Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-12-20
1992-11-24
Lee, Mary C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142328, 514318, 514253, 514322, 514339, 514406, 544 60, 544140, 544371, 544131, 544364, 546194, 546199, 546271, 5483595, A61K 31535, A61K 31445, C07D23154, C07D21108
Patent
active
051661527
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to tricyclic 3-oxopropanenitrile derivatives, to a process for their preparation and to pharmaceutical compositions containing them.
The compounds of the invention have the general formula (I) ##STR2## wherein X represents an oxygen atom or a --S(O).sub.n -- group, where n is zero, 1 or 2; unsubstituted or substituted by one or two substituents chosen independently from halogen, trifluoromethyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, nitro, amino, formylamino and C.sub.2 -C.sub.8 alkanoylamino; ##STR3## group wherein R' and R", the same or different, is C.sub.1 -C.sub.6 alkyl or R' and R", taken together with the nitrogen atom to which they are linked, form a heterocyclic ring which is selected from N-pyrrolidinyl, N-piperazinyl, hexahydroazepin-1-yl, thiomorpholino, morpholino and piperidino and which is unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; ##STR4## group wherein R.sub.d is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.c is hydrogen, phenyl or the side-chain of an .alpha.-aminoacid; ##STR5## group, wherein R.sub.c is as defined above; e.degree.) a ##STR6## a --CH.sub.2 OCO(CH.sub.2).sub.n COOR.sub.d or a --NHCO(CH.sub.2).sub.n COOR.sub.d group wherein n and R.sub.d are as defined above; --CH.sub.2 COOH group; --CH.sub.2 CH.sub.2 OH, C.sub.2 or C.sub.3 alkoxycarbonyl or a --(CH.sub.2).sub.p --R'.sub.3 group wherein p is 1 or 2 and R'.sub.3 is COOH or C.sub.2 -C.sub.7 alkoxycarbonyl; ##STR7## group wherein R' and R" are as defined above; or k.degree.) a ##STR8## group wherein R' and R" are as defined above; l.degree.) a C.sub.2 -C.sub.7 alkoxycarbonyl group substituted by a ##STR9## group wherein R' and R" are as defined above; each of R.sub.2 and R.sub.3 is independently; ##STR10## group wherein R.sub.a represents hydrogen or C.sub.1 -C.sub.20 alkyl and R.sub.b represents C.sub.1 -C.sub.20 alkyl, a ##STR11## group where R.sub.c and R.sub.d are as defined above or a --(A).sub.m --R.sub.5 group wherein m is zero or 1, A is a C.sub.1 -C.sub.6 alkylene chain and R.sub.5 is: independently from halogen, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy; independently chosen from halogen, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, amino, nitro, formylamino, C.sub.2 -C.sub.8 alkanoylamino, di(C.sub.1 -C.sub.6 alkyl)-amino, hydroxy, formyloxy and C.sub.2 -C.sub.8 alkanoyloxy; alkoxycarbonyl or a ##STR12## group wherein R' and R" are as defined above and optionally by another substituent chosen from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, amino, nitro, formylamino, C.sub.2 -C.sub.8 alkanoylamino, hydroxy, formyloxy and C.sub.2 -C.sub.8 alkanoyloxy, or 3-isoxazolyl and which is unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; R.sub.1 is hydrogen, then Q is only a ##STR13## group in which R.sub.a is as defined above and either R.sub.b is a ##STR14## group wherein R.sub.c and R.sub.d are as defined above or R.sub.b is a") a --(CH.sub.2).sub.z --R'.sub.5 group wherein z is zero, 1 or 2 and R'.sub.5 is as R.sub.5 as defined above under d'), e') or f') or b") a ##STR15## or --A'--R.sub.5 group, wherein A' is a C.sub.3 -C.sub.6 alkylene chain and R.sub.5 is as defined above.
The present invention includes within its scope all possible isomers, stereoisomers and optical isomers and their mixtures, and the metabolites and the metabolic precursors or biprecursors of the compounds of formula (I). It has to be noticed that the compounds of formula (I) may be represented also by a tautomeric structure, namely the enol structure of formula (Ia) ##STR16## wherein X, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Q are as defined above.
However, the compounds of formula (Ia), which fall within the scope of the present invention too, are described in the present specification as compounds of formula (I).
A halogen atom is preferably chlorine or fluorine.
The alkyl, alkylene, alkanoyloxy, alkoxy and alkanoylamino groups may be branched or straight chain groups.
A C.sub.1 -C.sub.20 alkyl group is preferably a C.sub.1 -C.sub.6 alkyl group.
A
REFERENCES:
patent: 3679699 (1972-07-01), Oppolzer
patent: 4268516 (1981-05-01), Lombardino et al.
patent: 4816467 (1989-03-01), Doria et al.
Doria Gianfederico
Ferrari Mario
Isetta Anna M.
Trizio Domenico
Farmitalia Carlo Erba S.r.l.
Gabilan Mary Susan H.
Lee Mary C.
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