IP Library Granted Patent US 8,324,180
Granted Patent B2
US 8,324,180 · App. 12/755,106 · Granted Dec 4, 2012

Compositions and methods for treating cancer

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Quick Facts
Patent No.
US 8,324,180
App. No.
12/755,106
Granted
Dec 4, 2012
Kind
B2
Abstract

Provided herein are compounds used to inhibit the deamination enzyme responsible for the inactivation of therapeutic compounds, and methods of using them.

Claims (49)

1. The compound of formula I:

wherein:

one of R 1 and R 2 is F, and the other is selected from H and F;

one of R 3 and R 4 is H, and the other is selected from H and OH;

where is a covalent bond or absent, and R 4 is absent when is a covalent bond;

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

2. The compound of claim 1 , wherein R 1 and R 2 are each F.

3. The compound of claim 2 , wherein said compound of formula I is a compound of formula II:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

4. The compound of claim 1 wherein said compound of formula I is a compound of formula VIII:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

5. The compound of formula VIII:

6. The compound of claim 2 , wherein said compound of formula I is a compound of formula III:

wherein:

one of R 3 and R 4 is H, and the other is selected from H and OH;

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

7. The compound of claim 1 , wherein said compound of formula I is a compound of formula IV:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

8. The compound of claim 7 , wherein said compound of formula IV is a compound of formula V:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

9. The compound of claim 1 , wherein said compound of formula I is a compound of formula VI:

or a pharmaceutically acceptable salt, a alkyl ester, or a C 2-6 alkenyl ester thereof.

10. The compound of claim 9 , wherein said compound of formula VI is a compound of formula VII:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

11. A pharmaceutical composition comprising a compound of formula I:

wherein:

one of R 1 and R 2 is F, and the other is selected from H and F;

one of R 3 and R 4 is H, and the other is selected from H and OH;

where is a covalent bond or absent, and R 4 is absent when is a covalent bond;

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof;

and a pharmaceutically acceptable excipient.

12. The pharmaceutical composition of claim 11 , wherein R 1 and R 2 are each F.

13. The pharmaceutical composition of claim 12 , wherein said compound of formula I is a compound of formula II:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

14. The pharmaceutical composition of claim 11 , wherein the compound of formula I is a compound of formula VIII:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

15. The pharmaceutical composition of claim 14 , wherein the compound is a compound of formula VIII:

16. The pharmaceutical composition of claim 12 , wherein said compound of formula I is a compound of formula III:

wherein:

one of R 3 and R 4 is H, and the other is selected from H and OH;

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

17. The pharmaceutical composition of claim 11 , wherein said compound of formula I is a compound of formula IV:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

18. The pharmaceutical composition of claim 17 , wherein said compound of formula IV is a compound of formula V:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

19. The pharmaceutical composition of claim 11 , wherein said compound of formula I is a compound of formula VI:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

20. The pharmaceutical composition of claim 19 , wherein said compound of formula VI is a compound of formula VII:

or a pharmaceutically acceptable salt, a C 1-6 alkyl ester, or a C 2-6 alkenyl ester thereof.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2025
From: OTSUKA PHARMACEUTICAL CO., LTD.
To: TAIHO PHARMACEUTICAL CO., LTD.
Reel/Frame 073115/0640 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 033794 FRAME: 0804. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 6, 2015
From: OTSUKA PHARMACEUTICAL CO., LTD.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 036335/0153 →
ASSIGNEE CHANGE OF ADDRESS Recorded Sep 23, 2014
From: EISAI INC.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 033794/0804 →
CORRECTIVE ASSIGNMENT TO CORRECT THE SUPPORTING LEGAL DOCUMENTATION PREVIOUSLY RECORDED ON REEL 032945 FRAME 0934. ASSIGNOR(S) HEREBY CONFIRMS THE ADDITION OF MISSING PAGES IDENTIFYING THE PROPERTIES ASSIGNED. Recorded Jun 5, 2014
From: EISAI INC.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 033086/0355 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2014
From: EISAI INC.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 032945/0934 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2010
From: BELYAKOV, SERGEI; DUVALL, BRIDGET; FERRARIS, DANA; HAMILTON, GREGORY; VAAL, MARK
To: EISAI INC.
Reel/Frame 024671/0572 →