Substituted derivatives of 20,21-dinoreburnamenine, their use as

Details Substituted derivatives of 20,21-dinoreburnamenine, their use as Substituted derivatives of 20,21-dinoreburnamenine, their use as

1989-07-18

1992-03-03

Rivers, Diana G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546 51, A61K 31445, C07D46100

Patent

active

050933370

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new substituted derivatives of 20,21-dinoreburnamenine, their preparation process and the new intermediates thus obtained, their use as medicaments and the pharmaceutical compositions containing them.
A subject of the invention is new compounds of formula (I): ##STR2## in which R.sub.1, R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, a halogen atom, an alkyl or alkoxy radical containing from 1 to 5 carbon atoms, a hydroxy, trifluoromethyl, nitro, amino, alkylamino or dialkylamino radical in which the alkyl radical contains from 1 to 5 carbon atoms, an acylamino radical in which the acyl radical represents the remainder of an aliphatic acid containing up to 6 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 not being able, at the same time, to represent a hydrogen atom and in which the group: ##STR3## represents either: the said products of formula (I) being in all the possible racemic or optically active forms, as well as the addition salts with mineral or organic acids of the said product of formula (I).
In the products of formula (I), the hydrogen atom in position 3 and the hydrogen atom in position 16 can each occupy one or other of the alpha and beta orientations, which determines the existence of cis and trans diastereoisomers. Also, the hydroxy radical in position 14 can be in alpha or beta form, when the group: ##STR4## represents ##STR5## in the products of formula (I).
When R.sub.1, R.sub.2 and R.sub.3 represent an alkyl radical, it is preferred to be a methyl, ethyl, n-propyl or isopropyl radical, but these substituents can also represent an n-butyl, isobutyl or n-pentyl radical.
When R.sub.1, R.sub.2 and R.sub.3 represent an alkoxy radical, it is preferred to be a methoxy or ethoxy radical, but they can also represent a linear, secondary or tertiary propoxy, isopropoxy or butoxy radical.
When R.sub.1, R.sub.2 and R.sub.3 represent a halogen atom, it is preferred to be a chlorine atom, but they can also represent a fluorine, bromine or iodine atom.
When R.sub.1, R.sub.2 and R.sub.3 represent an alkylamino radical, it is preferred to be a methylamino, ethylamino or propylamino radical.
When R.sub.1, R.sub.2 and R.sub.3 represent a dialkylamino radical, it is preferred to be a dimethylamino or diethylamino radical.
When R.sub.1, R.sub.2 and R.sub.3 represent an acylamino radical, it is preferred to be an acetylamino, propionylamino or butyrylamino radical.
The addition salts with mineral or organic acids of the products of formula (I) can be, for example, the salts formed with the following acids: hydrochloric, hydrobromic, hydriodic, nitric, sulphuric, phosphoric, propionic, acetic, formic, benzoic, maleic, fumaric, succinic, tartaric, citric, oxalic, glyoxylic, aspartic, ascorbic; alkylmonosulphonic acids such as methanesulphonic acid, ethanesulphonic acid, propanesulphonic acid; alkyldisulphonic acids such as methanedisulphonic acid, alpha,beta-ethanedisulphonic acid; arylmonosulphonic acids such as benzenesulphonic acid; and aryldisulphonic acids.
A subject of the invention is in particular the compounds of formula (I) characterized in that R.sub.1, R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom or a methyl, ethyl, methoxy or ethoxy radical, a chlorine atom, a hydroxy, trifluoromethyl or nitro radical, in all the possible racemic or optically active isomer forms, as well as the addition salts with mineral or organic acids.
A subject of the invention is also in particular the compounds of formula (I) characterized in that one of the three substituents R.sub.1 or R.sub.2 or R.sub.3 represents, in position 10 or 11, a methyl, ethyl, methoxy or ethoxy radical, a chlorine atom, a hydroxy, trifluoromethyl or nitro radical, the two other substituents representing a hydrogen atom, in all the possible racemic or optically active isomer forms, as well as the addition salts with mineral or organic acids.
The invention also relates in particular to the compounds of formula (I) characterized in that two of the three substituents R.sub.1, R.s

REFERENCES:
patent: 3755335 (1973-08-01), Thal et al.
patent: 4045443 (1977-08-01), Pfaffli
patent: 4291038 (1981-09-01), Farcilli et al.
patent: 4356305 (1982-10-01), Szantay et al.
patent: 4501740 (1985-02-01), Clemence et al.

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