US4125709A
Expired / Lapsed
US
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Polyhydroxy-alkyl-3,5-disubstituted-2,4,6-triiodocarbanilates
Assignee: Mallinckrodt Inc
•
Filing: 1974-10-04
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Granted: 1978-11-14
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Expires: 1994-10-04
Abstract
Abstract Certain polyhydroxy-alkyl-3,5-disubstituted-2,4,6-triiodocarbanilates are useful as x-ray contrast agents. Representative of this class of compounds is the compound 1-[N-(2,4,6-triiodo-3-N,N-dimethylcarbamyl-5-N-methylcarbamyl)carbanil yl]-L-sorbose.
Inventors
- 👤 Kenneth R. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 13:49
CPC Classifications
C; C07; C07H; C07H9/00; C07H9/02; C07H9/04; A; A61; A61K; A61K49/00; A61K49/04; A61K49/0433; A61K49/0438; C07C; C07C265/00; C07C265/12; C07H13/00; C07H13/12
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
98 words
A compound of the formula: ##STR25## wherein X and Y are each selected from the group consisting of lower alkoxy, hydroxy-(lower alkoxy), lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), hydroxy-lower acylamino, N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkylsulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl) carbamyl, lower alkoxy-(lower acylamino), lower alkoxyalkoxy-(lower acylamino), hydroxy and hydroxy-lower alkyl and Z is the monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said monovalent residue containing not more than 7 carbon atoms in its chain or ring.
Claim 2
Dependent Claim
98 words
A compound of the formula: ##STR25## wherein X and Y are each selected from the group consisting of lower alkoxy, hydroxy-(lower alkoxy), lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), hydroxy-lower acylamino, N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkylsulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl) carbamyl, lower alkoxy-(lower acylamino), lower alkoxyalkoxy-(lower acylamino), hydroxy and hydroxy-lower alkyl and Z is the monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said monovalent residue containing not more than 7 carbon atoms in its chain or ring.
Claim 3
Dependent Claim
50 words
A compound as set forth in claim 1 wherein one of X and Y is selected from the group consisting of hydrogen and a member of the group set forth in claim 1 and the other of X and Y is ##STR26## where Z is as defined in claim 1.
Claim 4
Dependent Claim
31 words
A compound as set forth in claim 1 wherein X and Y are each selected from the group consisting of lower acylamino, N-(lower alkyl)-lower acylamino, carbamyl, N-(lower alkyl)carbamyl and N,N-di-(lower alkyl)carbamyl.
Claim 5
Dependent Claim
34 words
A compound as set forth in claim 1 wherein X is N-methylcarbamyl, Y is N,N-dimethylcarbamyl and Z is the monovalent residue of the linear polyol which is the ketose L-sorbose, attached at the 1-position.
Claim 6
Dependent Claim
34 words
A compound as set forth in claim 1 wherein X is N-methylcarbamyl, Y is N-methylacetamido and Z is the monovalent residue of the linear polyol which is the aldose galactose, substituted at the 6-position.
Claim 7
Dependent Claim
131 words
A compound of the formula: ##STR27## wherein X and Y are each selected from the group consisting of lower alkoxy, lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkysulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl)carbamyl, lower alkoxy-(lower acylamino), lower alkoxy-alkoxy-(lower acylamino) functions and ester, acetal or ketal derivatives of hydroxy, hydroxy-lower alkyl, hydroxy-(lower alkoxy) and hydroxy-lower acylamino and Z p is selected from the group consisting of ester, acetal and ketal derivatives of a monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said derivatives containing at least one hydroxyl group in an unprotected form and said monovalent residue containing not more than 7 carbon atoms in its chain or ring.
Claim 8
Dependent Claim
131 words
A compound of the formula: ##STR27## wherein X and Y are each selected from the group consisting of lower alkoxy, lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkysulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl)carbamyl, lower alkoxy-(lower acylamino), lower alkoxy-alkoxy-(lower acylamino) functions and ester, acetal or ketal derivatives of hydroxy, hydroxy-lower alkyl, hydroxy-(lower alkoxy) and hydroxy-lower acylamino and Z p is selected from the group consisting of ester, acetal and ketal derivatives of a monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said derivatives containing at least one hydroxyl group in an unprotected form and said monovalent residue containing not more than 7 carbon atoms in its chain or ring.
Claim 9
Dependent Claim
26 words
A compound as set forth in claim 6 wherein said derivatives contain not more than one primary and one secondary hydroxyl group in an unprotected form.
Claim 10
Dependent Claim
51 words
A compound as set forth in claim 6 wherein one of X and Y is selected from the group consisting of hydrogen and a member of the group set forth in claim 6 and the other of X and Y is ##STR28## where Z p is as defined in claim 6.
Claim 11
Dependent Claim
31 words
A compound as set forth in claim 6 wherein X and Y are each selected from the group consisting of lower acylamino, N-(lower alkyl)-lower acylamino, carbamyl, N-(lower alkyl)carbamyl and N,N-di-(lower alkyl)carbamyl.
Claim 12
Dependent Claim
192 words
In a method for preparing a compound of the formula: ##STR29## wherein X and Y are each selected from the group consisting of lower alkoxy, hydroxy-(lower alkoxy), lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), hydroxy-lower acylamino, N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkylsulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl) carbamyl, lower alkoxy-(lower acylamino), lower alkoxy-alkoxy-(lower acylamino), hydroxy and hydroxy-lower alkyl and Z is the monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said monovalent residue containing not more than 7 carbon atoms in its chain or ring, the step which comprises reacting a compound of the formula: ##STR30## wherein X and Y are as defined above and R' is selected from the group consisting of isocyanate and carbamyl chloride functions, with a compound selected from the group consisting of the ester, acetal and ketal derivatives of a polyol selected from the group consisting of linear and branched chain polyols, said derivatives containing at least one hydroxyl group in an unprotected form and said polyol containing not more than 7 carbon atoms in its chain or ring.
Claim 13
Dependent Claim
192 words
In a method for preparing a compound of the formula: ##STR29## wherein X and Y are each selected from the group consisting of lower alkoxy, hydroxy-(lower alkoxy), lower alkoxy-(lower alkoxy), lower acylamino, lower acylamino-(lower alkyl), lower acylamino-(lower acylamino), hydroxy-lower acylamino, N-(lower alkyl)-lower acylamino, lower alkylsulfonamido, N-(lower alkyl)-lower alkylsulfonamido, 3,3-bis-(lower alkyl)-ureido, lower perfluoroacylamino, carbamyl, N-(lower alkyl)carbamyl, N,N-di-(lower alkyl) carbamyl, lower alkoxy-(lower acylamino), lower alkoxy-alkoxy-(lower acylamino), hydroxy and hydroxy-lower alkyl and Z is the monovalent residue of a polyol selected from the group consisting of linear and branched chain polyols, said monovalent residue containing not more than 7 carbon atoms in its chain or ring, the step which comprises reacting a compound of the formula: ##STR30## wherein X and Y are as defined above and R' is selected from the group consisting of isocyanate and carbamyl chloride functions, with a compound selected from the group consisting of the ester, acetal and ketal derivatives of a polyol selected from the group consisting of linear and branched chain polyols, said derivatives containing at least one hydroxyl group in an unprotected form and said polyol containing not more than 7 carbon atoms in its chain or ring.
Claim 14
Dependent Claim
34 words
A method as set forth in claim 10 wherein the product of said reaction is converted into a compound of the formula: ##STR31## wherein X, Y and Z are as defined in claim 10.
Claim 15
Dependent Claim
60 words
A method as set forth in claim 10 wherein one of X and Y is selected from the group consisting of hydrogen and a member of the group set forth in claim 10 and the other of X and Y is ##STR32## where Z is the monovalent residue of a polyol selected from the group set forth in claim 10.
Claim 16
Dependent Claim
31 words
A method as set forth in claim 10 wherein X and Y are each selected from the group consisting of lower acylamino, N-(lower alkyl)-lower acylamino, carbamyl, N-(lower alkyl)carbamyl and N,N-di-(lower alkyl)carbamyl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-13 | 1982-05-15 | 1982-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-13 | 1986-05-15 | 1986-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-13 | 1990-05-15 | 1990-11-14 | $7700.00 | Window Closed / Lapsed |