US2001020087A1PendingUtilityA1
Imidazolinone haptens and antigens and enzyme conjugates prepared therefrom
Est. expiryNov 3, 2014(expired)· nominal 20-yr term from priority
C07K 16/44C07D 401/04Y10S530/809Y10S424/807Y10S530/808G01N 33/5308G01N 33/535
53
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Claims
Abstract
The present invention provides an imidazolinone hapten having the structural formula Further provided are an antigen and an enzyme conjugate which are prepared from the imidazolinone hapten. The haptens, antigens and enzyme conjugates provided are useful in immunoassays for determining the presence and concentration of an imidazolinone compound in the presence of one or more other imidazolinone compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An imidazolinone hapten having the structural formula
wherein
R is hydrogen or C 1 -C 4 alkyl;
R 1 is C 1 -C 4 alkyl;
R 2 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and when R 1 and R 2 are taken together with the carbon atom to which they are attached they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl;
Y and Z are each independently hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 halo-alkyl, nitro, cyano, C 1 -C 4 alkylamino, di(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylsulfonyl or phenyl optionally substituted with one C 1 -C 4 alkyl group, C 1 -C 4 alkoxy group or halogen atom; and when taken together, Y and Z may form a ring in which YZ are represented by the structure: -(CH 2 ) n -, where n is an integer of 3 or 4; or
where R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy;
A is N or CH;
W is C 3 -C 12 alkylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom,
C 3 -C 12 alkenylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom, or
C 3 -C 12 alkynylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom; and
W 1 is C 1 -C 12 alkylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom,
C 2 -C 12 alkenylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom, or
C 3 -C 12 alkynylene optionally substituted with one or two C 1 -C 3 alkyl groups, C 1 -C 3 alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom.
2 . The imidazolinone hapten according to claim 1 wherein
R is hydrogen or methyl;
R 1 is methyl;
R 2 is isopropyl;
Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxyalkyl;
Z is hydrogen; and when taken together, Y and Z may form a ring in which YZ is represented by the structure: —CH═CH—CH═CH—;
A is N or CH;
W is C 3 -C 12 alkylene or C 3 -C 12 alkenylene; and
W 1 is C 1 -C 12 alkylene or C 2 -C 12 alkenylene.
3 . The imidazolinone hapten according to claim 2 wherein
R is hydrogen or methyl;
R 1 is methyl;
R 2 is isopropyl;
Y is hydrogen, methyl, ethyl or methoxymethyl;
Z is hydrogen; and when taken together, Y and Z may form a ring in which YZ is represented by the structure: —CH═CH—CH═CH—;
A is N;
W is C 3 -C 6 alkylene or C 3 -C 6 alkenylene; and
W 1 is C 1 -C 6 alkylene or C 2 -C 6 alkenylene.
4 . The imidazolinone hapten according to claim 3 ,
6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoic acid.
5 . The imidazolinone hapten according to claim 3 ,
2-(5-ethyl-2-pyridyl) -4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-valeric acid.
6 . The imidazolinone hapten according to claim 3 ,
4-[5-ethyl-2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]butyric acid.
7 . The imidazolinone hapten according to claim 3 ,
2-(5-ethyl-2-pyridyl) -4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonic acid, (E)-.
8 . The imidazolinone hapten according to claim 3 ,
2-(5-ethyl-2-pyridyl) -4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetic acid.
9 . The imidazolinone hapten according to claim 3 ,
4-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-N-methylnicotinamido]butyric acid.
10 . An antigen having the structural formula
wherein
R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 1 ;
X is an integer from about 1 to 40; and
Q is a protein.
11 . The antigen according to claim 10 wherein the protein is selected from the group consisting of cationized bovine serum albumin, keyhole limpet hemocyanin, ovalbumin, bovin serum albumin, thyroglobulin, human serum albumin and fibrinogen.
12 . The antigen according to claim 10 wherein R, R 1 , R 2 , Y, Z, A, is and W 1 are as described in claim 2 .
13 . The antigen according to claim 12 wherein R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 3 .
14 . The antigen according to claim 13 having the structural formula
wherein
X is an integer from about 1 to 40; and
KLH is keyhole limpet hemocyanin.
15 . The antigen according to claim 13 having the structural formula
wherein
X is an integer from about 1 to 40; and
cBSA is cationized bovine serum albumin.
16 . The antigen according to claim 13 having the structural formula
wherein
X is an integer from about 1 to 40; and
KLH is keyhole limpet hemocyanin.
17 . The antigen according to claim 13 having the structural formula
wherein
X is an integer from about 1 to 40; and
cBSA is cationized bovine serum albumin.
18 . The antigen according to claim 13 having the structural formula
wherein
X is an integer from about 1 to 40; and
OVA is ovalbumin
19 . An enzyme conjugate having the structural formula
wherein
R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 1 ;
and E is an enzyme.
20 . The enzyme conjugate according to claim 19 wherein the enzyme is selected from the group consisting of alkaline phosphatase, horseradish peroxidase, urease, glucose oxidase and galactosidase.
21 . The enzyme conjugate according to claim 19 wherein R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 2 .
22 . The enzyme conjugate according to claim 21 wherein R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 3 .
23 . The enzyme conjugate according to claim 22 having the structural formula
wherein E is alkaline phosphatase.
24 . A compound having the structural formula
wherein
R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 1 ;
and R 7 is C 1 -C 4 alkyl.
25 . The compound according to claim 24 wherein R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 2 .
26 . The compound according to claim 25 wherein R, R 1 , R 2 , Y, Z, A, W and W 1 are as described in claim 3 ; and
R 7 is methyl or ethyl.
27 . The compound according to claim 26 , methyl 6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoate.
28 . The compound according to claim 26 , methyl 4-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]butyrate.
29 . The compound according to claim 26 , ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonate, (E)-.
30 . The compound according to claim 26 , ethyl 2-(5-ethyl-2-pyridyl) -4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetate.
31 . The compound according to claim 26 , ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-valerate.Join the waitlist — get patent alerts
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