EP0194843A2
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EP
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Complexes of technetium-99m with propylene amine oximes
Assignee: GE Healthcare Ltd
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Filing: 1986-03-10
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Granted: —
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Expires: 2006-03-10
Abstract
Abstract A family of propylene amine oxime ligands has the formula 2 wherein preferably R 1 is C1-C4 alkyl or phenyl and each of R, R 2 , R 3 and R 4 is H or C1-C4 alkyl. The technetium-99m complexes of these ligands are lipophilic neutral complexes useful as diagnostic radiopharmaceuticals and particularly for brain scanning. The ligands show stereoisomerism. The preparation and properties of the d1- and mesostereoisom- ers, and of the d- and 1-enantiomers, are described. The 1-enantiomer and the d1-stereoisomer of the preferred compound (2, R=R 1 =R 2 =CH 3 , R 3 = R 4 = H ) show good retention in the brain.
Inventors
- 👤 Lewis Rueben Canning
- 👤 David Peter Nowotnik
- 👤 Rudi Dominique Neirinckx
- 👤 Ian Michael Piper
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 20:39
CPC Classifications
A; A61; A61K; A61K51/00; A61K51/02; A61K51/04
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
173 words
A lipophilic macrocyclic complex, useful as a diagnostic radiopharmaceutical, of Technetium-99m with a pronylene amine oxime ligand having the formula 2:- wherein each group may be the same or different at different positions in the molecule and where R is H, alkyl, aryl, cycloalkyl, CF 3 , CONX 2 or C 6 H 4 OCH 3 . R is alkyl, aryl, cycloalkyl or CF 3 , or R and R together form part of a cycloalkyl ring, each of R 2 , R 3 and R 4 is H, alkyl, aryl, cycloalkyl or CF 3 , and X is H, CH 3 , C 2 H 5 or C 6 H 5 , wherein the ligand of formula 2 is in the form of a single stereoisomer or of a mixture of 2 or more such stereoisomers, provided that, where R is methyl and R is methyl and R 2 , R 3 and R 4 are hydrogen, a mixture of 3 such stereoisomers contains an artificially high concentration of one of them.
Claim 2
Dependent Claim
173 words
A lipophilic macrocyclic complex, useful as a diagnostic radiopharmaceutical, of Technetium-99m with a pronylene amine oxime ligand having the formula 2:- wherein each group may be the same or different at different positions in the molecule and where R is H, alkyl, aryl, cycloalkyl, CF 3 , CONX 2 or C 6 H 4 OCH 3 . R is alkyl, aryl, cycloalkyl or CF 3 , or R and R together form part of a cycloalkyl ring, each of R 2 , R 3 and R 4 is H, alkyl, aryl, cycloalkyl or CF 3 , and X is H, CH 3 , C 2 H 5 or C 6 H 5 , wherein the ligand of formula 2 is in the form of a single stereoisomer or of a mixture of 2 or more such stereoisomers, provided that, where R is methyl and R is methyl and R 2 , R 3 and R 4 are hydrogen, a mixture of 3 such stereoisomers contains an artificially high concentration of one of them.
Claim 3
Dependent Claim
37 words
A complex as claimed in claim 1, wherein R is H or C1-C4 alkyl, R 1 is C1-C4 alkyl or phenyl, and, each of R 2 , R 3 and R 4 is H or C1-C4 alkyl.
Claim 4
Dependent Claim
45 words
A complex as claimed in claim 1 or claim 2, wherein the two groups R are the same, the two groups R are the same, the two groups R 2 are the same, and the four groups R 3 and R 4 are the same.
Claim 5
Dependent Claim
36 words
A complex as claimed in claim 1, claim 2 or claim 3, wherein the ligand is in the form of a dl-diastereoisomer or of a mixture of isomers containing an artificially high concentration of the dl-diastereoisomer.
Claim 6
Dependent Claim
15 words
A complex as claimed in claim 1, wherein the ligand is 4, 8-diaza-3,6,6,9-tetramethylundecane-2,10-dione bis oxime.
Claim 7
Dependent Claim
13 words
A complex as claimed in claim 5, wherein the ligand is the dl-diastereoisomer.
Claim 8
Dependent Claim
13 words
A complex as claimed in claim 5, wherein the ligand is the 1-enantiomer.
Claim 9
Dependent Claim
13 words
A complex as claimed in claim 5, wherein the ligand is the d-enantiomer.
Claim 10
Dependent Claim
157 words
A propylene amine oxime ligand having the formula 2:- wherein each group may be the same or different at different positions in the molecule and where'R is H, alkyl, aryl, cycloalkyl, CF 3 , CONX 2 or C 6 H 4 OCH 3 . R is alkyl, aryl, cycloalkyl or CF 3 , or R and R 1 together form part of a cycloalkyl ring, each of R 2 , R 3 and R 4 is H, alkyl, aryl, cycloalkyl or CF 3 , and X is H, CH 3 , C 2 H 5 or C 6 H 5 , wherein the ligand of formula 2 is in the form of a single stereoisomer or of a mixture of 2 or 3 such stereoisomers, provided that, where R is methyl and R 1 is methyl and R 2 is hydrogen or methyl, a mixture of.3 such stereoisomers contains an artificially high concentration of one of them.
Claim 11
Dependent Claim
157 words
A propylene amine oxime ligand having the formula 2:- wherein each group may be the same or different at different positions in the molecule and where'R is H, alkyl, aryl, cycloalkyl, CF 3 , CONX 2 or C 6 H 4 OCH 3 . R is alkyl, aryl, cycloalkyl or CF 3 , or R and R 1 together form part of a cycloalkyl ring, each of R 2 , R 3 and R 4 is H, alkyl, aryl, cycloalkyl or CF 3 , and X is H, CH 3 , C 2 H 5 or C 6 H 5 , wherein the ligand of formula 2 is in the form of a single stereoisomer or of a mixture of 2 or 3 such stereoisomers, provided that, where R is methyl and R 1 is methyl and R 2 is hydrogen or methyl, a mixture of.3 such stereoisomers contains an artificially high concentration of one of them.
Claim 12
Dependent Claim
12 words
A ligand as claimed in claim 9 which is 4,8-diaza-3,6,6,9-tetramethylundecane-2,10-dione bis oxime.
Claim 13
Dependent Claim
13 words
A ligand as claimed in claim 10 in the form of the dl-diastereoisomer.
Claim 14
Dependent Claim
13 words
A ligand as claimed in claim 10 in the form of the 1-enantiomer.
Claim 15
Dependent Claim
13 words
A ligand as claimed in claim 10 in the form of the d-enantiomer.
References Cited (Backward Citations)
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