

ethyl 4-(4-(2-(diethyl)lamino)ethyl)-1,4- diazepan-1-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

140

ethyl 4-(4-(2- (diethyl)lamino)ethoxy)piperidin-1-yl)-3- ((4-methoxyphenyl)sulfonyl)quinoline-6- carboxylate

141

ethyl 4-(1H-imidazol-1-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

142

ethyl 4-(1H-benzo[d][1,2,3]triazol-1-yl)- 3-((4-methoxyphenyl)sulfonyl)quinoline- 6-carboxylate

143

4-([1,4′-bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl-N- methyl)quinoline-6-carboxamide

144

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (4-methyl-1,4-diazepan-1-yl)quinoline-6- carboxylate

145

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl)-4-(4- methoxyphenyl)piperidin-4-ol

146

1-(3-((4-ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl)-4-(3- methoxyphenyl)piperidin-4-ol

147

4-(benzo[d][1,3]dioxol-5-yl)-1-(3-((4- ethylphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

148

ethyl 3-((4-ethylphenyl)sulfonyl)-4-(4- hydroxy-4-(4-methoxyphenylpiperidin- 1-yl)quinoline-6-carboxylate

149

ethyl 3-((4-ethylphenyl)sulfonyl-4-(4- hydroxy-4-(3-methoxyphenyl)piperidin- 1-yl)quinoline-6-carboxylate

150

4-(3-methoxyphenyl)-1-(3-((4- methoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)piperidin-4-ol

151

3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (trifluoromethoxy)quinoline

152

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

153

1′-(3-((3,4-dimethoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

154

3-((3,4-dimethoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylthio)quinoline

155

ethyl 4-(dibutylamino)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

156

ethyl 4-(bis(2-hydroxyethyl)amino)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

157

ethyl 4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)quinoline-6- carboxylate

158

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)quinoline-6- carboxylate

159

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylthio)quinoline

160

3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylthio)quinoline

161

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- hydroxy-[1,4′-bipiperidin]-1′- yl)quinoline-6-carboxylate

162

1′-(3-((4-butoxyphenyl)sulfonyl-6- (methylthio)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

163

3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylsulfinyl)quinoline

164

3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylsulfonyl)quinoline

165

N,N-diethyl)l-3-((4- methoxyphenyl)sulfonyl-4-(4-methyl- 1,4-diazepan-1-yl)quinoline-6- carboxamide

166

N-(2-(diethyl)lamino)ethyl)-3-((4- methoxyphenyl)sulfonyl)-4-(4-methyl- 1,4-diazepan-1-yl)quinoline-6- carboxamide

167

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinoline

168

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

169

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfonyl)quinoline

170

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfonyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

171

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)piperidin-1- yl)quinoline-6-carboxylate

172

ethyl 3-((4-butoxyphenyl)sulfonyl-4-(4- (4-methylpiperazin-1-yl)piperidin-1- yl)quinoline-6-carboxylate

173

ethyl 4-(4-(azepan-1-yl)piperidin-1-yl)-3- ((4-ethoxyphenyl)sulfonyl)quinoline-6- carboxylate

174

ethyl 4-(3-hydroxy-[1,4′-bipiperidin]-1′- yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

175

ethyl 4-(4-(hydroxymethyl)-[1,4′- bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxylate

176

ethyl 4-(4-(azepan-1-yl)piperidin-1-yl)-3- ((4-butoxyphenyl)sulfonyl)quinoline-6- carboxylate

177

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(3- hydroxy-[1,4′-bipiperidin]-1′- yl)quinoline-6-carboxylate

178

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (hydroxymethyl)-[1,4′-bipiperidin]-1′- yl)quinoline-6-carboxylate

179

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (4-(2-(piperidin-1-yl)ethyl)-1,4-diazepan- 1-yl)quinoline-6-carboxylate

180

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (4-(2-(pyrrolidin-1-yl)ethyl)-1,4- diazepan-1-yl)quinoline-6-carboxylate

181

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (2-(piperidin-1-yl)ethyl)-1,4-diazepan-1- yl)quinoline-6-carboxylate

182

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (2-(pyrrolidin-1-yl)ethyl)-1,4-diazepan-1- yl)quinoline-6-carboxylate

183

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (1H-1,2,4-triazol-1-yl)quinoline-6- carboxylate

184

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (1H-1,2,3-triazol-1-yl)quinoline-6- carboxylate

185

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- (1H-tetrazol-1-yl)quinoline-6-carboxylate

186

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1H-tetrazol-1-yl)quinoline-6-carboxylate

187

4-(3-((4-butoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)thiomorpholine

188

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1H-1,2,4-triazol-1-yl)quinoline-6- carboxylate

189

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1H-1,2,3-triazol-1-yl)quinoline-6- carboxylate

190

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1H-1,2,4-triazol-1-yl)quinoline-6- carboxylate

191

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- thiomorpholinoquinoline-6-carboxylate

192

3-((4-butoxyphenyl)sulfonyl)-N- isopropyl-4-(4-methyl-1,4-diazepan-1- yl)quinoline-6-carboxamide

193

3-((4-butoxyphenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-N- ((4R,5S,6R)-2,4,5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3- yl)quinoline-6-carboxamide

194

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1H-imidazol-1-yl)quinoline-6- carboxylate

195

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(1- oxidothiomorpholino)quinoline-6- carboxylate

196

ethyl 3-((4-butoxyphenyl)sulfonyl)-4- (1,1-dioxidothiomorpholino)quinoline-6- carboxylate

197

4-(3-((4-butoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)thiomorpholine 1-oxide

198

4-(3-((4-butoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinolin-4- yl)thiomorpholine 1,1-dioxide

199

3-((4-butoxyphenyl)sulfonyl)-N,N- diethyl)l-4-(4-methyl-1,4-diazepan-1- yl)quinoline-6-carboxamide

200

3-((4-butoxyphenyl)sulfonyl)-N-(2- hydroxyethyl)-4-(4-methyl-1,4-diazepan- 1-yl)quinoline-6-carboxamide

201

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-N,N- diethyl)quinoline-6-carboxamide

202

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-N-(2- hydroxyethyl)quinoline-6-carboxamide

203

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-N- ethyl)quinoline-6-carboxamide

204

4-(1H-imidazol-1-yl)-3-((4- methoxyphenyl)sulfonyl)-N-((4R,5S,6R)- 2,4,5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3- yl)quinoline-6-carboxamide

205

4-(1H-benzo[d][1,2,3]triazol-1-yl)-3-((4- methoxyphenyl)sulfonyl)-N-((4R,5S,6R)- 2,4,5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3- yl)quinoline-6-carboxamide

206

3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)-4-(4-(2-(piperidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

207

3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)-4-(4-(2-(pyrrolidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

208

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-3-ol

209

3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(piperidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

210

3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(pyrrolidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

211

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (4-methyl-1,4-diazepan-1-yl)piperidin-1- yl)quinoline-6-carboxylate

212

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- morpholinopiperidin-1-yl)quinoline-6- carboxylate

213

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (4-fluorophenyl)piperazin-1-yl)quinoline- 6-carboxylate

214

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (4-(2-hydroxyethyl)piperazin-1- yl)piperidin-1-yl)quinoline-6-carboxylate

215

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- phenyl-[1,4′-bipiperidin]-1′-yl)quinoline- 6-carboxylate

216

ethyl 4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3- ((4-butoxyphenyl)sulfonyl)quinoline-6- carboxylate

217

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- thiomorpholinopiperidin-1-yl)quinoline- 6-carboxylate

218

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylthio)quinoline

219

4-([1,4′-bipiperidin]-1′-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

220

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- methyl-1,4-diazepan-1-yl)-6- (methylsulfinyl)quinoline

221

4-([1,4′-bipiperidin]-1′-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulflnyl)quinoline

222

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-[1,4′- bipiperidin]-3-ol

223

1′-(3-((4-(heplyloxy)phenyl)sulfonyl)-6- (methylthio)quinolin-4-yl-[1,4′- bipiperidin]-4-ol

224

1′-(3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-ol

225

ethyl 3-((4-methoxyphenyl)sulfonyl)-4- ((4-methylpiperazin-1- yl)amino)quinoline-6-carboxylate

226

3-((4-methoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (methylthio)quinolin-4-amine

227

3-((4-methoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (methylsulfinyl)quinolin-4-amine

228

3-((4-methoxyphenyl)sulfonyl)-N-(4- methylpiperazin-1-yl)-6- (methylsulfonyl)quinolin-4-amine

229

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4- yl)piperidin-4-yl)morpholine

230

2-(4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

231

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylthio)quinoline

232

1′-(3-((4-butoxyphenyl)sulfonyl-6- (methylthio)quinolin-4-yl)-4- phenyl-[1,4′-bipiperidin]-4-ol

233

3-((4-butoxyphenyl)sulfonyl)-4-(4-(4-(4- fluorophenyl)piperazin-1-yl)piperidin-1- yl)-6-(methylthio)quinoline

234

3-((4-butoxyphenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)piperidin-1-yl)- 6-(methylthio)quinoline

235

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)morpholine

236

2-(4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

237

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinoline

238

1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-4-phenyl- [1,4′-bipiperidin]-4-ol

239

3-((4-butoxyphenyl)sulfonyl)-4-(4-(4-(4- fluorophenyl)piperazin-1-yl)piperidin-1- yl)-6-(methylsulfinyl)quinoline

240

(1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)methanol

241

3-((4-butoxyphenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

242

N,N-diethyl)l-2-(4-((4-(4-methyl-1,4- diazepan-1-yl)-6-(methylthio)quinolin-3- yl)sulfonyl)phenoxy)ethan-1-amine

243

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-piperidin-4- yl)thiomoroholine

244

ethyl 3-((4-butoxyphenyl)sulfonyl)-4-(4- (1-oxidothiomoroholino)piperidin-1- yl)quinoline-6-carboxylate

245

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)thiomorpholine

246

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)piperidin-1-yl)- 6-(methylthio)quinoline

247

1′-(3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-[1,4′- bipiperidin]-3-ol

248

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)-4-(4-(2-(piperidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

249

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-methyl-1,4-diazepan-1-yl)piperidin-1- yl)-6-(methylthio)quinoline

250

2-(4-(1-(3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

251

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

252

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- methylpiperazin-1-yl)-6- (methylthio)quinoline

253

3-((4-(heptyloxy)phenyl)sulfonyl-4-(4- (4-methylpiperazin-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

254

1′-(3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-3-ol

255

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(piperidin-1- yl)ethyl)-1,4-diazepan-1-yl)quinoline

256

3-((4-(heplyloxy)phenyl)sulfonyl)-4-(4- (4-methyl-1,4-diazepan-1-yl)piperidin-1- yl)-6-(methylsulfinyl)quipoline

257

2-(4-(1-(3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

258

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

259

3-((4-heptyloxy)phenyl)sulfonyl)-4-(4- methylpiperazin-1-yl)-6- (methylsulfinyl)quinoline

260

3-((4-methoxyphenyl)sulfonyl)-4-((4- methylpiperazn-1-yl)amino)-N- ((4R,5S,6R)-2,4,5-trihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-3- yl)quinoline-6-carboxamide

262

1′-(3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-4-phenyl- [1,4′-bipiperidin]-4-ol

263

1′-(3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-4-phenyl- [1,4′-bipiperidin]-4-ol

264

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

265

1′-(3-((4-(decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-3-ol

266

3-((4-(decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(piperidin-1- yl)ethyl)-1,4-diazepan-l-yl)quinoline

267

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

268

2-(4-(1-(3-((4- (decyloxy)phenyl)sulfonyl-6- methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

269

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (decyloxy)phenyl)sulfonyl-6- (methylsulfinyl)quinoline

270

1′-(3-((4-(decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-4-phenyl- [1,4′-bipiperidin]-4-ol

271

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-(2-mPEGoxyethyl)piperazin-1- yl)piperidin-1-yl)-6- (methylthio)quinoline

272

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)-4-(4-(2-(pyrrolidin-1- yl)ethyl)piperazin-1-yl)quinoline

273

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (1-methylpiperidin-4-yl)piperazin-1-yl)- 6-(methylthio)quinoline

274

4-(4-(1-benzylpyrrolidin-3-yl)piperazin- 1-yl)-3-((4-(heptyloxy)phenyl)sulfonyl)- 6-(methylthio)quinoline

275

4-(4-((1-benzylpiperidin-4- yl)methyl)piperazin-1-yl)-3- ((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

276

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(pyrrolidin-1- yl)ethyl)piperazin-1-yl)quinoline

277

4-(4-(1-ethylpiperidin-4-yl)piperazin-1- yl)-3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

278

4-(4-(1-benzylpyrrolidin-3-yl)piperazin-1- yl)-3-((4-(heptyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinoline

279

4-(4-((1-benzylpiperidin-4- yl)methyl)piperazin-1-yl)-3- ((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

280

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-(2-mPEGoxyethyl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

281

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylthio)-4-(4-(2-(piperidin-1- yl)ethyl)piperazin-1-yl)quinoline

282

3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(2-(piperidin-1- yl)ethyl)piperazin-1-yl)quinoline

283

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(1- ethylpiperidin-4-yl)piperazin-1-yl)-6- (methylsulfinyl)quinoline

284

2-(4-(1-(3-((4-((3,7- dimethyloctyl)oxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

285

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

286

4-(1′-(3-((4-(decyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)morpholine

287

3-((4(decyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)-[1,4′- bipiperidin]-1yl)-6- (methylsulfinyl)quinoline

288

1″-(3-((4-(decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl-[1,4′:1′,4″- terpiperidin]-3-ol

289

4-([1,4′:1,4″-terpiperidin]-1″-yl)-3-((4- ((3,7- dimethyloctyl)oxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

290

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (decyloxy)-3-fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinoline

291

2-(4-(1-(3-((4-(decyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

292

2-(4-(1′-(3-((4- (decyloxy)phenyl)sulfonyl-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethan-1- ol

293

N,N-diethyl)l-6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin- amine

294

N-ethyl-N-isopropyl-6,7-dimethoxy-3- ((4-methoxyphenyl)sulfonyl)quinolin-4- amine

295

N,N-dibutyl-6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- amine

296

N1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- N1,N2,N2-triethylethane-1,2-diamine

297

N1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- N2,N2-diethyl)lethane-1,2-diamine

298

N1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)-N3,N3-diethyl)lpropane-1,3-diamine

299

N1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)-N4,N4-diethyl)lbutane-1,4-diamine

300

N3-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)-N1,N1-diethyl)lbutane-1,3-diamine

301

2-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperazin-1-yl)ethan-1-ol

302

3-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperazin-1-yl)-N,N-diethyl)lpropan-1- amine

303

1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-4-ol

304

(1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-3-yl)methanol

305

1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)pyrrolidin-3-ol

306

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-((1S,4S)-5- methyl-2,5-diazabicyclo[2,2,1]heptan-2- yl)quinoline

307

4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- N,N-dimethyl-1,4-diazepane-1- carboxamide

308

1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 4-phenylpiperidin-4-ol

309

methyl 4-(1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)benzoate

310

4-(1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)-N-methylbenzamide

311

6,7-dimethoxy-4-(4-(4- methoxyphenyl)piperidin-1-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline

312

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-(4-(4- (pyrrolidin-1-ylmethyl)phenyl)piperidin- 1-yl)quinoline

313

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-(3- phenylpyrrolidin-1-yl)quinoline

314

4-(3-(benzo[d][1,3]dioxol-5- yl)pyrrolidin-1-yl)-6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinoline

315

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-(4- phenylpiperazin-1-yl)quinoline

316

6,7-dimethoxy-4-(4-(4- methoxyphenyl)piperazin-1-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline

317

ethyl 4-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperazin-1-yl)benzoate

318

4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1-(4-methoxyphenyl)piperazin-2-one

319

N-cyclohexyl-4-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperazin-1-yl)benzamide

320

4-([1,4′-bipiperidin]-1′-yl)-6,7- dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinoline

321

1-(1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)pyrrolidin-2-one

322

(1-(1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)pyrrolidin-2- yl)methanol

323

2-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1,4-diazepan-1-yl)ethan-1-ol

324

7-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1-isobutyldecahydropyrido[4,3- e][1,4]oxazepine

325

1-((4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1,4-diazepan-1-yl)methyl)cyclopentan-1- ol

326

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-(4-(oxelan-3- yl)-1,4-diaxepan-1-yl)quinoline

327

6-chloro-2-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1,4-diazepan-1-yl)benzo[d]thiazole

328

1-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 4-methyl-1,4-diazepan-5-one

329

6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)-4-(4- (tetrahydro-2H-thiopyran-4-yl)-1,4- diazepan-1-yl)quinoline

330

4-(4-(6,7-dimethoxy-3-((4- methoxyphenyl)sulfonyl)quinolin-4-yl)- 1,4-diazepan-1-yl)tetrahydro-2H- thiopyran 1,1-dioxide

331

4-([1,4′-bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl)-N,N- dimethylquinoline-6-carboxamide

332

3-((4-methoxyphenyl)sulfonyl)-N,N- dimethyl-4-(4-(2-oxopyrrolidin-1- yl)piperidin-1-yl)quinoline-6-carboxamid

333

4-(4-(2-(dimethylamino)-2-oxoethyl)-1,4- diazepan-1-yl)-3-((4- methoxyphenyl)sulfonyl)-N,N- dimethyl)quinoline-6-carboxamide

334

4-([1,4′-bipiperidin]-1′-yl)-3-((4- methoxyphenyl)sulfonyl)-N- methylquinoline-6-carboxamide

335

3-((4-methoxyphenyl)sulfonyl)-N- methyl-4-(4-methyl-1,4-diazepan-1- yl)quinoline-6-carboxamide

336

4-(4-(2-(hydroxymethyl)pyrrolidin-1- yl)piperidin-1-yl)-3-((4- methoxyphenyl)sulfonyl)-N- methylquinoline-6-carboxamide

337

4([1,4′-bipiperidin]-1′-yl)-N-(2- (diethyl)lamino)ethyl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxamide

338

N-(2-(diethyl)lamino)ethyl)-4-(1- isobutyloctahydropyrido[4,3- e][1,4]oxazepin-7(5H)-yl)-3-((4- methoxyphenyl)sulfonyl)quinoline-6- carboxamide

339

2-(4-(1-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

340

2-(4-(1′-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethan-1- ol

341

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

342

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

343

1″-(3-((4-(dodecyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinolin- 4-yl)-[1,4′:1′,4″-terpiperidin]-3-ol

344

2-(4-(1-(6-(methylsulfinyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)piperidin-4-yl)piperazin-1-yl)ethan- 1-ol

345

2-(4-(1′-(6-(methylsulfinyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)-[1,4′-bipiperidin]-4-yl)piperazin-1- yl)ethan-1-ol

346

4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

347

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methyl(λ 1 -oxidanyl)-λ 3 -sulfanyl)-3- ((4-(tetradecyloxy)phenyl)sulfonyl)quinoline

348

1″-(6-(methyl(λ 1 -oxidanyl)-λ 3 -sulfanyl)- 3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)-[1,4′:1,4″-terpiperidin]-3-ol

349

1-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)piperidin-4- yl)pyrrolidin-2-one

350

(1-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)piperidin-4- yl)pyrrolidin-2-yl)methanol

351

2-(4-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-1,4-diazepan- 1-yl)ethan-1-ol

352

7-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-1- isobutyldecahydropyrido[4,3- e][1,4]oxazepine

353

4-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-N-(2,2,2- trifluoroethyl)-1,4-diazepane-1- sulfonamide

354

1-((4-(3-((4-butoxyphenyl)sulfonyl-6- (methylthio)quinolin-4-yl)-1,4-diazepan- 1-yl)methyl)cyclopentan-1-ol

355

3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)-4-(4-(oxelan-3-yl)-1,4- diazepan-1-yl)quinoline

356

2-(4-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-1,4-diazepan- 1-yl)-6-chlorobenzo[d]thiazole

357

1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-4-methyl-1,4- diazepan-5-one

358

3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)-4-(4-(tetrahydro-2H- thiopyran-4-yl)-1,4-diaxepan-1- yl)quinoline

359

4-(4-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)-1,4-diazepan- 1-yl)tetrahydro-2H-thiopyran 1,1-dioxide

360

3-((4-methoxyphenyl)sulfonyl)-N- methyl-4-methylamino)quinoline- 6-carboxamide

361

1-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylthio)quinolin-4-yl)piperidin-4- yl)pyrrolidin-2-one

362

2-(4-(1-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

363

4-([1,4′:1,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)-3-fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinoline

364

1″-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

365

2-(4-(1-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

366

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((3- fluoro-4-(tetradecyloxy)phenylsulfonyl)- 6-(methylsulfinyl)quinoline

367

1″-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

368

2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

369

2-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

370

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

371

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

372

1″-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl-[1,4′:1′,4″- terpiperidin]-4-ol

373

1″-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-4-ol

374

1″-(3-((4-(dodecyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinolin-4-yl)- [1,4′:1′,4″-terpiperidin]-4-ol

375

1″-(6-(methylsulfinyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)-[1,4′:1′,4″-terpiperidin]-4-ol

376

2-(4-(1-(3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

377

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

378

1″-(3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

379

3-((4-methoxyphenyl)sulfonyl)-N,N- dimethyl-4-(4-methyl-1,4-diazepan-1- yl)quinoline-6-carboxamide

380

2-(4-(1-(6-(methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)piperazin-1-yl)ethanol

381

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinoline

382

1″-(6-(methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinolin-4- yl)-[1,4,:1′,4″-terpiperidin]-4-ol

383

1″-(6-(methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinolin-4- yl)-[1,4′:1′,4″-terpiperidin]-3-ol

384

2-(4-((4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methylsulfinyl)quinolin-3- yl)sulfonyl)phenoxy)-N,N- diethyl)lethanamine

385

2-(4-(1′-(3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)pipeiazin-1-yl)ethanol

386

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

387

2-(4-(1′-(3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

388

3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

389

1′-(3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

390

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

391

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

392

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

393

4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)quinoline

394

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

395

3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

396

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

397

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

398

4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

399

3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

400

4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)thiomorpholine

401

1-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-ylethanone

402

3-((3-fluoro-4- (tetradecyloxylphenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfonyl)quinoline

403

(S)-1″-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6-((S)- methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

404

(S)-1″-(3-((4- (dodecyloxy)phenyl)sulfollyl)-6-((R)- methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

405

(R)-1″-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6-((S)- methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

406

(R)-1″-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6-((R)- methylsulfinyl)quinolin-4-yl)-[1,4′:1′,4″- terpiperidin]-3-ol

407

(R)-2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazn-1-yl)ethanol

408

(S)-2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

409

(R)-2-(4-(1′′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

410

(S)-2-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

411

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

412

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- isopropylpipeiazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

413

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

414

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

415

3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

416

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

417

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

418

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

419

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

420

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

421

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

422

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

423

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

424

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

425

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

426

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1yl)-6- (methylsulfinyl)quinoline

427

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpipendin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

428

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- methylpiperazn-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

429

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

430

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

431

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

432

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazn-1-yl-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

433

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

434

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)pipeiaxip-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

435

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

436

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

437

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

438

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

439

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

440

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

441

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

442

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

443

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

444

3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

445

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- methylsulfinyl)quinoline

446

3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

447

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

448

3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

449

4-(4-(4-(1-ethylpiperidin-4-yl)piperazn- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

450

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)-2,3- difluorophenyl)sulfonyl-6- (methylsulfinyl)quinoline

451

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-ethylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

452

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

453

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

454

4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

455

(R)-4-(4-(4-methylpiperazn-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

456

(S)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

457

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

458

(S)-4-(4-(4-ethylpiperazn-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

459

(R)-4-(4-(4-cyclopropylpiperazin-1-yl)- [1,4′-bipiperidin]-1′-yl)-6- (methylsulfinyl)-3-((4- (octadecyloxy)phenyl)sulfonyl)quinoline

460

(S)-4-(4-(4-cyclopropylpiperazin-1-yl)- [1,4′-bipiperidin]-1′-yl)-6- (methylsulfinyl)-3-((4- (octadecyloxy)phenyl)sulfonyl)quinoline

461

3-((4-(icosyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

462

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

463

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

464

(S)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

465

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

466

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-ethylpiperazn-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

467

(R)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

468

(S)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl-6- (methylsulfinyl)quinoline

469

(R)-3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

470

(S)-3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

471

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

472

(S)-4-(4-(4-ethylpiperazin-1-yl-[1,4′- bipiperidin]-1′-yl-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

473

(R)-3-((4-(dodecyloxy)phenyl)sulfonyl)- 4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

474

(S)-3-((4-(dodecyloxy)phenyl)sulfonyl)- 4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsutriny)quinoline

475

(R)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

476

(S)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

477

(R)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

478

(S)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

479

(R)-4-([1,4′:1′,4′′-terpiperidin]-1″-yl)-3- ((4-(dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

480

(S)-4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3- ((4-(dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

481

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylthio)quinoline

482

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfonyl)quinoline

483

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

484

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

485

(R)-4-(4-(4-(1-ethylpiperidin-4- yl)piperazin-1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfonyl)quinoline

486

(S)-4-(4-(4-(1-ethylpiperidin-4- yl)piperazin-1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfonyl)quinoline

487

(R)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

488

(S)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

489

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetracosyloxy)phenyl)sulfonyl)quinoline

490

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-(methylsulfinyl)-3- ((4- (tetracosyloxy)phenyl)sulfonyl)quinoline

491

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (hexacosyloxy)phenyl)sulfonyl)-6- (methylsulfonyl)quinoline

492

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexacosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

493

3-((4-(icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(4-propylpiperazin- 1-yl-[1,4′-bipiperidin]-1′-yl)quinoline

494

4-(4-(4-butylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

495

3-((4-(docosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(4-propylpiperazin- 1-yl)-[1,4′-bipiperidin]-1′-yl)quinoline

496

4-(4-(4-butylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl-3-((4- (docosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

497

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylthio)quinoline

498

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfonyl)quinoline

499

4-(4-(4-(1-ethylpiperidin-4-yl)piperazn- 1-yl)piperidin-1-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

500

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

501

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3- ((4-(hexadecyloxy)phenyl)sulfonyl)-6- methoxyquinoline

502

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3- ((4-(hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

503

4-(4-(4-(1-ethylolneridin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

504

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

505

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- methoxyquinoline

506

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

507

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-(methylthio)-3- ((4-(octadecyloxy)phenyl)sulfonyl)quinoline

508

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

509

4-(4-(4-(1-ethylolneridin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-methoxy-3-((4- (octadecyloxy)phenyl)sulfonyl)quinoline

510

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (octadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

511

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- methylthio)quinoline

512

4-(4-(4-(1-ethylolneridin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

513

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- methoxyquinoline

514

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- methoxyquinoline

515

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

516

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfiny)quinoline

517

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- methoxyquinoline

518

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

519

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl-6- (methylthio)quinoline

520

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

521

4-(4-(4-(1-ethylolneridin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- methoxyquinoline

522

4-(4-(4-(I-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

523

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylthio)quinoline

524

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfonyl)quinoline

525

3-((4-(docosyloxy)phenyl)sulfonyl-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6-methoxyquinoline

526

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

527

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylthio)quinoline

528

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

529

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6-methoxyquinoline

530

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

531

3-((4-(docosyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

532

3-((4-(docosyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

533

3-((4-(docosyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

534

3-((3,5-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

535

3-((2,3-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

536

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

537

3-((3,5-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

538

3-((2,3-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

539

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

540

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

541

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

542

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

543

3-((2,6-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

544

3-((2,6-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

545

3-(42,6-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

546

3-((4-(docosyloxy)-2,6- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

547

3-((2,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

548

3-((2,5-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

549

3-((2,5-difluoro-4- (icosyloxy)phenyl)sulfonyl-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline and

550

3-((4-(docosyloxy)-2,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

29. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2021
From: SUN, PU
To: ATENGEN, INC
Reel/Frame 056738/0270 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2021
From: SUN, HUI; AU, ADRIAN CHICHUEN; CHENG, GUO; ZHONG, MING
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 056738/0559 →
Continuity (2)
Provisional Application 62916983 · Oct 18, 2019
Related Publication 20210147385A1 · May 20, 2021
Cited By (2)
US 12,590,298 US 12,612,385