FIELD: chemistry.
SUBSTANCE: invention relates to a novel compound having glucosylceramide synthase (GCS) inhibitory activity, specifically to a compound of formula 1, where L is -O-, Y and Z are independently -CR1R2 or -O-, R1 and R2 independently represent hydrogen; or C1-C6-alkyl; or R1 and R2 form C3-C10-cycloalkyl together with the carbon atom to which they are attached, X is hydrogen; halogen or C1-C6-alkoxy, W is a bond or -CH=CH-, ring A is 6–12 membered aryl selected from the group consisting of phenyl, naphthalenyl or biphenyl; 5–12 membered heteroaryl selected from the group consisting of benzodioxolyl, pyridinyl, thiophenyl, quinolinyl, isoquinolinyl, benzofuranyl, benzo[b]thiophenyl, quinoxalinyl and furanyl; C3-C10-cycloalkyl or 3–12-membered heterocycle selected from the group consisting of 2,3-dihydrobenzodioxynyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, chromanil and 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl, and X1, X2, X3 and X4 are independently hydrogen; cyano; halogen; C1-C6-alkyl; C1-C6-alkoxy-C1-C6-alkyl; C1-C6-alkyl substituted with 1–3 halogens; C3-C10-cycloalkyl; morpholinyl; C1-C6-alkoxy; C1-C6-alkoxy substituted with 1–3 halogens; C1-C6-alkoxy-C1-C6-alkoxy; morpholinyl-C1-C6-alkoxy; mono- or di-C1-C6-alkylamino-C1-C6-alkoxy; C3-C10-cycloalkyl-C1-C6-alkoxy; C1-C6-alkylthio; amino; mono- or di-C1-C6-alkylamino or C1-C6-alkylcarbonyl. Invention also relates to a pharmaceutical composition and a method of inhibiting glucosylceramide synthase based on said compound.
EFFECT: obtaining alternative compounds which can be used to treat diseases mediated by glucosylceramide synthase.
15 cl, 8 tbl, 387 ex
<Formula 1>
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