Patent ID: 6172078
Filing Date: 2001-01-09
Classification: C07D

Abstract:
A quinolinomorphinan compound or pharmacologically acceptable acid addition salt thereof represented by the following formula (II): ##STR138##wherein R.sup.1 is represents hydrogen, alkyl having 1 to 5 carbon atoms, cycloalkylalkyl having 4 to 7 carbon atoms, cycloalkenylalkyl having 5 to 7 carbon atoms, aryl having 6 to 12 carbon atoms, aralkyl having 7 to 13 carbon atoms, alkenyl having 2 to 7 carbon atoms, alkanoyl having 1 to 5 carbon atoms, furan-2-ylalkyl (wherein an alkyl moiety has 1 to 5 carbons atoms), or thiophene-2-ylalkyl (wherein an alkyl moiety has 1 to 5 carbon atoms);R.sup.2 and R.sup.3 independently represent hydrogen, hydroxy, alkoxy having 1 to 5 carbon atoms, alkanoyloxy having 1 to 5 carbon atoms, aralkyloxy having 7 to 13 carbon atoms, or arylcarbonyloxy having 7 to 13 carbon atoms;m represents an integer of 0 to 4;R.sup.5 is each of m substituents on the benzene ring, which independently represent R.sup.18, or two R.sup.5 substituted at adjacent carbons form together a fused ring structure A (wherein residual 0 to 2 substituents R.sup.5 independently represent R.sup.18 or another fused ring structure A);the fused ring structure A is a benzo, indeno, naphtho, pyrido, or cycloalkeno having 5 to 7 carbon atoms, which is substituted by 0 to 4 substituents R.sup.9, or unsubstituted dioxoleno;R.sup.9 and R.sup.18 (1) independently represent fluoro, chloro, bromo, iodo, nitro, hydroxy, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, isothiocyanato, trifluoromethyl, trifluoromethoxy, cyano, phenyl, hydroxyalkyl having 1 to 3 carbon atoms, SR.sup.6, SOR.sup.6, SO.sub.2 R.sup.6, (CH.sub.2).sub.k CO.sub.2 R.sup.7, SO.sub.2 NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, (CH.sub.2).sub.k NR.sup.7 R.sup.8, or (CH.sub.2).sub.k N(R.sup.7)COR.sup.8 (wherein k represents an integer of 0 to 5, R.sup.6 represents alkyl having 1 to 5 carbon atoms, and R.sup.7 and R.sup.8 independently represent hydrogen, alkyl having 1 to 5 carbon atoms, or cycloalkylalkyl having 4 to 6 carbon atoms), and/or (2) R.sup.9 and R.sup.18 substituted at adjacent carbons with a ring junction therebetween form together any one of ethano, propano and o-benzeno bridged structures R.sup.9 --R.sup.18 ;R.sup.4 represents hydrogen, alkyl having 1 to 5 carbon atoms, hydroxyalkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms (which may be substituted by at least one substituent R.sup.17), NR.sup.10 R.sup.11, OR.sup.12 COOR.sup.13 or CONR.sup.14 R.sup.15, or any one of bridged structures R.sup.4 --R.sup.5 of N(R.sup.16)CO, N(R.sup.16)C(.dbd.NH), N(R.sup.16)CH.sub.2, o-benzeno, ethano, propano, and butano, which are formed together by R.sup.4 and R.sup.5 substituted at the peri position;R.sup.17 represents fluoro, chloro, bromo, iodo, nitro, amino, hydroxy, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, alkanoyloxy having 1 to 5 carbon atoms, trifluoromethyl, trifluoromethoxy or cyano;R.sup.10, R.sup.11, R.sup.12 and R.sup.16 independently represent hydrogen, alkyl having 1 to 5 carbon atoms, cycloalkylalkyl having 4 to 7 carbon atoms, aralkyl having 7 to 13 carbon atoms, or alkanoyl having 1 to 5 carbon atoms; and R.sup.13, R.sup.14 and R.sup.15 independently represent hydrogen, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, or aralkyl having 7 to 13 carbon atoms; (wherein when R.sup.4 is hydrogen, and (1) when m is 1, R.sup.5 is R.sup.18 which represents hydroxy, and (2) when m is an integer of 2 to 4, R.sup.5 is R.sup.18 at least one of which represents hydroxy, or two R.sup.5 form together a fused ring structure A, and the residual 0 to 2 R.sup.5 independently represent R.sup.18 (wherein when the fused ring structure A is benzo, pyrido, or cycloalkeno having 5 to 7 carbon atoms, at least one R.sup.18 represents hydroxy, or at least one R.sup.9 and one R.sup.18 substituted at adjacent carbons with ring junction therebetween form together a bridged structure R.sup.9 --R.sup.18 which is any one of ethano, propano and o-benzeno), or must form another fused ring structure A); andformula (II) includes (+) form, (-) form and (.+-.) form.