Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one and use...

C - Chemistry – Metallurgy – 07 – D

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C07D 271/113 (2006.01) A61K 31/4245 (2006.01) A61P 3/10 (2006.01) C07D 413/10 (2006.01) C07D 413/12 (2006.01) C07D 413/14 (2006.01)

Patent

CA 2401953

The invention relates to substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-ones of formula (I), wherein R1 means substituted C1-C6-alkyl and C3-C9-cycloalkyl, R2, R3, R4 and R5 mean hydrogen, halogen, nitro, C1-C4-alkyl, C1-C9-alkyloxy, substituted C6-C10-aryl-C1-C4-alkyloxy, C6-C10-aryloxy, C6-C10-aryl, C3-C8- cycloalkyl or O-C3-C8-cycloalkyl or 2-oxo-pyrrolidin-1-yl, 2,5-dimethylpyrrol- 1-yl or NR6-A-R-7, on the condition that R2, R3, R4 and R5 do not mean simultaneously mean hydrogen and at least one of the radicals R2, R3, R4 or R5 represents the radical 2-oxo-pyrrolidin-1-yl, 2,5-dimethylpyrrol-1-yl or NR6-A- R7, with R6 = hydrogen, C1-C4-alkyl or substituted C6-C10-aryl-C1-C4-alkyl, A = a simple bond, COn, SOn or CONH, n = 1 or 2, R7 = hydrogen, substituted C1- C18-alkyl,C2-C18-alkenyl, C6-C10-aryl-C1-C4-alkyl, C5-C8-cycloalkyl-C1-C4- alkyl, C5-C8-cycloalkyl, C6-C10-aryl-C2-C6-alkenyl, C6-C10-aryl, diphenyl, diphenyl-C1-C4-alkyl, indanyl or the group Het-(CH2)r-, with r = 0, 1,2 or 3 and Het = a saturated and unsaturated 5-7 membered heterocycle which can be benzoanellated and substituted. The invention also relates to a method for producing the same. The inventive compounds have an inhibitory effect on hormone-sensitive lipase, HSL.

L'invention concerne des 3-phényl-5-alcoxi-1,3,4-oxdiazol-2-ones substituées de formule (1) dans laquelle R?1¿ désigne alkyle C¿1?-C¿6? substitué et cycloalkyle C¿3?-C¿9?, R?2¿,R?3¿,R?4¿ et R?5¿ désignent hydrogène, halogène, nitro, alkyle C¿1?-C¿4?, alkyloxy C¿1?-C¿9?, aryle C¿6?-C¿10-?alkyloxy C¿1?-C¿4? substitué, aryloxy C¿6?-C¿10?, aryle C¿6?-C¿10?, cycloalkyle C¿3?-C¿8? ou cycloalkyle O-C¿3?-C¿8?, ou 2-oxo-pyrrolidine-1-yle, 2,5-diméthylpyrrol-1-yle ou NR?6¿-A-R?7¿, sous réserve que R?2¿,R?3¿,R?4¿ et R?5¿ ne désignent pas simultanément hydrogène et qu'au moins un des restes R?2¿,R?3¿,R?4¿ ou R?5¿ ne désigne pas simultanément hydrogène et qu'au moins un des restes R?2¿,R?3¿,R?4¿ ou R?5¿ désigne le reste 2-oxo-pyrrolidine-1-yle, 2,5-diméthylpyrrol-1-yle ou NR?6¿-A-R?7¿, R?6¿ = hydrogène, alkyle C¿1?-C¿4? ou aryle C¿6?-C¿10?-alkyle C¿1?-C¿4? substitué, A = une liaison simple, CO¿n?, SO¿n? ou CONH, n = 1 ou 2, R?7¿ = hydrogène, alkyle C¿1?-C¿18? substitué, alkényle C¿2?-C¿18?, aryle C¿6?-C¿10?-alkyle C¿1?-C¿4?, cycloalkyle C¿5?-C¿8?-alkyle C¿1?-C¿4?, cycloalkyle C¿5?-C¿8?, aryle C¿6?-C¿10?-alkényle C¿2?-C¿6?, aryle C¿6?-C¿10?, diphényle, diphényle-alkyle C¿1?-C¿4?, indanyle, ou le groupe Het-(CH¿2?)r-, où r = 0,1,2 ou 3 et Het = hétérocycle saturé ou insaturé ayant entre 5 et 7 chaînons, qui peut être annelé en benzène et susbtitué. L'invention concerne également un procédé permettant de les préparer. Ces composés présenten un effet inhibiteur de la lipase hormonosensible, HSL.

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