EP0103628A4 - Stabilisation de solutions de sels diazoiques. - Google Patents
Stabilisation de solutions de sels diazoiques.Info
- Publication number
- EP0103628A4 EP0103628A4 EP19830901291 EP83901291A EP0103628A4 EP 0103628 A4 EP0103628 A4 EP 0103628A4 EP 19830901291 EP19830901291 EP 19830901291 EP 83901291 A EP83901291 A EP 83901291A EP 0103628 A4 EP0103628 A4 EP 0103628A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- surfactant
- liquid composition
- stability
- diazonium salt
- brij
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000012954 diazonium Substances 0.000 title claims abstract description 25
- 150000001989 diazonium salts Chemical class 0.000 title claims abstract description 25
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000004094 surface-active agent Substances 0.000 claims abstract description 32
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- 210000001124 body fluid Anatomy 0.000 claims abstract description 9
- 239000010839 body fluid Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 12
- -1 fatty alcohol ethers Chemical class 0.000 claims description 9
- KKEBXNMGHUCPEZ-UHFFFAOYSA-N 4-phenyl-1-(2-sulfanylethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCS)CC1C1=CC=CC=C1 KKEBXNMGHUCPEZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- QFXJYJSYVMLCKA-UHFFFAOYSA-N (4-nitrophenoxy)methanamine Chemical compound NCOC1=CC=C([N+]([O-])=O)C=C1 QFXJYJSYVMLCKA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002280 amphoteric surfactant Substances 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical class CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims description 2
- CKQAOGOZKZJUGA-UHFFFAOYSA-N 1-nonyl-4-(4-nonylphenoxy)benzene Chemical class C1=CC(CCCCCCCCC)=CC=C1OC1=CC=C(CCCCCCCCC)C=C1 CKQAOGOZKZJUGA-UHFFFAOYSA-N 0.000 claims description 2
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 9
- 239000000243 solution Substances 0.000 description 18
- 238000011084 recovery Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000003929 Transaminases Human genes 0.000 description 3
- 108090000340 Transaminases Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000005615 azonium group Chemical group 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- GZCWLCBFPRFLKL-UHFFFAOYSA-N 1-prop-2-ynoxypropan-2-ol Chemical compound CC(O)COCC#C GZCWLCBFPRFLKL-UHFFFAOYSA-N 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- 108010051457 Acid Phosphatase Proteins 0.000 description 2
- 102000013563 Acid Phosphatase Human genes 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YNXICDMQCQPQEW-UHFFFAOYSA-N 1-naphthyl dihydrogen phosphate Chemical compound C1=CC=C2C(OP(O)(=O)O)=CC=CC2=C1 YNXICDMQCQPQEW-UHFFFAOYSA-N 0.000 description 1
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241000720950 Gluta Species 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 102100035703 Prostatic acid phosphatase Human genes 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
Definitions
- This invention relates to a method for enhancing the stability of certain diazonium salt solutions used in clinical laboratory determinations of enzyme levels in various body fluids.
- Diazotized aromatic amines are conventionally added to clinical tests as an indicator means to determine the concentrations of various components in body fluids.
- Acid phosphatase is present in the prostate gland of humans and, in cases of cancer to the prostate, the enzyme is released into the blood stream. Cancer of the prostate, therefore, can be diagnosed by tests, such as that disclosed in United States Patent No. 3,002,893, which measure serum acid phosphatase. This is determined by a process in which serum is incubated with a buffered phenolic phosphate ester substrate, and after incubation, an azonium salt of an aromatic amine containing from one to two a ino groups per molecule is added. This azonium salt reacts with the enzyme-liberated phenol, and the resultant color of the test solution is proportional to the prostatic acid phosphatase activity in the serum being tested.
- Gluta ic-oxalacetic transaminase enzyme levels in blood serum or other body fluids is indicative of certain types of cellular destruction as found in, for example, yocar- dial infarction, intrahepatic lymphoma or carcinoma, and
- a method for determining glutamic-oxalacetic transa inase levels in body fluids is disclosed in United States Patent No. 3,069,330. As discussed in United States Patent No. 3,069,330, the level of glutamic- oxalacetic transaminase enzyme is determined by a process in which a body fluid is incubated with a buffered mixture of L-aspartic acid and o-ketoglutaric acid.
- an azonium salt capable of coupling with the oxal ⁇ acetic acid formed by enzymatic action on the substrate is added, and the resultant color of the test solution is proportional to the glutamic-oxalacetic transaminase level in the fluid being tested.
- diazonium salts are also conventionally used as indicators for the detection and quantitation of 2-napthol (and other phenols) and for bilirubin.
- diazonium salts for these and other clinical tests using colorimetric determinations can be stabilized as solids in the form of double salts of zinc chloride and the like, they are normally hydroscopic and, therefore, if not kept in tightly sealed containers they will absorb moisture from the air and become unstable.
- the diazotized aromatic amines used as colorimetric indi ⁇ cators are also unstable in solutions. While stability of these diazonium salt solutions can be enhanced by keeping the solution cold, dark, and at an acid pH, even under these conditions significant deterioration as evidenced by discoloration, precipitate formation, and loss of reactivity is seen in a relatively short time.
- This classification of surfactants includes the polyethoxylated fatty alcohol ethers such as polyoxyethylene 23 lauryl ether sold under the tradename of Brij 35 by ICI Americas, Inc.
- polyethylene glycol p-nonylphenyl ethers such as that sold under the tradename of Igepal CO 630 by GAF of Wayne, New Jersey
- ethoxylated tridecyl alcohol sold under the tradename of Lipal 610 by Drew Chemical Corporation of Boonton, New Jersey.
- Polyethoxylated fatty acid esters such as that sold under the tradename of Myrj by ICI Americas, Inc., and polyethoxylated sorbitan fatty acid esters such as that sold under the tradename of Tween by ICI Americas, Inc. , also show the ability to enhance diazonium salt solution stability.
- the Myrj and Tween surfactants are not very stable in an acid environment, however, and should be avoided if the solution is to be kept at an acidic pH.
- surfactants which may be used in the practice of the present invention are those classified as cationic surfactants such as Monaquat PTD sold by Mona Industries of Paterson, New Jersey, and described in United States Patent No. 4,209,449.
- Amphoteric surfactants such as Miranol H2M sold by Hiranol Chemical Company, Inc. of Irvington, New Jersey may also be used in the practice of the present invention. Surfactants tested which are
- Table 1 shows the enhanced recovery of diazotized 5-nitro- 2-aminomethoxybenzene (Fast Red B, one of the many conven ⁇ tional diazonium salt solutions used as colorimetric clinical reagents) from solutions prepared by adding Fast Red B to a 0.3N hydrochloric acid solution in a 1 mg to 1 ml proportion. In all instances shown, the experimental solutions were kept at 37°C.
- Fluor Red B diazotized 5-nitro- 2-aminomethoxybenzene
- Table 1 shows the enhanced stability obtained with the addition of amphoteric, cationic, and nonionic surfactants to diazonium salt solutions.
- the effect noted for the sodium lauryl sulfate surfactant listed in the table carries to all those anionic surfactants tested - although an initial enhancement may occur, this rapidly decreases to an effect which differs little from that found in those solutions to which no surfactant has been added.
- Table 1 The data contained in Table 1 indicates that differing concentrations of the same surfactant have differing effects upon the recovery of the diazonium salt from solution. This concentration phenomena was studied, therefor, for a number of different surfactants. The results of a number of these studies are tabulated in the following tables.
- SUBSTITUTE SHEET OMPI appears consistent for other non-ionic, amphoteric, and cationic surfactants tested. Although stability for diazonium salt solutions is enhanced over a broad concen ⁇ tration of surfactant, because of the maximum point of stability, a preferred concentration range of surfactant would be 0.04% to 4.0%. More preferred ranges, however, would be 0.2% to 2.0%, or 0.4% to 2.0%.
- Table 5 shows the effect of adding 0.8% Brij 35 to a 0.05% diazotized 5-nitro-2- aminomethoxybenzene solution in 0.1N hydrochloric acid.
- Diazotized sulfanilic acid solutions that is the indica- tor means for clinical determination of bilirubin, was also tested to determine the stability of this reagent with the addition of surfactant.
- the surfactant chosen was Brij 35 at 1.0%, and stability was examined at both room temperature and at 4°C. As shown in Table 6, stability is also improved by the addition of surfactant to this test reagent.
- the present invention is directed to a means of stabilizing diazonium salt solutions, especially those solutions or reagents which are used in clinical determinations.
- each reagent may vary in accordance with the determination to be made, the addi ⁇ tion of a relatively small amount (that is from about 0.01 to 4.0%) of an amphoteric, cationic, or nonionic surfac ⁇ tant has been found to greatly enhance the stability of the reagent.
- a particularly stable reagent useful in the quanitification of alpha-naphthol released from alpha- naphthylphosphate in an assay for the enzyme acid phospha ⁇ tase for example, consists of a diazonium salt solution containing 0.05 grams of diazotized 5-nitro-o-anisidine and 0.8 grams of Brij 35 in 100 ml. of 0.3N hydrochloric acid.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35704282A | 1982-03-11 | 1982-03-11 | |
| US357042 | 1982-03-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0103628A1 EP0103628A1 (fr) | 1984-03-28 |
| EP0103628A4 true EP0103628A4 (fr) | 1984-09-19 |
Family
ID=23404061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19830901291 Withdrawn EP0103628A4 (fr) | 1982-03-11 | 1983-03-10 | Stabilisation de solutions de sels diazoiques. |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0103628A4 (fr) |
| DK (1) | DK517183D0 (fr) |
| IT (1) | IT1166502B (fr) |
| WO (1) | WO1983003254A1 (fr) |
| ZA (1) | ZA831707B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2154735B (en) * | 1984-01-27 | 1987-07-15 | Menarini Sas | Reagent for determining blood glucose content |
| IT1177513B (it) * | 1984-01-27 | 1987-08-26 | Menarini Sas | Reattivo liquido pronto per l'uso per la determinazione del contenuto di glucosio nel sangue |
| CA1293676C (fr) * | 1985-09-26 | 1991-12-31 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Detection de la bilirubine et reactifs correspondants |
| DE3900615C1 (fr) * | 1989-01-11 | 1990-02-08 | Hartung Laboratoire, Encamp, Ad | |
| US5149272A (en) * | 1991-05-30 | 1992-09-22 | Boehringer Mannheim Corporation | Assay for total and direct billirubin |
| US5981206A (en) * | 1992-05-20 | 1999-11-09 | Johnson & Johnson Clinical Diagnostic Systems, Inc. | Dry analytical element and method for the detection of prostatic acid phosphatase |
| CA2161574A1 (fr) * | 1994-11-15 | 1996-05-16 | James Noffsinger | Methode pour determiner par colorimetrie la concentration des leucocytes dans un fluide biologique |
| WO1996017251A1 (fr) * | 1994-12-02 | 1996-06-06 | Nitto Boseki Co., Ltd. | Procede de determination quantitative de bilirubine |
| US5935861A (en) * | 1997-11-21 | 1999-08-10 | Boehringer Mannheim Corporation | Diazonium ion assay reagents and methods for their use |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038031A (en) * | 1975-10-02 | 1977-07-26 | Miles Laboratories, Inc. | Test composition, device and method for detecting bilirubin |
| US4087331A (en) * | 1977-01-12 | 1978-05-02 | Coulter Electronics, Inc. | Colorimetric method for determining gamma-glutamyl transpeptidase and compositions useful therein |
| US4119401A (en) * | 1977-06-07 | 1978-10-10 | Technicon Instruments Corporation | Total bilirubin assay |
| JPS5594348A (en) * | 1979-01-08 | 1980-07-17 | Koji Takeuchi | Preparation of azo compound |
| DE2910199A1 (de) * | 1979-03-15 | 1980-09-25 | Hoechst Ag | Verfahren zur herstellung von diazoniumsalzloesungen |
| JPS5610255A (en) * | 1979-07-05 | 1981-02-02 | Terumo Corp | Bilirubin detecting test piece |
| DD148878A3 (de) * | 1979-12-05 | 1981-06-17 | Gerhard Knoechel | Verfahren zur herstellung von diazoniumverbindungen schwer diazotierbarer aromatischer amine |
| JPS56153255A (en) * | 1980-04-28 | 1981-11-27 | Katayama Kagaku Kogyo Kk | Reagent for measuring bilirubin in body fluid |
| US4370318A (en) * | 1980-07-07 | 1983-01-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin-related compounds as immunopotentiator |
-
1983
- 1983-03-10 WO PCT/US1983/000315 patent/WO1983003254A1/fr not_active Application Discontinuation
- 1983-03-10 EP EP19830901291 patent/EP0103628A4/fr not_active Withdrawn
- 1983-03-11 IT IT20041/83A patent/IT1166502B/it active
- 1983-03-11 ZA ZA831707A patent/ZA831707B/xx unknown
- 1983-11-11 DK DK5171/83A patent/DK517183D0/da not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| No further relevant documents disclosed * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA831707B (en) | 1984-10-31 |
| IT8320041A0 (it) | 1983-03-11 |
| DK517183A (da) | 1983-11-11 |
| WO1983003254A1 (fr) | 1983-09-29 |
| EP0103628A1 (fr) | 1984-03-28 |
| DK517183D0 (da) | 1983-11-11 |
| IT1166502B (it) | 1987-05-06 |
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