10H-PHENOTHIAZINE FERROPTOSIS INHIBITORS, THEIR PRODUCTION METHOD AND THEIR USE Russian patent published in 2023 - IPC C07D279/20 C07D417/06 C07D417/14 A61K31/5415 A61K31/551 A61P9/10 

Abstract RU 2787366 C2

FIELD: medicine.

SUBSTANCE: invention relates to a compound of the formula I, where, if a dotted line is a bond, R1 is selected from 6-element monocyclic unsaturated cycloalkyl and 6-element unsaturated heterocyclic group, all of which are substituted with mR2; m is an integer in the range of 0-3; R2 is selected from a group consisting of substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, unsubstituted 6-element monocyclic saturated cycloalkyl, substituted or unsubstituted 6-7-element saturated heterocyclic group, unsubstituted 6-element monocyclic unsaturated cycloalkyl, amino, hydroxyl, nitro, cyano, -C(O)OR51, -N(H)C(O)R51, -C(O)R51, -S(O)(O)R51, -C(O)N(H)R51; R51 is selected from a group consisting of H, C1-C8 alkyl, amino, unsubstituted 6-element monocyclic unsaturated cycloalkyl, unsubstituted 6-element saturated heterocyclic group, -NR52R53; R52 and R53, each independently, are selected from H, substituted or unsubstituted 6-element saturated heterocyclic group, substituted or unsubstituted C1-C8 alkyl, unsubstituted 4-element saturated cycloalkyl; an alkyl substitute is halogen, substituted or unsubstituted 6-element saturated heterocyclic group; an alkoxyl substitute is halogen, 6-element monocyclic unsaturated cycloalkyl; a substitute of the saturated heterocyclic group is C1-C8 alkyl; a heteroatom of the unsaturated heterocyclic group is N, and a number of heteroatoms is 1 or 2; a heteroatom of the saturated heterocyclic group is N or O, and a number of heteroatoms is 1 or 2; when the dotted line is absent, R1 is selected from a group consisting of 6-element monocyclic unsaturated cycloalkyl, benzo(5-6-element saturated)heterocyclic group, benzo(5-element unsaturated)heterocyclic group, naphthyl, antryl, 6-element unsaturated heterocyclic group, 6-element monocyclic saturated cycloalkyl, all of which are substituted with nR3, and -S(O)(O)R1’; n is an integer in the range of 0-2; R3 is selected from a group consisting of halogen, cyano, hydroxyl, amino, nitro, unsubstituted 6-element monocyclic unsaturated cycloalkyl, phenoxyl, substituted 6-element saturated heterocyclic group, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, -C(O)OR51, -NR52R53; R1’ is selected from 5-7-element saturated heterocyclic group, which is substituted with pR4; p is an integer in the range of 0-2; R4 is selected from a group consisting of hydroxyl, substituted or unsubstituted C1-C8 alkyl, -C(O)R51, -N(H)C(O)OR51, -S(O)(O)R51, -C(O)OR51, unsubstituted 6-element unsaturated heterocyclic group, unsubstituted 6-element saturated heterocyclic group, and substituted or unsubstituted 6-element monocyclic unsaturated cycloalkyl; R51 is selected from a group consisting of C1-C10 alkyl, 5-element saturated heterocyclic group, and benzo(6-element saturated)heterocyclic group; R52 and R53, each independently, are selected from 6-element monocyclic unsaturated cycloalkyl, C1-C8 alkyl; an alkyl substitute is halogen, benzo(6-element saturated)heterocyclic group, substituted or unsubstituted 6-element monocyclic unsaturated cycloalkyl, 6-element saturated heterocyclic group, hydroxyl, -N(H)C(O)OR51, -C(O)R51, -NR52R53; an alkoxyl substitute is 6-element monocyclic unsaturated cycloalkyl, halogen; a substitute of unsaturated cycloalkyl is halogen, C1-C6alkoxyl, cyano, nitro, substituted or unsubstituted C1-C8alkyl; a substitute of the saturated heterocyclic group is C1-C8 alkyl; a heteroatom of the saturated heterocyclic group is O, N, or S, and a number of heteroatoms is 1 or 2; a heteroatom of the unsaturated heterocyclic group is N or O, and a number of heteroatoms is 1. The invention also relates to methods for the production of the specified compounds.

EFFECT: new compounds are obtained, which have an inhibitory effect on ferroptosis and which can be used in medicine as drugs for the treatment of stroke.

11 cl, 2 dwg, 3 tbl, 7 ex

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RU 2 787 366 C2

Authors

Yan, Shenyan

Li, Linli

Dates

2023-01-09Published

2019-03-25Filed