Claims
- 1. An N-glycidylanthracycline derivative of the following formula I, ##STR17## in which R.sup.1 is hydrogen or a hydroxyl group,
- R.sup.2 is hydrogen, a hydroxyl group or an alkyloxy (C.sub.1 -C.sub.4) group,
- R.sup.3 is hydrogen, a hydroxyl group or a structure of the formula II ##STR18## R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH,
- R.sup.5 is hydrogen, a hydroxyl group, a methoxycarbonyl group or a structure of the formula II,
- R.sup.6 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group or a tetrahydropyranyl group,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or a mono- or di-methyloxy-substituted benzyl group, and
- R.sup.8 is a structure of the formula III or IV ##STR19## or the salts thereof with an inorganic or organic acid; and in which either one or both of R.sup.3 and R.sup.5 is a structure of the formula II.
- 2. N-glycidylanthracycline derivative as claimed in claim 1 in which
- R.sup.1 is hydrogen or a hydroxyl group,
- R.sup.2 is hydrogen, a hydroxyl group or a methoxy group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH,
- R.sup.5 is hydrogen, a hydroxyl group, a methoxycarbonyl group or a structure of the formula II,
- R.sup.6 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group or a tetrahydropyranyl group,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group and
- R.sup.8 is a structure of the formula III or IV.
- 3. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen or a hydroxyl group,
- R.sup.2 is hydrogen, a hydroxyl group or a methoxy group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH,
- R.sup.5 is hydrogen, a hydroxyl group or a methoxy-carbonyl group,
- R.sup.8 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group or a tetrahydropyranyl group,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group and
- R.sup.8 is a structure of the formula III or IV.
- 4. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen,
- R.sup.2 is hydrogen, a hydroxyl group or a methoxy group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH,
- R.sup.5 is hydrogen, a hydroxyl group or a methoxy-carboyl group,
- R.sup.6 is hydrogen or a tetrahydropyranyl group,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group and
- R.sup.8 is a structure of the formula III or IV.
- 5. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen,
- R.sup.2 is hydrogen, a hydroxyl group or a methoxy group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH,
- R.sup.5 is hydrogen, a hydroxyl group or a methoxy-carbonyl group,
- R.sup.6 is hydrogen or a tetrahydropyranyl group,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group and
- R.sup.8 is a structure of the formula III or IV.
- 6. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen,
- R.sup.2 is a hydroxyl group or a methoxy group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.3 or COCH.sub.2 OH,
- R.sup.5 is hydrogen or a hydroxyl group,
- R.sup.6 is hydrogen,
- R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4) or an allyl group and
- R.sup.8 is a structure of the formula III or IV.
- 7. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen,
- R.sup.2 is a hydroxyl group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3,
- R.sup.5 is a hydroxyl group,
- R.sup.6 is hydrogen,
- R.sup.7 is a methyl group and
- R.sup.8 is a structure of the formula III or IV.
- 8. N-glycidylanthracycline derivative as claimed in claim 1, in which
- R.sup.1 is hydrogen,
- R.sup.2 is a hydroxyl group,
- R.sup.3 is a structure of the formula II,
- R.sup.4 is CH.sub.2 CH.sub.3,
- R.sup.5 is a hydroxyl group,
- R.sup.6 is hydrogen,
- R.sup.7 is a methyl group and
- R.sup.8 is a structure of the formula III.
- 9. A pharmaceutical composition comprising a compound as claimed in claim 1 together with a pharmaceutically acceptable carrier.
Priority Claims (1)
Number |
Date |
Country |
Kind |
40 36 155.1 |
Nov 1990 |
DEX |
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Parent Case Info
This application is a continuation, of application Ser. No. 08/358,676, filed Dec. 19, 1994, abandoned, which was a continuation of Ser. No. 08/198,378, filed Feb. 18, 1994, abandoned, which was a continuation of application Ser. No. 08/071,347, filed Jun. 3, 1993 abandoned, which was a continuation of application Ser. No. 07/789,986, filed Nov. 12, 1991, abandoned.
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4408063 |
Baldwin et al. |
Oct 1983 |
|
4877870 |
Umezawa et al. |
Oct 1989 |
|
4948880 |
Hermentin et al. |
Aug 1990 |
|
Non-Patent Literature Citations (4)
Entry |
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Yuhsuke Kawakami, Tamio Asai, Kiyoshi Umeyama, and Yuya Yamashita Selectively Deuterated and Optically Active Cyclic Ethers, J. Orig. Chem, vol. 47, Jun. 1, 1981, pp. 3581-3585. |
Janice M. Klunder, Soo Y. Ko, and K. Barry Sharpless, Asymmetric Epoxidation of Allyl Alcohol: Efficient Routes to Homochiral .beta.-Adrenergic Blocking Agents, J. Orig. Chem, vol. 51, Apr. 15, 1986, pp. 3710-3712. |
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Continuations (4)
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Number |
Date |
Country |
Parent |
358676 |
Dec 1994 |
|
Parent |
198378 |
Feb 1994 |
|
Parent |
71347 |
Jun 1993 |
|
Parent |
789986 |
Nov 1991 |
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