IP Library Granted Patent US 8,951,987
Granted Patent B2
US 8,951,987 · App. 14/088,465 · Granted Feb 10, 2015

Certain compounds, compositions and methods

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Quick Facts
Patent No.
US 8,951,987
App. No.
14/088,465
Granted
Feb 10, 2015
Kind
B2
Abstract

The present invention provides certain tetrahydrouridine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of making and using such compounds.

Claims (34)

1. A composition comprising:

(i) a compound of Formula I or a pharmaceutically acceptable salt thereof:

wherein the carbon marked by an asterisk may have an (R) or an (S) configuration; and wherein R 1 and R 2 are fluoro;

(ii) a CDA substrate drug; and

(iii) at least one additional chemotherapeutic agent;

as a combination for simultaneous, separate, or sequential administration.

2. The composition of claim 1 , wherein the CDA substrate drug is selected from decitabine, 5-azacytidine, gemcitabine, ara-C, tezacitabine, 5-fluoro-2′-deoxycytidine, and cytochlor.

3. The composition of claim 1 , wherein the CDA substrate drug is 5-azacytidine, gemcitabine, or ara-C.

4. The composition of claim 1 , wherein the CDA substrate drug is decitabine.

5. The composition of claim 1 , wherein the compound of Formula I is Compound 1a or a pharmaceutically acceptable salt thereof:

6. The composition of claim 1 , wherein the compound of Formula I is Compound 1a:

7. The composition of claim 1 , wherein the chemotherapeutic agent is selected from an alkylating agent, an antimetabolite, a platinating agent, a topoisomerase inhibitor, a tubulin agent, and a signaling inhibitor.

8. The composition of claim 1 , wherein the chemotherapeutic agent is selected from doxorubicin, cyclophosphamide, estramustine, carmustine, mitomycin, bleomycin, 5-fluoro-uracil, capecitabine, gemcitabine, nelarabine, fludarabine, methotrexate, cisplatin, oxaliplatin, carboplatin, topotecan, irinotecan, etoposide, paclitaxel, docetaxel, vinorelbine, vinblastine, vincristine, other taxanes, epothilones, kinase inhibitors, antibodies, farnesyltransferase inhibitors, tamoxifen, anti-mitotic agents, polo-like kinase inhibitors, and aurora kinase inhibitors.

9. A pharmaceutical composition comprising the composition of claim 1 and a pharmaceutically acceptable excipient.

10. The composition of claim 4 , wherein the compound of Formula I is Compound 1a or a pharmaceutically acceptable salt thereof:

11. A method for treating cancer in a mammal in need thereof, comprising:

(i) administering to said mammal a compound of Formula I or a pharmaceutically acceptable salt thereof:

wherein the carbon marked by an asterisk may have an (R) or an (S) configuration; and wherein R 1 and R 2 are fluoro;

(ii) administering to said mammal a CDA substrate drug; and

(iii) administering to said mammal at least one additional therapeutic agent.

12. The method of claim 11 , wherein the CDA substrate drug is selected from decitabine, 5-azacytidine, gemcitabine, ara-C, tezacitabine, 5-fluoro-2′-deoxycytidine, and cytochlor.

13. The method of claim 11 , wherein the CDA substrate drug is 5-azacytidine, gemcitabine, or ara-C.

14. The method of claim 11 , wherein the CDA substrate drug is decitabine.

15. The method of claim 11 , wherein the chemotherapeutic agent is selected from an alkylating agent, an antimetabolite, a platinating agent, a topoisomerase inhibitor, a tubulin agent, and a signaling inhibitor.

16. The method of claim 11 , wherein the chemotherapeutic agent is selected from doxorubicin, cyclophosphamide, estramustine, carmustine, mitomycin, bleomycin, 5-fluoro-uracil, capecitabine, gemcitabine, nelarabine, fludarabine, methotrexate, cisplatin, oxaliplatin, carboplatin, topotecan, irinotecan, etoposide, paclitaxel, docetaxel, vinorelbine, vinblastine, vincristine, other taxanes, epothilones, kinase inhibitors, antibodies, farnesyltransferase inhibitors, tamoxifen, anti-mitotic agents, polo-like kinase inhibitors, and aurora kinase inhibitors.

17. The method of claim 11 , wherein the cancer is selected from hematological cancers and solid cancers.

18. The method of claim 11 , wherein the cancer is a myelodysplastic syndrome, leukemia, acute myeloid leukemia or chronic myeloid leukemia.

19. The method of claim 11 , wherein the cancer is a solid cancer selected from pancreatic cancer, ovarian cancer, peritoneal cancer, non small cell lung cancer, metastatic breast cancer, bladder cancer, squamous cell carcinoma, transitional cell carcinoma, adenocarcinoma, gynecological cancer, fallopian tube carcinoma, liver cancer, hepatocellular carcinoma, lung cancer, cervical carcinoma, genitourinary tract cancer, and gastrointestinal cancer.

20. The method of claim 11 , wherein the compound of Formula I is Compound 1a or a pharmaceutically acceptable salt thereof:

21. The method of claim 11 , wherein the compound of Formula I is Compound 1a:

22. The method of claim 14 , wherein the compound of Formula I is Compound 1a or a pharmaceutically acceptable salt thereof:

23. The method of claim 11 , wherein the compound is administered at substantially the same time with the CDA substrate drug, prior to the CDA substrate drug or after the CDA substrate drug.

24. The method of claim 11 , wherein the compound and the CDA substrate drug are administered in a single unit dosage form or in multiple, seperate unit dosage forms.

25. The method of claim 11 , wherein the therapeutic agent is administered in a separate unit dosage form.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2024
From: OTSUKA PHARMACEUTICAL CO., LTD.
To: TAIHO PHARMACEUTICAL CO., LTD.
Reel/Frame 067988/0681 →
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 Nov 26, 2013
From: HAMILTON, GREGORY S.; TSUKAMOTO, TAKASHI; FERRARIS, DANA V.; DUVALL, BRIDGET; LAPIDUS, RENA
To: MGI PHARMA, INC.
Reel/Frame 031674/0359 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2013
From: MGI PHARMA, INC.
To: EISAI CORPORATION OF NORTH AMERICA
Reel/Frame 031674/0367 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2013
From: EISAI CORPORATION OF NORTH AMERICA
To: EISAI INC.
Reel/Frame 031674/0352 →