Claims
- 1. A compound according to formula (I)
- 2. The compound according to claim 1 wherein
R9 is 67and one of R11, R12, and R13 is selected from the group of phenyl, —C(CH3)3, —CHCHC(CH3)3, —O-phenyl, —(CH2)m-phenyl where m is an integer from 1 to 10, —CHCH)n-phenyl where n is an integer from 1 to 4, 68where X is oxygen, sulfur, or nitrogen, 69
- 3. The compound according to claim 2 wherein R11 and R12 are hydrogen and R13 is phenyl or
- 4. The compound according to claim 3 wherein the compound is 6,7-bis-hydroxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline or 6,7-bis-methoxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline.
- 5. The compound according to claim 3 wherein the compound is 1-[1,1′;4′,1″]terphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol.
- 6. The compound according to claim 2 wherein the compound is 1-(4′-fluoro-biphenyl-4-ylmethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline, 1-biphenyl-3-ylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline, 6,7-dimethoxy-1-(4′-methyl-biphenyl-4-ylmethyl)- 1,2,3,4-tetrahydro-isoquinoline, 6,7-dimethoxy-1-(3′-methoxy-biphenyl-4-ylmethyl)-1,2,3,4-tetrahydro-isoquinoline, or 1-(4-benzo [b]thiophen-2-yl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol.
- 7. The compound according to claim 1 wherein the compound is a racemic mixture.
- 8. The compound according to claim 1 wherein the compound is a substantially pure (−)-isomer or (+)-isomer.
- 9. The compound according to claim 1 wherein the compound is in the form of a salt.
- 10. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1.
- 11. A compound according to formula (II)
- 12. The compound according to claim 11 wherein R1 and R2 are hydroxyl or methoxy, and R3 is hydrogen.
- 13. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 11.
- 14. A method of destroying a target cell comprising:
providing a compound according to claim 1 and contacting a target cell with the compound under conditions effective to destroy the target cell.
- 15. The method according to claim 14 wherein the target cell is a cancer cell.
- 16. The method according to claim 14 wherein the cancer cell is selected from the group consisting of brain cancer cells, lung cancer cells, breast cancer cells, cervical cancer cells; prostate cancer cells, and combinations thereof.
- 17. The method according to claim 14 wherein the cancer cell is a glioma cell or glioblastoma cell.
- 18. The method according to claim 14 wherein the compound is 6,7-bis-hydroxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline, 6,7-bis-methoxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline, or 1-[1,1′;4′,1″]terphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol.
- 19. A method of treating or preventing a cancerous condition comprising:
providing a compound according to claim 1 and administering an effective amount of the compound to a patient under conditions to treat an existing cancerous condition or prevent development of a cancerous condition.
- 20. The method according to claim 19 wherein the cancerous condition is selected from the group consisting of brain cancer, lung cancer, breast cancer, cervical cancer, prostate cancer, and combinations thereof.
- 21. The method according to claim 20 where the brain cancer is characterized by the presence of glioma cells, glioblastoma cells, or a combination thereof.
- 22. The method according to claim 19 wherein the compound is compound is 6,7-bis-hydroxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline, 6,7-bis-methoxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline, or 1-[1,1′;4′,1″]terphenyl-4-ylmethyl-1,2,3, 4-tetrahydro-isoquinoline-6,7-diol.
- 23. The method according to claim 19 wherein said administering is carried out orally, topically, transdermally, parenterally, subcutaneously, intravenously, intramuscularly, intraperitoneally, by intranasal instillation, by intracavitary or intravesical instillation, by inhalation, intravaginally, intracranially, intraocularly, intraarterially, intralesionally, or by application to mucous membranes.
- 24. A method of destroying a target cell comprising:
providing a compound according to claim 11 and contacting a target cell with the compound under conditions effective to disrupt cellular metabolism and destroy the target cell.
- 25. The method according to claim 24 wherein the target cell is a cancer cell.
- 26. The method according to claim 24 wherein the cancer cell is selected from the group consisting of brain cancer cells, lung cancer cells, breast cancer cells, cervical cancer cells, prostate cancer cells, and combinations thereof.
- 27. The method according to claim 24 wherein the cancer cell is a glioma cell or glioblastoma cell.
- 28. A method of treating or preventing a cancerous condition comprising:
providing a compound according to claim 11 and administering an effective amount of the compound to a patient under conditions to treat an existing cancerous condition or prevent development of a cancerous condition.
- 29. The method according to claim 28 wherein the cancerous condition is selected from the group consisting of brain cancer, lung cancer, breast cancer, cervical cancer, prostate cancer, and combinations thereof.
- 30. The method according to claim 28 where the brain cancer is characterized by the presence of glioma cells, glioblastoma cells, or a combination thereof.
- 31. The method according to claim 28 wherein said administering is carried out orally, topically, transdermally, parenterally, subcutaneously, intravenously, intramuscularly, intraperitoneally, by intranasal instillation, by intracavitary or intravesical instillation, by inhalation, intravaginally, intracranially, intraocularly, intraarterially, intralesionally, or by application to mucous membranes.
- 32. A method of preparing a tetrahydroisoquinoline compound
- 33. A method of preparing a tetrahydroisoquinoline compound according to claim 1 comprising:
treating a precursor of formula (IB) 75under conditions effective to form a six-membered N-hetero ring fused with the phenyl, thereby forming the compound of formula (I).
- 34. The method according to claim 33 further comprising:
reacting 76with (R9R10C)COCl under conditions effective to prepare the compound according to formula (IB).
- 35. A method of preparing a compound according to claim 11, wherein R3 is hydrogen, the method comprising:
treating a compound having the structure 77under conditions effective to open the N-hetero ring between C-1 and the phenyl ring, thereby forming the compound according to formula (II).
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Patent Application Serial No. 60/363,952, filed Mar. 13, 2002, which is hereby incorporated by reference in its entirety.
Provisional Applications (1)
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Number |
Date |
Country |
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60363952 |
Mar 2002 |
US |