GB823068A - Condensation products from glucosides - Google Patents

Condensation products from glucosides

Info

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
Application number
GB14759/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB823068A publication Critical patent/GB823068A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms

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  • 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.
GB14759/56A 1955-05-13 1956-05-11 Condensation products from glucosides Expired GB823068A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (6)

* Cited by examiner, † Cited by third party
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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