US4716222A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Substrates for hydrolases
Assignee: BIOMED LABORDIAGNOSTIK GmbH
•
Filing: 1985-04-05
•
Granted: 1987-12-29
•
Expires: 2005-04-05
Abstract
Abstract Chromogenic substrates of the formula A-O-B are described, in which A represents the radical in the ion A-O- of a compound A-OH, whose absorbance is measured photometrically after hydrolysis of A-O-B, while B is the radical in a compound B-OH which makes the compound specific for the reaction with a given enzyme, and where A-OH is a hydroxynitropyridine, a hydroxynitrobenzopyranone, a dibenzox(or thi)azine or a dibenzopyranone or a derivative thereof, and B is a sugar or sugar derivative, an amino acid or an oligopeptide or an inorganic acid. These compounds can be used for the detection and determination of hydrolases.
Inventors
- 👤 Kurt Wallenfels
- 👤 Ahmed M. Fathy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:58
CPC Classifications
C; C07; C07H; C07H21/00; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6527; C07F9/6533; C07F9/65335; C07F9/655; C07F9/6552; C07F9/65522; C07H17/00; C07H17/02; C07H17/04; C07H17/06; C07H17/065; C07H17/075; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0802; C07K5/0804; C07K5/0806; C12; C12Q; C12Q1/00; C12Q1/34; C12Q2334/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
218 words
A compound of the formula A--O--B, in which A represents the radical in the ion A--O - of a heterocyclic compound A--OH with an acid pK a , whose absorbance is measured photometrically after hydrolysis of A--O--B, while B is the radical in a compound B--OH which makes the compound specific for the reaction with a given enzyme, and where A--OH is selected from the group consisting of: a. a compound of the formula I ##STR5## in which R 1 can be OH, NO 2 or halogen, and R 3 , R 4 and R 5 can be H or NO 2 , at the most two NO 2 being present, b. a compound of the formula II ##STR6## in which R 1 can be H or alkyl with 1-12 carbon atoms, and R 2 , R 3 or R 4 can be H or NO 2 , one or two NO 2 being present, c. a compound of the formula III ##STR7## in which R 1 can be 0 or an electron pair, R 2 can be O, S or N(CH 3 ) 2 , and R 3 can be O or S and d. a compound of the formula IV ##STR8## in which R 1 can be aryl, and B--OH is a sugar or sugar derivative.
Claim 2
Dependent Claim
218 words
A compound of the formula A--O--B, in which A represents the radical in the ion A--O - of a heterocyclic compound A--OH with an acid pK a , whose absorbance is measured photometrically after hydrolysis of A--O--B, while B is the radical in a compound B--OH which makes the compound specific for the reaction with a given enzyme, and where A--OH is selected from the group consisting of: a. a compound of the formula I ##STR5## in which R 1 can be OH, NO 2 or halogen, and R 3 , R 4 and R 5 can be H or NO 2 , at the most two NO 2 being present, b. a compound of the formula II ##STR6## in which R 1 can be H or alkyl with 1-12 carbon atoms, and R 2 , R 3 or R 4 can be H or NO 2 , one or two NO 2 being present, c. a compound of the formula III ##STR7## in which R 1 can be 0 or an electron pair, R 2 can be O, S or N(CH 3 ) 2 , and R 3 can be O or S and d. a compound of the formula IV ##STR8## in which R 1 can be aryl, and B--OH is a sugar or sugar derivative.
Claim 3
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(β-D-Maltotriosyl)-4-methyl-8-nitrobenzopyran-2-one.
Claim 4
Dependent Claim
114 words
A compound of the formula A--O--B, in which A represents the radical in the ion A--O - of a heterocylic compound A--OH with an acid pK a , whose absorbance is measured photometrically after hydrolysis of A--O--B, while B is the radical in a compound B--OH which makes the compound specific for the reaction with a given enzyme, and where A--OH is a compound of the formula II ##STR9## in which R 1 can be H or alkyl with 1-12 carbon atoms, and R 2 , R 3 , or R 4 can be H or NO 2 , one or two NO 2 being present, and B--OH is a sugar or sugar derivative.
Claim 5
Dependent Claim
114 words
A compound of the formula A--O--B, in which A represents the radical in the ion A--O - of a heterocylic compound A--OH with an acid pK a , whose absorbance is measured photometrically after hydrolysis of A--O--B, while B is the radical in a compound B--OH which makes the compound specific for the reaction with a given enzyme, and where A--OH is a compound of the formula II ##STR9## in which R 1 can be H or alkyl with 1-12 carbon atoms, and R 2 , R 3 , or R 4 can be H or NO 2 , one or two NO 2 being present, and B--OH is a sugar or sugar derivative.
Claim 6
Dependent Claim
28 words
A compound according to claim 3, wherein R 1 is H or alkyl with 1-3 carbon atoms, B--OH is glucose, a multidextrin, galactose, glucuronic acid, N-acetyl-glucosamine or fucose.
Claim 7
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(alpha-D-Glucopyranosyl)-4-methyl-8-nitrobenzo-pyran-2-one.
Claim 8
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(beta-D-Glucopyranosyl)-4-methyl-8-nitrobenzo-pyran-2-one.
Claim 9
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(2-Acetamido-3-deoxy-beta-D-glucopyranosyl)-4-methyl-8-nitrobenzopyran-2-one.
Claim 10
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(1-beta-D-Glucuronopyranosyl)-4-methyl-8-nitrobenzopyran-2-one
Claim 11
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(alpha-D-Maltotriosyl)-4-methyl-8-nitrobenzo-pyran-2-one.
Claim 12
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(beta-D-Maltotetraosyl)-4-methyl-8-nitro-benzo-pyran-2-one.
Claim 13
Dependent Claim
15 words
A compound of the formula II according to claim 1, identified by the name 2H-7-O-(beta-Galactopyranosyl)-4-methyl-8-nitrobenzopyran-2-one.
Claim 14
Dependent Claim
66 words
A compound according to claim 1, wherein in formula II R 1 is H or alkyl with 1-3 carbon atoms, in formula IV aryl is phenyl, CN or alkyl with 1-12 or 13 carbon atoms, and B--OH is glucose, a maltodextrin, galactose, glucuronic acid, N-acetylglucosamine or fucose, the protective group is toluenesulfonyl or a compound selected from the carbobenzyloxy (CBZ) group such as N-tosylalanine or CBZ-glycine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-28 | 1991-06-29 | 1991-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-28 | 1995-06-29 | 1995-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-28 | 1999-06-29 | 1999-12-29 | $7700.00 | Window Closed / Lapsed |