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US4457866A Expired / Lapsed US ⏱️ 0.0 years remaining

Chromogenic compounds and their use as enzyme substrates

Assignee: Siemens Healthcare Diagnostics GmbH Germany
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Filing: 1982-10-19
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Granted: 1984-07-03
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Expires: 2002-10-19
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Abstract

Abstract What are disclosed are chromogenic peptides useful as substrates for the detection and determination of enzymes having a hydrolytic action and methods for detecting and determining enzymes with such peptides.

Inventors

  • 👤 Hermann E. Karges
  • 👤 Helmut Heber
  • 👤 Rainer Uhmann
  • 👤 Volker Teetz
  • 👤 Rolf Geiger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 08:16
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/06; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/06026; C07K5/06034; C07K5/06052; C07K5/06078; C07K5/06086; C07K5/06095; C07K5/06104; C07K5/08; C07K5/0802; C07K5/0804; C07K5/0808; C07K5/0812; C07K5/10; C07K5/1002; C07K5/1005; C07K5/1013; C07K5/1016; C12; C12Q; C12Q1/00; C12Q1/34; C12Q1/37; C12Q2337/00; C12Q2337/10; C12Q2337/12; Y; Y10; Y10S; Y10S530/00; Y10S530/802; Y10S930/00; Y10S930/01; Y10S930/28

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 180 words
A compound of the formula W--P--B--X--NH--R wherein W is R 1 CO-- wherein R 1 is C 1 -C 6 aliphatic hydrocarbon, C 6 -C 10 aromatic hydrocarbon, C 7 -C 10 araliphatic hydrocarbon; or C 6 -C 10 alkaryl, or W is R 2 OCO-- wherein R 2 is C 1 -C 6 aliphatic hydrocarbon, C 7 -C 10 araliphatic hydrocarbon, or alkyl 1-6 sulfonylalkyl 2-6 , or W is benzenesulfonyl or C 7 -C 10 alkarylsulfonyl; P is valine, serine, Phe-Pro, Val-Glu-Gly, Val-Leu, Gly-Pro-Glu-Gly, or Ile-Glu-Gly, side chain groups of which may be substituted by protective groups; B is arginine, lysine, phenylalanine, tyrosine, or homoarginine; X is an L-amino acid selected from the group consisting of phenylalanine, tyrosine, valine, leucine, serine, glycine, and Leu-Phe, side chain groups of which may be substituted by protective groups; and R is an aromatic hydrocarbon, which may be substituted; wherein X--NH--R is a chromogenic group which is cleaved by hydrolytic enzymatic action to form a compound H 2 N--R, the amount of which can be measured by photometric, spectrophotometric, or fluorescence-photometric methods.
Claim 2
Dependent Claim 180 words
A compound of the formula W--P--B--X--NH--R wherein W is R 1 CO-- wherein R 1 is C 1 -C 6 aliphatic hydrocarbon, C 6 -C 10 aromatic hydrocarbon, C 7 -C 10 araliphatic hydrocarbon; or C 6 -C 10 alkaryl, or W is R 2 OCO-- wherein R 2 is C 1 -C 6 aliphatic hydrocarbon, C 7 -C 10 araliphatic hydrocarbon, or alkyl 1-6 sulfonylalkyl 2-6 , or W is benzenesulfonyl or C 7 -C 10 alkarylsulfonyl; P is valine, serine, Phe-Pro, Val-Glu-Gly, Val-Leu, Gly-Pro-Glu-Gly, or Ile-Glu-Gly, side chain groups of which may be substituted by protective groups; B is arginine, lysine, phenylalanine, tyrosine, or homoarginine; X is an L-amino acid selected from the group consisting of phenylalanine, tyrosine, valine, leucine, serine, glycine, and Leu-Phe, side chain groups of which may be substituted by protective groups; and R is an aromatic hydrocarbon, which may be substituted; wherein X--NH--R is a chromogenic group which is cleaved by hydrolytic enzymatic action to form a compound H 2 N--R, the amount of which can be measured by photometric, spectrophotometric, or fluorescence-photometric methods.
Claim 3
Dependent Claim 22 words
A compound as in claim 1 wherein R is nitrophenyl, naphthyl, nitronanphthyl, methoxynaphthnyl, phenyl, methylnitrophenyl, dinitrophenyl, quinolyl, nitroquinolyl, or a salt thereof.
Claim 4
Dependent Claim 23 words
A compound as in claim 1 wherein R is nitrophenyl or is nitrophenyl substituted by halogen, trifluoromethyl, carboxyl, methoxy, sulfonic acid, or cyano.
Claim 5
Dependent Claim 25 words
A compound as in claim 1 wherein R is dimethoxycarbonylphenyl, pyridine, nitrobenzothiazole, pyrazine, triazole, benzopyrazole, chrysene, naphthyl, methoxynaphthyl, azulene, or aminocoumarin, which may be substituted.

References Cited (Backward Citations)

US3884896A Cited
US3886136A Cited
US4016042A Cited
US4028318A Cited
US4137225A Cited
US4119620A Cited
US4279810A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-07-03 1988-01-02 1988-07-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-07-03 1992-01-02 1992-07-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-07-03 1996-01-02 1996-07-03 $7700.00 Window Closed / Lapsed

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