Bipyridyl derivatives

Details Bipyridyl derivatives Bipyridyl derivatives

2002-05-15

2003-08-05

Davis, Zinna Northington (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06603007

ABSTRACT:

This application is a 371 of PCT/JP00/07628 filed Oct. 30, 2000.
TECHNICAL FIELD
The present invention relates to novel dipyridyl derivatives serving as an important intermediate in the fields of pharmaceuticals, agrichemicals, ligands, silver halide photosensitive materials, liquid crystals, surfactants, electrophotography and organic electroluminescence.
BACKGROUND ART
In recent years, pyridine derivatives have attracted attentions in a wide range of fields. In the fields of pharmaceuticals and agrichemicals, pyridine derivatives exhibit, as an endothelin antagonist, have high affinity for endothelin receptors (Japanese Patent Laid-Open No. Hei 9-162449, Japanese Patent Laid-Open No. Hei 10-194972, Japanese Patent Laid-Open No. Hei 11-92458). The affinity for the receptors are however insufficient and there is a strong demand for the creation of endothelin antagonists having more potent affinity for the receptor. As pharmaceuticals having a cerebral nerve protecting action such as remedies for aftereffects of cerebral infarction, compounds having, as a basic skeleton, a dipyridyl skeleton in its chemical structure have been researched and developed briskly. For example, in WO9852922, such a compound is disclosed.
In the fields of ligands, the research of dendrimer-type polynuclear metal complexes contained in dendrimer type compounds has proceeded at a brisk pace, because they exhibit new properties as the polynuclear metal complex when the mutual action between subunits is strong. As one of the studies, a polynuclear complex (Chemistry and Chemical Industry, 52(7), 890(1999), J. Am. Chem. Soc., 120, 5480(1998)) is synthesized, and the polynuclear complex is used a photo- and redox-active ruthenium (II) polypyridine complex as a sub-unit and as a bridging ligand, a pyrazine having an electron mutual action between skeletons, and its electrochemical properties are reported. There is a possibility of such a dendrimer-type polynuclear metal complex being used for artificial conversion process of solar energy and it is expected much as a promising substance.
Usefulness of the pyridine derivatives as a ligand of various reaction catalysts is also expected. For example, as described in GB2328686 or Journal of Synthetic Organic Chemistry, Japan, 56(9), 78(1998), they are expected to serve as a reactive accelerator when used as a ligand of a metal copper catalyst in the Ullmann type reaction.
In the fields of silver halide photosensitive materials, pyridine derivatives and various pyridinium compounds obtained by quaternizing these derivatives have been widely used as a nucleating development accelerator or crystal habit modifier. They are disclosed, for example, in Japanese Patent Laid-Open No. Hei 6-242534 or Japanese Patent Laid-Open No. Hei 8-227117.
In the field of liquid crystals, since incorporation of a pyridine derivative in the molecular structure of a liquid-crystal compound makes it possible for the resulting compound to exhibit various excellent properties of liquid crystal, studies on it have been made briskly. For example, such a study is disclosed, for example, in Japanese Patent Laid-Open No. Hei 8-295884, Japanese Patent Laid-Open No. Hei 9-25567, Japanese Patent Laid-Open No. Hei 9-110856, Japanese Patent Laid-Open No. Hei 10-7596 or Japanese Patent Laid-Open No. Hei 10-237002.
In the field of organic electroluminescence (EL) attracting attentions as a next-generation display material, absence of effective electron transporting materials has come to be a problem (for electron transporting materials, introduction of &pgr; electron system having high electron acceptance is indispensable). It has recently been reported that silole derivatives (silole (silacyclopentadiene) is a silicon homologue of cyclopentadiene) whose lowest unoccupied molecular orbit (LUMO) is low and electron acceptance is high, particularly 2,5-dipyridylsilole having as an aryl group a 2-pyridyl group has markedly high electron transporting properties and these electron transporting properties are superior to those of tris(8-hydroxyquinoline)aluminum Alq which has been regarded as one of the best electron transporting materials (Journal of Synthetic Organic Chemistry, Japan, 56(6), 50(1998), J. Am. Chem. Soc., 118, 11974(1996)). In the molecular design of the silole &pgr; electron system, particularly, a 2,5-diarylsilole derivative, how to control its electron structure and physical properties (for example, control by the substituent on the 2,5-aryl group) has drawn attentions.
In the field of electrophotography, the pyridine derivatives are used as a portion of the pigment of recording materials as disclosed, for example, in Japanese Patent Laid-Open No. Hei 3-282478 or Japanese Patent Laid-Open No. Hei 10-265690. Since they have a substituent permitting formation of two conformations in the pigment, they are used for the purpose of improving image stability, particularly, fixing property or light resistance. Pyridine derivatives are thus briskly studied also in this field. With a recent rapid increase in the amount of information, optical storage media of a large capacity have been highlighted. This field is therefore regarded promising as an application field of pyridine derivatives.
An object of the present invention is to provide novel dipyridyl derivatives which are useful substances or intermediates in the fields of pharmaceuticals, agrichemicals, ligands, silver halide photosensitive materials, liquid crystals, surfactants, electrophotography and organic electroluminescence.
DISCLOSURE OF THE INVENTION
As a result of extensive investigation, the present inventors have succeeded in obtaining novel dipyridyl derivatives useful in the fields of pharmaceuticals, agrichemicals, ligands, silver halide photosensitive materials, liquid crystals, surfactants, electrophotography and organic electroluminescence and completed the following inventions.
(1) A dipyridyl derivative represented by the following formula (A):
wherein A1 and A2 may be the same or different and each represents an alkyl or aryl group; A1 and A2 may be coupled together to form a ring; and A3 represents one of the following structures:
wherein A4 and A5 may be the same or different and each represents a hydrogen atom, an alkyl group or an aryl group.
(2) The dipyridyl derivative according to the above (1), wherein in A1, A2, A4 or A5 of the formula (A), the alkyl group has 1 to 4 carbon atoms and the aryl group is a phenyl or naphthyl group.
(3) The dipyridyl derivative according to the above (2), wherein in the formula (A), A1 and A2 are the same.
(4) A dipyridyl derivative represented by the following formula (B):
wherein one of B1 and B2 represents a hydrogen atom, and the other represents an alkyl or aryl group, and B3 and B4 may be the same or different and each represents a hydrogen atom, an alkyl group or an aryl group,
with the proviso that when B3 and B4 simultaneously represent a hydrogen atom, the following cases are excluded:
(i) one of B1 and B2 represents an alkyl group having 3 or less carbon atoms, and
(ii) B1 represents a phenyl group, and with the further proviso that when B2 represents a hydrogen atom, the following case are excluded:
(i) each of B1 and B3 (substituted at the 6-position) represents a phenyl group and B4 represents a hydrogen atom, or
(ii) B1, B3 (substituted at the 2-position) and B4 (substituted at the 6-position) each represents a methyl group.
(5) The dipyridyl derivative according to the above (4), wherein in B1, B2, B3 or B4 of the formula (B), the alkyl group has 1 to 4 carbon atoms and the aryl group is a phenyl or naphthyl group.
(6) A dipyridyl derivative represented by the following formula (C):
wherein one of C1 and C2 represents a hydrogen atom and the other one represents an alkyl or aryl group; and C3 and C4 may be the same or different and each represents a hydrogen atom, an alkyl group or an aryl group, with the proviso that when C3 and C4 simultaneously represent a hydrogen atom, C1 or C2 does not represent a methyl group.
(7) The dipyridyl derivative according to the ab

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