Title:
【発明の名称】アントラサイクリングリコシド類およびその製法
Document Type and Number:
Japanese Patent JPH0735392
Kind Code:
B2
Abstract:
A new process for the preparation of 6-deoxyanthracyclinones of general formula I: I wherein R represents a hydrogen atom, a hydroxy group or a lower alkoxy group is described. The process provides a total synthesis of the 6-deoxyanthracyclinones of formula I using 1,2,3,6-tetrahydro-phthalate as starting material. The obtained racemic mixture of the compounds of formula I, if desired, can be submitted to optical resolution by the conventional method of conversion to diastereomeric derivatives using a chiral resolving agent. Alternatively, the racemic mixture can be used as such for the condensation with a suitably protected halosugar derivative to obtain alpha glycosidic derivatives of formula XV: XV wherein R1 represents a hydrogen atom or a hydroxy group, one of R2 and R3 represents a hydrogen atom, the other of R2 and R3 represents a hydrogen atom or a hydroxy group and X is a hydrogen atom or a trifluoro acetyl group. The N-trifluoroacetyl 7S:9S and 7R:9R derivatives of the alpha -glycosides of formula XV can be separated by chromatography on silica gel to obtain, after mild alkaline hydrolisis the wanted 7S:9S alpha -glycosides (R1=H) as free bases and can eventually be transformed into their corresponding doxorubicin derivatives (R1=OH) by known procedures.
Inventors:
Franchi Esco Anjierutsuchi
Sergio Penco
Hermes Vuanottei
Huederico Alcamone
Sergio Penco
Hermes Vuanottei
Huederico Alcamone
Application Number:
JP22001992A
Publication Date:
April 19, 1995
Filing Date:
August 19, 1992
Export Citation:
Assignee:
Farmitalia Carlo Erba Societa a Responsorabilita Limitata
International Classes:
A61K31/70; A61K31/7028; A61K31/7034; C07C50/38; A61K31/704; A61P35/00; C07C45/00; C07C46/00; C07C50/36; C07C67/00; C07D407/04; C07H15/252; (IPC1-7): C07H15/252
Attorney, Agent or Firm:
Chika Takagi (2 outside)
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