Chemistry: analytical and immunological testing – Heterocyclic carbon compound – Hetero-o
Reexamination Certificate
2000-03-13
2001-05-08
Owens, Amelia (Department: 1612)
Chemistry: analytical and immunological testing
Heterocyclic carbon compound
Hetero-o
C549S396000, C548S239000, C514S374000, C514S456000
Reexamination Certificate
active
06228653
ABSTRACT:
BACKGROUND OF INVENTION
1. Field of Invention
The present invention relates to 1,2-dioxetane derivatives fused to a pyran ring and the use thereof. Since the present compounds are highly stable under an ambient conditions and emit light with a very high quantum efficiency, they can be used as chemiluminescent reagents for various assays such as immunoassay.
2. Related Art
Various 1,2-dioxetane derivatives have been synthesized, and those derivatives having at the position 3 a spiroadamantyl group are known to be useful as a substrate for chemiluminescence (see Japanese Examined Patent Publication (Kokoku) Nos. 5-21918 and 5-45590). In addition, Japanese Unexamined Patent Publication (Kokai) No. 9-216887 discloses compounds whose thermal stabilities are remarkably higher than the above-mentioned compounds, and which are useful for chemiluminescence.
However, to be useful as chemiluminescent reagents in clinical tests and the like, not only high thermal stability, but also high light-emission efficiency is required.
DISCLOSURE OF THE INVENTION
Accordingly, the present invention provides 1,2-dioxetane derivatives having not only high thermal stability but also high quantum efficiency for high emission.
More specifically, the present invention relates to a 1,2-dioxetane derivative represented by the general formula:
wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
independently represent a hydrogen atom, an alkyl group or an aryl group; or one or more than one pair of R
2
and R
3
, R
4
and R
5
, and R
6
and R
7
can together form a cyclic alkyl group; and
Ar represents
a group represented by the formula (A):
wherein R
8
represents a hydroxyl group, an alkoxyl group, an aralkyloxy group, a group represented by —Osi(R
10
R
11
R
12
) (wherein R
10
, R
11
and R
12
independently represents an alkyl group), or a phosphate group; R
9
represents a hydrogen atom, an alkyl group, an aryl group, a hydroxyl group, an alkoxyl group, an aryloxy group, or an aralkyloxy group; and V represents an oxygen atom or a sulfur atom,
a group represented by the formula (B):
wherein R
8
has the same meaning as defined for R
8
in the above formula (A); W represents a nitrogen atom or C—R
13
(wherein R
13
represents a hydrogen atom, an alkyl group, an aryl group, an alkoxyl group, or an aralkyloxy group); and X represents an oxygen atom or a sulfur atom,
or a group represented by the formula (C):
wherein R
8
has the same meaning as defined for R
8
in the above formula (A); R
14
represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxyl group, or a group represented by the formula (R
14′
):
wherein Y represents an oxygen atom, a sulfur atom, or a group represented by N—R
15
; and Z represents a hydrogen atom, an alkyl group, an aryl group or a group represented by —OR
16
, —SR
17
or the formula:
wherein R
15
represents a hydrogen atom, an alkyl group, an aryl group, a hydroxyl group, or an alkoxyl group; and R
16
, R
17
, R
18
and R
19
represent a hydrogen atom, an alkyl group or an aryl group; or one or more than one pair of R
15
and R
16
, R
15
and R
17
, R
15
and R
18
, and R
18
and R
19
can together form a ring and this ring may contain two or more heteroatoms.
The 1,2-dioxetane derivative of the present invention is a compound capable of deriving chemiluminescence and can be used as a substrate for immunoassay.
The present invention further provides an assay reagent comprising the above-mentioned 1,2-dioxetane derivative.
The present invention further provides an assay method using the above-mentioned 1,2-dioxetane derivatives.
DETAILED DESCRIPTION OF THE INVENTION
The alkyl group for the substituents R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
is an optionally substituted straight-chain or branched alkyl group having 1 to 20 carbon atoms. The alkyl group is preferably a lower alkyl group having 1 to 6 carbon atoms, and more preferably a lower alkyl group having 1 to 4 carbon atoms. The alkyl group is exemplified by methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosanyl. The lower alkyl group is exemplified by straight-chain or branched alkyl having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, a straight-chain or branched pentyl, or a straight-chain or branched hexyl.
The substituent for the alkyl group is, for example, a hydroxy group, an alkoxy group, an aryl group or a heterocyclic group. The alkoxy group is, for example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxyethoxy, methoxypropoxy, ethoxyethoxy, ethoxypropoxy or methoxyethoxyethoxy. The aryl is, for example, a phenyl or naphthyl, and the heterocyclic group includes, for example, furyl, thienyl or pyridyl group.
The aryl group for the substituents R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
is aromatic hydrocarbon group for example, phenyl or naphthyl. The aryl may be a heteroaryl group such as furyl, thienyl, pyridyl group or the like. The aryl group can be substituted with for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, a straight-chain or branched pentyl, or a straight-chain or branched hexyl.
One or more than one pair of R
2
and R
3
, R
4
and R
5
, and “R
6
and R
7
” together can form a cycloalkyl group having 3-8 carbon atoms. The cycloalkyl group has preferably 5-7 carbon atoms. The cycloalkyl is exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or the like. The cycloalkyl group may be optionally substituted by one or more substituents such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, a straight-chain or branched pentyl, a straight-chain or branched hexyl, phenyl or naphthyl.
Ar in the general formula (I) can be as follows:
Formula (A):
wherein R
8
represents a hydroxyl group, an alkoxyl group, an aralkyloxy group, a group represented by —OSi(R
10
R
11
R
12
) (wherein R
10
, R
11
and R
12
independently represents an alkyl group), or a phosphate group; R
9
represents a hydrogen atom, an alkyl group, an aryl group, a hydroxyl group, an alkoxyl group, an aryloxy group, or an aralkyloxy group; and V represents an oxygen atom or a sulfur atom;
Formula (B):
wherein R
8
has the same meaning as defined for R
8
in the above formula (A); W represents a nitrogen atom or C—R
13
(wherein R
13
represents a hydrogen atom, an alkyl group, an aryl group, an alkoxyl group, or an aralkyloxy group); and X represents an oxygen atom or a sulfur atom;
Formula (C):
wherein R
8
has the same meaning as defined for R
8
in the above formula (A); R
14
represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxyl group, or a group represented by the formula (R
14′
):
wherein Y represents an oxygen atom, a sulfur atom, or a group represented by N—R
15
; and Z represents a hydrogen atom, an alkyl group, an aryl group or a group represented by —OR
16
, —SR
17
or the formula:
wherein R
15
represents a hydrogen atom, an alkyl group, an aryl group, a hydroxyl group, or an alkoxyl group; and R
16
, R
17
, R
18
and R
19
represent a hydrogen atom, an alkyl group or an aryl group; or one or more than one pair of R
15
and R
16
, R
15
and R
17
, R
15
and R
18
, and R
18
and R
19
can together form a ring and this ring may contain two or more heteroatoms.
In the alkoxyl group as R
8
, the alkyl moiety has the same meaning as defined above for alkyl group as R
1
to R
7
. The alkoxy group is preferably a lower alkoxy group having 1 to 6 carbon atoms, and is exemplified by methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, straight-chain or branched pentyloxy such as n-pentyloxy, isopentyloxy, straight chain or branched hexyloxy such as n-hexyloxy, isohexyloxy, methoxyethoxy, methoxypropoxy, ethoxyethyoxy, ethoxypropoxy, methoxyethoxyethoxy, or the like.
In the aralkyloxy for R
8
in the formula (A), (B) and (C), the aryl moiety has the same meaning as defined above for the aryl as R
1
to R
6
. The alkylene moiety
Matsumoto Masakatsu
Watanabe Nobuko
Nixon & Vanderhye
Owens Amelia
Tosoh Corporation
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