Patent ID: 6022906
Filing Date: 2000-02-08
Classification: B33Y,C07C,C07D,G03F

Abstract:
Compounds of the formula I, II, III or IV whereina is an integer 1, 2 or 4;Ar is a phenyl, biphenyl or benzoylphenyl group, which is unsubstituted or substituted by 1 to 5 of the radicals halogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl-C.sub.1 -C.sub.3 alkyl, --COOH, --COO(C.sub.1 -C.sub.4 alkyl), --OR.sub.7, --SH, --SR.sub.8, --SOR.sub.8, --SO.sub.2 R.sub.8, --CN, --SO.sub.2 NH.sub.2, --SO.sub.2 NH(C.sub.1 -C.sub.4 alkyl), --SO.sub.2 --N(C.sub.1 -C.sub.4 alkyl).sub.2, --NR.sub.9 R.sub.10, --NHCOR.sub.9, or by a group of the formula V, ##STR47## or Ar is a group of the formula VI or VII ##STR48## Ar.sub.1 if a is 1 has the same meanings as Ar; if a is 2, Ar.sub.1 is a divalent aromatic radical of the formula VIII or VIIIa ##STR49## if a is 4, Ar.sub.1 is a tetravalent aromatic radical of the formula VIIIb ##STR50## Ar.sub.2 is ##STR51## these groups are unsubstituted or substituted by 1 to 5 of the radicals halogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl-C.sub.1 -C.sub.3 alkyl, --COOH, --COO(C.sub.1 -C.sub.4 alkyl), --OR.sub.7, --SH, --SR.sub.8, --SOR.sub.8, --SO.sub.2 R.sub.8, --CN, --SO.sub.2 NH.sub.2, --SO.sub.2 NH(C.sub.1 -C.sub.4 alkyl), --SO.sub.2 --N(C.sub.1 -C.sub.4 alkyl).sub.2, --NR.sub.9 R.sub.10, --NHCOR.sub.9, or by a group of the formula V as defined above, or Ar.sub.2 is a group of the formula VIa or VIIa ##STR52## X is a direct bond, --O--, --S-- or --N(R.sub.6)--; Y is hydrogen, C.sub.1 -C.sub.12 alkyl, which is unsubstituted or substituted by 1 to 5 OH, OR.sub.6, COOR.sub.6, SH, N(R.sub.6).sub.2 or halogen or substituted 1 to 5 times by a group of the formula Ia ##STR53## or Y is C.sub.2 -C.sub.20 alkyl, which is interrupted by 1 to 9 --O--, --N(R.sub.6)--, --S--, --SS--, --X--C(.dbd.O)--, --X--C(.dbd.S)--, --C(.dbd.O)--X--, --X--C(.dbd.O)--X--, --C(.dbd.S)--X--, ##STR54## wherein the interrupted C.sub.2 -C.sub.20 alkyl can further be substituted by 1 to 5 SH, or Y is benzyl which is unsubstituted or substituted once or twice by --CH.sub.2 SH and said benzyl may further be substituted by C.sub.1 -C.sub.4 alkyl, or Y is Ar (as defined above), or a group ##STR55## or Y is a heterocyclic 5-7 membered aliphatic or aromatic ring, comprising 1 to 4 N, O or/and S-atoms, or Y is a 8-12 membered bicyclic aliphatic or aromatic ring system, comprising 1 to 6 N, O or/and S-atoms, which mono- or bicyclic rings can further be substituted by SH or 1-5 times by a group of the formula Ia, or Y is a group ##STR56## q is 1 or 2; r is 1, 2 or 3;p is 0 or 1;t is 1 to 6;u is 2 or 3;R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.8 alkyl, which is unsubstituted or substituted by OH, C.sub.1 -C.sub.4 alkoxy, SH, CN, --COO(C.sub.1 -C.sub.8 alkyl), (C.sub.1 -C.sub.4 alkyl)--COO-- or --N(R.sub.3)(R.sub.4), or R.sub.1 and R.sub.2 independently of one another are C.sub.3 -C.sub.6 alkenyl, phenyl, chlorophenyl, R.sub.7 --O-phenyl, R.sub.8 --S-phenyl or phenyl-C.sub.1 -C.sub.3 -alkyl, wherein said C.sub.3 -C.sub.6 alkenyl, phenyl, chlorophenyl, R.sub.7 --O-phenyl, R.sub.8 --S-phenyl or phenyl-C.sub.2 -C.sub.3 -alkyl are unsubstituted or substituted by 1 to 5 SH, or R.sub.1 and R.sub.2 together are unbranched or branched C.sub.2 -C.sub.9 alkylene, C.sub.3 -C.sub.9 oxaalkylene or C.sub.3 -C.sub.9 azaalkylene, wherein said C.sub.2 -C.sub.9 alkylene, C.sub.3 -C.sub.9 oxaalkylene or C.sub.3 -C.sub.9 azaalkylene are unsubstituted or substituted by 1 to 5 SH or R.sub.1 and R.sub.2 independently of one another are a radical of the formula IX or X ##STR57## R.sub.3 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.4 alkyl, which is substituted by OH, SH, C.sub.1 -C.sub.4 alkoxy, CN or --COO(C.sub.1 -C.sub.4 alkyl), or R.sub.3 is C.sub.3 -C.sub.5 alkenyl, C.sub.5 -C.sub.12 -cycloalkyl or phenyl-C.sub.1 -C.sub.3 alkyl;R.sub.4 is C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.4 alkyl, which is substituted by OH, SH, C.sub.1 -C.sub.4 alkoxy, CN or --COO(C.sub.1 -C.sub.4 alkyl), or R.sub.4 is C.sub.3 -C.sub.5 alkenyl, C.sub.5 -C.sub.12 -cycloalkyl, phenyl-C.sub.1 -C.sub.3 alkyl, unsubstituted phenyl or phenyl, which is substituted by halogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy or --COO(C.sub.1 -C.sub.4 alkyl);or R.sub.4 together with R.sub.2 is C.sub.1 -C.sub.7 alkylene, phenyl-C.sub.1 -C.sub.4 alkylene, o-xylylene, 2-butenylene or C.sub.2 -C.sub.3 oxaalkylene or C.sub.2 -C.sub.3 azaalkylene;or R.sub.3 and R.sub.4 together are C.sub.3 -C.sub.7 alkylene, which can be interrupted by --O--, --S--, --CO-- or --N(R.sub.6)-- and which C.sub.3 -C.sub.7 alkylene can be substituted by OH, C.sub.1 -C.sub.4 alkoxy or --COO(C.sub.1 -C.sub.4 alkyl);R.sub.5 is C.sub.1 -C.sub.6 alkylene, xylylene, cyclohexylene, wherein said C.sub.1 -C.sub.6 alkylene, xylylene, cyclohexylene are unsubstituted or substituted by 1 to 5 SH, or R.sub.5 is a direct bond;R.sub.6 is hydrogen, unsubstituted or OH--, SH-- or HS--(CH.sub.2).sub.q --COO-substituted C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkyl, which is interrupted by --O--, --NH-- or --S--, or R.sub.6 is C.sub.3 -C.sub.5 alkenyl, phenyl-C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.sub.2 CN, unsubstituted or OH- or SH-substituted C.sub.1 -C.sub.4 alkyl-CO--CH.sub.2 CH.sub.2 --, unsubstituted or OH- or SH-substituted C.sub.2 -C.sub.8 alkanoyl or R.sub.6 is benzoyl;Z is a divalent radical of the formula ##STR58## --N(R.sub.17)-- or --N(R.sub.17)--R.sub.18 --N(R.sub.17)--; U is unbranched or branched C.sub.1 -C.sub.7 alkylene;V and W independently of one another are a direct bond, --O--, --S-- or --N(R.sub.6)--, provided that V and W are not both a direct bond simultaneously;M is O, S or N(R.sub.6);R.sub.7 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 -alkenyl, cyclohexyl, hydroxycyclohexyl, or R.sub.7 is C.sub.1 -C.sub.4 alkyl, which is mono- or polysubstituted with Cl, Br, CN, SH, --N(C.sub.1 -C.sub.4 alkyl).sub.2, piperidino, morpholino, OH, C.sub.1 -C.sub.4 alkoxy, --OCH.sub.2 CH.sub.2 CN, --OCH.sub.2 CH.sub.2 COO(C.sub.1 -C.sub.4 alkyl), --OOCR.sub.19, --COOH, --COO(C.sub.1 -C.sub.8 alkyl), --CONH(C.sub.1 -C.sub.4 alkyl), --CON(C.sub.1 -C.sub.4 alkyl).sub.2, ##STR59## --CO(C.sub.1 -C.sub.4 alkyl) or ##STR60## or R.sub.7 is 2,3-epoxypropyl, --(CH.sub.2 CH.sub.2 O).sub.m H, unsubstituted phenyl, or phenyl which is substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or --COO(C.sub.1 -C.sub.4 alkyl), or R.sub.7 is phenyl-C.sub.1 -C.sub.3 alkyl, tetrahydropyranyl, tetrahydrofuranyl, --COOR.sub.19, --COO(C.sub.1 -C.sub.8 alkyl), --CONH(C.sub.1 -C.sub.4 alkyl), --CON(C.sub.1 -C.sub.8 alkyl).sub.2, --Si(R.sub.20)(R.sub.21).sub.2, or --SO.sub.2 R.sub.22 ;R.sub.8 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, cyclohexyl, hydroxycyclohexyl, or R.sub.8 is C.sub.1 -C.sub.4 alkyl, which is mono- or polysubstituted with Cl, Br, CN, SH, --N(C.sub.1 -C.sub.4 alkyl).sub.2, piperidino, morpholino, OH, C.sub.1 -C.sub.4 alkoxy, --OCH.sub.2 CH.sub.2 CN, --OCH.sub.2 CH.sub.2 COO(C.sub.1 -C.sub.4 alkyl), --OOCR.sub.19, --COOH, --COO(C.sub.1 -C.sub.8 alkyl), --CON(C.sub.1 -C.sub.4 alkyl).sub.2, ##STR61## --CO(C.sub.1 -C.sub.4 alkyl) or ##STR62## or R.sub.8 is 2,3-epoxypropyl, phenyl-C.sub.1 -C.sub.3 alkyl, phenyl-C.sub.1 -C.sub.3 hydroxyalkyl, unsubstituted phenyl or phenyl which is mono- or poly-substituted by halogen, SH, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or --COO(C.sub.1 -C.sub.4 alkyl), or R.sub.8 is 2-benzothiazyl, 2-benzimidazolyl, --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --SH or --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 --SH;R.sub.9 and R.sub.10 independently of one another are hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.4 alkyl, which is substituted by OH, SH, C.sub.1 -C.sub.4 alkoxy, CN or --COO(C.sub.1 -C.sub.4 alkyl), or R.sub.9 and R.sub.10 independently of one another are C.sub.3 -C.sub.5 alkenyl, cyclohexyl, phenyl-C.sub.1 -C.sub.3 alkyl, unsubstituted phenyl or phenyl which is mono- or poly-substituted by C.sub.1 -C.sub.12 alkyl or halogen, or R.sub.9 and R.sub.10 together are C.sub.2 -C.sub.7 alkylene which can be interrupted by --O--, --S-- or --N(R.sub.18)--;R.sub.11 and R.sub.12 independently of one another are a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --O--, --S--, --CO-- or --N(R.sub.6)--; provided that R.sub.11 and R.sub.12 are not a direct bond at the same time;R.sub.13 is hydrogen, C.sub.1 -C.sub.8 alkyl or phenyl wherein C.sub.1 -C.sub.8 alkyl or phenyl are unsubstituted or substituted by 1 to 5 SH;R.sub.14, R.sub.15 and R.sub.16 independently of one another are hydrogen or unsubstituted or SH-substituted C.sub.1 -C.sub.4 alkyl;R.sub.17 is hydrogen, unsubstituted or SH-substituted C.sub.1 -C.sub.8 alkyl or unsubstituted or SH-substituted phenyl;R.sub.18 is unbranched or branched C.sub.2 -C.sub.16 alkylene, which can be interrupted by 1 to 6 --O--, --S-- or --N(R.sub.17)-- or substituted by 1 to 5 groups SH;R.sub.19 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or phenyl;R.sub.20 and R.sub.21 independently of one another are C.sub.1 -C.sub.4 alkyl or phenyl;R.sub.22 is C.sub.1 -C.sub.18 alkyl, phenyl or phenyl substituted by C.sub.1 -C.sub.14 alkyl;Ar.sub.3 is phenyl, naphthyl, furyl, thienyl or pyridiyl, wherein said radicals are unsubstituted or substituted by halogen, SH, OH, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkyl, which is substituted by OH, halogen, SH, --N(R.sub.17).sub.2, C.sub.1 -C.sub.12 alkoxy, --COO(C.sub.1 -C.sub.18 alkyl), --CO(OCH.sub.2 CH.sub.2).sub.n OCH.sub.3 or --OCO(C.sub.1 -C.sub.4 alkyl), or said radicals are substituted by C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.4 alkoxy, which is substituted by --COO(C.sub.1 -C.sub.18 alkyl) or --CO(OCH.sub.2 CH.sub.2).sub.n OCH.sub.3, or said radicals are substituted by --(OCH.sub.2 CH.sub.2).sub.n OH, --(OCH.sub.2 CH.sub.2).sub.n OCH.sub.3, C.sub.1 -C.sub.8 alkylthio, phenoxy, --COO(C.sub.1 -C.sub.18 alkyl), --CO(OCH.sub.2 CH.sub.2).sub.n OCH.sub.3, phenyl or benzoyl;n is 1 to 20;m is 2 to 20;provided that at least one of the radicals Ar, Ar.sub.1, Ar.sub.2, Ar.sub.3, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 or Y is substituted by 1 to 5 SH groups, or provided that Y contains at least one --SS-- group; and provided that if R.sub.3 and R.sub.4 are morpholino and R.sub.1 and R.sub.2 simultaneously are methyl, Ar.sub.1 is not phenyl substituted by SR.sub.8, with R.sub.8 being H or --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 SH or CH.sub.2 CH.sub.2 CH.sub.2 SH; or an acid addition salt of a compound of the formula I, II, III or IV.