US4075214A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of leurosidine and novel leurosidine 4'-ethers and esters
Assignee: Eli Lilly and Co
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Filing: 1976-05-17
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Granted: 1978-02-21
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Expires: 1996-05-17
Abstract
Abstract Vincaleukoblastine (VLB, vinblastine) is converted to leurosidine, its 4' epimer, by reaction with thionyl chloride to form a bis-sulfite ester followed by treatment of the bis-sulfite ester with silver perchlorate. The bis-sulfite ester is covertible to novel 4' ethers by treatment with a lower alkanol or 4' esters of leurosidine perchlorate with acetic anhydride.
Inventors
- 👤 Allen S. Katner
- 👤 Gerald E. Gutowski
- 👤 Jean C. Miller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 19:15
CPC Classifications
C; C07; C07D; C07D519/00; C07D519/04
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
16 words
A compound of the formula ##STR4## wherein R' is methoxy, ethoxy, propoxy or an azide group.
Claim 2
Dependent Claim
16 words
A compound of the formula ##STR4## wherein R' is methoxy, ethoxy, propoxy or an azide group.
Claim 3
Dependent Claim
61 words
A process for preparing leurosidine and its 4'-lower alkoxy ethers which comprises reacting VLB with thionyl chloride in pyridine to form a 4'-bis-sulfite ester of VLB and then reacting said bis-sulfite ester with silver perchlorate in the presence of water or of a lower alkanol to form a compound of the formula ##STR5## wherein R' is hydroxy, methoxy, ethoxy, or propoxy.
Claim 4
Dependent Claim
61 words
A process for preparing leurosidine and its 4'-lower alkoxy ethers which comprises reacting VLB with thionyl chloride in pyridine to form a 4'-bis-sulfite ester of VLB and then reacting said bis-sulfite ester with silver perchlorate in the presence of water or of a lower alkanol to form a compound of the formula ##STR5## wherein R' is hydroxy, methoxy, ethoxy, or propoxy.
Claim 5
Dependent Claim
11 words
A compound according to claim 1, said compound being leurosidine 4'-azide.
Claim 6
Dependent Claim
11 words
A compound according to claim 1, said compound being 4'-methoxy leurosidine.
Claim 7
Dependent Claim
7 words
VLB 4'-bis-sulfite ester of the formula ##STR6##
Claim 8
Dependent Claim
7 words
VLB 4'-bis-sulfite ester of the formula ##STR6##
References Cited (Backward Citations)
US3205220A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-20 | 1981-08-22 | 1982-02-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-20 | 1985-08-22 | 1986-02-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-20 | 1989-08-22 | 1990-02-21 | $7700.00 | Window Closed / Lapsed |