Claims
- 1. A taxane having the formula:
- 2. The taxane of claim 1 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 3. The taxane of claim 1 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 4. The taxane of claim 1 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 5. The taxane of claim 1 wherein R14 is hydrido.
- 6. The taxane of claim 5 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 7. The taxane of claim 5 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 8. The taxane of claim 5 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 9. The taxane of claim 1 wherein R2 is benzoyloxy.
- 10. The taxane of claim 9 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 11. The taxane of claim 9 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 12. The taxane of claim 9 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 13. The taxane of claim 1 wherein R14 is hydrido and R9 is keto.
- 14. The taxane of claim 13 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 15. The taxane of claim 13 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1 -C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 16. The taxane of claim 13 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 17. The taxane of claim 1 wherein R2 is benzoyloxy and R9 is keto.
- 18. The taxane of claim 17 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 19. The taxane of claim 17 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 20. The taxane of claim 17 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 21. The taxane of claim 1 wherein R14 is hydrido and R2 is benzoyloxy.
- 22. The taxane of claim 21 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 23. The taxane of claim 21 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 24. The taxane of claim 21 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 25. The taxane of claim 1 wherein R14 is hydrido, R9 is keto, and R2 is benzoyloxy.
- 26. The taxane of claim 25 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 27. The taxane of claim 25 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1 -C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl or X5is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 28. The taxane of claim 25 wherein X5is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 29. The taxane of claim 25 wherein X5 is —COOX10 and X10 is t-butyl.
- 30. The taxane of claim 29 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, cycloalkyl or alkenyl.
- 31. The taxane of claim 29 wherein X3 is furyl or thienyl.
- 32. The taxane of claim 29 wherein X3 is cycloalkyl.
- 33. A taxane having the formula
- 34. The taxane of claim 33 wherein X3 is furyl, thienyl, pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 35. The taxane of claim 33 wherein R10 is R10aCOO— and R10a is a heterosubstituted methyl group wherein the heteroatom may be substituted to form a alkoxy, alkenoxy, aryloxy, hydroxy, acyloxy, ester or ether.
- 36. The taxane of claim 33 wherein R10 is R10aCOO— and R10a is a heterosubstituted methyl group wherein the heteroatom may be substituted to form a alkoxy or aryloxy.
- 37. The taxane of claim 34 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 38. The taxane of claim 34 wherein X3 is furyl or thienyl.
- 39. The taxane of claim 38 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 40. The taxane of claim 38 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 41. The taxane of claim 34 wherein X3 is cycloalkyl.
- 42. The taxane of claim 41 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 43. The taxane of claim 41 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 44. The taxane of claim 34 wherein X3 is isobutenyl.
- 45. The taxane of claim 44 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 46. The taxane of claim 44 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 47. The taxane of claim 34 wherein R10 is alkoxyacetyloxy or acyloxyacetyloxy.
- 48. The taxane of claim 47 wherein X3 is furyl, thienyl, pyridyl, C1-C8 alkyl or C2-C8 alkenyl.
- 49. The taxane of claim 48 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 50. The taxane of claim 48 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 51. The taxane of claim 47 wherein X3 is cycloalkyl.
- 52. The taxane of claim 51 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 53. The taxane of claim 51 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 54. The taxane of claim 47 wherein X3 is furyl or thienyl.
- 55. The taxane of claim 54 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 56. The taxane of claim 54 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 57. The taxane of claim 34 wherein X3 is furyl or thienyl, and X5is —COX10 wherein X10 is phenyl, or X5 is —COOX10 wherein X10 is t-butyl.
- 58. The taxane of claim 34 wherein X3 is substituted or unsubstituted furyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 wherein X10 is t-butyl.
- 59. The taxane of claim 34 wherein X3 is substituted or unsubstituted thienyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 wherein X10 is t-butyl.
- 60. The taxane of claim 34 wherein X3 is isobutenyl, and X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 61. The taxane of claim 34 wherein X3 is alkyl, and X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 62. The taxane of claim 34 wherein X3 is furyl or thienyl, X5 is —COOX10 and X10 is t-butyl.
- 63. The taxane of claim 34 wherein X3 is isobutenyl or cycloalkyl, X5 is —COOX10 and X10 is t-butyl.
- 64. A pharmaceutical composition comprising the taxane of claim 1 and at least one pharmaceutically acceptable carrier.
- 65. The pharmaceutical composition of claim 64 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 or C2-C8 alkynyl.
- 66. The pharmaceutical composition of claim 65 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 67. The pharmaceutical composition of claim 65 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 68. The pharmaceutical composition of claim 65 wherein X3 is substituted or unsubstituted furyl or thienyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 69. The pharmaceutical composition of claim 65 wherein X3 is furyl or thienyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 wherein X10 is t-butyl.
- 70. The pharmaceutical composition of claim 65 wherein X3 is alkyl or isobutenyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 wherein X10 is t-butyl.
- 71. The pharmaceutical composition of claim 65 wherein X3 is fury or thienyl, X5 is —COOX10 and X10 is t-butyl.
- 72. The pharmaceutical composition of claim 65 wherein X3 is isobutenyl or alkyl, X5 is —COOX10 and X10 is t-butyl.
- 73. A pharmaceutical composition comprising the taxane of claim 34 and at least one pharmaceutically acceptable carrier.
- 74. A pharmaceutical composition comprising the taxane of claim 38 and at least one pharmaceutically acceptable carrier.
- 75. A composition for oral administration comprising the taxane of claim 1 and at least one pharmaceutically acceptable carrier.
- 76. The pharmaceutical composition of claim 75 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 or C2-C8 alkynyl.
- 77. The pharmaceutical composition of claim 76 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 78. The pharmaceutical composition of claim 76 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 79. The pharmaceutical composition of claim 76 wherein X3 is substituted or unsubstituted furyl or thienyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 80. A composition for oral administration comprising the taxane of claim 34 and at least one pharmaceutically acceptable carrier.
- 81. A composition for oral administration comprising the taxane of claim 38 and at least one pharmaceutically acceptable carrier.
- 82. A method of inhibiting tumor growth in a mammal, said method comprising orally administering a therapeutically effective amount of a pharmaceutical composition comprising the taxane of claim 1 and at least one pharmaceutically acceptable carrier.
- 83. The method of claim 82 wherein X3 is 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl.
- 84. The method of claim 83 wherein X5 is —COX10 and X10 is substituted or unsubstituted phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, or X5 is —COOX10 and X10 is substituted or unsubstituted C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl.
- 85. The method of claim 83 wherein X5 is —COX10 and X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 86. The method of claim 83 wherein X3 is substituted or unsubstituted furyl or thienyl, and X5 is —COX10 wherein X10 is phenyl, or X5 is —COOX10 and X10 is t-butyl.
- 87. A method of inhibiting tumor growth in a mammal, said method comprising orally administering a therapeutically effective amount of a pharmaceutical composition comprising the taxane of claim 34 and at least one pharmaceutically acceptable carrier.
- 88. A method of inhibiting tumor growth in a mammal, said method comprising orally administering a therapeutically effective amount of a pharmaceutical composition comprising the taxane of claim 38 and at least one pharmaceutically acceptable carrier.
- 89. A taxane having the formula
- 90. A taxane having the formula
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of application Ser. No. 09/775,912 filed Feb. 2, 2001, which claimed priority from U.S. provisional application Serial No. 60/179,669, filed on Feb. 2, 2000.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60179669 |
Feb 2000 |
US |
Continuations (1)
|
Number |
Date |
Country |
Parent |
09775912 |
Feb 2001 |
US |
Child |
10609301 |
Jun 2003 |
US |