IP Library Granted Patent US 11,174,232
Granted Patent B2
US 11,174,232 · App. 16/867,761 · Granted Nov 16, 2021

Substituted heterocyclyl derivatives as CDK inhibitors

Inventors: Susanta Samajdar (Bangalore, IN); Ramulu Poddutoori (Karimnagar, IN); Chetan Pandit (Bangalore, IN); Subhendu Mukherjee (Hooghly, IN); Rajeev Goswami (Deharadun, IN)
Assignee: Aurigene Discovery Technologies Limited
C07D231/40A61K31/415A61K31/416A61K31/4155A61K31/4439A61K31/454A61K31/4545A61K31/4725A61K31/496A61K31/497A61K31/5377A61K45/06C07D231/56C07D401/04C07D401/12C07D401/14C07D403/12C07D413/12C07D471/04
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Quick Facts
Patent No.
US 11,174,232
App. No.
16/867,761
Granted
Nov 16, 2021
Kind
B2
Abstract

The present invention provides substituted heterocyclylderivatives of formula (I), which are therapeutically useful, particularly as selective transcriptional CDK inhibitors including CDK7, CDK9, CDK12, CDK13 and CDK18, more particularly transcriptional CDK7 inhibitors. These compounds are useful in the treatment and prevention of diseases and/or disorders associated with selective transcriptional CDKs in a mammal. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of the substituted heterocyclyl derivatives of formula (I) or a pharmaceutically acceptable salt or a stereoisomer thereof.

Claims (445)

1. A compound of formula (IB):

or a pharmaceutically acceptable salt or a stereoisomer thereof;

wherein,

ring B is phenyl, piperidinyl, pyridinyl, 1,2,3,6-tetrahydropyridinyl, piperazinyl, pyrazinyl, pyrazolyl, morpholinyl, indolinyl or pyrrolidinyl;

R 2 is (C 1 - C 6 )alkyl or (C 3 - C 10 )cycloalkyl;

R 3 is hydrogen or (C 1 - C 6 )alkyl;

R 4 at each occurrence is halo;

R 5 is

wherein R 5 ′ is hydrogen, halo, methoxymethyl or —CH 2 —NR a R b ; R 5 ″ is H;

R a and R b are each independently (C 1 - C 6 )alkyl, (C 1 - C 6 )alkoxy or methoxyethyl; alternatively, R a and R b together with the nitrogen atom to which they are attached form an optionally substituted 5 to 6 membered ring containing 0-2 additional heteroatoms that are independently N, O or S; wherein the optional substituent is one or more halo, cyano, cyano(C 1 -C 6 )alkyl, methoxymethyl or —COO-(C 1 -C 6 )alkyl or a combination thereof;

R 6 at each occurrence is halo, (C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy;

L 1 is *—CR c R d —C(O)— or absent; wherein * is point of attachment with phenyl ring;

R c and R d independently are hydrogen or (C 1 -C 6 )alkyl; alternatively, R c and R d together with the carbon atom to which they are attached form a (C 3 -C 10 )cycloalkyl ring;

L2 is —C(O)NH— or absent;

m is 0 or 1; and

q is 0 to 2.

2. The compound of claim 1 , having formula (ID):

or a pharmaceutically acceptable salt thereof or a stereoisomer thereof.

3. The compound of claim 1 , having formula (IE):

or a pharmaceutically acceptable salt thereof or a stereoisomer thereof;

wherein, L 1 is *—CR c R d —C(O)—; wherein * is point of attachment with the phenyl ring.

4. The compound of claim 1 , having a compound of formula (IF):

or a pharmaceutically acceptable salt thereof or a stereoisomer thereof;

wherein,

R 3 is hydrogen;

R5 is

wherein R 5 ′ is hydrogen, methoxymethyl or —(CH 2 )—NR a R b ; R 5 ″ is H;

R a and R b are each independently (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy or methoxyethyl;

alternatively, R a and R b together with the nitrogen atom to which they are attached form an optionally substituted 5 to 6 membered heterocyclic ring containing 0-2 additional heteroatoms that are independently N, O or S; wherein the optional substituent is one or more halo, cyano, cyano(C 1 -C 6 )alkyl, methoxymethyl or —COO-(C 1 -C 6 )alkyl or a combination thereof;

L 1 is *—CR c R d —C(O)—; wherein * is point of attachment with phenyl ring;

R c and R d independently are hydrogen or (C 1 -C 6 )alkyl; alternatively, R c and R d together with the carbon atom to which they are attached form a (C 3 -C 10 )cycloalkyl ring; and

m is 0 and R4 is absent.

5. The compound according to claim 1 , wherein ring B is phenyl or pyridinyl.

6. The compound according to claim 1 , wherein R 2 is cyclopropyl.

7. The compound according to claim 1 , wherein R 5 is

8. The compound according to claim 7 , wherein R 5 ′ is (CH 2 ) 2 —NR a R b ; wherein R a and R b are each independently (C 1 -C 6 )alkyl; alternatively, R a and R b together with the nitrogen atom to which they are attached form an optionally substituted 5 to 6 membered heterocyclic ring containing 0-2 additional heteroatoms that are independently O, S or N; wherein the optional substituent independently is one or more halo.

9. The compound according to claim 8 , wherein R a and R b together with the nitrogen atom to which they are attached form a 5 to 6 membered heterocyclic ring containing 0-2 additional heteroatoms that are independently O, S or N.

10. The compound according to claim 1 , wherein L 1 is *—CR c R d —C(O)—; wherein * is the point of attachment with the phenyl ring.

11. The compound according to claim 1 , wherein L 2 is absent.

12. The compound of claim 1 selected from the group consisting of:

Compound

No.

IUPAC name

1

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-2-enamide;

2

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide (Isomer-1 of compound-1);

3

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide (Isomer-2 of compound-1);

4

(E)-N-(5′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-2′-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

5

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-4′-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

7

(E)-N-(3′-(2-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-2-oxoethyl)-[1,1′-biphenyl]-4-

yl)-4-(dimethylamino)but-2-enamide;

8

(E)-4-(dimethylamino)-N-(3′-(1-((5-ethyl-

1H-pyrazol-3-yl)amino)-1-oxopropan-2-

yl)-[1,1′-biphenyl]-4-yl)but-2-enamide;

9

(E)-N-(3′-(1-((5-(tert-butyl)-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-2-enamide;

13

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxobutan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-2-enamide;

14

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

15

(E)-N-(3′-(1-((5-cyclobutyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)-4-(dimethylamino)but-2-enamide;

16

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)-4-(dimethylamino)but-

2-enamide;

17

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-2-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

18

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)acrylamide;

19

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-3-fluoro-[1,1′-

biphenyl]-4-yl)acrylamide;

20

N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)acrylamide;

21

N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)acrylamide

(Isomer-1 of compound-20);

22

N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)acrylamide

(Isomer-2 of compound-20);

23

N-(5′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-2′,3-difluoro-

[1,1′-biphenyl]-4-yl)acrylamide;

24

N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)acrylamide;

25

2-(4′-acrylamido-3′-fluoro-[1,1′-biphenyl]-

3-yl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-

3-methylbutanamide;

26

2-(3-(5-acrylamidopyridin-2-yl)phenyl)-

N-(5-cyclopropyl-1H-pyrazol-3-

yl)butanamide;

27

2-(4′-acrylamido-3′-fluoro-[1,1′-biphenyl]-

3-yl)-N-(5-cyclopropyl-1H-pyrazol-3-

yl)butanamide;

28

(E)-N-(3′-(1-((5-cyclopentyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

29

(E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-

(3-(1-(4-(dimethylamino)but-2-

enoyl)indolin-5-yl)phenyl)propanamide;

30

N-(3′-(1-((5-cyclopropyl-4-methyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-4-yl)acrylamide;

31

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxobutan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-(dimethylamino)but-

2-enamide;

32

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-(diethylamino)but-2-enamide;

33

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-(pyrrolidin-1-yl)but-

2-enamide;

34

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-morpholinobut-2-enamide;

35

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)-4-morpholinobut-2-enamide;

36

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-3-methyl-1-oxobutan-2-

yl)phenyl)pyridin-3-yl)-4-(dimethylamino)but-

2-enamide;

37

(E)-4-((6-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)amino)-N,N-

dimethylbut-2-enamide;

38

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-yl)phenyl)-

2-fluoropyridin-3-yl)-4-(dimethylamino)but-

2-enamide;

39

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)-4-(piperidin-1-yl)but-

2-enamide;

40

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(piperidin-1-yl)but-

2-enamide;

41

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-methoxybut-2-enamide;

42

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-

2-enamide;

43

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-3-methyl-1-oxobutan-2-yl)-3-

fluoro-[1,1′-biphenyl]-4-yl)-4-

(dimethylamino)but-2-enamide;

45

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(3-fluoropyrrolidin-

1-yl)but-2-enamide;

46

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-3-

fluoropyrrolidin-1-yl)but-2-enamide;

47

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-3-fluoropyrrolidin-

1-yl)but-2-enamide (Isomer-1 of

compound-46);

48

E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-3-fluoropyrrolidin-

1-yl)but-2-enamide (Isomer-2 of

compound-46);

49

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((R)-3-

fluoropyrrolidin-1-yl)but-2-enamide

50

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((R)-3-fluoropyrrolidin-

1-yl)but-2-enamide (Isomer-1 of

compound-49);

51

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((R)-3-fluoropyrrolidin-

1-yl)but-2-enamide (Isomer-2 of

compound-49);

55

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(diethylamino)but-

2-enamide;

56

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-3-methyl-1-oxobutan-2-

yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-

2-enamide;

57

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(3-fluoropiperidin-

1-yl)but-2-enamide;

58

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)phenyl)-

2-fluoropyridin-3-yl)-4-morpholinobut-2-enamide;

59

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)phenyl)-

6-fluoropyridin-2-yl)-4-morpholinobut-2-enamide;

60

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-3-yl)-4-morpholinobut-2-enamide;

61

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-yl)-[1,1′-

biphenyl]-3-yl)-4-morpholinobut-2-enamide;

62

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-

(methoxy(methyl)amino)but-2-enamide;

63

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)phenyl)-

3-fluoropyridin-2-yl)-4-morpholinobut-2-enamide;

64

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)phenyl)-

2-fluoropyridin-3-yl)-4-(3-fluoropyrrolidin-

1-yl)but-2-enamide;

65

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)-3-methoxy-

[1,1′-biphenyl]-4-yl)acrylamide;

66

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)-3-methyl-[1,1′-

biphenyl]-4-yl)acrylamide;

67

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)-3,5-dimethyl-

[1,1′-biphenyl]-4-yl)acrylamide;

68

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((2-

methoxyethyl)(methyl)amino)but-2-enamide;

69

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(1H-imidazol-

1-yl)but-2-enamide;

70

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-2-

(methoxymethyl)pyrrolidin-1-yl)but-2-enamide;

71

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-2-

(methoxymethyl)pyrrolidin-1-yl)but-2-enamide

(Isomer-1 of compound-70);

72

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((S)-2-

(methoxymethyl)pyrrolidin-1-yl)but-2-enamide

(Isomer-2 of compound-70);

73

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-2-methoxy-

[1,1′-biphenyl]-4-yl)acrylamide;

74

N-((5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)methyl)acrylamide;

75

N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-2-methyl-[1,1′-

biphenyl]-4-yl)acrylamide;

76

2-(3-(1-acryloylindolin-5-yl)phenyl)-

N-(5-cyclopropyl-1H-pyrazol-3-

yl)propanamide;

77

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-((2S,4S)-4-

fluoro-2-(methoxymethyl)pyrrolidin-1-yl)but-

2-enamide;

78

(E)-4-(3-cyanopyrrolidin-1-yl)-N-(5-(3-(1-

((5-cyclopropyl-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)phenyl)pyridin-2-yl)but-

2-enamide;

79

N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyrazin-2-yl)acrylamide;

80

(E)-N-(3′-(1-((5-cyclopropyl-1H-pyrazol-3-

yl)amino)-1-oxopropan-2-yl)-3-fluoro-

[1,1′-biphenyl]-4-yl)-4-((S)-3-

fluoropyrrolidin-1-yl)but-2-enamide;

81

methyl ((E)-4-((5-(3-(1-((5-cyclopropyl-1H-

pyrazol-3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)amino)-4-oxobut-

2-en-1-yl)-L-prolinate;

82

(E)-4-((S)-2-(cyanomethyl)pyrrolidin-1-yl)-

N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)but-2-enamide;

83

4-acrylamido-N-(3-((5-ethyl-1H-pyrazol-

3-yl)amino)phenyl)benzamide;

84

(E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-

(3-(1-(4-(dimethylamino)but-2-enoyl)-

1,2,3,6-tetrahydropyridin-4-yl)phenyl)propanamide;

85

(E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-

2-(3-(1-(4-(dimethylamino)but-2-

enoyl)piperidin-4-yl)phenyl)propanamide;

86

N-(3′-(2-((5-methyl-1H-pyrazol-3-yl)amino)-

2-oxoethyl)-[1,1′-biphenyl]-4-

yl)acrylamide;

87

N-(3′-(1-((5-ethyl-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)-[1,1′-biphenyl]-4-

yl)acrylamide;

88

N-(3′-(1-((5-(tert-butyl)-1H-pyrazol-3-yl)amino)-

1-oxopropan-2-yl)-[1,1′-biphenyl]-

4-yl)acrylamide;

89

(E)-N-(3-((1H-indazol-3-yl)amino)phenyl)-

4-(4-(dimethylamino)but-2-

enamido)benzamide;

90

N-(3′-(1-((1H-indazol-3-yl)amino)-

1-oxopropan-2-yl)-[1,1′-biphenyl]-4-

yl)acrylamide;

91

(E)-N-(3′-(1-((1H-indazol-3-yl)amino)-1-

oxopropan-2-yl)-[1,1′-biphenyl]-4-yl)-4-

(dimethylamino)but-2-enamide;

92

(E)-N-(6-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyrazin-2-yl)-4-(pyrrolidin-1-

yl)but-2-enamide;

93

(S,E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-morpholinobut-

2-enamide;

94

(E)-N-(5-cyclopropyl-1H-pyrazol-3-

yl)-1-(3-(6-(4-(pyrrolidin-1-yl)but-2-

enamido)pyridin-3-yl)phenyl)cyclopropane-

1-carboxamide; and

95

(E)-N-(5-(3-(1-((5-cyclopropyl-1H-pyrazol-

3-yl)amino)-2-methyl-1-oxopropan-2-

yl)phenyl)pyridin-2-yl)-4-(pyrrolidin-1-yl)but-

2-enamide;

or a pharmaceutically acceptable salt or a stereoisomer thereof.

13. A pharmaceutical composition comprising the compound of claim 1 , or a pharmaceutically acceptable salt or a stereoisomer thereof and at least one pharmaceutically acceptable carrier or excipient.

14. A pharmaceutical composition comprising the compound of claim 12 , or pharmaceutically acceptable salt or a stereoisomer thereof, and at least one pharmaceutically acceptable carrier or excipient.

Assignments (2)
CHANGE OF NAME Recorded Apr 13, 2023
From: AURIGENE DISCOVERY TECHNOLOGIES LIMITED
To: AURIGENE ONCOLOGY LIMITED
Reel/Frame 063312/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2021
From: SAMAJDAR, SUSANTA; PODDUTOORI, RAMULU; PANDIT, CHETAN; MUKHERJEE, SUBHENDU; GOSWAMI, RAJEEV
To: AURIGENE DISCOVERY TECHNOLOGIES LIMITED
Reel/Frame 057693/0589 →
Priority Claims (2)
IN 2803/CHE/2015 · Jun 4, 2015 · national
IN 6214/CHE/2015 · Nov 18, 2015 · national
Continuity (2)
Continuation 15579246
Related Publication 20200262793A1 · Aug 20, 2020
Cited By (1)
US 12,331,023