Patent US5315035A successfully refreshed from Google Patents.
US5315035A
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Aniline derivatives useful as color formers
Assignee: Roche Diagnostics GmbH
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Filing: 1991-12-23
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Granted: 1994-05-24
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Expires: 2011-12-23
Abstract
Abstract The present invention is concerned with aniline derivatives of the general formula: <IMAGE> (I) wherein R1 is hydrogen or a lower alkyl or aryl, R2 is hydrogen or a lower alkyl which can be substituted by hydroxyl, amino carboxyl, lower alkoxycarbonyl, lower alkanoylamide lower alkyl or aryl or by a group of the structure <IMAGE> is which R5 and R6 have the meanings given hereinafter, R3 is a hydrogen or halogen atom or a carboxyl group, R4 and R'4, which can be the same or different, are hydrogen or halogen, carboxyl or lower alkoxy or lower alkyl radicals which are preferably in the m-position, R5 is hydrogen or a lower alkyl and R6 is hydroxyl or a lower alkoxy, lower alkyl or aryl radical; and of the salts thereof with acids and bases useful as a color former in the Trinder reaction for the detection of hydrogen peroxide or hydrogen peroxide-forming systems or peroxidase or peroxidate-acting substances or together with an oxidation agent for the detection of aromatic amines or of systems forming such amines.
Inventors
- 👤 Gunter Frey
- 👤 Gerd Zimmermann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 18:55
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C12; C12Q; C12Q1/00; C12Q1/34; C07F9/30; C07F9/301; C07F9/32; C07F9/3205; C07F9/3211; C07F9/3804; C07F9/3808; C07F9/40; C07F9/4003; C07F9/4006; C07F9/547; C07F9/553; C07F9/572; C07F9/5728; C07F9/576; C07F9/60; C07F9/6564; C07F9/6581; C07F9/6584; C12Q1/26; C12Q1/28; C12Q2326/00; Y; Y10; Y10T; Y10T436/00; Y10T436/17; Y10T436/173845; Y10T436/20; Y10T436/206664
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
175 words
An aniline derivative of the formula: ##STR25## wherein R 1 is hydrogen, C 1 -C 6 alkyl, C 6 -C 10 aryl or C 6 -C 10 aryl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, fluorine, chlorine or bromine; R 2 is hydrogen; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted by hydroxyl, amino, carboxyl, lower alkoxycarbonyl, lower alkanoylamido, C 6 -C 10 aryl lower alkyl with 1 to 6 carbon in the alkyl, or C 6 -C 10 aryl, or substituted by a group of the structure: ##STR26## in which R' 6 is hydroxyl, C 1 -C 6 alkyl or C 6 -C 10 aryl; R 3 is fluorine, chlorine or bromine or carboxyl; R 4 and R' 4 , which can be the same or different, are hydrogen, fluorine, chlorine, bromine, iodine, carboxyl, C 1 -C 6 alkoxy or C 1 -C 6 alkyl; and the salts thereof with acids and bases with the proviso that, R 4 and R' 4 cannot simultaneously be hydrogen.
Claim 2
Dependent Claim
175 words
An aniline derivative of the formula: ##STR25## wherein R 1 is hydrogen, C 1 -C 6 alkyl, C 6 -C 10 aryl or C 6 -C 10 aryl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, fluorine, chlorine or bromine; R 2 is hydrogen; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted by hydroxyl, amino, carboxyl, lower alkoxycarbonyl, lower alkanoylamido, C 6 -C 10 aryl lower alkyl with 1 to 6 carbon in the alkyl, or C 6 -C 10 aryl, or substituted by a group of the structure: ##STR26## in which R' 6 is hydroxyl, C 1 -C 6 alkyl or C 6 -C 10 aryl; R 3 is fluorine, chlorine or bromine or carboxyl; R 4 and R' 4 , which can be the same or different, are hydrogen, fluorine, chlorine, bromine, iodine, carboxyl, C 1 -C 6 alkoxy or C 1 -C 6 alkyl; and the salts thereof with acids and bases with the proviso that, R 4 and R' 4 cannot simultaneously be hydrogen.
Claim 3
Dependent Claim
10 words
The derivative of claim 1 wherein R 2 is hydrogen.
Claim 4
Dependent Claim
14 words
The derivative of claim 1 wherein R 2 is C 1 -C 6 alkyl.
Claim 5
Dependent Claim
22 words
The derivative of claim 1, wherein the substituent on R 2 when R 2 is C 1 -C 6 alkyl is ##STR27##
Claim 6
Dependent Claim
13 words
The derivative of claim 1, wherein R 3 is fluorine, chlorine or bromine.
Claim 7
Dependent Claim
10 words
The derivative of claim 1, wherein R 3 is carboxyl.
Claim 8
Dependent Claim
27 words
The derivative of claim 1, wherein R 4 and R 4 ' are individually selected from the group consisting of hydrogen, and C 1 -C 6 alkyl.
Claim 9
Dependent Claim
24 words
The derivative of claim 1 wherein R 4 and R 4 ' are individually selected from the group consisting of fluorine, chlorine and bromine.
Claim 10
Dependent Claim
27 words
The derivative of claim 1 wherein R 4 and R 4 ' are individually selected from the group consisting of carboxyl and C 1 -C 6 alkoxy.
Claim 11
Dependent Claim
60 words
An aniline derivative selected from the group consisting of α-(N-methyl-anilino)-benzyl-phosphonic acid, (3-chloro-N-methyl-anilino)-methane-phosphonic acid, (3-methyl-N-methyl-anilino)-methane-phosphonic acid, (3-methoxy-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-chloro-N-methyl-anilino)-methane-phosphonic acid, (N-ethylanilino)-methane-phosphonic acid, (N-benzylanilino)-methane-phosphonic acid, (N-propylanilino)-methane-phosphonic acid, (N-[2'-carboxyethyl]anilino-methane-phosphonic acid, (N-[2'-ethoxycarbonylethyl]anilino-methane-phosphonic acid, (4-fluoro-N-ethylanilino)-methane-phosphonic acid, (N-phenyl]-anilino)-methane-phosphonic acid, (N-[2-aminoethyl]anilino)-methane-phosphonic acid, 1-(N-methylanilino)-ethane-phosphonic acid, N-hydroxyethyl-anilino-methane-phosphonic acid, ([N-methyl-anilino]-methyl)-methyl-phosphonic acid, (N-methyl-anilino)-methane-phosphonic acid monomethylester, (N-[2-acelamido-ethyl]anilino)-methane-phosphonic acid, and the salt thereof with an acid or a base.
Claim 12
Dependent Claim
60 words
An aniline derivative selected from the group consisting of α-(N-methyl-anilino)-benzyl-phosphonic acid, (3-chloro-N-methyl-anilino)-methane-phosphonic acid, (3-methyl-N-methyl-anilino)-methane-phosphonic acid, (3-methoxy-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-chloro-N-methyl-anilino)-methane-phosphonic acid, (N-ethylanilino)-methane-phosphonic acid, (N-benzylanilino)-methane-phosphonic acid, (N-propylanilino)-methane-phosphonic acid, (N-[2'-carboxyethyl]anilino-methane-phosphonic acid, (N-[2'-ethoxycarbonylethyl]anilino-methane-phosphonic acid, (4-fluoro-N-ethylanilino)-methane-phosphonic acid, (N-phenyl]-anilino)-methane-phosphonic acid, (N-[2-aminoethyl]anilino)-methane-phosphonic acid, 1-(N-methylanilino)-ethane-phosphonic acid, N-hydroxyethyl-anilino-methane-phosphonic acid, ([N-methyl-anilino]-methyl)-methyl-phosphonic acid, (N-methyl-anilino)-methane-phosphonic acid monomethylester, (N-[2-acelamido-ethyl]anilino)-methane-phosphonic acid, and the salt thereof with an acid or a base.
Claim 13
Dependent Claim
27 words
An aniline derivative selected from the group consisting of (3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-ethyl-anilino)-methane-phosphonic acid and the salt thereof with an acid or a base.
Claim 14
Dependent Claim
27 words
An aniline derivative selected from the group consisting of (3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid, (4-fluoro-N-ethyl-anilino)-methane-phosphonic acid and the salt thereof with an acid or a base.
Claim 15
Dependent Claim
6 words
A compound consisting of (3-methyl-N-methyl-anilino)-methane-phosphonic acid.
Claim 16
Dependent Claim
6 words
A compound consisting of (3-methyl-N-methyl-anilino)-methane-phosphonic acid.
Claim 17
Dependent Claim
6 words
A compound consisting of (4-fluoro-N-methyl-anilino)-methane-phosphonic acid.
Claim 18
Dependent Claim
6 words
A compound consisting of (4-fluoro-N-methyl-anilino)-methane-phosphonic acid.
Claim 19
Dependent Claim
7 words
A compound consisting of (4 -fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid.
Claim 20
Dependent Claim
7 words
A compound consisting of (4 -fluoro-3-methyl-N-methyl-anilino)-methane-phosphonic acid.
Claim 21
Dependent Claim
6 words
A compound consisting of (4-fluoro-N-ethyl-anilino)-methane-phosphonic acid.
Claim 22
Dependent Claim
6 words
A compound consisting of (4-fluoro-N-ethyl-anilino)-methane-phosphonic acid.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-05-23 | 1997-11-22 | 1998-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-05-23 | 2001-11-22 | 2002-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-05-23 | 2005-11-22 | 2006-05-24 | $7700.00 | Window Closed / Lapsed |