Patent ID: 6468958
Filing Date: 2002-10-22
Classification: A61K,A61Q,C07D,C08K

Abstract:
A biphenyl-substituted triazine compound of the formula in whichR1 is hydrogen; C1-C24alkyl or C5-C12cycloalkyl; or R1 is C1-C24alkyl or C5-C12cycloalkyl, each of which is substituted by halogen, â€”R4, â€”OR5, â€”N((R5)2, &boxH;NR5, &boxH;O, â€”CON(R5)2, â€”COR5, â€”COOR5, â€”OCOR5, â€”OCON(R5)2, â€”CN, â€”NO2, â€”SR5,â€”SOR5, â€”SO2R5, â€”P(O)(OR5)2, a morpholinyl, piperidyl, 2,2,6,6-tetramethylpiperidyl, piperazinyl or N-methylpiperazinyl-group, or combinations thereof; and/or R1 is C1-C24alkyl or C5-C12cycloalkyl which is interrupted by 1 to 6 phenylene, â€”Oâ€”, â€”NR5â€”, â€”CONR5â€”, â€”COOâ€”, â€”OCOâ€”, â€”CH(R5)â€”, â€”C(R5)2â€” or â€”COâ€” groups or combinations thereof; C2-C24alkenyl; halogen; â€”SR3, SOR3; SO2R3; â€”SO3H; â€”SO3M; or a radical of the formula R3 is C1-C20alkyl; C3-C18alkenyl; C5-C12cycloalkyl; C7-C15phenylalkyl; or C6-C12aryl which is unsubstituted or substituted by 1 to 3 C1-C4alkyl groups; R4 is C6-C12aryl; or C6-C12aryl which is substituted by halogen, C1-C8alkyl, C1-C8alkoxy or combinations thereof; C5-C12cycloalkyl; C7-C15phenylalkyl; or C7-C15phenylalkyl which is substituted in the phenyl ring by 1 to 3 halogen atoms, C1-C8alkyl, C1-C8alkoxy or combinations thereof or C2-C8alkenyl; R5 is R4; hydrogen; C1-C24alkyl; or a radical of the formula T is hydrogen; C1-C8alkyl; C2-C8alkyl which is substituted by hydroxyl or acyloxy; oxyl; hydroxyl; â€”CH2CN;, C1-C18alkoxy; C5-C12cycloalkoxy; C3-C6alkenyl; C7-C9phenylalkyl; C7-C9phenylalkyl which is substituted one, two or three times in the phenyl ring by C1-C4alkyl; or aliphatic C1-C8alkanoyl; R6 to R15 independently of one another are hydrogen; hydroxyl; â€”Câ‰¡N; C1-C20alkyl; C1-C20alkoxy; phenyl-C1-C20alkoxy; C7-C20phenylalkyl; C4-C12cycloalkyl; C4-C12cycloalkoxy; halogen; halo-C1-C5alkyl; carboxyl; acylamino; acyloxy; C1-C12alkoxycarbonyl; aminocarbonyl; â€”Oâ€”Y; or Oâ€”Z; or R11 and R12, together with the phenyl radical, form a cyclic radical containing 2 to 4 carbon atoms which is interrupted by oxygen or â€”NR5â€”; M is alkali metal; p 1 or 2; q is 0; if p is 1, X, Y and Z independently of one another are hydrogen; C3-C50alkyl which is interrupted by oxygen and/or substituted by R2 or OR2; ((CH2)mâ€”CH2â€”Oâ€”)nâ€”R2; â€”(CH2â€”CH((CH2)mâ€”R2)â€”Oâ€”)nâ€”Râ€²2; â€”(CH((CH2)mâ€”R2)â€”CH2â€”Oâ€”)nâ€”Râ€²2; â€”(CH2)nâ€”R2; â€ƒC4-C12cycloalkyl which is substituted by R2; â€”OR2-substituted C4-C12cycloalkyl; â€”CH((CH2)nâ€”R2)â€”COâ€”Oâ€”(CH2)mâ€”Râ€²2; â€”CH((CH2)nâ€”R2)â€”COâ€”(NRâ€²)â€”(CH2)mâ€”Râ€²2; â€”COâ€”(CH2)nâ€”R2; â€”COâ€”Oâ€”(CH2)nâ€”R2, â€”CH2â€”CH(â€”O(CO)â€”R2)â€”Râ€²2; â€”COâ€”NRâ€²â€”(CH2)nâ€”R2; C6-C12aryl; allyl; C4-C20alkenyl; C4-C20alkenyl which is interrupted by oxygen; C4-C12cycloalkenyl; C4-C12cycloalkenyl which is interrupted by oxygen; or C3-C20alkynyl; R2 and Râ€²2, independently of one another are Rx if attached to a carbon atom and are Ry 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; and X is C2-C12alkylene; â€”COâ€”(C2-C12alkylene)â€”COâ€”; CO-phenylene-COâ€”; CO-biphenylene-COâ€”; COâ€”Oâ€”(C2-C12alkylene)â€”Oâ€”COâ€”; â€”COâ€”O-phenylene-Oâ€”COâ€”; â€”COâ€”O-biphenylene-Oâ€”COâ€”; â€”COâ€”NRâ€²â€”(C2-C12alkylene)â€”NRâ€²â€”COâ€”; â€”COâ€”NRâ€²-phenylene-NRâ€²â€”COâ€”; â€”COâ€”NRâ€²-biphenylene-NRâ€²â€”COâ€”; â€”CH2â€”CH(OH)â€”CH2â€”; â€”CH2â€”CH(OR2)â€”CH2â€”; â€”CH2â€”CH(OH)â€”CH2â€”Oâ€”Dâ€”Oâ€”CH2â€”CH(OH)â€”CH2; â€”CH2â€”CH(OR2)â€”CH2â€”Oâ€”Dâ€”Oâ€”CH2â€”CH(OR2)â€”CH2â€”; D is C2-C12alkylene; C4-C50alkylene which is interrupted by oxygen; phenylene; biphenylene or phenylene-E-phenylene; E is â€”Oâ€”; â€”Sâ€”; â€”SO2â€”; â€”CH2â€”; â€”COâ€”; or â€”C(CH3)2â€”; Rx is hydrogen; hydroxyl; C1-C20alkyl; C4-C12cycloalkyl; C1-C20alkoxy; C4-C12cycloalkoxy; C4-C12cycloalkyl or C4-C12cycloalkoxy each of which is interrupted by oxygen; C6-C12aryl; pyridyl; pyrimidinyl; triazinyl; pyrrolyl; furyl; thiophenyl; quinolyl; â€”ORz; NHRz; Rz; CONRâ€²Râ€³; C2-C20alkenyl; C4-C12cycloalkenyl; C4-C12cycloalkenyl which is interrupted by oxygen; C3-C20alkynyl; 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, â€”NH2, â€”NHR5, â€”NR5Râ€²5, where Râ€²5 is defined as R5 above, halogen, C1-C20alkyl, C1-C20alkoxy, C4-C12cycloalkyl, C4-C12cycloalkoxy, C2-C20alkenyl, C4-C12cycloalkyl, C3-C20alkynyl, C6-C12aryl, C2-C18acylamino, C2-C18acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, methacrylamino, Ry is hydrogen; C1-C20alkyl; C4-C12cycloalkyl; C4-C12cycloalkyl which is interrupted by oxygen; C6-C12aryl; pyridyl; pyrimidinyl; triazinyl; pyrrolyl; furyl; thiophenyl; quinolyl; Rz; C2-C20alkenyl; C4-C12cycloalkenyl; C4-C12-cycloalkenyl which is interrupted by oxygen; or C3-C20alkynyl; or is any of the above alkyl, cycloalkyl, aryl, hetero-aryl, alkenyl, cycloalkenyl or alkynyl, which is substituted by hydroxyl, â€”NH2, â€”NHR5, â€”NR5Râ€²5, where Râ€²5 is defined as R5 above, halogen, C1-C20alkyl, C1-C20alkoxy, C4-C12cycloalkyl, C4-C12cycloalkoxy, C2-C20alkenyl, C4-C12cycloalkyl, C3-C20alkynyl, C6-C12aryl, C2-C18acylamino, C2-C18acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, methacrylamino, Rz is â€”CORâ€²; â€”COORâ€²; â€”CONRâ€²Râ€³; â€”COâ€”CH&boxH;CH2; â€”COâ€”C(CH3)&boxH;CH2; Râ€² and Râ€³ independently of one another are hydrogen; C1-C20alkyl; C4-C50alkyl which is interrupted by oxygen; C4-C12cycloalkyl; C4-C12cycloalkyl which is interrupted by oxygen; C2-C20alkenyl; C4-C20alkenyl which is interrupted by oxygen; or C6-C12aryl; or are any of the above alkyl, O-interrupted alkyl, cycloalkyl, O-interrupted cycloalkyl, alkenyl, O-interrupted alkenyl, aryl, which is substituted by hydroxyl, â€”NH2, â€”NHR5, â€”NR5Râ€²5, where Râ€²5 is defined as R5 above, halogen, C1-C20alkyl, C1-C20alkoxy, C4-C12cycloalkyl, C4-C12cycloalkoxy, C2-C20alkenyl, C4-C12cycloalkyl, C3-C20alkynyl, C6-C12aryl, C2-C18acylamino, C2-C18acyloxy, carboxyl, acryloxy, acrylamino, methacryloxy, â€ƒand with the proviso that the compound 2-(2-hydroxyphenyl)-4-phenyl-6-(1-biphenyl)-1,3,5-triazine is not included; and with the proviso that R12 and R13 are not hydroxyl or allyloxy.