Claims
- 1. An anthracycline glycoside of the formula ##STR35## wherein R.sup.1 represents hydrogen, hydroxyl, tetrahydropyranyloxy, C.sub.2 -C.sub.7 alkanoyloxy or phenylacetyloxy and R.sup.2 represents hydrogen, C.sub.1 -C.sub.8 alkyloxyethyl, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, with the provisos that (1) when R.sup.1 is hydrogen or hydroxyl, R.sup.2 is not hydrogen and (2) when R.sup.1 is tetrahydropyranyloxy, R.sup.2 is hydrogen or tetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 2. An anthracycline glycoside of the formula ##STR36## wherein R.sup.1 represents a hydrogen atom, a hydroxyl group or a tetrahydropyranyloxy group and R.sup.2 represents a hydrogen atom or a tetrahydropyranyl group, providing that when R.sup.1 is a hydrogen atom or a hydroxyl group, R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
- 3. An anthracycline glycoside of the formula ##STR37## wherein R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
- 4. The compound according to claim 3 which is 4'-O-tetrahydropyranyl daunomycin (isomer a), or a nontoxic acid addition salt thereof.
- 5. The compound according to claim 3 which is 4'-O-tetrahydropyranyl daunomycin (isomer b), or a nontoxic acid addition salt thereof.
- 6. The anthracycline glycoside of the formula ##STR38## wherein R.sup.1 is a tetrahydropyranyloxy group and R.sup.2 is hydrogen, or a nontoxic acid addition salt thereof.
- 7. An anthracycline glycoside of the formula ##STR39## wherein R.sup.1 is tetrahydropyranyloxy and R.sup.2 is tetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 8. The compound according to claim 7 which is 4',14-bis(O-tetrahydropyranyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 9. The compound according to claim 7 which is 4',14-bis(O-tetrahydropyranyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 10. An anthracycline glycoside of the formula ##STR40## wherein R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
- 11. The compound according to claim 10 which is 4'-O-tetrahydropyranyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 12. The compound according to claim 10 which is 4'-O-tetrahydropyranyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 13. An anthracycline glycoside of the formula ##STR41## wherein R.sup.1 is a hydrogen atom, a hydroxyl group, an alkoanoyloxy group having from 2 to 7 carbon atoms inclusive or a phenylacetyloxy group and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, with the proviso that when R.sup.1 is hydrogen or hydroxyl, R.sup.2 is not tetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 14. An anthracycline glycoside according to claim 13 wherein R.sup.1 is acetyloxy, isobutyloyloxy or phenylacetyloxy and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 15. An anthracycline glycoside according to claim 13 wherein R.sup.1 is hydrogen or hydroxyl and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, 6-methoxytetrahydropyranyl, or 6-acetoxymethyltetrahydropyranyl, or a nonotoxic acid addition salt thereof.
- 16. The compound of claim 13 which is 14-O-acetyl-4'-O-tetrahydropyranyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 17. The compound of claim 13 which is 14-O-acetyl-4'-O-tetrahydropyranyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 18. The compound of claim 13 which is 14-O-isobutyloyl-4'-O-tetrahydropyranyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 19. The compound of claim 13 which is 14-O-isobutyloyl-4'-O-tetrahydropyranyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 20. The compound of claim 13 which is 14-O-phenylacetyl-4'-O-tetrahydropyranyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 21. The compound of claim 13 which is 14-O-phenylacetyl-4'-O-tetrahydropyranyl adriamycin (isomber b), or a nontoxic acid addition salt thereof.
- 22. The compound of claim 13 which is 14-O-acetyl-4'-O-tetrahydrofuranyl adriamycin, or a nontoxic acid addition salt thereof.
- 23. The compound of claim 13 which is 4'-O-tetrahydrofuranyl adriamycin, or a nontoxic acid addition salt thereof.
- 24. The compound of claim 13 which is 4'-O-tetrahydrofuranyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 25. The compound of claim 13 which is 4'-O-tetrahydrofuranyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 26. The compound of claim 13 which is 14-O-phenylacetyl-4'-O-(6-acetoxymethyltetrahydropyranyl)adriamycin, or a nonotoxic acid addition salt thereof.
- 27. The compound of claim 13 which is 4'-O-(6-acetoxymethyltetrahydropyranyl)adriamycin, or a nontoxic acid addition salt thereof.
- 28. The compound of claim 13 which is 14-O-phenylacetyl-4'-O-(1-ethyloxyethyl)adriamycin, or a nontoxic acid addition salt thereof.
- 29. The compound of claim 13 which is 4'-O-(1-ethyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 30. The compound of claim 13 which is 4'-O-(1-ethyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 31. The compound of claim 13 which is 14-O-acetyl-4'-O-(1-butyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 32. The compound of claim 13 which is 14-O-acetyl-4'-O-(1-butyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 33. The compound of claim 13 which is 4'-O-(1-butyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 34. The compound of claim 13 which is 4'-O-(1-butyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 35. The compound of claim 13 which is 14-O-acetyl-4'-O-(1-isobutyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 36. The compound of claim 13 which is 14-O-acetyl-4'-O-(1-isobutyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 37. The compound of claim 13 which is 4'-O-(1-isobutyloxyethyl)adriamycin (isomer a), or a nonotoxic acid addition salt thereof.
- 38. The compound of claim 13 which is 4'-O-(1-isobutyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 39. The compound of claim 13 which is 14-O-acetyl-4'-O-(6-methylheptyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 40. The compound of claim 13 which is 14-O-acetyl-4'-O-(6-methylheptyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 41. The compound of claim 13 which is 4'-O-(6-methylheptyloxyethyl)adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 42. The compound of claim 13 which is 4'-O-(6-methylheptyloxyethyl)adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 43. The compound of claim 13 which is 14-O-acetyl-4'-O-cyclohexyloxyethyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 44. The compound of claim 13 which is 14-O-acetyl-4'-O-cyclohexyloxyethyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 45. The compound of claim 13 which is 4'-O-cyclohexyloxyethyl adriamycin (isomer a), or a nontoxic acid addition salt thereof.
- 46. The compound of claim 13 which is 4'-O-cyclohexyloxyethyl adriamycin (isomer b), or a nontoxic acid addition salt thereof.
- 47. The compound of claim 13 which is 4'-O-(tetrahydrofuranyl)daunomycin, or a nontoxic acid addition salt thereof.
- 48. The compound of claim 13 which is 4'-O-(6-acetoxymethyltetrahydropyranyl)daunomycin, or a nontoxic acid addition salt thereof.
- 49. The compound of claim 13 which is 4'-O-(6-methoxytetrahydropyranyl)daunomycin (isomer a), or a nontoxic acid addition salt thereof.
- 50. The compound of claim 13 which is 4'-O-(6-methoxytetrahydropyranyl)daunomycin (isomber b), or a nontoxic acid addition salt thereof.
- 51. The compound of claim 13 which is 4'-O-(6-carbomethoxytetrahydropyranyl)daunomycin, or a nonotoxic acid addition salt thereof.
- 52. The compound of claim 13 which is 4'-O-(1-ethyloxyethyl)daunomycin (isomer a), or a nontoxic acid addition salt thereof.
- 53. The compound of claim 13 which is 4'-O-(1-ethyloxyethyl)daunomycin (isomer b), or a nontoxic acid addition salt thereof.
- 54. The compound of claim 13 which is 4'-O-(1-isobutyloxyethyl)daunomycin (isomer a), or a nontoxic acid addition salt thereof.
- 55. The compound of claim 13 which is 4'-O-(1-isobutyloxyethyl)daunomycin (isomer b), or a nontoxic acid addition salt thereof.
- 56. The compound of claim 13 which is 4'-O-(1-butyloxyethyl)daunomycin (isomer a), or a nontoxic acid addition salt thereof.
- 57. The compound of claim 13 which is 4'-O-(1-butyloxyethyl)daunomycin (isomer b), or a nontoxic acid addition salt thereof.
- 58. An anthracycline glycoside of the formula ##STR42## wherein R.sup.3 is phenylacetyloxy or alkanoyloxy having from 2 to 7 carbon atoms inclusive and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 59. An anthracycline glycoside of the formula ##STR43## wherein R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, 6-methoxytetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
- 60. An anthracycline glycoside of the formula ##STR44## wherein R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
Priority Claims (3)
Number |
Date |
Country |
Kind |
53-94348 |
Aug 1978 |
JPX |
|
54-11702 |
Feb 1979 |
JPX |
|
54-110255 |
Aug 1979 |
JPX |
|
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part application of our prior, copending application Ser. No. 928,627 filed July 27, 1978, now abandoned.
US Referenced Citations (6)
Number |
Name |
Date |
Kind |
3590028 |
Arcamone et al. |
Jun 1971 |
|
3616242 |
Belloc et al. |
Oct 1971 |
|
3803124 |
Arcamone et al. |
Apr 1974 |
|
4012448 |
Smith et al. |
Mar 1977 |
|
4020270 |
Arcamone et al. |
Apr 1977 |
|
4025623 |
Arcamone et al. |
May 1977 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
1003383 |
Sep 1965 |
GBX |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
928627 |
Jul 1978 |
|