C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 401/06 (2006.01) A61K 31/40 (2006.01) A61K 31/435 (2006.01) A61K 31/535 (2006.01) A61K 31/54 (2006.01) C07D 207/08 (2006.01) C07D 207/09 (2006.01) C07D 401/14 (2006.01) C07D 403/06 (2006.01) C07D 413/06 (2006.01) C07D 413/14 (2006.01)
Patent
CA 2144294
(Pyrrolidinyl)phenyl carbamates of the formula (1,2) Image wherein Image a. R is hydrogen, loweralkyl, a group of the formula a group of the formula Image a group of the formula Image a group of the formula Image Image a group of the formula a group of the formula Image or a group of the formula Image wherein X is -CH2-, -O- , or -S- , Y is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, or trifluoromethyl, and m is 1 to 5, n is 1 to 5, and p is 1,2,3,4, or 5; b. R1 and R2 are independently hydrogen or loweralkyl; c. R3 and R4 are independently hydrogen, loweralkyl, phenyl or phenyl substituted by one or more loweralkyl, loweralkoxy, hydroxy, halogen, or trifluoromethyl groups, or taken together with the nitrogen atom to which they are bound form a pyrrolidinyl, piperidinyl, morpholinyl, or thiomorpholinyl group, or a group of the formula Image d. R7 is H2 or = O; the optical isomers, or pharmaceutically acceptable salts thereof. The present invention also relates to intermediate compounds of the formula (3,4) Image wherein a. R is a group of the formula Image a group of the formula Image a group of the formula Image a group of the formula Image or a group of the formula Image wherein Y is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, or trifluoromethyl, and m is 1 to 5, n is 1 to 5, and p is 1,2,3,4, or 5; b. R1 and R2 are independently hydrogen or loweralkyl; c. R5 is hydrogen or loweralkyl; d. R7 is H2 or = O; or the optical isomers thereof, or pharmaceutically acceptable salts thereof. The present invention also relates to intermediate compounds of the formula (3,4) as shown above, wherein: a. R is a group of the formula Image or a group of the formula Image wherein X is -CH2-,-0-, or -S-; Y is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, or trifluoromethyl, and m is 1 to 5, n is 1 to 5; b. R1 and R2 are independently hydrogen or loweralkyl; c. R5 is hydrogen or loweralkyl; d. R7 is H2 or =0; with the proviso that when R1 and R2 are hydrogen, R5 is CH3 and R7 is H2, the resulting methoxy group cannot be 4-OCH3; or the optical isomers therof, or pharmaceutically acceptable salts thereof. Processes for the preparation of the compounds of formula (1,2) or (3,4) and their use in relieving memory dysfunction are disclosed.
Nemoto Peter
Wettlaufer David
Aventis Pharmaceuticals Inc.
Bereskin & Parr
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