Patent DE-102009034189-A1 (DE)
Title: New (aza)phthalocyanine compounds useful e.g. to prepare a composition for photodynamic chemotherapy of tumors, as a part of an active layer to prepare and operate photovoltaic cells, and as main or addition components in printing ink
Inventor: BERTHOLD HERWIG
IPC: C07D209/44
Filed: 2009-07-17
Abstract: (Aza)phthalocyanine compounds (I) are new. (Aza)phthalocyanine compounds of formula (I) are new. M : H bonded to two corresponding nitrogen ring atoms, M 1>-(L 1>) p, M 2>or (L 1>) p, where M 1>-(L 1>) 0is a divalent metal atom comprising Ca, Mg, Mn 3>+>, Fe 3>+>, Co, Ni, Cu, Zn or Sn, M 1>-(L 1>) 1is a trivalent metal atom (where M 1>is Al, Ga, Fe 2>+>, Mn 3>+>or V 3>+>), M 1>-(L 1>) 2is a tetravalent metal atom (where M 1>is Si, Ge, Fe 4>+>, Mn 4>+>or V 5>+>); p : 0-2; M 2>an oxide or sulfide of a pentavalent metal atom e.g. Mn=O, Ti=O, V=O, Mn=S, Ti=S, V=S or a hexavalent metal atoms e.g. Mn 4>+>as [O=Mn=O] 2>+>; L 1>halo, preferably Cl, Br, I, triflyl corresponding to -O-SO 2-CF 3, aryl-O-, 1-10C-alkyl-O-, 1-6C-haloalkoxy, -CN, -O((CR 3>) vO) w-H or -(OCH 2CH 2) w-O-R 6>; w : 1-10; v : 2 or 3; R : pairwise vicinal for R 1>or R 2>; Y 1>N or C-R 3>; R 3>H, halo, 1-6C-alkyl, 1-6C-haloalkyl, 1-6C-alkoxy or 1-6C-haloalkoxy, where halo is F, Cl (both preferred), Br or I; R 1>formyl, -R 4>-OH, -R 4>-O-Si(R 5>) 3, -R 4>-O-R 6>, -R 4>-O-X 1>-R 7>, -R 4>-O-L-R 7>, -R 4>-O-X 1>-L-X 2>or -R 4>-O-X 1>-L-X 3>-R 7>, where two pairwise adjacent R 1>is -CH 2-O-Si(R 5>) 2-O-CH 2- and together with a C atom forms a benz-annelated or pyrazine-annelated 7,7-disubstituted [1,3,2]-dioxasilepin-ring of formula (II); L : 1-6C-alkylene, 2-6C-alkenylene, 2-6C-alkynylene, 3-7C-cycloalkylene, 1-6C-alkyl-3-10C-cycloalkylene or -[(CR 3>R 3>) nO] m-; n : 2-6; m : 1-4; R 2>halo, ethynyl, X 2>, -O-Si(R 5>) 3, -R 6>, -O-R 6>, -S-R 6>, -L-X 2>or -L-R 6>or two pairwise adjacent R 2>is -O-Si(R 5>) 2-O- and together with C atoms forms benz-annelated or pyrazine-annelated 2,2-disubstituted[1,3,2]-dioxasilol ring of formula (III); R 4>1-6C-alkylene, preferably CH 2; either R 5>1-10C-alkyl, 1-10C-haloalkyl, aryl, 1-6C-alkylaryl or benzyloxy, preferably CH 3, isopropyl, tert-butyl, benzyl, benzyloxy or phenyl; or 2R 5>+Si : trimethylsilyl-, tetramethylsilyl- or pentamethylsilyl-ring; R 6>H, 1-6C-alkyl, 1-6C-haloalkyl, -[(CR 3>R 3>) nO] m-R 3>, 3-6C-alkenyl, 3-6C-alkynyl, 3-10C-cycloalkyl, heterocyclyl, aryl or hetaryl; X 1>a bond, C(=O), -C(=O)O-, -C(=S)O-, -C(=O)NH-, -C(=O)NR 6>-, -C(=S)NH-, -C(=S)NR 6>- or a group of formula (IVaa) or (IVbb); L 2>3-7C-alkylene, where one of the methyl groups bonded at N is optionally replaced by -NH-, -O-, -S- or -NR 6>; R 7>R 6>or a carbohydrate residue; X 2>COOH, -COOR 6>, -CONH 2, -CONR 5>R 6>, -OH, -SH, -NH 2, -NR 6>R 6>, -NHR 6>or a group of formula (V); and X 3>a bond, -O-, -NH-, -NR 6>-, -S-, -[1H]-triazol-4-yl, -[1H]-triazol-5-yl, -C(=O)O-, -(C=O)NH-, -OC(=O)O-, -OC(=O)NH-, -NHC(=O)O- or -NHC(=O)NH-. Where (I) excludes: the compounds described in G. Pawlowski, et al. Synthesis. 1980, 4, 287in which M is Cu or 2H, Y 1>is CH, R is R 1>, R 4>is -CH 2O-, R 6>is -CH 2-CH 3, -phenyl, -CH 2-CF 3or -CH 2-CH 2-O-CH 2CH 3, or the compounds described in Jpn. Kokai Tokkyo Koho 1989, 8. JP 01-197739 Ain which M is Fe, Y 1>is CH, R is R 1>or -CH 2-CH 2-OH. [Image] [Image] ACTIVITY : Cytostatic. MECHANISM OF ACTION : None given.