Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1994-03-24
1996-11-05
Kumar, Shailendra
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514352, 514353, 514581, 514582, 546304, 546306, 564 18, 564 19, 564 20, 564 34, 564 36, A61K 31175, C07C28106
Patent
active
055718434
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR93/00328, filed Apr. 1, 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 an NHNHCONHR.sub.4 group where R.sub.4 =phenyl or phenyl substituted by OH or C.sub.1 -C.sub.4 alkyl and =H, pyridyl, phenyl or phenyl substituted by one, two or three 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 or hydroxyethyl, or as hereinbefore, or .dbd.N--N.dbd.C(SCH.sub.3)--NHR.sub.6 where R.sub.6 denotes phenyl or phenyl substituted by one, two or three 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 or hydroxyethyl or .dbd.NNHCXNHR.sub.5 or .dbd.NNHCXN (phenyl).sub.2 group, where X and R.sub.5 have the same meanings as hereinbefore, or hereinbefore, in which case R and R.sub.1 together form an .dbd.NNHCXNHR.sub.5 group or .dbd.NNHCXNHR.sub.5 group where X and R.sub.5 have the same meanings as hereinbefore, or an .dbd.N--NH--CX--N (phenyl).sub.2.
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), ##STR4## 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 (.dbd.N--OH, oxygen), ##STR5## where R.sub.2, R.sub.3, X and R.sub.5 have the same meanings as in formula (I), and ##STR6## where R.sub.2, R.sub.3, X and R.sub.5 have the same meanings as in formula (I).
Formula (I) hereinbefore includes: ##STR7## (b) compounds having the formula: ##STR8## (c) compounds having the formula: ##STR9## where one out of R and R.sub.1 denotes NHNHCONHR.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, ##STR10## (e) compounds having the formula: ##STR11## (f) compounds having the formula: ##STR12## (g) compounds having the formula: ##STR13## (h) compounds having the formula: ##STR14## (i) compounds having the formula: ##STR15## (j) compounds having the formula: ##STR16## (k) compounds having the formula: ##STR17## (l) compounds having the formula: ##STR18## and (m) compounds having the formula: ##STR19## in which the symbols R.sub.2, R.sub.3, R.sub.4, R.sub.5 and X have the same meanings as in formula (I).
In formulae (I') to (I"") and (Ia) to (Im) hereinbefore, R.sub.2 is inter alia in position 5 and R.sub.3 in position 6.
Also, in formulae (I') to (I"") and (Ia) to (Im), the pair (R.sub.2, R.sub.3) may inter alia be (H, H), (5--OCH.sub.3,H), (5--OH, H) or (5--OCH.sub.3, 6--OCH.sub.3).
The invention also covers salts of the salt-forming compounds among those described hereinbefore. These salts comprise addition salts of mineral acids such as hydrochloric, hydrobromic, sulphuric or phosphoric acid, and addition salts of organic acids such as acetic, propionic, oxalic or citric acid.
The invention also covers all possible stereoisomers of formula (I) derivatives and mixtures of such stereoisomers, as well as the metabolites of these derivatives.
The invention also covers methods of preparing formula (I) derivatives. These methods are described in diagrams 1 to 6 hereinafter, in which the symbols R to R.sub.6 and X, unless stated otherwise, have the same meanings as in formula (I). ##STR20##
In the diagrams hereinbefore, 1 to 9 denote the methods used and have the following meanings:
1 Condensation in a solvent such as etha
REFERENCES:
patent: 3280185 (1966-10-01), Wendt et al.
Matthies et. al, Synthesis, 1972, 154-155.
CA 107890, 1967 (Abstract only).
Varma et. al, J. Pharmaceutical Sciences, 1967, 775-776.
CA 120286 s, 1974 (Abstract only).
CA 43946 q, 1976 (Abstract only).
CA 9584 q, 1975 (Abstract only).
CA 55040 (e & f), 1970 (Abstract only).
Ishai et. al, J. Org. Chem. vol. 38, No. 12, 1973, 2251-52.
Cugnon de Sevricourt Michel P.
Dacquet Catherine G.
Finet Michel A.
Le Marquer Florence J.
Robba Max F.
Innothera
Kumar Shailendra
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