ARYLQUINAZOLINES Russian patent published in 2019 - IPC C07D405/14 C07D401/10 C07D471/04 C07D405/10 C07D409/10 C07D417/10 C07D417/14 C07D409/14 C07D413/14 C07D487/04 A61K31/517 A61K31/519 A61K31/5377 A61P35/00 

FIELD: chemistry.

SUBSTANCE: invention relates to a novel compound of formula (I), a physiologically acceptable salt thereof and/or a stereoisomer having the properties of DNA-dependent protein kinase (DNA-PC). In formula (I)

,

X is CH, CF, S or N, Y is CH, S or N, Z is C or N, , if Z = C, then forms a double bond together with a simple bond, or is absent, if Z = N, n is equal to 1 or 2, where if n = 1, then X = S, and if n = 2, then both X = CH, or X, bonded to the pyrimidine ring, is CF, and X, which is not bonded to the pyrimidine ring, is CH, or one X is CH, and the other X is N; m is equal to 1 or 2, where if m = 1, then Y = S, and if m = 2, then both Y = CH, or one Y is CH, and other Y is N; R¹, R², R³, R⁴ independently of each other are H, Hal, CN, OH, CONH₂, CONH (LA) or LA; R⁵ is H, Hal, CN or C≡CH; Cyc is phenyl which can be unsubstituted or mono- or disubstituted independently by R⁶, or is Het¹; Het¹ is a mono- or bicyclic 5–10-member heterocycle having 1–3 N, 0 and/or S atoms, or 1–4 N atoms, which can be unsubstituted or mono-, di- or tri-substituted independently by R⁶, or can be monosubstituted with Het²; R⁶ is Hal, LA, oxo, CN or NH₂; LA is a straight or branched alkyl having 1–5 C atoms, which can be saturated or partially unsaturated, in which 1–3 H atoms can be replaced by Hal, and/or one H atom can be replaced with CN or Het², and/or one or two CH₂ groups can be replaced by O, NH, N (CH₃) or CO; Het² is 3–5-member aliphatic homo- or heterocycle having 0, 1, 2 or 3 N, 0 and/or S atoms which is unsubstituted; Hal is F, Cl, Br or I; where value H covers ¹H and deuterium. Method of producing a compound of formula (I) and/or a physiologically acceptable salt and/or stereoisomer thereof involves the following steps: (a) reacting a compound of formula (V)

, ,

in which LG is a common leaving group, such as Hal, and R⁵, X, n and Z have values given in cl. 1, with a compound of formula (IV), in which A is a boronic acid or a boronic acid ester, and R¹, R², R³, R⁴, Cyc, Y and m have values specified in cl. 1, to obtain a compound of formula (I), and optionally (b) converting a base or an acid of the compound of formula (I) into one of its salts.

EFFECT: compounds can be used in preparing a drug for sensitizing malignant cells to anti-cancer agents and/or ionizing radiation.

18 cl, 8 tbl, 469 ex