FIELD: chemistry.
SUBSTANCE: invention relates to the field of organic chemistry, specifically to a heterocyclic compound of formula I, where R1a: H or halogen; R1b: halogen, C1-4-alkyl (optionally substituted with three halogens), C1-4-alkoxy group (optionally substituted with three halogens); X: -S-, -O- or -N=CH-; W: N or CR3, when W is N, R2 is H or -CN, when W is CR3, one of R2 or R3 represents H, -CN, halogen, C1-4-alkyl (optionally substituted with one substituent selected from OH or CN), -C(=O)CH3, -C(=O)CF3, -C(=O)OCH3, -C(=O)NH2, -NHC(=O)CH3, and the other one is H or C1-4-alkyl; R4: C1-4-alkyl; R5: C1-4-alkyl optionally substituted with one or three substituents selected from CN, halogen or -C(=O)NH2; one of R6a or R6b is selected from H, -CH3 and halogen, and the other is H; Cy: 4–6 membered monocyclic heterocycloalkyl containing 1-2 heteroatoms selected from O, N and S, or 5-6 membered heterocycloalkenyl containing 1 double bond containing 1-2 heteroatoms independently selected from O, N and S; R7: OH, oxo, halogen and C1-4-alkyl; the subscript a is 0, 1, or 2; R8: -(L1-W1)m-L2-G1, where L1 is absent or represents -C(=O)-, -NRi, -NRhC(=O)- or -SO2-; W1: C1-4alkylene; the subscript m is 0 or 1; L2 is absent or represents -O-, -C(=O)-, -C(=O)O-, -OC(=O)-, -C(=O)-C(=O)-, -C(=O)-C(=O)NRa-, -NRb-, -C(=O)NRc-, -SO2- or -SO2NRe-; G1: H, -CN, C1-4-alkyl (optionally substituted with one or three substituents selected from -CN, OH, halogen or phenyl), C3-6-cycloalkyl (optionally substituted with -NH2), 5-membered heterocycloalkenyl containing 1 double bond, containing 2 heteroatoms independently selected from O and N (optionally substituted with one substituent selected from groups R9), 4–6 membered monocyclic heterocycloalkyl containing 1-2 heteroatoms independently selected from O and N (optionally substituted with one or two substituents independently selected from the groups R9), or a 5-membered heteroaryl containing 1–4 heteroatoms independently selected from O, N, and S (optionally substituted with one substituent independently selected from the groups R10), R9: oxo or R10; R10: -OH, halogen, -CN, C1-4-alkyl (optionally substituted with one substituent selected from OH or phenyl), C3-cycloalkyl, -SO2CH3, -C(=O)C1-4-alkoxy, -C(=O)C1-4-alkyl or -NRgC(=O)C1-4-alkyl; and each Ra, Rb, Rc, Re, Rg, Rh and Ri is independently selected from H and C1-4-alkyl. Invention also relates to specific compounds, a pharmaceutical composition based on a compound of formula I and use thereof.
I.
EFFECT: obtaining novel heterocyclic compounds with autotaxin inhibitory activity.
15 cl, 9 tbl, 6 ex
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Authors
Dates
2018-12-25—Published
2014-03-07—Filed