Patent US3963697A successfully refreshed from Google Patents.
US3963697A
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Labelled cardiotonic glycosides for use in radioimmunoassay
Assignee: Curtis Nuclear Corp
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Filing: 1974-08-29
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Granted: 1976-06-15
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Expires: 1994-08-29
Abstract
Abstract Disclosed are radioactive cardiotonic glycosides and a process of making such glycosides, the compounds being useful for radioimmunoassay of body fluids for cardiotonic glycoside content. The novel synthesis comprises reaction of a hydroxyl group of the sugar with a dicarboxylic acid derivative such as a diacid, diacid anhydride or a diacyl halide and thereafter reacting the free carboxylic group with a compound which will undergo electrophilic substitution reactions. A radioactive isotope, preferably 125 I, is reacted via electrophilic substitution with the compound to form the radioactive cardiotonic glycoside.
Inventors
- 👤 Robert F. Coombes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 18:50
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/58; G01N33/60; C; C07; C07J; C07J19/00; C07J19/005
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
52 words
A radioactive glycoside useful in radioimmunoassay of the formula: ##SPC8## wherein R 1 and R 2 are selected from the group consisting of hydroxyl or hydrogen and R 3 is selected from the group consisting of mono-, di-, tri-, and tetrasaccharides bonded to an 125 L-labeled substituent through a sugar hydroxyl group.
Claim 2
Dependent Claim
52 words
A radioactive glycoside useful in radioimmunoassay of the formula: ##SPC8## wherein R 1 and R 2 are selected from the group consisting of hydroxyl or hydrogen and R 3 is selected from the group consisting of mono-, di-, tri-, and tetrasaccharides bonded to an 125 L-labeled substituent through a sugar hydroxyl group.
Claim 3
Dependent Claim
35 words
The compound of claim 1 wherein R 3 is a mono- or oligo- saccharide with monomeric constituents selected from the group consisting of rhamnose, antiarose, digitalose, thevetose, talomethylose, digitoxose, cymarose, oleandrose, sarmentose, boivinose, and diginose.
Claim 4
Dependent Claim
85 words
A radioactive glycoside useful in radioimmunoassay of the formula: ##SPC9## wherein R 1 and R 2 are H or OH, R 4 is glucose, hydrogen or X, and R 5 is hydrogen, acetyl or X, X being an 125 I-substituted aromatic moiety conjugated to the glycoside chain via the condensation residue of a dicarboxylic acid, acid halide or acid anhydride, provided that one of R 4 or R 5 is X unless R 4 is glucose, in which case glucose is likewise conjugated to X.
Claim 5
Dependent Claim
85 words
A radioactive glycoside useful in radioimmunoassay of the formula: ##SPC9## wherein R 1 and R 2 are H or OH, R 4 is glucose, hydrogen or X, and R 5 is hydrogen, acetyl or X, X being an 125 I-substituted aromatic moiety conjugated to the glycoside chain via the condensation residue of a dicarboxylic acid, acid halide or acid anhydride, provided that one of R 4 or R 5 is X unless R 4 is glucose, in which case glucose is likewise conjugated to X.
Claim 6
Dependent Claim
26 words
The compound of claim 3 wherein the dicarboxylic acid derivative of the radioactive phenol bears a radioactive isotope ortho to the hydroxyl of the phenol ring.
Claim 7
Dependent Claim
14 words
The compound of claim 3 wherein the phenol is tyrosine or a tyrosine derivative.
Claim 8
Dependent Claim
12 words
The compound of claim 5 wherein the phenol is tyrosine methyl ester.
Claim 9
Dependent Claim
25 words
The compound of claim 3 wherein said residue is selected from the group consisting of succinyl, carbonyl, oxaloyl, malonyl, glutaryl, adipoyl, pimeloyl, maleyl or phthaloyl.
Claim 10
Dependent Claim
76 words
The compound of claim 3 wherein X is of the formula: ##EQU1## wherein R 6 is selected from the group consisting of C 1 to C 6 alkyl, vinylene, and phenylene, R 7 is selected from the group consisting of H and C 1 to C 6 alkyl, R 8 and R 9 are selected from the group consisting of H and 125 I, at least one of R 8 and R 9 being 125 I.
Claim 11
Dependent Claim
8 words
The compound 125 I-(3'"-succinyl digoxin tyrosine methyl ester).
Claim 12
Dependent Claim
8 words
The compound 125 I-(3'"-succinyl digoxin tyrosine methyl ester).
Claim 13
Dependent Claim
8 words
The compound 125 I-(4'"succinyl digoxin tyrosine methyl ester).
Claim 14
Dependent Claim
8 words
The compound 125 I-(4'"succinyl digoxin tyrosine methyl ester).
Claim 15
Dependent Claim
8 words
The compound 125 I-(3'"-succinyl digitoxin tyrosine methyl ester).
Claim 16
Dependent Claim
8 words
The compound 125 I-(3'"-succinyl digitoxin tyrosine methyl ester).
Claim 17
Dependent Claim
7 words
The compound 125I-(4'"-succinyl digitoxin tyrosine methyl ester).
Claim 18
Dependent Claim
7 words
The compound 125I-(4'"-succinyl digitoxin tyrosine methyl ester).
Claim 19
Dependent Claim
6 words
The compound 125 I-(3'"-succinyl digoxin tyrosine)
Claim 20
Dependent Claim
6 words
The compound 125 I-(3'"-succinyl digoxin tyrosine)
Claim 21
Dependent Claim
6 words
The compound 125 I-(4'"-succinyl digoxin tyrosine).
Claim 22
Dependent Claim
6 words
The compound 125 I-(4'"-succinyl digoxin tyrosine).
Claim 23
Dependent Claim
6 words
The compound 125 I-(3'"-succinyl digitoxin tyrosine).
Claim 24
Dependent Claim
6 words
The compound 125 I-(3'"-succinyl digitoxin tyrosine).
Claim 25
Dependent Claim
6 words
The compound 125 I-(4'"-succinyl digitoxin tyrosine).
Claim 26
Dependent Claim
6 words
The compound 125 I-(4'"-succinyl digitoxin tyrosine).
Claim 27
Dependent Claim
117 words
A process of synthesizing a radioactive glycoside useful for radioimmunoassay comprising the steps of reacting a steroid glycoside of the general formula: ##SPC10## wherein R 1 and R 2 are selected from the group consisting of H or hydroxyl, R 4 is selected from the group consisting of H or glucose and R 5 is selected from the group consisting of hydrogen or acetyl with a reagent selected from the group consisting of a diacid, diacid anhydride or a diacidhalide to provide the corresponding dicarboxylic acid derivative conjugated at a sugar hydroxyl and further reacting the resulting dicarboxylic acid derivative with an aromatic moeity activated toward electrophilic substitution effecting electrophilic substitution of said moiety with 125 I.
Claim 28
Dependent Claim
117 words
A process of synthesizing a radioactive glycoside useful for radioimmunoassay comprising the steps of reacting a steroid glycoside of the general formula: ##SPC10## wherein R 1 and R 2 are selected from the group consisting of H or hydroxyl, R 4 is selected from the group consisting of H or glucose and R 5 is selected from the group consisting of hydrogen or acetyl with a reagent selected from the group consisting of a diacid, diacid anhydride or a diacidhalide to provide the corresponding dicarboxylic acid derivative conjugated at a sugar hydroxyl and further reacting the resulting dicarboxylic acid derivative with an aromatic moeity activated toward electrophilic substitution effecting electrophilic substitution of said moiety with 125 I.
Claim 29
Dependent Claim
20 words
The process of claim 17 wherein the aromatic moiety selected from the group consisting of tyrosine or a tyrosine ester.
Claim 30
Dependent Claim
26 words
The process of claim 17 wherein the diacid or diacidanhydride is selected from the group consisting of succinnic acid, glutaric acid, succinic anhydride or glutaric anhydride.
Claim 31
Dependent Claim
12 words
The compound of claim 3 wherein said aromatic moiety is a phenol.
Claim 32
Dependent Claim
18 words
The compound of claim 20 wherein 125 I is ortho to the hydroxy substituent of the phenol ring.
References Cited (Backward Citations)
US3843628A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-15 | 1979-12-15 | 1980-06-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-15 | 1983-12-15 | 1984-06-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-15 | 1987-12-15 | 1988-06-15 | $7700.00 | Window Closed / Lapsed |