GB1163106A - 4'-Demethyl-Epipodophyllotoxin Derivatives - Google Patents
4'-Demethyl-Epipodophyllotoxin DerivativesInfo
- Publication number
- GB1163106A GB1163106A GB53218/66A GB5321866A GB1163106A GB 1163106 A GB1163106 A GB 1163106A GB 53218/66 A GB53218/66 A GB 53218/66A GB 5321866 A GB5321866 A GB 5321866A GB 1163106 A GB1163106 A GB 1163106A
- Authority
- GB
- United Kingdom
- Prior art keywords
- demethyl
- epipodophyllotoxin
- vii
- organic solvent
- acetyl
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1,163,106. 4<SP>1</SP> - Demethyl - epipodophyllotoxin derivatives. SANDOZ Ltd. 28 Nov., 1966 [14 Dec., 1965 (3); 12 Oct., 1966], No. 53218/66. Heading C2C. 4<SP>1 </SP>- Demethyl - epipodophyllotoxin derivatives of the general Formula I in which R is phenyl, 2-furyl or 2-thienyl radical are prepared by reacting 4<SP>1</SP>-demethyl-epipodophyllotoxin- #-D-glucoside (II) with an aldehyde, RCHO, in the presence of an acid catalyst. The compound (II) is obtained by hydrogenolysis of tetra - O - acetyl - 4<SP>1</SP> - carbobenzyloxy - 4<SP>1</SP>- demethyl - epipodophyllotoxin - # - D - glucoside (IV) to split off the carbobenzyloxy group followed by alcoholysis in the presence of anhydrous zinc acetate to remove the acetyl radicals or these steps may be reversed. The compound (IV) is obtained either by condensing 4<SP>1 </SP>- carbobenzyloxy - 4<SP>1</SP> - demethylepipodophyllotoxin (VII) with α-acetobromoglucose in an inert organic solvent in the presence of zinc oxide or mercury oxide or by condensing VII or the corresponding podophyllotoxin with 2,3,4,6-tetra-O-acetyl-#- D- glucose in an inert organic solvent, at a temperature below 0 C. and in the presence of boron trifluoride ethyl etherate. The compound VII or the corresponding podophyllotoxin is prepared by reacting 41-demethyl-epipodophyllotoxin or 4<SP>1 </SP>- demethylpodophyllotoxin with benzylchloroformate at - 20 to - 5 C. in the presence of a tertiary organic base in an inert anhydrous organic solvent. Pharmaceutical compositions having cytostatic activity and containing compounds of Formula I are administered orally, parenterally or in a suppository.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1723065A CH507934A (en) | 1965-12-14 | 1965-12-14 | Epipodophyllotoxinglucosides |
| CH1723265A CH469000A (en) | 1965-12-14 | 1965-12-14 | Process for the production of new glucosides |
| CH1722965 | 1965-12-14 | ||
| CH1470366 | 1966-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1163106A true GB1163106A (en) | 1969-09-04 |
Family
ID=27429581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53218/66A Expired GB1163106A (en) | 1965-12-14 | 1966-11-28 | 4'-Demethyl-Epipodophyllotoxin Derivatives |
Country Status (15)
| Country | Link |
|---|---|
| AT (2) | AT298681B (en) |
| BE (1) | BE691066A (en) |
| CH (2) | CH507934A (en) |
| DK (2) | DK120849B (en) |
| ES (1) | ES334424A1 (en) |
| FI (2) | FI47357C (en) |
| FR (1) | FR6310M (en) |
| GB (1) | GB1163106A (en) |
| IL (3) | IL27042A (en) |
| NL (1) | NL6617379A (en) |
| NO (1) | NO120371B (en) |
| OA (1) | OA02648A (en) |
| SE (2) | SE370072B (en) |
| SU (1) | SU414788A3 (en) |
| YU (1) | YU33197B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713246A (en) * | 1984-03-19 | 1987-12-15 | Bristol-Myers Company | Etoposide oral dosage form |
| US4965348A (en) * | 1989-05-19 | 1990-10-23 | Bristol-Myers Company | Dimeric epipodophyllotoxin glucoside derivatives |
| US5036055A (en) * | 1989-06-07 | 1991-07-30 | Bristol-Myers Company | Acylated derivatives of etoposide |
-
1965
- 1965-12-14 CH CH1723065A patent/CH507934A/en not_active IP Right Cessation
- 1965-12-14 CH CH1723265A patent/CH469000A/en unknown
-
1966
- 1966-11-28 GB GB53218/66A patent/GB1163106A/en not_active Expired
- 1966-12-06 OA OA52682A patent/OA02648A/en unknown
- 1966-12-09 NL NL6617379A patent/NL6617379A/xx unknown
- 1966-12-10 YU YU2331/66A patent/YU33197B/en unknown
- 1966-12-12 IL IL27042A patent/IL27042A/en unknown
- 1966-12-12 AT AT1053668A patent/AT298681B/en active
- 1966-12-12 IL IL34853A patent/IL34853A/en unknown
- 1966-12-12 BE BE691066D patent/BE691066A/xx not_active IP Right Cessation
- 1966-12-12 FI FI663294A patent/FI47357C/en active
- 1966-12-12 ES ES334424A patent/ES334424A1/en not_active Expired
- 1966-12-12 AT AT1142266A patent/AT295048B/en not_active IP Right Cessation
- 1966-12-12 SU SU1118481A patent/SU414788A3/ru active
- 1966-12-13 SE SE03842/70A patent/SE370072B/xx unknown
- 1966-12-13 NO NO165984A patent/NO120371B/no unknown
- 1966-12-13 DK DK646366AA patent/DK120849B/en not_active IP Right Cessation
- 1966-12-13 SE SE17094/66A patent/SE337595B/xx unknown
-
1967
- 1967-03-10 FR FR98340A patent/FR6310M/fr not_active Expired
-
1968
- 1968-03-15 DK DK112368AA patent/DK118826B/en not_active IP Right Cessation
-
1970
- 1970-07-06 IL IL34853A patent/IL34853A0/en unknown
-
1971
- 1971-06-24 FI FI711801A patent/FI47358C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DK118826B (en) | 1970-10-12 |
| SU414788A3 (en) | 1974-02-05 |
| OA02648A (en) | 1970-12-15 |
| IL34853A (en) | 1971-04-28 |
| CH507934A (en) | 1971-05-31 |
| IL27042A (en) | 1971-04-28 |
| FI47358C (en) | 1973-11-12 |
| NO120371B (en) | 1970-10-12 |
| FI47358B (en) | 1973-07-31 |
| SE370072B (en) | 1974-09-30 |
| FI47357C (en) | 1973-11-12 |
| AT295048B (en) | 1971-12-27 |
| ES334424A1 (en) | 1968-03-01 |
| IL34853A0 (en) | 1970-09-17 |
| YU33197B (en) | 1976-06-30 |
| CH469000A (en) | 1969-02-28 |
| FR6310M (en) | 1968-09-16 |
| BE691066A (en) | 1967-06-12 |
| SE337595B (en) | 1971-08-16 |
| AT298681B (en) | 1972-05-25 |
| NL6617379A (en) | 1967-06-15 |
| DK120849B (en) | 1971-07-26 |
| FI47357B (en) | 1973-07-31 |
| YU233166A (en) | 1975-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 416 | Proceeding under section 16 patents act 1949 | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE | Patent expired |