Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-05-16
1996-02-13
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548184, C07D27754, A61K 31425
Patent
active
054911583
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/02607 filed Sep. 25, 1993.
The present invention relates to novel thiosemicarbazonethiones of formula I ##STR2## wherein R.sub.1 is lower alkyl, lower alk-2-en-1-yl or also lower alk-2-yn-1-yl, alkyl or, taken together, are lower alkylidene, heterocyclyl-lower alkyl, or is also lower alkyloxycarbonyl-lower alkyl, and the salts thereof, to a process for the preparation of these 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 is typically C.sub.3 -C.sub.5 alk-2-en-1-yl, preferably allyl or methallyl.
Lower alk-2-yn-1-yl is typically 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 alkylidene is typically C.sub.1 -C.sub.4 alkylidene, preferably methylene or also ethylidene.
Lower alkoxy is 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, halo-lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen 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.
Unsaturated heterocyclyl-lower alkyl is typically heteroaryl-lower alkyl.
Heteroaryl in composite radicals such as heteroaryl-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, 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 and, preferably, 5 or 6 ring members. Heteroaryl is preferably an azacyclic, thiacyclic, oxacyclic, thiazacyclic, thiadiazacyclic, oxazacyclic, diazacyclic, triazacyclic and tetrazacyclic radical.
Heteroaryl 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-yl, tetrazolyl, e.g. 1- or 5-tetrazolyl, oxazolyl, e.g. 2-oxazolyl, isoxazolyl, e.g. 3- or 4-isoxazolyl, thiazolyl, e.g. 2-thiazolyl, isothiazolyl, e.g. 3- or 4-isothiazolyl or 1,2,4- or 1,3,4-thiadiazolyl, e.g. 1,2,4-thiadiazol-3-yl or 1,3,4-thiadiazol-2-yl; or bicyclic diazacyclic, oxazacyclic or thiazacyclic radicals such as benzimidazolyl, e.g. benzimidazolyl, benzoxazolyl, e.g. 2-benzoxazolyl, or benzthiazolyl, e.g. 2-benzthiazolyl.
Heteroaryl radicals are unsubstituted or they carry substituents. Suitable substituents at the ring carbon atoms are typically those cited above in connection with the aryl radicals and, additionally, oxo (.dbd.O). Ring nitrogen atoms may be substituted by lower alkyl, aryl-lower alkyl, lower alkanoyl, benzoyl, carboxy, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkanoyloxy or oxido ( )
Heteroaryl is preferably pyridyl, t
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Ciba-Geigy Corporation
Gerstl Robert
Kaiser Karen G.
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