FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to novel tetrahydroisoquinolines that are useful in treatment of different neurological and psychic disorders, for example, ADHD. Invention describes a derivative of tetrahydroisoquinoline represented by the formula (IA-IF): wherein carbon atom designated as * is in R- or S-configuration; R1 represents (C1-C6)-alkyl; R2 represents hydrogen atom (H), (C1-C6)-alkyl; R3 represents H, -S(O)nNR11R12, (C1-C6)-alkyl or if R represents (C1-C6)-alkyl then the indicated group is substituted optionally with 1-3 substitutes chosen independently from the following groups in each case: (C1-C6)-alkyl, -OR9 and -NR9R10 under condition that in compounds represented by the formula (IA) radical R3 represents (C1-C6)-alkyl that is substituted optionally with 1-3 substitutes chosen independently among the following groups in each case: (C1-C6)-alkyl, -OR9 and -NR9R10; R4 represents H, (C1-C6)-alkyl, and when R4 represents (C1-C6)-alkyl then indicated group is substituted optionally with 1-3 substitutes chosen independently from the following groups in each case: (C1-C3)-alkyl, halogen atom, -OR9 and -NR9R10 under condition that in compounds represented by the formula (ID) radical R4 represents (C1-C6)-alkyl that is optionally substituted, and wherein both R3 and R are not hydrogen atom; each R5, R6 and R7 in compounds represented by each formula (IA), (IB), (IC), (ID), (IE) and (IF) represents independently H, halogen atom, -OR11, -NR11C(O)R12 and (C1-C6)-alkyl, and when each radical among R5, R6 and R7 represents (C1-C6)-alkyl then indicated group is substituted optionally with 1-3 substitutes chosen independently in each case from the following groups: (C1-C3)-alkyl, halogen atom under condition that in compounds represented by the formula (IE) at least one radical among R5 or R7 represents fluorine, chlorine atom or methyl group; R8 represents H or halogen atom under condition that in compounds represented by the formula (IF) radical R represents halogen atom; each R9 and R10 represents independently H, (C1-C4)-alkyl; R11 represents H, (C1-C4)-alkyl, and when R11 represents (C1-C4)-alkyl then indicated group is substituted optionally with 1-3 substitutes chosen independently in each case from the following groups: halogen atom, (C1-C4)-alkyl; R12 represents H, (C1-C4)-alkyl; n = 2, and its pharmaceutically acceptable salt or solvate. Also, invention describes a pharmaceutical composition, a method for treatment of disorder caused or associated with deficiency in serotonin, noradrenaline or dopamine, a method for inhibition of synaptic uptake of noradrenaline, a method for inhibition of synaptic uptake of serotonin, a method for inhibition of synaptic uptake of dopamine and a set comprising, among them, a compound by cl. 1. Invention provides synthesis of novel compounds possessing the useful biological properties.
EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved method of treatment and inhibition.
44 cl, 5 tbl, 94 ex
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Authors
Dates
2007-02-20—Published
2000-11-03—Filed