Condensed pyrazole 3-oxo-propanenitrile derivatives

Details Condensed pyrazole 3-oxo-propanenitrile derivatives Condensed pyrazole 3-oxo-propanenitrile derivatives

1994-02-24

1995-06-13

Ramsuer, Robert W.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514253, 514322, 514338, 514403, 544140, 544371, 546199, 546271, 5483591, 5483595, A61K 31415, C07D23154, C07D49504

Patent

active

054243084

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to condensed pyrazole 3-oxo-propanenitrile 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: ##STR3## group wherein R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl or a ##STR4## group wherein each of R' and R" independently 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; or
R.sub.1 represents C.sub.1 -C.sub.6 alkyl, pyridyl or phenyl, the phenyl being 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; each of R.sub.2 and R.sub.3 is independently: ##STR5## wherein R' and R" are as defined above; e') CH.sub.2 OH, CHO, COOH or C.sub.2 -C.sub.7 alkoxycarbonyl; ##STR6## 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 or an .alpha.-aminoacid; ##STR7## group, wherein R.sub.c is as defined above; h') a ##STR8## a --CH.sub.2 OCO(CH.sub.2).sub.n COOR or a --NHCO(CH.sub.2).sub.n COOR group, wherein n is as defined above and R is hydrogen or C.sub.1 -C.sub.6 alkyl; --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; ##STR9## group wherein R' and R" are as defined above; or m') a ##STR10## group wherein R' and R" are as defined above; or n') a C.sub.2 -C.sub.7 alkoxycarbonyl group substituted by a ##STR11## group, wherein R' and R" are as defined above; and
Q represents hydrogen, carboxy, C.sub.2 -C.sub.7 alkoxycarbonyl or a ##STR12## 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 ##STR13## group wherein R and R.sub.c 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, CH.sub.2 OH, COOH, C.sub.2 -C.sub.7 alkoxycarbonyl, formyloxy, C.sub.2 -C.sub.8 alkanoyloxy and a ##STR14## group wherein R' and R" are as defined above; d") 2-thienyl, 2-furyl or 1-(C.sub.1 -C.sub.6 alkyl)-pyrrol-2-yl; or 3-isoxazolyl and which is unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; and the pharmaceutically acceptable salts thereof.
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 bioprecursors of the compounds of formula (I). It has be to be noticed that the compounds of formula (I) may be represented also by a tautomeric structure, namely the enol structure of formula (Ia) ##STR15## wherein
X, R.sub.1, R.sub.2, R.sub.3 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 C.sub.1 -C.sub.6 alkyl group is e.g., methyl, ethyl, propyl, isopropyl, butyl or tert.butyl, more preferably methyl, ethyl or tert.butyl.
A C.sub.3 or C.sub.4 alkenyloxy group is preferably allyloxy.
A C.sub.1 -C.sub.6 alkoxy group is, e.g., methoxy

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patent: 4140785 (1979-02-01), Hoffman et al.
patent: 4420476 (1983-12-01), Philipp et al.
patent: 4431657 (1984-02-01), Philipp et al.
patent: 4816467 (1989-03-01), Doria et al.
patent: 5206258 (1993-04-01), Doria et al.

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