Pyridazine compounds as glycogen synthase kinase 3 inhibitors

Details Pyridazine compounds as glycogen synthase kinase 3 inhibitors Pyridazine compounds as glycogen synthase kinase 3 inhibitors

C - Chemistry, Metallurgy

07

D

C07D 487/04 (2006.01) A61K 31/55 (2006.01) A61K 31/551 (2006.01) A61P 25/28 (2006.01) C07D 471/14 (2006.01)

Patent

CA 2614385

Disclosed are pyridazine compounds of the formula I which are useful for inhibiting glycogen synthase kinase 3 (GSK-3), methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds: In formula (I) indicates a single bond or a double bond; X is O, S or N-R5; R1, R2 are independently selected from the group consisting of H, NH2, NH-C1-C6-alkyl, OH, =O, (i.e. a carbonyl group), C1-C6-alkoxy, halogen, methyl, C2-C4-alkyl, C3- C4-cycloalkyl, C3-C4-alkenyl, fluorinated C1- C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-alkenyl, formyl, C1- C3-alkylcarbonyl, and an aromatic radical Ar, R1 and R2 together with the carbon atoms, to which they are attached, form a fused, saturated or unsaturated 5-, 6- or 7-membered C-bound carbocyclic or heterocyclic ring comprising 1 heteroatom, selected from nitrogen, oxygen and sulfur as ring member and O, 1 or 2 further heteroatoms, independently selected from O, S and N, as ring members, wherein the fused ring is unsubstituted or may carry 1 , 2 or 3 substituents selected, independently of each other, from the group of radicals R4 as defined below; R3 is hydrogen OH, halogen, CN, nitro, C1-C6- alkyl, fluorinated C1-C6-alkyl, C1-C6- hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, fluorinated C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, fluorinated C3-C7-cycloalkyl, C1-C6-alkoxy, C1-C6- hydroxyalkoxy, C1C6-alkoxy- C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6- alkylthio, fluorinated-C1-C6 alkylthio, C1C6-alkylsulfinyl, fluorinated C1-C6- alkylsulfinyl, C1-C6- alkylsulfonyl, fluorinated C1-C6 alkylsulfonyl, C1C6- alkylcarbonyl, fluorinated C1C6-alkylcarbonyl, C1 -C6-alkylcarbonylamino, fluorinated C1-C6- alkylcarbonylamino, carboxy, C1-C6-alkyloxycarbonyl, fluorinated C1-C6- alkoxycarbonyl, NRaRb, C(O)-NReRf, NH-C(O)-N ReRf, NRaRb-C1-C6-alkylene, O- NRaRb, etc. and wherein R4 and R5 are as defined in the specification and the claims.

L'invention porte sur des composés pyridazine de la formule (1) qui sont utilisés pour inhiber la glycogène synthase kinase 3 (GSK-3), sur des procédés de fabrication desdits composés, sur des compositions contenant les composés, et sur des procédés de traitement faisant appel auxdits composés. Dans la formule (1),---- indique une liaison simple ou double; X est O, S ou N-R5; R1 et R2 sont choisis indépendamment dans le groupe composé de H, NH2, NH-C1-C6-alkyle, OH, =O, (c'est-à-dire un groupe carbonyle), C1-C6-alcoxy, halogène, méthyle, C2-C4-alkyle, C3-C4-cycloalkyle, C3-C4-alcényle, C1-C4-alkyle fluoré, C3-C4-cycloalkyle fluoré, C3-C4-alcényle fluoré, formyle, C1-C3-alkylcarbonyle, et un radical aromatique Ar, R1 et R2, avec les atomes de carbone auxquels ils sont attachés, forment un noyau carbocyclique ou hétérocyclique lié à C à 5, 6 ou 7 chaînons, saturé ou insaturé, fusionné comprenant comme élément de noyau 1 hétéroatome choisi entre l'azote, l'oxygène et le soufre et 0, 1 ou 2 hétéroatomes supplémentaires, choisis indépendamment entre O, S et N, comme éléments de noyau, le noyau fusionné étant non substitué ou pouvant porter 1, 2 ou 3 substituants choisis, indépendamment l'un de l'autre, dans le groupe de radicaux R4 tel que défini ci-après; R3 est hydrogène OH, halogène, CN, nitro, C1-C6-alkyle, C1-C6-alkyle fluoré, C1-C6-hydroxyalkyle, C1-C6-alcoxy-C1-C6-alkyle, C2-C6-alcényle, C2-C6-alcényle fluoré, C2-C6-alkynyle, C3-C7-cycloalkyle, C3-C7-cycloalkyle fluoré, C1-C6-alcoxy, C1-C6-hydroxyalcoxy, C1C6-alcoxy-C1-C6-alcoxy, C1-C6-alcoxy fluoré, C1-C6-alkylthio, C1-C6-alkylthio fluoré, C1C6-alkylsulfinyle, C1-C6-alkylsulfinyle fluoré, C1-C6-alkylsulfonyle, C1-C6-alkylsulfonyle fluoré, C1C6-alkylcarbonyle, C1C6-alkylcarbonyle fluoré, C1-C6-alkylcarbonylamino, C1-C6-alkylcarbonylamino fluoré, carboxy, C1-C6-alkyloxycarbonyle, C1-C6-alcoxycarbonyle fluoré, NRaRb, C(O)-NReRf, NH-C(O)-N ReRf, NRaRb-C1-C6-alkylène, O-NRaRb, etc.; et R4 et R5 sont tels que définis dans la description et les revendications.

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