GB1360163A - Cardiotonic glucoside derivatives process for their preparation and their applications - Google Patents

Cardiotonic glucoside derivatives process for their preparation and their applications

Info

Publication number
GB1360163A
GB1360163A GB2780572A GB2780572A GB1360163A GB 1360163 A GB1360163 A GB 1360163A GB 2780572 A GB2780572 A GB 2780572A GB 2780572 A GB2780572 A GB 2780572A GB 1360163 A GB1360163 A GB 1360163A
Authority
GB
United Kingdom
Prior art keywords
compound
compounds
osyl
reaction
formula
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
GB2780572A
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.)
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
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 Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR
Publication of GB1360163A publication Critical patent/GB1360163A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

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

1360163 Glucoside derivatives ANVARAGENCE NATIONALE DE VALORISATION DE LA RECHERCHE 14 June 1972 [14 June 1971] 27805/72 Heading C2C Novel compounds (1) and (11) in which X is > C = 0, or > CH(OH), R is hydrogen, C 1 -C 5 alkyl or cycloalkyl radical with 5 or 6 C atoms, R 1 is hydrogen or 0-"osyl" and "osyl" is hexosyl or deoxyhexosyl (and the enolic forms of compounds in which X is > C = 0) are prepared by (a) reacting a compound VI in which R 2 is hydrogen or hydroxyl with an acylated "osylation" reagent and (b) deacylating the intermediate formed to form a compound of Formula I in which X is >C = 0 or a compound of Formula II with the 0-"osyl" group and optionally (i) reducing a compound I in which X is >C=0, or (ii) reducing the corresponding compound obtained in stage (a) followed by deacylation in order to form a compound I in which X is >CH(OH). The acylated osylation reagent is 1-α-bromo-2,3,4,6-tetraacetyl - D - glucopyranose and deacylation is carried out in the cold with a methanolic solution of sodium hydroxide. Preferred compounds are those of Formula I in which X is >C = 0 and those of Formula II in which R is H and R 1 is osyl or R is ethyl and R 1 is H and osyl is D-glucopyranosyl in all three compounds. Novel starting compounds VI are prepared by the reaction of chloroacetyl chloride with to form reaction of this compound with sodium acetate forms reaction of this compound with zinc powder and ethyl bromoacetate to form which dehydrates and cyclizes to this compound is hydrolysed to the corresponding chloride of the last mentioned acid is subjected to a Friedel Crafts reaction with anisole to form which is demethylated to form a compound VI wherein R 2 is H, or the Friedel Crafts reaction may be carried out with resorcin to give a compound VI in which R 2 is OH (R has the significance indicated above). Compounds I and II are cardiotonic agents and form with a suitable vehicle a therapeutic composition which may be administered orally or parenterally.
GB2780572A 1971-06-14 1972-06-14 Cardiotonic glucoside derivatives process for their preparation and their applications Expired GB1360163A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7121529A FR2141532B1 (en) 1971-06-14 1971-06-14

Publications (1)

Publication Number Publication Date
GB1360163A true GB1360163A (en) 1974-07-17

Family

ID=9078612

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2780572A Expired GB1360163A (en) 1971-06-14 1972-06-14 Cardiotonic glucoside derivatives process for their preparation and their applications

Country Status (4)

Country Link
CH (1) CH544751A (en)
DE (1) DE2228948A1 (en)
FR (1) FR2141532B1 (en)
GB (1) GB1360163A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI67386C (en) * 1979-06-21 1985-03-11 Hoffmann La Roche FOERFARANDE FOER FRAMSTAELLNING AV NYA THERAPEUTIC EQUIPMENT
FR2492830A1 (en) * 1980-10-29 1982-04-30 Sori Soc Rech Ind NOVEL COMPOUNDS BELONGING TO THE BENZOYL- AND A-HYDROXYBENZYL-PHENYL-OSIDES FAMILY, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC APPLICATION

Also Published As

Publication number Publication date
FR2141532A1 (en) 1973-01-26
CH544751A (en) 1973-11-30
FR2141532B1 (en) 1974-08-23
DE2228948A1 (en) 1972-12-21

Similar Documents

Publication Publication Date Title
EP1097937B1 (en) N-acyl derivatives of the LL-E33288 antitumor antibiotics
US4345068A (en) Process for the preparation of 4'-epidaunorubicin, 3',4'-diepidaunorubicin, their doxorubicin analogs, and intermediates used in said process
Rosenthal et al. Branched-chain sugar nucleosides. Synthesis of 3′-C-ethyl (and 3′-C-butyl) uridine
GB1228096A (en)
GR78094B (en)
FI67386B (en) FOERFARANDE FOER FRAMSTAELLNING AV NYA THERAPEUTIC EQUIPMENT
ES8101622A1 (en) Anthracycline derivatives, a process for their preparation and pharmaceutical compositions containing them.
AU7988782A (en) Indanyl derivatives
GB1360163A (en) Cardiotonic glucoside derivatives process for their preparation and their applications
ES420630A1 (en) N-(furyl-methyl)-3-oxy-morphinans and salts thereof
JPS57176995A (en) Novel anthracyclinone glycoside and its preparation
Maehr et al. Chemistry of the gentamycins. I. Characterization and gross structure of gentamycin A
GB1154424A (en) New Derivatives of Steroids and a method of preparation thereof
Chittenden Acetalation studies. Part VI. Concerning the effects of ultrasound on the benzylidenation of some alkyl D‐glycopyranosides
IE38665B1 (en) 2,2,10,17-tetramethyl steroids a process for their preparation and compositions containing them
KR840008369A (en) Method for preparing phenem compound
JPS5634695A (en) Novel anthracycline derivative and its preparation
ES8205816A1 (en) Cardenolide-bis-digitoxoside derivatives, process for their preparation and their utilization as medicines.
GB1309670A (en) Pyranosides
MacDonald et al. Derivatives of D-gluco-Dialdohexose
ES8403915A1 (en) Beta-lactam derivatives, a process for their preparation and compositions containing them.
WO1985003706A1 (en) Punaglandins and pharmaceutical use thereof
US3314946A (en) 16alpha, 17alpha-acetonides of 19-nor pregnane derivatives and intermediates in the preparation thereof
US3255177A (en) Methyl n-acyl-3, 4-o-isopropylidene-thiolincosaminides
IE35536B1 (en) Adenosine-5'-carboxylic acid esters

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee