Tetraphenylbacteriochlorin derivatives and compositions containing the same
AssigneesSan-Ei Gen F.F.I., Inc., Shigenobu Yano
InventorsShigenobu Yano, Toyoji Kakuchi, Yuji Mikata
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Abstract
Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): [wherein R1, R2, R3 and R4, independently from each other, are a residue of a monosaccharide represented by the formulae: (wherein, R is a hydrogen or a protecting group)], or its salt. The tetraphenylbacteriochlorin derivative or its salt has a large molar extinction coefficient at long wavelengths which are expected to have a high tissue-penetrating property, and exhibits high selectivity to tumor cells and hydrophilicity.
Claims3
A process for preparing a tetraphenylbacteriochlorin derivative (I) represented by the following formula:
- where R′ is a residue of a monosaccharide represented by the formula:
- where R is a hydrogen atom, or its salt comprising the steps of:
- i) reacting a pyrrole with a benzaldehyde derivative represented by the formula (III):
- in the presence of a metal compound containing a metal selected from the group I transition metals of the periodic table of elements, to obtain a tetraphenylporphyrin derivative represented by the formula (IV):
- where M represents a metal selected from the group I transition metals of the periodic table and R′ is as defined above, and its salt;
- ii) demetallizing the resulting tetraphenylporphyrin derivative (IV) and its salt to obtain a tetraphenylporphyrin derivative represented by the formula (V):
- where R′ is as defined above,
- and its salt;
- and
- iii) reducing the tetraphenylporphyrin derivative of formula (V) with a reducing agent selected from the group consisting of hydrazone, semicarbane and p-toluenesulfonylhydrazide to obtain a tetraphenylbacteriochiorin derivative (I) or its salt.
Dependencies are inferred from the claim text.