FIELD: chemistry.
SUBSTANCE: invention relates to a compound of formula I: I or its pharmaceutically acceptable enantiomer or salt. In formula I: each of X1 and X2 independently represents H or halogen, R1, R2 and R3 independently represent H, Q is H, A1 and A2 together form a 5-membered condensed ring structure containing SO2NR5CR9'R9, where in the specified structure R9' represents H, or each of R9' and R9 represents methyl, and when R9' is H, R9 represents a hydrogen atom, cyclopropyl or C1-C6alkyl optionally substituted with one, two or three substituents selected from halogen, C1-C4alkyl, OH, oxo, NH2, NHCH3, N(CH3)2, NHCOOCH3, NHCOCH3 and N(CH3)COCH3; or -CH2NHSO2CH3 group or -C(O)OCH3. Group R5 independently represents: (1') H, (2') straight or branched C1-C6alkyl, possibly substituted with up to three substituents, inclusive, selected from one or more hydroxyl, OR9, CONR9R10, NR9COR10, NR9R10, SO2R9, SO2NR9R10, NR9SO2R10 and SOR9; or group -CH2-CH2NHCOOCH2CH3, (3') heterocyclyl or group C1-C3alkyl-heterocyclyl, wherein said heterocyclyl is optionally substituted with up to three substituents, which are selected from one or more halogen, hydroxyl, oxo, OR9, NR9R10, CO-alkyl and C1-C6alkyl, or a group -(piperazin-1-yl)propan-1-one, (4') C3-C6cycloalkyl, possibly substituted by up to three substituents, inclusive, selected from halogen, hydroxyl, OR9, CONR9R10, NR9COR10, NR9R10, SO2R9, SO2NR9R10, NR9SO2R10 and SO2R9, where each of R9 and R10 independently represents a hydrogen atom or C1-C6alkyl, (5') C1-C3alkyl-heteroaryl, wherein heteroaryl is optionally substituted with -CH3 group or -CH3 and -OH groups, and where heteroaryl is an aromatic ring containing 5-6 atoms, in which one or more carbon atoms are replaced by nitrogen atoms. Pharmaceutical composition, a drug, and a method of treatment are also provided.
EFFECT: compounds of the invention may be used to treat and/or prevent cancer or inhibit TDO2.
15 cl, 2 tbl, 153 ex
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Authors
Dates
2018-11-13—Published
2016-03-17—Filed