Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-03-24
1997-07-15
Haley, Jacqueline
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549487, C07D21387
Patent
active
056483813
DESCRIPTION:
BRIEF SUMMARY
This is a National Stage application of PCT/FR93/00329 filed 1, Apr. 1993 and published as WO 93/20046 on 14 Oct. 1993.
The invention relates to novel derivatives of indan-1,2-dione and indan-1,2,3-trione, methods of preparation thereof and use thereof in therapy.
More specifically, these derivatives have the formula: ##STR2## in which R.sub.2 and R.sub.3 independently denote H, C.sub.1 -C.sub.4 alkoxy or OH, and the pair (A, B) denotes either: halogen, (C.sub.1 -C.sub.4 alkyl) NH, N-morpholino(C.sub.1 -C.sub.4 alkyl) NH, 1-(pyridyl)-4-piperazino or 1-(phenyl)-4-piperazino in which the phenyl ring is optionally substituted by a halogen, and the other denotes a group chosen from among the following: -C.sub.4 alkyl substituted by a halogen, substituted by one or two groups chosen from among the following: amino, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl or OH; thienyl; furyl; pyridyl; indolyl-2-methyl; indolyl-3-methyl; or 5-phenyl-2-(N-pyrrolyl)thienyl, or halogen and the other represents NHCOR.sub.4 where R.sub.4 =phenyl or C.sub.1 -C.sub.4 alkyl; derivatives in which one out of R and R.sub.1 denotes (C.sub.1 -C.sub.4 alkyl)NH and the other denotes NHCOR.sub.4 where R.sub.4 =C.sub.1 -C.sub.4 alkyl; and derivatives in which one out of R and R.sub.1 denotes OH and the other denotes NHNHCOR.sub.5 where R.sub.5 =pyridyl or phenyl substituted by a C.sub.1 -C.sub.4 alkoxy group, and acetylaminophenyl, pyrazinyl or pyrrolyl, groups chosen from among C.sub.1 -C.sub.4 alkyl, halogen and C.sub.1 -C.sub.4 alkoxy; methyl sulphonyl phenyl; or N-methyl methane sulphanomidophenyl, halogen atom or phenyl substituted by a halogen atom or an OH group, or phenylamino substituted by a halogen atom or an OH group, .dbd.NNHCOR'.sub.5 group where R'.sub.5 =pyridyl or phenyl substituted by C.sub.1 -C.sub.4 alkoxy and derivatives in which R and R.sub.1 together form an .dbd.N--NHR.sub.6 group where R.sub.6 =phenyl or phenyl substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl or alkoxy group; or =H, phenyl or phenyl substituted by one or two groups chosen from among OH, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, methylene dioxy, acetoxy and hydroxyethyl, in which case R and R.sub.1 together form an .dbd.N--OH group.
Formula (I) hereinbefore includes: ##STR3## where R, R.sub.1, R.sub.2 and R.sub.3 have the same meanings as in formula (I) when the pair (A, B) therein denotes (oxygen, oxygen), and ##STR4## where, R, R.sub.1, R.sub.2, R.sub.3, X and R.sub.10 have the same meanings as in formula (I), when the pair (A, B) therein denotes (.dbd.NNHCXNHR.sub.10, oxygen).
Formula (I) hereinbefore includes: ##STR5## where R.sub.4 =C.sub.1 -C.sub.4 alkyl substituted by a halogen. (b) compounds having the following formula: ##STR6## where R.sub.5 .noteq.pyridyl and phenyl substituted by a C.sub.1 -C.sub.4 alkoxy group. ##STR7## (d) compounds having the formula: ##STR8## where R.sub.4 =C.sub.1 -C.sub.4 alkyl substituted by a halogen. (e) compounds having the formula: ##STR9## (f) compounds having the formula: ##STR10## (g) compounds having the formula: ##STR11## where one out of R and R.sub.1 denotes NHCOR.sub.4 and the other denotes (C.sub.1 -C.sub.4 alkyl) NH, N-morpholino (C.sub.1 -C.sub.4 alkyl) NH, 1-(pyridyl)-4-piperazino or 1-(phenyl)-4-piperazino in which the phenyl ring is optionally substituted by a halogen, except for compounds in which one out of R and R.sub.1 denotes NHCOR.sub.4 where R.sub.4 =C.sub.1 -C.sub.4 alkyl and the other denotes (C.sub.1 -C.sub.4 alkyl) NH. ##STR12## where one out of R and R.sub.1 denotes NHNHCOR.sub.5 and the other denotes (C.sub.1 -C.sub.4 alkyl) NH, N-morpholino (C.sub.1 -C.sub.4 alkyl), NH, 1-(pyridyl)-4-piperazino or 1-(phenyl)-4-piperazino in which the phenyl ring is optionally substituted by a halogen. ##STR13## where one out of R and R.sub.1 denotes NHNHCOCONH.sub.2 and the other denotes (C.sub.1 -C.sub.4 alkyl) NH, morpholino (C.sub.1 -C.sub.4 alkyl) NH, 1-(pyridyl)-4-piperazino or 1-(phenyl)-4-piperazino in which the phenyl ring is optionally substituted by a
REFERENCES:
patent: 3280185 (1966-10-01), Wendt et al.
Cugnon de Sevricourt Michel P.
Dacquet Catherine G.
Finet Michel A.
Le Marquer Florence J.
Robba Max F.
Haley Jacqueline
Innothera
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