Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-27
1995-04-11
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 14, 549 20, 549 22, 549 30, 549 39, 549 59, 549 60, 549357, 549370, 549378, 549414, 549415, 549448, 549472, C07D41110, C07D40910, C07D40710, C07D33502
Patent
active
054059682
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel polyketonmethine dyes of the general formula I ##STR3## where
A is a group of the formula A1 or A2 ##STR4##
R.sup.1 is a 5- or 6-membered cycloaliphatic radical which contains one or two hetero atoms from the group --NR.sup. 4--, --O-- and --S-- and which may be fused to an isoaromatic or heteroaromatic group, where carry halogen, C.sub.1 -C.sub.4 -alkyl or -alkoxy as substituents, or a C.sub.1 -C.sub.20 -alkyl group whose carbon chain may be interrupted by from one to five oxygen atoms in ether function and which may carry the following substituents: hydroxyl, phenyl, 1,3-dioxan-2-yl, 1,3-dioxolan-2-yl, --NHR.sup.5, --NHCOR.sup.5, --CONHR.sup.5, --OCONHR.sup.5, --N.sup..sym. (R.sup.5).sub.3.An.sup..THETA., --SO.sub.3 H or --SO.sub.3.sup..THETA. Ka.sup.108, where alkyl radicals R.sup.4 or phenyl and the radicals R.sup.5 in the substituent --N.sup..sym. (R.sup.5).sub.3 may be identical or different,
R.sup.2 and R.sup.3 are identical or different C.sub.1 -C.sub.10 -alkyl groups or together one of the radicals R.sup.1, provided that in the case of the group A1 radicals R.sup.1 of the formulae ##STR5## in which X is oxygen, sulfur, selenium, --N(CH.sub.3).sub.2 or ##STR6## and which may be substituted by alkyl, aryl or amino groups shall be excluded and in the case of the group A2 radicals R.sup.1 of the formulae ##STR7## in which Y is oxygen or sulfur shall be excluded, m and n are=identical or different integers from 0 to 3.
Dyes which absorb in the infrared region are of interest for many applications. They are frequently used as sensitizers for electrophotographic layers and for photopolymerizations and as laser light sensitive dyes in optical recording media.
If the dyes are additionally suitable for generating singlet oxygen, they are also of interest for use in photodynamic tumor therapy, which is based on the selective accumulation of dyes in cancer tissue and makes possible not only precise localization but also effective treatment even at an early stage of the tumor.
The irradiation of dye-enriched tumor tissue leads, probably via formation of singlet oxygen, to the selective destruction of the tumor tissue. Since the light transmissivity of body tissue rises steeply with increasing wavelength and for IR radiation of 800 nm is several powers of ten greater than for visible light, semiconductor lasers which emit light in the near IR region and dyes which show high absorption in that region are particularly suitable radiation sources for tumor therapy.
U.S. Pat. No. 5,002,812 and JP-A-242 288 (1989) describe the use of methine dyes having a cyclopentanetrione group based on benzofused indoline or on 3-ethylbenzothiazole and pyridine-, pyran- and thio-pyrans in optical recording media.
U.S. Pat. No. 3,140,951 discloses methine dyes with a cyclohexanetetrone group based on 3-ethyl-benzoxazole and -benzothiazole, 1-ethyl-3,3-dimethyl-2-indole and 1-ethyl-2(1H)- and -4(1H)-quinoline, which, however, are used there as desensitizers for photographic emulsions.
It is an object of the present invention to find dyes which absorb in the infrared region and have favorable application properties.
We have found that this object is achieved by the polyketomethine dyes I.
The radical R.sup.1 is a 5- or 6-membered cycloaliphatic radical which contains one or two hetero atoms from the group --NR.sup.4 --, --O-- and --S-- and which can be fused linearly or angularly with an isoaromatic or heteroaromatic group. Examples of preferred radicals R.sup.1 are: ##STR8##
Examples of particularly preferred radicals R.sup.1 are: ##STR9##
A very particularly preferred radical R.sup.1 is ##STR10##
The fused benzene and naphthalene nuclei are preferably unsubstituted. However, they may also carry C.sub.1 -C.sub.5 -alkyl, -alkoxy, halogen, --SO.sub.3 H or --SO.sub.3.sup..crclbar. Ka.sup..sym. as substituents.
Suitable for use as radical R.sup.4 are C.sub.1 -C.sub.20 -alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-p
REFERENCES:
Chemical Abstracts 112(20) 189117p of JP 88-71515, 1989.
Albert Bernhard
Kessel Knut
Martin Hans-Dieter
Silber Stefan
BASF - Aktiengesellschaft
M. Mach D. Margaret
Rotman Alan L.
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