Patent ID: 6294532
Filing Date: 2001-09-25
Classification: A61P,C07D

Abstract:
A compound of the formula I: ##STR43##wherein:ring Z is a 6-membered heterocyclic ring containing 1 to 3 nitrogen atoms with the proviso that the group at the 4-position of the quinazoline ring is not a substituted or unsubstituted group selected from 4,5,7-triazaoxindol-3-yl and 4,6,7-triazaoxindol-3-yl;R.sup.1 represents hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxymethyl, di(C.sub.1-4 alkoxy)methyl or C.sub.1-4 alkanoyl;R.sup.2 represents hydroxy, halogeno, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkanoyloxy, trifluoromethyl, 2,2,2-trifluoroethyl, cyano, amino, nitro, C.sub.2-4 alkanoyl, C.sub.1-4 alkanoylamino, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, carbamoyl, N-C.sub.1-4 alkylcarbamoyl, N,N-di(C.sub.1-4 alkyl)carbamoyl, aminosulphonyl,N-C.sub.1-4 alkyl-aminosulphonyl, N,N-di(C.sub.1-4 alkyl)aminosulphonyl orC.sub.1-4 alkylsulphonylamino or R.sup.2 is selected from one of the following four groups:1) R.sup.4 X.sup.1 wherein X.sup.1 represents a direct bond, --O--, --NR.sup.5 --, C.sub.1-3 alkyl, C.sub.2-4 alkanoyl, --CONR.sup.6 R.sup.7 --, --SO.sub.2 NR.sup.8 R.sup.9 -- or --SO.sub.2 R.sup.10 -- (wherein R.sup.5, R.sup.6 and R.sup.8, each independently represents hydrogen or C.sub.1-2 alkyl and R.sup.7, R.sup.9 and R.sup.10 each independently represents C.sub.1-4 alkyl and wherein R.sup.4 is linked to R.sup.7, R.sup.9 or R.sup.10) and R.sup.4 represents phenyl or a 5 or 6-membered heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may be saturated or unsaturated and which phenyl or heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C.sub.1-4 alkoxycarbonyl;2) X.sup.2 C.sub.2-4 alkylX.sup.3 C.sub.1-3 alkyl (wherein X.sup.2 is --O-- or --NR.sup.11 -- (wherein R.sup.11 is hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and X.sup.3 is --O--, --NR.sup.12 --, --S--, --SO-- or --SO.sub.2 -- (wherein R.sup.12 is hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl);3) C.sub.1-2 alkylX.sup.4 C.sub.2-3 alkylX.sup.5 C.sub.1-3 alkyl (wherein X.sup.4 and X.sup.5 which may be the same or different are each --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.13 -- (wherein R.sup.13 is hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl); and4) C.sub.1-3 alkylX.sup.6 C.sub.1-3 alkyl (wherein X.sup.6 is --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.14 -- (wherein R.sup.14 is hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl);n is an integer from 0 to 3;m is an integer from 0 to 4; andR.sup.3 represents hydroxy, halogeno, nitro, trifluoromethyl, C.sub.1-3 alkyl, cyano, amino or R.sup.15 X.sup.7, wherein X.sup.7 represents a direct bond, --O--, --CH.sub.2 --, --S--, --SO--, --SO.sub.2 --, --NR.sup.16 CO--, --CONR.sup.17 --, --SO.sub.2 NR.sup.18 --, --NR.sup.19 SO.sub.2 -- or --NR.sup.20 -- (wherein R.sup.16, R.sup.17, R.sup.18, R.sup.19 and R.sup.20 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl), and R.sup.15 is selected from one of the following seventeen groups:1) hydrogen or C.sub.1-5 alkyl which may be unsubstituted or which may be substituted with one or more groups selected from hydroxy, fluoro and amino;2) C.sub.1-5 alkylX.sup.8 COR.sup.21, wherein X.sup.8 represents --O-- or --NR.sup.22 -- (in which R.sup.22 represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.22 represents C.sub.1-3 alkyl, --NR.sup.23 R.sup.24 -- or --OR.sup.25 -- (wherein R.sup.23, R.sup.24 and R.sup.25 which may be the same or different each represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl);3) C.sub.1-5 alkylX.sup.9 R.sup.26, wherein X.sup.9 represents --O--, --S--, --SO--, --SO.sub.2 --, --OCO--, --NR.sup.27 CO--, --CONR.sup.28 --, --SO.sub.2 NR.sup.29 --, --NR.sup.30 SO.sub.2 -- or --NR.sup.31 -- (wherein R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.26 represents hydrogen, C.sub.1-3 alkyl, cyclopentyl, cyclohexyl or a 5 or 6-membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which C.sub.1-3 alkyl group may bear one or two substituents selected from oxo, hydroxy, halogeno and C.sub.1-4 alkoxy and which cyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl and C.sub.1-4 alkoxy;4) C.sub.1-5 alkylX.sup.10 C.sub.1-5 alkylX.sup.11 R.sup.32, wherein X.sup.10 and X.sup.11 which may be the same or different are each --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.33 CO--, --CONR.sup.34 --, --SO.sub.2 NR.sup.35 --, --NR.sup.36 SO.sub.2 -- or --NR.sup.37 -- (wherein R.sup.33, R.sup.34, R.sup.35, R.sup.36 and R.sup.37 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.32 represents hydrogen or C.sub.1-3 alkyl;5) R.sup.38, wherein R.sup.38 is a 5 or 6-membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl and C.sub.1-4 alkoxy;6) C.sub.1-5 alkylR.sup.38, wherein R.sup.38 is as defined herein;7) C.sub.2-5 alkenylR.sup.38, wherein R.sup.38 is as defined herein;8) C.sub.2-5 alkynylR.sup.38, wherein R.sup.38 is as defined herein;9) R.sup.39, wherein R.sup.39 represents a pyridone group, a phenyl group or a 5 or 6-membered aromatic heterocyclic group with 1 to 3 heteroatoms selected from O, N and S, which pyridone, phenyl or heterocyclic group may carry up to 5 substituents selected from hydroxy halogeno, amino, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 hydroxyalkyl, C.sub.1-4 aminoalkyl, C.sub.1-4 alkylamino, C.sub.1-4 hydroxyalkoxy, carboxy, trifluoromethyl, cyano, --CONR.sup.40 R.sup.41 and --NR.sup.42 COR.sup.43 -- (wherein R.sup.40, R.sup.41, R.sup.42 and R.sup.43, which may be the same or different, each represents hydrogen, C.sub.1-4 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl);10) C.sub.1-5 alkylR.sup.39, wherein R.sup.39 is as defined herein;11) C.sub.2-5 alkenylR.sup.39, wherein R.sup.39 is as defined herein;12) C.sub.2-5 alkynylR.sup.39, wherein R.sup.39 is as defined herein;13) C.sub.1-5 alkylX.sup.12 R.sup.39, wherein X.sup.12 represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.44 CO--, --CONR.sup.45 --, --SO.sub.2 NR.sup.46 --, --NR.sup.47 SO.sub.2 -- or --NR.sup.48 -- (wherein R.sup.44, R.sup.45, R.sup.46, R.sup.47 and R.sup.48 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.39 is as defined herein;14) C.sub.2-5 alkenylX.sup.13 R.sup.39, wherein X.sup.13 represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.49 CO--, --CONR.sup.50 --, --SO.sub.2 NR.sup.51 --, --NR.sup.52 SO.sub.2 -- or --NR.sup.53 -- (wherein R.sup.49, R.sup.50, R.sup.51, R.sup.52 and R.sup.53 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.39 is as defined herein;15) C.sub.2-5 alkynylX.sup.14 R.sup.39, wherein X.sup.14 represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.54 CO--, --CONR.sup.55 --, --SO.sub.2 NR.sup.56 --, --NR.sup.57 SO.sub.2 -- or --NR.sup.58 -- (wherein R.sup.54, R.sup.55, R.sup.56, R.sup.57 and R.sup.58 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.39 is as defined herein;16) C.sub.1-3 alkylX.sup.15 C.sub.1-3 alkylR.sup.39, wherein X.sup.15 represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.59 CO--, --CONR.sup.60 --, --SO.sub.2 NR.sup.61 --, --NR.sup.62 SO.sub.2 -- or --NR.sup.63 -- (wherein R.sup.59, R.sup.60, R.sup.61, R.sup.62 and R.sup.63 each independently represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxyC.sub.2-3 alkyl) and R.sup.39 is as defined herein); and17) C.sub.1-3 alkylX.sup.15 C.sub.1-3 alkylR.sup.38, wherein X.sup.15 and R.sup.38 are as defined herein;and salts thereof.