BENZOIMIDAZOLES AS PROLYL HYDROXYLASE INHIBITORS Russian patent published in 2014 - IPC C07D403/04 C07D487/04 A61K31/4184 A61P7/06 A61P9/10 

FIELD: chemistry.

SUBSTANCE: invention relates to the field of organic chemistry, namely to benzoimidazole derivatives of formula (I), as well as to their enantiomers, diastereoisomers, racemates and pharmaceutically acceptable salts, where n equals from 2 to 4, each of R¹ substituents is independently selected from H, halogen, -C_1-4alkyl, -C_1-4pergaloalkyl, trifluoro-C_1-4alkoxy, -NO₂, -CN, CO₂H, -OC_1-4alkyl, -SC_1-4alkyl, -S(C_1-4alkyl)-R^c, -S(O)₂(C_1-4alkyl)-R^c, -S(O)-C_1-4alkyl, -SO₂-C_1-4alkyl, -S-R^c, -S(O)-R^c, -SO₂-R^c, -SO₂-NH-R^c, -O-R^c, -CH₂-O-R^c, -C(O)NH-R^c, -NR^aR^b, benzyloxy, phenyl, optionally substituted with one-two R^d, cyanobiphenyl-4-ylmethylsulpfanyl, cyanobiphenyl-4-ylmethanesulphonyl, or -S-(CH₂)₂-morpholine and two adjacent groups R¹ can bind with formation of an aromatic 5-6-membered ring, optionally substituted with one methyl group or two atoms of halogen, optionally containing one or two S or N; R^a and R^b each independently represents C_1-4alkyl, -C(O)C_1-4alkyl, -C(O)-R^c, -C(O)CH₂-R^e, C_1-4alkyl-R^e, -SO₂-R^c, -SO₂-C_1-4alkyl, phenyl, benzyl; or R^a and R^b together with a nitrogen atom, which they are bound with, form a monocyclic 5-6- membered heterocycloalkyl ring, optionally containing one heteroatom, selected from O; R^c represents -C_3-8cycloalkyl, phenyl, optionally substituted with one-two R^d, benzyl, optionally substituted with one-three R^d; morpholine; R^d independently represents halogen, -OH, -C_1-4alkyl or -C_1-4perhalogenalkyl, trifluorine C_1-4alcoxy, -OC_1-4alkyl, or -O-benzyl optionally substituted with halogen, R^e represents -C₆heterocycloalkyl, optionally containing one or two of O or N atoms, optionally substituted with a methyl group; R² and R³ both represent H, -CF₃ or C_1-3alkyl; each of Z represents a C or N atom, on condition that simultaneously not more than two Z represent N. The invention also relates to particular compounds, a pharmaceutical composition, based on formula (I) compound or a particular said compound, a method of treating diseases, mediated by propyl hydroxylase activity.

EFFECT: novel derivatives of benzimidazole, possessing an inhibiting activity with respect to PHD are obtained.

11 cl, 1 tbl, 186 ex