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US3968112A
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Synthesis of penniclavine and elymoclavine
Assignee: Eli Lilly and Co
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Filing: 1975-08-11
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Granted: 1976-07-06
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Expires: 1995-08-11
Abstract
Abstract Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.
Inventors
- 👤 Edmund C. Kornfeld
- 👤 Nicholas J. Bach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:39
CPC Classifications
C; C07; C07D; C07D457/00; C07D457/02; C07D457/10
Claims Analysis
Total Claims: 2
Claim 1
Independent Claim
102 words
The process which comprises reducing with a metal hydride in an inert solvent a compound of the formula ##SPC8## wherein alk and alk' are the same or different (C 1 -C 3 ) alkyl groups to yield an 8-hydroxymethyl-8-ergolene of the formula ##SPC9## wherein alk has the same meaning as hereinabove; rearranging said 8-hydroxymethyl-8-ergolene in aqueous acid, in an alkanolic (alkOH) acid or in an acidic (alkCOOH) medium to yield, respectively, penniclavine (R=H), an 8α-alkylpenniclavine ether (R=alk) or 8α-alkanoyl penniclavine ester (R=alk--CO) of the formula ##SPC10## wherein R is H, alk or alk-CO, and alk is (C 1 -C 3 ) alkyl.
Claim 2
Dependent Claim
102 words
The process which comprises reducing with a metal hydride in an inert solvent a compound of the formula ##SPC8## wherein alk and alk' are the same or different (C 1 -C 3 ) alkyl groups to yield an 8-hydroxymethyl-8-ergolene of the formula ##SPC9## wherein alk has the same meaning as hereinabove; rearranging said 8-hydroxymethyl-8-ergolene in aqueous acid, in an alkanolic (alkOH) acid or in an acidic (alkCOOH) medium to yield, respectively, penniclavine (R=H), an 8α-alkylpenniclavine ether (R=alk) or 8α-alkanoyl penniclavine ester (R=alk--CO) of the formula ##SPC10## wherein R is H, alk or alk-CO, and alk is (C 1 -C 3 ) alkyl.
References Cited (Backward Citations)
US3879554A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-06 | 1980-01-05 | 1980-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-06 | 1984-01-05 | 1984-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-06 | 1988-01-05 | 1988-07-06 | $7700.00 | Window Closed / Lapsed |