Dicarbonyl derivatives and methods of use
View Patent ↗Derivatives of dicarbonyl compounds having antitumor and antibiotic activity which can be used as anticancer agents.
1. A compound or pharmaceutically acceptable salt thereof having the formula (I)
wherein
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently a hydrogen atom or an alkyl, alkenyl, alkynyl, or aryl comprising 1 to 30 carbon atoms and which is unsubstituted or substituted by at least one of hydroxy, cyano, mercapto, halogen, —OR 7 , SR 7 , —NR 7 R 8 , —CONR 7 R 8 , or —OCONR 7 R 8 , wherein
R 7 and R 8 are a hydrogen atom; an alkyl, alkenyl, or alkynyl comprising 1 to 20 carbon atoms; a cyclic or heterocyclic group comprising 5 or 6 ring atoms of which from 0 to 3 are nitrogen and/or oxygen and/or sulphur hetero-atoms, said cyclic or heterocyclic group being unsubstituted or substituted by at least one of hydroxy, cyano, mercapto, halogen, or an alkyl group comprising 1 to 6 carbon atoms; and X and Y are respectively O, NR 7 or S, wherein when X and Y are O, and if R 2 , R 4 are hydrogen, R 1 -R 3 or both R 1 -R 3 and R 5 -R 6 form a cyclic or an acyclic alkenyl; when X and Y are O, and if R 2 , R 4 form a single bond, R 1 is
wherein Ar is an aryl or heteroaryl.
2. The compound of claim 1 , wherein X and Y are O, and R 6 is —NR 7 R 8 .
3. The compound of claim 1 , wherein X and Y are O.
4. The compound of claim 1 , wherein the compound has the following formula:
5. The compound of claim 4 , wherein R 7 and R 8 are C 1 -C 10 alkyl and C 6 -C 10 aryl, respectively.
6. The compound of claim 1 , wherein the compound has the following formula:
7. The compound of claim 6 , wherein R 7 and R 8 are C 1 -C 10 alkyl and C 6 -C 10 aryl, respectively.
8. The compound of claim 7 , wherein X is H, 3-OMe, 4-OMe, or 3,4-di-OMe.
9. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
10. The pharmaceutical composition of claim 9 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
11. The pharmaceutical composition of claim 10 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
12. The pharmaceutical composition of claim 10 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
13. A pharmaceutical composition comprising the compound of claim 2 and a pharmaceutically acceptable carrier.
14. The pharmaceutical composition of claim 13 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral, parenteral, intravenous, and combinations thereof.
15. The pharmaceutical composition of claim 14 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
16. The pharmaceutical composition of claim 14 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
17. A pharmaceutical composition comprising the compound of claim 3 and a pharmaceutically acceptable carrier.
18. The pharmaceutical composition of claim 17 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral, parenteral, intravenous, and combinations thereof.
19. The pharmaceutical composition of claim 18 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
20. The pharmaceutical composition of claim 18 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
21. A pharmaceutical composition comprising the compound of claim 4 and a pharmaceutically acceptable carrier.
22. The pharmaceutical composition of claim 21 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
23. The pharmaceutical composition of claim 22 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
24. The pharmaceutical composition of claim 22 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
25. A pharmaceutical composition comprising the compound of claim 5 and a pharmaceutically acceptable carrier.
26. The pharmaceutical composition of claim 25 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
27. The pharmaceutical composition of claim 26 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
28. The pharmaceutical composition of claim 26 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
29. A pharmaceutical composition comprising the compound of claim 6 and a pharmaceutically acceptable carrier.
30. The pharmaceutical composition of claim 29 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
31. The pharmaceutical composition of claim 30 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
32. The pharmaceutical composition of claim 30 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, and tonicity adjusting agents.
33. A pharmaceutical composition comprising the compound of claim 7 and a pharmaceutically acceptable carrier.
34. The pharmaceutical composition of claim 33 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral, and parenteral administration.
35. The pharmaceutical composition of claim 34 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
36. The pharmaceutical composition of claim 34 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.
37. A pharmaceutical composition comprising the compound of claim 8 and a pharmaceutically acceptable carrier.
38. The pharmaceutical composition of claim 37 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
39. The pharmaceutical composition of claim 38 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
40. The pharmaceutical composition of claim 38 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.
41. The compound of claim 8 , wherein X is H.
42. The compound of claim 8 wherein X is 3-OMe.
43. The compound of claim 8 wherein X is 4-OMe.
44. The compound of claim 8 wherein X is 3, 4-di-OMe.
45. A pharmaceutical composition comprising the compound of claim 41 and a pharmaceutically acceptable carrier.
46. The pharmaceutical composition of claim 45 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
47. The pharmaceutical composition of claim 46 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
48. The pharmaceutical composition of claim 46 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.
49. A pharmaceutical composition comprising the compound of claim 42 and a pharmaceutically acceptable carrier.
50. The pharmaceutical composition of claim 49 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
51. The pharmaceutical composition of claim 50 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
52. The pharmaceutical composition of claim 50 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.
53. A pharmaceutical composition comprising the compound of claim 43 and a pharmaceutically acceptable carrier.
54. The pharmaceutical composition of claim 53 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
55. The pharmaceutical composition of claim 54 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
56. The pharmaceutical composition of claim 54 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.
57. A pharmaceutical composition comprising the compound of claim 44 and a pharmaceutically acceptable carrier.
58. The pharmaceutical composition of claim 57 , wherein the composition is suitable for delivery via routes of administration selected from the group consisting of oral and parenteral administration.
59. The pharmaceutical composition of claim 58 , wherein said composition is suitable for oral delivery and further comprises one or more ingredients selected from the group consisting of a diluent, an edible carrier, a binder, an excipient, a disintegrating agent, a lubricant, a glidant, and a sweetening agent.
60. The pharmaceutical composition of claim 58 , wherein said composition is suitable for parenteral delivery and comprises one or more ingredients selected from the group consisting of a sterile diluent, antimicrobial agents, antioxidants, buffers, tonicity and adjusting agents.