US 8,946,212 B2Granted

Annelated N-heterocyclic sulfonamides with oxadiazolone headgroup, processes for their preparation and their use as pharmaceuticals

AssigneeSanofi-Aventis

InventorsStefanie Keil, Matthias Urmann, Wolfgang Wendler, Maike Glien, Hans Matter, Eugen Falk

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Abstract

Annelated N-heterocyclic sulfonamides with oxadiazolone headgroup, processes for their preparation and their use as pharmaceuticals The invention relates to annelated N-heterocyclic sulfonamides with oxadiazolone headgroup and to their physiologically acceptable salts and physiologically functional derivatives showing PPARdelta or PPARdelta and PPARalpha agonist activity. What is described are compounds of the formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparations. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistance is involved and demyelinating and other neurodegenerative disorders of the central and peripheral nervous system.

Claims17

Dependent claims

Compound of the formula I:

wherein
Y is O;
R1 is H, halogen, (C1-C8)alkyl, (C0-C4)alkylene-(C3-C7)cycloalkyl, (C0-C4)alkylene-(C5-C10)heteroaryl, (C0-C4)alkylene-O—(C0-C8)alkyl, (C0-C4)alkylene-(C6-C10)aryl, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R2 is H, (C1-C8)alkyl, halogen, (C0-C4)alkylene-O—(C0-C8)alkyl, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R5 is H, (C1-C8)alkyl, (C0-C4)alkylene-(C3-C7)cycloalkyl, (C0-C4)alkylene-(C6-C10)aryl, (C0-C4)alkylene-(C5-C10)heteroaryl, (C0-C4) alkylene-N(R10)(R11), wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R6 is H, (C1-C8)alkyl, (C0-C4)alkylene-(C3-C7)cycloalkyl, (C0-C4)alkylene-(C6-C10)aryl, (C0-C4)alkylene-(C5-C10)heteroaryl, (C0-C4)alkylene-N(R10)(R11), wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R7 is H, halogen, (C1-C8)alkyl, (C0-C4)alkylene-O—(C0-C4)alkylene-H, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R8 is H, halogen, (C1-C8)alkyl, (C0-C4)alkylene-O—(C0-C4)alkylene-H, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F, whereby R8 is only attached to carbon;
R9 is H, halogen, (C1-C8)alkyl, (C0-C4)alkylene-(C3-C7)cycloalkyl, (C0-C4)alkylene-O—(C0-C8)alkyl, (C0-C4)alkylene-(C6-C10)aryl, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R10 is H, (C1-C8)alkyl, (C0-C4)alkylene-O—(C0-C8)alkyl, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
R11 is H, (C1-C8)alkyl, (C0-C4)alkylene-O—(C0-C8)alkyl, wherein alkyl and alkylene are unsubstituted or 1- to 3-fold substituted by F;
and
X1, X2, X3, X4 and X5 are CH;
in all its stereoisomeric forms and mixtures in any ratio, or its physiologically acceptable salts and tautomeric forms.

11 more elements

Dependencies are inferred from the claim text.