Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-02-23
1992-01-14
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514255, 514283, 544125, 544361, 546 51, A61K 31535, A61K 3141, C07D41300, C07D47100
Patent
active
050811207
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new derivatives of 20,21-dinoreburnamenine substituted at position 15 by an aminated group, and their salts, their preparation process and the intermediates thus obtained, their use as medicaments and the pharmaceutical compositions containing them.
The invention relates to new compounds of formula (I): ##STR3## in which R.sub.1 and R.sub.2, ident different, represent a hydrogen atom, an alkyl radical containing 1 to 5 carbon atoms, a --(CH.sub.2)n--OH radical, in which n is between 2 and 5, an aryl or arylalkyl radical containing 7 to 12 carbon atoms, these two radicals being optionally substituted, a ##STR4## radical in which R.sub.3 is an alkyl radical containing 1 to 5 carbon atoms, an aryl or arylalkyl radical containing 7 to 12 carbon atoms, these two radicals being optionally substituted, R.sub.1 and R.sub.2, however, not being able to represent an aryl radical simultaneously, or R.sub.1 and R.sub.2 form, together with the nitrogen atom to which they are linked, a saturated or unsaturated heterocyclic radical which can contain a second heteroatom chosen from oxygen, sulphur and nitrogen atoms, this latter being optionally substituted by an alkyl radical containing 1 to 5 carbon atoms, an aryl radical, an arylalkyl radical containing 7 to 12 carbon atoms, these radicals being optionally substituted, R.sub.4 and R.sub.5, identical or different, represent a hydrogen atom, a halogen atom, an alkyl or alkoxy radical containing 1 to 5 carbon atoms, a hydroxy, trifluoromethyl or nitro radical, the said products of formula (I) being in all the possible enantiomeric and diastereoisomeric forms and in the form of addition salts with acids.
The term alkyl radical preferably represents a methyl, ethyl, n-propyl or isopropyl radical, but also an n-butyl, isobutyl or n-pentyl radical. The term aryl radical preferably means a phenyl or naphthyl radical and the term arylalkyl radical containing 7 to 12 carbon atoms preferably means a benzyl or phenethyl radical. The aryl and aryl -alkyl radicals are optionally substituted by 1, 2 or 3 radicals chosen from the group formed by halogen atoms, and the following radicals: methyl, ethyl, methoxy, ethoxy, trifluoromethyl, amino and nitro.
When R.sub.1 and R.sub.2 form, together with the nitrogen atom, a heterocycle, it is preferably, for example, one of the following cycles: pyrrolidino, piperidino, morpholino, piperazinyl, methylpiperazinyl, ethylpiperazinyl, propylpiperazinyl, phenylpiperazinyl, or benzylpiperazinyl, when R.sub.1 and R.sub.2 represent these last two radicals, the phenyl and benzyl radicals can be optionally substituted by the substituents already mentioned previously.
When R.sub.4 and R.sub.5 represent an alkoxy radical, it is preferably a methoxy or ethoxy radical, but they can also represent a propoxy, an isopropoxy, or a linear, secondary or tertiary butoxy radical.
When R.sub.4 and R.sub.5 represent an alkyl radical, it is preferably a methyl radical; it can also be an ethyl, propyl, isopropyl, or linear or branched butyl radical.
When R.sub.4 and R.sub.5 represent a halogen atom, it is preferred to be a chlorine atom, but they can also represent a fluorine, bromine or iodine atom.
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 or beta orientations, which determines the existence of cis and trans diastereoisomers. Furthermore, the nitrogen atom linked to the carbon in position 15 can be in alpha or beta form.
The invention relates in particular to the compounds of formula (I) characterized in that R.sub.1 and R.sub.2, identical or different, represent a hydrogen atom, a methyl or ethyl radical, a ##STR5## radical in which R.sub.3 is a methyl, ethyl, phenyl or benzyl radical optionally substituted by one or more chlorine atoms, or a --CH.sub.2 --CH.sub.2 --OH radical, or R.sub.1 and R.sub.2 form, together with the nitrogen atom, a pyrrolidinyl, morpholinyl or piperazinyl radical, the nitrogen atom of which is substituted by a methy
REFERENCES:
patent: 4123535 (1978-10-01), Pfaffli
Szantay, Csaba et al., Chemical Abstract 100(25) 210, 238t and copy of CAS on line structure, Abstract of DE 3323606 A1 12 Jan. 84.
Degryse Mauricette
Francois Clemence
Haesslein Jean L.
Petit Francis
Grumbling Matthew V.
Roussel Uclaf
Shah Mukund J.
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