Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-04-16
1995-02-07
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514253, 514258, 544118, 544263, 548239, 546286, 546318, 558411, 549 61, 549474, C07D48704
Patent
active
053877470
DESCRIPTION:
BRIEF SUMMARY
The present invention relates, by way of novel products, to the triazolopyrimidine derivatives of general formula (I) below and their tautomeric forms and, where appropriate, their addition salts, in particular the pharmaceutically acceptable addition salts.
The compounds in question have a very valuable pharmacological profile insofar as they possess antagonistic properties towards the angiotensin II receptors, and antiproliferative properties. They are therefore particularly indicated for the treatment and prevention of cardiovascular diseases and in particular for the treatment of hypertension, for the treatment of cardiac insufficiency and for the treatment and prevention of diseases of the arterial wall, especially atherosclerosis.
The present invention further relates to the method of preparing said products and to their uses in therapeutics.
These triazolopyrimidine derivatives and their tautomeric forms have general formula (I): ##STR2##
In formula (I): integer from 1 to 6 and R is a lower alkyl radical having 1 to 6 carbon atoms or a benzyl radical; or defined above; and OR.sub.4, SR.sub.4, NR.sub.5 R.sub.6 and NH(CH.sub.2).sub.n -NR.sub.5 R.sub.6, in which: cycloalkyl radical; being the hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms; or -cycloalkyl radical; or are attached, form a heterocycle selected from morpholine, pyrrolidine or piperidine; and -cycloalkyl radical; identical or different, are the hydrogen atom, a lower alkyl radical having 1 to 6 carbon atoms or a C.sub.3 -C.sub.7 -cycloalkyl radical; and ##STR3## in which: Z is CH or N or Z' is S or O;
The above-mentioned derivatives must also be considered in their tautomeric form.
In the case where R.sub.2 is an azide group, the compounds may be considered in the tricyclic tetrazolo-[1,5-c]-1,2,4-triazolo[1,5-a]pyrimidine form according to the equilibrium well known in the literature (cf. Temple and Montgomery, J. Org. Chem., 30, 826 (1965)).
The above-mentioned derivatives can take the form of addition salts, in particular the pharmaceutically acceptable addition salts.
Advantageously, the derivatives of the invention have general formula (I) given above in which: integer from 1 to 6 and R is a lower alkyl radical having 1 to 6 carbon atoms or a benzyl radical; or defined above; and OR.sub.4, SR.sub.4, NR.sub.5 R.sub.6 and NH(CH.sub.2).sub.n --NR.sub.5 R.sub.6, in which: and R' is a lower alkyl radical having 1 to 6 carbon atoms; are attached, form a heterocycle selected from morpholine, pyrrolidine or piperidine; and identical or different, are the hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms; and ##STR4##
In the description and the claims, lower alkyl radical is understood as meaning a linear or branched hydrocarbon chain having from 1 to 6 carbon atoms. A lower alkyl radical is for example a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl or isohexyl radical.
C.sub.3 -C.sub.7 -Cycloalkyl radical is understood as meaning a saturated cyclic hydrocarbon radical, preferably a cyclopropyl, cyclobutyl, cyclohexyl or cycloheptyl radical.
Halogen is understood as meaning a chlorine, bromine, iodine or fluorine atom.
In one embodiment, R.sub.1 is an n-propyl group.
In another embodiment, R.sub.1 is an N-diethylamino group.
In another embodiment, R.sub.1 is an n-butyl group.
In one embodiment, R.sub.2 is a hydroxyl group.
In another embodiment, R.sub.2 is an n-propyl group.
In another embodiment, R.sub.2 is an N-diethylamino group.
In one embodiment, R.sub.3 is a 2-(1H-tetrazol-5yl)phenyl group.
In one embodiment, X is the nitrogen atom.
In one embodiment, Y is the group CH.
In another embodiment, Y is the group C--CH.sub.3.
In another embodiment, Y is the group C--NH.sub.2.
The particularly preferred compounds of the invention are selected from the products of the formulae ##STR5##
In general terms, the method of preparing the compounds of formula (I) comprises: ##STR6## in which: X, Y and R.sub.3 are as defined above; and to 6 carbon atoms and in the other case a l
REFERENCES:
patent: 5177074 (1993-01-01), Allen et al.
patent: 5217973 (1993-06-01), Brumagniez et al.
patent: 5231094 (1993-07-01), Brumagniez et al.
patent: 5250521 (1993-10-01), Allen et al.
Bru-Magniez Nicole
Gungor Timur
Teulon Jean-Marie
Daus Donald G.
Laboratoires UPSA
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