Cyanopyrrolidine derivatives as inhibitors of dpp-iv

Details Cyanopyrrolidine derivatives as inhibitors of dpp-iv Cyanopyrrolidine derivatives as inhibitors of dpp-iv

C - Chemistry, Metallurgy

07

D

C07D 207/16 (2006.01) A61K 31/401 (2006.01) A61K 31/4439 (2006.01) A61P 3/10 (2006.01) A61P 29/00 (2006.01) A61P 31/18 (2006.01) A61P 35/04 (2006.01) A61P 37/02 (2006.01) A61P 43/00 (2006.01) C07D 401/06 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01)

Patent

CA 2428271

A cynaopyrrolidine derivative and pharmaceutical compositions containing same for inhibiting dipeptidyl peptidase IV to treat conditions such as diabetes mellitus and immune diseases. The derivative is represented by Formula (1): (see formula 1) wherein R1 is a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms; R2 is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms; or R1 and R2 together form an oxo, a hydroxyimino group, an alkoxyimino group having 1 to 5 carbon atoms or an alkylidene group having 1 to 5 carbon atoms; R3 and R4 are each a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms; or R3 and R4 together form an oxo, a hydroxyimino group, an alkoxyimino group having 1 to 5 carbon atoms or an alkylidene group having 1 to 5 carbon atoms; X is an oxygen atom or a sulfur atom; Y is -CR5R6- wherein R5 and R6 are the same or different, and are each a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms or an optionally substituted alkenyl group having 2 to 10 carbon atoms; or -CR7R8- CR9R10- wherein R7, R8, R9 and R10 are the same or different, and each a hydrogen atom, a halogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms; or R7 and R9 together with the carbon atom to which they are attached form an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, an optionally substituted cycloalkenyl group having 4 to 8 carbon atoms; an optionally substituted bicycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted bicycloalkenyl group having 5 to 10 carbon atoms; and Z is a hydrogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms, or Y and Z together with the nitrogen atom to which they are attached form an optionally substituted cyclic amino group having 2 to 10 carbon atoms; or a pharmaceutically acceptable salt thereof.

La présente invention concerne des dérivés de cyanopyrrolidine représentés par la formule générale (1), ou les sels pharmaceutiquement acceptables de ceux-ci: dans laquelle R1 représente halogéno, hydroxyle, ou un autre élément du même genre, et R2 représente hydrogène, halogéno, ou un autre élément du même genre, ou encore, R1 et R2 sont réunis pour former oxo, hydroxyimino, ou un autre élément du même genre; R3 et R4 représentent chacun hydrogène, halogéno, ou un autre élément du même genre, ou encore, R3 et R4 sont réunis pour former oxo, hydroxyimino, ou un autre élément du même genre; X représente oxygène ou soufre; Y représente -CR5R6- (R5 et R6 étant chacun et indépendamment l'un de l'autre hydrogène, halogéno, ou un autre élément du même genre) ou -CR7R8-CR9R10- (R7, R8, R9, et R10 représentant chacun et indépendamment les uns des autres hydrogène, halogéno ou un autre élément du même genre, ou encore, R7 et R9 ensemble avec les atomes de carbone à proximité formant C3-8 cycloalkyle ou un autre élément du même genre); et Z représente hydrogène, C1-10 alkyle, ou un autre élément du même genre, ou encore. Y et Z ensemble avec l'atome d'azote à proximité formant C2-10 amino cyclique ou un autre élément du même genre.

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