C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/277.1, 260/2
C07D 221/10 (2006.01) C07D 401/06 (2006.01)
Patent
CA 1101860
ABSTRACT Tetrahydro-3-substituted benzo[c]quinoline-9(8H) ones useful as intermediates in the production of CNS agents and of the formula Image ...III wherein R0 is oxo or alkylenedioxy of two to four carbon atoms; R1 is hydrogen or an acyl group selected from benzoyl, alkanoyl having from one to five carbon atoms or -CO-(CH2)p-NR2R3 wherein p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is the same or different and is hydrogen or alkyl having from one to four carbon atoms; R? and R3 when taken together with the nitro- gen to which they are attached form a 5- or 6-membered heterocyclic ring, said ring being piperidino, pyrrolo, pyrrolidino, morpholino or N-alkylpiperazino having from one to four carbon atoms in the alkyl group; R4 is hydro- gen, alkyl having from 1 to 6 carbon atoms or -(CH2)z-C6H5 wherein z is an integer from 1 to 4; R5 is hydrogen, methyl or ethyl; R6 is hydrogen, formyl, alkanoyl having from two to five carbon atoms, alkyl having from one to six carbon atoms; -(CH2)x-C6H5 wherein x is an integer from 1 to 4, or -CO(CH2)x-1-C6H5; Z is alkylene having from one to nine carbon atoms, or -(alk1)m-X-(alk2)n- where each of (alk1) and (alk2) is the same or different and is alkylene having from one to nine carbon atoms, with the proviso that the summation of carbon atoms in (alk1) plus (alk2) is not greater than nine, each of m and n is 0 or 1, and X is O, S, SO or SO2; and W is hydrogen, methyl, pyridyl Image wherein W1 is hydrogen, fluro or chloro may be obtained by reacting a compound of the formula: Image ...VII wherein R1 is hydrogen, benzyl, methyl or ethyl; R4, R5, Z and W are as defined above and R7 is hydrogen or formyl, with a base, and, when required to produce a compound where R0 is alkylenedioxy ketalizing the compound obtained and when required to pro- duce a compound wherein R1 is other than hydrogen esterifying the product wherein R1 is hydrogen.
344747
Gowling Lafleur Henderson Llp
Pfizer Inc.
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