GB1320361A - 22-substituted cardenolideglycosides - Google Patents
22-substituted cardenolideglycosidesInfo
- Publication number
- GB1320361A GB1320361A GB2819670A GB2819670A GB1320361A GB 1320361 A GB1320361 A GB 1320361A GB 2819670 A GB2819670 A GB 2819670A GB 2819670 A GB2819670 A GB 2819670A GB 1320361 A GB1320361 A GB 1320361A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- hydroxyl
- compounds
- tetrahydropyranyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 cardenolide glycosides Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- TYYDXNISHGVDGA-UHFFFAOYSA-N Corotoxigenin Natural products CC12CCC3C(CCC4CC(O)CCC34C=O)C1CCC2C5=CC(=O)OC5 TYYDXNISHGVDGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
1320361 22-Substituted cardenolide glycosides DR KARL THOMAE GmbH 10 June 1970 [10 June 1969] 28196/70 Heading C2U [Also in Division C3] The invention comprises compounds of formula wherein R 1 is H, OH, acyloxy, 2<SP>1</SP>-tetrahydropyranyloxy or trimethylsiloxy; X is F, Cl, C 1-4 alkyl or C 1-4 alkoxy; and A is a group of formula wherein R 2 is H, acyl, 2<SP>1</SP>-tetrahydropyranyl or trimethylsilyl. Preparation thereof is by base-catalysed intramolecular cyclization of compounds of formula wherein R<SP>1</SP> 1 is H or protected hydroxy; X is as defined above; A<SP>1</SP> is a group as defined above for A wherein R 2 is a hydroxyl-protecting group; and R 3 is C 1-4 alkyl. When the resultant product contains a hydroxyl-protecting group other than acyl, 2<SP>1</SP>-tetrahydropyranyl or trimethylsilyl (e.g. benzyl), then said group must be removed to give a compound of Formula I. Removal of protecting groups in general may be effected by acid or base hydrolysis or by hydrogenolysis. A free hydroxyl group (R 1 or OR 2 ) in the product may thereafter be acylated. The starting materials are prepared as described in Specification 1,320,362. The inventive compounds are said to be cardioactive, and may be made up with carriers into pharmaceutical compositions for oral, rectal and parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691929427 DE1929427C (en) | 1969-06-10 | 22 Fluorocardohd glycosides and medicinal products containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1320361A true GB1320361A (en) | 1973-06-13 |
Family
ID=5736593
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2819670A Expired GB1320361A (en) | 1969-06-10 | 1970-06-10 | 22-substituted cardenolideglycosides |
| GB5279472A Expired GB1320362A (en) | 1969-06-10 | 1970-06-10 | 21-phosphonoalkanoyloxy-pregnanes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5279472A Expired GB1320362A (en) | 1969-06-10 | 1970-06-10 | 21-phosphonoalkanoyloxy-pregnanes |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT300205B (en) |
| BE (1) | BE751768A (en) |
| BG (1) | BG17306A3 (en) |
| CH (1) | CH549563A (en) |
| DK (1) | DK128900B (en) |
| ES (1) | ES380440A1 (en) |
| FI (1) | FI47182C (en) |
| FR (1) | FR2052944B1 (en) |
| GB (2) | GB1320361A (en) |
| IE (1) | IE34292B1 (en) |
| IL (1) | IL34690A (en) |
| NL (1) | NL7008408A (en) |
| PL (1) | PL81115B1 (en) |
| RO (1) | RO58404A (en) |
| SE (1) | SE360357B (en) |
| ZA (1) | ZA703907B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788669A (en) * | 1971-09-11 | 1973-03-12 | Thomae Gmbh Dr K | NEW CARDENOLIDE-GLUCOSIDES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1013910A (en) * | 1962-11-28 | 1965-12-22 | Manuf De Produits Pharmaoeutiq | New derivative of gitoxin, the use and preparation thereof |
| CH459190A (en) * | 1965-02-01 | 1968-07-15 | Sandoz Ag | Process for the production of a new cardenolide |
-
1970
- 1970-06-04 BG BG014854A patent/BG17306A3/en unknown
- 1970-06-05 ES ES380440A patent/ES380440A1/en not_active Expired
- 1970-06-05 RO RO63560A patent/RO58404A/ro unknown
- 1970-06-08 FI FI701616A patent/FI47182C/en active
- 1970-06-09 FR FR7021111A patent/FR2052944B1/fr not_active Expired
- 1970-06-09 DK DK298770AA patent/DK128900B/en unknown
- 1970-06-09 IE IE749/70A patent/IE34292B1/en unknown
- 1970-06-09 CH CH863270A patent/CH549563A/en not_active IP Right Cessation
- 1970-06-09 PL PL1970141186A patent/PL81115B1/pl unknown
- 1970-06-09 IL IL34690A patent/IL34690A/en unknown
- 1970-06-09 ZA ZA703907A patent/ZA703907B/en unknown
- 1970-06-09 AT AT518170A patent/AT300205B/en not_active IP Right Cessation
- 1970-06-10 SE SE08079/70A patent/SE360357B/xx unknown
- 1970-06-10 GB GB2819670A patent/GB1320361A/en not_active Expired
- 1970-06-10 NL NL7008408A patent/NL7008408A/xx unknown
- 1970-06-10 BE BE751768D patent/BE751768A/en unknown
- 1970-06-10 GB GB5279472A patent/GB1320362A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BG17306A3 (en) | 1973-07-25 |
| GB1320362A (en) | 1973-06-13 |
| NL7008408A (en) | 1970-12-14 |
| IL34690A (en) | 1974-06-30 |
| SE360357B (en) | 1973-09-24 |
| ES380440A1 (en) | 1972-09-01 |
| RO58404A (en) | 1975-09-15 |
| IE34292L (en) | 1970-12-19 |
| PL81115B1 (en) | 1975-08-30 |
| DK128900B (en) | 1974-07-22 |
| FI47182C (en) | 1973-10-10 |
| ZA703907B (en) | 1971-02-24 |
| CH549563A (en) | 1974-05-31 |
| BE751768A (en) | 1970-12-10 |
| IE34292B1 (en) | 1975-04-02 |
| FR2052944A1 (en) | 1971-04-16 |
| IL34690A0 (en) | 1970-08-19 |
| AT300205B (en) | 1972-07-25 |
| DE1929427A1 (en) | 1971-01-07 |
| FI47182B (en) | 1973-07-02 |
| FR2052944B1 (en) | 1974-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |