FIELD: chemistry; pharmaceutics.
SUBSTANCE: group of inventions relates to organic chemistry and pharmaceutics and includes a compound of formula (I), its stereoisomer, pharmaceutically acceptable salts, methods of producing a compound of formula (I), use of intermediate compounds of formulas (VIII), (IX), (XIV), (XV) to obtain a compound of formula (I), as well as a pharmaceutical composition containing the compound of formula (I). In formula (I) Ry and Ry' are hydrogen; Ry'' is hydrogen; Ry''' and Ry'''' are hydrogen; W is nitrogen or -CRw-; where Rw is hydrogen; w1, w2, w3 and w4 are independently selected from the group consisting of nitrogen and CH; where all of w1, w2, w3 and w4 represent CH, or where one or two of w1, w2, w3 and w4 are nitrogen, while the rest are CH; R1 is selected from a group consisting of hydrogen, halogen, C1-6 alkyl, -OR8, -NR8R8', haloC1-6alkyl, haloC1-6alkoxy, -CN, C3-6cycloalkyl and phenyl, wherein said C1-6alkyl may be substituted with C3-6cycloalkyl or phenyl; R8 and R8' are independently selected from a group, consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl and 5–6 membered heterocyclyl containing one heteroatom selected from the group consisting of nitrogen, oxygen and sulphur, where said C3-6cycloalkyl and heterocyclyl can be substituted with C1-6alkyl; R2 is selected from hydrogen, halogen, C1-6alkyl, -OR21, -NR21R21', -CN, halogenC1-6alkyl and halogenC1-6alkoxy; where R21 and R21' independently selected from hydrogen and C1-6alkyl; R3 is selected from hydrogen, halogen, C1-6alkyl, -OR31, -NR31R31', -CN, halogenC1-6alkyl and halogenC1-6alkoxy; where R31 and R31' are independently selected from hydrogen and C1-6alkyl; R4 is selected from hydrogen, C1-6alkyl or C3-6cycloalkyl, where said C1-6alkyl can be substituted with C3-6cycloalkyl, 5-member heteroaryl containing one heteroatom selected from the group consisting of nitrogen, oxygen and sulphur, and -OR41 and C(O)OR41, where R41 is selected from hydrogen and C1-6alkyl; R4 and Ry, taken together with the nitrogen and carbon atoms to which they are bonded, respectively, can form a heterocyclyl containing five or six member atoms, which can be substituted with C1-6alkyl; R5, R5', R5'' and R5''', R6, R6', R6'' and R6''', R7, R9 and R9' are as specified in the patent claim; where n equals 1, 2 or 3.
EFFECT: compounds of formula (I) have bidirectional pharmacological activity with respect to binding to a subunit α2δ-1 voltage-dependent calcium channel and σ1-receptor.
16 cl,1 tbl, 270 ex
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Authors
Dates
2025-01-15—Published
2020-10-05—Filed