EP0195413A2
Expired / Lapsed
EP
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Substituted pyridine derivatives
Assignee: Baxter Healthcare Corp
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Filing: 1986-03-18
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Granted: —
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Expires: 2006-03-18
Abstract
Abstract It is disclosed that aryl-substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl] pyridines in which the aryl groups are substituted with one or more electron-releasing groups are an advantageous ligand for forming fluorescent chelates with rare earth metals. The pyridine moieties can be linked to target molecules, especially biologically active target molecules to provide fluorescent tagging for use in fluoroassay techniques. The pyridine moieties are disclosed as tetraacids, as salts and as esters. Preparation processes and precursors including the corresponding aryl-substituted 2,6-dicarboxypyridines as acids, salts and esters, are disclosed as well.
Inventors
- 👤 Ron L. Hale
- 👤 Dennis W. Solas
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 17:47
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/24; C07D213/36; C07D213/38; C07D405/00; C07D405/14; C07D473/00; C07D473/02; C07D473/04; C07D473/06; C07D473/08; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/532; G01N33/533; Y; Y10; Y10S; Y10S436/00; Y10S436/80
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
14 words
A fluorescently detectable molecule characterized as comprising a substituted aryl - substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl]pyridine moiety.
Claim 2
Dependent Claim
14 words
A fluorescently detectable molecule characterized as comprising a substituted aryl - substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl]pyridine moiety.
Claim 3
Dependent Claim
13 words
The fluorescently detectable molecule of claim 1 additionally comprising a biologically active material.
Claim 4
Dependent Claim
45 words
The fluorescently detectable molecule of one or both of the claims 1-2 wherein the substituted aryl group is an aryl group substituted with one or more electron-releasing groups, e.g. selected from among lower alkoxies, lower alkyls, aminos, dialkylaminos, aryls (including aralkyls) and aryloxys (including aralkyloxys).
Claim 5
Dependent Claim
145 words
The fluorescently detectable molecule of one or more of the claims 1-3 wherein said substituted aryl-substituted 2,6-bis[ N ,N-di(carboxylalkyl)aminoalkyl]pyridine moiety has the formula wherein n and n' are independently the integers 1 or 2, e.g.both being 1, Ar is an aryl, n" is an integer equal to the number of available bonding sites on Ar, M is hydrogen or metal ion, and the n" Rs, R' and R'' are each independently selected from hydrogen; electron-releasing groups including lower alkoxy, lower alkyl, amino, dialkylamino, aryl (including aralkyl) and aryloxy (including aralkyloxy); and a linking group including a covalent bond and a bridge group capable of providing a link to the remainder of the molecule subject to the provisos that at least one of the n" Rs is an electron-releasing group and that at least one of R', R" and the n" Rs is a linking group.
Claim 6
Dependent Claim
23 words
The fluorescently detectable molecule of claim 4 wherein Ar is phenyl and at least one of the n" Rs is a lower alkoxy.
Claim 7
Dependent Claim
36 words
The fluorescently detectable molecule of one or both of the claims 4-5, wherein the M's comprise one or more metal 1 ions including a rare earth metal ion in complex combination with the four carboxyl groups.
Claim 8
Dependent Claim
30 words
The fluorescently detectable molecule of one or more of the claims 1-6 wherein the remainder of the molecule to which the pyridine moiety is linked is a biologically active material.
Claim 9
Dependent Claim
125 words
A fluorescently detectable molecule of one or more of the claims 1-7, characterized as comprising a substituted aryl-substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl]pyridine moiety of the formula wherein M is hydrogen or metal ion, e.g. all M's being hydrogen, n and n' are independently the integers 1 or 2, e.g. both . being 1, the 5 Rs, R' and R" are each independently selected from a covalent bond, hydrogen and electron-releasing groups including lower alkoxy, lower alkyl, amino, dialkylamino, aryl and aryloxy, e.g. R' and R" being hydrogen, subject to the proviso that at least one or more of the 5 Rs is an . electron-releasing group and that at least one of R' and R" and the 5 Rs provides a link to the remainder of the molecule.
Claim 10
Dependent Claim
30 words
The fluorescently detectable molecule of claim 8 wherein the Ms comprise one or more metal ions including a rare earth metal ion in complex combination with the four carboxyl groups.
Claim 11
Dependent Claim
23 words
The fluorescently detectable molecule of one or both of the claims 8-9 wherein the remainder of the molecule comprises a biologically active material.
Claim 12
Dependent Claim
50 words
A fluorescently detectable specific binding reagent having the structure wherein M is metal ion or hydrogen, e.g. each M being hydrogen or a metal ion, n * is an integer from 1 to 4, Alk is a 1 to 4 carbon alkyl and M B is a biologically active material.
Claim 13
Dependent Claim
50 words
A fluorescently detectable specific binding reagent having the structure wherein M is metal ion or hydrogen, e.g. each M being hydrogen or a metal ion, n * is an integer from 1 to 4, Alk is a 1 to 4 carbon alkyl and M B is a biologically active material.
Claim 14
Dependent Claim
27 words
The reagent of claim 11 wherein M comprises one or more metal ions including a rare earth metal ion in complex combination with the four carboxyl groups.
Claim 15
Dependent Claim
70 words
A substituted aryl-substituted 2,6- bis[N,N-di(carboxyalkyl)aminoalkyl]pyridine compound of the formula wherein n and n' are independently the integers 1 or 2, e.g. both being 1, and R, R' and R" are independently selected from hydrogens, and electron-releasing groups including lower alkoxies, lower alkyls, aminos, dialkylaminos, aryls (including aralkyls) and aryloxys (including aralkyloxys),and Ar is an aryl, and n" is an integer equal to the number of available bonding sites on Ar.
Claim 16
Dependent Claim
70 words
A substituted aryl-substituted 2,6- bis[N,N-di(carboxyalkyl)aminoalkyl]pyridine compound of the formula wherein n and n' are independently the integers 1 or 2, e.g. both being 1, and R, R' and R" are independently selected from hydrogens, and electron-releasing groups including lower alkoxies, lower alkyls, aminos, dialkylaminos, aryls (including aralkyls) and aryloxys (including aralkyloxys),and Ar is an aryl, and n" is an integer equal to the number of available bonding sites on Ar.
Claim 17
Dependent Claim
19 words
The compound of claim 13, wherein at-least one of the R', R" and the n" Rs is an amine.
Claim 18
Dependent Claim
22 words
The compound of one or both of the claims 13-14 wherein one of R', R" and the n Rs is an amine.
Claim 19
Dependent Claim
13 words
The compound of claim 15 wherein said amine is converted to an isothiocyanate.
Claim 20
Dependent Claim
27 words
The compound of one or more of the claims 11-16 wherein R and R" are hydrogens and Ar is phenyl such that the compound has the formula
Claim 21
Dependent Claim
76 words
A substituted aryl-substituted 2,6-dicarboxy pyridine compound of the formula wherein Ar is an aryl, n" is an integer equal to the number of available bonding sites on Ar, R, R' and R" are independently selected from hydrogen, and electron-releasing groups including lower alkoxy, lower alkyl, amino; dialkylamino, aryl and aryloxy, and R * and R ** are independently selected from among hydrogens and lower alkyls, e.g. one of them or both being hydrogen or lower alkyls.
Claim 22
Dependent Claim
76 words
A substituted aryl-substituted 2,6-dicarboxy pyridine compound of the formula wherein Ar is an aryl, n" is an integer equal to the number of available bonding sites on Ar, R, R' and R" are independently selected from hydrogen, and electron-releasing groups including lower alkoxy, lower alkyl, amino; dialkylamino, aryl and aryloxy, and R * and R ** are independently selected from among hydrogens and lower alkyls, e.g. one of them or both being hydrogen or lower alkyls.
Claim 23
Independent Claim
31 words
The method for detecting the presence of the molecule of one or more of the claims 1-12 which comprises photometrically exciting said molecule and detecting a fluorescent emission from said molecule.
Claim 24
Dependent Claim
50 words
The method of claim 19 wherein said exciting is carried out with a pulse of radiation, said pulse having a pluse duration which is short compared to the fluorescent decay lifetime of said molecule and detecting the fluorescence of said molecule after the fluorescence of ambient substances has substantially decayed.
References Cited (Backward Citations)
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