Pancreatic lipase inhibitor compounds, their synthesis and use

Details Pancreatic lipase inhibitor compounds, their synthesis and use Pancreatic lipase inhibitor compounds, their synthesis and use

C - Chemistry, Metallurgy

07

D

C07D 498/04 (2006.01) A61K 31/5365 (2006.01) A61K 31/542 (2006.01) A61P 3/04 (2006.01) A61P 3/06 (2006.01) A61P 3/10 (2006.01) C07D 265/12 (2006.01) C07D 279/08 (2006.01) C07D 333/36 (2006.01) C07D 333/38 (2006.01) C07D 409/12 (2006.01) C07D 498/02 (2006.01) C07D 513/02 (2006.01) C07D 513/04 (2006.01)

Patent

CA 2471098

The subject invention features compounds having the structure:, wherein X is O, S, CH2 or NR5; Y is O or S; R1 is H, substituted or unsubstituted C1~C15 alkyl, C1-C8 alkylaryl, -C(O)OR4, -C(O)NR4R5, -CR6R6'OR4,-CR6R6'OC(O)R4, - CR6R6'OC(O)NHR7, -C(O)NR1oR11, -C(O)NR8R9 NR8R9, -N(R5)C(O)NHR5, or CH2R4; R2 is a substituted or unsubstituted, straight chain C1-C30 alkyl or branched C3 C30 alkyl, aryl, alkylaryl, arylalkyl, heteroarylalkyl or cycloalkyl; R3 is H or substituted or unsubstituted C1-C6 alkyl or C3-C10 cycloalkyl; R4 is H or a substituted or unsubstituted, straight chain or branched, C6-C30 alkyl, aryl, - CH2-aryl, aryl -C1-C15 alkyl, heteroaryl-C1-C15alkyl or C3-C10 cycloalkyl; R5 is H or a substituted or unsubstituted, straight chain or branched, C6-C30 alkyl, aryl C1-C30alkyl, heteroarylalkyl or cycloalkyl; R6 and R6' are each independently H, substituted or unsubstituted C1-C6 alkyl, dialkyl or C3-C10 cycloalkyl or together form a 3-7 membered ring system; R7 is H or substituted or unsubstituted C1-C12 alkyl or C3-C10 cycloalkyl; R8 and R9 are each independently H, substituted or unsubstituted C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylaryl, or NR8R9 together form a substituted piperazine or piperidine ring or a dihydro-1H-isoquinoline ring system, or a specific enantiomer thereof, or a specific tautomer, or a pharmaceutically acceptable salt thereof and a method for treating diabetes or obesity by administering a therapeutically effective amount of the compounds of the invention.

L'invention concerne des composés de structure (I) ou un énantiomère spécifique ou un tautomère spécifique ou un sel pharmaceutiquement acceptable de ces composés. Dans ladite structure, X représente O, S, CH¿2? ou NR¿5? ; Y représente O ou S ; R¿1? représente H, un alkyle C¿1?-C¿15?, alkylaryle C¿1?-C¿8?, -C(O)OR¿4?, -C(O)NR¿4?R¿5?,-CR¿6?R¿6'?OR¿4?, -CR¿6?R¿6'?OC(O)R¿4?, -CR¿6?R¿6'?OC(O)NHR¿7?, -C(O)NR¿10?R¿11?, -C(O)NR¿8?R¿9?NR¿8?R¿9?, -N(R¿5?)C(O)NHR¿5?, ou CH¿2?R¿4?, substitué ou non ; R¿2? représente un alkyle C¿1?-C¿30? à chaîne linéaire ou un alkyle C¿3?-C¿30?, aryle, alkylaryle, arylalkyle, hétéroarylalkyle ou cycloalkyle à chaîne ramifiée, substitué ou non ; R¿3? représente H ou un alkyle C¿1?-C¿6? ou un cycloalkyle C¿3?-C¿10?, substitué ou non ; R¿4? représente H ou un alkyle C¿6?-C¿30?, aryle, -CH¿2?-aryle, aryl-C¿1?-C¿15?alkyle, hétéroaryl-C¿1?-C¿15?alkyle ou cycloalkyle C¿3?-C¿10?, à chaîne linéaire ou ramifiée, substitué ou non ; R¿5? représente H ou un alkyle C¿6?-C¿30?, aryl-C¿1?-C¿30?alkyle hétéroarylalkyle ou cycloalkyle, à chaîne linéaire ou ramifiée, substitué ou non ; R¿6? et R¿6'? représentent indépendamment l'un de l'autre H, un alkyle C¿1?-C¿6?, dialkyle ou cycloalkyle C¿3?-C¿10?, substitué ou non, ou forment un système cyclique à 3-7 chaînons ; R¿7? représente H ou un alkyle C¿1?-C¿12? ou un cycloalkyle C¿3?-C¿10?, substitué ou non ; R¿8? et R¿9? représentent indépendamment l'un de l'autre H, un alkyle C¿1?-C¿6?, alkoxy C¿1?-C¿6? ou alkylaryle C¿1?-C¿6?, substitué ou non, ou NR¿8?R¿9? forment un cycle pipérazine ou pipéridine substitué ou un système cyclique dihydro-1H-isoquinoline. L'invention se rapporte en outre à un procédé de traitement du diabète ou de l'obésité consistant à administrer une dose thérapeutiquement efficace desdits composés.

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