C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/277.1, 260/2
C07D 221/10 (2006.01) C07D 215/233 (2006.01) C07D 221/12 (2006.01) C07D 401/00 (2006.01) C07D 405/00 (2006.01)
Patent
CA 1178274
Abstract 9-Amino-1-hydroxyoctahydrobenzo[c]quinoline deri- vatives of formula Image ---(I) and pharmaceutically acceptable acid addtion salts thereof wherein R is hydrogen, COR7 or SO2R6 where R7 is hydrogen, alkyl, having from one to five carbon atoms; alkenyl and alkynyl each having from two to six carbon atoms; trifluoromethyl, benzyl, furyl, thienyl, pyridyl or R9C6H4 wherein R9 is H, NH2, F, Cl, Br CH3 or OCH3; R8 is alkyl having from one to five carbon atoms or R9C6H4; R1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or -CO-(CH3)p-NR2R3 wherein p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R2 and R3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino or N-alkylpiperazino having from one to four carbon atoms in the alkyl group; R4 is hydrogen, alkyl having from 1 to 6 carbon atoms or -(CH2)3-C6H5 wherein r is an integer from 1 to 4; R5 is hydrogen, methyl or ethyl; R6 is hydrogen, -(CH2Iy-carbalkoxy having from one to four carbon atoms in the alkoxy group and wherein y to 0 or an integer from 1 to 4, carbobenzyloxy, 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 (a) alkylene having from one to nine carbon atoms; (b) -(alk1)m-X-(alk2)n- wherein each of (alk1) and (alk2) 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 to 1; X is O, S, SO and SO2; and W is hydrogen, methyl, pyridyl, piperidyl, Image W1 wherein W1 is selected from the group consisting of hydrogen, fluoro and chloro; and Image wherein W2 is hydrogen or Image W1; a is an integer from 1 to 5 and b is 0 or an integer from 1 to 5; with the proviso that the sum of a and b is not greater than 5; useful in mammals as analgesics, tranquilizers, anti- amatic agents, diuretics, anticonvulsants, antidiarrheals, antitussives, in treatment of glaucoma, and intermediates therefore.
382558
Limited Pfizer
Smart & Biggar
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