Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-07-25
1997-05-06
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544 54, 544 55, A61K 3154, C07D27906
Patent
active
056271808
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP 94/03778, filed Nov. 15, 1994.
The present invention relates to novel substituted thiosemicarbazonethiones containing 6-ring members of formula I ##STR2## wherein R.sub.1 is lower alkyl, lower alk-2-en-1-yl, lower alk-2-yn-1-yl, or aryl-lower alkyl, R.sub.2 is hydrogen, lower alkyl, lower alk-2-en-1-yl, lower alk-2-yn-1-yl, aryl, aryl-lower alkyl, unsaturated or saturated heterocyclyl-lower alkyl, lower alkoxycarbonyl-lower alkyl or the group --C(.dbd.O)-R.sub.3 or --C(.dbd.S)-R.sub.3, wherein R.sub.3 is lower alkyl, aryl, aryl-lower alkyl, aryl-lower alkenyl, heteroaryl (hetaryl), aryloxy, aryl-lower alkoxy or lower alk-2-en-1-yloxy, and the salts thereof, to a process for the preparation of said compounds, to pharmaceutical compositions containing them, and to the use thereof as medicaments.
In this specification, radicals and compounds qualified by the term "lower" will be taken to mean those containing preferably up to and including 7, preferably up to and including 4, carbon atoms.
Lower alk-2-en-1-yl will typically be C.sub.3 -C.sub.5 alk-2-en-1-yl, preferably allyl or methallyl.
Lower alk-2-yn-1-yl will typically be C.sub.3 -C.sub.5 alk-2-yn-1-yl, preferably prop-2-yn-1-yl or also but-2-yn-1-yl.
Lower alkyl is C.sub.1 -C.sub.4 alkyl, typically methyl, ethyl, propyl or butyl.
Lower alkoxy is typically n-propoxy, isopropoxy, n-butoxy or tert-butoxy, preferably ethoxy and, most preferably, methoxy.
Aryl by itself and as moiety of composite radicals such as aryl-lower alkyl is typically phenyl or naphthyl, for example 1- or 2-naphthyl, or substituted phenyl or naphthyl, typically phenyl or naphthyl which are substituted by lower alkyl, hydroxy-lower alkyl, halo-lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, cyano and/or nitro. Aryl is preferably unsubstituted phenyl or phenyl which is substituted as indicated above, and is most preferably phenyl.
Aryl-lower alkyl is preferably phenyl-lower alkyl and, most preferably, benzyl.
Lower alkoxycarbonyl-lower alkyl will typically be methoxy- or ethoxycarbonylmethyl or also methoxy- or ethoxycarbonylethyl.
Lower alkanoyloxy is typically propionyloxy or pivaloyloxy, and is preferably acetoxy.
Hydroxy-lower alkyl will typically be 2- or 3-hydroxy-lower alkyl such as 2-hydroxypropyl, 3-hydroxypropyl or 3-hydroxy-2-methylpropyl.
Halogen will be taken to mean halogen having an atomic number of up to and including 35, typically chloro or fluoro, and also bromo.
Halo-lower alkyl will typically be 2- or 3-halo-lower alkyl such as 2-halopropyl, 3-halopropyl or 3-halo-2-methylpropyl.
Unsaturated heterocyclyl-lower alkyl is typically heteroaryl-lower alkyl (hetaryl-lower alkyl).
Hetaryl in composite radicals such as hetaryl-lower alkyl is preferably a monocyclic and also bicyclic or polycyclic heterocyclic radical having aromaticity. Bicyclic and polycyclic heteroaryl may be comprised of a plurality of heterocyclic rings or, preferably, may consist of one heterocycle and one or more than one, conveniently one or two and preferably one, fused carbocyclic ring, preferably a benzene ring. Each individual ring typically contains 3, 5, 6 or 7 ring members and, preferably, 5 or 6 ring members. Hetaryl is preferably an azacyclic, thiacyclic, oxacyclic, thiazacyclic, thiadiazacyclic, oxazacyclic, diazacyclic, triazacyclic and tetrazacyclic radical.
Hetaryl is most preferably monocyclic monoazacyclic, monothiacyclic or monooxacyclic radicals such as pyrryl, e.g. 2-pyrryl or 3-pyrryl, pyridyl, e.g. 2-, 3- or 4-pyridyl, thienyl, e.g. 2- or 3-thienyl, or furyl, e.g. 2-furyl; bicyclic monoazacyclic, monooxacyclic or monothiacyclic radicals such as indolyl, e.g. 2- or 3-indolyl, quinolinyl, e.g. 2- or 4-quinolinyl, isoquinolinyl, e.g. 1-isoquinolinyl, benzofuranyl, e.g. 2- or 3-benzofuranyl, or benzothienyl, e.g. 2-or 3-benzothienyl; monocyclic diazacyclic, triazacyclic, tetrazacyclic, oxazacyclic, thiazacyclic or thiadiazacyclic radicals such as imidazolyl, e.g. 2-imidazolyl, pyrimidinyl, e.g. 2- or 4-pyrimidinyl, triazolyl, e.g. 1,2,4-triazol-3
Ciba-Geigy Corporation
Kaiser Karen G.
Mathias Marla J.
Raymond Richard L.
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