C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
167/231, 260/279
C07D 401/04 (2006.01) A61K 31/44 (2006.01) C07D 413/04 (2006.01) C07D 417/04 (2006.01)
Patent
CA 1340458
The present invention relates to novel compounds of the following formula, where the dotted line designates an optional bond: (see fig. I) wherein "het" designates a five membered heterocyclic ring which may include 1 or 2 double bonds and 1-4 heteroatoms selected from nitrogen, oxygen or sulphur,provided that "het" may not designate an oxadiazole; R1 is selected from hydrogen, lower alkyl, optionally substituted with phenyl which may be substituted with halogen, lower alkyl, or lower alkoxy, or a group R6-CO-NH-CH2- or R6-O-CO-, wherein R6 is lower alkyl, branched or unbranched, or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy, or lower acyloxy; R2 and R3 are the same or different, each representing hydrogen, lower alkyl, cycloalkyl (3-6 C-atoms), lower alkenyl, lower alkadienyl, lower alkynyl, optionally substituted with hydroxy, halogen or phenyl, in which the phenyl group may be substituted with halogen, trifluoromethyl, lower alkyl, hydroxy or lower alkoxy; R2 and R3 may further, respectively, be selected from trifluoromethyl or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy or lower acyloxy, or R2 and R3 may, respectively, be a group OR7 or SR7 wherein R7 is defined as R2 or R3, and if "het" includes 2 or more carbon atoms, R4 and R5 are the same or different, and each is defined as R2 or R3, and if "het" includes only one carbon atom, there is only one substituent, R4, on the heterocyclic ring, and R4 is defined as R2 or R3, as well as individual stereo isomers and pharmaceutically acceptable acid addition salts thereof. The invention moreover relates to methods for the preparation of the compounds of formula 1, to novel intermediates, to pharmaceutical compositions containing same and to methods for the treatment of disorders, caused by malfunction of the acetylcholine (AcCh) or muscarinic system, by administering a non-toxic effective amount of a compound of formula I.
570135
Bogeso Klaus Peter
Jensen Klaus Gundertofte
Moltzen Ejner Knud
Pedersen Henrik
H. Lundbeck A/s
Perley-Robertson Hill & Mcdougall Llp
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