US4269819A
Expired / Lapsed
US
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2,4,6-Triiodobenzonitrile derivatives and X-ray contrast media comprising them
Assignee: Bayer Pharma AG
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Filing: 1979-07-12
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Granted: 1981-05-26
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Expires: 1999-07-12
Abstract
Abstract 2,4,6-Triiodobenzonitriles of the formula <IMAGE> wherein Z is a direct bond or alkylene, X is -COOH or -NR1R2 wherein R1 is H or hydrocarbon or hydroxy-hydrocarbon and R2 is lower acyl, and Y is H or -COOH, and their simple esters, amides and pharmaceutically acceptable salts, are useful as X-ray contrast agents and can be prepared by diazotizing the corresponding 2,4,6-triiodoanilines followed by reaction with a metal cyanide.
Inventors
- 👤 Heinz Gries
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:54
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/49; C07C255/57
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
184 words
A compound of the formula ##STR6## wherein Z is a direct bond or alkylene or alkenylene of up to 7 carbon atoms; X is --COOH or ##STR7## wherein R 1 is a hydrogen atom or alkyl or hydroxy alkyl of up to 4 carbon atoms or a corresponding hydroxy alkyl group, and R 2 is the acyl radical of a hydrocarbon carboxylic acid of 2 to 5 carbon atoms or of a corresponding hydroxy carboxylic acid, and Y is a hydrogen atom or --COOH; and the physiologically acceptable salts with bases, and the corresponding esters and acid amides of the above compounds wherein at least one of X and Y is (a) of the formula --CO--OR wherein R is hydrocarbon of 1-4 carbon atoms or a corresponding hydrocarbon group substituted by one or more hydroxy groups, or (b) of the formula --CO--NR 3 --R 4 wherein R 3 and R 4 each is a hydrogen atom or alkyl of 1-4 carbon atoms or corresponding alkyl substituted by 1-3 hydroxy groups, or (c) of the formula --CO--NH--R 5 wherein R 5 is methyl or ethyl.
Claim 2
Dependent Claim
184 words
A compound of the formula ##STR6## wherein Z is a direct bond or alkylene or alkenylene of up to 7 carbon atoms; X is --COOH or ##STR7## wherein R 1 is a hydrogen atom or alkyl or hydroxy alkyl of up to 4 carbon atoms or a corresponding hydroxy alkyl group, and R 2 is the acyl radical of a hydrocarbon carboxylic acid of 2 to 5 carbon atoms or of a corresponding hydroxy carboxylic acid, and Y is a hydrogen atom or --COOH; and the physiologically acceptable salts with bases, and the corresponding esters and acid amides of the above compounds wherein at least one of X and Y is (a) of the formula --CO--OR wherein R is hydrocarbon of 1-4 carbon atoms or a corresponding hydrocarbon group substituted by one or more hydroxy groups, or (b) of the formula --CO--NR 3 --R 4 wherein R 3 and R 4 each is a hydrogen atom or alkyl of 1-4 carbon atoms or corresponding alkyl substituted by 1-3 hydroxy groups, or (c) of the formula --CO--NH--R 5 wherein R 5 is methyl or ethyl.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein Y is H.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein Y is --COOH.
Claim 5
Dependent Claim
12 words
A compound of claim 1 wherein wherein Z is a direct bond.
Claim 6
Dependent Claim
13 words
A compound of claim 4 wherein X is --NR 1 R 2 .
Claim 7
Dependent Claim
12 words
A compound of claim 5 wherein R 1 is a hydrogen atom.
Claim 8
Dependent Claim
15 words
A compound of claim 1 wherein Z is alkylene of up to 4 carbon atoms.
Claim 9
Dependent Claim
13 words
A compound of claim 7 wherein X is --NR 1 R 2 .
Claim 10
Dependent Claim
12 words
A compound of claim 8 wherein R 1 is a hydrogen atom.
Claim 11
Dependent Claim
7 words
5-Cyano-2,4,6-triiodoisophthalic acid, a compound of claim 1.
Claim 12
Dependent Claim
8 words
5-Cyano-2,4,6-triiodoisophthalic acid monomethylamide, a compound of claim 1.
Claim 13
Dependent Claim
8 words
5-Cyano-2,4,6-triiodoisophthalic acid bis(2-hydroxyethyl)amide, a compound of claim 1.
Claim 14
Dependent Claim
7 words
5-Cyano-2,4,6-triiodobenzoic acid, a compound of claim 1.
Claim 15
Dependent Claim
7 words
β-(2,4,6-Triiodo-3-cyanophenyl-)α-ethylpropionic acid, a compound of claim 1.
Claim 16
Dependent Claim
7 words
5-Cyano-3-acetylamino-2,4,6-triiodobenzoic acid, a compound of claim 1.
Claim 17
Dependent Claim
7 words
3-Cyano-5-acetylaminomethyl-2,4,6-triiodobenzoic acid, a compound of claim 1.
Claim 18
Dependent Claim
8 words
5-Cyano-2,4,6-triiodoisophthalic acid mono-N-(2-hydroxyethyl)amide, a compound of claim 1.
Claim 19
Dependent Claim
8 words
5-Cyano-2,4,6-triiodoisophthalic acid monoamide, a compound of claim 1.
Claim 20
Dependent Claim
30 words
An X-ray contrast agent adapted for oral or intravenous administration comprising a radiopaque amount per unit dosage of a compound of claim 1, in admixture with a pharmaceutically acceptable carrier.
Claim 21
Dependent Claim
27 words
A method for conducting a radiological examination of a patient which comprises administering systemically thereto prior to examination a radiopaque amount of a compound of claim 1.
References Cited (Backward Citations)
DE1467994A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-25 | 1984-11-24 | 1985-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-25 | 1988-11-24 | 1989-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-25 | 1992-11-24 | 1993-05-26 | $7700.00 | Window Closed / Lapsed |