Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-09-15
1999-11-23
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544283, 544287, 544293, 546152, 546153, 546156, 546159, 546168, 546170, 546171, 546178, 560 45, 564167, 564443, 514311, 514312, 514313, 514619, 514630, 514646, A61K 31505, C07D23988, C07D23993, C07D23994
Patent
active
059901160
DESCRIPTION:
BRIEF SUMMARY
The present invention concerns new organic compounds, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals especially for the treatment of proliferative and/or inflammatory disorders and cancer.
More particularly the invention concerns compounds of the formula ##STR2## wherein R.sub.1 and R.sub.2 are the same or different and represent hydroxy, alkoxy, acyloxy, alkyl or acyl, whereby R.sub.2 is in the 5- or 6-position, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydroxy or acyloxy, and formula ##STR3## wherein R.sub.6 represents hydrogen, alkyl, alkoxy or amino and X represents oxygen, hydroxyimino or alkoxyimino, R.sub.4 represents a group of formula ##STR4## wherein R.sub.7 and R.sub.8 are the same or different and represent hydrogen, alkyl, acyl or alkoxycarbonyl, or --CH.sub.2 NR.sub.5 --, whereby the heteroatom adheres to ring B and R.sub.5 represents hydrogen, alkyl or acyl, R.sub.3 and R.sub.4 form together with the adjacent ring B a condensed ring system of formula ##STR5## wherein the symbol represents a single or a double bond, R.sub.9 represents hydrogen, alkylthio, alkyl, alkoxycarbonyl, acyl, amino, acylamino, diacylamino, alkylamino, dialkylamino, cyano, hydroxy, alkoxy or mercapto, Y represents N or CR.sub.11, R.sub.10 represents hydrogen, alkyl, acyl or optionally substituted phenylalkyl, R.sub.11 represents hydrogen, alkoxycarbonyl, cyano or acyl, Z represents O or S and V represents NH, if the symbol represents a single bond, and N, if the symbol represents a double bond, with the proviso that, if R.sub.9 represents hydroxy or mercapto and Y represents N, the compounds exist predominantly in the tautomeric form of formula ##STR6## wherein R.sub.9 ' represents O or S, in free form or, where such forms exist, in salt form, herein briefly named "compounds of the invention".
The compounds of the invention possess interesting pharmacological, in particular antiproliferative, antiinflammatory and antitumor activity.
Alkyl as such or as part of a substituent such as alkoxy preferably is of 1 to 4 carbon atoms, it particularly is methyl or ethyl. Acyl preferably is the residue of a carboxylic acid, in particular an alkyl, arylalkyl or aryl carboxylic acid, whereby aryl preferably is phenyl, and the alkylene part of acyl, including the carbonyl group, preferably is of 1 to 5 carbon atoms. A preferred acyl moiety is acetyl.
In a preferred group of compounds of the invention R.sub.1 and R.sub.2 independently are alkoxy of 1 to 4 carbon atoms, W represents --CH.sub.2 CH.sub.2 -- and R.sub.3 and R.sub.4 represent a condensed ring system as defined above.
A preferred group are compounds of formula ##STR7## wherein R.sub.1p and R.sub.2p are the same or different and represent hydroxy, alkoxy, acyloxy, alkyl or acyl, whereby R.sub.2p is in the 5- or 6-position, with the proviso that R.sub.1p and R.sub.2p are not simultaneously hydroxy or acyloxy, R.sub.9p represents hydrogen, alkyl, alkoxycarbonyl, acyl, amino, acylamino, diacylamino, alkylamino, dialkylamino, cyano, alkoxy or hydroxy, Y.sub.p represents N or CH and R.sub.10p represents hydrogen, alkyl or acyl, with the proviso that, if R.sub.9p represents hydroxy and Y.sub.p represents N, the compounds exist predominantly in the tautomeric form of formula ##STR8## in free form, or where such forms exist, in salt form.
A further preferred group are compounds of formula ##STR9## wherein R.sub.1o and R.sub.20 are the same or different and represent alkyl, acyl or alkoxy, and R.sub.6o, R.sub.7o, R.sub.8o and X.sub.o have the same significance as R.sub.6, R.sub.7, R.sub.8 and X, in free form or, where such forms exist, in salt form.
Unless otherwise stated alkyl moieties are preferably straight or branched chains having 1 to 12, especially 1 to 8 carbon atoms, particularly 1 to 6 and expecially 1 to 4. Any lower alkyl present as or in a substituent is straight or branched-chain and has preferably 1 to 4, especially 1 or 2 carbon atoms.
A further preferred group of compounds of the i
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Derwent Abstract: Japan Tobacco, 97-415263/38.
Nagpal et al., "New Dermatological Agents for the Treatment of Psoriasis," Annual Reports in Medicinal Chemistry, vol. 32, Ch. 20, pp. 201-210, 1997.
Goodman & Gilman's, "The Parmacological Basis of Therapeutics," Academic Press, Ninth Edition, Ch. 64, pp. 1607-1608, 1996.
Kessinger Ann M.
Loeschorn Carol A.
Novartis AG
Raymond Richard L.
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