AMINOPYRIDINE DERIVATIVES AND THEIR USE AS ALK-2 SELECTIVE INHIBITORS Russian patent published in 2024 - IPC C07D405/14 C07D401/10 C07D401/12 C07D401/14 C07D409/14 C07D411/14 

FIELD: pharmaceutics.

SUBSTANCE: invention relates to a method of producing a compound of formula (I) or a pharmaceutically acceptable salt thereof, where R₁ is C₃-C₇cycloalkyl, optionally substituted once or more than once with a substituent independently selected from hydroxyl, halogen and C₁-C₃alkyl; and bridged C₅-C₁₀cycloalkyl, optionally substituted once or more than once with a substituent independently selected from hydroxyl and hydroxyC₁-C₃alkyl; L is a bond, (CH₂)_n, -CH(CH₃)-, -O-(CH₂)_n-, -C(O)- or -C(O)-NH-(CH₂)_n-; n is equal to 1, 2 or 3; R₂ and R₃ are independently selected from H, halogen and C₁-C₃alkyl; R₄ is 5–7 membered N-containing heterocyclic non-aromatic ring, optionally containing one or more additional heteroatoms selected from N, O or S, where said ring is optionally substituted once or more than once with R₇; R₇ is independently selected from C₁-C₃alkyl, hydroxyC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkyl, halogenC₁-C₃alkoxyC₁-C₃alkyl, C₂-C₄alkynyl, cyanoC₁-C₃alkyl and (CH₂)_m-R₈; m is 0, 1, 2 or 3; and R₈ is selected from 4-, 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring containing one or more heteroatoms selected from N, O or S, wherein said ring is optionally substituted once or more than once with a substituent independently selected from oxo, SO₂C₁-C₃alkyl and halogenC₁-C₃alkyl; and C₃-C₆cycloalkyl, optionally substituted once or more times with halogen; comprising steps of (a) coupling a compound of formula (II), where L, n, R₁, R₂ and R₃, R₄, R₇, m and R₈ are given above; with a compound of formula R₁-NH₂, to obtain a compound of formula (I); and (b) isolating the compound of formula (I) or a pharmaceutically acceptable salt thereof. Invention also relates to a method of producing a compound of formula (I) or a pharmaceutically acceptable salt thereof, comprising step (a) of combining a compound of formula (VI), where each R is hydrogen or, taken together, form a pinacol, with a compound of formula (V), where L, n, R₁, R₂ and R₃, R₄, R₇, m and R₈ are given above, to obtain a compound of formula (I); and (b) isolating the compound of formula (I) or a pharmaceutically acceptable salt thereof.

EFFECT: obtaining compounds used as ALK-2 inhibitors.

14 cl, 5 tbl, 19 dwg, 94 ex

(I), (II), (VI), (V)