Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-08-20
1994-11-15
Cintins, Marianne M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514335, 514336, 514339, 514346, 514357, 546265, 546284, 546300, 546331, A61K 3144, C07D21353, C07D40112, C07D41112
Patent
active
053648536
DESCRIPTION:
BRIEF SUMMARY
This invention relates to new therapeutically useful thioformamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
The thioformamide derivatives of the present invention are those compounds of formula (I), hereinafter depicted wherein: R represents an alkyl group; A represents a phenyl group which is optionally substituted, by one or more substituents selected from, for example, halogen atoms and cyano, nitro, trifluoromethyl, carbamoyl, carboxyl, alkoxycarbonyl and alkylsulphonyl groups or, preferably, a heterocyclyl group, preferably selected from quinolin-3-yl, isoquinolin-4-yl, pyridazin-4-yl, pyrimidin-5-yl, pyrazin-3-yl, indol-3-yl, thiazol-5-yl, and, more especially, pyridyl, e.g. pyrid-3-yl or pyrid-4-yl, optionally substituted by an alkyl or alkoxy group, or by a halogen atom; Y represents a direct bond or an ethylene or, preferably, methylene group; and either:
(1) R.sup.1 represents hydrogen and R.sup.2 represents:
i) a group of formula --CXNHR.sup.3, wherein R.sup.3 is an alkyl group and X is a group of formula .dbd.NSO.sub.2 R.sup.4, wherein R.sup.4 is alkyl or phenyl; or
ii) a group of formula --SO.sub.2 R.sup.5, wherein R.sup.5 represents:
a) a naphthyl or phenyl group optionally substituted by one or more halogen atoms, hydroxy, alkoxy, C.sub.3-6 cycloalkoxy, alkyl, C.sub.2-4 alkenyl, cyano, nitro, trifluoromethyl, carboxy, alkoxycarbonyl, amino, alkylamino, dialkylamino, alkoxycarbonylamino, alkanoylamino, dialkanoylamino, benzoylamino, carbamoyl, N-(optionally hydroxyalkyl)carbamoyl or N,N-di(optionally hydroxyalkyl)carbamoyl groups, or amino or carbamoyl groups N,N-disubstituted by a C.sub.3-6 alkylene chain one or more of whose methylene groups may have been replaced by an oxygen or sulphur atom or by an imino or alkylimino group;
b) a pyridyl or thienyl group; or
c) an alkyl group optionally substituted by one or more halogen atoms, phenyl, naphthyl, pyridyl, hydroxy, alkoxy, C.sub.3-6 cycloalkoxy, alkyl, C.sub.2-4 alkenyl, cyano, nitro, trifluoromethyl, carboxy, alkoxycarbonyl, amino alkylamino, dialkylamino, alkoxycarbonylamino, alkanoylamino, dialkanoylamino, benzoylamino, carbamoyl, N-(optionally hydroxyalkyl)carbamoyl or N,N-di(optionally hydroxyalkyl)carbamoyl groups, or amino or carbamoyl groups N,N-disubstituted by a C.sub.3-6 alkylene chain, one or more of whose methylene groups may have been replaced by an oxygen or sulphur atom or an imino or alkylimino group;
(2) R.sup.1 and R.sup.2 both independently represent a group of formula --SO.sub.2 R.sup.5, as defined above; or
(3) R.sup.1 and R.sup.2 together with the nitrogen to which they are attached from a group of formula (IA) wherein each group R.sup.9 is independently hydrogen or alkyl and Q is oxygen, sulphur or a group of formula NR.sup.9 or (CH.sub.2.sup.9).sub.n, wherein n is 0, 1 or 2;
wherein all alkyl groups and moieties, including those in alkoxy, alkoxycarbonyl and alkanoyl groups, are straight-chain or branched, and, unless otherwise specified, contain one to about six carbon atoms; and salts thereof.
Particularly important classes of compounds of formula (I) exhibit one or more of the following features:
i) R represents a methyl or ethyl group;
ii) A represents a pyrid-3-yl or pyrid-4-yl group;
iii) Y represents a methylene group;
iv) R.sub.1 represents a hydrogen atom;
v) R.sup.3 represents a methyl group;
vi) R.sup.4 represents a methyl or phenyl group;
vii) R.sup.5 represents:
a) a phenyl or naphthyl (especially 1-naphthyl) group optionally substituted by one or more halogen (especially fluorine or chlorine) atoms or nitro, cyano, alkoxy (especially methoxy) or dialkylamino (especially dimethylamino) groups;
b) a pyrid-3-yl or thien-2-yl group; or
c) an alkyl group of up to 4 carbon atoms; and/or
viii) the group of formula (IA) is a 3,5-dioxomorpholino group; the other symbols being as hereinbefore defined, and their pharmaceutically acceptable salts.
The presence of an axocyclic aminoethyl group on the ring creates an isomeric centre in the molecule which in
Palfreyman Malcolm N.
Vicker Nigel
Cintins Marianne M.
Oehler Ross J.
Rhone-Poulenc Rorer Limited
Spivack Phyllis G.
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