GB1347589A - Dehydrocardenolides - Google Patents
DehydrocardenolidesInfo
- Publication number
- GB1347589A GB1347589A GB5048872A GB5048872A GB1347589A GB 1347589 A GB1347589 A GB 1347589A GB 5048872 A GB5048872 A GB 5048872A GB 5048872 A GB5048872 A GB 5048872A GB 1347589 A GB1347589 A GB 1347589A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- nov
- formula
- radical
- acetoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1347589 19-Acetoxycardadienolides WARNER-LAMBERT CO 2 Nov 1972 [3 Nov 1971] 50488/72 Heading C2U The invention comprises compounds of formula (wherein R 1 is an optionally substituted tetrahydropyran-2-yl or glycosyl radical, Ac is acetyl, and the dotted lines denote compulsory #<SP>4</SP>- or #<SP>5</SP>-unsaturation) and their preparation from compounds of formula by reaction with a trialkyl orthoacetate in the presence of an acid catalyst. The resulting #<SP>4</SP>/#<SP>5</SP> mixture may be resolved by chromatography or fractional crystallization. When the radical R 1 contains a vicinal cis-diol grouping (as in helveticosol or convallatoxol), the axial hydroxyl group is acetylated concurrently. Compounds I are interconvertible (within R 1 ) by ketalization, alkylation and acylation of hydroxy groups, or by saponification of acetoxy groups (the latter being effected without hydrolysing the 19-acetoxy group). Compounds II are prepared by complex metal hydride reduction of the corresponding 19-oxocompounds. Compounds I are said to be cardioactive, and may be made up with carriers into pharmaceutical compositions for oral, parenteral and rectal administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712154649 DE2154649C3 (en) | 1971-11-03 | 1971-11-03 | Process for the preparation of 19-acetoxy-delta to the power of 4 / delta to the power of 5 -dehydrocardenolides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1347589A true GB1347589A (en) | 1974-02-27 |
Family
ID=5824097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5048872A Expired GB1347589A (en) | 1971-11-03 | 1972-11-02 | Dehydrocardenolides |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH585231A5 (en) |
| DE (1) | DE2154649C3 (en) |
| FR (1) | FR2158429B1 (en) |
| GB (1) | GB1347589A (en) |
| NL (1) | NL7214813A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES415515A1 (en) * | 1972-06-05 | 1976-05-01 | Warner Lambert Co | Novel delta 4/delta 5-dehydrocardenolides and process for their preparation |
-
1971
- 1971-11-03 DE DE19712154649 patent/DE2154649C3/en not_active Expired
-
1972
- 1972-11-02 NL NL7214813A patent/NL7214813A/xx not_active Application Discontinuation
- 1972-11-02 GB GB5048872A patent/GB1347589A/en not_active Expired
- 1972-11-02 FR FR7238725A patent/FR2158429B1/fr not_active Expired
- 1972-11-03 CH CH1606172A patent/CH585231A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2158429B1 (en) | 1976-07-02 |
| DE2154649B2 (en) | 1973-08-16 |
| CH585231A5 (en) | 1977-02-28 |
| FR2158429A1 (en) | 1973-06-15 |
| NL7214813A (en) | 1973-05-07 |
| DE2154649C3 (en) | 1974-03-14 |
| DE2154649A1 (en) | 1973-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |