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- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20100168064
- Publication Date: July 1, 2010
- Appl. No: 12/448088
- Application Filed: December 07, 2007
- Assignees: China Medical University (Taichung, TW)
- Claim: 1. A phosphate derivative of 2-aryl-4-quinolone having the following formulas Ia, Ib or Ic: [chemical expression included] wherein R2′, R3′, R4′, R5′ and R6′ independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, (CH2)nNR8R9, [chemical expression included] wherein n is an integer of 0-4, Y is O or S, X is F, Cl, or Br, and R8 and R9 independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2m+1) or (CH2)nCH3, wherein n and Y are defined as above, and m is an integer of 0-4; R2, R3, R4 and R5 independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, (CH2)nNR8R9, [chemical expression included] or R3 and R4 together is —Y(CH2)nY—, wherein n, Y, X, R8 and R9 are defined as above; and R1 and R1′ independently are H, Li+, Na+, K+, N+R8R9R10R11 or benzyl wherein R10 and R11 independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2m+1) or (CH2)nCH3, n, m, R8 and R9 are defined as above.
- Claim: 2. The phosphate derivative according to claim 1, which has the formula Ia.
- Claim: 3. The phosphate derivative according to claim 2, wherein R2′, R3′, R4′, R5′ and R6′ are all H; or one of R2′, R3′, R4′, R5′ and R6′ is F, OCH3 or (CH2)nNR8R9, and the others thereof are H, wherein R8 and R9 independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2n+1) or (Ch2)nCH3. wherein n is an integer of O-4, Y is O or S, and m is an integer of 0-4.
- Claim: 4. The phosphate derivative according to claim 2, wherein R2, R3, R4, and R5 are all H; or one of R2, R3, R4, and R5 is F, OCH3, Y(CH2)nCH3 or (CH2)nNR8R9, and the others thereof are H; or R2 and R5 are H, and R3 and R4 together is —O(CH2)nO—, wherein R8 and R9. independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2n+1) or (Ch2)nCH3. wherein n is an integer of O-4, Y is O or S, and m is an integer of 0-4.
- Claim: 5. The phosphate derivative according to claim 2, wherein R1 and R1′ are both H or both Na+.
- Claim: 6. The phosphate derivative according to claim 5, wherein R2 and R5 are H, and R3 and R4 together is —O(CH2)O—; and R2′, R3′, R4′ and R5′ are all H, and R6′ is F.
- Claim: 7. The phosphate derivative according to claim 5, wherein R2 and R5 are H, and R3 and R4 together is —O(CH2)O—; and R2′, R3′, R4′ and R6′ are all H, and R5′ is F.
- Claim: 8. The phosphate derivative according to claim 5, wherein R4 is F, and R2, R3 and R5 are H; and R2′, R3′, R4′, R5′ and R6′ are all H.
- Claim: 9. The phosphate derivative according to claim 5, wherein R2, R3, R4 and R5 are all H; and R2′, R3′, R4′, R5′ and R6′ are all H.
- Claim: 10. The phosphate derivative according to claim 5, wherein R4 is OCH3, and R2, R3 and R5 are H; and R5′ is F, and R2′, R3′, R4′ and R6′ are H.
- Claim: 11. The phosphate derivative according to claim 5, wherein R2 and R5 are H, and R3 and R4 together is —O(CH2)O—; and R2′, R3′, R4′ and R6′ are all H, and R5′ is OCH3.
- Claim: 12. The phosphate derivative according to claim 5, wherein R4 is CH2N(C2H5)2, and R2, R3 and R5 are H; and R6′ is F, and R2′, R3′, R4′ and R5′ are H.
- Claim: 13. The phosphate derivative according to claim 5, wherein R4 is CH2N(C2H5)2, and R2, R3 and R5 are H; and R2′, R3′, R4′, R5′ and R6′ are all H.
- Claim: 14. The phosphate derivative according to claim 5, wherein R4 is OCH3, and R2, R3 and R5 are H; and R5′ is CH2N(C2H5)2, and R2′, R3′, R4′ and R6′ are H.
- Claim: 15. The phosphate derivative according to claim 1, which has the formula Ib.
- Claim: 16. The phosphate derivative according to claim 15, wherein R2, R3, R4, and R5 are all H; or one of R2, R3, R4 and R5 is F or OCH3, and the others thereof are H; or R2 and R5 are H, and R3 and R4 together is —O(CH2)nO—, wherein n is an integer of O-4.
- Claim: 17. The phosphate derivative according to claim 15, wherein R2′, R3′ and R4′ are all H; or one of R2′, R3′ and R4′ is F or OCH3, and the others thereof are H.
- Claim: 18. The phosphate derivative according to claim 15, wherein R1 and R1′ are benzyl.
- Claim: 19. The phosphate derivative according to claim 18, wherein R2′, R3′, R4′, R2 and R5 are all H, and R3 and R4 together is —O(CH2)O—.
- Claim: 20. A method for killing solid cancer cells, which comprises administering to a subject a therapeutically effective amount of a phosphate derivative of 2-aryl-4-quinolone as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the solid cancer cells comprise human breast cancer, colon cancer, lung cancer, melanoma, ovarian cancer, renal cancer, stomach cancer, prostate cancer, ileocecal carcinoma, glioblastoma, bone cancer, epidermoid carcinoma of the nasopharynx, hepatoma or leukemia cancer.
- Claim: 21. The method according to claim 20, wherein the solid cancer cells are human breast cancer, colon cancer, lung cancer, renal cancer, hepatoma, or leukemia cancer
- Claim: 22. The method according to claim 21, wherein the solid cancer cells are human breast cancer or colon cancer.
- Claim: 23. A compound of 2-selenophene 4-quinolone having the following formulas IIb or IIc: [chemical expression included] wherein R2′, R3′ and R4′ independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, or (CH2)nNR8R9, wherein n is an integer of 0-4, Y is O or S, X is F, Cl, or Br, and R8 and R9 independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2m+1) or (CH2)nCH3, wherein n and Y are defined as above, and m is an integer of 0-4; R2, R3, R4 and R5 independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, (CH2)nNR8R9, [chemical expression included] or R3 and R4 together is —Y(CH2)nY—, wherein n, Y, X, R8 and R9 are defined as above.
- Claim: 24. The compound according to claim 23, wherein R2, R3, R4, and R5 are all H; or one of R2, R3, R4 and R5 is F or OCH3, and the others thereof are H; or R2 and R5 are H, and R3 and R4 together is —O(CH2)nO—, wherein n is defined as in claim 19.
- Claim: 25. The compound according to claim 24, wherein R2′, R3′ and R4′ are all H; or one of R2′, R3′ and R4′ is F or OCH3, and the others thereof are H.
- Claim: 26. The compound according to claim 23 which has the formula IIb.
- Claim: 27. The compound according to claim 26, wherein R2′, R3′, R4′, R2 and R5 are all H, and R3 and R4 together is —O(CH2)O—.
- Claim: 28. A method for killing solid cancer cells, which comprises administering to a subject a therapeutically effective amount of a compound of 2-selenophene 4-quinolone as in claim 23, or a pharmaceutically acceptable salt thereof, wherein the solid cancer cells comprise human breast cancer, colon cancer, lung cancer, melanoma, ovarian cancer, renal cancer, stomach cancer, prostate cancer, ileocecal carcinoma, glioblastoma, bone cancer, epidermoid carcinoma of the nasopharynx, hepatoma or leukemia cancer.
- Claim: 29. The method according to claim 28, wherein the solid cancer cells are human breast cancer, colon cancer, lung cancer, renal cancer, hepatoma, or leukemia cancer.
- Claim: 30. A compound of 2-phenyl-4-quinolone having the following formula IIa: [chemical expression included] wherein R2′, R3′, R4′, R5′ and R6′ independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, (CH2)nNR8R9, [chemical expression included] wherein n is an integer of 0-4, Y is O or S, X is F, Cl, or Br, and R8 and R9 independently are H, (CH2)nYH, (CH2)nN(CnH2n+1)(CmH2m+1) or (CH2)nCH3, wherein n and Y are defined as above, and m is an integer of 0-4; R2, R3, R4 and R5 independently are H, (CH2)nCH3, (CH2)nYH, Y(CH2)nCH3, Y(CH2)nYH, Y(CH2)nNR8R9, X, (CH2)nNR8R9, [chemical expression included] or R3 and R4 together is —Y(CH2)nY—, wherein n, Y, X, R8 and R9 are defined as above; provided that one of R2, R3, R4 and R5 is (CH2)qNR8R9, or one of R2′, R3′, R4′, R5′ and R6′ is (CH2)qNR8R9, wherein q is an integer of 1-4, and R8 and R9 are defined as above.
- Claim: 31. The compound according to claim 30, wherein R4 is CH2)qNR8R9, and R2, R3 and R5 are H, wherein q, R8 and R9 are defined as in claim 30.
- Claim: 32. The compound according to claim 30, wherein R5′ is CH2)qNR8R9, and R2′, R3′, R4′ and R6′ are H, wherein q, R8 and R9 are defined as in claim 30.
- Claim: 33. The compound according to claim 31, wherein R4 is CH2N(C2H5)2, R6′ is F, and R2′, R3′, R4′ and R6′ are H.
- Claim: 34. The compound according to claim 31, wherein R4 is CH2N(C2H5)2, R2′, R3′, R4′, R5′ and R6′ are all H.
- Claim: 35. The compound according to claim 32, wherein R4 is OCH3, and R2, R3 and R5 are H; and R5′ is CH2N(C2H5)2, and R2′, R3′, R4′ and R6′ are H.
- Claim: 36. A method for killing solid cancer cells, which comprises administering to a subject a therapeutically effective amount of a compound of 2-phenyl 4-quinolone as in claim 30 or a pharmaceutically acceptable salt thereof, wherein the solid cancer cells comprise human breast cancer, colon cancer, lung cancer, melanoma, ovarian cancer, renal cancer, stomach cancer, prostate cancer, ileocecal carcinoma, glioblastoma, bone cancer, epidermoid carcinoma of the nasopharynx, hepatoma or leukemia cancer.
- Claim: 37. The method according to claim 36, wherein the solid cancer cells are leukemia cancer.
- Current U.S. Class: 514/81
- Current International Class: 61; 07; 61; 61; 61; 07; 07
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