1,2-dioxetane derivative

Chemistry: molecular biology and microbiology – Measuring or testing process involving enzymes or... – Involving antigen-antibody binding – specific binding protein...

Reexamination Certificate

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C436S537000, C436S805000, C544S148000, C548S159000, C548S217000, C549S058000, C549S435000

Reexamination Certificate

active

06218135

ABSTRACT:

TECHNICAL FIELD
This invention relates to novel 1,2-dioxetane derivatives, and more particularly to 1,2-dioxetane derivatives of value as chemiluminescent materials which can be used in immunological assay systems and other uses.
BACKGROUND ART
A variety of 1,2-dioxetane derivatives have so far been synthesized, and it is known that compounds having a spiroadamantyl group in the 3-position are particularly useful chemiluminescent materials (e.g. Japanese Kokai Publication Hei-5-21918 and Japanese Kokai Publication Hei-5-45590).
Furthermore, as compounds synthesized by the present inventors, the compounds disclosed in Japanese Kokai Publications Hei-8-245615, Hei-8-169885, and Hei-8-165287 are known. However, those 1,2-dioxetane derivatives do not have good thermal stability. The Japanese Kokai Publication Hei-9-216887 referred to above discloses a compound with improved thermal stability.
In regard of such 1,2-dioxetane derivatives, much research has been undertaken as inferable from the above list of publications and new compounds have also been created. Therefore, it is necessary for applying to a clinical examination and other fields to have a substance with a good thermal stability, easiness of handling, and high in emission efficiency.
However, those known compounds, e.g. compounds described in Japanese Kokai Publication Hei-9-216887 have the drawback that their chemiluminescent emission efficiencies are considerably sacrificed in the presence of protic solvents. Therefore, when used in immunoassays in a clinical examination, for instance, those compounds failed to give a practically useful intensity of emission when the assay system includes a protic solvent. Therefore, it is necessary to have a substance capable of increasing the intensity of emission, the so-called enhancer, to coexist in the system. Therefore, a compound showing high emission efficiency without coexisting enhancer in the system even in a protic solvent is more available.
Furthermore, in a clinical examination performed using an automatic instrument, for instance, compounds differing in emission wavelength from the conventional chemiluminescent materials should be of great use, for the detection and determination of a plurality of test items can be simultaneously performed. Moreover, if the difference in color be of the order which can be visually detected, such compounds should be of great convenience and are expected to find application in a variety of uses.
SUMMARY OF THE INVENTION
In view of the above state of the art, the present invention has for its object to provide a compound which is easy to handle, thermally stable, and high in emission efficiency.
Further, the present invention has for its object to provide a compound not only which is easy to handle, thermally stable, and high in emission efficiency, but also which has a different wavelength from conventional 1,2-dioxetane derivatives' (400 to 500 nm), emission of which can be identified with conventional derivatives' with equipments, and which can be identified with conventional derivatives visually.
Furthermore, the present invention has for its object to provide a compound not only which is easy to handle, thermally stable, and high in emission efficiency, but also which can show high emission efficiency without coexisting enhancer in the system even in a protic solvent.
The present invention is related to a 1,2-dioxetane derivative of general formula (I).
[wherein R
1
, R
2
, R
3
, R
4
and R
5
each independently represents hydrogen, alkyl or aryl; a pair of R
2
and R
3
and a pair of R
4
and R
5
may respectively be joined to each other to form a cycloalkyl group; Ar represents a group of formula (A)
(R
6
represents hydroxyl, alkoxyl, aralkyloxy, —OSi(R
8
R
9
R
10
) (where R
8
, R
9
and R
10
each independently represents alkyl) or a phosphate group; R
7
represents hydrogen, alkyl, aryl, hydroxyl, alkoxyl, aryloxy or aralkyloxy; V represents oxygen or sulfur), formula (B)
(wherein R
6
is the same as in formula (A); W represents nitrogen or C—R
11
(where R
11
represents hydrogen, alkyl, alkoxyl, aryl or aralkyloxy); X represents oxygen or sulfur), or formula (C)
(wherein R
6
is the same as in formula (A); Y represents oxygen, sulfur or N—R
12
; Z represents hydrogen, alkyl, aryl, OR
13
, SR
14
or a group of the formula;
R
12
represents hydrogen, alkyl, aryl, hydroxyl, or alkoxyl group. R
13
, R
14
, R
15
and R
16
each independently represents hydrogen, alkyl or aryl; a pair of R
12
and R
13
, a pair of R
12
and R
14
, a pair of R
12
and R
15
, and a pair of R
15
and R
16
may respectively be joined to each other to form a ring, which ring may contain 2 or more hetero-atoms)].
DETAILED DESCRIPTION OF THE INVENTION
As the term is used in this specification, “alkyl” includes but is not limited to straight-chain and branched-chain alkyl groups each containing 1 to 20 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosanyl, etc. and groups formed as the above-mentioned groups are bound to each other in a branching manner in suitable combinations. Those alkyl groups may have one or more substituent groups.
The substituent group mentioned above includes but is not limited to hydroxyl, alkoxyl, and aryl. The alkoxyl mentioned above includes but is not limited to the alkoxyl groups formed as 1 to 5 alkoxy groups each containing 1 to 20 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxyethoxy, methoxypropoxy, ethoxyethoxy, ethoxypropoxy, methoxyethoxyethoxy, etc., are bound together in a linear fashion or in a branched fashion. The aryl group mentioned above includes but is not limited to aromatic hydrocarbon groups each containing 6 to 20 carbon atoms such as phenyl, naphthyl, etc. and heteroaryl groups each containing 1 to 5 nitrogen, oxygen or sulfur atoms as ring atoms, such as furyl, thienyl, pyridyl, and so on.
As the term is used in this specification, “alkoxyl” includes the same alkoxyl groups as the above-mentioned alkoxyl groups with which said alkyl may be optionally substituted.
Further in this specification, “aryl” includes the same aryl groups as the above-mentioned aryl groups with which said alkyl may be optionally substituted.
As the term is used in this specification, “aralkyloxy” means an aralkyloxy group of 7 to 20 carbon atoms, such as benzyloxy, phenethyloxy, etc.
As the term is used in this specification “halogen” includes fluorine, chlorine and bromine, etc.
Referring to the above general formula (I), Ar is preferably a group of formula (a):
[R
6
, R
7
, and V are as defined in the formula (A)], formula (b):
[R
6
, W and X are as defined in the formula (B)], or formula (c):
[R
6
, Y and Z are as defined in the formula (C)].
Referring, further, to the above general formula (I), R
1
, R
2
and R
3
each is preferably alkyl, more preferably alkyl of 1 to 4 carbon atoms, and R
4
and R
5
each is preferably hydrogen.
When Ar in general formula (I) represents a group of the above formula (C), preferably Y is oxygen and Z is a group of the following formula,
wherein a pair of R
15
and R
16
is joined to each other to form a 3- through 7-membered ring. More preferably, Z is a ring of the following formula.
When Ar in the general formula (I) represents a group of the above formula (C), preferably Y is N—R
12
, Z is OR
13
, and a pair of R
12
and R
13
is joined to each other to form a 3- through 7-membered ring. More preferably, R
12
and R
13
taken together represents a ring of the following formula.
The 1,2-dioxetane derivative of general formula (I), the compound of the invention, can be produced from a dihydrofuran ring derivative having an aryl group substituted by R
61
, which can be represented by the following general formula (II).
[wherein R
1
to R
5
are as defined in the general formula (I); R
61
represents alkoxyl or aralkyloxy; (R
61
)Ar is a group of formula (A

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