Benzothiadiazepine compounds, a process for their preparation and pharmaceutical compositions containing them
Compounds of formula (I): wherein: R 1 and R 2 , which may be the same or different, each represent a hydrogen or halogen atom or an alkyl, alkoxy, alkylthio, acyl, alkoxycarbonyl, carboxy, hydroxy, hydroxyalkyl, cyano, nitro, amino, substituted or unsubstituted aminocarbonyl, aminosulphonyl, alkylsulphonylaminoalkyl, N-hydroxy-carboximidamide or benzyloxy group, R 3 represents a hydrogen atom or an alkyl, cycloalkyl or cycloalkylalkyl group, R 4 represents a hydrogen atom or a substituted or unsubstituted alkyl group Medicinal products containing the same which are useful in treating or preventing conditions treatable by an AMPA receptor modulator and/or an NMDA receptor antagonist.
1. A compound of formula (I):
wherein:
R 1 and R 2 , which may be the same or different, each represent a hydrogen atom; a halogen atom; a linear or branched (C 1 -C 6 )alkyl group which is unsubstituted or substituted by one or more halogen atoms; a linear or branched (C 1 -C 6 )alkoxy group; a linear or branched (C 1 -C 6 )alkylthio group; a linear or branched (C 1 -C 6 )alkoxycarbonyl group; a carboxy group; a linear or branched (C 1 -C 6 )acyl group; a hydroxy group; a linear or branched (C 1 -C 6 )hydroxyalkyl group; a cyano group; a nitro group; an amino group which is unsubstituted or substituted by one or more linear or branched (C 1 -C 6 )alkyl groups; an amino group which is substituted by a linear or branched (C 1 -C 6 )acyl group; an aminocarbonyl group which is unsubstituted or substituted by one or more linear or branched (C 1 -C 6 )alkyl groups; an aminosulphonyl group which is unsubstituted or substituted by one or more linear or branched (C 1 -C 6 )alkyl groups; a (C 1 -C 6 )alkyl-sulphonylamino-(C 1 -C 6 )alkyl group in which the alkyl moieties are linear or branched; an N-hydroxycarboximidamide group; or a benzyloxy group,
R 3 represents a hydrogen atom; a linear or branched (C 1 -C 6 )alkyl group; a (C 3 -C 8 )cycloalkyl group or a (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl group in which the alkyl moiety is linear or branched,
R 4 represents a hydrogen atom or a linear or branched (C 1 -C 6 )alkyl group which is unsubstituted or substituted by one or more halogen atoms,
or an optical isomer or addition salt thereof with a pharmaceutically acceptable acid or base.
2. The compound of claim 1 , wherein R 1 represents a hydrogen atom, a hydroxy group, a hydroxymethyl group, an ethoxycarbonyl group, an amino group or an N-methylaminocarbonyl group.
3. The compound of claim 1 , wherein R 1 is in the meta or para position.
4. The compound of claim 1 , wherein R 2 and R 4 represent hydrogen atoms.
5. The compound of claim 1 , wherein R 3 represents a hydrogen atom or a methyl group.
6. The compound of claim 1 , which is selected from:
8-phenoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide;
ethyl 3-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]-benzoate;
3-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]-N-methyl-benzamide;
{3-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]phenyl}-methanol;
4-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]phenol;
4-[(5-methyl-1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]-phenol;
4-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]aniline,
and addition salts thereof with a pharmaceutically acceptable acid or base.
7. A compound of formula (VI):
8. A pharmaceutical composition comprising as active ingredient a compound of claim 1 , in combination with one or more pharmaceutically acceptable, non-toxic, inert carriers.