Carminomycinone precurses and analogues

Details Carminomycinone precurses and analogues Carminomycinone precurses and analogues

1985-06-18

1989-04-18

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

260365, C07H 1524, C07C 4966

Patent

active

048228737

DESCRIPTION:

BRIEF SUMMARY
This invention relates to organic compounds including anthracyclines and anthracyclinones. In a specific aspect this invention relates to carminomycinone and analogues and derivatives thereof including daunomycinone and analogues and derivatives thereof, to novel organic compounds which are useful in the synthesis of carminomycinone and its analogues and derivatives, to methods of production of organic compounds which are valuable precursors in the production of carminomycinone and its derivatives and analogues and to methods of production of analogues of anthracyclines.
Reference will be made to the accompanying drawings which are structural drawings of various chemical compounds and reaction schemes.
The compounds of formula I ##STR1## are named; according to the substituents borne, as set out below. The three glycosides are isolated and administered as salts, usually hydrochlorides. All amino compounds referred to throughout this specification and claims are considered to include salts as well as free bases.


______________________________________ R' R" R'" ______________________________________ Daunomycin CH.sub.3 H alpha-L-daunosaminyl Adriamycin CH.sub.3 OH alpha-L-daunosaminyl Carminomycin H H alpha-L-daunosaminyl Daunomycinone CH.sub.3 H H Adriamycinone CH.sub.3 OH H Carminomycinone H H H ______________________________________
Modified compounds with different glycosidic residues including oligosaccharides, and with different aglycones are known, in particular those where the glycosidic sugar is 4'-deoxy-, 4'-epi-, or N-trifluoroacetyl-daunosamine and/or where the aglycone lacks the oxy substituent at position 4 or 11.
At least the compounds daunomycin and adriamycin are therapeutically useful. The other compounds at least have utility as intermediates in the production of pharmaceuticals.
The present invention provides compounds of formula III ##STR2## and tautomeric forms thereof wherein:
R.sub.1 -R.sub.4 are H, alkyl, aryl, alkaryl, halogen, hydroxy, alkoxy, aryloxy, aralkoxy, acyloxy, amino or alkylamino; Ra is H, halogen, alkoxy, aryloxy or acyloxy; and R.sub.b is H, halogen, alkoxy, aryloxy or acyloxy.
Provided that if R.sub.1 -R.sub.4 and R.sub.a are all, H, R.sub.b is not H or chloro. and provided that if R.sub.1 -R.sub.4 are all H and R.sub.a is chloro or bromo R.sub.b is not chloro.
Preferred compounds of formula III are those wherein:
The present invention also provides compounds of formula IV ##STR3## and tautomeric forms thereof wherein:
R.sub.1 is H, alkyl, aralkyl or acyl;
R.sub.2 is H, halogen, alkoxy, aryloxy or acyloxy; or
R.sub.3 is H, halogen, alkoxy, aryloxy or acyloxy.
Preferred compounds of formula IV are those wherein:
The present invention also provides compounds of formula II ##STR4## and tautomeric forms thereof wherein: R.sub.1 -R.sub.4 have the meaning given above;
R.sub.8 has the same meaning as given to R.sub.1 -R.sub.4 or may be glycosyloxy; alternatively may be alkoxycarbonyl, aryloxycarbonyl or carboxy; aryloxy or acyloxy;
R.sub.10 and R.sub.11 taken together are oxo or ethylenedioxy (provided that if R.sub.10 and R.sub.11 taken together are ethylenedioxy then if R.sub.4 is hydrogen or methoxy, R.sub.b is not hydrogen or acetoxy); or
R.sub.10 is hydroxy; and R.sub.11 is hydroxyalkyl or dihydroxyalkyl or --CO--R.sub.15 where R.sub.15 is H, alkyl, aryl, aralkyl, hydroxyalkyl.
Preferred compounds of formula II are those wherein: together are oxo; and R.sub.10 is hydroxy; and R.sub.11 is hydroxyalkyl, dihydroxyalkyl or R.sub.11 is --CO--R.sub.15 where R.sub.15 is H, alkyl, aryl, aralkyl, hydroxyalkyl; or glycosyloxy; R.sub.9 and R.sub.12 are H and R.sub.10 is hydroxy; and R.sub.11 is --CO--R.sub.15 where R.sub.15 is H, alkyl, aryl, aralkyl, hydroxyalkyl; or R.sub.11 is hydroxyalkyl, dihydroxyalkyl.
The present invention also provides compounds of formula II and tautomeric forms thereof wherein: --OSO.sub.2 O--; R.sub.b is hydroxy, alkoxy, aralkoxy or acyloxy; R.sub.8 -R.sub.15 are as defined above. or are H R.sub.x is

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