Antitumor and antileukaemic substances, their preparation and ph

Details Antitumor and antileukaemic substances, their preparation and ph Antitumor and antileukaemic substances, their preparation and ph

1996-12-19

1998-02-10

Reamer, James H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ketone doai

514719, 568327, 568633, A61K 3112

Patent

active

057169942

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to 3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-vinyl-2,3,3a,4,7,7a-hexahydroi nden-4-one of formula (I): ##STR3## and 3-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-7-methyl-1-vinylindan of formula (II): ##STR4## as well as their stereoisomeric forms, the process for producing them from the plant Ottelia alismoides and pharmaceutical compositions containing them.
More particularly, the present invention relates to the product of formula (I) which has the following characteristics: 1500, 1435, 1270, 1125 and 1025 cm.sup.-1.
mass spectrum in ppm): J=2 and 8 Hz, 1H); 5.94 (d, J=9 Hz, 1H); 5.78 (m, 1H); 5053 (s, 1H); 5.32 (m, 2H); 4.98 (d, J=10 Hz, 1H); 4.95 (d, J=17 Hz, 1H); 3.88 (s, 3H); 3.07 (m, 1H); 2.88 (dd, J=6 and 8 Hz, 1H); 2.80 (t, J=8 and 8 Hz, 1H); 2.62 (m, 1H); 2.51 (m, 2H); 1.74 (m, 1H); 1.58 (m, 1H).
More particularly, the present invention relates to the product of formula (II) which has the following characteristics: 1126 and 1029 cm.sup.-1. in ppm; (d, J=8 and 13, 1H0; 3.16 (dd, J=6 and 13, 1H); 3.58 (m, 1H); 3.83 (m, 1H); 3.88 (m, 1H); 4.25 (s, 1H); 4.98 (d, J=8, 1H); 5.01 (d, J=16, 1H); 5.58 (s, 1H); 5.78 (dd, J=8 and 16, 1H); 6.53 (d, J=7, 1H); 6.69 (dd, J=7 and 1, 1H); 6.79 (d, J=7, 1H); 6.82 (dd, J=1, 1H); 6.85 (d, J=7, 1H) (.epsilon.=48800) (c=10.1 g/cm.sup.3 ; methanol) methanol-hydrochloric acid) mg/cm.sup.3 ; methanol-potassium hydroxide) ,4,7,7a-hexahydroinden-4-one and 3-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-7-methyl-1-vinylindan can be obtained from the plant Ottelia alismoides by extraction by means of a suitable solvent followed by the separation of the 3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-vinyl-2,3,3a,4,7,7a-hexahydroi nden-4-one or of the 3-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-7-methyl-1-vinylindan from the extract obtained.
Ottelia alismoides, which belongs to the Hydrocharitaceae family, is a submerged or partially floating aquatic plant. Ottelia alismoides has radical leaves which form, for the immersed part, a shrunken crown. The long floating part is petiolate, oval and lanceolate, oblong or cordate. The flowers are hermaphrodites and solitary, sessile with a long pedunculate spathe, and consist of three linear and oblong sepals and three large ovoid or orbicular petals.
According to the invention, Ottelia alismoides, in the form of the whole plant, generally dried and finely ground, is treated once or several times with a solvent chosen from aliphatic alcohols containing 1 to 4 carbon atoms and the aliphatic esters containing 1 to 6 carbon atoms to give, after concentration, a dry extract which is taken up in an aliphatic hydrocarbon containing 5 to 8 carbon atoms or a cycloaliphatic hydrocarbon containing 5 to 7 carbon atoms in order to obtain a solution from which the insoluble matter is separated by filtration and which, after concentration, gives a dry extract from which 3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-vinyl-2,3,3a,4,7,7a-hexahydroi nden-4-one or 3-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-7-methyl-1-vinylindan is separated by applying chromatographic techniques.
For the implementation of the process according to the invention for the production of the product of formula (I), it is particularly advantageous to carry out the extraction of the whole plant by means of ethanol and to treat the dry extract obtained with an aliphatic hydrocarbon such as hexane.
For the implementation of the process according to the invention for the production of the product of formula (II), it is particularly advantageous to carry out the extraction of the whole plant by means of methyl tert-butyl ether and to treat the dry extract obtained with an aliphatic hydrocarbon such as heptane combined with a nitrile such as acetonitrile.
The separation of 3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-vinyl-2,3,3a,4,7,7a-hexahydroi nden-4-one or of 3-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-7-methyl-1-vinylindan from the extract derived from the treatment with an aliphatic hydrocarbon optionally combined with a nitrile is generally carried out by high-performance

REFERENCES:
patent: 4882439 (1989-11-01), Jones

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