quinoxaline

Examples of starting compounds of the formula (22) are 4-aminobenzimidazolin-2-one, 5-aminobenzimidazolin-2-one, 1-N-(4'-sulfophenyl)-5-aminobenzimidazolin-2-one, 1-N-(3'-sulfophenyl)-5-aminobenzimidazolin-2-one, 1-N-(6',8'-disulfonaphth-2'-yl)-5-aminobenzimidazolin-2-one, 6-aminoquinoxaline-2,3-dione, 7-methyl-6-aminoquinoxaline-2,3-dione, 7-methoxy-6-aminoquinoxaline-2,3-dione, 7-ethoxy-6-aminoquinoxaline-2,3-dione, 4-N-(4'-sulfophenyl)-6-amino-quinoxaline-2,3-dione, 4-N-(3'-sulfophenyl)-6-aminoquinoxaline-2,3-dione, 4-N-(2',5'-disulfophenyl)-6-aminoquinoxaline-2,3-dione, 4-N-(6',8'-disulfonaphth-2'-yl)-6-aminoquinoxaline-2,3-dione, 4-N-(4',6',8'-trisulfonaphth-2'-yl)-6-aminoquinoxaline-2,3-dione, 5-aminooxazoline-2-one, 6-chloro-5-aminooxazolin-2-one, 6-amino-quinazoline-2,4-dione, 7-aminoquinazolin-2,4-dione, 7-amino-3,4-dihydro-quinolin-2-one, 6-amino-1,3-dihydroindol-2-one, 5-amino- 1,2-benzisothiazolin-3-one 1 ,1-dioxide, 6-amino- 1,2-benzisothiazolin-3-one 1,1-dioxide, 5-aminophthalimide, 5-amino-N'-(4'-sulfophenyl)phthalimide, 5-amino-N'-(3'-sulfophenyl)phthalimide, 5-amino-N'-(5',7'-disulfo-naphth-2'-yl)phthalimide, 5-amino-N'-(6',8'-disulfonaphth-2'-yl)-phthalimide, 7-aminochinolin-2-one, 7-amino-4-methylquinolin-2-one, 7-amino-4-ethylquinolin-2-one, 7-amino-4-phenylquinolin-2-one, 4-(N-methyl)aminobenzimidazolin-2-one, 4- N-(?-sulfoethyl)amino!-benzimidazolin-2-one, 7-(N-ethylamino)quinolin-2-one and 7-(N-ethyl-amino)-3,4-dihydroquinolin-2-one.

Ausgangsverbindungen der allgemeinen Formel (22) sind beispielsweise 4-Amino-benzimidazolin-2-on, 5-Amino-benzimidazolin-2-on, 1-N-(4'-Sulfophenyl)-5-amino-benzimidazolin-2-on, 1-N-(3'-Sulfophenyl)-5-amino-benzimidazolin-2-on, 1-N-(6',8'-Disulfo-naphth-2'-yl)-5-amino-benzimidazolin-2-on, 6-Amino-chinoxalin-2,3-dion, 7-Methyl-6-amino-chinoxalin-2,3-dion, 7-Methoxy-6-amino-chinoxalin-2,3-dion, 7-Ethoxy-6-amino-chinoxalin-2,3-dion, 4-N-(4'-Sulfophenyl)-6-amino-chinoxalin-2,3-dion, 4-N-(3'-Sulfophenyl)-6-amino-chinoxalin-2,3-dion, 4-N-(2',5'-Disulfophenyl)-6-amino-chinoxalin-2,3-dion, 4-N-(6',8'-Disulfo-naphth-2'-yl)-6-amino-chinoxalin-2,3-dion, 4-N-(4',6',8'-Trisulfo-naphth-2'-yl)-6-amino-chinoxalin-2,3-dion, 5-Amino-oxazolin-2-on, 6-Chlor-5-amino-oxazolin-2-on, 6-Amino-chinazolin-2,4-dion, 7-Amino-chinazolin-2,4-dion, 7-Amino-3,4-dihydro-chinolin-2-on, 6-Amino-1,3-dihydro-indol-2-on, 5-Amino-1,2-benzisothiazolin-3-on-1,1-dioxid, 6-Amino-1,2-benzisothiazolin-3-on-1,1-dioxid, 5-Amino-phthalimid, 5-Amino-N'-(4'-Sulfophenyl)-phthalimid, 5-Amino-N'-(3'-sulfophenyl)-phthalimid, 5-Amino-N'-(5',7'-disulfo-naphth-2'-yl)-phthalimid, 5-Amino-N'-(6',8'-disulfo-naphth-2'-yl)-phthalimid, 7-Amino-chinolin-2-on, 7-Amino-4-methyl-chinolin-2-on, 7-Amino-4-ethyl-chinolin-2-on, 7-Amino-4-phenyl-chinolin-2-on, 4-(N-Methyl)-amino-benzimidazolin-2-on, 4-[N-(?-Sulfoethyl)-amino]-benzimidazolin-2-on, 7-(N-Ethyl-amino)-chinolin-2-on und 7-(N-Ethyl-amino)-3,4-dihydro-chinolin-2-on.

The compound of claim 1, which is: a) 4-(4-phenoxyanilino)benzo[g]quinoline-3-carbonitrile, b) 4-(3-chloro-4-fluoroanilino)-benzo[g]quinoline-3-carbonitrile, c) 4-(4-chloro-5-methoxy-2-methylanilino)benzo[g]quinoline-3-carbonitrile, d) 7,8-dimethoxy-4-(4-phenoxyanilino)benzo[g]quinoline-3-carbonitrile, e) 4-(4-chloro-5-methoxy-2-methylanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile, f) 4-(3-chloro-4-fluoroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonibrile, g) 4-(2,4-dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile, h) 4-(2,4-dichloroanilino)-7,8-dihydroxybenzo[g]quinoline-3-carbonitrile, i) 8-(3,4,5-trimethoxyanilino)-3H-[1,2,3]triazolo[4,5-g]quinoline-7-carbonitrile, j) 9-(4-chloro-5-methoxy-2-methylanilino)pyrido[2,3-g]quinoxaline-8-carbonitrile, k) 8-(5-methoxy-2-methylanilino)-2-{[2-(4-morpholinyl)ethyl]amino}imidazo[4,5-g]quinoline-7-carbonitrile, l) 2-{[2-(4-morpholinyl)ethyl]amino}-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, m) 2-amino-8-(4-phenoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, n) 8-(3-bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile, o) 8-(2-bromo-4-chlorophenylamino)imidazo[4,5-g]quinoline-7-carbonitrile, p) 8-(2-bromo4-chloro-5-medioxyphenyhmino)imidazo[4,5-g]quinoline-7-carbonitrile, q) 8-(2-chloro-5-methoxyphenylamino)imidazo[4,5-g]quinoline-7-carbonitrile, r) 8-(3-hydroxy-4-methylphenylamino)imidazo[4,5-g]quinoline-7-carbonitrile, s) 8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, t) 8-(4-phenoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, u) 2-(chloromethyl)-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, v) 2-(4-morpholinylmethyl)-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]quinoline-7-carbonitrile, w) 844-Woro-5-methoxy-2-methylanilino)-3-[2-(4-morpholinyl)ethyl]-3H-imidazo[4,5-g]quinoline-7-carbonitrile, x) 3-[2-(4-morpholinyl)ethyl]-8-(4-phenoxyanilino)-3H-imidazo[4,5-g]quinoline-7-carbonitrile, y) 8-[(4-chloro-5-methoxy-2-methylphenyl)amino]-thiazolo[4,5-g]quinolino-7-carboiutrile, z) 4-(3-bromophenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, aa) 4-(4-chloro-2-fluorophenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, bb) 4-(2,4-dichlorophenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, cc) 4-(2,4-dichloro-5-methoxyphenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, dd) 4-(4-phenoxyphenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, ee) 4-(3-hydroxy-4-methylphenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, ff) 4-(4-chloro-2-fluorophenoxy)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, gg) 4-(4-chloro-5-methoxy-2-methylphenylamino)-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, hh) 8-amino-4-(4-chloro-5-methoxy-2-methylanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile, ii) 4-(3-bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile, jj) 6-amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile, kk) 4-(3-bromophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile, ll) 4-(4-chloro-2-fluorophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile, mm) 4-(3-hydroxy-4-methylphenylamino)benzo[4,5]furo[3,2-b]pyridine-3-cabonitrile, nn) 4-(4-phenoxyphenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile, oo) 4-(4-chloro-2-fluorophenoxy)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile, pp) 4-(2,4-dichloroanilino)-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile, qq) 4-(3-bromoanilino)-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile, rr) 8-amino-4-(3-bromoanilino)[1]benzotheno[3,2]pyridine-3-carbonitrile, ss) N-[4-(3-bromoanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-8-yl]acrylamide, tt) N-[4-(3-bromoanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-6-yl]acrylamide, uu) 4-(2,4-dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile, vv) 4-(2,4-dichloroanilino)-8-methoxybenzo[g]quinoline-3-carbonitrile, ww) 4-(2,4-dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile, xx) 4-(2,4-dichloroanilino)-8-hydroxybenzo[g]quinoline-3-carbonitrile, yy) 4-(2,4-dichloroanilino)-7-[2-(dimethylamino)ethoxy] benzo[g]quinoline-3-carbonitrile, zz) 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile, aaa) 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile, bbb) 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-molpholinyl)ethoxy]benzo[g]quinohne-3-carbomtnle, ccc) 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ddd) 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile, eee) 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile, fff) 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ggg) 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, hhh) 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, iii) 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, jjj) 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, kkk) 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, lll) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, mmm) 8-(2-Chloroethoxy)4-[3-cbloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxybenzo[g]quinoline-3-carbonitrile, nnn) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, ooo) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-8-(3-chloropropoxy)-7-methoxybenzo[g]quinoline-3-carbonitrile, ppp) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(3-morpholin-4-yl-propoxy)benzo[g]quinoline-3-carbonitrile, qqq) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-[2-(4-methylpiperazin-1-yl)ethoxy]-benzo[g]quinoline-3-carbonitrile, rrr) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-[1,2,3]triazol-2-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, sss) 4-[3-Chloro-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-[1,2,3]triazol-1-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, ttt) 4-(2,4-Dichloro-5-methoaryphenylamino)-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, uuu) 8-(3-Chloropropoxy)-4-(2,4-dichloro-5-methoxyphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile, vvv) 4-(2,4-Dichloro-5-methoxyphenylamino)-7-methoxy-8-(3-morpholin-4-yl-propoxy)benzo[g]quinoline-3-carbonitrile, www) 4-(2,4-Dichloro-5-methoxyphenylamino)-7-methoxy-8-(2-[1,2,3]triazol-2-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, xxx) 4-(2,4-Dichloro-5-methoxyphenylamino)-7-methoxy-8-(2-[1,2,3]triazol-1-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, yyy) 4-(2,4-Dichloro-5-methoxyanilino)-7,8-dimethoxybenzo[b] [1,8]naphthyridine-3-carbonitrile, zzz) 8-(2-Chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile, aaaa) 4-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile, bbbb) 8-(2-Chloroethoxy)-4-{3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]anilino}-7-methoarybenzo[b][1,8]naphthyridine-3-carbonitrile, cccc) 4-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile, dddd) 4-{3-Chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]amlino}-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile, eeee) 4-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[b] [1,8]naphthyridine-3-carbonitrile, ffff) 8-(2-Chloroethoxy)-4-(4-chloro-5-methoxy-2-methylanilino)-7-ethoxybenzo[g]quinoline-3-carbonibrile, gggg) 8-(2-Chloroethoxy)-4-(2-chloro-4-fluoro-5-methoxyanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile, hhhh) 7-(2-Chloroethoxy)-4-(2-chloro-4-fluoro-5-methoxyanilino)-8-methoxybenzo[g]quinoline-3-carbonitrile, iiii) 8-(2-Chloroethoxy)-4-(2-chloro-5-methoxy-4-methylphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile, jjjj) 7-(2-Chloroethoxy)-4-(2-chloro-5-methoxy-4-methylphenylamino)-8-methoxybenzo[g]quinoline-3-carbonitrile, kkkk) 7-(2-Chloroethoxy)-4-(3-chloro-4-fluoroanilino)-8-methoxybenzo[g]quinoline-3- carbonitrile, llll) 8-(2-Chloroethoxy)-4-(3-chloro-4-fluoroanilino)-7-methoacybenzo[g]quinoline-3-carbonitrile, mmmm) 4-(4-Benzyloxy-3-chlorophenylamino)-7-(2-chloroethoxy)-8-methoxybenzo[g]quinoline-3-carbonitrile, nnnn) 4-(4-Benzyloxy-3-chlorophenylamino)-8-(2-chloroethoxy)-7-methoxybenzo[g]quinoline-3-carbonitrile, oooo) 7-(2-Chloroethoxy)-4-(3-chloro-4-phenoxyphenylamino)-8-methoxybenzo[g]quinoline-3-carbonitrile, pppp) 8-(2-Chloroethoxy)-4-(3-cbloro-4-phenoxyphenylamino)-7-methoxybenzo[g]quinoline-3-carbonitrile, qqqq) 4-(4-Chloro-5-methoxy-2-methylanilino)-8-ethoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, mr) 4-(4-Chloro-5methoxy-2methylanilino)-7-ethoxy-8-[2-(4-mozphoHnyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ssss) ({2[4-(4-Chloro-5-methoxy-2-methylphenylamino)-3-cyano-8-ethoxybenzo[g]quinoline-7-yloxy]-ethyl}-ethoxycarbonylmethyl-amino)-acetic acid ethyl ester, tttt) ({2-[4-(4-Chloro-5-methoxy-2-methylphenylamino)-3-cyano-7-ethoxybenzo[g]quinoline-8-yloxy]-ethyl}-ethoxycarbonylmethylamino)-acetic acid ethyl ester, uuuu) 2-(Carbamoylmethyl-{2-[4-{4-chloro-5-methoxy-2-methylphenylamino)-3-cyano-7-ethoxybenzo[g]quinolin-8-yloxy]-ethyl}-amino)-acetamide, vvvv) 4-(2,4-Dichloroanilino)-7-methoxy-8-[2-(4-moipholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, wwww) 4-(2,4-Dichloroanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, xxxx) 8-Methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]quinoline-3-carbonitrile, yyyy) 7-Methoxy-8-[2-(4-methyl-1 piperazinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]quinoline-3-carbonitrile, zzzz) 7-Methoxy-8-[2-(4-morpholinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]quinoline-3-carbonitrile, aaaaa) 8-Methoxy-7-[2-(4-morpholinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]quinoline-3-carbonitrile, bbbbb) 4-(2-Chloro-4-fluoro-5-methoxyanilino)-8-methoxy-7-[2(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ccccc) 4-(2-Chloro-5-methoxy-4-methylanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ddddd) 4-(2-Chloro-5-methoxy-4-methylanilino)-7-methoxy-8-[2-(4-methyl-I- piperazinyl)ethoxy]benzo[g]quinoliue-3-carbonitrile, eeeee) 4-(2,4-Dichloro-5-methoxyanilino)-7-[2-(4-hydroxy-1-piperidinyl)ethoxy]-8- methoxybenzo[g]quinoline-3-carbonitrile, fffff) 4-(3-Chloro-4-fluoroanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, ggggg) 4-(2,4-Dichloro-5-methoxyanilino)-8-[2-(4-hydroxy-1-piperidinyl)ethoxy]-7- methoxybenzo[g]quinoline-3-carbonitrile, hhhhh) 4-(2-Chloro-5-methoxy-4-methylanivino)-8-methoxy-7-[2-(4-hydroxy-1-piperidinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, iiiii) 4-(2-Chloro-5-methoxy-4-methylanilino)-7-methoxy-8-[2-(4-hydroxy-1-piperidinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, jjjjj) 4-(2-Chloro-4-fluoro-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, kkkkk) 4-(2-Chloro-4-fluoro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, lllll) 4-(2-Chloro-4-fluoro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1- piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, mmmmm) 4-(3-Chloro-4-fluoroanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile, nnnnn) 4-(3-Chloro-4-pheaoxyphenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, ooooo) 4-(3-Chloro-4-phenoxyphenylamino)-8-methoxy-7-(2-morpholin4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, ppppp) 4-(2-Chloro-5-methoxy-4-methylphenylamino)-8-methoxy-7-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, qqqqq) 4-(2-Chloro-5-methoxy-4-methylphenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, rrrrr) 4-(4-Benzyloxy-3-chlorophenylamino)-8-methoxy-7-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, sssss) 4-(4-Benzyloxy-3-chlorophenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile, ttttt) 8-(Benzyloxy)-4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-7-methoxybenzo[g]quinoline-3-caibonitrile, uuuuu) 4-[(2-Chloro-4-fluoro-5-methoxyphenyl)amino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, or a pharmaceutically acceptable salt thereof.

Verbindung nach Anspruch 1, die Folgendes ist: a) 4-(4-Phenoxyanilino)benzo[g]chinolin-3-carbonitril, b) 4-(3-Chlor-4-fluoranilino)benzo[g]chinolin-3-carbonitril, c) 4-(4-Chlor-5-methoxy-2-methylanilino)benzo[g]chinolin-3-carbonitril, d) 7,8-Dimethoxy-4-(4-phenoxyanilino)benzo[g]chinolin-3-carbonitril, e) 4-(4-Chlor-5-methoxy-2-methylanilino)-7,8-dimethoxybenzo[g]chinolin-3-carbonitril, f) 4-(3-Chlor-4-fluoranilino)-7,8-dimethoxybenzo[g]chinolin-3-carbonitril, g) 4-(2,4-Dichloranilino)-7,8-dimethoxybenzo[g]chinolin-3-carbonitril, h) 4-(2,4-Dichloranilino)-7,8-dihydroxybenzo[g]chinolin-3-carbonitril, i) 8-(3,4,5-Trimethoxyanilino)-3H-[1,2,3]triazolo[4,5-g]chinolin-7-carbonitril, j) 9-(4-Chlor-5-methoxy-2-methylanilino)pyrido[2,3-g]chinoxalin-8-carbonitril, k) 8-(5-Methoxy-2-methylanilino)-2-{[2-(4-morpholinyl)ethyl]amino}imidazo[4,5-g]chinolin-7-carbonitril, l) 2-{[2-(4-Morpholinyl)ethyl]amino}-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, m) 2-Amino-8-(4-phenoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, n) 8-(3-Bromphenylamino)imidazo[4,5-g]chinolin-7-carbonitril, o) 8-(2-Brom-4-chlorphenylamino)imidazo[4,5-g]chinolin-7-carbonitril, p) 8-(2-Brom-4-chlor-5-methoxyphenylamino)imidazo[4,5-g]chinolin-7-carbonitril, q) 8-(2-Chlor-5-methoxyphenylamino)imidazo[4,5-g]chinolin-7-carbonitril, r) 8-(3-Hydroxy-4-methylphenylamino)imidazo[4,5-g]chinolin-7-carbonitril, s) 8-(3,4,5-Trimethoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, t) 8-(4-Phenoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, u) 2-(Chlormethyl)-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, v) 2-(4-Morpholinylmethyl)-8-(3,4,5-trimethoxyanilino)imidazo[4,5-g]chinolin-7-carbonitril, w) 8-(4-Chlor-5-methoxy-2-methylanilino)-3-[2-(4-morpholinyl)ethyl]-3 H -imidazo[4,5-g]chinolin-7-carbonitril, x) 3-[2-(4-Morpholinyl)ethyl]-8-(4-phenoxyanilino)-3H-imidazo[4,5-g]chinolin-7-carbonitril, y) 8-[(4-Chlor-5-methoxy-2-methylphenyl)amino]-thiazolo[4,5-g]chinolin-7-carbonitril, z) 4-(3-Bromphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, aa) 4-(4-Chlor-2-fluorphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, bb) 4-(2,4-Dichlorphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, cc) 4-(2,4-Dichlor-5-methoxyphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, dd) 4-(4-Phenoxyphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, ee) 4-(3-Hydroxy-4-methylphenylamino)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, ff) 4-(4-Chlor-2-fluorphenoxy)benzo[4,5]thieno[3,2-b]pyridin-3-carbonitril, gg) 4-(4-Chlor-5-methoxy-2-methylphenylamino)-8-nitrobenzo[4,5]thieno-[3,2-b]pyridin-3-carbonitril, hh) 8-Amino-4-(4-chlor-5-methoxy-2-methylanilino)[1]benzothieno[3,2-b]pyridin-3-carbonitril, ii) 4-(3-Bromanilino)-6-nitro[1]benzothieno[3,2-b]pyridin-3-carbonitril, jj) 6-Amino-4-(3-bromanilino)[1]benzothieno[3,2-b]pyridin-3-carbonitril, kk) 4-(3-Bromphenylamino)benzo[4,5]furo[3,2-b]pyridin-3-carbonitril, ll) 4-(4-Chlor-2-fluorphenylamino)benzo[4,5]furo[3,2-b]pyridin-3-carbonitril, mm) 4-(3-Hydroxy-4-methylphenylamino)benzo[4,5]furo[3,2-b]pyridin-3-carbonitril, nn) 4-(4-Phenoxyphenylamino)benzo[4,5]furo[3,2-b]pyridin-3-carbonitril, oo) 4-(4-Chlor-2-fluorphenoxy)benzo[4,5]furo[3,2-b]pyridin-3-carbonitril, pp) 4-(2,4-Dichloranilino)-8-nitro[1]benzothieno[3,2-b]pyridin-3-carbonitril, qq) 4-(3-Bromanilino)-8-nitro[1]benzothieno[3,2-b]pyridin-3-carbonitril, rr) 8-Amino-4-(3-bromanilino)[1]benzothieno[3,2-b]pyridin-3-carbonitril, ss) N-[4-(3-Bromanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-8-yl]acrylamid, tt) N-[4-(3-Bromanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-6-yl]acrylamid, uu) 4-(2,4-Dichloranilino)-7-methoxybenzo[g]chinolin-3-carbonitril, vv) 4-(2,4-Dichloranilino)-8-methoxybenzo[g]chinolin-3-carbonitril, ww) 4-(2,4-Dichloranilino)-7-hydroxybenzo[g]chinolin-3-carbonitril, xx) 4-(2,4-Dichloranilino)-8-hydroxybenzo[g]chinolin-3-carbonitril, yy) 4-(2,4-Dichloranilino)-7-[2-(dimethylamino)ethoxy]benzo[g]chinolin-3-carbonitril, zz) 4-(4-Chlor-5-methoxy-2-methylanilino)-7-methoxy-8-(chlorethoxy)benzo[g]chinolin-3-carbonitril, aaa) 4-(4-Chlor-5-methoxy-2-methylanilino)-8-methoxy-7-(chlorethoxy)benzo[g]chinolin-3-carbonitril, bbb) 4-(4-Chlor-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ccc) 4-(4-Chlor-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ddd) 4-(2,4-Dichlor-5-methoxyanilino)-7-methoxy-8-(chlorethoxy)benzo[g]chinolin-3-carbonitril, eee) 4-(2,4-Dichlor-5-methoxyanilino)-8-methoxy-7-(chlorethoxy)benzo[g]chinolin-3-carbonitril, fff) 4-(2,4-Dichlor-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ggg) 4-(2,4-Dichlor-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, hhh) 4-(2,4-Dichlor-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, iii) 4-(2,4-Dichlor-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, jjj) 4-(4-Chlor-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, kkk) 4-(4-Chlor-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, lll) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-8-hydroxy-7-methoxybenzo[g]chinolin-3-carbonitril, mmm) 8-(2-Chlorethoxy)-4-[3-chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxybenzo[g]chinolin-3-carbonitril, nnn) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, ooo) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-8-(3-chlorpropoxy)-7-methoxybenzo[g]chinolin-3-carbonitril, ppp) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(3-morpholin-4-yl-propoxy)benzo[g]chinolin-3-carbonitril, qqq) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-[2-(4-methylpiperazin-1-yl)ethoxy]-benzo[g]chinolin-3-carbonitril, rrr) 4-[3-Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-[1,2,3]triazol-2-yl-ethoxy)benzo[g]chinolin-3-carbonitril, sss) 4-[3[Chlor-4-(1-methyl-1 H -imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-[1,2,3]triazol-1-yl-ethoxy)benzo[g]chinolin-3-carbonitril, ttt) 4-(2,4-Dichlor-5-methoxyphenylamino)-8-hydroxy-7-methoxybenzo[g]chinolin-3-carbonitril, uuu) 8-(3-Chlorpropoxy)-4-(2,4-dichlor-5-methoxyphenylamino)-7-methoxybenzo[g]chinolin-3-carbonitril, vvv) 4-(2,4-Dichlor-5-methoxyphenylamino)-7-methoxy-8-(3-morpholin-4-yl-propoxy)benzo[g]chinolin-3-carbonitril, www) 4-(2,4-Dichlor-5-methoxyphenylamino)-7-methoxy-8-(2-[1,2,3]triazol-2-yl-ethoxy)benzo[g]chinolin-3-carbonitril, xxx) 4-(2,4-Dichlor-5-methoxyphenylamino)-7-methoxy-8-(2-[1,2,3]triazol-1-yl-ethoxy)benzo[g]chinolin-3-carbonitril, yyy) 4-(2,4-Dichlor-5-methoxyanilino)-7,8-dimethoxybenzo[b][1,8]naphthyridin-3-carbonitril, zzz) 8-(2-Chlorethoxy)-4-(2,4-dichlor-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridin-3-carbonitril, aaaa) 4-(2,4-Dichlor-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridin-3-carbonitril, bbbb) 8-(2-Chlorethoxy)-4-{3-chlor-4-[(1-methyl-1 H -imidazol-2-yl)sulfanyl]anilino}-7-methoxybenzo[b][1,8]naphthyridin-3-carbonitril, cccc) 4-(2,4-Dichlor-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[b][1,8]naphthyridin-3-carbonitril, dddd) 4-{3-Chlor-4-[(1-methyl-1 H -imidazol-2-yl)sulfanyl]anilino}-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridin-3-carbonitril, eeee) 4-(2,4-Dichloranilino)-7,8-dimethoxybenzo[b][1,8]naphthyridin-3-carbonitril, ffff) 8-(2-Chlorethoxy)-4-(4-chlor-5-methoxy-2-methylanilino)-7-ethoxybenzo[g]chinolin-3-carbonitril, gggg) 8-(2-Chlorethoxy)-4-(2-chlor-4-fluor-5-methoxyanilino)-7-methoxybenzo[g]chinolin-3-carbonitril, hhhh) 7-(2-Chlorethoxy)-4-(2-chlor-4-fluor-5-methoxyanilino)-8-methoxybenzo[g]chinolin-3-carbonitril, iiii) 8-(2-Chlorethoxy)-4-(2-chlor-5-methoxy-4-methylphenylamino)-7-methoxybenzo[g]chinolin-3-carbonitril, jjjj) 7-(2-Chlorethoxy)-4-(2-chlor-5-methoxy-4-methylphenylamino)-8-methoxybenzo[g]chinolin-3-carbonitril, kkkk) 7-(2-Chlorethoxy)-4-(3-chlor-4-fluoranilino)-8-methoxybenzo[g]chinolin-3-carbonitril, llll) 8-(2-Chlorethoxy)-4-(3-chlor-4-fluoranilino)-7-methoxybenzo[g]chinolin-3-carbonitril, mmmm) 4-(4-Benzyloxy-3-chlorphenylamino)-7-(2-chlorethoxy)-8-methoxybenzo[g]chinolin-3-carbonitril, nnnn) 4-(4-Benzyloxy-3-chlorphenylamino)-8-(2-chlorethoxy)-7-methoxybenzo[g]chinolin-3-carbonitril, oooo) 7-(2-Chlorethoxy)-4-(3-chlor-4-phenoxyphenylamino)-8-methoxybenzo[g]chinolin-3-carbonitril, pppp) 8-(2-Chlorethoxy)-4-(3-chlor-4-phenoxyphenylamino)-7-methoxybenzo[g]chinolin-3-carbonitril, qqqq) 4-(4-Chlor-5-methoxy-2-methylanilino)-8-ethoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, rrrr) 4-(4-Chlor-5-methoxy-2-methylanilino)-7-ethoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ssss) ({2[4-(4-Chlor-5-methoxy-2-methylphenylamino)-3-cyano-8-ethoxybenzo[g]chinolin-7-yloxy]-ethyl}-ethoxycarbonylmethyl-amino)-essigsäureethylester, tttt) ({2-[4-(4-Chlor-5-methoxy-2-methylphenylamino)-3-cyano-7-ethoxybenzo[g]chinolin-8-yloxy]-ethyl}ethoxycarbonylmethylamino)-essigsäureethylester, uuuu) 2-(Carbamoylmethyl-{2-[4-(4-chlor-5-methoxy-2-methylphenylamino)-3-cyano-7-ethoxybenzo[g]chinolin-8-yloxy]-ethyl}-amino)-acetamid, vvvv) 4-(2,4-Dichloranilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, wwww) 4-(2,4-Dichloranilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, xxxx) 8-Methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]chinolin-3-carbonitril, yyyy) 7-Methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]chinolin-3-carbonitril, zzzz) 7-Methoxy-8-[2-(4-morpholinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]chinolin-3-carbonitril, aaaaa) 8-Methoxy-7-[2-(4-morpholinyl)ethoxy]-4-(3,4,5-trimethoxyanilino)benzo[g]chinolin-3-carbonitril, bbbbb) 4-(2-Chlor-4-fluor-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ccccc) 4-(2-Chlor-5-methoxy-4-methylanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ddddd) 4-(2-Chlor-5-methoxy-4-methylanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, eeeee) 4-(2,4-Dichlor-5-methoxyanilino)-7-[2-(4-hydroxy-1-piperidinyl)ethoxy]-8-methoxybenzo[g]chinolin-3-carbonitril, fffff) 4-(3-Chlor-4-fluoranilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, ggggg) 4-(2,4-Dichlor-5-methoxyanilino)-8-[2-(4-hydroxy-1-piperidinyl)ethoxy]-7-methoxybenzo[g]chinolin-3-carbonitril, hhhhh) 4-(2-Chlor-5-methoxy-4-methylanilino)-8-methoxy-7-[2-(4-hydroxy-1-piperidinyl)ethoxy]benzo[g]chinolin-3-carbonitril, iiiii) 4-(2-Chlor-5-methoxy-4-methylanilino)-7-methoxy-8-[2-(4-hydroxy-1-piperidinyl)ethoxy]benzo[g]chinolin-3-carbonitril, jjjjj) 4-(2-Chlor-4-fluor-5-methoxyanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, kkkkk) 4-(2-Chlor-4-fluor-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, lllll) 4-(2-Chlor-4-fluor-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]chinolin-3-carbonitril, mmmmm) 4-(3-Chlor-4-fluoranilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]chinolin-3-carbonitril, nnnnn) 4-(3-Chlor-4-phenoxyphenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, ooooo) 4-(3-Chlor-4-phenoxyphenylamino)-8-methoxy-7-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, ppppp) 4-(2-Chlor-5-methoxy-4-methylphenylamino)-8-methoxy-7-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, qqqqq) 4-(2-Chlor-5-methoxy-4-methylphenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, rrrrr) 4-(4-Benzyloxy-3-chlorphenylamino)-8-methoxy-7-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, sssss) 4-(4-Benzyloxy-3-chlorphenylamino)-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]chinolin-3-carbonitril, ttttt) 8-(Benzyloxy)-4-[(2-chlor-4-fluor-5-methoxyphenyl)amino]-7-methoxybenzo[g]chinolin-3-carbonitril, uuuuu) 4-[(2-Chlor-4-fluor-5-methoxyphenyl)amino]-8-hydroxy-7-methoxybenzo[g]chinolin-3-carbonitril, oder ein pharmazeutisch annehmbares Salz davon.

Het, which is selected from the group pyridine, pyrimidine, pyrazine, quinoline, benzimidazole, benzothiazole, isoquinoline, chromane, isochromane, cinnoline, quinazoline, quinoxaline, phthalazine, pyridoimidazoles, pyrroline, pyrrolidine, tetrahydropyridine, indazole, piperidine, imidazolidine, 1,3-oxazolidine, 4,5-dihydro-1,3-thiazole, 1,3-thiazolidine, piperazine, indoline, isoindoline, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and wherein Het is unsubstituted or mono-, di- or trisubstituted independently of one another by R ; A compound of the formula I as claimed in one or more of claims 1 to 4, wherein the compound of the formula I is 3-(2-Amino-6-methyl-pyrimidin-4-ylamino)-N-(4-amino-2-methyl-quinolin-6-yl)-propionamide, 2-Amino-4-[3-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-phenylamino]-1,6-dimethyl-pyrimidin-1-ium, 2-Amino-4-[4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-benzylamino]-1,6-dimethyl-pyrimidin-1-ium, Pyrazine-2-carboxylic acid 4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)- benzylamide, 6-Amino-N-[4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-benzyl]-nicotinamide, 6-Pyrrolidin-1-yl-pyrazine-2-carboxylic acid 4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)- benzylamide, 2-Amino-4-[(4-([(4-amino-2-methyl-6-quinolinyl)carbonyl]amino) phenyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(3-{[(4-amino-2-methyl-6-quinolinyl)carbonyl]amino}phenyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(4-{([(4-amino-2-methyl-6-quinolinyl)carbonyl]amino}benzyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(4-{[(4-amino-2-methyl-6-quinolinyl)carbonyl]amino}benzyl)amino]-6-methylpyrimidine, 4-Amino-N-[4-({[(6-chloro-3-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-quinolinecarboxamide, 4-Amino-2-methyl-N-(4-{[(2-pyridinylcarbonyl)amino]methyl}phenyl)-6-quinolinecarboxamide, 4-Amino-N-[4-({[(2-chloro-4-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-quinolinecarboxamide, 4-Amino-N-[4-({[(3-bromo-5-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-quinolinecarboxamide, 4-Amino-N-[4-({[(3-amino-2-pyrazinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-[(2-pyridinylcarbonyl)amino]phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-{4-[(3-pyridinylcarbonyl)amino]phenyl}-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-chloro-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(5-bromo-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-3-pyrazinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4- {[(2-amino-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-hydroxy-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-pyrazinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2,3-dichloro-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[3-(aminosulfonyl)-4-chlorobenzoyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-{4-[(3-dimethylaminobenzoyl)amino]phenyl}-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-methyl-1H-benzimidazol-5-yl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[4-(4-piperidinytoxy) benzoyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-1H-benzimidazol-5-yl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-1,2-benzthiazol-6-yl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-amino-N-{4-[(1H-benzimidazol-5-ylcarbonyl)amino]phenyl}-2- methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-6-quinolinyl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{[(2-amino-6-quinolinyl)carbonyl]amino}-2-methoxyphenyl)-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(2-methoxy-4-{[(2-methyl-1H-benzimidazol-5-yl)carbonyl]amino}phenyl)-2-methyl-6-quinolinecarboxamide, 1,4-Di- {[(3-amino-2-methylquinolin-6-yl)carbonyl]amino}benzene, 4-Amino-N- {4-[(1H-indazol-6-ylamino)methyl]phenyl}-2-methyl-6-quinolinecarboxamide, 4-Amino-N-(4-{([(2-amino-1,3-benzothiazol-6-yl)carbonyl]amino}cyclohexyl)-2-methyl-6-quinolinecarboxamide or 4-Amino-N-(4- {[(2-amino-6-quinolinyl)carbonyl]amino} cyclohexyl)-2-methyl-6-quinolinecarboxamide.

(C -C )-Cycloalkyl, D ist -NH-CO-, -CO-NH- oder -NH-; E ist 1. ein unsubstiuiertes oder unabhängig voneinander mit R mono-, di- oder trisubstituiertes Aryl ausgewählt aus der Gruppe Phenyl, Naphthyl, Biphenylyl, Fluorenyl und Anthracenyl, oder 2. ein unsubstituiertes oder unabhängig voneinander mit R mono-, di- oder trisubstituiertes Het ausgewählt aus der Gruppe Aziridin, Oxiran, Azetidin, Pyrrol, Furan, Thiophen, Dioxol, Imidazol, Pyrazol, Oxazol, Isoxazol, Thiazol, Isothiazol, 1,2,3-Triazol, 1,2,4-Triazol, Pyridin, Pyran, Thiopyran, Pyridazin, Pyrimidin, Pyrazin, 1,4-Dioxin, 1,2-Oxazin, 1,3-Oxazin, 1,4-Oxazin, 1,2-Thiazin, 1,3-Thiazin, 1,4-Thiazin, 1,2,3-Triazin, 1,2,4-Triazin, 1,3,5-Triazin, Azepin, 1,2-Diazepin, 1,3-Diazepin, 1,4-Diazepin, Indol, Isoindol, Benzofuran, Benzothiophen, 1,3-Benzodioxol, Benzo[1,4]dioxin, 4H-Benzo[1,4]oxazin, Indazol, Benzimidazol, Benzoxazol, Benzthiazol, Chinolin, Isochinolin, Chroman, Isochroman, Cinnolin, Chinazolin, Chinoxalin, Phthalazin, Pyridoimidazole, Pyridopyridine, Pyridopyrimidine oder Ringsysteme, die durch Annelieren oder Kondensieren der aufgelisteten Heterozyklen mit einem carbozyklischen Ring entstehen, wie z.B. benzo-annellierte, cyclopenta-annellierte, cyclohexa-annellierte oder cyclohepta-annellierte Derivate dieser Heterozyklen, Pyrrolin, Pyrrolidin, Tetrahydrofuran, Tetrahydrothiophen, Dihydropyridin, Tetrahydropyridin, Piperidin, 1,3-Dioxolan, 2-Imidazolin, Imidazolidin, 4,5-Dihydro-1,3-oxazol, 1,3-Oxazolidin, 4,5-Dihydro-1,3-thiazol, 1,3-Thiazolidin, Perhydro-1,4-dioxan, Piperazin, Perhydro-1,4-oxazin (= Morpholin), 2,3-Dihydrobenzo[1,4]dioxin, Indolin, Isoindolin, 3,4-Dihydro-2H-benzo[1,4]oxazin, Perhydro-1,4-thiazin, Perhydroazepin, 1,2,3,4-Tetrahydrochinolin, 1,2,3,4-Tetrahydroisochinolin Verbindung der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 3, wobei n ist die ganze Zahl 0 oder 1; m ist die ganze Zahl 0 oder 1; o ist die ganze Zahl 0 oder 1; R1 ist Methyl; R2 ist Amino; A ist -NH-CO- oder -CO-NH-; B ist Phenyl, wobei Phenyl unsubstituiert oder mono-, di- oder trisubstituiert, unabhängig voneinander mit R 3 ist, D ist -NH-CO-, -CO-NH- oder -NH-; E ist 1. Phenyl, wobei Phenyl unsubstituiert oder mono-, di- oder trisubstituiert, unabhängig voneinander durch R ist, oder 2. ein unsubstituiertes oder unabhängig voneinander mit R mono-, di- oder trisubstituiertes Het ist, das ausgewählt ist aus der Gruppe Pyridin, Pyrimidin, Pyrazin, Chinolin, Benzimidazol, Benzothiazol, Isochinolin, Chroman, Isochroman, Cinnolin, Chinazolin, Chinoxalin, Phthalazin, Pyridoimidazolen, Pyrrolin, Pyrrolidin, Tetrahydropyridin, Indazol, Piperidin, Imidazolidin, 1,3-Oxazolidin, 4,5-Dihydro-1,3-thiazol, 1,3-Thiazolidin, Piperazin, Indolin, Isoindolin, 1,2,3,4-Tetrahydrochinolin, 1,2,3,4-Tetrahydroisochinolin Verbindung der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4, wobei die Verbindung der Formel I ist 3-(2-Amino-6-methyl-pyrimidin-4-ylamino)-N-(4-amino-2-methyl-chinol in-6-yl)-propionamid, 2-Amino-4-[3-(4-amino-2-methyl-chinolin-6-ylcarbamoyl)-phenylamino]-1,6-dimethyl-pyrimidin-1-ium, 2-Amino-4-[4-(4-amino-2-methyl-chinolin-6-ylcarbamoyl)-benzylamino]-1,6-dimethyl-pyrimidin-1-ium, Pyrazin-2-carbonsäure-4-(4-amino-2-methyl-chinolin-6-ylcarbamoyl)-benzylamid, 6-Amino-N-[4-(4-amino-2-methyl-chinolin-6-ylcarbamoyl)-benzyl]-nicotinamid, 6-Pyrrolidin-1-yl-pyrazin-2-carbonsäure-4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-benzylamid, 2-Amino-4-[(4-{[(4-amino-2-methyl-6-chinolinyl)carbonyl]amino} phenyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(3-{[(4-amino-2-methyl-6-chinolinyl)carbonyl]amino}phenyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(4-{[(4-amino-2-methyl-6-chinolinyl)carbonyl]amino}benzyl)amino]-1,6-dimethylpyrimidin-1-ium, 2-Amino-4-[(4-{[(4-amino-2-methyl-6-chinolinyl)carbonyl]amino}benzyl)amino]-6-methylpyrimidin, 4-Amino-N-[4-({[(6-chloro-3-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-chinolincarbonsäureamid, 4-Amino-2-methyl-N-(4-{[(2-pyridinylcarbonyl)amino]methyl}phenyl)-6-chinolincarbonsäureamid, 4-Amino-N-[4-({[(2-chloro-4-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-[4-({[(3-bromo-5-pyridinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-[4-({[(3-amino-2-pyrazinyl)carbonyl]amino}methyl)phenyl]-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-{4-[(2-pyridinylcarbonyl)amino]phenyl}-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-{4-[(3-pyridinylcarbonyl)amino]phenyl}-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-chloro-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäuream id, 4-Amino-N-(4-{[(5-bromo-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-3-pyrazinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-3-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-hydroxy-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-pyrazinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2,3-dichloro-5-pyridinyl)carbonyl]amino}phenyl)-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-(4-{[3-(aminosulfonyl)-4-chlorobenzoyl]amino}phenyl)-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-{4-[(3-dimethylaminobenzoyl)amino]phenyl}-2-methyl-6-chinoline carbonsäureamid, 4-Amino-N-(4-{[(2-methyl-1H-benzimidazol-5-yl)carbonyl]amino} phenyl)-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-(4-{[4-(4-piperidinyloxy) benzoyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-1H-benzimidazol-5-yl)carbonyl]amino}phenyl)-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-1,2-benzthiazol-6-yl)carbonyl]amino}phenyl)-2-methyl-6-chinolincarbonsäureamid, 4-amino-N-{4-[(1H-benzimidazol-5-ylcarbonyl)amino]phenyl}-2- methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-6-chinolinyl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-6-chinolinyl)carbonyl]amino}-2-methoxyphenyl)-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-(2-methoxy-4-{[(2-methyl-1H-benzimidazol-5-yl)carbonyl]amino}phenyl)-2-methyl-6- chinolincarbonsäureamid, 1,4-Di-{ [(3-amino-2-methylchinolin-6-yl)carbonyl]amino}benzol, 4-Amino-N-{4-[(1H-indazol-6-ylamino)methyl]phenyl}-2-methyl-6-chinolincarbonsäureamid, 4-Amino-N-(4-{[(2-amino-1,3-benzothiazol-6-yl)carbonyl]amino}cyclohexyl)-2-methyl-6- chinolincarbonsäureamid, oder 4-Amino-N-(4-{[(2-amino-6-chinolinyl)carbonyl]amino}cyclohexyl)-2-methyl-6-chinolincarbonsäureamid.

Process according to Claim 1 and/or 2, characterised in that the alkyl, aryl or heteroaryl radicals R1 and R2 denote methyl, ethyl, propyl, iso -propyl, butyl, iso -butyl, sec -butyl, tert -butyl, cyclopentyl, cyclohexyl, cycloheptyl, N-methylpiperazinyl, morpholino and substituted or unsubstituted benzene, naphthalene, anthracene, pyrene, biphenyl, fluorene, spiro-9,9'-bifluorene, phenanthrene, triptycene; pyridine, furan, thiophene, pyrrole, quinoline, quinoxaline, pyrimidine and pyrazine.

Verfahren gemäß Anspruch 1 und / oder 2, dadurch gekennzeichnet, daß die Alkyl-, Aryl- bzw. Heteroarylreste R1 und R2 Methyl-, Ethyl-, Propyl-, iso -Propyl-, Butyl-, iso -Butyl-, sec -Butyl-, tert -Butyl-, Cyclopentyl-, Cyclohexyl-, Cycloheptyl-, N-Methylpiperazinyl-, Morpholino- und und substituiertes oder unsubstituiertes Benzol, Naphthalin, Anthracen, Pyren, Biphenyl, Fluoren, Spiro-9,9'-bifluoren, Phenanthren, Triptycen, Pyridin, Furan, Thiophen, Pyrrol, Chinolin, Chinoxalin, Pyrimidin und Pyrazin bedeuten.

Het selected from the group aziridine, oxirane, azetidine, pyrrole, furan, thiophene, dioxole, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, 1,2,3-triazole, 1,2,4-triazole, pyridine, pyran, thiopyran, pyridazine, pyrimidine, pyrazine, 1,4-dioxine, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, 1,2-thiazine, 1,3-thiazine, 1,4-thiazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, azepine, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, indole, isoindole, benzofuran, benzothiophene, 1,3-benzodioxole, benzo[1,4]dioxine, 4H-benzo[1,4]oxazine, indazole, benzimidazole, benzoxazole, benzothiazole, quinoline, isoquinoline, chromane, isochromane, cinnoline, quinazoline, quinoxaline, phthalazine, pyridoimidazoles, pyridopyridines, pyridopyrimidines or ring systems which result from the listed heterocycles by fusion or condensation of a carbocyclic ring, for example benzo-fused, cyclopenta-fused, cyclohexa-fused or cyclohepta-fused derivatives of these heterocycles, pyrroline, pyrrolidine, tetrahydrofuran, tetrahydrothiophene, dihydropyridine, tetrahydropyridine, piperidine, 1,3-dioxolane, 2-imidazoline, imidazolidine, 4,5-dihydro-1,3-oxazol, 1,3-oxazolidine, 4,5-dihydro-1,3-thiazole, 1,3-thiazolidine, perhydro-1,4-dioxane, piperazine, perhydro-1,4-oxazine (= morpholine), 2,3-dihydrobenzo[1,4]dioxine, indoline, isoindoline, 3,4-dihydro-2H-benzo[1,4]oxazine, perhydro-1,4-thiazine, perhydroazepine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and wherein Het is unsubstituted or mono-, di- or trisubstituted independently of one another by R ; R is A compound of the formula I as claimed in one or more of claims 1 to 3, wherein n is the integer zero or 1, m is the integer zero or 1, o is the integer zero or 1, R1 is methyl; R2 is amino; A is -NH-CO- or -CO-NH-; B is phenyl, wherein phenyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R 3 , D is -NH-CO-, -CO-NH- or -NH-; E is 1. phenyl, wherein phenyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R , or 2.

Verbindung der Formel I gemäß Anspruch 1, wobei n ist die ganze Zahl 0 oder 1; m ist die ganze Zahl 0 oder 1; o ist die ganze Zahl 0 oder 1; R1 ist -(C 1 -C 4 )-Alkyl; R2 ist -NR 4 R 5 , wobei R 4 und R 5 identisch oder unterschiedlich sind und ein Wasserstoffatom oder -(C 1 -C 4 )-Alkyl sind; A ist -NH-CO- oder -CO-NH-; B ist 1. eine kovalente Bindung, 2. ein monozyklisches oder bizyklisches, 6- bis 14-gliedriges unsubstituiertes oder unabhängig voneinander mit R mono-, di- oder trisubstituiertes Aryl oder 3.

Agent according to Claim 1, characterized in that the reactive carbonyl compound of the general formulae B1-B17 is chosen from benzaldehyde, 4-methoxybenzaldehyde, 4-hydroxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 2,5-dimethoxybenzaldehyde, 3-hydroxy-4-methoxybenzaldehyde, 4-nitrobenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 4-(dimethylamino)benzaldehyde, (2 E )-3-[4-(dimethylamino)phenyl]-2-propenal, 2,4,6-trihydroxybenzaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methylisonicotine aldehyde, all-trans-retinal, 3,5-dioxo-1,2-diphenyl-4-pyrazolidinecarbaldehyde, (2 E ,4 E )-5-phenyl-2,4-pentadienal, pentanedial, 4-(methylsulphanyl)benzaldehyde, 1-naphthaldehyde, (2 E )-3-(4-nitrophenyl)-2-propenal, 3-phenoxybenzaldehyde, terephthalaldehyde, 3-hydroxy-1-oxo-1 H -cyclopenta[ a ]-naphthalene-2-carbaldehyde, 3-hydroxy-1-oxo-1 H -cyclopenta[ b ]-quinoxaline-2-carbaldehyde, 3-hydroxy-4-methyl-1-oxo-1,3a,4,8b-tetrahydrocyclopenta[ b ]indole-2-carbaldehyde, 4-hydroxy-6-oxo-6H-cyclopenta[ b ]thiophene-5-carbaldehyde, 3-hydroxy-5-nitro-1-oxo-1 H -indene-2-carbaldehyde, 4,6-dichloro-3-hydroxy-1-oxo-1 H -indene-2-carbaldehyde, 7-hydroxy-5-oxo-5 H -cyclopenta[ c ]pyridine-6-carbaldehyde, 7-hydroxy-5-oxo-5 H -cyclopenta[ b ]pyridine-6-carbaldehyde, 3-hydroxy-1-oxo-1 H -indene-2-carbaldehyde, 5-(dimethylamino)-3-hydroxy-1-oxo-1 H- indene-2-carbaldehyde, 3-hydroxy-4,5-dimethoxy-1-oxo-1 H -indene-2-carbaldehyde, 3-hydroxy-5-methoxy-1-oxo-1 H -indene-2-carbaldehyde, 3-methyl-5-(4-morpholinyl)-1-phenyl-1 H -pyrazole-4-carbaldehyde, 3-methyl-1-phenyl-5-(1 H -pyrrol-1-yl)-1 H -pyrazole-4-carbaldehyde, 3-methyl-1-phenyl-5-(1-pyrrolidinyl)-1 H -pyrazol-4-carbaldehyde, 3-methyl-1-(2-pyridinyl)-5-(1-pyrrolidinyl)-1 H -pyrazole-4-carbaldehyde, 3-methyl-1-(2-pyridinyl)-5-(1 H -pyrrol-1-yl)-1 H -pyrazole-4-carbaldehyde, 4-methoxy-1-naphthaldehyde, 1 H -indole-3-carbaldehyde, bis[4-(dimethylamino)-phenyl]methanethione, 2,4-dihydroxybenzaldehyde, 1-methyl-1 H -indole-3-carbaldehyde and 3,4-dihydroxybenzaldehyde.

Mittel nach Anspruch 1, dadurch gekennzeichnet, dass die reaktionsfähige Carbonylverbindung der allgemeinen Formeln B1-B17 ausgewählt ist aus Benzaldehyd, 4-Methoxybenzaldehyd, 4-Hydroxybenzaldehyd, 3,4-Dimethoxybenzaldehyd, 2,5-Dimethoxybenzaldehyd, 3-Hydroxy-4-methoxybenzaldehyd, 4-Nitrobenzaldehyd, 4-Hydroxy-3-methoxybenzaldehyd, 4-(Dimethylamino)benzaldehyd, (2 E )-3-[4-(Dimethylamino)phenyl]-2-propenal, 2,4,6-Trihydroxybenzaldehyd, 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyd, all-trans-Retinal, 3,5-Dioxo-1,2-diphenyl-4-pyrazolidincarbaldehyd, (2 E ,4 E )-5-Phenyl-2,4-pentadienal, Pentandial, 4-(Methylsulfanyl)benzaldehyd, 1-Naphthaldehyd, (2 E )-3-(4-Nitrophenyl)-2-propenal, 3-Phenoxybenzaldehyd, Terephthalaldehyd, 3-Hydroxy-1-oxo-1 H -cyclopenta[ a ]-naphthalin-2-carbaldehyd, 3-Hydroxy-1-oxo-1 H -cyclopenta[ b ]-chinoxalin-2-carbaldehyd, 3-Hydroxy-4-methyl-1-oxo-1,3a,4,8b-tetrahydrocyclopenta[ b ]indol-2-carbaldehyd, 4-Hydroxy-6-oxo-6 H- Cyclopenta[ b ]thiophen-5-carbaldehyd, 3-Hydroxy-5-nitro-1-oxo-1 H -inden-2-carbaldehyd, 4,6-Dichlor-3-hydroxy-1-oxo-1 H -inden-2-carbaldehyd, 7-Hydroxy-5-oxo-5 H -cyclopenta[ c ]pyridin-6-carbaldehyd, 7-Hydroxy-5-oxo-5 H -cyclopenta[ b ]pyridin-6-carbaldehyd, 3-hydroxy-1-oxo-1 H -inden-2-carbaldehyd, 5-(Dimethylamino)-3-hydroxy-1-oxo-1 H -inden-2-carbaldehyd, 3-Hydroxy-4,5-dimethoxy-1-oxo-1 H -inden-2-carbaldehyd, 3-Hydroxy-5-methoxy-1-oxo-1 H- inden-2-carbaldehyd, 3-Methyl-5-(4-morpholinyl)-1-phenyl-1 H -pyrazol-4-carbaldehyd, 3-Methyl-1-phenyl-5-(1 H -pyrrol-1-yl)-1 H -pyrazol-4-carbaldehyd, 3-Methyl-1-phenyl-5-(1-pyrrolidinyl)-1 H -pyrazol-4-carbaldehyd, 3-Methyl-1-(2-pyridinyl)-5-(1 -pyrrolidinyl)-1 H -pyrazol-4-carbaldehyd, 3-Methyl-1-(2-pyridinyl)-5-(1 H -pyrrol-1-yl)- 1 H -pyrazol-4-carbaldehyd, 4-Methoxy-1-naphthaldehyd, 1 H -Indol-3-carbaldehyd, Bis[4-(dimethylamino)-phenyl]methanthion, 2,4-Dihydroxybenzaldehyd, 1-Methyl-1 H -indol-3-carbaldehyd und 3,4-Dihydroxybenzaldehyd.

Examples of fungicides which may be combined with the novel compounds are: sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, znc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zinc N,N'-propylenebisdithioccarbamate and N,N'-polypropylenebis(thiocarbamoyl) disulfide; nitro derivatives, such as dinitro(1-methylheptyl)-phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and diisopropyl 5-nitroisophthalate; heterocyclic substances, such as 2-heptadecylimidazol-2-yl acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithio[4,5-b]quinoxaline, methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)-benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfonic acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, 2,5-dimethyl-N-cyclohexylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethylacetal, piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide), 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(N-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol, ?-(2-chlorophenyl)-?-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene, and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate, methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate, N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone, methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboxamide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, 2,4-difluoro-?-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol.

Fungizide, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, sind beispielsweise: Schwefel, Dithiocarbamate und deren Derivate, wie Ferridimethyldithiocarbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisdithiocarbamat, Manganethylenbisdithiocarbamat, Mangan-Zink-ethylendiamin-bis-dithiocarbamat, Tetramethylthiuramdisulfide, Ammoniak-Komplex von Zink-(N,N-ethylen-bis-dithiocarbamat), Ammoniak-Komplex von Zink-(N,N?-propylen-bis-dithiocarbamat), Zink-(N,N?-propylen-bis-dithiocarbamat), N,N?-Polypropylen-bis-(thiocarbamoyl)-disulfid; Nitroderivate, wie Dinitro-(1-methylheptyl)-phenylcrotonat,

Examples of fungicides which may be combined with the novel compounds are: sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zinc N,N'-propylenebisdithiocarbamate and N,N'-polypropylenebis(thiocarbamyl) disulfide; nitro derivatives, such as dinitro(1-methylheptyl)-phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and diisopropyl 5-nitroisophthalate; heterocyclic substances, such as 2-heptadecylimidazol-2-yl acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithio[4,5-b]quinoxaline, methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)-benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, 2,5-dimethyl-N-cyclohexylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethylacetal, piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide), 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol, 1-(4-phenylphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, ?-(2-chlorophenyl)-?-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene, and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate, methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate, N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone, methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, 2,4-difluoro-?-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, and 1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole. Use examples For comparison purposes, cis-2-(1,2,4-triazol-1-ylmethyl)-2-(4-chlorophenyl)-3-phenyloxirane (A)-disclosed in DE-3 218 130.2--and cis-2-(1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane--disclosed in DE-3 536 529.3--were used.

Anwendungsbeispiele Als Vergleichswirkstoffe werden cis-2-(1,2,4-Triazol-1-yl-methyl)-2-­ (4-chlorphenyl)-3-phenyl-oxiran (A) - bekannt aus DE-3 218 130.2 - und cis-2-(1,2,4-Triazol-1-ylmethyl)-2-(4-fluorphenyl)-3-(2-chlorphenyl)-­ oxiran (B) - bekannt aus DE-3 536 529.3 - verwendet.