Pyridazino[4,5-b]indolizines

C - Chemistry – Metallurgy – 07 – D

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260/263, 260/264

C07D 471/04 (2006.01) C07D 519/00 (2006.01)

Patent

CA 2008571

Abstract of the Disclosure The compound of the formula: Image in which R1 is hydrogen, alkoxy, cyano, halo, nitro, amino, or mono- or dialkylamino; R2 is hydrogen, alkyl, phenyl, benzyl, 2-thienyl, 3-thienyl or 2-, 3- or 4-pyridinyl; R3 is hydrogen, alkyl or phenyl; R4 is N-methyl-pyrrolidin-2-yl, 2-, 3- or 4-pyridinyl, 3- quinuclidinyl or Image where n is 1 to 5; m is 0 to 3; and R8 is hydrogen or alkyl of 1 to 6 carbon atoms; or R4 is Image wherein: a) n is 2, R5 taken with R3 is ethylene and R6 is -CHO, alkyl, unsubstituted or substituted phenyl, pyrimidinyl, pyridinyl, or pyrazinyl, where the substituents are alkyl, alkoxy, halo, cyano, nitro or trifluoromethyl; b) n is 1 to 5, and R5 and R6, taken together are polymethylene which may be alkyl substituted or R5 and R6 aremorpholino, 3-azabicyclo[3.2.2]nonan-3-yl, pyrrol-1-yl, pyrrolidin-1-yl, pyrrolidin-2- on-1-yl, pyrrolidin-2-thion-1-yl, imidazol-1-yl, alkyl-piperidin-1-yl or a piperazin-1-yl moiety in the 4-position of which is hydrogen, -CHO, alkyl or unsubstituted or substituted phenyl, pyrimidinyl, pyridinyl, or pyrazinyl, alkoxy, halo, cyano, nitro or trifluoromethyl; or c) n is 1 to 5, and R5 and R6 are, independently, hydrogen, alkyl, phenyl, 3-quinuclidinyl, 2-adamantyl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.3.1]nonan- 9-yl or 2-, 3- or 4- pyridinyl; or a pharmaceutically acceptable salt thereof are M1 receptor agonists useful in treatment of dementias involving the cholinergic system.

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