EP0254051A2
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EP
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Chemiluminescent 1,2-dioxetane compounds
Assignee: Applied Biosystems Inc
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Filing: 1987-06-23
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Granted: —
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Expires: 2007-06-23
Abstract
Abstract Novel light producing 1,2-dioxetanes are described of the formula wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.
Inventors
- 👤 Arthur P. Schaap
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-28 15:36
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; C07C; C07C37/00; C07C37/01; C07C37/055; C07C37/62; C07C51/00; C07C51/15; C07D207/00; C07D207/46; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C07D321/00; C07D407/00; C07D407/02; C07D407/10; C07D407/12; C07D417/00; C07D417/02; C07D417/12; C07D493/00; C07D493/02; C07D493/10; C07D495/00; C07D495/02; C07D495/04; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F9/00; C07F9/02; C07F9/547; C07F9/6536; C07F9/6539; C07F9/6541; C07F9/655; C07F9/6551; C07F9/65512; C07F9/6552; C07F9/65522; C07F9/6558; C07F9/65586; C07F9/6561; C07H; C07H15/00; C07H15/20; C07H15/203; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/18; C07C2603/56; C07C2603/58; C07C2603/70; C07C2603/74
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
92 words
I. A stable 1,2-dioxetane compound of the formula wherein ArOX an aryl group having an aryl ring substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove X by an activating agent so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced.
Claim 2
Dependent Claim
163 words
A stable 1,2-dioxetane compound of the formula wherein R 1 and R 2 together and R 3 and R 4 together can be joined as spirofused alkylene and aryl rings, wherein at least one of R 1 and R 2 or R 3 and R 4 is an aryl group, having an aryl ring substituted with an X oxy-group which forms an unstable oxide intermediate 1,2 dioxetane compound when triggered to remove X by an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula: wherein those of R 1 , R 2 , R 3 or R 4 which are unsubstituted by an X-oxy group are carbon containing organic groups which provide stability for the stable 1,2-dioxetane compound and wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate.
Claim 3
Dependent Claim
148 words
A stable dioxetane compound of the formula: wherein R 1 is selected from alkyl, alkoxy, aryloxy, dialkyl or aryl amino, trialkyl or aryl silyloxy and aryl groups including spirofused aryl groups with R 2 , wherein R 2 is an aryl group which can include R 1 and is substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when activated by an activating agent to remove X selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors so that the unstable-1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula: wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate and wherein R 3 and R 4 are selected from aryl and alkyl groups which can be joined together as spirofused polycyclic alkyl and polycyclic aryl groups.
Claim 4
Dependent Claim
142 words
A stable 1,2-dioxetane compound of the formula: wherein R 1 is selected from lower alkyl containing I to 8 carbon atoms, R 2 is selected from aryl, biaryl and fused ring polycyclic aryl groups which can be substituted or unsubstituted , and R 3 C -is selected from polycyclic alkyl groups containing 6 to 30 carbon atoms, wherein OX is an oxy group subtituted on an aryl ring which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove X by an activating agent selected from acid, base, salt, enzyme and inorganic and organic catalysts, and electron donor sources and X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate and wherein (I) decomposes in the presence of an activating agent to produce light and carbonyl containing compounds of the formula and
Claim 5
Dependent Claim
30 words
The compound of Claim 4 wherein OX group is selected from hydroxyl, trialkyl or aryl silyloxy, inorganic oxy acid salt, phosphate salt, sulfate salt, oxygen-pyranoside, aryl and alkyl carboxyl esters.
Claim 6
Dependent Claim
11 words
The compound of Claim 5 wherein -is a spirofused adamantyl group.
Claim 7
Dependent Claim
15 words
The compound of Claim 5 wherein R 2 is selected from naphthyl and phenyl groups.
Claim 8
Dependent Claim
11 words
The compound of Claim 5 wherein R, is a methyl group.
Claim 9
Dependent Claim
47 words
The compound of Claim 4 wherein R, is a methyl group, R 2 is a naphthyl group and -is an adamantyl group and wherein OX is selected from hydroxyl, trialkyl or aryl silyloxy, inorganic oxy acid salt, phosphate salt, sulfate salt, oxygen-pyranoside, aryl and alkyl carboxyl esters.
Claim 10
Dependent Claim
104 words
A stable 1,2-dioxetane compound of the formula: wherein ArOX is a spirofused aryl group containing a ring substituted X-oxy group, wherein OX forms an unstable oxide intermediate 1,2-dioxetane compound when triggered by an activating agent to remove X selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors, wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing derivatives of the formula and wherein -is selected from polycyclic alkyl groups containing 6 to 30 carbon atoms.
Claim 11
Dependent Claim
11 words
II. The compound of Claim 10 wherein -is an adamantyl group.
Claim 12
Dependent Claim
18 words
The compound of Claim 10 wherein ArOX is a fluorenyl group fused to the 1,2-dioxetane compound at C9.
Claim 13
Dependent Claim
18 words
The compound of Claim 10 wherein ArOX is a xanthenyl group fused to the 1,2-dioxetane compound at C9.
Claim 14
Dependent Claim
27 words
The compound of Claim 10 wherein -is an adamantyl group and ArOX is selected from a xanthane and fluorenyl groups fused to the 1,2-dioxetane compound at C9.
Claim 15
Dependent Claim
25 words
The compound of Claim 10 wherein -is an adamantyl group and wherein ArOX is a hydroxyl fluorenyl group fused to the 1,2-dioxetane compound at C9.
Claim 16
Dependent Claim
15 words
The compound of Claim 15 wherein the hydroxyl fluorenyl group is a 2-hydroxyl fluorenyl group.
Claim 17
Dependent Claim
25 words
The compound of Claim 10 wherein is an adamantyl group and wherein ArOX is a hydroxyl xanthenyl group fused to the 1,2-dioxetane compound at C9.
Claim 18
Dependent Claim
15 words
The compound of Claim 17 wherein the hydroxyl xanthenyl group is a 3-hydroxyl xanthenyl group.
Claim 19
Dependent Claim
39 words
The compound of Claim 10 wherein ArOX is selected from xanthanyl and fluorenyl groups and wherein OX is selected from hydroxyl, trialkyl or aryl silyloxy, inorganic oxy acid salt, phosphate salt, sulfate salt, oxygen-pyranoside, aryl and alkyl carboxyl esters.
Claim 20
Dependent Claim
13 words
The compound of Claim 19 wherein OX is selected from phosphate and sulfate.
Claim 21
Dependent Claim
11 words
The compound of Claim 19 wherein OX is a silyloxy group.
Claim 22
Dependent Claim
11 words
The compound of Claim 19 wherein OX is alkyl carbonyl ester.
Claim 23
Dependent Claim
10 words
The compound of Claim 19 wherein OX is oxygen pyranoside.
Claim 24
Independent Claim
109 words
The method for generating light which comprises: (a) providing a stable 1,2-dioxetane of the formula wherein ArOX an aryl group having an aryl ring substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove. X by an activating agent so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced; and (b) decomposing the stable 1,2-dioxetane with the activating agent.
Claim 25
Independent Claim
179 words
The method for generating light which comprises: (a) providing a stable 1,2-dioxetane compound of the formula wherein Ri and R 2 together and R 3 and R 4 together can be joined as spirofused alkylene and aryl rings, wherein at least one of R 1 and R 2 or R 3 and R 4 is an aryl group, having an aryl ring substituted with an X oxy-group which forms an unstable oxide intermediate 1,2 dioxetane compound when triggered to remove X by an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula: wherein those of Ri, R 2 , R 3 or R 4 which are unsubstituted by an X-oxy group are carbon containing organic groups which provide stability for the stable 1,2-dioxetane compound and wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate; and (b) decomposing the stable 1,2-dioxetane with the activating agent.
Claim 26
Independent Claim
164 words
The method for generating light which comprises: (a) providing a stable dioxetane compound of the formula: wherein R 1 is selected from alkyl alkoxy,. aryloxy dialkylamino trialkyl or aryl silyloxy and aryl groups including spirofused aryl groups with R 2 , wherein R 2 is an aryl group which can include R 1 and is substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when activated by an activating agent to remove X selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors o that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula: wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate and wherein R3 and R 4 are selected from aryl and alkyl groups which can be joined together as spirofused polycyclic alkyl and polycyclic aryl groups; and (b) decomposing the stable 1,2-dioxetane with the activating agent.
Claim 27
Dependent Claim
154 words
In a process for producing a compound of the formula wherein ArOX an aryl group having an aryl ring substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove X by an activating agent so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced which comprises: (a) reacting a carbonyl containing compound of the formula: with a compound of the formula: wherein Ar silyloxy is an aryl ring substituted silyloxy group in a polar organic solvent in the presence of a metal hydride, a transition metal salt and a tertiary amine base; and (b) separating the stable 1,2-dioxetane wherein OX is a silyloxy group.
Claim 28
Dependent Claim
18 words
The process of Claim 27 wherein the solvent is tetrahydrofuran and the metal hydride is lithium aluminum hydride.
Claim 29
Dependent Claim
18 words
The process of Claim 28 wherein the transition metal salt is titanium chloride and the base is triethylamine.
Claim 30
Dependent Claim
12 words
The process of Claim 27 conducted at the temperature of refluxing tetrahydrofuran.
Claim 31
Dependent Claim
19 words
The process of Claim 27 wherein in addition the silyl in the silyloxy group is replaced with another substituent.
Claim 32
Dependent Claim
28 words
The process of Claim 31 wherein the substituent with oxy is hydroxyl, alkyl or aryl carbonyl, alkyl, aryl or an inorganic oxy group derived from an oxy acid.
Claim 33
Dependent Claim
2 words
4-(6-hydroxy-2-naphthyl-4-methoxy spiro[I,2-dioxetane-3,2'adamantane].
Claim 34
Dependent Claim
2 words
4,-(6-tert-butyldimethylsilyloxy-2-naphthyl)-4-methoxy spiro[I,2-dioxetane-3,2'adamantane].
Claim 35
Dependent Claim
3 words
4-(6-acetoxyl-2-naphthyl)-4-methoxy spiro [I,2-dioxetane-3,2'adamantane].
Claim 36
Dependent Claim
1 words
Dispiro[adamantane-2,3'-[1,2]dioxetane-4',9'-(3-phosphate-9H-xanthene].
Claim 37
Dependent Claim
1 words
Dispiro[adamantane-2,3'-[1,2]dioxetane-4',9'(3-hydroxy-9H-xanthene].
Claim 38
Dependent Claim
1 words
Dispiro[adamantane-2,3'-[I,2]dioxetane-4',9"-(3-tert-butyldimethylsilyloxy-9H-xanthene].
Claim 39
Dependent Claim
2 words
Dispiro[adamantane-2,3'[1,2]dioxetane 4',9"-(3-acetoxy-9H-xanthene].
Claim 40
Dependent Claim
2 words
Dispiro[adamantane-2,3'[1,2,dioxetane 4',9"-(2-hydroxy-9H-fluorene].
Claim 41
Dependent Claim
3 words
Dispiro[adamantane,2,3'-[I,2-dioxetane 4',9"-(2-tert-butyldimethylsilyloxy-9H fluorene].
References Cited (Backward Citations)
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