IP Library › Granted Patent US 9,511,070
Granted Patent B2
US 9,511,070 · App. 14/422,543 · Granted Dec 6, 2016

Heterocyclyl carboxamides for treating viral diseases

Inventor: Eliezer Huberman (Chicago, IL)
Assignee: NovaDrug, LLC
A61K31/519A61K31/445A61K31/45A61K31/454A61K31/4545A61K31/4709A61K31/496A61K31/497A61K31/506
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Quick Facts
Patent No.
US 9,511,070
App. No.
14/422,543
Granted
Dec 6, 2016
Kind
B2
Abstract

Methods, uses, medicaments, and unit doses for treating viral diseases are described herein. The methods, uses, medicaments, and unit doses include (a) substituted piperidine and piperazine carboxamides, or a pharmaceutically acceptable salt thereof and (b) one or more pharmaceutically acceptable carriers, excipients or diluents, or combinations thereof. Viral diseases include hepatitis C virus, HIV, BVDV, and Coronavirus infections.

Claims (1016)

1. A method for treating an HCV or BVDV infection in a host animal, the method comprising the step of administering to the host animal a therapeutically effective amount of one or more compounds of the formula

or a pharmaceutically acceptable salt thereof; and wherein:

the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Com-

bina-

tion

Mode

Ar 1

X

R 2

1

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

2

4-(3-MeC 6 H 4 )C 6 H 4

CH 2

4-OH-3-MeO—C 6 H 3

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-

CH 2

2-MeO—C 6 H 4

yl)C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

7

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-MeO—C 6 H 4

8

3-(3-FC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

9

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-(n-Bu)-imidazol-4-yl

10

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2,3-Methylenedioxy-C 6 H 3

11

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3-OH—C 6 H 4

12

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-OH-6-MeO—C 6 H 3

13

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

14

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3-Me-4-MeO—C 6 H 3

15

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3-MeO—C 6 H 4

16

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-F-2-MeO—C 6 H 3

17

3-(2-Indolyl)C 6 H 4

CH 2

(1-i-Pr-pyrazol-4-yl)

18

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

t-Bu

19

3-(2-Furyl)C 6 H 4

CH 2

Quinolin-8-yl

20

3-(2-Me-1,3,4-

C(═O)

2-Furyl

thiazol-5-yl)C 6 H 4

21

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

4-OH-3-MeO—C 6 H 3

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-

CH 2

3-MeO—C 6 H 4

ylC 6 H 4

24

4-benzimidazol-2-

CH 2

5-Et-furan-2-yl

ylC 6 H 4

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

26

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

27

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

28

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

29

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Et

30

4-benzimidazol-2-

CH 2

3-MeO—C 6 H 4

ylC 6 H 4

31

4-(3,5-Me 2 -pyrazol-

CH 2 CH═CH

2-MeO—C 6 H 4

1-yl)C 6 H 4

(E)

32

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-Et-5-Me-imidazol-4-yl

33

3-(3-MeOC 6 H 4 )C 6 H 4

CH 2

CH═C(Me) 2

34

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

3-MeO—C 6 H 4

35

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

naphtha-1-yl

36

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

37

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Pr-5-Me-pyrazol-4-yl

38

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Me

39

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl

40

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-3,5-Me 2 -pyrazol-4-yl

41

2-PhO-pyridin-5-yl

CH 2

Ph

42

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-Et-pyrazol-4-yl

43

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

44

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

1-Pr-5-Me-pyrazol-4-yl

45

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-5-MeO—C 6 H 3

46

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-pyrazol-4-yl

47

2-PhO-pyridin-5-yl

CH 2

5-Cl-thien-2-yl

48

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2,3-(MeO) 2 —C 6 H 3

49

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

4-HO-3-MeO—C 6 H 3

50

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

5-(i-Bu)-pyrazol-3-yl

51

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

52

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2,5-Me 2 —C 6 H 3

53

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Benzo-2,1,3-thiadiazol-5-yl

54

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

55

4-(benzimidazol-2-

CH 2

Cyclohexen-4-yl

yl)C 6 H 4

56

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

57

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

5-Me-furan-2-yl

58

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-Et-5-Me-pyrazol-4-yl

59

4-(benzimidazol-2-

CH 2

3-FC 6 H 4

yl)C 6 H 4

60

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Et-pyrazol-4-yl

61

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

Pyridin-2-yl

62

4-(Benzimidazol- 2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

64

4-(2-F—PhO)Ph

—

65

3-(3-F—Ph)Ph

—

66

3-Br—Ph

—

and one or more pharmaceutically acceptable carriers, excipients, or diluents, or combinations thereof.

2. The method of claim 1 , wherein the viral infection is a HCV infection.

3. The method of claim 1 , wherein the viral infection is a BVDV infection.

4. The method of claim 1 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Com-

bina-

tion

Mode

Ar 1

X

R 2

1

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-yl)C 6 H 4

CH 2

2-MeO—C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

7

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-MeO—C 6 H 4

8

3-(3-FC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

9

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-(n-Bu)-imidazol-4-yl

10

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2,3-Methylenedioxy-C 6 H 3

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

26

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

27

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

28

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

29

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Et

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

33

3-(3-MeOC 6 H 4 )C 6 H 4

CH 2

CH═C(Me) 2

38

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Me

39

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl

40

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-3,5-Me 2 -pyrazol-4-yl

41

2-PhO-pyridin-5-yl

CH 2

Ph

42

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-Et-pyrazol-4-yl

43

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 2 -pyrazin-2-yl

45

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-5-MeO—C 6 H 3

47

2-PhO-pyridin-5-yl

CH 2

5-Cl-thien-2-yl

49

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

4-HO-3-MeO—C 6 H 3

51

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

54

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

56

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

58

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-Et-5-Me-pyrazol-4-yl

60

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Et-pyrazol-4-yl

62

4-(Benzimidazol-2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

64

4-(2-F—PhO)Ph

—

65

3-(3-F—Ph)Ph

—

5. The method of claim 1 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-yl)C 6 H 4

CH 2

2-MeO—C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

39

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl

62

4-(Benzimidazol-2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

65

3-(3-F—Ph)Ph

—

6. The method of claim 2 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

1

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

2

4-(3-MeC 6 H 4 )C 6 H 4

CH 2

4-OH-3-MeO—C 6 H 3

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-yl)C 6 H 4

CH 2

2-MeO—C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

7

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-MeO—C 6 H 4

8

3-(3-FC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

9

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-(n-Bu)-imidazol-4-yl

10

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2,3-Methylenedioxy-C 6 H 3

11

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3-OH—C 6 H 4

12

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-OH-6-MeO—C 6 H 3

13

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

14

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3-Me-4-MeO—C 6 H 3

15

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3-MeO—C 6 H 4

16

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-F-2-MeO—C 6 H 3

17

3-(2-Indolyl)C 6 H 4

CH 2

(1-i-Pr-pyrazol-4-yl)

18

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

t-Bu

19

3-(2-Furyl)C 6 H 4

CH 2

Quinolin-8-yl

20

3-(2-Me-1,3,4-thiazol-5-yl)C 6 H 4

C(═O)

2-Furyl

21

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

4-OH-3-MeO—C 6 H 3

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

26

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

27

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

28

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

29

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Et

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

31

4-(3,5-Me 2 -pyrazol-1-yl)C 6 H 4

CH 2 CH═CH(E)

2-MeO—C 6 H 4

32

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-Et-5-Me-imidazol-4-yl

33

3-(3-MeOC 6 H 4 )C 6 H 4

CH 2

CH═C(Me) 2

34

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

3-MeO—C 6 H 4

35

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

naphtha-1-yl

36

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

37

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Pr-5-Me-pyrazol-4-yl

38

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Me

39

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl

40

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-3,5-Me 2 -pyrazol-4-yl

41

2-PhO-pyridin-5-yl

CH 2

Ph

42

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-Et-pyrazol-4-yl

43

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

44

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

1-Pr-5-Me-pyrazol-4-yl

45

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-5-MeO—C 6 H 3

46

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-pyrazol-4-yl

47

2-PhO-pyridin-5-yl

CH 2

5-Cl-thien-2-yl

48

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2,3-(MeO) 2 —C 6 H 3

49

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

4-HO-3-MeO—C 6 H 3

50

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

5-(i-Bu)-pyrazol-3-yl

51

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

52

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2,5-Me 2 -C 6 H 3

53

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Benzo-2,1,3-thiadiazol-5-yl

54

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

55

4-(benzimidazol-2-yl)C 6 H 4

CH 2

Cyclohexen-4-yl

56

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

57

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

5-Me-furan-2-yl

58

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-Et-5-Me-pyrazol-4-yl

59

4-(benzimidazol-2-yl)C 6 H 4

CH 2

3-FC 6 H 4

60

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Et-pyrazol-4-yl

61

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

Pyridin-2-yl.

7. The method of claim 2 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

1

3-(3-FC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-yl)

CH 2

2-MeO—C 6 H 4

C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

7

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-MeO—C 6 H 4

8

3-(3-FC 6 H 4 )C 6 H 4

CH 2

4-OH—C 6 H 4

9

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-(n-Bu)-imidazol-4-yl

10

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2,3-Methylenedioxy-C 6 H 3

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

26

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

27

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

28

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

29

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Et

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

33

3-(3-MeOC 6 H 4 )C 6 H 4

CH 2

CH═C(Me) 2

38

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

Me

39

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl

40

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-(i-Pr)-3,5-Me 2 -pyrazol-

4-yl

41

2-PhO-pyridin-5-yl

CH 2

Ph

42

3-(3-ClC 6 H 4 )C 6 H 4

CH 2

1-Et-pyrazol-4-yl

43

3-(3-FC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

45

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-HO-5-MeO—C 6 H 3

47

2-PhO-pyridin-5-yl

CH 2

5-Cl-thien-2-yl

49

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

4-HO-3-MeO—C 6 H 3

51

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

3,5,6-Me 3 -pyrazin-2-yl

54

3-(3-FC 6 H 4 )C 6 H 4

CH 2

2-HO-3-MeO—C 6 H 3

56

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-allyl-3-Me-pyrazol-4-yl

58

3-(3-FC 6 H 4 )C 6 H 4

CH 2

1-Et-5-Me-pyrazol-4-yl

60

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

1-Et-pyrazol-4-yl.

8. The method of claim 2 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

3

4-(2-FC 6 H 4 O)C 6 H 4

CH 2

2-OH-4-MeO—C 6 H 3

4

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

Quinolin-8-yl

5

4-(Benzimidazol-2-yl)C 6 H 4

CH 2

2-MeO—C 6 H 4

6

2-(3-MeOC 6 H 4 )C 6 H 4

CH 2

4-OH-3,5-Me 2 —C 6 H 2

39 

4-(2-FC 6 H 4 O)C 6 H 4

—

1-Et-piperidin-4-yl.

9. The method of claim 3 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

62

4-(Benzimidazol-2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

64

4-(2-F—PhO)Ph

—

65

3-(3-F—Ph)Ph

—

66

3-Br—Ph

—

10. The method of claim 3 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

62

4-(Benzimidazol-2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

64

4-(2-F—PhO)Ph

—

65

3-(3-F—Ph)Ph

—

11. The method of claim 3 , wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

30

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

62

4-(Benzimidazol-2-yl)Ph

—

63

3-(Indol-2-yl)Ph

—

65

3-(3-F—Ph)Ph

—

12. A method for treating an HIV infection in a host animal, the method comprising the step of administering to the host animal a therapeutically effective amount of one or more compounds of the formula

or a pharmaceutically acceptable salt thereof; wherein the one of more compounds each comprise a combination mode of Ar 1 , X, and R 2 , said combination mode selected from the group consisting of:

Combination

Mode

Ar 1

X

R 2

22

3-indol-2-ylC 6 H 4

C(O)

C≡C—CH 3

23

4-benzimidazol-2-ylC 6 H 4

CH 2

3-MeO—C 6 H 4

24

4-benzimidazol-2-ylC 6 H 4

CH 2

5-Et-furan-2-yl

25

3-indol-2-ylC 6 H 4

C(O)

thiazol-5-yl

30

4-benzimidazol-2-ylC6H4

CH 2

3-MeO—C 6 H 4

and one or more pharmaceutically acceptable carriers, excipients, or diluents, or combinations thereof.

13. A method for treating a coronavirus infection in a host animal, the method comprising the step of administering to the host animal a therapeutically effective amount of one or more compounds selected from the group consisting of:

or a pharmaceutically acceptable salt thereof and one or more pharmaceutically acceptable carriers, excipients, or diluents, or combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2015
From: HUBERMAN, ELIEZER
To: NOVADRUG, LLC
Reel/Frame 035027/0713 →
Continuity (3)
Provisional Application 61695869 · Aug 31, 2012
Provisional Application 61779595 · Mar 13, 2013
Related Publication 20150238489A1 · Aug 27, 2015