Patent ES-8602008-A1 (ES)
Title: Benzothiopyranopyridinones and their salts, their preparation and use as medicaments, and compositions containing them.
IPC: C07D495/04
Filed: 1985-01-02
Abstract: EP--99303 A 2-R 6-D 7-C 8-B 9-A- 1,2,3,4-tetra-hydro -10H-(1)-benzothiopyrano (3,2-c) pyridin-10-one derivs. of formula (I) and their salts are new. In (I) A, B, C, D independently are H, opt. branched 1-6C alkyl, opt. branched 1-6C alkoxy, nitro, amino, 2-7C acylamino or halo or one of A and B or C and D together with the C atoms to which they are joined forms a fused benzene ring. R is H or R1 R1 is opt. branched 1-9C alkyl or opt. branched 2-9C alkenyl (opt. substd. by hydroxy), 3-9C cycloalkyl, phenyl, 7-9C aralkyl or -(CH2)n-Z n is 1-4 and Z is 3-9C cycloalkyl, 3-9C cycloalkenyl, dioxanyl, 2-oxobenzimidazolyl, benzoyl (opt. halo substd.) 2-7C alkoxycarbonyl, cyano or carbamoyl). - Dopamine and alpha 2 receptor antagonists, with weak affinity for muscarinic and alpha 1 receptors. The cpds. have anti-dopaminergic and also antidepressant and/or antipsychotic properties with minimum secondary effects on the autonomous nervous system and minimum extra pyramidal effects. They are used to depression, behavioural troubles, anxiety, neurotic states, etc.. They are pref. administered orally, in daily doses of 0.25-1000 mg, esp. 0.25-400 mg.. EPAB- EP--99303 B Benzothiopyranopyridinones and their salts, characterised in that they respond to the formula (I) in which A, B, C and D, idential or different, represent a hydrogen atom, a linear or branched alkyl radical containing from 1 to 6 carbon atoms, a linear or branched alkoxy radical containing from 1 to 6 carbon atoms, a nitro radical, an amino radical, an acylamino radical containing from 2 to 7 carbon atoms or a halogen atom, or one of the groups A and B or C and D represents, together with the carbon atoms to which they are bonded, a benzene ring and the other is defined as above. R represents a hydrogen atom or a radical R' in which R' represents a linear or branched alkyl radical, containing from 1 to 9 carbon atoms or a linear or branched alkenyl radical containing from 2 to 9 carbon atoms, possible substituted by a hydroxy radical, a cycloalkyl radical containing from 3 to 9 carbon atoms, a phenyl radical, an aralkyl radical containing from 7 to 9 carbon atoms or a group -(CH2)n-Z in which n is an integer varying from 1 to 4 and Z represents a cycloalkyl or cycloalkenyl radical containing from 3 to 9 carbon atoms, a dioxanyl radical, a 2-oxo-benzimidazolyl radical, a benzoyl radical possible substituted by a halogen atom, an alkoxycarbonyl radical containing from 2 to 7 carbon atoms, a cyano radical or a carbamoyl radical. - (30pp) - EP--99303 B 2-R 6-D 7-C 8-B 9-A- 1,2,3,4-tetra-hydro -10H-(1)-benzothiopyrano (3,2-c) pyridin-10-one derivs. of formula (I) and their salts are new. In (I) A, B, C, D independently are H, opt. branched 1-6C alkyl, opt. branched 1-6C alkoxy, nitro, amino, 2-7C acylamino or halo or one of A and B or C and D together with the C atoms to which they are joined forms a fused benzene ring. R is H or R1 R1 is opt. branched 1-9C alkyl or opt. branched 2-9C alkenyl (opt. substd. by hydroxy), 3-9C cycloalkyl, phenyl, 7-9C aralkyl or -(CH2)n-Z n is 1-4 and Z is 3-9C cycloalkyl, 3-9C cycloalkenyl, dioxanyl, 2-oxobenzimidazolyl, benzoyl (opt. halo substd.) 2-7C alkoxycarbonyl, cyano or carbamoyl). - Dopamine and alpha 2 receptor antagonists, with weak affinity for muscarinic and alpha 1 receptors. The cpds. have anti-dopaminergic and also antidepressant and/or antipsychotic properties with minimum secondary effects on the autonomous nervous system and minimum extra pyramidal effects. They are used to depression, behavioural troubles, anxiety, neurotic states, etc.. They are pref. administered orally, in daily doses of 0.25-1000 mg, esp. 0.25-400 mg.. (Dwg.0/0) GBAB- GB2123419 B Compounds of formula (I) wherein: A, B, C and D, which may be the same or different, each represents a hydrogen atom, a straight or branched C1-6 alkyl group, a straight or branched C1-6 alkoxy group, a nitro group, an amino group, a C2-7 acylamino group, or a halogen atom or one of the pairs of groups A and B or C and D together with the carbon atoms to which they are attached represent a benzene ring, and the other pair is as defined above and R represents a hydrogen atom, a group R' (wherein R' represents a straight or branched C1-9 alkyl or C2-9 alkenyl group (optionally substituted by a hydroxyl group), a C3-9 cycloalkyl group, a phenyl group, a C7-9 aralkyl group or a group -(CH2)n-Z (wherein n is an integer from 1 to 4 and Z represents a C3-9 cycloalkyl or cycloalkenyl group, a dioxanyl group, a 2-oxo-benzimidazolyl group, a benzoyl or halo-substituted benzoyl group, a C2-7 alkoxycarbonyl group, a cyano group or a carbamoyl group)) and salts thereof. USAB- US4547507 A Benzothiopyranopyridinones of formula (I) are new. In (I), A-B,C and D are each H, 1-6C alkyl or -alkoxy, NO2, halo, NH2, 2-7C acylamino or A and B or C and D together with attached C atoms form benzene ring R is 1-9C alkyl, 2-9C alkenyl opt. substd., OH, 3-9C cycloalkyl, Ph 7-9C aralkyl and -(CH2)n-Z with n, 1-4 and Z, 3-9C cyclo-alkyl or -alkenyl, dioxanyl 2-oxobenzimidazolyl, benzoyl opt. halo substd., 2-7C alkoxycarbonyl. - (I) are prepd. by reacting (II) with (III) in which X is 1-8C alkyl by heating in polyphosphoric acid or (I) with R. H is reacted with Hal-R' or with CH2-CH-Z' with Z' CN, carbamoyl or alkoxycarbamoyl.