Claims
- 1. A compound having the formula:
- 2. The compound of claim 1, having the formula:
- 3. The compound of claim 2, having the formula:
- 4. The compound of claim 3, wherein R1 is CH3, R3 is ═O, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 5. The compound of claim 4, wherein R2 is OC(O)H.
- 6. The compound of claim 4, wherein R2 is H.
- 7. The compound of claim 4, wherein R2 is OH.
- 8. The compound of claim 4, wherein R2 is —O-benzene.
- 9. The compound of claim 4, wherein R2 is OCOCH3.
- 10. The compound of claim 4, wherein R2 is —O-t-butyldimethylsilyl.
- 11. The compound of claim 4, wherein R2 is —O-Pivaloyl.
- 12. The compound of claim 3, wherein R1 is H, R3 is ═O, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 13. The compound of claim 12, wherein R2 is —O-pivaloyl.
- 14. The compound of claim 3, wherein R1 is H, R3 is ═O, R4 is benzene3, R5 is OCH3, R6 is ═O, and R7 is H.
- 15. The compound of claim 3, wherein R1 is H, R3 is ═O, R4 is H, R5 is OCH3, R6 is ═O, and R7 is H.
- 16. The compound of claim 3, wherein R1 is H, R3 is ═O, R4 is H, R5 is H, R6 is ═O, and R7 is H.
- 17. The compound of claim 3, wherein R3 is ═O, R4 is H, R5 is halogen, R6 is ═O, and R7 is H.
- 18. The compound of claim 2, having the formula:
- 19. The compound of claim 18, wherein R1 is CH3, R3 is ═O, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 20. The compound of claim 19, wherein R2 is OC(O)H.
- 21. The compound of claim 19, wherein R2 is H.
- 22. The compound of claim 19, wherein R2 is OH.
- 23. The compound of claim 19, wherein R2 is —O-benzene.
- 24. The compound of claim 19, wherein R2 is OCOCH3.
- 25. The compound of claim 19, wherein R2 is —O-t-butyldimethylsilyl.
- 26. The compound of claim 19, wherein R2 is —O-Pivaloyl.
- 27. The compound of claim 18, wherein R1 is H, R3 is ═O, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 28. The compound of claim 27, wherein R2 is —O-pivaloyl.
- 29. The compound of claim 18, wherein R1 is H, R3 is ═O, R4 is benzene3, R5 is OCH3, R6 is ═O, and R7 is H.
- 30. The compound of claim 18, wherein R1 is H, R3 is ═O, R4 is H, R5 is OCH3, R6 is ═O, and R7 is H.
- 31. The compound of claim 18, wherein R1 is H, R3 is ═O, R4 is H, R5 is H, R6 is ═O, and R7 is H.
- 32. The compound of claim 18, wherein R1 is H, R3 is ═O, R4 is H, R5 is halogen, R6 is ═O, and R7 is H.
- 33. A compound having the formula:
- 34. The compound of claim 33, having the formula:
- 35. The compound of claim 34, having the formula:
- 36. The compound of claim 35, wherein R1 and CH3, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 37. The compound of claim 36, wherein R2 is OC(O)H.
- 38. The compound of claim 36, wherein R2 is H.
- 39. The compound of claim 36, wherein R2 is OH.
- 40. The compound of claim 36, wherein R2 is —O-benzene.
- 41. The compound of claim 36, wherein R2 is OCOCH3.
- 42. The compound of claim 36, wherein R2 is —O-t-butyldimethylsilyl.
- 43. The compound of claim 36, wherein R2 is —O-Pivaloyl.
- 44. The compound of claim 35, wherein R1 is H, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 45. The compound of claim 44, wherein R2 is —O-pivaloyl.
- 46. The compound of claim 35, wherein R1 is H, R4 is benzene3, R5 is OCH3, R6 is ═O, and R7 is H.
- 47. The compound of claim 35, wherein R1 is H, R4 is H, R5 is OCH3, R6 is ═O, and R7 is H.
- 48. The compound of claim 35, wherein R1 is H, R4 is H, R5 is H, R6 is ═O, and R7 is H.
- 49. The compound of claim 35, wherein R1 is H, R4 is H, R5 is halogen, R6 is ═O, and R7 is H.
- 50. The compound of claim 34, having the formula:
- 51. The compound of claim 50, wherein R1 is CH3, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 52. The compound of claim 51, wherein R2 is OC(O)H.
- 53. The compound of claim 51, wherein R2 is H.
- 54. The compound of claim 51, wherein R2 is OH.
- 55. The compound of claim 51, wherein R2 is O-benzene.
- 56. The compound of claim 51, wherein R2 is OCOCH3.
- 57. The compound of claim 51, wherein R2 is —O-t-butyldimethylsilyl.
- 58. The compound of claim 51, wherein R2 is —O-Pivaloyl.
- 59. The compound of claim 50, wherein R1 is H, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H.
- 60. The compound of claim 59, wherein R2 is —O-pivaloyl.
- 61. The compound of claim 50, wherein R1 is H, R4 is benzene3, R5 is OCH3, R6 is ═O, and R7 is H.
- 62. The compound of claim 50, wherein R1 is H, R4 is H, R5 is OCH3, R6 is ═O, and R7 is H.
- 63. The compound of claim 50, wherein R1 is H, R4 is H, R5 is H, R6 is ═O, and R7 is H.
- 64. The compound of claim 50, wherein R1 is H, R4 is H, R5 is halogen, R6 is ═O, and R7 is H.
- 65. A compound having the formula:
- 66. A compound having the formula:
- 67. A method of producing the compound of claim 1, comprising reacting a compound having the formula A as follows
- 68. The method of claim 67, wherein the reaction is performed in the presence of N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride.
- 69. The method of claim 67, wherein the reaction is performed in the presence of Dess-Martin periodinate.
- 70. The method of claim 69, wherein the reaction is further performed in the presence of CH2Cl2.
- 71. A method of producing the compound of claim 33, comprising reacting the compound of claim 1 with camphor sulfonic acid (CSA) in the presence of toluene.
- 72. A pharmaceutical composition for treating a tumor in a subject, comprising a pharmaceutically effective amount of the compound of claim 1 or 33 and a pharmaceutically acceptable carrier.
- 73. A method of inhibiting proliferation of tumor cells which comprises contacting the cells under suitable conditions with an effective amount of the compound of claim 1 or 33.
- 74. A method of treating a patient having a tumor characterized by proliferation of neoplastic cells which comprises administering to the patient an effective amount of the compound of claim 1 or 33.
- 75. The method of claim 74, wherein the effective amount is from about 0.5 mg to about 5 mg per day.
- 76. The method of claim 75, wherein the effective amount is from about 1 mg to about 3 mg per day.
- 77. The method of claim 76, wherein the effective amount is about 2 mg per day.
- 78. The compound of claim 65, having the formula:
- 79. A compound as in claim 78, wherein R4 is CH3 and R5 is CH3 (compound 1).
- 80. A compound as in claim 78, wherein R4 is Bn and R5 is H (compound 3).
- 81. The compound of claim 66 having the formula:
- 82. The compound of claim 66, having the formula:
- 83. The compound of claim 82, having the formula:
- 84. A compound having the formula:
- 85. The compound of claim 84, having the formula:
- 86. The compound of claim 85, having the formula:
- 87. The compound of claim 86, wherein R1 is H, R2 is OH, R3 is H, R4 is H, R5 is H, R6 is ═O, and R7 is H (Compound 113).
- 88. The compound of claim 86, wherein R3 is H, R4 is CH3, R5 is OCH3, and R1 is H.
- 89. The compound of claim 88, wherein R2 is OH.
- 90. The compound of claim 89, wherein R6 is H and R1 is CH3 (Compound 107).
- 91. The compound of claim 89, wherein R6 is ═O and R1 is H (Compound 104).
- 92. The compound of claim 88, wherein R2 and R6 are joined as an ester bond.
- 93. The compound of claim 92, wherein R1 is H (Compound 105).
- 94. The compound of claim 92, wherein R1 is CH3 (Compound 106).
- 95. The compound of claim 84, having the formula:
- 96. The compound of claim 95, wherein R1 is H. R2 is OH, R6 is ═O, and R7 is H.
- 97. The compound of claim 96, wherein R4 is CH3, R5 is OCH3.
- 98. The compound of claim 97, wherein R3 is OH (Compound 109).
- 99. The compound of claim 97, wherein R3 is H (Compound 111).
- 100. The compound of claim 96, wherein R3 is H, R4 is H and R5 is H (Compound 112).
- 101. The compound of claim 95, wherein R1 is H, R2 is OH, R3 is ═O, R4 is CH3, R5 is OCH3, R6 is ═O, and R7 is H. (Compound 108).
- 102. The compound of claim 50, wherein R1 is H, R2 is OH, R4 is CH3, R5 is CH3, R6 is ═O, and R7 is H (Compound 110).
- 103. The method of claim 67, wherein the compound having formula B is:
- 104. A method of producing the compound of claim 84, comprising reacting a compound having the formula A as follows:
- 105. The method of claim 104, wherein the compound having the formula C is:
- 106. The method of claim 104, wherein the reaction is performed in the presence of N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride.
- 107. The method of claim 104, wherein the reaction is performed in the presence of Dess-Martin periodinate.
- 108. The method of claim 107, wherein the reaction is further performed in the presence of CH2Cl2.
- 109. The method of claim 104, wherein the reaction is performed in the presence of H2, 10% Pd/C, Ethanol-ascetic acid and hydrochloric acid.
- 110. A method of producing the compound of claim 1, comprising reacting the compound of claim 33 with H2, 10% Pd/C, Ethanol-ascetic acid in the presence of hydrochloric acid.
- 111. The compound of claim 33, wherein R2 is an ether, ester, amide, an aromatic ring or is covalently bound to R6.
- 112. A method of preparing the compound in claim 1, comprising reacting the compound in claim 111 with H2, 10% Pd/C, Ethanol-ascetic acid in the presence of hydrochloric acid.
- 113. The compound of claim 50, wherein R2 is an ether, ester, amide, an aromatic ring or is covalently bound to R6.
- 114. A method of preparing the compound in claim 18, comprising reacting the compound in claim 113 with H2, 10% Pd/C, Ethanol-ascetic acid in the presence of hydrochloric acid.
- 115. A pharmaceutical composition for treating a tumor in a subject, comprising a pharmaceutically effective amount of the compound of claim 84 or 95 and a pharmaceutically acceptable carrier.
- 116. A method of inhibiting proliferation of tumor cells which comprises contacting the cells under suitable conditions with an effective amount of the compound of claim 84 or 95.
- 117. A method of treating a patient having a tumor characterized by proliferation of neoplastic cells which comprises administering to the patient an effective amount of the compound of claim 84 or 95.
- 118. The method of claim 117, wherein the effective amount is from about 0.5 mg to about 5 mg per day.
- 119. The method of claim 118, wherein the effective amount is from about 1 mg to about 3 mg per day.
- 120. The method of claim 119, wherein the effective amount is about 2 mg per day.
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Application No. 60/177,071, filed Jan. 19, 2000.
Government Interests
[0002] This invention has been made with government support under National Institutes of Health Grant Nos. CA-28824 and HL-25848. Accordingly, the U.S. Government may have certain rights in the invention.
Provisional Applications (1)
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Number |
Date |
Country |
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60177071 |
Jan 2000 |
US |