IP Library Granted Patent US 9,220,695
Granted Patent B2
US 9,220,695 · App. 14/408,748 · Granted Dec 29, 2015

Polyenolic zinc-binding agents (pezbins) actively promote inactivation of cancer stem cells and potentiate cytotoxic anti-tumor drug substances

Inventors: Lorne M. Golub (Smithtown, NY); Francis Johnson (Setauket, NY); Galina I. Botchkina (Stony Brook, NY); Iwao Ojima (Port Jefferson, NY)
Assignee: The Research Foundation for The State University of New York
A61K31/167A61K31/136A61K31/216A61K31/337A61K31/444A61K45/06
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Quick Facts
Patent No.
US 9,220,695
App. No.
14/408,748
Granted
Dec 29, 2015
Kind
B2
Abstract

The present invention provides a method of inhibiting the growth of or promoting differentiation and destruction of cancer stem cells (CSCs) comprising contacting the cancer stem cells with a compound having the structure: or a pharmaceutically acceptable salt thereof.

Claims (106)

1. A method of inhibiting the growth of or promoting differentiation of cancer stem cells (CSCs) comprising contacting the cancer stem cells with a compound having the structure:

wherein

bond α and β are each, independently, present or absent;

X is CR 5 or N; Y is CR 10 or N;

R 1 is H, CF 3 , halogen, —NO 2 , —OCF 3 ,  OR 12 , —NHCOR 12 , —CONR 12 R 13 , —CSNR 12 R 13 , —C(═NH)NR 12 R 13 —SR 12 , —SO 2 R 13 , —COR 14 , —CSR 14 , —C(═NR 12 )R 14 , —C(═NR 12 )NR 13 R 14 , —SOR 12 , —SONR 12 R 13 , —SO 2 NR 12 R 13 , —P(O)R 12 , —PH(═O)OR 12 —P(═O)(OR 12 )(OR 13 ), or —P(OR 12 )(OR 13 ),

wherein R 12 and R 13 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 14 is C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroaryl, heterocyclyl, methoxy, —OR 15 , —NR 16 R 17 , or

 wherein R 15 is H, C 3-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl;

R 16 and R 17 are each, independently, H, C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 18 , R 19 , R 21 , and R 22 are each independently H, halogen, —NO 2 , —CN, —NR 23 R 24 , —SR 23 , —SO 2 R 23 , —CO 2 R 23 , —OR 25 , CF 3 , —SOR 23 , —POR 23 , —C(═S)R 23 , —C(═NH)R 23 , —C(═N)R 23 , —P(═O)(OR 23 )(OR 24 ), —P(OR 23 )(OR 24 ), —C(═S)R 23 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 23 , R 24 , and R 25 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 20 is halogen, —NO 2 , —CN, —NR 26 R 27 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 26 and R 27 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, H, halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —OR 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein when R 1 is H, then R 3 , R 4 , R 5 , R 8 , R 9 , or R 10 , is halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein each occurrence of alkyl, alkenyl, or alkynyl is branched or unbranched, unsubstituted or substituted;

or a pharmaceutically acceptable salt thereof.

2. A method of down-regulating cancer stem cell-relevant transcription factors comprising contacting the cancer stem cell with a compound having the structure:

wherein

bond α and β are each, independently, present or absent;

X is CR 5 or N; Y is CR 10 or N;

R 1 is H, CF 3 , halogen, —NO 2 , —OCF 3 , —OR 12 , —NHCOR 12 , —CONR 12 R 13 , —CSNR 12 R 13 , —C(═NH)NR 12 R 13 —SR 12 , —SO 2 R 13 , —COR 14 , —CSR 14 , —C(═NR 12 )R 14 , —C(═NR 12 )NR 13 R 14 , —SOR 12 , —SONR 12 R 13 , —SO 2 NR 12 R 13 , —P(O)R 12 , —PH(═O)OR 12 —P(═O)(OR 12 )(OR 13 ), or —P(OR 12 )(OR 13 ),

wherein R 12 and R 13 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 14 is C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroaryl, heterocyclyl, methoxy, —OR 15 , —NR 16 R 17 , or

 wherein R 15 is H, C 3-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl;

R 16 and R 17 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 18 , R 19 , R 21 , and R 22 are each independently H, halogen, —NO 2 , —CN, —NR 23 R 24 , —SR 23 , —SO 2 R 23 , —CO 2 R 23 , —OR 25 , CF 3 , —SOR 23 , —POR 23 , —C(═S)R 23 , —C(═NH)R 23 , —C(═N)R 23 , —P(═O)(OR 23 )(OR 24 ), —P(OR 23 )(OR 24 ), —C(═S)R 23 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 23 , R 24 , and R 25 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 20 is halogen, —NO 2 , —CN, —NR 26 R 27 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 26 and R 27 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, H, halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —OR 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein when R 1 is H, then R 3 , R 4 , R 5 , R 8 , R 9 , or R 10 , is halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein each occurrence of alkyl, alkenyl, or alkynyl is branched or unbranched, unsubstituted or substituted;

or a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , further comprising contacting the cancer stem cell with a chemotherapeutic agent.

4. The method of claim 2 , wherein the cancer stem cell-relevant transcription factor is CDX2, DLX2, EGR3, FOXP3, GLI2, HOXA2, HOXA7, HOXB3, HOXB8, HOXC10, HOXC9, HOXC6, HOXC4, HOXC5, IRX4, JUN, KLF2, NFATC1, NR2F2, PITX3, POU5F1, RUNX1, WT1, c-MYC, or SOX-2.

5. The method of claim 2 , wherein the cancer stem cell-relevant transcription factor is each of CDX2, DLX2, EGR3, FOXP3, GLI2, HOXA2, HOXA7, HOXB3, HOXB8, HOXC10, HOXC9, HOXC6, HOXC4, HOXC5, IRX4, JUN, KLF2, NFATC1, NR2F2, PITX3, POU5F1, RUNX1, WT1, c-MYC, and SOX-2.

6. The method of claim 2 , wherein the cancer stem cell-relevant transcription factors are at least five (5) transcription factors selected from the group consisting of CDX2, DLX2, EGR3, FOXP3, GLI2, HOXA2, HOXA7, HOXB3, HOXB8, HOXC10, HOXC9, HOXC6, HOXC4, HOXC5, IRX4, JUN, KLF2, NFATC1, NR2F2, PITX3, POU5F1, RUNX1, WT1, c-MYC, and SOX-2.

7. A method of inhibiting the growth of a tumor comprising cancer stem cells (CSCs) by contacting the tumor with a compound having the structure:

wherein

bond α and β are each, independently, present or absent;

X is CR 5 or N; Y is CR 10 or N;

R 1 is H, CF 3 , halogen, —NO 2 , —OCF 3 , —OR 12 , —NHCOR 12 , —CONR 12 R 13 , —CSNR 12 R 13 , —C(═NH)NR 12 R 13 —SR 12 , —SO 2 R 13 , —COR 14 , —CSR 14 , —C(═NR 12 )R 14 , —C(═NR 12 )NR 13 R 14 , —SOR 12 , —SONR 12 R 13 , —SO 2 NR 12 R 13 , —P(O)R 12 , —PH(═O)OR 12 —P(═O)(OR 12 )(OR 13 ), or —P(OR 12 )(OR 13 ),

wherein R 12 and R 13 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 14 is C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroaryl, heterocyclyl, methoxy, —OR 15 , —NR 16 R 17 , or

 wherein R 15 is H, C 3-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl;

R 16 and R 17 are each, independently, H, C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 18 , R 19 , R 21 , and R 22 are each independently H, halogen, —NO 2 , —CN, —NR 23 R 24 , —SR 23 , —SO 2 R 23 , —CO 2 R 23 , —OR 25 , CF 3 , —SOR 23 , —POR 23 , —C(═S)R 23 , —C(═NH)R 23 , —C(═N)R 23 , —P(═O)(OR 23 )(OR 24 ), —P(OR 23 )(OR 24 ), —C(═S)R 23 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 23 , R 24 , and R 25 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 20 is halogen, —NO 2 , —CN, —NR 26 R 27 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 26 and R 27 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, H, halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —OR 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein when R 1 is H, then R 3 , R 4 , R 5 , R 8 , R 9 , or R 10 , is halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein each occurrence of alkyl, alkenyl, or alkynyl is branched or unbranched, unsubstituted or substituted;

or a pharmaceutically acceptable salt thereof.

8. The method of claim 7 , wherein the compound inhibits the growth of cancer stem cells and/or promotes the differentiation of cancer stem cells.

9. The method of claim 7 , further comprising contacting the tumor with a chemotherapeutic agent.

10. The method of claim 3 , wherein the growth of cancer stem cells is not inhibited by, or the differentiation of cancer stem cells is not promoted by, or the cancer stem cell-relevant transcription factors are not inhibited by, the chemotherapeutic agent.

11. The method of claim 9 , wherein the tumor is resistant to a chemotherapeutic agent due to the presence of cancer stem cells in the tumor.

12. The method of claim 7 , wherein the compound has the structure

or a pharmaceutically acceptable salt thereof.

13. The method of claim 9 , wherein the chemotherapeutic agent is SBT-1214.

14. The method of claim 3 , wherein the chemotherapeutic agent is puromycin, 5-fluorocytidine, 2′-deoxy-5-fluorocytidine, 5′-deoxy-5-fluorocytidine, 5′-deoxy-5-fluorocytidine, gemcitabine, cytarabine, cladribine, troxacitabine, abiraterone acetate, abraxane, adriamycin, afinitor, alimta, aloxi, amboclorin, aminolevulinic acid, anastrozole, aprepitant, aromasin, axitinib, azacitidine, bendamustine hydrochloride, bexarotene, bleomycin, bortezomib, cabazitaxel, capecitabine, cerubidine, clofarabine, clofarex, crizotinib, dacarbazine, dasatinib, daunorubicin hydrochloride, decitabine, degarelix, dexrazoxane hydrochloride, docetaxel, doxil, deoxorubicin, ellence, epirubicin hydrochloride, eribulin mesylate, erlotinib hydrochloride, etoposide, evacet, everolimus, fludara, fludarabine phosphate, fluorouracil, fulvestrant, gefitinib, gemcitabine hydrochloride, imatinib mesylate, imiquimod, irinotecan hydrochloride, ixabepilone, lapatinib ditosylate, lenalidomide, letrozole, leucovorin calcium, leuprorelin, levulan, lomustine, lupron, matulane, methotrexate, mitomycin C, navelbine, nelarabine, nexavar, nilotinib, nolvadex, palonosetron hydrochloride, pazopanib hydrochloride, pemetrexed disodium, pralatrexate, prednisone, procarbazine hydrochloride, raloxifene hydrochloride, ruxolitinib phosphate, sorafenib tosylate, sunitinib malate, tamoxifen citrate, taxol, taxotere, temozolomide, temsirolimus, topotecan hydrochloride, toremifene, vandetanib, vemurafenib, vinblastine sulfate, vincristine sulfate, vinorelbine tartrate, vismodegib, wellcovorin, xalkori, zevalin, zinecard, zoledronic acid, paclitaxel, anthracendione, cyclophosphamide, etoposide, LB100, cis-platin, or oxaliplatin.

15. The method of claim 7 , wherein the cancer stem cells are colon cancer stem cells or prostate cancer stem cells.

16. A method of treating a patient suffering from cancer comprising administering to the patient a compound having the structure:

wherein

bond α and β are each, independently, present or absent;

X is CR 5 or N; Y is CR 10 or N;

R 1 is H, CF 3 , halogen, —NO 2 , —OCF 3 , —OR 12 , —NHCOR 12 , —CONR 12 R 13 , —CSNR 12 R 13 , —C(═NH)NR 12 R 13 —SR 12 , —SO 2 R 13 , —COR 14 , —CSR 14 , —C(═NR 12 )R 14 , —C(═NR 12 )NR 13 R 14 , —SOR 12 , —SONR 12 R 13 , —SO 2 NR 12 R 13 , —P(O)R 12 , —PH(═O)OR 12 —P(═O)(OR 12 )(OR 13 ), or —P(OR 12 )(OR 13 ),

wherein R 12 and R 13 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 14 is C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroaryl, heterocyclyl, methoxy, —OR 15 , —NR 16 R 17 , or

 wherein R 15 is H, C 3-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl;

R 16 and R 17 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 18 , R 19 , R 21 , and R 22 are each independently H, halogen, —NO 2 , —CN, —NR 23 R 24 , —SR 23 , —SO 2 R 23 , —CO 2 R 23 , —OR 25 , CF 3 , —SOR 23 , —POR 23 , —C(═S)R 23 , —C(═NH)R 23 , —C(═N)R 23 , —P(═O)(OR 23 )(OR 24 ) —P(OR 23 )(OR 24 ), —C(═S)R 23 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 23 , R 24 , and R 25 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 20 is halogen, —NO 2 , —CN, —NR 26 R 27 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 26 and R 27 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, H, halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —OR 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein when R 1 is H, then R 3 , R 4 , R 5 , R 8 , R 9 , or R 10 , is halogen, —NO 2 , —CN, —NR 28 R 29 , —NHR 28 R 29 + , —SR 28 , —SO 2 R 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, or —C(═O)-heterocyclyl; and

wherein each occurrence of alkyl, alkenyl, or alkynyl is branched or unbranched, unsubstituted or substituted;

or a pharmaceutically acceptable salt thereof.

17. The method of claim 16 , further comprising administering to the patient a chemotherapeutic agent.

18. The method of claim 16 , wherein the compound has the structure:

wherein R 14 is C 2-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroaryl, heterocyclyl, methoxy, —OR 15 , —NR 16 R 17 , or

 wherein R 15 is H, C 3-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl;

R 16 and R 17 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 18 , R 19 , R 21 , and R 22 are each independently H, halogen, —NO 2 , —CN, —NR 23 R 24 , —SR 23 , —SO 2 R 23 , —CO 2 R 23 , —OR 25 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 23 , R 24 , and R 25 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 20 is halogen, —NO 2 , —CN, —NR 26 R 27 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 26 and R 27 are each, independently, H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

R 2 , R 3 , R 4 ,R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, H, halogen, —NO 2 , —CN, —NR 28 R 29 , —SR 28 , —SO 2 R 28 , —OR 28 , —CO 2 R 28 , CF 3 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl;

wherein R 28 and R 29 are each, H, CF 3 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl; and

wherein each occurrence of alkyl, alkenyl, or alkynyl is branched or unbranched, unsubstituted or substituted; and

or a salt thereof.

19. The method of claim 17 , wherein the compound has the structure

and the chemotherapeutic agent is SBT-1214.

20. The method of claim 17 , wherein the compound has the structure

and the chemotherapeutic agent is puromycin, 5-fluorocytidine, 2′-deoxy-5-fluorocytidine, 5′-deoxy-5-fluorocytidine, 5′-deoxy-5-fluorocytidine, gemcitabine, cytarabine, cladribine, troxacitabine, abiraterone acetate, abraxane, adriamycin, afinitor, alimta, aloxi, amboclorin, aminolevulinic acid, anastrozole, aprepitant, aromasin, axitinib, azacitidine, bendamustine hydrochloride, bexarotene, bleomycin, bortezomib, cabazitaxel, capecitabine, cerubidine, clofarabine, clofarex, crizotinib, dacarbazine, dasatinib, daunorubicin hydrochloride, decitabine, degarelix, dexrazoxane hydrochloride, docetaxel, doxil, deoxorubicin, ellence, epirubicin hydrochloride, eribulin mesylate, erlotinib hydrochloride, etoposide, evacet, everolimus, fludara, fludarabine phosphate, fluorouracil, fulvestrant, gefitinib, gemcitabine hydrochloride, imatinib mesylate, imiquimod, irinotecan hydrochloride, ixabepilone, lapatinib ditosylate, lenalidomide, letrozole, leucovorin calcium, leuprorelin, levulan, lomustine, lupron, matulane, methotrexate, mitomycin C, navelbine, nelarabine, nexavar, nilotinib, nolvadex, palonosetron hydrochloride, pazopanib hydrochloride, pemetrexed disodium, pralatrexate, prednisone, procarbazine hydrochloride, raloxifene hydrochloride, ruxolitinib phosphate, sorafenib tosylate, sunitinib malate, tamoxifen citrate, taxol, taxotere, temozolomide, temsirolimus, topotecan hydrochloride, toremifene, vandetanib, vemurafenib, vinblastine sulfate, vincristine sulfate, vinorelbine tartrate, vismodegib, wellcovorin, xalkori, zevalin, zinecard, zoledronic acid, paclitaxel, anthracendione, cyclophosphamide, etoposide, LB100, cis-platin, or oxaliplatin.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2015
From: GOLUB, LORNE M.; BOTCHKINA, GALINA I.; OJIMA, IWAO
To: THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK
Reel/Frame 034776/0487 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2015
From: JOHNSON, FRANCIS
To: CHEM-MASTER INTERNATIONAL, INC.
Reel/Frame 034776/0522 →
Continuity (2)
Provisional Application 61666504 · Jun 29, 2012
Related Publication 20150150834A1 · Jun 4, 2015