IP Library Granted Patent US 8,980,890
Granted Patent B2
US 8,980,890 · App. 12/950,764 · Granted Mar 17, 2015

Compositions and methods of treating cell proliferation disorders

Inventor: David G. Hangauer, Jr. (Lancaster, NY)
Assignee: Kinex Pharmaceuticals, LLC
C07D213/56C07C233/13C07C233/22C07D213/64C07D213/74C07D213/89C07D239/26C07D239/34C07D401/12C07D403/04
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Quick Facts
Patent No.
US 8,980,890
App. No.
12/950,764
Granted
Mar 17, 2015
Kind
B2
Abstract

The invention relates to compounds and methods for treating cell proliferation disorders.

Claims (40)

1. A compound according to Formula I:

or a pharmaceutically acceptable salt, tautomer, or prodrug thereof, wherein:

T is a bond;

X y is CY, N, or N—O;

X z is CZ;

Y is hydrogen, hydroxyl, halogen, lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkoxy, O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl-aryl, or O-benzyl;

X a is CR a , N, or N—O;

X b is CR b , N, or N—O;

X c is CR c , N, or N—O;

X d is CR d , N, or N—O;

X e is CR e , N, or N—O;

R a , R b , R c , R d , R e , R 4 , R 5 , and R 6 are, independently, hydrogen, hydroxyl, halogen, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkoxy, O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl-aryl, O-benzyl, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-OH, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl, COOH, COO-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl, SO 2 H, SO 2 -lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 )alkyl,

W is H, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, or C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-aryl;

V is a bond, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —O—CH 2 —, —OCH 2 CH 2 —, or —OCH 2 CH 2 CH 2 —;

R 7 , R 8 , R 9 , R 10 , and R 11 are, independently, hydrogen, hydroxyl, halogen, unsubstituted C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, unsubstituted C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkoxy, O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl-aryl, O-benzyl, unsubstituted C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-OH, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-O—C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl,

R 1 , R 2 , and R 3 are independently H or C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl;

n is 1, or 2; and

m is 1,

wherein at least one of X a , X b , X c , X d and X e is N; provided that when X a is N, X e is not N.

2. The compound of claim 1 , wherein X y is CY.

3. The compound of claim 1 , wherein Y is hydrogen.

4. The compound of claim 1 , wherein Z is

5. The compound of claim 1 , wherein R b is C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkoxy.

6. The compound of claim 1 , wherein R b is

wherein W is H, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, or C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-aryl; and V is a bond, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —O—CH 2 —, —OCH 2 CH 2 —, or —OCH 2 CH 2 CH 2 —.

7. The compound of claim 6 , wherein V is a bond.

8. The compound of claim 1 , wherein X a is N, X b is CR b , X c is CR c , X d is CR d and X e is CR e .

9. The compound of claim 1 , wherein said compound is a pharmaceutically acceptable salt.

10. A composition comprising a compound according to claim 1 and at least one pharmaceutically acceptable excipient.

11. A compound, selected from:

12. A compound according to Formula II:

or a pharmaceutically acceptable salt, tautomer, or prodrug thereof, wherein:

R b , R 4 , R 5 , R 8 , and R 10 are, independently, hydrogen, hydroxyl, halogen, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkoxy, O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl-aryl, O-benzyl, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-OH, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-O-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl, COOH, COO-lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl, SO 2 H, or SO 2 -lower (C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 ) alkyl,

W is H, C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl, or C 1 , C 2 , C 3 , C 4 , C 5 , or C 6 alkyl-aryl; and

V is a bond, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —O—CH 2 —, —OCH 2 CH 2 —, or —OCH 2 CH 2 CH 2 —.

13. The compound of claim 1 , having the formula:

or a pharmaceutically acceptable salt, tautomer or prodrug thereof.

14. A composition comprising the compound according to claim 13 and at least one pharmaceutically acceptable excipient.

15. The compound of claim 1 , having the formula:

16. A compound selected from:

Assignments (9)
SECURITY INTEREST Recorded Sep 16, 2022
From: ATHENEX, INC.
To: SAGARD HEALTHCARE ROYALTY PARTNERS, LP, AS ADMINISTRATIVE AGENT
Reel/Frame 061119/0681 →
SECURITY INTEREST Recorded Sep 16, 2022
From: ATNX SPV, LLC
To: SAGARD HEALTHCARE ROYALTY PARTNERS, LP, AS ADMINISTRATIVE AGENT
Reel/Frame 061119/0920 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2022
From: ATHENEX, INC.
To: ATNX SPV, LLC
Reel/Frame 061071/0086 →
SECURITY INTEREST Recorded Jun 22, 2020
From: ATHENEX, INC.
To: OAKTREE FUND ADMINISTRATION, LLC
Reel/Frame 053005/0657 →
RELEASE OF SECURITY INTEREST Recorded Jun 19, 2020
From: PERCEPTIVE CREDIT HOLDINGS II, LP
To: ATHENEX, INC.
Reel/Frame 052990/0677 →
PATENT SECURITY AGREEMENT Recorded Jul 3, 2018
From: ATHENEX, INC.
To: PERCEPTIVE CREDIT HOLDINGS II, LP
Reel/Frame 047247/0812 →
CHANGE OF NAME Recorded Sep 21, 2015
From: KINEX PHARMACEUTICALS, INC.
To: ATHENEX, INC.
Reel/Frame 036644/0296 →
CHANGE OF NAME Recorded Sep 10, 2015
From: KINEX PHARMACEUTICALS, LLC
To: KINEX PHARMACEUTICALS, INC.
Reel/Frame 036585/0786 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2011
From: HANGAUER, DAVID G., JR.
To: KINEX PHARMACEUTICALS, LLC
Reel/Frame 026001/0128 →
Continuity (6)
Continuation 11796200 · Apr 26, 2007
Continuation 11321419 · Dec 28, 2005
Provisional Application 60639834 · Dec 28, 2004
Provisional Application 60704551 · Aug 1, 2005
Provisional Application 60727341 · Oct 17, 2005
Related Publication 20110065705A1 · Mar 17, 2011