Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-07-25
1997-06-24
Reamer, James H.
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
Patent
active
056417764
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel substituted thiosemicarbazone derivatives 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, aryl, aryl-lower alkyl, lower alk-2-en-1-yl, lower alk-2-yn-1-yl, unsaturated or saturated heterocyclyl-lower alkyl, lower alkoxycarbonyl-lower alkyl or the group --C(.dbd.O)--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.
Although some of the compounds falling under formula I above are already disclosed in DE-OS-2 632 747 as starting compounds for the preparation of azines from 6-membered thiaza heterocycles of formula II in DE-OS-2 632 747, no single compound is characterised by physical data or even specifically mentioned in an Example, so that none of the compounds embraced by formula I above may be claimed as known. The compounds embraced by general formula II of DE-OS-2 632 747 have not been prepared with the substituents named herein and are simply mentioned as starting compounds without any particulars whatever relating to pharmacological activity.
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. preferably allyl or methallyl. preferably prop-2-yn-1-yl or also but-2-yn-1-yl. butyl. 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. benzyl. ethoxycarbonylmethyl or also methoxy- or ethoxycarbonylethyl. preferably acetoxy. 2-hydroxypropyl, 3-hydroxypropyl or 3-hydroxy-2-methylpropyl. including 35, typically chloro or fluoro, and also bromo. 2-halopropyl, 3-halopropyl or 3-halo-2-methylpropyl. (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. Heteroaryl is preferably an azacyclic, thiacyclic, oxacyclic, thiazacyclic, thiadiazacyclic, oxazacyclic, dimcyclic, 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-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-
REFERENCES:
patent: 4697020 (1987-09-01), Storni et al.
patent: 5229405 (1993-07-01), Feige et al.
Campbell Ronald J.
Ciba-Geigy Corporation
Kaiser Karen G.
Reamer James H.
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