FIELD: medicine; pharmaceuticals.
SUBSTANCE: invention relates to a compound of formula (I):
(I),
where ring A is a monocyclic, bridged cyclic or spirocyclic 5–12-member nitrogen-containing saturated heterocyclic group, having 1 to 2 nitrogen atoms and 0 to 1 oxygen atoms as heteroatoms, ring B is a monocyclic or bicyclic 5–12-member unsaturated hydrocarbon or monocyclic or bicyclic 5–12-member unsaturated heterocyclic group which can be substituted with oxo, which has 0 to 3 nitrogen atoms, 0 to 1 sulfur atoms and 0 to 2 oxygen atoms as heteroatoms and which has at least one of nitrogen, sulfur and oxygen, X is O or S, R1 is nitro or cyano, R2 is halogen, R3 is amino, mono- or di (C1-C6 alkyl) amino, (C3-C6 cycloalkyl) amino or C1-C6 alkyl, R4 is halogen; nitro; cyano; carboxy; C1-C6 alkyl, optionally substituted with 1–3 substitutes selected from halogen, carboxy, C1-C6 alkoxy, hydroxy, (C2-C7 acyl) oxy, amino, optionally substituted with C2-C7 acyl, C3-C6 cycloalkyl substituted with hydroxy, or carbamoyl, optionally mono- or disubstituted with C1-C6 alkyl; C2-C6 alkenyl; C1-C6 alkoxy optionally substituted with 1 substituent selected from hydroxy, C1-C6 alkyl, optionally substituted with hydroxy, or monocyclic 6–10-member unsaturated hydrocarbon; C3-C6 cycloalkyl, optionally substituted with 1 substituent selected from C1-C6 alkyl, optionally substituted hydroxy, carbamoyl, substituted with monocyclic 6–10-member unsaturated hydrocarbon, (C1-C6 alkoxy) (C1-C6 alkyl) or C3-C6 cycloalkyl substituted with hydroxy; mono- or di (C1-C6 alkyl) amino; or carbamoyl, optionally substituted with 1 or 2 substitutes, which are C1-C6 alkyl, where, if two or more substituents are present, the substituents can be identical or different, l is integer from 0 to 2, m is integer from 0 to 2 and n is integer from 0 to 5, where, if l is equal to 2, two R2 can be identical or different, if m is equal to 2, two R3 can be identical or different and if n equals from 2 to 5, from two to five R4 can be identical or different.
EFFECT: disclosed compounds are inhibitors of LSD1 and exhibit anti-tumor activity.
12 cl, 39 tbl, 281 ex
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Authors
Dates
2020-07-15—Published
2016-11-25—Filed