IP Library › Granted Patent US 8,399,683

Granted Patent B2

US 8,399,683 · App. 13/063,219 · Granted Mar 19, 2013

IAP inhibitors

Inventors: Stephen M. Condon (Glenmoore, PA); Matthew G. Laporte (Honeybrook, PA)

Assignee: TetraLogic Pharmaceuticals

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Quick Facts

Patent No.: US 8,399,683
App. No.: 13/063,219
Granted: Mar 19, 2013
Kind: B2

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Abstract

The present invention describes compounds, processes for their preparation, pharmaceutical compositions containing them, and their use in therapy.

Claims (253)

1. A compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1a and R1b are each independently selected from H, alkyl, or substituted alkyl;

R2 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R6 is selected from H, alkyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl; or R6 has the following formula (IA):

where R8 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

and R9 is selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heterocycloalkyl, substituted heterocycloalkyl, heteroaryl, or substituted heteroaryl; or R9 has the following formula (IB):

where R10a and R10b are independently selected from H, alkyl, or substituted alkyl;

and R11 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R7 is selected from H, or a 3-indolyl of the formula (IC):

where R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H or hydroxy.

2. A compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroaryl, or substituted heteroaryl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R1a and R1b are each independently selected from H, alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R2 is alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

R6 is selected from H; alkylsulfonyl; arylsulfonyl; alkyl; substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkoxy, amino, nitro, cycloalkyl, aryl, heteroaryl optionally substituted with lower alkyl or halogen, alkylsulfonyl and arylsulfonyl; cycloalkyl; substituted cycloalkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; aryl; substituted aryl, wherein the substituents are selected from the group consisting of alkyl, halogen, hydroxy, mercapto, carboxyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, nitro, alkylsulfonyl and arylsulfonyl; heterocycloalkyl; substituted heterocycloalkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; heteroaryl; or substituted heteroaryl, wherein the substituents are selected from the group consisting of halogen, hydroxy, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; or R6 has the following formula (IA):

where R8 is alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl

and R9 is selected from H, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroaryl, or substituted heteroaryl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; or, R9 has the following formula (IB):

where R10a and R10b are independently selected from H, alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; and

R11 is selected from H, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroaryl, or substituted heteroaryl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R7 is selected from H, or a 3-indolyl of the formula (IC):

where R3 is selected from H, alkyl, or substituted alkyl, where the substituents are selected from the group consisting of halogen, hydroxy, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R4 is selected from H, halogen, alkyl, or substituted alkyl, where the substituents are selected from the group consisting of halogen, hydroxy, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl, where the substituents are selected from the group consisting of halogen, hydroxy, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; and

R12 is selected from H or hydroxy.

3. A compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, or substituted alkenyl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cyclopropyl, alkoxy, amino, and nitro; and

4. A compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, or lower alkyl;

R1a and R1b are each independently selected from H, or lower alkyl;

R2 is selected from H; lower alkyl; cycloalkyl, or substituted lower alkyl wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

R6 is selected from H; lower alkylsulfonyl; alkyl; substituted alkyl, wherein the alkyl substituents are selected from the group consisting of hydroxy, oxo, halogen, alkoxy, cycloalkyl, aryl, and heteroaryl optionally substituted with lower alkyl or halogen; cycloalkyl; or heteroaryl optionally substituted with lower alkyl or halogen; or R6 has the following formula (IA):

wherein R8 is selected from H, lower alkyl, cycloalkyl, or substituted lower alkyl wherein the substituents are selected from the group consisting of hydroxy, and alkoxy; and

R9 is selected from H, or lower alkyl; or R9 has the following formula (IB):

where R10a and R10b are independently selected from H, or lower alkyl;

and R11 is selected from H, or lower alkyl;

R7 is selected from H, or a 3-indolyl of the formula (IC):

where R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

5. A compound of claim 1 having the structure of formula (I-S):

or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1 is selected from alkyl, or substituted alkyl;

R2 is selected from alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R6 is selected from H, alkylsulfonyl, arylsulfonyl, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl; or R6 has the following formula (IA*):

where R8 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

where R10 is selected from alkyl, or substituted alkyl;

and R11 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R7 is selected from H, or a 3-indolyl of the formula (IC):

where R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H or hydroxy.

6. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein:

R1 is alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

where R10 is selected from alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro; and

R7 is selected from H, or a 3-indolyl of the formula (IC):

R12 is selected from H or hydroxy.

7. A compound of claim 6 , or a pharmaceutically acceptable salt thereof, wherein:

R1 is selected from alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cyclopropyl, alkoxy, amino, and nitro.

8. A compound of claim 6 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, or lower alkyl;

R1 is lower alkyl;

R2 is selected from lower alkyl; cycloalkyl; or substituted lower alkyl, wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

R6 is selected from H; lower alkylsulfonyl; alkyl; substituted alkyl, wherein the substituents are selected from the group consisting of hydroxy, oxo, halogen, alkoxy, cycloalkyl, aryl, and heteroaryl optionally substituted with lower alkyl or halogen; cycloalkyl; or heteroaryl optionally substituted with lower alkyl or halogen; or R6 has the following formula (IA*):

where R8 is selected from lower alkyl, cycloalkyl, or substituted lower alkyl, wherein the substituents are selected from the group consisting of hydroxy, and alkoxy; and

R9 is selected from H, or lower alkyl; or R9 has the following formula (IB*):

where R10 is lower alkyl; and

R11 is selected from H, or lower alkyl;

R7 is selected from H, or a 3-indolyl of the formula (IC):

where R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

9. A compound of claim 1 having the structure of Formula (II):

or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1a, R1b, R10a and R10b are independently selected from H, alkyl, or substituted alkyl;

R2 and R8 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

where R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H, or hydroxy.

10. A compound of claim 9 , or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroaryl, or substituted heteroaryl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R1a, R1b, R10a and R10b are independently selected from H, alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R2 and R8 are independently selected from alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

R12 is selected from H, or hydroxy.

11. A compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, alkyl, substituted alkyl, alkenyl, or substituted alkenyl; wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cyclopropyl, alkoxy, amino, and nitro; and

12. A compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, or lower alkyl;

R1a, R1b, R10a and R10b are independently selected from H, or lower alkyl;

R2 and R8 are independently selected from H, lower alkyl, cycloalkyl, or substituted lower alkyl, wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

where R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

13. A compound of claim 9 having the structure of Formula (II-S):

or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1 and R10 are independently selected from alkyl, or substituted alkyl;

R2 and R8 are independently selected from alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

where R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H or hydroxy.

14. A compound of claim 13 , or a pharmaceutically acceptable salt thereof, wherein:

R1 and R10 are independently selected from alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

R12 is selected from H or hydroxy.

15. A compound of claim 13 , or a pharmaceutically acceptable salt thereof, wherein:

16. A compound of claim 14 , or a pharmaceutically acceptable salt thereof, wherein:

R and R11 are independently selected from H, or lower alkyl;

R1 and R10 are independently selected from lower alkyl;

R2 and R8 are independently selected from lower alkyl; cycloalkyl; or substituted lower alkyl, wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

R7 is selected from H, or a 3-indolyl of the formula (IIC):

where R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

17. A compound of claim 1 having the structure of Formula (III):

or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1a and R1b are each independently selected from H, alkyl, or substituted alkyl;

R2 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

where R8 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

where R10a and R10b are independently selected from H, alkyl, or substituted alkyl;

and R11 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H or hydroxy.

18. A compound of claim 17 , or a pharmaceutically acceptable salt thereof, wherein:

R1a and R1b are each independently selected from H, alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R2 is selected from H, alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

where R8 is selected from alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

R3 is selected from H, alkyl, or substituted alkyl, where the substituents are selected from the group consisting of halogen, hydroxy, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R12 is selected from H, or hydroxy.

19. A compound of claim 18 , or a pharmaceutically acceptable salt thereof, wherein:

20. A compound of claim 18 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, or lower alkyl;

R1a and R1b are each independently selected from H, or lower alkyl;

R2 is selected from H; lower alkyl; cycloalkyl, or substituted lower alkyl wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

R6 is selected from H; lower alkylsulfonyl; lower alkyl; substituted lower alkyl, wherein the alkyl substituents are selected from the group consisting of hydroxy, oxo, halogen, alkoxy, cycloalkyl, aryl, and heteroaryl optionally substituted with lower alkyl or halogen; cycloalkyl; or heteroaryl optionally substituted with lower alkyl or halogen; or R6 has the following formula (IIIA):

wherein R8 is selected from H; lower alkyl; cycloalkyl, or substituted lower alkyl wherein the substituents are selected from the group consisting of hydroxy, and alkoxy; and

R9 is selected from H, or lower alkyl; or R9 has the following formula (IIIB):

where R10a and R10b are independently selected from H, or lower alkyl;

and R11 is selected from H, or lower alkyl;

R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

21. A compound of claim 17 having the structure of formula (III-S):

or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R1 is selected from alkyl, or substituted alkyl;

R2 is selected from alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

where R8 is selected from H, alkyl, substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

where R10 is selected from alkyl, or substituted alkyl;

and R11 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

R3 is selected from H, alkyl, or substituted alkyl;

R4 is selected from H, halogen, alkyl, or substituted alkyl; and

each R5 is independently selected from H, halogen, alkyl, or substituted alkyl; and

R12 is selected from H, or hydroxy.

22. A compound of claim 21 , or a pharmaceutically acceptable salt thereof, wherein:

R1 is selected from alkyl, or substituted alkyl, wherein the substitutents are selected from the group consisting of halogen, hydroxy, oxo, mercapto, carboxyl, alkyl, cycloalkyl, aryl, alkoxy, amino, heteroaryl, and nitro;

R2 is selected from alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or substituted alkyl, wherein the substituents are selected from the group consisting of halogen, hydroxy, oxo, alkoxy, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

R12 is selected from H, or hydroxy.

23. A compound of claim 22 , or a pharmaceutically acceptable salt thereof, wherein:

24. A compound of claim 22 , or a pharmaceutically acceptable salt thereof, wherein:

R is selected from H, or lower alkyl;

R1 is lower alkyl;

R2 is selected from lower alkyl, cycloalkyl, or substituted lower alkyl, wherein the substituents are selected from the group consisting of hydroxy, and alkoxy;

where R8 is selected from lower alkyl; cycloalkyl, or substituted lower alkyl wherein the substituents are selected from the group consisting of hydroxy, and alkoxy; and

R9 is selected from H, or lower alkyl; or R9 has the following formula (IIIB*):

where R10 is lower alkyl; and

R11 is selected from H, or lower alkyl;

R3 is selected from H, or aralkyl;

R4 is selected from H, or halogen; and

each R5 is independently selected from H, or halogen; and

R12 is H, or hydroxy.

25. A compound of claim 1 , selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

26. A compound of claim 1 , selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

27. A compound of claim 1 , selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

28. A pharmaceutical composition comprising a compound, or a pharmaceutically acceptable salt thereof, of claim 1 and a pharmaceutically acceptable excipient.

29. A method for inducing apoptosis in a cell comprising contacting the cell with a compound, or a pharmaceutically acceptable salt thereof, of claim 1 , in an amount sufficient to induce apoptosis in the cell.

30. The method of claim 29 wherein the cell is a cancer cell.

31. A method of treating a patient having cancer selected from the group consisting of: sarcomas, bladder cancers, ovarian cancers, breast cancers, brain cancers, pancreatic cancers, colon cancers, blood cancers, skin cancers, lung cancers and bone cancers, the method comprising administering a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof sufficient for inducing apoptosis, of claim 1 , to a patient in need thereof.

32. The method of claim 31 wherein the cancers are selected from the group consisting of: colorectal cancer, renal carcinoma, ovarian carcinoma, pancreatic carcinoma, prostate carcinoma, breast carcinoma, melanoma, glioblastoma, acute myeloid leukemia (AML), small cell lung carcinoma, non-small cell lung carcinoma, rhabdomyosarcoma, and basal cell carcinoma.

33. The method of claim 31 further comprising administering a second therapy selected from radiation, chemotherapy, immunotherapy, photodynamic therapy, or combinations thereof.

34. A method of treating a patient having an autoimmune disease selected from the group consisting of: systemic lupus erythematosus, psoriasis and idiopathic thrombocytopenic purpura (Morbus Werlhof); the method comprising administering a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof sufficient for inducing apoptosis, of claim 1 , to a patient in need thereof.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2015

From: TETRALOGIC PHARMACEUTICALS CORPORATION

To: TETRALOGIC BIRINAPANT UK LTD

Reel/Frame 036264/0713 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2011

From: CONDON, STEPHEN M.; LAPORTE, MATTHEW G.

To: TETRALOGIC PHARMACEUTICALS CORPORATION

Reel/Frame 026424/0410 →

Continuity (2)

Provisional Application 61097762 · Sep 17, 2008

Related Publication 20110237517A1 · Sep 29, 2011