GB1205965A - Epipodophyllotoxin glucoside derivatives - Google Patents
Epipodophyllotoxin glucoside derivativesInfo
- Publication number
- GB1205965A GB1205965A GB5384467A GB5384467A GB1205965A GB 1205965 A GB1205965 A GB 1205965A GB 5384467 A GB5384467 A GB 5384467A GB 5384467 A GB5384467 A GB 5384467A GB 1205965 A GB1205965 A GB 1205965A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epipodophyllotoxin
- demethyl
- carbobenzoxy
- glucoside
- tetra
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,205,965. Epipodophyllotoxin glucosides. SANDOZ Ltd. 27 Nov., 1967 [13 Dec., 1966 (5)], No. 53844/67. Heading C2C. Novel compounds of Formula (I) in which (a) R 1 signifies H and R 2 alkyl of more than 2C, alkenyl, cycloalkyl (C 5-6 ), or aryl, aralkyl or aralkenyl in which the aromatic ring may be substituted, preferably by one or more hydroxy, alkoxy, alkyl, nitro, or halo radicals, (b) R 1 and R 2 each signify alkyl, or (c) R 1 and R 2 together with the carbon atom to which they are attached signify a C 5-6 saturated cycloaliphatic ring are prepared by reacting compounds of general Formula (II) in which R 3 is H or carbobenzoxy with a compound R 1 (R 2 )C=O or a ketal or acetal thereof with CH 3 OH, C 2 H 5 OH or HOCH 2 CH 2 OH in the presence of an acid catalyst and any carbobenzoxy radical which may be present is split off. Intermediates prepared are 4<SP>1</SP>-demethyl-epipodophyllotoxin by isomerization of 41-demethyl - podophyllotoxin; 4<SP>1</SP> - carbobenzoxy - 4<SP>1</SP> - demethyl-epipodophyllotoxin from the formernamed intermediate; tetra - O - acetyl - 41 - carbobenzoxy - 4<SP>1</SP>- demethyl - epipodophyllotoxin- #-D-glucoside from the previous intermediate and 2,3,4,6 - tetra - O - acetyl - # - D - glucose; tetra - O - acetyl - 4<SP>1 </SP>- demethyl - epipodophyllotoxin - # - D - glucoside by hydrogenolysis of the last-named intermediate; and 4<SP>1</SP>-demethylepipodophyllotoxin - # - D - glucoside from the previous intermediate. Pharmaceutical compositions comprise a compound of Formula (I) in admixture with a suitable carrier or diluent and can be administered orally, enterally or parenterally. They have a cytostatic effect in vitro on mastocytoma cells and fibroblast cultures and a strong effect towards experimental tumours.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1775266A CH484101A (en) | 1966-12-13 | 1966-12-13 | Process for the production of new glucosides |
| CH1775366A CH481094A (en) | 1966-12-13 | 1966-12-13 | Process for the production of new glucosides |
| CH1775966A CH481097A (en) | 1966-12-13 | 1966-12-13 | Process for the preparation of a new glucoside |
| CH1775466A CH481913A (en) | 1966-12-13 | 1966-12-13 | Process for the production of new glucosides |
| CH1775666A CH481096A (en) | 1966-12-13 | 1966-12-13 | Process for the production of new glucosides |
| CH1775566A CH481095A (en) | 1966-12-13 | 1966-12-13 | Process for the preparation of new glucosides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1205965A true GB1205965A (en) | 1970-09-23 |
Family
ID=27543911
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5384467A Expired GB1205965A (en) | 1966-12-13 | 1967-11-27 | Epipodophyllotoxin glucoside derivatives |
| GB1946270A Expired GB1205966A (en) | 1966-12-13 | 1967-11-27 | 4'-DEMETHYL-EPIPODOPHYLLOTOXIN-beta-D-ETHYLIDENE-GLUCOSIDE |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1946270A Expired GB1205966A (en) | 1966-12-13 | 1967-11-27 | 4'-DEMETHYL-EPIPODOPHYLLOTOXIN-beta-D-ETHYLIDENE-GLUCOSIDE |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT285062B (en) |
| BE (1) | BE707822A (en) |
| CA (1) | CA952103A (en) |
| CH (7) | CH544752A (en) |
| CS (1) | CS152448B2 (en) |
| DE (1) | DE1643521C3 (en) |
| DK (1) | DK131429B (en) |
| FI (1) | FI48585C (en) |
| FR (2) | FR1572185A (en) |
| GB (2) | GB1205965A (en) |
| NL (1) | NL6716635A (en) |
| SE (1) | SE348192B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326753A (en) * | 1990-01-19 | 1994-07-05 | Nippon Kayaku Kabushiki Kaisha | Freeze-dried composition containing a 2-dimethylamino etoposide derivative |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713246A (en) * | 1984-03-19 | 1987-12-15 | Bristol-Myers Company | Etoposide oral dosage form |
| US4904768A (en) * | 1987-08-04 | 1990-02-27 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-phosphate derivatives |
| US4935504A (en) * | 1987-12-18 | 1990-06-19 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-acyl derivatives |
| US5463040A (en) * | 1994-06-28 | 1995-10-31 | Teva Pharmaceutical Industries, Ltd. | Method of preparing etoposide |
| US6207673B1 (en) | 1997-03-12 | 2001-03-27 | The University Of North Carolina At Chapel Hill | Covalent conjugates of topoisomerase I and topoisomerase II inhibitors |
-
1966
- 1966-12-13 CH CH1445369A patent/CH544752A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775466A patent/CH481913A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775266A patent/CH484101A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775666A patent/CH481096A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775966A patent/CH481097A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775366A patent/CH481094A/en not_active IP Right Cessation
- 1966-12-13 CH CH1775566A patent/CH481095A/en not_active IP Right Cessation
-
1967
- 1967-11-27 GB GB5384467A patent/GB1205965A/en not_active Expired
- 1967-11-27 GB GB1946270A patent/GB1205966A/en not_active Expired
- 1967-12-07 NL NL6716635A patent/NL6716635A/xx unknown
- 1967-12-09 DE DE1967S0113215 patent/DE1643521C3/en not_active Expired
- 1967-12-11 FR FR1572185D patent/FR1572185A/fr not_active Expired
- 1967-12-11 CS CS877367A patent/CS152448B2/cs unknown
- 1967-12-11 CA CA007,216A patent/CA952103A/en not_active Expired
- 1967-12-11 BE BE707822D patent/BE707822A/xx not_active IP Right Cessation
- 1967-12-12 SE SE1706767A patent/SE348192B/xx unknown
- 1967-12-12 FI FI331067A patent/FI48585C/en active
- 1967-12-12 AT AT1119667A patent/AT285062B/en not_active IP Right Cessation
- 1967-12-12 DK DK620967A patent/DK131429B/en not_active IP Right Cessation
-
1968
- 1968-03-08 FR FR142954A patent/FR8031M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326753A (en) * | 1990-01-19 | 1994-07-05 | Nippon Kayaku Kabushiki Kaisha | Freeze-dried composition containing a 2-dimethylamino etoposide derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1643521C3 (en) | 1978-09-21 |
| FR1572185A (en) | 1969-06-27 |
| AT285062B (en) | 1970-10-12 |
| FI48585C (en) | 1974-11-11 |
| CA952103A (en) | 1974-07-30 |
| CH544752A (en) | 1974-01-15 |
| SE348192B (en) | 1972-08-28 |
| CS152448B2 (en) | 1973-12-19 |
| CH481097A (en) | 1969-11-15 |
| DE1643521B2 (en) | 1978-01-19 |
| NL6716635A (en) | 1968-06-14 |
| DK131429C (en) | 1975-12-15 |
| CH481096A (en) | 1969-11-15 |
| FR8031M (en) | 1970-08-03 |
| GB1205966A (en) | 1970-09-23 |
| CH481095A (en) | 1969-11-15 |
| FI48585B (en) | 1974-07-31 |
| DE1643521A1 (en) | 1971-04-08 |
| BE707822A (en) | 1968-06-11 |
| CH481094A (en) | 1969-11-15 |
| CH484101A (en) | 1970-01-15 |
| DK131429B (en) | 1975-07-14 |
| CH481913A (en) | 1969-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1152226A (en) | Novel Gona-1,3,5(10)-Trienes, processes for their preparation, and compositions incorporating them | |
| GB1205965A (en) | Epipodophyllotoxin glucoside derivatives | |
| GB1162248A (en) | Epipodophyllotoxin Derivatives | |
| GB1268230A (en) | Steroid glycosides and process for their manufacture | |
| GB1223461A (en) | Pteridine derivatives | |
| GB1173780A (en) | Stabilizers for Organic Materials | |
| GB1479362A (en) | 3,17,18-trihydroxy-1,3,5(10)-oestratrienes and their derivatives | |
| KAWAHARA et al. | A novel dimeric steroid, calvasterone from the fungus Calvatia cyathiformis | |
| ES348727A1 (en) | 3-(2'-chloroethylthio)-6-formyl-9alpha-fluoro-steroids | |
| GB1532551A (en) | Furo(3,4-6)furone derivatives and their preparation | |
| FR2112131A1 (en) | 2-and 3-glucose-2-yl-demethylthiololchicines - antimitotic agents,prepared from colchicine | |
| GB1242372A (en) | A new oestratriol and a process for its manufacture | |
| GB1239073A (en) | ||
| Suzuki | Studies on Streptomyces Antibiotic, Cycloheximide. XI. Preparation and Chemical Structure of the Oxidation Products (ψ-Cycloheximides) from Dihydrocycloheximides | |
| GB1164412A (en) | Derivatives of 2alpha,3alpha-Epithiosteroids and process for the preparation thereof | |
| GB1327745A (en) | Steroid glycosides and a process for their manufacture | |
| GB1193951A (en) | 03-C2-4 Alkyl-Gonane Compounds | |
| GB1347589A (en) | Dehydrocardenolides | |
| ES375061A1 (en) | Sulphamido-steroids and the preparation thereof | |
| GB1430188A (en) | Diaza-oxa-bicyclodecane derivatives | |
| GB1193099A (en) | Estratrienes, Processes for their Preparation, and Compositions Incorporating them | |
| GB1319372A (en) | 2 2 substituted cardenolide glycosides | |
| GB1248529A (en) | Pentol derivatives, process for their manufacture and compositions containing them | |
| GB1229334A (en) | ||
| GB1189217A (en) | 09-nor-Testosterone Phenoxyacetate and 6-Methyl Derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |