C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 401/06 (2006.01) A61K 31/44 (2006.01) A61K 31/495 (2006.01) C07D 213/50 (2006.01) C07D 213/55 (2006.01) C07D 213/57 (2006.01) C07D 213/61 (2006.01) C07D 237/08 (2006.01) C07D 239/26 (2006.01) C07D 403/06 (2006.01) C07D 405/06 (2006.01) C07D 405/08 (2006.01) C07D 409/08 (2006.01)
Patent
CA 2128233
2128233 9314085 PCTABS00024 Compounds of formula (I) have been shown to enhance the release of the neurotransmitter acetylcholine, and thus may be useful in the treatment of diseases of man, such as in Alzheimer's disease and other conditions involving learning and cognition, where subnormal levels of this neurochemical are found. The compounds of this invention can be described as shown in formula (I) where Q is (a) or (b), A and B are independently selected from the group including H, R4, -OH and -OCOR4, or A and B together form =O, =S, =CH2, =CHR4, =C(R4), =NOH, =NOR4, 1,3-dioxane, 1,3-dioxolane, 1,3-dithiane or 1,3-dithiolane; R1 is 4-, 3-, or 2-pyridyl, pirimidyl, pyrazinyl, 2-fluoro-4-pyridyl or 3-fluoro-4-pyridyl; R2 is alkyl of 1 to 10 carbons, cycloalkyl of 3 to 8 carbons, 2-, 3-, or 4-pyridyl, Phe or Phe-W; Phe is a phenyl group; W is F, Cl, Br, R4, -OH, -OR4, -NO2, -NH2, -NHR4, -NR4R4, -CN, -S(O)m-R4; R3 is H, F, Cl, Br, -CN, -OH, -NO2, -NH2, -CF3, -NHR4, -NR4R4, R4, -OR4, -S(O)m-R4; R4 and R4' are alkyl of 1 to 4 carbons, CH2Phe-W or Phe-W; R5 is -(CH2)n-Y or -OCOR4; Y is H, OH, NH2, -NHR4, -NR4R4, -NHCOR4, -NHCO2R4, F, Cl, Br, OR4, -S(O)mR4, -CO2H, -CO2R4, -CN, -CONR4R4, -CONHR4, -CONH2, -COR4; -CH=CHCO2R4, OCOR4, Phe, Phe-W, -C=CCO2R4, -CH=CHR4, or -C=CR4; m is 0, 1 or 2; n is 1 to 7; provided that, when Q is oxindole and R5 is (CH2)nY, then Y is other than OH; and physiologically suitable salts thereof.
Earl Richard Alan
Voss Matthew Ernst
Wilkerson Wendell Wilkie
Dimock Stratton Llp
Du Pont Pharmaceuticals Company
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