FIELD: pharmacology.
SUBSTANCE: invention relates to new N-(pyrid-4-yl)amides and N-(pyrimidin-4-yl)amides of formula (1) or their pharmaceutically acceptable salts having the properties of androgen receptor inhibitor (AR). The compounds can be used for pharmaceutical or cosmetic composition to treat androgen-dependent disease or disorder. These diseases include dermatological diseases or disorders such as diseases or disorders of sebaceous gland (glands); acne; hyperseborrhea; greasy skin; seborrheic dermatitis; hyperpilosity or hirsutism; atopic dermatitis or androgenic alopecia. In N-(pyrid-4-yl)amides and N-(pyrimidin-4-yl) amides of formula (1) 
, R1 is C1-6 alkyl, C3-7cycloalkyl, C1-6alkyloxy, -S(O)m-C1-6alkyl, C1-6fluoroalkyl, C1-6fluoroalkyloxy, C1-6alkyl-OH, -(CH2)iC1-6alkyloxy, -(CH2)j1-O-C1-6fluoroalkyl, CORa, CN, NO2, NR5R6 or halogen atom; R2 ishydrogen atom, methyl, methoxy or bromine atom; R3 and R4 are the same or different and represent hydrogen atom, C1-12alkyl, C3-9cycloalkyl, C1-6fluoroalkyl, -C1-6alkyl-OH, -(CH2)p-C1-6alkyloxy, -(CH2)q-C3-9cycloalkyl, -(CH2)rC1-6fluoroalkyl, -(CH2)s-O-C1-6fluoroalkyl, phenyl, heteroaryl, heterocyclyl group, -(CH2)t-phenyl or -(CH2)v-heteroaryl, where each phenyl and heteroaryl are optionally substituted with 1-3 same or different groups of Rc; as well as R3 and R4 together with carbon atom carrying them can form C3-9cycloalkyl group or heterocyclyl group, such as tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydro-1-oxo-thiopyranyl or tetrahydro-1.1-dioxo-thiopyranyl; Rc is C1-6alkyl, C3-7cycloalkyl, C1-6alkiloxi, -S(O)u-C1-6alkyl, C1-6fluoroalkyl, C1-6fluoroalkyloxy, C1-6alkyl-OH, CORd, CN, NO2, NR9R10, OH or halogen atom; Ra and Rdare the same or different and represent C1-6alkyl, C1-6alkyloxy or NR7R8; R5, R6, R7, R8, R9 and R10 are the same or different and represent hydrogen atom, C1-6alkyl, C3-7cycloalkyl or -(CH2)w-C3-7cycloalkyl; as well as R5 and R6 together with nitrogen atom carrying them can form heterocyclyl group; as well as R7 and R8 together with nitrogen atom carrying them can form heterocyclyl group; as well as R9 and R10 together with nitrogen atom carrying them can form heterocyclyl group; i, j, p, q, r, s, t, v and w are different or the same and represent 1, 2 or 3; n and u are different or the same and represent 0, 2 or 2; and X represents CH or N.
EFFECT: improved properties of compounds.
22 cl, 4 tbl, 80 ex
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