IP Library Granted Patent US 10,442,783
Granted Patent B2
US 10,442,783 · App. 12/938,609 · Granted Oct 15, 2019

2,3-disubstituted chromen-4-one compounds as modulators of protein kinases

Inventors: Meyyappan Muthuppalaniappan (Hyderabad, IN); Srikant Viswanadha (Hyderabad, IN); Govindarajulu Babu (Hyderabad, IN); Swaroop Kumar V. S. Vakkalanka (La Chaux-de-Fonds, CH)
Assignee: RHIZEN PHARMACEUTICALS SA
C07D311/36A61K31/352A61K31/4178A61K31/4184A61K31/437A61K31/519A61K31/52A61K31/522A61K31/5377A61K45/06C07D405/06C07D413/10C07D413/14C07D471/04C07D473/08C07D473/34C07D473/38C07D473/40C07D487/04Y02A50/422
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Quick Facts
Patent No.
US 10,442,783
App. No.
12/938,609
Granted
Oct 15, 2019
Kind
B2
Abstract

The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

Claims (101)

1. A compound of the formula:

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

R is selected from −OR a , substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group; where R a is selected from hydrogen, and substituted or unsubstituted (C 1-6 )alkyl;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

q is 1 or 2; and

Cy 2 is substituted or unsubstituted heteroaryl.

2. A compound of claim 1 , wherein R is substituted or unsubstituted C 1-6 alkyl, or —O(unsubstituted C 1-6 alkyl).

3. A compound of claim 2 , wherein R is methoxy.

4. A compound of claim 1 , wherein Cy 1 is substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

5. A compound of claim 1 , wherein Cy 1 is selected from:

6. A compound of claim 1 , wherein R 1 and R 2 represent hydrogen or substituted or unsubstituted C 1-6 alkyl.

7. A compound of claim 1 , wherein L 1 is absent.

8. A compound of claim 1 , wherein Cy 2 is

wherein

X is CR 3 ; and

R 3 is independently selected from hydrogen, hydroxy, halogen, carboxyl, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted heterocyclylalkyl ring, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted guanidine, —COOR x , —C(O)R x , —C(S)R x , —C(O)NR x R y , —C(O)ONR x R y , —NR y R z , —NR x CONR y R z , —N(R x )SOR y , —N(R x )SO 2 R y , —NR x C(O)OR y , —NR x R y , —NR x C(O)R y —, —NR x C(S)R y , —NR x C(S)NR y R z , —SONR x R y —, —SO 2 NR x R y —, —OR x , —OR x C(O)NR y R z , —OR x C(O)OR y —, —OC(O)R x , —OC(O)NR x R y , —R x NR y C(O)R z , —R x OR y , —R x C(O)OR y , —R x C(O)NR y R z , —R x C(O)R x , —R x OC(O)R y , —SR x , —SOR x , —SO 2 R x , —ONO 2 , wherein R x , R y and R z in each of the above groups can be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted heterocyclylalkyl ring, substituted or unsubstituted heteroarylalkyl, or substituted or unsubstituted heterocyclic ring, or any two of R x , R y and R z may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 membered ring, which may optionally include heteroatoms which may be the same or different and are selected from O, NR f (wherein R f is hydrogen or substituted or unsubstituted alkyl) or S.

9. A compound of the formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from −OR a , substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group, where R a is selected from hydrogen, and substituted or unsubstituted (C 1-6 )alkyl;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

q is 1 or 2; and

Cy 2 is

10. A pharmaceutical composition comprising a compound of formula (I-A)

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from —OR a , substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group, where R a is selected from hydrogen, and unsubstituted (C 1-6 )alkyl;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is selected from substituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2;

and a pharmaceutically acceptable carrier.

11. The pharmaceutical composition of claim 10 , further comprising one or more additional therapeutic agents selected from anti-cancer agents, anti-inflammatory agents, immunosuppressive agents, steroids, non-steroidal anti-inflammatory agents, antihistamines, analgesics, and mixtures thereof.

12. A method of inhibiting a catalytic activity of a PI3 kinase present in a cell, comprising contacting the cell with an effective amount of a compound of claim 1 .

13. The method of claim 12 , wherein the inhibition takes place in a subject suffering from a disease or disorder which is cancer, bone disorder, inflammatory disease, immune disease, nervous system disease, metabolic disease, respiratory disease, thrombosis, or cardiac disease.

14. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 1 .

15. The method of claim 14 , further comprising the step of administering simultaneously or sequentially to a subject in need thereof at least one other anti-cancer agent.

16. A compound of formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is selected from a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q —, —O—, or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2.

17. A compound of formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from —OR x (wherein R x is hydrogen or unsubstituted (C 1-6 )alkyl), substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form an oxo group (═O) or a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2.

18. A compound of formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from —OR x (wherein R x is hydrogen or unsubstituted (C 1-6 )alkyl), substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both W and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2.

19. The compound of claim 18 , wherein Cy 2 is selected from substituted aryl and substituted or unsubstituted heteroaryl.

20. A compound of formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, substituted or unsubstituted heterocyclic group, and —OR x wherein R x is unsubstituted (C 1-6 )alkyl;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2.

21. A compound selected from 2-((6-amino-9H-purin-9-yl)methyl)-6-methoxy-3-phenyl-4H-chromen-4-one and pharmaceutically acceptable salts thereof.

22. The pharmaceutical composition of claim 10 , wherein Cy 2 is selected from substituted or unsubstituted heteroaryl.

23. The compound of claim 16 , wherein Cy 2 is selected from substituted or unsubstituted heterocyclic group and substituted or unsubstituted heteroaryl.

24. The compound of claim 17 , wherein Cy 2 is selected from substituted heteroaryl.

25. The compound of claim 17 , wherein R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl.

26. A compound of formula

or a tautomer thereof, N-oxide thereof, or pharmaceutically acceptable salt thereof, wherein

each occurrence of R is independently selected from —OR x (wherein R x is unsubstituted (C 1-6 )alkyl), substituted or unsubstituted C 1-6 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;

R 1 and R 2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C 1-6 alkyl, or both R 1 and R 2 directly bound to a common atom, may be joined to form an oxo group (═O) or a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the carbon atom to which R 1 and R 2 are bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR a and S, where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl;

Cy 1 is a monocyclic group selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

Cy 2 is selected from substituted aryl and substituted or unsubstituted heteroaryl;

L 1 is absent or selected from —(CR a R b ) q — or —C(═Y)—, where each occurrence of R a and R b may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C 1-6 )alkyl, and —OR c (wherein R c is substituted or unsubstituted (C 1-6 )alkyl) or when R a and R b are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring (including the common atom to which R a and R b are directly bound), which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NR d (wherein R d is hydrogen or substituted or unsubstituted (C 1-6 )alkyl) or S;

Y is selected from O, S, and NR a , where R a is selected from hydrogen and substituted or unsubstituted (C 1-6 )alkyl; and

q is 1 or 2.

27. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 9 .

28. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of composition of claim 10 .

29. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 16 .

30. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 17 .

31. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 18 .

32. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 20 .

33. A method of treating a subject diagnosed with chronic lymphocytic leukemia (CLL), non-Hodgkin's lymphoma (NHL), acute myeloid leukemia (AML), multiple myeloma (MM), small lymphocytic lymphoma (SLL), or indolent non-Hodgkin's lymphoma (I-NHL), comprising the step of administering to the subject an effective amount of compound of claim 26 .

Assignments (5)
CHANGE OF ADDRESS Recorded Oct 6, 2021
From: RHIZEN PHARMACEUTICALS AG
To: RHIZEN PHARMACEUTICALS AG
Reel/Frame 057836/0286 →
CHANGE OF ADDRESS Recorded Mar 22, 2021
From: RHIZEN PHARMACEUTICALS SA
To: RHIZEN PHARMACEUTICALS SA
Reel/Frame 056775/0375 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2012
From: INCOZEN THERAPEUTICS PVT. LTD.
To: RHIZEN PHARMACEUTICALS SA
Reel/Frame 027928/0920 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2011
From: MUTHUPPALANIAPPAN, MEYYAPPAN; VISWANADHA, SRIKANT; BABU, GOVINDARAJULU
To: INCOZEN THERAPEUTICS PVT. LTD.
Reel/Frame 025663/0420 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2011
From: VAKKALANKA, SWAROOP KUMAR V.S.
To: RHIZEN PHARMACEUTICALS SA
Reel/Frame 025663/0447 →
Priority Claims (2)
IN 2690/CHE/2009 · Nov 5, 2009 · national
IN 1429/CHE/2010 · May 24, 2010 · national
Continuity (2)
Provisional Application 61364661 · Jul 15, 2010
Related Publication 20110118257A1 · May 19, 2011