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2,5-Methano-benzo-(g)-quinoline-3-carboxylate cpds. - and their conversion into analgesic and analgesic antagonist 2,6-methano-3-benzazocine derivs. (BE 20.3.78)
2,5-Methano-benzo-(g)-quinoline-3-carboxylate cpds. - and their conversion into analgesic and analgesic antagonist 2,6-methano-3-benzazocine derivs. (BE 20.3.78)
New 2,5-Methanobenzo(g)quinoline-3-carboxylate esters are of formula (I): In (I) R1 is H, lower alkyl, lower alkenyl, lower alkynyl, halo-(lower alkenyl), cycloalkyl, (cycloalkyl)-(lower alkyl), 2- or 3-furylmethyl, 2- or 3-furylmethyl ring-substd. by 1-3 methyl gps., phenyl-(lower alkyl), phenyl-(lower alkyl) ring mono- or disubstd. by halogen, lower alkyl, OH, lower alkanoyloxy, lower alkoxy, lower alkylmercapto, CF3, amino and/or lower alkanoylamino, or methylenedioxyphenyl-(lower alkyl); R2, R2', R2" and R2"' are all H, or three of these residues are H and the other is halogen, lower alkyl, OH, lower alkanoyloxy, lower alkoxy, lower alkylmercapto, CF3, NO2, amino, lower alkanoylamino, lower alkoxycarbonylamino or phenyl, or two adjacent residues are methylenedioxy and the remainder are H. R3 is H or lower alkyl; R4 is H, lower alkyl, (lower alkoxy)-(lower alkyl), hydroxy-(lower alkyl), (lower alkylthio)-(lower alkyl), (lower alkylsulphinyl)-(lower alkyl), phenylthio(lower alkyl), phenylsulphinyl-(lower alkyl), lower alkenyl or halo-(lower alkenyl; or R3+R4 is -(CH2)n- in which n is 3 or 4; R5 is lower alkyl, (lower alkylthio)-lower alkyl), (lower alkoxy)-(lower alkyl), lower alkoxy, cycloalkyl, cycloalkyl-(lower alkyl), 2- or 3-furyl, 2- or 3-furyl-(CH2)m-, (m = 2, 3 or 4), 2- or 3-furyl or 2- or 3-(furyl)-(CH2)m- ring-substd. by 1-3 methyl gps., phenyl, phenyl-(CH2)m-, or phenyl or phenyl-(CH2)m- ring mono- or disubstd. by halogen, lower alkyl, OH, lower alkanoyloxy, lower alkoxy, lower alkylmercapto, CF3, amino and/or lower alkanoylamino, or methylenedioxyphenyl or -phenyl-(CH2)m-; and Alk is lower alkyl. (I) are useful as intermediates which are useful as analgesics and analgesic antagonists. Specific (I) is ethyl 3-(1-oxohexyl)-7-methoxy-1,4aalpha, 5alpha-trimethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo(g- )quinoline-3-carboxylate.
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