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US4350674A
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Substituted acetanilidoiminodiacetic acid compounds, diagnostic agents containing such compounds labeled with technetium-99m, and methods for making and using such compounds and agents
Assignee: CIS Bio International SA
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Filing: 1980-05-16
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Granted: 1982-09-21
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Expires: 2000-05-16
Abstract
Abstract What are disclosed are (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid and a method for its preparation from chloroacetic acid (2,3,4,5,6-pentafluoroanilide); (4-n-pentylacetanilido)-iminodiacetic acid and a method for its preparation from chloroacetic acid (4-n-pentylanilide); diagnostic agents for visualizing the heptobiliary system containing these substituted acetanilidoiminodiacetic acid compounds labeled with technetium-99m; and methods for making and using such diagnostic agents.
Inventors
- 👤 Michael Molter
- 👤 Gerhard Kloss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 22:26
CPC Classifications
A; A61; A61K; A61K51/00; A61K51/02; A61K51/04; A61K2123/00
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
3 words
Chloroacetic acid (2,3,4,5,6-pentafluoroanilide).
Claim 2
Dependent Claim
3 words
Chloroacetic acid (2,3,4,5,6-pentafluoroanilide).
Claim 3
Dependent Claim
17 words
A method for making the compound of claim 1 which comprises reacting 2,3,4,5,6-pentafluoroaniline with chloroacetic acid chloride.
Claim 4
Dependent Claim
6 words
(2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid or a salt thereof.
Claim 5
Dependent Claim
6 words
(2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid or a salt thereof.
Claim 6
Independent Claim
29 words
A method for making (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid which comprises reacting chloroacetic acid (2,3,4,5,6-pentafluoroanilide) with iminodiacetic acid in an alkaline medium to form a (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetate and recovering the free acid therefrom.
Claim 7
Independent Claim
29 words
A method for making (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid which comprises reacting chloroacetic acid (2,3,4,5,6-pentafluoroanilide) with iminodiacetic acid in an alkaline medium to form a (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetate and recovering the free acid therefrom.
Claim 8
Dependent Claim
21 words
A diagnostic agent for visualizing the heptobiliary system, which agent comprises a physiological saline solution of (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid labelled with technetium-99m.
Claim 9
Dependent Claim
21 words
A diagnostic agent for visualizing the heptobiliary system, which agent comprises a physiological saline solution of (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid labelled with technetium-99m.
Claim 10
Dependent Claim
37 words
A method for visualizing the heptobiliary system of a patient for purposes of scintigraphic examination, which method comprises intravenously administering to said patient an amount, effectively detectable by scintigraphy, of a diagnostic agent as in claim 5.
Claim 11
Dependent Claim
3 words
Chloroacetic acid (4-n-pentylanilide).
Claim 12
Dependent Claim
3 words
Chloroacetic acid (4-n-pentylanilide).
Claim 13
Dependent Claim
17 words
A method for making the compound of claim 7 which comprises reacting 4-n-pentylaniline with chloroacetic acid chloride.
Claim 14
Dependent Claim
6 words
(4-n-pentylacetanilido)-iminodiacetic acid or a salt thereof.
Claim 15
Dependent Claim
6 words
(4-n-pentylacetanilido)-iminodiacetic acid or a salt thereof.
Claim 16
Independent Claim
29 words
A method for making (4-n-pentylacetanilido)-iminodiacetic acid which comprises reacting chloroacetic acid (4-n-pentylanilide) with iminodiacetic acid in an alkaline medium to form a (4-n-pentylacetanilido)-iminodiacetate and recovering the free acid therefrom.
Claim 17
Independent Claim
29 words
A method for making (4-n-pentylacetanilido)-iminodiacetic acid which comprises reacting chloroacetic acid (4-n-pentylanilide) with iminodiacetic acid in an alkaline medium to form a (4-n-pentylacetanilido)-iminodiacetate and recovering the free acid therefrom.
Claim 18
Dependent Claim
21 words
A diagnostic agent for visualizing the heptobiliary system, which agent comprises a physiological salt solution of (4-n-pentylacetanilido)-iminodiacetic acid labelled with technetium-99m.
Claim 19
Dependent Claim
21 words
A diagnostic agent for visualizing the heptobiliary system, which agent comprises a physiological salt solution of (4-n-pentylacetanilido)-iminodiacetic acid labelled with technetium-99m.
Claim 20
Dependent Claim
37 words
A method for visualizing the hepatobiliary system of a patient for purposes of scintigraphic examination, which method comprises intravenously administering to said patient an amount, effectively detectable by scintigraphy, of a diagnostic agent as in claim 11.
Claim 21
Independent Claim
75 words
A method for making a diagnostic agent for liver function studies, which method comprises preparing an aqueous solution of a tin (II) compound and member selected from the group consisting of (2,3,4,5,6-pentafluoroacetanilido-iminodiacetic acid (PFIDA) and (4-n-pentylacetanilido)-iminodiacetic acid (PIDA) in a molar ratio from 1:10 to 1:200, adjusting the pH of the aqueous solution to a value between 4 and 9, and adding a physiological saline solution containing from 0.1 l to 100 millicuries of technetium-99m.
Claim 22
Independent Claim
75 words
A method for making a diagnostic agent for liver function studies, which method comprises preparing an aqueous solution of a tin (II) compound and member selected from the group consisting of (2,3,4,5,6-pentafluoroacetanilido-iminodiacetic acid (PFIDA) and (4-n-pentylacetanilido)-iminodiacetic acid (PIDA) in a molar ratio from 1:10 to 1:200, adjusting the pH of the aqueous solution to a value between 4 and 9, and adding a physiological saline solution containing from 0.1 l to 100 millicuries of technetium-99m.
Claim 23
Dependent Claim
25 words
A method as in claim 13 wherein said tin (II) compound is SnO, SnCl 2 .2H 2 O, SnSO 4 , Sn-tartrate, Sn-oxalate, or Sn-acetate.
Claim 24
Dependent Claim
22 words
A method as in claim 13 wherein the concentration of PFIDA or PIDA in said agent is from 0.1 to 200 mg/ml.
Claim 25
Dependent Claim
22 words
A method as in claim 13 wherein the concentration of PFIDA or PIDA in said agent is from 10 to 50 mg/ml.
Claim 26
Dependent Claim
22 words
A method as in claim 13 wherein the pH of said aqueous solution is adjusted to a value between 5.5 and 6.5.
Claim 27
Independent Claim
126 words
A method for making a labelling unit comprising a carrier for technetium-99m and adaptable for conversion to a diagnostic agent for visualizing the heptobiliary system by the addition thereto of a solution of technetium-99m, which method comprises preparing an aqueous solution of a tin (II) compound and a member selected from the group consisting of (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid and (4-n-pentylacetanilido)-iminodiacetic acid (PIDA) in a molar ratio from 1:10 to 1:200, adjusting the pH of the aqueous solution to a value between 4 and 9, dividing the aqueous solution into a plurality of portions each containing from 0.01 to 5 mg of said tin (II) compound and from 1 to 200 mg of PFIDA or PIDA, and lyophilizing said portions to provide a plurality of said labelling units.
Claim 28
Independent Claim
126 words
A method for making a labelling unit comprising a carrier for technetium-99m and adaptable for conversion to a diagnostic agent for visualizing the heptobiliary system by the addition thereto of a solution of technetium-99m, which method comprises preparing an aqueous solution of a tin (II) compound and a member selected from the group consisting of (2,3,4,5,6-pentafluoroacetanilido)-iminodiacetic acid and (4-n-pentylacetanilido)-iminodiacetic acid (PIDA) in a molar ratio from 1:10 to 1:200, adjusting the pH of the aqueous solution to a value between 4 and 9, dividing the aqueous solution into a plurality of portions each containing from 0.01 to 5 mg of said tin (II) compound and from 1 to 200 mg of PFIDA or PIDA, and lyophilizing said portions to provide a plurality of said labelling units.
Claim 29
Dependent Claim
33 words
A method as in claim 18 wherein said plurality of portions each containing from 0.1 to 0.5 mg of said tin (II) compound and from 10 to 50 mg of PFIDA or PIDA.
Claim 30
Dependent Claim
18 words
A method as in claim 18 wherein said pH is adjusted to a value between 5.5 and 6.5.
Claim 31
Dependent Claim
42 words
A method for making a diagnostic agent for liver function studies, which method comprises adding from 1 to 10 ml of a physiological saline solution containing from 0.1 to 100 milliCuries of technetium-99m pertechnetate to a labelling unit as in claim 18.
Claim 32
Dependent Claim
19 words
A method as in claim 21 wherein said saline solution contains from 1 to 10 milliCuries of technetium-99 pertechnetate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-20 | 1986-03-22 | 1986-09-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-20 | 1990-03-22 | 1990-09-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-20 | 1994-03-22 | 1994-09-21 | $7700.00 | Window Closed / Lapsed |