GB823068A - Condensation products from glucosides - Google Patents
Condensation products from glucosidesInfo
- Publication number
- GB823068A GB823068A GB14759/56A GB1475956A GB823068A GB 823068 A GB823068 A GB 823068A GB 14759/56 A GB14759/56 A GB 14759/56A GB 1475956 A GB1475956 A GB 1475956A GB 823068 A GB823068 A GB 823068A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glucoside
- podophyllotoxin
- benzylidene
- derivatives
- thenylidene
- 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)
Abstract
The invention comprises compounds of the formula <FORM:0823068/IV (a)/1> (R1 represents H or an alkyl group containing from 1-6 carbon atoms, and R2 denotes alkyl, aryl, or a heterocyclic residue), and their preparation by condensing the corresponding glucoside with an aldehyde R2CHO, preferably in the presence of a water-binding agent, particularly zinc chloride, anhydrous copper sulphate, or small quantities of concentrated sulphuric or hydrochloric acid, or p-toluene sulphonic acid. An inert solvent, e.g. dioxane or dimethylformamide may be used and the water produced in the reaction removed by azeotropic distillation with an immiscible solvent. In examples: (1) podophyllotoxin glucoside is shaken with benzaldehyde and fused zinc chloride, excess aldehyde distilled off the residue treated with aqueous chloroform, the organic layer separated, dried and distilled, yielding podophyllotoxin-benzylidine glucoside, purified by crystallization from ethanol; similarly (2) to (4) and (6) to (13), are prepared the p-methoxy - benzylidene-, p - methylbenzylidene-, thenylidene-, ethylidene- and salicylidene-derivatives of podophyllotoxin glucoside; the benzylidene-derivatives of a - and b -peltatin glucosides and of 41-demethyl-41-ethylpodophyllotoxin glucoside; and the benzylidene, anisylidene- and thenylidene derivatives of 41 - demethyl - podophyllotoxin glucoside; (5) podophyllotoxin glucoside is refluxed in anhydrous furfural containing a little nitric acid under reduced pressure and excess furfural removed, yielding furfurylidene glucoside, purified by crystallization from ethanol. Specifications 768,919, 777,662 and 777,900 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH823068X | 1955-05-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB823068A true GB823068A (en) | 1959-11-04 |
Family
ID=4539643
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB14759/56A Expired GB823068A (en) | 1955-05-13 | 1956-05-11 | Condensation products from glucosides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB823068A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3502770A (en) * | 1966-03-21 | 1970-03-24 | Sandoz Ag | Preparation of composition from podophyllum extracts |
US3524844A (en) * | 1965-09-21 | 1970-08-18 | Sandoz Ag | Epipodophyllotoxin glucoside derivatives |
US4868291A (en) * | 1987-08-20 | 1989-09-19 | Bristol-Myers Company | 4'-deshydroxyepipodophyllotoxin glucosides: synthesis and use |
US4888419A (en) * | 1987-08-31 | 1989-12-19 | Bristol-Myers Company | 3'-demethoxyepipodophyllotoxin glucoside derivatives |
WO1994027614A1 (en) * | 1993-05-28 | 1994-12-08 | Conpharm Ab | Use of lignan derivatives for the preparation of pharmaceutical compositions for the treatment of states of amyloidosis |
-
1956
- 1956-05-11 GB GB14759/56A patent/GB823068A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3524844A (en) * | 1965-09-21 | 1970-08-18 | Sandoz Ag | Epipodophyllotoxin glucoside derivatives |
US3502770A (en) * | 1966-03-21 | 1970-03-24 | Sandoz Ag | Preparation of composition from podophyllum extracts |
US4868291A (en) * | 1987-08-20 | 1989-09-19 | Bristol-Myers Company | 4'-deshydroxyepipodophyllotoxin glucosides: synthesis and use |
US4888419A (en) * | 1987-08-31 | 1989-12-19 | Bristol-Myers Company | 3'-demethoxyepipodophyllotoxin glucoside derivatives |
WO1994027614A1 (en) * | 1993-05-28 | 1994-12-08 | Conpharm Ab | Use of lignan derivatives for the preparation of pharmaceutical compositions for the treatment of states of amyloidosis |
US5637571A (en) * | 1993-05-28 | 1997-06-10 | Conpharm Ab | Use of lignan derivatives for the preparation of pharmaceutical compositions for the treatment of states of amyloidosis |
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