Patent ID: 6255483
Filing Date: 2001-07-03
Classification: A61K,A61Q,C07D,C08K

Abstract:
A biphenyl-substituted triazine compound of the formula ##STR53##in whichR.sub.1 is hydrogen; C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.12 cycloalkyl; or R.sub.1 is C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.12 cycloalkyl, each of which is substituted by halogen, --R.sub.4, --OR.sub.5, --N((R.sub.5).sub.2, .dbd.NR.sub.5, .dbd.O, --CON(R.sub.5).sub.2, --COR.sub.5, --COOR.sub.5, --OCOR.sub.5, --OCON(R.sub.5).sub.2, --CN, --NO.sub.2, --SR.sub.5, --SOR.sub.5, --SO.sub.2 R.sub.5, --P(O)(OR.sub.5).sub.2, a morpholinyl, piperidyl, 2,2,6,6-tetramethylpiperidyl, piperazinyl or N-methylpiperazinyl-group, or combinations thereof; and/or R.sub.1 is C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.12 cycloalkyl which is interrupted by 1 to 6 phenylene, --O--, --NR.sub.5 --, --CONR.sub.5 --, --COO--, --OCO--, --CH(R.sub.5)--, --C(R.sub.5).sub.2 -- or --CO-- groups or combinations thereof; C.sub.2 -C.sub.24 alkenyl; halogen; --SR.sub.3, SOR.sub.3 ; SO.sub.2 R.sub.3 ; --SO.sub.3 H; --SO.sub.3 M; or a radical of the formula ##STR54##R.sub.3 is C.sub.1 -C.sub.20 alkyl; C.sub.3 -C.sub.18 alkenyl; C.sub.5 -C.sub.12 cycloalkyl; C.sub.7 -C.sub.15 phenylalkyl; or C.sub.6 -C.sub.12 aryl which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;R.sub.4 is C.sub.6 -C.sub.12 aryl; or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy or combinations thereof; C.sub.5 -C.sub.12 cycloalkyl; C.sub.7 -C.sub.15 phenylalkyl; or C.sub.7 -C.sub.15 phenylalkyl which is substituted in the phenyl ring by 1 to 3 halogen atoms, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy or combinations thereof or C.sub.2 -C.sub.8 alkenyl;R.sub.5 is R.sub.4 ; hydrogen; C.sub.1 -C.sub.24 alkyl; or a radical of the formula ##STR55##T is hydrogen; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.8 alkyl which is substituted by hydroxyl or acyloxy; oxyl; hydroxyl; --CH.sub.2 CN; C.sub.1 -C.sub.18 alkoxy; C.sub.5 -C.sub.12 cycloalkoxy; C.sub.3 -C.sub.6 alkenyl; C.sub.7 -C.sub.9 phenylalkyl; C.sub.7 -C.sub.9 phenylalkyl which is substituted one, two or three times in the phenyl ring by C.sub.1 -C.sub.4 alkyl; or aliphatic C.sub.1 -C.sub.8 alkanoyl;R.sub.6 to R.sub.15 independently of one another are hydrogen; hydroxyl; --C.ident.N; C.sub.1 -C.sub.20 alkyl; C.sub.1 -C.sub.20 alkoxy; phenyl-C.sub.1 -C.sub.20 alkoxy; C.sub.7 -C.sub.20 phenylalkyl; C.sub.4 -C.sub.12 cycloalkyl; C.sub.4 -C.sub.12 cycloalkoxy; halogen; halo-C.sub.1 -C.sub.5 alkyl; carboxyl; acylamino; acyloxy; C.sub.1 -C.sub.12 alkoxycarbonyl; aminocarbonyl; --O--Y; or O--Z; or R.sub.11 and R.sub.12, together with the phenyl radical, form a cyclic radical containing 2 to 4 carbon atoms which is interrupted by oxygen or --NR.sub.5 --;M is alkali metal;p 1 or 2;q is 1;if p is 1,X, Y and Z independently of one another are hydrogen; C.sub.3 -C.sub.50 alkyl which is interrupted by oxygen and/or substituted by R.sub.2 or OR.sub.2 ; ((CH.sub.2).sub.m --CH.sub.2 --O--).sub.n --R.sub.2 ; --(CH.sub.2 --CH.sub.2).sub.m --R.sub.2)--O--).sub.n --R'.sub.2 ; --(CH((CH.sub.2).sub.m --R.sub.2)--CH.sub.2 --O--).sub.n --R'.sub.2 ; --(CH.sub.2).sub.n --R.sub.2 ; ##STR56##C.sub.4 -C.sub.12 cycloalkyl which is substituted by R.sub.2 ; --OR.sub.2 -substituted C.sub.4 -C.sub.12 cycloalkyl; --CH((CH.sub.2).sub.n --R.sub.2)--CO--O--(CH.sub.2).sub.m --R'.sub.2 ; --CH((CH.sub.2).sub.n --R.sub.2)--CO--(NR')--(CH.sub.2).sub.m --R'.sub.2 ; --CO--(CH.sub.2).sub.n --R.sub.2 ; --CO--O--(CH.sub.2).sub.n --R.sub.2, --CH.sub.2 --CH(--O(CO)--R.sub.2)--R'.sub.2 ; --CO--NR'--(CH.sub.2).sub.n --R.sub.2 ; C.sub.6 -C.sub.12 aryl; allyl; C.sub.4 -C.sub.20 alkenyl; C.sub.4 -C.sub.20 alkenyl which is interrupted by oxygen; C.sub.4 -C.sub.12 cycloalkenyl; C.sub.4 -C.sub.12 cycloalkenyl which is interrupted by oxygen; or C.sub.3 -C.sub.20 alkynyl;R.sub.2 and R'.sub.2, independently of one another are R.sub.x if attached to a carbon atom and are R.sub.y if attached to an atom other than carbon;n 0 to 20;m 0 to 20;and, if p is 2,Y and Z, independently of one another are as defined for when p is 1; andX is C.sub.2 -C.sub.12 alkylene; --CO--(C.sub.2 -C.sub.12 alkylene)-CO--; --CO-phenylene-CO--; CO-biphenylene-CO--; CO--O--(C.sub.2 -C.sub.12 alkylene)-O--CO--; --CO--O-phenylene-O--CO--; --CO--O-biphenylene-O--CO--; --CO--NR'--(C.sub.2 -C.sub.12 alkylene)-NR'--CO--; --CO--NR'-phenylene-NR'--CO--; --CO--NR'-biphenylene-NR'--CO--; --CH.sub.2 --CH(OH)--CH.sub.2 --; --CH.sub.2 --CH(OR.sub.2)--CH.sub.2 --; --CH.sub.2 --CH(OH)--CH.sub.2 --O--CH.sub.2 --CH(OH)--CH.sub.2 ; --CH.sub.2 --CH(OR.sub.2)--CH.sub.2 --O--D--O--CH.sub.2 --CH(OR.sub.2)--CH.sub.2 --;D is C.sub.2 -C.sub.12 alkylene; C.sub.4 -C.sub.50 alkylene which is interrupted by oxygen; phenylene; biphenylene or phenylene-E-phenylene;E is --O--; --S--; --SO.sub.2 --; --CH.sub.2 --; --CO--; or --C(CH.sub.3).sub.2 --;R.sub.x is hydrogen; hydroxyl; C.sub.1 -C.sub.20 alkyl; C.sub.4 -C.sub.12 cycloakyl; C.sub.1 -C.sub.20 alkoxy; C.sub.4 -C.sub.12 cycloalkoxy; C.sub.4 -C.sub.12 cycloalkyl or C.sub.4 -C.sub.12 cycloalkoxy each of which is interrupted by oxygen; C.sub.6 -C.sub.12 aryl; pyridyl; pyrimidinyl; triazinyl; pyrrolyl; furyl; thiophenyl; quinolyl; --OR.sub.z ; NHR.sub.z ; R.sub.z ; CONR'R""; C.sub.2 -C.sub.20 alkenyl; C.sub.4 -C.sub.12 cycloalkenyl; C.sub.4 -C.sub.12 cycloalkenyl which is interrupted by oxygen; C.sub.3 -C.sub.20 alkynyl; or is any of the above alkyl, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, oxygen interrupted cycloalkyl or cycloalkenyl or cycloalkoxy, aryl, heteroaryl, alkenyl or alkynyl which is substituted by hydroxyl, --NH.sub.2, --NHR.sub.5, --NR.sub.5 R'.sub.5, where R'.sub.5 is defined as R.sub.5 above, halogen, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.4 -C.sub.12 cycloalkyl, C.sub.4 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.20 alkenyl, C.sub.4 -C.sub.12 cycloalkyl, C.sub.3 -C.sub.20 alkynyl, C.sub.6 -C.sub.12 aryl, C.sub.2 -C.sub.18 acylamino, C.sub.2 -C.sub.18 acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, methacrylamino, ##STR57##R.sub.y is hydrogen; C.sub.1 -C.sub.20 alkyl; C.sub.4 -C.sub.12 cycloalkyl; C.sub.4 -C.sub.12 cycloalkyl which is interrupted by oxygen; C.sub.6 -C.sub.12 aryl; pyridyl; pyrimidinyl; triazinyl; pyrrolyl; furyl; thiophenyl; quinolyl; R.sub.z ; C.sub.2 -C.sub.20 alkenyl; C.sub.4 -C.sub.12 -cycloalkenyl; C.sub.4 -C.sub.12 -cycloalkenyl which is interrupted by oxygen; or C.sub.3 -C.sub.20 alkynyl; or is any of the above alkyl, cycloalkyl, aryl, hetero-aryl, alkenyl, cycloalkenyl or alkynyl, which is substituted by hydroxyl, --NH.sub.2, --NHR.sub.5, --NR.sub.5 R'.sub.5, where R'.sub.5 is defined as R.sub.5 above, halogen, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.4 -C.sub.12 cycloalkyl, C.sub.4 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.20 alkenyl, C.sub.4 -C.sub.12 cycloalkyl, C.sub.3 -C.sub.20 alkynyl, C.sub.6 -C.sub.12 aryl, C.sub.2 -C.sub.18 acylamino, C.sub.2 -C.sub.18 acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, methacrylamino, ##STR58##R.sub.z is --COR'; --COOR'; --CONR'R""; --CO--CH.dbd.CH.sub.2 ; --CO--C(CH.sub.3).dbd.CH.sub.2 ; R' and R"" independently of one another are hydrogen; C.sub.1 -C.sub.20 alkyl; C.sub.4 -C.sub.50 alkyl which is interrupted by oxygen; C.sub.4 -C.sub.12 cycloalkyl; C.sub.4 -C.sub.12 cycloalkyl which is interrupted by oxygen; C.sub.2 -C.sub.20 alkenyl; C.sub.4 -C.sub.20 alkenyl which is interrupted by oxygen; or C.sub.6 -C.sub.12 aryl; or are any of the above alkyl, O-interrupted alkyl, cycloalkyl, O-interrupted cycloalkyl, alkenyl, O-interrupted alkenyl, aryl, which is substituted by hydroxyl, --NH.sub.2, --NHR.sub.5, --NR.sub.5 R'.sub.5, where R'.sub.5 is defined as R.sub.5 above, halogen, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkoxy, C.sub.4 -C.sub.12 cycloalkyl, C.sub.4 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.20 alkenyl, C.sub.4 -C.sub.12 cycloalkyl, C.sub.3 -C.sub.20 alkynyl, C.sub.6 -C.sub.12 aryl, C.sub.2 -C.sub.18 acylamino, C.sub.2 -C.sub.18 acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, methacrylamino, ##STR59##and with the proviso that the compound 2-(2-hydroxyphenyl)-4-phenyl-6-(1-biphenyl)-1,3,5-triazine is not included.