The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Feb. 02, 1993
Filed:
Dec. 20, 1991
Pharmachemie B.V., Haarlem, NL;
Abstract
The invention provides novel cyclic triketone compounds of the formulae ##STR1## wherein S is H, alkyl or alkoxy and R* is a group of the formule ##STR2## wherein R.sup.1 is methyl and R.sub.2 is an alkyl group containing at least 2 carbon atoms or R.sup.1 is an alkyl group having 1-4 carbon atoms and R.sup.2 is an aryl group, a hetero aryl group, a --CH.sub.2 OR' group, a --CH.sub.2 N<group, a --CH.sub.2 SR' group or a --CH.sub.2 CH.dbd.CH.sub.2 group, wherein R' and R' are alkyl groups having 1-4 carbon atoms. These compounds can be used for preparing daunomycinone and derivatives thereof. Daunomycinone is used for preparing daunomycin and adriamycin. By introducing chirality at C-1 of ring A in the preparation of said novel compounds by using a novel diene of formula (1) in a Diels-Alder reaction for said preparation, the chirality of C-3 is established in the subsequent reaction with LiC.tbd.CSi(CH.sub.3).sub.3 in the synthesis of daunomycinone and deriviatives thereof. ##STR3## This last reaction leads to the desired compound wherein OH at C-3 and OR at C-1 are in the cis-position with respect to each other.